Synthesis and Polymerization of N-(4-Tetrahydropyranyl-oxyphenyl)maleimide

Satoru Amou, Shin Nishimura, Akio Takahashi, Tokio Hagiwara, Hiroshi Hamana, Tadashi Narita

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Abstract

N-(4-Tetrahydropyranyl-oxy-phenyl)maleimide (THPMI) was prepared and polymerized by radical or anionic initiators. THPMI could be polymerized by 2,2′-azobis(isobutyronitrile) (AIBN) and potassium tert-butoxide. Radical polymers (poly(THPMI)r) were obtained in 15-50% yields for AIBN in THF at 65°C after 2-5 h. The yield of anionic polymers (poly(THPMI)a) obtained from potassium tert-butoxide in THF at 0°C after 20 h was 91%. The molecular weights of poly(THPMI)r and poly(THPMI)a were Mn = 2750-3300 (Mw/Mn = 1.2-3.3) and Mn = 11300 (Mw/Mn = 6.0), respectively. The difference in molecular weights of the polymers was due to the differences in the termination mechanism of polymerization and the solubility of these polymers in THF. The thermal decomposition temperatures were 205 and 365°C. The first decomposition step was based on elimination of the tetrahydropyranyl group from the poly(THPMI). Positive image patterns were obtained by chemical amplification of positive photoresist composed of poly(THPMI) and 4-morpholinophenyl diazonium trifluoromethanesulfonate used as an acid generator.

Original languageEnglish
Pages (from-to)341-347
Number of pages7
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume37
Issue number3
DOIs
Publication statusPublished - Feb 1 1999
Externally publishedYes

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Polymerization
Polymers
Potassium
Molecular weight
Photoresists
Amplification
Pyrolysis
Solubility
Decomposition
Acids
maleimide
Temperature

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

Synthesis and Polymerization of N-(4-Tetrahydropyranyl-oxyphenyl)maleimide. / Amou, Satoru; Nishimura, Shin; Takahashi, Akio; Hagiwara, Tokio; Hamana, Hiroshi; Narita, Tadashi.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 37, No. 3, 01.02.1999, p. 341-347.

Research output: Contribution to journalArticle

Amou, Satoru ; Nishimura, Shin ; Takahashi, Akio ; Hagiwara, Tokio ; Hamana, Hiroshi ; Narita, Tadashi. / Synthesis and Polymerization of N-(4-Tetrahydropyranyl-oxyphenyl)maleimide. In: Journal of Polymer Science, Part A: Polymer Chemistry. 1999 ; Vol. 37, No. 3. pp. 341-347.
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