WO2004055123A1 - Energy curable, water washable printing inks suitable for waterless lithographic printing - Google Patents
Energy curable, water washable printing inks suitable for waterless lithographic printing Download PDFInfo
- Publication number
- WO2004055123A1 WO2004055123A1 PCT/US2003/039092 US0339092W WO2004055123A1 WO 2004055123 A1 WO2004055123 A1 WO 2004055123A1 US 0339092 W US0339092 W US 0339092W WO 2004055123 A1 WO2004055123 A1 WO 2004055123A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- water
- pigment
- ethylenically unsaturated
- water insoluble
- resin
- Prior art date
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
- 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
- This invention relates to energy curable printing ink's suitable for waterless lithographic printing that can form a water resistant or a water insoluble printed image, yet are water washable before curing when being removed from ink trains such as rollers and offset blankets of the printing press .
- energy curable inks are extremely stable on rollers since no loss of solvent or water takes place.
- Energy curable inks are also very low in VOC s . They have excellent film properties and are widely used to produce high quality prints .
- a combination of no fountain solution (waterless lithography) , low VOC energy curable inks and water washability on printers before curing (low VOC washes) could combine to give high performance, very low VOC inks that are desirous under current conditions in the market.
- the present invention provides an energy curable, varnish composition
- an energy curable, varnish composition comprising: (a) water soluble ethylenically unsaturated reactive oligomers and monomers; (b) water insoluble ethylenically unsaturated reactive oligomers and monomers; and (c) a resin selected from the group consisting of a water soluble non-reactive resin, a water insoluble acid or base functional resin and water insoluble ethylenically unsaturated reactive resin, wherein said water insoluble resins contain acid functional groups.
- the present invention also provides an energy curable, water washable, printing ink composition suitable for waterless lithographic printing comprising: (a) water soluble ethylenically unsaturated reactive oligomers and monomers; (b) water insoluble ethylenically unsaturated reactive oligomers and monomers; (c) a resin selected from the group consisting of a water soluble non-reactive resin, a water insoluble acid or base functional resin and water insoluble ethylenically unsaturated reactive resin, wherein said water insoluble resins contain acid functional groups; and (d) a. pigment.
- the present invention further provides a method of preparing an energy curable, water washable, printing ink composition suitable for waterless lithographic printing comprising mixing: (a) water soluble ethylenically unsaturated reactive oligomers and monomers; (b) water insoluble ethylenically unsaturated reactive oligomers and monomers; (c) a resin selected from the group consisting of a water soluble non-reactive resin, a water insoluble acid or base functional resin and water insoluble ethylenically unsaturated reactive resin, wherein said water insoluble resins contain acid functional groups; and(d)a pigment.
- the present invention also provides a method of waterless lithographic printing comprising using an energy curable, water washable, printing ink composition which comprises: (a) water soluble ethylenically unsaturated reactive oligomers and monomers; (b) water insoluble ethylenically unsaturated reactive oligomers and monomers; (c) a resin selected from the group consisting of a water soluble non-reactive resin, a water insoluble acid or base functional resin and water insoluble ethylenically unsaturated reactive resin, wherein said water insoluble resins contain acid functional groups; and (d) a pigment .
- an energy curable, water washable, printing ink composition which comprises: (a) water soluble ethylenically unsaturated reactive oligomers and monomers; (b) water insoluble ethylenically unsaturated reactive oligomers and monomers; (c) a resin selected from the group consisting of a water soluble non-reactive resin, a water insoluble
- an energy curable, water washable, printing ink composition suitable for waterless lithographic printing that is stable on conventional ink trains and exhibits good optical printing density and water resistance to the final film without increasing the tack of the formulation can be prepared in a formulation that comprises: (a) water soluble ethylenically unsaturated reactive oligomers and monomers; (b) water insoluble ethylenically unsaturated reactive oligomers and monomers; (c) a resin selected from the group consisting of a water soluble non-reactive resin, a water insoluble acid or base functional resin and water insoluble ethylenically unsaturated reactive resin, wherein said water insoluble resins contain acid functional groups; and(d) a pigment.
- the printing ink composition is an energy curable, lithographic printing ink composition and is water-washable before curing and water resistance after curing.
- the amount of water soluble ethylenically unsaturated reactive oligomers and monomers present is between 30 and 85 parts
- the amount of water insoluble ethylenically unsaturated reactive oligomers and monomers is between 10 and 45 parts
- the amount of the acid functional groups in the water insoluble resins is about 5 to 25 parts.
