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WO2004026978A1 - Compositions d'encres sechant sous l'effet de rayonnements utilisees pour l'impression a jet d'encre - Google Patents

Compositions d'encres sechant sous l'effet de rayonnements utilisees pour l'impression a jet d'encre Download PDF

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Publication number
WO2004026978A1
WO2004026978A1 PCT/GB2003/003836 GB0303836W WO2004026978A1 WO 2004026978 A1 WO2004026978 A1 WO 2004026978A1 GB 0303836 W GB0303836 W GB 0303836W WO 2004026978 A1 WO2004026978 A1 WO 2004026978A1
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WO
WIPO (PCT)
Prior art keywords
meth
acrylate
ink
compounds
mono
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.)
Ceased
Application number
PCT/GB2003/003836
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English (en)
Inventor
Andrew Stuart Overend
Janette Cordwell
Matthew Lloyd Parry
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
Priority to AU2003263312A priority Critical patent/AU2003263312A1/en
Priority to GB0503494A priority patent/GB2406858B/en
Publication of WO2004026978A1 publication Critical patent/WO2004026978A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • C09D11/36—Inkjet printing inks based on non-aqueous solvents
    • 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
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing

Definitions

  • Ink jet printing is a non-contact method by which droplets of ink are ejected through a fine nozzle onto a substrate.
  • ink jet printing There are many demanding performance requirements for inks used in ink jet printing. For example they should provide sharp, non-feathered images having good water, solvent- light- and ozone fastness, attractive colour and high optical density.
  • Further desirable properties for ink jet printing inks include a fast dry time (to facilitate high-speed printing), a low viscosity to enable the inks to be used in a wide range of ink jet printers, excellent mechanical resistance (to avoid the prints being rubbed off), low curl and good adhesion to a range of substrates.
  • organic solvents are included in ink jet printing inks to lower their viscosity.
  • US 4,303,924 discloses radiation curable ink jet printing inks containing organic solvent and large proportions of trifunctional monomers.
  • WO 02/38688 discloses low viscosity radiation curable compositions which are free from solvent and have low proportions of difunctional and tri- or higher functional monomers.
  • a non- aqueous, substantially solvent-free, radiation curable ink having a viscosity less than 30m Pa.s at 60°C, comprising: (i) a colorant (ii) a photo-initiator; and (iii) a mixture of (meth)acrylate compounds; wherein:
  • the mixture of (meth)acrylate compounds comprises c% of one or more mono (meth)acrylate compounds, d% of one or more di (meth)acrylate compounds and e% of one or more compounds having three or more
  • the value of Formula (1) is from 40 to 60, more preferably from 42.6 to 57, especially from 49 to 55.8.
  • the amount of colorant in the ink is preferably from 0.1 to 14%, more preferably from 1 to 10% and especially from 1.1 to 8% by weight, relative to the total weight of the ink.
  • the colorant is not white.
  • Preferred colorants are yellow, magenta, cyan, black, blue, indigo, violet, green, orange, red and mixtures comprising two or more thereof.
  • the ink is free from titanium dioxide.
  • the colorant is preferably a dye, a pigment or a mixture thereof. More preferably the colorant is a pigment.
  • Preferred dyes and pigments are free from ionic groups, for example disperse dyes and water-insoluble pigments are especially preferred colorants.
  • Preferred pigments are organic or inorganic.
  • the pigment is preferably in the form particles which are small enough to pass through the very fine nozzles used in the phntheads of ink jet printers. Typically these nozzles are half the diameter of a human hair.
  • the average particle size of the pigment is preferably from 0.003 to 15 ⁇ m, more preferably from 0.004 to 5 ⁇ m and especially from 0.005 to 1 ⁇ m.
  • Pigment particle sizes outside these ranges may be used where printheads have particularly large nozzle diameters.
  • Very fine dispersions of pigments and methods for their preparation are disclosed in, for example, EP 0 776 952, US 5,538,548, US 5,443,628, EP 0 259 130, US 5,285,064, EP 0 429 828 and EP 0 526 198.
  • inorganic pigments include carbon black, titania, iron oxide, zinc oxide and mixtures thereof.
  • organic pigments include phthalocyanines, anthraquinones, perylenes, carbazole, monoazo and disazobenzimidazolones, isoindolinones, monoazonaphthols, diarylidepyrazolones, rhodamines, indigoids, quinacridones, diazopyranthrones, dinitranilines, pyrazolones, dianisidines, pyranthrones, tetrachloroisoindolinones, dioxazines, monoazo acrylides, anthrapyrimidines and mixtures thereof.
  • carbon black pigments examples include Regal 400R, MogulTM L, ElftexTM 320 from Cabot Co., or Carbon Black FW18, Special Black 250, Special Black 350, Special Black 550, PrintexTM 25, PrintexTM 35, PrintexTM 55 and PrintexTM 150T from Degussa Co., and Pigment Black 7. Further examples of pigments include CI. Pigment Yellow 17, CI. Pigment Blue 27. CI. Pigment Red 49:2, CI. Pigment Red 81 :1 , CI. Pigment Red 81 :3, CI. Pigment Red 81 :x, CI. Pigment Yellow 83, CI. Pigment Red 57: 1 , CI. Pigment Red 49:1 , CI. Pigment Violet 23, CI.
