WO2009007968A2 - Compositions d'encre - Google Patents

Compositions d'encre Download PDF

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Publication number
WO2009007968A2
WO2009007968A2 PCT/IL2008/000948 IL2008000948W WO2009007968A2 WO 2009007968 A2 WO2009007968 A2 WO 2009007968A2 IL 2008000948 W IL2008000948 W IL 2008000948W WO 2009007968 A2 WO2009007968 A2 WO 2009007968A2
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WO
WIPO (PCT)
Prior art keywords
oil
ink composition
based ink
composition according
straight
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PCT/IL2008/000948
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English (en)
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WO2009007968A3 (fr
Inventor
Avraham Zach
Oleg Dardyk
Yelena Yusupov
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Bordeaux Digital Printink Ltd.
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Publication of WO2009007968A2 publication Critical patent/WO2009007968A2/fr
Publication of WO2009007968A3 publication Critical patent/WO2009007968A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/36—Inkjet printing inks based on non-aqueous solvents

Definitions

  • the present invention relates to ink compositions, more specifically to oil based ink compositions comprising, in addition to pigment(s), and polymer(s), a mixture of organic solvents for use in inkjet printing systems.
  • Ink jet printing systems are widely used for printing high quality images on different substrates, also known as recording media.
  • droplets of black or colored inks are ejected with high frequency from nozzles in the ink jet print-head and are deposited directly onto the substrate to produce a high quality image.
  • InkJet print-heads produce droplets either continuously or on demand. Continuous production requires that the ink supply is pressurized sufficiently to create a jet, but only a fraction of the ink droplets are ejected onto the substrate, whilst the rest of the droplets are recirculated. In the so-called drop-on-demand inkjet method, the ejecting process is computer controlled. Generally, the quality of images printed by on-demand systems is higher than that produced by the continuous printing methods.
  • the drop on-demand ink jet print-heads generally work on either a piezoelectric or a thermal basis.
  • piezoelectric drop-on-demand inkjet PIJ
  • individual droplets are squeezed out of a small chamber by forcefully changing its shape by means of a piezoelectric element.
  • thermal inkjet TIJ
  • the ink is heated in a vaporization chamber.
  • a rapidly expanding vapor front forces the ink out of the vaporization chamber through an adjacent nozzle.
  • TIJ allows using aqueous inks in which water is the principal solvent
  • the PIJ method allows using either water based inks or oil based inks in appropriate organic solvents.
  • Oil based inks are advantageous in that the images produced thereby, have high water resistance. This allows their usage (on appropriate substrates) outside, in humid or rainy environments, without lamination. Another advantage of such inks is their ability to wet and adhere to polyvinyl chloride (PVC) substrates, it is known that cellulose based papers and cards are not appropriate substrates for long term exposure to the elements.
  • PVC polyvinyl chloride
  • inks For assuring good printing stability inks must have a low viscosity. Typically a viscosity of less then 20 mPas at 25 C is required.
  • the ink should include solvents having high boiling points and low evaporation rates to reduce the risk of the ink drying at the edges of the print-head nozzles which invariably results in clogging.
  • the printed image should have good drying characteristics even when printed onto a relatively non absorbent substrate, such as, for example, onto PVC films.
  • United States Patent No. US 6,663,702 to Day describes inks for use in ink-jet printers for printing on to impervious or non-porous substrates such as, for example, glass, ceramics, plastics such as, for example, polycarbonate, polyvinyl chloride, cellulose acetate butyrate, and metals.
  • the ink comprises a resin and two solvents selected from ethyl lactate and an ester of an aliphatic alcohol or a monocarboxylic acid. Each ester has a different evaporation rate, but both dry quickly without the need for heating.
  • the oil based printing inks described by Day contain a resin, a relatively fast evaporating solvent which is a good solvent for that resin and a relatively slow evaporating solvent which is a poorer solvent for that resin.
  • the inks also comprise a film forming resin which is soluble in both solvents.
  • the good solvent for the resin has a higher evaporation rate than the poorer solvent, it has been found to cause settling of solid components at the edges of nozzles resulting in blockage of the print-head.
  • the oil- based ink compositions described do not have good fixing properties on PVC media.
  • the relatively fast evaporating solvents are somewhat "harmful" to the environment, have a foul odor, and may be a health hazard, thus their usage in inkjet printing is problematic.
  • the ink has good storage stability. It is a further object of preferred embodiments of the invention that the ink has good alcohol resistance.
