Active energy ray-curable composition and antistatic film

Patent metadata

Field	Value
Publication number	US-9914788-B2
Application number	US-201715468413-A
Country	US
Kind code	B2
Filing date	Mar 24, 2017
Priority date	Sep 29, 2014
Publication date	Mar 13, 2018
Grant date	Mar 13, 2018

Abstract

Provided are an active energy ray-curable composition that has good antistatic properties, scratch resistance, and transparency after curing, and an antistatic film using the same. The active energy ray-curable composition of the present invention is an active energy ray-curable composition, including a photopolymerization initiator A represented by the following Formula (I) and an antistatic compound B,

in Formula (I), V 1 , V 2 , V 3 , and V 4 each independently represent a hydrogen atom or a substituent, and n represents an integer of 1 to 5.

First claim

What is claimed is:

1. An active energy ray-curable composition, comprising:
a photopolymerization initiator A represented by the following Formula (I);
an antistatic compound B; and
a polymerizable compound C which is different from the antistatic compound B and contains an ethylenically unsaturated group,
wherein the polymerizable compound C is a methacrylic or acrylic compound,
the polymerizable compound C is a polymerizable compound C-1 represented by the following Formula (7) and/or a polymerizable compound C-2 having a hydrophilic group,

in Formula (I), V 1 , V 2 , V 3 , and V 4 each independently represent a hydrogen atom or a substituent, and n represents an integer of 1 to 5:
CH 2 ═C(R 4 )COO(AO) n R 5   (7)

in Formula (7), R 4 represents a hydrogen atom or CH 3 , R 5 represents a hydrogen atom or a hydrocarbon group having 6 to 25 carbon atoms which may have a substituent, A represents an alkylene group having 2 to 5 carbon atoms which may have a substituent, and n represents an integer of 3 to 50.

2. The active energy ray-curable composition according to claim 1 , wherein the antistatic compound B is at least one polymerizable compound selected from the group consisting of compounds represented by the following Formulae (1) to (5),

in Formulae (1) to (5), R 1 's each independently represent a hydrogen atom, a halogen atom, a cyano group, a monovalent hydrocarbon group, —COO—C 2 , or —COO—C 2 bonded through a hydrocarbon, and C 2 represents a hydrogen atom or a hydrocarbon group which may have a substituent,
in Formulae (1) to (5), Z's each independently represent —COO—, —CONH—, —OCO—, —CH 2 OCO—, —CH 2 COO—, —O—, —SO 2 —, —CO—, —CONHCOO—, —CONHCONH—, —CONHSO 2 —, —CON(P 3 )—, —SO 2 N(G)-, —C 6 H 4 —, or an alkylene group having 1 to 30 carbon atoms, and G represents a hydrogen atom or a hydrocarbon group,
in Formulae (1) to (5), A's each independently represent a single bond or a divalent or higher valent linking group, and j's each independently represent an integer of 0 to 30,
in Formula (1), Y + represents a cationic group, X − represents an anionic group, u represents an integer of 1 to 3, and r represents an integer of 1 to 4,
in Formula (2), R 2 represents an alkylene group having 2 to 5 carbon atoms which may have a substituent, R 3 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which may have a substituent, and m represents an integer of 2 to 200,
in Formula (3), Q + represents an ammonium cation, a sulfonium cation, an iodonium cation, a phosphonium cation, or a pyridinium cation, L 1 represents a single bond or a divalent or higher valent linking group, T − represents COO − , SO 3 − or OPO(O − )(ORp), and Rp represents an alkyl group, and p represents an integer of 1 to 3,
in Formula (4), L 2 represents a single bond or a divalent or higher valent linking group, U + represents an ammonium or phosphonium cation which may have a substituent, and q represents an integer of 1 to 3, and
in Formula (5), J − represents COO − , OPO(OH)O − or SO 3 − , V + represents a cationic group, and w represents an integer of 1 to 3.

3. The active energy ray-curable composition according to claim 2 , wherein the antistatic compound B is a cationic polymerizable compound represented by Formula (1).

4. The active energy ray-curable composition according to claim 2 , wherein the antistatic compound B is a cationic polymerizable compound represented by Formula (1) and is an ammonium salt represented by the following Formula (6),

in Formula (6), R 1 represents a hydrogen atom, a halogen atom, a cyano group, a monovalent hydrocarbon group, —COO—C 2 , or —COO—C 2 bonded through a hydrocarbon, and C 2 represents a hydrogen atom or a hydrocarbon group which may have a substituent,
Z represents, —COO—, —CONH—, or —CH 2 —, A represents a single bond or a divalent or higher valent linking group, and j represents an integer of 0 to 10, and
L 3 , L 4 , and L 5 each independently represent an alkyl group, alkenyl group, alkynyl group, aryl group or heterocyclic group having 1 to 20 carbon atoms which may have a substituent, and at least two of L 3 , L 4 , and L 5 may be bonded to each other to form a ring.

5. The active energy ray-curable composition according to claim 1 , wherein the hydrophilic group is a hydroxy group or a carboxyl group.

6. The active energy ray-curable composition according to claim 1 , wherein the content of the photopolymerization initiator A is 0.5 to 10 parts by mass with respect to 100 parts by mass of the total polymerizable compound contained in the composition.

7. The active energy ray-curable composition according to claim 6 , wherein the content of the antistatic compound B is 10 to 60 parts by mass with respect to 100 parts by mass of the total polymerizable compound contained in the composition.

8. The active energy ray-curable composition according to claim 7 , wherein the content of the polymerizable compound C-1 is 10 to 50 parts by mass with respect to 100 parts by mass of the total polymerizable compound contained in the composition.

9. The active energy ray-curable composition according to claim 7 , wherein the content of the polymerizable compound C-2 is 5 to 20 parts by mass with respect to 100 parts by mass of the total polymerizable compound contained in the composition.

10. The active energy ray-curable composition according to claim 1 , wherein the photopolymerization initiator A has n of 1 in Formula (I).

11. The active energy ray-curable composition according to claim 1 , which is used in an antistatic agent.

12. An antistatic film comprising an antistatic layer formed by applying the active energy ray-curable composition according to claim 1 onto a substrate and curing the applied composition by active energy rays.

13. An antistatic film comprising an antistatic layer formed by applying the active energy ray-curable composition according to claim 2 onto a substrate and curing the applied composition by active energy rays.

Assignees

• Fujifilm Corp

Inventors

• Yamashita Masako

Classifications

• C08J7/0427

  with only one layer of a composition containing a polymer binder (with more layers C08J7/042) · CPC title

• C08F22/1006

  of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate · CPC title

• C08F2/50 Primary

  with sensitising agents · CPC title

• C08F120/60

  containing nitrogen in addition to the carbonamido nitrogen · CPC title

• C08J2453/00

  Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers · CPC title