WO2008052831A2 - Préparations de pigment solides et sans formaldéhyde - Google Patents

Préparations de pigment solides et sans formaldéhyde Download PDF

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Publication number
WO2008052831A2
WO2008052831A2 PCT/EP2007/059332 EP2007059332W WO2008052831A2 WO 2008052831 A2 WO2008052831 A2 WO 2008052831A2 EP 2007059332 W EP2007059332 W EP 2007059332W WO 2008052831 A2 WO2008052831 A2 WO 2008052831A2
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Prior art keywords
formaldehyde
solid
carbonyl
ketone
hydrogenated
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PCT/EP2007/059332
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German (de)
English (en)
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WO2008052831A3 (fr
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Andreas Wenning
Peter Denkinger
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Evonik Degussa Gmbh
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Publication of WO2008052831A2 publication Critical patent/WO2008052831A2/fr
Publication of WO2008052831A3 publication Critical patent/WO2008052831A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0008—Coated particulate pigments or dyes with organic coatings
    • C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/0003—Compounds of molybdenum
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/0006—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black containing bismuth and vanadium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/0096—Compounds of antimony
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/04—Compounds of zinc
    • C09C1/043—Zinc oxide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/10—Compounds of cadmium
    • C09C1/12—Cadmium sulfoselenide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/14—Compounds of lead
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/14—Compounds of lead
    • C09C1/20—Lead chromate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/34—Compounds of chromium
    • C09C1/346—Chromium oxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/44—Carbon
    • C09C1/48—Carbon black

