Russian Chemical Reviews 68 (9) 781 ± 799 (1999) Aryl (meth)acrylates and polymers based on them V G Syromyatnikov, L P Paskal', I A Savchenko Contents I. Introduction II. Methods for the synthesis of aryl (meth)acrylates III. Polymerisation of aryl (meth)acrylates IV. Aryl (meth)acrylates in copolymerisation reactions V. Structure and properties of poly[aryl (meth)acrylates] VI. Chemical and photochemical properties of poly[aryl (meth)acrylates] and their copolymers VII. Practical application of aryl (meth)acrylates Abstract. Data on the synthesis, polymerisation and copolymer- isation of aryl (meth)acrylates are generalised and systematised. Chemical and photochemical properties of the polymers and copolymers are considered. Basic directions of practical applica- tion of poly[aryl (meth)acrylates] and copolymers are demon- strated.The bibliography includes 449 references. I. Introduction Aryl (meth)acrylates H2C=C(R)CO2Ar (hereinafter R=H, Me) occupy a special place in the series of (meth)acrylates due, first of all, to the diversity of functional groups which may be introduced into the aromatic ring of these monomers and the derived polymers. Specificity of physical properties of poly[aryl (meth)acrylates] is determined by the enhanced rigidity of the polymeric chains (because of the presence of aromatic rings). Aryl (meth)acrylates are easily copolymerised with most of the known monomers, which opens broad prospects for their application. Until recently, the results of numerous studies on the synthesis and properties of aryl (meth)acrylates have not been generalised.The present review is intended to fill this gap. II. Methods for the synthesis of aryl (meth)acrylates Earlier methods for the synthesis of aryl (meth)acrylates were rather complicated and were not of a general character. Thus phenyl acrylate (PA) was prepared by direct esterification of phenol with acrylic acid in the presence of trifluoroacetic anhy- dride 1 and also by the Reppe reaction, i.e., by the reaction of acetylene and carbon monoxide with phenol.2 Phenyl 3 and naphthyl acrylates 4 were obtained by pyrolysis of 2-acetoxypro- pionates MeCH2(OAc)CO2Ar. The systematic studies of the methods for the preparation of aryl acrylates were initiated by Magagnini and Pizzirani 5 who investigated the reactions of V G Syromyatnikov, L P Paskal', I A Savchenko Taras Shevchenko Kiev University, ul.Vladimirskaya 60, 252033 Kiev, Ukraine. Fax (38-044) 225 12 73. Tel. (38-044) 221 02 82 (V G Syromyatnikov), (38-044) 221 02 29 (L P Paskal') Received 21 August 1998 Uspekhi Khimii 68 (9) 861 ± 880 (1999); translated by V D Gorokhov #1999 Russian Academy of Sciences and Turpion Ltd UDC 541.64 : 547.564.4 781 781 783 785 788 790 792 acryloyl chloride with phenols. In addition to PA, these authors described acrylates of isomeric cresols, chlorophenols, thymol, hydroxybiphenyl and 4-methoxyphenol. It should be noted that the reactions were carried out under conditions precluding the addition of hydrogen chloride to the double bond.In earlier attempts of the synthesis of acrylates by this method, this addition took place; therefore, b-chloropropionates were the major prod- ucts. Conducting of these reactions in the presence of triethyl- amine allowed a considerable increase in the yields of methacrylates of substituted phenols. This method was success- fully used to prepare isomeric phenol di(meth)acrylates,6 2-biphenylyl acrylate 7 and 4-biphenylyl (meth)acrylate 8 and mono- and di(meth)acrylates of substituted 2,2 0-methylenebis- phenols.9 Aryl (meth)acrylates are usually synthesised by the reaction of phenols with (meth)acryloyl chloride in the presence of hydrogen chloride acceptors. This process may be carried out in inert solvents in the presence of Na2CO3,10 in pyridine,11 in ethanolic solution of KOH12 or triethylamine.7 It is also convenient to use the Schotten ± Baumann reaction, which involves the acylation of phenolates with (meth)acryloyl chloride in aqueous solutions at reduced temperature in the presence of an excess of alkali.13 This reaction occurs efficiently at the interface of the aqueous and organic phases.14 Monomers based on halogenated 2,2-di(4- hydroxyphenyl)propanes 15 and hydroxyphenyl derivatives of 2H-benzotriazole 16 were prepared in this manner.The methods described above have allowed the preparation of numerous alkyl- (see Refs 4, 6, 13, 17, 18), halogeno- (see Refs 4, 6, 11, 14) and nitro-substituted 4, 10, 19 phenyl (meth)acrylates (PMA). At the same duration and temperature of the reaction, the yields of esters decreased in the following order: meta- isomer>para-isomer>ortho-isomer>disubstituted phenol.10 Optimum conditions were found for the preparation of 2,6-dimethylphenyl acrylate, 2,4,6-trichloro-, 2,4,6-tribromo-, 2,4,6-trimethyl-, 2,6-diisopropyl- and 2,6-di(tert-butyl)-phenyl methacrylates, 2,4,5-trichlorophenyl acrylate 21 and meth- acrylate.22 PMA with substituents in the aromatic ring containing the aldehyde and ketone,23 carboxy,24, 25 benzyl,26 tetracyanocyclo- butyl 27 and dioxolane 28 groups have been described. Special mention should be made of (meth)acrylates of hydroxyphenyl- acetic 29 and hydroxybenzoic 24, 25 acids as well as of surfactant salts 30 of the general formula CH2=CMeC(O)OC6H4(CH2)nX [n=3, 7;X=CO2Na,N+(CnH2n+1)3Z7;Z=Cl, Br, I,MeSO4].782 Bun,32 ± 34, 36 4-(Meth)acryloyloxybenzoic acids form liquid-crystalline pol- ymers upon polymerisation and give birth to a large number of mesomorphic monomers and polymers.31 Of all monomers of this type, the best studied are the esters of the general formula CH2=CRC(O)OYC(O)OYR 0 (R 0=H,32 Me,33 OR00; R00=Me,32 ± 35, Pr,34 n-C6H13 37 and Alk(C87C16) 36 (hereinafter Y=1,4-C6H4).Monomers with more complex structures have been also described, e.g., meth- acrylates with the mesogenic side groups YC(O)OYOC(O)YOR0 (R0=H, Alk);38 or thermotropic bisacrylates R0XR0 (X=(CH2)n; R0=CH2=CHC(O)O. n=6 ± 10, 12; .YC(O)OYC(O)O.39 It should be noted that mesomorphic mono- mers are also found among aryl (meth)acrylates with a different character of substitution.These are acrylates and methacrylates of hydroxybiphenyl with alkyl 40 and alkoxy 41, 42 substituents or the CN group 43 at the position 40. It is noteworthy that poly(4,40- biphenylene diacrylate) does not possess liquid-crystalline proper- ties.44 The group of mesomorphic monomers also includes easily polymerisable acrylates of azomethines derived from 4-hydroxy- benzaldehyde. Polymers with Schiff's bases as the pendent groups can be obtained by polymer-analogous transformations from polyacryloyl chloride and the corresponding hydroxybenzylide- neaniline.45 A large group of this type of monomers of the general formulaCH2=CRC(O)OYCH=NX [X=Alk(C17C4), C6H4Z; Z=OH, OMe, OEt, NMe2, NEt2, NHPh, naphthyl, pyridyl] has been proposed 46 for the preparation of non-aqueous dispersions of polymers used in polygraphy.4-(4-Acryloyloxybenzylideneamino)phenyl acrylate 44 and N-(4-cyanobenzylidene)-4-acryloyloxyaniline are azomethines based on 4-aminophenol.47 Mesomorphic monomers (as well as the derived polymers) are rarely found among methacryloylazo- methines.48 (Meth)acrylates of hydroxyazobenzenes 49 ± 51 and hydroxy- azoxybenzenes 52 were used to prepare liquid-crystalline poly- mers. Azo-monomers possess, as a rule, alkyl, alkoxy or aryl substituents in the para-position relative to the azo group. The respective polymers are lyotropic or thermotropic liquid crystals, which undergo reversible changes under the action of UV radiation.53 Liquid-crystalline polymers based on 4,4 0-(bisac- ryloyloxy)azoxybenzene 44 are also obtained by the reaction of 4-hydroxyazobenzene with poly(acryloyl chloride).54 Comb-like polymers with liquid-crystalline properties were obtained by polymerisation of hydroquinone mono(meth)acrylates esterified at the second OH group with 4-n-alkoxybenzoic acids.55 ± 58 The results of studies on liquid-crystalline polymers derived from aryl (meth)acrylates have been described rather comprehen- sively in monographs.59, 60 Syntheses of (meth)acrylates of derivatives of condensed aromatic systems (naphthalene, anthracene, phenanthrene) have been described.61 Syntheses of a- and b-naphthyl esters of some a,b-unsaturated acids,62 2-(b-substituted acryloyl)-1-methacry- loyloxynaphthalenes, which are cross-linking agents,63 and 4-benzoylamino-a-naphthyl methacrylate,64 which is an efficient thermostabiliser, are documented.Monomeric dyes of the anthra- quinone series were obtained by the reaction of unsaturated acid chlorides with 4-amino-1,5-dihydroxy-2,6-diisobutyl-, 5-(3-ami- nophenylthio)-1,5-dihydroxy-2,6-diisobutyl- and 4,5-diamino- 1,8-dihydroxy-2,7-diisobutylanthraquinones.65 Copolymerisa- tion of these dyes with styrene and butyl methacrylate yields polymers self-coloured in yellow, red and blue. Kimura et al.66 have described 2- and 9-fluorenyl methacrylates. Upon their polymerisation in the presence of a telogen, the degree of telomerisation of the second monomer is lower.A number of monomers based on fluoranthene, including 3-fluoranthenyl methacrylate, produce polymers of the donor type, which form charge-transfer complexes possessing electrical properties with tetracyanoquinodimethane and tetracyanoethylene.67 Methacrylates of the 8-hydroxyquinoline series 68 of the general formula V G Syromyatnikov, L P Paskal', I A Savchenko R00 X=H, Br, Cl, I; R0=C(O)CMe CH2; R00=H, Br, Cl, CH2OMe, CH2OEt X N OR0 were synthesised in order to obtain subsequently medicinal preparations with prolonged action.69, 70 Halogens were shown to favour polymerisation. Methacrylates of hydroxyphenyl deriv- atives of other nitrogen-containing heterocycles are also known, e.g., 1,3-diphenyl-5-(4-methacryloyloxyphenyl)-2-pyrazoline.71 Of these, the most complex are acrylate and methacrylate of 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin 72 (the respec- tive polymers possess semiconducting properties and adsorb oxygen at temperatures below 200 K) and of 5-(4-acryloyloxy- phenyl)-15-phenyl-2,8,12,18-tetraethyl-3,7,13,17-tetramethylpor- phyrin.73 Some monomers contain the methacryloyloxy group bound directly to the heterocyclic ring, e.g., 2-pyridyl methacrylate.74 Aryl (meth)acrylates with the nitrogen-containing heterocyclic substituents in the para- and meta-positions of the benzene ring have been described.75 The initial N-(hydroxyphenyl)imides were obtained by condensation of aminophenols with the correspond- ing anhydrides. Monomers were synthesised by acylation with unsaturated acid chlorides.As regards aryl (meth)acrylates with nitrogen-containing substituents in the phenyl group, monomers with the nitro (see Refs 4, 10, 19) and cyano 76 groups have been described; a number of monomers with the azo (see Refs 77, 78), azoxy and azomethine groups 79 ± 82 are also known. 4-Azidophenyl methacrylate,83 salicinide,84 N-benzyl- and N-phenyl-4-hydroxybenzamide acryl- ates and methacrylates 85 were synthesised. 4-Aminophenyl methacrylate proved to be sensitive to oxida- tion, which reduces the possibility of its practical application.86 However, 3-(N,N-dimethylamino)phenyl methacrylate is fairly stable,76 it forms charge-transfer complexes with electron accept- ors and is promising for the synthesis of polymeric photosemi- conductors.Many reactive monomers, e.g., acylaminophenyl methacry- lates of the general formula R0C(O)NHC6H4OC(O)CR=CH2 (R0=H, Me, Et, Pr, Bu, C5H11, PhCH=CH, O2NC6H4 and BrC6H4) were obtained by N-acylation of isomeric aminophenols with equimolecular amounts of carboxylic acid chlorides (in anhydrous acetone, methanol or DMF) with subsequent esterifi- cation by the Schotten ± Baumann reaction with acryloyl or methacryloyl chlorides.87 ± 90 If 4-, 3- or 2-aminophenols are esterified with methacrylic acid, both functional groups react to give 4-, 3- or 2-(meth)acryloylaminophenyl (meth)acrylates.These reactive monomers undergo cross-linking in the polymerisa- tion.14, 91, 92 Di- and tri(meth)acryloyl derivatives of 2,4-diamino- phenol (amidol) were synthesised by successive acylation.92 Diacryloyl and di(meth)acryloyl derivatives of nitroamino- phenols O2N OC(O)CR CH2 NHCOCR CH2 were prepared 93 by acylation of 2-amino-4-nitro- and -5-nitro- phenols with unsaturated acid chlorides in tetrahydrofuran in the presence of triethylamine. Based on 4-amino-a-naphthol, azonaphthyl methacry- lates,94, 95 CMeC(O)O N N R0 CH2 R0=H, OMe, Br, NO2,Aryl (meth)acrylates and polymers based on them imidonaphthyl methacrylates 94 and 4-benzoylamino-a-naphthyl methacrylate 95 were synthesised. Thus, aryl (meth)acrylates with diverse functional groups in the aryl residue have been prepared to date.III. Polymerisation of aryl (meth)acrylates Aryl (meth)acrylates are relatively easily polymerised by a radical mechanism, the polymerisation rate being mainly determined by steric effects of substituents.96 Thus ortho-substituted PMA are appreciably less reactive than the para-isomers, the chemical nature of the substituent does not play any substantial role, which has been confirmed by the results of polymerisation of nitro- and methoxyphenyl methacrylates.13, 97, 98 Polymerisation was carried out in block and in different solvents in the presence of benzoyl peroxide. Since the electronic effect of the nitro and methoxy groups is opposite, one could expect that the rates of polymerisation of o- and p-nitrophenyl methacrylates and o- and p-methoxyphenyl methacrylates would be different; however, polymerisation of para-derivatives occurred faster in both cases. The EPR spectra of radicals devoid of ortho-substituents, e.g., poly(phenyl methacrylate) (PPMA) and poly(4-methylphenyl methacrylate), are identical, whereas the spectra of radicals of 2,6-diisopropylphenyl methacrylate and 2,6-di-tert-butylphenyl methacrylate revealed differences related to the shielding of the growing end of the polymeric chain by the ortho-substituents and the a-methyl group.99 The overall rate constant of the bulk polymerisation of alkylphenyl methacrylates (alkyl=Et, Pri, But) is higher for the para-substituted monomers than for the ortho-substituted ones and is virtually independent of the substituent size, whereas for the ortho-isomers this constant decreases with the increase in the substituent size.100 The reaction order with regard to the initiator (dilauryl peroxide) is 0.5 for non-substituted PMA, while it is 0.64 ± 0.94 for the sterically hindered monomers. The presence of methyl groups in the ortho-position (e.g., in 2,6-dimethylphenyl methacrylate) decreases appreciably the ceiling temperature of polymerisation (down to 73 8C) compared to that of non- substituted PMA (140 8C).101 The overall activation energy (kJ mol71) increases in the following order: 2,6-diisopropyl- phenyl methacrylate (45.7)<4-tert-butylphenyl methacrylate (49.9)<4-(1,1,3,3-tetramethylbutyl)phenyl methacrylate (59.6)< 4-methyl-, 4-ethyl- and 4-isopropylphenyl methacrylates (70 ± 76).102,103 Substitution of the cyclohexyl radical for the phenyl radical in the molecule of aryl methacrylate affects the polymerisation rate.For example, methacrylate of thymol, which contains a bulky isopropyl residue, is polymerised with difficulty, while methacry- late of menthol (hydrogenated thymol) analogous to the preced- ing monomer is polymerised easily under the same conditions.13 This is rationalised by the non-planarity of the cyclohexane ring and, consequently, by a lower rigidity of this monomer molecule compared to the methacrylate of thymol. Block polymerisation of substituted PMA is accompanied by gel-effect, which is observed in 2,4,6-tribromophenyl, 4-tolyl, 4-cyclohexylphenyl and 4-methoxyphenyl methacrylates at 35%, 35%, 15% and 2% conversions of the monomer, respectively [the concentration of the polymerisation initiator, viz., azobisisobu- tyronitrile (AIBN) is 0.4%].104 The kinetic parameters of PMA polymerisation in block and in solvent (60 8C, AIBN) were compared with those for alkyl methacrylates.105 The overall polymerisation rate has an order of 0.5 with respect to the initiator and 1 with respect to the monomer, i.e., it is described by the usual equation of radical polymerisation. The ratio of the chain termination constant (kt) to the squared chain propagation constant (kp) increases in the following order: (phenyl<isobutyl &n-butyl<ethyl<methyl) methacrylate.According to the radiometric analysis of the initiator fragments, the share of disproportionation in PMA is 89% [72% in methyl methacrylate (MMA)]. The initiation rate of radical polymerisation of PMA by 783 t AIBN depends slightly on the nature of the solvent, while kp (litre mol71 s71) increases in the following series of solvents: benzene (176)<fluorobenzene (180)<chlorobenzene (223)< anisole (230)<bromobenzene (235)<benzonitrile (243).106 The magnitude of kp was found to correlate with the difference in chemical shifts of b-alkene protons of monomers depending on the solvent. TheMOLCAO method was used to calculate the stabilisation energy in the formation of complexes of a radical with a solvent; kp was found to decrease with the increase in the complexation energy.It was shown later that this trend holds for MMA107 and PMA.108 The rate of radiation-induced polymerisation of PMA is proportional to the radiation dose to the power 0.65;109 in the temperature range 20 ± 34 8C, the activation energy of the process is equal to 14.15 kJ mol71, kp/k0:5=0.0198. At high degrees of conversion, a three-dimensional network is formed owing to the involvement of the terminal double bonds. Investigation of the influence of substituents on the radical polymerisation of PA has shown that the rate of this process increases in the order: methyl acrylate<2-chlorophenyl acryl- ate<PA<4-chlorophenyl acrylate.110 This is rationalised by changes in the flexibility of the propagating polymer chains. The increase in the overall polymerisation rate (toluene, 60 8C, lauryl peroxide) was found to increase in the following series:111 (2-tert- butyl- < 2-isopropyl- & 2-propyl- < 2-ethyl- < 2-methyl- < PMA < 4-methyl- < 4-isopropyl- < 4-tert-butyl-< 4-propyl- phenyl) methacrylate. The reaction order with regard to lauryl peroxide is 0.51 ± 0.87 depending on the monomer concentration.In the radical polymerisation of 2,4,5-trichlorophenyl meth- acrylate 112 in dioxane (kp=2.736103, kt = 7.226107 litre mol71 s71), the polymerisation rate is proportional to the monomer concentration to the power 1.5, which is explained by the possible formation of complexes of the monomer with the solvent molecules.In the case of radical polymerisation of nitro- phenyl methacrylates, at a low monomer concentration (0.01 mol litre71) one observes an inhibitory effect of the intra- and intermolecular chain transfer, the former being preva- lent.113 ± 115 For this reason, 2,6-dinitrophenyl, 2-methyl-4,6- dinitrophenyl and picryl methacrylates are not polymerised under these conditions, and the conversion of 2,4-dinitrophenyl methacrylate hardly reaches 2.6% in 2 h. The reaction orders of 4-biphenyl methacrylate polymerisation (inDMFwith AIBN) are 0.55 and 1.1 with respect to the initiator and monomer respec- tively; the total activation energy is 58 kJ mol71 (see Ref. 8). Replacement of an alkyl substituent by the electron-with- drawing acyl substituent in the benzene ring leads to an increase in the polymerisation rate of substituted phenyl (meth)acrylates because of the lower activation energy of the C=C bond cleavage.17 DTA studies of thermal bulk polymerisation of 4-acetylphenyl acrylate and methacrylate have shown116 that this process is the first-order reaction with respect to the mono- mer, the activation energies are equal to 228.1 and 120.5 kJ mol71, respectively.High polymerisation rates were observed for acylaminophenyl (meth)acrylates;87, 88 however, the rate of polymerisation decreased with increase in the length of the acyl radical. On the other hand, 4-diethylaminophenyl acrylate and methacrylate polymerised at a lower rate than non-substi- tuted PMA.89 Radical polymerisation of mixed diesters of 2,20-methylenedi- phenols with methacrylic and crotonic acids 117 OR00 OR0 R000 CH2 , Me NO2 whereR0 and/orR00 are methacrylic and crotonic acid residues and R000=H, Me, But, resulted in soluble polymers where R0 = R00 (polymerisation involved the methacryloyl group alone),784 insoluble dimethacrylates where R0 and R00 were the methacrylic acid residues and no polymerisation occurred where R0 and R00 were the crotonic acid residues.(Meth)acryloyl derivatives of N-hydroxyphenyl-substituted phthalimide 118 R0C6H4OC(O)CR=CH2 (R0=phthalimido) II IV III Monomer I R H H MeMe para meta meta para Position of R0 and alicyclic diacylamines 118, 119 polymerise at high rates and are more reactive than PMA, which seems to be due to the electron- withdrawing character of the imide fragment.The reactivity of monomers decreases in the following order: I >III>II>IV> p-acetylaminophenyl methacrylate (p-AAPMA), acrylates being more reactive than the corresponding methacrylates and the para- isomers more reactive than the meta-isomers.118 The reactivity of m-phthalimidophenyl (meth)acrylates 120 R00 O R000 N R000 O OC(O)CR0 CH2 R000 Monomer R000 R00 R0 Me I H H H II Me H H III H Cl Cl IV Me Cl Cl V Me Br Br VI NO2 H decreases with in the series: IV>V>II>m-AAPMA>VI, i.e., with the weakening of the electron-withdrawing character of the phthalimido group.The reduced reactivity of the monomer with the nitro group in the phthalimide cycle may be explained by its inhibitory action. The polymerisation rate of imidonaphthyl (meth)acrylates is lower than that of analogous imidophenyl methacrylates, and, according to Vretik et al., 94 this is due to the reduced reactivity of radicals because of a stronger electronic conjugation in the naphthyl-containing system. The most reactive of all the naph- thyl (meth)acrylates studied proved to be bismethacrylate with an additional cycloalkene double bond. This compound was obtained by the reaction of endic dianhydride with 1-amino-4- methacryloyloxynaphthalene.94 Irrespective of the initiation mode (thermal or photo-initia- tion),m-(succinimido)phenyl methacrylate (m-SIPMA) and acryl- ate (m-SIPA) occupy an intermediate position with regard to their reactivity between m-phthalimidophenyl methacrylate (m-PTIPMA) and acrylate (m-PTIPA), and acetylaminophenyl methacrylate (m-AAPMA) and acrylate (m-AAPA): m-PTIPMA>m-SIPMA>m-AAPMA>PMA;m-PTIPA> m-SIPA>m-AAPA>PA, i.e., there is correlation between the electron-withdrawing properties of the substituent and polymer- isability of substituted phenyl (meth)acrylates.121 High reactivity of these aryl (meth)acrylates allows the introduction of the above- mentioned heterocyclic fragments into the side chains of macro- molecules in order to impart definite photochemical, biological and other properties to the polymeric materials.Based on imidoaryl (meth)acrylates,122, 123 R0 O R00 X N n O X=OC(O)CR=CH2; R0, R00=NO2, NH2; n=1, 2; V G Syromyatnikov, L P Paskal', I A Savchenko O R0 X N n O X=NH2, OC(O)CR=CH2; R0=NO2; n=1, 2 homopolymers were obtained with the controllable intramolecu- lar energy transfer. In such polymers, movement of singlet or triplet excitons from one part of the macromolecule to another or from one unit chain to another is observed. The prerequisite for such a transfer is the presence of isolated aromatic systems with different excitation energies in each of the neighbouring units; the initial excitation should be generated in a definite element of the system. Such compounds are promising for the design of micro- electronic devices in which advantage is taken of photophysical processes at the molecular level.124 Polymerisability of bifunctional monomers deserves special mention.Cross-linked polymers are formed upon polymerisation of p- and m-phenylene di(meth)acrylates; o-phenylene diacrylate can undergo cyclopolymerisation 7 with the formation of ladder polymers; the extent of cyclisation increases with the decrease in the monomer concentration and the increase in the polymer- isation temperature.125 At a monomer concentration above 0.5 mol litre71, an insoluble polymer is formed. The intramolec- ular chain growth in the cyclopolymerisation follows mostly the `head-to-tail' mechanism, and a small number of units are formed by the `head-to-head' mechanism.Radical polymerisation of 2-allylphenyl (meth)acrylates is a two-step process:126 at an 18%± 30% monomer conversion, a soluble low-molecular-mass polymer is formed, which is then cross-linked. The low molecular mass of the product and the absence of the gel-effect are associated probably with the ability of the allyl group to undergo chain transfer. A detailed study of the polymerisation of 2-allylphenyl acrylate in toluene at 60 8C in the presence of AIBN revealed high content of the residual double bonds in the pendent allyl groups of the polymer.127 Subsequent cyclopolymerisation occurs due to the reaction of theC=Cbonds of the acryloyl and allyl groups. Cyclopolymerisation of 2-allylphenyl, 2-(o-allylphenoxy)ethyl and 4-(o-allylphe- noxy)butyl acrylates catalysed by alkylaluminium chlor- ides 127 ± 129 yields 8-, 11- and 13-membered rings; however, the catalyst's activity is insignificant for the formation of the 15-membered ring from 6-(o-allylphenoxy)hexyl acrylate.Polymerisation of ortho-, meta- and para-(meth)acryloyl- aminophenyl (meth)acrylates initiated by AIBN occurs with the formation of cross-linked polymers.92 A decrease in the reactivity in the order meta-> ortho->para-aminophenol di(meth)acryl- ates is associated with the character of conjugation in these monomers. Tri(meth)acryloyl derivatives of 2,4-diaminophenol (amidol) are more reactive than the corresponding (meth)acryloylaminophenyl (meth)acrylates, whereas di(meth)- acryl derivatives of amidol (with a free OH group) do not polymerise.Upon polymerisation of monomers based on 2-amino-4- and -5-nitrophenols, no formation of cross-linked polymer is observed even at a 60% conversion,93 as is the case of polymerisation of di(meth)acryloyl derivatives of 2-aminophenol. The presence of the nitro group decreases the number of active centres in the system resulting in the higher probability of chain transmission and formation of cyclolinear structures in macro- molecules. Cinnamoylaminophenyl (meth)acrylates 90 H2C=CRC(O)OYNHCOCH=CHPh polymerise at a lower rate than di(meth)acryloyl derivatives of isomeric aminophenols; the early chain termination at low conversions appears to be due to the inability of the cinnamoyl C=C bond, which acts as a trap for free radicals, to polymerise.This conclusion is prompted by comparison of the IR spectra ofAryl (meth)acrylates and polymers based on them the monomer and the polymer. Photosensitivity of such mono- mers (photoinitiator, benzoin), like that of 4-cinnamoylamino- phenol, confirms the non-reactivity of the cinnamoyl double bond in radical polymerisation and its capability of photoaggrega- tion.130 The nitro group in 4-nitrophenyl cinnamate or in 4-nitro-1-naphthyl cinnamate exerts a photosensitising effect. These monomers are light-sensitive and belong to the group of self-sensitised ones.131 Poly(4-cinnamoylphenyl methacrylate) obtained in the presence of benzoyl peroxide as an initiator with a degree of conversion of 78% is insoluble in common organic solvents.132 In contrast to MMA, radical telomerisation of aryl (meth)acrylates with the use of bromotrichloromethane as the telogen is not accompanied by the formation of lactones;133 however, the distribution with regard to the degree of polymer- isation and tacticity are analogous.Pyrolysis of telomers at 150 ± 200 8C leads to the formation of unsaturated compounds and in part lactones. The behaviour of 4-methacryloyl- and 4-acryloyloxybenzoic acids is highly specific under thermal treatment.134 At 250 8C (above the upper limit of polymerisation temperature), the former undergoes polycondensation with the elimination of methacrylic acid and formation of a rigid-chain polymer, viz., poly(4-hydroxy- benzoate). The latter undergoes simultaneous polymerisation and polycondensation.In the polymerised state, both acids undergo polycondensation upon thermal treatment. Methacrylic monomers with the azo group based on amino- phenols 77, 135, and 4-amino-a-naphthol 136 N N R0 CMeC(O)O CH2 NHCOMe R0=H, Me, NO2; N N R0 OC(O)CMe CH2 R0=H, Br, OMe, NO2 attract attention because of the possibility of using them for the preparation of `self-coloured' polymers containing dye residues incorporated into the polymeric chain. Of the monomers based on azo compounds of 3-aminophenol, only the azo-coupling prod- ucts at the para-position relative to the methacryloyl group can polymerise. The monomers based on 4-amino-a-naphthol are incapable of radical homopolymerisation because of a decreased reactivity of their radicals due to high electronic conjugation in the azo system.However, they copolymerise with styrene forming coloured polymers. Copolymers of trans-4-(phenylazo)-1-naph- thyl acrylate and trans-4-(phenylazo)phenyl acrylate with (7)-menthyl acrylate are optically active.137 The data on ionic polymerisation of aryl (meth)acrylates are scarce. They are known to polymerise by an anionic mechanism. Polymerisation of PMA on organolithium catalysts proceeds more slowly than that of alkyl methacrylates;138 this process is characterised by the existence of a `limit' of monomer conversion and the fact that the degree of polymerisation does not increase as the process proceeds further.Anionic polymerisation of PMA, cresyl acrylate 139, 140 and 4-(a,a-dimethylbenzyl)phenyl metha- crylate 141 in the presence of n-butyllithium, as well as anionic polymerisation of p-cresyl methacrylate 142 with naphthyllithium, butyllithium and LiAlH4 in the hydrogen atmosphere are docu- mented. Reduction of the polymers thus obtained with lithium aluminium hydride yields poly(a-methylallyl alcohol) (in the case of p-cresyl methacrylate) and polyallylic alcohol (in the case of p-cresyl acrylate). Phenyl (meth)acrylate also polymerises readily with alkylaluminium chlorides by an anionic mechanism.143 Some PA, e.g., 4-nitrophenyl acrylate, do not polymerise by an anionic mechanism.140 785 Comparative studies of radical and anionic polymerisation of 9-fluorenyl and 9-phenylfluorenyl methacrylates 144 in THF or toluene at temperatures from 778 to 760 8C in the presence of AIBN or butyllithium revealed substantial differences in the reaction course.Upon initiation with AIBN, the yield of poly- mers amounted to 60% ± 95%, the degree of polymerisation ranged from 9 to 37 with Mw/Mn=1.8 ± 3.6, while upon initia- tion with butyllithium, the yield of polymers ranged from 3% to 40%, andMw/Mn=1.9 ± 2.0. IV. Aryl (meth)acrylates in copolymerisation reactions Aryl (meth)acrylates copolymerise easily with most monomers. For example, copolymers of PMA with ethylene 145 and buta- diene 146 have been described. But of greatest interest are numer- ous data 147, 148 on copolymerisation of substituted phenyl (meth)acrylates with styrene, acrylonitrile and MMA.Parame- ters of copolymerisation (AIBN, in bulk or in benzene at 60 8C) of PMAand its derivatives with substitutions in the ring with styrene are presented in Table 1. It was noted that the reactivity of monomers towards styrene radical (1/r1) is determined by the polar (s) and resonance (Er) effects of substituents and is satisfactorily described by the modified Hammett equation 149 log 1 à rs á gEr r1 for r=0.21 and g=1. Low values of the copolymerisation constants r1 and r2 point to the tendency of aryl methacrylates for the alternation with styrene in the copolymerisation. The electron-donor substituents in PMA decrease polarity (e2), while the electron-withdrawing substituents, especially those in the para-position, increase polarity.This is accompanied by a decrease in the frequencies of stretching vibrations of the 7C=C7 and C=O groups.150 Linear correlation is observed between the Hammett constants and the e2 criteria as well as between logQ2 (Q2 is the criterion of the monomer reactivity) and Er.147 In the case of p- andm-nitrophenyl methacrylates, the linear dependences are distorted because of the inhibitory effect of the nitro group. Introduction of several functional groups enhances the effect, as is observed for the criteria Q2 and e2 in 2,4,6- tribromophenyl and pentabromophenyl methacrylates.151, 152 The azo group manifests rather strong acceptor properties (e2=1.0).153 ortho-Substituents, e.g., the carboxy group, strongly increase the values of Q2 but virtually do not affect the e2 values, which is well explained by considering the increased steric hindrances.154, 155 In copolymerisation with styrene, 2-naphthyl methacrylate (2-NMA) manifests a weaker (compared to PMA) trend for alternation, which is, however, enhanced in polar solvents (e.g., in acetonitrile).156 ± 158 Irrespective of the solvent nature, the polydispersity and molecular mass increase with the increase in the content of 2-NMA.In complex aromatic systems, the methacryloyloxyphenyl group behaves in the usual manner, as it does in PMA.159 Parameters of copolymerisation of substituted PA with styrene are presented in Table 2. Comparison of the data presented in Tables 1 and 2 shows that the values of the para- meters Q and e are higher for PA than for the corresponding MA, which is associated with the absence of the effect of the a-methyl group.160 For example, e2 is equal to 1.32 for 2,4,6-tribromophenyl acrylate 161 ± 163 and to 0.91 for the