WO2007141090A1 - Préparations solides de pigment - Google Patents

Préparations solides de pigment Download PDF

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Publication number
WO2007141090A1
WO2007141090A1 PCT/EP2007/053982 EP2007053982W WO2007141090A1 WO 2007141090 A1 WO2007141090 A1 WO 2007141090A1 EP 2007053982 W EP2007053982 W EP 2007053982W WO 2007141090 A1 WO2007141090 A1 WO 2007141090A1
Authority
WO
WIPO (PCT)
Prior art keywords
ketone
solid pigment
pigment preparations
preparations according
pigments
Prior art date
Application number
PCT/EP2007/053982
Other languages
German (de)
English (en)
Inventor
Andreas Wenning
Original Assignee
Evonik Degussa Gmbh
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 Evonik Degussa Gmbh filed Critical Evonik Degussa Gmbh
Publication of WO2007141090A1 publication Critical patent/WO2007141090A1/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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0092—Dyes in solid form
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C09B67/0063—Preparation of organic pigments of organic pigments with only macromolecular substances

Definitions

  • the invention relates to solid pigment preparations consisting of at least one pigment and a resin, their preparation process and their use in paints, lacquers, adhesives, inks or printing inks.
  • These solid pigment preparations are used in coating materials such as, for example, paints, lacquers, adhesives, inks or printing inks for the coating of objects from, for example, As metals and plastics. These coating compositions are suitable for all customary application methods that are used in modern metal and plastic coating and the printing ink industry, such. As the spray application, the electrostatic spray application and printing by means of various printing processes.
  • colored coating materials are prepared in such a way that first of all a liquid pigment preparation is produced, which is then painted with a master paint.
  • fillers and pigments are dispersed in liquid media.
  • it is generally used dispersants, so as to reduce the mechanical shear forces required for effective dispersion of the solids and at the same time to achieve the highest possible fill levels.
  • the dispersants promote the breaking up of agglomerates, wet and / or occupy the surface of the particles to be dispersed as surface-active compounds and stabilize them against undesired reagglomeration.
  • wetting and dispersing agents facilitate the incorporation of pigments and fillers in the manufacture of paints and coatings, which, as important formulation constituents, substantially determine the optical appearance and the physicochemical properties of coatings. For one optimal utilization, these solids must be evenly distributed in paints and coatings, on the other hand, the once reached distribution must be stabilized.
  • the stabilizing component is also often perceived by binder components. Such binders are also valuable components for coating materials because they contribute to faster drying and increasing the hardness of the resulting films.
  • solvent-based coating materials usually solvent-based pigment preparation based on various wetting and dispersing agents are prepared, which are dissolved with various solvent-based masterbatches.
  • solvent-based pigment preparations based on various wetting agents and dispersants are prepared, which are then dissolved with various aqueous masterbatches.
  • the universal pigment preparations described in DE 10 2005 012 316 also have broad compatibility with binders used and solubility in organic solvents used and in water. In addition, foaming in aqueous pigment preparations is suppressed.
  • liquid pigment preparations In addition to water, organic solvents and dispersants, all these liquid pigment preparations generally contain further auxiliaries, for example
  • Drying inhibitors drying inhibitors, rheology additives, anti-skinning agents, biocides or agents for
  • the pigment preparations described in EP 702,062 are conditioned. However, to improve the texture of the pigments, inorganic salts of rosin resins are used, which on the one hand remain in the pigment preparation and can lead to disturbances in the organic coating. On the other hand, the dispersion is not optimal, so that when using phthalocyanine pigments must be ground several times wet.
  • EP 902 061 describes vinylpyrrolidone homopolymers or copolymers for the preparation of stir-in pigment preparations. These pigment preparations are particularly suitable for coloring aqueous industrial coatings or solvent-free plastics.
  • WO 2004/078852 describes a pigment preparation in which finely divided organic pigment particles are combined with inorganic pigment particles and these particles additionally have an organic macromolecular coating.
  • the present invention has for its object to find solid pigment preparations whose composition is as simple as possible and which can be distributed by a particularly easy dispersibility in application media of various kinds, especially by simple stir-in liquid application media.