Definitions

  • the invention relates to solid, virtually formaldehyde-free pigment preparations consisting of at least one pigment and a resin, their preparation processes 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 Be laminating compositions are suitable for all conventional 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 agents and dispersants facilitate the incorporation of pigments and fillers in the production of paints and coatings, which, as important formulation constituents, essentially determine the optical appearance and the physicochemical properties of Be coatings. For optimum utilization, these solids must be evenly distributed in paints and varnishes, on the other hand, the distribution once achieved must be stabilized.
  • the stabilizing component is in many cases also 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 OZ 6490 (DE 10 2005 012 316) based on the combination of block copolymeric styrene oxide-containing polyalkylene oxides and ketone-aldehyde resins likewise 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 of these liquid pigment preparations generally contain other auxiliaries, such as anti-drying agents, rheology additives, anti-skinning agents, biocides, or agents for increasing the freeze-resistance.
  • auxiliaries such as anti-drying agents, rheology additives, anti-skinning agents, biocides, or agents for increasing the freeze-resistance.
  • solid pigment preparations have been developed which can be dissolved in water or in organic solvents by simple stirring.
  • EP 0 702 055 describes this Dispersing pigments in organic binders of high molecular weight, so-called stir-in pigments, for the production of colored, solvent-borne coatings.
  • stir-in pigments for the production of colored, solvent-borne coatings.
  • these pigments are not stabilized against reagglomeration, so that disturbances such as by specks are not reliably avoided.
  • the pigment preparations described in EP 0 702 062 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 0 902 061 describes vinylpyrrolidone homopolymers or copolymers for preparing stir-in pigment preparations. These pigment preparations are particularly suitable for coloring aqueous industrial coatings or solvent-free plastics.
  • US 6734231 describes a process for preparing a pigment composition by mixing a pigment and a urea-aldehyde resin or urea-ketone resin and then extruding. These resins are not free of formaldehyde.
  • EP 0 432 480 describes masterbatches of mixtures of three essentials
  • Components a) acrylate resins, ketone resins or aldehyde resins, b) citric acid esters, acetyl citric acid esters or tartaric acid esters and c) dyes and / or pigments and
  • 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 that are free of formaldehyde whose composition is as simple as possible and by a particularly easy dispersibility in application media of various kinds, especially by simple stirring (stir-in) distributed in liquid application media are.
  • solid, formaldehyde-free pigment preparations in solvent-based or solvent-free applications, high color strength and flocculation stability should be present.
  • the object underlying the invention could surprisingly be achieved by the use of at least one of the resins B) in combination with at least one pigment.
  • the invention relates to solid, formaldehyde-free pigment preparations, essentially containing
  • 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, indanthrene, isoamidoline (on), isoindolinone, flavanthrone, pyranthrone or isoviolanthrone series. Mixtures or solid solutions of such pigments are also possible. Especially suitable are pigments from the group of the azo, dioxazine, pyrrolo (especially the diketopyrrolopyrrole pigments), quinacridone phthalocyanine, indanthrene or isoindolinone pigments.
  • Important organic pigments are those described in the Color Index. These include, for example, the group of CI. Pigment Red 202, CI. Pigment Red 122, CI. Pigment red 144, CI. Pigment Red 170, CI. Pigment red 177, CI. Pigment Red 179, CI. Pigment Red 254, CI. Pigment red 255, CI. Pigment red 264, CI. Pigment brown 23, CI. Pigment Yellow 13, CI. Pigment Yellow 74, CI. Pigment Yellow 83, CI. Pigment Yellow 109, CI. Pigment Yellow 110, CI. Pigment Yellow 147, CI. Pigment Yellow 191.1, CI. Pigment Orange 48, CI. Pigment Orange 49, CI.
  • Pigment Orange 61 CI. Pigment orange 71, CI. Pigment Blue 15, CI. Pigment Blue 60, CI. Pigment Violet 19, CI. Pigment Violet 23, CI. Pigment Violet 37, CI. Pigment Green 7, CI. Pigment green 36.
  • suitable inorganic pigments are metal oxides, mixed metal oxides, antimony yellow, lead chromates, lead chromate sulfates, lead molybdate, ultramarine blue, cobalt blue, Manganese blue, chrome oxide green, hydrated chrome oxide green, cobalt green, metal sulfides, cadmium sulfoselenides, 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.
  • Such resins B) are known, for example, from DE 102006026758.3, DE 102006026760.5, DE 102006009079.9, DE 102006009080.2 and are preferably used in the context of this invention. Also suitable are their reaction products with at least one aromatic, aliphatic and / or cycloaliphatic di- or polyisocyanate as component B) in the solid pigment preparations.
  • Suitable ketones for the preparation of the carbonyl-hydrogenated ketone resins and the carbonyl-hydrogenated 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 mixture.
  • 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.
  • suitable ketones usually all CH-acidic ketones, can be used.
  • aldehyde component of the carbonyl-hydrogenated 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-aldehyde 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.
  • Carbonyl-hydrogenated resins of 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).
  • non-hydrogenated ketone / aldehyde resins can be used, but then have lower light fastness.
  • the resins of ketone and aldehyde are hydrogenated in the presence of a catalyst with hydrogen at pressures of up to 300 bar.
  • the carbonyl group of the ketone-aldehyde resin is converted into a secondary hydroxy group.
  • a part of the hydroxy groups can be split off, so that methylene groups result.
  • Suitable ketones for the preparation of the carbonyl-hydrogenated and ring-hydrogenated ketone-aldehyde resins are all ketones which, in addition to C-H-acidic protons, have aromatic groups, in particular arylalkyl ketones, such as, for example, As methyl naphthyl ketone, acetophenone and / or its derivatives such.
