IP Library Granted Patent US 10,190,261
Granted Patent B2
US 10,190,261 · App. 15/633,133 · Granted Jan 29, 2019

Strengthening resins for paper products

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 10,190,261
App. No.
15/633,133
Granted
Jan 29, 2019
Kind
B2
Abstract

Resin compositions, products made therewith, and methods for making such resin compositions and products. The resin composition can include a polyamide-epihalohydrin resin, a cationic styrene maleimide resin, and a urea-formaldehyde resin. The polyamide-epihalohydrin resin can include a reaction product of a polyamidoamine and an epihalohydrin. The cationic styrene maleimide resin can include a reaction product of a styrene maleic anhydride copolymer and an amine compound. The product can include a fiber web and an at least partially cured resin composition. The resin composition, prior to curing, can include a polyamide-epihalohydrin resin, a cationic styrene maleimide resin, and a urea-formaldehyde resin. The polyamide-epihalohydrin resin can include a reaction product of a polyamidoamine and an epihalohydrin. The cationic styrene maleimide resin can include a reaction product of a styrene maleic anhydride copolymer and an amine compound.

Claims (55)

1. A fiber mixture, comprising:

a plurality of fibers; and

a resin composition comprising:

about 10 wt % to about 80 wt % of a polyamide-epihalohydrin resin comprising a reaction product of a polyamidoamine and an epihalohydrin;

about 10 wt % to about 80 wt % of a cationic styrene maleimide resin comprising a reaction product of a styrene maleic anhydride copolymer and an amine compound; and

about 10 wt % to about 80 wt % of a urea-formaldehyde resin, wherein the weight percent values of the polyamide-epihalohydrin resin, the cationic styrene maleimide resin, and the urea-formaldehyde resin are based on a combined solids weight of the polyamide-epihalohydrin resin, the cationic styrene maleimide resin, and the urea-formaldehyde resin.

2. The fiber mixture of claim 1 , wherein the plurality of fibers comprises cellulosic fibers, synthetic fibers, or a mixture thereof.

3. The fiber mixture of claim 1 , wherein the plurality of fibers comprises cellulosic fibers.

4. The fiber mixture of claim 1 , wherein the resin composition comprises about 15 wt % to about 70 wt % of the cationic styrene maleimide resin, about 15 wt % to about 70 wt % of the polyamide-epihalohydrin resin, and about 15 wt % to about 70 wt % of the urea-formaldehyde resin, wherein the weight percent values of the polyamide-epihalohydrin resin, the cationic styrene maleimide resin, and the urea-formaldehyde resin are based on a combined solids weight of the polyamide-epihalohydrin resin, the cationic styrene maleimide resin, and the urea-formaldehyde resin.

5. The fiber mixture of claim 1 , wherein the resin composition comprises about 16 wt % to about 42 wt % of the cationic styrene maleimide resin, about 16 wt % to about 42 wt % of the polyamide-epihalohydrin resin, and about 16 wt % to about 42 wt % of the urea-formaldehyde resin, wherein the weight percent values of the polyamide-epihalohydrin resin, the cationic styrene maleimide resin, and the urea-formaldehyde resin are based on a combined solids weight of the polyamide-epihalohydrin resin, the cationic styrene maleimide resin, and the urea-formaldehyde resin.

6. The fiber mixture of claim 1 , wherein:

the polyamide-epihalohydrin resin has a weight average molecular weight of about 20,000 to about 3,000,000;

the cationic styrene maleimide resin has a weight average molecular weight of about 3,000 to about 200,000; and

the urea-formaldehyde resin has a weight average molecular weight of about 2,000 to about 500,000.

7. The fiber mixture of claim 1 , wherein:

the polyamide-epihalohydrin resin has a weight average molecular weight of about 20,000 to about 3,000,000, an azetidinium ion ratio of about 0.55 to about 0.80, and a charge density of about 1.5 mEq/g to about 3 mEq/g of solids;

the cationic styrene maleimide resin has a weight average molecular weight of about 3,000 to about 200,000 and a styrene to maleimide molar ratio of about 1:1 to about 5:1; and

the urea-formaldehyde resin has a weight average molecular weight of about 2,000 to about 500,000 and a formaldehyde to urea molar ratio of about 0.5:1 to about 1.2:1.

8. The fiber mixture of claim 1 , wherein the cationic styrene maleimide resin comprises a copolymer of styrene and dimethylaminopropylamine maleimide acetate.