  • the ink has a low odor.
  • an oil-based ink composition comprising: (i) at least one pigment; (ii) at least one polymer; (iii) an organic solvent comprising a nitrogen containing heterocyclic compound and (iv) a mixture comprising a plurality of dicarboxylic acid esters, and
  • the plurality of dicarboxylic acid esters have the following general formula: ROC(O)-(CHR 2 ) n -C(O)OR 3 General formula (1)
  • saturated aliphatic alcohol derivative is selected from the list of:
  • R and R 3 independently represents a straight or branched chain (Ci - C 6 ) alkyl group;
  • R 1 represents a straight or branched (Ci - C 4 ) alkylene group;
  • n is an integer of 1 to 8.
  • a preferred compound of general formula (1) is defined such that:
  • R and R 3 represents a straight or branched (Cj - C 4 ) alkyl group;
  • R 2 represents a hydrogen atom;
  • n is an integer of 2 to 4.
  • a preferred compound of general formula (2) is defined such that: R represents a straight or branched (C 1 - C 4 ) alkyl group; R 1 represents a straight or branched (C 2 - C 3 ) alkylene chain; and R 2 represents a hydrogen atom or a straight or branched (Ci - C 4 ) alkyl group.
  • a preferred compound of general formula (3) is defined such that: R is selected from the list of straight and branched (Ci - C 4 ) alkyl groups; R 1 is selected from the list of straight and branched (C 2 - C 3 ) alkyl groups; R 3 is selected from the list of straight and branched (Ci - C 3 ) alkyl groups, and n is an integer from 1 to 3.
  • a preferred compound of general formula (4) is defined such that: R is selected from the list of straight and branched (C 2 - C 3 ) alkyl groups.
  • a preferred compound of general formula (5) is defined such that: R represents a straight or branched (Ci - C 5 ) alkyl group.
  • alkyl implies a straight or branched chain having saturated radicals including, but not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secondary butyl and tertiary butyl.
  • alkylene means a straight or branched unsubstituted saturated hydrocarbon wherein a hydrogen atom is removed from each of the terminal carbons such as methylene, ethylene, methylethylene, propylene, butylene and the like.
  • the nitrogen containing heterocyclic compound is a pyrrolidone derivative. More specifically, the pyrrolidone derivative is a (Ci - C 6 ) alkyl pyrrolidone, such as, for example, methyl pyrrolidone, ethyl pyrrolidone, propyl pyrrolidone and hexyl pyrrrolidone.
  • alkyl pyrrolidone is selected from the list comprising N- methyl-2-pyrrolidone and N-ethyl-2-pyrrolidone.
  • Preferred ink compositions comprise between 5% and 30% of the nitrogen containing heterocyclic compound by weight.
  • More preferred ink compositions comprise between 10% and 25% of the nitrogen containing heterocyclic compound by weight.
  • the at least two dicarboxylic acid esters are selected from the list of dimethyl esters of succinic acid, dimethyl esters of glutaric acid, dimethyl esters of adipic acid, dibutyl esters of succinic acid, dibutyl esters of glutaric acid and dibutyl esters of adipic acid.
  • Preferred ink compositions comprise between 5% and 70% of the dicarboxylic acid esters. More preferably, ink compositions comprise between 10% and 50% of the dicarboxylic acid esters.
  • the ink composition is characterized by a combined weight percentage of the nitrogen containing heterocyclic compound and dicarboxylic acid esters being between 15% and 80%.
  • the ink composition further comprises at least 5% by weight of the saturated aliphatic alcohol derivative.
  • the saturated aliphatic alcohol derivative has a boiling point in the range 140 - 200 C, and preferably has a boiling point in the range 150 - 190 C.
  • the oil based ink composition is characterized by a flash point of at least 63°C.
  • the ink composition of preferred embodiments of the invention is suitable for application by an ink jet printer onto a PVC substrate.
  • a further aspect of the invention is directed to a composition comprising an organic solvent comprising:
  • the organic solvent essentially contains a nitrogen containing heterocyclic compound and a mixture of dicarboxylic acid esters together with a saturated aliphatic alcohol derivative that is typically a polyalkylene glycol derivative or an alkyl lactate derivate. It has been surprisingly found that the combination of a nitrogen-containing heterocyclic compound, such as N-methyl-2- pyrrolidone or N-ethyl-2-pyrrolidone together with a mixture of dicarboxylic acid esters and such a glycol derivative or alkyl lactate can dissolve PVC film and penetrate into the surface of a PVC layer. Oil-based pigmented inks based on this combination of solvents has been shown to have excellent leveling, fixing and drying properties on a wide range of printing media, particular PVC film, without requiring a receptive layer.
  • Ink compositions in accordance with preferred embodiments are characterized by having high boiling points and low evaporation rates. These characteristics help to prevent the solidification of inks at the edges of ink-jet nozzles.
