IP Library Granted Patent US 10,526,489
Granted Patent B2
US 10,526,489 · App. 15/640,741 · Granted Jan 7, 2020

Methods for reducing the solubility of phenolic resins using latent acids

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Quick Facts
Patent No.
US 10,526,489
App. No.
15/640,741
Granted
Jan 7, 2020
Kind
B2
Abstract

Resin compositions having a reduced solubility and methods for making and using same are provided. In at least one specific embodiment, the resin composition can include a phenolic resin, a latent acid, a catalyst, and a liquid medium. The catalyst can be a base compound and can be present in an amount of about 2 wt % to about 7 wt %, based on the combined weight of the phenolic resin, the latent acid, the catalyst, and the liquid medium.

Claims (40)

1. A resin composition, comprising: a phenolic resin, a latent acid, a base compound, and a liquid medium, wherein the resin composition comprises the base compound in an amount sufficient such that the resin composition has a pH of at least 7.5 when an acid component dissociates from the latent acid.

2. The resin composition of claim 1 , wherein the resin composition comprises about 25 wt % to about 65 wt % of the phenolic resin, about 0.01 wt % to about 10 wt % of the latent acid, about 1 wt % to about 12 wt % of the base compound, and about 32 wt % to about 70 wt % of the liquid medium, based on a combined weight of the phenolic resin, the latent acid, the base compound, and the liquid medium.

3. The resin composition of claim 1 , wherein the resin composition comprises about 25 wt % to about 45 wt % of the phenolic resin, about 0.01 wt % to about 3 wt % of the latent acid, about 1 wt % to about 7 wt % of the base compound, and about 45 wt % to about 65 wt % of the liquid medium, based on a combined weight of the phenolic resin, the latent acid, the base compound, and the liquid medium.

4. The resin composition of claim 1 , wherein the phenolic resin comprises a phenol formaldehyde resin having a formaldehyde to phenol molar ratio of about 1.9:1 to about 2.6:1.

5. The resin composition of claim 1 , wherein the latent acid comprises the acid component and a base component, wherein the acid component comprises a phosphorous-containing acid, a sulfur-containing acid, a nitrogen-containing acid, an organic mineral acid, a halogen-containing acid, conjugate bases thereof, alkaline salts thereof, rare earth salts thereof, or a mixture thereof, and wherein the base component comprises a primary amine, a secondary amine, or a tertiary amine.

6. The resin composition of claim 1 , wherein the latent acid comprises hydroxylamine sulfate, hydroxylamine phosphate, hydroxylamine phenol sulfonate, hydroxylamine p-toluene sulfonate, or any mixture thereof.

7. The resin composition of claim 1 , wherein the latent acid comprises an amine salt of triethylamine and sulfuric acid.

8. The resin composition of claim 1 , wherein the base compound comprises an alkali metal hydroxide, an alkali earth metal hydroxide, or a mixture thereof.

9. The resin composition of claim 1 , wherein the base compound comprises ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, triethylenetetraamine, diethylenetriamine, triethylamine, urea, or a mixture thereof.

10. The resin composition of claim 1 , wherein the resin composition comprises the base compound in an amount sufficient such that the resin composition has a pH of at least 8 when the acid component dissociates from the latent acid.

11. The resin composition of claim 1 , wherein:

the phenolic resin comprises a phenol formaldehyde resin having a formaldehyde to phenol molar ratio of about 1.9:1 to about 2.6:1,

the latent acid comprises hydroxylamine sulfate, hydroxylamine phosphate, hydroxylamine phenol sulfonate, hydroxylamine p-toluene sulfonate, or any mixture thereof,

the base compound comprises ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, triethylenetetraamine, diethylenetriamine, triethylamine, urea, or a mixture thereof,

the liquid medium comprises water,

the resin composition has a pH of greater than 9, and

the resin composition comprises about 25 wt % to about 65 wt % of the phenolic resin, about 0.01 wt % to about 10 wt % of the latent acid, about 1 wt % to about 12 wt % of the base compound, and about 32 wt % to about 70 wt % of the liquid medium, based on a combined weight of the phenolic resin, the latent acid, the base compound, and the liquid medium.

