Photocurable composition and hard coating agent

Patent metadata

Field	Value
Publication number	US-9982080-B2
Application number	US-201314374233-A
Country	US
Kind code	B2
Filing date	Mar 5, 2013
Priority date	Mar 27, 2012
Publication date	May 29, 2018
Grant date	May 29, 2018

Abstract

A photocurable composition contains at least one ultraviolet absorber represented by Formula (1), and a hard coating agent including the photocurable composition.

wherein R 1 , R 2 and R 3 may be the same as or different from each other and represent a branched or linear alkyl group with 1-20 carbon atoms and is substituted with a (meth)acryloyloxy group; the alkyl group may be substituted with a hydroxyl group, an alkoxy group having 1-8 carbon atoms, or an acyloxy group having 1-8 carbon atoms; the alkyl group may be interrupted by an oxygen atom, a sulfur atom, a carbonyl group, an ester group, an amide group, or an imide group; and R 4 , R 5 and R 6 may be the same as or different from each other and represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group having 1-12 carbon atoms, or an alkoxy group having 1-12 carbon atoms.

First claim

The invention claimed is:

1. A photocurable composition comprising:
one or more kinds of ultraviolet absorbers represented by the following Formula (1):

wherein R 1 , R 2 and R 3 may be the same as or different from each other and represent a branched or linear alkyl group that has from 3 to 8 carbon atoms and is substituted with a (meth)acryloyloxy group; the alkyl group may be substituted with a hydroxyl group, the alkyl group may be interrupted by one or more selected from an oxygen atom, a carbonyl group, an ester group, and an amide group; and R 4 , R 5 and R 6 may be the same as or different from each other and represent a hydrogen atom, or an alkyl group having from 1 to 12 carbon atoms; and
one or more kinds selected from the group consisting of photocurable monomer, photocurable oligomer, and photocurable polymer, and one or more kinds of photopolymerization initiator, the photopolymerization initiator being one or more kinds selected from the group consisting of (1) benzophenone or its derivatives, (2) acetophenone derivatives, (3) thioxanthone or its derivatives, (4) benzyl or its derivatives, (5) benzoin or its derivatives, (6) oxime-based compounds, (7) α-hydroxy ketone-based compounds, (8) α-aminoalkylphenone-based compounds, (9) phosphine oxide-based compounds and (10) titanocene compounds, wherein
the photocurable composition forms a film having a transmission at 380 nm of 7.01% to 20.6%, and a transmission at 365 nm of from 0.98% to 6.8%.

2. The photocurable composition according to claim 1 , wherein the photocurable monomer, the photocurable oligomer, and the photocurable polymer have at least one (meth)acryloyl group.

3. A hard coating agent comprising the photocurable composition according to claim 1 .

4. A hard coated film comprising a hard coating layer formed on a base film using the hard coating agent according to claim 3 .

5. A hard coating agent comprising the photocurable composition according to claim 2 .

6. A hard coated film comprising a hard coating layer formed on a base film using the hard coating agent according to claim 5 .

7. The photocurable composition according to claim 1 , wherein R 1 , R 2 and R 3 may be the same as or different from each other and represent a branched or linear alkyl group selected from the group consisting of n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-amyl, 1,2-dimethylpropyl, n-hexyl, cyclohexyl, 1,3-dimethylbutyl, 1-isopropylpropyl, 1,2-dimethylbutyl, n-heptyl, 2-heptyl, 1,4-dimethylpentyl, tert-heptyl, 2-methyl-1-isopropylpropyl, 1-ethyl-3-methylbutyl, n-octyl, tert-octyl, 2-ethylhexyl, and 2-methylhexyl.

8. A hard coating agent comprising the photocurable composition according to claim 7 .

9. A hard coated film comprising a hard coating layer formed on a base film using the hard coating agent according to claim 8 .

