ortho-Benzoquinone을 기반으로 하는 청색광 차단 수화젤 콘택트렌즈 제조

원희재; 김병선; 조병기; Hee Jae Won; Byung Sun Kim; Byoung-Ki Cho

Polymer(Korea), Vol.44, No.6, 868-874, November, 2020

DOI10.7317/pk.2020.44.6.868 Export Citation

ortho-Benzoquinone을 기반으로 하는 청색광 차단 수화젤 콘택트렌즈 제조

Blue-Light Blocking Hydrogel Contact Lenses Based on ortho-Benzoquinone

원희재, 김병선¹, 조병기^†

단국대학교 화학과
¹호서대학교 화학공학과

Hee Jae Won, Byung Sun Kim¹, and Byoung-Ki Cho^†

Department of Chemistry, Dankook University, Cheonan 31116, Korea
¹Department of Chemical Engineering, Hoseo University, Cheonan 31499, Korea

E-mail:

초록

Catechol 단량체를 dopamine과 methacrylic anhydride와의 반응을 통해 합성하였다. 이후, 2-hydroxy ethylmethacrylate(HEMA), ethylene glycol dimethacrylate(EGDMA), 2-methacryloyloxyethyl phosphorylcholine (MPC)과 공중합한 후, 염기 조건에서 산화반응을 수행하여 ortho-benzoquinone을 기반으로 하는 갈색 투명한 청색광 차단 수화젤 렌즈를 제조하였다. 제조 시, catechol 단량체의 첨가량에 따라, 청색광 차단 정도를 조절할 수 있었으며, 최대 38%까지 청색광을 차단하였다. 또한 UV-A 및 UV-B 영역도 차단하는 효과를 보였다. 제조된 렌즈들은 87% 이상의 평균 가시광선 투과율을 보였다. 함수율과 접촉각은 각각 60% 이상, 60° 미만의 수치를 나타내어, 렌즈 내부 및 표면에서의 친수성이 우수하다는 것을 알 수 있었다.

Catechol monomer was synthesized by the reaction of dopamine and methacrylic anhydride. Then, it was copolymerized with 2-hydroxy ethylmethacrylate (HEMA), ethylene glycol dimethacrylate (EGDMA), 2-methacryloyloxyethyl phosphorylcholine (MPC). Subsequent oxidation reaction under a basic condition produced transparent and brownish blue-light blocking hydrogel contact lenses (BB Lenses) based on ortho-benzoquinone. Degree of the blue-light blocking could be controlled depending on the amount of catechol monomer at the initial mixing step of monomers. The maximum blue light blocking ratio was determined to be 38%, and the BB lenses also blocked UV-A and UV-B. The BB lenses exhibited high luminous transmittances more than 87%. The water content and contact angle values were more than 60% and less than 60°, respectively, indicating excellent hydrophilicity both interior and surface of lenses

Keywords:hydrogel;contact lenses;blue-light blocking;ortho-benzoquinone;hydrophilicity

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[2] Kang S, Hong JE, Choi EJ, J. Korean Ophthalmic Opt. Soc., 21, 69 (2016)

[3] Sliney DH, Freasier BC, Appl. Opt., 12, 1 (1973)

[4] Kim CJ, Choi SW, Yang SJ, Oh SY, Choi EJ, J. Korean Ophthalmic Opt. Soc., 19, 135 (2014)

[5] Jung MS, Choi EJ, J. Korean Ophthalmic Opt. Soc., 23, 57 (2018)

[6] Madrakian T, Afkhami A, Khalafi L, Mohammadnejad M, J. Braz. Chem. Soc., 17, 1259 (2006)

[7] Zhao Y, Gan Y, Zhang L, Chu Z, Liu F, Zhang W, Anal. Methods, 10, 775 (2018)

[8] Liu R, Mahurin SM, Li C, Unocic RR, Idrobo JC, Gao H, Pennycook SJ, Dai S, Angew. Chem.-Int. Edit., 50, 6799 (2011)

[9] Hirota K, Murakami K, Nemoto K, Miyake Y, Fems Microbiol. Lett, 37, 248 (2005)

[10] Lewis AL, Colloids Surf. B: Biointerfaces, 18, 261 (2000)

[11] Goda T, Matsuno R, Konno T, Takai M, Ishihara K, Colloids Surf. B: Biointerfaces, 63, 64 (2008)

[12] Patil N, Falentin-Daudre C, Jerome C, Detrembleur C, Polym. Chem., 6, 2919 (2015)

[13] Ye KH, Sung AY, J. Korean Chem. Soc., 54, 460 (2010)

[14] Kim HJ, Ryu GC, Jeong KS, Jun J, Macromol. Res., 23(1), 74 (2015)

[15] Cuthbertson FM, J. Cataract Refract. Surg., 35, 1281 (2009)

[16] Song TH, Cho CK, Lee SE, Kim SR, Park M, J. Korean Ophthalmic Opt. Soc., 24, 29 (2019)

[17] Wei Q, Zhang F, Li J, Li B, Zhao C, Polym. Chem., 1, 1430 (2010)

[18] Song KS, Kim TH, Sung AY, J. Korean Chem. Soc., 57, 300 (2013)

[19] Lin CH, Cho HL, Yeh YH, Yang MC, Colloids Surf. B: Biointerfaces, 136, 735 (2015)