  • Pigment Black 1 1 CI. Pigment Metal 1 , CI. Pigment Metal 2, CI. Pigment Yellow 128, CI. Pigment Yellow 93, CI. Pigment Yellow 74, CI. Pigment Yellow 138, CI. Pigment Yellow 139, CI. Pigment Yellow 154, CI. Pigment Yellow 185, CI. Pigment Yellow 180, CI. Pigment Red 122, CI. Pigment Red 184, and bridged aluminium phthalocyanine pigments.
  • the especially preferred pigments are Pigment Yellow 128, 93, 17, 74, 138, 139, 154, 185, 180; Pigment Red 122, 57:1 , 184; Pigment Blue 15:3, 15:4 and carbon black.
  • Preferred dyes include azo, diazo, xanthene, anthraquinone, triaryl methane, azine, thiazine, phthalocyanine and nigrosine types.
  • Dyes may be used singly or in combination with other dyes and/or pigments. Dyes are preferably disperse or solvent soluble, examples of which may be selected from The Colour Index especially the 3 rd edition, 1982, pages 147-263. Dyes can be metalised or non-metalised.
  • the ink optionally further contains a dispersant.
  • a dispersant is often not necessary because the dye may be soluble in the formulation.
  • the pigment is self-dispersible (e.g. the pigment carries dispersing groups or is surface modified to be self-dispersible) no further dispersant is needed.
  • a dispersant is preferably included in the ink to assist storage stability.
  • Suitable dispersants include, for example, polyester, polyurethane and polyacrylate dispersants, especially those in the form of high molecular weight block copolymer.
  • dispersants examples include DisperbykTM (ex BYK Chemie) and SolsperseTM (ex Avecia) dispersants.
  • DisperbykTM Ex BYK Chemie
  • SolsperseTM Ex Avecia
  • a detailed list of non-polymeric as well as some polymeric dispersants appears in, for example, McCutcheon's Functional Materials, North American Edition, Manufacturing Confectioner Publishing Co., Glen Rock, N.J., pp.110- 129 (1990), the entire disclosure of which is incorporated herein by reference.
  • Dispersants suitable for use with pigments are also disclosed in DE 19636382, US 5,720,802, US 5,713,993, PCT/GB95/02501 , US 5,085,689 and GB 2303376. When the ink contains a dispersant this is preferably present in an amount of 50 to 150% by weight relative to the weight of colorant.
  • self-dispersing pigments include surface treated carbon blacks carrying carboxy, sulphonate and/or ethylene oxide groups.
  • the pigment and dispersant are preferably added to the ink as a mixture.
  • a mixture of a pigment and a dispersant may be made by milling pigment in a small amount of the (meth)acrylate components c), d) and e) with a milling media, e.g. glass beads.
  • the pigment dispersion is then typically screened and "let down" by slowly adding the remaining ink components.
  • the amount of photo-initiator in the ink is preferably 0.1 to 15%, more preferably 3 to 12% by weight, relative to the total weight of the ink.
  • Preferred photo-initiators include alpha diketones, monoketals of alpha-diketones or ketoaldehydes, acyloins and their corresponding ethers, chromophore-substituted halo-s-triazines, and chromophore- substituted halomethyl-oxadiozoles.
  • photo-initiators include acetophenone, propiophenone, 2-phenyl-acetophenone, 2-chloro-2-phenyl-acetophenone, 2-2-dichloro-2-phenyl-acetophenone, 2-butoxy-2-phenyl acetophenone, 2,2-dimethoxy-2- phenyl-acetophenone, 2,2-diethoxy-acetophenone, 2-methylol-2-methoxy-2-phenyl- acetophenone, benzophenone, 4-trichloromethyl benzophenone, indenone, 1-3- indanedione, fluorenone, xanthone, thioxanthone, 2-chlorothioxanthone, anthraquinone, 2-ethylanthraquinone, biacetyl, glyoxal, 1 ,2-indanedione, p-chlorophenyl-glyoxal, benzil, campho
  • photo-initiators particularly suitable for use in the present invention include SpeedcureTM ITX, and IrgacureTM 369.
  • the ink optionally further contains one or more co-initiators or amine synergists in order to improve cure rate. Examples include isopropylthioxanthone, ethyl-4-(dimethylamine) benzoate, 2-ethyl hexyl dimethylaminobenzoate and dimethylaminoethyl methacrylate.
  • the photo-initiator is other than a cationic photo-initiator.
  • the photo-initiator is a free radical photo-initiator.
  • the photo-initiator is soluble in the ink.
  • a single photo-initiator may be used although it is preferable that the photo-initiator is a mixture of two or more photo-initiators because this can lead to a broader spectral response, improved depth of cure and improved cure rate with opacifying pigments such as carbon black.
  • the ink further comprises a stabiliser to improve the storage stability of the ink and prevent premature curing.
  • the stabiliser is preferably an antioxidant, a radical trap, a radical quencher or the like, e.g. a phenol, thiol, quinone, hydroquinone, amine, xanthate or an N-alkyl or N-aryl aniline. Too much stabiliser will prevent cure entirely.
  • preferred amounts of stabiliser are from 0 to 10%, more preferably from 0.01 to 5%, and especially from 0.1 to 3% by weight relative to the total weight of the ink. Mixtures of stabilisers are preferable for the best ink storage lifetime.
  • the ink is curable by actinic radiation or particle beam, especially by UV or electron beam radiation.
  • Mono (meth)acrylate compounds have one (and only one) acrylate or methacrylate group. This group is, as is known in the art, is polymerisable when irradiated in the presence of a photo-initiator.
