# US 2006/0065155 A1 · Cosolvents in printing fluids

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- Number: US 2006/0065155 A1
- Document ID: US20060065155A1
- Status: Published application
- Kind: A1
- Application number: 10/951,411
- Filed: 2004-09-27
- Published: 2006-03-30
- Earliest claimed: 2004-09-27
- Assignees: Hewlett-Packard Development Company, L.P.
- Inventors: Gary Byers; Richard Anderson; Mark Choy
- Web page: https://patentgrep.com/patent/US20060065155A1

## CPC

- C09D 11/30: Inkjet printing inks
- C09D 11/03: characterised by features other than the chemical nature of the binder
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

An aqueous printing fluid, comprising a cosolvent, the cosolvent or mixture of compounds comprising at least one inner salt compound having a sp3-hybridized nitrogen cation and an associated anionic charge either isolated on an N-substituted oxygen anion bound directly to the sp3-hybridized nitrogen cation or isolated among the oxygens of a carboxylate group; a method of avoiding paper curl in printed paper by using the above-described aqueous printing fluid; and a printer system for avoiding paper curl in printed paper through using the above-described aqueous printing fluid.

## Claims

### Claim 1

An aqueous printing fluid comprising at least one anti-curl cosolvent, wherein the at least one anti-curl cosolvent comprises at least one inner salt compound having a sp3-hybridized nitrogen cation and an associated anionic charge which is either isolated on an oxygen anion bound directly to the sp3-hybridized nitrogen cation or isolated among the oxygens of a carboxylate group.

### Claim 2 (depends on 1)

The aqueous printing fluid of claim 1, wherein the at least one anti-curl cosolvent forms a blended solution with at least one non-ionic, water-soluble blend cosolvent.

### Claim 3 (depends on 2)

The aqueous printing fluid of claim 2, wherein the at least one blend cosolvent has a neat solvent vapor pressure of no more than 4×10−2 mm Hg and is capable of strong H-bonding interactions for disrupting fiber-to-fiber H-bonds in cellulose-based paper.

### Claim 4 (depends on 3)

The aqueous printing fluid of claim 3, wherein the at least one blend cosolvent has a neat solvent vapor pressure of no more than 1×10−4.

### Claim 5 (depends on 2)

The aqueous printing fluid of claim 2, wherein the aqueous printing fluid comprises from 5 to 60% of the blended solution of the at least one anti-curl cosolvent and the at least one blend cosolvent and the weight ratio of the inner salt anti-curl cosolvent(s) to blend cosolvent(s) in the blended solution ranges from 3:97 to 99:1.

### Claim 6 (depends on 1)

The aqueous printing fluid of claim 1, wherein the at least one inner salt compound comprises an ammonium N-oxide moiety.

### Claim 7 (depends on 5)

The aqueous printing fluid of claim 5, wherein the at least one inner salt compound comprises an ammonium N-oxide moiety with three alkyl groups attached to the nitrogen, and wherein each alkyl group independently comprises up to 6 carbons, each alkyl group being either a straight-chain, a branched chain, or a 5 to 7-membered ring comprising at least 4 carbons.

### Claim 8 (depends on 7)

The aqueous printing fluid of claim 7, wherein the 5 to 7-membered ring comprises at least one hetero atom selected from the group consisting of oxygen and nitrogen.

### Claim 9 (depends on 8)

The aqueous printing fluid of claim 8, wherein the 5 to 7-membered ring is a morpholine ring.

### Claim 10 (depends on 7)

The aqueous printing fluid of claim 7, wherein at least one of the three alkyl groups comprises at least one water-solubilizing substituent.

### Claim 11 (depends on 10)

The aqueous printing fluid of claim 10, wherein the at least one water-solubilizing substituent is selected from the group consisting of a hydroxyl group, a carbonyl group, an amide group, a sulfone group, a sulfoxide group, a polyethylene glycol moiety and an ammonium-N-oxide moiety.

### Claim 12 (depends on 6)

The aqueous printing fluid of claim 6, wherein the at least one inner salt compound is selected from the group consisting of N-MethylMorpholine-N-Oxide (MMNO); N-EthylMorpholine-N-Oxide (EMNO); N,N-DiMethylButylAmmonium-N-Oxide (DMBANO) and N,N,N-TriMethylAmmonium-N-Oxide (TMANO).

### Claim 13 (depends on 1)

The aqueous printing fluid of claim 1, wherein the at least one inner salt compound comprises a betaine moiety.

### Claim 14 (depends on 13)

The aqueous printing fluid of claim 13, wherein the betaine moiety is Betaine (N,N,N-Trimethyl Glycinate).

### Claim 15 (depends on 1)

The aqueous printing fluid of claim 1, wherein the at least one inner salt compound comprises an amino acid.

### Claim 16 (depends on 15)

The aqueous printing fluid of claim 15, wherein the amino acid is selected from the group consisting of α-Glycine, β-Alanine and γ-Aminobutyric acid.

### Claim 17 (depends on 2)

The aqueous printing fluid of claim 2, wherein the aqueous printing fluid comprises at least 10 weight percent of the anti-curl cosolvent or the blended solution of the anti-curl cosolvent and the blend cosolvent.

