EP1084202A1 - Composition a base de polymere acrylique dispersible dans l'eau - Google Patents

Composition a base de polymere acrylique dispersible dans l'eau

Info

Publication number
EP1084202A1
EP1084202A1 EP99907746A EP99907746A EP1084202A1 EP 1084202 A1 EP1084202 A1 EP 1084202A1 EP 99907746 A EP99907746 A EP 99907746A EP 99907746 A EP99907746 A EP 99907746A EP 1084202 A1 EP1084202 A1 EP 1084202A1
Authority
EP
European Patent Office
Prior art keywords
water
acrylic polymer
composition according
ink
parts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99907746A
Other languages
German (de)
English (en)
Inventor
Stephen George Hexagon House YEATES
Barry Huston Hexagon House MEYRICK
Mark Hexagon House P.O. Box 42 HOLBROOK
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Avecia Ltd
Original Assignee
Avecia Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Avecia Ltd filed Critical Avecia Ltd
Publication of EP1084202A1 publication Critical patent/EP1084202A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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 containing certain acrylic polymers and to their use in ink jet printing.
  • Ink jet printing methods involve a non-impact printing technique for printing an image onto a substrate using ink droplets ejected through a fine nozzle onto a substrate without bringing the nozzle into contact with the substrate.
  • ink jet printing There are many demanding performance requirements for colorants and inks used in ink jet printing. For example they desirably provide sharp, non-feathered images having good water-fastness, light-fastness and optical density.
  • the inks are often required to dry quickly when applied to a substrate to prevent smudging, but they should not form a crust over the tip of an ink jet nozzle because this will stop the printer from working.
  • the inks should also be stable to storage over time without decomposing or forming a precipitate which could block the fine nozzle.
  • the most popular ink jet printers are the thermal and piezoelectric ink jet printers.
  • inks which are suitable for both thermal and piezo ink jet printers, have high colour strength and produce images having a high light-fastness and water-fastness when printed on a substrate. Many inks will not work in thermal ink jet printers, tending to foul the heater element and block the nozzles.
  • composition comprising a water-dissipatable acrylic polymer water, colorant, a water- miscible organic solvent and a water-immiscible organic solvent.
  • the water-dissipatable acrylic polymer has preferably been obtained from the polymerisation of one or more olefinically unsaturated monomers having water dispersing groups, optionally in the presence of one or more olefinically unsaturated monomers which are free from water dispersing groups.
  • the number average molecular weight (Mn) of the acrylic polymer is less than 25,000, more preferably is less than 20,000, especially less than 15,000.
  • the Mn of the acrylic polymer may be measured by gel permeation chromatography ("gpc").
  • the gpc method used for determining Mn preferably comprises applying the acrylic polymer to a chromatography column packed with cross-linked polystyrene/divinyl benzene, eluting the column with tetrahydrofuran at a temperature of 40°C and assessing the Mn of the acrylic polymer compared to a number of a polystyrene standards of a known Mn.
  • Suitable cross-linked polystyrene/divinyl benzene chromatography columns are commercially available from Polymer Laboratories. If the gpc method for determining Mn does not work for any reason, for example the polymer has an unexpected interaction with the gpc column give an unrealistic result, the Mn may be determined using alternative methods, for example by vapour phase osmometry.
  • the acrylic polymer preferably has an acid value of from 0 to 300mgKOH/g, more preferably 20 to 250mgKOH/g, especially 50 to 225mgKOH/g.
  • the dispersing groups provide the facility of self-dispersibility and solubility to the acrylic polymer in ink media, especially in water.
  • the dispersing groups may be ionic, non-ionic or a mixture of ionic and non-ionic dispersing groups.