  • (Meth)acrylate groups are represented by the formula:
  • R is H or methyl
  • the mono (meth)acrylate compound is preferably a monomer.
  • mono (meth)acrylate monomers include cyclic trimethylolpropane formal (meth)acrylate, ethoxylated tetra hydrofurfuryl (meth)acrylate, phenoxy ethyl (meth)acrylate, trimethylol propane formal (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, monomethoxy neopentyl glycol propoxylate mono (meth)acrylate, monomethoxy tripropylene glycol mono (meth)acrylate, 2-(2-ethoxyethoxy) ethyl (meth)acrylate, iso- decyl (meth)acrylate, iso-octyl (meth)acrylate, iso-nonyl (meth)acrylate, tridecyl (meth)acrylate, iso-bomyl (meth)acrylate, eth
  • Preferred mono (meth)acrylate monomers include lauryl (meth)acrylate, tetrahydro furfuryl (meth)acrylate, 2-(2-ethoxyethoxy)ethyl (meth)acrylate, iso-octyl (meth)acrylate, iso-decyl (meth)acrylate, tridecyl (meth)acrylate, dodecyl (meth)acrylate, isobomyl (meth)acrylate, cyclic trimethylol propane formal (meth)acrylate.
  • the one or more monomer (meth)acrylate compounds is or comprises isobomyl acrylate.
  • Di (meth)acrylate compounds have two (and only two) groups selected from acrylate and methacrylate.
  • Preferred di (meth)acrylate compounds are di (meth)acrylate monomers, for example di(meth)acrylates of 1 ,4 butane diol, 1-6 hexane diol, neopentyl glycol, mono, di, tri and poly ethylene glycols, mono, di, tri and poly propylene glycols, mono methoxy ethoxylated trimethylolpropane, propoxylated neopentyl glycol, ethoxylated neopentyl glycol, 1 ,2 butylene glycol and ethoxylated hexane diol.
  • the one or more di(meth)acrylate compounds is or comprises 1 ,6 hexane diol diacrylate.
  • the compound(s) having three or more (meth) acrylate groups have three or more groups selected from acrylate and methacrylate.
  • the compound having three or more (meth)acrylate groups is preferably a monomer, oligomer or polymer, preferred examples of which include trimethylol propane tri(meth)acrylate, ethoxylated trimethylol propane tri(meth)acrylate, propoxylated trimethylol propane tri(meth)acrylate, glycerol tri(meth)acrylate, propoxylated glycerol tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, ditrimethylol propane tetra (meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, ethoxylated di-pentaerylthritol tetra (meth)acrylate, tetra methylol methane t
  • the one or more compounds comprising three or more (meth)acrylate groups is or comprises trimethylol propane triacrylate and/or ethoxylated trimethylol propane triacrylate.
  • Inks which contain acrylates polymerise more quickly than those containing methacrylates when exposed to actinic or particle beam radiation. Consequently, the amount of methacrylate is preferably not greater than 20%, more preferably not greater than 10% and especially not greater than 5% of component (iii). It is particularly preferred that component (iii) contains no methacrylate.
  • the ink further comprises a polymer or oligomer containing no (meth)acrylate groups.
  • a polymer or oligomer containing no (meth)acrylate groups is present in the ink at from 0 to15%, more preferably from 0 to 10% and most preferably from 0 to 5% by weight relative to the total weight of the ink.
  • Inks of the present invention are substantially solvent free. That is to say no solvent or water is present in the ink except for trace amounts which may be present as impurities in any of the ink components. Preferably any such residues are less than 2%, more preferably less than 0.5% and especially less than 0.01 % by weight relative to the total weight of ink. As hereinbefore described inks of the present invention are particularly suitable for use in ink jet printing. A preferred ink jet type for inks of the present invention is piezo ink jet printing.
  • the viscosity of the inks of the present invention are preferably 1 to 30 mPa.s, more preferably from 2 to 25 mPa.s at 60°C
  • the ink composition may optionally have a higher viscosity at room temperature provided that the final ink meets the above viscosity requirements at the above temperature.
  • the surface tension of the ink of the present invention is preferably below 40 dynes/cm.
  • Inks of the present invention are preferably free from particulate impurities that would tend to block an ink jet nozzle.
  • the ink is preferably filtered through a filter with a pore size of less than 10um, more preferably less than 34m and especially less than 14 .
  • a particularly preferred ink according to the invention is a non-aqueous, substantially solvent-free, radiation curable ink having a viscosity of 1 to 30m Pa.s at 60°C comprising:
  • the mixture of (meth)acrylate compounds comprises c% of one or more mono (meth)acrylate compounds, d% of one or more di (meth)acrylate compounds and e% of one or more compounds having three or more (meth)acrylate groups, wherein the values of c%, d% and e% are by weight relative to the total weight of the mono (meth )acry late compounds, di (meth)acrylate compounds and compounds having three or more (meth)acrylate groups and are such that the value of Formula (1 ) is from 40 to 60:
  • the photo-initiator is present in the ink in an amount of 3 to 12% by weight relative to the total weight of ink;
