IP Library Granted Patent US 7,419,724
Granted Patent B2
US 7,419,724 · App. 10/626,387 · Granted Sep 2, 2008

Two-part polyurethane adhesives for structural finger joints and method therefor

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Quick Facts
Patent No.
US 7,419,724
App. No.
10/626,387
Granted
Sep 2, 2008
Kind
B2
Abstract

One aspect of the present invention is an adhesive composition formed from two packs. One pack includes an isocyanate-functional prepolymer formed by reacting a polyisocyanate with an alcohol (e.g., polyol). The isocyanate equivalents from the polyisocyanate exceed the hydroxyl equivalents from the alcohol. The second pack is an aqueous polymer emulsion. These two packs are combined to form the novel adhesive composition. Another aspect of the invention is a method for joining together two surfaces of wood products by application of an adhesive thereto. The first step in this method is to mist with water the wood product surfaces to be joined. An adhesive composition then is applied to the misted wood product surfaces. Alternatively, the water misting can be replaced with an aqueous emulsion being part of the adhesive composition. Finally, the adhesive composition is cured.

Claims (27)

1. A laminated wood product adhesively joined with the cured residue of an adhesive, which comprises:

(a) an isocyanate-functional prepolymer formed by reacting a polyisocyanate with an alcohol, where the isocyanate equivalents from the polyisocyanate exceeds the hydroxyl equivalents from the alcohol; and

(b) an aqueous polymer emulsion, the weight ratio of (a) to (b) ranging from about 95/5 to about 60/40.

2. The laminated wood product of claim 1 , wherein said adhesive has been cured by heat or radio frequency (RF) curing.

3. The laminated wood product of claim 1 , wherein said alcohol is selected from one or more of acrylates, esters, vinyls, castor oils, or polymers, containing active alcohol groups.

4. The laminated wood product of claim 3 , wherein said alcohol is selected from one or more of aliphatic and aromatic polyether polyols optionally alkylated, or caprolactone-based polyols.

5. The laminated wood product of claim 4 , wherein said alcohol is a block polyethylene or polypropylene oxide homo- or co-polymer ranging in molecular weight from about 300 to about 3,000.

6. The laminated wood product of claim 1 , wherein said isocyanate-terminated prepolymer is made from an isocyanate component selected from hexamethylene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), m- and p-phenylene diisocyanates, bitolylene diisocyanate, cyclohexane diisocyanate (CHDI), bis-isocyanatomethyl)cyclohexane (H 6 XDI), dicyclohexylmethane diisocyanate (H 12 MDI), dimer acid diisocyanate (DDI), trimethyl hexamethylene diisocyanate, lysine diisocyanate and its methyl ester, isophorone diisocyanate, methyl cyclohexane diisocyanate, 1,5-napthalene diisocyanate, xylylene and xylene diisocyanate and methyl derivatives thereof, polymethylene polyphenyl isocyanates, chlorophenylene-2,4-diisocyanate, polyphenylene diisocyanates, isophorone diisocyanate (IPDI), hydrogenated methylene diphenyl isocyanate (HMDI), tetramethyl xylene diisocyanate (TMXDI), hexamethylene diisocyanate (HDI), or oligomers thereof, and mixtures thereof.

7. The laminated wood product of claim 1 , wherein said isocyanate prepolymer contains a defoamer and an inhibitor.

8. The laminated wood product of claim 1 , wherein the weight ratio of said isocyanate-functional prepolymer to said aqueous polymer emulsion ranges from about 90/10 to about 70/30.

9. The laminated wood product of claim 1 , wherein said aqueous polymer emulsion is one or more of acrylic emulsions, vinyl emulsions, styrene-butadiene polymeric emulsion latices, polyvinyl alcohol emulsions, polyurethane dispersions, polyvinyl acetate-ethylene copolymer emulsions, or carboxylated acrylic latexes.

10. The laminated wood product of claim 1 , wherein the wood to be joined has a moisture content of less than about 10% by weight.

11. A method for adhesively joining wood product surfaces, which comprises:

(1) providing an adhesive composition comprising:

(a) an isocyanate-functional prepolymer formed by reacting a polyisocyanate with an alcohol, where the isocyanate equivalents from the polyisocyanate exceeds the hydroxyl equivalents from the alcohol; and

(b) an aqueous polymer emulsion,

(2) applying said aqueous adhesive composition to said wood product surfaces; and

(3) curing said adhesive composition.

