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WO2015162747A1 - Composition de résine de polyuréthane pour encre, et encre d'impression - Google Patents

Composition de résine de polyuréthane pour encre, et encre d'impression Download PDF

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Publication number
WO2015162747A1
WO2015162747A1 PCT/JP2014/061529 JP2014061529W WO2015162747A1 WO 2015162747 A1 WO2015162747 A1 WO 2015162747A1 JP 2014061529 W JP2014061529 W JP 2014061529W WO 2015162747 A1 WO2015162747 A1 WO 2015162747A1
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WO
WIPO (PCT)
Prior art keywords
ink
resin
resin composition
printing
group
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Ceased
Application number
PCT/JP2014/061529
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English (en)
Japanese (ja)
Inventor
貴司 中井
正典 岩橋
茂和 高橋
富宏 大橋
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DIC Graphics Corp
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DIC Graphics Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by DIC Graphics Corp filed Critical DIC Graphics Corp
Priority to PCT/JP2014/061529 priority Critical patent/WO2015162747A1/fr
Publication of WO2015162747A1 publication Critical patent/WO2015162747A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • 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
    • C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds

Definitions

  • the present invention relates to a printing ink suitable for solvent recovery and reuse in which the solvent is an organic solvent and / or water, and the volatile solvent is easily recovered during printing. Furthermore, the present invention relates to a printing ink suitable for solvent recovery and reuse in which 95% or more of the solvent is composed of a single organic solvent and water, and the recovery of the volatile solvent is facilitated during printing.
  • the solvent species is designed to have a composition of toluene alone, and the volatile solvent is recovered and reused. This is because, in the case of a single solvent composition, the recovered solvent can also be obtained in a single composition, so that it can be easily reused as an adhesive or ink dilution solvent.
  • an ink in which an alcohol-soluble urethane urea resin having a hydroxyl group is used to promote recovery and reuse (for example, see Patent Document 1).
  • this technique has insufficient pigment dispersibility.
  • linear urethane prepolymer (A) having an isocyanate group bonded to carbon of an aliphatic hydrocarbon at both ends and further having a carboxyl group in the molecular side chain;
  • the object of the present invention is to provide an ink resin composition excellent in printability, in particular, excellent in plate fog, and excellent in pigment dispersion stability without adding a pigment dispersant, and the composition. It is to provide printing ink.
  • the present invention relates to an ink resin composition containing a polyurethane resin (a) reacted with a compound (I) having an amino group and / or an imino group covalently bonded to carbon in the resin, and the composition.
  • a printing ink contained, a printed matter using the printing ink, and a laminate laminate using the printing ink.
  • the present invention it is possible to provide a printing ink having a good plate fogging property and a good pigment stability, and a printed material or laminate laminate.
  • the urethane resin used in the present invention is not particularly limited as long as a component having an amino group, an imino group and a derivative thereof is bonded to a side chain or a main chain, and various urethane resins can be used.
  • a urethane resin is produced by reacting polyols and polyisocyanates, a compound (I) having an amino group and / or an imino group covalently bonded to carbon in the resin [hereinafter referred to as compound (I) ].
  • compound (I) a compound having an amino group and / or an imino group covalently bonded to carbon in the resin
  • compound (I) A method in which polyols and polyisocyanates are reacted in excess of isocyanate groups, and the resulting isocyanate-terminated urethane resin is reacted with compound (I).
  • polyols examples include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 2-ethyl-2butyl-1,3-propanediol, 1, 3-butanediol, 1,4-butanediol, neopentyl glycol, pentanediol, 3-methyl-1,5-pentanediol, hexanediol, octanediol, 1,4-butynediol, 1,4-butylenediol, diethylene glycol Saturated, such as triethylene glycol, polypropylene glycol, dipropylene glycol, glycerin, trimethylolpropane, trimethylolethane, 1,2,6-hexanetriol, 1,2,4-butanetriol, sorbitol, pentaesitol Bad Japanese low mo
  • polyisocyanate compound examples include 1,5-naphthylene diisocyanate, 4,4′-diphenylmethane diisocyanate (MDI), 4,4′-diphenyldimethylmethane diisocyanate, 4,4′-dibenzyl isocyanate, and dialkyldiphenylmethane diisocyanate.
  • MDI 4,4′-diphenylmethane diisocyanate
  • MDI 4,4′-diphenylmethane diisocyanate
  • 4,4′-diphenyldimethylmethane diisocyanate 4,4′-dibenzyl isocyanate
  • dialkyldiphenylmethane diisocyanate examples include 1,5-naphthylene diisocyanate, 4,4′-diphenylmethane diisocyanate (MDI), 4,4′-diphenyldimethylmethane diisocyanate, 4,4′-dibenzyl isocyan
