A Study on the Copolymerization Kinetics of Phenylethyl Acrylate and Phenylethyl Methacrylate

Hanna Lee; Giyoong Tae; Young Ha Kim

Macromolecular Research, Vol.16, No.7, 614-619, October, 2008

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A Study on the Copolymerization Kinetics of Phenylethyl Acrylate and Phenylethyl Methacrylate

Hanna Lee, Giyoong Tae , and Young Ha Kim^†

Dept. of Materials Science and Engineering, Research Center for Biomolecular Nanotechnology, Gwangju Institute of Science and Technology, Gwangju 500-712, Korea

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Copolymers of phenyl alkyl acrylates/methacrylates are used clinically as soft materials for the foldable intraocular lens (IOL) to treat cataracts. In this study, copolymers of 2-phenylethyl acrylate (PEA) and 2-phenylethyl methacrylate (PEMA) of various compositions were prepared using free radical polymerization in solution. The composition of the copolymers was determined by 1H-NMR analysis. The reactivity ratios of the monomers were calculated using the conventional Fineman-Ross or Kelen-Tudos method. The reactivity ratio of PEA (r1) and PEMA (r2) were estimated to be 0.280 and 2.085 using the Kelen-Tudos method, respectively. These values suggest that PEMA is more reactive in copolymerization than PEA, and the copolymers will have a higher content of PEMA units. The glass transition temperature (Tg) of the copolymers increased with increasing PEMA content. The molecular weight and polydispersity indices (Mw/Mn) of the polymers were determined by GPC. Overall, these results are expected to be quite useful in applications to foldable soft IOL materials.

Keywords:2-phenylethyl acrylate (PEA);2-phenylethyl methacrylate (PEMA);reactivity ratios;intraocular lens (IOL)

[References]

Imafuku S, Hamano M, Iwamoto H, European Pat. No. WO96/25962.
Chehade M, Elder MJ, Australian and New Zealand J.Ophthalmol, 25, 255 (1997)
Arnold PN, J. Cataract. Refract. Surg., 16, 646 (1990)
Kohnen T, J. Cataract. Refract. Surg., 22, 1255 (1996)
Sowinski K, Misiuk-Hojo M, Szalinski M, Polimery wmedycynie, 37, 35 (2007)
Chao Q, Chin. Ophthalmic. Res., 22, 666 (2004)
Yamanaka A, Yokoyama Y, Iwamoto H, J. Artif. Organs., 9, 67 (2006)
Hayashi K, Hayashi H, Nakao F, Hayashi F, J. Cataract.Refract. Surg., 22, 743 (1996)
Mamalis N, Davis B, Nilson CS, Hickman MS, Leboyer RM, J. Cataract. Refract. Surg., 30, 2209 (2004)
Jaffe GJ, Am. J. Ophthalmol., 124, 692 (1997)
McCulley JP, Eye and Contact Lens, 29, 155 (2003)
Barrett PR, J. Cataract. Refract. Surg., 25, 72 (1999)
Oh KT, J. Cataract. Refract. Surg., 22, 667 (1996)
Shugar JK, J. Cataract. Refract. Surg., 22, 1355 (1996)
Shugar JK, Lewis C, Lee A, J. Cataract. Refract. Surg., 22, 1368 (1996)
Egan CA, Kottos PJ, Francis IC, Kappagoda MB, Schumacher RS, Boytel KA, Haylen MJ, Alexander S, J.Cataract. Refract. Surg., 22, 1272 (1996)
Stulting RD, Lahners WJ, Carr JD, Cornea, 19, 741 (2000)
Koch DD, Alcon AcrySof acrylic intraocular lens, Martin RG, Gills JP, and Sanders DR, Eds., Foldable Intraocular Lenses, Thorofare NJ, Slack Inc, 1993, pp 161-177
Oshika T, Suzuki Y, Kizaki H, Yaguchi S, J. Cataract.Refract. Surg., 22, 104 (1996)
Lloyd AW, Faragher RGA, Denyer SP, Biomaterials, 22, 769 (2001)
Fineman M, Ross SP, J. Polym. Sci., 5, 259 (1950)
Kelen T and Tudos F, Macromol J. Sci. Pure Appl. Chem., A9, 1 (1975)
Chikhaoui-Grioune D, Benaboura A, Jerome R, Eur.Polym. J., 43, 3849 (2007)
Cohen J, Cohen P, West SG, and Aiken LS, Applied multiple regression/correlation analysis for the behavioral sciences, 3rd ed., Hillsdale, New Jersey, Lawrence Erlbaum Associates, 2003
Dainton FS, Ivin KJ, Quart. Rev., 12, 61 (1958)
Busfield WK, Lee RM, Makromol. Chem., 176, 2017 (1975)
Fox TJ, Bull. Am. Phys. Soc., 1, 123 (1956)
Teramachi S, Hasegawa A, Atasuka M, Yamashita A, Takemoto N, Macromolecules, 11, 1206 (1978)
Arun A, Reddy BSR, J. Polym. Sci. A: Polym. Chem., 41(11), 1632 (2003)
Senthilkumar U, Ganesan K, Reddy BSR, J. Polym.Res., 10, 21 (2006)