### Claim 18 (depends on 1)

The aqueous printing fluid of claim 1, wherein the aqueous printing fluid is an inkjet ink.

### Claim 19 (depends on 18)

The aqueous printing fluid of claim 18, wherein the inkjet ink comprises pigment colorant.

### Claim 20 (depends on 18)

The aqueous printing fluid of claim 18, wherein the inkjet ink comprises dye colorant.

### Claim 21 (depends on 1)

The aqueous printing fluid of claim 1, wherein the aqueous printing fluid is a fixer fluid.

### Claim 22 (depends on 20)

The aqueous printing fluid of claim 20, wherein the at least one inner salt compound is an ammonium-N-oxide moiety, which when mixed with a strong acid, gives an ammonium-N-oxide conjugate acid with an approximate pKa=4-5 and a buffering capacity in aqueous solution near pH 4-5.

### Claim 23

A method of avoiding paper curl in printed paper comprising:
a) preparing an aqueous printing fluid comprising at least one anti-curl cosolvent, wherein the at least one anti-curl cosolvent comprises at least one inner salt compound having a sp3-hybridized nitrogen cation and an associated anionic charge which is either isolated on an oxygen anion bound directly to the sp3-hybridized nitrogen cation or isolated among the oxygens of a carboxylate group;
b) printing the paper with the aqueous printing fluid; and
c) drying the aqueous printing fluid onto the paper.

### Claim 24 (depends on 23)

The method of claim 23, wherein the at least one anti-curl cosolvent forms a blended solution with at least one non-ionic, water-soluble blend cosolvent,

### Claim 25 (depends on 23)

The method of claim 23, wherein the at least one blend cosolvent havs a neat solvent vapor pressure of no more than 4×10−2 mm Hg and is capable of strong H-bonding interactions for disrupting fiber-to-fiber H-bonds in cellulose-based paper.

### Claim 26 (depends on 25)

The method of claim 25, wherein the at least one blend cosolvent has a neat solvent vapor pressure of no more than 1×10−4.

### Claim 27 (depends on 24)

The method of claim 24, wherein the aqueous printing fluid comprises from 5 to 60% of the blended solution of the at least one anti-curl cosolvent and the at least one blend cosolvent and the weight ratio of the inner salt anti-curl cosolvent(s) to blend cosolvent(s) in the blended solution ranges from 3:97 to 99:1.

### Claim 28 (depends on 23)

The method of claim 23, wherein the at least one inner salt compound comprises an ammonium N-oxide moiety.

### Claim 29 (depends on 28)

The method of claim 28, wherein the at least one inner salt compound comprises an ammonium-N-oxide moiety with three alkyl groups attached to the nitrogen, and wherein each alkyl group independently comprises up to 6 carbons, each alkyl group being either a straight-chain, a branched chain, or a 5 to 7-membered ring comprising at least 4 carbons.

### Claim 30 (depends on 29)

The method of claim 29, wherein the 5 to 7-membered ring comprises at least one hetero atom selected from the group consisting of oxygen and nitrogen.

### Claim 31 (depends on 30)

The method of claim 30, wherein the 5 to 7-membered ring is a morpholine ring.

### Claim 32 (depends on 29)

The method of claim 29, wherein at least one of the three alkyl groups comprises at least one water-solubilizing substituent.

### Claim 33 (depends on 32)

The method of claim 32 wherein the at least one water-solubilizing substituent is selected from the group consisting of a hydroxyl group, an amide group, a carbonyl group, a sulfone group, a sulfoxide group, a polyethylene glycol moiety and an ammonium-N-oxide moiety.

### Claim 34 (depends on 28)

The method of claim 28, wherein the at least one inner salt compound is selected from the group consisting of N-MethylMorpholine-N-Oxide (MMNO); N-EthylMorpholine-N-Oxide (EMNO); N,N-DiMethylButylAmmonium-N-Oxide (DMBANO) and N,N,N-TriMethylAmmonium-N-Oxide (TMANO).

### Claim 35 (depends on 23)

The method of claim 23, wherein the at least one inner salt compound comprises a betaine moiety.

### Claim 36 (depends on 35)

The method of claim 35, wherein the betaine moiety is Betaine (N,N,N-Trimethyl Glycinate).

### Claim 37 (depends on 23)

The method of claim 23, wherein the at least one inner salt compound consisting of an amino acid.

### Claim 38 (depends on 37)

The method of claim 37, wherein the amino acid is selected from the group consisting of α-Glycine, β-Alanine and γ-Aminobutyric acid.

### Claim 39 (depends on 24)

The method of claim 24, wherein the aqueous printing fluid comprises at least 10 weight percent of the anti-curl cosolvent or the mixture of the anti-curl cosolvent and the blend cosolvent.

### Claim 40 (depends on 23)

The method of claim 23, wherein the aqueous printing fluid is an inkjet ink.

### Claim 41 (depends on 40)

The method of claim 40, wherein the inkjet ink comprises pigment colorant.

### Claim 42 (depends on 40)

The method of claim 40, wherein the inkjet ink comprises dye colorant.

