WO2007072804A1 - Composition d'encre non aqueuse pour imprimantes à jets d'encre et imprimés obtenus au moyen de celle-ci - Google Patents

Composition d'encre non aqueuse pour imprimantes à jets d'encre et imprimés obtenus au moyen de celle-ci Download PDF

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Publication number
WO2007072804A1
WO2007072804A1 PCT/JP2006/325240 JP2006325240W WO2007072804A1 WO 2007072804 A1 WO2007072804 A1 WO 2007072804A1 JP 2006325240 W JP2006325240 W JP 2006325240W WO 2007072804 A1 WO2007072804 A1 WO 2007072804A1
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group
compound
ink composition
polymer
organic solvent
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PCT/JP2006/325240
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English (en)
Japanese (ja)
Inventor
Tatsurou Tsuchiya
Hideo Shibata
Masanori Kano
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Sakata Inx Corp.
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Priority to JP2007551089A priority Critical patent/JP5001855B2/ja
Publication of WO2007072804A1 publication Critical patent/WO2007072804A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
    • B41M5/52—Macromolecular coatings
    • B41M5/5254—Macromolecular coatings characterised by the use of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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 has good wettability and fixability to a base sheet whose printing surface is mainly a vinyl chloride polymer or an ethylene vinyl acetate copolymer, and has high ejection stability.
  • the present invention relates to a non-aqueous ink jet ink composition suitable for producing large-sized billboard advertisements that can be maintained for a long time, and a printed matter obtained by using the ink composition.
  • the ink jet method has a feature that it can be easily printed on sheets of paper, polymers, metals, and other hard and soft materials that can be used as a substrate for printing.
  • billboard advertisements installed outdoors are required to be lightweight, excellent in strength and durability, resistant to rain, and inexpensive, so it is easy to print on polymer sheets with these characteristics. It will be a very big advantage.
  • an ultra-wide format inkjet printer with a printing width of 2, OOOmm or more has recently appeared, making it easier to print large-format prints that have been supported by pasting together. You can now make signboards!
  • the surface of the polymer sheet is impermeable, drying mainly depends on the evaporation rate of the solvent, but an organic solvent having an excessive evaporation rate decreases the ejection stability in the ink jet system. Therefore, it is an important issue to efficiently obtain a printed material with good power on how to achieve the balance. Also, if the fixability of the ink film on the printing substrate is not good, the ink film immediately peels off the printing substrate force, making it impossible to maintain a clear printed product for a long period of time.
  • the fixability of the ink depends mainly on the performance of the fixative resin (binder resin). However, the organic solvent must dissolve the fixative resin, and in this case, the fixability depends on the organic solvent used. It depends indirectly on the physical properties.
  • the fixability is improved, so the fixability is directly related to the physical properties of the organic solvent used. It can be said that it depends on the situation. Since there are a wide variety of polymer sheets, it is necessary to design them individually according to the type of polymer used as a printing substrate in order to satisfy the above conditions and obtain a good ink composition. .
  • a polymer sheet called turbolin is often used for billboard advertisements.
  • Tarpaulin is a composite sheet in which polyester or polyamide is used as a core material, and vinyl polymers such as polysalt polybutyl and ethylene acetate butyl copolymer are laminated on both sides.
  • the ink for printing with tarpaulin is made of a material having good wettability, drying property, fixing property, etc. with respect to the above-mentioned bull polymer as a material of the sheet surface. It is necessary to use it.
  • 2005-23298 is intended for a polysilicic resin sheet as a printing substrate, but is exemplified as a suitable binder resin. There is a limit to improving the fixability of system resin, polyester resin, polyurethane resin, nitrocellulose and the like.
  • the salt-vinyl resin similar to the base material has a good fixing property, but for the solvent specifically exemplified in JP-A-2005-23298, There is a problem that the ink does not exhibit sufficient solubility and becomes the most important ink with low ejection stability when used in an ink jet system.
  • the invention described in the above Japanese Patent Application Laid-Open No. 2005-36199 is also directed to a vinyl chloride polymer sheet, but for that purpose, it depends only on the evaporation rate of the organic solvent. In addition, it cannot be said that there is some effect on the ink performance that becomes satisfactory only when the conditions of specific mathematical formulas (1) to (3) are satisfied. However, performance such as wettability and fixability that changes in any way due to factors that have nothing to do with the evaporation rate of organic solvents (the water resistance and light resistance described as effective in this invention also change) As for the technology for obtaining a high level of performance, it is completely disclosed.
  • the problem to be solved by the present invention is that the wettability and the fixability are good for a substrate whose printing surface is mainly a vinyl chloride polymer or an ethylene acetate butyl copolymer, It is an object of the present invention to provide a non-aqueous inkjet ink composition having excellent ejection stability during inkjet printing and after a long rest period.
  • the present invention provides the following non-aqueous inkjet ink composition and a printed matter obtained using the same.
  • a binder resin a group power consisting of a salt vinyl polymer, a salt vinyl bisacetate butyl copolymer and an ethylene acetate butyl copolymer is selected.
  • a non-aqueous inkjet ink composition characterized by
  • R 1 and R 2 are each independently an alkyl group having 1 to 3 carbon atoms, ⁇ is an integer of 3 to 6, and ⁇ Xs are each independently a hydrogen atom or a methyl group] .
  • Item (1) or (2) above wherein at least one of triethylene glycol dimethyl ether and triethylene glycol jetyl ether is used as the polyalkylene glycol dialkyl ether represented by the general formula (I).
  • Item 10 A non-aqueous ink jet ink composition according to the item.
  • the colorant is a pigment having a functional group that reacts with a carbodiimide group
  • the non-aqueous inkjet ink composition contains a force carbodiimide compound having a carbodiimide group as a pigment dispersant.
  • the non-aqueous inkjet ink composition of the present invention contains a binder resin, a colorant, and an organic solvent.
  • the binder resin constituting the non-aqueous ink jet ink composition of the present invention is selected from a group power consisting of a chlorinated bull-based polymer, a vinyl chloride-vinyl acetate-based copolymer, and an ethylene-vinyl acetate-based copolymer. At least one vinyl polymer is used.
