WO2000036030A1 - Compositions pour encre et leur utilisation pour une impression par jet d'encre - Google Patents

Compositions pour encre et leur utilisation pour une impression par jet d'encre Download PDF

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Publication number
WO2000036030A1
WO2000036030A1 PCT/GB1999/004061 GB9904061W WO0036030A1 WO 2000036030 A1 WO2000036030 A1 WO 2000036030A1 GB 9904061 W GB9904061 W GB 9904061W WO 0036030 A1 WO0036030 A1 WO 0036030A1
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Prior art keywords
water
composition according
surfactant
ink jet
dye
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PCT/GB1999/004061
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English (en)
Inventor
Mark Holbrook
Susan Louise Buckley
Ann Elizabeth Griffiths
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Avecia Limited
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Application filed by Avecia Limited filed Critical Avecia Limited
Priority to GB0112969A priority Critical patent/GB2361009A/en
Priority to AU15743/00A priority patent/AU1574300A/en
Publication of WO2000036030A1 publication Critical patent/WO2000036030A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks

Definitions

  • This invention relates to compositions, to inks and to their use in ink jet printing.
  • Ink jet printing methods involve printing an image onto a substrate using ink droplets emitted from a small nozzle without bringing the nozzle into contact with the substrate.
  • ink jet printers have become popular because they are quieter and more versatile than impact printers, for example conventional basket typewriters are noisy and the images they can print are restricted to the shapes moulded onto the end of each mechanical lever.
  • the most popular ink jet printers are the thermal and piezoelectric.
  • WO 98/14524 of Zeneca describes ink compositions comprising water, a water- dissipatable polyester, a dye and various solvents.
  • ink jet printing inks are stated as having good properties, there is a continual need to improve the performance of ink jet printing inks.
  • low viscosities are desirable because thermal ink jet printers can have difficulties in firing high viscosity inks.
  • the quality of printed text is also of commercial importance in terms of edge sharpness, optical density, light fastness, mottle and ink penetration. If inks penetrate too much then undesirable "strike through” occurs where the printed image is visible on the reverse side of printed paper.
  • Ink jet printing inks are also required to have good storage stability and operability, i.e. low tendency to block the tiny nozzles used in ink jet print heads.
  • surfactants can improve the properties of compositions such as those described in WO 98/14524 and other polymer-containing ink jet printing inks.
  • composition comprising a water-dissipatable polymer, dye, surfactant, water and organic solvent, wherein the surfactant comprises :
  • the water-dissipatable polymer preferably bears non-ionic and/or ionic water dispersing groups, preferably ionised carboxy and/or sulphonate groups, especially ionised sulphonate groups, because these assist water dissipatability of the polymer.
  • non-ionic and/or ionic water dispersing groups preferably ionised carboxy and/or sulphonate groups, especially ionised sulphonate groups, because these assist water dissipatability of the polymer.
  • Such groups can be chain pendant and/or terminal.
  • the water-dissipatable polymer is preferably a water-dissipatable acrylic, polyurethane or polyester, more preferably a water-dissipatable polyester.
  • the water-dissipatable polyester can be prepared using conventional polymerisation procedures known to be effective for polyester synthesis.
  • the acid component may be selected from one or more polybasic carboxylic acids, e.g. di- and tri-carboxylic acids or ester-forming derivatives thereof, for example acid halides, anhydrides or esters.
  • the hydroxyl component may be one or more polyhyd c alcohols or phenols (polyols), for example, diols, triols, etc.
  • polyols polyhyd c alcohols or phenols
  • the reaction to form a polyester may be conducted in one or more stages. It is also possible to introduce in-chain unsaturation into the polyester by, for example, employing as part of the acid component an olefinically unsaturated dicarboxylic acid or anhydride.
  • Polyesters bearing ionised sulphonate groups may be prepared by using at least one monomer having two or more functional groups which will readily undergo an ester condensation reaction (e.g. carboxyl groups, hydroxyl groups or esterifiable derivatives thereof) and one or more sulphonic acid groups (for subsequent neutralisation after polyester formation) or ionised sulphonate groups (i.e. neutralisation of the sulphonic acid groups already having been effected in the monomer) in the synthesis of the polyester. In some cases it is not necessary to neutralise sulphonic acid groups since they may be sufficiently strong acid groups as to be considerably ionised in water even without the addition of base.
  • ester condensation reaction e.g. carboxyl groups, hydroxyl groups or esterifiable derivatives thereof
  • sulphonic acid groups for subsequent neutralisation after polyester formation
  • ionised sulphonate groups i.e. neutralisation of the sulphonic acid groups already having been effected in the monomer
  • the sulphonic acid or ionised sulphonate containing monomer is a dicarboxylic acid monomer having at least one ionised sulphonate substituent (thereby avoiding any need to effect neutralisation subsequent to polyester formation).
