WO2015190345A1 - Composition d'encre aqueuse résistant aux milieux alcalins - Google Patents

Composition d'encre aqueuse résistant aux milieux alcalins Download PDF

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Publication number
WO2015190345A1
WO2015190345A1 PCT/JP2015/065851 JP2015065851W WO2015190345A1 WO 2015190345 A1 WO2015190345 A1 WO 2015190345A1 JP 2015065851 W JP2015065851 W JP 2015065851W WO 2015190345 A1 WO2015190345 A1 WO 2015190345A1
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WO
WIPO (PCT)
Prior art keywords
acrylic acid
acid copolymer
meth
alkali
value
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Application number
PCT/JP2015/065851
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English (en)
Japanese (ja)
Inventor
山田　雅生
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Dic株式会社
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株式会社 filed Critical Dic株式会社
Priority to JP2015544231A priority Critical patent/JP5858320B1/ja
Priority to CN201580002304.4A priority patent/CN105658740B/zh
Publication of WO2015190345A1 publication Critical patent/WO2015190345A1/fr

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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
    • C09D11/02—Printing inks
    • C09D11/023—Emulsion 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
    • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof

Definitions

  • the present invention relates to a water-based ink composition having high alkali resistance and excellent printability and workability, particularly an ink composition suitable for water-based ink use for gravure printing and flexographic printing, and a method for producing the composition About.
  • an ethylene-acrylic acid copolymer is known as a new resin component that solves these problems.
  • a method of blending a special surfactant (acetylene diols) at a specific ratio (for example, Patent Document 1) when dispersing the pigment in the resin component has been proposed and exhibits a certain effect, but the type of pigment changes. However, the dispersion effect is reduced, and when the pigment concentration is increased, the pigment is settled and the function is not sufficiently exhibited.
  • an object of the present invention is to provide an alkali-resistant water-based ink composition using an ethylene-acrylic acid copolymer as a resin component, without depending on the type of pigment, and without using a special surfactant.
  • An object of the present invention is to provide an alkali-resistant ink composition having good pigment dispersibility.
  • the present inventor has obtained a pigment dispersion using a neutralized water dispersion of a basic compound of an acrylic acid copolymer having a specific SP value, an ethylene-acrylic
  • the present invention was completed by finding that the dispersion stability of an ink composition containing an acid copolymer was good.
  • the present invention relates to water obtained by neutralizing an acrylic acid copolymer having an SP value of 20.4 to 20.7 (J / cm 3 ) 1/2 in turbidity titration method with ammonia and / or alkanolamine.
  • an alkali-resistant water-based ink composition comprising an aqueous dispersion prepared by dispersing a pigment in a dispersion and then neutralizing an ethylene-acrylic acid copolymer with an alkanolamine.
  • the present invention also provides an alkali-resistant water-based ink composition in which the acrylic acid copolymer is a copolymer of an aromatic compound having a vinyl group, a (meth) acrylic acid ester, and (meth) acrylic acid. .
  • the present invention also provides an alkali-resistant water-based ink composition containing a (meth) acrylic acid ester having 12 to 18 carbon atoms in an alcohol constituting the ester group of the (meth) acrylic acid ester.
  • the present invention also provides an alkali-resistant water-based ink composition in which the acrylic acid copolymer has an acid value of 50 mgKOH / g or more.
  • the alkali-resistant water-based ink composition according to the present invention has excellent dispersibility between the pigment and the ethylene-acrylic acid copolymer, the obtained ink has excellent stability and printability, and the printed matter has excellent alkali resistance. .
  • the acrylic copolymer used for dispersing the pigment used in the alkali-resistant water-based ink composition of the present invention has an SP value of 20.4 to 20.7 (J / cm 3 ) 1/2 in the turbidity titration method.
