Polymerizable composition for plastic lens and method of preparing plastic lens using same

Patent metadata

Field	Value
Publication number	US-10865307-B2
Application number	US-201815887177-A
Country	US
Kind code	B2
Filing date	Feb 2, 2018
Priority date	Feb 3, 2017
Publication date	Dec 15, 2020
Grant date	Dec 15, 2020

Abstract

An embodiment relates to a polymerizable composition for a plastic lens. The polymerizable composition for a plastic lens according to the embodiment comprises a nonhalogenated tin-based catalyst and a diketone compound as a low-temperature reaction rate controlling agent. Accordingly, the polymerizable composition has a more stable pot life so that the polymerization rate can be appropriately controlled, thereby improving the reactivity and the workability, and that the generation of bubbles are prevented, thereby improving the transparency of the resin.

First claim

The invention claimed is:

1. A polymerizable composition for a plastic lens, which comprises:
a bi- or higher functional isocyanate compound;
a bi- or higher functional thiol compound having at least one sulfide bond or at least one ester bond;
a catalyst comprising a nonhalogenated tin-based catalyst, said nonhalogenated tin-based catalyst being contained in an amount of 5 ppm to 1,000 ppm based on the total weight of the isocyanate compound and the thiol compound; and
a diketone-based low-temperature reaction rate controlling agent in an amount of 5 to 90% by weight based on the weight of the nonhalogenated tin-based catalyst.

2. The polymerizable composition for a plastic lens of claim 1 , which satisfies the following Equation 1 , when the changes in viscosity (Y) are measured with respect to time (X) at 10° C.:
Δln Y =b ×ΔX   Equation 1

wherein Δln Y is ln Y X −ln Y 0 , Y 0 is the initial (x =0) viscosity (cps) of the polymerizable composition at a temperature of 10° C., Y X is the viscosity (cps) of the polymerizable composition at a temperature of 10° C. after X hour(s) elapse, ΔX is from 0.01 hour to 30 hours, and b is from 0.1 hour −1 to 0.5 hour −1 .

3. The polymerizable composition for a plastic lens of claim 1 , wherein the nonhalogenated tin-based catalyst is any one of the following (i) - (vi):
(i) a dialkyltin dicarboxylate;
(ii) a dialkyltin dialkoxide;
(iii) a dialkyltin dithioalkoxide;
(iv) a dialkyltin oxide;
(v) a dialkyltin sulfide; and
(vi) a mixture comprising two or more of (i)-(v).

4. The polymerizable composition for a plastic lens of claim 1 , wherein the diketone-based low-temperature reaction rate controlling agent comprises a diketone compound, and the diketone compound is selected from the group consisting of acetylacetone, perfluoroacetylacetone, benzoyl-2-furanoyl methane, 1,3-bis(3-pyridyl)-1,3-propanedione, benzoyltrifluoroacetone, benzoylacetone, di(4-bromo)benzoylmethane, d,d-dicamphoryl methane, 4,4-dimethoxydibenzoylmethane, 2,6-dimethyl-3,5-heptanedione, dinaphthoylmethane, dipivaloylmethane, di(perfluoro-2-propoxypropionyl)methane, 1,3-di(2-thienyl)-1,3-propanedione, 3-(trifluoroacetyl)-d-camphor, 6,6,6-trifluoro-2,2-dimethyl -3,5-hexanedione, 1,1,1,2,2,6,6,7,7,7-decafluoro-3,5-heptanedione, 6,6,7,7,8,8,8-heptafluoro -2,2-dimethyl-3,5-octanedione, 2-furyl trifluoroacetone, hexafluoroacetylacetone, 3-(heptafluorobutyryl)-d-camphor, 4,4,5,5,6,6,6-heptafluoro-1-(2-thienyl)-1,3-hexanedione, 4-methylbenzoyl-2-furanoyl methane, 6-methyl-2,4-heptanedione, 2-naphthoyl trifluoroacetone, 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2,4-pentanedione, 3-phenyl-2,4-pentanedione, pivaloyl trifluoroacetone, 1-phenyl-3-(2-thienyl)-1,3-propanedione, 3-(tert-butylhydroxymethylene) -d-camphor, trifluoroacetylacetone, 1,1,1,2,2,3,3,7,7,8,8,9,9,9-tetradecafluoro-4,6-nonanedione, 2,2,6,6-tetramethyl-3,5-heptanedione, 4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione, 2,2,6,6-tetramethyl-3,5-octanedione, 2,2,6-trimethyl-3,5-heptanedione, 2,2,7-trimethyl-3,5-octanedione, 2-thenoyl trifluoroacetone, or a mixture thereof.