  • alkyl carboxylic acid ester groups may be used in place of the carboxylic acid groups as ester-forming groups). Such a monomer will therefore be part of the acid component used in the polyester synthesis.
  • Preferred polybasic carboxylic acids which can be used to form the polyester have two or three carboxylic acid groups.
  • Specific examples include adipic acid, fumaric acid, maleic acid, succinic acid, itaconic acid, sebacic acid, nonanedioic acid, decanedioic acid, 1 ,4- cyclohexanedicarboxylic acid, 1 ,3-cyclohexanedicarboxylic acid, 1 ,2- cyclohexanedicarboxylic acid, terephthalic acid, isophthalic acid, phthalic acid and tetrahydrophthalic acid and their acid chlorides.
  • Anhydrides include succinic, maleic, phthalic and hexahydrophthalic anhydrides.
  • Preferred polyols which can be used to form the polyester include those having from 2 to 6, more preferably 2 to 4 and especially 2 hydroxyl groups per molecule.
  • Suitable polyols having two hydroxy groups per molecule include diols such as 1 ,2- ethanediol, 1 ,3-propanediol, 1 ,4-butanediol, 1 ,6-hexanediol, 2,2-dimethyl-1 ,3- propanediol (neopentyl glycol), the 1 ,2-, 1 ,3- and 1 ,4-cyclohexanediols and the corresponding cyclohexane dimethanols, diethylene glycol, dipropylene glycol, and diols such as alkoxylated bisphenol A products, e.g.
  • Suitable polyols having three hydroxy groups per molecule include triols such as thmethylolpropane (1 ,1 ,1-tris (hydroxymethyl)ethane).
  • Suitable polyols having four or more hydroxy groups per molecule include pentaerythritol (2,2-bis(hydroxymethyl)-1 ,3- propanediol) and sorbitol (1 ,2,3,4,5,6-hexahydroxyhexane).
  • Compounds having two or more groups which readily undergo an ester condensation reaction and have one or more sulphonate groups are dicarboxylic acid monomers having at least one ionised sulphonate group.
  • dicarboxylic acid monomers having at least one ionised sulphonate group examples include aromatic dicarboxylic acids having an ionised sulphonate group, for example those of the formula:
  • M is a cation (preferably sodium, lithium or potassium); and each R c independently is H, a cation or C 1 . 4 -alkyl (preferably methyl or ethyl).
  • R c independently is H, a cation or C 1 . 4 -alkyl (preferably methyl or ethyl).
  • M and R c are as defined above.
  • Particularly preferred is the mono sodium salt, this material being known as sodio-5-sulphoisophthalic acid (SSIPA).
  • each R d independently is alkylene, preferably C 2 . 4 - alkylene.
  • Preferred compounds of the above formula are: wherein M is as hereinbefore defined.
  • Polyesters bearing ionised carboxy groups can be prepared by various means. For example, if the hydroxyl component of the reactants is stoichiometrically in excess of the acid component, a hydroxyl-terminated polyester can be formed, which may be subsequently converted to a carboxy terminated polyester by wholly or partially reacting the hydroxyl groups with an appropriate reagent (e.g. an acid anhydride or a dicarboxylic acid). Alternatively, terminal carboxy functionality may be directly introduced by employing an appropriate stoichiometric excess of the acid component reactants. In another alternative, chain-pendant carboxy groups may be introduced by using reagents such as dimethylol propionic acid (DMPA) since if appropriate reaction condition are employed (e.g.
  • DMPA dimethylol propionic acid
  • the hindered carboxy group thereof does not take part to any significant extent in the ester-forming reactions during the polyester synthesis and the DMPA effectively behaves as a simple diol.
  • Chain- pendant and/or terminal carboxy groups could also be introduced by employing a tri- or higher functionality carboxylic acid or anhydride in the polyester synthesis, for example, trimellitic acid or anhydride. Combinations of the above procedures could also be used. It is thus seen that terminal or side-chain carboxy groups or both can be introduced as desired. These can be fully or partially neutralised with an appropriate base to yield ionised carboxy groups.
  • the counter ions used may be as for the ionised sulphonate groups described above (apart from H + since the carboxylic acid groups themselves are normally insufficiently ionised to provide a significant amount of ionised carboxy groups - although F substituents would increase acid strength), with alkali metal ions such as Na + , Li + and K + again being particularly preferred, and ammonium and organic amine derived cations less preferred because some have an undesirable odour.
