WO2000066669A1 - Vernis a base de polyester pour encres polymerisables aux uv - Google Patents

Vernis a base de polyester pour encres polymerisables aux uv Download PDF

Info

Publication number
WO2000066669A1
WO2000066669A1 PCT/US2000/011475 US0011475W WO0066669A1 WO 2000066669 A1 WO2000066669 A1 WO 2000066669A1 US 0011475 W US0011475 W US 0011475W WO 0066669 A1 WO0066669 A1 WO 0066669A1
Authority
WO
WIPO (PCT)
Prior art keywords
component
resin
acid
rosin
polyester
Prior art date
Application number
PCT/US2000/011475
Other languages
English (en)
Inventor
Ignace M. Badou
Original Assignee
Flint Ink Corporation
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 Flint Ink Corporation filed Critical Flint Ink Corporation
Priority to AU46759/00A priority Critical patent/AU4675900A/en
Publication of WO2000066669A1 publication Critical patent/WO2000066669A1/fr

Links

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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C09D163/04—Epoxynovolacs

Definitions

  • the present invention relates to varnishes and compositions for inks, especially UV curable inks; to methods for printing with such varnishes and compositions; and to printed articles obtained by such methods.
  • Printing inks typically include one or more varnishes, or resins, and one or more colorants as principal components.
  • Printing ink varnishes must meet a number of performance requirements that include both requirements related to the printing process, such as suitable consistency and tack to print sharp, clean images, suitable length to avoid fly or mist, or proper drying characteristics, as well as requirements related to the desired print quality, such as gloss, chemical resistance, durability, or color.
  • the ink composition may include other components such as organic solvents, water, rheology modifiers, and so on that may affect body, tack, or drying characteristics.
  • UV curable ink compositions include a component having reactive unsaturation, one or more resins, and a colorant.
  • UV curable is used in this specification to refer to compositions having reactive unsaturation, it should be understood that the same compositions could be cured by other means, such as by exposure to electron beam or heat.
  • UV curable ink compositions are employed in a variety of printing processes, including letterpress printing, lithographic printing, flexographic printing, gravure and other intaglio processes, screen printing, and ink-jet digital printing.
  • ink misting commonly refers to ink droplets that become airborne during the printing process, for example at the point where the rotating inked rollers separate.
  • ink misting can result in the formation of ink filaments that may break to produce ink droplets.
  • UV curing inks typically are low viscosity compositions that include components prone to misting. While the mist can be annoying and cause contamination at low levels, higher amounts of misting can potentially create environmental and/or safety problems.
  • the relative amounts of ink misting for particular inks can be determined by comparing the inks on an inkometer, employing standard testing procedures.
  • the epoxide-functional hyperbranched polyesters are used as additives in conventional epoxy resins.
  • Hyperbranched alkyds are described as products of hyperbranched polyesters and tall oil fatty acids.
  • the resins are used in coatings. Ink applications and the problems of printing with high speed presses are not mentioned.
  • the reference does not address problems of ink compositions or high speed printing. Applicants have discovered that printing inks employing the novel vinyl resins of the invention have surprisingly high resistance to misting and slinging on high speed presses while avoiding a large increase in viscosity. Yet another problem that is encountered in lithographic printing is separation of the printing ink and the fountain solution in those situations when the print area is either a very small percentage or a very large percentage of the plate area. In particular, when the non- print area is small so that only a small amount of fountain solution is taken up, the water may be emulsified in the ink and not be released on printing. Scumming will result when there is not enough water to clean the face of the printing plate. The compositions of the present invention are surprisingly effective in printing large print areas without scumming.
  • the invention provides a polyester-based varnish ink compositions, particularly UV-curable compositions, containing the polyester-based varnish.
  • the polyester-based varnish contains a polyester resin of which a minor portion (less than half of the polyester resin by weight, preferably up to about 20% by weight of the resin) is highly branched.