corresponding methacrylate.Copolymers of PA with MMA164 are characterised by the predominance of MMA units (r>1) in the macromolecule. In this case, the reactivity of substituted PA165 is determined by their ability to form p-complexes with the double bond ofMMA, which decreases in the series: PA>2-chlorophenyl acrylate>4-chloro- phenyl acrylate. The values of parameter e increase in the same order (up to 1.46 for the latter member).786 Table 1.Parameters of copolymerisation of substituted PMA with styrene. Substituent in PMA 7 7 7 0.30 0.60 0.45 0.40 0.38 0.22 0.36 0.36 0.34 0.35 0.27 0.26 0.70 0.60 0.66 0.50 0.49 0.16 0.13 1.18 0.41 0.47 0.39 0.14 0.10 0.39 2.53 0.34 0.54 0.31 1.23 4.45 0.75 0.18 0.03 3.66 0.21 0.28 4-Chloro 3-Chloro 2-Chloro 4-Nitro 3-Nitro 2-Nitro 2,4,6-Trichloro Pentachloro 2,4,6-Tribromo Pentabromo 4-Methyl 4-Methoxy 2-Methoxy 4-Formyl 4-Acetyl 2-Isopropyl 2,6-Diisopropyl 2-Carboxy 2-Carboxy (DMSO) 2-Methoxycarbonyl 2-Phenyl 4-Phenylazo 2,4,6-Tricyano 4-(1,3-Diphenyl)-2-pyrazolyl-5 4,4-Bishydroxyphenyl-o-carboranyl 2-Naphthyl (dioxane) 2-Naphthyl (acetone) 4-Cinnamoylamino 4-Acetylamino 3-Acetylamino 3-Butyrylamino 4-Methacryloylamino 3-Methacryloylamino 4-Nitro-2-methacryloylamino 3-Methyltetrahydrophthalimido 3,5-Bis(N,N-dimethylamino) Note.The subscripts 1 and 2 in the parameters refer to the first (styrene) and the second (PMA) monomers, respectively; here and in other tables, the solvent for copolymerisation is indicated in parentheses. Table 2. Parameters of copolymerisation of substituted PA with styrene. Substituent in PA r2 r1 0.37 0.50 0.36 0.15 0.25 0.29 0.14 0.08 0.90 2.11 0.09 0.26 0.20 0 0.49 0.61 0.20 0.53 0.06 0.64 1.08 0.35 0.31 0.55 0.83 2.34 0.05 0.88 72,6-Dimethyl 2,4,6-Trichloro 2,4,6-Tribromo Pentachloro Pentabromo 2,4,6-Tricyano 2-Carboxy (DMF) 2-Carboxy (DMSO) 2-Carboxy (benzene) 4-Cinnamoylamino 4-Propylamino 4-Bityrylamino 4-Nitro-2-acryloyl- amino Note.The subscripts 1 and 2 in the parameters refer to the first (styrene) and the second (PA) monomer, respectively. Er r1 s 0.10 0.08 70.41 0.35 7 0.226 0.373 0.560 0.778 0.710 0.650 1.07 70.03 0.11 0.170 0.268 0.21 0.516 0.22 0.21 0.40 0.19 0.18 0.13 7 7 0.19 2.00 7 7 0.20 7 7 0.09 0.30 0.28 7 7 0.33 7 7 0.27 0.15 7 7 0.34 7 7 0.39 7 7 0.16 7 7 0.80 7 7 0.27 7 7 0.57 7 7 0.29 7 7 0.18 7 7 0.26 7 7 0.56 7 7 0.49 7 7 0.63 7 7 0.62 7 7 0.29 7 7 0.63 7 7 0.38 7 7 0.14 7 7 0.26 7 7 0.023 7 7 0.55 7 7 0.32 Ref.Q2 1/r1 e2 0.50 0.91 0.82 2.70 0.96 2.77 0.71 42.00 1.09 7.14 1.31 1.18 0.19 11.11 0.81 5.00 1.03 2.04 0.85 5.00 1.50 16.60 3.90 0.43 0.42 3.21 1.11 20 20 91 1.32 161 1.11 7 7 163 1.14 161 76 0.30 160 0.70 155 1.02 154 90 0.53 148 1.20 7 7 148 0.97 148 20.00 4.86 V G Syromyatnikov, L P Paskal', I A Savchenko 1/r1 r2 3.33 4.55 4.76 2.50 5.26 5.56 7.69 5.26 0,50 5.00 11.10 3.33 3.57 3.03 3.70 6.67 2.94 2.56 6.25 1.25 3.70 1.75 3.45 5.55 3.85 1.78 2.04 1.58 1.61 2.81 1.59 2.67 7.14 3.85 43.48 1.82 3.13 It was noted 165 that the presence of aromatic substituents in copolymers of MMA with phenyl (meth)acrylates increases the number of hetero- and isotactic sequences in macromolecules. As in the case of 4-phenylazophenyl methacrylate,153 copolymers of MMA with 2-methacryloyloxybenzoic acid are enriched in the units of the latter (r1=0.74, r2=1.22).The rate of copolymerisa- tion decreases with the increase in the content of the second component.166 For 4-acetylphenyl methacrylate, the influence of the penultimate unit 167 was observed, which is due to strong steric hindrances and high polarisability of the aromatic oxo group. Constants of copolymerisation of a number of substituted phenyl (meth)acrylates with acrylonitrile are presented in Table 3; their reactivity towards the acrylonitrile radical varies depending on the nature of the substituent group and its position in the ring.168 The trend for alternation is not strong, the values of r1 fit well the dependence log 1 a ¢§0:98Os a 1:66DsU, r1 where s is the Hammett polar constant, Ds is the difference between the Brown and Hammett constants for substituents.Accumulation of substituents in the ring of phenyl acrylates decreases even more strongly the trend for alternation, as is seen in the example of 2,4,6-tribromophenyl acrylate.169 However, the Ref. e2 Q2 1.17 1.35 1.36 0.83 1.27 1.47 1.90 1.40 0.31 1.27 2.35 1.23 1.23 1.13 1.20 1.82 0.75 0.79 2.22 0.54 1.18 0.66 1.28 1.56 1.15 0.14 0.70 0.69 0.58 1.75 147 147 147 20 147 147 20 20 152 151 151 147 147 20 23 147 20 20 154 155 154 20 153 76 71 159 158 158 90 148 148 148 148 148 148 119 0.51 0.72 0.77 0.83 0.98 0.86 0.95 0.86 70.20 0.91 1.14 0.45 0.53 0.43 0.61 0.82 0.90 0.66 0.50 0.25 0.63 0.43 1.00 0.82 0.71 0.57 0.54 0.24 0.48 0.31 7 70.33 1.13 1.39 0.77 0.67 0.75 1.08 1.53 0.66 12.37 0.56 1.03Aryl (meth)acrylates and polymers based on them Table 3.Parameters of copolymerisation of substituted phenyl (meth)- acrylates with acrylonitrile.a r2 r1 Substituent in phenyl meth- acrylates Acrylates 0.36 0.94 0.86 1.16 1.02 0.80 2.05 0.46 0.33 1.26 1.12 0.82 0.73 0.96 74-Chloro 3-Chloro 2-Chloro 4-Bromo 4-Methyl 2,4,6-Tribromo Methacrylates 0.98 0.12 0.96 0.20 0.28 0.02 0.84 0.04 0.52 0.02 0.51 0.03 2,4,6-Tribromo Pentabromo 2-Naphthyl (chloroform) 2-Naphthyl (benzene) 2-Naphthyl (acetone) 2-Naphthyl (acetonitrile) Note.The subscripts 1 and 2 in the parameters refer to the first (acrylonitrile) and the second (PMA) monomer, respectively. a For acrylonitrile e1=1.2, Q1=0.6. trend for alternation was observed for 2,4,6-tribromophenyl and pentabromophenyl methacrylates.170 Copolymerisation of 2-NMA with acrylonitrile in chloroform or benzene proceeds with the formation of donor ± acceptor complexes between the monomers; therefore, the values of r1 and r2 differ in different solvents.171, 172 Complexation was also found to occur in the copolymerisation of 2-NMA with monomethyli- taconate;173, 174 thus the alternation of monomers of this pair is different in different solvents: in chloroform, r1=2.440.19, r2=1.200.28; in dioxane, r1=0.490.04, r2=0.970.29; in acetone, r1=0.150.01, r2=0.280.03 and in acetonitrile, r1=0.100.01, r2=0.350.14.Such changes in the copolymer- isation constants reflect interactions between the monomer molecules and the corresponding solvent. The constants of copolymerisation of PMA with methacrylic acid (MAA) are as follows: r1=0.40 and r2=0.52 (benzene), r1=0.21 and r2=1.52 (DMF/benzene), which points to a lower reactivity ofMAAand higher reactivity ofPMAin the presence of DMF, which appears to act as a complexation agent.175 Copoly- mers of pentachlorophenyl acrylate with acrylic acid (AA) are enriched in the AA units.163 In 2-butanone, PMA and glycidyl methacrylate give a copolymer enriched in PMA (r1=0.840.51, r2=1.570.56).176 Optically active copolymers were obtained upon copolymerisation of phenyl, benzyl and 1-naphthyl meth- acrylates with maleic anhydride in the presence of b-cyclodex- trin.177 Copolymerisation of N-vinylpyrrolidone with 2-carboxyphenyl acrylate 160 and 2,4,5-trichlorophenyl acryl- ate 178 was also studied; in the latter case, copolymers with a high degree of alternation were obtained.In copolymerisation of p- and m-phenylene diacrylates with styrene, a copolymer with acrylate pendent groups is formed in the initial stages; these groups then react with styrene to form a cross- linked copolymer, which precipitates from the reaction mixture in the form of a gel.o-Phenylene diacrylate forms a non-cross-linked ladder copolymer with styrene due to cyclopolymerisation. The smallest values of the polarity criterion e were obtained for the ortho-isomer.6 The values of the copolymerisation constants for isomeric phenylene diacrylates (PDA) are presented in Table 4. Ref. e2 Q2 1/r1 1.4 0.36 0.37 70.77 168 70.47 168 168 70.12 168 7 7 168 7 7 168 0.07 0.11 7 7 169 2.17 3.03 0.79 0.89 1.22 1.37 1.04 0.08 170 0.64 171 0.79 172 0.78 1.09 18.30 5.0 3.57 50.0 0.98 172 46.40 25.0 0.94 172 21.80 50.0 1.09 172 53.00 33.3 787 Table 4.The values of copolymerisation constants for phenylene diacryl- ates (FDA) and styrene. Solvent r1 e2 Q2 r2 FDA isomer ortho- meta- para- 0.37 0.49 0.90 0.72 0.82 0.70 0.74 0.83 0.78 0.46 0.79 1.00 THF benzene THF benzene THF benzene 0.48+0.19 0.45+0.19 0.17+0.02 0.15+0.04 0.21+0.07 0.35+0.09 0.55+0.15 0.42+0.28 0.33+0.06 0.67+0.11 0.35+0.06 0.30+0.08 Note. The subscripts 1 and 2 in the parameters refer to the first (styrene) and the second (FDA) monomer, respectively. In radical copolymerisation of p-chlorophenyl methacrylate with ethylene glycol, 2,2-di(4-hydroxydiphenyl)propane and hydroquinone dimethacrylates,179, 180 the most reactive is ethyl- ene glycol dimethacrylate as the second monomer, which is devoid of the mesomeric effect.The copolymer produced both upon catalytic and photochemical initiation is enriched in this com- pound (r1=0.290.03 and r2=1.310.06). Methacrylamide 181 and peroxide monomers can be used for subsequent cross-linking in copolymerisation with PMA. The constants of copolymerisation of PMA with tert-butyl p-vinyl- perbenzoate are as follows: r1=1.35, r2=0.32.182 Copolymerisation of aryl methacrylates in donor ± acceptor complexes bears a special character. For example, complexes of monomers and polymers of carbazolyl methacrylates with dini- trophenyl-containing monomers and polymers were obtained.183 Charge-transfer complexes (CTC) are formed in copolymerisation of the donor monomers, viz., N-(2-hydroxyethyl)carbazolyl acryl- ate (1) and -methacrylate (2) with the acceptor monomers, viz., 2,4-dinitrophenyl acrylate (3) and methacrylate (4).114, 183, 184 The extent of intramolecular charge transfer in copolymers (according to the chemical shift values of aromatic protons in the 1H NMR spectra of 3 and 4) increases as the content of 4 in the alternating diads with 1 is increased and is larger in the 2 ± 3 copolymer than in the 1 ± 3 copolymer. In copolymers containing only methacrylate units, no intramolecular CTC are revealed, the most stable CTC are formed in copolymers having only acrylate units.In copoly- merisation of 1 with 4, the intermonomeric CTC are not added as a whole,184 and the relative reactivity is determined solely by the sequence of distribution of units rather than by the configuration factors. With the increase in the temperature, the CTC present in the copolymer disintegrate due to the higher segmental mobility.Intramolecular CTC are also formed in the copolymerisation of picryl (meth)acrylate (incapable of homopolymerisation) with N- (2-hydroxyethyl)carbazolyl (meth)acrylate. The copolymerisation constants indicate that the most stable CTC are formed in dioxane.185 ± 187 Photoconductivity of poly(N-vinylcarbazole) increases when electron-acceptor comonomers forming CTC are used, e.g., isomeric 2,2-dicyanovinylphenyl (meth)acrylates (NC)2C=CHC6H4OC(O)CR=CH2 (see Ref.188). Mixing of poly(N-vinylcarbazole) with the same amount of the low-molec- ular-weight acceptor leads to a less pronounced effect. Directed intramolecular transfer of electronic triplet excita- tions was studied in a copolymer of 1-naphthyl acrylate (1-NA) and 4-acetylphenyl methacrylate.189 The copolymer contains two p-electronic systems in which unidirectional transfer of electronic excitation is brought about. Upon selective excitation of the singlet level of 4-acetylphenyl methacrylate units, phosphores- cence of only 1-NA units is observed. Such a molecular structure can function as a specific exciton gate.190 ± 192 In a ternary styrene ± acrylonitrile ± 2,4,6-tribromophenyl (meth)acrylate system, the third component decreases the molec- ular mass and thermal stability of the terpolymers formed.193 ± 195 In copolymerisation of phenyl, 4-butylphenyl, 4-nitrophenyl and788 1-naphthyl acrylates with SO2 and also in three-component copolymerisation of these monomers with hept-1-ene (see Ref.196), the maximum content of sulfonyl monomeric units in copolymers ranges from 13% to 24% depending on the inductive steric effects. The composition of terpolymers varies within a wide range depending on the molar ratio of reagents and conversion. It is also possible to copolymerise PMA one with another.197 Changes in the enthalpy and parameters of PMA copolymerisa- tion with 2-methylphenyl and 2-ethylphenyl methacrylates were studied in the temperature range 80 ± 100 8C.The problems of the relationship between the structure of polymeric carriers based on cross-linked PA polymers and their copolymers with styrene and the reactivity of such carriers were reviewed.198 V. Structure and properties of poly[aryl (meth)acrylates] Esterification of atactic, syndiotactic and isotactic polyacrylic acids with phenols yields only atactic polymers. This points to the spatial isomerisation of the tertiary carbon atom in the course of esterification and the impossibility of obtaining stereoregular poly(aryl methacrylates) by polymer-analogous transformations. Radical polymerisation of PMA yields an atactic polymer which contains nonetheless more syndiotactic structural blocks than the structurally similar poly(benzyl methacrylate) and poly(2-phenylethyl methacrylate).199 This is related to the higher polarity (s=0.6) of the phenyl groups than that of the alkyl groups (s varies from 70.3 to 0.215) rather than to their higher rigidity or small volume.Jimmy et al.200 studied the influence of the side groups and the size of the polymer coil of poly(benzyl methacrylate), poly(triphenylmethyl methacrylate) and poly(diphenylmethyl methacrylate). The overall activation energy of radical polymerisation of PMA is equal to 69.0 kJ mol71, which is somewhat lower than that for poly(methyl methacrylate) (PMMA).201 In polymerisation with AIBN in the temperature range 30 ± 100 8C, a Bernoulli distribu- tion of stereochemical structures in the PPMA chains is observed.The content of iso- and syndiotactic triads in them decreases as the temperature increases, which is characteristic of a,a-disubstituted monomers. The triads are disposed in the chain in an isolated manner. The phenyl radical is oriented with its maximum polar- isability axis along the direction of the main trans-chain.202 In poly(aryl methacrylates), the content of isotactic, atactic and syndiotactic triads is 15%, 40% and 45%, respectively.203 The use of high-frequency NMR spectroscopy (500 MHz for 1H and 125 MHz for 13C) allowed calculation of isotactic parameters for poly(phenyl acrylate) (PPA) (Pm=0.44) and poly(4-fluorophenyl acrylate) (Pm=0.48) 204 obtained by radical polymerisation. Isotactic PPA can be obtained by anionic polymerisation in the presence of butyllithium.140 Kempf and Harwood 205 have shown that PPMA of a predetermined configuration can nonetheless be obtained from polymethacrylic acid if certain conditions are met. Studies of the influence of solvents on the microstructure of poly(1-naphthyl methacrylate) and poly(2-naphthyl methacry- late) (1-PNMA and 2-PNMA, respectively) in comparison with poly[cumylphenyl meth)acrylate] and PMMA have shown 206 ± 208 that the polymerisation of 2-NMA in methanol, acetonitrile and nitromethane occurs heterogeneously.Even in the presence of non-polar solvents, the percentage of isotactic triads in 1-PNMA and 2-PNMA is higher and the percentage of syndiotactic triads is lower than in PMMA. Syndiotacticity of 2-PNMA is higher than that of 1-PNMA.In solvents with higher dielectric constants, PNMA with a still higher content of isotactic triads is obtained. Poly(1-naphthyl methacrylate) possesses a higher heterotacticity than 2-PNMA. In copolymerisation of 2-NMA with MMA (r1=1.930.16, r2=0.330.08), syndiotactic addition proved to be preferential.209 The behaviour of PA is analogous.210 However, PPMA, poly(p-cresyl methacrylate), 2- and 4-methoxy- phenyl methacrylates, obtained by polymerisation in the presence V G Syromyatnikov, L P Paskal', I A Savchenko of butyllithium at low temperatures in toluene, have an isotactic structure with 90% of isotriads,211 while syndiotactic polymers are formed in THF.212 The temperature characteristics of poly[aryl (meth)acrylates] are determined by their structural peculiarities. As was indicated above,4 the thermostability is determined by the character of the substitution: in the para-substituted poly[aryl (meth)acrylates] the glass transition temperature (Tg) is always lower than in the ortho- substituted ones.This is explained by the shielding effect of ortho- substituents on the ester bond. Tg increases with the increase in the size of substituents and their polarity. Thus PPA, poly(o-tolyl acrylate) and its para-isomer have Tg values of 56.5, 51.5 and 24.5 8C, respectively. For 1-PNMA and 2-PNMA, Tg values are 135 and 119 8C, respectively.214 The relationship between Tg and molecular mass (M) of poly(o-alkylphenyl methacrylates) is non- linear and may be described