  • Aromatic diisocyanates such as tetraalkyldiphenylmethane diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, tolylene diisocyanate; butane-1,4-diisocyanate, hexamethylene diisocyanate, isopropylene diisocyanate, methylene diisocyanate, 2, Aliphatic diisocyanates such as 2,4-trimethylhexamethylene diisocyanate and lysine diisocyanate Fats such as cyclohexane-1,4-diisocyanate, xylylene diisocyanate, isophorone diisocyanate, dimeryl diisocyanate, dicyclohexylmethane-4,4′-diisocyanate, 1,3-bis (isocyanatemethyl) cyclohexane, methylcyclohexane diisocyanate, norbornane di
  • Examples of the compound (I) having an amino group and / or imino group covalently bonded to carbon in the resin used in the present invention include polyethyleneimine, polyvinylamine, polyallylamine, polyornithine, polylysine and polyamidoamine.
  • the polyallylamine polymerizes N, N-dimethylallylamine, N, N-diethylallylamine, N, N-dipropylallylamine, N, N-dibutylallylamines as monomers forming N, N-dialkylallylamine units. Is obtained. Examples of these include, for example, various products of PAA manufactured by Knitbow Medical Co., Ltd.
  • the polyethyleneimine is obtained by polymerizing ethyleneimine. Examples of these include Nippon Catalytic Epomin Co., Ltd.
  • the polyvinylamine can be obtained, for example, by hydrolyzing a polymer of N-vinylcarboxylic acid amide. Examples of these include, for example, various products of Dianitics Co., Ltd.
  • Examples of the polyamidoamine include an anamide manufactured by Air Products.
  • the polyornithine and polylysine can be obtained by polycondensation of carboxyl group and amino group in ornithine and lysine, respectively.
  • the polyvinylamine or polyamidoamine has an amino group or imino group in the molecule, it reacts easily with the urethane resin in which the isocyanate group remains by using active hydrogen of these functional groups.
  • the polyurethane resin (a) in the present invention is not particularly limited as long as it has a urethane structure in the skeleton, and includes polyurethane, polyurethane polyurea and the like.
  • the polyurethane resin (a) that can be dissolved in a single organic solvent, a mixture of a polyester diol (A) and a polyether diol (B), and an isocyanate compound It is a polyurethane polyurea resin obtained by reacting the urethane prepolymer obtained by reacting (C) with the compound (I), the chain extender (D) and the reaction terminator (E).
  • the mixing ratio [(A) / (B)] (weight ratio of solid content) of the polyester diol (A) and the polyether diol (B) is 15 or more because the heat resistance of the cured product is good. It is preferably 85 or less, and [(A) / (B)] is particularly preferably 30/70 to 70/30, because the cured product has good substrate adhesion.
  • the polyester diol (A) preferably has a number average molecular weight of 400 or more because of good coating film adhesion and solubility in an alcohol solvent. Is preferably a number average molecular weight of 3000 or less.
  • polyether diol (B) preferably has a number average molecular weight of 400 to 4,000.
  • the ratio (NCO / OH) of the hydroxyl group (OH) in the polyester diol (A) and the polyether diol (B) to the isocyanate group (NCO) in the isocyanate compound (C) is 2.0 to 3.0. It is preferable. When the ratio is less than 2.0, sufficient alkali resistance tends not to be obtained. When the ratio is more than 3.0, the solubility of the resulting prepolymer tends to decrease.
  • the above-described polyurethane polyurea resin preferably has one or more of hydroxyl group, carboxyl group and thiol group in the molecule.
  • dimethylolpropionic acid 2,2-dimethylolacetic acid, 2,2-dimethylolbutyric acid, 2,2-dimethylolpentanoic acid, dimethylolalkanoic acid such as dihydroxypropionic acid, dihydroxysuccinic acid And dihydroxybenzoic acid.
  • dimethylolpropionic acid and 2,2-dimethylolbutyric acid are preferable from the viewpoint of reactivity and solubility.
  • the dihydroxycarboxylic acid needs to be blended in the range of 0.5 to 4.0% by weight of the total amount of the dihydroxycarboxylic acid based on the total polyol including the dihydroxycarboxylic acid. If the total solid content is less than 0.5% by weight, the effect of reducing the trapping failure is poor. If the total solid content exceeds 4.0% by weight, the viscosity of the resin is remarkably increased or gelation is desirable. This is not preferable because the pigment / resin ratio cannot be achieved so as to achieve both the printing viscosity and the physical properties of the ink film.
  • an alkanolamine having 2 to 20 carbon atoms (mono-, di- or triethanolamine, isopropanolamine, aminoethylethanolamine, etc.) is preferable.
  • Examples of the compound having a thiol group include 1-mercapto-1,1-methanediol, 1-mercapto-1,1-ethanediol, 3-mercapto-1,2-propanediol (thioglycerin), 2-mercapto -1,2-propanediol, 2-mercapto-2-methyl-1,3-propanediol, 2-mercapto-2-ethyl-1,3-propanediol, 1-mercapto-2,2-propanediol, 2 -Mercaptoethyl-2-methyl-1,3-propanediol, 2-mercaptoethyl-2-ethyl-1,3-propanediol, and the like are preferable.
  • the compound (I) used in the present invention is preferably contained in an amount of 0.1 to 2% by weight of the polyurethane resin from the viewpoint of improving plate fogging in addition to drying and adhesion.
  • the amino group-containing chain extender (D) used for the urethane prepolymer includes ethylenediamine, propylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, isophorone.
