WO2003018698A1 - Liant pour encre d'imprimerie et composition d'encre d'imprimerie contenant celui-ci - Google Patents

Liant pour encre d'imprimerie et composition d'encre d'imprimerie contenant celui-ci Download PDF

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Publication number
WO2003018698A1
WO2003018698A1 PCT/JP2002/008708 JP0208708W WO03018698A1 WO 2003018698 A1 WO2003018698 A1 WO 2003018698A1 JP 0208708 W JP0208708 W JP 0208708W WO 03018698 A1 WO03018698 A1 WO 03018698A1
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WO
WIPO (PCT)
Prior art keywords
printing ink
parts
binder
diol
weight
Prior art date
Application number
PCT/JP2002/008708
Other languages
English (en)
Japanese (ja)
Inventor
Hideyuki Kishi
Takuya Miho
Original Assignee
Daicel Chemical Industries, Ltd.
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 Daicel Chemical Industries, Ltd. filed Critical Daicel Chemical Industries, Ltd.
Priority to KR10-2003-7012056A priority Critical patent/KR20040028728A/ko
Publication of WO2003018698A1 publication Critical patent/WO2003018698A1/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
    • C09D11/10—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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
    • C08G18/4269—Lactones

Definitions

  • the present invention relates to a printing ink binder and a printing ink composition containing the same.
  • polyurethane is often used as a binder for printing ink used in such printing ink.
  • printing inks using polyurethane as a binder have excellent adhesion to polyester films and nylon films alone.Adhesion to films is inadequate.
  • toluene-based printing inks have been used in which chlorinated polypropylene resins are blended with polyurethane.
  • Japanese Patent Application Laid-Open No. 9-33885 discloses a molecular weight of 500 to 3,3,5-trimethyl-1,6-hexanediol or 3,5,5-trimethyl-1,6-hexanediol.
  • Polypropylene, polyester and polyamide foil as printing materials containing, as a binder, a polyurethane resin obtained by reacting a polymer polyol containing 50,000 or more polyester glycols at 50% by weight or more with a diisocyanate compound.
  • the invention relates to a composition for printing ink having excellent adhesion to any film of ILM.
  • Japanese Unexamined Patent Publication No. 522223/1993 discloses a binder for a printing ink mainly containing a polyurethane obtained by reacting a polymer diol, a diisocyanate compound and a chain extender, as a component of the polyurethane.
  • the invention describes a binder for printing inks using 1,2-ethyl-12-alkyl-1,3-propanediol.
  • JP-A-2000-26782 discloses a binder for a printing ink mainly containing a polyurethane obtained by reacting a polymer diol, a diisocyanate compound and an amine chain extender. It describes a binder for printing ink containing 2,4-dialkyl-1,5-pentyldiol as a component of the polymer diol, and a printing ink composition containing the binder.
  • Japanese Patent Publication No. 1-162848 discloses that when an organic diisocyanate is reacted with a compound having two or more active hydrogens in a molecule to produce a polyurethane, the above-mentioned compound having active hydrogen is used.
  • An average molecular weight of 500 to 50,000, obtained by an ester exchange reaction between a polyester polyol synthesized by a dehydration esterification reaction of neopentyldaricol and adipic acid and ⁇ -force prolactone A process for producing a polyurethane having excellent elastic recovery using a polyprolactone polyester polyol having a prolactone content of 40 to 95% by weight is described.
  • the present invention solves the above-described problems, and has excellent adhesiveness to various plastic films such as polyester, nylon, and polyolefin as a printing substrate, and is particularly suitable for a non-aromatic solvent-based printing ink.
  • An object of the present invention is to provide a printing ink composition comprising a binder for printing and the binder for printing ink.
  • the present inventors have conducted intensive studies to provide a printing ink composition that can solve the above-mentioned problems, and as a result, used a polyurethane resin containing a specific diol as a component as a binder for printing ink. In such a case, they have found that such a problem can be solved, and have completed the present invention. Disclosure of the invention
  • the present invention relates to a polymer diol, a diisocyanate compound and an amine-based chain extender, wherein the polymer diol comprises 2,2-dialkyl-1,3-propanediol (A), a dibasic acid component (B) and a lactone.
  • the present invention provides a binder for printing ink containing 50% by weight or more of a polyester diol comprising the compound (C).
  • a binder for printing ink wherein the polyester diol contains 5 to 80% by weight of a lactone (C). Further, the present invention provides the binder for printing ink of the above invention, wherein the number average molecular weight of the polyester diol is from 500 to 50,000. Further, the binder for a printing ink according to the invention, wherein the polyurethane has a number average molecular weight of 5,000 to 100,000, and the binder for a non-aromatic solvent type printing ink according to the invention. Provided are a binder for printing ink, a printing ink composition containing the binder for printing ink of the invention, and a printing ink composition of the invention using a non-aromatic solvent.
  • the binder for a printing ink of the present invention contains, as a main component, a polyurethane obtained by reacting a polymer diol, a diisocyanate compound, and an amine-based chain extender.
  • polyesterdiol composed of 2,2-dialkyl-1,3-propanediol (A), a dibasic acid component (B) and a lactone (C) was used. % Or more.
  • This polyester diol is prepared by various known methods. It can be obtained by condensation.
  • 2,2-Dialkyl-1,3-propanediol which is one of the constituent components of the polyester diol (hereinafter sometimes abbreviated as “diol”) used in the present invention.
  • propanediol (A;) As long as it is a 1,3-propanediol derivative having an alkyl group having 1 to 5 carbon atoms. Specifically, 2,2-getyl-1,3-propanediol, 2_n-butyl-2-ethyl_1,3-propanediol and the like are preferably used. It is desirable to use propanediol (A) alone, but when propanediol (A) is the main component, various other known diols can be used in combination.
  • diols may be contained in a range of 40% by weight or less of the polyester diol.
