• Bulletin of the Korean Chemical Society
• /
• v.30 no.10
• /
• pp.2227-2232
• /
• 2009

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.

• Polymer(Korea)
• /
• v.27 no.5
• /
• pp.470-476
• /
• 2003

In order to obtain high refractive plastic materials, 1,2 -ethylenedisulfanylbis(2-mercaptomethyl-1-ethanthiol) (ESTT) was newly prepared in good yield by the reaction of 1,2-ethylenedisulfanylbis(2-bromomethyl-1-ethanthiol) (ESTB) with thiourea followed by hydrolysis using an aqueous ammonia solution and characterized by $^1$H-NMR (-SH at 1.7 ppm), $\^$13/C-NMR(-CH$_2$SH at 28.4 ppm) and FT-IR (-SH at 2540 cm$\^$-1/) spectroscopy, etc. Polythiourethanes (PTU) were obtained from the combinations of ESTT with each of 4,4＇-methylenebis(phenylisocyanate) (MDI), tolyene 2,4-diisocyanate (TDI), isophorone diisocyanate (IPDI), mxylene diisocyanate (XDI), and 1,6-diisocyanatohexane (HMDI) in the presence of dibutyltin dilaurylate as a catalyst, in a casting mold, and characterized by FT-IR (existence of N=C=O) spectroscopy and elemental analyzer (sulfur content). Accordingly, their thermal, mechanical and optical properties were investigated by using DSC, TGA, hardness tester and refractometer: both the melting point on DSC and crystallinity on X -ray diffraction (XRD) for specimens of PTUs were not observed. PTUs with T$\_$g/s above 110 $^{\circ}C$ showed good hardness (Shore D) in the range of 86 to 89. Thermal stabilities of PTUs obtained by using ESTT and each of diisocyanates containing aromatic rings were especially good. Also, the optical transmittances of amorphous PTUs through UV-visible source in the range of 400 to 600 nm were good. PTUs showed refractive indexes above 1.60, and their refractive indexes gradually increased with increase of sulfur contents.

• Journal of Korean Ophthalmic Optics Society
• /
• v.13 no.3
• /
• pp.1-6
• /
• 2008

Purpose: Plastic optical monomer materials having ultra high refractive index have an income of the whole quantity from advanced nations to domestic companies which are related to plastic optical lens. It is necessary to develop novel plastic optical lens materials in order to overcome a FTA provision and revitalize a stagnating optical lens industry in the interior optical lens industries. The new plastic optical lens materials against the substitution effect of income should be gradually demanded. This work will be synthesized novel super high refractive monomer resin materials of urethane lens series and studied the properties of optical lens using it. Methods: ETS-4 (2-(2-mercaptoethylthio)-3-{2-[3-mercapto-2-(2-mercaptoethylthio)propyl thio]ethylthio}propane -1-thiol), which is optical lens monomer resin having super high refractive index, was synthesized and identified its structure and property by elemental analysis, EI-MS, TGA, FT-IR spectroscopy, $^1H$ and $^{13}C$ NMR spectroscopies. After mixing evenly from mixed monomer resin and diisocyanate series, it was casting in glass mold. After thermal curing, the obtained optical lenses were measured and compared with the refractive index and Abbe number for studies of their optical properties. Results: We have synthesized the novel ultra high refractive index monomer resin, ETS-4, and have identified its structure and property by elemental analysis, EI-MS, TGA, FT-IR spectroscopy, $^1H$ and $^{13}C$ NMR spectroscopies. The existence of three isomers for EST-4 was identified by $^{13}C$ NMR spectroscopy. The refractive index ($N_d$ at $25^{\circ}C$) of monomer resin in liquid state obtained from the Abbe refractometer was 1.647. The refractive indexes of raw plastic optical lenses prepared from the mixed ETS-4 monomer and diisocyanate series were in the range of 1.656~1.680. Conclusions: Novel super high refractive index plastic optical lens monomer was synthesized and analysed, the optical lenses prepared using it were colorless transparency and excellent properties. It is of utility for the industrialization.