곁사슬에 기능성기를 갖는 양친매성 스티렌 공중합체의 합성에 관한 연구

이정복; 김창배

Journal of the Korean Industrial and Engineering Chemistry, Vol.5, No.5, 801-807, October, 1994

Export Citation

곁사슬에 기능성기를 갖는 양친매성 스티렌 공중합체의 합성에 관한 연구

A Study on the Synthesis of Amphiphilic Styrene Copolymers having Functional Groups on the Side Chain

이정복, 김창배

초록

락토오스 치환 스티렌 단량체, N-(p-vlnylbenzyl)-D-lactonamide(VLA)는 락토오스락톤과 p-비닐벤질아민과의 아미드화반응을 따라 제조하였고, 비오틴 치환 스티렌 당량체, N-(p-vlnylbenzyl)-biotinamide(VBA)는 비오틴의 카르복실기를 N, N'-dicyclohexylcarbodiimide 존재하에서 N-hydroxysuccinimide와 반응하여 활성화된 비오틴을 제조한 것을 이어서 p-비닐벤질아민과 아미드화시켜 합성하였다 합성한 이들 단량체(VLA와 VBA)의 반응 몰비를 바꿔가면서 라디칼 중합에 의하여 공중합체인 poly(vlnytbenzyl-lactonamide-co-vlnylbenzylbiotinamide), p(VLA-co-VBA)을 합성하였고, 67∼71%의 수율을 얻었다. 합성된 공중합체들은 친수성의 락토오스 부위와 소수성의 비닐벤질 부위 그리고 소량의 biotin 부위를 함께 갖고 있는 양친매성 중합체였음을 기기분석으로 확인하였다.

Lactose substituted styrene monomer, N-(p-vlnylbenzyl)-D-lactonamide(VLA) was prepared by coupling the lactose lactone with p-vlnylbenzylamine. The carboxyl group of biotin was activated with N-hydroxysuccinimide in the presence of N, N'-dicyclohexylcarbodiimide. Subsquently, biotin substituted styrene monomer, N-(p-vinylbenzyl)-biotinamide(VBA) was prepared by amidation of the activated biotin with p-vinylbenzylamine. Poly(vlnylbenzylactonamide-co-vlnylbenzylbiotinamide), p(VLA-co-VBA) were synthesized through radical polymerization from the synthetic monomers(VLA-VBA) by uslng various mole ratio. The percentages of yield were 67∼71%. The copolymers were found amphlphilic which had hydrophilic lactose, hydrophobic vinylbenzyl and biotin site within the structure. IR and ¹³C-NMR analysis on the monomers and copolymer were carried out.

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[1] Takemoto K, J. Macromol. Sci.-Rev. Macromol. Chem. Phys., 5, 29 (1970)

[2] Merrifield RB, J. Am. Chem. Soc., 85, 2149 (1963)

[3] Kawana M, Emoto S, Tetrahedron Lett., 13, 4855 (1972)

[4] Wulff G, Vesper W, GrobeEinsler R, Arhan A, Makromol. Chem., 178, 2799 (1977)

[5] Maconochie G, Sharples A, Thompsson G, Eur. Polym. J., 7, 499 (1971)

[6] Kobayashi K, Sumitomo H, Polym. Bull., 1, 121 (1978)

[7] Sumitomo H, Hasegawa M, Polym. Prepr., 29, 56 (1980)

[8] Bader H, Ringsdorf H, Skura J, Angew. Chem.-Int. Edit., 20, 91 (1981)

[9] Kochetkov NK, Dmitriev BA, Chernyak AY, Levinsky AB, Carbohydr. Res., 110, C16 (1982)

[10] Sharon N, "Complex Carbohydrates, Their Chemistry, Biochemistry, and Functions," Addison Weslery, Reading, Mass. (1975)

[11] Kobayashi K, Sumitomo H, Ina Y, Polym. J., 17, 567 (1988)

[12] Kobayashi K, Sumitomo H, Itoigawa T, Macromolecules, 20, 96 (1987)

[13] Kobayashi K, Sumotomo H, Kobayashi A, Akaike T, J. Macromol. Sci.-Chem., A25, 655 (1988)

[14] Akaike T, Kobayashi A, Kobayashi K, Sumitomo H, J. Bioactive Compatible Polym., 4, 51 (1989)

[15] Wakil SG, Titchener EB, Gibson DM, Biochim. Biophys. Acta, 29, 225 (1958)

[16] Lynen F, Knappe J, Lorch E, Jutting G, Ringelmann E, Angew. Chem.-Int. Edit., 71, 481 (1959)

[17] Sebrell WH, Harris RS, "The Vitamins," 2, 261, 2nd., Chater 5(Biotin), Academic Press, New York (1968)

[18] Kobayashi K, Sumitomo H, Ina Y, Polym. J., 15, 667 (1983)

[19] Kondo S, Ohtsuka T, Ogura K, Tsuda K, J. Macromol. Sci.-Chem., A13, 767 (1979)

[20] Backer JM, Wilchek M, Katchalski E, Proc. Nat. Acad. Sci. U.S., 68, 2604 (1971)

[21] Moore S, Link KP, J. Biol. Chem., 133, 293 (1940)

[22] Kemp W, "NMR in Chemistry (A Multinuclear Introduction)," 266, Macmillan Publishers Ltd., London (1986)

[23] Yaku E, Tsuji S, Koshijima T, Holzforschung, 33, 54 (1979)

[24] Chung DC, Kostelnik RJ, Elias HG, Makromol. Chem., 178, 691 (1977)

[25] Berne BJ, Pecora R, "Applications to Dynamic Light Scattering, Biology, Chemistry and Physics," Wiley-Interscience, New York (1976)