Adhesive composition

Patent metadata

Field	Value
Publication number	US-9683146-B2
Application number	US-201414916032-A
Country	US
Kind code	B2
Filing date	Aug 7, 2014
Priority date	Sep 3, 2013
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

Abstract

Provided is an adhesive composition which is flexible, and exhibits excellent adhesion durability. The adhesive composition comprises (a) a 2-cyanoacrylic acid ester, (b) a polymer having a hydrolyzable silyl group, (c) an elastomer, and (d) an acid catalyst, in which the contents of the components (b), (c), and (d) are from 5 to 200 parts by mass, from 5 to 50 parts by mass, and from 0.0005 to 0.5 parts by mass, respectively, relative to 100 parts by mass of the component (a). Further preferably, the composition contains 0.001 to 5 parts by mass of (e) an onium salt relative to 100 parts by mass of the component (a).

First claim

The invention claimed is:

1. An adhesive composition which comprises (a) a 2-cyanoacrylic acid ester, (b) a polymer having a hydrolyzable silyl group, (c) an elastomer, and (d) an acid catalyst, in which the contents of the components (b), (c), and (d) are from 5 to 200 parts by mass, from 5 to 50 parts by mass, and from 0.0005 to 0.5 parts by mass, respectively, relative to 100 parts by mass of the component (a).

2. The adhesive composition according to claim 1 , wherein the main chain chemical structure of the polymer (b) having a hydrolyzable silyl group is at least one polymer selected from the group consisting of oxyalkylene polymer, vinyl polymer, polyester polymer, polyurethane polymer, and polycarbonate polymer.

3. The adhesive composition according to claim 1 , wherein the polymer (b) having a hydrolyzable silyl group has a number average molecular weight of from 500 to 50,000.

4. The adhesive composition according to claim 1 , wherein the elastomer (c) is a copolymer made from a monomer capable of forming a polymer poorly soluble to 2-cyanoacrylic acid ester and a monomer capable of forming a polymer soluble to 2-cyanoacrylic acid ester.

5. The adhesive composition according to claim 1 , wherein the elastomer (c) is a copolymer made from a monomer capable of forming a polymer poorly soluble to 2-cyanoacrylic acid ester, a monomer capable of forming a polymer soluble to 2-cyanoacrylic acid ester, and a monomer containing a carboxyl group.

6. The adhesive composition according to claim 4 , wherein the monomer capable of forming a polymer poorly soluble to 2-cyanoacrylic acid ester is at least one selected from ethylene, propylene, isoprene, and butadiene, and the monomer capable of forming a polymer soluble to 2-cyanoacrylic acid ester is at least one selected from acrylic acid esters and methacrylic acid esters.

7. The adhesive composition according to claim 1 , wherein the acid catalyst (d) is an acid having a pKa of 4 or lower at 25° C.

8. The adhesive composition according to claim 1 , wherein the acid catalyst (d) is at least one selected from the group consisting of sulfonic acid, phosphoric acid, phosphoric acid monoesters, phosphoric acid diesters, phosphorous acid, and phosphorous acid esters.

9. The adhesive composition according to claim 1 , which further comprises an onium salt (e) represented by the following general formula (1):
C + A −   (1)

wherein C + is an onium cation, and A − is a hydrogen sulfate anion, a hydrogen sulfite anion, a sulfonate anion represented by R 1 SO 3 − wherein R 1 represents an alkyl group, perfluoroalkyl group, cycloalkyl group, vinyl group, aryl group, perfluoroaryl group, aralkyl group or halogen atom; or a bis(substituted sulfonyl)imide anion represented by (R 2 SO 2 ) 2 N − wherein R 2 represents an alkyl group, perfluoroalkyl group, or aryl group; tetrafluoroborate anion, or hexafluorophosphate anion.

10. The adhesive composition according to claim 9 , wherein the cation of the onium salt (e) is at least one onium cation selected from the group consisting of quaternary ammonium cation, imidazolium cation, pyridinium cation, and tertiary sulfonium cation.

11. The adhesive composition according to claim 9 , which contains the onium salt (e) in an amount of from 0. 001 to 5 parts by mass, relative to 100 parts by mass of the 2-cyanoacrylic acid ester (a).

12. The adhesive composition according to claim 1 , wherein the main chain chemical structure of the polymer (b) having a hydrolyzable silyl group is at least one polymer selected from the group consisting of oxyalkylene polymer, vinyl polymer, polyester polymer, polyurethane polymer, and polycarbonate polymer; the elastomer (c) is a copolymer made from a monomer capable of forming a polymer poorly soluble to 2-cyanoacrylic acid ester and a monomer capable of forming a polymer soluble to 2-cyanoacrylic acid ester; the acid catalyst (d) is at least one selected from the group consisting of sulfonic acid, phosphoric acid, phosphoric acid monoesters, phosphoric acid diesters, phosphorous acid, and phosphorous acid esters; and an onium salt (e) represented by the following general formula (1):
C + A −   (1)

wherein C + is an onium cation, and A − is a hydrogen sulfate anion, a hydrogen sulfite anion, a sulfonate anion represented by R 1 SO 3 − wherein R 1 represents an alkyl group, perfluoroalkyl group, cycloalkyl group, vinyl group, aryl group, perfluoroaryl group, aralkyl group or halogen atom; or a bis(substituted sulfonyl)imide anion represented by (R 2 SO 2 ) 2 N − wherein R 2 represents an alkyl group, perfluoroalkyl group, or aryl group; tetrafluoroborate anion, or hexafluorophosphate anion.

Assignees

• Toagosei Co Ltd

Inventors

• Ishiazaki Kenichi
• Ando Yushi

Classifications

• C09J143/00

  Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Adhesives based on derivatives of such polymers · CPC title

• C08L33/14

  of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08L21/00

  Compositions of unspecified rubbers · CPC title

• C09J4/06

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00 · CPC title

• C09J143/04

  Homopolymers or copolymers of monomers containing silicon · CPC title