Alternating cyclopolymerization of allyl trans-cinnamate and maleic anhydride

Rzaev, Zakır M. O.; Akovali, G.; Medyakova, L.V.

doi:10.1016/0032-3861(94)90489-8

Cited by 7 publications

(9 citation statements)

References 8 publications

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“…It is known that most functional macromolecules with carbonyl groups (ester and ketone type) in side chain, and alternating copolymers of mono-and bifunctional monomers (vinyl and allyl derivatives ofacrylic, maleic and cinnamic acids, etc) have a high sensitivity towards various type of irradiations such as UV, E-beams and X-rays [15][16][17] and their thin films or coatings have a wide range of use in microelectronics as resists of negative and positive type [18][19][20][21][22].…”

Section: Photochemical Reactionsmentioning

confidence: 99%

Complex-radical copolymerization of vinylcyclohexyl ketones with maleic anhydride and N-p-tolylmaleimide

Rzaev

Akovali²,

Kuliyeva³

et al. 2016

Eur Chem Tech J

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Some features of the formation and photochemical reactions of cyclohexylketone containing macromolecules including copolymers of vinylcyclohexyl ketone (VCHK) and its derivatives (V-α-Cl-CHK and V-δ-C1-CHK) with maleic anhydride (MA) and N-p-tolylmaleimide (TMI) have been revealed. It has been established that keto-enol tautomerism is the only reaction realized in the vinylcyclohexylketone molecules having mobile hydrogen atom at α -position in the cyclohexane ring, enol form of which is formed by charge-transfer complexes with anhydride or imide of maleic acid as acceptor monomers. The kinetic parameters of these reactions, including complex-formation and copolymerization constants, as well as the ratios of chain growth rates for the participation of monomeric charge-transfer complexes and free monomers, are all determined. It is shown that an alternative copolymerization is realized with the monomer systems containing VCHK and V-δ -C1-CHK, which are carried out through a complex-mechanism due to the keto-enol tautomerism; while random copolymer enriched with vinyl ketone units is formed with the system containing oc-substituted VCHK. It is found that characteristics of photochemical reactions of alternating copolymer synthesized depend on the type of substitutation in the vinyl ketone molecule; unlink VCHK-MA(TMI) and V-δ-C1-CHK-MA(TMI) copolymers case which easily crosslink upon UVirradiation, and the N-substituted derivatives of these copolymers which decompose under similar condition.

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Section: Photochemical Reactionsmentioning

confidence: 99%

Complex-radical copolymerization of vinylcyclohexyl ketones with maleic anhydride and N-p-tolylmaleimide

Rzaev

Akovali²,

Kuliyeva³

et al. 2016

Eur Chem Tech J

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“…Earlier investigations had shown that kinetic regularities of alternating copolymerization of maleic anhydride (acceptor, A) with allyl monomers affording high‐molecular weight products are reasonably intelligible, in terms of the formation of CTCs in the initial monomer mixture leading to inhibition of degradative chain transfer 7. 71–77…”

Section: Functional Macromonomers and Hyperbranched Macromolecular Armentioning

confidence: 99%

“…Analogous inhibition of degradative chain transfer by CTCs was observed in complex‐radical copolymerization of several bifunctional monomers with an allyl group in such molecules as allyl(metha)acrylates,73 monoallyl maleate,84, 85 methylallyl maleate (fumarate)74 and allyl trans‐cinnamate 75. 76…”

Section: Functional Macromonomers and Hyperbranched Macromolecular Armentioning

confidence: 99%

“…Complex‐radical cyclocopolymerization of selective bifunctional monomers containing two polymerizable double bonds of electron‐donor (allyl or vinyl) and electron‐acceptor (vinylene) type with MA (acceptor) or styrene (or vinyl acetate) as a typical electron‐donor monomer allow to design and synthesize alternating unsaturated cyclocopolymers–‘macromonomers’6, 72–75, 84, 85, 88, 116–118 which easily can be transformed into hyperbranched macromolecular architectures.…”

Section: Functional Macromonomers and Hyperbranched Macromolecular Armentioning

confidence: 99%

“…Several studies have been denoted to the synthesis of photocrosslinkable multifunctional macromonomers based on maleate (fumarate),73, 84, 85 maleimide88, 116 cinnamate74, 75 and acrylates72, 127–129 copolymers, the acrylate/polyimide system130 and maleimide modified acrylate 131. These copolymers show a high sensitivity to different kinds of irradiation such as photo‐irradiation, E‐beams and X‐rays and are easily transferred to their insoluble form that allows one to use them as negative resists in nanolithography 74.…”