  • ink compositions that include only one of the above mentioned solvents do not perform satisfactorily, particularly when used for printing onto PVC for use our of doors. Either such inks do not provide print stability and ejectability from print-head nozzles, and/or don't display acceptable fixing and drying properties, and/or the print quality on the recording substrate, is inadequate.
  • Nitrogen-containing heterocyclic compounds are environmentally and user safe and are practically odor free.
  • N-methyl- 2-pyrrolidone (boiling point 202 C) and N-ethyl-2pyrrolidone (boiling point 210 C) have been found to perform well, and may be used to produce inks having good fixing properties and low odor.
  • the ink compositions of the present invention include a mixture of dicarboxylic acid esters, typically two or more dicarboxylic acid esters selected from the following: dimethyl or dibutyl esters of succinic, glutaric and adipic acids.
  • dicarboxylic acid esters typically two or more dicarboxylic acid esters selected from the following: dimethyl or dibutyl esters of succinic, glutaric and adipic acids.
  • Each of the compounds is included in the ink composition in a measurable quantity, typically at least 0.2 % by weight of the composition.
  • These di-esters are effective solvents of a large range of polymers, including the binder resins that are used in ink formulations of the present invention. Since these solvents also dissolve PVC, they accelerate the drying of inks of the invention on PVC substrates.
  • Dimethyl di-esters have a distillation range of 196 - 230 C, while dibutyl di-esters have a higher distillation range of 275 - 289 C. These compounds are known to be very safe, readily biodegradable and have low odor.
  • VOC Volatile organic compounds
  • ink compositions in accordance with the present invention generally include the nitrogen-containing heterocyclic compound in a concentration of 5 to 30% by weight, and typically 10% to 25% by weight of the ink composition taken as a whole.
  • the mixture of dicarboxylic acid esters in the inks of the invention is typically in the range of 5% to 70% by weight, and most typically in the range of between 10% and 50% by weight.
  • the total percentage of nitrogen-containing heterocyclic compound and dicarboxylic acid esters accounts for 15 - 80% by weight and preferably 20-70% by weight of the ink compositions of preferred embodiments of the invention.
  • oil-based pigmented ink compositions of preferred embodiments of the present invention also contain at least 5% by weight of at least one solvent that is either a (poly)alkylene glycol derivative group or an alkyl lactate derivative, having a boiling point range of 140 - 200 ° C.
  • this additional solvent has a boiling point in the range of 150 -190 ° C.
  • Suitable (Poly)alkylene glycol derivatives include the following groups of solvents:
  • solvent groups 1 and 2 it is preferable to use dialkyl ethers, because these solvents are able to dissolve various resins, have low viscosity, emit low odors and are safe to handle.
  • solvents are diethylene glycol diethyl ether and dipropylene glycol dimethyl ether.
  • Solvents from groups 3 and 4 are glycol ether derivatives of acetic and propionic acids. These solvents are characterized by being effective solvents of the binders that are used in ink compositions of preferred embodiments of the present invention. Solvents that has been shown to perform well, include butylene glycol monomethyl ether acetate and ethylene glycol monoethyl ether propionate. These solvents are not harmful and have low odor.
  • solvents from group 5 include ethylene glycol diacetate, propylene glycol diacetate. These solvents are effective at dissolving the binders included in preferred ink compositions of the present invention, have low odor and high flash point.
  • Alkyl lactates are good solvents for various binder resins, are safe and have low odor.
  • Alkyl lactates that may be used in some embodiments of the present invention include ethyl lactate, n-propyl lactate and butyl lactate, for example.
  • Solvents from the (poly)alkylene glycol derivative group and the alkyl lactate group as described hereinabove may be used singly or in a mixture thereof.
  • Ink compositions in accordance with the present invention typically contain at least 5% by weight of these solvents and preferably 20-70% by weight.
  • Appropriate selection of solvents from the (poly)alkylene glycol derivative group and the alkyl lactate group is an effective way of ensuring that the flash point of ink compositions in accordance with preferred embodiments of the invention will remain at or above 63 C. It will be noted that it may be possible to use solvents that themselves have a flash point lower than 63 C in combination with other solvents having higher flash points but to ensure that the flash point of the total ink composition remains at or above 63 C.
  • solvents that are not harmful to the environment, have regulatory approval and are not hazardous to personnel. Such solvents should also have a low odor. Inks in accordance with preferred embodiments of the invention are safe to use in the printing process and are readily and safely transported.
  • Inorganic and organic pigments which are generally used in inkjet inks may be used in oil-based ink compositions of the present invention. These compositions may contain one or more pigments and are generally selected as having the required color and light fastness.