  • the water-dissipatable polyester may optionally have hydrophilic non-ionic segments, for example within the polyester backbone (i.e. in-chain incorporation) or as chain-pendant or terminal groups. Such groups may act to contribute to the dispersion stability or even water-solubility of the polyester.
  • polyethylene oxide chains may be introduced into the polyester during its synthesis by using as part of the hydroxyl component, ethylene oxide-containing mono, di or higher functional hydroxy compounds, especially polyethlene glycols and alkyl ethers of polyethylene glycols, examples of which include: R e -O-(CH 2 CH 2 O) n -H HO-(CH 2 CH 2 O) n -H
  • R e is C ⁇ -alkyl, preferably C 1 . 4 -alkyl, more preferably methyl; n is 1 to 500; and p is 1 to 100.
  • a small segment of a polyethylene oxide chain could be replaced by a propylene oxide or butylene oxide chain in such non-ionic groups, but should still contain ethylene oxide as a major part of the chain.
  • the amount of ionised sulphonate and/or carboxy groups present in the polyester should be sufficient to provide or contribute to water-dissipatability of the polyester, although it should not be so high as to render the resulting polyester unacceptably water- sensitive. This amount will depend, inter alia, on factors such as the hydrophilicity/ hydrophobicity of units provided by other monomers in the polyester synthesis or any surfactants (if used), and also the relative proportions of ionised sulphonate/carboxy groups. With regard to the last mentioned point, ionised sulphonate groups are more effective at providing or contributing to water-dissipatability than ionised carboxy groups and so can be used at considerably lower levels in comparison to ionised carboxy groups.
  • the polyester is wholly or predominantly sulphonate stabilised (by which is meant the water dissipatability-providing groups are provided wholly or predominately by ionised sulphonate groups).
  • the ionised sulphonate group content is preferably within the range from 7.5 to 100 milliequivalents (more preferably 10 to 75 milliequivalents and particularly 11 to 56 milliequivalents) per 100 g of polyester.
  • SSIPA as the monomer for providing the ionised sulphonate groups
  • the amount of this monomer used in the polyester synthesis based on the weight of all the monomers used in the polyester synthesis, will usually be within the range from 2 to 20% by weight (more usually 3 to 15% by weight).
  • the carboxylic acid value (AV) of the polyester which is predominantly sulphonate stabilised i.e. an AV based on the carboxylic acid groups only (i.e. excluding sulphonate groups) will generally be within the range of from 0 to 100 mgKOH/g, more preferably 0 to 50 mgKOH/g, especially 0 to 25 mgKOH/g, more especially 0 to 10mgKOH/g.
  • the carboxylic acid value AV of the polyester is preferably within the range of from 20 to 140 mgKOH/g (more preferably 30 to 100 mgKOH/g).
  • the polyester is either predominantly sulphonate-stabilised or predominantly carboxylate stabilised (preferably the former).
  • the polyethylene oxide chain content should preferably not exceed 25% by weight (and more preferably should not exceed 15% by weight), based on the total weight of the polyester, in order to avoid unacceptable water-sensitivity. Therefore the amount is preferably 0 to 25% by weight (more preferably 0 to 15% by weight) based on the total weight of polyester.
  • the water-dissipatable polyester preferably has a number average molecular weight Mn of up to 30,000.
  • the Mn is preferably in the range from 1000 to 30,000, more preferably 1500 to 25,000, especially 2000 to 20,000. These Mn lead to particularly good storage stability for the resultant inks.
  • the measurement of Mn is well known to those skilled in the art, and may for example be effected using gel permeation chromatography in conjunction with a standard polymer such as polystyrene or polymethylmethacrylate of known molecular weight.
  • the water-dissipatable polyester preferably has a hydroxyl number of from 0 to 225mg KOH/g, more preferably 0 to 125mg KOH/g, especially from 0 to 50mgKOH/g.
  • the Tg of the water-dissipatable polyester (i.e. the temperature at which the polymer changes from a glassy, brittle state to a plastic, rubbery state) is preferably in the range -38°C to 105°C, more preferably -20 to 70°C, especially -10°C to 60°C.
  • esterification polymerisation processes for making the polyesters for use in invention composition are known and need not be described here in more detail. Suffice to say that they are normally carried out in the melt using catalysts, for example a tin- based catalyst, and with the provision for removing any water or alcohol formed from the condensation reaction.
  • catalysts for example a tin- based catalyst
  • the water-dissipatable polyester may be dissipated in water by adding the solidified melt directly into water.
  • the solidified melt is preferably in a form such as flake (which can often be obtained directly from the melt) or communised solid (obtained for example by grinding).
  • water can be added directly to the hot polyester melt until the desired solids content/viscosity is reached.
  • the polyester may be dissipated in water by adding an aqueous pre-dissipation (or organic solvent solution) of the polyester to the water phase.
