# US 9,040,736 B2 · Stabilized isocyanate group-containing ethylenically unsaturated compound

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- Number: US 9,040,736 B2
- Document ID: US9040736B2
- Status: Granted
- Kind: B2
- Application number: 13/984,391
- Filed: 2012-02-02
- Published: 2013-11-28
- Granted: 2015-05-26
- Earliest claimed: 2011-02-15
- Assignees: Showa Denko K.K.
- Applicants: Norihito Nishimura; Shinichi Yorozuya
- Inventors: Norihito Nishimura; Shinichi Yorozuya
- Web page: https://patentgrep.com/patent/US9040736B2

## CPC

- C07C 263/18: Separation; Purification; Stabilisation; Use of additives
- C07C 265/04: of a saturated carbon skeleton
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

An object of the present invention is to improve the stability of an ethylenically unsaturated compound having an isocyanate group in the molecule by preventing a polymerization of the ethylenically unsaturated compound. The present invention relates to a stabilizing composition for an isocyanate group-containing ethylenically unsaturated compound, comprising: an isocyanate group-containing ethylenically unsaturated compound (A) which comprises one or more isocyanate groups and one or more ethylenically unsaturated groups in the molecule; and a stabilizing agent (B) which is a compound in which at least one of the ethylenically unsaturated groups in the compound (A) is replaced with an alkyl group which may have a substituent.

## Claims

### Claim 1

A stabilizing composition for an isocyanate group-containing ethylenically unsaturated compound, comprising:
an isocyanate group-containing ethylenically unsaturated compound (A) which comprises one or more isocyanate groups and one or more ethylenically unsaturated groups represented by following formula (1); and
a stabilizing agent (B) which is a compound having the same structure as compound (A) except that at least one of the ethylenically unsaturated groups represented by formula (1) in the compound (A) is replaced with a structure represented by following formula (2) or (3):
—CR1═CR2R3 (1)
wherein R1 to R3 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an aromatic group;
—CR4R5—CR6R7R8 (2)
wherein R4 to R8 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an aromatic group;
—CR9R10R11 (3)
wherein R9 to R11 each independently represent a hydrogen atom or an aromatic group; and
wherein none of R1 to R11 includes a substituent.

### Claim 2 (depends on 1)

The stabilizing composition according to claim 1, comprising the stabilizing agent (B) in an amount of 0.005% by mass to 5% by mass.

### Claim 3 (depends on 1)

The stabilizing composition according to claim 1, wherein the compound (A) is a compound comprising one or more groups represented by the following formula (4):
—O—(CO)—CR1═CR2R3 (4),
wherein R1 to R3 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an aromatic group, and wherein none of R1 to R3 includes a substituent.

### Claim 4 (depends on 1)

The stabilizing composition according to claim 1, wherein the compound (A) is a compound represented by the following formula (5):
CR2R3═CR1—(CO)—O—R12—NCO (5),
wherein R1 to R3 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an aromatic group, and none of R1 to R3 includes a substituent; and R12 represents a straight or branched chain alkylene group having 1 to 10 carbon atoms or —R13PhR14— (R13 and R14 represent a single bond or an alkylene group having 1 to 3 carbon atoms; and Ph represents a phenylene group.

### Claim 5 (depends on 1)

The stabilizing composition according to claim 1, wherein the compound (A) is 2-acryloyloxyethyl isocyanate, 2-methacryloyloxyethyl isocyanate, 1,1-(bisacryloyloxymethyl)ethyl isocyanate or 2-(isocyanatoethyloxy)ethyl methacrylate.

### Claim 6 (depends on 1)

The stabilizing composition according to claim 1, wherein the compound (A) is 2-acryloyloxyethyl isocyanate and the stabilizing agent (B) is at least one compound selected from the group consisting of 2-n-propionyloxyethyl isocyanate and 2-acetoxyethyl isocyanate.

### Claim 7 (depends on 1)

The stabilizing composition according to claim 1, wherein the compound (A) is 2-methacryloyloxyethyl isocyanate and the stabilizing agent (B) is at least one compound selected from the group consisting of 2-isobutyroyloxyethyl isocyanate and 2-n-propionyloxyethyl isocyanate.