Chemical Modification of Poly(styrene-alt-maleic anhydride) with Antimicrobial 4-Aminobenzoic Acid and 4-Hydroxybenzoic Acid

Jae-Hoon Jeong; Youn-Seop Byoun; Seok-Bum Ko; Youn-Sik Lee

Journal of Industrial and Engineering Chemistry, Vol.7, No.5, 310-315, September, 2001

Jae-Hoon Jeong, Youn-Seop Byoun¹, Seok-Bum Ko², and Youn-Sik Lee^†

School of Chemical Engineering and Technology, The Research Institute of Industrial Technology, Chonbuk National University, Chonju 561-756, Korea
¹Department of Industrial Chemistry, Howon University, Kunsan 573-718, Korea
²Department of Chemical Education, Chonbuk National University, Chonju 561-756, Korea

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Poly(styrene-alt-maleic anhydride) (SMA) is one of the most appropriate intermediate polymers that can be converted into bioactive polymers as its succinic anhydride units can react with any bioactive agents with low molecular weights containing amino and hydroxy groups. In this study, SMA was reacted with antimicrobial 4-aminobenzoic acid and 4-hydroxybenzoic acid to obtain P-1 and P-2, respectively, with reasonably high yields. The glass transition temperatures of P-1 and P-2 were higher than that of SMA due to hydrogen-bonding interactions. The polymers became crosslinked on heating at about 300 ℃. The new polymers were found to exhibit excellent bacteriocidal activities even though their antifungal activites were not satisfactory.

Keywords:poly(styrene-co-maleic anhydride);bioactive agent;4-aminobenzoic acid;4-hydroxybenzoic acid;antimicrobial polymer

[References]

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Nayaka PL, Lenka S, Polymeric Materials Encyclopedia, Salamone, J.C. Ed, Vol. 1, p 264, CRC Press (1996)
Daunkan R, J. Kopeck. Adv. Polym. Sci., 57, 51 (1984)
McCormick CL, U.S. Patent, 4,267,280 (1981)
McCormick CL, U.S. Patent, 4,267,281 (1981)
Tani N, Van Dress M, Anderson JM, "Controlled Release of Pesticides and Pharmaceuticals", D.H. Lews Ed., Plenum Press, New York (1981)
Richard RME, Xing DKL, Klng TP, J. Appl. Bacteriology., 78, 209 (1995)
Palmqvist E, Grage H, Meinander NQ, Hahn-Hagerdal B, Biotechnol. Bioeng., 63(1), 46 (1999)
Gump W, "Disinfectants and antiseptics", in Encyclopedia of Chemical Technology, 3rd Ed. vol. 7, pp. 793-832, John Wiley & Sons, Inc. (1979)
Derand H, Wesslen B, J. Polym. Sci. A: Polym. Chem., 33(3), 571 (1995)
Wang MT, Zhu XG, Wang SX, Zhang LD, Polymer, 40(26), 7387 (1999)
Vermeesch I, Groeninckx G, J. Appl. Polym. Sci., 53(10), 1365 (1994)
Schmidt-Naake G, Klak M, Chem. Eng. Technol., 23(9), 772 (2000)
Shibaki K, "Handbook of Bactericide and Fungicide", Kibodou, Tokyo (1986)
AATCC Test Method 100-1999
Cleveland CS, Guigley KS, Painter PC, Coleman MM, Macromolecules, 33(11), 4278 (2000)
Snyder RW, Thomson B, Bartges B, Czerniawski D, Painter PC, Macromolecules, 22, 4166 (1989)
Thomson T, Park Y, Painter PC, Snyder RW, Macromolecules, 22, 4159 (1989)
de Gooijer JM, de Haan A, Scheltus M, Schmieder-van der Vondervoort L, Koning C, Polymer, 40(23), 6493 (1999)

[Referenced By]

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[1] Sauvet G, Dupond S, Kazmierski K, Chojnowski J, J. Appl. Polym. Sci., 75(8), 1005 (2000)

[2] Nayaka PL, Lenka S, Polymeric Materials Encyclopedia, Salamone, J.C. Ed, Vol. 1, p 264, CRC Press (1996)

[3] Daunkan R, J. Kopeck. Adv. Polym. Sci., 57, 51 (1984)

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

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

[6] Tani N, Van Dress M, Anderson JM, "Controlled Release of Pesticides and Pharmaceuticals", D.H. Lews Ed., Plenum Press, New York (1981)

[7] Richard RME, Xing DKL, Klng TP, J. Appl. Bacteriology., 78, 209 (1995)

[8] Palmqvist E, Grage H, Meinander NQ, Hahn-Hagerdal B, Biotechnol. Bioeng., 63(1), 46 (1999)

[9] Gump W, "Disinfectants and antiseptics", in Encyclopedia of Chemical Technology, 3rd Ed. vol. 7, pp. 793-832, John Wiley & Sons, Inc. (1979)

[10] Derand H, Wesslen B, J. Polym. Sci. A: Polym. Chem., 33(3), 571 (1995)

[11] Wang MT, Zhu XG, Wang SX, Zhang LD, Polymer, 40(26), 7387 (1999)

[12] Vermeesch I, Groeninckx G, J. Appl. Polym. Sci., 53(10), 1365 (1994)

[13] Schmidt-Naake G, Klak M, Chem. Eng. Technol., 23(9), 772 (2000)

[14] Shibaki K, "Handbook of Bactericide and Fungicide", Kibodou, Tokyo (1986)

[15] AATCC Test Method 100-1999

[16] Cleveland CS, Guigley KS, Painter PC, Coleman MM, Macromolecules, 33(11), 4278 (2000)

[17] Snyder RW, Thomson B, Bartges B, Czerniawski D, Painter PC, Macromolecules, 22, 4166 (1989)

[18] Thomson T, Park Y, Painter PC, Snyder RW, Macromolecules, 22, 4159 (1989)

[19] de Gooijer JM, de Haan A, Scheltus M, Schmieder-van der Vondervoort L, Koning C, Polymer, 40(23), 6493 (1999)