[Referenced By]

[Related Articles]

[1] Imafuku S, Hamano M, Iwamoto H, European Pat. No. WO96/25962.

[2] Chehade M, Elder MJ, Australian and New Zealand J.Ophthalmol, 25, 255 (1997)

[3] Arnold PN, J. Cataract. Refract. Surg., 16, 646 (1990)

[4] Kohnen T, J. Cataract. Refract. Surg., 22, 1255 (1996)

[5] Sowinski K, Misiuk-Hojo M, Szalinski M, Polimery wmedycynie, 37, 35 (2007)

[6] Chao Q, Chin. Ophthalmic. Res., 22, 666 (2004)

[7] Yamanaka A, Yokoyama Y, Iwamoto H, J. Artif. Organs., 9, 67 (2006)

[8] Hayashi K, Hayashi H, Nakao F, Hayashi F, J. Cataract.Refract. Surg., 22, 743 (1996)

[9] Mamalis N, Davis B, Nilson CS, Hickman MS, Leboyer RM, J. Cataract. Refract. Surg., 30, 2209 (2004)

[10] Jaffe GJ, Am. J. Ophthalmol., 124, 692 (1997)

[11] McCulley JP, Eye and Contact Lens, 29, 155 (2003)

[12] Barrett PR, J. Cataract. Refract. Surg., 25, 72 (1999)

[13] Oh KT, J. Cataract. Refract. Surg., 22, 667 (1996)

[14] Shugar JK, J. Cataract. Refract. Surg., 22, 1355 (1996)

[15] Shugar JK, Lewis C, Lee A, J. Cataract. Refract. Surg., 22, 1368 (1996)

[16] Egan CA, Kottos PJ, Francis IC, Kappagoda MB, Schumacher RS, Boytel KA, Haylen MJ, Alexander S, J.Cataract. Refract. Surg., 22, 1272 (1996)

[17] Stulting RD, Lahners WJ, Carr JD, Cornea, 19, 741 (2000)

[18] Koch DD, Alcon AcrySof acrylic intraocular lens, Martin RG, Gills JP, and Sanders DR, Eds., Foldable Intraocular Lenses, Thorofare NJ, Slack Inc, 1993, pp 161-177

[19] Oshika T, Suzuki Y, Kizaki H, Yaguchi S, J. Cataract.Refract. Surg., 22, 104 (1996)

[20] Lloyd AW, Faragher RGA, Denyer SP, Biomaterials, 22, 769 (2001)

[21] Fineman M, Ross SP, J. Polym. Sci., 5, 259 (1950)

[22] Kelen T and Tudos F, Macromol J. Sci. Pure Appl. Chem., A9, 1 (1975)

[23] Chikhaoui-Grioune D, Benaboura A, Jerome R, Eur.Polym. J., 43, 3849 (2007)

[24] Cohen J, Cohen P, West SG, and Aiken LS, Applied multiple regression/correlation analysis for the behavioral sciences, 3rd ed., Hillsdale, New Jersey, Lawrence Erlbaum Associates, 2003

[25] Dainton FS, Ivin KJ, Quart. Rev., 12, 61 (1958)

[26] Busfield WK, Lee RM, Makromol. Chem., 176, 2017 (1975)

[27] Fox TJ, Bull. Am. Phys. Soc., 1, 123 (1956)

[28] Teramachi S, Hasegawa A, Atasuka M, Yamashita A, Takemoto N, Macromolecules, 11, 1206 (1978)

[29] Arun A, Reddy BSR, J. Polym. Sci. A: Polym. Chem., 41(11), 1632 (2003)

[30] Senthilkumar U, Ganesan K, Reddy BSR, J. Polym.Res., 10, 21 (2006)