WO2010057839A1 - Encre d'impression contenant du n-vinylcaprolactame et d'autres monomères de n-vinylamide - Google Patents

Encre d'impression contenant du n-vinylcaprolactame et d'autres monomères de n-vinylamide Download PDF

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Publication number
WO2010057839A1
WO2010057839A1 PCT/EP2009/065185 EP2009065185W WO2010057839A1 WO 2010057839 A1 WO2010057839 A1 WO 2010057839A1 EP 2009065185 W EP2009065185 W EP 2009065185W WO 2010057839 A1 WO2010057839 A1 WO 2010057839A1
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WO
WIPO (PCT)
Prior art keywords
printing ink
printing
weight
formula
vinylcaprolactam
Prior art date
Application number
PCT/EP2009/065185
Other languages
German (de)
English (en)
Inventor
Yvonne Heischkel
Markus Christian Biel
Matthias Fies
Wolfgang Staffel
Original Assignee
Basf Se
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 Basf Se filed Critical Basf Se
Priority to EP09749150A priority Critical patent/EP2358832A1/fr
Publication of WO2010057839A1 publication Critical patent/WO2010057839A1/fr

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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
    • C09D11/02—Printing inks
    • 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
    • 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

  • the invention relates to a printing ink which comprises N-vinylcaprolactam and at least one N-vinylamide monomer of the formula
  • R1 represents a hydrogen atom or a C1 to C4 alkyl group and R2 represents a
  • Hydrogen atom or an organic radical having a maximum of 10 carbon atoms contains.
  • Printing inks are often advantageously solvent-free. This eliminates the need to remove solvents after printing. Even without solvent, the ink should be liquid at room temperature.
  • printing inks often contain so-called reactive diluents, these are low molecular weight compounds, which become a part of the resulting coating after curing. The choice of reactive diluent also has an effect on the performance properties of the resulting printed substrates.
  • the adhesion to the most diverse materials to be printed is good.
  • the adhesion to non-polar substrates, e.g. with plastic surfaces is good.
  • the object of the present invention therefore, printing inks, which have a low viscosity and therefore are solvent-free processable and have very good performance properties, in particular good adhesion to non-polar substrates is of importance.
  • the printing ink of the invention contains N-vinylcaprolactam and at least one N-vinylamide monomer of the formula
  • R1 represents a hydrogen atom or a C1 to C4 alkyl group and R2 represents a hydrogen atom or an organic radical having a maximum of 10 carbon atoms.
  • R 1 is a hydrogen atom or a methyl group.
  • R2 may represent a hydrogen atom or any organic radical containing a maximum of 10 carbon atoms (C atoms); the radical R2 may contain heteroatoms such as nitrogen, oxygen or sulfur.
  • R2 is a hydrogen atom or a C1 to C10, in particular a C1 to C4 alkyl group such as methyl, ethyl, n-propyl or n-butyl.
  • N-vinylamide monomer of the formula I is N-vinylformamide, N-vinylacetamide or N-vinyl-N-methylacetamide. Very particular preference is given to N-vinylformamide.
  • the printing ink preferably contains N-vinylcaprolactam and N-vinylamide monomers of the formula I in an amount of from 0.5 to 60% by weight, more preferably from 1 to 50% by weight, based on the total printing ink.
  • the content of N-vinylcaprolactam and the N-vinylamide monomers of the formula I is generally not greater than 50% by weight, in particular 40% by weight, based on the printing ink.
  • the printing ink preferably contains N-vinylcaprolactam in an amount of 5 to 85% by weight and N-vinylamide monomers of the formula I in an amount of 15 to 95% by weight, the percentages by weight being based on the total by weight of N-vinylcaprolactam and N-Vinylamidmonomeren of formula I are related.