12. The method of claim 11 , wherein said alcohol is selected from one or more of acrylates, esters, vinyls, castor oils, or polymers, containing active alcohol groups.

13. The method of claim 12 , wherein said alcohol is selected from one or more of aliphatic and aromatic polyether polyols optionally alkylated, or caprolactone-based polyols.

14. The method of claim 13 , wherein said active hydrogen group component is a block polyethylene or polypropylene oxide homo- or co-polymer ranging in molecular weight from about 300 to about 3,000.

15. The method of claim 11 , wherein said isocyanate-terminated prepolymer is made from an isocyanate component selected from hexamethylene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), m- and p-phenylene diisocyanates, bitolylene diisocyanate, cyclohexane diisocyanate (CHDI), bis-(isocyanatomethyl)cyclohexane (H 6 XDI), dicyclohexylmethane diisocyanate (H 12 MDI), dimer acid diisocyanate (DDI), trimethyl hexamethylene diisocyanate, lysine diisocyanate and its methyl ester, isophorone diisocyanate, methyl cyclohexane diisocyanate, 1,5-napthalene diisocyanate, xylylene and xylene diisocyanate and methyl derivatives thereof, polymethylene polyphenyl isocyanates, chlorophenylene-2,4-diisocyanate, polyphenylene diisocyanates, isophorone diisocyanate (IPDI), hydrogenated methylene diphenyl isocyanate (HMDI), tetramethyl xylene diisocyanate (TMXDI), hexamethylene diisocyanate (HDI), or oligomers thereof, and mixtures thereof.

16. The method of claim 11 , wherein said isocyanate prepolymer contains a defoamer and an inhibitor.

17. The method of claim 11 , wherein the weight ratio of said isocyanate-functional prepolymer to said aqueous polymer emulsion ranges from about 95/5 to about 60/40.

18. The method of claim 17 , wherein the weight ratio of said isocyanate-functional prepolymer to said aqueous polymer emulsion ranges from about 90/10 to about 70/30.

19. The method of claim 11 , wherein said aqueous polymer emulsion is one or more of acrylic emulsions, vinyl emulsions, styrene-butadiene polymeric emulsion latices, polyvinyl alcohol emulsions, polyurethane dispersions, polyvinyl acetate-ethylene copolymer emulsions, or carboxylated acrylic latexes.

20. The method of claim 19 , wherein said curing is by heat curing or radio frequency curing.

Assignments (10)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2022
From: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC
To: ARKEMA FRANCE
Reel/Frame 060740/0862 →
CORRECTIVE ASSIGNMENT TO CORRECT THE REMOVE PATENT NUMBER 6763859 PREVIOUSLY RECORDED ON REEL 016408 FRAME 0950. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded May 9, 2014
From: ASHLAND INC.
To: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC
Reel/Frame 032867/0391 →
RELEASE OF PATENT SECURITY AGREEMENT Recorded Mar 18, 2013
From: THE BANK OF NOVA SCOTIA
To: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; ISP INVESTMENTS INC.; HERCULES INCORPORATED
Reel/Frame 030025/0320 →
SECURITY AGREEMENT Recorded Sep 16, 2011
From: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; HERCULES INCORPORATED; AQUALON COMPANY; ISP INVESTMENT INC.
To: THE BANK OF NOVA SCOTIA, AS ADMINISTRATIVE AGENT
Reel/Frame 026918/0052 →
RELEASE OF PATENT SECURITY AGREEMENT Recorded Sep 15, 2011
From: BANK OF AMERICA, N.A.
To: ASHLAND, INC.; ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; HERCULES INCORPORATED
Reel/Frame 026927/0247 →
SECURITY AGREEMENT Recorded Apr 14, 2010
From: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; HERCULES INCORPORATED
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 024225/0289 →
RELEASE OF SECURITY INTEREST Recorded Apr 13, 2010
From: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
To: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; HERCULES INCORPORATED
Reel/Frame 024218/0928 →
SECURITY AGREEMENT Recorded Dec 3, 2008
From: ASHLAND LICENSING AND INTELLECTUAL PROPERTY...; AQUALON COMPANY; HERCULES INCORPORATED
To: BANK OF AMERICA, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 021924/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 17, 2005
From: ASHLAND INC.
To: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC
Reel/Frame 016408/0950 →