  • the polyester-based varnish is prepared by reacting a low molecular weight polyester oligomer product, which is preferably nonlinear, with a novolac epoxy resin, preferably a novolac epoxy resin having a functionality of from about two to about twelve, and especially a novolac epoxy resin having a functionality of about six to about ten.
  • the polyester-based varnish has a relatively low viscosity in spite of the presence of a high molecular weight, branched portion.
  • the polyester-based varnish of the invention is prepared by reacting a polyester oligomer having residual acid functionality with a novolac epoxy resin.
  • the number average molecular weight of the polyester oligomer is preferably up to about 5000, more preferably from about 800 to about 5000, and even more preferably from about 1000 to about 3500.
  • the number average molecular weight of the polyester- based varnish, prepared from the polyester oligomer and the novolac epoxy resin is preferably up to about 10,000, and more preferably from about 1000 to about 10,000.
  • the number average molecular weight values as used herein designate a number average molecular weight determined by light scattering.
  • the polyester oligomer is the reaction product of a polycarboxylic acid component, a polyol component, and a rosin component.
  • the polyester oligomer is preferably nonlinear.
  • the polyester oligomer may be prepared in one step by reacting the polycarboxylic acid component, polyol component, and rosin component together all at once, or in two steps by first reacting the polyol component with the polycarboxylic acid component, and then reacting the product with the rosin component.
  • the polyester product has at least some residual acid functionality.
  • the two-step reaction scheme is desirable when the polyol component or the polycarboxylic acid component includes a material that boils or sublimes at a low temperature.
  • Other methods are also known of avoiding loss of low-boiling or subliming materials during polyester reactions.
  • the polycarboxylic acid component is reacted with the polyol component.
  • the reaction is carried out to an acid number at which a portion of the hydroxyl groups remain unreacted.
  • the polyol component is employed in an amount of from about 1 equivalent to about 2 equivalents hydroxyl, more preferably from about 1.1 equivalents to about 1.7 equivalents hydroxyl, even more preferably from about 1.2 equivalents to about 1.4 equivalents hydroxyl, and yet more preferably from about 1.3 equivalents to about 1.4 equivalents hydroxyl, for each equivalent of acid in the polycarboxylic acid component.
  • the acid equivalents are in excess, but the reaction between the polycarboxylic acid component and the polyol component is not carried out to completion, so that a sufficient number of hydroxyl groups remain for the desired extent of reaction with the rosin component.
  • the polyol component used to prepare the polyester oligomer has an average functionality of more than about 2.
  • the polyol component has an average functionality of up to about 3, and more preferably about 3.
  • the desired average functionality of the polyol component may be achieved by using predominantly or only one or more triols when a functionality of about three is desired, but the desired average functionality may also be achieved by using a combination of polyols or a combination of polyols and mono-functional alcohols.
  • suitable alcohols with a functionality of three or more include, without limitation, trimethylolpropane, trimethylolethane, glycerin, trihydroxyhexane, glucose, sorbitol, quinic acid, pentaerythritol, dipentaerythritol, and combinations of these.
  • the polyol component can include polyols having only one hydroxyl group or having two hydroxyl groups when the amount of higher functionality alcohols is adjusted so that the average functionality is more than about 2.
  • diols and mono-functional alcohols include, without limitation, butanol, hexanol, dodecyl alcohol, lauryl alcohol, alkylene glycols and polyalkylene glycols such as ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and neopentyl glycol, 1 ,4-butanediol, 1 ,6-hexanediol, 1 ,4-cyclohexane dimethanol, 2,2,4-trimethyl-1 ,3-pentanediol, and combinations thereof.
  • the carboxylic acid component includes carboxylic acid- functional compounds and/or anhydrides of carboxylic acid compounds.
  • the polycarboxylic acid component includes at least one carboxylic acid compound or anhydride compound that has a functionality 2 or higher.
  • the carboxylic acid component when the polyol component has an average functionality of more than about 2, also includes at least one monofunctional acid or anhydride of a monofunctional acid.