  • the content of N-vinylcaprolactam can be at least 20, particularly preferably at least 40 and very particularly preferably at least 60% by weight, the maximum content is preferably 80% by weight or else 75% by weight of N-vinylcaprolactam.
  • the content of N-vinylamide monomers of the formula I may preferably be at least 20 or else at least 25% by weight; the maximum content of N-vinylamide monomers may preferably be 80% by weight, more preferably 60% by weight and most preferably at least 40% by weight.
  • N-vinylcaprolactam and the N-vinylamide monomers of the formula I can be added separately to the printing ink of the invention.
  • a mixture is prepared in advance from the N-vinylcaprolactam and the one or more N-vinylamide monomers of the formula I used (monomer mixture).
  • the above amounts of 5 to 85% by weight of N-vinylcaprolactam and 15 to 95% by weight of N-vinylamide monomers and the corresponding preferable ranges.
  • the monomer mixture at 20 0 C, 1 bar liquid consists in particular to more than 80 wt .-% of N-vinylcaprolactam and N-vinylamide monomers of the formula I.
  • the monomer mixture is still liquid at a very high content of N-vinylcaprolactam (at 21 0 C, 1 bar).
  • NVC N-vinylcaprolactam
  • NVF N-vinylformamide
  • VIMA N-vinylcaprolactam
  • NVC N-vinylcaprolactam
  • VIMA N-vinyl-N-methylacetamide
  • the monomer mixture may contain further constituents, for example further monomers or else additives such as stabilizers etc.
  • the monomer mixture is preferably a mixture which contains more than 80% by weight, in particular more than 90% by weight or more than 95% by weight, of N-vinylcaprolactam and N-vinylcaprolactam.
  • R 1 is a hydrogen atom or a C 1 to C 4 alkyl group and R 2 is a hydrogen atom or an organic radical having a maximum of 10 carbon atoms, and which optionally contains further additives, in particular at least one stabilizer.
  • Suitable stabilizers are all customary stabilizers which prevent premature polymerization in the case of N-vinylcaprolactam and N-vinylamides of the formula I.
  • mixtures of stabilizers are also suitable.
  • stabilizers may be mentioned nitroxyl compounds, such as 1-oxyl-2,2,6,6-tetramethylpiperidine, 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine, phenol derivatives having at least one substituent in the alpha position to the phenol group such as 2,6-di-tert-butyl-4-methylphenol, tocopherols, quinones and hydroquinones, such as hydroquinone monomethyl ether, N-oxyl compounds, aromatic amines and phenylenediamines, imines, sulfonamides, oximes, hydroxylamines, urea derivatives, phosphorus-containing compounds, sulfur-containing compounds, Complexing agents based on tetraazaannulenes (TAA)
  • Phosphorus containing compounds are e.g. Triphenylphosphine, triphenyl phosphite, hypophosphorous acid, trinonyl phosphite, triethyl phosphite or diphenylisopropylphosphine.
  • the monomer g mixture is preferably a mixture which contains more than 80% by weight, in particular more than 90% by weight or more than 95% by weight, of N-vinylcaprolactam and N Vinylformamide is present and which optionally contains further additives, in particular at least one stabilizer.
  • the printing ink of the invention can be prepared in any manner from the individual components. Preferred is a process in which first the above monomer mixture containing N-vinylcaprolactam, an N-vinylamide monomer of the formula I and optionally at least one stabilizer is prepared and then adding this monomer mixture in any order to the other components of the ink.
  • the ink may contain other ingredients.
  • N-vinylcaprolactam, the N-vinylamide monomers of the formula I and, if appropriate, further monomers, oligomers and polymers are collectively also referred to as binders.
  • Further monomers preferably have a molecular weight of less than 300, in particular less than 200, g / mol. They serve in particular as reactive diluents.
  • Possible monomers are e.g. selected from C 1 -C 20 -alkyl (meth) acrylates, vinyl esters of carboxylic acids containing up to 20 carbon atoms, vinylaromatics having up to 20 carbon atoms, ethylenically unsaturated nitriles, vinyl ethers of alcohols containing from 1 to 10 carbon atoms.
