[go: up one dir, main page]

WO2008012245A2 - Préparations pigmentaires sous forme de comprimés - Google Patents

Préparations pigmentaires sous forme de comprimés Download PDF

Info

Publication number
WO2008012245A2
WO2008012245A2 PCT/EP2007/057403 EP2007057403W WO2008012245A2 WO 2008012245 A2 WO2008012245 A2 WO 2008012245A2 EP 2007057403 W EP2007057403 W EP 2007057403W WO 2008012245 A2 WO2008012245 A2 WO 2008012245A2
Authority
WO
WIPO (PCT)
Prior art keywords
pigment
weight
water
acid
additive
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2007/057403
Other languages
German (de)
English (en)
Other versions
WO2008012245A3 (fr
Inventor
Hansulrich Reisacher
Marco Schmidt
Dieter Flick
Michaela Müller-Halanke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of WO2008012245A2 publication Critical patent/WO2008012245A2/fr
Publication of WO2008012245A3 publication Critical patent/WO2008012245A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B18/00—Use of agglomerated or waste materials or refuse as fillers for mortars, concrete or artificial stone; Treatment of agglomerated or waste materials or refuse, specially adapted to enhance their filling properties in mortars, concrete or artificial stone
    • C04B18/02—Agglomerated materials, e.g. artificial aggregates
    • C04B18/028—Agglomerated materials, e.g. artificial aggregates temporarily agglomerated, e.g. agglomerates which fall apart during mixing with the other mortar or concrete ingredients
    • 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
    • C09D17/00—Pigment pastes, e.g. for mixing in paints

