Method for preparing thioepoxy-based optical material and polymerizable composition thereof

1. A polymerizable composition comprising a thioepoxy compound (A) and a compound (B) formed as a by-product in the preparation of the thioepoxy compound (A) wherein the compound (B) is at least one of 2,3-epoxypropyl(2,3-epithiopropyl)sulfide and 2,3-epoxypropyl(2,3-epithiopropyl)disulfide represented by Formula 1 and is present in an amount of 4.5 to 15% of the total weight of the compounds (A) and (B):

2. The polymerizable composition according to claim 1 , further comprising a phosphonium salt as a polymerization catalyst.

3. The polymerizable composition according to claim 1 , further comprising a polyisocyanate compound.

4. The polymerizable composition according to claim 1 , further comprising a polythiol compound.

5. The polymerizable composition according to claim 1 , further comprising a polyisocyanate compound, a polythiol compound, and a phosphonium salt as a polymerization catalyst.

6. The polymerizable composition according to claim 1 , wherein the thioepoxy compound is selected from the group consisting of bis(2,3-epithiopropyl)sulfide, bis(2,3-epithiopropyl)disulfide, 1,3-bis(β-epithiopropylthio)cyclohexane,1,4-bis(β-epithiopropylthio)cyclohexane, 1,3-bis(β-epithiopropylthiomethyl)cyclohexane, 1,4-bis(β-epithiopropylthiomethyl)cyclohexane, 2,5-bis(β-epithiopropylthiomethyl)-1,4-dithiane, 2,5-bis(β-epithiopropylthioethylthiomethyl)-1,4 -dithiane, 2-(2-β-epithiopropylthioethylthio)-1,3-bis (β-epithiopropylthio)propane, and mixtures thereof.

7. The polymerizable composition according to claim 3 , wherein the polyisocyanate compound is selected from the group consisting of isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexyl methanediisocyanate, xylylene diisocyanate, 3,8-bis(isocyanatomethyl)tricyclo[5,2,1,0 2 ′ 6 ]decane, 3,9-bis(isocyanatomethyl)tricyclo[5,2,1,0 2 ′ 6 ]decane, 4,8-bis(isocyanatomethyl)tricyclo [5,2,1,0 2 ′ 6 ]decane, 2,5-bis(isocyanatomethyl)bicyclo[2,2,1]heptane, 2,6-bis(isocyanatomethyl)bicyclo[2,2,1]heptane, and mixtures thereof.

8. The polymerizable composition according to claim 4 , wherein the polythiol compound is bis(2-mercaptoethyl)sulfide.

9. The polymerizable composition according to claim 1 , further comprising an olefinic compound as a reactive resin modifier.

10. The polymerizable composition according to claim 1 , further comprising, as an internal release agent, at least one phosphate compound selected from the group consisting of 4-PENPP [polyoxyethylene nonylphenol ether phosphate (5% by weight of 5-mol ethylene oxide adduct, 80% by weight of 4-mol ethylene oxide adduct, 10% by weight of 3-mol ethylene oxide adduct, and 5% by weight of 1-mol ethylene oxide adduct)], 8-PENPP [polyoxyethylene nonylphenol ether phosphate (3% by weight of 9-mol ethylene oxide adduct, 80% by weight of 8-mol ethylene oxide adduct, 5% by weight of 7-mol ethylene oxide adduct, 6% by weight of 6-mol ethylene oxide adduct, and 6% by weight of 5-mol ethylene oxide adduct)], 12-PENPP [polyoxyethylene nonylphenol ether phosphate (3% by weight of 13-mol ethylene oxide adduct, 80% by weight of 12-mol ethylene oxide adduct, 8% by weight of 11-mol ethylene oxide adduct, 3% by weight of 9-mol ethylene oxide adduct, and 6% by weight of 4-mol ethylene oxide adduct)], 16-PENPP [polyoxyethylene nonylphenol ether phosphate (3% by weight of 17-mol ethylene oxide adduct, 79% by weight of 16-mol ethylene oxide adduct, 10% by weight of 15-mol ethylene oxide adduct, 4% by weight of 14-mol ethylene oxide adduct, and 4% by weight of 13-mol ethylene oxide adduct)], 20-PENPP [polyoxyethylene nonylphenol ether phosphate (5% by weight of 21-mol ethylene oxide adduct, 78% by weight of 20-mol ethylene oxide adduct, 7% by weight of 19-mol ethylene oxide adduct, 6% by weight of 18-mol ethylene oxide adduct, and 4% by weight of 17-mol ethylene oxide adduct)], 4-PPNPP [polyoxypropylene nonylphenol ether phosphate (5% by weight of 5-mol propylene oxide adduct, 80% by weight of 4-mol propylene oxide adduct, 10% by weight of 3-mol propylene oxide adduct, and 5% by weight of 1-mol propylene oxide adduct)], 8-PPNPP [polyoxypropylene nonylphenol ether phosphate (3% by weight of 9-mol propylene oxide adduct, 80% by weight of 8-mol propylene oxide adduct, 5% by weight of 7-mol propylene oxide adduct, 6% by weight of 6-mol propylene oxide adduct, and 6% by weight of 5-mol propylene oxide adduct)], 12-PPNPP [polyoxypropylene nonylphenol ether phosphate (3% by weight of 13-mol propylene oxide adduct, 80% by weight of 12-mol propylene oxide adduct, 8% by weight of 11-mol propylene oxide adduct, 3% by weight of 9-mol propylene oxide adduct, and 6% by weight of 4-mol propylene oxide adduct)], 16-PPNPP [polyoxypropylene nonylphenol ether phosphate (3% by weight of 17-mol propylene oxide adduct, 79% by weight of 16-mol propylene oxide adduct, 10% by weight of 15-mol propylene oxide adduct, 4% by weight of 14-mol propylene oxide adduct, and 4% by weight of 13-mol propylene oxide adduct)], and 20-PPNPP [polyoxypropylene nonylphenol ether phosphate (5% by weight of 21-mol propylene oxide adduct, 78% by weight of 20-mol propylene oxide adduct, 7% by weight of 19-mol propylene oxide adduct, 6% by weight of 18-mol propylene oxide adduct, and 4% by weight of 17-mol propylene oxide adduct)].

