Aqueous pigment dispersions based on polyurethane dispersants having components to interact with cellulose

Patent metadata

Field	Value
Publication number	US-9315690-B2
Application number	US-201214368671-A
Country	US
Kind code	B2
Filing date	Dec 27, 2012
Priority date	Dec 30, 2011
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

Aqueous pigment dispersions based on polyurethane dispersants having components capable of interacting with cellulose are described. These components include a heterocycle pendent and or terminal to the polymer chain. The heterocycle is selected based on its Hansen solubility parameters.

First claim

What is claimed is:

1. An aqueous pigment dispersion comprising a colorant and a polyurethane dispersant, wherein said polyurethane dispersant comprises at least one compound of the general structure of Formula I:

each Y is independently O, S or NR 4 ;
each W is N, O or S;
n is an integer from 2 to 30;
each R 1 is independently C 1 -C 20 alkyl optionally substituted with one or more R 5 , OR 6 , SR 6 or NR 7 R 8 , or C 6 -C 40 aryl optionally substituted with one or more R 5 , OR 6 , SR 6 or NR 7 R 8 ;
each R 2 is comprised of difunctional isocyanate reactants Z 1 , Z 2 and Z 3 , wherein
Z 1 is a difunctional isocyanate reactant substituted with an aqueous dispersing ionic group, and Z 1 is present in between 5 to 40 weight percent of total weight of the polyurethane dispersant;
Z 2 is a difunctional or trifunctional isocyanate reactant selected from the group consisting of diol, diamine, amino alcohol, diamine alcohol, and amino dialcohol, and Z 2 is present in between 0 to 40 weight percent of total weight of the polyurethane dispersant; and
Z 3 is a difunctional isocyanate reactant substituted with R 3 , and Z 3 is present in between 5 to 40 weight percent of total weight of the polyurethane dispersant; and
each R 3 is independently a monocyclic or bicyclic heterocycle containing N, S or O atoms on the ring bonding via a carbon or heteroatom to Y or Z 2 either directly or via a linking group containing 1-10 carbon atoms, wherein said heterocycle is selected from the group consisting of imidazolidinone, oxazolidinone, thiazolidinone, triazole, thiazole, pyridazine, and glycoside, and wherein the carbon atoms on the ring of said heterocycle are optionally substituted with one or more R 5 , OR 6 , SR 6 or NR 7 R 8 , and the N atom or atoms on the ring of said heterocycle are optionally substituted with R 5 or —R 9 OR 6 ;
each R 5 is independently C 1 -C 20 alkyl, C 3 -C 20 cycloalkyl or C 6 -C 40 aryl;
each R 6 is independently H, C 1 -C 20 alkyl, C 3 -C 20 cycloalkyl or C 6 -C 40 aryl; and
each R 7 and R 8 are independently H, C 1 -C 20 alkyl, C 2 -C 20 cycloalkyl or C 6 -C 40 aryl; and
each R 9 is C 1 -C 5 alkyl.

2. The pigment dispersion of claim 1 wherein R 2 further comprises Z 4 , and Z 4 is a difunctional or trifunctional isocyanate reactant selected from the group consisting of a diol that contains a sulfone and a diamine that contains a sulfone.

3. The pigment dispersion of claim 2 wherein Z 4 is a diol that contains a sulfone.

4. The aqueous pigment dispersion of claim 1 wherein said polyurethane dispersant is substituted with one or more crosslinkable moieties, and said crosslinkable moieties are selected from the group consisting of acetoacetoxy, acid, amine, epoxy, hydroxyl, blocked isocyanates, and mixtures thereof.

5. The aqueous pigment dispersion of claim 4 wherein said polyurethane dispersant with substituted crosslinkable moieties is reacted with a crosslinking agent, and wherein said crosslinking agent is selected from a group consisting of acetoacetoxy, acid, amine, anhydride, epoxy, hydroxyl, isocyanates, blocked isocyanates and mixtures thereof.

6. The aqueous pigment dispersion of claim 1 wherein said heterocycle is oxazolidinone.

7. The aqueous pigment dispersion of claim 1 wherein said heterocycle is imidazolidinone.

8. The aqueous pigment dispersion of claim 1 wherein said heterocycle is thiazole.

9. The aqueous pigment dispersion of claim 1 wherein said heterocycle is pyridazine.

10. The aqueous pigment dispersion of claim 1 wherein said heterocycle is glycoside.

Assignees

• Du Pont

Inventors

• Roberts C Chad
• Jackson Christian
• Mcintyre Patrick F

Classifications

• C08G18/4858 Primary

  Polyethers containing oxyalkylene groups having more than four carbon atoms in the alkylene group · CPC title

• C08G18/6692

  with compounds of group C08G18/34 · CPC title

• C09D11/326

  characterised by the pigment dispersant · CPC title

• C08G18/765

  alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring · CPC title

• C09D175/04

  Polyurethanes · CPC title