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

Patent metadata

Field	Value
Publication number	US-11401237-B2
Application number	US-201917269386-A
Country	US
Kind code	B2
Filing date	Aug 16, 2019
Priority date	Aug 20, 2018
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

The invention relates to a composition excellent in stability during storage and stability during utilization, and relates to a method of producing the composition. The composition includes a compound (A) represented by general formula (1) and a compound (B) represented by general formula (2), and includes 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),(R1—COO)n—R2—(NCO)m  (1)(R1—COO)n—R2—(R3—R1)m  (2)wherein in general formulae (1) and (2), R1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contains an ether group; R1 and R2 in the general formula (1) are the same as R1 and R2 in the general formula (2); in general formula (2), R3 is —NHC(═O)—; 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 0.2 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 —(R 3 —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 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);
in the general formula (2), R 3 is —NHC(═O)—; 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 of claim 1 , wherein a content of the compound (A) in the composition is 95.0% by mass or more.

4. A method of producing a composition, comprising steps of:
producing a mixture which comprises a compound (A) represented by general formula (1) and a compound (B) represented by general formula (2) and which comprises more than 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A); and
purifying the mixture by distillation process at a reflux ratio of 2.0 to 4.0, a pressure of 1.0 to 10.0 kPa and a distillation temperature of 90 to 140° C.,
(R 1 —COO) n —R 2 —(NCO) m   (1)

(R 1 —COO) n —R 2 —(R 3 —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),
in general formula (2), R 3 is —NHC(═O)—; and
n and m each represent an integer of 1 or 2.

5. The method of producing a composition according to claim 4 , wherein in the composition obtained by the purifying step,
a content of the compound (B) with respect to 100 parts by mass of the compound (A) is 0.00002 to 0.2 parts by mass.

6. A method of producing an unsaturated compound, comprising 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-butanone oxime-O-(carbamoylethyl-2 acrylate), 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl methacrylate, and 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl acrylate.

Assignees

• Showa Denko Kk

Inventors

• Nishimura Norihito
• Ohno Katsutoshi

Classifications

• C07C269/02

  from isocyanates with formation of carbamate groups · CPC title

• C07D231/12

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07C231/10

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

• C07C263/10

  by reaction of amines with carbonyl halides, e.g. with phosgene · CPC title

• C07C275/10 Primary

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