  • the one or more mono (meth)acrylate compounds are selected from the group consisting of cyclic trimethylolpropane formal (meth)acrylate, ethoxylated tetra hydrofurfuryl (meth)acrylate, phenoxy ethyl (meth)acrylate, trimethylol propane formal (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, monomethoxy neopentyl glycol propoxylate mono (meth)acrylate, monomethoxy t propylene glycol mono (meth)acrylate, 2-(2-ethoxyethoxy) ethyl (meth)acrylate, iso-decyl (meth)acrylate, iso-octyl (meth)acrylate, iso-nonyl (meth)acrylate, tridecyl (meth)acrylate, iso-bomyl (meth)acrylate, ethoxyl nonyl
  • the one or more di (meth)acrylate compounds are selected from the group consisting of di(meth)acrylates of 1 ,4 butane diol, 1-6 hexane diol, neopentyl glycol, mono, di, tri and poly ethylene glycols, mono, di, tri and poly propylene glycols, mono methoxy ethoxylated trimethylolpropane, propoxylated neopentyl glycol, ethoxylated neopentyl glycol, 1 ,2 butylene glycol and ethoxylated hexane diol and mixtures thereof; and
  • the one or more compounds having three or more (meth)acrylate groups are selected from the group consisting of trimethylol propane tri(meth)acrylate, ethoxylated trimethylol propane tri(meth)acrylate, propoxylated trimethylol propane tri(meth)acrylate, glycerol tri(meth)acrylate, propoxylated glycerol tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, ditrimethylol propane tetra (meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, ethoxylated di- pentaerylthritol tetra (meth)acrylate, tetra methylol methane tetra
  • the mixture of (meth)acrylate compounds is preferably present in the ink in an amount of from 70 to 95.9%, more preferably from 75 to 95.9%, and especially from 78 to 95.9% by weight relative to the total weight of ink. Any difference between the weight of components (i), (ii) and (iii) and 100% is made up by other customary ink additives, e.g. flow control agents, dispersants, biocides, rheology modifiers and so on other than water or organic solvent.
  • customary ink additives e.g. flow control agents, dispersants, biocides, rheology modifiers and so on other than water or organic solvent.
  • Inks of the present invention may contain further components in addition to components (i) to (iii) specified above, for example preservatives, biocides, rheology modifiers, surfactants, levelling agents, antifoaming agents, anti-kogation agents and combinations thereof.
  • a process for printing an image onto a substrate comprising applying thereto an ink according to the first aspect of the present invention by means of an ink jet printer and curing the ink, preferably using an electron beam or more preferably using ultra violet light.
  • Printed substrates obtained by this process form a further feature of the present invention.
  • Preferred substrates are metal, plastic, ceramic, glass, wood, printed circuit boards and plain and coated papers.
  • Preferred applications include printing for home/office use, packaging, labelling and barcodes, particularly wide format graphics, printed circuit board manufacture, signage, wall coverings and decorative laminates.
  • an ink jet printer cartridge comprising a chamber and an ink wherein the ink is present in the chamber and is as defined in the first aspect of the invention.
  • a radiation curable ink was prepared containing the following components:
  • a millbase was prepared by bead milling RegalTM 250R pigment with a small amount of SartomerTM 256 and SartomerTM 238 together with SolsperseTM 32000 and 5000 dispersants until a fine particle dispersion was formed. The remaining components were then added in the dark and the mixture was homogenised and then filtered through a 1 micron WhatmanTM syringe filter.
  • a radiation curable ink was prepared (in an analogous manner to Example 1 ) containing the following components:
  • the percentages of mono acrylate , di acrylate and tri acrylate compounds by weight relative to the total weight of such compounds are such that the value of Formula (1 ) was 84.79.
  • Example 1 and Comparative Example 1 were each coated onto sheen cards using an 8 ⁇ m K-bar coater.
  • the coatings were cured using Fusion Systems apparatus fitted with a "D" 300W/inch bulb using cure energy in the range UV A 0.37 - 0.74, UV B 0.172 - 0.99 and UV C 0.07 - 0.11 at belt/cure speeds of 25M/min or 15M/min.
  • the Reflectance Optical Density (ROD) of the cured coated sheen cards was measured using an XRite 938 Spectrodensitometer using density status T, illuminant D50 and 2° observer.
  • the Chemical Resistance (% loss) was determined by performing 5 x MEK (methyl ethyl ketone) double rubs on the coated cured sheen cards and then measuring the ROD in the rubbed region. The Chemical Resistance (% loss) value was then expressed via
  • the surface tension of the inks were determined at 25°C using a Kruss Surface Tension Balance.
  • the hardness of the print was assessed in the conventional manner using pencils of different hardness, where the hardness is determined as the lowest hardness value that forms a scratch in the print.
  • Example 1 has better chemical resistance and a faster cure speed than Comparative Example 1 whilst still retaining a low viscosity suitable for ink jet printing. Furthermore, Example 1 has better pencil hardness and a higher ROD than Comparative Example 1.
  • the ink described in Example 1 was readily jetted through a Spectra Galaxy printhead. Further inks of the present invention were prepared (in an analogous manner to
  • Example 1 containing:
  • Such inks showed excellent printing performance through a Spectra Galaxy printhead and had very good chemical resistance.

