Reactive polyurethane dispersions

Patent metadata

Field	Value
Publication number	US-10640599-B2
Application number	US-201716335372-A
Country	US
Kind code	B2
Filing date	Jan 31, 2017
Priority date	Jan 31, 2017
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

The present disclosure is drawn to a reactive polyurethane dispersion including a polymer strand having a polymer backbone that has two ends terminating at a first capping unit and a second capping unit. The polymer backbone can include polymerized monomers including a reactive diol and a diisocyanate. The reactive diol can be an acrylate-containing diol, a methacrylate-containing diol, or combination thereof. The first capping unit can be an acrylate-containing monoalcohol or a methacrylate-containing monoalcohol reacted with an isocyanate group of the diisocyanate. The second capping unit can be 3-(cyclohexylamino)-1-propanesulfonic acid or 2-(cyclohexylamino)ethanesulfonic acid reacted with an isocyanate group of the diisocyanate.

First claim

What is claimed is:

1. A reactive polyurethane dispersion, comprising a polymer strand comprising a polymer backbone having two ends terminating at a first capping unit and a second capping unit, wherein the polymer backbone comprises polymerized monomers including:
a reactive diol, and
a diisocyanate;
wherein the first capping unit is either an acrylate-containing monoalcohol reacted with an isocyanate group of the diisocyanate or a methacrylate-containing monoalcohol reacted with an isocyanate group of the diisocyanate;
wherein the second capping unit is either 3-(cyclohexylamino)-1-propanesulfonic acid reacted with an isocyanate group of the diisocyanate or 2-(cyclohexylamino)ethanesulfonic acid reacted with an isocyanate group of the diisocyanate; and
wherein the reactive diol is selected from:

or a combination thereof.

2. The reactive polyurethane dispersion of claim 1 , wherein the polymer backbone is devoid of ionic stabilizing groups.

3. The reactive polyurethane dispersion of claim 1 , wherein the reactive polyurethane dispersion has a NCO/OH mole ratio of 1.2 to 10.

4. The reactive polyurethane dispersion of claim 1 , wherein the reactive polyurethane dispersion has an acid number of 20 mg KOH/g to 100 mg KOH/g.

5. The reactive polyurethane dispersion of claim 1 , wherein the reactive polyurethane dispersion has a double bond density of 1.5 mmol/g to 10 mmol/g.

6. The reactive polyurethane dispersion of claim 1 , wherein the diisocyanate is selected from:

or a combination thereof.

7. The reactive polyurethane dispersion of claim 1 , wherein the acrylate-containing monoalcohol or a methacrylate-containing monoalcohol is selected from:

or a combination thereof.

8. The reactive polyurethane dispersion of claim 1 , wherein a majority of polymer strands in the reactive polyurethane dispersion have a first capping unit that is an acrylate-containing monoalcohol or a methacrylate-containing monoalcohol reacted with an isocyanate group of the diisocyanate and a second capping unit that is 3-(cyclohexylamino)-1-propanesulfonic acid or 2-(cyclohexylamino)ethanesulfonic acid reacted with an isocyanate group of the diisocyanate.

9. A UV-curable ink composition, comprising:
a colorant;
a photoinitiator; and
a reactive polyurethane dispersion, comprising a polymer strand comprising a polymer backbone having two ends terminating at a first capping unit and a second capping unit, wherein the polymer backbone comprises polymerized monomers including:
a reactive diol, and
a diisocyanate;

wherein the first capping unit is either an acrylate-containing monoalcohol reacted with an isocyanate group of the diisocyanate or methacrylate-containing monoalcohol reacted with an isocyanate group of the diisocyanate;
wherein the second capping unit is either 3-(cyclohexylamino)-1-propanesulfonic acid reacted with an isocyanate group of the diisocyanate or 2-(cyclohexylamino)ethanesulfonic acid reacted with an isocyanate group of the diisocyanate; and
wherein the reactive diol is selected from:

or a combination thereof.

10. The UV-curable ink composition of claim 9 , wherein the UV-curable ink composition has a pH of 7.0 to 11.5.

11. The UV-curable ink composition of claim 10 , wherein the pH does not decrease by more than 1.0 when the UV-curable ink composition is exposed to accelerated shelf life (ASL) at 50° C. in open air for 1 week.

12. The UV-curable ink composition of claim 9 , wherein the polymer backbone is devoid of ionic stabilizing groups.

13. A method of making a reactive polyurethane dispersion, comprising:
reacting a diisocyanate with a reactive diol to form a first pre-polymer;
reacting the first pre-polymer with a reactive group selected from an acrylate-containing monoalcohol, a methacrylate-containing monoalcohol, or combination thereof, to form a second pre-polymer;
reacting the second pre-polymer with 3-(cyclohexylamino)-1-propanesulfonic acid, 2-(cyclohexylamino)ethanesulfonic acid, or a combination thereof, to form a polymer strand; and
dispersing the polymer strand in water to form the reactive polyurethane dispersion;
wherein the reactive diol is selected from:

or a combination thereof.

14. The method of claim 13 , further comprising adding a colorant and a photoinitiator to the reactive polyurethane dispersion to form a UV-curable ink composition.

15. The reactive polyurethane dispersion of claim 7 , wherein the first capping unit is compound (XV) reacted with an isocyanate group of the diisocyanate.

16. The UV-curable ink composition of claim 9 , wherein the photoinitiator has the general formula:

where R 1 to R 4 are independently a hydrogen atom, an unsubstituted alkyl, a substituted alkyl, an unsubstituted alkenyl, a substituted alkenyl, an unsubstituted aryl, a substituted aryl, an unsubstituted aralkyl, a substituted aralkyl, a halogen atom, —NO 2 , —O—R d , —CO—R d , —CO—O—R d , —O—CO—R d , —CO—NR d R e , —NR d R e , —NR d —CO—R e , —NR d —CO—R e , —NR d —CO—NR e R f , —SR d , —SO—R d , —SO 2 —R d , —SO 2 —O—R d , —SO 2 NR d R e , or a perfluoroalkyl group; where R d , R e , and R f are independently a hydrogen atom, an unsubstituted alkyl, a substituted alkyl, an unsubstituted alkenyl, a substituted alkenyl, an unsubstituted aryl, a substituted aryl, an unsubstituted aralkyl, or a substituted aralkyl; where X is selected from —O—, —S—, —NH—, and —NR—, where R is selected from CH 3 , CH 2 CH 3 , and CH 2 CH 2 CH 3 ; where R 5 is an organic group that includes a polyether chain.

Assignees

• Hewlett Packard Development Co

Inventors

• Zhou Zhang-Lin
• Stramel Rodney David
• Lane Gregg A

Classifications

• C08G18/73

  acyclic · CPC title

• C08G18/288

  Compounds containing at least one heteroatom other than oxygen or nitrogen · CPC title

• C08G18/3206

  aliphatic · CPC title

• C09D11/101

  Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing · CPC title

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title