Polyurethane-based binder dispersion

Patent metadata

Field	Value
Publication number	US-11319454-B2
Application number	US-201716461627-A
Country	US
Kind code	B2
Filing date	Feb 27, 2017
Priority date	Feb 27, 2017
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

A polyurethane-based binder dispersion is described. The polyurethane based binder dispersion comprises: a polyurethane, which comprises: (A) a polyisocyanate; (B) a first polyol having a chain with two hydroxyl functional groups at one end of the chain and no hydroxyl groups at an opposed end of the chain; (C) a second polyol having a chain with two hydroxyl functional groups at both ends of the chain; (D) a carboxylic acid functional group with two hydroxyl functional groups; and (E) a compound shown in formula (1): m(M+) n(X)—R—Y— (1), wherein m is 0 or 1, M is a metal, n is 2 to 10, X is an amino group, R is a C1 to C18 alkyl group, a C6 to C30 aromatic compound or a C4 to C20 aliphatic cyclic compound, and Y is SO3- or SO3H, with the proviso that when m is 0, Y is SO3H and when m is 1, Y is SO3-.

First claim

What is claimed is:

1. A polyurethane-based binder dispersion comprising:
a polyurethane, which comprises:
(A) a polyisocyanate;
(B) a first polyol having a chain with two hydroxyl functional groups at one end of the chain and no hydroxyl groups at an opposed end of the chain;
(C) a second polyol having a chain with one hydroxyl functional group at each end of the chain;
(D) a carboxylic acid functional group with two hydroxyl functional groups;
(E) a compound shown in formula (1) below
m (M+) n (X)—R—Y  (1)

wherein
m is 0 or 1;
M is a metal;
n is 2 to 10;
X is an amino group,
R is a C1 to C18 alkyl group, a C6 to C30 aromatic compound or a C4 to C20 aliphatic cyclic compound, and
Y is SO 3− or SO 3 H
with the proviso that when m is 0, Y is SO 3 H and when m is 1, Y is SO 3− , wherein (E) is present in the polyurethane-based binder dispersion in an amount of from about 10 wt % to about 15 wt % based on the total weight of the polyurethane-based binder dispersion; and
(F) an optional homopolymer or copolymer of poly(ethylene glycol) having one or two hydroxyl functional groups or one or two amino functional groups at one end of its chain, and
water,
wherein the polyurethane is dispersed in the water.

2. The polyurethane-based binder dispersion of claim 1 wherein in the formula (1):
m is 1;
M is sodium, potassium, magnesium, calcium, or lithium;
n is 2 to 4;
X is the amino group;
R is the C1 to C8 alkyl group; and
Y is SO 3− .

3. The polyurethane-based binder dispersion of claim 1 , wherein (A) is present in the polyurethane-based binder dispersion in an amount of from about 20 wt % to about 35 wt % based on the total weight of the polyurethane-based binder dispersion.

4. The polyurethane-based binder dispersion of claim 1 , wherein (A) is isophorone diisocyanate (IPDI), 2,2,4-trimethyl-hexamethylene-diisocyanate (TMDI), dicyclohexylmethane-4,4-diisocyanate (H12MDI), hexamethylene-1,6-diisocyanate (HDI), or mixtures thereof.

5. The polyurethane-based binder dispersion of claim 1 , wherein (B) is present in the polyurethane-based binder dispersion in an amount of from about 30 wt % to about 60 wt % based on the total weight of the polyurethane-based binder dispersion.

6. The polyurethane-based binder dispersion of claim 1 , wherein:
(B) is formed from a free radical polymerization of a monomer in the presence of a mercaptan including two hydroxyl functional groups or two carboxylic functional groups;
the monomer is selected from the group consisting of an alkylester of acrylic acid, an alkylester of methacrylic acid, an acid group containing monomer, acrylamide, an acrylamide derivative, methacrylamide, a methacrylamide derivative, styrene, a styrene derivative, acrylonitrile, vinylidene chloride, a fluorine containing acrylate, a fluorine containing methacrylate, a siloxane containing acrylate, a siloxane containing methacrylate, vinyl acetate, N-vinylpyrrolidone, and combinations thereof; and
the mercaptan is selected from the group consisting of 1,2-propanediol (thioglycerol), 1-mercapto-1,1-ethanediol, 2-mercapto-1,3-propanediol, 2-mercapto-2-methyl-1,3-propanediol, 2-mercapto-2-ethyl-1,3-propanediol, 1-mercapto-2,3-propanediol, 2-mercaptoethyl-2-methyl-1,3-propanediol, and thioglycolic acid.