  • Preferred ionic dispersing groups include cationic quaternary ammonium groups and acid groups, for example phosphoric acid groups, sulphonic acid groups and carboxylic acid groups.
  • the dispersing groups may be incorporated into the acrylic polymer in the form of monomers or oligomers bearing the appropriate dispersing groups.
  • One may also react an acrylic polymer which is not water-dissipatable with monomers or oligomers which make the acrylic polymer water-dissipatable.
  • the acid groups may be subsequently, or during formation of the polymer, fully or partially neutralised with a base containing a cationic charge to give a salt. If the acid dispersing groups are used in combination with a non-ionic dispersing group, neutralisation may not be required.
  • the conversion of any free acid groups into the corresponding salt may be effected during the preparation of the acrylic polymer and/or during the preparation of an ink from the acrylic polymer.
  • the base used to neutralise any acid dispersing groups is ammonia, an amine or an inorganic base.
  • Suitable amines are tertiary amines, for example triethylamine or thethanolamine.
  • Suitable inorganic bases include alkaline hydroxides and carbonates, for example lithium hydroxide, sodium hydroxide, or potassium hydroxide.
  • a quaternary ammonium hydroxide, for example N + (CH 3 ) 4 OH " can also be used.
  • a base is used which gives the required counter ion desired for the composition which is prepared from the acrylic polymer.
  • suitable counter ions include Li + , Na + , K + , NH 4 + and substituted ammonium salts (including tetra substituted amines, e.g. (CH 3 ) 4 N + ).
  • Non-ionic dispersing groups may be in-chain, pendant or terminal groups.
  • Preferably non-ionic dispersing groups are pendant polyoxyalkylene groups, more preferably polyoxyethylene groups.
  • the non-ionic groups may be introduced into the acrylic polymer in the form of a compound bearing non-ionic dispersing groups and at least one (although preferably only one) copolymerisable olefinically unsaturated group.
  • the nature and level of dispersing groups in the acrylic polymer influences whether a solution, dispersion, emulsion or suspension is formed on dissipation of the acrylic polymer.
  • the dispersing group content of the acrylic polymer may vary within wide limits but is preferably sufficient to enable the acrylic polymer to form stable ink-jet printing inks in water and aqueous media.
  • the acrylic polymer is preferably soluble in water, although minor amount of the acrylic polymer may be insoluble in water and exist as dissipated particles when mixed with aqueous media or water.
  • the proportion of insoluble, water-dissipatable acrylic polymer is less than 50%, preferably less than 40% and most preferably less than 30% by weight relative to the total weight of the acrylic polymer.
  • the size of insoluble acrylic polymer particulates when dissipated in an ink is preferably less than 100nm, and more preferably less than 60nm.
  • the acrylic polymer is prepared by polymerisation (a) olefinically unsaturated monomers providing dispersing groups in the presence of (b) olefinically unsaturated monomers which are free from dispersing groups it is preferred that the amount of (b) is from 1 to 95%, more preferably from 2 to 90% by weight relative to the weight of (a) + (b).
  • the acrylic polymer may be prepared in a conventional manner by polymerising the olefinically unsaturated monomers providing dispersing groups either alone or in the presence of olefinically unsaturated monomers which are free from dispersing groups.
  • the polymerisation may be continued until reaction between the monomers is complete.
  • the acrylic polymer may be prepared by polymerising an acrylic oligomer having water dispersing groups and one olefinically unsaturated terminal group in the presence of one or more olefinically unsaturated monomers which are free from water dispersing groups and/or olefinically unsaturated monomers having water dispersing groups.