- the water soluble oligomer is selected from the group consisting of an acrylate oligomer, a methacrylate oligomer, epoxy acrylate, an epoxy methacrylate, a polyether acrylate, a polyether methacrylate, a polyester acrylate, a polyester methacrylate, a polyurethane acrylate, a polyurethane methacrylate, a mela ine acrylate, or a melamine methacrylate.
- the acrylate is an aromatic or aliphatic acrylate or methacrylate and preferably the compound is a diacrylate ester of an alkanolglycidyl ether such as 1, 4- butanedioldiglycidyl ether, an ethoxylated aromatic epoxide and ethoxylated trimethylolpropane triacrylate, ethoxylated trimethylolpropane trimethacrylate, ethoxylated aliphatic or aromatic epoxy acrylate, ethoxylated aliphatic or aromatic epoxy methacrylate, polyoxyethylene glycol diacrylate; polyoxyethyleneglycol di- methacrylate.
- an alkanolglycidyl ether such as 1, 4- butanedioldiglycidyl ether
- an ethoxylated aromatic epoxide and ethoxylated trimethylolpropane triacrylate ethoxylated trimethylolpropane trimethacrylate
- the ethoxylated aromatic epoxide contains 6 to 20 ethoxy groups.
- the compounds may contain two or more terminal, or pendent, -ethylenically unsaturated groups which are linked through a polymeric backbone, or through similar linking groups to a central aliphatic or aromatic backbone.
- the water soluble oligomer can contain two or more acrylate oligomer groups or methacrylate oligomer groups .
- acrylate oligomer examples include but are not limited to epoxy acrylate, epoxy methacrylate, polyether acrylate, polyether methacrylate, polyester acrylate, polyester methacrylate, polyurethane acrylate, polyurethane methacrylate, melamine acrylate, melamine methacrylate, polyethylene glycol diacrylate and polyethylene glycol dimethacrylate oligomers .
- Suitable water soluble oligomers also include aliphatic and aromatic epoxy acrylates and epoxy methacrylates, aliphatic compounds preferably being employed. These include, for example, the reaction products of acrylic acid or methacrylic acid with aliphatic glycidyl ethers.
- water soluble oligomers are polyether acrylates and methacrylates, polyester acrylates and methacrylates and polyurethane acrylates and methacrylates.
- Polyetherols employed in this context are preferably alkoxylated, especially ethoxylated and/or propoxylated, mono-, di-, tri- or polyfunctional alcohols.
- Suitable water soluble oligomers are melamine acrylates and methacrylates. These are obtained, for example, by esterifying the free methylol groups of the resins with acrylic acid or methacrylic acid, or by transetherification of etherified melamine compounds with hydroxyalkyl methacrylates, for example hydroxyethyl, hydroxypropyl and hydroxybutyl methacrylate, hydroxybutyl acrylate.
- water soluble oligomers are, in general, thickeners which contain unsaturated groups.
- These include on the one hand polyurethane thickeners, which contain ., .-ethylenically unsaturated double bonds as a result of the incorporation of the above mentioned hydroxyalkyl methacrylates, hydroxyalkyl acrylates.
- polyacrylate thickeners which are obtained by polymer-analogous reaction of, for example, hydroxyl-containing polymers, or polymers containing acid groups, with epoxide- containing methacrylates, acrylates for example glycidyl methacrylate, glycidyl acrylate, or of hydroxyl-containing polymers of esterification with methacrylic acid, acrylic acid or reaction with methacrylic anhydride, acrylic anhydride or by reaction with NCO-terminated methacrylates, methacrylates for example methacryloyl isocyanate, isocyanatoethyl methacrylate, isocyanatoethyl acrylate etc.
- They additionally include polyvinyl alcohols, which are modified, for example, by reaction with methacrylic anhydride, acrylic anhydride or by esterification with methacrylic acid, acrylic acid with groups containing double bonds.
- copolymers comprising maleic anhydride as co-monomer, the polymer being modified by ring opening of the anhydride' with the above mentioned hydroxyalkyl methacrylates, hydroxyalkyl acrylates or with hydroxy vinyl ethers, for example butanediol monovinyl ether, cyclohexanedi ethanol monovinyl ether etc., with double bonds.
- Particularly preferred water soluble oligomers include diacrylate esters of an alkanolglycidyl ethers; wherein the alkanol has 2 or 3 hydroxy groups, such as a diacrylate of 1, 4-butanedioldiglycidyl ether; a triacrylate of trimethylolpropane-diglycidyl ether, or a mixture thereof; and ethoxylated acrylic oligomers, such as an ethoxylated trimethylolpropanetriacrylate; an ethoxylated trimethylolpropane diacrylate; or a mixture thereof; wherein the ethoxylated oligomer contains 9-12 ethoxy groups.