  • organic pigments that may be used in oil-based ink composition according to the present invention include (poly)azo pigments, phthalocyanine pigments, quinacridone pigments, quinophthalone pigments, iso-indolinone pigments, benzimidazolone pigments and diketopyrrolidone pigments.
  • Appropriate pigments for use in preferred embodiments of the present invention have good light fastness, weather resistance and color density.
  • Such pigments include CI Pigment Blue 15, 15:3, 15:4 which may be used in cyan inks, CI Pigment Red 122, 202, 254 and CI Pigment Violet 19 which are useful for magenta inks, CI Pigment Yellow 83, 110, 150, 151, 155 which are useful for yellow inks, and carbon black pigment (CI Pigment Black 7) is appropriate for use in black inks.
  • the amount of pigment in typical ink compositions is generally between 0.2% and
  • a dispersant agent may be used to ensure a stable pigment dispersion in oil-based ink compositions of the invention.
  • effective dispersants include Solsperse 20000, 32000, 32500, 33000, 33500, 35000, 35500 and 38500 which are available from Noveon Div. Lubrizol Ltd; Disperbyk; 161, 163, 167, 168. 190 and 2050 available from BYK-Chemie Gmbh, and EFKA 7477, 7496 and 4340 which are available from EFKA additives.
  • the content ratio of the dispersant to the pigment is selected to give an appropriate dispersion stability of pigment, and is generally in the range of from 10% to 150%, and typically in the range of from 30% to 120%.
  • Oil-based ink compositions in accordance with embodiments of the present invention contain one or more binder resins.
  • the binder resin is added in order to impart fixing properties and adhesion to polyvinyl-chloride substrates and to provide desired viscosity and flow ability.
  • the binder resin is preferably water-insoluble.
  • any resin that is soluble in the solvent mixture of present invention may be used, but in preferred embodiments of the present invention the binder resin should be at least one resin selected from the group consisting of vinyl chloride- vinyl acetate copolymer resin and acrylic resins. These binder resins can be used either singly or in combination.
  • preferable acrylic resins are methyl methacrylate homopolymers, methyl methacrylate and butyl methacrylate copolymers, such as Johncryl polymers manufactured by Johnson Polymer Corporation and the Paraloid series of Rohm and Haas Company.
  • vinyl chloride-vinyl acetate copolymer resin include UCAR Solution Vinyl Resins manufactured by Dow Chemical Company the Vynnol resins of WackerChemie GmbH and the like.
  • the binder resin is contained in the range of 1-10% by weight in typical inkjet inks of the invention, and preferably from 2 to 8% by weight of the total ink composition.
  • additives such as antioxidants, plasticizers, UV inhibitors and surface-active agents may be added.
  • oil-based ink compositions of the present invention are optimized to have specific viscosities and surface tension.
  • the viscosity is typically 2 to 20 mPas (at 25 C), and preferably 3 - 14 mPas.
  • the surface tension is typically in the range of from 20 to 40 mN/m (at 25 C).
  • the oil-based ink composition of preferred embodiments of the present invention are free from the problem of solidification of ink at the edges of nozzles in print-heads, have fast fixation and drying of ink on PVC substrate without a special receptive layer, have low odor and are very safe to use.
  • ink compositions are detailed. These examples are provided by way of disclosing the best modes of the invention and should not be construed as limiting in any way. Furthermore, although specific manufacturing techniques are given, it will be appreciated that ink compositions according to present invention may be fabricated by other methods that provide the required product quality.
  • polymeric pigment dispersant Solsperse 32000 was preliminary dissolved in a corresponding mixture of dicarboxylic acid esters of a concentration of 40%.
  • Pigment Red 202 (Cinquasia Magenta RT-235D available from CIBA Specialty Chemicals) was preliminary dispersed in mixture "A" of dicarboxylic acid esters (dimethyl adipate - 20 parts, dimethyl glutarate - 60 parts, dimethyl succinate - 20 parts) with addition of Solsperse 32000.
  • the pigment (30 parts) was dispersed in high shear mixer.
  • the obtained product is milled in Willy A. Bachofen nanomill with zirconia beads (diameter 0.3 mm) for 2 hours.
  • Binder resins UCAR solution VYHH and Paraloid B-66 were preliminary dissolved in N-methyl-2-pyrrolidone in a concentration of 20%..
  • An oil-based ink composition was prepared in the manner hereinabove with reference to Example 1, but with Pigment Blue 15:4 (Irgalite Blue GLVO available from CIBA Specialty Chemicals), which was dispersed in dicarboxylic acid esters mixture "B" (dimethyl glutarate - 99 parts and dimethyl succinate - 1 part).
  • Pigment Blue 15:4 Irgalite Blue GLVO available from CIBA Specialty Chemicals