by the following equation:215 Tg=Tg(0)+klnP, where Tg(0) is the temperature characteristic of the monomeric unit and P is the degree of polymerisation.For the infinitely large PPMA molecules, Tg=118 8C, while for poly(2,6-dimethyl- phenyl methacrylate) (PMPMA) Tg=177 8C. In copolymers of phenyl, 2-chlorophenyl and 4-chlorophenyl acrylates with MMA, Tg decreases with the increase in the concentration of MMA.216 In this case, the concentration dependence of Tg obeys Johnson's equation, which considers the contribution of diads in the polymer chain to the glass transition effect. A comparative calorimetric study of substituted PPA 217 and poly(vinyl benzoates) made it possible to establish that the dependence of specific heat capacity (Cp) on temperature in the range of glassy state is described by the equation Cp=A+BT+CT2+DT2.The increase in Cp in the glassy state was observed for all substituted polymers with increase in the volume of substituents. For a number of alkyl- and alkoxy-substituted PPA the values of Tg were found and the heat capacity jumps in the glass transition region and coefficients A, B, C and D in the proposed equation were determined. Thermal stability of poly(aryl methacrylates) was studied by the TGA method;218 the curves for poly(tolyl methacrylates) (PTMA) and poly(benzyl methacrylate) are S-shaped and similar to the curves for PMMA. For PPMA, the process was charac- terised by several ranges of decomposition. ortho-PTMA proved to be the most stable isomer.Effective activation energies of thermal destruction for the polymers studied vary from 81 to 159 kJ mol71 (210 kJ mol71 for PMMA). Thermal destruction of poly(2-methacryloyloxybenzoic acid) 219 occurs in three steps in temperature ranges of 140 ± 220, 250 ± 330 and 350 ± 450 8C with mass losses (according to TGA data) of 33%± 35%, 30% and 30%, respectively, which corre- sponds to the stoichiometric content of salicylic acid in the polymer in the first two stages. The effective activation energy in the first stage is 79 kJ mol71. Upon destruction, fragments of the glutaric anhydride type accumulate first in the polymer (up to 330 8C); after this, the macrochains undergo disintegration. Copolymers of PMA with MMA are more thermostable than the homopolymers;220 monomers are the main degradation products.At a low content of PMA, oligomers containing anhydride groups are also formed; with the increase in the PMA content the ability to form anhydrides drops. In contrast to homopolymers, the destruction of copolymers is characterised by relatively short kinetic chains of depolymerisation and the cleavage of the principal bonds in the macrochain. Among the copolymers of acrylonitrile with 2,3-dibromopropyl, pentabro- mophenyl and 2,4,6-tribromophenyl acrylates, the highest ther- mostability was observed for copolymers with the latter.221 In studies of poly[aryl (meth)acrylates], a prominent place is occupied by the investigations of properties of their dilute solutions. By measuring the swelling degree, solubility para-Aryl (meth)acrylates and polymers based on them meters (d) were determined and their dependence on the character of forces of interaction of polymer with solvent was confirmed.222 Chloroform, tetrachloroethane, chlorobenzene and ethyl acetate are the best solvents for poly(aryl methacrylates).The values of d for poly(alkylphenyl methacrylates) were determined in 20 sol- vents of different nature, considerably differing in their polarities (the contribution of dp) and ability to form hydrogen bonds (the contribution of dH), and in the widest possible range of the chain flexibility parameter s. The magnitude of dH decreases slightly with the enhancement of the `paraffinic character' of the sol- vent.223 The influence of alkyl residues is weakly manifested and the values of dH found differ somewhat from the calculated ones.Investigation of properties of dilute solutions by the osmometry and viscosimetry methods showed that the ortho-substituents in the benzene ring of the side chain increase appreciably the rigidity of the polymer. For PMPMA, the solubility parameter in toluene is equal to 9.6 cal71/2 cm3/2 (see Ref. 224). The power index a in the dependence [Z]& Maw , where [Z] is the specific viscosity, increases as the thermodynamic quality of the solvent is enhanced (a is equal to 0.5 in toluene, 0.59 in THF and 0.69 in chlorobenzene). It was established that <r20 >1/2 (characteristic chain ratio) and Tg increase upon transi- tion from PPMA to PMPMA.For poly(2,6-diisopropylphenyl methacrylate), the solubility parameter in toluene is also equal to 9.6 cal71/2 cm3/2 (see Ref. 225), while the Mark ± Hauwink equa- tion ([Z]=KMan ) (25 8C) has the following form for THF [Z]=1.0261074M0:71, n for toluene [Z]=1.2261074M0:69, n and the THF: water mixture (90.9 : 9.1) [Z]=8.5161074M0:50, n for the ratio of the mean squared distance between the ends of the polymer coil and the molecular mass of the polymer (see Ref. 225) <r20 >=0.677M1/2. For p-AAPMA226 in DMF at 25 8C [Z] =1.4061073M0:85. n Investigation of the influence of temperature on the thermo- dynamic properties and undisturbed dimensions ofPPMAmacro- molecules in isobutyl methyl ketone showed 227 that for all fractions an anomalous dependence of [Z] on temperature takes place at 20 ± 35 8C, which becomes more pronounced with the increase in the molecular mass.The value of the coefficient K in the Mark ± Hauwink equation is maximum at 25 8C, which implies changes in the character of hydrodynamic interactions inside the macromolecular coil, whereas the value of a is a minimum at the same temperature, which means drastic deterio- ration of the solvent quality. These phenomena point to a conformational transition associated with the increased chain flexibility resulting from the changes in specific interactions between the phenyl groups. The side chains in PMMA, poly(isobutyl acrylate) and poly(cyclohexyl methacrylate) have a strong influence on the temperature of the conformational transition and changes in the undisturbed dimensions of the chains, which is accompanied by the appearance of a jump in the temperature dependence of viscosity, refraction index and partial specific volume of polymers.228 Gargallo et al.229 analysed the influence of the size and the nature of the side groups in poly(alkylphenyl methacrylates) on the magnitude of partial volumes.The intramolecular character of the conformational transition is confirmed in the example of poly(4-tert-octylphenyl methacrylate).230 It was established for PPMA solutions that the conformational transition occurs owing to the changes in specific near-order interactions between the phenyl rings in the pendent 789 groups of the polymer studied.231 Comparison of magnitudes and orientation of dipole moments related to the pendent groups of poly(chlorophenyl acrylates) revealed their strong dependence on the position of the substituent in the benzene ring.232 The example ofPPMAwith the phenyl benzoate side groups showed 233 that the influence of thermodynamic quality of the solvent on the dipole moment is characteristic of polymers with highly rigid polymeric chains and strong intramolecular interactions of the side groups.For poly(2-biphenylyl methacrylate), rather insignificant (5% ± 18%) variation of [Z] in different organic solvents was observed,234 whereas in other poly(aryl methacrylates) the varia- tion of [Z] is 21% ± 61%, which is due to the presence of the bulky o-biphenylyl group localised close to the basic chain.In poly(4- biphenylyl methacrylate),235 the undisturbed dimensions of the chain calculated by the Stockmayer ± Fixman method with con- sideration of the dependence of [Z] onMproved to be three times as large as those in the case of free rotation in the main valent chain, which is indicative of an appreciable inhibition of rotation in poly(aryl methacrylates). For this polymer, the temperature coefficient of undisturbed dimensions of the chain was determined (2.361073 at 13 ± 40 8C and 1.261073 at 40 ± 60 8C);236 similar calculations were performed for the ortho-isomer and for poly(2,4,5-trichlorophenyl methacrylate).237 In the case of poly(2-biphenylyl methacrylate), the value of the chain flexibility parameter s (2.8) was larger than that for poly(4-biphenylyl methacrylate) (s=2.7), which points to a larger flexibility of the former due to a close position of the o-diphenylyl groups to the basic chain.238 Studies of the mobility in poly(2-biphenylyl methacrylate) by the DSC method pointed to the occurrence of four relaxation processes with the temperature increase, viz., g, b, a and r.The processes of a- and b-relaxation are related to vitrification and subvitrification, respectively.239 For PPA, it was found that the values of temperature coefficients of the undisturbed dimensions range from 73.461073 to 74.761073, the upper critical temperature of dissolutionYin ethyl lactate is 14 8C and the values of [Z] increase with the temperature increase within the range 7 ± 77 8C.240 As for PMMA, the constants of the Mark ± Hauwink equation for PPMA fit the van Krevelen equation.241 The use of the light scattering method in ethyl lactate for PPA allowed determination of values ofMw, second virial coefficients A2, mean squared radii of inertia <S2> and coefficients of swelling at different temper- atures.242 This method was also applied to study PNMA solu- tions 243, 244 in comparison with polystyrene.The ratios of the threshold concentration c0 in light scattering measurement to the second virial coefficient A2 for these polymers were the same and equal (in non-polar solvents) to 0.93. For dilute solutions of homopolymers with the main methacrylate chain and methoxy- biphenyl mesogenic groups and their copolymers,245 the constants in the Mark ± Hauwink equation, parameters of Flory ± Huggins interaction and the mean squared distances between the chain ends<r2>were determined. The latter parameter is greater than that in PMMA, which indicates an appreciable increase in the rigidity of the polymethacrylate chain upon introduction of the mesogenic side groups.As regards PMA copolymers 246 and substituted PMA,247 for them, too, the values of K, a and Y were found in certain solvents, and the undisturbed dimensions of the polymer coils and parameters of the chain rigidity were calculated. The data on electrical properties of poly(aryl (meth)acrylates) are scanty.The spectra of dielectric losses at different temper- atures were studied for specimens ofPPMAand polymers of o-,m- and p-PTMA 248 and for polymethoxy-substituted PMA.249 Three relaxation processes were found to occur. The high-temperature process (a-relaxation) occurs in the glass transition range and is related to the micro-Brownian mobility in the basic chain of the polymer. The maximum temperature of this process increases in the following order:m-PTMA<o-PTMA<PPMA<p-PTMA; the crystallinity of polymers increases in the same order. In the middle-temperature range, b-relaxation is observed due to the micro-Brownian mobility of the side groups, which is particularly790 manifested in o-PTMA.Increased activation energies of this process were observed for specimens of higher crystallinity (PPMA and p-PTMA). The low-temperature g-relaxation is associated with the motion of the tolyl and methoxyphenyl pendent groups. Investigation of the dielectric relaxation of poly(phenyl and chlorophenyl acrylates) revealed that the inten- sity of the b-process in PPA and poly(4-chlorophenyl acrylate) is lower than in poly(2-chlorophenyl acrylate) and poly(3-chloro- phenyl acrylate); in the last two polymers the intensity of b-process is higher than that of a-process. a-Relaxation is determined by the free volume and is well described by the binding model;250 in polymers the time of dielectric relaxation is always shorter than the time of mechanical relaxation.251 Noticeable changes in the electrical characteristics of poly- ethylene in strong fields (electrical strength and I ±V character- istics in the pre-breakdown voltage range) are observed when small amounts (1% ± 2%) of comonomers, such as pentabromo- phenyl and 2,4,6-tribromophenyl methacrylates, were intro- duced.252 The maximum value of breakdown voltage is observed at the content of the former additive of 0.1% ± 0.2%, the doping action is produced by units of the above-mentioned PMA.Such an effect is not exerted by benzyl methacrylate. In a magnetic field, a noticeable effect of the increase in spontaneous orientation of PPMA may be observed only in mesomorphic polymers, in particular in those with the phenyl benzoate pendent groups.253 Poly[aryl (meth)acrylates] are very transparent (transmission coefficient >90%) and possess good mechanical properties.254 Therefore, copolymers containing up to 99% of these monomers are used as materials for manufacturing lenses.255 Some of them, in particular 1- and 2-NMA, determine the high refraction index of copolymers.256 Some aryl (meth)acrylates and their polymers may exist in the liquid-crystalline state with characteristic anisotropy of optical properties.31, 257 Their polymeric nature is manifested in consid- erable enhancement of thermal stability of the mesophase, its temperature range is restricted by the glass-transition and clar- ification temperatures and is determined to a considerable extent by the nature of the basic chain and its flexibility.258 In such polymers, structures of various mesophases and different variants of the packing of mesogenic groups can be realised. Most polymers can form lamellar structures of the smectic type.Nematic structures arise in polymers with shorter substituents and flexible hinges. In particular, all polymers with the lateral mesogenic groups possess nematic mesomorphism.259 Clarifica- tion temperatures of polymers with the same mesogenic groups but different chemical composition of the basic chain coincide, whereas in these cases the Tg values decrease with the increase in flexibility of the basic chain or the length of the terminal fragments of the mesogenic pendent groups.For all the polymers having one mesogenic side unit per elementary unit of the chain, it was established that the global anisotropy is independent of steric inhibition of the a-methyl groups. A decrease in temperature results in a basic polymer chain extension normally to its mesogenic units, which thus acquires an elongated shape.260 According to the results of X-ray diffraction analysis, the macromolecules of polymers of phenyl and 4-alkoxyphenyl esters of acryloyloxybenzoates,261 which form anisotropic systems on cooling of melts or concentrated solu- tions, represent cylinders 8 ± 10 nm long and 2.5 ± 3.9 nm in diameter formed by aperiodic helices. Acrylic polymers that contain mesogenic phenyl benzoate groups with short alkyl substituents form only nematic meso- phases.262, 263 In studies of the comb-like liquid-crystalline poly- mers, which differ in the nature of the basic chain (acrylate or methacrylate) but contain identical phenyl benzoate groups,264, 265 the low- and high-temperature smectic phases of polyacrylate are referred to the smectic types B and A, respec- tively.For polymethacrylates, the following scheme of polymorphic transformation was proposed: smectic F ?smec- V G Syromyatnikov, L P Paskal', I A Savchenko tic C?smectic A?isotropic liquid. Investigation of conforma- tional changes in poly(methacryloyloxyphenyl 4-n- alkoxybenzoates) 266 in the temperature range including the glassy, liquid-crystalline and isotropic states revealed that the conformational changes are observed in the glassy state 40 ± 80 8C before the transition to the liquid-crystalline state depending on the alkyl chain length and that they are accompanied by the homeotropic orientation in the polymeric films.Poly(biphenylyl acrylate) prepared by the reaction of polyacryloyl chloride with 4-hydroxybiphenyl forms a smectic mesophaseAat 144 8C, which is totally destroyed at 250 8C. The mesophase ± isotropic transi- tion is nearly fully reproduced in repeated cycles of heating.267 Poly(4-acryloyloxyazobenzene) is in turn in the mesomorphic state at 100 ± 240 8C. Polyacrylates and polymethacrylates that contain the cyano-substituted aromatic azomethine and cyanobi- phenyl mesogenic groups form liquid-crystalline phases of the nematic type and also of the smectic type A and C.268, 269 In polymethacrylate with the biphenyl fragments as mesogens in the side chains, a poorly ordered smectic phase exists at 136 ± 157 8C and above these temperature, the isotropic phase.270 Thus, among poly[aryl (meth)acrylates] it is possible to find polymers that have mesophases in different temperature ranges.Such polymers are capable of reflecting selectively light in the IR, UV and visible parts of the spectrum, manifesting