  • reaction terminator examples include dialkylamines such as di-n-butylamine and alcohols such as ethanol and isopropyl alcohol. Furthermore, amino acids such as glycine and L-alanine can be used as a reaction terminator when it is desired to introduce a carboxyl group into the polyurethane polyurea resin.
  • the carboxylic acid is introduced into the resin by using dihydroxycarboxylic acid, the ink coating film is hardly dissolved by the ionic bond with the amino group introduced at the resin terminal, which is preferable in terms of improving the trapping failure. .
  • Examples of the white colorant used in the printing ink of the present invention include organic and inorganic pigments and dyes used in general inks, paints, recording agents and the like. Specific examples include titanium oxide, zinc oxide, aluminum oxide, calcium carbonate, zinc sulfide, magnesium oxide, barium sulfate, magnesium sulfate, chromium oxide, and silica. In particular, it is preferable to use titanium oxide from the viewpoints of colorability, hiding properties, chemical resistance, weather resistance, and the like.
  • Non-white inorganic pigments include pigments such as carbon black, aluminum, mica (mica), and bengara (iron (III) oxide).
  • Aluminum is generally in the form of a powder or paste, but is preferably used in the form of a paste from the viewpoint of easy handling and safety for the human body, and a leafing or non-leafing type is used depending on the demand for brightness and density.
  • Examples of the colored colorant used in the printing ink of the present invention include organic and inorganic pigments and dyes used in general inks, paints, and recording agents.
  • pigments such as azo, phthalocyanine, dioxazine, quinacridone, anthraquinone, perinone, perylene, thioindigo, isoindolinone, quinophthalone, azomethine azo, diketopyrrolopyrrole, isoindoline, etc. Can be mentioned.
  • the colorant is preferably contained in a proportion of 1 to 50% by mass with respect to the total weight of the printing ink in order to develop a sufficient concentration and coloring power in the printing ink.
  • These colorants can be used alone or in combination of two or more.
  • the resin alone can be dispersed, but a dispersant can be used in combination for further dispersing the pigment stably.
  • a dispersant can be used in combination for further dispersing the pigment stably.
  • cationic, anionic, nonionic, amphoteric surfactants can be used.
  • the amount of the dispersant used is preferably 0.05% by mass or more with respect to the total weight of the ink from the viewpoint of the storage stability of the ink and 5% by mass or less from the viewpoint of the suitability for lamination. Further, it is particularly preferably contained in the range of 0.1 to 2% by mass.
  • the printing ink of the present invention can be produced by dissolving or dispersing a resin, a colorant and the like in a solvent. Specifically, a pigment dispersion in which a pigment is dispersed in an organic solvent with the resin, and if necessary, with the dispersant is manufactured, and other compounds are blended with the obtained pigment dispersion as necessary. Thus, an ink can be produced.
  • the particle size distribution of the pigment dispersion can be optimized by appropriately adjusting the diameter of the grinding media of the dispersion grinder, the filling rate, the dispersion treatment time, the discharge speed of the pigment dispersion, the viscosity of the pigment dispersion, and the like. it can.
  • the disperser generally used, for example, a roller mill, a ball mill, a pebble mill, an attritor, a sand mill and the like can be used.
  • the viscosity of the printing ink produced by the above method is 10 mPa ⁇ s or more at a liquid temperature of B-type viscometer at 25 ° C., from the viewpoint of preventing the precipitation of the pigment and dispersing it appropriately. From the viewpoint, it is preferably in the range of 1000 mPa ⁇ s or less.
  • the printing ink of the present invention can be used in known printing methods such as gravure printing and flexographic printing.
  • it is diluted with a diluent solvent to a viscosity and concentration suitable for gravure printing, and is supplied to each printing unit alone or mixed.
  • the printing ink of the present invention can be obtained as a printed matter and a covering by applying the printing and application to the various film and sheet-like substrates using the above printing method, and drying and fixing by oven drying.
  • Film and sheet base materials include polyolefin resins such as polyethylene and polypropylene, polyester resins such as polyethylene terephthalate, polycarbonate and polylactic acid, polystyrene resins such as polystyrene, AS resin and ABS resin, nylon, polyamide and poly Examples include vinyl chloride, polyvinylidene chloride, cellophane, paper, aluminum, and composite materials thereof.
  • the base material may be subjected to vapor deposition coating treatment and / or polyvinyl alcohol coating treatment on the surface of metal oxide or the like, and may further be subjected to surface treatment such as corona treatment.
