Synthesis and Thermal Properties of Comb‐Like Maleimide Copolymers Containing Polymethylene and Poly(Ethylene Oxide) Side Chains as the N‐Substituents

Takeda, K.; Omayu, Akitoshi; Matsumoto, Akikazu

doi:10.1002/macp.201300331

Cited by 8 publications

(6 citation statements)

References 43 publications

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“…This indicated that the AAB-type sequence was predominantly produced during the copolymerization of the RMIs with bulky DIB under the penultimate unit control, [17][18][19] being different from the formation of alternating copolymers with isobutene under terminal control. [11][12][13] The AMI content varied in a range of 12-43 mol% in the copolymers. The carbon-to-carbon double bond of the maleimide ring had a reactivity 10 3 times higher than that of the allyl moiety in the side group, resulting in the selective participation of the maleimide double bonds in propagation during the copolymerization.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4][5][6] The RMIs also copolymerize with electron-donating monomers, such as styrene, vinyl ethers, and olefins, to give alternating copolymers with excellent thermal stability and a high glass transition temperature (T g ). [7][8][9][10][11] Especially, the copolymerization of the RMIs with isobutene provided an alternating copolymer with excellent thermal stability, high transparency, and high modulus and strength. [12,13] The introduction of polar groups and cyclic structures into the olefin repeating units led to further increases in their thermally stability and the T g values.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Thermoresistant Maleimide Copolymers and their Crosslinked Polymers

Yamamoto

Okamura

Matsukawa

et al. 2014

J. Photopol. Sci. Technol.

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We fabricated thermosetting maleimide polymers with excellent thermal and optical properties by the sequence-controlled radical copolymerization of N-allylmaleimide (AMI) and N-(2-ethylhexyl)maleimide (EHMI) with diisobutylene (DIB) and postpolymerization reactions. The AAB-type maleimides/DIB copolymers randomly containing an allyl group in the side chain were thermally or photochemically cured using pentaerythritol tetrakis(3-mercaptobutyrate) as a polyfunctional thiol by thiol/ene reaction. The organic-inorganic hybrid was also fabricated by the thiol/ene reaction of the maleimide copolymers containing allyl side groups combined with surface-modified silica nanoparticles. The produced organic-inorganic hybrid was dispersed in tetrahydrofuran. The transparent films of the maleimide copolymers containing the hybrid were obtained by casting and drying. The crosslinked polymers and the organic-inorganic hybrid obtained in this study exhibited excellent thermal stability as well as the high transparency.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Thermoresistant Maleimide Copolymers and their Crosslinked Polymers

Yamamoto

Okamura

Matsukawa

et al. 2014

J. Photopol. Sci. Technol.

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“…2,2′‐Azobisisobutyronitrile (AIBN) was purchased from Wako Pure Chemical Industries, Ltd., Osaka, Japan, and used after recrystallization from methanol. AMI and EHMI were synthesized according to the method reported in the literature . Commercially‐available DIB and solvents were distilled before use.…”

Section: Methodsmentioning

confidence: 99%

“…The produced AAB‐type copolymers exhibited higher T g values due to a high content of the RMI units and the bulky structure of the olefin repeating units. It should also be noted that the RMI copolymers including an allyl group in the side chain were successfully fabricated during the copolymerization of N ‐allylmaleimide (AMI) with isobutene or DIB . The soluble copolymers of AMI with isobutene or DIB were produced during the copolymerization under the conditions with a low AMI concentration, while an increase in the AMI concentration readily resulted in the formation of insoluble polymers.…”

Section: Introductionmentioning

confidence: 99%

Heat resistant and transparent organic–inorganic hybrid materials composed of N‐allylmaleimide copolymer and random‐type SH‐modified silsesquioxane

