2-cyanoacrylate-based adhesive composition

Patent metadata

Field	Value
Publication number	US-10793749-B2
Application number	US-201716313113-A
Country	US
Kind code	B2
Filing date	Jun 23, 2017
Priority date	Jun 28, 2016
Publication date	Oct 6, 2020
Grant date	Oct 6, 2020

Abstract

To provide a 2-cyanoacrylate-based adhesive composition not only exhibiting an excellent adhesion rate to a metal and a thermoplastic elastomer low in polarity, but also being excellent in storage stability. A 2-cyanoacrylate-based adhesive composition containing a 2-cyanoacrylic acid ester, and a compound having a sulfur atom-containing heteroallene structure.

First claim

What is claimed is:

1. A 2-cyanoacrylate-based adhesive composition comprising:
(a) a 2-cyanoacrylic acid ester; and
(b) a compound having a sulfur atom-containing heteroallene structure, represented by the following Formula (1):
R n —X═C═S  (1)

wherein X represents S O, N or C, R represents a hydrogen atom or at least one selected from the group consisting of an alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group, an alkenyl group, an alkynyl group, an aralkyl group and an aryl group, each of the groups may have a substituent, n denotes 0 in a case in which X represents an S atom or an O atom, n denotes 1 in a case in which X represents an N atom, n denotes 2 in a case in which X represents a C atom, and R's may be the same as or different from each other in a case in which two R's are present.

2. The 2-cyanoacrylate-based adhesive composition according to claim 1 , wherein (b) the compound having a sulfur atom-containing heteroallene structure is at least one compound selected from the group consisting of carbon disulfide, carbonyl sulfide and a compound having an isothiocyanate group.

3. The 2-cyanoacrylate-based adhesive composition according to claim 1 , wherein (b) the compound having a sulfur atom-containing heteroallene structure is a compound having an isothiocyanate group.

4. The 2-cyanoacrylate-based adhesive composition according to claim 1 , wherein a content of (b) the compound having a sulfur atom-containing heteroallene structure is from 0.0002 to 3 parts by mass with respect to 100 parts by mass of (a) the 2-cyanoacrylic acid ester.

5. The 2-cyanoacrylate-based adhesive composition according to claim 1 , further comprising (c) an onium salt represented by the following Formula (2):
C + A −   (2)

wherein C + represents at least one onium cation selected from the group consisting of a quaternary ammonium cation, a quaternary phosphonium cation, an imidazolium cation, a pyridinium cation and a tertiary sulfonium cation, and A − represents at least one anion selected from the group consisting of: a hydrogen sulfate anion; a hydrogen sulfite anion; a sulfonic acid anion represented by R 1 SO 3 − in which R 1 represents an alkyl group, a perfluoroalkyl group having from 1 to 10 carbon atoms, a cycloalkyl group, a vinyl group, an aryl group, a perfluoroaryl group, an aralkyl group or a halogen atom; and a bis(substituted sulfonyl)imide anion represented by (R 2 SO 2 ) 2 N − in which R 2 represents an alkyl group, a perfluoroalkyl group, an aryl group or a halogen atom.

6. The 2-cyanoacrylate-based adhesive composition according to claim 5 , wherein the cation of (c) the onium salt is at least one onium cation selected from the group consisting of a quaternary ammonium cation, an imidazolium cation, a pyridinium cation and a tertiary sulfonium cation, and the anion thereof is at least one selected from the group consisting of a hydrogen sulfate anion, a perfluoroalkanesulfonic acid anion, a bis(fluorosulfonyl)imide anion and a bis(perfluoroalkanesulfonyl)imide anion.

7. The 2-cyanoacrylate-based adhesive composition according to claim 5 , wherein a content of (c) the onium salt is from 0.001 to 2 parts by mass with respect to 100 parts by mass of (a) the 2-cyanoacrylic acid ester.

8. The 2-cyanoacrylate-based adhesive composition according to claim 1 , further comprising (d) a compound having a clathrate ability.

9. The 2-cyanoacrylate-based adhesive composition according to claim 8 , wherein (d) the compound having a clathrate ability is at least one compound selected from the group consisting of polyalkylene oxides, crown ethers and calixarenes.

10. The 2-cyanoacrylate-based adhesive composition according to claim 8 , wherein a content of (d) the compound having a clathrate ability is from 0.001 to 3 parts by mass with respect to 100 parts by mass of (a) the 2-cyanoacrylic acid ester.

Assignees

• Toagosei Co Ltd

Inventors

• Ishizaki Kenichi
• Ando Yushi

Classifications

• C09J4/00 Primary

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C09J11/06

  organic · CPC title

• C08F220/36

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title