Definitions

  • the present invention relates to pigment preparations in tablet form, obtainable by dry blending a solid pigment preparation (A) with a tablet disintegrant (B) and, if desired, one or more further adjuvants from the group of release agents (C), binders (D) and water-soluble surface-active additives (E) without particle comminution and subsequent compaction.
  • the invention relates to the preparation of the pigment preparations in tablet form and their use for coloring coating systems containing liquid phase as water, organic solvents or mixtures of water and organic solvents, and for mass coloration of wood and construction materials.
  • Solid pigment preparations in powder or granular form which can be distributed in liquid application media by stirring or shaking (so-called stir-in pigments), are becoming increasingly interesting due to their easier handling compared to liquid pigment preparations.
  • stir-in pigments are becoming increasingly interesting due to their easier handling compared to liquid pigment preparations.
  • the pigment tablets known from JP-A-03-221570 are likewise obtained by dry grinding of the pigment coated with surface-active additive with an acid / carbonate disintegrant and tabletting of the millbase.
  • pigment preparations in tablet form which are distinguished by advantageous application properties, in particular easy meterability and at the same time easy dispersibility in the application media. Accordingly, pigment preparations have been found in tablet form which are prepared by dry blending a solid pigment preparation (A) with a tablet explosive (B) and, if desired, one or more other adjuvants from the group of release agents (C), binder (D) and water-soluble surfactants Additive (E) without particle size reduction and subsequent compacting are available.
  • the pigment preparations of the invention are characterized by particularly simple handling because of their tablet form. They are easily and dust-free dispensable and surprisingly show the stir-in properties of the underlying pigment preparations despite the compacting that has been carried out.
  • the shape and size of the tablets can be adapted to the particular application.
  • suitable diameters are e.g. in the range of 0.2 to 3 cm, the height of the tablets is usually 0.2 to 1 cm.
  • the tablets may also have a different shape, for example a briquette-like shape.
  • the pigment preparations according to the invention in tablet form contain as essential constituents solid pigment preparations (A) as well as additives customary for tablets.
  • the solid pigment preparations (A) typically have the following constituents:
  • (A1.2) contains 0 to 95 wt .-% of a non-inherent filler
  • the coloring component (A1) of the pigment preparations (A) is based on a pigment (A1.1) which may be present in combination with a filler (A1.2) having no intrinsic color.
  • inorganic or organic pigments may be contained in the pigment preparations (A).
  • the pigment preparations also mixtures of various inorganic or various organic pigments or mixtures of inorganic and organic pigments.
  • the pigments are in finely divided form. Accordingly, the pigments usually have mean particle sizes of 0.1 to 5 ⁇ m.
  • inorganic pigments color, black and white pigments (color pigments) as well as luster pigments can be used.
  • Typical organic pigments are colored and black pigments.
  • Suitable organic pigments are, for example:
  • Disazo condensation pigments Cl. Pigment Yellow 93, 95 and 128;
  • Anthanthrone pigments C Pigment Red 168; Anthraquinone pigments: C Pigment Yellow 147, 177 and 199; C Pigment Violet 31;
  • Anthrapyrimidine pigments C Pigment Yellow 108; Quinacridone pigments: C Pigment Orange 48 and 49; C Pigment Red 122, 202, 206 and 209; C Pigment Violet 19;
  • Diketopyrrolopyrrole pigments C Pigment Orange 71, 73 and 81; C Pigment Red 254, 255, 264, 270 and 272; Dioxazine pigments: C Pigment Violet 23 and 37; C Pigment Blue 80;
  • Flavanthrone pigments C Pigment Yellow 24; - Indanthrone pigments: C.. Pigment Blue 60 and 64;
  • - metal complex pigments C.. Pigment Red 257; C.. Pigment Yellow 1 17, 129, 150, 153 and 177; C.. Pigment Green 8; - Perinone pigments: C.. Pigment Orange 43; C.. Pigment Red 194;
  • Thioindigo pigments C. Pigment Red 88 and 181; C. Pigment Violet 38;
  • Triaryl carbonium pigments C. Pigment Blue 1, 61 and 62; C. Pigment Green 1; C. Pigment Red 81, 81: 1 and 169; C. Pigment Violet 1, 2, 3 and 27;
  • Suitable inorganic pigments are:
  • titanium dioxide CI Pigment White 6
  • zinc white colored zinc oxide
  • Zinc sulfide lithopone
  • Black pigments iron oxide black (CI Pigment Black 11), iron manganese black, spinel black (CI Pigment Black 27); Carbon black (CI Pigment Black 7);
  • Cerium sulphide (CI Pigment Orange 75); Iron oxide yellow (CI Pigment Yellow 42); Nickel titanium yellow (Cl.
  • Pigment Yellow 53 Cl. Pigment Yellow 157, 158, 159, 160, 161, 162, 163, 164 and 189); Chromium titanium yellow; Spinel phases (CI Pigment Yellow 1 19); Cadmium sulfide and cadmium zinc sulfide (CI Pigment Yellow 37 and 35); Chrome yellow (CI Pigment Yellow 34); Bismuth vanadate (CI Pigment Yellow 184).
  • the luster pigments are single-phase or multi-phase platelet-shaped pigments whose color play is characterized by the interplay of interference, reflection and absorption phenomena. Examples which may be mentioned aluminum platelets and one or more times, in particular coated with metal oxides aluminum, iron oxide and mica platelets.
  • the pigment (A1.1) may be present in combination with a non-inherent colorant, in particular an inorganic filler (A1.2).
  • colorless or white fillers generally have a refractive index ⁇ 1.7.
  • the refractive index of chalk is 1, 55, of barite 1, 64, of kaolin 1, 56, of talc 1, 57, of mica 1, 58 and of silicates 1, 55.
  • the fillers (A1.2), like the pigments (A1.1), are insoluble in the application medium and originate, in particular, from the following chemical classes, with examples of products of natural origin as well as products of synthetic origin being listed by way of example:
  • Oxides and hydroxides of course: alumina and magnesia; synthetic: aluminum hydroxide and magnesium hydroxide;