  • Example 2 Only VYHH was used as binder resin; a solution of which was added to obtain the dispersion during mixing. The resulting mixture was diluted with residual dicarboxylic acid esters mixture "B” and dipropylene glycol dimethyl ether (boiling point - 175 C). The final ink formulation of Example 2 is shown in table 1 in absolute amounts.
  • An oil-based ink composition was prepared in the same manner as in Example 1.
  • the pigment used was Pigment Yellow 150 (Cromophtal Yellow LA2 available from Ciba Specialty Chemicals), which was dispersed in dicarboxylic acid esters mixture "C” (dimethyl glutarate - 75 parts, and dimethyl adipate - 25 parts).
  • dicarboxylic acid esters mixture "C” dimethyl glutarate - 75 parts, and dimethyl adipate - 25 parts.
  • resin solutions were added to the dispersion obtained, during the mixing process.
  • the mixture was diluted with residual dicarboxylic acid esters mixture "C", ethylene glycol monoethyl ether propionate (boiling point - 170 C) and n-propyl lactate (boiling point - 170 C).
  • the final ink formulation according to Example 3 is shown in absolute amounts in Table 1.
  • An oil-based ink composition was prepared in the same manner as for Example 2, but with Pigment Black 7 (Mogul L available from Cabot Corporation), which was dispersed in dicarboxylic acid esters mixture "D" (dimethyl glutarate - 67 parts, dimethyl succinate - 33 parts).
  • Pigment Black 7 Pigment L available from Cabot Corporation
  • Binder resin Paraloid B-66 was first dissolved in N-ethyl-2-pyrrolidone (20% by weight) and was then added to the obtained dispersion during mixing. The mixture was then diluted with residual dicarboxylic acid esters mixture "D", ethylene glycol monoethyl ether propionate (boiling point - 170 ° C) and dipropylene glycol dimethyl ether (boiling point -175
  • An oil-based ink composition was prepared in the same manner as in Example 4, but both resin solutions were used.
  • the pigment was dispersed in dicarboxylic acid esters mixture "D", the residual of which was added after addition of resin solutions.
  • dicarboxylic acid esters mixture "E” dibutyl glutarate- 60 parts, dibutyl succinate - 20 parts, dibutyl adipate -20 parts
  • dipropylene glycol monomethyl ether (boiling point - 190 C)
  • propylene glycol diacetate (boiling point - 191 C) were added.
  • the final ink formulation according example 5 is shown in table 1 in absolute amounts.
  • Table 1 The amounts in table 1 are shown in parts by weight.
  • An oil-based ink composition was prepared in the same manner as that used in the preparation of example 2, but the binder resin was dissolved in dicarboxylic acid ester mixture "B" and propylene glycol diacetate in a ratio 1 :1.
  • the ink composition included also
  • Comparative example 2 An oil-based ink composition was prepared in the same manner as that used in the preparation of example 3, but Pigment Yellow 150 was dispersed in N-propyl lactate.
  • the ink composition included 3 parts dicarboxylic acid ester mixture "C”.
  • the final ink formulation according to comparative example 2 is shown in table 2 in absolute amounts.
  • Comparative example 3 An oil-based ink composition was prepared in the same manner as that used in the preparation of example 4, but the ink composition also included 25 parts of dipropylene glycol monomethyl ether acetate (boiling point - 209 C). The final ink formulation according to comparative example 3 is shown in table 2 in absolute amounts.
  • Comparative example 4 An oil-based ink composition was prepared in the same manner as in example 5, but instead of dipropylene glycol diacetate the ink composition included 25 parts butyl acetate (boiling point - 126 ° C) and 11.2 parts dipropylene glycol dimethyl ether. The final ink formulation according to comparative example 4 is shown in table 2 in absolute amounts. Comparative example 5
  • An oil-based ink composition was prepared in the same manner as that used in the preparation of example 1, but the ink composition included 35 parts N-ethyl-2-pyrrolidone.
  • the final ink formulation according to comparative example 5 is shown in table 2 in absolute amounts. Comparative example 6
  • An oil-based ink composition was prepared in the same manner as that used in the preparation of example 2, but binder resin VYHH was dissolved in dicarboxylic acid ester mixture "B” and N-methyl-2-pyrrolidone in ratio 1 :1.
  • the ink composition included 73 parts dicarboxylic acid esters mixture "B".
  • the final ink formulation according to comparative example 6 is shown in Table 2 in absolute amounts.
  • An oil-based ink composition was prepared in the same manner as in example 3, but the ink composition included 55 parts dicarboxylic acid esters mixture "C” and 30 parts N- methyl-2-pyrrolidone, in other words 85 parts of combination of a nitrogen containing heterocyclic compound and mixture of dicarboxylic acid esters.
  • the final ink formulation according to comparative example 7 is shown in table 2 in absolute amounts.
  • a viscosity of ink composition was measured with DV- 1+ viscometer (available from Brookfield Engineering Laboratories) at 25 C. Cone rotation speed was 30 rpm for ink compositions of examples 1, 4 and comparative example 1, and 12 rpm for ink compositions of examples 2, 3, 5 and comparative examples 2, 3, 6, 7.
  • a flash point was measured according to ASTM D-93-99b, closed cup method