  • solid pigment preparations By using these solid pigment preparations in solventborne or solventless applications, high color strength and flocculation stability should be present.
  • the object underlying the invention has surprisingly been achieved by the use of at least one non-carbonyl-hydrogenated ketone resin and / or a non-carbonyl-hydrogenated ketone / aldehyde resin in combination with at least one pigment.
  • component A it is possible to use organic or inorganic pigments and also carbon blacks.
  • Suitable organic pigments are, for example, azo pigments, azomethine pigments, metal complex pigments, anthraquinoid pigments, phthalocyanine pigments, polycyclic pigments, in particular those of the thioindigo, quinacridone, dioxazine, pyrrolo, naphthalenetetracarboxylic acid, perylene, indanthrone, Isoamidoline (on), isoindolinone, flavanthrone, pyranthrone or isoviolanthrone series. Mixtures or solid solutions of such pigments are also possible.
  • pigments from the group of the azo, dioxazine, pyrrolo (especially the diketopyrrolopyrrole pigments), quinacridone phthalocyanine, indanthrone or isoindolinone pigments are particularly suitable organic pigments.
  • Highly suitable organic pigments are those described in the Color Index. These include, for example, the group of Cl. Pigment Red 202, Cl. Pigment Red 122, Cl. Pigment red 144, Cl. Pigment Red 170, Cl. Pigment Red 177, Cl. Pigment red 179, Cl. Pigment Red 254, Cl. Pigment red 255, Cl. Pigment Red 264, Cl. Pigment Brown 23, Cl. Pigment Yellow 13, Cl. Pigment Yellow 74, Cl. Pigment Yellow 83, Cl.
  • suitable inorganic pigments are metal oxides, mixed metal oxides, antimony yellows, lead chromates, lead chromate sulphates, lead molybdate, ultramarine blue, cobalt blue, manganese blue, chrome oxide green, hydrated chromium oxide green, cobalt green, metal sulphides, cadmium sulphoselenides, zinc ferrites or bismuth vanadates, alone or in mixtures.
  • carbon blacks gas blacks, black carbon blacks or furnace carbon black, alone or in mixtures, can be used. These carbon blacks can additionally be post-oxidized and / or beaded.
  • Suitable ketones for the preparation of the ketone resins and ketone / aldehyde resins are all ketones, in particular acetone, acetophenone, methyl ethyl ketone, tert-butyl methyl ketone, heptanone-2, pentanone-3, methyl isobutyl ketone, cyclopentanone, cyclododecanone, mixtures of 2,2 , 4- and 2,4,4-trimethylcyclopentanone, cycloheptanone and cyclooctanone, cyclohexanone and all alkyl-substituted cyclohexanones having one or more alkyl radicals having a total of 1 to 8 carbon atoms, individually or in admixture.
  • alkyl-substituted cyclohexanones there may be mentioned 4-tert-amylcyclohexanone, 2-sec-butylcyclohexanone, 2-tert-butylcyclohexanone, 4-tert-butylcyclohexanone, 2-methylcyclohexanone and 3,3,5-trimethylcyclohexanone.
  • ketones usually all C-H-acidic ketones.
  • aldehyde component of the ketone / aldehyde resins are in principle unbranched or branched aldehydes, such as.
  • formaldehyde acetaldehyde, n-butyraldehyde, iso-butyraldehyde, valeric aldehyde and dodecanal.
  • all the aldehydes mentioned in the literature as suitable for ketone resin syntheses can be used.
  • formaldehyde is used alone or in mixtures.
  • the required formaldehyde is usually used as about 20 to 40 wt .-% aqueous or alcoholic (eg, methanol or butanol) solution.
  • alcoholic eg, methanol or butanol
  • Other uses of formaldehyde such.
  • para-formaldehyde or trioxane are also possible.
  • Aromatic aldehydes, such as. B. benzaldehyde may also be included in admixture with formaldehyde.
  • Acetophenone, cyclohexanone, 4-tert-butylhexanone, 3,3,5-trimethylcyclohexanone and also heptanone alone or in mixture and formaldehyde are particularly preferably used as starting compounds for component B).
  • Such ketone-aldehyde resins are described for example in DD 12 433, DD 123 481, DE 12 56 898, DE 13 00 256, DE 28 31 613 and DE 44 04 809.
  • the vinylpyrrolidone homopolymers or copolymers described in EP 902 061 have a molecular weight of 5000 to 300 000 g / mol. With a molecular weight of less than 3000 g / mol, the ketone resins or ketone / aldehyde resins used according to the invention have a significantly lower molecular weight.
  • inorganic fillers can be used. They are usually powdery, practically insoluble in the application medium substances. They are predominantly made from naturally occurring minerals by mining, Purification, grinding and subsequent classification won in grain fractions. But even synthetic products, such as sulfates or carbonates, are used as fillers, for example, when it comes to purity (brightness) or special fineness. In contrast to pigments, fillers generally have a low hiding power. In addition to the increase in volume (cheapening) they show in the film very special effects, such. As reflection, surface texture, abrasion or stone chip resistance. Their use is dictated by their particle size, particle size distribution, particle shape, particle structure, hardness, density, color, wettability, abrasiveness, surface adsorption, refractive index, chemical composition, purity, durability and price.