transitions induced by electric and magnetic fields, and in some cases they even possess ferroelectrical properties.258 Owing to such electrical and other effects, the field of application of these polymers in modern technology is extended. VI. Chemical and photochemical properties of poly[aryl (meth)acrylates] and their copolymers Chemical properties of poly[aryl (meth)acrylates] and their monomers are determined primarily by the presence of the ester group, the aromatic ring and its substituents.The rate of hydrolysis of the pendent groups in PPMA at different temper- atures in aqueous DMSO is described by three different constants corresponding to the hydrolysis of the ester groups of the polymer with the adjacent 0, 1 and 2 hydrolysed ester groups.271 The activation energies that correspond to these constants are equal to 40.6, 58.2 and 74.0 kJ mol71, respectively. Alkaline hydrolysis of PPMA with p-Cl, p-OMe, p-Me and m-NO2 substituents in the aromatic ring is of the pseudo-first order;272 the first two constants increase with the higher KOH concentration, whereas the third constant remains virtually unchanged.The values of these constants correlate well with the values of the Hammett constants for substituents. Enzymatic hydrolysis of the side ester groups in copolymers of 4-nitrophenyl methacrylate with acrylamide 273 in the presence of lipase did not take place, whereas esterase and a-chymotrypsin acted very slowly. The rate of alkaline hydrolysis increased with the higher content of acrylamide in the copolymer, which was due to the influence of acrylamide units on the reactivity of ester groups in the 4-nitrophenyl fragments. The action of a-chymo- trypsin on 2-biphenylyl methacrylate (BPMA) and its copolymers induced hydrolytic liberation of hydroxybiphenyl; the Michaelis constant for the copolymers was lower than for the homopolymer and decreased in the following series of comonomers: methacry- loylglycine>vinyl acetate>methacryloylalanine>styrene.274 The catalytic effect of a-chymotrypsin was weaker in the case of poly(2-biphenylyl acrylate).275 The possibility of modifying poly- mers and copolymers of 2,4,5-trichlorophenyl acrylate 276 and 4-nitrophenyl methacrylate 277 ± 279 through their aminolysis has been demonstrated. Optimisation of the reaction conditions makes it possible to introduce various substituents, for example, perfluoroalkyl groups,280 into the phenyl groups of PPMA.Reactive functional groups can be subjected to further transformations 281 and be used for the chelate formation.282, 283Aryl (meth)acrylates and polymers based on them Chemical transformations of poly[aryl (meth)acrylates] under the action of different types of radiation are rather diverse. Investigation of the photobehaviour of phenyl-containing meth- acrylate polymers showed 284 that the lifetime of the singlet state in polymers is shorter than in model small molecules, which is related to the higher sensitivity of this parameter to steric hindrances.A high yield of long-living triplet states was observed in the presence of naphthalene rings.285 The acetyl groups favour quenching of the triplet. 2,4-Diacetyl-1-naphthyl methacrylate units induce quenching even at their content *1 mol.% with a quantum yield of 0.4.286 In poly(2-naphthyl methacrylate), insignificant migration of the singlet energy occurs.287 Because of a large difference in the energies of the excited singlet and triplet states, the singlet energy transfer to the ketone traps in a copolymer of 2-NMA with arylvinyl aromatic ketones and the triplet energy is transferred from these traps again to the naphthalene chromo- phores.The fluorescence (FL) spectrum of 2-PNMA 288 is characterised by the presence of two bands which are attributed to monomeric (340 nm) and excimeric (400 nm) luminescence. The luminescence spectrum of copolymers strongly depends on the amount of a comonomer. In copolymers with MMA, the correlation between the excimeric and monomeric fluorescences is determined basically by the molar fraction of naphthyl methacry- late units.289 The ratio of intensities of excimeric and monomeric fluorescences is taken as the compatibility parameter of copoly- mers of naphthyl and anthryl methacrylates with MMA and n-butyl methacrylate (BMA).290, 291 In copolymers of PMA,292 the band of excimeric FL is at 355 nm.The FL spectra of copolymers of vinyl 3-(1- and 2-naphthyl)acrylate with vinyl hexanoate and vinyl acetate were analysed in order to reveal the monomeric and excimeric FL of the naphthalene groups at 340 and 390 nm, respectively. It was shown 293 that the excimer is formed by two naphthalene groups bound to cyclobutane in the 1,2 or 1,3 positions cis-arranged relative to the cyclobutane ring.The curves of FL decay are well described by three exponents attributed to three fluorescence centres: excimers, monomeric chromophores capable of transition to the excimer form and isolated monomeric chromophores incapable of excimer forma- tion.Copolymers of 2-[(2,4,6-tricyanophenyl)thio]ethyl metha- crylate with 3,5-bis(N,N-dimethylamino)phenyl methacrylate which are obtained in bulk phase and form rigid films possess photoconductivity. The photocurrent in such films was observed upon illumination with light with wavelengths of 200 ± 700 nm.294 Photodestruction of PPMA in vacuum and in air occurs with the random scission of macrochains and is intensified under short- wave UV irradition.295 The presence of chlorine atoms in the phenyl radical accelerates photodestruction. For 1-PNMA and its copolymers with BMA it was established that in contrast to thermodestruction leading to depolymerisation, the photo- and radiation destructions involve processes of the basic chain scission, the photodestruction rate depending on the intramolec- ular excimer formation.296 For this reason, the quantum yield of the chain scission decreases monotonically (down to 0.015) with the increase in the content of 1-NMA units. Excimers are not formed for the BMA±NMA±BMA sequences.297, 298 Upon irradiation with electrons (20 keV) and UV light, the perfluoro- alkylated PPA is cross-linked in contrast to the non-perfluoro- alkylated one which is destroyed under these conditions.299 In the presence of oxygen, photooxidation of poly[aryl (meth)acrylates] occurs with the formation of carbonyl groups.Investigation of the photooxidation of 2-NMA copolymers with styrene, MMA and acrylonitrile revealed 300 that where the content of 2-NMA was 7 mass %, the concentration of carbonyl groups was considerably higher than in polystyrene (0% ofNMA) or in copolymers with 13% or 26% of 2-NMA. The number- average molecular mass is also most strongly decreased in copolymers with 7% of 2-NMA. On the whole, poly[phenyl (meth)acrylates] are regarded as radiation-resistant materials;301 however, their resistance is 791 sharply decreased upon introduction of halogens into the aro- matic rings. Upon irradiation of poly(4-chlorophenyl methacry- late) with ionic beams,302, 303 the primary process is the elimination of the chlorine atom with the formation of reactive centres in the basic chain under the action of atomic chlorine.Recombination of these two types of polymeric radicals leads to the cross-linking of the polymer. The radiation yield of the basic chain scission in the radiolysis of MMA copolymers with trichloro- and tetrabromophenyl methacrylates 304 is strongly enhanced by small amounts of the latter, which is related to the important role of the processes of dissociative electron capture. The yield drops dramatically with the increase in the concentra- tion of chlorine-containing monomer to 17% when the processes of cross-linking become noticeable. An analogous behaviour is displayed by halogen-substituted PPMA upon irradiation with a beam of electrons.305 Homopolymers of 4-acryloyloxyazobenzoate and 4-meth- acryloyloxyazobenzene copolymers with methyl acrylate 306 and MMA,307 respectively, possess photochromic properties.The azo group in their units undergoes trans ± cis-isomerisation under UV irradiation (l=370 nm). The increase in absorption is observed at l<280 nm and l>400 nm. Photoisomerisation occurs as the first-order reaction and is reversible, the rate constant for this reaction is independent of temperature. The reverse dark reaction (thermal cis ± trans-isomerisation) is also of the first order. In homopolymers, the kinetics of photoisomerisation is of a more complex character.For them, this is an energetically more favourable process than for copolymers, which may be explained by the interaction of pendent groups. The absorption band of the azobenzene group corresponds to the p ± p*-transition and is shifted from 321.5 to 324 nm with the decrease in the content of the trans-isomer.307 Like other phenyl esters, PA and PMA as well as their polymers and copolymers undergo the photochemical Fries rearrangement under the action of UV light 308 ± 313 COR0 COR0 OCOR0 hn OH + OH R1=CR=CH2. The rearrangement is inhibited after transformation of certain amount of phenyl esters into o- and p-hydroxyphenyl ketones (a 2 : 1 mixture). The ketones were identified by the appearance of absorption maxima at 265 ± 270 and 294 nm in the UV spectra of irradiated monomers or new absorption bands at 1620 and 1660 cm71 in the IR spectra of UV-irradiated poly[phenyl (meth)acrylates].The stability of the polymer with respect to further UV irradiation is associated with the formation of hydroxy ketones on its surface and their photoshielding effect due to higher extinction coefficients. It is known 314 that 2-hydroxybenzophenones are good light stabilisers. It is pre- sumed that their light-stabilising effect is related to the fast tautomerism of excited states. Spectral measurements showed 315 that under prolonged action of the UV light the molecules of m- and p-(N-acylamino)phenyl (meth)acrylates undergo the Fries rearrangement involving mainly the ester groups rather than the acylamino groups and resulting in the appearance of the hydroxy and amino groups, respectively.OC(O)CR CH2 H O CCR CH2 hn O NHC(O)R0 NHC(O)R0792 OC(O)CR CH2 H O CCR CH2 O hn NHC(O)R0 NHC(O)R0 R0=Me, Et, Pr. Poly(1- and 2-naphthyl methacrylates) also undergo photo- chemical transformations by the Fries reaction upon UV irradi- ation.316, 317 This reaction may be of practical value for the modification of polymeric materials. Yet another type of light- sensitive polymers, viz., poly(methacryloyloxybenzylidene- acetophenones) 318, 319 and copolymers of 4-methacryloyloxyben- zylideneacetophenone with BMA,320 have been described. Upon UVirradiation, they become insoluble in organic solvents because of photodimerisation resulting in the formation of cyclobutane structures.Spectral sensitisation of such copolymers is possible with triplet sensitisers, viz., 5-nitroacenaphthene, picramide, N- acetyl-4-nitronaphthylamine and some quinones. Evidently, this process is similar to the photoaggregation of cinnamates. The polymers containing 4-acryloyloxybenzophenone units are highly efficient photoinitiators of polymerisation.321 ± 323 After light absorption, the units of this monomer pass into the singlet- excited state with subsequent intercombinational conversion into p,p-triplet state and transition to n,p-triplet state, which may be quenched by oxygen molecules or be deactivated in the presence of a hydrogen donor with the formation of ketyl radicals.323 Homopolymer is the most efficient as the polymeric photoinitia- tor and its copolymers with 4-dimethylaminostyrene are also highly active.321 Some PMA copolymers possess unusual photoluminescent properties, whereas the corresponding low-molecular-mass com- pounds and homopolymers do not luminesce under experimental conditions.324 The large diversity of properties opens wide possibilities for the application of poly[phenyl (meth)acrylates].VII. Practical application of aryl (meth)acrylates The data on liquid-crystalline aryl (meth)acrylates were generalised in a number of monographs (see, e.g., Refs 59, 60), and this allows us not to go into details of this information. At present, several types of phenyl (meth)acrylates are produced in small quantities and their variety increases continually.An analysis of most recent scientific and patent publications shows that these monomers and polymers, novel for modern industries, will find wide uses basically as modifiers of properties of polymers produced on a large scale. In order to manufacture lenses with high refractive indices (up to 1.67), thermal stability, resistance to shock and solvents and surface hardness, use is made of copolymers of the known monomers (MMA, styrene, etc.) with 3%±40% of PMA,325 ± 328 halogenoaryl methacrylates,329 ± 332 tribromophenyl methacryl- ate,333 ± 337 brominated phenyl acrylates,338 as well as 1- and 2-naththyl (meth)acrylates and benzylphenyl methacrylate.339, 340 Pentachlorophenyl (meth)acrylates may be used as comonomers in the manufacture of light-conducting fibres.341 PMA and PA may be the components of oxygen-permeable plastics intended for manufacturing contact lenses.342 Poly(fluorophenyl acrylates) are used for manufacturing glass for aircraft port-holes.343 Halogen-containing phenyl (meth)acrylates [e.g., 2,4,6-tribro- mophenyl (meth)acrylate] were recommended as components of rubbers 344 and plastics 345 in order to increase their fire resistance.For the same purpose, pentabromophenyl (meth)acrylates are incorporated as the third component into a styrene ± acrylonitrile copolymer.346, 347 V G Syromyatnikov, L P Paskal', I A Savchenko Aryl (meth)acrylates are introduced into plastics to improve their service properties, e.g., shock resistance.348 Poly[3-pentade- cylphenyl (meth)acrylates] are used as pressure-sensitive adhesives for binding various porous materials.349 2,2-Di(4-hydroxy- phenyl)propane di(meth)acrylates exert a particularly noticeable effect on general properties of plastics.350 ± 352 It is proposed to use di(meth)acryloyl derivatives of dihydroxybiphenyl oxides as cross-linking agents for polymeric materials.Fluoro-substituted diacrylates, for example, 1,3-bis(hydroxy-hexafluoropropan-2-yl)benzene diacrylate, are used for making coatings.353 It is proposed to use alkoxylated dimethacrylates of bisphenol-A,354 ± 356 xylylene dimethacry- lates 357 and aryl or naphthyl (meth)acrylates 358, 359 in composi- tions for photo-solidified coatings and glues. High-strength solidifying compositions may be prepared using hydroxyaryl (meth)acrylates that can form urethanes with diisocyanates or isocyanatoethyl methacrylate.360 PMA and its derivatives and 2-NMA (510%) are incorpo- rated into copolymers used in the production of precision optical devices and video discs for recording information.361 ± 364 Low- hygroscopic methacrylic polymers with the water absorption 40.58% at 50 8C have been patented.365 Polymeric surfactants based on copolymers of hydrophilic and hydrophobic monomers are highly effective.366 These include di(meth)acrylates of hydro- quinone containing in its ring such substituents as halogens, alkyls (C1±C20) and biphenyl.Copolymers which are components of hydrosol compositions with improved adhesive capacity and cohesive strength may contain 2-acryloyloxynaphthalene-2-sul- fonic acid along with other monomeric acids.367 Emulsifying monomers of the general formula SO3Na CHC(O)O H2C C12H25 accelerate polymerisation and increase the yield of the target polymer.368 The adhesively strong coatings resistant to the action of water and ethanol were obtained based on film-forming aryl (meth)acrylate copolymers.369, 370 Aqueous dispersions of such copolymers applied onto the polymer surface prevent sweating of plasticising agents from them.Phenyl (meth)acrylates are used for the modification of well- known polymeric products. In order to prepare self-coloured polypropylene, polycaprolactam or polyethylene terephthalate fibres 371 and films,372 these are grafted (with the aid of UV light) to azo monomers, for example, Me N N OC(O)CH N N CH2.Azo monomers are also used in the synthesis of polymeric luminophores.373 Units of tribromophenyl methacrylate are incorporated into polystyrene in order to improve its colour- ability.374 Coloured polymeric films were prepared by dispersing dyes based on 3,3 0-diethoxydicarbocyanine iodide in PPMA.375 Phenyl (meth)acrylates containing groups with antioxidant or UV-stabilising activities may be introduced into macromolecules as intrachain stabilisers.376, 377 This method of stabilisation is more efficient than the conventional introduction of antioxidants because it prevents their losses from polymers due to volatilisation during processing or diffusion in the course of their service.p-Anilinophenyl methacrylate 378 may be regarded as one of the efficient