  • SP value 20.4 to 20.7 (J / cm 3 ) 1/2 in the turbidity titration method.
  • the method for measuring the SP value by this turbidity titration method is described in W. Suh, D.H. H. The method is proposed by Clarke et al. In the following [Document 1], [Document 2], and the like.
  • Procedure 1 Solidification of aqueous resin (Preparation of SP value measurement sample) (1) Add 300 ml of ion-exchanged water to a 500 ml beaker and dissolve 20 g of the aqueous dispersion resin while magnetically stirring. (2) Concentrated hydrochloric acid is added dropwise until the pH of the aqueous solution becomes 4. (3) The resin component is isolated by filtration under reduced pressure, and washed with ion exchange water until the waste liquid pH becomes 7. (4) The washed resin component powder is vacuum dried at 40 ° C. for 8 hours. Procedure 2.
  • L titration of low polarity solvent (n-hexane) (cm 3 )
  • H titration of highly polar solvent (water) (cm 3 )
  • ⁇ SL Volume fraction of dissolved solvent (THF) with respect to the sum of dissolved solvent (THF) and titration solvent (n-hexane)
  • ⁇ L Titration solvent with respect to the sum of dissolved solvent (THF) and titration solvent (n-hexane) ( n-Hexane) volume fraction
  • ⁇ SH volume fraction of dissolving solvent (THF) with respect to the sum of dissolving solvent (THF) and titration solvent (ion exchange water)
  • ⁇ H dissolving solvent (THF) and titration solvent (ion) Volume fraction of titration solvent (ion exchange water) with respect to the sum of exchange water)
  • the calculated SP value can be known.
  • an approximate copolymer composition can be determined before preparing an acrylic acid copolymer. Therefore, it is possible to theoretically design the outline of the acrylic acid copolymer composition having a specific SP value used in the present invention.
  • the SP value of the copolymer is represented by the following formula.
  • ⁇ copolym SP value of copolymer [(J / cm 3 ) 1/2 ]
  • Mi indicates the mole fraction of the monomer component i component
  • ⁇ Mi 1 ⁇ unit_i: SP value of the monomer units i component [(J / cm 3) 1/2]
  • the acrylic acid copolymer used for dispersing the pigment used in the alkali-resistant water-based ink composition of the present invention has an SP value of 20.4 to 20.7 (J / cm 3 ) 1/2 in the turbidity titration method.
  • the SP value ( ⁇ unit — i ) of the constituent monomer of the acrylic acid copolymer and its unit component is, for example, styrene [18.4], ⁇ -methylstyrene, although not particularly limited.
  • the monomer unit component which does not exist as a literature value can estimate the SP value by the Fedors method described in the following [Document 3] or the like.
  • the SP value calculated from the calculation cannot be directly applied to the present invention because the SP value of each monomer is slightly different depending on the literature. In order to carry out the present invention, it is necessary to determine the SP value by the turbidity titration method described above.
  • the constituent monomer of the acrylic acid copolymer used in the alkali-resistant water-based ink composition of the present invention includes, for example, styrene, ⁇ -methylstyrene, 2-methylstyrene as the vinyl group-containing aromatic.
  • Examples of other constituent monomers (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, ( N-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, capryl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, (meth) acrylic acid Myristyl, cetyl (meth) acrylate, stearyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, (meth) acrylic Isobornyl acid, glycidyl (meth)
  • acrylic acid and methacrylic acid as the (meth) acrylic acid monomer.
  • these may be used alone or in combination of two or more.
  • the amount of the (meth) acrylic acid monomer used at that time is affected by the type of organic solvent and the ratio of the organic solvent to water in the aqueous process, but the solid content acid value ( mgKOH / g) can be made aqueous if it is about 20 or more, but from the viewpoint of reducing the amount of the organic solvent, the amount which becomes at least 50 with such an acid value is preferably the same acid. An amount that is 80 or more is appropriate.
  • the constituent components of these acrylic acid copolymers are not limited to the exemplified monomers, and other monomers may be added at all.
  • the acrylic acid copolymer can be produced by a known method.