10. The photocurable composition according to claim 1 , wherein R 1 , R 2 and R 3 may be the same as or different from each other and represent a branched or linear alkyl group that has from 3 to 6 carbon atoms and is substituted with a (meth)acryloyloxy group.

11. The photocurable composition according to claim 1 , wherein the photopolymerization initiator is present at 0.1 to 10% by mass in the solid components of the photocurable composition.

12. A photocurable composition comprising:
one or more kinds of ultraviolet absorbers represented by the following Formula (1):

wherein R 1 , R 2 and R 3 may be the same as or different from each other and represent a branched or linear alkyl group that has from 3 to 20 carbon atoms and is substituted with a (meth)acryloyloxy group; the alkyl group may be substituted with a hydroxyl group, the alkyl group may be interrupted by one or more selected from an oxygen atom, a carbonyl group, an ester group, and an amide group; and R 4 , R 5 and R 6 may be the same as or different from each other and represent a hydrogen atom, or an alkyl group having from 1 to 12 carbon atoms; and
one or more kinds selected from the group consisting of photocurable monomer, photocurable oligomer, and photocurable polymer, and one or more kinds of photopolymerization initiator, the photopolymerization initiator being one or more kinds selected from the group consisting of (1) benzophenone or its derivatives, (2) acetophenone derivatives, (3) thioxanthone or its derivatives, (4) benzyl or its derivatives, (5) benzoin or its derivatives, (6) oxime-based compounds, (7) α-hydroxy ketone-based compounds, (8) α-aminoalkylphenone-based compounds, (9) phosphine oxide-based compounds and (10) titanocene compounds, wherein
the photocurable composition forms a film having a transmission at 380 nm of 7.01% to 20.6%, and a transmission at 365 nm of from 0.98% to 6.8%.

13. The photocurable composition according to claim 12 , wherein the photocurable monomer, the photocurable oligomer, and the photocurable polymer have at least one (meth)acryloyl group.

14. A hard coating agent comprising the photocurable composition according to claim 12 .

15. The photocurable composition according to claim 12 , wherein R 1 , R 2 and R 3 may be the same as or different from each other and represent a branched or linear alkyl group selected from the group consisting of n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-amyl, 1,2-dimethylpropyl, n-hexyl, cyclohexyl, 1,3-dimethylbutyl, 1-isopropylpropyl, 1,2-dimethylbutyl, n-heptyl, 2-heptyl, 1,4-dimethylpentyl, tert-heptyl, 2-methyl-1-isopropylpropyl, 1-ethyl-3-methylbutyl, n-octyl, tert-octyl, 2-ethylhexyl, and 2-methylhexyl, 2-propylhexyl, 10 n-nonyl, isononyl, n-decyl, isodecyl, n-undecyl, isoundecyl, n-dodecyl, isododecyl, n-tridecyl, isotridecyl, n-tetradecyl, isotetradecyl, n-pentadecyl, isopentadecyl, n-hexadecyl, isohexadecyl, n-heptadecyl, isoheptadecyl, n-octadecyl, isooctadecyl, n-nonadecyl, isononadecyl, n-icosyl, and isoicosyl, and is substituted with a (meth)acryloyloxy group.

16. The photocurable composition according to claim 12 , wherein the photopolymerization initiator is present at 0.1 to 10% by mass in the solid components of the photocurable composition.

Assignees

• Adeka Corp

Inventors

• Kamimoto Tetsuo
• Masuda Satoshi
• Sato Fumihiko
• Ishima Yosuke

Classifications

• C08F222/225

  the ester chains containing seven or more carbon atoms · CPC title

• C08K5/3492 Primary

  Triazines · CPC title

• C09D7/48

  Stabilisers against degradation by oxygen, light or heat · CPC title

• C08F290/067

  Polyurethanes; Polyureas · CPC title

• C09D5/32

  Radiation-absorbing paints {(protection against X-, gamma- or corpuscular radiation G21F)} · CPC title