### Claim 43 (depends on 23)

The method of claim 23, wherein the aqueous printing fluid is a fixer fluid.

### Claim 44 (depends on 43)

The method of claim 43, wherein the at least one inner salt compound is an ammonium-N-oxide moiety, which when mixed with a strong acid gives ammonium-N-oxide conjugate acid with an approximate pKa=4-5 and a buffering capacity in aqueous solution near pH=4-5.

### Claim 45

A printer system for avoiding paper curl in printed paper comprising: an aqueous printing fluid depositing system including an aqueous printing fluid comprising at least one anti-curl cosolvent, wherein the at least one anti-curl cosolvent comprises at least one inner salt compound having a sp3-hybridized nitrogen cation not and an associated anionic charge which is either isolated on an oxygen anion bound directly to the sp3-hybridized nitrogen cation or isolated among the oxygens of a carboxylate group.

### Claim 46 (depends on 45)

The printer system of claim 45, wherein the at least one anti-curl cosolvent forms a blended solution with at least one non-ionic, water-soluble blend cosolvent,

### Claim 47 (depends on 46)

The printer system of claim 46, wherein the at least one blend cosolvent has a neat solvent vapor pressure of no more than 4×10−2 mm Hg and is capable of strong H-bonding interactions for disrupting fiber-to-fiber H-bonds in cellulose-based paper.

### Claim 48 (depends on 47)

The printer system of claim 47, wherein the at least one blend cosolvent has a neat solvent vapor pressure of no more than 1×10−4.

### Claim 49 (depends on 46)

The printer system of claim 46, wherein the aqueous printing fluid comprises from 5 to 60% of blended solution of the at least one anti-curl cosolvent and the at least one blend co-solvent and the weight ratio of the inner salt anti-curl cosolvent(s) to blend cosolvent(s) in the blended solution ranges from 3:97 to 99:1.

### Claim 50 (depends on 45)

The printer system of claim 45, wherein the at least one inner salt compound comprises an ammonium-N-oxide moiety.

### Claim 51 (depends on 50)

The printer system of claim 50, wherein the at least one inner salt compound comprises an ammonium-N-oxide moiety with three alkyl groups attached to the nitrogen, and wherein each alkyl group independently comprises up to 6 carbons, each alkyl group being either a straight-chain, a branched chain, or a 5 to 7-membered ring comprising at least 4 carbons.

### Claim 52 (depends on 51)

The printer system of claim 51, wherein the 5 to 7-membered ring comprises at least one hetero atom selected from the group consisting of oxygen and nitrogen.

### Claim 53 (depends on 52)

The printer system of claim 52, wherein the 5 to 7-membered ring is a morpholine ring.

### Claim 54 (depends on 51)

The printer system of claim 51, wherein at least one of the three alkyl groups comprises at least one water-solubilizing substituent.

### Claim 55 (depends on 54)

The printer system of claim 54, wherein the at least one water solubilizing substituent is selected from the group consisting of a hydroxyl group, a carbonyl group, an amide group, a sulfone group, a sulfoxide group, a polyethylene glycol moiety and an ammonium-N-oxide moiety.

### Claim 56 (depends on 50)

The printer system of claim 50, wherein the at least one inner salt compound is selected from the group consisting of N-MethylMorpholine-N-Oxide (MMNO); N-EthylMorpholine-N-Oxide (EMNO); N,N-DiMethylButylAmmonium-N-Oxide (DMBANO) and N,N,N-TriMethylAmmonium-N-Oxide (TMANO).

### Claim 57 (depends on 45)

The printer system of claim 45, wherein the at least one inner salt compound comprises a betaine moiety.

### Claim 58 (depends on 57)

The printer system of claim 57, wherein the betaine moiety is Betaine (N,N,N-Trimethyl Glycinate).

### Claim 59 (depends on 45)

The printer system of claim 45, wherein the at least one inner salt compound comprises an amino acid.

### Claim 60 (depends on 59)

The printer system of claim 59, wherein the amino acid is selected from the group consisting of α-Glycine, β-Alanine and γ-Aminobutyric acid.

### Claim 61 (depends on 46)

The printer system of claim 46, wherein the aqueous printing fluid comprises at least 10 weight percent of the anti-curl cosolvent or the blended solution of the anti-curl cosolvent and the blend cosolvent.

### Claim 62 (depends on 45)

The printer system of claim 45, wherein the aqueous printing fluid is an inkjet ink.

### Claim 63 (depends on 62)

The printer system of claim 62, wherein the inkjet ink comprises pigment colorant.

### Claim 64 (depends on 62)

The printer system of claim 62, wherein the inkjet ink comprises dye colorant.

### Claim 65 (depends on 45)

The printer system of claim 45, wherein the aqueous printing fluid is a fixer fluid.

### Claim 66 (depends on 65)

The printer system of claim 65, wherein the at least one inner salt compound is an ammonium N-oxide moiety mixed with a strong acid to give an ammonium-N-oxide conjugate acid with an approximate pKa=4-5 and a buffering capacity in aqueous solution near pH=4-5.