  • Silica and silicates natural: quartz, Christobalite, kieselguhr, talc, kaolin, silica, mica, wollastonite and feldspar; synthetic: fumed silica, precipitated silica, aluminosilicates and calcined aluminosilicates;
  • Carbonates natural: calcium and magnesium carbonates, such as calcite, chalk, dolomite and magnesite; synthetic: precipitated calcium carbonate;
  • Sulphates natural: barium and calcium sulphates, such as barite and gypsum; synthetic: precipitated barium sulfate.
  • the fillers (A1.2) can have a wide variety of particle shapes. For example, they may be spheres, cubes, platelets or fibers. Natural-based fillers typically have particle sizes in the range of about 1 to 300 microns. Thus, natural chalk based commercial products, e.g. a dso value of usually 1 to 160 microns. Particle sizes below 1 ⁇ m are generally only present in the case of fillers produced synthetically, in particular by precipitation methods.
  • Preferred fillers (A1.2) are carbonates and sulfates, with natural and precipitated chalk and barium sulfate being particularly preferred. These products are commercially available for example under the name Omyacarb ® and Omyalite ® (Fa. Omya) and Blanc fixe (Messrs. Sachtleben) available.
  • the coloring component (A1) of the pigment preparations (A) contains 5 to 100% by weight of pigment (A1.1) and 0 to 95% by weight of filler (A1.2).
  • the pigment preparations (A) comprise at least one water-soluble surface-active additive.
  • nonionic and / or anionic water-soluble surface-active additives are suitable here.
  • nonionic additives are based on polyethers (additives (A2.1)).
  • polyethylene oxides preferably C 2 -C 4 -alkylene oxides and phenyl-substituted C 2 -C 4 -alkylene oxides
  • polyethylene oxides preferably polypropylene oxides and poly (phenylethyleneoxides)
  • block copolymers in particular polypropylene oxide and polyethylene oxide blocks or poly (phenylethylene oxide) and polyethylene oxide blocks having polymers, and also random copolymers of these alkylene oxides suitable.
  • polyalkylene oxides can be prepared by polyaddition of the alkylene oxides onto starter molecules, such as saturated or unsaturated aliphatic and aromatic alcohols, saturated or unsaturated aliphatic and aromatic amines, saturated or unsaturated aliphatic carboxylic acids and carboxylic acid amides, and aromatic carboxylic acid amides and sulfonic acid amides.
  • starter molecules such as saturated or unsaturated aliphatic and aromatic alcohols, saturated or unsaturated aliphatic and aromatic amines, saturated or unsaturated aliphatic carboxylic acids and carboxylic acid amides, and aromatic carboxylic acid amides and sulfonic acid amides.
  • the aromatic starter molecules may be substituted by C 1 -C 20 -alkyl or C 7 -C 30 -aralkyl.
  • alkylene oxide 1 to 300 mol, preferably 3 to 150 mol, of alkylene oxide are used per mole of starter molecule; in the case of aromatic starter molecules, the amounts of alkylene oxide are above all from 2 to 100 mol, preferably from 5 to 50 mol and in particular from 10 to 30 mol.
  • the polyaddition products may have a terminal OH group or be end group-capped, for example present as C 1 -C 6 alkyl ethers.
  • Suitable aliphatic alcohols generally contain 6 to 26 C atoms, preferably 8 to 18 C atoms, and may be unbranched, branched or cyclic. Examples which may be mentioned are octanol, nonanol, decanol, isodecanol, undecanol, dodecanol, 2-butyloctanol, tridecanol, isotridecanol, tetradecanol, pentadecanol, hexadecanol (cetyl alcohol), 2-hexyldecanol, heptadecanol, octadecanol (stearyl alcohol), 2-heptylundecanol , 2-octyldecanol, 2-nonyltridecanol, 2-decyltetradecanol, oleyl alcohol and 9-octadecenol, as well as mixtures of these alcohols, such as Cs / do,
  • the alkylene oxide adducts to these alcohols usually have average molecular weights M n of from 200 to 5,000.
  • the alkyl-substituted products which are substituted in particular by C 1 -C 12 -alkyl, preferably C 4 -C 12- or C 1 -C 4 -alkyl are also suitable
  • the aralkyl-substituted products in particular C 7 -C 30 -aralkyl, substituted phenols, such as hexylphenol, heptylphenol, octylphenol, nonylphenol, isononylphenol, undecylphenol, dodecylphenol, di- and tributylphenol and dinonylphenol, and bisphenol A and its reaction products with styrene all in the ortho positions to both OH groups by a total of 4 phenyl-1-ethyl radicals substituted bisphenol A, called.
  • Suitable aliphatic amines correspond to the aliphatic alcohols listed above. Of particular importance here are the saturated and unsaturated fatty amines, which preferably have 14 to 20 carbon atoms. Examples of aromatic amines are aniline and its derivatives.
  • Particularly suitable aliphatic carboxylic acids are saturated and unsaturated fatty acids, which preferably contain 14 to 20 C atoms, and hydrogenated, partially hydrogenated and unhydrogenated resin acids and also polybasic carboxylic acids, for example dicarboxylic acids, such as maleic acid.
  • Suitable carboxylic acid amides are derived from these carboxylic acids.
  • the alkylene oxide adducts to the monohydric amines and alcohols are of particular interest.
  • divalent to pentavalent amines are preferred which in particular of the formula H 2 N- (R 1 -NR 2 ) n -H (R 1 : C 2 -C 6 -alkylene; R 2 : hydrogen or d-) C ⁇ -alkyl; n: 1 to 5).
  • ethylenediamine diethylenetriamine, triethylenetetramine, tetraethylenepentamine, propylenediamine-1,3-dipropylenetriamine, 3-amino-1-ethyleneaminopropane, hexamethylenediamine, dihexamethylenetriamine, 1,6-bis (3-aminopropylamino) hexane and N-methyldipropylenetriamine, with hexamethylenediamine and diethylenetriamine being particularly preferred, and ethylenediamine being most preferred.
  • these amines are first reacted with propylene oxide and then with ethylene oxide.
  • the content of the block copolymers of ethylene oxide is usually about 10 to 90% by weight.
  • the polybasic amine-based block copolymers generally have average molecular weights M n of from 1,000 to 40,000, preferably from 1,500 to 30,000.
  • dihydric to pentahydric alcohols are preferred.
  • examples are C 2 -C 6 -alkylene glycols and the corresponding di- and polyalkylene glycols, such as ethylene glycol, propylene glycol-1, 2 and -1, 3, butylene glycol-1, 2 and -1, 4, hexylene glycol-1, 6, dipropylene glycol and Polyethylene glycol, glycerol and pentaerythritol called, with ethylene glycol and polyethylene glycol are particularly preferred and propylene glycol and dipropylene glycol are very particularly preferred.
