IP Library Granted Patent US 9,416,294
Granted Patent B2
US 9,416,294 · App. 13/826,730 · Granted Aug 16, 2016

Curable epoxide containing formaldehyde-free compositions, articles including the same, and methods of using the same

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,416,294
App. No.
13/826,730
Granted
Aug 16, 2016
Kind
B2
Abstract

A composition is disclosed that includes a water insoluble polymer, a polycarboxy functional polymer, and a water insoluble epoxide functional compound, the water insoluble polymer including at least one of polyvinyl acetate, vinyl acetate copolymer, styrene copolymer, acrylate copolymer, and polyurethane.

Claims (67)

1. A composition comprising:

a water insoluble polymer having a Tg of at least about 25° C. and comprising polyvinyl acetate, vinyl acetate copolymer, styrene copolymer, acrylate copolymer, polyurethane, or a combination thereof;

a polycarboxy functional polymer;

a water insoluble epoxide functional compound; and

organic solvent.

2. The composition of claim 1 , comprising

a first part comprising

an emulsion comprising the water insoluble polymer, and

the polycarboxy functional polymer; and

a second part comprising the water insoluble epoxide functional compound.

3. The composition of claim 1 comprising an emulsion comprising the water insoluble polymer.

4. The composition of claim 3 comprising

from about 35% by weight to about 95% by weight of the water insoluble polymer based on solids,

from about 3% by weight to about 50% by weight of the polycarboxy functional polymer based on solids, and

from about 1% by weight to about 50% by weight of the water insoluble epoxide functional compound based on solids.

5. The composition of claim 3 comprising

from about 35% by weight to about 90% by weight of the water insoluble polymer based on solids,

from about 5% by weight to about 70% by weight of the polycarboxy functional polymer based on solids, and

from about 4% by weight to about 40% by weight of the water insoluble epoxide functional compound based on solids.

6. The composition of claim 3 wherein the water insoluble polymer further comprises functional groups.

7. The composition of claim 3 further comprising a catalyst.

8. The composition of claim 7 , wherein the catalyst is present in the emulsion.

9. The composition of claim 7 , Wherein the catalyst comprises a phase transfer catalyst.

10. The composition of claim 7 , wherein the catalyst comprises a tetra-alkyl ammonium halide.

11. The composition of claim 7 , wherein the catalyst comprises methyltrioctyl-ammonium chloride, tetra-n-butylammonium bromide, or a combination thereof.

12. The composition of claim 1 comprising

from about 35% by weight to about 95% by weight of the water insoluble polymer based on solids,

from about 3% by weight to about 50% by weight of the polycarboxy functional polymer based on solids, and

from about 1% by weight to about 50% by weight of the water insoluble epoxide functional compound based on solids.

13. The composition of claim 1 comprising

from about 35% by weight to about 90% by weight of the water insoluble polymer based on solids,

from about 5% by weight to about 70% by weight of the polycarboxy functional polymer based on solids, and

from about 4% by weight to about 40 weight of the water insoluble epoxide functional compound based on solids.

14. The composition of claim 1 , wherein the water insoluble polymer further comprises functional groups.

15. The composition of claim 14 , wherein the functional groups comprise epoxide, carboxyl, hydroxyl, amino, amido, siloxy, or a combination thereof.

16. The composition of claim 14 , wherein the functional groups comprise carboxyl groups.

17. The composition of claim 1 , wherein the water insoluble polymer comprises carboxy functional polyvinyl acetate copolymer.

18. The composition of claim 1 , wherein the water insoluble polymer comprises polyvinyl acetate, polyvinyl acetate copolymer, or a combination thereof.

19. The composition of claim 1 wherein the water insoluble polymer, the polycarboxy functional polymer, and the water insoluble epoxide functional compound are soluble in the organic solvent.

20. The composition of claim 1 , wherein the composition further comprises water.

21. The composition of claim 1 , wherein the water insoluble polymer, the polycarboxy functional polymer, the water insoluble epoxide functional compound, or a combination thereof, is soluble in organic solvent.

