IP Library Granted Patent US 10,118,983
Granted Patent B2
US 10,118,983 · App. 15/094,550 · Granted Nov 6, 2018

Treated aldehyde-based resins containing polyamines and methods for making and using same

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Quick Facts
Patent No.
US 10,118,983
App. No.
15/094,550
Granted
Nov 6, 2018
Kind
B2
Abstract

Treated aldehyde-based resins containing one or more polyamines and methods for making and same. The treated aldehyde-based resin can be or include an aldehyde-based resin and a polyamine. The polyamine can be or include one or more aromatic polyamines, one or more poly(C 2 -C 5 alkylene) polyamines, or a mixture thereof. The treated aldehyde-based resin can include about 0.05 wt % to about 10 wt % of the polyamine, based on a solids weight of the aldehyde-based resin.

Claims (41)

1. A treated aldehyde-based resin, comprising:

an aldehyde-based resin;

a polyamine comprising an aromatic polyamine, wherein the aromatic polyamine comprises 1,3-diaminobenzene, 1,4-diaminobenzene, 1,3-xylylenediamine, 1,4-xylylenediamine, 3,4′-diaminodiphenyl ether, 4,4′-diaminodiphenyl ether, an isomer thereof, or any mixture thereof, wherein the treated aldehyde-based resin comprises about 0.05 wt % to 0.7 wt % of the polyamine, based on a solids weight of the aldehyde-based resin; and

an additive comprising a wax, a dibasic ester, or a mixture thereof.

2. The treated aldehyde-based resin of claim 1 , wherein the treated aldehyde-based resin comprises about 0.05 wt % to 0.6 wt % of the polyamine, based on a solids weight of the aldehyde-based resin.

3. The treated aldehyde-based resin of claim 1 , wherein the treated aldehyde-based resin comprises about 0.05 wt % to 0.5 wt % of the polyamine, based on a solids weight of the aldehyde-based resin.

4. The treated aldehyde-based resin of claim 1 , wherein the aldehyde-based resin comprises a phenol-formaldehyde resin, a urea-formaldehyde resin, a melamine-formaldehyde resin, a resorcinol-formaldehyde resin, a melamine-urea-formaldehyde resin, a phenol-urea-formaldehyde resin, a phenol-melamine-formaldehyde resin, a phenol-resorcinol-formaldehyde resin, a copolymer thereof, or any mixture thereof.

5. The treated aldehyde-based resin of claim 1 , wherein the aldehyde-based resin comprises a phenol-formaldehyde novolac resin, a copolymer thereof, or a mixture thereof.

6. The treated aldehyde-based resin of claim 1 , wherein the aromatic polyamine comprises 1,4-diaminobenzene.

7. The treated aldehyde-based resin of claim 1 , wherein the aromatic polyamine comprises 1,3-diaminobenzene, 1,3-xylylenediamine, 1,4-xylylenediamine, 3,4′-diaminodiphenyl ether, 4,4′-diaminodiphenyl ether, an isomer thereof, or any mixture thereof.

8. The treated aldehyde-based resin of claim 1 , wherein the polyamine further comprises a poly(C 2 -C 5 alkylene) polyamine, and wherein the poly(C 2 -C 5 alkylene) polyamine comprises diethylenetriamine, dipropylenetriamine, dibutylenetriamine, an isomer thereof, or any mixture thereof.

9. The treated aldehyde-based resin of claim 1 , wherein the additive comprises the mixture of the wax and the dibasic ester.

10. A method for making a treated aldehyde-based resin, comprising:

combining an aldehyde-based resin, a polyamine, and an additive to produce a mixture, wherein the polyamine comprises an aromatic polyamine, wherein the aromatic polyamine comprises 1,3-diaminobenzene, 1,4-diaminobenzene, 1,3-xylylenediamine, 1,4-xylylenediamine, 3,4′-diaminodiphenyl ether, 4,4′-diaminodiphenyl ether, an isomer thereof, and wherein the mixture comprises about 0.05 wt % to 0.7 wt % of the polyamine, based on a solids weight of the aldehyde-based resin, and wherein the additive comprises a wax, a dibasic ester, or a mixture thereof;

heating the mixture to a temperature of about 110° C. to about 200° C. to produce the treated aldehyde-based resin; and

cooling the treated aldehyde-based resin to a temperature of less than 50° C.