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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

La présente invention concerne une encre non aqueuse, sensiblement dénuée de solvant, séchant sous l'effet de rayonnements qui présente une viscosité inférieure à 30m Pa.s à 60°C et qui comprend: (iv) un colorant (v) un photo-initiateur; et (vi) un mélange de composés (méth)acrylate. Cette encre se caractérise en ce que: (a) le colorant est présent dans l'encre suivant une quantité comprise entre 0,1 et 14,9 % en poids par rapport au poids total de l'encre; et (b) le mélange de composés (méth)acrylate comprend c% d'au moins un composé mono (méth)acrylate, d% d'au moins un composé di (méth)acrylate et e% d'au moins un composé comportant au moins trois groupes (méth)acrylate, les valeurs de c%, d% et e% étant définies en poids par rapport au poids total des composés mono (méth)acrylate, des composés di (méth)acrylate et des composés comportant au moins trois groupes (méth)acrylate et sont telles que la valeur de la formule (1) est inférieure ou égale à 60: c% + 0,628 (d% + e%) (sin60 tan60) Formule (1)
PCT/GB2003/003836 2002-09-20 2003-09-04 Compositions d'encres sechant sous l'effet de rayonnements utilisees pour l'impression a jet d'encre Ceased WO2004026978A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003263312A AU2003263312A1 (en) 2002-09-20 2003-09-04 Radiation curable inkjet inks compositions
GB0503494A GB2406858B (en) 2002-09-20 2003-09-04 Radiation curable inkjet inks compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0221894A GB0221894D0 (en) 2002-09-20 2002-09-20 Compositions
GB0221894.9 2002-09-20