11. A method for producing a thioepoxy optical material, comprising polymerizing the polymerizable composition according to claim 1 .

12. The method according to claim 11 , wherein the thioepoxy compound (A) is selected from the group consisting of bis(2,3-epithiopropyl)sulfide, bis(2,3-epithiopropyl)disulfide, 1,3-bis(β-epithiopropylthio)cyclohexane, 1,4-bis(β-epithiopropylthio)cyclohexane, 1,3-bis(β-epithiopropylthiomethyl)cyclohexane, 1,4-bis(β-epithiopropylthiomethyl)cyclohexane, 2,5-bis(β-epithiopropylthiomethyl)-1,4-dithiane, 2,5-bis(β-epithiopropylthioethylthiomethyl)-1,4-dithiane, 2-(2-(β-epithiopropylthioethylthio)-1,3-bis(β-epithiopropylthio)propane, and mixtures thereof.

13. The method according to claim 11 , wherein the polymerizable composition further comprises a phosphonium salt as a polymerization catalyst.

14. The method according to claim 11 , wherein the polymerizable composition further comprises bis(2-mercaptoethyl)sulfide as a polythiol compound.

15. The method according to claim 11 , wherein the polymerizable composition further comprises, as an internal release agent, at least one phosphate compound selected from the group consisting of 4-PENPP [polyoxyethylene nonylphenol ether phosphate (5% by weight of 5-mol ethylene oxide adduct, 80% by weight of 4-mol ethylene oxide adduct, 10% by weight of 3-mol ethylene oxide adduct, and 5% by weight of 1-mol ethylene oxide adduct)], 8-PENPP [polyoxyethylene nonylphenol ether phosphate (3% by weight of 9-mol ethylene oxide adduct, 80% by weight of 8-mol ethylene oxide adduct, 5% by weight of 7-mol ethylene oxide adduct, 6% by weight of 6-mol ethylene oxide adduct, and 6% by weight of 5-mol ethylene oxide adduct)], 12-PENPP [polyoxyethylene nonylphenol ether phosphate (3% by weight of 13-mol ethylene oxide adduct, 80% by weight of 12-mol ethylene oxide adduct, 8% by weight of 11-mol ethylene oxide adduct, 3% by weight of 9-mol ethylene oxide adduct, and 6% by weight of 4-mol ethylene oxide adduct)], 16-PENPP [polyoxyethylene nonylphenol ether phosphate (3% by weight of 17-mol ethylene oxide adduct, 79% by weight of 16-mol ethylene oxide adduct, 10% by weight of 15-mol ethylene oxide adduct, 4% by weight of 14-mol ethylene oxide adduct, and 4% by weight of 13-mol ethylene oxide adduct)], 20-PENPP [polyoxyethylene nonylphenol ether phosphate (5% by weight of 21-mol ethylene oxide adduct, 78% by weight of 20-mol ethylene oxide adduct, 7% by weight of 19-mol ethylene oxide adduct, 6% by weight of 18-mol ethylene oxide adduct, and 4% by weight of 17-mol ethylene oxide adduct)], 4-PPNPP [polyoxypropylene nonylphenol ether phosphate (5% by weight of 5-mol propylene oxide adduct, 80% by weight of 4-mol propylene oxide adduct, 10% by weight of 3-mol propylene oxide adduct, and 5% by weight of 1-mol propylene oxide adduct)], 8-PPNPP [polyoxypropylene nonylphenol ether phosphate (3% by weight of 9-mol propylene oxide adduct, 80% by weight of 8-mol propylene oxide adduct, 5% by weight of 7-mol propylene oxide adduct, 6% by weight of 6-mol propylene oxide adduct, and 6% by weight of 5-mol propylene oxide adduct)], 12-PPNPP [polyoxypropylene nonylphenol ether phosphate (3% by weight of 13-mol propylene oxide adduct, 80% by weight of 12-mol propylene oxide adduct, 8% by weight of 11-mol propylene oxide adduct, 3% by weight of 9-mol propylene oxide adduct, and 6% by weight of 4-mol propylene oxide adduct)], 16-PPNPP [polyoxypropylene nonylphenol ether phosphate (3% by weight of 17-mol propylene oxide adduct, 79% by weight of 16-mol propylene oxide adduct, 10% by weight of 15-mol propylene oxide adduct, 4% by weight of 14-mol propylene oxide adduct, and 4% by weight of 13-mol propylene oxide adduct)], and 20-PPNPP [polyoxypropylene nonylphenol ether phosphate (5% by weight of 21-mol propylene oxide adduct, 78% by weight of 20-mol propylene oxide adduct, 7% by weight of 19-mol propylene oxide adduct, 6% by weight of 18-mol propylene oxide adduct, and 4% by weight of 17-mol propylene oxide adduct)].

16. A thioepoxy optical material obtained by polymerization of the polymerizable composition according to claim 1 .

17. An optical lens composed of the optical material according to claim 16 .