  • Salt-bulb polymers include salt-bulb homopolymers (polysalt-bulls) and other small amounts of copolymerizable monomers such as vinyl acetate, ethylene, And a copolymer with a salty vinylidene, etc.).
  • the salt butyl-vinyl acetate copolymer and ethylene acetate butyl copolymer those usually used in this type of ink can be used without particular limitation.
  • the molecular weight of Noinda rosin is preferably about 2,000 to 100,000 in terms of weight average molecular weight from the viewpoints of solubility in solvents, viscosity of the resulting ink composition, ejection stability, and the like. If at least the surface layer is printed on a base material having a vinyl chloride polymer (especially polysalt vinyl) or ethylene acetate vinyl copolymer, the salt resin polymer (especially polysalt polymer) is used as a binder resin. ⁇ ⁇ Bull) is preferred.
  • the amount of the above-mentioned Noinda rosin is preferably in the range of 1 to 15% by mass, more preferably 1 to 7% by mass, based on the total amount of the non-aqueous inkjet ink composition. If the amount of the binder resin used is less than the above range, the fixing property to the substrate is not sufficient. On the other hand, if the amount exceeds the above range, the solid content increases excessively, so that the discharge stability is lowered.
  • a resin other than the above binder resin for example, an acrylic resin, a styrene acrylic resin, a styrene maleic resin, a rosin resin, a rosin Ester resin, petroleum resin, coumarone indene resin, terpene phenol resin, phenol resin, urethane resin, melamine resin, urea resin, epoxy resin, cellulose resin, xylene resin Fat, alkyd resin, aliphatic hydrocarbon resin, petital resin, maleic acid resin, fumaric acid resin, etc.
  • an acrylic resin for example, an acrylic resin, a styrene acrylic resin, a styrene maleic resin, a rosin resin, a rosin Ester resin, petroleum resin, coumarone indene resin, terpene phenol resin, phenol resin, urethane resin, melamine resin, urea resin, epoxy resin, cellulose resin, xylene resin Fat, alkyd resin, aliphatic
  • the colorant constituting the non-aqueous inkjet ink composition of the present invention the dyes used in conventional non-aqueous inkjet ink compositions, and z or Pigments can be used without particular limitation.
  • a dye when used as a colorant, a conventionally known dye can be used, and specific examples include CI Direct Black 17, 19, 22, 32, 38, 51, 71. C.I.Direct Yellow 4, 26, 44, 50, CI Direct Red 1, 4, 23, 3 31, 37, 39, 75, 80, 81, 83 , 225, 226, 227, CI direct blue 1, 1, 15, 41, 71, 86, 87, 106, 108, 199, etc., and CI Acid Black 1, 2, 24, 26, 31, 52, 107, 109, 110, 119, 154, CI Acid Yellow 1, 7, 17, 19, 19, 19, 23, 25, 29, 38, 42, 49, 61, 72, 78, 110, 127, 135, 141, 142, CI Acid Red 8, 9, 14, 14, 18.
  • Food dyes such as CI Food Yellow 3, Malachite Green (CI 420 00), Vik HJ Ablue FB (CI 44045), Methyl Biolet® FN (CI 42535), Mouth Damine F4G (CI 45160), Rhodamine 6GCP (CI 45160 ) And other basic dyes. These dyes can be used singly or in combination of two or more, and the amount used is preferably in the range of 2 to 15% by weight, more preferably 5% to the total amount of the non-aqueous inkjet ink composition. ⁇ 10% by weight. When the amount of the dye used is less than the above range, the coloring power tends to be insufficient. On the other hand, when the amount exceeds the above range, the solid content tends to increase, and thus the discharge stability tends to decrease.
  • inorganic pigments include carbon black, titanium oxide, zinc white, zinc oxide, tribon, iron oxide, aluminum oxide, silicon dioxide, kaolinite, montmorillonite, talc, barium sulfate, calcium carbonate.
  • organic pigments examples include azo, azomethine, polyazo, phthalocyanine, quinatalidone, anthraquinone, indigo, indigo, quinophthalone, benzimidazolone, isoindoline, iso Organic pigments such as indolinone are listed.
  • color index pigment black 7, pigment blue 15, 15: 1, 15: 3, 15: 4, 15: 6, 60, Pigment Green 7, 36, Pigment Red 9, 48, 49, 52, 53, 57, 97, 122, 149, 168, 177, 178, 179, 206, 207, 209, 242, 254, 255, Pigment Neolet 19, 23, 29, 30, 37, 40, 50, Pigment Yellow 12, 13, 14, 17, 20, 24, 74, 83, 86, 93, 94, 95, 109, 110, 117, 120, 125, 128, 137, 13 8, 139, 147, 148, 150, 151, 154, 155, 166, 168, 180, 185, pigment orange 36, 43, 51, 55, 59, 61, 71, 74 etc.
  • These pigments can be used singly or in combination of two or more, and the amount used is preferably 1 to: LO mass% with respect to the total amount of the non-aqueous inkjet ink composition, and more Preferably it is 2-7 mass%. If the amount of the pigment used is less than the above range, the coloring power tends to be insufficient. On the other hand, if it exceeds the above range, the viscosity tends to increase and the fluidity of the ink tends to decrease.
  • the colorant used in the non-aqueous inkjet ink composition of the present invention it is preferable to use a pigment among the above colorants from the viewpoint of light resistance.
  • a pigment When a pigment is used, it has a group (for example, a carboxyl group, a sulfonic acid group, a hydroxyl group, etc.) that reacts with a carpositimide group as a pigment from the viewpoint of stably dispersing the pigment in an organic solvent. It is preferable to use a calpositimide compound having a carposimide group among the pigment dispersants described later as a pigment dispersant.
  • polyalkylene glycol dialkyl ether represented by the general formula (I) is used in the non-aqueous ink jet ink composition. Use by containing 15-30% by mass of the total organic solvent.
