IP Library Granted Patent US 7,259,115
Granted Patent B2
US 7,259,115 · App. 10/723,145 · Granted Aug 21, 2007

Curable extruded adhesive laminate system for manufacturing collapsible structures

Assignee: Cooley, Incorporated
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Quick Facts
Patent No.
US 7,259,115
App. No.
10/723,145
Granted
Aug 21, 2007
Kind
B2
Abstract

The invention is a heat curable extruded adhesive laminate system for producing collapsible tanks. The laminate is a composite of a fabric; an extruded linear hydroxyl adhesive having an uretdione that serves as a latent thermally activated curing component, and a high cyrstallinity thermoplastic polyurethane. In the system, panels cut from the adhesive laminate are assembled and seamed in a compression press operating at about 260° F. to about 350° F. The bonding process takes about 20-45 minutes, which causes the latent thermally activated curing component to cure the adhesive. Following compression heating in the press, the resulting seams have a strength that exceeds the minimum acceptable performance of 25 lbs/in, after being immersed in water and/or fuel at 160° F. for six weeks.

Claims (45)

1. A heat curable extruded adhesive laminate system, said system comprising:

a fabric;

an extruded adhesive having an activation temperature of approximately 55° C.-60° C. that is a thermoplastic polyurethane with pendent hydroxyl groups, said adhesive comprising a uretdione with an activation temperature in excess of 300° F. and a cross-linking enhancer, where said extruded adhesive is coated onto the fabric; and

an extruded thermoplastic polyurethane resin having a Shore A Durometer greater than 88, said thermoplastic resin coated onto the extruded adhesive;

wherein said laminate is a composite that at a subsequent time is assembled into a collapsible structure by application of heat and compression, said structure being hydrolytically stable and substantially inert following assembly; and

wherein the cross-linking enhancer is a compound with at least two hydroxyl groups.

2. A heat curable extruded adhesive laminate system, according to claim 1 , said system further comprising heating at least a portion of the composite to a temperature from about 260° F. to about 350° F. in a compression press.

3. The heat curable extruded adhesive laminate system, as claimed in claim 1 , wherein said structure is a collapsible tank.

4. The heat curable extruded adhesive laminate system, as claimed in claim 1 , wherein said thermoplastic polyurethane with pendant hydroxyl groups has a medium to a high level of crystallinity.

5. The heat curable extruded adhesive laminate system, as claimed in claim 1 , wherein the uretdione is comprised of a dimer of a diisocyanate, a multi-uretdione adduct or a combination thereof.

6. The heat curable extruded adhesive laminate system, as claimed in claim 5 , wherein the uretdione is selected from the group consisting of dimers of toluene diisocyanate (TDI), methylene diisocyanate (MDI), xylene diisocyanate (XDI), isophorone diisocyanate (IPDI), hydrogenated methylene diisocyanate (H 12 MDI), and hexamethylene diisocyanate (HMDI).

7. The heat curable extruded adhesive laminate system, as claimed in claim 1 , wherein the cross-linking enhancer is selected from the group consisting of: a hydroxyalkylamide; glycols; abitol; butylene glycol; cyclohexanedimethanol; diethylene glycol; dipentaerythritol; dipropylene glycol; glycerine; hexylene glycol; hydrogenated Bisphenol A; methyl 1,2 propanediol; neopentylglycol; propylene glycol; sorbitol; triethylene glycol; trimethylolpropane; tripentaerythritol, alkoxy and hydroxyl alkoxy cellulose, simple sugars like fructose, sucrose, glucose and starches.

8. A heat curable extruded adhesive laminate system, according to claim 1 , wherein the extruded adhesive with a latent thermally activated curing component is further comprised of a hydrolytic stabilizer.

9. The heat curable extruded adhesive laminate system for producing collapsible tanks, as claimed in claim 8 , wherein the hydrolytic stabilizer is selected from the group consisting of masterbatches of bis(2,6-di-2-propylphenyl) carbodiimide, polycarbodiimide and epoxidized soy bean oil.

10. The heat curable extruded adhesive laminate system, as claimed in claim 1 , wherein the thermoplastic resin is compounded to include other additives such as reinforcing fibers, extenders, fillers, antioxidants, UV stabilizers, thermal stabilizers, flame retardants, glass beads, colorants, antimicrobial agents, dyes, pigments, processing aides (i.e. waxes, fluorinated compounds, silicone compounds, surfactants, polymeric processing aides), density modifiers such as phenolic beads, desiccants, buffers, and IR absorbent compounds to facilitate heating (i.e. carbon blacks, graphite, metal oxides).

11. The heat curable extruded adhesive laminate system, as claimed in claim 1 , wherein the said extruded adhesive is further compounded to include other additives such as reinforcing fibers, extenders, antioxidants, UV stabilizers, thermal stabilizers, flame retardants, fillers, glass beads, colorants, antimicrobial agents, dyes, pigments, processing aides (i.e. waxes, fluorinated compounds, silicone compounds, surfactants, polymeric processing aides), density modifiers such as phenolic beads, desiccants, buffers, and IR absorbent compounds to facilitate heating (i.e. carbon blacks, graphite, metal oxides).