  • suitable fillers for use in the solid pigment preparations according to the invention are those based on kaolin, talc, mica, other silicates, quartz, cristobalite, wollastonite, perlite, diatomaceous earth, fiber fillers, aluminum hydroxide, barium sulfate and / or calcium carbonate.
  • the invention also provides a process for the preparation of solid pigment preparations, essentially containing A) from 40 to 99% by weight of at least one pigment,
  • a suspension of the pigment A), the ketone resin or the ketone / aldehyde resin B) and optionally the inorganic filler C ) is prepared in an organic solvent and / or water, the suspension is dispersed in a suitable aggregate and the solid pigment preparation is isolated.
  • dispersing aggregates are in particular ball mills,
  • Agitator ball mills with horizontal or vertical arrangement or radial agitator mills into consideration For example, it is also possible to use a Dispermat, a Skandex mixer, a Red Devil, a single-roller chair, a three-roll chair or a bead mill.
  • the isolation of the solid pigment preparation can be carried out with the usual drying equipment, for example in a fluidized bed, a spray dryer, a belt dryer or a vacuum dryer.
  • the deagglomeration of the agglomerates contained therein within the scope of the preparation of the pigment preparation according to the invention takes place, for example, by means of hammer mills, pin mills, impact mills or classifier mills, but can also already be integrated into the drying process, eg. B ,. in the form of a Mahltrocknung.
  • the invention therefore also provides the use of solid pigment preparations, essentially containing
  • solid pigment preparations according to the invention can be incorporated in all solvent-containing and solvent-free coating systems known to the person skilled in the art, such as paints, inks, adhesives, inks or printing inks.
  • these systems may be physically drying, oxidatively drying, or otherwise reactive in 1K or 2K paints.
  • nitrocellulose there are a variety of physically drying resins such as nitrocellulose, polyvinyl butyral, VC copolymers, acrylates, methacrylates, cellulose esters, cellulose ethers, hydrocarbon resins, phenolic resins, rosins, maleate resins, polystyrene resins, silicone resins, rubber based paint resins such as cyclo rubber, chlorinated rubber, chlorinated polyolefins or oligobutadienes , Polyolefins, polyvinyl esters, polyvinyl alcohols, polyvinyl acetals, epoxies, amino resins, amido resins and polyester resins.
  • Oxidatively drying coating materials are, for example, alkyd resins.
  • 1 K coating materials are based, for example, on (meth) acrylate, epoxy, polyvinyl acetate, polyester or polyurethane resins. These resins may also be unsaturated, ie contain acrylate or methacrylate double bonds such as, for example, (meth) acrylated (meth) acrylate resins, epoxy (meth) acrylate resins, polyester (meth) acrylate resins, polyether (meth) acrylate resins or polyurethane (meth) acrylate resins.
  • (meth) acrylated (meth) acrylate resins epoxy (meth) acrylate resins
  • polyester (meth) acrylate resins polyester (meth) acrylate resins
  • polyether (meth) acrylate resins or polyurethane (meth) acrylate resins 1 K
  • Coating materials are also those based on hydroxyl-containing polyacrylate or polyester resins with melamine resins or blocked polyisocyanate resins as crosslinkers.
  • 2K coating materials are, for example, those based on polyepoxide systems or of hydroxyl-containing polyacrylate or polyester resins with non-blocked polyisocyanate resins as crosslinkers.
  • auxiliary agents and additives known to the person skilled in the art can be used in the coating systems. These include, for example, defoamers, deaerators, rheology aids, surface additives, the z. Lubricity, scratch resistance, anti-blocking, flow and gloss, substrate wetting additives, driers, stabilizers or biocides.
  • the starting materials listed in the table were stirred with the aid of 2 mm glass beads in the Dispermat CV for 20 min at 2400 U / min and a surface temperature of 25 0 C. Subsequently, the white Mittelölalkydlack was dried for 24 h at room temperature. The ratio of binder (solid) to white pigment was 1: 0.8.
  • the coating composition based on the solid pigment preparation according to the invention and a solvent-containing white alkyd paint exhibited a high gloss and good mechanical and coloristic properties. These properties were with a
  • Coating composition comparable on the basis of a solvent-containing pigment preparation.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne des préparations solides de pigment, comprenant au moins un pigment et une résine, son procédé de fabrication et son utilisation dans des colorants, des peintures, des adhésifs, des encres ou des encres d'imprimerie.
PCT/EP2007/053982 2006-06-09 2007-04-24 Préparations solides de pigment WO2007141090A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200610026762 DE102006026762A1 (de) 2006-06-09 2006-06-09 Feste Pigmentpräparationen
DE102006026762.1 2006-06-09

