Photopolymerization initiator, polymerizable composition, ink jet recording method, and acylphosphine oxide compound

Patent metadata

Field	Value
Publication number	US-10590264-B2
Application number	US-201916278714-A
Country	US
Kind code	B2
Filing date	Feb 19, 2019
Priority date	Sep 7, 2016
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

Abstract

An acylphosphine oxide compound represented by Formula 1-1 or Formula 2-1 which can be used as a photopolymerization initiator. In Formula 1-1 and Formula 2-1, A represents an m-valent group, L's each independently represent a single bond or a divalent linking group, R 1 's each independently represent an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, R 2 and R 3 each independently represent an alkyl group, an aryl group, or an alkoxy group, m represents an integer of 3 or more, n1's each independently represent an integer of 0 to 4, and n2's each independently represent an integer of 0 to 5.

First claim

What is claimed is:

1. A photopolymerization initiator which is an acylphosphine oxide compound represented by Formula 1-1 or Formula 2-1,

wherein, in Formula 1-1 and Formula 2-1, A represents an m-valent group, L's each independently represent a single bond or a divalent linking group, R 1 's each independently represent an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, R 2 and R 3 each independently represent an alkyl group, an aryl group, or an alkoxy group, m represents an integer of 3 or more, n1's each independently represent an integer of 0 to 4, and n2's each independently represent an integer of 0 to 5.

2. The photopolymerization initiator according to claim 1 ,
wherein A is an m-valent group obtained by bonding two or more structures selected from the group consisting of a carbon atom, an m-valent hydrocarbon group having 1 to 30 carbon atoms, a mono- or higher-valent hydrocarbon group having 1 to 30 carbon atoms, an oxygen atom, a nitrogen atom, and a sulfur atom.

3. The photopolymerization initiator according to claim 1 ,
wherein A is an m-valent group having a ring structure, an m-valent hydrocarbon group having 1 to 3 carbon atoms, or a carbon atom.

4. The photopolymerization initiator according to claim 1 ,
wherein A is an m-valent group not having any of an amino bond, a thioether bond, and a halogen atom, and L is a divalent linking group not having any of an amino bond, a thioether bond, and a halogen atom or a single bond.

5. The photopolymerization initiator according to claim 1 which is an acylphosphine oxide compound represented by Formula 1-2 or Formula 2-2,

wherein, in Formula 1-2 and Formula 2-2, A represents an m-valent group, L's each independently represent a single bond or a divalent linking group, R 2 and R 3 each independently represent an alkyl group, an aryl group, or an alkoxy group, R 11 to R 13 each independently represent an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and m represents an integer of 3 or more.

6. The photopolymerization initiator according to claim 1 ,
wherein m is an integer of 3 to 5.

7. The photopolymerization initiator according to claim 1 ,
wherein the acylphosphine oxide compound is a compound having a C n symmetry; here, n represents an integer of 3 to 24.

8. A polymerizable composition comprising:
the photopolymerization initiator according to claim 1 ; and
a polymerizable compound.

9. An ink jet recording method comprising:
a step of jetting the polymerizable composition according to claim 8 onto a recording medium using an ink jet method; and
a step of curing the polymerizable composition by irradiating the jetted polymerizable composition with active radiation.

10. An acylphosphine oxide compound represented by Formula 1-1 or Formula 2-1,

wherein, in Formula 1-1 and Formula 2-1, A represents an m-valent group, L's each independently represent a single bond or a divalent linking group, R 1 's each independently represent an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, R 2 and R 3 each independently represent an alkyl group, an aryl group, or an alkoxy group, m represents an integer of 3 or more, n1's each independently represent an integer of 0 to 4, and n2's each independently represent an integer of 0 to 5.

11. The acylphosphine oxide compound according to claim 10 ,
wherein A is an m-valent group having a ring structure, an m-valent hydrocarbon group having 1 to 3 carbon atoms, or a carbon atom.

12. The acylphosphine oxide compound according to claim 10 ,
wherein A is an m-valent group not having any of an amino bond, a thioether bond, and a halogen atom, and L is a divalent linking group not having any of an amino bond, a thioether bond, and a halogen atom or a single bond.

13. The acylphosphine oxide compound according to claim 10 represented by Formula 1-2 or Formula 2-2,

wherein, in Formula 1-2 and Formula 2-2, A represents an m-valent group, L's each independently represent a single bond or a divalent linking group, R 2 and R 3 each independently represent an alkyl group, an aryl group, or an alkoxy group, R 11 to R 13 each independently represent an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and m represents an integer of 3 or more.

14. The acylphosphine oxide compound according to claim 10 ,
wherein m is an integer of 3 to 5.

15. The acylphosphine oxide compound according to claim 10 having a C n symmetry, wherein n represents an integer of 3 to 24.

Assignees

• Fujifilm Corp

Inventors

• Tsuyama Hiroaki
• Yokoi Kazuhiro
• Araki Kenjiro

Classifications

• C08K5/5317

  Phosphonic compounds, e.g. R—P(:O)(OR')2 · CPC title

• C07F9/5337

  Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se) · CPC title

• C09D11/101

  Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing · CPC title

• C08K5/5397 Primary

  Phosphine oxides · CPC title

• C08F2/50 Primary

  with sensitising agents · CPC title