- a particularly preferred water soluble oligomer is the diacrylate ester of 1, -butanedioldiglycidyl ether, which is available from BASF Corporation, Charlotte NC, as aromer R 8765 aliphatic epoxy acrylate.
- the water soluble, ethylenically unsaturated resin can contain carboxylic acid groups, acrylic groups including but not limited to methacrylic groups, polyamide resins, acrylic resins, acrylated acrylic resin, amino resins, polyester resins, urethane resins, starch, polysulfonate resins, phenolic resins and melamine resins.
- the polymer of the water soluble, ethylenically unsaturated resin may optionally - containing free radical polymerizable functionalities, for example, the class of compounds meeting these requirements would include . copolymers of the general structure:
- Ri and R 2 are independently selected from the group consisting of hydrogen, C ⁇ -C 2 o alkyl, C 6 -C ⁇ 0 aryl, C 7 -C 14 alkaryl, C 4 -C 12 cycloalkyl and halogen such as chlorine, fluorine and bromine; and preferably are independently selected from hydrogen, methyl, phenyl, benzyl, or C-C 6 cycloalkyl;
- R 3 , R 4 and R 5 are' independently selected from the group consisting of hydrogen and C 1 -C5 alkyl; and preferably and independently selected from hydrogen and/or methyl;
- R ⁇ is selected from the group consisting of alkyl, aralkyl, alkyl substituted aralkyl and oxyalkylated derivatives of same containing 2 to 4 carbon atoms in each oxyalkylene group, which group may be 1 to 20 and preferably 1 to 6 repeating units;
- A is a linear or branched divalent C ⁇ -C 2 o
- the water soluble, ethylenically unsaturated resin can further contain polyacrylamides, polyamides, polyvinyl alcohol, polyglycols, polyethylene or polypropylene oxide, poly (N-vinyl -4 methyl-2-oxazalidone, polyvinylpyrrolidone, co-polymers of polyvinylpyrrolidone and vinyl acetate, of polyvinyl acetate, guar or xanthan gum, polysaccharides, polyethyleneamine, sodium salt of polyurethane or polyester, polystyrene sodium sulfonate salts, polyacrylic and polymethacrylic acids, carboxylmethyl cellulose or a combination thereof.
- the water insoluble, ethylenically unsaturated resin can contain long chain aliphatic resins, aromatic resins, phenol formaldehyde resins, melamine resins, hydrocarbon resins and rosins, or a combination thereof.
- the water insoluble, ethylenically unsaturated resin may be a ring opening polymerizable composition, a free radical addition polymerizable composition, or a combination of ring opening and free radical polymerization.
- a ring opening polymerizable composition upon energy initiation it forms a polymer typically bound by ester, or ether linkages.
- the water insoluble, ethylenically unsaturated resin is a free radical addition polymerizable composition
- the water insoluble, ethylenically unsaturated resin comprises a liquid compound having terminal ethylenic unsaturation .
- the water insoluble, ethylenically unsaturated resin is a free radical polymerizable system comprising an ethylenically unsaturated mono- or multi- functional monomer.
- the monomer is a lower molecular weight ethylenically unsaturated compound which forms a polymer directly upon initiation by free radicals generated by absorbed energy.
- an oligomeric or polymeric component which can be further polymerized may also be present. In such cases the further polymerizable material will be soluble in, or dispersible in the monomer vehicle.
- the monomeric compounds have one, two or more terminal ethylenically unsaturated groups .
- Such monomeric compounds are: N-vinyl pyrrolidinone; dipropylene glycol diacrylate; tripropylene glycol diacrylate; butanediol diacrylate; hexanediol diacrylate; trimethylol propane triacrylate; ethoxylated trimethylol propane triacrylate; glycerol-propoxy triacrylate; pentaerythritrol triacrylate; dipropylene glycol dimethacrylate; tripropylene glycol dimethacrylate; butanediol dimethacrylate; hexanediol dimethacrylate; trimethylol propane trimethacrylate; di- (3-methacryloxy-2- hydroxypropyl ether) of bispenol-A; di (2metharyloxyethyl ether) of bisphenol-A; di- (3-acryloxy-2-hydroxypropyl ether) of bisphenol-A; di- (2- acryloxyethyl ether
- the monomer composition contains a combination of multi-functional acrylic monomers along with a monomer containing a single terminal ethylenic group .
- the inks of this invention contain an oligomeric or polymeric material
- said materials typically possess ethylenic unsaturation which can react with the ethylenically unsaturated monomers.
- oligomers are acrylated epoxy resins; acrylated polyurethanes; acrylated polyesters; and the like.