thermostabilisers of this type for polyethylene.376 Copolymers of dienes and vinylarenes (styrene) are stabilised by introducing up to 1.5% of a complex acrylate 379Aryl (meth)acrylates and polymers based on them CR00R000 OC(O)CR0 OH But But CH2 Me Me R0, R00, R000=H, Alk(C1±C16), Ar, cyclo-Alk(C5±C9), AlkAr(C7±C12). Monomeric amines of the type of 4-hydroxydiphenylamine (meth)acrylate belong to the group of non-sweating and non- washed off antioxidants for rubbers.380 2-tert-Butyl-6-(3-tert- butyl-2-hydroxy-5-methylbenzyl)-4-methylphenyl acrylate is a high-temperature thermostabiliser belonging to the group of polymer-bound antioxidants of the phenol type.381, 382 Aminophenyl (meth)acrylate derivatives have been used as antioxidants 383 NH XC(O)CR CHR00 R0 R0=H, Me, OMe; R00=H, Me, Ph; X=NH, O.Such antioxidants are not washed off from rubbers by solvents, are not evaporated and do not cause their bleaching, which is highly important in the technology of rubber processing. (meth)acrylates, Acylaminophenyl imidophenyl (meth)acrylates and imidonaphthyl (meth)acrylates 384, 385 are efficient light stabilisers for styrene. The mechanism of stabilisa- tion is associated with the intramolecular energy transfer in molecules under the action of UV light. Aryl methacrylates introduced into the polystyrene macromolecule in the amount of 5 mass% undergo the Fries photorearrangement, which is accel- erated owing to the intramolecular energy transfer of triplet excitations from the phenyl to the naphthalene moieties of the molecule.The photorearrangement rate is an order of magnitude higher in naphthyl (meth)acrylates than in phenyl (meth)acrylates. The use of monomers providing for self-stabilisation upon exposure to natural conditions is rather promising for the preparation of copolymers.316 Under the action of light, the Fries rearrangement occurs in films, for example, of copolymers of 1-NMA or 2-NMA with styrene or MMA, with the formation of structures of the type of 2-acetyl-1-naphthol with absorption at 320 ± 400 nm.Even at a degree of conversion of *5%, one observes a substantial decrease in the photorearrangement rate, which leads to the increased light-resistance of NMA units situated at a distance of *2.6 nm from the photoproduct.386 The application of such light stabilisers is advisable for coatings and fibres. Polymeric absorbers can also be obtained by copoly- merisation of monomers which contain light-stabilising fragments or groups, e.g., of phenyl 5-(meth)acryloyloxysalicylate with vinyl acetate, vinylidene chloride and vinyl chloride and of 2-hydroxy- 4-(meth)acryloyloxybenzophenone with MMA.387, 388 The effect of light stabilisation is also achieved by grafting these monomers to polystyrene, polypropylene and polyethylene; the activity of methacrylate is higher and this is explained by additional stabilisation of the radical owing to hyperconjugation with the methyl group.389 An analogous effect is also observed for di(meth)acryloyl derivatives of 2,4-dihydroxybenzophenone.390 To prepare transparent articles with improved UV absorption and weather resistance, it is proposed to introduce phenyl (meth)acrylates with benzotriazole substituents into copoly- mers.391, 392 HO N OC(O)CR CH2 N X0 N X00 X0, X00=H, Hal, Alk, Ar.The photochemical behaviour of numerous monomers and polymers with benzotriazole fragments has been described in 793 several publications.393 ± 395 It was shown that the light-protective effect of polymeric UV absorbers depends on the nature of the groups which determine the nearest environment of the fragment and their influence on the strength of the intramolecular hydrogen bond in the benzotriazole fragment. Polyethylene used for manufacturing a packing material containing 4-acryloyloxy- benzophenone units (from 0.1% to 40%), which is destroyed under the action of light in 120 h, has been patented.396 Monomers with the nitro groups, for example, 4-nitrophenyl methacrylate 397 or 4-nitro-1-naphthyl methacrylate can be used as photosensitisers. Monomers with 4-dialkylaminobenzyl- ideneacetophenone residues, e.g., 4-(4-dimethylaminobenzyl- idenecarbonyl)phenyl methacrylate can be used as 398 photoinitiators, including the intrachain ones,399, 400 sensitive to light with a wavelength of 488 nm. Aryl (meth)acrylates undergo photopolymerisation, which makes them promising components of photopolymerisable com- positions (PPC) for printed circuit boards and photoresists.Di(meth)acrylates of the general formula H2C=CRC(O)NH± C6H4OC(O)CR=CH2 are introduced into PPC for improving the technology of manufacturing offset type forms,401 upgrading printing-technical properties of compositions for obtaining thin copying layers.402 It was proposed to introduce 3-acetylamino- phenyl acrylate into PPC for the same purpose.403 Dimethacry- lates of isomeric aminophenols are also used as light-sensitive compounds in compositions for ideally transparent planographic printed circuit boards.404 Two preparative methods for obtaining light-sensitive polymers containing p-phenylene diacrylate groups (PDAG) have been described.Under the action of radiation from an argon laser, PDAG is photodimerised with a quantum yield of 0.44, which allows one to use these polymers as resists.405 Comparison of the reactivities of PA in UV-compositions with alicyclic and aliphatic analogues (including diacrylates) showed its highest efficiency.406 A copolymer of 4-nitrophenyl methacrylate with 2-cinnamoyloxyethyl methacrylate is an efficient negative photoresist with a sensitivity of 17 ± 34 mJ cm72 and a resolution of 1.5 ± 3 mm for a layer 0.5 ± 1 mm thick.407 Homo- and copoly- mers of 4- or 2-tert-butoxycarbonyloxyphenyl (meth)acrylates are used as binding agents in irradiation-sensitive polymer mixtures and depending on the development technique of the irradiated photoresists, negatives or positives are obtained.408 The use of phenyl acrylates in resists for X-ray microlithography with the plasma-based development makes it possible to attain submicron resolution (*0.5 mm) at a sensitivity of 2.5 mJ cm72 (see Ref.409). The content of aryl (meth)acrylate in X-ray resists reaches 30%.410 Positive photoresists with high sensitivity and resolution are obtained by polymerisation of esters of 2-cyanoa- crylic acid in the presence of sulfur-containing compounds.411 Irradiation of poly(halogenophenyl methacrylates) with elec- trons induces their cross-linking;412 therefore, such polymers may be used as negative electron resists.Poly(4-chlorophenyl meth- acrylate) is an example. However, the increase in the number of chlorine atoms in the ring makes destructive processes more pronounced and the resist may become negative. Poly(phenyl methacrylates) with the perfluoalkyl groups are also regarded as negative electron resists. The sensitivities of C3F7- and n-C6F13- containing polymers are 20 and 7 mC cm72, respectively.413 In the case of copolymers, the fluorine atoms may be present in comonomer units. For example, a copolymer of PMA containing up to 50% of a-trifluoromethylacrylic acid is an electron resist with a sensitivity of 10 mC cm72 at a zero residual thick- ness.414, 415 The halogen-free poly[aryl (meth)acrylates] are pos- itive electron resists with an insufficiently high electron sensitivity.It is 50 mC cm72 for PPMA, 200 mC cm72 for PNMA, 65 mC cm72 for poly(fluorenyl methacrylate), 550 mC cm72 for poly(anthryl methacrylate) and differs considerably from that for PMMA (10 mC cm72).416 Introduction of halogen, e.g., by chloromethylation, changes drastically the situation.417 Elec- tron-ray resists become negative with a sensitivity of 3.7 ± 11.0 mC cm72; their sensitivity increases up to a 20%794 content of chloromethyl groups. The crucial role in the cross- linking process is played by recombination of free radicals formed as the result of cleavage of the carbon7halogen bond. In contrast to vinyl and epoxide polymers, virtually no postradiational chain polymerisation, which decreases the resolution obtained, occurs in 2-PNMA.In this particular case it reaches 0.5 mm. This polymer may be sensitised to the action of light with l=365 nm (3% of Michler's ketone), the resultant sensitivity is*100 mJ cm72. The above-considered polymers may be used in the so-called hybrid lithography, where relatively large details of microrelief are obtained under the action of UV light, while fine details are obtained with the aid of a well-focused electron beam. Copolymers of ethylene with halogenoalkyl-substituted PMA are excellent dielectrics.418, 419 Polymers of 4-hydroxystyrene or its halogen derivatives esterified with methacryloyl chloride,420 exhibit good dielectric properties, heat and fire resistance. These are also suitable for manufacturing bases for semiconductor devices.As in the case of copolymers of styrene with 2,4,5- trichlorophenyl acrylate,421 modification of functional groups makes it possible to prepare electron-conducting metallocom- plexes. Polymethacrylates, containing aromatic amino groups in the side chain, were found to possess the hole-type photoconduc- tivity with rather high mobility of charges comparable to that in polyvinylcarbazole.422 There are data on piezoelectrical 423 and magnetic 424 proper- ties of poly[aryl (meth)acrylates]. Specific behaviour of such polymers with liquid-crystalline properties in electric and light fields allows prediction of their wide use in electronics and optics, in particular, in birefringent and colour displays using the `guest ± host' effect, phase lenses and high-resolution laser devices.425, 426 Like phenols, phenyl (meth)acrylates are antiseptics. Intro- duction of chlorine atoms into the aromatic rings increases biocidal activity; however, the low rate of the ester bond hydrolysis 427 of poly[aryl (meth)acrylates], e.g., 2,4,5-trichloro- phenyl methacrylate, may lead to the total loss of this activity.Nonetheless, materials based on copolymers of styrene with pentachlorophenyl acrylate,428, 429 p-chloro-, p-cresyl or biphe- nylyl acrylate and analogous copolymers with MMA and acryl- ates 429 possess noticeable antimicrobial activities. Homo- and copolymers of pentachlorophenyl methacrylate 430 and 2-car- boxyphenyl methacrylate 431 are analogous in this respect.It is proposed to use polymers of 2- and 4-(meth)acryloyloxy- phenylacetic acids 432, 433 and their alkyl esters as bactericidal agents for the purification of sewage. High fungicidal activity is displayed by copolymers of penta- chlorophenyl (meth)acrylate 434 with vinyl acetate, ethyl and butyl acrylates, MMA and MAA. Their emulsions possess good film- forming properties and may be used as components of fungus- resistant dyes 434 for indoor and outdoor work, while copolymers with acrylamide 435 are applied for impregnation of paper. It is proposed to use 2,2-bis(4-methacryloyloxyphenyl)- propane in compositions for fillings in dentistry.436 ± 438 Dentists also make use of solidified compositions which possess enhanced adhesion to metals and the dental tissue and contain from 0.5% to 10% of hydroxybenzoic (meth)acrylate 439 or aromatic di(meth)- acrylates.440 A hemocompatible polymeric material for coating blood-contacting surfaces was obtained from dimethyl (2-hydr- oxyethyl)ammonium salt of poly(2-acryloyloxybenzoic acid).441 Some phenyl methacrylates, e.g., 4-azidophenyl methacrylate, are components of copolymers possessing hemoglobin functions.442 Others, e.g., 4-nitrophenyl acrylate, are introduced into polymeric carriers for the isolation of biologically specific molecules such as proteins, which may be used for radiodiagnostics of thrombi, antigens and tumours 443 or for immobilisation of enzymes, amino acids, proteins 444, 445, e.g., serum albumin.446, 447 Polymers based on 2,4,5-trichlorophenyl, 4-nitrophenyl or 2,4-dinitrophenyl (meth)acrylates are X-ray contrasting preparations.448 Introduction of residues of unsaturated acids into medicinal substances and subsequent polymerisation yield drugs with prolonged action.69 ± 70 Resorption of polymers of acrylic acid V G Syromyatnikov, L P Paskal', I A Savchenko with b-naphthyl acrylate as potential coatings of such medicinal preparations was studied by liquid chromatography by monitor- ing the liberation of the b-naphthol upon hydrolysis of the copolymer.449 Thus, aryl (meth)acrylates possess a very broad spectrum of useful properties and their further studies are highly advisable.References 1. A H Ahlbrecht, D W Codding J.Am. Chem. Soc. 75 984 (1953) 2. W Reppe Ann. Chem. 582B 1 (1953) 3. E M Filachione, I H Lengel, W P Ratchford J. Am. Chem. Soc. 72 839 (1950) 4. G Pizzirani, P L Magagnini Chim. Ind. (Ital.) 50 1218 (1968) 5. P L Magagnini, G Pizzirani Gazz. Chim. Ital. 96 1035 (1966) 6. C Azuma, N Ogata Polym. J. 4 628 (1973) 7. T Ishikawa, S Asai Bull. Chem. Soc. Jpn. 56 2177 (1983) 8. O R G A van Ekenstein, H J H Altena, Y Y Tan Eur. Polym. J. 25 111 (1989) 9. V Blhmer, R Funk, J Kielkiewicz, W Vogt Makromol. Chem. 185B 1905 (1984) 10. N N Lebedev, L V Andrianova Zh. Obshch. Khim. 25 210 (1955) a 11. I A Arbuzova, L I Medvedeva, S A Plotkina Zh. Obshch. Khim. 26 1127 (1956) a 12. G Sumrell, P G Campbell, G E Ham, Ch H Schram J.Am. Chem. Soc. 81 4310 (1959) 13. M M Koton, T N Sokolova, N I Savitskaya, T M Kiseleva Zh. Obshch. Khim. 28 417 (1958) a 14. S Patal,W Bentov, M Reighmann J. Am. Chem. Soc. 74 845 (1952) 15. USSR P. 759 504; Byull. Izobret. (32) 100 (1980) 16. S Li, A C Albertsson, A Gupta,W Bassett, O Vogl Monatsh. Chem. 115 853 (1984) 17. M G Zhenevskaya, T V Sheremet'eva,M M Koton Izv. Akad. Nauk SSSR, Ser. Khim. 331 (1964) b 18. D Filipovic, L Vrhovac, J Velickovic J. Serb. Chem. Soc. 53 85 (1988) 19. J M J Frechet, F Mikes, D Vyprachticky, Lam Hoang, J Labsky Makromol. Chem. 189 671 (1988) 20. B Jamada, T Tanaka, T Otsu Eur. Polym. J. 25 117 (1989) 21. B S R Reddy, R Arshady,M H George Macromolecules 16 1813 (1983) 22. O G Abdullaev, O G Tsoi, T I Kalendareva, S Sh Rashidova Uzb.Khim. Zh. 11 (1987) 23. Zh I Buloichik, T A Kovgan, A M Lazareva, A V Pavlov Vysokomol. Soedin., Ser. B 30 99 (1988) c 24. V Z Annenkova, V M Annenkova, K A Abzaeva, M G Voronkov Zh. Prikl. Khim. 58 1191 (1985) d 25. B V Lebedev, N K Lebedev, E G Kiparisova, K A Esayan, L K Golova, Yu B Amerik Vysokomol. Soedin., Ser. A 26 909 (1984) c 26. F J Viersen, Tan Y Yong, von Bolhuis Fre, J M Zwiers Renso Makromol. Chem. 186 1987 (1985) 27. A B Padias, H K Hall Am. Chem. Soc. Polym. Prepr. 31 595 (1990) 28. O A Abdiev, N B Mutallimova, S D Murshudova, I M Akhmedov, in Radikal'naya Polimerizatsiya (Tez. Dokl.), Gor'kii, 1989 [Radical Polymerisation (Abstracts of Reports), Gor'kii, 1989] p. 51; Ref. Zh.Khim. 23 S 628 (1989) 29. F Hrabak,M Bezdek, H Pivcova, V Kubanek Collect. Czech. Chem. Commun. 52 1494 (1987) 30. V V Egorov,V P Zubov Usp. Khim. 56 2065 (1987) [Russ. Chem. Rev. 56 1153 (1987)] 31. A V Volokhina, Yu N Godovskii, G I Kudryavtsev Zhidkokristalli- cheskie Polimery (Mesomorphic Polymers) (Moscow: Khimiya, 1988) 32. J Horvath, F Cser, G Hardy Magy. Kem. Foly. 91 167 (1985) 33. J Horvath, K Nyitrai, G Hardy Eur. Polym. J. 21 251 (1985) 34. G Hardy, S V Bushin, I N Shtennikova Acta Chim. Hung. 123 (3±4) 83 (1986) 35. F Cser, K Nyitrai, P Forgacs Magy. Kem. Foly. 89 29 (1983) 36. J Horvath, F Cser, G Hardy Magy. Kem. Foly. 91 529 (1985) 37. T I Borisova, L L Burshtein, I I Konstantinov, V P Malinovskaya, Yu B Amerik Vysokomol.Soedin., Ser. B 29 782 (1987) c 38. V N Tsvetkov, I N Shtennikova, N V Pogodina Mol. Cryst. Liq. Cryst. 133 169 (1986) 39. G Galli,M Laus, A S Angeloni Makromol. Chem. 187 289 (1986)Aryl (meth)acrylates and polymers based on them 40. S Basu, A Rawas, H H Sutherland Mol. Cryst. Liq. Cryst. 132 23 (1986) 41. R Duran, D Guillon, P Gramain, A Skoulios Makromol. Chem. Rapid. Commun. 8 321 (1987) 42. R Duran, D Guillon, P Gramain, A Skoulios J. Phys. (Fr.) 48 2043 (1987) 43. J C Dubois, J C Lavenu, A Zann Am. Chem. Soc. Polym. Prepr. 