2-cyanoacrylate adhesive composition

Patent metadata

Field	Value
Publication number	US-9688840-B2
Application number	US-201515124316-A
Country	US
Kind code	B2
Filing date	Feb 27, 2015
Priority date	Mar 11, 2014
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

Abstract

An adhesive composition is provided which is excellent in adhesion rate on non-polar hard-to-bond materials and bond gap curability, and further is good in storage stability. It is a 2-cyanoacrylate-based adhesive composition which includes (a) a 2-cyanoacrylic acid ester and (b) an onium salt represented by the following general formula (1):

n C + A − n -X  (1)

wherein, in formula (1), C + represents an onium cation, A − represents at least one anion selected from the group consisting of —SO 3 − , —OSO 3 − and a specific imide anion, X represents a linking group which connects at least two anions together, and n is an integer of 2 or more.

First claim

The invention claimed is:

1. A 2-cyanoacrylate-based adhesive composition which comprises (a) a 2-cyanoacrylic acid ester and (b) an onium salt represented by the following formula (1):
n C + A − n -X  (1)

wherein, in formula (1),
C + represents an onium cation,
A − represents at least one anion selected from the group consisting of —SO 3 − , —OSO 3 − and an imide anion represented by the following formula (2),
X represents a linking group comprising an organic group, which connects at least two anions together, and
n is an integer of 2 or more,

wherein, in formula (2), R 1 represents a fluorine atom, alkyl group, cycloalkyl group, perfluoroalkyl group, aryl group, aralkyl group, alkenyl group or alkynyl group.

2. The 2-cyanoacrylate-based adhesive composition according to claim 1 , wherein the cation of the onium salt (b) is at least one onium cation selected from a group consisting of a quaternary ammonium cation, a quaternary phosphonium cation, an imidazolium cation, a pyridinium cation, and a tertiary sulfonium cation.

3. The 2-cyanoacrylate-based adhesive composition according to claim 1 , wherein the anion of the onium salt (b) is at least one anion selected from a group consisting of —SO 3 − , —OSO 3 − , a fluorosulfonylimide anion and a perfluoroalkylsulfonylimide anion.

4. The 2-cyanoacrylate-based adhesive composition according to claim 1 , wherein the linking group X in formula (1) is a divalent linking group.

5. The 2-cyanoacrylate-based adhesive composition according to claim 4 , wherein the linking group X in formula (1) is at least one divalent linking group selected from the group consisting of an alkylene group, a cycloalkylene group, an arylene group and a biphenyl group.

6. The 2-cyanoacrylate-based adhesive composition according to claim 1 , wherein the content of the onium salt (b) is 10 to 20,000 ppm relative to 100 parts by mass of the 2-cyanoacrylic acid ester (a).

7. The 2-cyanoacrylate-based adhesive composition according to claim 1 , wherein the organic group contains an aromatic ring, a double bond, a triple bond, a cyclic structure, an ester bond, an ether bond, a thioether bond, a siloxane bond, or a combination thereof.

8. The 2-cyanoacrylate-based adhesive composition according to claim 1 , wherein the linking group comprises a divalent, trivalent or tetravalent organic group.

9. The 2-cyanoacrylate-based adhesive composition according to claim 8 , wherein said organic group comprises a hydrocarbon group.

10. The 2-cyanoacrylate-based adhesive composition according to claim 8 , wherein said organic group comprises a divalent hydrocarbon group.

11. The 2-cyanoacrylate-based adhesive composition according to claim 8 , wherein said organic group comprises a trivalent hydrocarbon group.

12. The 2-cyanoacrylate-based adhesive composition according to claim 8 , wherein said organic group comprises a tetravalent hydrocarbon group.

13. The 2-cyanoacrylate-based adhesive composition according to claim 8 , wherein the cation of the onium salt (b) is at least one onium cation selected from a group consisting of a quaternary ammonium cation, a quaternary phosphonium cation, an imidazolium cation, a pyridinium cation, and a tertiary sulfonium cation.

14. The 2-cyanoacrylate-based adhesive composition according to claim 8 , wherein the anion of the onium salt (b) is at least one anion selected from the group consisting of —SO 3 − , —OSO 3 − , a fluorosulfonylimide anion and a perfluoroalkylsulfonylimide anion.

15. The 2-cyanoacrylate-based adhesive composition according to claim 8 , wherein the anion of the onium salt (b) is at least one anion selected from the group consisting of —SO 3 − and —OSO 3 − .

16. The 2-cyanoacrylate-based adhesive composition according to claim 8 , wherein the content of the onium salt (b) is 10 to 20,000 ppm relative to 100 parts by mass of the 2-cyanoacrylic acid ester (a).

17. The 2-cyanoacrylate-based adhesive composition according to claim 1 , wherein the linking group comprises a hydrocarbon group, wherein the hydrocarbon group optionally includes a substituent, an aromatic ring, a double bond, a triple bond, a cyclic structure, an ester bond, an ether bond, a thioether bond, a siloxane bond or a combination thereof, wherein said substituent comprises an alkanoyl group, a halogen atom, a silyl group, a nitro group, an azide group, a cyano group, or a nitroso group.

18. A 2-cyanoacrylate-based adhesive composition which comprises
(a) a 2-cyanoacrylic acid ester; and
(b) an onium salt represented by the following formula (1):
n C + A − n -X  (1)

wherein
C + represents an onium cation comprising at least one onium cation selected from a group consisting of a quaternary ammonium cation, a quaternary phosphonium cation, an imidazolium cation, a pyridinium cation, and a tertiary sulfonium cation,
A − represents at least one anion selected from the group consisting of —SO 3 − , —OSO 3 − and an imide anion,
X represents a linking group comprising a divalent organic group, which connects at least two anions together,
n is an integer of 2 or more, and
said imide anion is represented by the following formula (2)

wherein R 1 represents a fluorine atom, alkyl group, cycloalkyl group, perfluoroalkyl group, aryl group, aralkyl group, alkenyl group or alkynyl group.

19. The 2-cyanoacrylate-based adhesive composition according to claim 18 , wherein the anion of the onium salt (b) is at least one anion selected from a group consisting of —SO 3 − , —OSO 3 − , a fluorosulfonylimide anion and a perfluoroalkylsulfonylimide anion.

20. The 2-cyanoacrylate-based adhesive composition according to claim 19 , wherein the divalent linking group X in general formula (1) comprises a divalent linking group selected from the group consisting of an alkylene group, a cycloalkylene group, an arylene group and a biphenyl group.

21. The 2-cyanoacrylate-based adhesive composition according to claim 18 , wherein the content of the onium salt (b) is 10 to 20,000 ppm relative to 100 parts by mass of the 2-cyanoacrylic acid ester (a).

Assignees

• Toagosei Co Ltd

Inventors

• Ishizaki Kenichi
• Ando Yushi

Classifications

• C08K5/42 Primary

  Sulfonic acids; Derivatives thereof · CPC title

• C08K5/3462

  Six-membered rings · CPC title

• C09J135/04

  Homopolymers or copolymers of nitriles (C09J135/06, C09J135/08 take precedence) · CPC title

• C09J2205/102

  Chemistry & Metallurgy · mapped topic

• C09J4/00

  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