5. The polymerizable composition for a plastic lens of claim 1 , wherein the diketone-based low-temperature reaction rate controlling agent comprises a diketone compound, and the diketone compound is a β-diketonate compound.

6. A process for preparing a polythiourethane-based plastic lens, which comprises:
providing a polymerizable composition for a plastic lens comprising a bi- or higher functional isocyanate compound; a bi- or higher functional thiol compound having at least one sulfide bond or at least one ester bond; a catalyst comprising a nonhalogenated tin-based catalyst;
and a diketone-based low-temperature reaction rate controlling agent in an amount of 5 to 90% by weight based on the weight of the nonhalogenated tin-based catalyst, wherein the nonhalogenated tin-based catalyst is employed in an amount of 5 ppm to 1,000 ppm based on the total weight of the isocyanate compound and the thiol compound; and
thermally curing the polymerizable composition in a mold.

7. The process for preparing a polythiourethane-based plastic lens of claim 6 , wherein the polymerizable composition is heated at a rate of 1° C./ min to 10° C./ min from an initial temperature between about 0 and about 30° C.

8. The process for preparing a polythiourethane-based plastic lens of claim 7 , wherein the polymerizable composition is heated to a temperature of 100 to 150° C. and then maintained for 5 to 30 hours.

9. A polymerizable composition for a plastic lens, which comprises:
a bi- or higher functional isocyanate compound;
a bi- or higher functional thiol compound having at least one sulfide bond or at least one ester bond;
a catalyst comprising a nonhalogenated tin-based catalyst, said nonhalogenated tin-based catalyst being contained in an amount of 5 ppm to 1,000 ppm based on the total weight of the isocyanate compound and the thiol compound; and
a low-temperature reaction rate controlling agent in an amount of 5 to 90% by weight based on the weight of the nonhalogenated tin-based catalyst,
wherein the polymerizable composition satisfies the following Equation 1, when the changes in viscosity (Y) are measured with respect to time (X) at 10° C.:
Δln Y =b ×ΔX   Equation 1

wherein Δln Y is ln Y X -ln Y 0 , Y 0 is the initial (x =0) viscosity (cps) of the polymerizable composition at a temperature of 10° C., Y X is the viscosity (cps) of the polymerizable composition at a temperature of 10° C. after X hour(s) elapse, ΔX is from 0.01 hour to 30 hours, and b is from 0.1 hour −1 to 0.5 hour −1 .

10. The polymerizable composition for a plastic lens of claim 9 , wherein the low-temperature reaction rate controlling agent reduces the reaction rate of the isocyanate compound and the thiol compound at a temperature of 0° C. to 50° C.

11. The polymerizable composition for a plastic lens of claim 10 , wherein the low-temperature reaction rate controlling agent comprises a diketone-based compound.

12. The polymerizable composition for a plastic lens of claim 9 , wherein the isocyanate compound is selected from the group consisting of 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, bis (4-isocyanatocyclohexyl)methane, bis(isocyanatomethyl)-bicyclo[2.2.1]heptane, isophorone diisocyanate, m-xylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, toluene diisocyanate, or a mixture thereof.

13. The polymerizable composition for a plastic lens of claim 12 , wherein the isocyanate compound is m-xylene diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, or a mixture thereof.

14. The polymerizable composition for a plastic lens of claim 9 , wherein the bi- or higher functional thiol compound having at least one sulfide bond is selected from the group consisting of 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiooctane, bis(mercaptoethyl) sulfide, 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio) propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiaethane, 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane, or a mixture thereof.

15. The polymerizable composition for a plastic lens of claim 9 , wherein the bi- or higher functional thiol compound having at least one ester bond is selected from the group consisting of trimethylpropane tri(3-mercaptoacetate), trimethylpropane tri (3-mercaptopropionate), pentaerythritol tetraki

Assignees

• Skc Co Ltd

Inventors

• Hong Seung Mo
• Myung Jung Hwan
• Shin Junghwan

Classifications

• C08G75/0268

  using disulfides · CPC title

• C08G75/045

  from mercapto compounds and unsaturated compounds · CPC title

• G02B1/041

  Lenses · CPC title

• B29L2011/0016

  Lenses · CPC title

• C08G18/24

  of tin · CPC title