IP Library Granted Patent US 12,091,586
Granted Patent B2
US 12,091,586 · App. 17/279,922 · Granted Sep 17, 2024

Two-pack curable adhesive composition

Inventors: Hirokazu Kageyama (Hiratsuka, JP); Kazushi Kimura (Hiratsuka, JP); Yutaro Yamamoto (Hiratsuka, JP)
Assignee: The Yokohama Rubber Co., Ltd.
C09J175/08C08G18/10C08G18/1816C08G18/4829C08G18/4845C08G18/4854C08G18/7671C08K3/04C08K3/26C08K3/36C08K5/12C08K13/02C09J11/04C09J11/06C08K2003/265C08K2201/014C09J2475/00
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Quick Facts
Patent No.
US 12,091,586
App. No.
17/279,922
Granted
Sep 17, 2024
Kind
B2
Abstract

The two-part curable adhesive composition contains a main agent (A) containing a urethane prepolymer (a1) and a residual polyisocyanate (a2), and a curing agent (B) containing a polyol compound (b1) and a polyamine compound (b2). The urethane prepolymer (a1) is made by reacting in an equivalent ratio of an isocyanate group in a raw material polyisocyanate to a hydroxy group in a polytetramethylene ether glycol being 2.05 or greater. The equivalent ratio of an isocyanate group in the main agent (A) to an active hydrogen group in the curing agent (B) is from 0.5 to 4.

Claims (23)

1. A two-part curable adhesive composition comprising a main agent (A) containing a urethane prepolymer (a1), and a curing agent (B) containing a polyol compound (b1) and a polyamine compound (b2),

the polyamine compound (b2) has a number average molecular weight of less than 500, and contains at least two amino groups and at least one aromatic group in each molecule,

the urethane prepolymer (a1) being made by reacting a raw material polyisocyanate and a polytetramethylene ether glycol in an equivalent ratio of an isocyanate group in the raw material polyisocyanate to a hydroxy group in the polytetramethylene ether glycol being 2.05 or greater, with all of the polytetramethylene ether glycol turning to a monomer unit for the urethane prepolymer (a1),

the main agent (A) further containing, in addition to the urethane prepolymer (a1), a residual polyisocyanate (a2) which is a remainder of the raw material polyisocyanate that did not react with the polytetramethylene ether glycol, and

an equivalent ratio of an isocyanate group in the main agent (A) to an active hydrogen group in the curing agent (B) being from 0.5 to 4.

2. The two-part curable adhesive composition according to claim 1 , wherein an equivalent ratio of an amino group in the polyamine compound (b2) to a hydroxy group in the polyol compound (b1) is from 1.5 to 6, and

an equivalent ratio of an isocyanate group in the main agent (A) to an amino group in the polyamine compound (b2) is from 0.8 to 4.

3. The two-part curable adhesive composition according to claim 1 , wherein a number average molecular weight of the polytetramethylene ether glycol is 500 or greater.

4. The two-part curable adhesive composition according to claim 1 , wherein a number average molecular weight of the polyol compound (b1) is 500 or greater.

5. The two-part curable adhesive composition according to claim 1 , wherein the polyol compound (b1) contains at least one of a monomer unit of polyethylene glycol or a monomer unit of polypropylene glycol in each molecule.

6. The two-part curable adhesive composition according to claim 1 , wherein the main agent (A) contains at least one selected from the group consisting of a filler, an anti-aging agent, a coloring agent, a viscosity modifier, and a plasticizer.

7. The two-part curable adhesive composition according to claim 1 , wherein the curing agent (B) contains at least one selected from the group consisting of a filler, an anti-aging agents, a coloring agent, a viscosity modifier, a plasticizer, and polyhydric alcohols having a number average molecular weight of less than 500.

8. The two-part curable adhesive composition according to claim 1 , wherein a cured product obtained by curing the two-part curable adhesive composition has a tensile strength of 15 MPa or greater, and an elongation at break of 150% or greater, as determined in accordance with JIS K6251.

9. The two-part curable adhesive composition according to claim 1 , wherein a cured product obtained by curing the two-part curable adhesive composition has a modulus of elasticity in tension of 50 MPa or greater.

10. The two-part curable adhesive composition according to claim 1 , wherein a mass ratio of the main agent (A) to the curing agent (B) is from 3:7 to 7:3.

11. The two-part curable adhesive composition according to claim 1 , having a workable life of from 30 seconds to 10 minutes.

12. A two-part curable adhesive composition comprising a main agent (A) containing a urethane prepolymer (a1), and a curing agent (B) containing a polyol compound (b1) and a polyamine compound (b2),

the polyamine compound (b2) has a number average molecular weight of less than 500, and contains at least two amino groups and at least one aromatic group in each molecule,

the urethane prepolymer (a1) being made by reacting a raw material polyisocyanate and a polytetramethylene ether glycol in an equivalent ratio of an isocyanate group in the raw material polyisocyanate to a hydroxy group in the polytetramethylene ether glycol, the equivalent ratio being adjusted such that a cured product obtained by curing the two-part curable adhesive composition has a tensile strength of 15 MPa or greater and an elongation at break of 150% or greater in accordance with JIS K6251, with all of the polytetramethylene ether glycol turning to a monomer unit for the urethane prepolymer (a1),

the main agent (A) further containing, in addition to the urethane prepolymer (a1), a residual polyisocyanate (a2) that is a remainder of the raw material polyisocyanate that did not react with the polytetramethylene ether glycol and

an equivalent ratio of an isocyanate group in the main agent (A) to an active hydrogen group in the curing agent (B) being from 0.5 to 4.

13. The two-part curable adhesive composition according to claim 2 , wherein the adhesive composition contains no catalyst that is an organometal compound or a tertiary amine.

14. The two-part curable adhesive composition according to claim 1 , wherein the adhesive composition contains no catalyst that is an organometal compound or a tertiary amine.

Assignments (2)
CHANGE OF ADDRESS FOR ASSIGNEE Recorded Nov 18, 2023
From: THE YOKOHAMA RUBBER CO., LTD.
To: THE YOKOHAMA RUBBER CO., LTD.
Reel/Frame 065626/0740 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2022
From: KAGEYAMA, HIROKAZU; KIMURA, KAZUSHI; YAMAMOTO, YUTARO
To: THE YOKOHAMA RUBBER CO., LTD.
Reel/Frame 058591/0697 →