REACTIVE POLYURETHANE DISPERSIONS

• US 20190284326A1
• Filed: 01/31/2017
• Published: 09/19/2019
• Est. Priority Date: 01/31/2017
• Status: Active Grant

• Current Assignee: Hewlett-Packard Development Company, L.P. (HP Inc.)
• Original Assignee: Hewlett-Packard Development Company, L.P. (HP Inc.)
• Inventors: ZHOU, Zhang-Lin, STRAMEL, Rodney David, LANE, Gregg A.
• Granted Patent: US 10,640,599 B2
• Time in Patent Office: Days
• CPC Class Codes: C08G 18/0828 containing sulfonate groups or groups forming them
• CPC Class Codes: C08G 18/0861 in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
• CPC Class Codes: C08G 18/246 containing also tin-carbon bonds
• CPC Class Codes: C08G 18/288 Compounds containing at least one heteroatom other than oxygen or nitrogen
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/675 Low-molecular-weight compounds
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/758 containing two or more cycloaliphatic rings
• CPC Class Codes: C08G 18/7671 containing only one alkylene bisphenyl group
• CPC Class Codes: C09D 11/101 Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
• CPC Class Codes: C09D 11/322 Pigment inks

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.

Claims

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 selected from an acrylate-containing diol, a methacrylate-containing diol, or combination thereof, and

a diisocyanate;

wherein the first capping unit is an acrylate-containing monoalcohol or a methacrylate-containing monoalcohol reacted with an isocyanate group of the diisocyanate; and

wherein the second capping unit is 3-(cyclohexylamino)-1-propanesulfonic acid or 2-(cyclohexylamino)ethanesulfonic acid reacted with an isocyanate group of the diisocyanate.

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 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 to 100.

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

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

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

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

9. 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.

10. 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 selected from an acrylate-containing diol, a methacrylate-containing diol, or combination thereof, and

a diisocyanate;

wherein the first capping unit is an acrylate-containing monoalcohol or a methacrylate-containing monoalcohol reacted with an isocyanate group of the diisocyanate; and

wherein the second capping unit is 3-(cyclohexylamino)-1-propanesulfonic acid or 2-(cyclohexylamino)ethanesulfonic acid reacted with an isocyanate group of the diisocyanate.

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

12. The UV-curable ink composition of claim 11, 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.

13. The UV-curable ink composition of claim 10, wherein the polymer backbone is devoid of ionic stabilizing groups.

14. 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, or combination thereof, 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.

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