  • arylalkyl ketones such as, for example, As methyl naphthyl ketone, acetophenone and / or its derivatives such.
  • the ring-hydrogenated resins have OH numbers of 50 to 450 mg KOH / g, preferably, 100 to 350 mg KOH / g, more preferably from 150 to 300 mg KOH / g.
  • the proportion of aromatic groups is below 50 wt .-%, preferably below 30 wt .-%, more preferably below 10 wt .-%. A method is described in DE 33 34 631.
  • Suitable aromatic, aliphatic and / or cycloaliphatic di- and / or polyisocyanates for the preparation of secondary products of hydrogenated ketone resins, carbonyl-hydrogenated ketone / aldehyde resins or carbonyl-hydrogenated and ring-hydrogenated ketone-aldehyde resins are diisocyanates or polyisocyanates, cyclohexane diisocyanate, methylcyclohexane diisocyanate, Ethylcyclohexane diisocyanate, phenylene diisocyanate, propylcyclohexane diisocyanate, methyldiethylcyclohexane diisocyanate, tolylene diisocyanate,
  • Another preferred class of polyisocyanates for the preparation of secondary products of the hydrogenated ketone resins, carbonyl-hydrogenated ketone / aldehyde resins or carbonyl-hydrogenated and ring-hydrogenated ketone / aldehyde resins are the compounds prepared by dimerization, trimerization, allophanatization, biuretization and / or urethanization of the simple diisocyanates with more as two isocyanate groups per molecule, for example the Usmetzungs reside these simple diisocyanates, such as.
  • IPDI, TMDI, HDI and / or Hi 2 MDI with polyhydric alcohols (eg glycerol, trimethylolpropane, pentaerythritol) or polyvalent polyamines, or the triisocyanurates obtained by trimerization of simple diisocyanates such as IPDI, HDI and H 12 MDI, are available.
  • polyhydric alcohols eg glycerol, trimethylolpropane, pentaerythritol
  • polyvalent polyamines eglycerol, trimethylolpropane, pentaerythritol
  • trimerization of simple diisocyanates such as IPDI, HDI and H 12 MDI
  • Ketone / aldehyde resins or carbonyl-hydrogenated and ring-hydrogenated ketone-aldehyde resins by further hydroxy-functional polymers such as B. hydroxy-functional polyesters and / or To replace polyacrylates. As a result, properties such. B. flexibility or hardness can be set more targeted (claim 2).
  • a suitable catalyst for preparing the resins of hydrogenated ketone resins and / or a carbonyl-hydrogenated ketone / aldehyde resins and / or a carbonyl-hydrogenated and ring-hydrogenated ketone-aldehyde resins based on aromatic ketones and at least one aromatic, aliphatic and / or cycloaliphatic di- and / or polyisocyanate are used.
  • Tin organyls such as dibutyltin dilaurate (DBTL) or dibutyltin diactate (DBTA) are known to be good catalysts.
  • Catalysts based on the metals bismuth, zirconium, iron or aluminum are also well suited, such as.
  • carboxylates, chelates and complexes are also well suited, such as.
  • B. tert. Amines for example, 1,4-diazabicyclo [2.2.2] octane (DABCO), l, 8-diazabicyclo [5.4.0] undec-7-ene (DBU), N, N-dimethylcyclohexylamine (DMCA) or l, 5-diazabicyclo [2.3.0] non-5-en (DBN).
  • DABCO 1,4-diazabicyclo [2.2.2] octane
  • DBU 8-diazabicyclo [5.4.0] undec-7-ene
  • DBU N, N-dimethylcyclohexylamine
  • DMCA N-dimethylcyclohexylamine
  • DBN 5-diazabicyclo [2.3.0] non-5-en
  • the melting range of the reaction products prepared from hydrogenated ketone resins and / or a carbonyl-hydrogenated ketone / aldehyde resins and / or a carbonyl-hydrogenated and ring-hydrogenated ketone-aldehyde resins based on aromatic ketones and at least one aromatic, aliphatic and / or cycloaliphatic di- and / or or or polyisocyanate is above 140 0 C, preferably above 145 0 C, more preferably above 150 0 C.
  • a typical product is synthetic resin 1201 from Degussa AG.
  • component C also fillers can be used. They are usually powdery, practically insoluble in the application medium substances. They are mainly obtained from naturally occurring minerals by mining, cleaning, grinding and subsequent classification 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, for example, those based on kaolin, talc, mica, other silicates, quartz, cristobalite, wollastonite, perlite, diatomaceous earth, fiber fillers, aluminum hydroxide, barium sulfate or calcium carbonate.
  • the invention also provides a process for the preparation of solid, formaldehyde-free pigment preparations, essentially containing
  • ball mills, stirred ball mills with a horizontal or vertical arrangement or radial agitator mills come into consideration as dispersing units.
  • dispersing units 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.
  • solid, formaldehyde-free 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, for example, physically drying, oxidatively drying, or otherwise reactive in IK or 2K paints.
  • oxidative Drying coating materials are, for example, alkyd resins.
  • 1K 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 (meth) acrylated (meth) acrylate resins, epoxy (meth) acrylate resins, polyester (meth) acrylate resins,
  • Polyether (meth) acrylate resins or polyurethane (meth) acrylate resins are also those based on hydroxyl-containing polyacrylate or polyester resins with melamine resins or blocked polyisocyanate resins as crosslinkers.
  • 2K-Be laminating substances 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 invention therefore also relates to the use of solid, formaldehyde-free pigment preparations, essentially containing A) from 40 to 99% by weight of at least one pigment,
  • the solid, formaldehyde-free pigment preparations according to the invention are distinguished by particularly easy dispersibility in application media of various kinds, especially by simple stir-in in liquid application media. By using these solid pigment preparations in solventborne or solventless applications such as powder coatings, coating systems are obtained which have high color strength, high gloss and good flocculation stability.
  • the hydrogenated resin was soluble in ethanol, dichloromethane, ethyl acetate, butyl acetate, isopropanol, acetone and diethyl ether. It was insoluble in nonpolar solvents such as n-hexane or white spirit.
  • the pigment preparations 2) and 3) were initially charged and the white stock paint (4) was added in portions with stirring.
  • Table 2 gives the coating compositions and their properties.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