  • R 1 and R 2 are each independently an alkyl group having 1 to 3 carbon atoms, n is an integer of 3 to 6, and n Xs are each independently a hydrogen atom or a methyl group] .
  • n is the number of repeating structural units represented by (—CH—CHX—O 2).
  • examples of the alkyl group having 1 to 3 carbon atoms represented by R 1 and R 2 include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • the amount of polyalkylene glycol dialkyl ether represented by the general formula (I) is less than the above range, good wettability and fixability tend not to be obtained, while if more than the above range, When using a substrate whose surface layer is made of a salty bulle polymer or an ethylene acetate bur copolymer as the substrate, the surface of the substrate may be melted too much, resulting in unevenness on the surface of the printed material. It tends to occur or cause a decrease in gloss.
  • polyalkylene glycol dialkyl ethers represented by the general formula (I) triethylene glycol dimethyl ether, triethylene glycol jetyl ether, and the like from the viewpoint of solubility of the resin and printability.
  • triethylene glycol dialkyl ether is preferred, and triethylene glycol dimethyl ether is preferred.
  • solvent other than the polyalkylene glycol dialkyl ether those conventionally used in non-aqueous ink jet ink compositions can be used.
  • an organic solvent in which the salt vinyl polymer and ethylene vinyl acetate copolymer in the surface layer of the substrate are soluble is used.
  • organic solvents include methyl ether. Noreketone, butinole acetate, dioxane, cyclohexane, cyclohexanone, ⁇ -latatam, 2-pyrrolidone, ⁇ -methyl-2-pyrrolidone, ⁇ , ⁇ ⁇ ⁇ ⁇ dimethylformamide, ⁇ , ⁇ dimethylacetamide, etc. Of these, those having a boiling point of 150 ° C or higher are preferably used.
  • the total amount of the organic solvent and the polyalkylene glycol dialkyl ether represented by the general formula (I) is 30% by mass with respect to the total organic solvent in the non-aqueous inkjet ink composition. It is preferable to use it within the following range.
  • Examples of the organic solvent used in the non-aqueous inkjet ink composition of the present invention include the above-mentioned organic solvents in which the salt vinyl polymer and the ethylene acetate butyl copolymer are soluble in the surface layer of the substrate.
  • An organic solvent can be used in combination with a salt vinyl polymer or ethylene vinyl acetate copolymer in the surface layer of the base material which is not dissolved at all or hardly dissolved.
  • Such an organic solvent is not particularly limited, but in order to stably eject ink as an ink composition for a non-aqueous ink jet, a solvent having a boiling point of 140 ° C. or higher is used. preferable.
  • the upper limit of the boiling point is not particularly limited, but is preferably 250 ° C. or less from the viewpoint of ink drying properties.
  • Specific examples include glycols such as ethylene glycol, diethylene glycolate, triethylene glycol, propylene glycol, and dipropylene glycol mononole, ethylene glycol monomethyl enoenoate acetate, and ethylene glycol monomethinoatenoate acetate.
  • Ethylene glycol monobutinoreate norecetate diethylene glycol nole monomethenoate ethere acetate, diethylene glycol nore monoethinoatenore acetate, diethylene glycol monobutyl ether acetate, propylene glycol nole monomethinoate noate acetate, dipropylene glycol Glycol alkyl ether acetates such as nomonomethyl ether acetate, ethylene glycol monobutinole Tenoré, propylene glycolenomonobutylenoateol, diethylene glycolenomonochinenoateolate, diethyleneglycolenomonobutinoylenotenole, diethyleneglycoldimethylether, diethyleneglycoljetylether, diethyleneglycolonebutinoateline, dipropyleneglycol Monomethyl ether, dipropylene glycolenomonoethylenole ether, dipropylene glycolenomonobutinor
  • non-inkjet ink composition of the present invention when a pigment is used as a colorant, it is preferable to use a pigment dispersant in combination with an organic solvent for the purpose of improving the dispersibility of the pigment.
  • pigment dispersant ionic or nonionic surfactants, anionic, power thione, or nonionic polymer compounds can be used.
  • the pigment dispersant is preferably a polymer compound.
  • a polymer compound for example, JP-A-2004-083872, republished WO2003Z076527, republished WO2004Z00 0950, calpositimide Compounds, Ajinomoto from Ajinomoto Co., Inc., SOLSPERSE from Zeneca, DISPERBY from Bicchemi, and F power from F Power Additives are preferred.
  • These pigment dispersants can be used alone or in combination.
  • a pigment having a group for example, a carboxyl group, a sulfonic acid group, a hydroxyl group, etc.
  • a pigment dispersant use should be made of a pigment having a group that reacts with a carpositimide group and a carpositimide compound having a carpositimide group in the molecule, which is a pigment dispersant capable of having a strong binding force due to a covalent bond. Is most preferred.
  • the carpositimide compound those having a side chain such as a polyester side chain, a polyether side chain, and a polyacryl side chain are more preferable than the point of pigment dispersion stability. In addition to the chain, it has a basic nitrogen-containing group.
  • carpositimide compound used in the present invention is not limited to this.
  • Preferred calpositimide compounds that can be used in the present invention are selected from the group consisting of a polyester chain, a polyether chain, and a polyacrylic chain by utilizing a reaction between a carpositimide group and a functional group capable of reacting with it.
  • Group force consisting of a polyester side chain, a polyether side chain and a polyacryl side chain, having at least one side chain selected, and having a carbodiimide equivalent of 100 to It is of 50000.
  • the carpositimide compound includes at least one side chain selected from a group power consisting of a polyester side chain, a polyether side chain, and a polyacryl side chain, and at least one basic group-containing group. In the molecule and has a calpositimide equivalent of 100 to 50,000.
  • such a reaction between a carposimide group and a functional group is sometimes referred to as a graft-in reaction, and the side chain introduced by the method is introduced as a grafted side chain.
  • the polyester side chain may be called a grafted polyester side chain
  • the polyether side chain may be called a grafted polyester side chain
  • the polyacrylic side chain may be called a grafted polyester side chain.
