Compound, photopolymerization initiator, photocurable composition and cured product thereof, and photocurable ink and print using the same

Patent metadata

Field	Value
Publication number	US-11479569-B2
Application number	US-201716645858-A
Country	US
Kind code	B2
Filing date	Oct 10, 2017
Priority date	Oct 10, 2017
Publication date	Oct 25, 2022
Grant date	Oct 25, 2022

Abstract

There are provided a compound represented by general formula (1), a photopolymerization initiator comprising this compound, a photocurable composition having this photopolymerization initiator and a photocurable compound as essential components, and a cured product formed by curing this photocurable composition, wherein in formula (1), R1 and R2 each independently represents an alkyl group or the like; R3 to R5 each independently represent a hydrogen atom, an alkyl group or the like; X1 represents a single bond or an alkylene group; and X2 represents a bonding group represented by general formulas (2) to (4), and wherein n represents an integer of 1 to 6, when n is an integer of 1, Y represents an alkyl group, an aryl group or the like.

First claim

What is claimed is:

1. A compound, characterized in that it is represented by general formula (1):

wherein in formula (1), R 1 and R 2 each independently represent an alkyl group, an aryl group, or an alkoxy group; R 3 to R 5 each independently represent a hydrogen atom, an alkyl group having a carbon atom number of 1 to 4, or an alkoxy group having a carbon atom number of 1 to 4; X 1 represents an optionally branched alkylene group having a carbon atom number of 1 to 6; and X 2 represents a bonding group represented by general formulas (2) to (4),

n represents an integer of 1 to 6; when n is an integer of 1, Y represents an aryl group, a structural moiety (y-3) represented by formula (y-3), a structural moiety (y-5) represented by formula (y-5), a structural moiety (y-8) represented by formula (y-8), a structural moiety (y-9) represented by formula (y-9); and when n is an integer of 2 to 6, Y represents a 2- to 6- valent linking group,

wherein in formula (y-3), R 6 represents an alkylene group having a carbon atom number of 2 to 4; R 7 represents a hydrogen atom or a phenyl group or an alkyl group having a carbon atom number of 1 to 4; and m represents an integer of 1 to 20,

wherein in formula (y-5), R 8 represents an alkylene group having a carbon atom number of 1 to 18 or an arylene group having a carbon atom number of 6 to 18; and R 9 represents an alkyl group having a carbon atom number of 1 to 18 or an aryl group having a carbon atom number of 6 to 18,

wherein in formula (y-8), R 6 represents an alkylene group having a carbon atom number of 2 to 4; R 12 represents a hydrogen atom or a methyl group; and 1 represents an integer of 2 to 20,

wherein in formula (y-9), R 7 represents an alkylene group having a carbon atom number of 1 to 18; and R 12 represents a hydrogen atom or a methyl group.

2. The compound according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by structural formula (M6), (M10), (M12), (M14), (M15), (M17), (M18), (M20), (M22), (M24), (M27), (M30) to (M34), (M36), or (M38):

3. A photopolymerization initiator, comprising the compound of claim 1 .

4. A photocurable composition, comprising the photopolymerization initiator of claim 3 and a photocurable compound as essential components.

5. A cured product, which is a cured product formed by curing the photocurable composition of claim 4 .

6. A photocurable ink, comprising the photocurable composition of claim 4 .

7. A print, characterized in that it is a print formed by printing the photocurable ink of claim 6 on a base material, wherein the print comprises a benzaldehyde compound (2a), an alkyl phosphine oxide compound (2b), or an alkyl phosphinic acid compound (2c), and wherein the migration concentration of the compound (2a) as measured by the following method is 50 ppb or less, the migration concentration of the compound (2b) as measured by the following method is 50 ppb or less, and the migration concentration of the compound (2c) as measured by the following method is 50 ppb or less, and
the method for measurement comprises the steps of:
performing overlapping in a manner of bringing the back side of a milk carton white board in a non-printed state into contact with a cured ink layer evenly printed on a milk carton board, and pressurizing at 25° C. for 48 hours under a press pressure of 40 kg/cm 2 ;
manufacturing a liquid container having a volume of 1000 ml from this milk carton white board in a non-printed state after pressurization;
injecting 1000 ml of an aqueous ethanol solution into this liquid container and enclosing the liquid container, wherein the aqueous ethanol solution is a mixed solution of 95 wt % ethanol and 5 wt % pure water;
keeping the liquid container at room temperature at 25° C. for 24 hours for extracting ink components transferred to the back side of the milk carton white board into the aqueous ethanol solution; and
withdrawing the aqueous ethanol solution from the liquid container, and quantifying dissolution concentrations of the compound (2a), the compound (2b), and the compound (2c) by a LC/MS/MS analysis as the migration concentrations.

8. The compound according to claim 1 , wherein Y is represented by formula Y5.

9. The compound according to claim 1 , wherein Y is represented by structural moiety Y8.

Assignees

• Dainippon Ink & Chemicals

Inventors

• Miyamoto Masanori
• Yamada Tomokazu
• Fang Yong
• Xiu Fangxi
• Deng Changjun

Classifications

• C09D11/03

  characterised by features other than the chemical nature of the binder · 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

• C09D11/322

  Pigment inks · CPC title

• C09D11/38

  characterised by non-macromolecular additives other than solvents, pigments or dyes · CPC title

• C07F9/5337 Primary

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