  • the water-dissipatable polyesters normally do not need an external surfactant when being dissipated into water, although such surfactants may be used to assist the dissipation if desired and in some cases can be useful in this respect because additional surfactants reduce the required amount of dissipating groups (i.e. sulphonate, and (mono alkoxy)polyalkylene chains if used).
  • Water-dissipatable polyesters can also be purchased from Eastman Kodak Company and Avecia Limited. Examples include Eastman AQ29D and AQ55W.
  • the water-dissipatable polymer may also be formed by performing free radical polymerisation of olefinically unsaturated monomers in the presence of a polyester. This gives what could be called a polyester-acrylic hybrid.
  • Olefinically unsaturated monomers which can be used include olefinically unsaturated carboxy functional monomers, e.g. acrylic acid, methacrylic acid, fumaric acid, itaconic acid and ⁇ -carboxyethyl acrylate; olefinically unsaturated monomers which are free from carboxy and hydroxy groups, e.g.
  • polyester 1 ,3-butadiene, isoprene, styrene, vinylidene halides, vinylidene esters and esters of acrylic acid and methacrylic acid, e.g. methyl (meth) acrylate, ethyl (meth)acrylate n-butyl (meth)acrylate and 2-ethyl hexyl (meth)acrylate; and olefinically unsaturated monomers having a hydroxy group e.g. N-methylol (meth)acrylamide and hydroxy C 2 . 8 -alkyl esters of (meth)acrylic acid.
  • a component which has unsaturation therein e.g.
  • the product from the polyesterification reaction will have unsaturation incorporated into its structure which can take part in the free radical polymerisation to give a graft copolymer.
  • the free radical polymerisation processes use a free-radical generating initiator system such as (for example) the redox radical initiator system tertiary butylhydroxide/isoascorbic acid and will take place in the aqueous phase, rather than in the melt.
  • the aqueous medium is water or a mixture of water and one or more organic solvent, more preferably a mixture comprising water, one or more water- immiscible organic solvent and one or more water-miscible organic solvent.
  • Preferred water-dissipatable acrylic polymers are as described in International patent application No. PCT/GB99/00705, page 1 , line 23 to page 6, line 17 which is incorporated herein by reference thereto.
  • Preferred water-dissipatable polyurethane polymers are as described in International patent application No. PCT/GB99/00655, page 1 , line 22 to page 4, line 39 which is incorporated herein by reference thereto.
  • Preferred dyes are essentially insoluble in water and are preferably soluble in organic solvents. Disperse and solvent soluble dyes are preferred, especially those carrying a branched alkylamino group because this results in compositions having particularly good light fastness.
  • Disperse and solvent soluble dyes are distinct from pigments in that pigments are insoluble in organic solvents whereas disperse and solvent soluble dyes are soluble in organic solvents.
  • Useful classes of disperse and solvent soluble dyes include water- insoluble anthraquinones, phthalocyanines, pyrrolines, triphenodioxazines, methines, benzodifuranones, coumarins, indoanilines, benzenoids, xanthenes, phenazines, solvent soluble sulphur dyes, quinophthalones, py dones, aminopyrazoles, pyrollidines, styrylics and azoics.
  • azoics examples are monoazo, disazo and trisazo disperse dyes and solvent soluble dyes; especially preferred azoics contain heterocyclic groups.
  • the Colour Index International lists suitable disperse and solvent soluble dyes, examples of which include Solvent Blue 63, Disperse Blue 24, Solvent Black 3, Solvent Black 35 and Disperse Red 60. Further examples of disperse dyes are given in the Colour Index, 3 rd Edition, Volume 2, pages 2483 to 2741 and further examples of solvent soluble dyes are given in Volume 3, pages 3566 to 3647 and each of these dyes is included herein in reference.
  • the dyes are preferably in a purified form, preferably over 90%, more preferably over 95%, especially over 98% pure.
  • Surfactants carrying sulpho (-SO 3 " ) groups include alkyl benzene sulphonic acid salts (e.g. ArylanTM surfactants from Akcros); aromatic sulphonic acid salts (e.g. EltesolTM surfactants from Albright & Wilson); and preferably mono- and di- alkyl (especially mono- and di- C 4 to C 18 -alkyl) sulphosuccinates and mono- and di-alkyl sulphosuccinamates (e.g. EmpiminTM surfactants from Albright & Wilson), mono- and di-alkyl (especially mono- and di- C 4 " to C 8 -alkyl), ethoxy succinates (e.g.
  • alkyl benzene sulphonic acid salts e.g. ArylanTM surfactants from Akcros
  • aromatic sulphonic acid salts e.g. EltesolTM surfactants from Albright & Wilson
  • Especially preferred anionic surfactants are di-isooctyl sulphosuccinates, especially the sodium, potassium, lithium and ammonium and substituted ammonium salts thereof.
