Preparation and Characterization of Hydrophilic Polymers Bearing 2-Phenylphenol Moieties as Microbicides

Seok-Hee Hyun; Min-Woo Kim; Ki-Heon Hong; Kyung-Eun Min; Woo-Sik Kim

Journal of Industrial and Engineering Chemistry, Vol.12, No.2, 229-234, March, 2006

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Preparation and Characterization of Hydrophilic Polymers Bearing 2-Phenylphenol Moieties as Microbicides

Seok-Hee Hyun, Min-Woo Kim¹, Ki-Heon Hong², Kyung-Eun Min¹, 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
²Department of Ophthalmic Optics, Gimcheon College, Kyungpook, Gimcheon 740-704, Korea

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2-Biphenylyl acrylate (BPA) was synthesized through the reaction of 2-phenylphenol (2PP), as amicrobicide, with acryloyl chloride. Hydrophilic copolymers with 2PP moieties were prepared by the radical copolymerization of BPA and acrylic acid (AA). From the compositions of the BPA and AA units in the copolymers, the monomer reactivity ratios were determined to be 0.54 for BPA and 0.60 for AA. This result indicates that the copolymers have na alternating tendency. The amount of 2PP released through the hydrolysis of the copolymers was examined by UV spectroscopy. The result showed that the release of 2PP increased opon increasing the hydrophilic AA content in the copolymers and upon increasing the pH of the release medium. Therefore, these results indicate that hydrophilic polymers bearing 2-phenylphenol moieties are controlled-release microbicides.

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

[References]

Pittman CU, Stahl GA, Winters H, J. Coat. Technol., 50, 636 (1978)
Mitamura H, Arimatsu Y, U. S. Patent 4,956,431, September 11 (1990)
Ghanem NA, Messiha NN, Ikladious NE, Shaaban AF, J. Appl. Polym. Sci., 26, 97 (1981)
Ghanem NA, Messiha NN, Abad El Malek MM, Illadious NE, Shaaban AF, J. Coat. Technol., 53, 57 (1981)
Shaaban AF, Mahmoud AA, Messiha NN, J. Appl. Polym. Sci., 36, 1191 (1988)
Mahmoud AA, Shaaban AF, Azab MM, Messiha NN, J. Appl. Polym. Sci., 44, 1861 (1992)
Elhamouly SH, Messiha NN, Elnour KN, J. Mater. Sci., 29(10), 2784 (1994)
Iida T, Sekiya T, Kageyama T, Sugizeki T, Moriya O, Chem. Lett., 1047 (1996)
Sghibartz CM, Faerg och Lack Scandinavia, 32, 25 (1986)
Kim WS, Lee SH, Kang IK, Park NK, Controll. Rele., 9, 281 (1989)
Arrage AA, Vasishtha N, Sundberg D, Baush G, Vincent HL, White DC, J. Ind. Microbiol., 15, 277 (1995)
Voulvoulis N, Scrimshaw MD, Lester JN, Appl. Organomet. Chem., 13, 135 (1999)
Hugues C, Bressy C, Bartolomeo P, Margaillan A, Eur. Polym. J., 39, 319 (2002)
Kim WS, Hyun SH, Lee DH, Min KE, Park LS, Seo KH, Kang IK, Polym.(Korea), 26(3), 293 (2002)
Deichman WB, Keplinger ML, in Patty's Industrial Hygiene and Toxicology; G. D. Clayton and F. E. Clayton Eds., p. 2616, Vol.2A, 3rd Edn., Ch.36, Wiley, New York (1981)
Sasaki YF, Kawaguchi S, Kamaya A, Ohshita M, Kabasawa K, Iwama K, Taniguchi K, Tsuda S, Mutation Res., 519, 103 (2002)
Ishikawa T, Asai S, Bull. Chem. Soc. Jpn., 56, 2177 (1983)
Kim WS, Jung SW, Jang JK, Kim GH, Lee JK, Polym.(Korea), 6, 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, in Encyclopedia of H. F. Mark, N. M. Bikales, C. G. Overberger, and G. Merges, Eds., p.211,2nd Edn., Vol.1, John Wiley and Sons, New York (1985)
Ritger PL, Peppas NA, J. Control. Release, 5, 37 (1987)

[Related Articles]

[1] Pittman CU, Stahl GA, Winters H, J. Coat. Technol., 50, 636 (1978)

[2] Mitamura H, Arimatsu Y, U. S. Patent 4,956,431, September 11 (1990)

[3] Ghanem NA, Messiha NN, Ikladious NE, Shaaban AF, J. Appl. Polym. Sci., 26, 97 (1981)

[4] Ghanem NA, Messiha NN, Abad El Malek MM, Illadious NE, Shaaban AF, J. Coat. Technol., 53, 57 (1981)

[5] Shaaban AF, Mahmoud AA, Messiha NN, J. Appl. Polym. Sci., 36, 1191 (1988)

[6] Mahmoud AA, Shaaban AF, Azab MM, Messiha NN, J. Appl. Polym. Sci., 44, 1861 (1992)

[7] Elhamouly SH, Messiha NN, Elnour KN, J. Mater. Sci., 29(10), 2784 (1994)

[8] Iida T, Sekiya T, Kageyama T, Sugizeki T, Moriya O, Chem. Lett., 1047 (1996)

[9] Sghibartz CM, Faerg och Lack Scandinavia, 32, 25 (1986)

[10] Kim WS, Lee SH, Kang IK, Park NK, Controll. Rele., 9, 281 (1989)

[11] Arrage AA, Vasishtha N, Sundberg D, Baush G, Vincent HL, White DC, J. Ind. Microbiol., 15, 277 (1995)

[12] Voulvoulis N, Scrimshaw MD, Lester JN, Appl. Organomet. Chem., 13, 135 (1999)

[13] Hugues C, Bressy C, Bartolomeo P, Margaillan A, Eur. Polym. J., 39, 319 (2002)

[14] Kim WS, Hyun SH, Lee DH, Min KE, Park LS, Seo KH, Kang IK, Polym.(Korea), 26(3), 293 (2002)

[15] Deichman WB, Keplinger ML, in Patty's Industrial Hygiene and Toxicology; G. D. Clayton and F. E. Clayton Eds., p. 2616, Vol.2A, 3rd Edn., Ch.36, Wiley, New York (1981)

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

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

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

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

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

[21] Nemec JW, Bauer W, in Encyclopedia of H. F. Mark, N. M. Bikales, C. G. Overberger, and G. Merges, Eds., p.211,2nd Edn., Vol.1, John Wiley and Sons, New York (1985)

[22] Ritger PL, Peppas NA, J. Control. Release, 5, 37 (1987)