  • a two-stage method comprising a first step of producing an acrylic acid copolymer in an organic solvent and a second step of producing an aqueous resin is known.
  • the production of the acrylic acid copolymer in the first step is obtained by so-called solution polymerization in which the monomer is polymerized in an organic solvent.
  • the organic solvent herein is not particularly limited, but only a typical one among them is exemplified, and various aromatic organic solvents such as toluene and xylene, ethyl acetate, Various water-insoluble organic solvents such as various ester solvents such as butyl acetate; methanol, ethanol, normal (n-) propanol, iso (i-) propanol, n-butanol, isobutanol, tertiary ( tert-) various alcohol solvents such as butanol, 3-methoxybutanol, 3-methyl-3-methoxybutanol; various ketone solvents such as acetone, methyl ethyl ketone, isobutyl ketone, cyclohexanone; ethylene glycol, ethylene glycol mono
  • the radical solution polymerization method is the simplest polymerization method. If only typical ones are exemplified as polymerization initiators that can be used when applying using such radical solution polymerization method, 2,2′-azobis (isobutyronitrile), 2,2′- Various azo compounds such as azobis (2,4-dimethylvaleronitrile) or 2,2′-azobis (2-methylbutyronitrile); or tert-butyl peroxypivalate, tert-butyl peroxybenzoate, tert-butylperoxy-2-ethylhexanoate, benzoyl peroxide, lauroyl peroxide, acetyl peroxide, di-tert-butyl peroxide, dicumyl peroxide, tert-butyl hydroperoxide, cumene hydroperoxide, Methyl ethyl ketone peroxide Such de or diisopropyl peroxy
  • an acrylic acid copolymer can be produced by radical polymerization according to a known and commonly used method.
  • the acrylic acid copolymer thus obtained can be partially or completely neutralized with a basic compound and dissolved in an aqueous medium by adding water.
  • the basic compound to be used in that case is appropriate to use ammonia or organic amines, which is recommended and particularly representative.
  • organic amines such as diisopropanolamine, 2-amino-2-methylpropanol, 2- (dimethylamino) -2-methylpropanol, morpholine, N-methylmorpholine, N-ethylmorpholine; or ammonia It is done.
  • a resin dissolved in an aqueous medium can be obtained.
  • the amount of the organic solvent contained in these resins can be reduced.
  • an operation such as addition of a water-soluble solvent or so-called solvent replacement with a water-soluble solvent is performed.
  • a resin in a form dissolved in an aqueous medium can be obtained by performing the treatment before or after neutralization and aqueous formation.
  • the ethylene-acrylic acid copolymer used in the alkali-resistant water-based ink composition of the present invention is preferably 70 to 95% by weight of ethylene and 5 to 30% by weight of acrylic acid.
  • the molecular weight of the ethylene-acrylic acid resin is preferably 5,000 to 10,000, the glass transition point is 0 ° C. or less, and the acid value is preferably 10 to 60.
  • the neutralizing agent for the ethylene-acrylic acid copolymer alkylamine, alkanolamine and the like are preferable, and the carboxyl group of the copolymer is neutralized to obtain an aqueous dispersion.
  • the added amount of the neutralizing agent is 0.8 equivalent or more with respect to 1 equivalent of the carboxyl group in the ethylene-acrylic acid copolymer, so that the dispersion stability of the copolymer and the re-solubility of the ink can be improved.
  • alkylamines examples include diethylamine and triethylamine, and examples of the alkanolamines include monoethanolamine, dimethylethanolamine, and diethylethanolamine, and dimethylethanolamine is preferable.
  • the acrylic acid copolymer used in the alkali-resistant water-based ink composition of the present invention is preferably 5% to 10% of the entire resin component contained in the ink. If it is less than this, it is difficult to disperse the pigment, so the pigment concentration must be reduced. On the other hand, if it exceeds this, the alkali resistance of the printed matter will be weakened.
  • a colorant inorganic pigments, organic pigments, extender pigments and the like used in general water-based ink compositions can be used.
  • the solvent water alone or an organic solvent miscible with water can be used.
  • the organic solvent include alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol and n-propyl alcohol, polyhydric alcohols such as propylene glycol and glycerin, propylene glycol monomethyl ether, propylene glycol monoethyl ether and propylene glycol mono n.
