IP Library Granted Patent US 11,708,514
Granted Patent B2
US 11,708,514 · App. 16/817,940 · Granted Jul 25, 2023

Solvent free liquid moisture curable polyurethane compositions with long open times and fast cure rates

Inventors: Yingjie Li (Elgin, IL); Shuhui Qin (Elgin, IL); Jeanne Li (Elgin, IL)
Assignee: Henkel AG & Co. KGaA
C09J175/04C08G18/3203C08G18/7664C09J11/06C09J11/08
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Quick Facts
Patent No.
US 11,708,514
App. No.
16/817,940
Granted
Jul 25, 2023
Kind
B2
Abstract

Disclosed is a liquid, solvent free, moisture curable polyurethane adhesive composition comprising the reaction products of at least one polyoxypropylene polyol having a hydroxyl functionality of at least three and ethylene oxide end-capping with one or more polyisocyanates having a weight average isocyanate functionality of greater than 2.3. The adhesive composition has a long open time and rapid cure time compared to currently available adhesives. The polyoxypropylene polyol preferably has a number average molecular weight of from 3,000 to 8,000. The composition finds special use in panel lamination applications.

Claims (26)

1. A liquid, solvent free, moisture curable polyurethane adhesive composition comprising:

an acid selected from phosphoric acid, trifluoromethane sulfonic acid, methane sulfonic acid and ethane sulfonic acid; and

the reaction products of:

a polyol component comprising at least one polyoxypropylene polyol having a hydroxyl functionality of from 3.0 to about 4.5 and ethylene oxide end-capping, wherein the polyol component is free of filler;

optionally one or more polyols selected from the group consisting of a non-polyoxypropylene polyol or a polyoxypropylene polyol that is not ethylene oxide end-capped or a polyoxypropylene polyol having a hydroxyl functionality outside the range of 3.0 to about 4.5; and

a polyisocyanate component comprising one or more polyisocyanates, wherein the one or more polyisocyanates have a weight average isocyanate functionality of from 2.3 to about 3.3.

2. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 wherein said one or more polyisocyanates having a weight average isocyanate functionality of at least 2.4 to about 3.3.

3. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 wherein said one or more polyisocyanates having a weight average isocyanate functionality of at least 2.5 to about 3.3.

4. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 wherein said at least one polyoxypropylene polyol is present in an amount of from 20 to 80% by weight based on the total weight of said composition.

5. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 wherein said at least one polyoxypropylene polyol is present in an amount of from 30 to 60% by weight based on the total weight of said composition.

6. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 wherein said one or more polyisocyanates is present in an amount of from 20 to 80% by weight based on the total weight of said composition.

7. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 wherein said one or more polyisocyanates is present in an amount of from 30 to 60% by weight based on the total weight of said composition.

8. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 wherein said at least one polyoxypropylene polyol has a number average molecular weight of from 3,000 to 8,000.

9. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 wherein said at least one polyoxypropylene polyol has a number average molecular weight of from 3,500 to 6,500.

10. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 , further comprising liquid mineral oil, liquid aromatic oil, and combinations thereof.

11. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 , comprising from 0.005 to 0.8 weight % based on the total composition weight of the acid.

12. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 wherein said one or more polyisocyanates comprises polymeric MDI or a mixture of polymeric MDI and MDI.

13. An assembly comprising the adhesive composition of claim 1 .

14. An assembly comprising cured reaction products of the adhesive composition of claim 1 .

15. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 wherein said composition is a two-component composition and wherein the two components are stored separately and combined immediately prior to use.

16. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 wherein said composition is a two-component composition and wherein the two components cannot be mixed and stored.

17. A liquid, solvent free, moisture curable polyurethane adhesive composition comprising the reaction products of:

one or more polyisocyanates, wherein the one or more polyisocyanates have a weight average isocyanate functionality of from 2.3 to about 3.3; and

at least one polyol, wherein all of the polyols in the reaction product are selected from the group consisting of polyoxypropylene polyol having a hydroxyl functionality of from 3.0 to about 4.5 and ethylene oxide end-capping; a non-polyoxypropylene polyol; a polyoxypropylene polyol that is not ethylene oxide endcapped; a polyoxypropylene polyol that is not ethylene oxide endcapped having a hydroxyl functionality outside the range of 3.0 to about 4.5; and combinations thereof;

wherein the adhesive composition is free of filler.

18. The liquid, solvent free, moisture curable polyurethane adhesive composition of claim 1 being free of filler.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059207/0627 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2020
From: LI, YINGJIE; QIN, SHUHUI; LI, JEANNE
To: HENKEL IP & HOLDING GMBH
Reel/Frame 053009/0993 →
Continuity (3)
Continuation PCTUS2018052167 · Sep 21, 2018
Provisional Application 62561759 · Sep 22, 2017
Related Publication 20200216728A1 · Jul 9, 2020