  • the average functionality of the carboxylic acid component is preferably from about 1.1 to about 2.1 equivalents per mole, more preferably from about 1.1 to about 1.5 equivalent per mole, and even more preferably from about 1.2 to about 1.4 equivalent per mole.
  • the polycarboxylic acid component could have an average functionality of more than about 2, and preferably up to about 3, and even more preferably about 3.
  • the polyol component would have an average functionality of less than about 2, preferably from about 1.1 to about 2.1 equivalents per mole, more preferably from about 1.1 to about 1.5 equivalent per mole, and even more preferably from about 1.2 to about 1.4 equivalent
  • suitable polyfunctional carboxylic acids or anhydrides of polyfunctional carboxylic acids include, without limitation, phthalic acid, isophthalic acid, trimellitic acid, succinic acid, glutaric acid, methylsuccinic acid, hexahydro-4-methylphthalic acid, cis- 1 ,2-cyclohexane dicarboxylic acid, diglycolic anhydride, 3-ethyl-3- methylgluconic acid, 1 ,2,4-benzene tricarboxylic acid, 1 ,4-cyclohexane dicarboxylic acid, adipic acid, succinic acid, suberic acid, pimelic acid, azelaic acid, sebacic acid, maleic acid, dodecanedioic acid, terephthalic acid, hexahydrophthalic acid, tetrahydrophthalic acid, methylhexahydrophthalic acid, endomethylenetetrahydrophthalic acid, methyl
  • Suitable monofunctional carboxylic acids or anhydrides of monofunctional carboxylic acids include, without limitation, benzoic acid, para-(tertiary butyl) benzoic acid, 2- ethylhexanoic acid, acrylic acid, methacrylic acid, crotonic acid, acetic acid, propionic acid, butyric acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, lauric acid, isostearic acid, stearic acid, hydroxystearic acid, linoleic acid, linolenic acid, oleic acid, octadecanoic acid, tetradecanoic acid, dimer fatty acid, trimer fatty acid, icosane, isomers thereof, and combinations of these.
  • Suitable catalysts may be used, if desired, such as protonic acids, Lewis acids, titanium alkoxides, metal oxides such as dialkyl tin(IV) oxides, dialkyl tin esters such as dialkyl tin acetates, and combinations of these.
  • suitable catalysts include, without limitation, magnesium oxide, antimony trioxide, dibutyl tin oxide, triflic acid, and so on.
  • a catalyst may typically be included in an amount of from about 0.05 percent to about 0.5 percent, the percentage based on the total weight of the reactants used in preparing the polyester precursor of the polyester oligomer.
  • the esterification reaction is carried out until the polycarboxylic acid component has reacted to the desired extent, preferably until the acid number of the reaction mixture decreases to below about 30 mg KOH/g based on total solid weight of the reactants. Typically, when the hydroxyl functionality is in excess, the reaction may be carried out to an acid number of from about 5 to about 25 mg KOH/g based on total solid weight of the reactants.
  • the hydroxyl-functional polyester precursor product is reacted with a rosin component.
  • Suitable materials for the rosin component include tall oil rosin, gum rosin, wood rosin, dimerized tall oil rosin, dimerized gum rosin, dimerized wood rosin, dimerized rosins formed from any combination of tall oil, gum, and wood rosins, and combinations of these. Also suitable for the rosin component are acid-modified or acid anhydride-modified rosins, monomeric and dimerized. The rosin component preferably contains at least about two acid groups per molecule. Modification of rosins with carboxylic acids or acid anhydrides having double bonds capable of undergoing Diels Alder addition is a well-known process.
  • the rosin component is reacted with the polyester precursor product of the first step in amounts of from about 10 to about 30 percent, based on the weight of the varnish. Preferably, about 20% of rosin component is included in the varnish.
  • the rosin component can be from about 15% to about 55%, preferably from about 25% to about 40%, of the total weight of the polyester oligomer reaction product of the polyester precursor product and rosin components.
  • the rosin component include dimerized rosin in amounts of from about 0.5 equivalent to about 2 equivalents per theoretical remaining hydroxyl equivalents of the polyester precursor product.
  • the reaction of the polyester precursor product with the rosin component is continued until a final acid number indicates completion, preferably an acid number of from about 10 to about 50, and more preferably from about 10 to about 25, mg KOH/g.
  • a final acid number indicates completion, preferably an acid number of from about 10 to about 50, and more preferably from about 10 to about 25, mg KOH/g.
