Synthesis of Functionalized Poly( N -(3-carboxyphenyl)maleimide- alt -styrene) and Its Heat-Resistance Mechanism
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Synthesis of Functionalized Poly(N-(3-carboxyphenyl)maleimide-alt-styrene) and Its Heat-Resistance Mechanism Qian Zhaoa,*, Yi-Kai Zhana, Yu-Fei Liua,b, Min Hea, and Yong-Ji Gonga a
College of Materials Science and Metallurgical Engineering, Guizhou University, Guiyang, 550025 China b National Engineering Research Center for Compounding and Modification of Polymeric Materials, Guiyang, 550000 China *e-mail: [email protected] Received November 5, 2019; revised February 10, 2020; accepted March 27, 2020
Abstract—Poly(N-(3-carboxyphenyl)maleimide-alt-styrene) with superior heat-resistance was synthesized by free radical copolymerization and its structure was confirmed by FTIR and NMR spectroscopy. To show the advantages in heat-resistance of the synthesized copolymers, the thermal properties of poly(N-phenylmaleimide-alt-styrene) and poly(N-phenylmaleimide-alt-maleic anhydride) with similar structures were determined. DSC/TG analysis showed that the synthesized copolymer exhibited the better thermal properties than two other copolymers due to the formation of a chemically crosslinked three-dimensional network during heating. DOI: 10.1134/S1560090420040119
INTRODUCTION N-Phenylmaleimide and its derivatives are often used as heat-resistant agents for copolymerization reactions such as anionic polymerization, photoinduced polymerization and radical polymerization due to simple preparation, entail low costs, and ability to provide environmental protection, among others [1–5]. The monomers capable to polymerize with Nphenylmaleimide include styrene [6–9], limonene [10], maleic anhydride [11], silicone oil [12] and methyl methacrylate [13]. Copolymers of N-phenylmaleimide are functional modifiers and can significantly improve the heat resistance, impact resistance, hot melt and processability of the resins. Thus, they are widely used in coatings [14], electrosensitive resins [15, 16], photosensitive resins [17, 18], medicine [19], and so on. Poly(N-phenylmaleimide) has a heat-stable rigid structure containing a benzene ring and a five-membered heterocyclic ring, allowing most of them to withstand temperatures above 300°C. However, it is insoluble, refractory, brittle, and difficult to operate [20]. Nevertheless, N-phenylmaleimide is considered as an ideal heat-resistant modified monomer for copolymerization with other monomers and production resins with high heat resistance and superior general properties [21]. Recently the synthesis of poly(N-phenylmaleimide-alt-maleic anhydride) with good heat-resistance
via free-radical polymerization with tert-butyl peroxybenzoate as the initiator was reported [22]. Also poly(N-phenylmaleimide-alt-styrene) was produced by using N-phenylbenzamide as the initiator [23]. Matsumoto et al. [24] used atom transfer radical polymerization to prepare a thermally stable, transparent, sequence-controlled N-substituted maleimide multicomponent copolymer with a narrow MWD and adjustable glass transition temperature Tg over a wide temperature range. The thiol-alkenyl reaction is c
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