Publications (1)

Publication Number Publication Date
WO2007141090A1 true WO2007141090A1 (fr) 2007-12-13

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Application Number Title Priority Date Filing Date
PCT/EP2007/053982 WO2007141090A1 (fr) 2006-06-09 2007-04-24 Préparations solides de pigment

Country Status (3)

Country Link
CN (1) CN101085876A (fr)
DE (1) DE102006026762A1 (fr)
WO (1) WO2007141090A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7700664B2 (en) 2004-04-27 2010-04-20 Degussa Ag Polymer compositions of carbonyl-hydrated ketone-aldehyde resins and polyisocyanates in reactive solvents
CN106192556A (zh) * 2016-07-13 2016-12-07 太原理工大学 珍珠岩粉作为造纸用填料/颜料及方法
CN107955398A (zh) * 2017-12-17 2018-04-24 李巧珍 一种表面包覆酞菁蓝复合颜料的制备方法
CN114907704A (zh) * 2022-06-30 2022-08-16 宇虹颜料股份有限公司 一种用于油墨或溶剂型涂料的超细颜料制备物的制作方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5463130B2 (ja) * 2009-12-10 2014-04-09 株式会社ミマキエンジニアリング インク
CN109054705A (zh) * 2018-06-22 2018-12-21 安徽索亚装饰材料有限公司 一种具有良好润湿性能的墙纸用胶黏剂
CN113617493A (zh) * 2021-06-29 2021-11-09 南京信彩科技有限公司 一种彩色油墨制备用原料研磨方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4404809A1 (de) * 1994-02-16 1995-08-17 Huels Chemische Werke Ag Keton-Aldehydharze mit breiter Verträglichkeit, Verfahren zu ihrer Herstellung und ihre Verwendung
DE19813394A1 (de) * 1998-03-26 1999-09-30 Merck Patent Gmbh Pigmentpräparation
EP1277808A2 (fr) * 2001-07-09 2003-01-22 Ciba SC Holding AG Compositions pigmentaires simple distribuables
WO2006082603A1 (fr) * 2005-02-07 2006-08-10 Inxel Trademark & Patents Sagl Enrobage de pigments organiques et inorganiques avec un aldehyde ou des resines cetoniques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4404809A1 (de) * 1994-02-16 1995-08-17 Huels Chemische Werke Ag Keton-Aldehydharze mit breiter Verträglichkeit, Verfahren zu ihrer Herstellung und ihre Verwendung
DE19813394A1 (de) * 1998-03-26 1999-09-30 Merck Patent Gmbh Pigmentpräparation
EP1277808A2 (fr) * 2001-07-09 2003-01-22 Ciba SC Holding AG Compositions pigmentaires simple distribuables
WO2006082603A1 (fr) * 2005-02-07 2006-08-10 Inxel Trademark & Patents Sagl Enrobage de pigments organiques et inorganiques avec un aldehyde ou des resines cetoniques

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7700664B2 (en) 2004-04-27 2010-04-20 Degussa Ag Polymer compositions of carbonyl-hydrated ketone-aldehyde resins and polyisocyanates in reactive solvents
CN106192556A (zh) * 2016-07-13 2016-12-07 太原理工大学 珍珠岩粉作为造纸用填料/颜料及方法
CN107955398A (zh) * 2017-12-17 2018-04-24 李巧珍 一种表面包覆酞菁蓝复合颜料的制备方法
CN114907704A (zh) * 2022-06-30 2022-08-16 宇虹颜料股份有限公司 一种用于油墨或溶剂型涂料的超细颜料制备物的制作方法

Also Published As

Publication number Publication date
CN101085876A (zh) 2007-12-12
DE102006026762A1 (de) 2008-01-10

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