  • mixtures of (meth) acrylic esters are suitable.
  • Vinyl esters of carboxylic acids having 1 to 20 carbon atoms are e.g. Vinyl laureate, stearate, vinyl propionate, vinyl versatate and vinyl acetate.
  • Suitable vinylaromatic compounds are vinyltoluene a- and p-methylstyrene, a-butylstyrene, 4-n-butylstyrene, 4-n-decylstyrene and preferably styrene.
  • nitriles are acrylonitrile and methacrylonitrile.
  • vinyl ethers there are e.g. Vinyl methyl ether or vinyl isobutyl ether. Vinyl ether is preferably from 1 to 4 C-containing alcohols.
  • Preferred compounds A1 are (meth) acrylate compounds and in particular the C1 to C10 alkyl acrylates and methacrylates, in particular C1 to C8 alkyl acrylates and methacrylates.
  • methyl acrylate, ethyl acrylate, n-butyl acrylate, n-hexyl acrylate, octyl acrylate and 2-ethylhexyl acrylate and mixtures of these monomers.
  • polar monomers having isocyanate, amino, amide, epoxy, hydroxyl or acid groups are also suitable as compounds A1.
  • Called e.g. Monomers with carboxylic acid, sulfonic acid or phosphonic acid groups (e.g., vinyl phosphonic acid). Preferred are carboxylic acid groups. Called e.g. Acrylic acid, methacrylic acid, itaconic acid, maleic acid or fumaric acid, acryloxypropionic acid.
  • hydroxyl-containing monomers in particular C1-C10 hydroxyalkyl (meth) acrylates, (meth) acrylamide and ureido-containing monomers such as ureido (meth) acrylates.
  • monomers A1 which may also be mentioned are mono (meth) acrylates of dihydric or polyhydric alcohols, e.g. Monoacrylic esters or monomethacrylic esters of ethylene glycol or propylene glycol.
  • reaction products of (meth) acrylic acid and monoepoxides e.g. Phenyl glycidyl ether or versatic acid glycidyl ether.
  • compounds having at least two ethylenically unsaturated, free-radically or ionically polymerizable groups are suitable. Preference is given to compounds having an average of 1, 5 to 6, in particular 2 to 4 polymerizable groups.
  • the above polymerizable group may be e.g. are N-vinyl, vinyl ether or vinyl ester groups, in particular are acrylic or methacrylic groups (short (meth) acrylic groups).
  • the weight-average molecular weight M w of the oligomers is preferably below 5000, more preferably below 3000 g / mol (determined by gel permeation chromatography with polystyrene as standard and tetrahydrofuran as eluent).
  • the oligomers are in particular (meth) acrylic compounds.
  • (meth) acrylates ie esters of acrylic acid or methacrylic acid.
  • (meth) acrylates may be mentioned (meth) acrylic acid esters and in particular acrylates of polyfunctional alcohols, in particular those which contain no further functional groups or at most ether groups in addition to the hydroxyl groups.
  • alcohols are, for example, bifunctional alcohols, such as ethylene glycol, propylene glycol, and their more highly condensed representatives, for example diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, etc., butanediol, pentanediol, hexanediol, neopentyl glycol, alkoxylated phenolic compounds such as ethoxylated or propoxylated bisphenols, cyclohexanedimethanol, trifunctional and higher-functional alcohols, such as glycerol, trimethylolpropane, butanetriol, trimethylolethane, pentaerythritol, ditrimethylolpropane, dipentaerythritol, sorbitol, mannitol and the corresponding alkoxylated, in particular ethoxy- and propoxylated alcohols ,
  • bifunctional alcohols such as ethylene glycol, prop
  • the alkoxylation products are obtainable in a known manner by reacting the above alcohols with alkylene oxides, in particular ethylene oxide or propylene oxide.
  • alkylene oxides in particular ethylene oxide or propylene oxide.
  • the degree of alkoxylation per hydroxyl group is 0 to 10, i. 1 mol of hydroxyl group may preferably be alkoxylated with up to 10 mol of alkylene oxides.
  • polyester (meth) acrylates which are the (meth) acrylic esters of polyesterols.