  • an acrylic oligomer which is free from water dispersing groups may be polymerised in the presence of one or more olefinically unsaturated monomers having water dispersing groups.
  • Preferred polymerisation methods include solution polymerisation, emulsion polymerisation, suspension polymerisation and solution/dispersion polymerisation and such general methods are well known in the art.
  • an initiator may be used to assist acrylic polymer formation.
  • Suitable initiators are free-radical generators.
  • catalysts include azobis compounds, peroxides, hydroperoxides, redox catalysts, etc., for example, potassium persulfate, ammonium persulfate, tert-butyl peroctoate, benzoyl peroxide, isopropyl percarbonate, 2,4-dichlorobenzoyl peroxide, methyl ethyl ketone peroxide, cumene hydroperoxide, dicumyl peroxide, azobisisobutyronitrile, azobis(2-amidino-propane)hydrochloride and the like.
  • 0.05 to 5% by weight of initiator is used relative to the total weight of the monomers.
  • the polymerisation is performed in the presence of an emulsifying agent.
  • the Mn of the acrylic polymer may be controlled by the addition of chain transfer agents and/or through the adjustment of the ratio of the concentration of monomers relative to the concentration of initiator during the course of the polymerisation.
  • Typical chain transfer agents are thiols, halocarbons and cobalt macrocycles.
  • Preferred olefinically unsaturated monomers providing ionic dispersing groups include acrylic acid, methacrylic acid, itaconic acid, maleic acid, monoalkyl itaconates (for example, monomethyl maleate, monoethyl maleate, monobutyl maleate and monooctyl maleate), citraconic acid, styrenesulfonic acid, vinylbenzylsulfonic acid, vinylsulfonic acid, acryloyloxyalkyl sulfonic acids (for example, acryloyloxymethyl sulfonic acid, acryloyloxyethyl sulfonic acid, acryloyloxypropyl sulfonic acid and acryloyloxybutyl sulfonic acid), methacryloyloxymethyl sulfonic acid, methacryloyloxyethyl sulfonic acid, methacryloyloxypropyl sulfonic acid and methacrylo
  • Preferred olefinically unsaturated monomers providing non-ionic dispersing groups include alkoxy polyethylene glycol (meth)acrylates, preferably having a number average molecular weight of from 350 to 2000.
  • alkoxy polyethylene glycol (meth)acrylates preferably having a number average molecular weight of from 350 to 2000.
  • monomers which are commercially available include ⁇ -methoxypolyethylene glycol acrylate (mean polymerisation degree of polyethylene glycol is about 9) and diethylene glycol vinyl ether.
  • Preferred olefinically unsaturated monomers which are free from dispersing groups include alkyl(meth)acrylates, optionally substituted styrenes, methacrylamides, allyl compounds, vinyl ethers, vinyl ketones, vinyl halides, olefins and unsaturated nit les.
  • Preferred alkyl(meth)acrylates contain less than twenty carbon atoms. Examples include methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl, sec-butyl acrylate, amyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, tert-octyl acrylate, 2-phenoxyethyl acrylate, 2-chioroethyl acrylate, 2- bromoethyl acrylate, 4-chlorobutyl acrylate, cyanoethyl acrylate, 2-acetoxyethyl acrylate, dimethylaminoethyl acrylate, benzyl acrylate, methoxybenzyl acrylate, 2- chlorocyclohexyl acrylate, acylate, cyclohe
  • Preferred optionally substitured styrenes include styrene, methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene, diethylstyrene, isopropylstyrene, butylstyrene, hexylstyrene, cyclohexylstyrene, decylstyrene, chloromethylstyrene, trifluoromethylstyrene, ethoxymethylstyrene, acetoxymethylstyrene, methoxystyrene, 4- methoxy-3-methylstyrene, dimethoxystyrene, chlorostyrene, dichlorostyrene, trichlorostyrene, tetrachlorostyrene, pentachlorostyrene, bromostyrene, dibromostyrene, iodosty
  • Preferred methacylamides contain less than 12 carbon atoms.
  • Examples include methylmethacrylamide, tert-butylmethacrylamide, tert-octylmethacrylamide, benzylmethacrylamide, cyclohexylmethacrylamide, phenylmethacrylamide, dimethylmethacrylamide, dipropylmethacrylamide, hydroxyethyl-N- methylmethacrylamide, N-methylphenylmethacrylamide, N-ethyl-N-phenylmethacrylamide and methacrylhydrazine.
