Composition, production method for composition, and production method for unsaturated compound

Patent metadata

Field	Value
Publication number	US-11891472-B2
Application number	US-201917269147-A
Country	US
Kind code	B2
Filing date	Aug 16, 2019
Priority date	Aug 20, 2018
Publication date	Feb 6, 2024
Grant date	Feb 6, 2024

Abstract

The composition comprises a compound (A) represented by general formula (1) and a compound (B) represented by general formula (2), and comprises 0.00002 to 2.0 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),

(R 1 —COO) n —R 2 —(NCO) m   (1)

(R 1 —COO) n —R 2 —NHC(═O)NH—R 2 —(OCO—R 1 ) m   (2)

wherein in general formulae (1) and (2), R 1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R 2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contain an ether group; R 1 and R 2 in the general formula (1) are the same as R 1 and R 2 in the general formula (2); and n and m each represent an integer of one or two.

First claim

The invention claimed is:

1. A composition comprising:
a compound (A) represented by general formula (1) and
a compound (B) represented by general formula (2),
wherein the composition comprises 0.00002 to 2.0 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),
(R 1 —COO) n —R 2 —(NCO) m   (1)

(R 1 —COO) n —R 2 —NHC(═O)NH—R 2 —(OCO—R 1 ) m   (2)

wherein in the general formulae (1) and (2),
R 1 is an ethylenically unsaturated group having 2 to 7 carbon atoms;
R 2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally comprises an ether group;
R 1 and R 2 in the general formula (1) are the same as R 1 and R 2 in the general formula (2); and
n and m each represent an integer of 1 or 2.

2. The composition according to claim 1 , wherein the compound (A) is at least one compound selected from the group consisting of 2-methacryloyloxyethyl isocyanate, 2-(isocyanatoethyloxy) ethyl methacrylate, 2-acryloyloxyethyl isocyanate, 2-(isocyanatoethyloxy) ethyl acrylate, and 1,1-bis(acryloyloxymethyl)ethyl isocyanate.

3. The composition according to claim 1 , wherein a content of the compound (A) in the composition is 95.0% by mass or more.

4. The composition according to claim 1 , wherein the content of the compound (A) in the composition is 97.0% by mass to 99.9% by mass.

5. The composition according to claim 1 , further comprising as an additive any one selected from the group consisting of hydroquinone, methoxyhydroquinone, catechol, p-tert-butylcatechol, cresol, 2,6-di-tert-butyl-4-methylphenol (BHT), and phenothiazine.

6. A method of producing an unsaturated compound, comprising the steps of:
mixing the composition according to claim 1 with a compound having active hydrogen; and
reacting the compound (A) contained in the composition with the compound having active hydrogen to obtain a reaction product.

7. The method of producing an unsaturated compound according to claim 6 , wherein the compound having the active hydrogen is an alcohol, a thiol, an amine or a carboxylic acid.

8. The method of producing an unsaturated compound according to claim 6 , wherein the reaction product is an unsaturated urethane compound, an unsaturated thiourethane compound, an unsaturated urea compound, or an unsaturated amide compound.

9. The method of producing an unsaturated compound according to claim 6 , wherein the reaction product is any one selected from the group consisting of 2-butanone oxime-O-(carbamoylethyl-2-methacrylate), 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl methacrylate, 2-butanone oxime-O-(carbamoylethyl-2-acrylate), and 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl acrylate.

10. The method of producing an unsaturated compound according to claim 6 , wherein a reaction temperature at which the compound (A) contained in the composition is reacted with the compound having the active hydrogen is −10 to 100° C.

Assignees

• Showa Denko Kk
• Resonac Corp

Inventors

• Nishimura Norihito
• Ohno Katsutoshi

Classifications

• C07C333/04

  having nitrogen atoms of thiocarbamic groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07C233/18

  having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton · CPC title

• C07C231/10

  from compounds not provided for in groups C07C231/02 - C07C231/08 · CPC title

• C07C275/10

  being further substituted by singly-bound oxygen atoms · CPC title

• C07C273/18

  of substituted ureas · CPC title