- the water insoluble, ethylenically unsaturated resin may also contain a preferred polymer such as an acrylic polymer or copolymer of C 1 -C alkyl acrylates or methacrylates, or acrylic or methacrylic acid, vinyl polymers and copolymers such as polyvinyl chloride, polyvinyl acetate, polyvinyl alcohol; polyvinylpyrolidone; cellulosic polymers and copolymers; and the like.
- a preferred polymer such as an acrylic polymer or copolymer of C 1 -C alkyl acrylates or methacrylates, or acrylic or methacrylic acid
- vinyl polymers and copolymers such as polyvinyl chloride, polyvinyl acetate, polyvinyl alcohol; polyvinylpyrolidone; cellulosic polymers and copolymers; and the like.
- the water used for washing the inks of the present composition before curing has its pH adjusted to be in the basic range, more preferably at a pH of about 8.5.
- water soluble resin is used in the inks of the present invention, water with about a neutral pH can be used for washing before curing and thus, no pH adjustment is usually required.
- the pigment may be one or more of any conventional organic or inorganic pigment selected from the group consisting of Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 17, Pigment Yellow 63, Pigment Yellow 65, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 75, Pigment Yellow 83, Pigment Yellow 97, Pigment Yellow 98, Pigment Yellow 106, Pigment Yellow 114, Pigment Yellow 121, Pigment Yellow 126, Pigment Yellow 127, Pigment Yellow 136, Pigment Yellow 174, Pigment Yellow 176, Pigment Yellow 188, Pigment Orange 5, Pigment Orange 13, Pigment Orange 16, Pigment Orange 34, Pigment Red 2, Pigment Red 9, Pigment Red 14, Pigment Red 17, Pigment Red 22, Pigment Red 23, Pigment Red 37, Pigment Red 38, Pigment Red 41, Pigment Red 42, Pigment Red 57:1, Pigment Red 112, Pigment Red 170, Pigment Red 210, Pigment Red 238, Pigment Blue 15, Pigment Blue 15:1, Pigment Blue 15:2, Pig
- White pigments such as titanium dioxide, zinc sulfide, zinc oxide may also be used in the inks of this invention.
- Pigment compositions which are also useful in the inks of this invention are described in U.S. Patents 4,946,508; 4,946,509; 5,024,894; and 5,062,894 each of which is incorporated herein by reference.
- Such pigment compositions are a blend of the pigment along with a poly (alkylene oxide) grafted pigment.
- the ultimate and quintessential goal of any printing is to transfer the ink uniformly onto the printing plate and then onto the printed substrate producing desired image.
- optical density print density
- print density targets for process colors yellow - 0.95 - 1.05, Magenta - 1.30
- Proofing machines such as the Prufbau are usually used to simulate printing. Several aspects of this simulation are typically evaluated.
- a standard volume of the ink is first applied onto the distribution roller and subjected to rigorous distribution at a given speed for a given period of time.
- the test protocol calls for 30 sec of distribution.
- the ink has to be converted into the uniform, evenly distributed layer on the top of the form roller.
- This roller is than transferred into the printing unit, and a print is produced with 800 N printing pressure at 3 m/s speed of the substrate carrier movement.
- the Print is UV or EB cured and print density is recorded.
- a well designed ink should produce a uniform image with target density.
- the target tack for the inks of the present invention is in the range between 20 and 21 at 1200 rpm.
- An inkometer is used to determine tack (Electronic Inkometer from Thwing Albert) .
- the ink is distributed for 1 min between 3 rollers and then the measurement is taken. Since the ink delivery system on the press can contain up to 13 distribution rollers, tack stability is very important.
- the main benefit of the energy curable inks is that they are extremely stable on rollers since no loss of solvent or water takes place.
- the inks of the present invention should have no more than a 1 point change in tack when submitted to the 10 min tack stability test (same 1200 rpm) .
- Inks of the present invention are prepared as follows. Ink ingredients are mixed together until a uniform mixture is obtained. This mixture is then ground on a 3 Roll mill until proper grinding specification is achieved (typically 2-3 passes on the mill) . The ink may be adjusted to the proper tack with a monomer if needed.
- An EB curable, water washable printing ink useful in the waterless lithographic printing process was formulated as follows: Yellow pigment (supplied by Sun Chemical Corp) 17%
- composition of the varnish identified above is as follows: Water soluble part: Laromer 8765 (from BASF) 41 parts
- This ink was printed using a Prufbau proofing machine to 1.08 print density and EB cured with the AEB electron beam processor set at 110 kV and 3 Mrads.
- the ink proof was than tested for water resistance by rubbing the printed surface with wet Q-tips .
