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忠臣, 西久保; 就司, 伊吹; 務, 水子; 恒郎, 高岡

doi:10.1295/koron.32.604

Cited by 14 publications

(2 citation statements)

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“…Addition reactions of oxiranes with certain protic reagents such as amines, alcohols, phenols, and carboxylic acids have been used2 in the field of synthetic organic chemistry. These reactions have been widely used for polymer syntheses,3, 4 chemical modifications of polymers,5 syntheses of functional polymers,6 and thermal crosslinking reactions7 of epoxy resins. Moreover, the ring‐opening polymerization of oxiranes8 with appropriate catalysts produces corresponding polyethers, such as poly(ethylene glycol), poly(propylene glycol), and poly(epichlorohydrin).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of polyethers with unsymmetrical structures by the polyaddition of 3‐ethyl‐3‐(glycidyloxymethyl)oxetane with diacyl chlorides

Nishikubo

Kameyama

Izawa

2000

J. Polym. Sci. A Polym. Chem.

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Polyethers with unsymmetrical structures in the main chains and pendant chloromethyl groups were synthesized by the polyaddition of 3‐ethyl‐3‐(glycidyloxymethyl)oxetane (EGMO) with certain diacyl chlorides with quaternary onium salts or pyridine as catalysts. The unsymmetrical polyaddition of EGMO containing two different cyclic ether moieties such as oxirane and oxetane groups with terephthaloyl chloride proceeded smoothly in toluene at 90 °C for 6 h to give polymer 1 with a number‐average molecular weight (Mn) of 51,700 in a 93% yield when tetrabutylammonium bromide (TBAB) was used as a catalyst. The polyaddition also proceeded smoothly under the same conditions when other quaternary onium salts, such as tetrabutylammonium chloride, tetrabutylammonium iodide, tetrabutylphosphonium chloride, and tetrabutylphosphonium bromide, and pyridine were used as catalysts. However, without a catalyst no reaction occurred under the same reaction conditions. Polyadditions of EGMO with isophthaloyl chloride and adipoyl chloride gave polymer 2 (Mn = 28,700) and polymer 3 (Mn = 25,400) in 99 and 65% yields, respectively, under the same conditions. The chemical modification of the resulting polymer, polymer 1, which contained reactive pendant chloromethyl groups, was also attempted with potassium 3‐phenyl‐2,5‐norbornadiene‐2‐carboxylate with TBAB as a phase‐transfer catalyst, and a polymer with 65 mol % pendant norbornadiene moieties was obtained. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 368–375, 2001

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Section: Introductionmentioning

confidence: 99%

Synthesis of polyethers with unsymmetrical structures by the polyaddition of 3‐ethyl‐3‐(glycidyloxymethyl)oxetane with diacyl chlorides

Nishikubo

Kameyama

Izawa

2000

J. Polym. Sci. A Polym. Chem.

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“…1 Previously, we reported the synthesis of photosensitive polymers by the addition reaction of poly(glycidyl methacrylate-co-methyl methacrylate) (PGMA) with carboxylic acids. 2 However, gel compounds were produced at the final stage of the reaction due to a side reaction of pendant epoxide groups with the resulting hydroxyl groups. Recently, we also reported 3 the synthesis of polymers having pendant cinnamic ester and chloromethyl groups by the addition reaction of PGMA with cinnamoyl chloride.…”

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Novel Synthesis of Self-Sensitized Photosensitive Polymers by Addition Reaction of Pendant Epoxide Groups in the Polymer with Some Cinnamic Esters

Nishikubo

Iizawa

Takahashi

et al. 1984

Polym J

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Preparation of polymers with pendant quinonoid groups and their photocrosslinking with visible light irradiation

Cha

Tsunooka

Tanaka

1986

J of Applied Polymer Sci

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synopsisPhotosensitive polymers with pendant quinonoid groups were prepared by the reaction of p-(benzoquinon-2-ylthio)acetic acid (QTAA) or p-(p-benzoquinon-2-ylt~o)be~ic acid (QTBA) with hydroxyethyl methacrylate-methyl methacrylate copolymer. The polymers showed a strong w -d absorption band at around 410 nm and were efficiently crosslinked by visible light irradiation. Somewhat higher photosensitivity of QTAA-bound polymer compared with that of QTBA-bound polymer suggested some contribution of intramolecular hydrogen abstraction of QTAA to the photocrosslinking.

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Cited by 14 publications

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Synthesis of polyethers with unsymmetrical structures by the polyaddition of 3‐ethyl‐3‐(glycidyloxymethyl)oxetane with diacyl chlorides

Synthesis of polyethers with unsymmetrical structures by the polyaddition of 3‐ethyl‐3‐(glycidyloxymethyl)oxetane with diacyl chlorides

Novel Synthesis of Self-Sensitized Photosensitive Polymers by Addition Reaction of Pendant Epoxide Groups in the Polymer with Some Cinnamic Esters

Preparation of polymers with pendant quinonoid groups and their photocrosslinking with visible light irradiation

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