Polyurethane-based binder dispersion

Patent metadata

Field	Value
Publication number	US-10005876-B2
Application number	US-201515544494-A
Country	US
Kind code	B2
Filing date	Jan 30, 2015
Priority date	Jan 30, 2015
Publication date	Jun 26, 2018
Grant date	Jun 26, 2018

Abstract

A binder dispersion includes water and polyurethane. The polyurethane is formed from polyisocyanate; polyol having two hydroxyl (OH) groups at one chain end, no OH groups at an opposed chain end, and a number average molecular weight (M n ) ranging from ˜500-˜5,000; an alcohol, diol or amine having a M n <500; and one of i) a carboxylic acid; ii) a sulfonate or sulfonic acid having one amino group; iii) i and ii; iv) i and a homopolymer or copolymer of poly(ethylene glycol) (PEG) having one or two OH or amino groups at one chain end; v) ii and a homopolymer or copolymer of PEG having one or two OH or amino groups at one chain end; or vi) i, ii, and a homopolymer or copolymer of PEG having one or two OH or amino groups at one chain end.

First claim

What is claimed is:

1. A polyurethane-based binder dispersion, comprising:
water; and
a polyurethane dispersed in the water, the polyurethane having been formed from:
a polyisocyanate;
a 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, and having a number average molecular weight ranging from about 500 to about 5,000;
an alcohol or a diol or an amine having a number average molecular weight less than 500; and one of
i) a carboxylic acid;
ii) a sulfonate or sulfonic acid having one amino functional group;
iii) a combination of i and ii;
iv) a combination of i and a 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;
v) a combination of ii and a 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; or
vi) a combination of i, ii, and a 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.

2. The polyurethane-based binder dispersion as defined in claim 1 wherein the sulfonate or sulfonic acid having the one amino functional group has, at most, one hydroxyl functional group in addition to the sulfonate or sulfonic acid.

3. The polyurethane-based binder dispersion as defined in claim 2 wherein the sulfonate or sulfonic acid is selected from the group consisting of taurine, 4-Aminotoluene-3-sulfonic acid, Aniline-2-sulfonic acid, Sulfanilic acid, 4-Amino-1-naphthalenesulfonic acid, 3-Amino-4-hydroxybenzenesulfonic acid, 2-Amino-1-naphthalenesulfonic acid, 5-Amino-2-methoxybenzenesulfonic acid, 2-(Cyclohexylamino)ethanesulfonic acid, and 3-Amino-1-propanesulfonic acid.

4. The polyurethane-based binder dispersion as defined in claim 1 wherein:
the polyol 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.

5. The polyurethane-based binder dispersion as defined in claim 4 wherein:
the alkylester of acrylic acid or the alkylester of methacrylic acid is selected from the group consisting of methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, tetrahydrofuryl (meth)acrylate, t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, hexyl (meth)acrylate, cyclohexyl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, 2-aziridinylethyl (meth)acrylate, aminomethyl acrylate, aminoethyl acrylate, aminopropyl (meth)acrylate, amino-n-butyl(meth)acrylate, N,N-dimethylaminoethyl(meth)acrylate, N,N-dimethylaminopropyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, and N,N-diethylaminopropyl (meth)acrylate; or
the acid group containing monomer is selected from the group consisting of acrylic acid, methacrylic acid, carboxyethyl (meth)acrylate, 2-(meth)acryloyl propionic acid, crotonic acid, and itaconic acid; or
the acrylamide derivative or the methacrylamide derivative is selected from the group consisting of hydroxyethylacrylamide, N,N-methylol(meth)acrylamide, N-butoxymethyl (meth)acrylamide, and N-isobutoxymethyl (meth)acrylamide; or
the styrene derivative is selected from the group consisting of alpha-methyl styrene, p-aminostyrene, and 2-vinylpyridine.

6. The polyurethane-based binder dispersion as defined in claim 4 wherein one of:
the monomer includes methyl methacrylate and butyl acrylate in a ratio of 1:1 and the mercaptan includes 10 wt % thioglycerol;
the monomer includes methyl methacrylate and 2-ethylhexyl acrylate in a ratio of 3:1 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes methyl methacrylate and 2-ethylhexyl acrylate in a ratio of 1:1 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes methyl methacrylate and 2-ethylhexyl acrylate in a ratio of 9:1 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes methyl methacrylate, 2-ethylhexyl acrylate, and methacrylic acid in a ratio of 5:4:1 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes methyl methacrylate and 2-ethylhexyl acrylate in a ratio of 1:1 and the mercaptan includes 10 wt % thioglycerol;
the monomer includes methyl methacrylate, 2-ethylhexyl acrylate, and methacrylic acid in a ratio of 10:8:3 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes methyl methacrylate and t-butyl acrylate in a ratio of 1:1 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes t-butyl methacrylate and 2-ethylhexyl acrylate in a ratio of 1:1 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes benzyl (meth)acrylate and 2-ethylhexyl acrylate in a ratio of 1:1 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes styrene and butyl acrylate in a ratio of 1:1 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes vinyl acetate and butyl acrylate in a ratio of 1:1 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes cyclohexyl methacrylate and butyl acrylate in a ratio of 1:1 and the mercaptan includes 5 wt % thioglycerol; or
the monomer includes tetrahydrofuryl methacrylate and butyl acrylate in a ratio of 1:1 and the mercaptan includes 5 wt % thioglycerol.

7. The polyurethane-based binder dispersion as defined in claim 1 wherein the polyurethane is formed from one of iv, v, or vi, and wherein the 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 is present in an amount ranging from greater than 5 wt % to about 20 wt % based on a total wt % of the polyurethane.

8. The polyurethane-based binder dispersion as defined in claim 7 wherein the homopolymer or copolymer of poly(ethylene glycol) has a number average molecular weight (M n ) ranging from about 500 to about 5000 and a water solubility greater than 30% v/v, and wherein the homopolymer or copolymer of poly(ethylene glycol) is one of:
a poly(ethylene glycol) copolymer selected from the group consisting of a copolymer of poly(ethylene) and poly(ethylene glycol) with the one hydroxyl functional group, a copolymer of poly(propylene glycol) and poly(ethylene glycol) with the one hydroxyl functional group, and a copolymer of poly(ethylene glycol) and poly(propylene glycol) with the one amino functional group; or
a poly(ethylene glycol) homopolymer selected from the group consisting of monoamine terminated poly(ethylene glycol), poly(ethylene glycol) monoethyl ether, poly(ethylene glycol) monopropyl ether, poly(ethylene glycol) monobutyl ether, poly(ethylene glycol) monomethyl ether, and two hydroxyl terminated at one end poly(ethylene glycol).

9. The polyurethane-based binder dispersion as defined in claim 1 wherein:
t

Assignees

• Hewlett Packard Development Co

Inventors

• Chen Tienteh
• Huang Bin

Classifications

• C08G18/3857

  having nitrogen in addition to sulfur · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C08G18/755 Primary

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

• C08G18/348

  Hydroxycarboxylic acids · CPC title

• C09D11/38

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