  • alkyldaricidyl ethers such as n-butyldaricidyl ether, 2-ethylhexyldaricidyl ether, and monocarboxylic acids such as versatic acid glycidyl ester
  • Glycidyl esters can also be used in an amount of up to 40% by weight of the polyester diol.
  • Dibasic acid component which is one of the constituent components of the polyester diol used in the present invention
  • those generally known as an acid component of a polyester as described below can be used.
  • dibasic acids such as adipic acid, maleic acid, fumaric acid, fumaric anhydride, isophthalic acid, terephthalic acid, succinic acid, malonic acid, daltaric acid, azelaic acid, sebacic acid, suberic acid, etc. Acid anhydride and dimeric acid.
  • adipic acid, azelaic acid and the like are preferably used.
  • the lactones (C) which are one of the components of the polyester diol used in the present invention include aptyrolactone, ⁇ -force prolactone, ⁇ 5-valerolactone, monomethyl- ⁇ -force prolactone, and trimethyl- ⁇ . Methylation of one-stroke prolactone ⁇ —Force prolactone and the like. Of these, ⁇ -force prolactone is preferred.
  • the content of the lactone (C) constituting the polyester diol of the present invention is preferably from 5 to 80% by weight of the polyester diol, and more preferably from 10 to 70% by weight. When the content of the lactone (C) is 5% by weight or less, the adhesive strength and the blocking resistance may decrease. On the other hand, when the content is 80% by weight or more, the printability tends to deteriorate due to the decrease in solubility.
  • the number average molecular weight of the polyester diol of the present invention comprising a diol containing 2,2-dialkyl-11,3-propanediol ( ⁇ ), a dibasic acid component ( ⁇ ) and a lactone (C) is as follows: It is appropriately determined in consideration of the solubility, drying property, blocking resistance, and the like of the obtained polyurethane, and preferably has a lower limit of 500, more preferably 700, and an upper limit of 500, more preferably 4. A value within the range of 0 0 0 is preferred. If the number average molecular weight is less than 50,000, printability tends to be inferior due to the decrease in solubility, while if it exceeds 50,000, drying properties and blocking resistance tend to decrease.
  • the method for producing the polyester diol is as follows: 2,2-dialkyl-1,3-propanediol (A) ⁇ + 1 mol, diacid component ( ⁇ ) ⁇ mol, lactones (C) 5 to 80% by weight % Can be produced, for example, according to the method described in JP-A-58-59212.
  • the diol ( ⁇ ), the dibasic acid component ( ⁇ ), and the lactone (C), for example, ⁇ -force prolactone are mixed and heated, and can be produced by a dehydration esterification reaction, a ring opening reaction, and a transesterification reaction.
  • One-pot method or polyester diol obtained by dehydration esterification of diol ( ⁇ ) and dibasic acid component ( ⁇ ), and separately from polyhydric alcohol by ring-opening reaction of ⁇ -force prolactone. It can also be produced by mixing a polyprolactone polyol, usually a polyprolactonediol, and then transesterifying the two. Further, it can be produced by ring-opening polymerization of ⁇ -force prolactone to a polyester polyol having a small molecular weight. Of these, the one-pot method is simple and preferred.
  • These reactions are preferably performed at 130 to 240 :, preferably 140 to 230, from the viewpoint of preventing coloring and from the viewpoint of preventing the depolymerization reaction of ⁇ -force prolactone.
  • the catalyst is usually added at 0.05 to 100 ppm by weight of the total monomer, Preferably, 0.1 to 100 ppm by weight is used.
  • the catalyst include organotitanium compounds such as tetrabutyl titanate and tetrapropyl titanate, dibutyltin laurate, tin octoate, dibutyltin oxide, stannous chloride, stannous bromide, and tin tin iodide. Tin compounds can be used.
  • the reaction is preferably carried out while passing an inert gas such as nitrogen from the viewpoint of preventing the obtained target product from being colored.
  • a low molecular weight diol having a number average molecular weight of less than 500 may be used in combination as long as the performance of the polyurethane of the present invention is not deviated.
  • Specific examples include 2,2-dialkyl-1,3-propanediol described in the section of the diol used in the polyester diol of the present invention and various other diols.
  • the amount of the low molecular weight diol is usually less than 10 parts by weight based on 100 parts by weight of the high molecular weight diol. If the amount is more than 10 parts by weight, the printability tends to decrease due to the decrease in solubility, and the adhesiveness to the nylon film tends to decrease.
  • diisocyanates of an aromatic, aliphatic or alicyclic type can be used as the diisocyanate compound.
  • an amine-based chain extender is used particularly in consideration of adhesiveness to a nylon film.
  • the amine-based chain extender specifically, aromatic, aliphatic or alicyclic
  • diamines include phenylenediamine, naphthylenediamine, ethylenediamine, propylenediamine, hexamethylenediamine, isophoronediamine, dicyclohexylmethane-14,4′-diamine, and the like.
  • amine-based chain extenders include diamines having a hydroxyl group in the molecule, such as diamine, di-2-hydroxypropylethylenediamine, and dimer diamine obtained by converting a carboxy group of dimer acid into an amino group.
  • a chain length terminator may be used as necessary.
  • the chain terminator include various known compounds such as amine-based and lower alcohol-based ones, and amine-based chain terminators are preferred because they can easily control the molecular weight.
  • the amine-based chain terminator include alkyl monoamines such as di-n-butylamine and hydroxyl monoamines such as genolenoamine.
  • the lower alcohol-based chain terminator include methanol and ethanol.
  • the method for producing the polyurethane used in the present invention is not particularly limited.For example, a polymer diol and a diisocyanate compound are reacted under the condition of an excess of isocyanate group, and a prepolymer having an isocyanate group at both terminals of the polymer diol is used.
  • any one-step method in which a high molecular diol, a diisocyanate compound, an amine-based chain extender and, if necessary, a chain terminator are reacted in a suitable solvent at once can be employed, but a uniform polymer solution can be used. It is preferable to employ the two-stage method in that it is easy to obtain.