7. The polyurethane-based binder dispersion of claim 1 , wherein (C) is present in the polyurethane-based binder dispersion in an amount of from about 8 wt % to about 20 wt % based on the total weight of the polyurethane-based binder dispersion.

8. The polyurethane-based binder dispersion of claim 1 , wherein (C) is poly(propyleneglycol), poly(tetrahydrofuran), poly(carbonate) polyol, or mixtures thereof.

9. The polyurethane-based binder dispersion of claim 1 , wherein (D) is present in the polyurethane-based binder dispersion in an amount of from about 2 wt % to about 8 wt % based on the total weight of the polyurethane-based binder dispersion.

10. The polyurethane-based binder dispersion of claim 1 , wherein (D) is dimethylolpropionic acid (DMPA), dimethylol butanoic acid (DMBA), or mixtures thereof.

11. The polyurethane-based binder dispersion of claim 1 , wherein (E) is ethyldiamineethylsulfonic acid or a salt thereof, ethyldiaminepropylsulfonic acid or a salt thereof, 5-amino-2-(aminomethyl)-1-pentanesulfonic acid or a salt thereof, 2,3-diamino-1-propanesulfonic acid or a salt thereof, 3-[bis(2-aminoethyl)amino]-1-propanesulfonic acid or a salt thereof, 2-[bis(2-aminoethyl)amino]-ethanesulfonic acid or a salt thereof, 2-[(2-aminoethyl)amino]-1-propanesulfonic acid or a salt thereof, 2-[[2-[(1-methylethyl)amino]ethyl]amino]-ethanesulfonic acid or a salt thereof, 2-[(2-aminoethyl)amino]-1-pentanesulfonic acid or a salt thereof, or mixtures thereof.

12. An inkjet ink composition comprising:
the polyurethane-based binder dispersion of claim 1 ;
at least one colorant;
at least one surfactant;
at least one co-solvent; and
water.

13. A method of using the polyurethane-based binder dispersion of claim 1 comprising:
adding the polyurethane-based binder dispersion of claim 1 to an inkjet ink composition comprising water, at least one colorant, at least one co-solvent, and at least one surfactant; and
optionally applying the inkjet ink composition containing the polyurethane-based binder dispersion to a media substrate.

14. A method of making a polyurethane-based binder dispersion comprising:
mixing a polyurethane with water to form a polyurethane-based binder dispersion, wherein the polyurethane comprises:
(A) a polyisocyanate in an amount of from about 20 wt % to about 35 wt % based on the total weight of the polyurethane-based binder dispersion;
(B) a first polyol having a chain with two hydroxyl functional groups at one end of the chain and no hydroxyl groups at an opposed end of the chain in an amount of from about 30 wt % to about 60 wt % based on the total weight of the polyurethane-based binder dispersion;
(C) a second polyol having a chain with one hydroxyl functional group at each end of the chain in an amount of from about 8 wt % to about 20 wt % based on the total weight of the polyurethane-based binder dispersion;
(D) a carboxylic acid functional group with two hydroxyl functional groups in an amount of from about 2 wt % to about 8 wt % based on the total weight of the polyurethane-based binder dispersion;
(E) a compound including a sulfonate or sulfonic acid functional group and having two or more amino functional groups, (E) being present in an amount of from about 10 wt % to about 15 wt % based on the total weight of the polyurethane-based binder dispersion, wherein (E) is shown in formula (1) below:
m (M+) n (X)—R—Y  (1)

wherein
m is 0 or 1;
M is a metal;
n is 2 to 10;
X is an amino group,
R is a C1 to C18 alkyl group, a C6 to C30 aromatic compound or a C4 to C20 aliphatic cyclic compound, and
Y is SO 3− or SO 3 H
with the proviso that when m is 0, Y is SO 3 H and when m is 1, Y is SO 3− ; and
(F) an optional homopolymer or copolymer of poly(ethylene glycol) having one or two hydroxyl functional groups or one or two amino functional groups at one end of its chain.

15. The polyurethane-based binder dispersion of claim 1 wherein the second polyol has a number average molecular weight of about 500 g/mol to about 3000 g/mol.

Assignees

• Hewlett Packard Development Co

Inventors

• Chen Tienteh
• Abelovski Benjamin
• Brandstein Or
• Yang Jun
• Lane Gregg A

Classifications

• C08G18/12

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title

• C09D11/38 Primary

  characterised by non-macromolecular additives other than solvents, pigments or dyes · CPC title

• C08G18/6625

  with compounds of group C08G18/34 · CPC title

• C08G18/44

  Polycarbonates · CPC title

• C09D175/08

  from polyethers · CPC title