IP Library Granted Patent US 10,513,644
Granted Patent B2
US 10,513,644 · App. 15/580,664 · Granted Dec 24, 2019

Two-pack curable urethane adhesive composition

Inventors: Megumi Abe (Hiratsuka, JP); Yuichi Matsuki (Hiratsuka, JP); Takanori Kido (Hiratsuka, JP)
C09J175/04C07C11/21C08G18/2027C08G18/248C08G18/282C08G18/632C08G18/6492C08G18/69C09J11/06C09J11/08
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Quick Facts
Patent No.
US 10,513,644
App. No.
15/580,664
Granted
Dec 24, 2019
Kind
B2
Abstract

A two-part curable urethane adhesive composition of the present technology contains a base agent containing a urethane prepolymer, and a curing agent containing a compound having two or more active hydrogen groups in each molecule. The curing agent contains at least one type of terpene compound selected from the group consisting of monoterpenes, hydrogenated monoterpenes, modified monoterpenes formed by modifying the monoterpenes or the hydrogenated monoterpenes with hydroxy groups, and oligomers having from 2 to 6 repeating units derived from the monoterpenes or the modified monoterpenes.

Claims (28)

1. A two-part curable urethane adhesive composition comprising:

a base agent containing a urethane prepolymer, and a curing agent containing a compound having two or more active hydrogen groups in each molecule;

the curing agent containing at least one type of terpene compound selected from the group consisting of monoterpenes, hydrogenated monoterpenes, modified monoterpenes formed by modifying the monoterpenes or the hydrogenated monoterpenes with hydroxy groups, and oligomers having from 2 to 6 repeating units derived from the monoterpenes or the modified monoterpenes.

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

the monoterpene is a compound represented by Formula (1), a compound represented by Formula (2), or a compound represented by Formula (3);

the hydrogenated monoterpene is a compound represented by Formula (4);

the modified monoterpene is a compound represented by Formula (5), a compound represented by Formula (6), or a compound represented by Formula (7); and

the oligomer is a compound represented by Formula (8), a compound represented by Formula (9), or a compound represented by Formula (10):

where, in Formulas (8) to (10), m represents a number from 2 to 6, n represents a number from 1 to 3, and m×n is a number from 2 to 6; and in Formula (9), R represents a hydrogen atom or an alkyl group having from 1 to 12 carbons.

3. The two-part curable urethane adhesive composition according to claim 1 , wherein a content of the terpene compound is from 1 to 30 mass % relative to the total mass of the curing agent.

4. The two-part curable urethane adhesive composition according to claim 1 , wherein the curing agent contains a polybutadiene diol as the compound having two or more active hydrogen groups in each molecule.

5. The two-part curable urethane adhesive composition according to claim 1 , wherein the curing agent contains a rosin diol as the compound having two or more active hydrogen groups in each molecule.

6. The two-part curable urethane adhesive composition according to claim 1 , wherein the base agent further contains an isocyanate silane compound.

7. The two-part curable urethane adhesive composition according to claim 1 , wherein the curing agent contains a polyol compound as the compound having two or more active hydrogen groups in each molecule; and

the two-part curable urethane adhesive composition is used for adhesion to a resin material using no primer.

8. The two-part curable urethane adhesive composition according to claim 1 , wherein the terpene compound is at least one type selected from the group consisting of monoterpenes, hydrogenated monoterpenes, and modified monoterpenes formed by modifying the monoterpenes or the hydrogenated monoterpenes with hydroxy groups.

9. The two-part curable urethane adhesive composition according to claim 2 , wherein a content of the terpene compound is from 1 to 30 mass % relative to the total mass of the curing agent.

10. The two-part curable urethane adhesive composition according to claim 2 , wherein the curing agent contains a polybutadiene diol as the compound having two or more active hydrogen groups in each molecule.

11. The two-part curable urethane adhesive composition according to claim 3 , wherein the curing agent contains a polybutadiene diol as the compound having two or more active hydrogen groups in each molecule.

12. The two-part curable urethane adhesive composition according to claim 9 , wherein the curing agent contains a polybutadiene diol as the compound having two or more active hydrogen groups in each molecule.

13. The two-part curable urethane adhesive composition according to claim 2 , wherein the curing agent contains a rosin diol as the compound having two or more active hydrogen groups in each molecule.

14. The two-part curable urethane adhesive composition according to claim 3 , wherein the curing agent contains a rosin diol as the compound having two or more active hydrogen groups in each molecule.

15. The two-part curable urethane adhesive composition according to claim 4 , wherein the curing agent contains a rosin diol as the compound having two or more active hydrogen groups in each molecule.

16. The two-part curable urethane adhesive composition according to claim 9 , wherein the curing agent contains a rosin diol as the compound having two or more active hydrogen groups in each molecule.

17. The two-part curable urethane adhesive composition according to claim 10 , wherein the curing agent contains a rosin diol as the compound having two or more active hydrogen groups in each molecule.

18. The two-part curable urethane adhesive composition according to claim 11 , wherein the curing agent contains a rosin diol as the compound having two or more active hydrogen groups in each molecule.

19. The two-part curable urethane adhesive composition according to claim 12 , wherein the curing agent contains a rosin diol as the compound having two or more active hydrogen groups in each molecule.

20. The two-part curable urethane adhesive composition according to claim 2 , wherein the base agent further contains an isocyanate silane compound.

Assignments (5)
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 →
DE-MERGER Recorded Dec 8, 2021
From: THE YOKOHAMA RUBBER CO., LTD.
To: SIKA HAMATITE CO., LTD.
Reel/Frame 060439/0022 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 7, 2020
From: ALLIGATOR VENTILFABRIK GMBH
To: WEGMANN AUTOMOTIVE GMBH
Reel/Frame 053434/0765 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 7, 2017
From: ABE, MEGUMI; MATSUKI, YUICHI; KIDO, TAKANORI
To: THE YOKOHAMA RUBBER CO., LTD.
Reel/Frame 044760/0036 →
Continuity (1)
Related Publication 20180163103A1 · Jun 14, 2018