  • the polycarboxylic acid component and the polyol component are included in the same amounts relative to each other as in the first step of the two-step process.
  • the rosin component is included in an amount of from about 10 to about 30 percent, based on the weight of the varnish, or from about 15% to about 55%, preferably from about 25% to about 40%, of the total weight of the reaction components.
  • the polyester oligomer is then further reacted with a novolac epoxy resin component to produce the polyester-based resin of the invention.
  • the novolac epoxy resin preferably has a functionality of from about 2 to about 12, more preferably from about 4 to about 8, and still more preferably from about 6 to about 8. In a particularly preferred embodiment, the novolac epoxy resin has a functionality of about 8.
  • the novolac epoxy resin may be epoxy phenol novolac resins or epoxy cresol novolac resins having the structure I:
  • each R 1 is independently H or methyl
  • each R 2 is independently H or a glycidyl group of structure II:
  • each L is independently a methylene group ( — CH 2 — ) or an isopropylene group ( — C(CH 3 ) 2 — ), and n is up to about 12, preferably from about 2 to about 6, and more preferably from about 4 to about 6.
  • the novolac epoxy resin has a structure (III):
  • the novolac resin may also be an aromatic novolac bisphenol A resin, having either the structure IV:
  • R 2 may be H or a glycidyl group, with the proviso that on average at least two R 2 groups per molecule are glycidyl groups, preferably from about two to about sixteen R 2 groups per molecule are glycidyl groups, and more preferably from about four to about eight R 2 groups per molecule are glycidyl groups, and still more preferably from about six to about eight R 2 groups per molecule are glycidyl groups; and m is up to about 4, preferably from 0 to about 2.
  • the novolac epoxy resin is preferably reacted with the polyester oligomer in an amount of 1 equivalent of epoxide to about 1.2 to about 3 equivalents of acid, preferably about 1 equivalent of epoxide to about 2 equivalents of acid.
  • the novolac epoxy resin is preferably from about 1 % to about 15%, more preferably from about 5% to about 10%, of the total weight of the novolac epoxy resin and polyester oligomer reactants.
  • the final acid number is preferably in the range of from 0 to about 40, preferably from about 10 to about 30, mg KOH/gram nonvolatile material.
  • the varnish may comprise from about 1 to about 10% by weight of the reacted novolac epoxy resin.
  • the polyester-based resin of the invention is nonlinear, by which 5 is meant that at least some molecules of the polyester-based resin is branched, although preferably some molecules are still linear.
  • the polyester-based resin of the invention preferably has a bimodal molecular weight distribution, with preferably at least about 10%, and up to about 40% by weight of the resin being highly branched and o having a number average molecular weight of from about 10,000 to about one million, with the balance of the resin having linear and/or weakly branched polymer molecules with a number average molecular weight of from about 600 to about 5000.
  • the ink prepared from the varnish will mist. While the lower number average molecular weight portion of the resin of the present invention would be expected to mist if used independently, surprisingly the resin of the invention that includes both the low number average molecular weight fraction and the more highly branched higher o number average molecular weight fraction does not mist on high speed presses.
  • the polyester-based resin of the invention can be combined with one or more UV-polymerizable monomers to make a varnish for UV curable inks.
  • the varnish may include from about 15% to about 80% 5 of the monomer(s) and from about 20% to about 85% of the polyester- based resin, especially those selected from polyfunctional acrylate monomers and polyfunctional methacrylate monomers.
  • polyfunctional in this context it is meant that the monomer has more than one site that undergoes reaction when the ink is cured.
  • suitable monomers include, without limitation, acrylates and methacrylates of polyols such as 1 ,6-hexanediol diacrylate, 1 ,6- hexanediol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, trimethylol propane triacrylate, trimethylol propane trimethacrylate, tetramethylol methane tetraacrylate, tetramethylol methane tetramethacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate; alkylene glycol
  • Suitable polymerizable diluents include low viscosity acrylate-functional polyester diluents having molecular weights of up to about 2000, such as alkoxylated diluents.