  • one or more kinds of calpositimide compounds can be used.
  • the “side chain” refers to a chain that is branched from the main chain when the carpositimide compound is used as the main chain.
  • one side chain formed by combining one or more of a polyester chain and a polyether chain belongs to both the “polyester side chain” and the “polyether side chain”.
  • a chain formed by combining at least one polyester chain and a polyacrylic chain belongs to both the “polyester side chain” and the “polyacrylic side chain”.
  • a combination of at least one ether chain and a polyaryl chain belongs to both the “polyether side chain” and the “polyacryl side chain”.
  • polyester chains and poly Those formed by combining one or more ether side chains and polyacryl chains belong to any of “polyester side chains”, “polyether side chains”, and “polyacryl side chains”.
  • a polyester chain, a polyether chain, and a polyaryl chain are mixed in one side chain as described above.
  • group power consisting of a polyester side chain, a polyether side chain, and a polyacryl side chain is selected. It is a side chain that satisfies the condition of “at least one kind of side chain”.
  • the "basic group nitrogen-containing group” includes not only those containing nitrogen that forms a quaternary ammonium ion in water, but also those containing nitrogen that act as a Lewis base.
  • a typical example is an amino group or a nitrogen-containing heterocyclic group.
  • carpositimide compound having a grafted side chain first, a polyester side chain, a polyether side chain and a polyacrylic compound are obtained by a grafted-in reaction based on a compound having two or more carboxylidimide groups in the molecule.
  • examples of the compound having two or more calpositimide groups in the molecule include compounds obtained by calpositimidizing a diisocyanate compound by decarboxylation reaction in the presence of a calpositimidization catalyst in an organic solvent.
  • diisocyanate compounds to be decarboxylated include hexamethylene diisocyanate, isophorone diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, Cyclohexane diisocyanate, dicyclohexylenomethane diisocyanate, xylylene diisocyanate, tetramethylene diisocyanate, tetramethylxylylene diisocyanate, etc., aliphatic, alicyclic, aromatic And araliphatic diisocyanate compounds.
  • a monoisocyanate compound may be used in combination.
  • monoisocyanate compounds include methyl isocyanate, ethyl isocyanate, propyl isocyanate, butyl isocyanate, octadecyl isocyanate, ferro-isocyanate, aliphatic, Alicyclic, aromatic, and araliphatic monoisocyanate compounds Can be mentioned.
  • usable organic solvents are those having a high boiling point and no active hydrogen that reacts with an isocyanate compound or a compound having a carpositimide group to be generated.
  • Aromatic hydrocarbons such as toluene, xylene, and jetylbenzene; ethylene glycoloresetic acetate, dipropylene glycol dibutyrate, hexylene glycoloresicetate, glyconoresiacetate, methinoreglycololeacetate, ethinoreglycol acetate
  • Glycol ether esters such as butyl butyl alcohol acetate, ethyl diglycol acetate, buty diglycol acetate; ketones such as ethyl butyl ketone, acetophenone, propiophenone, diisoptyl ketone, cyclohexanone; amyl acetate Propyl propionate, and aliphatic esters such as butyric Echir
  • examples of usable carpositimide catalysts include phospholenes, phospholenides, and the like. Specifically, 1-ethyl-3-methyl-3 phospholene oxide, 1-phenol 3- Examples thereof include methyl 3-phospholene oxide, 1-ferro-3-methyl 2-phospholene oxide, and the like.
  • a method for performing a decarboxylation reaction of an isocyanate group using these materials a known method can be used.
  • the reaction can be performed at a reaction temperature of 100 to 200 ° C in a nitrogen atmosphere.
  • examples of other methods for obtaining the above compound having a carposimide group include, for example, US Pat. No. 2941956, JP-B-47-33279, JP-A-5-178954, JP-A-6-56950 And the like.
  • a compound obtained by decarboxylation of K ( ⁇ 3) moles of diisocyanate compound is represented by the following general formula (1) 1 and ( ⁇ 1
  • a compound obtained by decarboxylation of 2 mol of diisocyanate compound and 2 mol of monoisocyanate compound can be represented by the following general formula (1) 2.
  • These are also referred to as polycarbozide imide compounds.
  • A is a residue excluding the isocyanate group of the diisocyanate one-toy compound used for the synthesis of the polycarposimide compound
  • A1 is a synthesis of the polycarposimide compound. It is a residue excluding the isocyanate group of the monoisocyanate compound used in.
  • a general formula (2) obtained by reacting a compound obtained by decarboxylating a K '( ⁇ 2) mole of diisocyanate compound with a diol compound having two hydroxyl groups ( A compound having two or more carpositimide groups represented by 2) can also be used.
  • This compound is also called a polycarbodiimide compound.
  • A is a residue excluding the isocyanate group of the diisocyanate compound used for the synthesis of the polycarbopositimide compound
  • B is a hydroxyl group of the diol compound having two hydroxyl groups.
  • m is an integer of 1 or more.
  • Such a compound represented by the general formula (1) 1 or (2) has an isocyanate group in the molecule, but it is also possible to react a compound having a functional group capable of reacting with the isocyanate group. Yes, it can be used as a compound having two or more carpositimide groups in the molecule that forms the carpositimide compound of the present invention.
  • a compound having a functional group capable of reacting with an isocyanate group a compound having a low reactivity with the remaining force rubodiimide group and selectively reacting with an isocyanate group first is preferable.
  • Low molecular monoalcohol compounds such as methanol and ethanol, polyester compounds having the above hydroxyl groups, polyalkylene glycol and monoalkyl ester compounds thereof, polymethyl metatalylate diol, polybutyl metatalylate diol, poly 2-ethylhexyl metatalylate
  • a hydroxyl group-containing compound such as a hydroxyl group-containing polyacryl compound such as a diol.
  • positive estenore, positive ethenore and polyacrylol having a formula weight of 500 to 5,000.
  • a polyester side chain, a polyether side chain or a polyacryl side chain is further introduced into the compound having two or more carposimide groups in the molecule obtained by the method as described above by a graft polymerization reaction.
