IP Library Granted Patent US 12,398,304
Granted Patent B2
US 12,398,304 · App. 17/804,623 · Granted Aug 26, 2025

Thermally conductive polyurethane adhesive composition

Inventors: Thomas Zoeller (Essen, DE); Nicole Schlingloff (Duesseldorf, DE); Eric Schmitz (Viersen, DE); Thomas Engels (Duesseldorf, DE)
Assignee: Henkel AG & Co. KGaA
C09J175/08C08G18/10C08G18/4825C08G18/72C08K3/013C08K9/06C09J5/04C09J11/04C08K3/22C08K2003/2227C08K2201/001
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Quick Facts
Patent No.
US 12,398,304
App. No.
17/804,623
Granted
Aug 26, 2025
Kind
B2
Abstract

The present invention relates to a thermally conductive polyurethane adhesive composition having excellent mechanical properties as well as improved performance after aging and a method of manufacturing the same. Further, the present invention relates to method of manufacturing an article comprising the thermally conductive polyurethane adhesive composition and articles obtainable by the described method.

Claims (37)

1. A two-part composition comprising:

a component A comprising:

A1) a polyol;

A2) a chain extender; and

A3) a surface-treated thermally conductive inorganic filler with a surface having isocyanate-reactive groups; and

a component B comprising an isocyanate-terminated compound,

wherein an adhesive composition is obtained from a mixture of the component A and the component B.

2. The two-part composition according to claim 1 , wherein the polyol is a polyether polyol.

3. The two-part composition according to claim 1 , wherein the polyol has a molecular weight M n of from 700 to 12,000 g/mol.

4. The two-part composition according to claim 1 , wherein the chain extender is a diol selected from the group consisting of 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 3-methyl-1,5-prentanediol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, neopentyl glycol, polybutylene glycol, cyclohexane-1,2-diol, cyclohexane-1,4-diol, 1,4-bis(hydroxymethyl)cyclohexane, dimer diols, and mixtures thereof.

5. The two-part composition according to claim 1 , wherein the chain extender has a molecular weight M n of from 60 to 600 g/mol.

6. The two-part composition according to claim 1 , wherein the thermally conductive inorganic filler is selected from the group consisting of metal oxides, metal hydroxides, metal silicates, metal sulfides, and combinations thereof.

7. The two-part composition according to claim 1 , wherein the thermally conductive inorganic filler is selected from the group consisting of aluminum oxide, aluminum hydroxide, aluminum silicate, and combinations thereof.

8. The two-part composition according to claim 1 , wherein the isocyanate-reactive groups comprise an isocyanate-reactive group selected from the group consisting of hydroxyl, amino, carboxyl, thiol, epoxy group, and combinations thereof.

9. The two-part composition according to claim 1 , wherein the isocyanate-reactive groups comprise an isocyanate-reactive group that is a hydrolyzed residue of an aminoalkoxysilyl compound or epoxidized alkoxysilyl compound.

10. The two-part composition according to claim 1 , wherein:

the isocyanate-reactive groups comprise an isocyanate-reactive group that is a hydrolyzed residue of an epoxidized alkylsilyl compound, the aminoalkylsilyl compound selected from the group consisting of γ-glycidoxypropyltrimethoxysilyl, γ-glycidoxypropyltriethoxysilyl, γ-glycidoxypropylmethyldimethoxysilyl, and γ-glycidoxypropylmethyldiethoxysilyl, or

the isocyanate-reactive groups comprise an isocyanate-reactive group that is a hydrolyzed residue of an aminoalkylsilyl compound, the aminoalkylsilyl compound selected from the group consisting of aminoethyltrimethoxysilyl, aminoethyltriethoxysilyl, aminopropyltrimethoxysilyl, aminopropyltriethoxysilyl, aminopropylmethyldimethoxysilyl, aminopropylmethyldiethoxysilyl, aminoethyl-γ-aminopropyl-trimethoxysilyl, and iminobis(propyltrimethoxysilyl), or

combinations thereof.

11. The two-part composition according to claim 1 , wherein the isocyanate-terminated compound is an aliphatic or aromatic isocyanate-terminated compound.

12. The two-part composition according to claim 1 , wherein the isocyanate-terminated compound is a mixture of aromatic (poly) isocyanates and/or aromatic (poly) isocyanate prepolymers.

13. The two-part composition according to claim 1 , wherein the ratio by mass of components A and B is from 10:1 to 1:5.

14. The two-part composition according to claim 1 , wherein the surface-treated thermally conductive inorganic filler is present in an amount of from 10 wt. % to 90 wt. %, based on the total weight of component A.

15. The two-part composition according to claim 1 , wherein the polyol and the chain extender are present in the component A in a weight ratio of from 20:1 to 4:1.

16. The two-part composition according to claim 1 , wherein the ratio by mass of components A and B is of from 5:1 to 1:1.

17. A cured adhesive product obtained by:

mixing the component A and the component B of the two-part composition according to claim 1 to form an adhesive composition; and

curing the adhesive composition.

18. The cured adhesive product according to claim 17 , having a thermal conductivity of at least 0.8 W/mK, determined according to ISO 22007-2 at 25° C.

19. A method of manufacturing an article comprising:

providing a first substrate having a bonding surface;

providing a second substrate having a bonding surface;

providing the component A and the component B of the two-part composition of claim 1 ;

mixing the component A and the component B to obtain an adhesive composition;

applying the adhesive composition onto the bonding surface of the first substrate; and

bringing the bonding surface of the second substrate into contact with the adhesive composition on the bonding surface of the first substrate.

20. The method of manufacturing an article of claim 19 , further comprising curing the mixed adhesive disposed between the bonding surface of the first substrate and the bonding surface of the second substrate.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2025
From: SCHMITZ, ERIC
To: HENKEL AG & CO. KGAA
Reel/Frame 071924/0659 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2025
From: SCHLINGLOFF, NICOLE
To: HENKEL AG & CO. KGAA
Reel/Frame 071924/0854 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 9, 2025
From: ZOELLER, THOMAS
To: HENKEL AG & CO. KGAA
Reel/Frame 070780/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 9, 2025
From: ENGELS, THOMAS
To: HENKEL AG & CO. KGAA
Reel/Frame 070780/0618 →
Priority Claims (1)
EP 19216133 · Dec 13, 2019 · regional
Continuity (2)
Continuation PCTEP2020083843 · Nov 30, 2020
Related Publication 20220290020A1 · Sep 15, 2022
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