  • the usual extrusion lamination (extrusion laminating) method in which molten polyethylene resin is laminated on the printed surface of the printed material through various anchor coating agents such as imine, isocyanate, polybutadiene, and titanium, and urethane on the printed surface
  • the printing ink of the present invention was used by a known laminating process such as a dry laminating method in which an adhesive such as a system is applied and a plastic film is laminated, or a direct laminating method in which a molten polypropylene is directly pressed and laminated on a printing surface. Laminate laminate is obtained
  • the printing ink of the present invention can easily recover and reuse the solvent vapor generated in the printing and drying processes. More preferably, a single alcohol solvent and a polyurethane polyurea resin soluble in the alcohol are used, and the alcohol component can be easily separated and recovered from the solvent vapor generated in the printing and drying processes.
  • the recovered solvent is a single alcohol, and unlike the ester solvent, there is no by-product such as carboxylic acid, and the purification process can be simplified.
  • urethane prepolymer (A1) 264.8 parts was added and reacted at 40 ° C. for 4 hours to give a polyurethane having a solid content of 30%, a weight average molecular weight of 11,200, and an amine value of 1.2 (mgKOH / g).
  • An alcohol solution (X1) of polyurea resin was obtained.
  • black ink was prepared by the method described later, and various performances were evaluated.
  • Azo initiator 2,2'-bis (N-phenylamidinyl) -2,2'-azopropane dihydrochloride (14 g) is dissolved in distilled water (20 ml) and added. Since it generates heat after 2 hours, it is cooled while stirring and kept at a liquid temperature of 48 to 52 ° C. Ten hours after the addition of the initiator, stirring was stopped, and the resulting solution was added to excess methanol to obtain a white polymer (polyallylamine hydrochloride) precipitate. The resulting precipitate is filtered off and washed with methanol to remove monoallylamine hydrochloride.
  • polyallylamine hydrochloride 30 g was dissolved in 270 g of distilled water, hydrochloric acid was removed through a strongly basic ion exchange resin (Amberlite-IRA-402), and the developing solution (polyallylamine aqueous solution) was freeze-dried. Polyallylamine (paa-6) was obtained. The resulting polyarylamine had a weight average molecular weight of 2,000.
  • Example 1 If 100 parts of 1.5 mm glass beads are charged in a glass bottle and Example 1 is taken as an example, 44 parts of IPA and 11 parts of MONARCH 460 (manufactured by Cabot Specialty Chemicals, Inc.) as carbon black are obtained in Production Example 1. After adding 40 parts of polyurethane polyurea resin X1 and 5 parts of water, dispersion was performed with a paint conditioner for 1 hour, and then glass beads were filtered with a wire mesh to obtain black ink XB-1.
  • MONARCH 460 manufactured by Cabot Specialty Chemicals, Inc.
  • Comparative Example 1 Using resin Y1 obtained in Comparative Production Example 1, an ink was prepared in the same procedure as in Example 1 at the blending ratio shown in Table 2.
  • Comparative Example 2 100 parts of 1.5mm glass beads in a glass bottle, 43 parts of IPA, 11 parts of MONARCH 460 (Cabot Specialty Chemicals, Inc.) as carbon black, 1 part of Floren G-700 (manufactured by Kyoeisha Chemical Co., Ltd.) Then, 40 parts of polyurethane polyurea resin Y1 and 5 parts of water were charged, and after dispersion for 1 hour with a paint conditioner, the glass beads were filtered with a wire mesh to obtain black ink YB-2.
  • the inks listed in Tables 1 and 2 are developed on a treated surface of a biaxially stretched polyethylene terephthalate film (E5102, 12 ⁇ m, manufactured by Toyobo Co., Ltd.) having a corona discharge treatment on one side by a bar coater # 4. After the Nichiban cellophane tape 18 mm width was brought into close contact with the color development surface, the cellophane tape was peeled off vigorously in the vertical direction, and the area ratio of the ink film adhering to the cellophane tape was visually evaluated.
  • a biaxially stretched polyethylene terephthalate film E5102, 12 ⁇ m, manufactured by Toyobo Co., Ltd.
  • the inks listed in Tables 1 and 2 were diluted with IPA, and diluted with Zaan Cup No. 3 manufactured by Koiso Co., Ltd. so as to be 16 seconds.
  • a gravure printing machine equipped with a semi-solid plate the adjusted ink is printed on the treated surface of a biaxially stretched polypropylene film (Pyrene P-2161 20 ⁇ m manufactured by Toyobo Co., Ltd.) that has been subjected to corona discharge treatment on one side. It was.
  • the printing speed is changed to 100 m / min, 150 m / min, and 200 m / min.
  • MONARCH 460 manufactured by Cabot Specialty Chemicals, Inc.
  • carbon black particle size 27 nm
  • BET specific surface area 84 m 2 / g Florene G-700 manufactured by Kyoeisha Chemical Co., Ltd.
  • the number average molecular weight and the weight average molecular weight were measured by the following methods. ⁇ GPC (polystyrene conversion) -Tosoh Co., Ltd. HLC8220 system-Conditions Separation column: Tosoh Co., Ltd. TSKgelGMHHR-N is used. Column temperature: 40 ° C. Moving layer: Tetrahydrofuran manufactured by Wako Pure Chemical Industries, Ltd. Flow rate: 1.0 ml / min. Sample concentration: 1.0% by weight. Sample injection volume: 100 microliters. Detector: differential refractometer.