  • allyl compounds include allyl acetate, allyl caproate, allyl caprylate, allyl laurate, allyl palmitate, allyl stearate, allyl benzoate, allyl acetoacetate, allyl lactate, allyloxyethanol, allyl butyl ether and allyl phenyl ether.
  • Preferred vinyl ethers contain less than 20 carbon atoms. Examples include methyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, octyl vinyl ether, decyl vinyl ether, ethylhexyl vinyl ether, methoxyethyl vinyl ether, ethoxyethyl vinyl ether, chloroethyl vinyl ether, 1-methyl-2,2-dimethylpropyl vinyl ether, 2-ethylbutyl vinyl ether, hydroxyethyl vinyl ether and dimethylaminoethyl vinyl ether.
  • Preferred vinyl ketones contain less than 12 carbon atoms. Examples include methyl vinyl ketone, phenyl vinyl ketone and methoxyethyl vinyl ketone.
  • Preferred vinyl halides include vinyl chloride, vinylidene chloride and chlorotrifluoro ethylene.
  • Preferred olefins include unsaturated hydrocarbons having less than 20 carbon atoms. Examples include dicyclopentadiene, ethylene, propylene, 1-butene,1-pentene, 1-hexene, 4-methyl-1-pentene, 1-heptene, 1-octene, 1-decene, 5-methyl-1-nonene, 5,5- dimethyl-1-octene, 4-methyl-1-hexene, 4,4-dimethyl-1-pentene, 5-methyl-1-hexene, 4- methyl-1-heptene, 5-methyl-1-heptene, 4,4-dimethyl-1-hexene, 5,5,6-trimethyl-1- heptene, 1-dodecene and 1-octadecene.
  • Preferred unsaturated nitriles include acrylonitrile and methacyrlonitrile
  • the preferred olefinically unsaturated monomers which are free from dispersing groups are the alkyl (meth)acrylates containing less than 20 carbon atoms, especially those specifically listed above.
  • the acrylic polymer of the present invention may be purified if desired in the usual way for colorants used in ink jet printing inks.
  • a mixture of the acrylic polymer and water may be purified by ion-exchange, filtration, reverse osmosis, dialysis, ultra-filtration or a combination thereof. In this way one may remove co-solvents used for the polymerisation, low molecular weight salts, impurities and free monomers.
  • the Colorant is preferably soluble in the acrylic polymer.
  • the colorant is soluble in organic solvents and insoluble in water, for example it is free from sulpho and carboxy groups.
  • the colorant is a dye, more preferably a dye which is soluble in organic solvents and insoluble in water, especially a disperse dye.
  • the colorant is preferably yellow, magenta, cyan or black.
  • the colorant may be a single coloured component or a mixture of coloured components, for example it may be a mixture of different dyes. By using a mixture of different dyes as the colorant one may achieve greater flexibility in colour of the ink.
  • Useful classes of colorants include anthraquinones, phthalocyanines, pyrrolines, triphenodioxazines, methines, benzodifuranones, coumarins, indoanilines, benzenoids, xanthenes, phenazines, solvent soluble sulphur dyes, quinophthalones, pyridones, aminopyrazoies, pyrollidines, styrylics and azoics.
  • Examples of preferred azoics are monoazo, disazo and trisazo disperse dyes each, of which are optionally metallised 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.
  • disperse dyes are given in the Colour Index, 3rd 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 by reference thereto.
  • Preferred colorants for use in the inks include: CuPc(SO 2 NHCH 2 CH 2 CH 2 N(CH 3 ) 27 (SO 3 H) 0.3 in which Pc is phthalocyanine; and
  • Suitable water-miscible organic solvents include C,- 5 -alkanols, e.g. methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol and isobutanol; amides, e.g. dimethylformamide and dimethylacetamide; ketones and ketone alcohols, e.g. acetone and diacetone alcohol; C 2 . 4 -ether, e.g. tetrahydrofuran and dioxane; alkylene glycols or thioglycols containing a C 2 -C 6 alkylene group, e.g.
  • C,- 5 -alkanols e.g. methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol and iso
  • poly(alkylene- glycol)s and thioglycol)s e.g. diethylene glycol, thiodiglycol, polyethylene glycol and polypropylene glycol
  • polyols e.g. glycerol and 1 ,2,6-hexanetriol
  • lower alkyl glycol and polyglycol ethers e.g.
