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-11795261-B2
Application number	US-202217963406-A
Country	US
Kind code	B2
Filing date	Oct 11, 2022
Priority date	Jan 27, 2020
Publication date	Oct 24, 2023
Grant date	Oct 24, 2023

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 cured product of two or more different optical monomers for an optical material, wherein:
at least one of the two or more different monomers for an optical material is an isocyanate compound containing an aromatic ring,
there are no striae of a length of 1.0 mm or more within a radius of 15 mm from a center of the cured product,
the cured product includes amine that is derived from an amine polymerization catalyst, and
the amine content, as measured by gas chromatography mass spectrometry, is from 0.001% by mass to 0.50% by mass.

2. The cured product 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.

3. A cured product of two or more different optical monomers for an optical material, wherein:
at least one of the two or more different monomers for an optical material is an isocyanate compound containing an aromatic ring,
there are no striae of a length of 1.0 mm or more within a radius of 15 mm from a center of the cured product,
the cured product includes an amine that is a polymerization catalyst,
the amine content, as measured by gas chromatography mass spectrometry, is from 0.001% by mass to 0.50% by mass,
the cured product is obtained by polymerizing the two or more different optical monomers in the presence of the amine, and
the amine satisfies the following Condition 1:

[Condition 1]
−Ea/R is from −7,100 to −2,900

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.

4. A cured product of two or more different optical monomers for an optical material, wherein:
at least one of the two or more different monomers for an optical material is an isocyanate compound containing an aromatic ring,
there are no striae of a length of 1.0 mm or more within a radius of 15 mm from a center of the cured product,
the cured product includes an amine that has a pKa value of from 4 to 8, and
the amine content, as measured by gas chromatography mass spectrometry, is from 0.001% by mass to 0.50% by mass.

5. The cured product according to claim 1 , wherein the amine contains at least one selected from the group consisting of 3,5-lutidine, 2,4,6-collidine, triethylenediamine, N,N-dimethylethanolamine, and N-ethylmorpholine.

6. The cured product according to claim 3 , wherein the amine contains at least one selected from the group consisting of 3,5-lutidine, 2,4,6-collidine, triethylenediamine, N,N-dimethylethanolamine, and N-ethylmorpholine.

7. The cured product according to claim 4 , wherein the amine contains at least one selected from the group consisting of 3,5-lutidine, 2,4,6-collidine, triethylenediamine, N,N-dimethylethanolamine, and N-ethylmorpholine.

Assignees

• Mitsui Chemicals Inc

Inventors

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

Classifications

• C08G18/10 Primary

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

• C08G18/18

  containing secondary or tertiary amines or salts thereof · CPC title

• C08G18/24

  of tin · CPC title

• C08G18/76

  aromatic · CPC title

• G02B1/04

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