Curable resin composition, cured article thereof, and optical material
View Patent ↗Provided is a curable resin composition which has excellent optical properties, heat resistance, transparency, low water absorbability, and mold release property in molding, and reduces the occurrence of a burr from a mold. Also provided are a cured product thereof and an optical material. The curable resin composition includes: a component (A): a soluble polyfunctional (meth)acrylic acid ester copolymer which is obtained by copolymerizing components including a monofunctional (meth)acrylic acid ester (a) having an alicyclic structure, a bifunctional (meth)acrylic acid ester (b), and 2,4-diphenyl-4-methyl-1-pentene (c), has a reactive (meth)acrylate group derived from (b) in a side chain and a structural unit derived from (c) at an end, has a Mw of 2,000 to 20,000, and is soluble in an organic solvent; a component (B): a polyfunctional (meth)acrylate; and a component (C): an initiator, in which the blending amounts (weight ratio) of the respective components are as follows: (B)/(A)=5 to 250/100, and (C)/[(B)+(A)]=0.1 to 10/100.
1. A curable resin composition, comprising:
a component (A): a soluble polyfunctional (meth)acrylic acid ester copolymer which is obtained by copolymerizing components including a monofunctional (meth)acrylic acid ester (a) having an alicyclic structure, a bifunctional (meth)acrylic acid ester (b), and 2,4-diphenyl-4-methyl-1-pentene (c), has a structural unit (b1) having a reactive (meth)acrylate group derived from the bifunctional (meth)acrylic acid ester (b) in a side chain and a structural unit derived from 2,4-diphenyl-4-methyl-1-pentene (c) at an end, has a weight-average molecular weight of 3000 to 10,000, and is soluble in toluene, xylene, tetrahydrofuran, dichloroethane, or chloroform,
wherein the amount of the structural unit derived from 2.4-diphenyl-4-methyl-1-pentene (c) introduced into the copolymer is, as a mole fraction M c represented by the following equation (1), 0.03 to 0.30, and the amount of the reactive (meth)acrylate group is, as a mole fraction M b1 represented by the following equation (2), 0.1 to 0.3,
M c =( c )/[( a )+( b )+( c )] (1)
M b1 =( b 1)/[( a )+( b )] (2)
wherein, (a), (b), and (c) represent mole numbers of the structural unit derived from the monofunctional (meth)acrylic acid ester (a) having an alicyclic structure, the structural unit derived from the bifunctional (meth)acrylic acid ester (b), and the structural unit derived from 2,4-diphenyl-4-methyl-1-pentene (c), respectively, and (b1) represents a mole number of the structural unit (b1) containing a reactive (meth)acrylate group;
a component (B): a polyfunctional (meth)acrylate; and
a component (C): an initiator,
wherein a blending amount of the component (B) is 5 to 250 parts by weight with respect to 100 parts by weight of the component (A), and a blending amount of the component (C) is 0.1 to 10 parts by weight with respect to a total of 100 parts by weight of the blending amount of the component (B) and a blending amount of the component (A), and
wherein the polyfunctional (meth)acrylate of Component (B) is a monomer having two or more (meth)acryloyl groups in a molecule, the polyfunctional (meth)acrylate monomer being copolymerizable with the Component (A).
2. A curable resin composition according to claim 1 , wherein the monofunctional (meth)acrylic acid ester (a) having an alicyclic structure comprises one or more kinds of monofunctional (meth)acrylic acid esters selected from the group consisting of isobornyl methacrylate, isobornyl acrylate, cyclohexyl methacrylate, cyclohexyl acrylate, dicyclopentenyl acrylate, dicyclopentenyloxyethyl acrylate, dicyclopentanyl acrylate, dicyclopentenyloxyethyl methacrylate, dicyclopentenyloxyethyl methacrylate, and dicyclopentanyl methacrylate.
3. A curable resin composition according to claim 1 , wherein the bifunctional (meth)acrylic acid ester (b) comprises one or more kinds of bifunctional (meth)acrylic acid esters selected from the group consisting of cyclohexanedimethanol diacrylate and dimethyloltricyclodecane diacrylate.
4. A resin cured product, which is obtained by curing the curable resin composition according to claim 1 .
5. An optical material, which is formed from the resin cured product according to claim 4 .
6. An optical material according to claim 5 , wherein the optical material comprises an optical plastic lens.
7. A resin cured product, which is obtained by curing the curable resin composition according to claim 2 .
8. An optical material, which is formed from the resin cured product according to claim 7 .
9. An optical material according to claim 8 , wherein the optical material comprises an optical plastic lens.
10. A resin cured product, which is obtained by curing the curable resin composition according to claim 3 .
11. An optical material, which is formed from the resin cured product according to claim 10 .
12. An optical material according to claim 11 , wherein the optical material comprises an optical plastic lens.