  • Preferred water-miscible organic solvents are Cj-e-alkyl mono ethers of C 2 - 6 -alkylene glycols and C
  • Suitable water-immiscible organic solvents include aromatic hydrocarbons, e.g. toluene, xylene, naphthalene, tetrahydronaphthalene and methyl naphthalene; chlorinated aromatic hydrocarbons, e.g. chlorobenzene, fluorobenzene, chloronaphthalene and bromonaphthalene; esters, e.g.
  • the composition according to the first aspect of the invention may be prepared by mixing the acrylic polymer, colorant, water, water-miscible organic solvent and water- immiscible organic solvent in any order. Suitable mixing techniques are well known in the art, for example agitation, ultrasonication or stirring of the components.
  • the acrylic polymer may be present in the composition in any form, especially suitable for use in inkjet printing (including a form suitable for dilution to give an ink jet printing ink), for example the form of a dispersion, emulsification, suspension, solution or a combination thereof.
  • the composition is prepared by mixing a dissipation of the acrylic polymer in a first liquid medium with a solution of the colorant in a second liquid medium, wherein the first liquid medium comprises water and optionally a water-miscible organic solvent and the second liquid medium comprises a water-immiscible organic solvent and optionally a water-miscible organic solvent.
  • the weight ratio of water-miscible organic solvent to water-immiscible organic solvent in the ink is preferably 19:1 to 1 :1 , more preferably 8:1 to 1 :1 , especially 5:1 to 1 :1.
  • the amount of colorant and water-dissipatable acrylic polymer contained in the composition will vary according to the depth of shade required. Typically, however, the composition will comprise:
  • the number of parts of the water-dissipatable acrylic polymer is calculated on a 100% solids basis. For example 50g of a 20% solids acrylic polymer is taken as 10g of acrylic polymer.
  • the composition optionally contains further ingredients of the type commonly used in ink jet printing inks, for example a biocide, for example Proxel GXL (Proxel is a trade mark of Zeneca Limited) or Kathon (Kathon is a trade mark of Rohm and Haas), a fungicide, a rheological agent, e.g. a wax (e.g. beeswax), a clay (e.g. bentonite), an IR absorber, for example Projet 900NP (Projet is a trade mark of Zeneca Limited), or a fluorescent brightener, for example C.I. Fluorescent Brightener 179 and/or UV absorber, for example hydroxy phenylbenzotriazole.
  • a biocide for example Proxel GXL (Proxel is a trade mark of Zeneca Limited) or Kathon (Kathon is a trade mark of Rohm and Haas)
  • a fungicide for example Proxel
  • the composition preferably has a pH from 3 to 11 , more preferably from 4 to 10.
  • the pH selected will depend to some extent on the desired cation for colorant and the materials used to construct the ink jet printer head.
  • the desired a pH may be obtained by the addition of an acid, base or a pH buffer. Where a base is used this is preferably the same base as was used to neutralise the anionic dispersing group during the preparation of the acrylic polymer.
  • the viscosity of the composition is preferably less than 20cp, more preferably less than 15cp, especially less than 10cp, at 20°C.
  • composition of the present invention may be used for piezoelectric, thermal and continuous inkjet printers. Many other compositions based on polymers work poorly or even not at all in thermal ink jet printers. Compositions of the invention form discrete droplets on the substrate with little tendency for diffusing. Consequently sharp images with excellent print quality and little if any bleed between colours printed side by side can be obtained. Furthermore the inks show good storage stability, wet and light fastness and fastness to both acidic and alkaline highlighter pens.
  • the composition has been filtered through a filter having a mean pore size less than 10 ⁇ m, more preferably less than 5 ⁇ m, especially less than 1 ⁇ m. In this way particulate matter which could otherwise block the printer-head is removed.