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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)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne une composition de résine utilisée pour une encre, ladite composition présentant une excellente aptitude à l'impression, et en particulier d'excellentes propriétés antibuée sur plaque, et présentant également une excellente stabilité de dispersion pigmentaire sans ajout d'agent dispersant. L'invention concerne également une encre d'impression utilisant la composition. La composition de résine selon la présente invention contient une résine de polyuréthane (a) obtenue en faisant réagir un composé (I) comportant un groupe amino et/ou un groupe imino et qui est lié par covalence au carbone de la résine. L'invention concerne également une encre d'impression utilisant la composition, ainsi qu'un matériau imprimé et un stratifié obtenus en utilisant l'encre d'impression.
PCT/JP2014/061529 2014-04-24 2014-04-24 Composition de résine de polyuréthane pour encre, et encre d'impression Ceased WO2015162747A1 (fr)

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PCT/JP2014/061529 WO2015162747A1 (fr) 2014-04-24 2014-04-24 Composition de résine de polyuréthane pour encre, et encre d'impression

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PCT/JP2014/061529 WO2015162747A1 (fr) 2014-04-24 2014-04-24 Composition de résine de polyuréthane pour encre, et encre d'impression

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019099761A (ja) * 2017-12-07 2019-06-24 Ｄｉｃグラフィックス株式会社 リキッドインキ組成物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0616989A (ja) * 1992-07-03 1994-01-25 Dainippon Ink & Chem Inc 印刷インキ組成物
JPH08311144A (ja) * 1995-05-16 1996-11-26 Dainippon Ink & Chem Inc 架橋ポリウレタン樹脂粒子の水性分散液
JP2013144732A (ja) * 2012-01-13 2013-07-25 Dic Graphics Corp 印刷インキ

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0616989A (ja) * 1992-07-03 1994-01-25 Dainippon Ink & Chem Inc 印刷インキ組成物
JPH08311144A (ja) * 1995-05-16 1996-11-26 Dainippon Ink & Chem Inc 架橋ポリウレタン樹脂粒子の水性分散液
JP2013144732A (ja) * 2012-01-13 2013-07-25 Dic Graphics Corp 印刷インキ

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019099761A (ja) * 2017-12-07 2019-06-24 Ｄｉｃグラフィックス株式会社 リキッドインキ組成物
JP7073696B2 (ja) 2017-12-07 2022-05-24 Ｄｉｃグラフィックス株式会社 リキッドインキ組成物

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