  • polyester compound having the above functional group first, (1) a ring-opening polymerization compound of a cyclic ester compound using an oxycarboxylic acid, a monoalcohol, a low molecular diol compound or the like as an initiator (For example, using mono- or polyoxycarboxylic acid such as lactic acid, caproic acid, 12-hydroxystearic acid, dimethylolpropionic acid, dimethylolbutanoic acid as an initiator, ⁇ -strength prolataton, ⁇ -butyrolataton, 2-methyl Polyesters containing a carboxyl group and a hydroxyl group obtained by ring-opening polymerization of cyclic ester compounds such as caprolataton, 4-methylcaprolataton, 13-propiolatatone, ⁇ -valerolataton, 13-methyl-1- ⁇ -valerolatataton Hydride compound: Low molecular mono-rich compound such as methanol or ethanol is
  • a self-polycondensation compound of an oxycarboxylic acid for example, containing a carboxyl group and a hydroxyl group obtained by polycondensation of monooxycarboxylic acid such as lactic acid, caproic acid, 12-hydroxystearic acid, etc. And polyester compounds).
  • a low molecular diol compound and a low molecular dicarboxylic acid compound for example, ethylene glycol, 1,3-propanediol, 1,4-butanediol) 1, 6-hexanediol and other linear glycols, 1,2-propanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, ethyl
  • Low molecular diol compound components such as branched glycols such as tilpropane diol, and aromatics such as saturated or unsaturated aliphatic dicarboxylic acids such as succinic acid, adipic acid, azelaic acid, sebacic acid and maleic acid, and phthalic acid
  • a polyester diol compound containing a hydroxyl group obtained by reacting a low molecular diol compound component such as a dicarboxylic acid in the presence of an
  • a phosphoric ester compound of a ring-opening polymer of a cyclic ester compound using a monoalcohol as an initiator for example, esterification reaction of the above-mentioned polyester mono-ol compound with phosphoric acid
  • a ring-opening polymerization compound of a cyclic ester compound using an amino group-containing sulfonic acid compound as an initiator for example, taurine
  • polyester diol compounds containing a sulfonic acid obtained by ring-opening polymerization of the above cyclic ester compound using an amino group-containing sulfonic acid compound such as
  • a sulfurous acid gas adduct of a ring-opening polymer of a cyclic ester compound using a monoalcohol as an initiator for example, adding a sulfurous acid gas to the above-mentioned polyester monool compound
  • polyester diol compounds containing sulfonic acid obtained in this manner.
  • Such a polyester compound is preferably a polyester compound obtained by ring-opening polymerization of poly-strength prolatatone.
  • Ring-opening polymerization compounds of cyclic ether compounds starting from oxycarboxylic acids, monoalcohols, low molecular diol compounds, etc. for example, lactic acid, cabronic acid, 12-hydroxy stearic acid, Obtained by ring-opening polymerization of cyclic ether compounds such as ethylene oxide, propylene oxide, trimethylene oxide, tetrahydrofuran, and tetrahydropyran using mono- or polyoxycarboxylic acids such as dimethylolpropionic acid and dimethylolbutanoic acid as initiators.
  • Polyether compound containing a carboxyl group and a hydroxyl group containing a hydroxyl group obtained by ring-opening polymerization of the above cyclic ether compound using a low molecular monool compound such as methanol or ethanol as an initiator Polyether monool compound; ethylene glycol, propylene And the initiator of low molecular Jiorui ⁇ of such glycol And a polyether diol compound containing a hydroxyl group obtained by ring-opening polymerization of the above cyclic ether compound.
  • a low molecular monool compound such as methanol or ethanol
  • a phosphate ester compound of a ring-opening polymer of a cyclic ether compound using a monoalcohol as an initiator for example, the polyether monool compound is subjected to an esterification reaction with phosphoric acid.
  • a ring-opening polymerization compound of a cyclic ether compound using an amino group-containing sulfonic acid compound as an initiator for example, an amino group-containing sulfonic acid compound such as taurine is used as an initiator
  • an amino group-containing sulfonic acid compound such as taurine
  • (meth) acrylic monomer power having at least one selected from the group consisting of a carboxyl group, a sulfonic acid group, a phosphoric acid group, a hydroxyl group and an amino group. Polymerization of a monomer component containing at least one selected.
  • (Meth) acrylic polymer for example, (meth) acrylic monomer having a carboxyl group: (meth) acrylic acid, crotonic acid, maleic acid, fumaric acid, cytocholanic acid (methylmaleic acid), itaconic acid, etc.
  • an acid group-free radically polymerizable unsaturated monomer containing at least one acid group-free (meth) acrylic monomer is added in the presence of an acid group-containing chain transfer agent.
  • an acid group-containing chain transfer agent examples thereof include polyacrylic compounds containing acid groups at the ends of the molecules obtained by polymerization.
  • a compound having the above functional group and including both a polyester chain and a polyether chain, a polyacryl compound having a polyester chain, and a polyacryl compound having a polyether chain may be used.
  • a compound obtained by reacting a cyclic ester compound using polyalkylene glycol or its monoalkyl ether compound as an initiator a compound obtained by reacting a cyclic ether compound with a hydroxyl-containing polyester compound, a polyester chain
  • examples thereof include (meth) acrylic monomers containing in the molecule and polyacrylic chain compounds obtained using (meth) acrylic monomers containing polyether chains in the molecule.
  • polyester compounds polyether compounds, and polyacryl compounds
  • a polyester compound containing one carboxyl group is further reacted with an acid anhydride such as phthalic anhydride, maleic anhydride, or succinic anhydride. After obtaining the compound, it is desirable to carry out a graft reaction.
  • an acid anhydride such as phthalic anhydride, maleic anhydride, or succinic anhydride.
  • the polyester compound, the polyether compound, or the polyacryl compound exemplified above, wherein at least one compound is introduced into the molecule by graft polymerization, must further have at least one carposimide group.