22. The composition of claim 1 , Wherein the polycarboxy functional polymer is water soluble.

23. The composition of claim 1 , wherein the polycarboxy functional polymer is derived from acrylic acid, methacrylic acid, hydroxyethyl acrylate, hydroxymethyl acrylate, furmaric acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, isooctyl acrylic acid, isocrotonic acid, cinamic acid, 2-methyl maleic acid, 2-methyl itaconic acid, methyleneglutaric acid, or a combination thereof.

24. The composition of claim 1 , wherein, when the composition is used to prepare a treated test substrate and the treated test substrate is tested according to the Wet Burst Strength test method, the treated substrate exhibits a wet burst strength of at least about 27 psi.

25. The composition of claim 1 , wherein when the composition is used to prepare a treated test substrate and the treated test substrate is tested according to the Wet Burst Strength test method, the treated substrate exhibits a wet burst strength of at least about 30 psi.

26. The composition of claim 1 , when the composition is used to prepare a treated test substrate and the treated test substrate is tested according to the Wet Burst Strength test method, the treated substrate exhibits a wet burst strength of at least about 38 psi.

27. The composition of claim 1 , wherein when the composition is used to prepare a treated test substrate and the treated test substrate is tested according to the Wet Burst Strength test method, the treated substrate exhibits a wet burst strength of at least about 40 psi.

28. The composition of claim 1 , wherein, when the composition is used to prepare a treated test substrate and the treated test substrate is tested according to the Wicking test method, the treated test substrate is free of wicking.

29. The composition of claim 1 , wherein the organic solvent comprises acetone, methylethyl ketone, methanol, ethanol, isopropanol or a combination thereof.

30. A composition comprising:

a water insoluble polymer comprising polyvinyl acetate, vinyl acetate copolymer, styrene copolymer, acrylate copolymer, polyurethane, or a combination thereof the water insoluble polymer having a Tg of at least about 25 °C.;

a water soluble polycarboxy functional, polyhydroxy functional polymer derived from monomers comprising carboxy functional monomer and α, β-ethylenically unsaturated hydroxy functional monomer; and

a water insoluble epoxide functional compound.

31. The composition of claim 30 further comprising an organic solvent comprising a primary alcohol.

32. The composition of claim 30 comprising

from about 35% by weight to about 95% by weight of the water insoluble polymer based on solids,

from about 3% by weight to about 50% by weight of the polycarboxy, polyhydroxy functional polymer based on solids, and

from about 1% by weight to about 50% by weight of the water insoluble epoxide functional compound based on solids.

33. The composition of claim 30 comprising

from about 35% by weight to about 90% by weight of the water insoluble polymer based on solids,

from about 5% by weight to about 50% by weight of the polycarboxy, polyhydroxy functional polymer based on solids, and

from about 4% by weight to about 40% by weight of the water insoluble epoxide functional compound based on solids.

34. A composition comprising:

a water insoluble polymer comprising polyvinyl acetate, vinyl acetate copolymer, styrene copolymer, acrylate copolymer, polyurethane, or a combination thereof, wherein the water insoluble polymer has a Tq of at least about 25° C.;

a polycarboxy functional polymer;

a water insoluble epoxide functional compound; and

organic solvent comprising a primary alcohol.

Assignments (4)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) Recorded Feb 15, 2023
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: H.B. FULLER COMPANY; H.B. FULLER CONSTRUCTION PRODUCTS INC.; ROYAL ADHESIVES AND SEALANTS, LLC; ADCO PRODUCTS, LLC
Reel/Frame 062761/0884 →
TERM LOAN SECURITY AGREEMENT Recorded Oct 25, 2017
From: H.B. FULLER COMPANY; H.B. FULLER CONSTRUCTION PRODUCTS INC.; ROYAL ADHESIVES AND SEALANTS, LLC; ADCO PRODUCTS, LLC
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 044616/0671 →
RCF SECURITY AGREEMENT Recorded Oct 25, 2017
From: H.B. FULLER COMPANY; H.B. FULLER CONSTRUCTION PRODUCTS INC.; ROYAL ADHESIVES AND SEALANTS, LLC; ADCO PRODUCTS, LLC
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 044616/0700 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 26, 2013
From: MILLER, WAYNE P.
To: H. B. FULLER COMPANY
Reel/Frame 030687/0781 →