12. A one pass heat curable extruded adhesive laminate system, said system comprising:

a fabric;

an extruded mixture comprised of a thermoplastic polyurethane resin having a Shore A Durometer greater than 88, a thermoplastic polyurethane adhesive having pendant hydroxyl groups, said adhesive having an activation temperature of approximately 55° C.-60° C. and comprising a uretdione with an activation temperature in excess of 300° F. and a cross-linking enhancer; wherein said extruded mixture is coated onto the fabric, thereby forming a one pass heat curable extruded adhesive laminate;

where said laminate is a composite that at a subsequent time is assembled into a collapsible structure by application of heat and compression, said structure being hydrolytically stable and substantially inert following assembly; and

wherein the cross-linking enhancer is a compound with at least two hydroxyl groups.

13. A one pass heat curable extruded adhesive laminate system, according to claim 12 , wherein said one pass system further comprising heating at least a portion of the composite to a temperature from about 260° F. to about 350° F. in a compression press.

14. The one pass heat curable extruded adhesive laminate system, as claimed in claim 12 , wherein said structure is a collapsible tank.

15. The one pass heat curable extruded adhesive laminate system, as claimed in claim 12 , wherein said thermoplastic polyurethane with pendant hydroxyl groups has a medium to a high level of crystallinity.

16. The one pass heat curable extruded adhesive laminate system, as claimed in claim 15 , wherein the uretdione is comprised of a dimer of a diisocyanate, a multi-uretdione adduct or a combination thereof.

17. The one pass heat curable extruded adhesive laminate system, as claimed in claim 16 , wherein the uretdione is selected from the group consisting of dimers of toluene diisocyanate (TDI), methylene diisocyanate (MDI), xylene diisocyanate (XDI), isophorone diisocyanate (IPDI), hydrogenated methylene diisocyanate (H 12 MDI), and hexamethylene diisocyanate (HMDI).

18. The one pass heat curable extruded adhesive laminate system, as claimed in claim 12 wherein the cross-linking enhancer is selected from the group consisting of: a hydroxyalkylamide; glycols; abitol; butylene glycol; cyclohexanedimethanol; diethylene glycol; dipentaerythritol; dipropylene glycol; glycerine; hexylene glycol; hydrogenated Bisphenol A; methyl 1,2 propanediol; neopentylglycol; propylene glycol; sorbitol; triethylene glycol; trimethylolpropane; tnpentaerythritol, alkoxy and hydroxyl alkoxy cellulose, simple sugars like fructose, sucrose, glucose and starches.

19. A one pass heat curable extruded adhesive laminate system, according to claim 12 , wherein the extruded mixture is further comprised of a hydrolytic stabilizer.

20. The one pass heat curable extruded adhesive laminate system, as claimed in claim 19 , wherein the hydrolytic stabilizer is selected from the group consisting of masterbatches of bis(2,6-di-2-propylphenyl)carbodiimide, polycarbodiimide and epoxidized soy bean oil.

21. The one pass heat curable extruded adhesive laminate system, as claimed in claim 12 , wherein the thermoplastic resin is compounded to include other additives such as reinforcing fibers, fillers, antioxidants, UV stabilizers, thermal stabilizers, flame retardants, glass beads, colorants, antimicrobial agents, dyes, pigments, processing aides (i.e. waxes, fluorinated compounds, silicone compounds, surfactants, polymeric processing aides), density modifiers such as phenolic beads, desiccants, buffers, and IR absorbent compounds to facilitate heating (i.e. carbon blacks, graphite, metal oxides).

22. The one pass heat curable extruded adhesive laminate system, as claimed in claim 12 , wherein the said extruded mixture is further compounded to include other additives such as reinforcing fibers, fillers, antioxidants, UV stabilizers, thermal stabilizers, flame retardants, glass beads, colorants, antimicrobial agents, dyes, pigments, processing aides (i.e. waxes, fluorinated compounds, silicone compounds, surfactants, polymeric processing aides), density modifiers such as phenolic beads, desiccants, buffers, and IR absorbent compounds to facilitate heating (i.e. carbon blacks, graphite, metal oxides).

23. The heat curable extruded adhesive laminate system, as claimed in claim 7 , wherein the hydroxyalkylamide is N,N,N′,N′-tetrakis(2-hydroxyethyl) adipamide, or N,N,N′,N′-tetrakis(2-hydroxypropyl)adipamide.

24. The heat curable extruded adhesive laminate system, as claimed in claim 23 , wherein the hydroxyalkylamide is combined with triglycidyl isocyanurate.

