Polymerizable composition for a plastic lens

Patent metadata

Field	Value
Publication number	US-10968309-B2
Application number	US-201816161456-A
Country	US
Kind code	B2
Filing date	Oct 16, 2018
Priority date	Oct 18, 2017
Publication date	Apr 6, 2021
Grant date	Apr 6, 2021

Abstract

Embodiments relate to a polymerizable composition for a plastic lens. The polymerizable composition for a plastic lens according to the embodiment further comprises a diketone compound for the purpose of controlling the strong activity of a halogenated tin-based catalyst. Further, the polymerizable composition is preliminarily polymerized at a low temperature of 5 to 20° C. for a certain period of time, specifically 1 to 20 hours. Since it is possible to stabilize the reaction rate of the composition and to properly control the viscosity of the composition, a more stable pot life is attained, thereby improving the workability. In addition, the generation of bubbles is prevented, thereby improving the transparency of the resin. Hence, the polymerizable composition can be advantageously used for fabricating various plastic lenses such as eyeglass lenses, camera lenses, and the like.

First claim

The invention claimed is:

1. A polymerizable composition, which comprises a polyiso(thio)cyanate compound;
a bi- or higher functional thiol compound having at least one sulfide bond or at least one ester bond;
a halogenated tin-based catalyst, and
a diketone compound in an amount of 5 to 150% by weight based on the weight of the catalyst, which satisfies the following Equation 1:
Δ ln Y=b×ΔX   [Equation 1]

wherein Δ ln Y is ln Y X −ln Y 0 ,
Y 0 is the initial viscosity (cps) of the polymerizable composition,
Y X is the viscosity (cps) of the polymerizable composition at a temperature of 10° C. after X hour(s) elapse,
ΔX is from 1 hour to 10 hours, and
b is the slope of a graph derived from the value of Δ ln Y measured with respect to X time and is 0.1 hour −1 to 0.3 hour −1 .

2. The polymerizable composition of claim 1 , which has an initial viscosity of 20 to 100 cps at 10° C.

3. The polymerizable composition of claim 1 , wherein the halogenated tin-based catalyst is used in an amount of 0.001 to 0.5 part by weight based on the total weight of the polyiso(thio)cyanate compound and the thiol compound.

4. The polymerizable composition of claim 1 , wherein the halogenated tin-based catalyst is selected from the group consisting of phenyltin trichloride, diphenyltin dichloride, triphenyltin chloride, tricyclohexyltin chloride, methyltin trichloride, dimethyltin dichloride, dibutyltin dichloride, trimethyltin chloride, butyltin trichloride, tributyltin chloride, di-tert-butyltin dichloride, butyltin chloride dihydroxide, tributyltin bromide, tributyltin iodide, trimethyltin bromide, triethyltin bromide, and a mixture thereof.

5. The polymerizable composition of claim 1 , wherein the diketone compound is selected from the group consisting of acetylacetone, perfluoroacetylacetone, benzoyl-2-furanoylmethane, 1,3-bis(3-pyridyl)-1,3-propanedione, benzoyltrifluoroacetone, benzoylacetone, di(4-bromo)benzoylmethane, d,d-dicamphorylmethane, 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-furyltrifluoroacetone, hexafluoroacetylacetone, 3-(heptafluorobutyryl)-d-camphor, 4,4,5,5,6,6,6-heptafluoro-1-(2-thienyl)-1,3-hexanedione, 4-methylbenzoyl-2-furanoylmethane, 6-methyl-2,4-heptanedione, 2-naphthoyltrifluoroacetone, 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2,4-pentanedione, 3-phenyl-2,4-pentanedione, pivaloyltrifluoroacetone, 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-thenoyltrifluoroacetone, and a mixture thereof.

6. A process for preparing a polythiourethane-based plastic lens, the process comprising:
providing a polymerizable composition for a plastic lens, which comprises a polyiso(thio)cyanate compound; a bi- or higher functional thiol compound having at least one sulfide bond or at least one ester bond, a halogenated tin-based catalyst, and a diketone compound in an amount of 5 to 150% by weight based on the weight of the catalyst;
preliminarily polymerizing the composition at a temperature of 5° C. to 20° C.; and
curing the preliminarily polymerized composition,
wherein the preliminary polymerization is carried out such that it satisfies the following Equation 1:
Δ ln Y=b×ΔX   [Equation 1]

wherein Δ ln Y is ln Y X −ln Y 0 ,
Y 0 is the initial viscosity (cps) of the polymerizable composition,
Y X is the viscosity (cps) of the polymerizable composition at a temperature of 10° C. after X hour(s) elapse,
ΔX is from 1 hour to 10 hours, and
b is the slope of a graph derived from the value of Δ ln Y measured with respect to X time and is 0.1 hour −1 to 0.3 hour −1 .

7. A plastic lens prepared by curing a polymerizable composition, which comprises a polyiso(thio)cyanate compound; a bi- or higher functional thiol compound having at least one sulfide bond or at least one ester bond; a halogenated tin-based catalyst and a diketone compound in an amount of 5 to 150% by weight based on the weight of the catalyst, and which satisfies the following Equation 1:
Δ ln Y=b×ΔX   [Equation 1]

wherein Δ ln Y is ln Y X −ln Y 0 ,
Y 0 is the initial viscosity (cps) of the polymerizable composition,
Y X is the viscosity (cps) of the polymerizable composition at a temperature of 10° C. after X hour(s) elapse,
ΔX is from 1 hour to 10 hours, and
b is the slope of a graph derived from the value of Δ ln Y measured with respect to X time and is 0.1 hour −1 to 0.3 hour −1 .

Assignees

• Skc Co Ltd

Inventors

• Hong Seung Mo
• Myung Jung Hwan
• Shin Junghwan

Classifications

• G02B1/041 Primary

  Lenses · CPC title

• C08G18/3876 Primary

  containing mercapto groups · CPC title

• C08G18/242

  organometallic compounds containing tin-carbon bonds · CPC title

• C08G18/3855 Primary

  having sulfur · CPC title

• C08G18/775 Primary

  sulfur · CPC title