Curable composition and polymer

Patent metadata

Field	Value
Publication number	US-2017198076-A1
Application number	US-201715467880-A
Country	US
Kind code	A1
Filing date	Mar 23, 2017
Priority date	May 31, 2011
Publication date	Jul 13, 2017
Grant date	—

Abstract

An object of the invention is to provide a curable composition having a HALS skeleton and capable of producing polymers having excellent weather resistance and outer appearance. The present invention provides a curable composition including at least a monomer component that contains a monomer (A) represented by a certain formula and a monomer (B) polymerizable with the monomer (A). In the curable composition, the content of the monomer (A) is 0.01 to 35 mol % in the monomer component, and the content of the monomer (B) is 65 to 99.99 mol % in the monomer component.

First claim

1 . A resin sheet produced by polymerizing an active energy ray curable composition, the curable composition comprising:
a monomer component comprising a monomer (A) of formula (1) and a monomer (B) polymerizable with the monomer (A), wherein a content of the monomer (A) is 0.01 to 35 mol % in the monomer component, and a content of the monomer (B) is 65 to 99.99 mol % in the monomer component,

wherein
R 1 is a hydrogen atom or a methyl group;
X is an imino group, a compound of formula (2) or a compound of formula (3); and
R 2 , R 3 and R 4 each independently are a hydrogen atom, a linear alkyl group comprising from 1 to 8 carbon atoms, a branched linear alkyl group comprising from 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group comprising from 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group comprising 6 to 12 carbon atoms; and
a combination of R 2 and R 3 , R 2 and R 4 , R 3 and R 4 , or R 2 , R 3 and R 4 optionally form a ring structure and the ring structure optionally has a substituted group,

wherein
n is an integer of 1 to 10;
R 5 and R 6 each are a hydrogen atom or a methyl group; and
at least one of R 5 and R 6 represents a hydrogen atom,

wherein n is an integer of 1 to 10.

2 . The resin sheet according to claim 1 , wherein the curable composition further comprises a polymer comprising a monomer (C) polymerizable with the monomer (A).

3 . The resin sheet according to claim 1 , wherein the monomer (B) contains methyl methacrylate at content of 50 mol % or more.

4 . The resin sheet according to claim 1 , wherein the curable composition further comprises at least one polymerization initiator (D) selected from the group consisting of benzoin, benzoin monomethyl ether, benzoin isopropyl ether, acetoin, benzophenone, p-methoxybenzophenone, diethoxyacetophenone, benzyl dimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, methyl phenyl glyoxylate, 2-hydroxy-2-methyl-1-phenylpropane-1-on, tetramethyl thiuram monosulphide, tetramethyl thiuram disulphide, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, 2,4,6-trimethylbenzoyl phenylethoxy phosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butanone-1 and camphorquinone.

5 . The resin sheet according to claim 1 , wherein the curable composition further comprises at least one ultraviolet absorber (E) selected from the group consisting of 2-hydroxy-4-octoxybenzophenone, 2,4-dihydroxybenzophenone, 2-(2-hydroxy-tert-butylphenyl) benzotriazole, and 2-[4-(octyl-2-methylethanoate)oxy-2-hydroxyphenyl]-4,6-[bis(2,4-dimethylphenyl)]-1,3,5-triazine.

6 . The resin sheet according to claim 1 , wherein a total light transmittance is from 85 to 100%, and a haze value is less than 5%.

7 . The resin sheet according to claim 2 , wherein a total light transmittance is from 85 to 100%, and a haze value is less than 5%.

8 . The resin sheet according to claim 3 , wherein a total light transmittance is from 85 to 100%, and a haze value is less than 5%.

9 . The resin sheet according to claim 4 , wherein a total light transmittance is from 85 to 100%, and a haze value is less than 5%.

10 . The resin sheet according to claim 5 , wherein a total light transmittance is from 85 to 100%, and a haze value is less than 5%.

11 . A cured coating film produced by applying an active energy ray curable composition comprising a monomer component comprising a monomer (A) of formula (1) and a monomer (B) polymerizable with the monomer (A) on a substrate, and subsequently polymerizing the curable composition, thereby obtaining the cured coating film,
wherein a content of the monomer (A) is 0.01 to 35 mol % in the monomer component, and a content of the monomer (B) is 65 to 99.99 mol % in the monomer component,

wherein
R 1 is a hydrogen atom or a methyl group;
X is an imino group, a compound of formula (2) or a compound of formula (3); and
R 2 , R 3 and R 4 each independently are a hydrogen atom, a linear alkyl group comprising from 1 to 8 carbon atoms, a branched linear alkyl group comprising from 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group comprising from 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group comprising 6 to 12 carbon atoms; and
a combination of R 2 and R 3 , R 2 and R 4 , R 3 and R 4 , or R 2 , R 3 and R 4 optionally form a ring structure and the ring structure optionally has a substituted group,

wherein
n is an integer of 1 to 10;
R 5 and R 6 each are a hydrogen atom or a methyl group; and
at least one of R 5 and R 6 represents a hydrogen atom,

wherein n is an integer of 1 to 10.

12 . The cured coating film according to claim 11 , wherein the curable composition further comprises a polymer comprising a monomer (C) polymerizable with the monomer (A).

13 . The cured coating film according to claim 11 , wherein the monomer (B) comprises methyl methacrylate at content of 50 mol % or more.

14 . The cured coating film according to claim 11 , wherein the curable composition further comprises at least one polymerization initiator (D) selected from the group consisting of benzoin, benzoin monomethyl ether, benzoin isopropyl ether, acetoin, benzophenone, p-methoxybenzophenone, diethoxyacetophenone, benzyl dimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, methyl phenyl glyoxylate, 2-hydroxy-2-methyl-1-phenylpropane-1-on, tetramethyl thiuram monosulphide, tetramethyl thiuram disulphide, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, 2,4,6-trimethylbenzoyl phenylethoxy phosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butanone-1 and camphorquinone. [0058]

15 . The cured coating film according to claim 11 , wherein the curable composition further comprises at least one ultraviolet absorber (E) selected from the group consisting of 2-hydroxy-4-octoxybenzophenone, 2,4-dihydroxybenzophenone, 2-(2-hydroxy-tert-butylphenyl) benzotriazole, and 2-[4-(octyl-2-methylethanoate)oxy-2-hydroxyphenyl]-4,6-[bis(2,4-dimethylphenyl)]-1,3,5-triazine. [0061]

16 . The cured coating film according to claim 11 , wherein a total light transmittance is from 85 to 100%, and a haze value is less than 5%.

17 . The cured coating film according to claim 12 , wherein a total light transmittance is from 85 to 100%, and a haze value is less than 5%.

18 . The cured coating film according to claim 13 , wherein a total light transmittance is from 85 to 100%, and a haze value is less than 5%.

19 . The cured coating film according to claim 14 , wherein a total light transmittance is from 85

Assignees

• Mitsubishi Rayon Co

Inventors

• Noda Tetsuya
• Nakaya Fuminori
• Okutsu Hajime

Classifications

• C08F220/14 Primary

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title

• C09D133/12

  Homopolymers or copolymers of methyl methacrylate · CPC title

• C08J2333/12

  Homopolymers or copolymers of methyl methacrylate · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08F222/103

  of trialcohols, e.g. trimethylolpropane tri(meth)acrylate · CPC title