IP Library Granted Patent US 10,144,818
Granted Patent B2
US 10,144,818 · App. 14/884,723 · Granted Dec 4, 2018

Resin 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 10,144,818
App. No.
14/884,723
Granted
Dec 4, 2018
Kind
B2
Abstract

Resins compositions and methods for making and using same. The resin composition can include a glyoxalated polyacrylamide resin and a polyamide-epihalohydrin resin. The polyamide-epihalohydrin resin can include a polyamine partially crosslinked with a bridging moiety and having azetidinium ions. The bridging moiety can be derived from a functionally symmetric crosslinker. A fiber product can include a plurality of fibers and the resin composition, where the resin composition can be at least partially cured.

Claims (40)

1. An aqueous two-component resin blend comprising about 25 wt % to about 75 wt % of a glyoxalated polyacrylamide resin component and a balance of about 25 wt % to about 75 wt % of a polyamide-epihalohydrin wet strength resin component, wherein said weight percentages are based on a combined solids weight of the polyamide-epihalohydrin wet strength resin component and the glyoxalated polyacrylamide resin component; wherein the polyamide-epihalohydrin wet strength resin component has azetidinium ions and comprises a polyamine partially crosslinked with a bridging moiety derived from a functionally symmetric crosslinker; and wherein the aqueous two-component resin blend has a solids content of about 15 wt % to about 25 wt %.

2. The aqueous two-component resin blend of claim 1 , wherein the aqueous two-component resin blend has a solids content of about 20 wt % to about 25 wt %.

3. The aqueous two-component resin blend of claim 1 , comprising about 30 wt % to about 70 wt % of the glyoxalated polyacrylamide resin component and a balance of about 30 wt % to about 70 wt % of the polyamide-epihalohydrin wet strength resin component, wherein said weight percentages are based on the combined solids weight of the polyamide-epihalohydrin wet strength resin component and the glyoxalated polyacrylamide resin component.

4. The aqueous two-component resin blend of claim 1 , wherein the aqueous two-component resin blend has an initial viscosity at a time the aqueous two-component resin blend is prepared, wherein about 5 minutes after the aqueous two-component resin blend is prepared the aqueous two-component resin blend has a second viscosity that is at least 20% greater than the initial viscosity, and wherein the aqueous two-component resin blend is maintained at a temperature of about 25° C. from the time the aqueous two-component resin blend is prepared until the second viscosity is measured.

5. The aqueous two-component resin blend of claim 1 , wherein the aqueous two-component resin blend has an initial viscosity at a time the aqueous two-component resin blend is prepared, wherein about 20 minutes after the aqueous two-component resin blend is prepared the aqueous two-component resin blend has a second viscosity that is at least 60% greater than the initial viscosity, and wherein the aqueous two-component resin blend is maintained at a temperature of about 25° C. from the time the aqueous two-component resin blend is prepared until the second viscosity is measured.

6. The aqueous two-component resin blend of claim 1 , wherein the polyamide-epihalohydrin wet strength resin component has an azet ratio of at least 0.7 to 1.0.

7. The aqueous two-component resin blend of claim 1 , wherein the azetidinium ions are formed by reacting an epihalohydrin and the polyamine partially crosslinked with the bridging moiety, and wherein the epihalohydrin comprises epichlorohydrin, epibromohydrin, epiiodohydrin, or any mixture thereof.

8. The aqueous two-component resin blend of claim 1 , wherein the polyamine has a chemical formula:

wherein R is a substituted or unsubstituted organic diyl group, and wherein w is an integer of 1 to about 10,000.

9. The aqueous two-component resin blend of claim 1 , wherein the functionally symmetric crosslinker comprises:

wherein R 4 is (CH 2 ) d , wherein d is 1, 2, or 3;

wherein e is from about 1 to about 100;

wherein f is from about 1 to about 100;

wherein x′+y′ is from about 1 to about 100;

wherein g is from about 1 to about 100;

wherein a j/k ratio is from about 10 to about 1000;

a copolymer of an acrylate, a methacrylate, an alkene, or a diene, with an azetidinium-functionalized monomer selected from

or any mixture thereof.

10. The aqueous two-component resin blend of claim 1 , wherein the functionally symmetric crosslinker comprises a diacrylate compound, a bis(acrylamide) compound, a diepoxide compound, a polyazetidinium compound, a bis(methacrylamide) compound, a poly(alkylene glycol) diglycidyl ether compound, a dialdehyde compound, a diisocyanate compound, a 1,3-dialkyldiazetidine-2,4-dione compound, a dianhydride compound, a diacyl halide compound, a dienone compound, a dialkyl halide compound, or any mixture thereof.

