IP Library Granted Patent US 12,163,061
Granted Patent B2
US 12,163,061 · App. 17/279,974 · Granted Dec 10, 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.
C09J175/12C08G18/10C08G18/324C08G18/44C08G18/4845
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,163,061
App. No.
17/279,974
Granted
Dec 10, 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 polycarbonate polyol 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 (26)

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 urethane prepolymer (a1) being made by reacting a raw material polyisocyanate and only a polycarbonate polyol as a reactant that is reacted with the raw material polyisocycnate in an equivalent ratio of an isocyanate group in the raw material polyisocyanate to a hydroxy group in the polycarbonate polyol being 2.05 or greater with all of the polycarbonate polyol turning to a monomer unit for the urethane prepolymer (a1) so that the monomer units included in the urethane prepolymer (a1) being only a monomer unit of the raw material polyisocyanate and the monomer unit of the polycarbonate polyol,

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 polycarbonate polyol,

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, and

the adhesive composition comprising no catalyst.

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

3. The two-part curable adhesive composition according to claim 1 , wherein a number average molecular weight of the polycarbonate polyol is 500 or greater and 3000 or less.

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 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.

7. 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.

8. 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.

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 tensile strength of 15 MPa or greater, and an elongation at break of 150% or greater, as determined in accordance with JIS K6251.

10. 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.

11. 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.

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

13. 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 urethane prepolymer (a1) being made by reacting a raw material polyisocyanate and only a polycarbonate polyol as a reactant that is reacted with the raw material polyisocycnate in an equivalent ratio of an isocyanate group in the raw material polyisocyanate to a hydroxy group in the polycarbonate polyol so that the monomer units included in the urethane prepolymer (a1) being only a monomer unit of the raw material polyisocyanate and the monomer unit of the polycarbonate polyol, 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 polycarbonate polyol 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 polycarbonate polyol,

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, and

the adhesive composition comprising no catalyst.

14. The two-part curable adhesive composition according to claim 1 , wherein a cured product obtained by curing the two-part curable adhesive composition consists of a first polymer phase obtained by adding the raw material polyisocyanate to the polycarbonate polyol and reacting with the active hydrogen group of the curing agent (B) and a second polymer phase obtained by reacting the residual polyisocyanate (a2) with the active hydrogen group of the curing agent (B).

15. The two-part curable adhesive composition according to claim 14 , wherein the cured product has an islands-in-the-sea structure in which the first polymer phase is a dispersed phase and the second polymer phase is a continuous phase.

16. The two-part curable adhesive composition according to claim 1 , wherein the equivalent ratio of the isocyanate group in the raw material polyisocyanate to the hydroxy group in the polycarbonate polyol is 4 or greater.

17. The two-part curable adhesive composition according to claim 1 , wherein the adhesive composition comprises no organometal compound and no tertiary amine as a catalyst.

18. The two-part curable adhesive composition according to claim 13 , wherein the adhesive composition comprises no organometal compound and no tertiary amine as a catalyst.

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 058591/0921 →