IP Library › Granted Patent US 12,319,850
Granted Patent B2
US 12,319,850 · App. 17/721,929 · Granted Jun 3, 2025

Polyurethane hot melt adhesive for low temperature application

Inventors: Joann Sutyak (Plainsboro, NJ); Benjamin Michael Biber (New Hope, PA); Jignesh P. Sheth (Bridgewater, NJ)
Assignee: Henkel AG & Co. KGaA
C09J175/06C08G18/12C08G18/2081C08G18/307C08G18/4202C08G18/4808C08G18/7671C09J175/08C08G2170/00C09J2301/304C09J2301/306
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Quick Facts
Patent No.
US 12,319,850
App. No.
17/721,929
Granted
Jun 3, 2025
Kind
B2
Abstract

Disclosed is a moisture reactive polyurethane hot melt adhesive composition that can be applied to substrates at a low coating weight even at application temperatures as low as 60 to 95° C. while retaining the advantageous high tack, green strength, cured bond strength and toughness of conventional high melting point polyurethane hot melt adhesives.

Claims (55)

1. A moisture curable, polyurethane, hot melt adhesive comprising an isocyanate functional prepolymer that is the reaction product of a mixture comprising:

3 to 30 wt. %, based on the total weight of the hot melt adhesive, of an amorphous polyester polyol having a Tg greater than 0° C.;

10 to 40 wt. %, based on the total weight of the hot melt adhesive, of at least one crystalline polyester polyol, wherein the at least one crystalline polyester polyol has a melting point in the range of from 20° C. to 100° C.;

wherein the weight ratio of crystalline polyester polyol: amorphous polyester polyol is in the range of 2:1 to 1:2;

10 to 30 wt. %, based on the total weight of the hot melt adhesive, of a diisocyanate;

5 to 50 wt. %, based on the total weight of the hot melt adhesive, of at least one polyether polyol;

a catalyst; and

either:

(i) 0.1 to 3 wt. %, based on the total weight of the hot melt adhesive, of a polyisocyanate having a functionality greater than 2, or

(ii) 0.1 to 10 wt. %, based on the total weight of the hot melt adhesive, of a thermoplastic polyurethane having hydroxyl functionality,

wherein:

the weight ratio of the total amount of the at least one crystalline polyester polyol to the total amount of the amorphous polyester polyol is of from 2:1 to 1:2, and

the hot melt adhesive has a green strength of at least 0.4 psi or more 5 minutes after application of the hot melt adhesive to a substrate at a temperature of from 60 to 95° C. and a coating weight of 10 gsf or less.

2. The moisture curable, polyurethane, hot melt adhesive of claim 1 , further comprising another amorphous polyester polyol having a Tg of from −60° C. to 0° C.

3. The moisture curable, polyurethane, hot melt adhesive of claim 1 , further comprising another crystalline polyester polyol different from the at least one crystalline polyester polyol and having a melting point of from 20° C. to 100° C.

4. The moisture curable, polyurethane, hot melt adhesive of claim 1 , further comprising another polyether polyol different from the at least one polyether polyol.

5. The moisture curable, polyurethane, hot melt adhesive of claim 1 , further comprising 10 to 30 wt. %, based on the total weight of the hot melt adhesive, of one or more additives.

6. The moisture curable, polyurethane, hot melt adhesive of claim 1 , wherein the hot melt adhesive is free of organometallic catalysts.

7. The moisture curable, polyurethane, hot melt adhesive of claim 1 , wherein the weight ratio of the total amount of the at least one crystalline polyester polyol to the total amount of the amorphous polyester polyol is 1:1.

8. The moisture curable, polyurethane, hot melt adhesive of claim 1 , wherein the hot melt adhesive has a Lauan board to vinyl foil green strength of 1.0 psi or more.

9. The moisture curable, polyurethane, hot melt adhesive of claim 1 , wherein the hot melt adhesive has an Azdel board to vinyl foil green strength of 0.4 psi or more.

10. The moisture curable, polyurethane, hot melt adhesive of claim 9 , wherein the hot melt adhesive has an Azdel board to vinyl foil green strength of 0.8 psi or more.