  • polyesterols are e.g. those into consideration, as can be prepared by esterification of polycarboxylic acids, preferably dicarboxylic acids, with polyols, preferably diols.
  • polycarboxylic acids preferably dicarboxylic acids
  • polyols preferably diols.
  • the starting materials for such hydroxyl-containing polyesters are known to the person skilled in the art.
  • dicarboxylic acids it is possible with preference to use succinic acid, glutaric acid, adipic acid, sebacic acid, o-phthalic acid, their isomers and
  • Hydrogenation products and esterifiable derivatives such as anhydrides or dialkyl esters of the acids mentioned are used. Also suitable are maleic acid, fumaric acid, tetrahydrophthalic acid or their anhydrides.
  • Suitable polyols are the abovementioned alcohols, preferably ethylene glycol, propylene glycol-1, 2 and -1, 3, butanediol-1, 4, hexanediol-1, 6, neopentyl glycol, cyclohexanedimethanol and polyglycols of the ethylene glycol and propylene glycol type.
  • Polyester (meth) acrylates can be used in several stages or even in one stage, e.g. in EP 279 303, are prepared from acrylic acid, polycarboxylic acid, polyol.
  • epoxy or urethane (meth) acrylates may be e.g. to act epoxy or urethane (meth) acrylates.
  • Epoxide (meth) acrylates are, for example, those obtainable by reaction of epoxidized olefins or poly- or mono- or diglycidyl ethers, such as bisphenol A diglycidyl ether, with (meth) acrylic acid.
  • the reaction is known to the person skilled in the art and described, for example, in R. Holman, UV and EB Curing Formulation for Printing Inks and Paints, London 1984.
  • Urethane (meth) acrylates are, in particular, reaction products of hydroxyalkyl (meth) acrylates with polyisocyanates or diisocyanates (also see R. Holmann, U.V. and E. B. Curing Formulation for Printing Inks and Paints, London 1984).
  • the above (meth) acrylate compounds may each also contain functional groups, e.g. Hydroxyl groups that are not esterified with (meth) acrylic acid.
  • oligomers are e.g. also low molecular weight unsaturated polyesters, which have in particular by a content of maleic acid or fumaric double bonds and are copolymerizable.
  • Preferred oligomers are liquid at 20 ° C., 1 bar.
  • the coating composition comprises (meth) acrylic compounds, in particular (meth) acrylic esters of polyhydric alcohols, in particular those which contain no further functional groups or at most ether groups in addition to the hydroxyl groups, in particular at 20 ° C., 1 bar of liquid (meth ) acrylic compounds having 2 to 4 (meth) acrylic groups.
  • Suitable polymers may include reactive groups, e.g. have polymerizable groups or functional groups, so that in the curing of a connection to the above monomers or oligomers. However, polymers without such groups are also considered, which then form an independent continuous phase or an interpenetrating network in the resulting coating.
  • Suitable polymers are e.g. Polyesters, polyadducts, in particular polyurethanes or polymers obtainable by free-radical polymerization. Particularly suitable are polymers obtainable by free-radical polymerization, preferably those which are at least 40% by weight to polymer, more preferably at least
  • the main monomers are selected from C1-C20 alkyl (meth) acrylates, vinyl esters of carboxylic acids containing up to 20 carbon atoms, vinyl aromatics having up to 20 carbon atoms, ethylenically unsaturated nitriles, vinyl halides, vinyl ethers having from 1 to 10 carbon atoms Alcohols, aliphatic hydrocarbons having 2 to 8 C Atoms and 1 or 2 double bonds or mixtures of these monomers. Examples of preferred monomers are listed above.
  • the printing ink preferably comprises further constituents of the binder, selected from compounds having a polymerizable, ethylenically unsaturated group (monomers), compounds other than the divinyl esters having at least two polymerizable, ethylenically unsaturated groups (oligomers) or polymers.
  • monomers compounds having a polymerizable, ethylenically unsaturated group
  • oligomers compounds having at least two polymerizable, ethylenically unsaturated groups