11. The method of claim 10 , wherein the mixture is heated to a temperature of about 120° C. to about 160° C. for about 10 minutes to about 60 minutes to produce the treated aldehyde-based resin, and wherein the treated aldehyde-based resin is cooled to a temperature of about 20° C. to about 30° C. to solidify the treated aldehyde-based resin.

12. The method of claim 10 , further comprising:

reacting formaldehyde and a reagent to produce the aldehyde-based resin, wherein the reagent comprises phenol, urea, or a mixture thereof; and

adding the polyamine to the aldehyde-based resin to produce the mixture.

13. A method for making a treated aldehyde-based resin, comprising:

heating a solid aldehyde-based resin to a temperature of about 110° C. to about 200° C. to produce a molten aldehyde-based resin;

combining the molten aldehyde-based resin and a polyamine to produce the treated aldehyde-based resin, wherein:

the polyamine comprises an aromatic polyamine, a poly(C 2 -C 5 alkylene) polyamine, or a mixture thereof,

the treated aldehyde-based resin comprises about 0.05 wt % to about 10 wt % of the polyamine, based on a solids weight of the aldehyde-based resin,

the polyamine is a solid when combined with the molten aldehyde-based resin, and

the molten aldehyde-based resin and the polyamine are at a temperature of about 110° C. to about 200° C. when combined with one another; and

cooling the treated aldehyde-based resin to a temperature of less than 50° C.

14. The method of claim 10 , wherein the aldehyde-based resin comprises a phenol-formaldehyde resin, a urea-formaldehyde resin, or a mixture thereof, and wherein the mixture comprises about 0.05 wt % to 0.6 wt % of the polyamine, based on a solids weight of the aldehyde-based resin.

15. The method of claim 10 , wherein the aromatic polyamine comprises 1,4-diaminobenzene.

16. The method of claim 10 , wherein the polyamine further comprises a poly(C 2 -C 5 alkylene) polyamine, and wherein the poly(C 2 -C 5 alkylene) polyamine comprises diethylenetriamine, dipropylenetriamine, dibutylenetriamine, an isomer thereof, or any mixture thereof.

17. A method for making a treated aldehyde-based resin, comprising:

combining formaldehyde and a reagent to produce a first mixture, wherein the reagent comprises phenol, urea, or a mixture thereof;

heating the first mixture to produce an aldehyde-based resin;

combining the aldehyde-based resin and an additive to produce a second mixture, wherein the additive comprises a wax, a dibasic ester, or a mixture thereof;

combining the second mixture and a polyamine to produce a third mixture, wherein the polyamine comprises an aromatic polyamine, a poly(C 2 -C 5 alkylene) polyamine, or a mixture thereof, and wherein the third mixture comprises about 0.05 wt % to 0.7 wt % of the polyamine, based on a solids weight of the aldehyde-based resin;

heating the third mixture to a temperature of about 110° C. to about 200° C. for about 5 minutes to about 90 minutes to produce the treated aldehyde-based resin; and

cooling the treated aldehyde-based resin to a temperature of less than 50° C. to solidify the treated aldehyde-based resin.

18. The method of claim 17 , wherein the formaldehyde is added to the reagent to produce the first mixture, and wherein the polyamine is added to the second mixture to produce the third mixture.

19. The method of claim 17 , wherein the first mixture is heated to a temperature of about 50° C. to about 100° C., and wherein the third mixture is heated to a temperature of about 110° C. to about 200° C.

20. The method of claim 17 , wherein the third mixture is produced by adding the polyamine and an additional amount of formaldehyde to the second mixture, and wherein the third mixture comprises about 0.05 wt % to 0.6 wt % of the polyamine, based on a solids weight of the aldehyde-based resin.

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 May 9, 2016
From: REDIGER, RICHARD A
To: GEORGIA-PACIFIC CHEMICALS LLC
Reel/Frame 038512/0906 →