Two-part curable composition

Patent metadata

Field	Value
Publication number	US-9994662-B2
Application number	US-201515533942-A
Country	US
Kind code	B2
Filing date	Dec 1, 2015
Priority date	Dec 12, 2014
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

The two-part curable composition has excellent curability, and exhibits flexibility and adhesion durability. The two-part curable composition includes a first reagent containing at least a 2-cyanoacrylic acid ester and a second reagent containing at least a polymer having a hydrolyzable silyl group, in which an elastomer and a curing catalyst for the above polymer are each contained in at least one of the first and second reagents in predetermined amounts. A preferable curing catalyst is a compound having a metal element and an organic group bonded to the metal element via oxygen, or an acid having a pKa of 4 or lower at 25° C. Preferably, a curing accelerator for 2-cyanoacrylic acid ester is contained in at least one of the first and second reagents.

First claim

The invention claimed is:

1. A two-part curable composition comprising a first reagent containing at least a Component (a) shown below and a second reagent containing at least a Component (c) shown below, in which Components (b) and (d) shown below are each contained in at least one of the first and second reagents, wherein
the contents of the Component (b) contained in the first and second reagents being 5-50 parts by mass relative to 100 parts of the Component (a) in terms of the Component (b) contained in the first reagent and being 5-50 parts by mass relative to 100 parts by mass of the Component (c) in terms of the Component (b) contained in the second reagent, and
the total amount of the Component (d) contained in the first and second reagents being 0.0005-10 parts by mass relative to 100 parts by mass of the Component (c), Component (a): a 2-cyanoacrylic acid ester;

Component (b): an elastomer;
Component (c): a polymer having a hydrolyzable silyl group; and
Component (d): a curing catalyst for the polymer (c).

2. The two-part curable composition according to claim 1 , wherein the elastomer 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.

3. The two-part curable composition according to claim 2 , wherein the monomer capable of forming a polymer poorly soluble to 2-cyanoacrylic acid ester is at least one selected from ethylene, propylene, isoprene, butadiene, chloroplene, 1-hexene and cyclopentene, and the monomer capable of forming a polymer soluble to 2-cyanoacrylic acid ester is at least one selected from acrylic acid esters, methacrylic acid esters, vinylchloride, vinylacetate, vinylether, styrene and acrylonitrile.

4. The two-part curable composition according to claim 1 , wherein the elastomer 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.

5. The two-part curable 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, butadiene, chloroplene, 1-hexene and cyclopentene, and the monomer capable of forming a polymer soluble to 2-cyanoacrylic acid ester is at least one selected from acrylic acid esters, methacrylic acid esters, vinylchloride, vinylacetate, vinylether, styrene and acrylonitrile.

6. The two-part curable composition according to claim 1 , wherein the main chain chemical structure of the polymer 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.

7. The two-part curable composition according to claim 6 , wherein the two part curable composition further comprises
a curing accelerator for 2-cyanoacrylic acid ester as the component (a) further contained in at least one of the first and second reagents, and wherein
the elastomer is (i) 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, or (ii) 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, and
the curing catalyst is (i) an acid having a pKa of 4 or lower at 25° C. or (ii) a compound having a metal element and an organic group bonded to the metal element via oxygen.

8. The two-part curable composition according to claim 1 , wherein the polymer having a hydrolyzable silyl group has a number average molecular weight of from 500 to 50,000.

9. The two-part curable composition according to claim 1 , wherein the curing catalyst is a compound having a metal element and an organic group bonded to the metal element via oxygen.

10. The two-part curable composition according to claim 9 , wherein the metal element of the curing catalyst is at least one selected from the group consisting of titanium, zirconium, hafnium, tin, aluminium and zinc.

11. The two-part curable composition according to claim 9 , wherein the organic group of the curing catalyst is at least one selected from the group consisting of alkoxy group, acetylacetone, acetoacetic ester, carboxyl group, and phenoxy group.

12. The two-part curable composition according to claim 1 , wherein the curing catalyst is an acid having a pKa of 4 or lower at 25° C.

13. The two-part curable composition according to claim 12 , wherein the acid 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.

14. The two-part curable composition according to claim 1 , wherein a curing accelerator for 2-cyanoacrylic acid ester as the component (a) is further contained in at least one of the first and second reagents.

15. The two-part curable composition according to claim 14 , in which the curing accelerator is an onium salt represented by the following general formula (1):
C + A −   (1)

wherein C + is an onium cation, and A − is one selected from the anion group consisting of:
a hydrogen sulfate anion, a hydrogen sulfite anion, a sulfonate anion represented by R 1 SO 3 − wherein R 1 is a group selected from the group consisting of an alkyl group, cycloalkyl group, vinyl group, aryl group, alkenyl group, alkynyl group and aralkyl group, or a halogen atom, and the aforementioned group may be substituted with a substituent,
a sulfate anion represented by R 2 OSO 3 − wherein R 2 is a group selected from the group consisting of an alkyl group, cycloalkyl group, vinyl group, aryl group, alkenyl group, alkynyl group and aralkyl group, and the aforementioned group may be substituted with a substituent,
a bis(substituted sulfonyl)imide anion represented by (R 3 SO 2 )(R 4 SO 2 )N − wherein R 3 and R 4 , which may be the same or different, are groups selected from the group consisting of an alkyl group, cycloalkyl group, vinyl group, aryl group, alkenyl group, alkynyl group and aralkyl group, or halogen atoms, and the aforementioned groups may be substituted with a substituent,
an imide anion represented by (R 5 CO)(R 6 CO)N − wherein R 5 and R 6 , which may be the same or different, are groups selected from the group consisting of an alkyl group, cycloalkyl group, vinyl group, aryl group, alkenyl group, alkynyl group and aralkyl group, or halogen atoms, and the aforementioned groups may be substituted with a substituent,
an sulfonylimide anion represented by (R 7 SO 2 )(R 8 CO)N − wherein R 7 and R 8 , which may be the same or different, are groups selected from the group consisting of an alkyl group, cycloalkyl group, vinyl group, aryl group, alkenyl group, alkynyl group and aralkyl group, or halogen atoms, and the aforementioned groups may be substituted with a substituent,
a perhalogenated lewis acid anion,
a tetrafluoroborate anion, a hexafluorophosphate anion, a halogen anion, a nitrate anion,
CN − , SCN − , OCN − , N(CN) 2 − ,
a phosphoric acid anion and a phosphate anion represented by (R 9 O) a PO 4-a (3-a)− wherein R 9 is a group selected from the group consisting of an alkyl group, cycloalkyl group, vinyl group, aryl group, alkenyl group, alkyny

Assignees

• Toagosei Co Ltd

Inventors

• Ishizaki Kenichi
• Ando Yushi

Classifications

• 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

• C08K5/057

  Metal alcoholates {(metal enolates C08K5/0091)} · CPC title

• C08F222/328

  Alpha-cyano-acrylic acid with more than one oxygen in the ester moiety · CPC title

• C08K5/5425

  containing at least one C=C bond · CPC title

• C09J201/00

  Adhesives based on unspecified macromolecular compounds · CPC title