  • suitable printing inks also contain (meth) acrylic compounds, in particular (meth) acrylic esters of polyfunctional alcohols, in particular those which contain no further functional groups or at most ethers in addition to the hydroxyl groups ,
  • the content of such (meth) acrylic compounds is preferably from 5 to 90% by weight, in particular from 15 to 80% by weight, based on the printing ink.
  • the ink may contain other ingredients.
  • pigments also effect pigments, dyes, fillers, stabilizers, e.g. UV absorbers, antioxidants or biocides, leveling agents, defoamers, wetting agents, antistatic agents, etc.
  • the ink may contain water or organic solvents. Preferred inks contain little or no water or organic solvent (at 20 0 C, 1 bar liquid, non-reactive compound).
  • the printing ink contains less than 20 parts by weight of water or organic solvents, particularly preferably less than 10 parts by weight and in particular less than 5 parts by weight of water or organic solvents, based on 100 parts by weight of printing ink , Most preferably, the printing ink contains essentially no water or other organic solvents.
  • the ink is radiation-curable.
  • the curing can then be carried out with high-energy electromagnetic radiation, in particular with UV light or electron beams.
  • the printing ink contains at least one photoinitiator.
  • the photoinitiator may be, for example, so-called ⁇ -splitters, which are photoinitiators in which a chemical bond is cleaved to form 2 radicals which initiate the further crosslinking or polymerization reactions.
  • acylphosphine oxides (Lucirin® brands of BASF), hydroxyalkylphenones (eg Irgacure® 184), benzoin derivatives, benzil derivatives, dialkyloxyacetophenones.
  • H-abstractors which detach a hydrogen atom from the polymer chain, e.g. these are photoinitiators with a carbonyl group. This carbonyl group slides into a C-H bond to form a C-C-O-H moiety.
  • Photoinitiators may be used alone or in admixture, with particular preference also being given to mixtures of photoinitiators having different modes of action.
  • Photoinitiators may also be bonded to an above polymer or oligomer, if present.
  • thermally activatable initiators such as peroxides, azo compounds, etc. may be added.
  • the printing ink generally contains at least one dye or pigment as further constituent.
  • the printing inks of the invention are suitable for printing a wide variety of substrates, e.g. with surfaces made of plastic, metal, wood or for paper.
  • the printing ink can be applied to the substrates by known printing methods and then cured, wherein the curing is preferably carried out by high-energy electromagnetic radiation (radiation hardening).
  • the printing ink is suitable as a radiation-curable printing ink.
  • the application of the printing ink is particularly preferably carried out by the screen printing method or inkjet printing method (ink-jet).
  • the printing inks of the invention have good performance properties, for example a high reactivity and in particular a good adhesion, especially a good adhesion to polymer films.
  • the monomer mixture used as a reactive diluent is liquid and can therefore be handled well, shows good adhesion to substrates with plastic surfaces and improved reactivity of the coating composition.
  • NVF N-vinylformamide
  • VIMA N-vinyl-N-methylacetamide
  • NVC N-vinyl caprolactam
  • Figure 1 shows the melting points of the binary mixtures as a function of the NVC concentration.
  • the mixtures described were used as reactive diluents in high-energy-curable printing inks.
  • a pigment paste was prepared from acrylate-containing oligomers, dispersants and pigment, which was then diluted by adding the monomers.
  • the inks were applied to the substrate by means of a doctor blade and exposed on a UV exposure unit equipped with a mercury high-pressure UV emitter with an energy of 120 W / m. liability
  • NVP N-vinylpyrrolidone (as another comparative example)
  • the above laromers are radiation-curable (meth) acrylic compounds from BASF.