  • Particularly preferred alkylene oxide adducts with at least bifunctional alcohols have a central polypropylene oxide block, that is to say they start from a propylene glycol or polypropylene glycol which is reacted first with further propylene oxide and then with ethylene oxide.
  • the content of the block copolymers of ethylene oxide is usually from 10 to 90% by weight.
  • the block copolymers based on polyhydric alcohols generally have average molecular weights M n of from 1 000 to 20 000, preferably from 1 000 to 15 000.
  • alkylene oxide are known and commercially available for example under the name Tetronic ®, Pluronic ® and Pluriol® ® (BASF), Atlas ® (Uniqema), emulsifier WN and 386 (Lanxess) and Soprophor ® (Rhodia) available.
  • water-soluble anionic surface-active agents which are particularly suitable as component (A2) are additives based on polymers of ethylenically unsaturated carboxylic acids (A2.2), additives based on polyurethanes (A2.3), additives based on acidic phosphoric acid. , Phosphonic acid, sulfuric acid and / or sulfonic acid esters of the abovementioned polyethers (A2.4) and additives based on polycondensation products of aromatic sulfonic acids and formaldehyde (A2.5).
  • mixtures of several additives that is to say both mixtures of different nonionic additives and mixtures of various anionic additives and also mixtures of nonionic and anionic additives.
  • Suitable anionic water-soluble surface-active additives based on polymers of unsaturated carboxylic acids (A2.2) are, in particular, additives from the group of the homo- and copolymers of ethylenically unsaturated monocarboxylic acids and / or ethylenically unsaturated dicarboxylic acids which additionally contain polymerized vinyl monomers containing no acid function can, the alkoxylation products of these homopolymers and copolymers and the salts of these homo- and copolymers and their alkoxylation.
  • Vinyl aromatics such as styrene, methylstyrene and vinyltoluene; Ethylene, propylene, isobutene, diisobutene and butadiene; Vinyl ethers, such as polyethylene glycol monovinyl ether;
  • Vinyl esters of linear or branched monocarboxylic acids such as vinyl acetate and vinyl propionate
  • Alkyl esters and aryl esters of ethylenically unsaturated monocarboxylic acids especially acrylic and methacrylic esters, such as methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, 2-ethylhexyl, nonyl, lauryl and hydroxyethyl (meth) acrylate and phenyl, naphthyl and benzyl (meth) acrylate
  • Dialkyl esters of ethylenically unsaturated dicarboxylic acids such as dimethyl, diethyl, dipropyl, diisopropyl, dibutyl, dipentyl, dihexyl, di-2-ethylhexyl, dinonyl, dilauryl and di-2-hydroxyethyl maleate and fum
  • Examples of preferred homopolymers of these monomers are, in particular, polyacrylic acids.
  • the copolymers of the monomers mentioned may be composed of two or more, in particular three, different monomers. There may be random copolymers, alternating copolymers, block copolymers and graft copolymers.
  • Preferred copolymers are styrene / acrylic acid, acrylic acid / maleic acid, acrylic acid / methacrylic acid, butadiene / acrylic acid, isobutene / maleic acid, diisobutene / maleic acid and styrene / maleic acid copolymers, each of which contains acrylic acid esters as additional monomer constituents and / or May contain maleic acid esters, called.
  • the carboxyl groups of the non-alkoxylated homo- and copolymers are at least partially in salt form to ensure water solubility.
  • Suitable examples are the alkali metal salts, such as sodium and potassium salts, and the ammonium salts.
  • the non-alkoxylated polymeric additives (A2.2) have average molecular weights Mw of 900 to 250,000.
  • molecular weight data are given by way of example for various polymers: polyacrylic acids: M w from 900 to 250,000; Styrene / acrylic acid copolymers: M w from 1 000 to 50 000; Acrylic acid / methacrylic acid copolymers: M w from 1,000 to 250,000; Acrylic acid / maleic acid copolymers: M w from 2,000 to 70,000.
  • polyether alcohols themselves, preferably polyethylene glycols and polypropylene glycols, and their one-sided end group-capped derivatives, especially the corresponding monoethers, such as monoaryl ethers, for example monophenyl ethers, and in particular mono-C 1 -C -alkyl ethers, for example ethylene-and propylene glycols etherified with fatty alcohols, and the polyetheramines which are obtained, for example, by conversion of a terminal OH group of corresponding polyether alcohols or by polyaddition of alkylene oxides to preferably primary aliphatic amines can be produced.
  • Polyethylene glycols, polyethylene glycol monoethers and polyether amines are preferred.
  • the average molecular weights M n of the polyether alcohols and their derivatives used are usually 200 to 10,000.
  • the surface-active properties of the additives (A2.2) can be adjusted in a targeted manner.
  • anionic surface-active additives are also known and commercially available for example under the name Sokalan ® (BASF), Joncryl ® (Johnson Polymer), Alcosperse ® (Alco), Geropon ® (Rhodia), Good-Rite ® (Goodrich ) Neoresin ® (Avecia), Orotan ® and Morez ® (Rohm & Haas), Disperbyk ® (Byk) and Tegospers ® (Goldschmidt) available.
  • these pigment preparations may furthermore contain polyurethane-based additives (A2.3).
  • polyurethane encompasses not only the pure reaction products of polyfunctional isocyanates (A2.3a) with isocyanate-reactive organic compounds containing hydroxyl groups (A2.3b), but also those reaction products which are obtained by the addition of further isocyanate-reactive compounds, e.g. of primary or secondary amino-bearing carboxylic acids are additionally functionalized.
  • additives are distinguished from other surface-active additives by their low ionic conductivity and their neutral pH.
  • Suitable polyfunctional isocyanates (A2.3a) for the preparation of the additives (A2.3) are in particular diisocyanates, but it is also possible to use compounds having three or four isocyanate groups. Both aromatic and aliphatic isocyanates can be used.