  • a side chain is introduced into the polyforce carbodiimide compound represented by the general formula (1) 1 by a graft reaction, the following general formula (3)
  • a carpositimide compound represented by the formula (K-1 m + n)
  • ⁇ is a residue excluding the isocyanate group of the diisocyanate compound used for the synthesis of the polycarbodiimide compound.
  • X is the same or different and is a trivalent linking group obtained by reacting a carpositimide group with a functional group capable of reacting with it.
  • Y is the same or different and is a polyester chain, a polyether chain or a polyacrylic chain. Yes, m and n each represent an integer of 1 or more.
  • the linking group formed from the reaction of a carbodiimide group and a carboxyl group is represented by the following general formulas (4), (5)
  • the linking group formed from the reaction between the group and the hydroxyl group is represented by the following general formulas (6) and (7)
  • the linking group formed from the reaction between the carpositimide group and the amino group is represented by the following general formula (8)
  • the linking group formed from the reaction between the carpositimide group and the sulfonic acid group is represented by the following general formula (9)
  • the linking group formed from the reaction between the carpositimide group and the phosphoric acid group is represented by the following general formula (10). expressed.
  • R represents a hydrogen atom or a hydrocarbon group having 1 or more carbon atoms.
  • the carpositimide compound represented by the general formula (3) has an isocyanate group in the molecule, but it is also possible to react a compound having a functional group capable of reacting with the isocyanate group.
  • the compound represented by the formula (11) can also be used as a carpositimide compound in the present invention.
  • Z 1 and Z 2 are each independently an active hydrogen of the functional group of a compound having a functional group capable of reacting with an isocyanate group, which may have a different structure.
  • A is a residue excluding the isocyanate group of the diisocyanate compound used in the synthesis of the polycarposimide compound.
  • X is the same or different, and a trivalent linking group obtained by reacting a carpositimide group with a functional group capable of reacting with it
  • Y is the same or different, and is a polyester chain, a polyether chain or a polyacryl chain, m and n each represents an integer of 1 or more.
  • a compound having a functional group capable of reacting with an isocyanate group a compound having a low reactivity with the remaining force rubodiimide group and selectively reacting with an isocyanate group first is preferable.
  • Low molecular monoalcohol compounds such as methanol and ethanol, polyester compounds containing the above hydroxyl groups, polyalkylene glycol and its monoalkyl ester compounds, polymethyl metatalylate diol, polybutyl metatalylate diol, poly 2-ethylhexyl meta
  • a hydroxyl group-containing compound such as a hydroxyl group-containing polyacryl compound such as tallylate diol.
  • a polyester chain, a polyether chain or a polyacryl chain having a formula weight of 500 to 5000 is preferably formed.
  • Conventional methods can be used for the reaction with a hydroxyl group or the like.
  • the above-mentioned carpositimide-based compound is a compound containing at least one carposimide group and a grafted polyester chain, a daffodied polyether chain, or a grafted polyacrylic chain, and reacts each reaction material. Even if the order in which they are made is different, the performance obtained is not different if the finally obtained compounds have the same molecular structure.
  • a compound having at least one chain selected from the group consisting of a polyester chain having a functional group that reacts with a carpositimide group, a polyether chain, and a polyacryl chain.
  • a carpositimide group compound having to introduce the side chain into the molecule, that is, to introduce a grafted polyester chain, a grafted polyether chain or a grafted polyacrylic chain
  • a functional group-containing polyester compound that reacts with a carbodiimide group, a functional group-containing polyether compound that reacts with a carbodiimide group, or a functional group-containing polyether compound that reacts with a carbodiimide group is synthesized and then reacted with a carbodiimide group.
  • a functional group-containing polyester compound that reacts with a carbodiimide group, a functional group-containing polyether compound that reacts with a carbodiimide group, or a functional group-containing polyether compound that reacts with a carbodiimide group is synthesized and then reacted with a carbodiimide group.
  • a compound into a molecule of a carpositimide compound after reacting a compound having a functional group that reacts with a carpositimide group and a carposimide group (compound having a), a polyester chain, a polyether chain, It can also be carried out by introducing into the molecule a compound that forms at least one selected group force consisting of acrylic chains.
  • a grafted polyester side chain or a grafted polyether side chain an oxycarboxylic acid is first reacted with a carpositimide group, and a hydroxyl group is introduced into the molecule of the force rubodiimide compound. Thereafter, a method of ring-opening polymerization of a cyclic polyester compound or a cyclic polyether compound and graft-bonding the polyester chain or the polyether chain may be used.
  • a method of grafting a polyacrylic chain after first reacting an oxycarboxylic acid with a carpositimide group to introduce a hydroxyl group into the molecule of the compound having a carposimide group may be.
  • Typical specific examples of the carboimide compound having the grafted side chain and having the basic group-containing group in the molecule include (1) the above general formula (1) 1 or (2 ), A tertiary amine amino group or a basic nitrogen that does not participate in the reaction between the isocyanate group of the polycarbodiimide compound, a hydroxyl group suitable as a functional group capable of selectively reacting with the isocyanate group, and a carpositimide group or an isocyanate group.
  • the calpositimide group of the polycarbopositimide compound of the above general formula (1) 1 or (2) And the isocyanate group of the compound in which at least one selected from the group force consisting of a polyester chain, a polyether chain, and a polyacrylic chain is introduced into the molecule using the reaction with a functional group capable of reacting with A compound having a hydroxyl group suitable as a functional group capable of selectively reacting with the isocyanate group, and a tertiary amino group or basic nitrogen-containing heterocyclic group not involved in the reaction between the carpositimide group and the isocyanate group.
  • the resulting polycarbopositimide compound having two or more calpositimide groups represented by the general formula (2) is a diol compound having two hydroxyl groups.
  • the reaction between the carpositimide group of this compound and a functional group capable of reacting with it Utilizing the group power consisting of polyester chain, polyether chain and polyacrylic chain, introduce at least one selected in the molecule And the like.
  • a compound having a functional group capable of reacting with an isocyanate group a compound having a low reactivity with the remaining force rubodiimide group and selectively reacting with an isocyanate group first is preferred.
