IP Library Granted Patent US 12,091,585
Granted Patent B2
US 12,091,585 · App. 16/973,699 · Granted Sep 17, 2024

Two-part urethane adhesive composition

Inventors: Yuichi Matsuki (Kanagawa, JP); Megumi Abe (Kanagawa, JP)
Assignee: SIKA TECHNOLOGY AG
C09J175/08C08G18/12C08G18/2081C08G18/3215C08G18/4812C08G18/4816C08G18/4829C08G18/4841C08G18/4866C08G18/667C08G18/724C08G18/7671C08G18/792C08K2003/265
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 12,091,585
App. No.
16/973,699
Granted
Sep 17, 2024
Kind
B2
Abstract

A two-part urethane adhesive composition that provides excellent initial adhesiveness and excellent long-term adhesiveness. An embodiment of the present invention is a two-part urethane adhesive composition including a main agent containing a urethane prepolymer having an isocyanate group, and a curing agent containing a compound (A) having two or more active hydrogen-containing groups per molecule, the compound (A) including a polyol compound (a1), the polyol compound (a1) having three active hydrogen-containing groups per molecule, having ethylene oxide at a terminal, having a number average molecular weight of greater than 1000 and 20000 or less, having a degree of unsaturation of 0.01 meq/g or less, and having molecular weight distribution (Mw/Mn) of 1.05 or less, and a molar ratio of a total amount of active hydrogen in the compound (A) with respect to an amount of the isocyanate group being 0.2 or greater and less than 0.8.

Claims (30)

1. A two-part urethane adhesive composition comprising:

a main agent containing a urethane prepolymer having an isocyanate group; and

a curing agent containing a compound (A) having two or more active hydrogen-containing groups per molecule;

the compound (A) comprising a polyol compound (a1) and a polyol compound (a2), the polyol compound (a1) having three active hydrogen-containing groups per molecule, having ethylene oxide at a terminal, having a number average molecular weight of greater than 1000 and 20000 or less, having a degree of unsaturation of 0.01 meq/g or less, and having molecular weight distribution (Mw/Mn) of 1.05 or less, and

the polyol compound (a2), having three or more active hydrogen-containing groups per molecule and having a number average molecular weight of from 200 to 1000, and

a molar ratio of a total amount of active hydrogen in the compound (A) with respect to an amount of the isocyanatc group being 0.2 or greater and less than 0.8,

wherein an amount (H1) of active hydrogen in the polyol compound (a1) is from 20 to 80 mol % with respect to a total of the amount (H1) and an amount (H2) of active hydrogen in the polyol compound (a2), and

the amount (H2) is from 80 to 20 mol % with respect to the total of the amount (H1) and the amount (H2).

2. The two-part urethane adhesive composition according to claim 1 , wherein each of the active hydrogen-containing groups in the polyol compound (a1) is a hydroxyl group,

the ethylene oxide in the polyol compound (a1) is represented by —(CH 2 CH 2 -0) r1 -, where the r1 moiety is 1 or 2 or greater, and

the hydroxy group and the —(CH 2 CH 2 -0) r1 - moiety are linked to form —(CH 2 CH 2 -0) r1 -H.

3. The two-part urethane adhesive composition according to claim 2 , wherein the polyol compound (a1) has three —(CH 2 CH 2 —O) r1 —H moieties per molecule.

4. The two-part urethane adhesive composition according to claim 1 , wherein, in the polyol compound (a1), each of the active hydrogen-containing groups is bonded to a linking group via the ethylene oxide.

5. The two-part urethane adhesive composition according to claim 1 , wherein the polyol compound (a2) has ethylene oxide at a terminal.

6. The two-part urethane adhesive composition according to claim 1 , wherein

each of the active hydrogen-containing groups in the polyol compound (a2) is a hydroxyl group,

the polyol compound (a2) has ethylene oxide at a terminal,

the ethylene oxide in the polyol compound (a2) is represented by —(CH 2 CH 2 -0) r2 -, where the r2 moiety is 1 or 2 or more, and

the hydroxy group and the —(CH 2 CH 2 -0) r2 - moiety are linked to form —(CH 2 CH 2 -0) r2 -H.

7. The two-part urethane adhesive composition according to claim 6 , wherein the polyol compound (a2) has four or more —(CH 2 CH 2 -0) r2 -H moieties per molecule.

8. The two-part urethane adhesive composition according to claim 1 , wherein

the polyol compound (a2) has ethylene oxide at a terminal and,

in the polyol compound (a2), each of the active hydrogen-containing groups is bonded to a linking group via the ethylene oxide.

9. The two-part urethane adhesive composition according to claim 1 , used for adhering of a base material.

10. The two-part urethane adhesive composition according to claim 9 , wherein the base material comprises a polyolefin.

11. The two-part urethane adhesive composition according to claim 1 , wherein

the composition further comprises an amine-based curing catalyst, and

the amine-based curing catalyst is contained at an amount of 0.05 to 0.5 parts by mass with respect to 100 parts by mass of the urethane prepolymer.

12. The two-part urethane adhesive composition according to claim 1 , wherein the compound A consists of the polyol compound (a1) and the polyol compound (a2).

13. The two-part urethane adhesive composition according to claim 1 , wherein the polyol compound (a2) has a number average molecular weight of from 200 to 500.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 21, 2024
From: SIKA JAPAN LTD.
To: SIKA TECHNOLOGY AG
Reel/Frame 066641/0001 →
MERGER Recorded Feb 5, 2024
From: SIKA HAMATITE CO., LTD.
To: SIKA JAPAN LTD.
Reel/Frame 066493/0072 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 23, 2021
From: THE YOKOHAMA RUBBER CO., LTD.
To: SIKA HAMATITE CO., LTD.
Reel/Frame 058198/0278 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 9, 2020
From: MATSUKI, YUICHI; ABE, MEGUMI
To: THE YOKOHAMA RUBBER CO., LTD.
Reel/Frame 054597/0072 →
Priority Claims (1)
JP 2018-113197 · Jun 13, 2018 · national
Continuity (1)
Related Publication 20210253920A1 · Aug 19, 2021