  • various known catalysts such as tin catalysts such as stannous octoate can be added.
  • the conditions for reacting the high molecular weight diol with the diisocyanate compound are not particularly limited, except that the isocyanate group is excessive, but the hydroxyl group isocyanate group is not required. Is preferably in the range of 1.5 to 13.5 in equivalent ratio.
  • the solvent used is generally an aromatic solvent such as benzene, toluene, or xylene which is well known as a printing ink solvent; methanol, ethanol, isopropanol, or the like.
  • alcohol solvents such as n-butanol
  • ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone
  • ester solvents such as ethyl acetate and butyl acetate; these may be used alone or in combination of two or more. Can be used as a mixture.
  • a non-aromatic solvent-type printing ink is obtained using the printing ink binder of the present invention, it is preferable to use a non-aromatic solvent also in producing the printing ink binder.
  • the number average molecular weight of the polyurethane used in the present invention obtained in this manner is preferably in the range of 50,000 to 100,000, more preferably in the range of 500,000 or less. Is good.
  • the number average molecular weight is less than 5,000, the drying properties, blocking resistance, film strength, oil resistance, etc. of the printing ink using this as a vehicle are liable to decrease.
  • it exceeds 000 the viscosity of the printing ink binder, which is the polyurethane resin solution, increases, and the gloss of the printing ink tends to decrease.
  • the resin solid content concentration of the polyurethane resin solution is not particularly limited, but may be appropriately determined in consideration of workability at the time of printing, and is usually 15 to 60% by weight, and the viscosity is 50 to 1%. It is practically preferable to adjust the value to the range of 0, 000 cP / 25.
  • the following resin may be used as a binder as an auxiliary component in addition to the polyurethane which is a main component of the present invention.
  • the polyurethane which is a main component of the present invention.
  • polyurethanes, polyamides, dinitrocellulose, polyacrylic esters, polypinyl chlorides, copolymers of vinyl chloride and vinyl acetate, rosin resins, ketone resins, etc., other than the present invention are mentioned.
  • a color mill, a solvent, and, if necessary, a surfactant, a wax, and other additives for improving the ink fluidity and the ink surface film are appropriately blended with the binder for the printing ink of the present invention, and a pole mill, an attritor, and a sand mill are used.
  • the printing ink composition of the present invention can be manufactured by kneading using an ordinary ink manufacturing apparatus such as the above.
  • the solvent those similar to those described in the production of the binder for printing ink can be used.
  • the printing ink composition of the present invention is used as a non-aromatic solvent-type printing ink
  • a non-aromatic solvent is used during production of the printing ink binder
  • a non-aromatic solvent is also used when producing a printing ink composition.
  • the amount of the binder in the printing ink composition is preferably such that the resin solid content is 3 to 20% by weight.
  • Kurapole P2010 polyester polyol of adipic acid having an average molecular weight of 2000 and 3-methylpentanediol, OH value 57.1 manufactured by Kuraray Co., Ltd. Parts and isophorone diisocyanate (54.9 parts) were charged and reacted with 12 O for 6 hours under a nitrogen stream to produce a prepolymer, and then 558 parts of methyl ethyl ketone were added to obtain 927 parts of a homogeneous urethane prepolymer solution.
  • the polyurethane resin solution D thus obtained had a resin solid content concentration of 30.1% and a viscosity of 2048 cp / 25.
  • the obtained polyurethane resin solution (without ink formulation) is applied to one side of various plastic films using Barco No. 1 (No. 4), air-dried (about 25), and then dried at 80 for 1 hour. After drying, the film was folded inward, a glass plate was placed thereon, and the film was further dried at 80 at 1 hour to obtain a laminated film. Then, after the laminate film was formed into a strip having a width of 25 mm, the peel strength was determined by a tensile tester. Table
  • PET film 50 m thickness
  • the binder for printing ink of the present invention and the printing ink composition containing the same can be used for various plastic films such as polyester, nylon film, polyethylene, polypropylene and the like, even when a non-aromatic solvent-based printing ink is used. And exhibits excellent adhesiveness. Further, as compared with the case where another similar polyester diol is used as the polymer diol in place of the polyester diol of the present invention, the binder for printing ink and the printing ink composition of the present invention have a non-aromatic solvent type. Print Re-dissolvability is good.
  • the binder for printing ink and the printing ink composition of the present invention are to be replaced with a binder and a printing ink composition for toluene-type printing ink in which a chlorinated polypropylene resin is blended with a conventional polyurethane. It is also preferable in terms of environmental impact.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne un liant pour encre d'imprimerie, lequel fait preuve d'une excellente adhérence à des films de différents plastiques tels que polyesters, nylons, et polyoléfines, utilisés en tant que matières destinées à recevoir l'encre, et qui convient plus spécifiquement à des encres d'imprimerie à base d'un solvant non aromatique. L'invention concerne également une composition d'encre d'imprimerie contenant ce liant d'encre d'imprimerie. Ce liant d'encre d'imprimerie comprend un polyuréthanne contenant au moins 50 % en poids de diol à poids moléculaire élevé, ce dernier étant un polyester diol obtenu à partir d'un 2,2-dialkyle-1,3-propanediol (A), d'un ingrédient acide dibasique (B) et d'une lactone (C).
PCT/JP2002/008708 2001-08-31 2002-08-29 Liant pour encre d'imprimerie et composition d'encre d'imprimerie contenant celui-ci WO2003018698A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR10-2003-7012056A KR20040028728A (ko) 2001-08-31 2002-08-29 인쇄 잉크용 바인더 및 그것을 함유하여 이루어진 인쇄잉크 조성물