Oban

Matsukawa

Matsumoto

2018

J. Polym. Sci. Part A: Polym. Chem.

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A thermally stable and transparent copolymer (PAED) composed of N‐allylmaleimide, N‐(2‐ethylhexyl)maleimide, and diisobutylene as the repeating units was produced by radical copolymerization in the presence of an azo initiator in chloroform at 60 °C. The thiol–ene reaction between the allyl groups included in the side chain of PAED and the mercapto groups (SH) included in a random‐type SH‐modified silsesquioxane (SQ) as the crosslinker provided PAED–SQ hybrid materials upon heating. The reaction process for this thermal curing was monitored from the intensity changes of characteristic peaks by IR spectroscopy as well as the gravimetric determination of the isolated insoluble fractions. The thermal, optical, and mechanical properties of the hybrids were investigated. The onset and maximum decomposition temperatures were 322–369 °C and 399–431 °C, respectively. The weight residue at 800 °C was 16–40 wt%, which depended on the amount of the SQ content in the feed. These organic–inorganic hybrid materials were highly transparent and exhibited refractive index of 1.522–1.524 and Abbe number of 40.0–45.8. The tensile test and dynamic mechanical analyses were also carried out to investigate the mechanical properties and the network structures of the hybrids. The addition of triallylisocyanurate (TAIC) to the curing system efficiently improved the conversion of the allyl and SH, leading to the more dense network structure and the higher strength and hardness of the cured hybrids. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 2294–2302

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“…The brittleness of the maleimide copolymers often becomes an obstacle for actual processing and applications. It is also noteworthy that the maleimide copolymers including an allyl group in the side chain were conveniently fabricated during the copolymerization of N ‐allylmaleimide with olefins . The allyl‐containing copolymers are useful as the precursor polymers for the synthesis of heat‐resistant network polymers by a thiol–ene reaction in the presence of multifunctional crosslinkers, but network structure formation is disadvantageous for the fabrication of transparent polymer films.…”

Section: Introductionmentioning

confidence: 99%

Control of thermal, mechanical, and optical properties of three‐component maleimide copolymers by steric bulkiness and hydrogen bonding

Nagase

Miyama

Matsumoto

2019

J. Polym. Sci. Part A: Polym. Chem.

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N‐substituted maleimides polymerize in the presence of a radical initiator to give polymers with excellent thermal stabilities and transparency. In this study, we synthesized various maleimide copolymers with styrenes and acrylic monomers to control their thermal and mechanical properties by the introduction of bulky substituents and intermolecular hydrogen bonding. Three‐component copolymers of N‐(2‐ethylhexyl)maleimide in combination with styrene, α‐methylstyrene (MSt), or 1‐methylenebenzocyclopentane (BC5) as the styrene derivatives, and n‐butyl acrylate, 2‐hydroxyethyl acrylate, 4‐hydroxybutyl acrylate, or acrylic acid as the acrylic monomers were prepared by radical copolymerization. These copolymers were revealed to exhibit excellent heat resistance by thermogravimetric analysis. Glass transition temperatures increased by the introduction of bulky MSt and BC5 repeating units. The mechanical properties of the copolymer films were improved by the introduction of intermolecular hydrogen bonding. Optical properties, such as transmittance, refractive index, Abbe number, and birefringence, were determined for the copolymers. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1569–1579

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Synthesis and Thermal Properties of Comb‐Like Maleimide Copolymers Containing Polymethylene and Poly(Ethylene Oxide) Side Chains as the N‐Substituents

Cited by 8 publications

References 43 publications

Synthesis and Characterization of Thermoresistant Maleimide Copolymers and their Crosslinked Polymers

Synthesis and Characterization of Thermoresistant Maleimide Copolymers and their Crosslinked Polymers

Heat resistant and transparent organic–inorganic hybrid materials composed of N‐allylmaleimide copolymer and random‐type SH‐modified silsesquioxane

Control of thermal, mechanical, and optical properties of three‐component maleimide copolymers by steric bulkiness and hydrogen bonding

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