  • Surfactants carrying sulphate groups include alcohol sulphates and ether sulphates, preferably hydroxy C 6-18 -alkyl sulphates and C 6 . 18 -O(CH 2 CH 2 O) x SO 3 H wherein X is from 1 to 10 inclusive.
  • Such surfactants are available under the Empicol trade mark from Albright & Wilson.
  • the preferred non-ionic surfactants include fatty alcohol alkoxylates (e.g. Synperonic A or 91 from ICI); fatty acid alkoxylates (e.g. EMPILAN BQTM surfactants from ICI).
  • Albright & Wilson alkyl and aryl phenol alkoxylates (e.g. EMPILAN NPTM surfactants from Albright & Wilson); also fatty acid esters of polyethylene glycols e.g. (Ethylan A series from Ackros); castor oil ethoxylates (e.g. DEHSCOFIX COTM surfactants from Albright & Wilson); sorbitan esters and their ethoxylates (e.g. SPANTM and TWEENTM surfactants from Aldrich); and ethylene oxide-propylene oxide block copolymers (e.g. SYNPERONIC PETM surfactants from ICITM), in each case being free from carbon - carbon triple bonds.
  • EMPILAN NPTM surfactants from Albright & Wilson
  • fatty acid esters of polyethylene glycols e.g. (Ethylan A series from Ackros)
  • castor oil ethoxylates e.g. DEHSCOFIX CO
  • the surfactant has a number average molecular weight below 1000.
  • compositions preferably exist as a solution, emulsion, micro-emulsion, dispersion or micelle.
  • the compositions are inks, especially inks suitable for use in a thermal and/or piezoelectric ink jet printers.
  • compositions contain less than 500ppm, more preferably less than especially 100ppm, especially less than 50ppm, more especially less than 20ppm in total of divalent, thvalent metal cations, metal cations and halide anions.
  • ppm means parts per million by weight relative to the weight of the composition.
  • Compositions of this purity may be prepared by purifying an impure composition, or the components which go into the composition, using standard purification techniques. Suitable techniques include reverse osmosis, ultrafiltration, ion exchange and combinations thereof.
  • compositions are prepared by mixing (i) a solution of the dye in water, an organic solvent or a mixture of water and an organic solvent; with (ii) a mixture of the water-dissipatable polymer and water, optionally containing an organic solvent; wherein said surfactant is present in (i) or (ii) or (i) and (ii). Addition of said surfactant after the dye solution and water-dissipatable polymer solution have been mixed works less well.
  • the compositions have a viscosity of less than 8, more preferably less than 6, especially less than 3 centipoise at 20°C.
  • the compositions have a surface tension less than 50mN/m, more preferably less than 40mN/m, at 20°C.
  • composition will comprise : (i) from 30 to 95 parts, more preferably from 40 to 80 parts of water;
  • surfactant comprises; (a) an anionic surfactant;
  • (c) a mixture comprising (a) and (b); and wherein all parts are by weight and the number of parts (i)+(ii) + (iii)+(iv)+(v) add up to 100.
  • the number of parts of the water-dissipatable polymer is calculated on a 100% solids basis. For example 50g of a 20% solids polymer is taken as 10g (or 10 parts) of polymer.
  • the organic solvent (as mentioned in (ii) above) preferably comprises a water- miscible organic solvent and a water-immiscible organic solvent because this leads to particularly good dye solubility and ink stability.
  • Suitable water-immiscible organic solvents are as described in WO 98/14524, page 1 1 , lines 16 to 30, which are incorporated herein by references thereto, and optionally substituted nicotinamides e.g. nicotinamide-N-oxide and nicotinamide; optionally substituted furfuryl alcohol e.g. 2,5-furandimethanol and furfuryl alcohol; optionally substituted tetrahydrofurfuryl alcohol, e.g.
  • Suitable water-miscible organic solvents are as described in WO 98/14524, page 11 , line 31 to page 12, line 7, which is incorporated herein by reference thereto.
  • the water-immiscible solvent preferably has a solubility in water at 20°C of up to 50g/l.
  • the water-miscible solvent preferably has a solubility in water at 20°C of more than 50g/l.
  • the ratio of water-miscible organic solvent to water-immiscible organic solvent is preferably 20:1 to 1 :2, more preferably 19:1 to 1 :1 , especially 8:1 to 1 :1 , more especially 5:1 to 1 :1.
  • compositions may be prepared by mixing the components thereof in any order.
  • the water-dissipatable polymer is coloured with the dye and the resultant coloured water-dissipatable polymer is then mixed with the remaining components of the composition.