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001263433A JP2003073601A (ja) 2001-08-31 2001-08-31 印刷インキ用バインダー及びそれを含有してなる印刷インキ組成物
JP2001-263433 2001-08-31

Publications (1)

Publication Number Publication Date
WO2003018698A1 true WO2003018698A1 (fr) 2003-03-06

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JP (1) JP2003073601A (fr)
KR (1) KR20040028728A (fr)
CN (1) CN1473181A (fr)
WO (1) WO2003018698A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1743911A1 (fr) * 2005-07-14 2007-01-17 DSM IP Assets B.V. Composition de polyuréthanne
CN103613736A (zh) * 2013-11-19 2014-03-05 张家港威迪森化学有限公司 一种聚氨酯胶粘剂的制备方法
CN104672421B (zh) * 2015-02-11 2017-06-06 黄山中泽新材料有限公司 复合油墨连接料聚氨酯树脂制备方法和凹版印刷用复合油墨
CN105017845A (zh) * 2015-07-14 2015-11-04 孙光英 一种防脱落印刷油墨组合物
CN105368131A (zh) * 2015-11-19 2016-03-02 佛山市新榜包装材料有限公司 一种pvc保护膜表印油墨黏结助剂

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09235501A (ja) * 1996-02-27 1997-09-09 Arakawa Chem Ind Co Ltd 印刷インキ用樹脂

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09235501A (ja) * 1996-02-27 1997-09-09 Arakawa Chem Ind Co Ltd 印刷インキ用樹脂

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JP2003073601A (ja) 2003-03-12
CN1473181A (zh) 2004-02-04
KR20040028728A (ko) 2004-04-03

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