  • methanol Low molecular monoalcohol compounds such as ethanol, polyester compounds having the above hydroxyl groups, polyalkylene glycols and monoalkyl ester compounds thereof, polymethyl methacrylate diol, polybutyl methacrylate diol, poly 2-ethyl
  • hydroxyl group-containing compounds such as hydroxyl group-containing polyacryl compounds such as xylmetatalylate diol.
  • examples of the compound having one hydroxyl group and a tertiary amino group include N, N-dialkylalkanolamines such as N, N-dimethylethanolamine and N, N-jetylethanolamine.
  • Examples include compounds, ethylene oxide adducts of secondary amine compounds, and reactants of secondary amine compounds and epoxy compounds.
  • Examples of the compound having two hydroxyl groups and a tertiary amino group include, for example, N-alkyldianolamine compounds such as N-methyljetanolamine and N-ethyljetanolamine, and primary amine compounds. And ethylene oxide adducts, reaction products of primary amine compounds and epoxy compounds, and the like.
  • examples of the compound having a hydroxyl group and a basic nitrogen-containing heterocyclic group include tertiary basic nitrogen such as hydroxypyridine, pyridinemethanol, pyridineethanol, pyridine, pyrazine, triazine, quinoline and the like.
  • tertiary basic nitrogen such as hydroxypyridine, pyridinemethanol, pyridineethanol, pyridine, pyrazine, triazine, quinoline and the like.
  • Compounds containing a heterocyclic ring and a hydroxyl group can be used.
  • heterocyclic compounds containing secondary basic nitrogen such as piperidine or piperazine can be used by alkylating to tertiary and adding a hydroxyl group.
  • the number average molecular weight of the carpositimide compound used in the present invention is preferably 1,000 or more and 1,000,000 or less. High number average molecular weight of carbodiimide compounds When it becomes too much, it becomes difficult to obtain an ink composition having an appropriate viscosity as a non-aqueous ink jet printing ink composition.
  • the dispersant is appropriately selected according to the type of pigment and the type of organic solvent to be used.
  • non-aqueous ink jet ink composition of the present invention various additives such as a plasticizer, a surface conditioner, an ultraviolet light inhibitor, a light stabilizer, and an antioxidant are used as necessary. can do.
  • the ink thread composition for non-aqueous inkjet according to the present invention includes, for example, a wet circulation mill, a bead mill, a ball mill, a sand mill, an attritor, a roll mill, an agitator, a Henschel mixer, a colloid mill, an ultrasonic homogenizer, and a high pressure homogenizer.
  • a wet circulation mill for example, a wet circulation mill, a bead mill, a ball mill, a sand mill, an attritor, a roll mill, an agitator, a Henschel mixer, a colloid mill, an ultrasonic homogenizer, and a high pressure homogenizer.
  • a disperser such as a pearl mill
  • the viscosity of the non-aqueous ink jet ink composition is 2 to: LOmPa's It can be obtained by adjusting as follows.
  • the content of the total organic solvent in the non-aqueous inkjet ink composition of the present invention is determined based on the total amount of the ink composition, binder resin, colorant (including pigment dispersant when a pigment is used), and if necessary. It is an amount obtained by subtracting the total amount of other additives, but it is preferable to appropriately change the ink viscosity to be within the above range.
  • SC-540 was loaded with the non-aqueous inkjet ink compositions of Examples 1 to 5 and Comparative Examples 1 and 2, and printed on a polychlorinated bull sheet (trade name: Capjet Dalos Burner, Film Lux). Printed materials of Examples 1 to 5 and Comparative Examples 1 and 2 were obtained.
  • Viscosity The viscosity at 25 ° C. of each of the non-aqueous ink jet ink compositions of Examples 1 to 5 and Comparative Examples 1 and 2 was measured using a viscometer (RE100L type manufactured by Toki Sangyo Co., Ltd.).
  • the non-aqueous inkjet ink composition of the present invention has good wettability and adhesion to a substrate whose printing surface is mainly composed of a vinyl chloride vinyl polymer or an ethylene vinyl acetate copolymer. Furthermore, it has excellent ejection stability during ink jet printing and even after a long pause.

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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)
  • Chemical Kinetics & Catalysis (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Ink Jet (AREA)

Abstract

