Waterborne polyamide and their chain extension with isocyanates to form cationic waterborne polyureas dispersions

Patent metadata

Field	Value
Publication number	US-10640616-B2
Application number	US-201515535797-A
Country	US
Kind code	B2
Filing date	Nov 13, 2015
Priority date	Dec 18, 2014
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

An improved process for forming polyamide dispersions in water utilizing carbon dioxide to facilitate dispersion of the polyamide is disclosed. The polyamides are generally below 30,000 or 40,000 g/mole molecular weight when dispersed, but can be chain extended with polyfunctional species such as polyisocyanates after dispersion. The dispersions are useful in coatings, adhesives, and inks. Composites and hybrids of these other polyamides with vinyl polymers are also disclosed and claimed.

First claim

What is claimed is:

1. A process to make a polyamide cationic dispersion in water comprising:
a) providing a polyamide prepolymer with a number average molecular weight from about 500 to about 50,000 g/mole having at least one terminal primary or secondary amine groups and at least 0.1 milliequivalents of cationic dispersing groups selected from salted tertiary amine and quaternized tertiary amine group(s) per gram of said prepolymer;
b) dispersing said polyamide prepolymer in water using the cationic dispersing groups; and
c) utilizing at least 0.1 equivalents of CO 2 per equivalent of total amines selected from primary and secondary amine terminal groups and water to plasticize said polyamide prepolymer during the dispersing step.

2. The process of claim 1 , further comprising a step of chain extending said amine terminated polyamide dispersion in water with a polyisocyanate to a number average molecular weight in excess of 100,000 g/mole.

3. The process of claim 1 , wherein said polyamide prepolymer comprises multiple amide linkages and wherein at least 50 mole % of the polyamide linkages are tertiary amide linkages.

4. The process of claim 1 , including from about 5 to about 50 wt. % of poly(C 2 -C 4 alkylene oxide) segments copolymerized into said amine-terminated polyamide.

5. The process of claim 1 , wherein said CO 2 is added to the polyamide prepolymer before the amine terminated polyamide prepolymer is dispersed in water.

6. The process of claim 1 , wherein said CO 2 is added to the water phase that the polyamide prepolymer is dispersed in.

7. A process for dispersing an amine-terminated prepolymer of number average molecular weight from about 500 to about 50,000 g/mole in a water solution comprising:
a) providing a primary or secondary amine terminated prepolymer having at least 0.1 milliequivalents/gram of cationic dispersing groups selected from salted tertiary amines and quaternized tertiary amines; and
b) dispersing said amine-terminated prepolymer in water with the aid of at least 0.1 equivalents of CO 2 per equivalent of amine-terminal groups on said amine terminated prepolymer, wherein said CO 2 and water present reduce the viscosity of the prepolymer phase such that it is easier to form smaller diameter, more colloidally stable dispersions of said prepolymer, than without said CO 2 .

8. The process of claim 7 , further comprising a step of chain extending said amine terminated polyamide dispersion in water with a polyfunctional reactant that can condense with said amine terminal groups to form a chemical bond, to increase the number average molecular weight of the resulting polymer to be in excess of 100,00 g/mole.

9. The process of claim 8 , wherein said polyfunctional reactant is a polyisocyanate.

10. The process of claim 7 , wherein sufficient cationic dispersing groups and sufficient CO 2 are used such that a prepolymer dispersion with a volume average particle diameter of less than 400 nanometers is formed.

11. The process of claim 10 , wherein said volume average particle diameter is less than 300 nanometers.

12. The process of claim 7 , wherein said amine terminated prepolymer also comprises from about 5 to about 50 wt. % of poly(C 2 -C 4 alkylene oxide) segments copolymerized into said prepolymer.

13. The process of claim 8 , wherein at least 50 mole % of said amine terminal groups are secondary amine terminal groups.

14. The process of claim 13 , wherein at least 70 mole % of said amine terminal groups are secondary amine terminal groups.

15. The process of claim 7 , wherein at least 1 equivalent of CO 2 groups are present per equivalent of amine terminal groups in said dispersing step.

16. The process of claim 7 , wherein said amine terminated prepolymer comprises at least 20 wt. % of repeating units with amide linkages attached to adjacent repeat units with amide linkages.

17. The process of claim 7 , wherein at least 60 mole % of said amide linkages linking said repeat units are tertiary amide linkages derived from reacting a secondary amine with a carboxylic acid.

18. A composition comprising the reaction product of claim 2 .

19. The composition of claim 18 , wherein said reaction product further includes a crosslinker or a coalescent.

20. The composition of claim 18 , used in an ink, coating, or adhesive.

Assignees

• Lubrizol Advanced Mat Inc

Inventors

• Erdodi Gabor
• Lai John Ta-Yuan
• Pourahmady Naser

Classifications

• C09D175/12

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C08G18/603 Primary

  Polyamides · CPC title

• C08G69/265

  from at least two different diamines or at least two different dicarboxylic acids · CPC title

• C09J175/12

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C08G18/758

  containing two or more cycloaliphatic rings · CPC title