11. The aqueous two-component resin blend of claim 10 , wherein the glyoxalated polyacrylamide resin component is prepared by:

reacting a first amount of glyoxal with a base polyacrylamide having pendant amide groups to produce a first intermediate glyoxalated polyacrylamide;

adding an acid to the first intermediate glyoxalated polyacrylamide to produce a second intermediate glyoxalated polyacrylamide having a reduced pH as compared to the first intermediate glyoxalated polyacrylamide; and

adding a second amount of glyoxal to the second intermediate glyoxalated polyacrylamide to produce the glyoxalated polyacrylamide resin component.

12. The aqueous two-component resin blend of claim 1 , wherein the glyoxalated polyacrylamide resin component is prepared by:

reacting a first amount of glyoxal with a base polyacrylamide having pendant amide groups to produce a first intermediate glyoxalated polyacrylamide;

adding an acid to the first intermediate glyoxalated polyacrylamide to produce a second intermediate glyoxalated polyacrylamide having a reduced pH as compared to the first intermediate glyoxalated polyacrylamide; and

adding a second amount of glyoxal to the second intermediate glyoxalated polyacrylamide to produce the glyoxalated polyacrylamide resin component.

13. The aqueous two-component resin blend of claim 1 , comprising about 50 wt % of the glyoxalated polyacrylamide resin component and a balance of about 50 wt % of the polyamide-epihalohydrin wet strength resin component, wherein said weight percentages are based on the combined solids weight of the polyamide-epihalohydrin wet strength resin component and the glyoxalated polyacrylamide resin component.

14. The aqueous two-component resin blend of claim 1 , comprising about 30 wt % to about 70 wt % of the glyoxalated polyacrylamide resin component and a balance of about 30 wt % to about 70 wt % of the polyamide-epihalohydrin wet strength resin component, wherein said weight percentages are based on the combined solids weight of the polyamide-epihalohydrin wet strength resin component and the glyoxalated polyacrylamide resin component; and the aqueous two-component resin blend has a solids content of about 20 wt % to about 25 wt %.

15. The aqueous two-component resin blend of claim 1 , comprising about 30 wt % to about 70 wt % of the glyoxalated polyacrylamide resin component and a balance of about 30 wt % to about 70 wt % of the polyamide-epihalohydrin wet strength resin component, wherein said weight percentages are based on the combined solids weight of the polyamide-epihalohydrin wet strength resin component and the glyoxalated polyacrylamide resin component; wherein the aqueous two-component resin blend has a solids content of about 20 wt % to about 25 wt %; and

wherein the glyoxalated polyacrylamide resin component is prepared by:

reacting a first amount of glyoxal with a base polyacrylamide having pendant amide groups to produce a first intermediate glyoxalated polyacrylamide;

adding an acid to the first intermediate glyoxalated polyacrylamide to produce a second intermediate glyoxalated polyacrylamide having a reduced pH as compared to the first intermediate glyoxalated polyacrylamide; and

adding a second amount of glyoxal to the second intermediate glyoxalated polyacrylamide to produce the glyoxalated polyacrylamide resin component.

16. A method for making a fiber product, comprising: combining the aqueous two-component resin blend of claim 1 with a plurality of fibers to produce a mixture; and

at least partially curing the aqueous two-component resin blend to produce a fiber product.

17. The method of claim 16 , wherein the aqueous two-component resin blend has a solids content of about 20 wt % to about 25 wt %.

18. The method of claim 16 , wherein the functionally symmetric crosslinker comprises a diacrylate compound, a bis(acrylamide) compound, a diepoxide compound, a polyazetidinium compound, a bis(methacrylamide) compound, a poly(alkylene glycol) diglycidyl ether compound, a dialdehyde compound, a diisocyanate compound, a 1,3-dialkyldiazetidine-2,4-dione compound, a dianhydride compound, a diacyl halide compound, a dienone compound, a dialkyl halide compound, or any mixture thereof.

19. The method of claim 16 , wherein the plurality of fibers comprises at least one material selected from bleached furnish, softwood, hardwood, paper pulp, mechanical pulp, or any mixture thereof.

20. The method of claim 16 , wherein the plurality of fibers comprises cellulosic fibers.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2018
From: GEORGIA-PACIFIC CHEMICALS LLC
To: ECOLAB USA INC.
Reel/Frame 045221/0768 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 19, 2015
From: RINGOLD, CLAY E.; TOWNSEND, DAVID F.; HAGIOPOL, CORNEL; JOHNSTON, JAMES W.
To: GEORGIA-PACIFIC CHEMICALS LLC
Reel/Frame 037082/0046 →