# US 10,308,756 B2 · Polymerizable composition for optical material and use thereof

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- Number: US 10,308,756 B2
- Document ID: US10308756B2
- Status: Granted
- Kind: B2
- Application number: 15/318,015
- Filed: 2015-07-07
- Published: 2017-05-11
- Granted: 2019-06-04
- Earliest claimed: 2014-07-08
- Assignees: Mitsui Chemicals, Inc.
- Applicants: Mitsui Chemicals, Inc.
- Inventors: Nobuo Kawato
- Web page: https://patentgrep.com/patent/US10308756B2

## CPC

- C08G 18/3876: {containing mercapto groups}
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/3228: {acyclic}
- C08G 18/3234: {cycloaliphatic}
- C08G 18/722: {Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates}
- C08G 18/724: {Combination of aromatic polyisocyanates with (cyclo)aliphatic polyisocyanates}
- C08G 18/73: acyclic
- C08G 18/757: {containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group}
- C08G 18/758: {containing two or more cycloaliphatic rings}
- G02B 1/04: made of organic materials, e.g. plastics (G02B1/08 takes precedence)
- G02B 1/041: {Lenses}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS

## Abstract

Provided is a polymerizable composition for an optical material including (A) an amine having two or more secondary amino groups, (B) an isocyanate having two or more isocyanato groups, and (C) a thiol having three or more mercapto groups, in which the ratio (a/b) of the molar number a of amino groups in the amine (A) with respect to the molar number b of isocyanato groups in the isocyanate (B) is in the range of 0.10 to 0.60.

## Claims

### Claim 1

A polymerizable composition for an optical material, comprising:
a prepolymer obtained by reacting (A) an amine having two or more secondary amino groups and (B) an isocyanate having two or more isocyanato groups; and (C) a thiol having three or more mercapto groups,
wherein the ratio (a/b) of the molar number a of amino groups in the amine (A) with respect to the molar number b of isocyanato groups in the isocyanate (B) is in the range of 0.10 to 0.60.

### Claim 2 (depends on 1)

The polymerizable composition for an optical material according to claim 1, wherein the amine (A) is comprised of one or more compounds selected from a secondary aliphatic amine and a secondary alicyclic amine.

### Claim 3 (depends on 1)

The polymerizable composition for an optical material according to claim 1, wherein the amine (A) has two or more secondary amino groups represented by the formula: —NHR, and two or more R's may be the same or different from each other and are selected from an isopropyl group, a 1,2,2-trimethylpropyl group, a tert-butyl group, a sec-butyl group, and a 1,3-dimethylbutyl group.

### Claim 4 (depends on 1)

The polymerizable composition for an optical material according to claim 1, wherein the molecular weight of the amine (A) is 600 or less.

### Claim 5 (depends on 1)

The polymerizable composition for an optical material according to claim 1, wherein the amine (A) is comprised of one or more compounds selected from N,N′-di-tert-butyl-ethylenediamine, N,N′-di(1,2,2-trimethylpropyl)-1,6-hexamethylenediamine, N,N′-di-isopropyl-m-xylylenediamine, N,N′-di-sec-butyl-m-xylylenediamine, N,N′-(cyclohexyl-1,3-diylbis(methylene))bis(isopropyl-2-amine), N,N′-(cyclohexyl-1,3-diylbis(methylene))bis(sec-propyl-2-amine), N,N′-(cyclohexyl-1,4-diylbis(methylene))bis(isopropyl-2-amine), N,N′-(cyclohexyl-1,4-diylbis(methylene))bis(sec-propyl-2-amine), N,N′-di-isopropyl-isophorone diamine, N,N′-di-sec-butyl-4,4′-methylene-bis(cyclohexylamine), N,N′-di-sec-butyl-4,4′-methylene-bis(2-methylcyclohexylamine), N,N′-di-isopropyl-2,5-diaminomethyl-bicyclo[2.2.1]heptane, N,N′-di-sec-butyl-2,5-diaminomethyl-bicyclo[2.2.1]heptane, N,N′-di-isopropyl-2,6-diaminomethyl-bicyclo[2.2.1]heptane, and N,N′-di-sec-butyl-2,6-diaminomethyl-bicyclo[2.2.1]heptane.