11. A moisture curable, polyurethane, hot melt adhesive comprising an isocyanate functional prepolymer that is the reaction product of a mixture comprising:

3 to 30 wt. %, based on the total weight of the hot melt adhesive, of an amorphous polyester polyol having a Tg greater than 0° C.;

10 to 40 wt. %, based on the total weight of the hot melt adhesive, of at least one crystalline polyester polyol, wherein the at least one crystalline polyester polyol has a melting point of from 20° C. to 100° C.;

either:

10 to 30 wt. %, based on the total weight of the hot melt adhesive, of a diisocyanate, or

5 to 50 wt. %, based on the total weight of the hot melt adhesive, of at least one polyether polyol;

a catalyst;

0.1 to 3 wt. %, based on the total weight of the hot melt adhesive, of a polyisocyanate having a functionality greater than 2; and

0.1 to 10 wt. %, based on the total weight of the hot melt adhesive, of a thermoplastic polyurethane having hydroxyl functionality,

wherein:

the weight ratio of the total amount of the at least one crystalline polyester polyol to the total amount of the amorphous polyester polyol is of from 2:1 to 1:2, and

the hot melt adhesive has a green strength of at least 0.4 psi or more 5 minutes after application of the hot melt adhesive to a substrate at a temperature of from 60 to 95° C. and a coating weight of 10 gsf or less.

12. A cured reaction product comprising the moisture curable, polyurethane, hot melt adhesive of claim 1 .

13. An article comprising the moisture curable, polyurethane, hot melt adhesive of claim 1 .

14. An article comprising the cured reaction product of claim 12 .

15. The moisture curable, polyurethane, hot melt adhesive of claim 1 , wherein the hot melt adhesive has a maximum viscosity of 12,000 cps at 95° C.

16. The moisture curable, polyurethane, hot melt adhesive of claim 15 , wherein the hot melt adhesive has a maximum viscosity of 5,000 cps at 95° C.

17. A method of coating a substrate, the method comprising:

heating the moisture curable, polyurethane, hot melt adhesive of claim 1 to a temperature of from 60 to 95° C.; and

coating the heated moisture curable, polyurethane, hot melt adhesive onto a coating surface of a first substrate at a coating weight of 10 grams per square foot (gsf) or less.

18. The moisture curable, polyurethane, hot melt adhesive of claim 11 , wherein the weight ratio of the total amount of the at least one crystalline polyester polyol to the total amount of the amorphous polyester polyol is 1:1.

19. The moisture curable, polyurethane, hot melt adhesive of claim 11 , further comprising one or more additives.

20. A moisture curable, polyurethane, hot melt adhesive comprising an isocyanate functional prepolymer that is the reaction product of a mixture comprising:

about 13.5 wt. %, based on the total weight of the hot melt adhesive, of an amorphous polyester polyol having a Tg greater than 0° C.;

about 25 wt. %, based on the total weight of the hot melt adhesive, of at least one crystalline polyester polyol, wherein the at least one crystalline polyester polyol has a melting point of from 20° C. to 100° C.;

about 18 wt. %, based on the total weight of the hot melt adhesive, of a diisocyanate;

about 15.5 wt. %, based on the total weight of the hot melt adhesive, of at least one polyether polyol;

a catalyst;

either:

(i) about 0.8 wt. %, based on the total weight of the hot melt adhesive, of a polyisocyanate having a functionality greater than 2, or

(ii) about 1.5 wt. %, based on the total weight of the hot melt adhesive, of a thermoplastic polyurethane having hydroxyl functionality; and

one or more additives, wherein:

the hot melt adhesive has a green strength of at least 0.4 psi or more 5 minutes after application of the hot melt adhesive to a substrate at a temperature of from 60 to 95° C. and a coating weight of 10 gsf or less.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2025
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 071030/0411 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2025
From: SHETH, JIGNESH P.
To: HENKEL IP & HOLDING GMBH
Reel/Frame 070999/0981 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2025
From: SUTYAK, JOANN
To: HENKEL IP & HOLDING GMBH
Reel/Frame 071000/0185 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2025
From: BIBER, BENJAMIN MICHAEL
To: HENKEL IP & HOLDING GMBH
Reel/Frame 071000/0550 →
Continuity (3)
Continuation PCTUS2020052613 · Sep 25, 2020
Provisional Application 62927931 · Oct 30, 2019
Related Publication 20220235249A1 · Jul 28, 2022
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