  • di- and triisocyanates examples include: 2,4-tolylene diisocyanate (2,4-TDI), 4,4'-diphenylmethane diisocyanate (4,4'-MDI), para-xylylene diisocyanate, 1,4-diisocyanatobenzene , Tetramethylxylylene diisocyanate (TMXDI), 2,4'-diphenylmethane diisocyanate (2,4'-MDI) and triisocyanatotoluene and isophorone diisocyanate (IPDI),
  • mixtures of isocyanates (A2.3a).
  • mixtures of structural isomers of 2,4-toluene diisocyanate and triisocyanatotoluene e.g. Mixtures of 80 mol% of 2,4-tolylene diisocyanate and 20 mol% of 2,6-tolylene diisocyanate; Mixtures of cis- and trans-cyclohexane-1,4-diisocyanate; Mixtures of 2,4- or 2,6-toluene diisocyanate with aliphatic diisocyanates, such as hexamethylene diisocyanate and isophorone diisocyanate.
  • Suitable isocyanate-reactive organic compounds are preferably compounds having at least two isocyanate-reactive hydroxyl groups per molecule. However, suitable compounds (A2.3b) are also compounds which have only one isocyanate-reactive hydroxy group per molecule. These monofunctionalized compounds can partially or completely replace the compounds containing at least two isocyanate-reactive hydroxyl groups per molecule in the reaction with the polyisocyanate (A2.3a).
  • isocyanate-reactive compounds (A2.3b) having at least two isocyanate-reactive hydroxyl groups per molecule.
  • polyetherdiols polyetherdiols, polyesterdiols, lactone-based polyesterdiols, diols and triols having up to 12 carbon atoms, dihydroxycarboxylic acids, dihydroxysulphonic acids, dihydroxyphosphonic acids, polycarbonatediols, polyhydroxyolefins and polysiloxanes having on average at least two hydroxyl groups per molecule.
  • Suitable polyether diols are, for example, homopolymers and copolymers of C 2 -C 4 -alkylene oxides, such as ethylene oxide, propylene oxide and butylene oxide, tetrahydrofuran, styrene oxide and / or epichlorohydrin, which are reacted in the presence of a suitable catalyst, e.g. Boron trifluoride, are available. Further suitable polyether diols are by (co) polymerization of these compounds in the presence of a starter having at least two normal hydrogen atoms, e.g.
  • polyether diols examples include polyethylene glycol, polypropylene glycol, polybutylene glycol and polytetrahydrofuran and also copolymers thereof.
  • the molecular weight M n of the polyether diols is preferably 250 to 5,000, more preferably 500 to 2,500.
  • Polyester diols suitable as isocyanate-reactive compound (A2.3b) are generally known.
  • Preferred polyester diols are the reaction products of diols with dicarboxylic acids or their reactive derivatives, e.g. Anhydrides or dimethyl esters.
  • Suitable dicarboxylic acids are saturated and unsaturated aliphatic and aromatic dicarboxylic acids which may carry additional substituents, such as halogen.
  • Preferred aliphatic dicarboxylic acids are saturated unbranched ⁇ , ⁇ -dicarboxylic acids containing from 3 to 22, especially 4 to 12, carbon atoms.
  • dicarboxylic acids examples include: succinic acid, glutaric acid, adipic acid, suberic acid, sebacic acid, 1,1'-dodecanedicarboxylic acid, maleic acid, maleic anhydride, fumaric acid, itaconic acid, phthalic acid, isophthalic acid, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, tetrachlorophthalic anhydride, endomethylenetetrahydrophthalic anhydride - drid, terephthalic acid, terephthalic acid dimethyl ester and dimethyl isophthalate.
  • Particularly suitable diols are saturated and unsaturated aliphatic and cycloaliphatic diols.
  • the particularly preferred aliphatic ⁇ , ⁇ -diols are unbranched and have 2 to 12, in particular 2 to 8, especially 2 to 4 C-atoms.
  • Preferred cycloaliphatic diols are derived from cyclohexane.
  • diols examples include: ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 4-butanediol, 2-methylpropane-1, 3-diol, 1, 5-pentanediol, neopentyl glycol, 1, 6-hexanediol, 1 , 8-octanediol, 1, 10-decanediol, 1, 12-dodecanediol, cis- and trans-but-2-ene-1, 4-diol, 2-butyne-1, 4-diol and cis- and trans-1 , 4-di (hydroxymethyl) cyclohexane.
  • the molecular weight M n of the polyester diols is preferably from 300 to 5,000.
  • Lactone-based polyesterdiols suitable as isocyanate-reactive compound (A2.3b) are based in particular on aliphatic saturated unbranched ⁇ -hydroxycarboxylic acids having 4 to 22, preferably 4 to 8, carbon atoms. Also suitable are branched .omega.-hydroxycarboxylic acids in which one or more Chb groups in the alkylene chain are replaced by -CH (Ci-C 4 -AlkVl) -.
  • ⁇ -hydroxycarboxylic acids examples include ⁇ -hydroxybutyric acid and ⁇ -hydroxyvaleric acid.
  • diols are also suitable as isocyanate-reactive compounds (A2.3b), the same preferences apply as above.
  • isocyanate-reactive compounds are triols which have, in particular, 3 to 12, in particular 3 to 8, C atoms.
  • An example of a particularly suitable triol is trimethylolpropane.
  • dihydroxycarboxylic acids which are suitable as isocyanate-reactive compounds (A2.3b) are aliphatic saturated dihydroxycarboxylic acids which preferably contain 4 to 14 C atoms. Especially suitable are dihydroxycarboxylic acids of the formula
  • DMPA dimethylolpropionic acid
  • isocyanate-reactive compounds are also suitable as isocyanate-reactive compounds (A2.3b) are the corresponding dihydroxysulfonic acids and dihydroxyphosphonic acids, such as 2,3-dihydroxypropane-phosphonic acid.
  • dihydroxycarboxylic acid is intended to include compounds which contain more than one carboxyl function (or anhydride or ester function). Such compounds are obtainable by reacting dihydroxy compounds with tetracarboxylic dianhydrides, such as pyromellitic dianhydride or cyclopentanetetracarboxylic dianhydride, in a molar ratio of 2: 1 to 1:05 in a polyaddition reaction and preferably have an average molecular weight M n of 500 to 10,000.
  • tetracarboxylic dianhydrides such as pyromellitic dianhydride or cyclopentanetetracarboxylic dianhydride
  • suitable polycarbonate diols are the reaction products of phosgene with an excess of diols, in particular unbranched saturated aliphatic ⁇ , ⁇ -diols having 2 to 12, especially 2 to 8, especially 2 to 4 carbon atoms ,
  • Polyhydroxyolefins suitable as isocyanate-reactive compound (A2.3b) are especially ⁇ , ⁇ -dihydroxyolefins, with ⁇ , ⁇ -dihydroxybutadienes being preferred.
  • the polysiloxanes which are furthermore suitable as isocyanate-reactive compound (A2.3b) contain on average at least two hydroxyl groups per molecule.
