Polymerizable composition for optical material, optical material obtained from the composition, and plastic lens

Patent metadata

Field	Value
Publication number	US-10921489-B2
Application number	US-201615757897-A
Country	US
Kind code	B2
Filing date	Sep 16, 2016
Priority date	Sep 16, 2015
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

A polymerizable composition for an optical material according to the present invention, including: a monomer mixture (A) including a polymerizable monomer having a (meth) acrylic group, a photochromic compound (B) which is at least one selected from compounds represented by Formulae (1) and (2); and an ultraviolet absorbing agent (C) which is at least one selected from compounds represented by Formulae (a) to (c).

First claim

The invention claimed is:

1. A polymerizable composition for an optical material, comprising:
a monomer mixture (A) including a polymerizable monomer having a (meth)acrylic group, where the monomer mixture (A) is a mixture of four monomers represented by Formulae (i), (ii), (iii), and (iv), respectively;
a photochromic compound (B) which is at least one selected from compounds represented by Formulae (1) and (2); and
an ultraviolet absorbing agent (C) which is at least one selected from compounds represented by Formulae (b) to (c),

in the formula (i), R represents a hydrogen atom or a methyl group, and a plurality of R's existing together may be identical to or different from each other, and m and n represent an integer of 0 to 20 and may be identical to or different from each other;

in the formula (ii), R represents a hydrogen atom or a methyl group, and a plurality of R's existing together may be identical to or different from each other, and p represents an integer of 0 to 20;

in the formula (iii), R represents a hydrogen atom or a methyl group, and q represents an integer of 0 to 20;
PC-L-Chain  (1)

PC-L-Chain-L′-PC′  (2)

wherein in Formula (1) or (2), PC and PC′ represent monovalent groups derived from compounds of Formulae (3) to (6), and PC and PC′ may be identical to or different from each other,

in Formulae (3) to (6), R 1 to R 18 represent hydrogen, a halogen atom, a carboxyl group, an acetyl group, a formyl group, an optionally substituted C1 to C20 aliphatic group, an optionally substituted C3 to C20 alicyclic group, and an optionally substituted C6 to C20 aromatic organic group, and may be identical to or different from each other, the aliphatic group, the alicyclic group, or the aromatic organic group may contain an oxygen atom and a nitrogen atom, and any one group included in the compounds represented by Formulae (3) to (6) is bonded to L or L′ which is a divalent organic group;
in Formula (1) or (2), L and L′ each represent a divalent organic group including one or more selected from an oxyethylene chain, an oxypropylene chain, a (thio)ester group, and a (thio)amide group, and in Formula (1) or (2), Chain represents a monovalent or divalent organic group including one or more selected from a polysiloxane chain and a polyoxyalkylene chain;

in Formula (b), Z 1 and Z 2 may be identical to or different from each other, and represent a C1 to C6 alkyl group and a C1 to C6 alkoxy group;

in Formula (c), Z 3 represents an optionally substituted C6 to C20 aromatic organic group and an optionally substituted C5 to C20 alicyclic group, and Z 4 and Z 5 may be identical to or different from each other and represent a C1 to C6 alkyl group and a C1 to C6 alkoxy group.

2. The polymerizable composition for an optical material according to claim 1 ,
wherein the ultraviolet absorbing agent (C) is at least one selected from 2-ethyl-2′-ethoxyoxanilide and dimethyl (p-methoxybenzylidene) malonate.

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

4. An optical material formed of the molded product according to claim 3 .

5. A plastic lens formed of the molded product according to claim 3 .

6. A plastic polarized lens comprising:
a polarizing film; and
a substrate layer formed of the molded product according to claim 4 formed on at least one surface of the polarizing film.

7. A method of manufacturing a plastic lens, comprising:
a step of collectively mixing a monomer mixture (A) including a polymerizable monomer having a (meth)acrylic group, where the monomer mixture (A) is a mixture of four monomers represented by Formulae (i), (ii), (iii), and (iv), respectively, a photochromic compound (B) which is at least one selected from compounds represented by Formulae (1) and (2), and an ultraviolet absorbing agent (C) which is at least one selected from the compounds represented by Formulae (b) to (c) to prepare a polymerizable composition for an optical material; and
a step of performing cast polymerization on the polymerizable composition for an optical material to form a lens substrate,

in the formula (i), R represents a hydrogen atom or a methyl group, and a plurality of R's existing together may be identical to or different from each other, and m and n represent an integer of 0 to 20 and may be identical to or different from each other;

in the formula (ii), R represents a hydrogen atom or a methyl group, and a plurality of R's existing together may be identical to or different from each other, and p represents an integer of 0 to 20;

in the formula (iii), R represents a hydrogen atom or a methyl group, and q represents an integer of 0 to 20;
PC-L-Chain  (1)

PC-L-Chain-L′-PC′  (2)

wherein in Formula (1) or (2), PC and PC′ represent monovalent groups derived from compounds of Formulae (3) to (6), and PC and PC′ may be identical to or different from each other,

in Formulae (3) to (6), R 1 to R 18 represent hydrogen, a halogen atom, a carboxyl group, an acetyl group, a formyl group, an optionally substituted C1 to C20 aliphatic group, an optionally substituted C3 to C20 alicyclic group, and an optionally substituted C6 to C20 aromatic organic group, and may be identical to or different from each other, the aliphatic group, the alicyclic group, or the aromatic organic group may contain an oxygen atom and a nitrogen atom, and any one group included in the compounds represented by Formulae (3) to (6) is bonded to L or L′ which is a divalent organic group;
in Formula (1) or (2), L and L′ each represent a divalent organic group including one or more selected from an oxyethylene chain, an oxypropylene chain, a (thio)ester group, and a (thio)amide group, and in Formula (1) or (2), Chain represents a monovalent or divalent organic group including one or more selected from a polysiloxane chain and a polyoxyalkylene chain;

in Formula (b), Z 1 and Z 2 may be identical to or different from each other, and represent a C1 to C6 alkyl group and a C1 to C6 alkoxy group;

in Formula (c), Z 3 represents an optionally substituted C6 to C20 aromatic organic group and an optionally substituted C5 to C20 alicyclic group, and Z 4 and Z 5 may be identical to or different from each other and represent a C1 to C6 alkyl group and a C1 to C6 alkoxy group.

8. A method of manufacturing a plastic polar

Assignees

• Mitsui Chemicals Inc

Inventors

• Kawaguchi Masaru
• Kawato Nobuo

Classifications

• C08F2/50

  with sensitising agents · CPC title

• G02C7/12

  Polarisers · CPC title

• G02C7/102

  Photochromic filters · CPC title

• G02B1/041 Primary

  Lenses · CPC title

• G02B1/04

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