  • -Ethers such as propyl ether and ethyl carbitol.
  • auxiliary ingredients include waxes such as paraffin wax, polyethylene wax, carnauba wax, oleic acid amide, stearic acid amide, erucic acid amide, etc. for imparting friction resistance, slipperiness, etc.
  • waxes such as paraffin wax, polyethylene wax, carnauba wax, oleic acid amide, stearic acid amide, erucic acid amide, etc.
  • Fatty acid amides, silicon-based and non-silicon-based antifoaming agents for suppressing foaming at the time of printing, various dispersants for improving pigment wetting, and the like can also be used as appropriate.
  • the alkali-resistant water-based printing ink composition according to the present invention is produced using an Eiger mill, a sand mill, a gamma mill, an attritor or the like generally used for the production of gravure and flexographic printing inks.
  • the alkali-resistant water-based printing ink according to the present invention can be printed on a plastic film, polyethylene-coated paper or the like by a printing method in which oil-based printing ink is generally used, that is, gravure printing, flexographic printing or the like.
  • Example 1 Mix 40 parts of the indigo pigment FASTOGEN BLUE LDB30 manufactured by DIC Corporation with 20 parts of the acrylic acid copolymer aqueous solution prepared in Reference Example 1, 4 parts of isopropyl alcohol, and 36 parts of water. Got. To this 26 parts of mill base was added 70 parts of an aqueous dispersion of ethylene-acrylic acid copolymer manufactured by Sumitomo Seika Co., Ltd., 3.8 parts of polyethylene wax, 3.8 parts of polyethylene wax, and 0.2 part of a silicone-based antifoaming agent. Cup No. 3 was adjusted by adding an aqueous diluent so as to be 16 seconds to obtain an aqueous ink.
  • Example 2 An acrylic acid copolymer aqueous solution was synthesized by the same operation as in Reference Example 1 except that the monomers and neutralizing agents shown in Table 1 were used.
  • the SP value of the solid content of the obtained acrylic acid copolymer was measured by the turbidity titration method and the turbidity titration method, it was 20.4 (J / cm 3 ) 1/2 and the solid content acid value was 82 mgKOH / g. there were.
  • a mill base and aqueous ink were obtained in the same manner as in Example 1.
  • Example 3 An acrylic acid copolymer aqueous solution was synthesized by the same operation as in Reference Example 1 except that the monomers and neutralizing agents shown in Table 1 were used.
  • the SP value of the solid content of the obtained acrylic acid copolymer was measured by turbidity titration method and turbidity titration method, it was 20.7 (J / cm 3 ) 1/2 , and the solid content acid value was 50 mgKOH / g. there were.
  • a mill base and aqueous ink were obtained in the same manner as in Example 1.
  • Example 4 A mill base was prepared in the same manner as in Example 1 except that the acrylic acid copolymer aqueous solution of Reference Example 1 was used and the pigment was changed to 40 parts of DIC Corporation yellow pigment SYMULER FAST YELLOW 5GF, and then an aqueous ink was obtained. .
  • Comparative Example 2 In the same manner as in Comparative Example 2, an acrylic acid copolymer aqueous solution was synthesized. When the SP value of the solid content of the obtained acrylic acid copolymer was measured by the turbidity titration method and the turbidity titration method, it was 20.3 (J / cm 3 ) 1/2 , and the solid content acid value was 100 mgKOH / g. there were. Using this aqueous resin, a mill base was obtained in the same manner as in Example 1. Next, adjustment of water-based ink was attempted in the same manner as in Example 1, but the ink was solidified immediately after the blending of Syxen L, and the ink could not be prepared.
  • a water-based ink was obtained in the same manner as in Example 1 except that 40 parts of Joncrill 711, which is a styrene-acrylic copolymer water-based resin, was used in place of Saixen L when blending the ink.
  • Joncrill 711 which is a styrene-acrylic copolymer water-based resin
  • Table 1 shows the composition of the acrylic acid copolymer aqueous solution on a weight basis.
  • Table 2 shows the formulation of mill base using each acrylic acid copolymer aqueous solution prepared on a weight basis.
  • Table 4 shows the evaluation results of the water-based ink produced.
  • the water-based ink of the present invention is excellent in storage stability, adhesion, re-solubility and alkali resistance.