- This ink film required more than 32 double rubs before any detrimental effect of wet rubbing could be seen on the print surface.
- the ink tack was measured as indicated above and was found to be in the range of 20 to 21 at 1200 rpm with less than 1 point change in tack when submitted to the 10 min tack stability test described above.
- Uncured ink was easily washed off the ink and printing rollers of the proofing machine with a water solution having pH of 8.5.
- Example 2 An EB curable, water washable printing ink was formulated as described in Example 1, however the pigment was Pigment red 23 (supplied by Sun Chemical Corporation) .
- This ink was printed using a Prufbau proofing machine to 1.50 print density with an AEB electron beam processor set at 110 kV and 3 Mrads. The ink proof was then tested for water resistance by rubbing the printed surface with wet Q-tips. The ink film would required more than 30 double rubs before any detrimental effect of wet rubbing could be seen on the print surface.
- the ink tack was measured as indicated above and was found to be in the range of 20 to 21 at 1200 rpm with less than 1 point change in tack when submitted to the 10 min tack stability test described above .
- Uncured ink was easily washed off the ink and printing rollers of the proofing machine with a water solution having pH of 8.5.
- Example 3 A UV curable, water washable printing ink was formulated as follows:
- Polyethylene glycol diacrylate 13 parts (from Sartomer Co.)
- This ink was printed using a Prufbau proofing machine to 1.45 print density and UV cured using laboratory UV curing unit having two medium pressure mercury lamp set at 200 watt/inch each and moving belt set at 200 fpm. The ink proof was then tested for water resistance by rubbing the printed surface with wet Q-tips. This ink would required more than 40 double rubs before any detrimental effect of wet rubbing could be seen on the print surface.
- the ink tack was measured as indicated above and was found to be in the range of 20 to 21 at 1200 rpm with less than 1 point change in tack when submitted to the 10 min tack stability test described above .
- Uncured ink was easily washed off the ink and printing rollers of the proofing machine with a water solution having pH of 8.5.
- Example 4 A UV curable, water washable printing ink was formulated as described in Example 3 but with Pigment Black 250 (obtained from Degussa) .
- This ink was printed using a Prufbau proofing machine to 1.70 print density and UV cured using a laboratory UV curing unit having two medium pressure mercury lamp set at 200 watt/inch each and moving belt set at 200 fpm. The ink proof was then tested for water resistance by rubbing the printed surface with wet Q-tips. This ink would required more than 20 double rubs before any detrimental effect of wet rubbing could be seen on the print surface.
- the ink tack was measured as indicated above and was found to be in the range of 20 to 21 at 1200 rpm with less than 1 point change in tack when submitted to the 10 min tack stability test described above .
- Uncured ink was easily washed off the ink and printing rollers of the proofing machine with a water solution having pH of 8.5.
- Example 5 An EB curable, water washable printing ink was prepared according to Example 1 but instead of non-reactive acid functional resin, Sarbax resin from Sartomer, ethylenically unsaturated with acid functionality was used in the ink varnish:
- the varnish composition is as follows:
- Johncryl 680 (from Johnson Polymer) 24 parts .
- This ink was printed using a Prufbau proofing machine to 1.08 print density with AEB electron beam processor set at 110 kV and 3 Mrads.
- the ink proof was than tested for water resistance by rubbing the printed surface with wet Q-tips.
- the ink would required more than 21 double rubs before any detrimental effect of wet rubbing could be seen on the print surface.
- the ink tack was measured as indicated above and was found to be in the range of 20 to 21 at 1200 rpm with less than 1 point change in tack when submitted to the 10 min tack stability test described above .
- Uncured ink was easily washed off the ink and printing rollers of the proofing machine with a water solution having pH of 8.5.
- Example 6 An EB curable, water washable printing ink was formulated as follows: Yellow pigment (supplied by Sun Chemical Corp.) 17% Additives (stabilizers, antimisting compounds) 5% Varnish 78%
- composition varnish composition is as follows:
- Polyethylene glycol diacrylate 13 parts (from Sartomer Co.)
- Polyvinylpyralidone (PVP 30) (from BASF) 7 parts Total 100 parts
- This ink was printed using a Prufbau proofing machine to 1.1 print density and EB cured with the AEB electron beam processor set at 110 kV and 3 Mrads.
- the ink proof was than tested for water resistance by rubbing the printed surface with wet Q-tips.
- the ink film required more than 30 double rubs before any detrimental effect of wet rubbing could be seen on the print surface.
- the ink tack was measured as indicated above and was found to be in the range of 20 to 21 at 1200 rpm with less than 1 point change in tack when submitted to the 10 min tack stability test described above .