### Claim 6 (depends on 1)

The polymerizable composition for an optical material according to claim 1, wherein the isocyanate (B) is comprised of one or more compounds selected from m-xylylene diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane, 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate, 4,4′-methylene-bis(cyclohexyl isocyanate), 1,5-pentane diisocyanate, 1,6-hexamethylene diisocyanate, 2,4-tolylene diisocyanate, and 2,6-tolylene diisocyanate.

### Claim 7 (depends on 1)

The polymerizable composition for an optical material according to claim 1, wherein the thiol (C) is comprised of one or more compounds selected from 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,1 1-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,1 1-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, trimethyloipropane tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), and pentaerythritol tetrakis(3-mercaptopropionate).

### Claim 8 (depends on 1)

A molded product obtained by polymerizing the polymerizable composition for an optical material according to claim 1.

### Claim 9 (depends on 8)

An optical material comprised of the molded product according to claim 8.

### Claim 10 (depends on 8)

A plastic lens made of the molded product according to claim 8.

### Claim 11

A method for producing a polymerizable composition for an optical material, comprising:
a step (i) of reacting an amine (A) and an isocyanate (B) to obtain a prepolymer; and
a step (ii) of adding and mixing a thiol (C) into the prepolymer,
wherein the ratio (a/b) of the molar number a of amino groups in the amine (A) with respect to the molar number b of isocyanato groups in the isocyanate (B) is in the range of 0.10 to 0.60.

### Claim 12 (depends on 11)

The method for producing a polymerizable composition for an optical material according to claim 11, wherein the amine (A) is one or more compounds selected from a secondary aliphatic amine and a secondary alicyclic amine.

### Claim 13 (depends on 11)

The method for producing a polymerizable composition for an optical material according to claim 11, wherein the amine (A) is comprised of a compound having two or more secondary amino groups represented by the formula: —NHR, and two or more R's may be the same or different from each other and are selected from an isopropyl group, a 1,2,2-trimethylpropyl group, a tert-butyl group, a sec-butyl group, and a 1,3-dimethylbutyl group.

### Claim 14 (depends on 11)

The method for producing a polymerizable composition for an optical material according to claim 11, wherein the molecular weight of the amine (A) is 600 or less.

### Claim 15 (depends on 11)

The method for producing a polymerizable composition for an optical material according to claim 11, wherein the amine (A) is comprised of one or more compounds selected from N,N′-di-tert-butyl-ethylenediamine, N,N′-di(1,2,2-trimethylpropyl)-1,6-hexamethylenediamine, N,N′-di-isopropyl-m-xylylenediamine, N,N′-di-sec-butyl-m-xylylenediamine, N,N′-(cyclohexyl-1,3-diylbis(methylene))bis(isopropyl-2-amine), N,N′-(cyclohexyl-1,3-diylbis(methylene))bis(sec-propyl-2-amine), N,N′-(cyclohexyl-1,4-diylbis(methylene))bis(isopropyl-2-amine), N,N′-(cyclohexyl-1,4-diylbis(methylene))bis(sec-propyl-2-amine), N,N′-di-isopropyl-isophorone diamine, N,N′-di-sec-butyl-4,4′-methylene-bis(cyclohexylamine), N,N′-di-sec-butyl-4,4′-methylene-bis(2-methylcyclohexylamine), N,N′-di-isopropyl-2,5-diaminomethyl-bicyclo[2.2.1]heptane, N,N′-di-sec-butyl-2,5-diaminomethyl-bicyclo[2.2.1]heptane, N,N′-di-isopropyl-2,6-diaminomethyl-bicyclo[2.2.1]heptane, and N,N′-di-sec-butyl-2,6-diaminomethyl-bicyclo[2.2.1]heptane.