  • the composition is an ink (especially an ink jet printing ink) or a liquid concentrate which may be used to prepare such an ink.
  • a further aspect of the invention provides a process for printing an image on a substrate comprising applying thereto a composition according to the first aspect of the present invention by means of an ink jet printer.
  • the ink jet printer preferably applies the composition to the substrate in the form of droplets which are ejected through a small nozzle onto the substrate.
  • printers are piezoelectric ink jet printers and thermal ink jet printers.
  • thermal ink jet printers programmed pulses of heat are applied to the composition in a reservoir by means of a resistor adjacent to the nozzle, thereby causing the composition to be ejected in the form of small droplets directed towards the substrate during relative movement between the substrate and the nozzle.
  • piezoelectric ink jet printers the oscillation of a small crystal causes ejection of the composition from the nozzle.
  • the substrate is preferably a paper, plastic, or textile material, more preferably a paper, an overhead projector slide or a textile material, especially paper.
  • Preferred papers are plain, coated or treated papers which may have an acid, alkaline or neutral character.
  • the substrate is a coated paper.
  • an ink jet printer cartridge containing a composition as hereinbefore defined.
  • AIBN is azo bisisobutyronitrile.
  • the mixture was allowed to cool, before removing the butyl acetate by rotary evaporation to yield a water-dissipatable acrylic polymer as a viscous resinous material.
  • Resin 1 (30g) was then added to a solution of ammonia (4g) in water (66g) and allowed to dissolve with mild agitation and heating to give a 30%w/w solids dissipation in water.
  • 3-BM is 3-butylmercaptan AIBN is azo bisisobutyronitrile
  • Resin 2 20 N/M N/M 9.5
  • Inks were prepared by the method of Example 1 , Stage 2, except that there was used the components in the amounts shown in the table below:
  • Resins 2, 3 and 4 had a solids content of 20% and Resins 5 and 6 had a solids content of 30%.
  • the dye is the same phthalocyanine dye as that used in Example 1.
  • Example 1 A sample of the phthalocyanine dye used in Example 1 (3g) was dissolved in a mixture of benzyl alcohol (10g) and 2-pyrrolidone (20g) using a sonicator. A mixture of Neocryl BT44 (20g, obtained from Zeneca Resins, 45%w/w dispersion in water) and water (47g) was added and the mixture was shaken to give Ink C1 having the formulation:
  • Neocryl BT44 20 (45% solids)
  • Example 2 A sample of the phthalocyanine dye used in Example 1 (1g) was dissolved in a mixture of benzyl alcohol (10g) and 2-pyrrolidone (20g) using a sonicator. Water (69g) was added and the mixture was shaken to give Ink C2 having the formulation:
  • Ink C2 was found to be unstable to storage overnight with the dye precipitating from soluble. Therefore a freshly prepared sample of ink was used for the tests described in Table 1 below.
  • Example 7 Ink Jet Printing Using the Inks
  • Inks 1 to 6 and Inks C1 and C2 were printed onto Conqueror High White Wove plain paper 100g/M 2 from Arjo Wiggins Limited using a Hewlett Packard thermal ink-jet printer.
  • the properties of the resultant prints are shown in Table 1 below.
  • the prints resulting from Inks 1 and C2 had very good colour strength and brightness (chroma) as indicated in Table 1 and showed very high water fastness. 0.5ml of water run down a test print only 5 minutes after printing produced virtually no stain on the white paper. However Ink C2 suffered from poor storage stability. 14
  • ROD is the reflected optical density of the resultant print.
  • Example 8 Further inks may be prepared having the formulations described in Tables 2 and
  • FRU fructose
  • Resin * Identifies which of the acrylic polymers as prepared in Examples 1 to 6 are used.
  • MIBK Methylisobutyl ketone
  • Resin 1 Resin 1 from Example 1 (30% dissipation in water)
  • Colorant 1 CuPc (S0 2 NHCH 2 CH 2 CH 2 N(CH 2 ) 3 ) 27 (SO 3 H) 03 wherein Pc is phthalocyanine.
  • Colorant 2 The pyridone dye drawn on page 6 above.

