3-인돌프로피온산 Moiety를 함유하는 친수성 고분자의 합성과 방출 특성

김우식; 김규환; 홍기헌; 박남규; 이재근; Woo-Sik Kim; Gyu-Hwan Kim; Ki-Heon Hong; Nam-Kyu Park; Jae-Keun Lee

Polymer(Korea), Vol.23, No.5, 639-644, September, 1999

Export Citation

3-인돌프로피온산 Moiety를 함유하는 친수성 고분자의 합성과 방출 특성

Synthesis and Release Behavior of Hydrophilic Polymers Containing 3-Indolepropionic Acid Moiety

김우식^†, 김규환, 홍기헌, 박남규¹, 이재근²

경북대학교 고분자공학과
¹(주)P&S
²경북대학교 화학과

Woo-Sik Kim^†, Gyu-Hwan Kim, Ki-Heon Hong, Nam-Kyu Park¹, and Jae-Keun Lee²

Department of Polymer Science, Kyungpook National University, Taegu 702-701, Korea
¹P&S Co. Ltd., Chungpook 369-800, Korea
²Department of Chemistry, Kyungpook National University, Taegu 702-701, Korea

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초록

식물성장 촉진제인 3-indolepropionic acid (IPA)를 서방형 물질로 만들기 위해 트리에틸아민을 촉매로 하여 클로로벤젠 용매중에서 90 ℃에서 IPA의 나트륨 염을 클로로메틸스티렌과 반응시켜 촉진제로 함유하는 단량체를 합성하였다. 이 단량체를 디메틸로름아미드 용매하, 70 ℃에서 친수성 단량체인 아크릴아미드 (AM)와 라디칼 공중합시켜 IPA moiety를 함유하는 고분자를 만들었다. 또, 공중합체로부터 가수분해되어 방출되는 IPA의 양을 측정하였다. 그 결과, 방출속도는 공중합체 중의 AM함량이 증가할수록 증가했고 또 방출용액의 온도가 상승할수록 증가했다. 또한 그 속도는 중성 영역에서 보다 산성 영역과 알칼리 영역에서 빨랐다. 이들 결과는 방출속도가 공중합체의 조성, 방출 용액의 온도 및 pH에 의해 조절될 수 있다는 것을 뜻한다.

A monomer containing 3-indolepropionic acid (IPA) was synthesized by reacting chloromethylstyrene with the sodium salt of IPA in chlorobenzene in the presence of triethylamine at 90 ℃. This monomer was copolymerized with various amount of acrylamide(AM) to obtain polymers of varing hydrophilicity. The polymerization was carried out in dimethylformamide at 70 ℃ using azobisisobutyronitrile (AIBN) as the initiator. The copolymers were placed in buffer solutions of various pH and the amount of IPA hydrolyzed from each polymer was determined at different temperatures. The release rate of IPA increased as the amount of AM in the copolymer and the temperature increased. The release rate was higher in acidic and basic solutions than in neutral solution. These results indicate that the release rate of IPA could be controlled by adjusting the amount of AM unit in the polymer, temperature and pH of the medium to which the polymer was exposed.

Keywords:3-indolepropionic acid;acrylamide;hydrophilic polymer;release rate

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[2] Boudreaux CJ, Bunyard WC, McCormick CL, J. Control. Release, 40, 223 (1996)

[3] McCormick CL, Zhang ZB, Anderson KW, J. Control. Release, 4, 97 (1986)

[4] McCormick CL, U.S. Patent, 4,267,280 (1981)

[5] McCormick CL, U.S. Patent, 4,267,281 (1981)

[6] Issa R, Akelah A, Rehab A, Solaso R, Chiellini E, J. Control. Release, 13, 1 (1990)

[7] Kim WS, Jung SW, Lee SK, Moon SI, Lee JK, Korea Polym. J., 5(4), 238 (1997)

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

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

[10] Tharp ID, Nottarf HA, Ind. Eng. Chem., 39, 1300 (1947)

[11] Biemann K, "Spectral Data for Structure Determination of Organic Compounds," Springer-Verlag, Berlin Heidelberg (1989)

[12] Tanaka H, Senju R, Kobunshi Ronbunshu, 33, 309 (1976)