  • Particularly suitable polysiloxanes have an average of 5 to 200 Si atoms (number average) and are especially substituted by Ci-Ci2-alkyl groups, in particular methyl groups.
  • isocyanate-reactive compounds which have only one isocyanate-reactive hydroxyl group include in particular aliphatic, cycloaliphatic, araliphatic or aromatic monohydroxycarboxylic acids and -sulfonic acids.
  • the polyurethane-based additives (A2.3) are prepared by reacting the compounds (A2.3a) and (A2.3b), the molar ratio of (A2.3a) to (A2.3b) generally being 2: 1 to 1 : 1, preferably 1, 2: 1 to 1: 1, 2, is.
  • isocyanate-reactive compounds for example dithiols, thioalcohols, such as thioethanol, amino alcohols, such as ethanolamine and N-methylethanolamine, or diamines, such as ethylenediamine, and thereby Polyurethanes which, in addition to the urethane groups, also carry isocyanurate groups, allophanate groups, urea groups, biuret groups, uretdione groups or carbodiimide groups.
  • isocyanate-reactive compounds are aliphatic, cycloaliphatic, araliphatic or aromatic carboxylic acids and sulfonic acids which carry at least two primary and / or secondary amino groups.
  • the carboxyl groups of the reaction products (A2.3) are at least partially in salt form to ensure water solubility.
  • Suitable examples are alkali metal salts, such as sodium and potassium salts, and ammonium salts.
  • the additives (A2.3) have average molecular weights M w of 500 to 250,000.
  • the surface-active properties of the additives (A2.3) can be adjusted in a targeted manner.
  • anionic surface-active additives are known and SN95 commercially for example under the name Borchi® ® GEN (Borchers).
  • Water-soluble anionic surface-active additives based on acidic phosphoric acid, phosphonic acid, sulfuric acid and / or sulfonic acid esters of polyethers are based in particular on the reaction products of the abovementioned polyethers (A2.1) with phosphoric acid, phosphorus pentoxide and phosphonic acid or sulfuric acid and sulfonic acid. In this case, the polyethers are converted into the corresponding phosphoric acid mono- or diesters and phosphonic acid esters or the sulfuric acid monoesters and sulfonic acid esters.
  • These acid esters are preferably in the form of water-soluble salts, in particular as alkali metal salts, especially sodium salts, and ammonium salts, but they can also be used in the form of the free acids.
  • Preferred phosphates and phosphonates are derived above all from alkoxylated, in particular ethoxylated, fatty and oxo alcohols, alkylphenols, fatty amines, fatty acids and resin acids.
  • Preferred sulfates and sulfonates are based in particular on alkoxylated, in particular ethoxylated, fatty alcohols, alkylphenols and amines polyhydric amines, such as hexamethylenediamine.
  • anionic surface-active additives are known and commercially available for example under the names Nekal ® (BASF), Tamol ® (BASF), Crodafos ® (Croda), Rhodafac ® (Rhodia), Maphos ® (BASF), Texapon ® (Cognis), Empicol ® (Albright & Wilson), Matexil ® (ICI), Soprophor ® (Rhodia) and Lutensit ® (BASF).
  • Nekal ® BASF
  • Tamol ® BASF
  • Crodafos ® Crodafos ® (Croda)
  • Rhodafac ® Rhodia
  • Maphos ® BASF
  • Texapon ® Cognis
  • Empicol ® Albright & Wilson
  • Matexil ® ICI
  • Soprophor ® Rosit ®
  • Lutensit ® BASF
  • Water-soluble anionic additives based on aromatic sulfonic acids and formaldehyde (A2.5) are based in particular on naphthalenesulfonic acid and are likewise preferably used in salt form, in particular as the sodium salt.
  • Their average molecular weight Mw is usually 4,000 to 15,000.
  • the additives (A2.5) are also known and are commercially available under the name Tamol ® (BASF).
  • Preferred pigment preparations (A) contain 45 to 90% by weight, preferably 55 to 90% by weight, of the coloring component (A1) and 10 to 55% by weight, preferably 10 to 45% by weight, of water-soluble surface-active additive as component (A2).
  • the solid pigment preparations (A) are typically prepared by first subjecting the pigment (A1.1) to a wet comminution in aqueous suspension containing at least part of the additive (A2), if desired a filler (A1.2) before or after the wet comminution of the pigment (A1.1) is added to the suspension and the suspension is then dried, if appropriate after addition of the remaining amount of additive (A2).
  • the pigment (A1.1) can be used here as a dry powder or in the form of a presscake.
  • the pigment (A1.1) used is preferably a finished product, i.
  • the primary grain size of the pigment is already set to the value desired for the application. This pigment finish is particularly recommended in the case of organic pigments, since the raw material obtained during pigment synthesis is generally not suitable for the application.
  • the adjustment of the primary grain size can also be carried out in the pigment synthesis, so that the resulting pigment suspensions can be used directly in the process according to the invention.
  • the finished pigment (A1.1) usually reagglomerates again during drying or on the filter unit, it is subjected to wet comminution in aqueous suspension, e.g. grinding in a stirred ball mill.
  • additive (A2) present in the finished pigment preparation (A) should be present, preferably the entire amount of additive (A2) is added before the wet comminution.
  • antioxidant (A3) which may also form part of the pigment preparations, it is expediently added before the wet comminution.
  • a filler (A1.2) is used, it can be added before or after the wet comminution. If it already has the desired particle size distribution, it is preferably dispersed in the pigment suspension only after the wet comminution of the pigment (A1.1). This applies in particular to fillers with a low hardness, such as chalk, which would be undesirably comminuted during the grinding of the pigment. Conversely, the still required comminution of a coarse-particle filler can be advantageously combined with the comminution of the pigment.
  • the solid pigment preparations (A) which are used as the basis for the pigment preparations according to the invention in tablet form can, depending on the respectively selected type of drying, be spray granulation and fluidized-bed drying, spray-drying,
  • the spray granulation is preferably carried out in a spray tower with a single-fluid nozzle.