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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)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Ink Jet (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition renfermant un polymère acrylique dispersible dans l'eau, de l'eau, un colorant, un solvant organique miscible avec l'eau et un solvant organique non miscible avec l'eau. La composition peut être utilisée dans des imprimantes thermiques et des imprimantes à jet d'encre piézo-électriques.
EP99907746A 1998-03-31 1999-03-09 Composition a base de polymere acrylique dispersible dans l'eau Withdrawn EP1084202A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9806793 1998-03-31
GBGB9806793.7A GB9806793D0 (en) 1998-03-31 1998-03-31 Composition
PCT/GB1999/000705 WO1999050365A1 (fr) 1998-03-31 1999-03-09 Composition a base de polymere acrylique dispersible dans l'eau

Publications (1)

Publication Number Publication Date
EP1084202A1 true EP1084202A1 (fr) 2001-03-21

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EP99907746A Withdrawn EP1084202A1 (fr) 1998-03-31 1999-03-09 Composition a base de polymere acrylique dispersible dans l'eau

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EP (1) EP1084202A1 (fr)
JP (1) JP2002509976A (fr)
AU (1) AU2737799A (fr)
GB (1) GB9806793D0 (fr)
WO (1) WO1999050365A1 (fr)

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Publication number Priority date Publication date Assignee Title
US6342094B1 (en) 2000-01-31 2002-01-29 Hewlett-Packard Company Miniemulsion techniques for ink jet inks
WO2002059222A1 (fr) * 2001-01-18 2002-08-01 Aprion Digital Ltd. Fluide d'impression par jet d'encre à base d'émulsion résine dans l'eau
US6821329B2 (en) 2001-10-31 2004-11-23 Hewlett-Packard Development Company, L.P. Ink compositions and methods of ink-jet printing on hydrophobic media
WO2004029165A1 (fr) * 2002-09-27 2004-04-08 Seiko Epson Corporation Composition d'encre a base d'eau, procede d'impression jet d'encre a partir de celle-ci, et imprime correspondant
EP1864823B1 (fr) 2005-03-31 2014-08-27 Seiko Epson Corporation Procede d'impression a jet d'encre utilisant une liquide d'amorce d'impression
JP2009155569A (ja) * 2007-12-27 2009-07-16 Kao Corp インクジェット記録用水分散体の製造方法
JP5360110B2 (ja) * 2011-03-29 2013-12-04 セイコーエプソン株式会社 プラスチックフィルム用インク組成物、それを用いたインクジェット記録法および記録物
JP6144549B2 (ja) * 2013-06-25 2017-06-07 キヤノンファインテック株式会社 インクジェット用の記録インクおよびインクジェット方式の記録方法
JP7005204B2 (ja) 2017-07-25 2022-01-21 キヤノン株式会社 水性インク、インクカートリッジ、及び画像記録方法

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US3607813A (en) * 1969-09-05 1971-09-21 Union Carbide Corp Printing ink compositions
US5139574A (en) * 1991-01-28 1992-08-18 Xerox Corporation Ink compositions
EP0769537B1 (fr) * 1995-10-18 2000-02-02 Seiko Epson Corporation Composition d'encre présentant une excellente résistance à l'eau

Non-Patent Citations (1)

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Title
See references of WO9950365A1 *

Also Published As

Publication number Publication date
AU2737799A (en) 1999-10-18
WO1999050365A1 (fr) 1999-10-07
JP2002509976A (ja) 2002-04-02
GB9806793D0 (en) 1998-05-27

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