Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Novel Polythiol for Plastic Optical Lens and its Ophthalmic Lens

  • Jang, Dong-Gyu (Department of Chemistry, College of Life Science and Nanotechnology, Hannam University) ;
  • Roh, Soo-Gyun (Optical Material Institute, Shin Dae Specialties Co., Ltd) ;
  • Kim, Jong-Hyo (Optical Material Institute, Shin Dae Specialties Co., Ltd) ;
  • Jin, Wen-Yi (Optical Material Institute, Shin Dae Specialties Co., Ltd) ;
  • Seo, Jin-Moo (Optical Material Institute, Shin Dae Specialties Co., Ltd) ;
  • Kwon, Myeong-Ja (Department of Chemistry, College of Life Science and Nanotechnology, Hannam University) ;
  • Lee, Soo-Min (Department of Chemistry, College of Life Science and Nanotechnology, Hannam University)
  • Published : 2009.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

Novel polythiol materials of urethane lens series for plastic optical lens were synthesized from polyol materials via thioisouronium of thiourea with c-HCl in refluxing aqueous solution, in which polythiol material was carried out from hydrolysis of thioisouronium by ammonia water. Their structure properties were identified by EA, EI-MS, FT-IR, $^1H\;and\;^{13}C$ NMR spectroscopies and TGA. Their ophthalmic lenses as polythiourethane material were prepared by thermal curing to an injected glass mold using the evenly solutions of diisocyanates series (TDI, XDI, HDI or IPDI) with polythiols. Polythiourethane shows that the strong stretching mode for SH group of polythiol disappeared in FT-IR spectra after thermosetting polymerization. Thermal deformation starting temperature of ophthalmic lenses was determined by TMA. Ophthalmic lenses made from characteristic polythiol and diisocyanate series have transparency, colorless and good impact strength, in which thermal resistance and impact strength of ophthalmic lenses were influenced by diisocyanate series. Physical properties of ophthalmic lens have contrast thermal resistance with impact strength. The property of thermal resistance and impact strength for respective ophthalmic lenses was examined by TMA and drop ball test.

Keywords

References

  1. Kanemura, Y.; Imai, M.; Sasagawa, K.; Kagimoto, N.; Nagata, T. Korea Patent 1987-0001768, 1987.
  2. Okazaki, M.; Kuma, S.; Kanemura, Y. Japan Patent 2001039944, 2001.
  3. Kawauchi, K.; Sasagawa, K.; Kobayashi, S. Japan Patent JP8157446, 1996.
  4. Morishiri, H.; Kobayashi, S. Japan Patent 2006001982, 2006.
  5. Kanemura, Y.; Sasagawa, K.; Imai, M.; Suzuki, T. Korean Patent 10-0055948, 1992.
  6. Morishiri, H.; Kobayashi, S. Japan Patent 2005350531, 2005.
  7. Okubo, T.; Honma, M.; Wang, M.; Takamatsu, T. Japan Patent 2004310001, 2004.
  8. Kanemura, Y.; Sasagawa, K.; Kobayashi, S. European Patent 0 528 590 A1, 1992.
  9. Vujasinovi, I.; Veljovi, J.; Minari-Majerski, K. J. Org. Chem. 2004, 69(24), 8550. https://doi.org/10.1021/jo048712l
  10. Szonyi, F.; Cambon, A. J. Fluorine Chem. 1987, 36(2), 195. https://doi.org/10.1016/S0022-1139(00)81027-1
  11. Wolf, R. E.; Hartman, J. J. R.; Storey, J. M. E.; Foxman, B. M.; Cooper, S. R. J. Am. Chem. Soc. 1987, 109(14), 4328. https://doi.org/10.1021/ja00248a031
  12. Zeng, L.; Miller, E. W.; Pralle, A.; Isacoff, E. Y.; Chang, C. J. J. Am. Chem. Soc. 2006, 128(1), 10. https://doi.org/10.1021/ja055064u
  13. Buter, J.; Kellogg, R. M. Organic Syntheses 1987, 65, 150. https://doi.org/10.15227/orgsyn.065.0150
  14. Guyon, V.; Guy, A.; Foos, J.; Lemaire, M.; Draye, M. Tetrahedron 1995, 51(14), 4065. https://doi.org/10.1016/0040-4020(95)00147-Z
  15. Jang, D. G.; Kim, J. H.; Lee, S. M.; Roh, S. G. J. Korean Oph. Opt. Soc. 2008, 13(3), 1.
  16. Okazaki, K.; Kanemura, Y.; Nagata, T. Korea Patent 10-0180926, 1998.

Cited by

  1. Hard coatings for CR-39 based on Al2O3–ZrO2 3-glycidoxypropyltrimethoxysilane (GPTMS) and tetraethoxysilane (TEOS) nanocomposites vol.79, pp.1, 2016, https://doi.org/10.1007/s10971-016-4006-3
  2. New thermoplastic poly(carbonate-urethane)s based on chain extenders with sulfur atoms vol.71, pp.7, 2017, https://doi.org/10.1007/s11696-016-0112-5