  • the suspension is sprayed here in the form of larger drops, the water evaporates.
  • the additives melt at the drying temperatures and thus lead to the formation of a largely spherical granules with a particularly smooth surface (BET values of generally ⁇ 15 m 2 / g, in particular ⁇ 10 m 2 / g).
  • the gas inlet temperature in the spray tower is generally from 180 to 300 0 C, preferably at 150 to 300 0 C.
  • the gas outlet temperature is usually 70 to 150 ° C, preferably 70 to 130 0 C.
  • the residual moisture of the pigment granules obtained in this case is preferably ⁇ 5% by weight.
  • the solid pigment preparations (A) are described, for example, in the earlier German patent applications 102005005975.9 and the literature cited therein. Suitable pigment preparations (A) are in the market under the trade names Xfast ® and Pigmosol ® (BASF), and Leanyl ® Gran and Levanox ® Gran (Lanxess) available.
  • the pigment preparations according to the invention in tablet form generally contain from 10 to 80% by weight of a solid pigment preparation (A).
  • Another component of the pigment preparations according to the invention in tablet form is a tablet disintegrant (B).
  • This may be a disintegrating, strongly adsorbing water disintegrant (B1) or a gas-forming disintegrant (B2), wherein the disintegrating disintegrants (B1) are preferred.
  • Suitable disintegrating disintegrants (B1) are polyvinyl pyrrolidones, starch, cellulose derivatives and dextrans, wherein polyvinylpyrrolidones (eg Kollidon ® CL (BASF)) are particularly suitable.
  • Gas-forming disintegrants (B2) are typically combinations of weak acids, such as ascorbic acid, tartaric acid, citric acid and boric acid, with water-soluble carbonates or, in particular, water-soluble bicarbonates.
  • the content of the pigment preparations of the invention on a disintegrant from the group (B1) is generally from 10 to 40 wt .-%, while disintegrating agents of Group (B2) are usually used in amounts of 0.9 to 20 wt .-% (0.1 to 10 wt .-% acid and 0.8 to 10 wt .-% water-soluble (hydrogen) carbonate).
  • the pigment preparations according to the invention may contain up to 20% by weight of a release agent (C), up to 40% by weight of a binder (D) and / or up to 40% by weight of an additional surface-active additive (wetting agent) ( E) included.
  • a release agent C
  • a binder D
  • wetting agent wetting agent
  • Suitable release agent (mold release agents also) (C) are finely divided silica (Aerosil ® (Degussa)), stearates, and siliceous fillers such as talc, mica and kaolin.
  • Examples of typical binders (D) are lignosulfonate and polyvinyl alcohol.
  • the wetting agents (E) will typically only be included as additional components in the pigment preparations according to the invention in special cases, in particular only if a special adaptation to the application medium is required.
  • the surface-active additives already present in the solid pigment preparations (A) forming the basis of the pigment preparations according to the invention generally suffice for the customary purposes of use.
  • This compatibility aid (E) are preferably non-adhesive and do not tend to absorb water, are suitable, for example, naphthalenesulfonic acid / formaldehyde condensation products, alkylnaphthalene sulfonic acids, and modified polyacrylic acids (Tamol ®, Nekal ® and Sokalan ® (BASF)).
  • the pigment preparations according to the invention in tablet form can advantageously be prepared by the process according to the invention which is characterized in that the solid pigment preparation (A) with a tablet disintegrant (B) and, if desired, one or more further auxiliaries (C), (D) and / or (E) mix dry without particle size reduction and the resulting mixture is then compacted.
  • the mixing of the components (A) to (E) can advantageously be carried out in case, vane, screw, tumble and fluid mixers, such as drum, ring, concrete, trough and partial mixers.
  • the compaction or tableting can be carried out in the usual way.
  • the pigment preparations according to the invention in tablet form are outstandingly suitable for coloring coating systems which contain, as the liquid phase, water, organic solvents or mixtures of water and organic solvents. contain as well as for mass coloration of wood and building materials. They are characterized in particular by their very compact and thus very easy to dose form and at the same time by their stir-in properties.
  • dyeable coating systems are: paints, e.g. Building coatings, industrial coatings, vehicle coatings, radiation-curable coatings; Paints, both exterior and interior, e.g. Wood paints, lime paints, glues, emulsion paints; Printing inks, e.g. Offset inks, flexographic inks, toluene inks, textile inks, radiation curable inks; Inks, including ink-jet inks; Color filter; Building materials (usually water is added only after dry mixing of building material and pigment granules), e.g. Silicate plaster systems, cement, concrete, mortar, gypsum; Asphalt, sealants; cellulosic materials, e.g. Paper, cardboard, cardboard, wood and wood-based materials that may be painted or otherwise coated; adhesives; film-forming polymeric protective colloids, such as those used in the pharmaceutical industry; cosmetic articles; Detergents, whereby building materials are to be particularly emphasized.
  • paints e.g
  • Pigment preparations according to the invention in tablet form were prepared as follows:
  • Example 65.5 g of a solid pigment preparation (A), 30.0 g Kollidon ® CL (B), 3.0 g of talc (C) and 1, 5 g of magnesium stearate (C) were mixed with a laboratory mixer Microton ® MB 550 (Fa. Kinematica) homogenized for about 10 s.
  • Example 60.0 g of solid pigment preparation (A) and 5.5 g of a naphthalenesulfonic acid / formaldehyde condensation product (E) were used, the other components remained unchanged.
  • the mixture obtained in each case was compressed in a rotary press PH 100/6 (Korsch AG) using the following pressing parameters to form tablets (diameter: 2.5 cm, height: 0.5 cm, weight: 2.5 g):
  • Example 1 Xfast ® Blue 7080
  • Example 2 3860
  • Example 3 Xfast red: green Xfast 8730
  • Example 4 Xfast Blue 7080
  • Example 5 Xfast red 3390
  • Example 6 Black Xfast 0066
  • Example 7 Pigmosol Blue 6900 ®
  • Example 8 Levanyl Black ® Gran