  • the varnish may then be used to prepare an ink composition by adding one or more additional materials. Additional monomer may also be added, for example to adjust the viscosity of the ink.
  • the ink composition of the invention includes at least about 15% by weight of UV-polymerizable monomers, based on the total weight of the ink composition. It is also preferred for the composition of the invention to include less than about 80% by weight of polymerizable polyfunctional monomers.
  • the varnish and ink compositions comprise from about 15%, by weight to about 40% by weight alkoxylated polyol polyacrylates such as propoxylated glycerin triacrylate. Propoxylated monoacrylates are not preferred although higher alkoxylated versions can be useful.
  • the amount and type of reactive monomer included will depend on the particular application, and can readily be optimized by straightforward experimentation. For instance, a larger monomeric component is included in flexographic inks than in lithographic inks.
  • Pigment is dispersed in the varnish by any suitable method, such as by mixing the pigment and the varnish in a three-roll mill or grinding in a mill charged with suitable media such as steel shot or ball or magnesium silicate beads.
  • the ink compositions of the invention containing the polyester- based varnish provide excellent pigment wetting, excellent flow characteristics, and the very low alcohol and water acceptance that are necessary for successful two-fluid lithographic printing.
  • Inks and coatings prepared using the compositions of the invention have high gloss and very good alcohol resistance, e.g., ethanol and isopropanol resistance.
  • the lithographic inks of the invention have unexpectedly improved water release characteristics, resulting in clean printing even when the print area is very small.
  • the ink is printed on a substrate, particularly a paper, and optionally cured or set by UV radiation, electron beam radiation, or heat to produce a printed substrate.
  • a mixture of 581 parts by weight isophthalic acid, 1342 parts by weight benzoic acid, and 1080 parts by weight of trimethylolpropane was charged to a suitable reactor and heated to 200°C with stirring. About 0.2% by weight dibutyl tin acetate, based on the total weight of the charge, was added when the temperature was at about 150°C. The temperature was gradually increased to 232°C over the course of about 2.25 hr. with removal of the by-product water. After an additional half-hour, the mixture was clear and had an acid value of less than 25 mg KOH/g.
  • dimerized rosin equivalent weight 340, DYMEREX® from Hercules, Inc.
  • magnesium oxide 0.3 parts by weight magnesium oxide
  • the temperature was increased to 252°C. After an additional 1.5 hr., the measured acid number was about 35 mg KOH/g. A total of 70 parts by weight water had been removed.
  • the contents of the reactor were then allowed to cool. After about 30 minutes, the temperature had dropped to 240°C.
  • a total of 430 parts by weight of EPON® SU-8 (a novolac epoxy resin having a functionality of 8, available from Shell Chemical Co., Houston, TX) was added to the reactor. The addition caused the temperature to drop to about 225°C.
  • OTA 480 a propoxylated glycerin triacrylate available from UCB
  • the contents of the reactor were stirred for about 15 minutes and then discharged and filtered.
  • the product included 60 parts by weight of the polyester oligomer- based varnish and 40 parts by weight of the triacrylate monomer.
  • Example 2 UV-Curable Ink Including Polyester-Based Varnish
  • the polyester-based varnish of Example 1 is used to make a UV-curable ink.
  • the varnish of Example 1 58 parts by weight, is combined with 9 parts by weight of a polyfunctional, UV-curing monomer, 0.5 part by weight of an inhibitor, 1 part by weight of an anti- misting additive, 19.5 parts by weight of carbon black pigment #7, 1 part by weight of a fumed silica, and 9 parts by weight of a mixture of photoinitiators in ketone solvent.
  • the tack is adjusted with 2-6% by weight of the polyfunctional monomer.
  • Comparative Example A UV-Curable Ink Without the Inventive Varnish
  • Example 2 An ink is prepared according to Example 2, but the polyester- based varnish of Example 1 is replaced with EBECRYL® 438 and the anti-mist additive is increased to 3 parts by weight. Testing of the Inks
  • Example 2 and Comparative Example A were printed lithographically and cured by UV radiation.
  • the ink sample of Example 2 exhibited less misting and better pigment wetting characteristics relative to the Comparative Example A.
  • the alcohol resistance was better for Example 2 (17 single rubs) than Comparative Example A (7 single rubs).
  • the cure and water pick up properties of Example 2 and Comparative Example A were similar.