9. The fiber mixture of claim 1 , wherein the cationic styrene maleimide resin has the chemical formula:

wherein:

R + is a cationic molecular group;

A − is an anion;

m is an integer of 1 to about 5; and

n is an integer of about 5 to about 800.

10. The fiber mixture of claim 9 , wherein the cationic molecular group is a cationic ammonium group, wherein the anion is a carboxylate, and the carboxylate is an acetate anion, a citrate anion, an oxalate anion, a lactate anion, a formate anion, or any mixture thereof.

11. The fiber mixture of claim 1 , wherein the cationic styrene maleimide resin has the chemical formula:

wherein:

R 1 is a substituted or unsubstituted organic diyl group;

R 2 , R 3 , and R 4 are independently selected from a hydrogen or a substituted or unsubstituted, linear or branched, cyclic, heterocyclic, or aromatic hydrocarbyl group;

A − is an anion;

m is an integer of 1 to about 5; and

n is an integer of about 5 to about 800.

12. The resin composition of claim 1 , wherein the cationic styrene maleimide resin has the chemical formula:

wherein:

A − is an anion; and

n 1 , n 2 , and n 3 are independently an integer of about 5 to about 800.

13. The fiber mixture of claim 1 , wherein the resin composition, based on a solids content thereof, is present in the fiber mixture in an amount of about 0.05 wt % to about 5 wt %, based on a dried weight of the plurality of fibers.

14. A process for making a fiber product, comprising:

combining a resin composition with a plurality of fibers to produce a fiber mixture, wherein the resin composition comprises:

about 10 wt % to about 80 wt % of a polyamide-epihalohydrin resin comprising a reaction product of a polyamidoamine and an epihalohydrin;

about 10 wt % to about 80 wt % of a cationic styrene maleimide resin comprising a reaction product of a styrene maleic anhydride copolymer and an amine compound; and

about 10 wt % to about 80 wt % of a urea-formaldehyde resin, wherein the weight percent values of the polyamide-epihalohydrin resin, the cationic styrene maleimide resin, and the urea-formaldehyde resin are based on a combined solids weight of the polyamide-epihalohydrin resin, the cationic styrene maleimide resin, and the urea-formaldehyde resin; and

at least partially curing the resin composition in the fiber mixture to form the fiber product.

15. The process of claim 14 , wherein the resin composition is at least partially cured by heating the fiber mixture to a temperature of about 80° C. to about 120° C. for about 2 minutes to about 20 minutes.

16. The process of claim 14 , wherein the resin composition, based on a solids content thereof, is present in the fiber mixture in an amount of about 0.05 wt % to about 5 wt %, based on a dried weight of the plurality of fibers.

17. The process of claim 14 , wherein the fiber product is in a form of a sheet and has a basis weight of about 40.7 g/m 2 to about 122.1 g/m 2 .

18. A fiber product, comprising:

a plurality of fibers; and

an at least partially cured resin composition, wherein, prior to curing, the resin composition comprises:

about 10 wt % to about 80 wt % of a polyamide-epihalohydrin resin comprising a reaction product of a polyamidoamine and an epihalohydrin;

about 10 wt % to about 80 wt % of a cationic styrene maleimide resin comprising a reaction product of a styrene maleic anhydride copolymer and an amine compound; and

about 10 wt % to about 80 wt % of a urea-formaldehyde resin, wherein the weight percent values of the polyamide-epihalohydrin resin, the cationic styrene maleimide resin, and the urea-formaldehyde resin are based on a combined solids weight of the polyamide-epihalohydrin resin, the cationic styrene maleimide resin, and the urea-formaldehyde resin.

19. The fiber product of claim 18 , wherein the resin composition, based on a solids content thereof, is present in the fiber product in an amount of about 0.05 wt % to about 5 wt %, based on a dried weight of the fiber product.

20. The fiber product of claim 18 , wherein the fiber product is in a form of a sheet and has a basis weight of about 40.7 g/m 2 to about 122.1 g/m 2 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 18, 2018
From: RINGOLD, CLAY E; HAGIOPOL, CORNEL; JOHNSTON, JAMES W.; POTTER, FREDERICK S.
To: GEORGIA-PACIFIC CHEMICALS LLC
Reel/Frame 045579/0042 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2018
From: GEORGIA-PACIFIC CHEMICALS LLC
To: ECOLAB USA INC.
Reel/Frame 045221/0768 →