25. The one pass heat curable extruded adhesive laminate system, as claimed in claim 18 , wherein the hydroxyalkylamide is N,N,N′,N′-tetrakis(2-hydroxyethyl) adipamide, or N,N,N′,N′-tetrakis(2-hydroxypropyl)adipamide.

26. The one pass heat curable extruded adhesive laminate system, as claimed in claim 25 , wherein the hydroxyalkylamide is combined with triglycidyl isocyanurate.

27. A heat curable co-extruded adhesive laminate system, said system comprising:

a fabric;

a co-extruded adhesive having an activation temperature of approximately 55° C.-60° C. that is a thermoplastic polyurethane with pendent hydroxyl groups, said adhesive comprising a uretdione with an activation temperature in excess of 300° F. and a cross-linking enhancer, where said extruded adhesive is coated onto the fabric;

a co-extruded thermoplastic polyurethane resin having a Shore A Durometer greater than 88, said thermoplastic polyurethane resin being co-extruded onto the co-extruded adhesive;

where said laminate is a composite that at a subsequent time is assembled into a collapsible structure by application of heat and compression, said structure being hydrolytically stable and substantially inert following assembly; and

wherein the cross-linking enhancer is a compound with at least two hydroxyl groups.

28. A heat curable co-extruded adhesive laminate system, according to claim 27 , wherein said co-extruded system further comprising heating at least a portion of the composite to a temperature from about 260° F. to about 350° F. in a compression press.

29. The heat curable co-extruded adhesive laminate system, as claimed in claim 27 , wherein said structure has seams which have a strength that exceeds the minimum acceptable performance for a collapsible water tank, said strength being 25 lbs/in, after being immersed in water and or fuel at 160° F. for six weeks.

30. The heat curable adhesive laminate system, as claimed in claim 1 , wherein said structure has seams which have a strength that exceeds the minimum acceptable performance for a collapsible water tank, said strength being 25 lbs/in, after being immersed in water and/or fuel at 160° F. for six weeks.

31. The one pass heat curable extruded adhesive laminate system, as claimed in claim 12 , wherein said structure has seams which have a strength that exceeds the minimum acceptable performance for a collapsible water tank, said strength being 25 lbs/in, after being immersed in water and/or fuel at 160° F. for six weeks.

Assignments (9)
RELEASE OF SECURITY INTEREST Recorded Jan 26, 2026
From: BANK OF AMERICA, N.A.
To: COOLEY, INCORPORATED; COOLEY GROUP HOLDINGS, INC.; K2 BUYER, INC.; COOLEY, INC.; K2 HOLDING, INC.
Reel/Frame 073576/0949 →
RELEASE OF SECURITY INTEREST Recorded Jul 11, 2024
From: WEBSTER BUSINESS CREDIT, A DIVISION OF WEBSTER BANK, N.A. (SUCCESSOR IN INTEREST TO WEBSTER BUSINESS CREDIT CORPORATION)
To: COOLEY, INCORPORATED; COOLEY GROUP HOLDINGS, INC.; COOLEY, INC. (F/K/A VINTEX INC.)
Reel/Frame 067970/0542 →
SECURITY AGREEMENT Recorded Jun 26, 2024
From: COOLEY, INCORPORATED; COOLEY GROUP HOLDINGS, INC.; K2 BUYER, INC.; COOLEY, INC.; K2 HOLDING, INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 067842/0927 →
RELEASE OF INTELLECTUAL PROPERTY SECURITY AGREEMENT RECORDED AT REEL 021617/FRAME 0193 Recorded Feb 5, 2021
From: PNC BANK, NATIONAL ASSOCIATION
To: COOLEY GROUP HOLDINGS, INC.; COOLEY, INCORPORATED; RISC, LLC
Reel/Frame 055231/0112 →
RELEASE OF SECURITY INTEREST Recorded Dec 31, 2020
From: WEBSTER BUSINESS CREDIT CORPORATION
To: COOLEY, INCORPORATED
Reel/Frame 054787/0441 →
SECURITY AGREEMENT Recorded Dec 30, 2020
From: COOLEY, INCORPORATED; COOLEY GROUP HOLDINGS, INC.; VINTEX INC.
To: WEBSTER BUSINESS CREDIT CORPORATION, AS AGENT
Reel/Frame 055680/0596 →
SECURITY AGREEMENT Recorded Jul 30, 2012
From: COOLEY, INCORPORATED
To: WEBSTER BUSINESS CREDIT CORPORATION, AS AGENT
Reel/Frame 028670/0453 →
SECURITY AGREEMENT Recorded Oct 1, 2008
From: COOLEY GROUP HOLDINGS, INC.; COOLEY, INCORPORATED; RISC, LLC
To: PNC BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 021617/0193 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2003
From: PANSE, DATTATREYA RAMESH
To: COOLEY, INCORPORATED
Reel/Frame 014730/0934 →
Continuity (1)
Related Publication 20050112971A1 · May 26, 2005