Landscapes

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

Abstract

L'invention concerne un vernis à base de polyester non linéaire et des compositions d'encres polymérisables aux UV contenant le vernis à base de polyester. Ce dernier est préparé en faisant réagir un oligomère de polyester, qui est, de préférence, non linéaire, avec une résine époxyde novolaque. Cette résine a, de préférence, une fonctionnalité allant d'environ 2 à environ 12. L'oligomère polyester est préparé à partir d'un composé d'acide polycarboxylique, un composé de polyol, et un composé de colophane.
PCT/US2000/011475 1999-05-04 2000-04-28 Vernis a base de polyester pour encres polymerisables aux uv WO2000066669A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU46759/00A AU4675900A (en) 1999-05-04 2000-04-28 Polyester based varnish for uv curable inks

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30480699A 1999-05-04 1999-05-04
US09/304,806 1999-05-04

Publications (1)

Publication Number Publication Date
WO2000066669A1 true WO2000066669A1 (fr) 2000-11-09

Family

ID=23178109

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/011475 WO2000066669A1 (fr) 1999-05-04 2000-04-28 Vernis a base de polyester pour encres polymerisables aux uv

Country Status (2)

Country Link
AU (1) AU4675900A (fr)
WO (1) WO2000066669A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1375569A1 (fr) * 2002-06-20 2004-01-02 Dainippon Ink And Chemicals, Inc. Compositions durcissables par irradiation comprenant des polyesters hyperbranchés à groupes acrylates terminaux
WO2013128132A1 (fr) * 2012-03-01 2013-09-06 Novance Resine alkyde en emulsion aqueuse, en particulier d'origine vegetale
CN103725173A (zh) * 2013-12-18 2014-04-16 江苏富邦纺织有限公司 一种醇酸树脂涂料配方
CN103725175A (zh) * 2014-01-27 2014-04-16 厦门双瑞船舶涂料有限公司 一种厚膜化改性醇酸涂料及其制备方法
CN105860788A (zh) * 2016-05-09 2016-08-17 上海漆盟化工有限公司 一种环保快干水性醇酸漆及其制备方法
US10139746B2 (en) 2014-03-25 2018-11-27 Hp Indigo B.V. Liquid electrophotographic varnish composition
EP3453745A1 (fr) * 2017-09-12 2019-03-13 Gleitsmann Security Inks GmbH Encre en creux de durcissement par énergie
RU2796367C2 (ru) * 2017-09-12 2023-05-22 Гляйтсманн Секьюрити Инкс Гмбх Радиационно-отверждаемая краска для глубокой печати

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2077279A (en) * 1980-06-02 1981-12-16 Sun Chemical Corp High-solids polyesters process for their preparation and use thereof
EP0112465A1 (fr) * 1982-11-25 1984-07-04 BASF Lacke + Farben AG Encre d'impression
JPS62295068A (ja) * 1986-06-16 1987-12-22 Fujikura Kasei Kk 静電荷像現像トナ−用樹脂
JPH0251516A (ja) * 1988-08-16 1990-02-21 Toyo Ink Mfg Co Ltd 活性エネルギー線硬化性樹脂，その樹脂を含む硬化性被覆組成物および印刷インキ用組成物
JPH03267946A (ja) * 1990-03-19 1991-11-28 Arakawa Chem Ind Co Ltd 電子写真用トナー組成物
US5112715A (en) * 1990-08-06 1992-05-12 Eastman Kodak Company Toner compositions containing a multi-purpose additive
US5212213A (en) * 1990-10-26 1993-05-18 Westvaco Corporation Radiation-curable rosin-based resins

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2077279A (en) * 1980-06-02 1981-12-16 Sun Chemical Corp High-solids polyesters process for their preparation and use thereof
EP0112465A1 (fr) * 1982-11-25 1984-07-04 BASF Lacke + Farben AG Encre d'impression
JPS62295068A (ja) * 1986-06-16 1987-12-22 Fujikura Kasei Kk 静電荷像現像トナ−用樹脂
JPH0251516A (ja) * 1988-08-16 1990-02-21 Toyo Ink Mfg Co Ltd 活性エネルギー線硬化性樹脂，その樹脂を含む硬化性被覆組成物および印刷インキ用組成物
JPH03267946A (ja) * 1990-03-19 1991-11-28 Arakawa Chem Ind Co Ltd 電子写真用トナー組成物
US5112715A (en) * 1990-08-06 1992-05-12 Eastman Kodak Company Toner compositions containing a multi-purpose additive
US5212213A (en) * 1990-10-26 1993-05-18 Westvaco Corporation Radiation-curable rosin-based resins

