IP Library Granted Patent US 10,738,025
Granted Patent B2
US 10,738,025 · App. 15/289,521 · Granted Aug 11, 2020

Modified polyphenol binder compositions and methods for making and using 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 10,738,025
App. No.
15/289,521
Granted
Aug 11, 2020
Kind
B2
Abstract

Modified polyphenol binder compositions and methods for making and using same are provided. In at least one specific embodiment, the binder composition can include at least one unsaturated monomer and at least one polyphenolic compound. The polyphenolic compound can include a lignin, a tannin, a novolac resin, a modified phenol formaldehyde resin, bis-phenol A, humic acid, or any mixture thereof.

Claims (36)

1. A binder composition, comprising:

a reaction product of an unsaturated monomer and at least two polyphenolic compounds, wherein:

each polyphenolic compound comprises a tannin, a lignin, a novolac resin, a modified phenol formaldehyde resin, bis-phenol A, or humic acid, and

the unsaturated monomer comprises an unsaturated glycidyl ether, an unsaturated glycidyl ester, an unsaturated mono-epoxide, an unsaturated methylol compound, or a mixture thereof, such that:

an ether linkage is formed between the unsaturated monomer and one of the at least two polyphenolic compounds when the unsaturated monomer comprises the unsaturated glycidyl ether, the unsaturated glycidyl ester, or the unsaturated mono-epoxide, or

a carbon-carbon bond is formed between the unsaturated monomer and one of the at least two polyphenolic compounds when the unsaturated monomer comprises the unsaturated methylol compound.

2. The binder composition of claim 1 , wherein the unsaturated monomer comprises an unsaturated glycidyl ether.

3. The binder composition of claim 1 , wherein the unsaturated monomer comprises an unsaturated glycidyl ester.

4. The binder composition of claim 1 , wherein the unsaturated monomer comprises an unsaturated mono-epoxide.

5. The binder composition of claim 1 , wherein the unsaturated monomer comprises an unsaturated methylol compound.

6. The binder composition of claim 1 , wherein the unsaturated monomer further comprises maleic anhydride.

7. The binder composition of claim 1 , wherein a weight ratio of the unsaturated monomer to the at least two polyphenolic compounds, on a solids basis, is about 0.1:100 to about 1:2.

8. The binder composition of claim 1 , wherein a weight ratio of the unsaturated monomer to the at least two polyphenolic compounds, on a solids basis, is about 0.1:100 to about 1:7.

9. The binder composition of claim 1 , wherein each polyphenolic compound comprises a lignin, a novolac resin, a modified phenol formaldehyde resin, or bis-phenol A, and wherein the unsaturated monomer comprises an unsaturated mono-epoxide, an unsaturated methylol compound, or a mixture thereof.

10. The binder composition of claim 1 , wherein the binder composition comprises about 0.05 wt % to about 50 wt % of the unsaturated monomer, based on a solids weight of the at least two polyphenolic compounds.

11. The binder composition of claim 1 , wherein the binder composition comprises about 0.1 wt % to about 15 wt % of the unsaturated monomer, based on a solids weight of the at least two polyphenolic compounds.

12. The binder composition of claim 1 , wherein at least one of the polyphenolic compounds comprises a lignin, a novolac resin, or bis-phenol A.

13. The binder composition of claim 1 , further comprising about 1 wt % to about 80 wt % of water, based on a solids weight of the at least two polyphenolic compounds.

14. A binder composition, comprising water and a reaction product of an unsaturated monomer and at least two polyphenolic compounds, wherein:

each polyphenolic compound comprises a tannin, a lignin, a novolac resin, a modified phenol formaldehyde resin, bis-phenol A, or humic acid, and

the unsaturated monomer comprises an unsaturated glycidyl ether, an unsaturated glycidyl ester, an unsaturated mono-epoxide, an unsaturated methylol compound, or a mixture thereof, such that:

an ether linkage is formed between the unsaturated monomer and one of the at least two polyphenolic compounds when the unsaturated monomer comprises the unsaturated glycidyl ether, the unsaturated glycidyl ester, or the unsaturated mono-epoxide, or

a carbon-carbon bond is formed between the unsaturated monomer and one of the at least two polyphenolic compounds when the unsaturated monomer comprises the unsaturated methylol compound, and

the binder composition comprises about 0.05 wt % to about 50 wt % of the unsaturated monomer and about 1 wt % to about 80 wt % of the water, based on a solids weight of the at least two polyphenolic compounds.

15. The binder composition of claim 14 , wherein at least one of the polyphenolic compounds comprises a lignin, a novolac resin, or bis-phenol A.

16. The binder composition of claim 14 , wherein the binder composition comprises about 0.1 wt % to about 15 wt % of the unsaturated monomer and about 40 wt % to about 70 wt % of the water, based on the solids weight of the at least two polyphenolic compounds.

17. A composite product, comprising:

a plurality of lignocellulose substrates and an at least partially cured binder composition, wherein the binder composition, prior to curing, comprises:

a reaction product of an unsaturated monomer and at least two polyphenolic compounds, wherein:

each polyphenolic compound comprises a tannin, a lignin, a novolac resin, a modified phenol formaldehyde resin, bis-phenol A, or humic acid, and

the unsaturated monomer comprises an unsaturated glycidyl ether, an unsaturated glycidyl ester, an unsaturated mono-epoxide, an unsaturated methylol compound, or a mixture thereof, such that:

an ether linkage is formed between the unsaturated monomer and one of the at least two polyphenolic compounds when the unsaturated monomer comprises the unsaturated glycidyl ether, the unsaturated glycidyl ester, or the unsaturated mono- epoxide, or

a carbon-carbon bond is formed between the unsaturated monomer and one of the at least two polyphenolic compounds when the unsaturated monomer comprises the unsaturated methylol compound.

18. The composite product of claim 17 , wherein the binder composition, prior to curing, comprises about 0.05 wt % to about 50 wt % of the unsaturated monomer, based on a solids weight of the at least two polyphenolic compounds.

19. The composite product of claim 17 , wherein the binder composition, prior to curing, further comprises water, and wherein the binder composition comprises about 0.1 wt % to about 15 wt % of the unsaturated monomer and about 40 wt % to about 70 wt % of the water, based on a solids weight of the at least two polyphenolic compounds.

20. The composite product of claim 17 , wherein the composite product is a particleboard, a fiberboard, a plywood, an oriented strand board, or a laminated veneer board.

Assignments (5)
ASSIGNMENT OF PATENT AND TRADEMARK SECURITY INTEREST Recorded May 12, 2025
From: MACQUARIE CAPITAL FUNDING LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 071276/0379 →
CHANGE OF NAME Recorded Mar 13, 2025
From: GEORGIA-PACIFIC CHEMICALS LLC
To: BAKELITE CHEMICALS LLC
Reel/Frame 070495/0222 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.; SURFACE TECH LLC
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0250 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.
To: MACQUARIE CAPITAL FUNDING LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0327 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2018
From: HAGIOPOL, CORNEL; ATKINSON, DEREK L.
To: GEORGIA-PACIFIC CHEMICALS LLC
Reel/Frame 046193/0372 →