Water-dispersible polyurethane

Patent metadata

Field	Value
Publication number	US-12359012-B2
Application number	US-202117800428-A
Country	US
Kind code	B2
Filing date	Mar 26, 2021
Priority date	Apr 10, 2020
Publication date	Jul 15, 2025
Grant date	Jul 15, 2025

Abstract

The present invention relates to an aqueous dispersion comprising dispersed particles comprising a polyurethane comprising at least the following building blocks derived from a) at least one organic polyisocyanate, b) at least one carboxylate group-bearing isocyanate-reactive compound, and c) at least one organic isocyanate-reactive polyol, wherein at least one of the carboxylate group-bearing compounds b) has the following structural formula O II (1) R 2 (R 3 )—N—C—R 1 -COO − wherein R 1 is a divalent aliphatic hydrocarbon radical having from 2 to 8 carbon atoms or a divalent cycloaliphatic hydrocarbon radical having from 6 to 8 carbon atoms or a divalent aromatic hydrocarbon radical having from 6 to 8 carbon atoms, R 2 and R 3 are 2-hydroxypropyl.

First claim

The invention claimed is:

1. An aqueous dispersion comprising dispersed particles comprising a polyurethane, wherein the polyurethane comprises at least the following building blocks derived from
a) at least one organic polyisocyanate,
b) at least one carboxylate group-bearing isocyanate-reactive compound for providing chain-pendant carboxylate ionic dispersing groups in the polyurethane, and
c) at least one organic isocyanate-reactive polyol,
wherein at least one of the carboxylate group-bearing compounds b) has the following structural formula

wherein
R1 is a divalent aliphatic hydrocarbon radical having from 2 to 8 carbon atoms or a divalent cycloaliphatic hydrocarbon radical having from 6 to 8 carbon atoms or a divalent aromatic hydrocarbon radical having from 6 to 8 carbon atoms,
R2 and R3 are 2-hydroxypropyl.

2. The aqueous dispersion according to claim 1 , wherein R1 is a divalent aliphatic hydrocarbon radical having from 3 to 6 carbon atoms or a divalent cycloaliphatic hydrocarbon radical having from 6 to 8 carbon atoms or a divalent aromatic hydrocarbon radical having from 6 to 8 carbon atoms.

3. The aqueous dispersion according to claim 1 , wherein the polyurethane is the reaction product of at least
A) at least one organic polyisocyanate,
B′) at least one carboxylic acid-bearing compound for providing chain-pendant carboxylate ionic dispersing groups in the polyurethane,
C) at least one organic isocyanate-reactive polyol, and
D) at least one neutralizing agent to neutralize at least a part of the carboxylic acid groups,
wherein at least one of the carboxylic acid-bearing compounds B′) has the following structural formula

wherein R1, R2 and R3 are as defined in claim 1 .

4. The aqueous dispersion according to claim 3 , wherein the carboxylic acid-bearing compound B′) with structural formula (2) is the reaction product of diisopropanol amine and a cyclic acid anhydride selected from the group consisting of glutaric anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride and any mixture thereof.

5. The aqueous dispersion according to claim 3 , wherein the carboxylic acid-bearing compound B′) with structural formula (2) is the reaction product of glutaric anhydride and diisopropanol amine.

6. The aqueous dispersion according to claim 3 , wherein at least 50 wt. % of component B′) is according to structural formula (2).

7. The aqueous dispersion according to claim 3 , wherein the polyurethane is the reaction product of at least
(I) an at least partially neutralized isocyanate-terminated polyurethane prepolymer formed by reacting at least (A), (B′), (C) and (D) with a neutralization degree of from 125 to 25%, and
(II) an active-hydrogen containing chain extending compound.

8. The aqueous dispersion according to claim 1 , wherein the polyurethane has an acid number from 5 to 30 mg KOH/g of the polyurethane.

9. The aqueous dispersion according to claim 1 , wherein the polyurethane is an uralkyd polymer comprising an unsaturated fatty acid residue containing ester polyol as polyol C) and wherein the amount of fatty acid residue is within the range of from 20 to 60 wt. %, relative to the total weight amount of components used to prepare the polyurethane from which the building blocks of the polyurethane are emanated.

10. The aqueous dispersion according to claim 1 , wherein the organic polyisocyanate A) is a polyisocyanate containing at least two free isocyanate groups.

11. The aqueous dispersion according to claim 1 , wherein the polyol C) is a polyester polyol, polyether polyol and/or polycarbonate polyol optionally in combination with fatty acid residue containing polyol.

12. The aqueous dispersion according to claim 1 , wherein the dispersed particles further include at least one vinyl polymer and said vinyl polymer is obtained in-situ by the free-radical addition polymerization of one or more vinyl monomer in the presence of a preformed aqueous dispersion of the polyurethane according to claim 1 and wherein the acid number of the polyurethane-vinyl polymer hybrid is within the range of from 5 to 30 mg KOH/g of the polymer hybrid.

13. The aqueous dispersion according to claim 1 , wherein the dispersed particles have a particle size determined according to the method identified in the specification of from 15 to 1000 nm, as determined by a nano particle size analyzer using a scattering angle of 90 degrees and the acid number of the dispersed polymer is from 5 to 30 mg KOH/g.

14. The aqueous dispersion according to claim 1 , wherein the dispersed particles are present in the aqueous dispersion in an amount of from 20 to 60 wt. %, with a viscosity of the dispersion determined according to the method identified in the specification below 1000 mPa.s.

15. A coating or paint composition comprising the aqueous dispersion according to claim 1 .

16. The aqueous dispersion according to claim 1 , wherein R1 is a divalent aliphatic hydrocarbon radical having 3 or 4 carbon atoms or a divalent cycloaliphatic hydrocarbon radical having from 6 to 8 carbon atoms or a divalent aromatic hydrocarbon radical having from 6 to 8 carbon atoms.

17. The aqueous dispersion according to claim 3 , wherein at least 90 wt. % of component B′) is according to structural formula (2).

18. The aqueous dispersion according to claim 1 , wherein the polyurethane has an acid number from 6 to 16 mg KOH/g of the polyurethane.

19. The aqueous dispersion according to claim 1 , wherein the polyurethane is an uralkyd polymer comprising an unsaturated fatty acid residue containing ester polyol as polyol C) and wherein the amount of fatty acid residue is within the range of from 30 to 45 wt. %, relative to the total weight amount of components used to prepare the polyurethane from which the building blocks of the polyurethane are emanated.

20. The aqueous dispersion according to claim 1 , wherein the organic polyisocyanate A) is a diisocyanate Y(NCO)2, wherein Y represents a divalent aliphatic hydrocarbon radical having from 4 to 10 carbon atoms, a divalent cycloaliphatic hydrocarbon radical having from 6 to 13 carbon atoms, a divalent aromatic hydrocarbon radical having from 6 to 13 carbon atoms or a divalent araliphatic hydrocarbon radical having from 7 to 15 carbon atoms.

Assignees

• Covestro Netherlands Bv

Inventors

• Coogan Richard George
• Marchetti Samantha
• Seil Nikole
• Tennebroek Ronald

Classifications

• C08G18/5039

  containing amide groups · CPC title

• C08G2150/00

  Compositions for coatings · CPC title

• C08G18/4238

  derived from dicarboxylic acids and dialcohols · CPC title

• C08G18/36

  Hydroxylated esters of higher fatty acids · CPC title

• C09D175/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title