Polymer(Korea), Vol.19, No.1, 47-54, January, 1995
Poly(ethylene-co-acrylic acid) 공중합체의 화학적 개질 및 광화학반응
Chemical Midification of Poly(ethylene-co-acrylic acid) Copolymer and Their Photochemical Reactions
초록
Poly(ethylene-co-acrylic acid) 공중합체에 SOCl2를 반응시켜 acyl chloride기를 도입시킨 다음 phenol, 아닐린, acetophenone oxime을 각각 반응시켜 개질시켰다. acyl chloride 기가 도입된 공중합체에 페놀을 Friedel-Crafts 반응시킨 결과 Phenyl ester화된 공중합체가 주로 얻어졌으며 여기에 자외선을 쪼이면 photo-Fries 전위반응이 일어나 케톤기가 생성되었다. N-phenylamide 기가 도입된 공중합체에 254nm의 자외선을 조사하면 아미드의 C-N 결합이 분해되어 페닐 케톤기가 생성되었고 광가교반응이 일어났다. 또한 acetophenone oxide 기가 도입된 공중합체에 자외선을 쪼이면 N-O 결합의 분해에 의해 생성된 라디칼끼리의 짝지음 반응으로 인해 광가교반응이 일어났고 수소추출반응에 의해 -COOH기가 생성되었다.
Acyl chloride group was introduced to poly(ethylene-co-acrylic acid) copolymer by the reaction with SOCl2. Three kinds of modified copolymer were prepared by reacting the chlorinated copolymer [ I ] with phenol aniline, and acetophenone oxide respectively. Phenyl esterified copolymer [ II ] was obtained by Friedel-Crafts acylation reaction of phenol with the chlorinated copolymer [ I ]. Upon irradiation of copolymer [ II ] with 254nm UV lights, a hydroxyphenyl ketone group was produced as a result of Photo-Fries rearrangement. Irradiation of N-phenylamidated copolymer [ III ] with 254nm UV light resulted the formation of aminophenyl ketone group and cross-linking via photocleavage of the amide C-N bond. Upon irradiation of acetophenone oxime esterfied copolymer [ IN ] with 254nm UV light, cross-linking by radical coupling reaction and formation of -COOH group by hydrogen abstraction reaction took place as a result of photocleavage of the N-O bond.
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