Publications (1)

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WO2004026978A1 true WO2004026978A1 (fr) 2004-04-01

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2396621A (en) * 2002-11-27 2004-06-30 Konica Minolta Holdings Inc Actinic ray curable ink jet solventless ink, image forming method using the same, and ink jet recording apparatus
WO2005047405A1 (fr) * 2003-11-12 2005-05-26 Vutek, Incorporated Compositions d'encre durcissables par exposition a un rayonnement et applications de celles-ci
EP1593718A1 (fr) * 2004-05-06 2005-11-09 Agfa-Gevaert Compositions d'encre durcissantes pour impression par jet d'encre
WO2007000566A1 (fr) * 2005-06-25 2007-01-04 Fujifilm Imaging Colorants Limited Procede
US7700263B2 (en) 2003-12-20 2010-04-20 Fujifilm Imaging Colorants Limited Substantially solvent-free and photoinitiator-free curable ink
US8083338B2 (en) 2004-05-06 2011-12-27 Agfa Graphics N.V. Radiation-curable ink-jet printing
US20120171434A1 (en) * 2009-09-08 2012-07-05 Sun Chemical B.V. Photoinitiator composition
US8585814B2 (en) * 2005-04-14 2013-11-19 Konica Minolta Medical & Graphic, Inc. Active ray curable ink-jet ink, image forming method and ink-jet recording apparatus using the same
EP3092268A4 (fr) * 2014-01-08 2017-08-23 Sun Chemical Corporation Encres durcissables sous l'effet d'une énergie présentant une adhérence améliorée, procédé de formulation
US10190018B2 (en) 2015-08-31 2019-01-29 Kateeva, Inc. Di- and mono(meth)acrylate based organic thin film ink compositions
WO2018195066A3 (fr) * 2017-04-21 2020-03-26 Kateeva, Inc. Compositions et techniques de formation de films minces organiques
WO2024118440A1 (fr) * 2022-12-01 2024-06-06 Sun Chemical Corporation Revêtements uv pour films et étiquettes monobandes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0608466D0 (en) 2006-04-27 2006-06-07 Sericol Ltd A printing ink