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 109, no. 6, 8 August 1988, Columbus, Ohio, US; abstract no. 46138, XP002145718 *
CHEMICAL ABSTRACTS, vol. 114, no. 14, 8 April 1991, Columbus, Ohio, US; abstract no. 123813, XP002145719 *
DATABASE WPI Section Ch Week 199203, Derwent World Patents Index; Class A89, AN 1992-019676, XP002145720 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1375569A1 (fr) * 2002-06-20 2004-01-02 Dainippon Ink And Chemicals, Inc. Compositions durcissables par irradiation comprenant des polyesters hyperbranchés à groupes acrylates terminaux
WO2013128132A1 (fr) * 2012-03-01 2013-09-06 Novance Resine alkyde en emulsion aqueuse, en particulier d'origine vegetale
FR2987623A1 (fr) * 2012-03-01 2013-09-06 Novance Resine alkyde en emulsion aqueuse, en particulier d'origine vegetale
CN103725173A (zh) * 2013-12-18 2014-04-16 江苏富邦纺织有限公司 一种醇酸树脂涂料配方
CN103725175A (zh) * 2014-01-27 2014-04-16 厦门双瑞船舶涂料有限公司 一种厚膜化改性醇酸涂料及其制备方法
US10139746B2 (en) 2014-03-25 2018-11-27 Hp Indigo B.V. Liquid electrophotographic varnish composition
CN105860788A (zh) * 2016-05-09 2016-08-17 上海漆盟化工有限公司 一种环保快干水性醇酸漆及其制备方法
EP3453745A1 (fr) * 2017-09-12 2019-03-13 Gleitsmann Security Inks GmbH Encre en creux de durcissement par énergie
WO2019052951A1 (fr) * 2017-09-12 2019-03-21 Gleitsmann Security Inks Gmbh Encre pour impression en creux à durcissement par énergie
RU2796367C2 (ru) * 2017-09-12 2023-05-22 Гляйтсманн Секьюрити Инкс Гмбх Радиационно-отверждаемая краска для глубокой печати

Also Published As

Publication number Publication date
AU4675900A (en) 2000-11-17

Similar Documents

Publication Publication Date Title
EP2694603B1 (fr) Composition durcissable sous l'action d'un rayonnement
CN111247192B (zh) 经由酸酐中间体制得的多胺聚酯分散剂
EP2297256B1 (fr) Encre pour l'impression intaglio comprenant des dendrimères
JP4511822B2 (ja) 活性エネルギー線硬化性乾式平版印刷インキ組成物、印刷方法およびその印刷物
CN112384576B (zh) 活性能量射线固化型胶版印刷用油墨组合物、以及使用了该油墨组合物的印刷物的制造方法
EP3484940B1 (fr) Composés (méth)acrylés à base de pet recyclé
JP2014517086A (ja) 照射硬化性組成物
EP3822324B1 (fr) Composition d'encre durcissable par rayonnement d'énergie active, destinée à l'impression offset et procédé de production d'un matériau imprimé l'utilisant
WO2000066669A1 (fr) Vernis a base de polyester pour encres polymerisables aux uv
EP1252244A1 (fr) Epoxy acrylates modifies par des resines
JP2000502741A (ja) 溶剤不含の、低放出性で硬化可能な塗料
US11932767B2 (en) Active energy ray curable ink composition and method for manufacturing printed matter using same
CN114929778A (zh) 聚酯树脂、平版印刷用油墨组合物、印刷物、及印刷物的制造方法
TW201609998A (zh) 包含惰性樹脂之放射線硬化性組成物
EP1268687A1 (fr) Encres d'impression en relief
JPH06263812A (ja) 共重合性光開始剤組成物および光硬化性被覆組成物
JP3413912B2 (ja) 紫外線硬化型インキ用樹脂組成物
EP1333073A1 (fr) Application de vernis en ligne, article imprimé comprenant couche d'encre offset et couche de laque
EP3373926B1 (fr) Agents de dispersion alcoxylés
JPS63367A (ja) 熱硬化性被覆用樹脂組成物
JPH11246635A (ja) 活性エネルギー線硬化性樹脂組成物
JP2021519358A (ja) 放射線硬化性組成物
JP2006016509A (ja) アクリルオリゴマーまたはそれを含む活性エネルギー線硬化性組成物およびその印刷物。
JP2000313850A (ja) ゲルワニスおよび活性エネルギー線硬化性被覆組成物
JPH0333168A (ja) 活性エネルギー線硬化性樹脂組成物および印刷インキ組成物

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK DZ EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP