Water-soluble composition, production method for cured product thereof, and cured product thereof, and acyl phosphinate

Patent metadata

Field	Value
Publication number	US-11649334-B2
Application number	US-201816493865-A
Country	US
Kind code	B2
Filing date	Mar 13, 2018
Priority date	Mar 15, 2017
Publication date	May 16, 2023
Grant date	May 16, 2023

Abstract

Provided are: a water-soluble composition which has excellent storage stability and is adaptable to a wide range of light sources and capable of forming a highly fine pattern; a method of producing a cured product of the same; a cured product of the same; and an acylphosphinate. The water-soluble composition contains: an acylphosphinate (A) represented by Formula (I) below, wherein X1 represents an aryl group having 6 to 15 carbon atoms; X2 represents a linear alkyl group having 1 to 8 carbon atoms or the like; Am+ represents an alkali metal ion or the like; and m represents a number of 1 to 3; and a compound (B) having a group represented by Formula (II) below, wherein R1 represents a hydrogen atom or the like; Z1 represents an oxygen atom or the like; R2 represents a hydrogen atom or the like; Z2 represents an alkylene group having 1 to 6 carbon atoms; n represents a number of 0 to 30; * means a bond; and, when the compound (B) has plural groups represented by Formula (II), plural R1′s, Z1′s, Z2′s and n's are each optionally the same or different.

First claim

The invention claimed is:

1. A water-soluble composition comprising:
an acylphosphinate (A) represented by the following Formula (I):

wherein, X 1 represents an aryl group having 6 to 15 carbon atoms;
hydrogen atoms in the group represented by X 1 are each optionally substituted with a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a linear halogenated alkyl group having 1 to 8 carbon atoms, a branched halogenated alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, a linear halogenated alkoxy group having 1 to 8 carbon atoms, or a branched halogenated alkoxy group having 3 to 8 carbon atoms;
X 2 represents a phenyl group;
A m+ represents N + HY 1 Y 2 Y 3 ;
Y 1 , Y 2 and Y 3 each independently represent a hydrogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or an arylalkyl group having 7 to 13 carbon atoms;
methylene groups in the groups represented by Y 1 , Y 2 and Y 3 are each optionally substituted with a sulfur atom or a carbonyl group;
one or more combinations of Y 1 and Y 2 , Y 1 and Y 3 , and Y 2 and Y 3 are bound with each other to form a ring and at least one hydrogen atom of Y 1 , Y 2 and Y 3 is substituted with a hydroxy group; and
m represents a number of 1 to 3; and
a compound (B) having a group represented by the following Formula (II):

wherein, R 1 represents a hydrogen atom or a methyl group;
Z 1 represents an oxygen atom or —NR 2 —;
R 2 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms;
Z 2 represents an alkylene group having 1 to 6 carbon atoms;
n represents a number of 0 to 30;
* means a bond; and
when the compound (B) has plural groups represented by the Formula (II), plural R 1′ s, Z 1′ s, Z 2′ s and n's are each optionally the same or different).

2. The water-soluble composition according to claim 1 , wherein X 1 in the Formula (I) is a 2,4,6-trimethylphenyl group.

3. The water-soluble composition according to claim 1 , wherein Z 1 in the Formula (II) is —NR 2 —.

4. The water-soluble composition according to claim 1 , further comprising a coloring agent (C).

5. A method of producing a cured product, comprising curing the water-soluble composition according to claim 1 by irradiation with light or heating.

6. A cured product obtained from the water-soluble composition according to claim 1 .

7. An acylphosphinate represented by the following Formula (I):

wherein, X 1 represents an aryl group having 6 to 15 carbon atoms;
hydrogen atoms in the group represented by X 1 are each optionally substituted with a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a linear halogenated alkyl group having 1 to 8 carbon atoms, a branched halogenated alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, a linear halogenated alkoxy group having 1 to 8 carbon atoms, or a branched halogenated alkoxy group having 3 to 8 carbon atoms;
X 2 represents a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, or an aryl group having 6 to 15 carbon atoms;
hydrogen atoms in the aryl group having 6 to 15 carbon atoms that is represented by X 2 are each optionally substituted with a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a linear halogenated alkyl group having 1 to 8 carbon atoms, a branched halogenated alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, a linear halogenated alkoxy group having 1 to 8 carbon atoms, a branched halogenated alkoxy group having 3 to 8 carbon atoms, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxyl group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a heterocycle-containing group;
a methylene group in the group represented by X 2 is optionally substituted with oxygen atom or a sulfur atom;
A m+ represents an alkali metal ion, an alkaline earth metal ion, or N + HY 1 Y 2 Y 3 ;
Y 1 , Y 2 and Y 3 each independently represent a hydrogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or an arylalkyl group having 7 to 13 carbon atoms;
methylene groups in the groups represented by Y 1 , Y 2 and Y 3 are each optionally substituted with a sulfur atom or a carbonyl group;
one or more combinations of Y 1 and Y 2 , Y 1 and Y 3 , and Y 2 and Y 3 are optionally bound with each other to form a ring; and
m represents a number of 1 to 3,
wherein,
in the Formula (I), X 2 is a phenyl group and A m+ is N + HY 1 Y 2 Y 3 , and
one or more combinations of Y 1 and Y 2 , Y 1 and Y 3 , and Y 2 and Y 3 are bound with each other to form a ring; and
wherein,
at least one hydrogen atom of Y 1 , Y 2 and Y 3 is substituted with a hydroxy group.

8. The water-soluble composition according to claim 2 , wherein Z 1 in the Formula (II) is —NR 2 —.

9. The water-soluble composition according to claim 2 , further comprising a coloring agent (C).

10. The water-soluble composition according to claim 3 , further comprising a coloring agent (C).

11. The water-soluble composition according to claim 1 , wherein said at least one hydrogen atom of Y 1 , Y 2 and Y 3 is substituted with the hydroxy group, on the ring formed by said one or more combinations of Y 1 and Y 2 , Y 1 and Y 3 , and Y 2 and Y 3 .

12. The acylphosphinate according to claim 7 , wherein said at least one hydrogen atom of Y 1 , Y 2 and Y 3 is substituted with the hydroxy group, on the ring formed by said one or more combinations of Y 1 and Y 2 , Y 1 and Y 3 , and Y 2 and Y 3 .

Assignees

• Adeka Corp

Inventors

• Irisawa Masatomi
• Hara Kenji

Classifications

• C08F20/56 Primary

  Acrylamide; Methacrylamide · CPC title

• C07F9/307

  Acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se) · CPC title

• G03F7/029

  Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur · CPC title

• C08F20/60

  containing nitrogen in addition to the carbonamido nitrogen · CPC title

• C08F220/58

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine} · CPC title