18 63 (1977) 44. A S Angeloni, M Laus, C Castellari, G Galli Makromol. Chem. 186 977 (1985) 45. C M Paleos, S E Filippakis J. Polym. Sci., Polym. Chem. Ed. 19 1427 (1981) 46. Jpn. Appl. 58-11 516; Ref.Zh. Khim. 12 S 348P (1984) 47. F Cser,K Nyitrai, J Horvath,G Hardy, in IUPAC MACRO'83, Sec. 1 (Abstracts of Reports), Bucharest, 1983 p. 4; Ref. Zh. Khim. 17 S 223 (1984) 48. V Frosini, P L Magagnini, B Bresci, A Marchetti, in The 26th International Symposium on Macromolecules. (Abstracts of Reports), Mainz, 1979 Vol. 2, p. 1020 49. K P Naikwadi, A L Jadhav, S Rokushika Makromol. Chem. 187 1407 (1986) 50. A MoÈ ller, U Czaika, V Bergmann, J Lindau, M Arnold, F Kuschel Z. Chem. 27 218 (1987) 51. V L Khodzhaeva, I I Konstantinov Vysokomol. Soedin., Ser. A 29 641 (1987) c 52. F Cser, K Nyitrai, E Seyfried, G Hardy Magy. Kem. Foly. 82 207 (1976) 53. Jpn. Appl. 60-192 712; Ref. Zh. Khim. 17 S 536P (1986) 54. C M Paleos, G Margomenou-Leonidopoulou, S E Filippakis, A Malliaris J.Polym. Sci., Polym. Chem. Ed. 20 2267 (1982) 55. Yu G Yanovskii, I I Konstantinov, Yu B Amerik, G V Vinogradov Vysokomol. Soedin., Ser. B 27 212 (1985) c 56. T I Borisova, L L Burshtein, V P Malinovskaya, L V Krasker, I I Konstantinov, Yu B Amerik Vysokomol. Soedin., Ser. A 26 2122 (1984) c 57. I N Shtennikova, E V Korneeva, G F Kolbina Vysokomol. Soedin., Ser. B 29B 463 (1987) c 58. I N Shtennikova, E V Korneeva, G F Kolbina Vysokomol. Soedin., Ser. A 30 2532 (1988) c 59. V Shibaev, Lui Lam (Eds) Liquid Crystalline and Mesomorphic Polymers Berlin: Springer, 1994) 60. WBrostow (Ed.) Mechanical and Termophysical Properties of Polymer Liquid Crystals (London: Chapmain and Hall, 1998) 61. T Matynia, P Penzek, A Wojcik Rocz.Chem. 48 525 (1974) 62. N Kh Maksudov, Z Sh Enileeva, L F Golovyashkina Uzb. Khim. Zh. 19 34 (1975) 63. H Kumazaki, T Nakaya,M Imoto J. Macromol. Sci. 10A 993 (1976) 64. L A Vretik, V V Zagnii,M V Kazimirova, A Yu Kolendo, I A Savchenko, V G Syromyatnikov Vest. Kievsk. Univ., Khim. 33 136 (1996) 65. M F Winnik, K C Ober Eur. Polym. J. 23 617 (1987) 66. T Kimura, T Yoshimura, H Morimoto,M Hamashima Polym. J. 19 1165 (1987) 67. R Pfander, H Hocker Makromol. Chem. Makromol. Symp. 4 119 (1986) 68. Li Fumian, Lin Wang, Li Yuiogin, Feng Xinde Polym. Commun. (1) 75 (1986) 69. G K Kirienko Zh. Vses. Khim. O-va imDI Mendeleeva 13 238 (1968) e 70. G K Kirienko, L I Aristov, A A Shamshurin Khim. Geterotsikl. Soedin. 823 (1969) f 71.F Linuma, H Mikawa, V Shirota Polym. J. 13 641 (1981) 72. M Kamachi, Cheng Xian Su, T Kida Macromolecules 20 2665 (1987) 73. A Kajiwara, M Kamachi Chem. Express 4 105 (1989) 74. K Yokota, M Sasaki, J Ishii J. Polym. Sci., Part A, Polym. Chem. 6 2935 (1968) 75. A Yu Kolendo, V G Syromyatnikov, L P Paskal', E L Shapoval, in Radikal'naya Polimerizatsiya (Tez. Dokl.), Gor'kii, 1989 [Radical Polymerisation (Abstracts of Reports), Gor'kii, 1989] p. 102; Ref. Zh. Khim. 23 S 628 (1989) 76. S Iwatsuki, T Itoh, Y Shimizu Macromolecules 18 1 (1985) 77. V V Klyushin, V G Syromyatnikov, S A Filipchenko, E V Yatsenko Vest. Kievsk. Univ., Khim. 22 47 (1981) 78. US P. 3 190 876; Chem. Abstr. 63 14 761 (1965) 795 79. V V Zagnii, V G Syromyatnikov Vest.Kievsk. Univ., Khim. 20 56 (1979) 80. V G Syromyatnikov, V V Zagnii, V P Naidenov, in Teoriya i Praktika Kataliticheskikh Reaktsii i Khimiya Polimerov (The Theory and Practice of Catalytic Reactions and the Chemistry of Polymers) (Cheboksary: Chuvashsk. State University, 1990) p. 38 81. V G Syromyatnikov, A V Botsman, V V Zagnii, T Prot Vest. Kievsk. Univ., Khim. 27 48 (1986) 82. V V Zagnii, V G Syromyatnikov, V G Sinyavskii Vest. Kievsk. Univ., Khim. 28 37 (1987) 83. A L Finkenaur, L Dickinson, C W Charles, J Chien Am. Chem. Soc. Polym. Prepr. 25 109 (1984) 84. Bolg. P. 30 998; Ref. Zh. Khim. 4 S 453P (1983) 85. Lu Chengxun, C G Overberger J. Polym. Sci., Polym. Chem. Ed. 22 2413 (1984) 86. H Ringsdorf, G Greber Makromol.Chem. 31 27 (1959) 87. V G Syromyatnikov, V Ya Pochinok, L P Paskal', in Sintez i Fizikokhimiya Polimerov (Synthesis and Physical Chemistry of Polymers) (Kiev: Naukova Dumka, 1971) No. 9, p. 3 88. L P Paskal', V G Syromyatnikov, V Ya Pochinok Vest. Kievsk. Univ., Khim. 16 65 (1975) 89. V G Syromyatnikov, L I Sholudchenko Vest. Kievsk. Univ., Khim. 26 28 (1985) 90. L P Paskal', V G Syromyatnikov Ukr. Khim. Zh. 48 204 (1982) 91. V V Korshak, G M Tseitlin, L D Raizer Zh. Org. Khim. 12 2264 (1976) g 92. L P Paskal', V G Syromyatnikov, T A Kalmykova Vest. Kievsk. Univ., Khim. 19 45 (1978) 93. V G Syromyatnikov, L P Paskal', T A Orlyuk Vest. Kievsk. Univ., Khim. 28 41 (1987) 94. L A Vretik, A Yu Kolendo, V G Syromyatnikov Ukr.Khim. Zh. 63 (7 ± 8) 124 (1997) 95. W Syromiatnikow, A Kolendo, I Sawczenko, L Wretik, L Paskal, W Zagnij, N Lysenko, T Prot Prace Nauk. Inst. Techn. Org. Politechniki Wroclawskiej 46 79 (1997) 96. L Vrhovac, D Filipovic, M Misic-Vukovic, J Velickovic Int. J. Chem. Kinet. 24 861 (1992) 97. A Gallardo, J S Roman Macromolecules 25 5836 (1992) 98. L Vrhovac, V Savov, G Pancic, J Velickovic, D Filipovic, in International Symposium on Mechanics and Kinetics of Polymer Reaction (Abstracts of Reports), Paris, 1990 p. 265 99. B Yamada, A Matsumoto, T Otsu J. Polym. Sci., Polym. Chem. Ed. 21 2241 (1983) 100. L Vrhovac, J Velickovic, J M Filipovic Makromol. Chem. 185 1637 (1984) 101. B Yamada, S Sugiyama, S Mori, T Otsu J. Macromol. Sci.15A 339 (1981) 102. I Katime, T Nuno, D Radic Thermochim. Acta (124) 263 (1988) 103. J M Filipovic,D M Petrovic-Djakov,L P Vrhovac, J S Velickovic J. Therm. Anal. 38 709 (1992); Ref. Zh. Khim. 1 S 204 (1993) 104. S Polowinski, S Tarkowska Makromol. Chem. 184 1571 (1983) 105. G Aypey, A C Haynes Eur. Polym. J. 9 1029 (1973) 106. M Kamachi, D J Liaw, S Nozakura Polym. J. 9 307 (1977) 107. M Kamachi, D J Liaw, S Nozakura Polym. J. 13 41 (1981) 108. D J Liaw, R-S Lin J. Macromol. Sci. 31A 715 (1994) 109. S Raghunath, M H Rao, K N Rao Radiat. Phys. Chem. 22 1011 (1983) 110. J S Roman, E L Madruga,M A Del Puerto J. Polym. Sci., Polym. Chem. Ed. 21 691 (1983) 111. L Vrhovac, J D Filipovic, J Velickovic J. Serb. Chem. Soc. 51 589 (1986) 112.O G Abdullaev, T I Kalendareva, S Sh Rashidova Uzb. Khim. Zh. 14 (1987) 113. Y Kadoma, T Toida, K Takeda, K Uno, J Iwakura J. Polym. Sci., Polym. Chem. Ed. 13 707 (1975) 114. C I Simionescu, V Percec, A Natansohn Polym. Bull. 3 529 (1980) 115. K Shin-ichi,M Katsuyuki, K Masayuki Chem. Pharm. Bull. 42 768 (1994) 116. T K Khanmamedov,O B Abdyev,G S Ovanesova,R M Aliguliev Azerb. Khim. Zh. (5) 76 (1981) 117. V Blhmer, R Funk,W Vogt Makromol. Chem. 185B 2195 (1984) 118. V G Syromyatnikov, A Yu Kolendo Vest. Kievsk. Univ., Khim. 29 56 (1988)796 119. A Yu Kolendo, V G Syromyatnikov, L P Paskal' Ukr. Khim. Zh. 56 647 (1990) 120. V G Syromyatnikov, E V Blazhko, A Yu Kolendo, L P Paskal', in Sintez i Modifikatsiya Polimerov (The Synthesis and Modification of Polymers) (Cheboksary: Chuvashsk.State University, 1989) p. 25 121. V G Syromyatnikov, A Yu Kolendo, L P Paskal', E L Shapovalova Vest. Kievsk. Univ., Khim. 31 44 (1990) 122. I A Savchenko, A Yu Kolendo, V N Yashchuk, V G Syromyatnikov, in XVII Ukrainskaya Konf. po Organicheskoi Khimii (Tez. Dokl.), Khar'kov, 1995 [The XVIIth Ukrainian Conference on Organic Chemistry (Abstracts of Reports), Khar'kov, 1995] p. 483 123. V G Syromyatnikov, V N Yashchuk Dokl. Akad. Nauk Ukr. (12) 56 (1995) 124. V G Syromyatnikov, V N Yashchuk, T Yu Ogul'chanskii, L A Vretik, A Yu Kolendo Dokl. Akad. Nauk Ukr. (9) 171 (1998) 125. O Tokahiro, O Takayuki J. Polym. Sci., Polym. Chem. Ed. 21 3169 (1983) 126. O F Solomon,M G Coreiovei, V Tararescu J.Appl. Polym. Sci. 11 1631 (1967) 127. K Yokota, N Hirayama, Y Takada Polym. J. 7 629 (1975) 128. K Yokota, T Kakuchi, Y Takada Polym. J. 10 19 (1978) 129. K Yokota, T Kakuchi, Y Takada Bull. Fac. Eng. Hokkaido Univ. (102) 45 (1981); Ref. Zh. Khim. 16 S 248 (1981) 130. S Singh,D Creed, C E Hoyle Proc. SPIE-Int. Soc. Opt. Eng. 1774 2 (1993) 131. T Nishikubo, T Iisawa, E Takahashi, F Nona Polym. J. 16 371 (1984) 132. K Subramanian, V R Reddy, V Krishnaswamy Makromol. Chem. Rapid. Commun. 12 211 (1991) 133. T Kimura, I Nakanishi, M Hamashima Polym. J. 18 689 (1986) 134. L K Golova, Y B Amerik Makromol. Chem. 182 1889 (1981) 135. V G Syromyatnikov, S A Filipchenko, V V Klyushin Vest. Kievsk. Univ., Khim. 23 28 (1982) 136.L A Vretik, A Yu Kolendo, V M Pas'ko, I A Savchenko, V G Syromyatnikov, L N Fedorova Vest. Kievsk. Univ., Khim. 33 139 (1996) 137. L Anglioline, D Caretti, C Carlini J. Polym. Sci. Part A, Polym. Chem 32 1159 (1994) 138. A A Korobkov, Z A Azimov Vysokomol. Soedin. 7 1326 (1965) c 139. H Kammerer, H Gueniffrey, C Pinazzi C. R. Hebd. Seances Acad. Sci., Ser. A 272 1714 (1971) 140. A Alaya, F Carriere, P Monjol, H Sekiguchi Eur. Polym. J. 21 663 (1985) 141. O R G A van Ekenstein, J J Jong Makromol. Chem. 192 2641 (1991) 142. H Gueniffrey, H Kammerer, C Pinazzi Makromol. Chem. 136 173 (1970) 143. K Yokota, T Hirabayashi J. Polym. Sci., Polym. Chem. Ed. 16 2077 (1978) 144. T Oishi, M Fujimoto, T Hirota, S Kajigaeshi J. Macromol. Sci. 23A 687 (1986) 145.Jpn. Appl. 61-278 508; Ref. Zh. Khim. 24 S 426P (1987) 146. K Yokota, T Kougo, T Hirabayashi Polym. J. 15 349 (1983) 147. T Otsu, T Ito,Y Fuju,M Imoto Bull. Chem. Soc. Jpn. 41 204 (1968) 148. L P Paskal', V Ya Pochinok, V G Syromyatnikov Ukr. Khim. Zh. 49 530 (1983) 149. A N Vereshchagin Induktivnyi Effekt. Konstanty Zamestitelei dlya Korrelyatsionnogo Analiza (Inductive Effect. Constants of Substituents for Correlation Analysis) (Moscow: Nauka, 1988) p. 111 150. T Otsu, T Ito,M Imoto J. Polym. Sci., Polym. Chem. Ed. 4 733 (1966) 151. K Saric, Z Janovic, O Vogl Croat. Chem. Acta 58 57 (1985) 152. E I Sembai, I A Sutyk, B I Budzan, I I Gavlo Vest. L'vovsk. Politekhn. Inst. (171) 142 (1983) 153. T-C Chiang, Z-B Xia Polym.Commun. 26 364 (1985) 154. F Hrabak,M Bezdek, V Hynkova, J Svobodova Makromol. Chem. 183 2675 (1982) 155. M Bezdek, V Hynkova, F Hrabak Makromol. Chem. 184 1967 (1983) 156. Bolg. P. 37 137; Ref. Zh. Khim. 18 S 476P (1986) 157. O Todorova, I Gitsov, V Sinigersky Polym. Bull. 15 511 (1986) V G Syromyatnikov, L P Paskal', I A Savchenko 158. H Boudevska, C Bratschkov, O Todorova, D Braun, W K Czerwinski Makromol. Chem. 188 1157 (1987) 159. L N Zaitseva, T D Korneeva, I A Khotina, P V Petrovskii, M M Teplyakov, in Sintez, Struktura i Svoistva Setchatykh Polimerov (Tez. Dokl.), Zvenigorod, 1988 [The Synthesis, Structure and Properties of Network Polymers (Abstracts of Reports), Zvenigorod, 1988] p. 198; Ref. Zh. Khim. 14 S 297 (1988) 160. M D B Desai, B S R Reddy, R Arshady,M H George Polymer 27 96 (1986) 161. K Saric, Z Janovic, O Vogl J.Macromol. Sci. 19A 837 (1983) 162. T Kovacic, K Saric, Z Janovic Polimeri 15 161 (1994) 163. A P Kiseleva, V G Kolesnikova, B I Budzan Vest. L'vovsk. Politekhn. Inst. (201) 54 (1986) 164. G Bauduin,Y Pietrasanta,A Rousseau,D Granierazema,D Bosc, M Guilbert Eur. Polym. J. 28 923 (1992) 165. J S Roman, E L Madruga,M A D Puerto J. Polym. Sci., Polym. Chem. Ed. 21 3303 (1983) 166. J S Roman, E L Madruga, L Pargada Polymer 28 315 (1987) 167. R Roussel, J C Galin J. Macromol. Sci. 11A 347 (1977) 168. A Miller, J Szafko J. Polym. Sci., Polym. Chem. Ed. 15 1595 (1977) 169. K Saric, Z Janovic, in The 28th Macromolecular Symposium of the IUPAC, Sect. 1 (Abstracts of Reports), Amherst, MA, 1982 p.124; Ref. Zh. Khim. 4 S 282 (1983) 170. Z Janovic, K Saric, O Vogl Croat. Chem. Acta 59 413 (1986) 171. H Boudevska, V Sinigersky, in IUPAC MACRO'83, Sec. 1 (Abstracts of Reports), Bucharest, 1983 p. 609; Ref. Zh. Khim. 17 S 219 (1984) 172. H Boudevska, V Sinigersky Makromol. Chem. 185 531 (1984) 173. Bolg. P. 34 826; Ref. Zh. Khim. 18 S 428P (1985) 174. H Boudevska, O Todorova Makromol. Chem. 185 353 (1984) 175. E Yun, L V Lobanova, A D Litmanovich, N A Plate Vysokomol. Soedin., Ser. A 12 2488 (1970) c 176. T Narasimhaswamy, S C Sumathi, B S R Reddy Polymer 32 3426 (1991) 177. N Kunieda, S Yamane, H Tagushi, M Kinoshita Makromol. Chem. Rapid. Commun. 4 (2) 57 (1983) 178. B S R Reddy, R Arshady,M H George Eur.Polym. J. 21 511 (1985) 179. I V Andreeva, M M Koton, V N Artem'eva, N V Kukarkina Vysokomol. Soedin., Ser. 20B 127 (1978) 180. I V Andreeva, M M Koton, V N Artem'eva, N V Kukarkina, T D Glumova Vysokomol. Soedin., Ser. A 19 1780 (1977) 181. E E Ergozhin, L N Prodius, B Kapparov Izv. Akad. Nauk Kaz. SSR, Ser. Khim. (2) 60 (1983) 182. K Schaefers, C Schneider J. Polym. Sci., Polym. Chem. Ed. 23 2879 (1985) 183. J Rodriguez-Parada, V Percec Am. Chem. Soc. Polym. Prepr. 25 83 (1984) 184. C I Simionescu, V Percec, A Natansohn J. Polym. Sci., Polym. Chem. Ed. 20 655 (1982) 185. V Percec, A Natansohn, C I Simionescu, in IUPAC Makro Mainz. The 26th International Symposium on Macromolecules (Abstracts of Reports) Mainz, 1979 Vol. 1, P.345; Ref. Zh. Khim. 19 S 150 (1980) 186. C I Simionescu, V Percec, A Natansohn Polymer 21 417 (1980) 187. V Percec, A Natansohn, C I Simionescu J. Macromol. Sci. 15A 405 (1981) 188. J E Mulvaney, R A Brand Macromolecules 13 244 (1980) 189. I A Savchenko, A Yu Kolendo, T Yu Ogul'chanskii, V N Yashchuk, V G Syromyatnikov Ukr. Khim. Zh. 61 (1 ± 2) 53 (1995) 190. T Yu Ogul'chanskii, V G Syromyatnikov, V N Yashchuk, I A Savchenko, A Yu Kolendo Ukr. Fiz. Zh. 40 (4) 286 (1995) 191. V Syromiatnikow, A Kolendo, I Sawczenko, W Jaszczuk, T Prot, J Szczerba Prace Nauk. Inst. Techn. Org. Politechniki Wroclawskiej 45 217 (1995) 192. V N Yashchuk, A Yu Kolendo, I A Savchenko, V G Syromyatnikov, T Yu Ogul'chanskii Nauch.Zap. Vys. Shkoly Akad. Nauk Ukr. (1) 141 (1998) 193. Z Janovic, K Saric, O Vogl J. Polym. Sci., Polym. Chem. Ed. 21 2713 (1983) 194. Z Janovic, K Saric, O Vogl J. Macromol. Sci. 22A 85 (1985) 195. Z Janovic, K Saric, in IUPAC MACRO'83, Sec. 1 (Abstracts of Reports), Bucharest, 1983 p. 37 196. Z Florjanzyk, E Zygadlo Polymer 32 2853 (1991)Aryl (meth)acrylates and polymers based on them 197. J M Filipovic,D M Petrovic-Djakov,L P Vrhovac, J S Velickovic J. Therm. Anal. 40 735 (1993) 198. T Narasimhaswamy, S C Sumathi, B S R Reddy J. Sci. Ind. Res. 52 159 (1993) 199. K Matsuzaki, T Kanai, K Yamawaki, K Rung Makromol. Chem. 174 215 (1973) 200. W M Jimmy, N Hadjichristidis, J S Lindner J. Polym. Sci., Part B, Polym. Phys 28 1881 (1990) 201.J S Roman, E L Madruga Eur. Polym. J. 17 15 (1981) 202. E A Grishchenko, A E Ruchin, N B Misharina, V S Skazka Vysokomol. Soedin., Ser. B 25 653 (1983) c 203. T Ojeda,R Deodato, L Gargallo, B Daphne Makromol. Chem. 181 2237 (1980) 204. B Vazquez, M Gurruchada, I Goni, E Narvarte, T S San Roman Polymer 36 3467 (1995) 205. K G Kempf, H Harwood Macromolecules 11 1038 (1978) 206. H Boudevska, C Brutchkov, V Kolova, Q T Pham Eur. Polym. J. 14 619 (1978) 207. H Boudevska, C Brutchkov Makromol. Chem. 180 1661 (1979) 208. C Brutchkov, V Sinigersky, L Markova,H Boudevska Eur. Polym. J. 21 569 (1985) 209. C I Simionescu, A Natansohn, V Percec Colloid Polym. Sci. 259 697 (1981) 210. J S Roman, E L Madruga Eur. Polym. J. 18 481 (1982) 211.B Vesslen, G Gunneby, G Hellstrom, P Soelding J. Polym. Sci. Polym. Symp. 42 457 (1973) 212. A D Litmanovich, N A Plate Vysokomol. Soedin., Ser. A 17 1112 (1975) c 213. M M Guseinov, T K Khapmamedov, F D Agaev Azerb. Khim. Zh. (3) 52 (1985) 214. E L Madruga, J S Roman Makromol. Chem. Rapid. Commun. 7 307 (1986) 215. L Gargallo, N Hamidi, D Radic Thermochim. Acta 114 319 (1987) 216. J S Roman, E L Madruga, J Guzman Polym. Commun. 25 373 (1984) 217. A Marchetti, G Levita, D Lupinacci Chim. Ind. (Ital.) 64 483 (1982) 218. J S Velickovic, D Djukanovic, in IUPAC MACRO'83, Sec. 2±3, 5 (Abstracts of Reports), Bucharest, 1983 p. 295; Ref. Zh. Khim. 17 S 296 (1984) 219. J S Roman, E L Madruga, L Pargada Polym. Degrad. Stab. 19 161 (1987) 220.S Zulfigar, M Zulfigar, K Tasneem, I C McNeill Polym. Degrad. Stab. 17 327 (1987) 221. Z Janovic, K Saric, O Vogl J. Macromol. Sci. 19A 1137 (1983) 222. J S Velickovic, D M Petrovic-Djakov, in IUPAC MACRO'83, Sec. 1 (Abstracts of Reports), Bucharest, 1983 p. 545; Ref. Zh. Khim. 20 S 46 (1984) 223. D M Petrovic-Djakov, J S Velickovic, B Plavsic-Milenko J. Serb. Chem. Soc. 50 (1) 31 (1985) 224. L Gargallo, N Hamidi, D Radic Polymer 31 924 (1990) 225. L Gargallo, N Hamidi, D Radic Polym. Int. (Br. Polym. J.) 24 1 (1991) 226. L P Paskal', V M Potapov, A F Samarin, V G Syromyatnikov Vest. Kievsk. Univ., Khim. 17 35 (1976) 227. I Katime, M T Garay Eur. Polym. J. 21 489 (1985) 228. I Katime, M T Garay, J Francois J. Chem. Soc., Faraday Trans.2 81 705 (1985) 229. L Gargallo, D Radic, N Hamidi, L Cardenas, A Horta J. Appl. Polym. Sci. 36 1495 (1988) 230. S Ponce, D Radic, L Gargallo, in IUPAC Makro Mainz. The 26th International Symposium on Macromolecules (Abstracts of Reports), Mainz, 1979 Vol. 1, p. 779; Ref. Zh. Khim. 18 S 50 (1981) 231. B Wandelt, J Szumilewicz Polymer 28 1791 (1987) 232. E Riande, E L Madruga, J S Roman, E Saiz Macromolecules 21 2807 (1988) 233. T I Borisova, L L Burshtein, V P Malinovskaya, T P Stepanova, I I Konstantinov Vysokomol. Soedin., Ser. B 30 821 (1988) c 234. J Alexopoulos, N Hadjichristidis Makromol. Chem. 179 549 (1978) 235. J Alexopoulos, N Hadjichristidis, A Vassiliadis Polymer 16 386 (1975) 236. N Hadjichristidis Makromol.Chem. 134 1043 (1983) 237. N Hadjichristidis, C Touloupis, S Karvounis Makromol. Chem. 183 611 (1982) 797 238. J Alexopoulos, N Hadjichristidis Makromol. Chem. 180 455 (1979) 239. R Diaz-Calleja, E Riande, J S Roman J. Phys. Chem. 96 6843 (1992) 240. P Gregory, B Huglin Malkolm, K H Khorasani Mohamad, M P Sasia Br. Polym. J. 20 1 (1988) 241. I Katime, M T Garay Polym. Commun. 