Copolymerization of <i>N</i>‐chlorophenylmaleimides with vinyl acetate

Konsulov, Vitan; Grozeva, Z.; Kelen, Tibor; Borbély, János

doi:10.1002/macp.1992.021930403

Cited by 8 publications

(6 citation statements)

References 11 publications

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“…N-(4-Chlorophenyl) maleimide was prepared by the reaction of maleic anhydride with 4-chloroaniline in acetone followed by dehydrocyclization of the resulting maleamic acid in the presence of acetic anhydride and sodium acetate. N-(4-Chlorophenyl) maleimide was recrystallized from ethanol (mp 114-115 • C [14]). Anhydrous sodium sulfide was prepared from nonahydrate sodium sulfide under vacuum in the presence of P 2 O 5 and gradually increasing the temperature to 105 • C.…”

Section: Methodsmentioning

confidence: 99%

Polyethers and polythioethers containing 1,4-dithiin-2,3;5,6-tetrayl diimide

Găină¹,

Gaina²

2005

Designed Monomers and Polymers

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New polythioethers containing a 1,4-dithiin-2,3;5,6-tetrayl diimide structure were synthesized by condensation of N-(p-chlorophenyl)-2,3-dichloromaleimide (2) with anhydrous sodium sulfide in molar ratio 2:3 or by condensation of bis(N,N -p-chlorophenyl)-1,4-dithiin-2,3:5,6-tetrayl diimide (3) with various bisphenols. The polyethers were prepared by condensation of 3 with various bisphenols. The monomer 3 was synthesized by nucleophilic substitution of 2 with nonahydrate sodium sulfide. IR and UV spectroscopy, as well as elemental analysis confirmed the structures. The polymers were characterized by viscosimetric measurements, softening points and thermogravimetric data. They showed good solubility in aprotic solvents and high thermal stability.

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Section: Methodsmentioning

confidence: 99%

Polyethers and polythioethers containing 1,4-dithiin-2,3;5,6-tetrayl diimide

Găină¹,

Gaina²

2005

Designed Monomers and Polymers

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“…The polymer compositions containing copolymers of halogen‐containing N ‐substituted maleimides were found to have flame retardant properties and high thermostability 122. 123 Thermosetting heat resistance bismaleimide‐containing resin compositions showing improved curability, adhesion, and processability, useful for printed circuit boards, contain alkylene or phenylene bismaleimides (63.3%), maleamic acid monoesters (27.2%), and unsaturated derivatives of maleic acid (9.5%). This monomer composition was mixed with glass filler, dicumyl peroxide and stearic acid, kneaded, transfer‐moulded at 175 °C, and postcured at 200 °C for 8 h to give a test piece showing of bending strength a 98 Mpa at 20 °C and 69.5 Mpa at 240 °C 124.…”

Section: Some Properties and Applicationsmentioning

confidence: 99%

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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“…During recent decades, the increasing requirements of high‐technology industries have been the driving force in the development of new synthetic and artificial polymer systems that combine thermal stability with specific functional properties. Copolymerization reactions involving N ‐phenylmaleimide ( N ‐PhMI) monomer have generated great interest because of the large number of possibilities that they offer in the preparation of new materials with improved properties, including flame and heat resistance as well as thermal and chemical stability 1–10. Maleimide polymers have good thermal stability with high glass transition temperatures due to their polar five‐membered imide ring structure,11 and interest in the synthesis of new types of these polymeric materials as well as the modification of the primary structure of the polymers continues to grow 12–14…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of hydrophilic copolymers of maleimide derivatives with 2‐hydroxyethyl methacrylate: electrochemical and thermal behavior

Pizarro

Marambio

Jeria‐Orell

et al. 2009

Polymer International

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BACKGROUND: The high‐technology industries have been the driving force in the development of new synthetic polymers that combine thermal stability with specific functional properties. In this study p‐chlorophenylmaleimide, p‐hydroxyphenylmaleimide and p‐nitrophenylmaleimide (R‐PhMI) with 2‐hydroxyethyl methacrylate (HEMA) were synthesized by free radical polymerization to obtain hydrophilic polymers, in order to study the effect of the p‐chloroaryl, p‐hydroxyaryl or p‐nitroaryl group on the copolymer composition, electrochemical behavior and thermal properties. RESULTS: The thermal behavior was correlated with the copolymer composition and functional groups, maleimide derivatives, on the copolymers. Thermal decomposition temperature (TDT) and glass transition temperature (Tg) were influenced by the functional groups of R‐PhMI moiety on the copolymer. The polymers showed an electrochemically irreversible reduction process under the conditions tested. CONCLUSION: Poly[(p‐chloromaleimide)‐co‐(2‐hydroxyethyl methacrylate)] copolymer shows a higher TDT than poly[(p‐hydroxymaleimide)‐co‐(2‐hydroxyethyl methacrylate)] or poly[(p‐nitromaleimide)‐co‐(2‐hydroxyethyl methacrylate)] (NPHE). Tg decreases in going from nitro to hydroxyl to chloro groups. The NPHE copolymer shows a lower stability, losing weight at 200 °C. The NPHE copolymer shows a well‐defined reduction wave which is similar to those of the other copolymers and it also shows an additional quasi‐reversible reduction wave corresponding to the nitrobenzene group. Copyright © 2009 Society of Chemical Industry

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Copolymerization of N‐chlorophenylmaleimides with vinyl acetate

Cited by 8 publications

References 11 publications

Polyethers and polythioethers containing 1,4-dithiin-2,3;5,6-tetrayl diimide

Polyethers and polythioethers containing 1,4-dithiin-2,3;5,6-tetrayl diimide

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

Synthesis and characterization of hydrophilic copolymers of maleimide derivatives with 2‐hydroxyethyl methacrylate: electrochemical and thermal behavior

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