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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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une encre d'impression qui contient du N-vinylcaprolactame et au moins un monomère de N-vinylamide de formule (I), dans laquelle R1 représente un atome d'hydrogène ou un groupe alkyle en C1 à C4 et R2 représente un atome d'hydrogène ou un radical organique contenant au maximum 10 atomes de C.
PCT/EP2009/065185 2008-11-21 2009-11-16 Encre d'impression contenant du n-vinylcaprolactame et d'autres monomères de n-vinylamide WO2010057839A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP09749150A EP2358832A1 (fr) 2008-11-21 2009-11-16 Encre d'impression contenant du n-vinylcaprolactame et d'autres monomères de n-vinylamide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP08169592 2008-11-21
EP08169592.6 2008-11-21

Publications (1)

Publication Number Publication Date
WO2010057839A1 true WO2010057839A1 (fr) 2010-05-27

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PCT/EP2009/065185 WO2010057839A1 (fr) 2008-11-21 2009-11-16 Encre d'impression contenant du n-vinylcaprolactame et d'autres monomères de n-vinylamide

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EP (1) EP2358832A1 (fr)
WO (1) WO2010057839A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9447295B2 (en) 2013-08-12 2016-09-20 Basf Se Ink-jet printing ink comprising N-vinyloxazolidinone
EP3327095A4 (fr) * 2015-07-20 2018-08-01 LG Chem, Ltd. Composition d'encre pour support d'impression tridimensionnelle et procédé de fabrication d'impression tridimensionnelle l'utilisant
WO2020064523A1 (fr) 2018-09-24 2020-04-02 Basf Se Composition durcissable par uv destinée à être utilisée dans une impression 3d

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US5360882A (en) * 1994-02-04 1994-11-01 Isp Investments Inc. Eutectic compositions of divinyl imidazolidone and vinyl caprolactam
JPH10219135A (ja) * 1997-02-03 1998-08-18 Toyo Ink Mfg Co Ltd 無溶剤型硬化性樹脂組成物及びその硬化方法
WO2002050186A1 (fr) * 2000-12-21 2002-06-27 Coates Brothers Plc Encre pour la decoration dans le moule
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US20070017415A1 (en) * 2005-03-17 2007-01-25 Seiko Epson Corporation Ink composition
WO2007036692A1 (fr) * 2005-09-30 2007-04-05 Xennia Technology Limited Impression a jet d’encre
EP1990380A1 (fr) * 2006-02-28 2008-11-12 Seiko Epson Corporation Composition d'encre photodurcissable, procede d'impression jet d'encre et imprimante jet d'encre

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US5360882A (en) * 1994-02-04 1994-11-01 Isp Investments Inc. Eutectic compositions of divinyl imidazolidone and vinyl caprolactam
JPH10219135A (ja) * 1997-02-03 1998-08-18 Toyo Ink Mfg Co Ltd 無溶剤型硬化性樹脂組成物及びその硬化方法
WO2002050186A1 (fr) * 2000-12-21 2002-06-27 Coates Brothers Plc Encre pour la decoration dans le moule
JP2004217823A (ja) * 2003-01-16 2004-08-05 Shin Etsu Chem Co Ltd 液状放射線硬化型樹脂組成物、光ファイバ用被覆組成物及び光ファイバ
US20070017415A1 (en) * 2005-03-17 2007-01-25 Seiko Epson Corporation Ink composition
WO2007036692A1 (fr) * 2005-09-30 2007-04-05 Xennia Technology Limited Impression a jet d’encre
EP1990380A1 (fr) * 2006-02-28 2008-11-12 Seiko Epson Corporation Composition d'encre photodurcissable, procede d'impression jet d'encre et imprimante jet d'encre

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DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 24 August 1998 (1998-08-24), KURIHASHI, TORU; MATSUMOTO, MASAYOSHI; KUWAHARA, MASAMI: "Electron-beam-curable solventless coatings or inks with high flexibility and adhesion and their curing method", XP002569586, Database accession no. 1998:535931 *
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9447295B2 (en) 2013-08-12 2016-09-20 Basf Se Ink-jet printing ink comprising N-vinyloxazolidinone
EP3327095A4 (fr) * 2015-07-20 2018-08-01 LG Chem, Ltd. Composition d'encre pour support d'impression tridimensionnelle et procédé de fabrication d'impression tridimensionnelle l'utilisant
US10954404B2 (en) 2015-07-20 2021-03-23 Lg Chem, Ltd. Ink composition for 3D printing support and 3D printing manufacturing method using the same
WO2020064523A1 (fr) 2018-09-24 2020-04-02 Basf Se Composition durcissable par uv destinée à être utilisée dans une impression 3d
US11999865B2 (en) 2018-09-24 2024-06-04 Basf Se UV curable composition for use in 3D printing

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