Method for manufacturing resin for urethane-based optical material, resin composition for same, and optical material manufactured thereby
A method of preparing an optical material by polymerizing a resin composition including a thiol group-containing compound and an isocyanate group-containing compound, particularly, a method of preparing a high-quality urethane-based optical material using a universal polyisocyanate compound. According to one aspect, a resin composition including a polythiol compound and a widely available polyisocyanate compound, as main components, and having a moisture content of 300 to 3,000 ppm is template-polymerized to prepare the optical material. A colorless, transparent, and high-quality urethane-based optical material may be efficiently prepared in high yield using a low-cost and widely available isocyanate compound through template-polymerization using a tape while minimizing generation of white tape residues and foaming.
1. A method of preparing a resin for a urethane-based optical material by template-polymerizing a resin composition in a glass mold constituted with a tape comprising a polythiol compound and a polyisocyanate compound,
wherein the resin composition has a moisture content of 350 to 3000 ppm, and
the polyisocyanate compound comprises at least one compound selected from the group consisting of isophorone diisocyanate, and hexamethylene diisocyanate.
2. The method according to claim 1 , wherein the polythiol compound has a moisture content of 700 to 6,000 ppm.
3. The method according to claim 2 , wherein the polythiol compound comprises at least one compound selected from the group consisting of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 2,3-bis(2-mercaptoethylthio)-3-propane-1-thiol, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, bis(2-mercaptoethyl)sulfide, tetrakis(mercaptomethyl)methane, 2-(2-mercaptoethylthio)propane-1,3-dithiol, 2-(2,3-bis(2-mercaptoethylthio)propylthio)ethanethiol, bis(2,3-dimercaptopropanyl)sulfide, bis(2,3-dimercaptopropanyl)disulfide, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 1,2-bis(2-(2-mercaptoethylthio)-3-mercaptopropylthio)ethane, bis(2-(2-mercaptoethylthio)-3-mercaptopropyl)sulfide, 2-(2-mercaptoethylthio)-3-2-mercapto-3-[3-mercapto-2-(2-mercaptoethylthio)-propylthio]propylthio-propane-1-thiol, 2,2-bis-(3-mercapto-propyonyloxymethyl)-butyl ester, 2-(2-mercaptoethylthio)-3-(2-(2-[3-mercapto-2-(2-mercaptoethylthio)-propylthio]ethylthio)ethylthio)propane-1-thiol, (4R,11S)-4,11-bis(mercaptomethyl)-3,6,9,12-tetrathiatetradecane-1,14-dithiol, (S)-3-((R-2,3-dimercaptopropyl)thio)propane-1,2-dithiol, (4R,14R)-4,14-bis(mercaptomethyl)-3,6,9,12,15-pentathiaheptane-1,17-dithiol, 3-((3-mercapto-2-((2-mercaptoethyl)thio)propyl)thio)propyl)thio)-2-((2-mercaptoethyl)thio)propane-1-thiol, 3,3′-dithiobis(propane-1,2-dithiol), (7R,11S)-7,11-bis(mercaptomethyl)-3,6,9,12,15-pentathiaheptane-1,17-dithiol, (7R,12S)-7,12-bis(mercaptomethyl)-3,6,9,10,13,16-hexathiaoctadecane-1,18-dithiol, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(3-mercaptopropionate), trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), bispentaerythritol-ether-hexakis(3-mercaptopropionate), 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptodimethylthio)ethyl)-1,3-dithiethane.
4. The method according to claim 1 , wherein the resin composition further comprises at least one iso(thio)cyanate compound selected from the group consisting of:
dicyclohexylmethane-4,4-diisocyanate (H 12 MDI), methylcyclohexane diisocyanate, tolylene diisocyanate, phenylene diisocyanate, 1,3,5-tris(6-isocyanatohexyl)-[1,3,5]-triazine-2,4,6-(1H,3H,5H)-trione (HDI trimer), o,m,p-xylylene diisocyanate, and tetramethylxylylene diisocyanate (TMXDI), and tetramethylxylylene diisocyanate (TMXDI).
5. A resin composition for a urethane-based optical material comprising:
a polythiol compound; and
a polyisocyanate compound comprising at least one compound selected from the group consisting of isophorone diisocyanate, and hexamethylene diisocyanate;
wherein the resin composition comprises a moisture content of 350-3000 ppm.
6. A resin for a urethane-based optical material prepared using the method according to claim 1 .
7. An optical lens comprising the resin for a urethane-based optical material according to claim 6 .
8. The optical lens according to claim 7 , wherein the optical lens comprises a lens for eyeglasses.