  • An oil-based ink composition was coated on glossy PVC substrate (available from Intercoat) using No 2 wire bar (available from RK Print Coat Instruments Ltd). The coated layer was dried at 25 ° C and its drying characteristics were evaluated according to the following criteria:
  • An oil-based ink composition was coated on glossy PVC substrate (available from Intercoat) using No 2 wire bar (available from RX Print Coat Instruments Ltd). The coated layer was drying at 25 C for 1 hour. After that the coated surface was rubbed with a finger and the fixing properties were evaluated according to the following criteria: A - No rubbing marks were observed
  • An oil-based ink composition was coated on glossy PVC substrate (available from Intercoat) using No 2 wire bar (available from RK Print Coat Instruments Ltd). The coated layer was drying at 25 C for 16 hours. After that the coated surface was wiped with a piece of cloth (available from Sano) soaked with 99% ethanol. The alcohol resistance was evaluated according to the following criteria:
  • oil-based ink compositions according to examples 1 , 4 and comparative examples 1, 4, 5 specified for one of the inkjet printing systems having Epson and other print-heads, which require inks with viscosity 3-5 mPas
  • oil-based ink compositions according to examples 2, 3, 5 and comparative examples 2, 3, 6, 7 specified for one of the inkjet printing systems having Xaar, Spectra, Konica-Minolta, Seiko and other print-heads, which require inks with viscosity 9-14 mPas.
  • Table 3 summarizing test evaluations of exemplary inks of the invention and comparative examples.
  • inks according to examples 1 - 5 have the required viscosity, good drying and fixing properties and high alcohol resistance.
  • the ink compositions according to examples 1-5 exhibited low odor. All the ink samples had a flash point exceeding 63 C. This guarantees safe transportation and handling.
  • the oil-based ink composition according to Example 1 which contains a low concentration of dicarboxylic acid esters mixture and a nitrogen containing heterocyclic compound has slightly low fixing properties. However the ink is nevertheless adequate for some inkjet printing applications.
  • the ink composition according to comparative Example 1 contains relatively little amount of nitrogen containing heterocyclic compound and it showed poor penetration into PVC substrates. Consequently, the drying, fixing and alcohol resistance were worse.
  • the ink composition according to comparative example 3 contains a solvent from a (poly)alkylene derivative group with high boiling point thus causing a deterioration in the drying and fixing.
  • the ink composition according to comparative example 4 contains a solvent with a flash point of 23 C, thus increasing the degree of product danger thus creating difficulties in handling and transportation.
  • the ink compositions according to comparative examples 5, 6 and 7 contain a high concentration of a combination of nitrogen-containing heterocyclic compound and dicarboxylic acid esters mixture. With such a concentration these solvents cannot be effectively absorbed by PVC substrate, and they remain on the surface. Because of their high boiling points there is a marked deterioration of the drying, fixing and alcohol resistance.
  • Color Painter 645 with Konika-Minolta print-heads. At first, thin lines and solid colors were printed and then exposed to drying temperatures of 35 C and 40 C.
  • the ink composition according to comparative example 3 did not print in a well defined manner and edges were somewhat blurred. The problem was more acute at the lower printing temperature of 35 C. With the other exemplary compositions of the invention described hereinabove, the printing quality was high and blurring was non-existent.
  • the ink compositions were tested in intensive printing for 3 days with intervals, and, following a pause of 5 days, the test pattern was performed a second time. It was found that the printing ink compositions of examples 1 - 5 performed well, without nozzle blocking.
  • the ink composition according to comparative example 2 featured absent nozzles on every print starting, especially after the five days stoppage. This was attributed to the low concentration of the solvent, specifically, the low concentration of the combination of nitrogen-containing heterocyclic compound and the dicarboxylic acid esters mixture.
  • oil based ink compositions with low odor, that avoid usage of volatile organic compounds with regulatory restrictions, and are environmentally friendly and suitable for printing onto PVC have been described.
  • These oil-based ink compositions include a solvent mixture that contains a nitrogen-containing heterocyclic compound and a dicarboxylic acid esters mixture.
  • composition comprising an organic solvent comprising:
  • a saturated aliphatic alcohol derivative will be useful as a flushing fluid, solvent or dilutent for inks of the invention and thus such as solvent without pigment and perhaps even without polymer is a basic embodiment of the invention.
  • compositions given hereinabove are given by way of non-limiting examples only. Other compositions will be obvious to the man of the art.