Section: Some Properties and Applicationsmentioning

confidence: 99%

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Hyperbranched macromolecules through donor‐acceptor type copolymerization of allyl–vinylene bifunctional monomers

Rzaev

2002

Polymer International

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Present review is an attempt to generalize and systematize the results accumulated in synthesis of cyclolinear and hyperbranched reactive macromolecules via radical alternating copolymerization of various bifunctional monomers containing donor and acceptor type double bonds. Synthesis of hyperbranched reactive macromolecules was carried out using complex‐radical cyclocopolymerization of donor‐acceptor type bifunctional monomers such as monoallyl ester of maleic acid (MAM), allyl acrylate (AA), allyl methacrylate (AM), allyl trans‐cinnamate (AC), methylallylmaleate (MeAM), methylallylfumarate (MAF) and allyl‐α‐(N‐maleimido)acetate (AMI), and maleic anhydride (MA) and styrene (St) as typical acceptor and donor comonomers, respectively. The kinetic parameters of these reactions, constants of cyclization, complex‐formation and copolymerization, as well as the ratios of chain growth rates for the participation of monomeric charge transfer complexes and free monomers, were all determined. It was demonstrated that in the studied systems, copolymerizations predominantly proceed according to alternating mechanism with formation of macromolecules having cyclolinear structure in the steady‐state and hyperbranched structure in the high conversion conditions. It was shown that formation of linear and hyperbranched macromolecules containing allyl or vinylene groups in the side chain occurs selectively carry out and depends on the nature of used comonomer. General schemes and proposed mechanism of hyperbranching and crosslinking reactions were also described. Some useful properties of synthesized reactive copolymers were discussed. © 2002 Society of Chemical Industry.

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Effects of complex formation and cyclization in radical copolymerization of allyl(metha)acrylates with maleic anhydride

Rzaev¹,

Akovali²,

Salamova³

1998

J. Polym. Sci. A Polym. Chem.

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Radical copolymerization of allyl acrylate (AA) and allyl methacrylate (AMA) as bifunctional monomers of donor (allyl)–acceptor (acryl) type with maleic anhydride (MA) as an acceptor monomer were carried out in metrhyl ethyl ketone (MEK) at 50–70°C in the presence of 2,2′‐azoisobutyronitrile (AIBN) as initiator. Constants of complex formation (Kc), cyclization (kcl), and copolymerization (r1, r2, r1c, r1c1, and r1c2) as well as energies of activation for cyclization (Eac) and copolymerization reactions (Ea), and orders for the monomer (m) and initiator (n) concentrations were determined. The following values were found, for AA and AMA, respectively: Kc = 0.038 and 0.11 L/mol in deutered acetone at 35 ± 0.1°C, kcl = 6.45 and 6.53, r1 = 0.083 ± 0.005 and 0.028 ± 0.002, r2 = 0.027 ± 0.002 and 0.063 ± 0.003 (by the Kelen–Tüdös method), r1c = 0.04 and 0.025, r1c1 = 0.128 and 0.176, r1c2 = 0.127 and 0.177 (by the Seiner–Litt equation), Eac = 28.9 and 28.7 kJ/mol, Ea = 67.0 and 87.9 kJ/mol, m = 1.53 and 1.45, and n = 0.50 and 0.52. The presence of cyclic, unsaturated, and anhydride fragments in the macromolecules was confirmed with FTIR data and chemical (iodometrical and potentiometric titrations) analysis. It was established that complex formation in the monomer systems studied is the main factor for alternating cyclocopolymerization leading to formation of copolymers containing lactone and linear‐unsaturated fragments in the macromolecular chain. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 1501–1508, 1998

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Alternating cyclopolymerization of allyl trans-cinnamate and maleic anhydride

Cited by 7 publications

References 8 publications

Complex-radical copolymerization of vinylcyclohexyl ketones with maleic anhydride and N-p-tolylmaleimide

Complex-radical copolymerization of vinylcyclohexyl ketones with maleic anhydride and N-p-tolylmaleimide

Hyperbranched macromolecules through donor‐acceptor type copolymerization of allyl–vinylene bifunctional monomers

Effects of complex formation and cyclization in radical copolymerization of allyl(metha)acrylates with maleic anhydride

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