Polymerizable composition for optical material, polymerizable prepolymer composition for optical material, cured product, and method of producing optical material

Patent metadata

Field	Value
Publication number	US-11499000-B2
Application number	US-202117431250-A
Country	US
Kind code	B2
Filing date	Jan 27, 2021
Priority date	Jan 27, 2020
Publication date	Nov 15, 2022
Grant date	Nov 15, 2022

Abstract

A polymerizable composition for an optical material containing two or more different monomers for an optical material, and a polymerization catalyst, in which at least one of the two or more different monomers for an optical material is an isocyanate compound containing an aromatic ring, a content of the polymerization catalyst with respect to a total of 100 parts by mass of the two or more different monomers for an optical material is from 0.010 parts by mass to 0.50 parts by mass, and the viscosity measured by a B-type viscometer at 25° C. and 60 rpm is from 10 mPa·s to 1,000 mPa·s.

First claim

The invention claimed is:

1. A polymerizable composition for an optical material, comprising two or more different monomers for an optical material, and a polymerization catalyst, wherein:
at least one of the two or more different monomers for an optical material is an isocyanate compound containing an aromatic ring,
a content of the polymerization catalyst with respect to a total of 100 parts by mass of the two or more different monomers for an optical material is from 0.010 parts by mass to 0.50 parts by mass,
a viscosity measured by a B-type viscometer at 25° C. and 60 rpm is from 10 mPa·s to 1,000 mPa·s, and
the two or more different monomers for an optical material contain a polythiol compound containing two or more mercapto groups.

2. The polymerizable composition for an optical material according to claim 1 , wherein a thixotropy ratio is 1.3 or less.

3. The polymerizable composition for an optical material according to claim 1 , comprising:
two or more different monomers for an optical material;
a polymerization catalyst; and
a prepolymer that is a polymer of the two or more different monomers for an optical material and that contains a polymerizable functional group.

4. The polymerizable composition for an optical material according to claim 1 , wherein the two or more different monomers for an optical material contain at least one active hydrogen compound selected from the group consisting of a polythiol compound containing two or more mercapto groups, a hydroxythiol compound containing one or more mercapto groups and one or more hydroxyl groups, a polyol compound containing two or more hydroxyl groups, and an amine compound.

5. The polymerizable composition for an optical material according to claim 1 , wherein the polymerization catalyst satisfies the following Condition 1:
−Ea/R is from −7,100 to −2,900  [Condition 1]

wherein Ea is an activation energy calculated by an Arrhenius plot from reaction rate constants of the two or more different monomers for an optical material at two or more different temperatures, and R is the gas constant 8.314 J/mol/K.

6. The polymerizable composition for an optical material according to claim 1 , wherein the polymerization catalyst contains at least one selected from the group consisting of a basic catalyst having a pKa value of from 4 to 8 and an organometallic catalyst.

7. A polymerizable prepolymer composition for an optical material, comprising a polymerization catalyst and a prepolymer that is a polymer of two or more different monomers for an optical material and that contains a polymerizable functional group, wherein:
at least one of the two or more different monomers for an optical material is an isocyanate compound containing an aromatic ring,
a viscosity measured with a B-type viscometer at 25° C. and 60 rpm is from 10 mPa·s to 2,000 mPa·s,
the two or more different monomers for an optical material contain a polythiol compound containing two or more mercapto groups, and
a content of the polymerization catalyst with respect to a total of 100 parts by mass of the prepolymer is from 0.015 parts by mass to 0.50 parts by mass.

8. The polymerizable prepolymer composition for an optical material according to claim 7 , wherein the two or more different monomers for an optical material comprise at least one active hydrogen compound selected from the group consisting of a polythiol compound containing two or more mercapto groups, a hydroxythiol compound containing one or more mercapto groups and one or more hydroxyl groups, a polyol compound containing two or more hydroxyl groups, and an amine compound.

9. The polymerizable prepolymer composition for an optical material according to claim 7 , wherein the polymerization catalyst satisfies the following Condition 1:
−Ea/R is from −7,100 to −2,900  [Condition 1]

wherein Ea is an activation energy calculated by an Arrhenius plot from reaction rate constants of the two or more different monomers for an optical material at two or more different temperatures, and R is the gas constant 8.314 J/mol/K.

10. The polymerizable prepolymer composition for an optical material according to claim 7 , wherein the polymerization catalyst contains at least one selected from the group consisting of a basic catalyst having a pKa value of from 4 to 8 and an organometallic catalyst.

11. A cured product of the polymerizable composition for an optical material according to claim 1 .

12. A method of producing an optical material, the method comprising:
a preparation process of preparing a polymerizable composition for an optical material containing two or more different monomers for an optical material, and a polymerization catalyst, wherein:
at least one of the two or more different monomers for an optical material is an isocyanate compound containing an aromatic ring, and the two or more different monomers for an optical material contain a polythiol compound containing two or more mercapto groups, and
a content of the polymerization catalyst with respect to a total of 100 parts by mass of the two or more different monomers for an optical material is from 0.010 parts by mass to 0.50 parts by mass;
a cast molding process in which a viscosity of the polymerizable composition for an optical material, measured with a B-type viscometer at 25° C. and 60 rpm, is adjusted to from 10 mPa·s to 1,000 mPa·s and the composition is cast molded into a mold; and
a curing process of curing the polymerizable composition for an optical material by polymerizing the two or more different monomers for an optical material in the polymerizable composition for an optical material in the mold.

13. A method of producing an optical material, the method comprising:
a preparation process of preparing a total of 100 parts by mass of two or more different monomers for an optical material and from 0.010 parts by mass to 0.50 parts by mass of a polymerization catalyst; and
a prepolymerization process of obtaining, by obtaining a prepolymer by mixing a portion of the two or more different monomers for an optical material and at least a portion of the polymerization catalyst and polymerizing at least a portion in the portion of the two or more different monomers for an optical material, a mixture containing the prepolymer,
wherein at least one of the two or more different monomers for an optical material is an isocyanate compound containing an aromatic ring, and the two or more different monomers for an optical material contain a polythiol compound containing two or more mercapto groups.

14. The method of producing an optical material according to claim 13 , the method comprising:
a process of producing a polymerizable composition for an optical material in which, by further adding at least a balance of the two or more different monomers for an optical material to the mixture containing the prepolymer, a polymerizable composition for an optical material containing the two or more different monomers for an optical material, the prepolymer, and the polymerization catalyst is obtained; and
a curing process in which, by curing the two or more different monomers for an optical material in the polymerizable composition for an optical material, an optical material that is a cured product of the polymerizable composition for an optical material is obtained.

15. The method of producing an optical material according to claim 12 , wherein the two or more different monomers for an optical material comprise at least one active hydrogen compound selected from the group consisting of a polythiol compound containing two or more mercapto groups, a hydroxythiol compound

Assignees

• Mitsui Chemicals Inc

Inventors

• Suesugi Kouji
• Ito Shinsuke
• Nakano Shotaro
• Matsui Yusuke

Classifications

• G02B1/041

  Lenses · CPC title

• C08G18/16

  Catalysts (catalysts in general B01J) · CPC title

• C08G18/3876 Primary

  containing mercapto groups · CPC title

• C08G18/10 Primary

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title