Abstract

Cette invention concerne une composition d'encre aqueuse résistant aux milieux alcalins qui utilise un copolymère d'éthylène-acide acrylique à titre de composant de résine, et qui présente une bonne dispersibilité de pigment, indépendamment du type de pigment sans l'aide d'un tensioactif spécial. Une composition d'encre aqueuse résistant aux milieux alcalis est en outre décrite, ladite composition étant obtenue par : dispersion d'un pigment dans une dispersion aqueuse qui est obtenue par neutralisation d'un copolymère d'acide acrylique, ayant une valeur SP, déterminée par un procédé de titrage turbimétrique, de 20,4 à 20,7 (J/cm3)1/2, avec de l'ammoniac et/ou une alcanolamine ; et ultérieurement, incorporation par mélange d'une dispersion aqueuse, qui est obtenue par neutralisation d'un copolymère d'éthylène-acide acrylique avec une alcanolamine, dans celle-ci.
PCT/JP2015/065851 2014-06-10 2015-06-02 Composition d'encre aqueuse résistant aux milieux alcalins WO2015190345A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2015544231A JP5858320B1 (ja) 2014-06-10 2015-06-02 耐アルカリ性水性インキ組成物
CN201580002304.4A CN105658740B (zh) 2014-06-10 2015-06-02 耐碱性水性墨液组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014-119562 2014-06-10
JP2014119562 2014-06-10

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WO2015190345A1 true WO2015190345A1 (fr) 2015-12-17

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CN (1) CN105658740B (fr)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018158986A (ja) * 2017-03-22 2018-10-11 東洋インキＳｃホールディングス株式会社 紙器用水性フレキソインキ組成物

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CN117143524A (zh) * 2023-07-20 2023-12-01 广东冠豪新材料研发有限公司 一种数码转印膜涂料及其制备方法与应用

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JPH0726188A (ja) * 1993-04-28 1995-01-27 Japan Small Corp プラスチックフィルム用水性印刷インキ組成物
JPH0726189A (ja) * 1993-04-28 1995-01-27 Japan Small Corp プラスチックフィルム用水性インキ組成物
JPH0741719A (ja) * 1993-07-27 1995-02-10 Dainippon Ink & Chem Inc 水性印刷インキの製造方法
JPH07247455A (ja) * 1994-03-09 1995-09-26 Sakata Corp 水性樹脂組成物用乾燥遅延剤および水性樹脂組成物の乾燥遅延方法
JP2011144335A (ja) * 2010-01-18 2011-07-28 Toyo Ink Sc Holdings Co Ltd 高耐アルカリ性水性インキ組成物

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JP2009108192A (ja) * 2007-10-30 2009-05-21 Canon Inc 水性インク、インクジェット記録方法、インクカートリッジ、インクカートリッジ、及びインクジェット記録装置
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JPH0726188A (ja) * 1993-04-28 1995-01-27 Japan Small Corp プラスチックフィルム用水性印刷インキ組成物
JPH0726189A (ja) * 1993-04-28 1995-01-27 Japan Small Corp プラスチックフィルム用水性インキ組成物
JPH0741719A (ja) * 1993-07-27 1995-02-10 Dainippon Ink & Chem Inc 水性印刷インキの製造方法
JPH07247455A (ja) * 1994-03-09 1995-09-26 Sakata Corp 水性樹脂組成物用乾燥遅延剤および水性樹脂組成物の乾燥遅延方法
JP2011144335A (ja) * 2010-01-18 2011-07-28 Toyo Ink Sc Holdings Co Ltd 高耐アルカリ性水性インキ組成物

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Publication number Priority date Publication date Assignee Title
JP2018158986A (ja) * 2017-03-22 2018-10-11 東洋インキＳｃホールディングス株式会社 紙器用水性フレキソインキ組成物

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JPWO2015190345A1 (ja) 2017-04-20
CN105658740B (zh) 2018-01-05
CN105658740A (zh) 2016-06-08

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