- Uncured ink was easily washed off the ink and printing rollers of the proofing machine with a water solution having pH of 7.0.
Landscapes
- 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)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR0316765-8A BR0316765A (en) | 2002-12-13 | 2003-12-10 | Water-free energy curable printing ink and varnish compositions and methods of production and use |
EP03813359A EP1581598A1 (en) | 2002-12-13 | 2003-12-10 | Energy curable, water washable printing inks suitable for waterless lithographic printing |
MXPA05006355A MXPA05006355A (en) | 2002-12-13 | 2003-12-10 | Energy curable, water washable printing inks suitable for waterless lithographic printing. |
AU2003296391A AU2003296391A1 (en) | 2002-12-13 | 2003-12-10 | Energy curable, water washable printing inks suitable for waterless lithographic printing |
JP2004560738A JP2006509886A (en) | 2002-12-13 | 2003-12-10 | Energy-curable and water-washable printing ink suitable for dry lithographic printing |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/319,061 US20040115561A1 (en) | 2002-12-13 | 2002-12-13 | Energy curable, water washable printing inks suitable for waterless lithographic printing |
US10/319,061 | 2002-12-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004055123A1 true WO2004055123A1 (en) | 2004-07-01 |
Family
ID=32506549
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2003/039092 WO2004055123A1 (en) | 2002-12-13 | 2003-12-10 | Energy curable, water washable printing inks suitable for waterless lithographic printing |
Country Status (9)
Country | Link |
---|---|
US (1) | US20040115561A1 (en) |
EP (1) | EP1581598A1 (en) |
JP (1) | JP2006509886A (en) |
CN (1) | CN100473701C (en) |
AU (1) | AU2003296391A1 (en) |
BR (1) | BR0316765A (en) |
MX (1) | MXPA05006355A (en) |
WO (1) | WO2004055123A1 (en) |
ZA (1) | ZA200504728B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1645605A1 (en) * | 2004-10-06 | 2006-04-12 | TETENAL AG & Co. KG. | Radiation-curable ink jet ink |
JP2008536004A (en) * | 2005-04-12 | 2008-09-04 | サン・ケミカル・コーポレーション | Energy-curable water-based hybrid system with improved properties |
WO2021089313A1 (en) | 2019-11-07 | 2021-05-14 | Basf Se | Water-washable compositions for use in 3d printing |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1535304A (en) * | 2001-07-20 | 2004-10-06 | Ucb | Radiation curable polymeric ink compositons |
GB2450975B (en) * | 2007-07-12 | 2010-02-24 | Ciba Holding Inc | Yellow radiation curing inks |
CN101945907B (en) * | 2008-03-18 | 2013-01-02 | 氰特表面技术有限公司 | Aqueous radiation curable polyurethane compositions |
CN101981141B (en) * | 2008-03-28 | 2013-11-06 | Dic株式会社 | Lithographic printing ink |
RU2517015C2 (en) * | 2008-12-22 | 2014-05-27 | Текносолюшнз Ассессория Лтда | Method of flexographic printing comprising ability of printing on wet layer |
ES2689544T3 (en) * | 2011-09-23 | 2018-11-14 | Sun Chemical Corporation | Additives to lithography inks to eliminate ink feedback |
CN102786839B (en) * | 2012-07-31 | 2014-07-09 | 佛山市三求电子材料有限公司 | Glass protecting ink and preparation method thereof |
CN103045013B (en) * | 2013-01-25 | 2015-05-20 | 深圳市万佳原丝印器材有限公司 | Ultraviolet full-shielding printing ink and preparation method thereof |
CA2902753C (en) | 2013-02-27 | 2019-04-09 | Crayola Llc | Rinsable inks and methods of making the same |
CN104073025A (en) * | 2013-03-29 | 2014-10-01 | 日本化药株式会社 | Coloring dispersion agent, ink composition, inkjet recording method and colored member |
CN103666047B (en) * | 2013-11-25 | 2016-04-13 | 铜陵方正塑业科技有限公司 | A kind of ultraviolet cured offset printing ink and preparation method thereof |
US10139746B2 (en) | 2014-03-25 | 2018-11-27 | Hp Indigo B.V. | Liquid electrophotographic varnish composition |
ES2902031T3 (en) * | 2014-11-20 | 2022-03-24 | Toray Industries | Procedure for the manufacture of printed material |
TW201720881A (en) * | 2015-09-17 | 2017-06-16 | Toray Industries | Lithographic printing ink, varnish for lithographic inks, and method for producing printed matter using said ink |
JP6299886B2 (en) * | 2015-11-25 | 2018-03-28 | 東レ株式会社 | Ink for lithographic printing |