  • Suitable methods for coloring the water-dissipatable polymer are described in WO 98/14524, page 10, line 16 to page 11 , line 12, which is incorporated herein by reference thereto.
  • compositions of the invention are particularly useful as ink jet printing inks, demonstrating a low tendency for blocking the nozzles of thermal ink jet printers, low viscosities (valuable for thermal ink jet printers), good quality of prints and good storage stability.
  • di-isooctyl sulphosuccinates are particularly beneficial in this regard.
  • the present invention there is provided a process for printing an image on a substrate comprising applying thereto a composition according to the first aspect of the invention by means of an ink jet printer.
  • the ink jet printer emits droplets of the ink onto a substrate from a nozzle without bringing the nozzle into contact with the substrate.
  • the ink jet printer is a thermal or piezoelectric ink jet printer.
  • the ink jet printer will be fitted with a printer head which is not adversely affected by the contents of the ink, e.g. it may be coated or otherwise treated to withstand the solvents contained in the ink.
  • the substrate is preferably a paper, an overhead projector slide or a textile material. Preferred textile materials are cotton, polyester and blends thereof.
  • Preferred papers are plain or treated papers and films which may have an acid, alkaline or neutral character.
  • Examples of commercially available treated papers include HP Premium Coated Paper (available from Hewlett Packard Inc), HP Photopaper (available from Hewlett Packard Inc), Stylus Pro 720 dpi Coated Paper, Epson Photo Quality Glossy Film (available from Seiko Epson Corp.), Epson Photo Quality Glossy Paper (available from Seiko Epson Corp.), Canon HR 101 High Resolution Paper (available from Canon), Canon GP 201 Glossy Paper (available from Canon), and Canon HG 101 High Gloss Film (available from Canon).
  • the process for printing an image thereon according to the invention preferably further comprises the step of heating the resultant printed textile, preferably to a temperature of 50°C to 250°C.
  • the inks of the present invention may also be used for the preparation of colour filters, for example those used in flat bed displays.
  • a third aspect of the present invention provides a paper, an overhead projector slide or a textile material printed with a composition according to the second aspect of the present invention or by means of a process according to the second aspect of the present invention.
  • a fourth aspect of the present invention provides an ink jet printer cartridge containing a composition according to the first aspect of the present invention.
  • Paper GB is Gilbert Bond paper from the Mead Corporation.
  • Paper WC is Wiggins Conqueror High White Wove 100g/m 2 from Arjo Wiggins
  • SolsperseTM 27000 is a non-ionic surfactant free from carbon-carbon triple bonds from Avecia Limited, England.
  • PE L72, PE L35 and PE 85 are ethylene oxide/propylene oxide block copolymer surfactants from ICI Ltd.
  • EmpiminTM MH and MKB are mono alkyl sulphosuccinamate surfactants from Albright & Wilson.
  • TweenTM 80 is an ethoxylated sorbitan ester surfactant from Aldrich.
  • SurfynolTM 465 is a non-ionic surfactant containing carbon-carbon triple bonds from
  • a water-dissipatable polymer was prepared as described for Resin 3 in WO 98/145254, (page 21 from "water-dissipatable polymer ("Resin 3")" to end of page 21).
  • This polymer is referred to as "Resin X” in the following Examples.
  • Components 1 to 5 were placed in a reaction flask purged with nitrogen. The components were stirred under nitrogen until a homogenous solution had formed. The mixture was then heated to 60°C and a solution of 6 in 7 was added. The mixture was kept at 65°C with agitation for 4 hours, after which a solution of 8 in 9 was added. The mixture was agitated at 65°C for a further 1 hour before cooling and stored in a bottle.
  • the resultant water-dissipatable acrylic polymer had a solids content of 20%, a Mn of 3460 and a Mw of 6319.
  • Components 1 to 7 were placed in a reaction flask purged with nitrogen. The contents were stirred under nitrogen until a homogenous solution had formed. The mixture was then heated to 65°C, a solution of 8 in 9 was added. The mixture was agitated at 65°C for 4 hours, after which a solution of 10 in 1 1 was added. The reaction was allowed to continue for a further 1 hour before cooling and bottling.
  • the resultant water-dissipatable acrylic polymer had a solid content of 20%, a Mn of 4264 and a Mw of 8157.
  • Resin Z - A 50:50 mixture of acrylic and polvurethane resins
  • Resin Z is a 50:50 mixture by weight of an acrylic polymer (Polymer A) and a polyurethane polymer mixture (polymer P) and was prepared as follows:
  • the resultant Polymer A has a pH of 7.19, solids content of 29.73%, Mn of 5811 and Mw of 13837.
  • DMPA, CHDM, PPG1000 and NMP were added to a reaction flask and stirred under N 2 .
  • IPDI was added and the mixture was heated to 50°C with continuous stirring under nitrogen gas.
  • DBTDL was added and the mixture heated to 90°C and held there for 3 hours.
  • the NCO content was measured periodically and when it reached 4.81 % the Jeffamine M1000 was added and the mixture stirred for a further hour at 90°C.
  • the mixture was dispersed in the mixture of ammonia and water with continuous stirring, followed by a further hour stirred without applying heat. Particulate matter was removed by filtering the dispersion through a cloth having a pore size of 50 ⁇ m, to give a first polyurethane polymer having a pH of 9.4, Mn 4343, Mw 6676, surface tension of
  • the first polyurethane (10g) was diluted with de-ionised water (15g) and mixed thoroughly with a dispersion of NeoRez R-985 (18.75g, a commercially available polyurethane dispersion from Avecia) in de-ionised water (56.25g).
  • the resultant mixture is polymer P.
  • step (i) Equal weights of the products of step (i) and step (ii) were blended together at room temperature and stirred until completely homogenous.
  • Dye (1 ) was prepared using stages 1a to 1 c described below:
  • Ethyl propionylacetate 72.14g was added dropwise over 30 minutes to a stirred mixture of tetrahydrofurfurylamine (122.92g) and water (18g) at room temperature. Ethyl cyanoacetate (56.6g) was then added. After heating to 90°C for 20 hours the solution was cooled and poured onto ice (150g) and acidified by addition of concentrated hydrochloric acid. The product was filtered off, washed with water and dried at 45°C under reduced pressure to give 67.5g of the desired product. Stage 1c
  • Example 2 The method of Example 1 was repeated except that in place of ethyl propionylacetate there was used ethyl acetoacetate (65.07g).
  • the resultant Dye 2 had a ⁇ max at 434nm.
  • Dye 4 may be prepared by mixing together the dye described in WO98/59008, Example 1 (3 parts) and the dye described in WO98/59007, Example 1 (2 parts), or alternatively by co-synthesis of these dyes
  • Dye 5 was prepared by the method described in International patent application number PCT/GB/99/02453, Example 1.
  • Dye 6 was prepared by the method described in GB 2335924, Example 1.
  • Table 1 The described in Table 1 were used to fill empty colour cartridges from an Olivetti JP450 ink jet printer. This printer was then used to print the inks on Xerox 4024 plain paper from Rank Xerox. The optical density of the prints (“ROD”) was measured and the print quality assessed visually.
  • ROD optical density of the prints
  • inks may be prepared having the formulations described in Tables 3 and 4 below wherein the following abbreviations are used. These inks may be applied to a substrate such as plain paper using an ink jet printer. TABLE 2
  • [2] measured on Atlas Ci35 Weatherometer. The values quoted are the ⁇ E after 100 hours irradiation, with lower figures representing better light fastness than higher figures.
  • FRU fructose
  • Resin The number of parts by weight of resin is shown in brackets.
  • the resins are preferably added as 20% w/w solution/dispersion in water.
  • MIBK Methylisobutyl ketone
  • Surfactant A is sodium dodecyl benzene sulphonate; surfactant B is Nonyl phenol
  • surfactant C is diisooctyl sulphosuccinate of the formula
  • surfactant D is Tergitol 15-S-7(a secondary alcohol ethoxylate)
  • XeroxTM 4024 - a plain paper from Rank Xerox CanonTM HG201 - a glossy ink jet film supplied by Canon EpsonTM Glossy Ink Jet Film - supplied by Epson
  • optical density (ROD), chroma (brightness) and light-fastness of the prints were measured.
  • optical density (ROD), chroma (brightness) and light fastness of the prints were measured as described above in relation to Examples 19 to 28.
  • XA Xerox Acid Paper
  • HG 201 Canon HG 201 - a glossy ink jet film from Canon
  • Ep.GI.Film Epson glossy ink jet film

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

Cette composition contient un polymère capable de se disperser dans l'eau, un colorant, un tensioactif, de l'eau et un solvant organique. Ce tensioactif est, (a), un tensioactif possédant un groupe sulpho ou sulfate ou (b), un tensioactif non ionique dépourvu de triples liaisons carbone-carbone ou encore, (c), un mélange de a et de b. Ces compositions se révèlent des plus utiles comme encres pour impression par jet d'encre ou sous forme de concentrés à partir desquels la préparation de ces encres est possible. Cette invention permet de produire des compositions et des encres de faible viscosité, aptes à être utilisées dans des imprimantes par jet d'encre.
PCT/GB1999/004061 1998-12-12 1999-12-03 Compositions pour encre et leur utilisation pour une impression par jet d'encre WO2000036030A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB0112969A GB2361009A (en) 1998-12-12 1999-12-03 Inks compositions and their use in ink jet printing
AU15743/00A AU1574300A (en) 1998-12-12 1999-12-03 Inks compositions and their use in ink jet printing

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9827291.7 1998-12-12
GBGB9827291.7A GB9827291D0 (en) 1998-12-12 1998-12-12 Compositions

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WO2000036030A1 true WO2000036030A1 (fr) 2000-06-22

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004094541A1 (fr) * 2003-04-22 2004-11-04 Clariant Gmbh Preparations de colorants a base d'eau pour l'impression a jet d'encre
EP1702013A1 (fr) * 2003-10-23 2006-09-20 Fuji Photo Film Co., Ltd. Encre et palettes d'encres pour enregistrement a jet d'encre
WO2007112244A2 (fr) * 2006-03-23 2007-10-04 Hewlett-Packard Development Company, L.P. Composition d'encre pour jet d'encre
EP2009070A1 (fr) 2007-06-29 2008-12-31 FUJIFILM Corporation Encre pour jet d'encre et son procédé de production, filtre couleur et son procédé de production, dispositif d'affichage et procédé de formation d'un film fonctionnel
CN108473804A (zh) * 2016-01-18 2018-08-31 蓝宝迪有限公司 用于喷墨印刷的水性喷墨油墨
EP3434740A1 (fr) * 2017-07-25 2019-01-30 Canon Kabushiki Kaisha Encre aqueuse, cartouche d'encre et procédé d'enregistrement d'images

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5441561A (en) * 1993-02-23 1995-08-15 Fuji Xerox Co., Ltd. Ink-jet recording ink and ink-jet recording methods thereof
JPH09157564A (ja) * 1995-12-07 1997-06-17 Fuji Xerox Co Ltd インクジェット記録用インク及びインクジェット記録 方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5441561A (en) * 1993-02-23 1995-08-15 Fuji Xerox Co., Ltd. Ink-jet recording ink and ink-jet recording methods thereof
JPH09157564A (ja) * 1995-12-07 1997-06-17 Fuji Xerox Co Ltd インクジェット記録用インク及びインクジェット記録 方法
US5883157A (en) * 1995-12-07 1999-03-16 Fuji Xerox Co., Ltd. Ink jet recording ink and ink jet recording method

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100357372C (zh) * 2003-04-22 2007-12-26 科莱恩产品（德国）有限公司 喷墨印刷用的水基着色剂制剂
WO2004094541A1 (fr) * 2003-04-22 2004-11-04 Clariant Gmbh Preparations de colorants a base d'eau pour l'impression a jet d'encre
EP1702013A4 (fr) * 2003-10-23 2009-03-25 Fujifilm Corp Encre et palettes d'encres pour enregistrement a jet d'encre
EP1702013A1 (fr) * 2003-10-23 2006-09-20 Fuji Photo Film Co., Ltd. Encre et palettes d'encres pour enregistrement a jet d'encre
US7776144B2 (en) 2003-10-23 2010-08-17 Fujifilm Corporation Ink and ink set for inkjet recording
WO2007112244A2 (fr) * 2006-03-23 2007-10-04 Hewlett-Packard Development Company, L.P. Composition d'encre pour jet d'encre
WO2007112244A3 (fr) * 2006-03-23 2008-02-07 Hewlett Packard Development Co Composition d'encre pour jet d'encre
US7872060B2 (en) 2006-03-23 2011-01-18 Hewlett-Packard Development Company, L.P. Inkjet ink composition
KR101354378B1 (ko) * 2006-03-23 2014-01-23 휴렛-팩커드 디벨롭먼트 컴퍼니, 엘.피. 잉크젯 잉크 조성물
EP2009070A1 (fr) 2007-06-29 2008-12-31 FUJIFILM Corporation Encre pour jet d'encre et son procédé de production, filtre couleur et son procédé de production, dispositif d'affichage et procédé de formation d'un film fonctionnel
CN108473804A (zh) * 2016-01-18 2018-08-31 蓝宝迪有限公司 用于喷墨印刷的水性喷墨油墨
EP3434740A1 (fr) * 2017-07-25 2019-01-30 Canon Kabushiki Kaisha Encre aqueuse, cartouche d'encre et procédé d'enregistrement d'images
US10513623B2 (en) 2017-07-25 2019-12-24 Canon Kabushiki Kaisha Aqueous ink, ink cartridge and image recording method

Also Published As

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AU1574300A (en) 2000-07-03
GB9827291D0 (en) 1999-02-03
GB0112969D0 (en) 2001-07-18
GB2361009A (en) 2001-10-10

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