L'invention concerne des préparations de pigment solides et pratiquement sans formaldéhyde, comprenant au moins un pigment et une résine, leur procédé de fabrication et leur utilisation dans des colorants, des peintures, des adhésifs, des encres ou des encres d'impression.
PCT/EP2007/059332 2006-11-03 2007-09-06 Préparations de pigment solides et sans formaldéhyde WO2008052831A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006051803.9 2006-11-03
DE200610051803 DE102006051803A1 (de) 2006-11-03 2006-11-03 Feste, formaldehydfreie Pigmentpräparationen

Publications (2)

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WO2008052831A2 true WO2008052831A2 (fr) 2008-05-08
WO2008052831A3 WO2008052831A3 (fr) 2008-12-18

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PCT/EP2007/059332 WO2008052831A2 (fr) 2006-11-03 2007-09-06 Préparations de pigment solides et sans formaldéhyde

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CN (1) CN101173114A (fr)
DE (1) DE102006051803A1 (fr)
WO (1) WO2008052831A2 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009047097A1 (fr) * 2007-10-05 2009-04-16 Evonik Degussa Gmbh Compositions d'encres d'imprimerie
WO2009047102A1 (fr) * 2007-10-05 2009-04-16 Evonik Degussa Gmbh Compositions de revêtement
US7700664B2 (en) 2004-04-27 2010-04-20 Degussa Ag Polymer compositions of carbonyl-hydrated ketone-aldehyde resins and polyisocyanates in reactive solvents

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110128637B (zh) * 2018-02-08 2021-11-16 广东华润涂料有限公司 酮醛改性树脂及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0838486A1 (fr) * 1996-10-23 1998-04-29 Hüls Aktiengesellschaft Dispersions aqueuses de résine
WO2005075584A1 (fr) * 2004-02-03 2005-08-18 Degussa Ag Utilisation de resines radiodurcissables a base de resines cetone aldehyde et/ou uree aldehyde
WO2006018341A1 (fr) * 2004-08-12 2006-02-23 Degussa Gmbh Produits de reaction exempts d'etain a point de fusion eleve, constitues de resines de cetone-aldehyde carbonyle-hydrogenees, de resines de cetone hydrogenees et de resines de cetone-aldehyde carbonyle-hydrogenees et a noyau hydrogene a base de cetones et de polyisocyanates aromatiques

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0838486A1 (fr) * 1996-10-23 1998-04-29 Hüls Aktiengesellschaft Dispersions aqueuses de résine
WO2005075584A1 (fr) * 2004-02-03 2005-08-18 Degussa Ag Utilisation de resines radiodurcissables a base de resines cetone aldehyde et/ou uree aldehyde
WO2006018341A1 (fr) * 2004-08-12 2006-02-23 Degussa Gmbh Produits de reaction exempts d'etain a point de fusion eleve, constitues de resines de cetone-aldehyde carbonyle-hydrogenees, de resines de cetone hydrogenees et de resines de cetone-aldehyde carbonyle-hydrogenees et a noyau hydrogene a base de cetones et de polyisocyanates aromatiques

Cited By (3)

* 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
WO2009047097A1 (fr) * 2007-10-05 2009-04-16 Evonik Degussa Gmbh Compositions d'encres d'imprimerie
WO2009047102A1 (fr) * 2007-10-05 2009-04-16 Evonik Degussa Gmbh Compositions de revêtement

Also Published As

Publication number Publication date
CN101173114A (zh) 2008-05-07
WO2008052831A3 (fr) 2008-12-18
DE102006051803A1 (de) 2008-05-08

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