CN105400282A (en) * | 2015-12-21 | 2016-03-16 | 王景泉 | Highlight insulation gold varnish and preparation method there |
US10487226B2 (en) * | 2016-05-25 | 2019-11-26 | Electronics For Imaging, Inc. | Low odor radiation curable ink compositions |
CN107502057A (en) * | 2017-09-26 | 2017-12-22 | 句容市后白镇迎瑞印花厂 | Good water soluble acrylic acid ink of a kind of water-resistance and preparation method thereof |
CN109401424A (en) * | 2018-09-20 | 2019-03-01 | 永修县利君科技有限公司 | A kind of cured high temperature sintering varnish of LED-UV cold light source and preparation method thereof |
CN110157239A (en) * | 2019-06-12 | 2019-08-23 | 浙江中烟工业有限责任公司 | Recessed sand oil of a kind of online volume of EB and preparation method thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5354366A (en) * | 1993-09-27 | 1994-10-11 | Deluxe Corporation | Ink composition and resins and methods relating thereto |
US6140386A (en) * | 1994-04-19 | 2000-10-31 | Vanderhoff; John W. | Aqueous coating compositions, methods for making same and uses thereof |
WO2001048102A1 (en) * | 1999-12-23 | 2001-07-05 | Sericol Limited | An ink for decoration of paper substrates for poster displays |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4354366A (en) * | 1980-07-11 | 1982-10-19 | Kidde, Inc. (Presto Lock Company Division) | Combination locks |
JPS61243869A (en) * | 1985-04-19 | 1986-10-30 | Taiyo Ink Seizo Kk | Resist ink composition |
TW311923B (en) * | 1992-01-27 | 1997-08-01 | Ciba Sc Holding Ag | |
US5308390A (en) * | 1992-09-17 | 1994-05-03 | Deluxe Corporation | Ink composition and method of making and using such composition |
JP3329877B2 (en) * | 1993-03-02 | 2002-09-30 | 互応化学工業株式会社 | Resist ink composition for manufacturing printed circuit board, resist film using the same, and printed circuit board |
US5703141A (en) * | 1995-09-25 | 1997-12-30 | Tarkett Ag | UV curable coatings |
US5725646A (en) * | 1996-03-13 | 1998-03-10 | Sun Chemical Corporation | Water-based offset lithographic printing ink |
US5778789A (en) * | 1996-03-13 | 1998-07-14 | Sun Chemical | Offset lithographic printing process with a water based ink |
JP3722309B2 (en) * | 1996-05-17 | 2005-11-30 | 日立化成工業株式会社 | Photosensitive resin composition, photosensitive laminate and method for producing flexible printed board |
US6500495B2 (en) * | 1997-02-27 | 2002-12-31 | Acushnet Company | Method for curing reactive ink on game balls |
JP3821912B2 (en) * | 1997-05-07 | 2006-09-13 | サカタインクス株式会社 | Active energy ray-curable waterless lithographic ink composition and method for producing printed matter using the same |
JPH11172150A (en) * | 1997-10-09 | 1999-06-29 | Dainippon Printing Co Ltd | Composition for non-conducting light trapping layer, non-conducting light-trapping layer and color filter |
US6806301B2 (en) * | 1998-11-30 | 2004-10-19 | Flint Ink Corporation | Lithographic printing inks |
JP2000178488A (en) * | 1998-12-14 | 2000-06-27 | Seiko Epson Corp | Ink composition and printer using the same |
JP2000319566A (en) * | 1999-05-11 | 2000-11-21 | Riso Kagaku Corp | U.v ink |
KR100305103B1 (en) * | 1999-05-19 | 2001-10-18 | 유광선 | UV-curing adhesive transfer ink |
JP3924993B2 (en) * | 1999-06-10 | 2007-06-06 | セイコーエプソン株式会社 | Ink for inkjet recording |
US20020121631A1 (en) * | 2000-10-31 | 2002-09-05 | Ata Rahman | Radiation curable coatings for printed surfaces |
US6772683B2 (en) * | 2002-02-19 | 2004-08-10 | Sun Chemical Corporation | Method and apparatus for wet trapping with energy-curable flexographic liquid inks |
ATE401379T1 (en) * | 2002-05-06 | 2008-08-15 | Sun Chemical Corp | SINGLE-PHASE ENERGY CURING WATER-BASED COMPOSITIONS |
US20040157959A1 (en) * | 2002-05-06 | 2004-08-12 | Jean Dominique Turgis | Homogenous aqueous energy curable metallic printing ink compositions |
EP1560888B1 (en) * | 2002-11-15 | 2008-07-30 | Markem Corporation | Radiation-curable inks |
-
2002
- 2002-12-13 US US10/319,061 patent/US20040115561A1/en not_active Abandoned
-
2003
- 2003-12-10 WO PCT/US2003/039092 patent/WO2004055123A1/en active Application Filing
- 2003-12-10 AU AU2003296391A patent/AU2003296391A1/en not_active Abandoned
- 2003-12-10 JP JP2004560738A patent/JP2006509886A/en active Pending
- 2003-12-10 MX MXPA05006355A patent/MXPA05006355A/en unknown
