Radiation curable polyurethane-based binder dispersion

Patent metadata

Field	Value
Publication number	US-10829583-B2
Application number	US-201515737744-A
Country	US
Kind code	B2
Filing date	Oct 28, 2015
Priority date	Oct 28, 2015
Publication date	Nov 10, 2020
Grant date	Nov 10, 2020

Abstract

A radiation curable polyurethane-based binder dispersion includes water and a radiation curable polyurethane dispersed in the water. The polyurethane is 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 acrylate or methacrylate, the acrylate or methacrylate having at least one hydroxyl functional group and having an acrylate functional group or a methacrylate functional group; an alcohol or a diol or an amine having a number average molecular weight less than 600; and a sulfonate or sulfonic acid having one or two amino functional groups.

First claim

What is claimed is:

1. A radiation curable polyurethane-based binder dispersion, comprising:
water; and
a radiation curable 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 acrylate or methacrylate, the acrylate or methacrylate having at least one hydroxyl functional group and having an acrylate functional group or a methacrylate functional group;
an alcohol or a diol or an amine having a number average molecular weight less than 600; and
a sulfonate or sulfonic acid having one or two amino functional groups.

2. The radiation curable polyurethane-based binder dispersion as defined in claim 1 , the radiation curable polyurethane having further been formed from:
i) a carboxylic acid having two or more hydroxyl functional groups; or
ii) 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
iii) a combination of i and ii.

3. The radiation curable polyurethane-based binder dispersion as defined in claim 1 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, 3-amino-1-propanesulfonic acid, 2-2-(aminoethyl)aminoethanesulfonic acid, 3-2-(aminoethyl)aminopropanesulfonic acid, N,N-Bis(2-hydroxyethyl)taurine, 4-(2-hydroxyethyl)piperazine-1-ethanesulfonic acid, and N-(2-acetamido)-2-aminoethanesulfonic acid.

4. The radiation curable 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 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 radiation curable 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, trifluoroethyl (meth)acrylate, t-butyl (meth)acrylate, t-butyl acrylate, n-butyl acrylate 2-ethylhexyl (meth)acrylate, 2-ethylhexyl acrylate, hexyl (meth)acrylate, cyclohexyl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, allyl (meth)acrylate, isobornyl (meth)acrylate, isobornyl acrylate, polyester (meth)acrylate, polycarbonate (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, diacetone 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 radiation curable polyurethane-based binder dispersion as defined in claim 4 wherein one of:
the monomer includes methyl methacrylate and n-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 allyl methacrylate and 2-ethylhexyl acrylate in a ratio of 7:3 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes acrylonitrile and n-butyl acrylate in a ratio of 6:4 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes benzyl methacrylate and 2-ethylhexyl acrylate in a ratio of 8:2 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes cyclohexyl methacrylate and 2-ethylhexyl acrylate in a ratio of 66:34 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes methyl methacrylate, 2-ethylhexyl acrylate, and diacetone acrylamide in a ratio of 50:45:5 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes isobornyl acrylate, methyl methacrylate and n-butylacrylate in a ratio of 20:57:23 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes isobornyl methacrylate and n-butyl acrylate in a ratio of 65:35 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes cyclohexyl methacrylate and 2-ethylhexyl acrylate in a ratio of 8:2 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes benzyl methacrylate and 2-ethylhexyl acrylate in a ratio of 19:1 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes t-butyl acrylate and n-butyl methacrylate in a ratio of 8:2 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes benzyl methacrylate, methyl methacrylate and n-butyl acrylate in a ratio of 2:6:2 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes cyclohexyl methacrylate, methyl methacrylate, and n-butyl acrylate in a ratio of 20:57:23 and the mercaptan includes 5 wt % thioglycerol;
the monomer includes isobornyl acrylate, methyl methacrylate and 2-ethylhexyl acrylate in a ratio of 20:57:23 and the mercaptan includes 5 wt % thioglycerol; or
the monomer includes styrene and n-butyl methacrylate in a ratio of 4:6 and the mercaptan includes 5 wt % thioglycerol.

7. The radiation curable polyurethane-based binder dispersion as defined in claim 1 wherein the acrylate or methacrylate is chosen from:
aliphatic diglycidyl compounds selected from the group consisting of 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, cyclohexanedimethanol diglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, hydrogenated bisphenol A diglycidyl ether (BGDA or BADGE), hydrogenated bisphenol F diglycidyl ether, and 1,6-hexanediylbis[oxy(2-hydroxy

Assignees

• Hewlett Packard Development Co

Inventors

• Chen Tienteh
• Huang Bin
• Abelovski Benjamin
• Sarkisian George

Classifications

• C08G18/288

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

• B41M5/0017

  Application of ink-fixing material, e.g. mordant, precipitating agent, on the substrate prior to printing, e.g. by ink-jet printing, coating or spraying · CPC title

• C08G18/6541

  the low-molecular compounds being compounds of group C08G18/34 · CPC title

• C08G18/0866

  the dispersing or dispersed phase being an aqueous medium · CPC title

• C09D175/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title