Method for producing (meth)acrylic acid amide compound, composition, and active energy ray-curable composition

Patent metadata

Field	Value
Publication number	US-11976020-B2
Application number	US-202117302798-A
Country	US
Kind code	B2
Filing date	May 12, 2021
Priority date	May 14, 2020
Publication date	May 7, 2024
Grant date	May 7, 2024

Abstract

A method for producing a (meth)acrylic acid amide compound, the method including: adding at least one selected from the group consisting of an amino group-containing compound and a neutralization salt of the amino group-containing compound to a mixture including (meth)acrylic acid halide and an organic solvent immiscible with water to allow the (meth)acrylic acid halide and at least one selected from the group consisting of the amino group-containing compound and the neutralization salt of the amino group-containing compound to react with each other, to produce the (meth)acrylic acid amide compound.

First claim

What is claimed is:

1. A method for producing a (meth)acrylic acid amide compound, the method comprising:
adding an aqueous solution of at least one compound selected from the group consisting of an amino group-containing compound and a neutralization salt of the amino group-containing compound,
to a mixture including (meth)acrylic acid halide and an organic solvent immiscible with water,
to allow the (meth)acrylic acid halide and at least one compound selected from the group consisting of the amino group-containing compound and the neutralization salt of the amino group-containing compound to react with each other,
to produce the (meth)acrylic acid amide compound.

2. The method according to claim 1 , further comprising adding an alkaline aqueous solution after adding the aqueous solution of the at least one compound selected from the group consisting of the amino group-containing compound and the neutralization salt of the amino group-containing compound to the mixture.

3. The method according to claim 1 , wherein solubility of the organic solvent in water is 30 g/100 mL or less.

4. The method according to claim 1 , wherein solubility of the organic solvent in water is 2 g/100 mL or greater but 30 g/100 mL or less.

5. The method according to claim 1 , wherein the organic solvent is at least one selected from the group consisting of ethyl acetate, toluene, cyclopentyl methyl ether, butyl acetate, and methyl ethyl ketone.

6. The method according to claim 1 , wherein the organic solvent is ethyl acetate.

7. The method according to claim 1 , wherein at least one compound selected from the group consisting of the amino group-containing compound and the neutralization salt of the amino group-containing compound is a compound including an amino group and a carboxylic acid ester structure.

8. The method according to claim 7 , wherein the compound comprising an amino group and a carboxylic acid ester structure is an amino acid derivative having sarcosine as a mother nucleus.

9. The method according to claim 7 , wherein the compound comprising an amino group and a carboxylic acid ester structure is an amino acid derivative having proline as a mother nucleus.

10. The method according to claim 1 , wherein the at least one compound selected from the group consisting of the amino group-containing compound and the neutralization salt of the amino group-containing compound is a compound including a carboxylic acid ester structure and an amino group which corresponds to an amino acid derivative having sarcosine or proline as a mother nucleus, and
wherein solubility of the organic solvent in water is 30 g/100 mL or less.

11. The method according to claim 10 , which includes the amino group which corresponding to a sarcosine mother-nucleus.

12. The method according to claim 10 , which includes the amino group which corresponding to a proline mother-nucleus.

13. The method according to claim 10 , wherein solubility of the organic solvent in water is 2 g/100 mL or greater but 30 g/100 mL or less.

14. The method according to claim 10 , wherein the organic solvent is at least one selected from the group consisting of ethyl acetate, toluene, cyclopentyl methyl ether, butyl acetate, and methyl ethyl ketone.

15. The method according to claim 10 , wherein the organic solvent is ethyl acetate.

16. The method according to claim 1 , wherein the reaction takes place in a non-homogenous reaction system including the solvent immiscible with water and water.

17. The method according to claim 16 , wherein an amidation reaction progresses at an interface between the organic solvent and water.

Assignees

• Morita Mitsunobu
• Kobayashi Masahide
• Suenaga Takenori
• Noguchi Soh
• Okada Takashi
• Ricoh Co Ltd

Inventors

• Morita Mitsunobu
• Kobayashi Masahide
• Suenaga Takenori
• Noguchi Soh
• Okada Takashi

Classifications

• C07C231/02 Primary

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title

• C08K5/20

  Carboxylic acid amides · CPC title

• C08L33/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title

• C07D207/16 Primary

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title