Photochromic curable composition, cured product thereof and laminate including the cured product

Patent metadata

Field	Value
Publication number	US-9890324-B2
Application number	US-201414770181-A
Country	US
Kind code	B2
Filing date	Feb 26, 2014
Priority date	Mar 4, 2013
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

A curable composition which comprises a carbonate-based polymerizable monomer represented by the following formula, other polymerizable monomers and a photochromic compound, can be used even under high-temperature and high-humidity conditions without any problems and provides a cured product having excellent photochromic properties.

wherein A and A′ are each a linear or branched alkylene group having 2 to 15 carbon atoms, “a” is an average value of 1 to 20, when there are a plurality of A's, A's may be the same or different, R 1 is a hydrogen atom or methyl group, and R 2 is a (meth)acryloyloxy group or hydroxyl group.

First claim

The invention claimed is:

1. A photochromic curable composition comprising (A) as a polymerizable (meth)acrylate component:
[A1] a polymerizable carbonate monomer represented by the following formula (1):

wherein A and A′ are each a linear or branched alkylene group having 2 to 15 carbon atoms, “a” is an average value of 1 to 20, when there are a plurality of A's, A's may be the same or different, R 1 is a hydrogen atom or methyl group, and R 2 is a (meth)acryloyloxy group or hydroxyl group;
[A2] a polyfunctional polymerizable monomer represented by the following formula (2):

wherein R 3 is a hydrogen atom or methyl group, R 4 is a hydrogen atom or alkyl group having 1 to 2 carbon atoms, R 5 is a trivalent to hexavalent organic group having 1 to 10 carbon atoms, “b” is an average value of 0 to 3, “c” is an integer of 3 to 6; and
[A3] another polymerizable (meth)acrylate monomer different from the above components [A1] and [A2], and
(B) a photochromic compound (B),
wherein the polymerizable (meth)acrylate component (A) contains 5 to 50 mass % of the component [A1], more than 30 mass % to 70 mass % or less of the component [A2] and 1 mass % or more to less than 65 mass % of the component [A3] (the total content of the components [A1], [A2] and [A3] is 100 mass %), and the photochromic compound (B) is contained in an amount of 0.0001 to 10 parts by mass based on 100 parts by mass of the polymerizable (meth)acrylate component (A).

2. The photochromic curable composition according to claim 1 , wherein the component [A3] contains [A3a] a bifunctional polymerizable monomer represented by the following formula (3):

wherein R 6 and R 7 are each a hydrogen atom or methyl group, “d” and “e” are each an integer of 0 or more, with the proviso that when both R 6 and R 7 are methyl groups, (d+e) is an average value of 2 or more to less than 7, when R 6 is a methyl group and R 7 is a hydrogen atom, (d+e) is an average value of 2 or more to less than 5, and when both R 6 and R 7 are hydrogen atoms, (d+e) is an average value of 2 or more to less than 3.

3. The photochromic curable composition according to claim 2 , wherein the component [A3] contains the component [A3a] in an amount of 20 to 100 mass % based on 100 mass % of the component [A3].

4. The photochromic curable composition according to claim 1 , wherein the component [A3] contains [A3b] a bifunctional polymerizable monomer represented by the following formula (4):

wherein R 8 and R 9 are each a hydrogen atom or methyl group, R 10 and R 11 are each a hydrogen atom or methyl group, B is any one of groups represented by the following formulas:

and “f” and “g” are each an integer of 1 or more, with the proviso that when both R 8 and R 9 are methyl groups, (f+g) is an average value of 2 or more to less than 7, when R 8 is a methyl group and R 9 is a hydrogen atom, (f+g) is an average value of 2 or more to less than 5, and when both R 8 and R 9 are hydrogen atoms, (f+g) is an average value of 2 or more to less than 3.

5. The photochromic curable composition according to claim 4 , wherein the component [A3] contains the component [A3b] in an amount of 20 to 100 mass % based on 100 mass % of the component [A3].

6. The photochromic curable composition according to claim 1 , wherein the component [A3] contains [A3c] a bifunctional polymerizable monomer represented by the following formula (14):

wherein R 8 and R 9 are each a hydrogen atom or methyl group, R 10 and R 11 are each a hydrogen atom or methyl group, B is any one of groups represented by the following formulas:

and “k” and “m” are each an integer of 1 or more, with the proviso that when both R 8 and R 9 are methyl groups, (k+m) is an average value of 7 to 30, when R 8 is a methyl group and R 9 is a hydrogen atom, (k+m) is an average value of 7 to 25, and when both R 8 and R 9 are hydrogen atoms, (k+m) is an average value of 7 to 20.

7. The photochromic curable composition according to claim 6 , wherein the component [A3] contains the component [A3c] in an amount of 30 to 100 mass % based on 100 mass % of the component [A3].

8. The photochromic curable composition according to claim 1 which further comprises (C) a polymerizable monomer having a polymerizable group different from a (meth)acrylate group in an amount of 0.1 to 20 parts by mass based on 100 parts by mass of the component (A).

9. The photochromic curable composition according to claim 1 , wherein the component (B) contains a photochromic compound having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton.

10. A photochromic cured product obtained by curing the photochromic curable composition of claim 1 .

11. A photochromic laminate having the photochromic cured product of claim 10 on a plastic lens substrate.

Assignees

• Tokuyama Corp

Inventors

• Shimizu Yasutomo
• Takenaka Junji
• Momoda Junji
• Mori Katsuhiro

Classifications

• C08F2/50

  with sensitising agents · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K9/02 Primary

  Organic tenebrescent materials · CPC title

• C08F290/061

  Polyesters; Polycarbonates · CPC title

• G02B1/10

  Optical coatings produced by application to, or surface treatment of, optical elements (G02B1/08 takes precedence) · CPC title