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

Abstract

L'invention porte sur une composition d'impression comprenant un solvant organique qui comprend: un composé hétérocyclique contenant de l'azote; un mélange comprenant une pluralité d'esters d'acides dicarboxyliques de formule générale ROC(O)-(CR2)n-CO(OR3), et un dérivé d'alcool aliphatique saturé.
PCT/IL2008/000948 2007-07-09 2008-07-09 Compositions d'encre WO2009007968A2 (fr)

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IL184508 2007-07-09
IL184508A IL184508A0 (en) 2007-07-09 2007-07-09 Ink compositions

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WO2009007968A2 true WO2009007968A2 (fr) 2009-01-15
WO2009007968A3 WO2009007968A3 (fr) 2010-02-25

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2458198A (en) * 2008-03-10 2009-09-16 Sericol Ltd Inkjet printer with solvent-based ink
US11878549B1 (en) * 2018-09-17 2024-01-23 John Sooklaris Substrate for painting, particularly alcohol ink painting

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040206270A1 (en) * 2001-10-25 2004-10-21 Luc Vanmaele Ink composition containing a particular type of dye, and corresponding ink-jet printing process
US20060073403A1 (en) * 2004-07-05 2006-04-06 Emiko Kataoka Azomethine dye and metal complex dye, as well as color toner and ink-jet ink using the same
US7132014B2 (en) * 2003-06-12 2006-11-07 Hitachi Maxell, Ltd. Oil-based pigmented ink composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040206270A1 (en) * 2001-10-25 2004-10-21 Luc Vanmaele Ink composition containing a particular type of dye, and corresponding ink-jet printing process
US7132014B2 (en) * 2003-06-12 2006-11-07 Hitachi Maxell, Ltd. Oil-based pigmented ink composition
US20060073403A1 (en) * 2004-07-05 2006-04-06 Emiko Kataoka Azomethine dye and metal complex dye, as well as color toner and ink-jet ink using the same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2458198A (en) * 2008-03-10 2009-09-16 Sericol Ltd Inkjet printer with solvent-based ink
US11878549B1 (en) * 2018-09-17 2024-01-23 John Sooklaris Substrate for painting, particularly alcohol ink painting

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IL184508A0 (en) 2008-01-20

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