2-비페닐릴아크릴레이트와 메타크릴산의 공중합체 제조와 2-페닐페놀의 방출

현석희; 김민우; 전일련; 손석호; 백창훈; 김우식; Seok-Hee Hyun; Min-Woo Kim; Il-Ryon Jeon; Seog-Ho Son; Chang-Hoon Baek; Woo-Sik Kim

Polymer(Korea), Vol.30, No.1, 80-84, January, 2006

Export Citation

2-비페닐릴아크릴레이트와 메타크릴산의 공중합체 제조와 2-페닐페놀의 방출

Preparation of Poly(2-biphenylyl acrylate-co-methacrylic acid) and Release of 2-Phenylphenol

현석희, 김민우¹, 전일련 ², 손석호³, 백창훈⁴, 김우식 ^{1, †}

경북대학교 공동실험실습관
¹경북대학교 고분자공학과
²경일대학교 제약공학부
³니카코리아(주) 연구소
⁴한국염색기술연구소

Seok-Hee Hyun, Min-Woo Kim¹, Il-Ryon Jeon², Seog-Ho Son³, Chang-Hoon Baek⁴, and Woo-Sik Kim^{1, †}

Center for Scientific Instruments, Kyungpook National University, Daegu 702-701, Korea
¹Department of Polymer Science, Kyungpook National University, Daegu 702-701, Korea
²School of Pharmaceutical Engineering, Kyungil University, Gyeongsang buk-do 712-701, Korea
³Research & Development Dept., Nicca Korea Co. Ltd, Daegu 702-815, Korea
⁴Korea Dyeing Technology Center, Daegu 703-834, Korea

E-mail:

초록

항균제인 2-페닐페놀을 아크릴로일클로라이드와 반응시켜 2-비페닐릴아크릴레이트(BPA)를 합성하고 이를 메타크릴산(MA)과 라디칼 공중합시켜 2-페닐페놀 moiety를 가지는 친수성 고분자를 합성하였다. 핵자기공명 스펙트라로부터 구한 이들 고분자중의 BPA와 MA 단량체의 조성을 사용하여 Kelen-Tudos 플로트로 결정한 단량체 반응성 비는 0.86과 1.21이였다. 이 결과는 제조된 poly(BPA-co-MA)가 이상적인 랜덤 공중합체라는 것을 뜻한다. 자외선 분광 광도계를 이용하여 이들 공중합체의 가수분해로 방출된 2-페닐페놀의 양을 측정하였다. 그 결과 pH가 증가함에 따라 그리고 공중합체중의 친수성의 MA의 양이 증가함에 따라 방출된 2-페닐페놀의 양이 증가하였다. 이들 결과는 제조한 고분자는 2-페닐페놀을 조절방출하는 고분자 항균제라는 것을 의미한다.

2-Biphenylyl acrylate (BPA) was synthesized by the reaction of acryloyl chloride with 2-phenylphenol (2PP). Hydrophilic copolymers with the moiety of the microbicide, 2PP, were prepared by the radical copolymerization of BPA and methacrylic acid (MA). From the compositions of the BPA unit and the MA unit in the copolymers, the monomer reactivity ratios were determined to be 0.86 for BPA and 1.21 for MA by means of Kelen-Tudos plot. This result indicates that the copolymers have a random structure. The amount of 2PP released through the hydrolysis of the copolymers was examined by UV spectrometry. The result showed that the release of 2PP increased with an increase in the hydrophilic MA content in the copolymers and with an increase in the pH of the release medium. Therefore, these results indicate that the hydrophilic polymers bearing 2-phenylphenol moiety can be controlled release microbicides.

Keywords:2-phenylphenol;microbicide;hydrophilic copolymer;reactivity ratio;release

[References]

Pittman CU, Stahl GA, Winters H, J. Coat. Technol., 50, 49 (1978)
Mitamura I, Arimatsu Y, U. S. Patent, 5,583,230 (1996)
Deichman WB, Keplinger ML, "Industrial Toxicology, Phenols and Phenolic Compoudns", in Patty's Industrial Hygiene and Toxicology, G. D. Clayton and F. E. Clayton, Editors, 3rd edn., Wiley, New York, Vol2A, p. 2616 (1981)
Sasaki YF, Kawaguchi S, Kamaya A, Ohshita M, Kabasawa K, Iwama K, Taniguchi K, Tsuda S, Mutation Research, 519, 103 (2002)
Ishikawa T, Asai S, Bull. Chem. Soc. Jpn., 56, 2177 (1983)
Hyun SH, Kim MW, Jeon IR, Kim WS, Polym.(Korea), 27(5), 443 (2003)
Hyun SH, Kim MW, Hong KH, Min KE, Kim WS, J. Ind. Eng. Chem., accepted.
Kim WS, Lee SH, Kang IK, Park NK, J. Control. Release, 9, 281 (1989)
Kim WS, Jung SW, Jang JK, Kim GH, Lee JK, Korea Polym. J., 6(5), 414 (1998)
Kelen T, Tudos F, J. Macromol. Sci. Chem., A9(1) (1975)
Kim SS, Lee SW, Haw JL, Huh W, Polym.(Korea), 26(1), 9 (2002)
Nemec JW, Bauer W, "Acrylic and Methacylic Acid Polymers", in Encyclopedia of Polymer Science and Engineering, H. F. Mark, N. M. Bikales, C. G. Overberger, G. Menges, and J. I. Kroschwitz, Editors, 2nd edn., John Wiley and Sons, New York, Vol 1, p 221 (1985)

[Related Articles]

[1] Pittman CU, Stahl GA, Winters H, J. Coat. Technol., 50, 49 (1978)

[2] Mitamura I, Arimatsu Y, U. S. Patent, 5,583,230 (1996)

[3] Deichman WB, Keplinger ML, "Industrial Toxicology, Phenols and Phenolic Compoudns", in Patty's Industrial Hygiene and Toxicology, G. D. Clayton and F. E. Clayton, Editors, 3rd edn., Wiley, New York, Vol2A, p. 2616 (1981)

[4] Sasaki YF, Kawaguchi S, Kamaya A, Ohshita M, Kabasawa K, Iwama K, Taniguchi K, Tsuda S, Mutation Research, 519, 103 (2002)

[5] Ishikawa T, Asai S, Bull. Chem. Soc. Jpn., 56, 2177 (1983)

[6] Hyun SH, Kim MW, Jeon IR, Kim WS, Polym.(Korea), 27(5), 443 (2003)

[7] Hyun SH, Kim MW, Hong KH, Min KE, Kim WS, J. Ind. Eng. Chem., accepted.

[8] Kim WS, Lee SH, Kang IK, Park NK, J. Control. Release, 9, 281 (1989)

[9] Kim WS, Jung SW, Jang JK, Kim GH, Lee JK, Korea Polym. J., 6(5), 414 (1998)

[10] Kelen T, Tudos F, J. Macromol. Sci. Chem., A9(1) (1975)

[11] Kim SS, Lee SW, Haw JL, Huh W, Polym.(Korea), 26(1), 9 (2002)

[12] Nemec JW, Bauer W, "Acrylic and Methacylic Acid Polymers", in Encyclopedia of Polymer Science and Engineering, H. F. Mark, N. M. Bikales, C. G. Overberger, G. Menges, and J. I. Kroschwitz, Editors, 2nd edn., John Wiley and Sons, New York, Vol 1, p 221 (1985)