Reactive polyurethane dispersions

Patent metadata

Field	Value
Publication number	US-10920074-B2
Application number	US-201716335541-A
Country	US
Kind code	B2
Filing date	Jan 31, 2017
Priority date	Jan 31, 2017
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

The present disclosure is drawn to reactive polyurethane dispersions. In one example, a reactive polyurethane dispersion can include 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, an acrylamide-containing diol, a methacrylamide-containing diol, or combination thereof. The first capping unit can be an acrylamide-containing monoalcohol or methacrylamide-containing monoalcohol reacted with an isocyanate group of the diisocyanate. The second capping unit can be an ionic stabilizing group.

First claim

What is claimed is:

1. A reactive polyurethane dispersion, comprising a polymer strand comprising a polymer backbone having two terminating ends comprising a first capping unit at a first terminating end and a second capping unit at a second terminating end, wherein the polymer backbone comprises polymerized monomers including:
a reactive diol selected from an acrylate-containing diol, a methacrylate-containing diol, an acrylamide-containing diol, a methacrylamide-containing diol, or combination thereof; and
a diisocyanate,
wherein the first capping unit is an acrylamide-containing monoalcohol or methacrylamide-containing monoalcohol reacted with an isocyanate group of the diisocyanate;
wherein the second capping unit is an ionic stabilizing group; and
wherein the reactive polyurethane dispersion has a NCO/OH ratio of 1.2 to 10.

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 an acid number of 20 to 100.

4. The reactive polyurethane dispersion of claim 1 , wherein the reactive polyurethane dispersion has a double bond density of 1.5 to 10.

5. The reactive polyurethane dispersion of claim 1 , wherein the acrylamide-containing monoalcohol or methacrylamide-containing monoalcohol is selected from:

or a combination thereof.

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

or a combination thereof.

7. The reactive polyurethane dispersion of claim 1 , wherein the reactive polyurethane dispersion is devoid of polymer strands having capping units that include acrylate groups or methacrylate groups.

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 acrylamide-containing monoalcohol or methacrylamide-containing monoalcohol reacted with an isocyanate group of the diisocyanate and a second capping unit that is an ionic stabilizing group.

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 terminating ends comprising a first capping unit at a first terminating end and a second capping unit at a second terminating end, wherein the polymer backbone comprises polymerized monomers including:
a reactive diol selected from an acrylate-containing diol, a methacrylate-containing diol, an acrylamide-containing diol, a methacrylamide-containing diol, or combination thereof, and
a diisocyanate,

wherein the first capping unit is an acrylamide-containing monoalcohol or methacrylamide-containing monoalcohol reacted with an isocyanate group of the diisocyanate; and
B wherein the second capping unit is an ionic stabilizing group.

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 selected from an acrylate-containing diol, a methacrylate-containing diol, an acrylamide-containing diol, a methacrylamide-containing diol, or combination thereof, to form a first pre-polymer;
reacting the first pre-polymer with an acrylamide-containing monoalcohol or methacrylamide-containing monoalcohol to form a second pre-polymer;
reacting the second pre-polymer with an acid-containing amine to form a polymer strand; and
dispersing the polymer strand in water to form the reactive polyurethane having a NCO/OH ratio of 1.2 to 10.

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. 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 selected from:

or a combination thereof; and
a diisocyanate,
wherein the first capping unit is an acrylamide-containing monoalcohol or methacrylamide-containing monoalcohol reacted with an isocyanate group of the diisocyanate; and
wherein the second capping unit is an ionic stabilizing group.

16. The reactive polyurethane dispersion of claim 15 , wherein the polymer backbone is devoid of ionic stabilizing groups.

17. The reactive polyurethane dispersion of claim 15 , wherein the reactive polyurethane dispersion has an acid number of 20 to 100, a double bond density of 1.5 to 10, or is devoid of polymer strands having capping units that include acrylate groups or methacrylate groups.

18. The reactive polyurethane dispersion of claim 15 , wherein the acrylamide-containing monoalcohol or methacrylamide-containing monoalcohol is selected from:

or a combination thereof.

19. A method of making a reactive polyurethane dispersion, comprising:
reacting a diisocyanate with a reactive diol selected from:

or a combination thereof, to form a first pre-polymer;
reacting the first pre-polymer with an acrylamide-containing monoalcohol or methacrylamide-containing monoalcohol to form a second pre-polymer;
reacting the second pre-polymer with an acid-containing amine to form a polymer strand; and
dispersing the polymer strand in water to form the reactive polyurethane.

20. The method of claim 19 , further comprising adding a colorant and a photoinitiator to the reactive polyurethane dispersion to form a UV-curable ink composition.

Assignees

• Hewlett Packard Development Co

Inventors

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

Classifications

• C08G18/758

  containing two or more cycloaliphatic rings · 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

• C08G18/672

  Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen · CPC title

• C08G18/8158

  with unsaturated compounds having only one group containing active hydrogen · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title