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5275646A (en) * 1990-06-27 1994-01-04 Domino Printing Sciences Plc Ink composition
WO1999029788A1 (fr) * 1997-12-05 1999-06-17 Xaar Technology Limited Compositions d'encre pour l'impression a jet d'encre sous cuisson electronique
WO1999029787A2 (fr) * 1997-12-05 1999-06-17 Xaar Technology Limited Compositions d'encre pour l'impression a jet d'encre sous cuisson electronique
US6114406A (en) * 1996-02-21 2000-09-05 Coates Brothers Plc Radiation curable ink composition
EP1323795A1 (fr) * 2001-12-20 2003-07-02 Ucb S.A. Compositions durcissables par irradiation, pour des encres pigmentées liquides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5275646A (en) * 1990-06-27 1994-01-04 Domino Printing Sciences Plc Ink composition
US6114406A (en) * 1996-02-21 2000-09-05 Coates Brothers Plc Radiation curable ink composition
WO1999029788A1 (fr) * 1997-12-05 1999-06-17 Xaar Technology Limited Compositions d'encre pour l'impression a jet d'encre sous cuisson electronique
WO1999029787A2 (fr) * 1997-12-05 1999-06-17 Xaar Technology Limited Compositions d'encre pour l'impression a jet d'encre sous cuisson electronique
EP1323795A1 (fr) * 2001-12-20 2003-07-02 Ucb S.A. Compositions durcissables par irradiation, pour des encres pigmentées liquides

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7104642B2 (en) 2002-11-27 2006-09-12 Konica Minolta Holdings, Inc. Active ray curable ink jet solventless ink, image forming method using the same, and ink jet recording apparatus
GB2396621A (en) * 2002-11-27 2004-06-30 Konica Minolta Holdings Inc Actinic ray curable ink jet solventless ink, image forming method using the same, and ink jet recording apparatus
GB2396621B (en) * 2002-11-27 2007-03-14 Konica Minolta Holdings Inc Active ray curable ink jet solventless ink,image forming method using the same, and ink jet recording apparatus
WO2005047405A1 (fr) * 2003-11-12 2005-05-26 Vutek, Incorporated Compositions d'encre durcissables par exposition a un rayonnement et applications de celles-ci
US7365105B2 (en) 2003-11-12 2008-04-29 Electronics For Imaging, Inc. Radiation curable ink compositions and applications thereof
US7579388B2 (en) 2003-11-12 2009-08-25 Electronics For Imaging, Inc. Radiation curable ink compositions and applications thereof
US7700263B2 (en) 2003-12-20 2010-04-20 Fujifilm Imaging Colorants Limited Substantially solvent-free and photoinitiator-free curable ink
EP1593718A1 (fr) * 2004-05-06 2005-11-09 Agfa-Gevaert Compositions d'encre durcissantes pour impression par jet d'encre
US8083338B2 (en) 2004-05-06 2011-12-27 Agfa Graphics N.V. Radiation-curable ink-jet printing
US8585814B2 (en) * 2005-04-14 2013-11-19 Konica Minolta Medical & Graphic, Inc. Active ray curable ink-jet ink, image forming method and ink-jet recording apparatus using the same
WO2007000566A1 (fr) * 2005-06-25 2007-01-04 Fujifilm Imaging Colorants Limited Procede
US20120171434A1 (en) * 2009-09-08 2012-07-05 Sun Chemical B.V. Photoinitiator composition
US9321853B2 (en) * 2009-09-08 2016-04-26 Sun Chemical Corporation Photoinitiator composition
EP3092268A4 (fr) * 2014-01-08 2017-08-23 Sun Chemical Corporation Encres durcissables sous l'effet d'une énergie présentant une adhérence améliorée, procédé de formulation
US10190018B2 (en) 2015-08-31 2019-01-29 Kateeva, Inc. Di- and mono(meth)acrylate based organic thin film ink compositions
WO2018195066A3 (fr) * 2017-04-21 2020-03-26 Kateeva, Inc. Compositions et techniques de formation de films minces organiques
US11844234B2 (en) 2017-04-21 2023-12-12 Kateeva, Inc. Compositions and techniques for forming organic thin films
WO2024118440A1 (fr) * 2022-12-01 2024-06-06 Sun Chemical Corporation Revêtements uv pour films et étiquettes monobandes

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GB0503494D0 (en) 2005-03-30
GB0221894D0 (en) 2002-10-30
TW200418938A (en) 2004-10-01

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