고분자 항균제의 합성 및 특성

오상택; 유종선; 민병권; 하창식; 조원제

Polymer(Korea), Vol.18, No.2, 276-281, March, 1994

Export Citation

고분자 항균제의 합성 및 특성

Synthesis and Biocidal Activities of Polymeric Bactericides

오상택, 유종선, 민병권, 하창식, 조원제

초록

항박테리아성 단량체인 2,4,4'-트리클로로-2'-~아크릴로일옥시디페닐 에테르(AcDP)를 트리에틸 아민 존재하의 건조 THF용매에서 2,4,4'-트리클로로-2'히드록시디페닐 에테르(DP)와 아크릴로일 클로리드로부터 합성하였다. 합성된 AcDP는 IR 및 ¹H-NMR 스펙트라로 확인하였다. AcDP의 단독중합체는 70℃의 톨루엔 용매하에서 개시제인 BPO를 사용하여 중합하였다. AcDP와 메틸메~타크릴레이트(MMA)의 공중합체를 70℃에서 합성하였다. Poly(AcDP) 및 polu(AcDP-co-MMA)는 IR과 ¹H-NMR 스펙트라로 확인하였다. Poly(AcDP) 및 poly(AcDP-co-MMA)의 중량 평균 분자량은 각각 4100 및 9200이었다. AcDP, poly(AcDP) 및 poly(AcDP-co-MMA)의 항박테리아성은 agar dish법으로 확인하였다. DP뿐만 아니라 AcDP 및 그 중합체의 Staphylococcus aureus에 대한 항박테리아성은 PMMA 및 polu(ethylene-co-vinyl acetate)와 같은 기준 물질에 비하여 매우 우수하였다. Staphylococcus aureus에 대한 항박테리아성의 크기는 DP>AcDP>poly(AcDP)>poly(AcDP-co-MMA) 순서이었다.

The bactericidal monomer, 2,4,4'-trichloro-2'-acryloyloxydiphenyl ether (AcDP) was synthesized from 2,4,4'-trichloro-2'-hydroxydiphenyl ether(DP) and acryloyl chloride in the presence of triethylamine in dry THF. The synthesized AcDP was identified by IR and ¹H-NMR spectra. The homopolymer of AcDP was obtained using BPO as an initiator in toluene at 70℃. Copolymer of AcDP and methyl methacrylate(MMA) was synthesized with an initiator at 70℃. Poly(AcDP) and poly(AcDP-co-MMA) were identified by IR and ¹H-NMR spectra. The weight average molecular weights of poly(AcDP) and poly(AcDP-co-MMA) were 4100 and 9200, respectively. The bactericldal activities of AcDP, poly(AcDP), and poly(AcDP-co-MMA) were studied using agar dish test. The bactericidal activities of AcDP and its polymers as well as DP against Staphylococcus aureus were very excellent compared to those of control polymers such as PMMA and poly(ethylene-co-vinyl acetate) The bactericidal activities were decreased in the order DP>AcDP>poly(AcDP)>poly(AcDP-co-MMA) against Staphylococcus aureus.

[References]

Pittman CC, J. Appl. Polym. Sci., 26, 2403 (1981)
Geigy JR, British Patent, 1,024,022, March 30 (1966)
Inoue Y, Bactericide and Fungicide for a Comfortable Environment, CMC, Tokyo (1992)
Inoue Y, Technology and Market of Bactericide and Fungicide, CMC, Tokyo (1990)
Shibasaki I, Handbook of Bactericide and Fungicide, Kihoudou, Tokyo (1986)
Apostolatos GN, Bohrer JC, Inamorato JT, U.S. Patent, 3,989,827 (1976)
Finzi G, Grimaldi G, Arch. Sci. Med., 137(4), 775 (1980)
Carol MR, Rutherford NJ, U.S. Patent, 4,832,861 (1989)
Meehan EJ, J. Polym. Sci., 1(3), 175 (1946)
Smakula A, Angew. Chem.-Int. Edit., 47, 777 (1934)

[Referenced By]

[1] Pittman CC, J. Appl. Polym. Sci., 26, 2403 (1981)

[2] Geigy JR, British Patent, 1,024,022, March 30 (1966)

[3] Inoue Y, Bactericide and Fungicide for a Comfortable Environment, CMC, Tokyo (1992)

[4] Inoue Y, Technology and Market of Bactericide and Fungicide, CMC, Tokyo (1990)

[5] Shibasaki I, Handbook of Bactericide and Fungicide, Kihoudou, Tokyo (1986)

[6] Apostolatos GN, Bohrer JC, Inamorato JT, U.S. Patent, 3,989,827 (1976)

[7] Finzi G, Grimaldi G, Arch. Sci. Med., 137(4), 775 (1980)

[8] Carol MR, Rutherford NJ, U.S. Patent, 4,832,861 (1989)

[9] Meehan EJ, J. Polym. Sci., 1(3), 175 (1946)

[10] Smakula A, Angew. Chem.-Int. Edit., 47, 777 (1934)