Curable composition, cured article obtained therefrom, and photochromic optical material and process for producing the same

Patent metadata

Field	Value
Publication number	US-9977161-B2
Application number	US-48489602-A
Country	US
Kind code	B2
Filing date	Mar 26, 2002
Priority date	Jul 27, 2001
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

A curable composition which provides a coating layer having high adhesion to a substrate and a hard coat layer and extremely excellent photochromic properties such as high color development intensity, high fading speed and excellent durability. This composition comprises (1) 100 parts by weight of radically polymerizable monomers including a silyl monomer such as γ-methacryloyloxypropyl trimethoxysilane and/or an isocyanate monomer such as 2-isocyanatoethoxy methacrylate, (2) 0.01 to 20 parts by weight of an amine compound and (3) 0.01 to 20 parts by weight of a photochromic compound. A photochromic optical material having excellent adhesion between a photochromic coating layer and a resin substrate and obtained by using this composition as a coating material and a process for producing the photochromic optical material.

First claim

The invention claimed is:

1. A curable composition comprising:
(1) 100 parts by weight of radically polymerizable monomers;
(2) 1 to 10 parts by weight of an amine compound represented by the following formula (17)

wherein R 06 is methyl, R 07 is a hydroxyl group, R 08 is a hydrogen atom or a hydroxyl group, A′ is an alkylene group having 2 to 6 carbon atoms, and A″ is a methylene group when R 08 is a hydrogen atom, or A″ is an alkylene group having 2 to 6 carbon atoms when R 08 is a hydroxyl group; and
(3) 0.01 to 20 parts by weight of a photochromic compound, said radically polymerizable monomers comprising (a) a radically polymerizable monomer having a group which forms a silanol group by hydrolysis, represented by the following formula:

wherein R 5 is a hydrogen atom or methyl group, R 6 is an alkylene group having 1 to 3 carbon atoms, R 7 is an alkoxyl group having 1 to 2 carbon atoms and a is an integer of 3, (b) a radically polymerizable monomer which is selected from the group consisting of glycidyl acrylate and glycidyl methacrylate, (c) a monomer having a homopolymer L-scale Rockwell hardness of 40 or less and represented by the following formula (13):

where R 26 is a hydrogen atom or methyl group, R 27 and R 28 are each independently a hydrogen atom or methyl group, I is a divalent organic residual group represented by the following formula:

i′ and j′ are each an integer that ensures that the average value of i′+j′ is 9 to 30, and (d) a monomer having a homopolymer L-scale Rockwell hardness of 60 or more and represented by the following formula (7):

wherein R 13 is a hydrogen atom or methyl group, R 14 is a hydrogen atom, R 15 is a tervalent to hexavalent organic residual group having 1 to 16 carbon atoms, f is an integer of 0 to 3, f is an integer of 0 to 1, and g is an integer of 3 to 6,
said radically polymerizable monomer (a) being in an amount of 1 to 10 wt % based on the total amount of all the radically polymerizable monomers, said radically polymerizable monomer (b) being in an amount of 0.1 to 20 wt % based on the total of all the radically polymerizable monomers excluding the radically polymerizable monomer (a), said monomer (c) being in an amount of 5 to 70 wt % based on all the radically polymerizable monomers excluding the radically polymerizable monomer (a), and said radically polymerizable monomer (d) being in an amount of 10 to 94.9 wt % based on all the radically polymerizable monomers excluding the radically polymerizable monomer (a), wherein
the curable composition has a viscosity at 25° C. of 20 to 500 cp.

2. The curable composition of claim 1 , wherein the radically polymerizable monomer (d) is in an amount of 10 to 43 wt % based on all the radically polymerizable monomers excluding the radically polymerizable monomer (a).

3. The curable composition of claim 1 which further comprises a photopolymerization initiator.

4. A photochromic cured product obtained by curing the curable composition of claim 1 or 3 .

5. A photochromic optical material comprising a substrate having at least one surface coated with a cured product of the curable composition of claim 1 or 3 .

6. The photochromic optical material according to claim 5 , wherein the substrate comprises at least one optical material selected from the group consisting of an allylic resin, a methacrylic resin, a polycarbonate resin, a thiourethane resin, a urethane resin and a thioepoxy resin.

7. The photochromic optical material according to claim 5 , wherein the substrate comprises at least one optical material selected from the group consisting of an allylic resin, a methacrylic resin, a thiourethane resin, and a thioepoxy resin.

8. The photochromic optical material according to claim 5 , wherein
at least one said surface of the substrate has been subjected to a plasma treatment,
the cured product of the curable composition is disposed on the surface of the substrate which has been subjected to the plasma treatment, and
the substrate comprises at least one optical material selected from the group consisting of an allylic resin, a methacrylic resin, a thiourethane resin, and a thioepoxy resin.

9. The photochromic optical material according to claim 5 , wherein
at least one said surface of the substrate has been subjected to a plasma treatment,
the cured product of the curable composition is disposed on the surface of the substrate which has been subjected to the plasma treatment, and
the substrate comprises at least one optical material selected from the group consisting of an allylic resin, a thiourethane resin, and a thioepoxy resin.

10. A process for producing a photochromic optical material comprising a substrate having at least one coated surface, the process comprising curing a film of the curable composition of claim 1 or 3 formed on at least one surface of the substrate by light or both light and heat.

11. The curable composition of claim 1 , further comprising a radically polymerizable monomer having an isocyanate group.

12. The curable composition of claim 1 , wherein the radically polymerizable monomer (a) is at least one silyl monomer selected from the group consisting of γ-methacryloyloxypropyl trimethoxysilane, γ-methacryloyloxypropyl triethoxysilane, (3-acryloxypropyl)trimethoxysilane, methacryloxymethyl triethoxysilane, and methacryloxymethyl trimethoxysilane.

13. The curable composition of claim 1 , wherein the radically polymerizable monomer (a) is γ-methacryloyloxypropyl trimethoxysilane.

14. A process for coating, which comprises a step of coating a substrate with a curable composition, wherein
the curable composition comprises:
(1) 100 parts by weight of radically polymerizable monomers;
(2) 1 to 10 parts by weight of an amine compound represented by the following formula (17)

wherein R 06 is methyl, R 07 is a hydroxyl group, R 08 is a hydrogen atom or a hydroxyl group, A′ is an alkylene group having 2 to 6 carbon atoms, and A″ is a methylene group when R 08 is a hydrogen atom, or A″ is an alkylene group having 2 to 6 carbon atoms when R 08 is a hydroxyl group; and
(3) 0.01 to 20 parts by weight of a photochromic compound, said radically polymerizable monomers comprising (a) a radically polymerizable monomer having a group which forms a silanol group by hydrolysis, represented by the following formula:

wherein R 5 is a hydrogen atom or methyl group, R 6 is an alkylene group having 1 to 3 carbon atoms, R 7 is an alkoxyl group having 1 to 2 carbon atoms and a is an integer of 3, (b) a radically polymerizable monomer which is selected from the group consisting of glycidyl acrylate and glycidyl methacrylate, (c) a monomer having a homopolymer L-scale Rockwell hardness of 40 or less and represented by the following formula (13):

Assignees

• Momoda Junji
• Mori Katsuhiro
• Tokuyama Corp

Inventors

• Momoda Junji
• Mori Katsuhiro

Classifications

• G02B5/23 Primary

  Photochromic filters · CPC title

• C08G18/8116

  esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C08F230/08

  containing silicon · CPC title

• C08L43/04 Primary

  Homopolymers or copolymers of monomers containing silicon · CPC title