12. The resin composition of claim 1 , further comprising a metal salt, wherein there metal salt comprises sodium nitrate, aluminum sulfate, ammonium hydrogen phosphate, ammonium persulfate, ammonium chloride, ammonium chloride, magnesium chloride, zinc chloride, ammonium nitrate, ammonium sulfate, or a mixture thereof.

13. The resin composition of claim 1 , further comprising a plurality of lignocellulose substrates.

14. A resin composition, comprising: about 25 wt % to about 65 wt % of a phenolic resin, about 0.01 wt % to about 10 wt % of a latent acid, about 1 wt % to about 12 wt % of a base compound, and about 32 wt % to about 70 wt % of a liquid medium, based on a combined weight of the phenolic resin, the latent acid, the base compound, and the liquid medium, wherein:

the phenolic resin comprises a phenol formaldehyde resin having a formaldehyde to phenol molar ratio of about 1.9:1 to about 2.6:1,

the latent acid comprises an amine salt of triethylamine and sulfuric acid,

the base compound comprises sodium hydroxide, potassium hydroxide, or a mixture thereof,

the liquid medium comprises water,

the resin composition has a pH of greater than 10, and

the resin composition comprises the base compound in an amount sufficient such that the resin composition has a pH of at least 7.5 when an acid component dissociates from the latent acid.

15. A method for making a composite product, comprising:

mixing a plurality of lignocellulose substrates and a resin composition to produce a resinated furnish, wherein the resin composition comprises a phenolic resin, a latent acid, a base compound, and a liquid medium; and

curing the resin composition in the resinated furnish to produce a composite product, wherein an acid component dissociates from the latent acid when the resin composition is cured, and wherein the resin composition maintains a pH of at least 7.5 when the acid component dissociates from the latent acid.

16. The method of claim 15 , wherein the resin composition comprises about 25 wt % to about 65 wt % of the phenolic resin, about 0.01 wt % to about 10 wt % of the latent acid, about 1 wt % to about 12 wt % of the base compound, and about 32 wt % to about 70 wt % of the liquid medium, based on a combined weight of the phenolic resin, the latent acid, the base compound, and the liquid medium.

17. The method of claim 15 , wherein the resin composition comprises about 25 wt % to about 45 wt % of the phenolic resin, about 0.01 wt % to about 3 wt % of the latent acid, about 1 wt % to about 7 wt % of the base compound, and about 45 wt % to about 65 wt % of the liquid medium, based on a combined weight of the phenolic resin, the latent acid, the base compound, and the liquid medium.

18. The method of claim 15 , wherein the resinated furnish is heated to a temperature of about 100° C. to about 300° C. to at least partially cure the resin composition and produce the composite product.

19. The method of claim 15 , wherein the resin composition further comprises a metal salt, wherein there metal salt comprises sodium nitrate, aluminum sulfate, ammonium hydrogen phosphate, ammonium persulfate, ammonium chloride, ammonium chloride, magnesium chloride, zinc chloride, ammonium nitrate, ammonium sulfate, or a mixture thereof.

20. The method of claim 15 , wherein:

the phenolic resin comprises a phenol formaldehyde resin having a formaldehyde to phenol molar ratio of about 1.9:1 to about 2.6:1,

the latent acid comprises an amine salt of triethylamine and sulfuric acid,

the base compound comprises sodium hydroxide, potassium hydroxide, or a mixture thereof,

the liquid medium comprises water,

the resin composition has a pH of greater than 10, and

the resin composition maintains a pH of at least 8 when the acid component dissociates from the latent acid.

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 26, 2018
From: BREYER, ROBERT A.; CANNON, MELISSA J.; JENNINGS, JESSICA D.; YEAGER, DANIEL C.; GOLLOB, LAWRENCE
To: GEORGIA-PACIFIC CHEMICALS LLC
Reel/Frame 046198/0419 →