L'invention concerne une composition d'encre non aqueuse pour imprimantes à jets d'encre, possédant une bonne mouillabilité et une bonne fixabilité sur une base dont la surface d'impression est composée principalement d'un polymère de chlorure de vinyle ou d'un copolymère d'acétate d'éthylène-vinyle et possédant également une excellente stabilité à l'éjection. L'invention concerne, plus précisément, une composition d'encre non aqueuse pour imprimantes à jets d'encre renfermant au moins un polymère de vinyle comme résine de liant sélectionné dans le groupe comprenant des polymères de chlorure de vinyle, des copolymères d'acétate de chlorure de vinyle-vinyle et des copolymères d'acétate d'éthylène-vinyle, un agent colorant et un solvant organique. Cette composition d'encre non aqueuse pour imprimantes à jets d'encre est caractérisée en ce que le solvant organique renferme un éther dialkyle glycol de polyalkylène de formule générale (I) dans une quantité comprise entre 15 et 30% en masse par rapport à la masse totale du solvant organique. Formule (I) R1-O-(-CH2-CHX-O-)n-R2 (I)
PCT/JP2006/325240 2005-12-20 2006-12-19 Composition d'encre non aqueuse pour imprimantes à jets d'encre et imprimés obtenus au moyen de celle-ci WO2007072804A1 (fr)

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JP2009013206A (ja) * 2007-06-29 2009-01-22 Fujifilm Corp インクジェットインク及びその製造方法、カラーフィルタ及びその製造方法、表示装置、並びに機能膜の形成方法
JP2009051904A (ja) * 2007-08-24 2009-03-12 General Technology Kk 油性インクジェットインク
JP2009074034A (ja) * 2007-02-23 2009-04-09 General Technology Kk 油性インクジェットインク
JP2009132846A (ja) * 2007-12-03 2009-06-18 Mimaki Engineering Co Ltd インクジェット用インク
JP2011122087A (ja) * 2009-12-11 2011-06-23 Mimaki Engineering Co Ltd インクジェット印刷用インク
JP2012052057A (ja) * 2010-09-03 2012-03-15 Seiko Epson Corp インクジェット記録用非水系インク組成物、インクセット、およびインクジェット記録方法
JP2012057043A (ja) * 2010-09-08 2012-03-22 Toyo Ink Sc Holdings Co Ltd 水性インキ組成物
CN102757695A (zh) * 2012-08-08 2012-10-31 王文滔 Eva油墨
JP2014047227A (ja) * 2012-08-29 2014-03-17 General Co Ltd 非水性インクジェットインク
WO2015020128A1 (fr) 2013-08-07 2015-02-12 サカタインクス株式会社 Composition d'encre pour jet d'encre non aqueuse et matière imprimée obtenue l'utilisant
JP2017141462A (ja) * 2017-03-22 2017-08-17 セイコーエプソン株式会社 インクジェット用非水系インク、およびインクジェット記録方法
WO2018030088A1 (fr) 2016-08-10 2018-02-15 サカタインクス株式会社 Composition d'encre non aqueuse
KR20180030558A (ko) 2015-07-30 2018-03-23 사카타 인쿠스 가부시키가이샤 비수성 잉크젯용 잉크 조성물
WO2018105696A1 (fr) 2016-12-09 2018-06-14 サカタインクス株式会社 Composition d'encre non aqueuse pour jet d'encre
US10767067B2 (en) 2016-04-28 2020-09-08 Sakata Inx Corporation Non-aqueous inkjet ink composition
US10781327B2 (en) 2015-02-24 2020-09-22 Seiko Epson Corporation Ink jet ink composition and ink jet recording method
US10800162B2 (en) 2016-01-27 2020-10-13 Seiko Epson Corporation Non-aqueous ink jet composition
US10899941B2 (en) 2016-08-19 2021-01-26 Sakata Inx Corporation Yellow ink composition for nonaqueous inkjet
US10919311B2 (en) 2015-02-24 2021-02-16 Seiko Epson Corporation Ink jet ink composition, ink jet recording method, and ink set
WO2021085511A1 (fr) 2019-10-30 2021-05-06 サカタインクス株式会社 Composition d'encre pour impression à jet d'encre non aqueux
WO2021085510A1 (fr) 2019-10-30 2021-05-06 サカタインクス株式会社 Composition d'encre pour jet d'encre non aqueux

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JP2009074034A (ja) * 2007-02-23 2009-04-09 General Technology Kk 油性インクジェットインク
JP2009013206A (ja) * 2007-06-29 2009-01-22 Fujifilm Corp インクジェットインク及びその製造方法、カラーフィルタ及びその製造方法、表示装置、並びに機能膜の形成方法
JP2009051904A (ja) * 2007-08-24 2009-03-12 General Technology Kk 油性インクジェットインク
JP2009132846A (ja) * 2007-12-03 2009-06-18 Mimaki Engineering Co Ltd インクジェット用インク
JP2011122087A (ja) * 2009-12-11 2011-06-23 Mimaki Engineering Co Ltd インクジェット印刷用インク
JP2012052057A (ja) * 2010-09-03 2012-03-15 Seiko Epson Corp インクジェット記録用非水系インク組成物、インクセット、およびインクジェット記録方法
JP2012057043A (ja) * 2010-09-08 2012-03-22 Toyo Ink Sc Holdings Co Ltd 水性インキ組成物
CN102757695A (zh) * 2012-08-08 2012-10-31 王文滔 Eva油墨
JP2014047227A (ja) * 2012-08-29 2014-03-17 General Co Ltd 非水性インクジェットインク
WO2015020128A1 (fr) 2013-08-07 2015-02-12 サカタインクス株式会社 Composition d'encre pour jet d'encre non aqueuse et matière imprimée obtenue l'utilisant
US11718100B2 (en) 2015-02-24 2023-08-08 Seiko Epson Corporation Ink jet ink composition, ink jet recording method, and ink set
US10919311B2 (en) 2015-02-24 2021-02-16 Seiko Epson Corporation Ink jet ink composition, ink jet recording method, and ink set
US10781327B2 (en) 2015-02-24 2020-09-22 Seiko Epson Corporation Ink jet ink composition and ink jet recording method
KR20180030558A (ko) 2015-07-30 2018-03-23 사카타 인쿠스 가부시키가이샤 비수성 잉크젯용 잉크 조성물
US10767065B2 (en) 2015-07-30 2020-09-08 Sakata Inx Corporation Non-aqueous inkjet ink composition
US10800162B2 (en) 2016-01-27 2020-10-13 Seiko Epson Corporation Non-aqueous ink jet composition
US10767067B2 (en) 2016-04-28 2020-09-08 Sakata Inx Corporation Non-aqueous inkjet ink composition
WO2018030088A1 (fr) 2016-08-10 2018-02-15 サカタインクス株式会社 Composition d'encre non aqueuse
US10899941B2 (en) 2016-08-19 2021-01-26 Sakata Inx Corporation Yellow ink composition for nonaqueous inkjet
KR20190088978A (ko) 2016-12-09 2019-07-29 사카타 인쿠스 가부시키가이샤 비수성 잉크젯용 잉크 조성물
WO2018105696A1 (fr) 2016-12-09 2018-06-14 サカタインクス株式会社 Composition d'encre non aqueuse pour jet d'encre
JP2017141462A (ja) * 2017-03-22 2017-08-17 セイコーエプソン株式会社 インクジェット用非水系インク、およびインクジェット記録方法
WO2021085511A1 (fr) 2019-10-30 2021-05-06 サカタインクス株式会社 Composition d'encre pour impression à jet d'encre non aqueux
WO2021085510A1 (fr) 2019-10-30 2021-05-06 サカタインクス株式会社 Composition d'encre pour jet d'encre non aqueux

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