27 (3) 74 (1986) 242. B Huglin Malkolm, K H Khorasani Mohamad,M P Sasia Polymer 29 1590 (1988) 243. V E Eskin, A I Kipner Vysokomol. Soedin., Ser. B 30 491 (1988) c 244. V E Eskin, A I Kipner Vysokomol. Soedin., Ser. B 30B 845 (1988) c 245. R Duran, C Strazielle Macromolecules 20 2853 (1987) 246. L Gargallo, D Radic, L H Tagle Polym. Bull. 17 15 (1987) 247. D Radic, L Gargallo J.Polym. Sci., Polym. Phys. Ed. 16 977 (1978) 248. Y Kihira, K Sugiyama Makromol. Chem. 187 2445 (1986) 249. Y Kihira, K Sugiyama J. Macromol. Sci. 26B 227 (1987) 250. R Diaz-Calleja, E Riande, J S Roman Macromolecules 24 264 (1991) 251. R Diaz-Calleja, E Riande, J S Roman Macromolecules 24 1854 (1991) 252. M Nikita, I Kanno, M Ieda, I Ishino IEEE Trans. Electr. Insul. 22 175 (1987) 253. H Roth, in 8 Tagung: Polymerphysik, Kurzfassung der Vortrage und Poster. Leipzig, Kurzfass. Vort. und Poster, 1986 p. 205; Ref. Zh. Khim. 15 S 163P (1987) 254. Jpn. Appl. 63-33 405; Ref. Zh. Khim. 14 S 417P (1989) 255. Jpn. Appl. 59-136 311; Ref. Zh. Khim. 16 S 368P (1985) 256. Jpn. Appl. 58-171 408; Ref. Zh. Khim. 17 S 409P (1984) 257.V I Tsvetkov Zhestkotsepnye Polimernye Molekuly (Rigid-Chain Polymer Molecules) (Leningrad: Nauka, 1986) p. 380 258. V P Shibaev, R V Tal'rose Wiss. Beitr. M. Luther. Univ. Hall-Wittenberg 17 96 (1986) 259. F Hessel, H Finkelmann Makromol. Chem. 189 2275 (1988) 260. F Wang, J R Reynolds Macromolecules 21 2889 (1988) 261. G Hardy, F Cser, K Nyitrai Magy. Kem. Foly. 86 456 (1980) 262. V P Shibaev,M V Kozlovskii, N A Plate Vysokomol. Soedin., Ser. A 29 1144 (1987) c 263. Ya S Freidzon, N I Boiko, V P Shibaev, N A Plate Vysokomol. Soedin., Ser. A 29 1464 (1987) c 264. V V Tsukruk, M V Kozlovskii, V P Shibaev, V V Shilov, Yu S Lipatov Vysokomol. Soedin., Ser. A 29 2630 (1987) c 265. V V Tsukruk, M V Kozlovskii, V V Shilov, V P Shibaev Kristallografiya 33 721 (1988) h 266.V L Khodzhaeva, I I Konstantinov, V S Grebneva Vysokomol. Soedin., Ser. A 28 720 (1986) c 267. C M Paleos, G Margomenou-Leonidopoulou, S E Filippakis, A Malliaris, in The 28th Macromolecular Symposium of the IUPAC, Sect. 1 (Abstracts of Reports), Amherst MA, 1982 p. 811 268. S G Kostromin, V V Sinitsyn, R V Tal'roze, V P Shibaev Vysokomol. Soedin., Ser. A 26 335 (1984) c 269. Yu S Lipatov, V V Tsukruk, V V Shilov, S G Kostromin, V P Shibaev Vysokomol. Soedin., Ser. B 29 411 (1987) c 270. P Zugenmaier, H Menzel Makromol. Chem. 189 2647 (1988) 271. S Polowinski, B Bortnowska-Barela J. Polym. Sci., Polym. Chem. Ed. 19 51 (1981) 272. B Bortnowska-Barela, S Polowinski J. Polym. Sci., Polym. Chem. Ed. 20 3267 (1982) 273.T Ouchi, M Nakai, T Azuma J. Macromol. Sci. 21A 29 (1984) 274. T Ishikawa, Y Tanaka Bull. Chem. Soc. Jpn. 58 1182 (1985) 275. T Ishikawa,M Otsuki, T Iwatsuki Bull. Chem. Soc. Jpn. 59 3621 (1986) 276. R Arshady Makromol. Chem. 185 2387 (1984) 277. F Mikes, J Labsky, D Vyprachticky Sb. SVCHT Praze. S. 16 163 (1987); Ref. Zh. Khim. 8 S 391 (1987) 278. M V Solovskii, N A Petukhova Vysokomol. Soedin., Ser. B 34 (8) 30 (1992) c 279. M V Solovskii Zh. Prikl. Khim. 67 1670 (1994) d 280. H Shuyama J. Fluor. Chem. 29 467 (1985) 281. V Z Annenkova, V M Annenkova, K A Abzaeva Vysokomol. Soedin., Ser. B 27 368 (1985) c 282. R Arshady Makromol. Chem. Rapid. Commun. 4 237 (1983) 283. Eur. Appl. 0 188 037; Ref. Zh. Khim. 9 S 515P (1987) 284.E A Abuin, E A Lissi, L Gargallo, D Radic Eur. Polym. J. 16 693 (1980) 285. D A Holden, A Safarzadeh-Amiri Macromolecules 20 1588 (1987)798 286. D A Holden, A Safarzadeh-Amiri Am. Chem. Soc. Polym. Prepr. 27 348 (1986) 287. D A Holden, S E Shephard, J E Guillet Macromolecules 15 1481 (1982) 288. G Zanocco, E Abuin, E Lissi, L Gargallo, D Radic Eur. Polym. J. 18 1037 (1982) 289. H Boudevska, C Brutchkov, H Astrong Eur. Polym. J. 19 737 (1983) 290. A Ledwith Pure Appl. Chem. 54 549 (1982) 291. W F Curtis, M A Gashgari Macromolecules 12 163 (1979) 292. B Wandelt, D S Birch, R E Imhof, R A Pathrick, in The 31st Macromolecular Symposium of the IUPAC, Sec. 1 (Abstracts of Reports), Merseburg, 1987 p. 175 293. Z Wang, F R W Mc Court, D A Holden Macromolecules 25 1576 (1992) 294.S Iwatsuki, T Itoh, K Takagi Macromolecules 25 4597 (1992) 295. S S Klimova, M I Frolova, S N Zhdankina Fiz. Khim. Osnovy Sint. Pererab. Polim. 58 (1986) 296. S Nishimoto, K Yamamoto, T Kagiya Polym. Photochem. 5 231 (1984) 297. S Nishimoto, K Yamamoto, T Kagiya Macromolecules 15 720 (1982) 298. S Nishimoto, K Yamamoto, T Kagiya Macromolecules 15 1180 (1982) 299. H Shuyama J. Chem. Soc. Jpn., Chem. Ind. Chem. 1869 (1985) 300. H Boudevska, C Bratschkov, O Todorova, E Bezdadea, D Braun Angew. Macromol. Chem. 148 27 (1987) 301. K Matsuzaki, T Kanai Cellul. Chem. Technol. 12 413 (1978) 302. M Wasche, T Gross, I von Lampe Polym. Bull. 14 147 (1985) 303. M Wasche, R Kunze, I von Lampe, H Kerkow, E Linke, iIn Proceedings of the 6th Tifany Symposium on Radiation Chemistry (Abstracts of Reports), Balaton-szeplak, Budapest, 1987 Vol.2, p. 491 304. P H Lu, G N Babu, J C W Chien J. Polym. Sci., Polym. Lett. Ed. 23 1421 (1985) 305. R Kunze, M Wasche, E Linke Polym. Bull. 15 285 (1986) 306. A Altomare, C Carlini, F Ciardelli, R Solaro, N Rosato J. Polym. Sci., Polym. Chem. Ed. 22 1267 (1984) 307. A Altomare, C Carlini, F Ciardelli, R Solaro Polym. J. 20 801 (1988) 308. E G Gilazhov, N L Ivanova, N V Zubko, I A Arbuzova Izv. Akad. Nauk Kaz. SSR, Ser. Khim. 28 (4) 81 (1978) 309. T Ogulchansky, L Vretik, V Yashchuk, V Syromyatnikov, A Kolendo Mol. Cryst. Liq. Cryst. 324 223 (1998) 310. M Koshiba, Y Yokoyama, Y Kamoshida, Y Harita J.Chem. Soc. Jpn., Chem. Ind. Chem. 200 (1984) 311. M Tsunooka, S Uenishi, M Tanaka Kobunshi Ronbunshu 44 745 (1987); Ref. Zh. Khim. 6 S 495 (1998) 312. T G Tessier, J M J Frechet, C G Wilson, H Ito ACS Symp. Ser., (Mater. Microlithogr.) 266 269 (1984) 313. J F Rabek Photodegradation of Polymers (Berlin: Springer, 1996) p. 212 314. I Rudnicka, Z Witkiewicz Polym. Tworz. Wielkoczasteczk. 31 291 (1986) 315. V G Syromyatnikov, L P Paskal', A Yu Kolendo Ukr. Khim. Zh. 55 855 (1989) 316. B Ranby, J F Rabek Photodegradation, Photooxidation and Photostabilisation of Polymers (New York: Wiley, 1975) 317. L Merle-Aubry, D A Holden, Y Merle, J E Guillet Macromolecules 13 1138 (1980) 318. Y Namariyama, T Suzuki, T Tomura, A Kinoshita,K Nakamura, K Honda Bull.Tech. Assoc. Graph. Arts. Jpn. 17 181 (1977) 319. Y Namariyama, M Nakazato, I Naito, A Kinoshita, K Nakamura, K Honda Kobunshi Ronbunshu 33 541 (1976); Ref. Zh. Khim. 7 S 251 (1977) 320. Y Namariyama, T Tomura, A Kinoshita, K Nakamura, K Honda Nippon Shashin Gakkaishi 40 73 (1977) 321. C Carlini, D Donati, F Gurzoni, in The 28th Macromolecular Symposium of the IUPAC, Sect. 1 (Abstracts of Reports), Amherst, MA, 1982 p. 132 322. C Ciardelli, D Donati, D G Francesco Polymer 24 599 (1983) 323. L Flamigni, F Barigelletti, P Bortolus, C Carlini Eur. Polym. J. 20 171 (1984) V G Syromyatnikov, L P Paskal', I A Savchenko 324. E Lissi, E Abuin, L Gargallo, D Radic J. Polym. Sci., Polym. Lett. Ed. 17 329 (1979) 325.Jpn. Appl. 58-76 410; Ref. Zh. Khim. 1 S 361P (1985) 326. Jpn. Appl. 2-208 309; Ref. Zh. Khim. 22 S 482P (1991) 327. Jpn. Appl. 59-184 210; Ref. Zh. Khim. 17 S 366P (1985) 328. Jpn. Appl. 64-81 807; Ref. Zh. Khim. 12 S 530P (1990) 329. Jpn. Appl. 61-123 614; Ref. Zh. Khim. 6 S 562P (1988) 330. Jpn. Appl. 1 182 310; Ref. Zh. Khim. 12 S 536P (1990) 331. Jpn. Appl. 1-256 505; Ref. Zh. Khim. 12 S 664P (1991) 332. Jpn. Appl. 63-193 914; Ref. Zh. Khim. 24 S 979P (1989) 333. Jpn. Appl. 62-91 507; Ref. Zh. Khim. 8 S 617P (1988) 334. Jpn. Appl. 63-191 813; Ref. Zh. Khim. 16 S 466P (1989) 335. Jpn. Appl. 63-170 404; Ref. Zh. Khim. 18 S 414P (1989) 336. Jpn. Appl. 2-150 410; Ref. Zh. Khim. 22 S 530P (1991) 337. Jpn. Appl.59-136 309; Ref. Zh. Khim.16 S 367P (1985) 338. Jpn. Appl. 59-136 310; Ref. Zh. Khim. 16 S 369P (1985) 339. Jpn. Appl. 59-96 109; Ref. Zh. Khim. 9 S 392P (1985) 340. US P. 5 278 268; Ref. Zh. Khim. 4 T 55P (1995) 341. BRD Appl. 3 636 400; Ref. Zh. Khim. 4 S 429P (1989) 342. US P. 4 216 303; Ref. Zh. Khim. 5 S 331P (1981) 343. C Wakselman, J P Lampin, H Molines, A Nonat, T Nguen, G Vignal Ann. Chim. Fr. 9 719 (1984) 344. Jpn. Appl. 57-117 517; Ref. Zh. Khim. 2 S 549P (1984) 345. Jpn. Appl. 61-81 410; Ref. Zh. Khim. 8 S 529P (1987) 346. K Saric, Z Janovic, O Vogl J. Macromol. Sci. 21A 267 (1984) 347. K Saric, Z Janovic, O Vogl Croat. Chem. Acta 60 91 (1987) 348. Jpn. Appl. 2 222 407; Ref. Zh. Khim. 12 S 420P (1992) 349. B S Sitaramam, P S Chatterjee J. Appl. Polym.Sci. 37 33 (1989) 350. Jpn. Appl. 58-120 618; Ref. Zh. Khim. 13 S 395P (1984) 351. Jpn. Appl. 57-198 717; Ref. Zh. Khim. 15 S 372P (1984) 352. Jpn. Appl. 61-247 711; Ref. Zh. Khim. 19 S 432P (1987) 353. US P. 4 356 296; Ref. Zh. Khim. 13 S 384P (1983) 354. US P. 4 694 029; Ref. Zh. Khim. 16 S 595P (1988) 355. Jpn. Appl. 62-22 804; Ref. Zh. Khim. 4 S 517P (1988) 356. US P. 5 302 679; Ref. Zh. Khim. 2 T 142P (1996) 357. Jpn. Appl. 60-23 403; Ref. Zh. Khim. 2 S 495P (1986) 358. Jpn. Appl. 2-55 710; Ref. Zh. Khim. 10 S 547P (1991) 359. Jpn. Appl. 49 367; Ref. Zh. Khim. 17U111P (1995) 360. Jpn. Appl. 63-37 114; Ref. Zh. Khim. 6 S 508P (1989) 361. Jpn. Appl. 62-4709; Ref. Zh. Khim. 5 S 536P (1988) 362. Jpn. Appl. 61-36 307; Ref. Zh. Khim. 7 S 600P (1987) 363.Jpn. Appl. 61-141716; Ref. Zh. Khim. 14 S 474P (1987) 364. Jpn. Appl. 62-7709; Ref. Zh. Khim. 6 S 563P (1988) 365. Jpn. Appl. 2289605; Ref. Zh. Khim. 5 S 490P (1991) 366. BRD Appl. 3 636 429; Ref. Zh. Khim. 11 S 506P (1988) 367. Jpn. Appl. 59-56 427; Ref. Zh. Khim. 9 S 395P (1985) 368. USSR P. 1 043 150; Byull. Izobret. (35) 108 (1983) 369. BRD Appl. 3 902 557; Ref. Zh. Khim. 15 S 475P (1991) 370. BRD Appl. 3 902 555; Ref. Zh. Khim. 15 S 474P (1991) 371. I Bellobono, S Calgari, E Selli Polymer Additives. Proceedings of the International Symposium, Las Vegas, 1982 p. 83 372. S Calgari, E Selli, I Bellobono J. Appl. Polym. Sci. 27 527 (1982) 373. N N Barashkov, O A Gunder Fluorestsiruyushchie Polimery (Fluorescent Polymers) (Moscow: Khimiya, 1987) p.223 374. Jpn. Appl. 61-171 709; Ref. Zh. Khim. 13 S 513P (1987) 375. T Hiraga, N Tanaka, K Hayamizu, T Moriya Bull. Electrotechn. Lab. 59 29 (1995) 376. I Muwteszu, I Tincul, C Csunderlih, I Iorga, in IUPAC MACRO'83, Sec. 2±3, 5 (Abstracts of Reports), Bucharest, 1983 p.185 377. GDR P. 262 434; Ref. Zh. Khim. 19 S 470P (1989) 378. Yu I Firsov, E P Yakubovskaya, L A Skripko, in VIII Vsesoyuz. Konf. po Sintezu i Issledovaniyu Effektivnosti Khimikatov dlya Polimernykh Materialov, Tambov, 1986 [The VIIIth All-Union Conference on Synthesis and Investigation of Effectiveness of Chemicals for Polymer Materials, Tambov, 1986] p. 60 379. US P. 4 956 408; Ref. Zh. Khim. 21 S 463P (1991) 380. J A Kuczkowski, J G Gillick Rubber Chem.Technol. 57 621 (1984) 381. S Yachido,M Sasaki, Y Takahashi Polym. Degrad. Stab. 22 63 (1988) 382. S Yachido, F Kojita,M Sasaki, K Ida, S Tanaka, K Inoue Polym. Degrad. Stab. 37 107 (1992) 383. R Levi Rev. Gen. Caoutchouc Plastique 51 243 (1974)Aryl (meth)acrylates and polymers based on them 384. V Syromyatnikov, A Kolendo, I Savchenko, V Yashchuk, L Paskal, T Prot React. Funct. Polym. 38 31 (1998) 385. V Syromyatnikov, V Yashchuk, A Kolendo, L Vretik, L Paskal, T Ogulchansky, A Rusin, I Savchenko Mol. Cryst. Liq. Cryst. 324 386. D A Holden, K Jordan, A Safarzadeh-Amiri Macromolecules 19 387. M Patel, J S Parmar,M R Patel,M M Patel J. Macromol. Sci. 23A 388. M Patel, J S Parmar,M R Patel,M M Patel J. Macromol. Sci. 24A 231 (1998) 895 (1986) 1363 (1986) 1085 (1987) 389. I S Bhardwaj, Y N Sharma, in The 28th Macromolecular Symposium of the IUPAC, Sect. 1 (Abstracts of Reports), Amherst, MA, 1982 p. 331 390. Y N Sharma, M K Nagvi, P S Gawande, I S Bhardwaj J. Appl. Polym. Sci. 27 2605 (1982) 391. US P. 4 413 095; Ref. Zh. Khim. 13 S 422P (1984) 392. US P. 4 528 311; Ref. Zh. Khim. 13 S 461P (1986) 393. F Xi, W Bassett, O Vogl Polym. Bull. 11 329 (1984) 394. R Liu, S Wu, S Li, F Xi, O Vogl Polym. Bull. 20 59 (1988) 395. Y Jiang, S Wu, A Sustie, F Xi, O Vogl Polym. Bull. 20 161 (1988) 396. Jpn. Appl. 56-115 306; Ref. Zh. Khim. 13 S 325P (1982) 397. E Takahashi, H Niikura, T Nishikubo Kobunshi Ronbunshu 42 93 (1985); Ref. Zh. Khim. 17 C 326 (1985) 398. J Uchida, T Nishikubo J. Chem. Soc. Jpn., Chem. Ind. Chem. 595 (1986) 399. K Ichimura, A Kameyama Makromol. Chem. 188 2983 (1987) 400. K Ichimura, A Kameyama,K Hayashi J. Appl. Polym. Sci. 34 2747 (1987) 401. A s 744425 SSSR; Byul. izobret. (24) 183 (1980) 402. A s 547713 SSSR; Byul. izobret. (7) 191 (1977) 403. A s 911443 SSSR; Byul. izobret. (9) 220 (1982) 404. US P. 3 890 150; Ref. Zh. Khim. 5 N 318 (1976) 405. K Ichimura, Y Nishio J. Polym. Sci. Part A, Polym. Chem. 25 1579 (1987) 406. C B Thanawalla, J G Victor J. Radiat. Cur. 12 (4) 2 (1985) 407. K I Przybilla, R Dammel, H Roscherf,W Spiess, G Pawlowski J. Photopolym. Sci. Technol. 4 421 (1991) 408. BRD P. 4 106 558A1; Ref. Zh. Khim. 14 S 267P (1993) 409. G N Taylor, T M Wolf, in The 28th Macromolecular Symposium of the IUPAC, Sec. 1 (Abstracts of Reports), Amherst, MA, 1982 p. 411 410. BRD P. 3 333 861; Ref. Zh. Khim. 9 S 465P (1986) 411. Jpn. Appl. 58-108 213; Ref. Zh. Khim. 15 S 375P (1984) 412. I Lampe, H Lorkowski 8 Tagung: Polymerphysik, Kurzfassung der Vortrage und Poster, Leipzig, 1986 p. 182; Ref. Zh. Khim. 13 S 438 (1987) 413. H Shuyama Sci. Rept Toyo Soda Mamuf. Co. 30 3 (1986); Ref. Zh. Khim. 12C452 (1986) 414. Jpn. Appl. 6 368 612; Ref. Zh. Khim. 17 S 381P (1989) 415. Jpn. Appl. 6 443 512; Ref. Zh. Khim. 8 S 479P (1990) 416. S Imamura, T Tamamura, O Kogure Polym. J. 16 391 (1984) 417. S Imamura, T Tamamura, K Sukegawa, O Kogure, S Sugawara J. Electrochem. Soc. 131 1122 (1984) 418. Jpn. Appl. 62-10 112; Ref. Zh. Khim. 6 S 518P (1988) 419. US P. 4 871 819; Ref. Zh. Khim. 7 S 490P (1991) 420. Jpn. Appl. 196 202; Ref. Zh. Khim. 8 S 584P (1990) 421. R Arshady, B S R Reddy,M H George Polymer 27 769 (1986) 422. M Stolka,D M Pai,D S Renber, J F Yanus J. Polym. Sci., Polym. 424. M Kamachi, H Akimoto, W Mori,M Kishita Polym. J. 16 23 Chem. Ed. 21 969 (1983) 423. M V Kozlovskii, V P Shibaev, N A Plate, in V Vsesoyuz. Konf. po Zhidkim Kristallam i ikh Prakticheskomu Ispol'zovaniyu (Tez. Dokl.), Ivanovo, 1985 [The Vth All-Union Conference on Liquid Crystals and Their Practical Use (Abstracts of Reports), Ivanovo, 1985] Vol. 2, p. 126; Ref. Zh. Khim. 9 S 136 (1986) (1984) 425. H Coles ,Ii Fine Chemical Electronics Industry (Abstracts of Reports), Bath, London, 1986 p. 97 426. G Attard, G Williams Nature (London) 326 544 (1987) 427. O G Abdullaev, O G Tsoi, T I Kalendareva, S Sh Rashidova, M I Shtil'man, P V Zamotaev Vysokomol. Soedin., Ser. B 31 271 (1989) c 428. A P Kiseleva, L S Chuiko, B I Budzan Vest. L'vovsk. Politekhn. Inst. (201) 5 (1986) 799 429. C Potin, A Pleurdeau, C M Bruneau Double-Liais. 32 (351 ± 352) 33 (1985) 430. C Potin, A Pleurdeau, C M Bruneau Makromol. Chem. 138 75 (1986) 431. B Bortnowska-Barela, A Polowinska, S Polowinski, V Vaskova, J Barton Acta Polym. 38 652 (1987) 432. Czech. P. 255 460; Ref. Zh. Khim. 16 S 457P (1989) 433. Czech. P. 255 835; Ref. Zh. Khim. 17 S 377P (1989) 434. L V Wake Austr. OCCA Proc. News 19 (1±2) 15 (1982); Ref. Zh. Khim. 17 S 397 (1982) 435. Jpn. Appl. 60-212 415; Ref. Zh. Khim. 19 S 466P (1986) 436. Jpn. Appl. 60-11 505; Ref. Zh. Khim. 23 S 453P (1985) 437. US P. 5 234 972; Ref. Zh. Khim. 13 T 218P (1995) 438. Jpn. Appl. 59-104 306; Ref. Zh. Khim. 9 S 391P (1985) 439. Jpn. Appl. 2-117 906; Ref. Zh. Khim. 9 S 462P (1991) 440. US P. 4 985 516; Ref. Zh. Khim. 14 S 341P (1992) 441. USSR P. 1 055 130; Byull. Izobret. (26) 260 (1985) 442. A L Finkenaur, L C Dickinson, J C W Chien Am. Chem. Soc. Polym. Prepr. 23 91 (1982) 443. US P. 4 556 689; Ref. Zh. Khim. 13 S 506P (1986) 444. Czech. P. 183 881; Ref. Zh. Khim. 13 S 363P (1981) 445. N A Lisovtseva, G F Zvereva, G V Dubinkina, in Vsesoyuz. Konf. po Radikal'noi Polimerizatsii (Tez. Dokl.), Gor'kii, 1989 [The All-Union Conference on Radical Polymerisation (Abstracts of Reports), Gor'kii, 1989] p. 19 446. V V Chupov, N A Lisovtseva, G F Zvereva, O V Noa, N A Plate Vest. Mosk. Univ., Ser. 2, Khim. 33 276 (1992) i 447. G F Zvereva, N A Lisovtseva, G V Dubinkina, in Vsesoyuz. Simpoz. po Sinteticheskim Polimeram Meditsinskogo Naznacheniya (Tez. Dokl.), Zvenigorod, 1991 [The All-Union Symposium on Synthetic Polymers of Medical Purpose (Abstracts of Reports), Zvenigorod, 1991] p. 22; Ref. Zh. Khim. 14 S 239 (1992) 448. Czech. P. 207 858; Ref. Zh. Khim. 16S543P (1984) 449. C Boudreaux, C Bunyard, C Mc Cormick Am. Chem. Soc. Polym. Prepr. 35 639 (1994) a�Russ. J. Gen. Chem. (Engl. Transl.) b�Russ. Chem. Bull. (Engl. Transl.) c�Polym. Sci. (Engl. Transl.) d�Russ. J. Appl. Chem. (Engl. Transl.) e�Mendeleev Chem. J. (Engl. Transl.) f�Chem. Heterocycl. Compd. (Engl. Transl.) g�Russ. J. Org. Chem. (Engl. Transl.) h�Crystallogr. Rep. (Engl. Transl.) i�Moscow Univ. Bul