- 2003-12-10 BR BR0316765-8A patent/BR0316765A/en not_active IP Right Cessation
- 2003-12-10 EP EP03813359A patent/EP1581598A1/en not_active Withdrawn
- 2003-12-10 CN CNB2003801060480A patent/CN100473701C/en not_active Expired - Fee Related
-
2005
- 2005-06-09 ZA ZA200504728A patent/ZA200504728B/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5354366A (en) * | 1993-09-27 | 1994-10-11 | Deluxe Corporation | Ink composition and resins and methods relating thereto |
US6140386A (en) * | 1994-04-19 | 2000-10-31 | Vanderhoff; John W. | Aqueous coating compositions, methods for making same and uses thereof |
WO2001048102A1 (en) * | 1999-12-23 | 2001-07-05 | Sericol Limited | An ink for decoration of paper substrates for poster displays |
Non-Patent Citations (1)
Title |
---|
See also references of EP1581598A1 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1645605A1 (en) * | 2004-10-06 | 2006-04-12 | TETENAL AG & Co. KG. | Radiation-curable ink jet ink |
JP2008536004A (en) * | 2005-04-12 | 2008-09-04 | サン・ケミカル・コーポレーション | Energy-curable water-based hybrid system with improved properties |
WO2021089313A1 (en) | 2019-11-07 | 2021-05-14 | Basf Se | Water-washable compositions for use in 3d printing |
Also Published As
Publication number | Publication date |
---|---|
ZA200504728B (en) | 2006-06-28 |
BR0316765A (en) | 2005-10-25 |
CN1726264A (en) | 2006-01-25 |
JP2006509886A (en) | 2006-03-23 |
US20040115561A1 (en) | 2004-06-17 |
AU2003296391A1 (en) | 2004-07-09 |
CN100473701C (en) | 2009-04-01 |
EP1581598A1 (en) | 2005-10-05 |
MXPA05006355A (en) | 2005-09-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200504728B (en) | Energy curable, water washable printing inks suitable for waterless lithographic printing | |
US10407580B2 (en) | Single phase water based energy curable compositions and method of preparing coatings and printing inks | |
CN101835853B (en) | Radiation curable inkjet printing methods | |
US7368485B2 (en) | Printing ink | |
JP5563216B2 (en) | Energy-curable water-based hybrid system with improved properties | |
JP6561126B2 (en) | Photosensitive composition, image forming method, and film forming method | |
US20050197418A1 (en) | Insoluble polymer compositions suitable for ink jet ink formulations | |
US20040029044A1 (en) | Photocurable composition | |
EP1561792A1 (en) | New ink compositions for ink jet printing | |
EP2041230A1 (en) | A printing ink | |
US20090214797A1 (en) | Inkjet ink composition, and inkjet recording method and printed material employing same | |
WO2018155174A1 (en) | Photocurable ink composition and image forming method | |
US20050080152A1 (en) | Radiation curable compositions for pigmented liquids inks | |
CA1268284A (en) | Radiation curable macromonomer printing inks | |
EP1699888A1 (en) | Homogenous aqueous energy curable metallic printing ink compositions | |
WO2018042193A1 (en) | A method of printing | |
EP3587510A1 (en) | Led curable compositions | |
CN115380085B (en) | Photo-curable aqueous ink composition for inkjet printing | |
JP2008069214A (en) | Ink composition, inkjet recording method, printed product and method for producing lithographic printing plate | |
JP7508965B2 (en) | Pigment composition and printing ink | |
JPS585948B2 (en) | water-based printing ink | |
WO1997019992A1 (en) | Acrylic emulsions useful in printing inks |
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 BZ CA CH CN CO CR CU CZ DE DK DM DZ EC 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 MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SC SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): BW GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2005/04728 Country of ref document: ZA Ref document number: 200504728 Country of ref document: ZA Ref document number: 2004560738 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/2005/006355 Country of ref document: MX Ref document number: 2003813359 Country of ref document: EP Ref document number: 20038A60480 Country of ref document: CN |
|
WWP | Wipo information: published in national office |
Ref document number: 2003813359 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: PI0316765 Country of ref document: BR |