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Civil Engineering (AREA)
  • Ceramic Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Structural Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

L'invention concerne des préparations pigmentaires sous forme de comprimés qui peuvent être obtenues en mélangeant à sec une préparation pigmentaire solide (A) avec un agent de désagrégation de comprimés (B) et si on le souhaite un ou plusieurs autres auxiliaires du groupe des agents de séparation (C), des liants (D) et des additifs tensioactifs solubles dans l'eau (E), sans broyage des particules, puis en pastillant ce mélange.
PCT/EP2007/057403 2006-07-24 2007-07-18 Préparations pigmentaires sous forme de comprimés Ceased WO2008012245A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP06117709 2006-07-24
EP06117709.3 2006-07-24

Publications (2)

Publication Number Publication Date
WO2008012245A2 true WO2008012245A2 (fr) 2008-01-31
WO2008012245A3 WO2008012245A3 (fr) 2008-04-24

Family

ID=38896048

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/057403 Ceased WO2008012245A2 (fr) 2006-07-24 2007-07-18 Préparations pigmentaires sous forme de comprimés

Country Status (1)

Country Link
WO (1) WO2008012245A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2159266A1 (fr) * 2008-09-01 2010-03-03 Lanxess Deutschland GmbH Granulés de pigments comprenant des auxiliaires filtrants anorganiques
CN109796795A (zh) * 2019-01-11 2019-05-24 芜湖市永格节能材料有限公司 一种耐酸碱盐腐蚀水性防锈漆的制备方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1015100A (en) * 1963-08-13 1965-12-31 Vitretex Central Africa Ltd Improvements relating to water-based or water-thinnable coating compositions
CH510098A (de) * 1968-12-11 1971-07-15 Agripat Sa Aufschäumende Farbstoff-Formulierungen
CH545842A (fr) * 1971-02-19 1974-02-15
CH630401A5 (en) * 1977-08-02 1982-06-15 Lonza Ag Solid tablets containing pigments, for colouring dispersions (emulsions) and lacquers (surface coatings)
JPH03221570A (ja) * 1990-01-26 1991-09-30 Pentel Kk 固形描画材
CA2122873A1 (fr) * 1993-05-04 1994-11-05 Terry M. Husher Trousse de coloriage d'oeufs
DE19731698A1 (de) * 1997-07-23 1999-01-28 Brockhues Chem Werke Ag Verfahren zur Einfärbung von Baustoffen und Asphalt
IT1317670B1 (it) * 2000-08-08 2003-07-15 Roberto Mosca Colorante e relativo uso.
FR2826369B1 (fr) * 2001-06-22 2005-02-04 Color Sa Colorants solubles en milieu aqueux et leur procede de fabrication
DE10319483A1 (de) * 2003-04-30 2004-11-18 Brockhues Gmbh & Co. Kg Schnell zerfallendes Pigmentkonzentrat
US20080060553A1 (en) * 2005-02-11 2008-03-13 Ewald Dorken Ag Chromophore Coating Systems, Especiallly Paints And Lacquers

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2159266A1 (fr) * 2008-09-01 2010-03-03 Lanxess Deutschland GmbH Granulés de pigments comprenant des auxiliaires filtrants anorganiques
CN109796795A (zh) * 2019-01-11 2019-05-24 芜湖市永格节能材料有限公司 一种耐酸碱盐腐蚀水性防锈漆的制备方法

Also Published As

Publication number Publication date
WO2008012245A3 (fr) 2008-04-24

Similar Documents

Publication Publication Date Title
EP1474485B1 (fr) Preparations pigmentaires
EP2234708B1 (fr) Fabrication d'une préparation de pigments solide sous forme de granulat par séchage par pulvérisation
EP1565531B1 (fr) Preparations de pigment solides, contenant des additifs tensioactifs anioniques hydrosolubles renfermant des groupes carboxylate
EP1517934B1 (fr) Compositions pigmentaires solides contenant des additifs tensioactifs anioniques ou non ioniques
EP2324081B1 (fr) Pate pigmentaire aqueuse universelle
US20150274977A1 (en) Solid pigment preparations containing water-soluble surface-active additives and anti-oxidants
DE112006000180B4 (de) Feste Pigmentzubereitungen, enthaltend wasserlösliche oberflächenaktive Additive auf Polyurethanbasis, Verfahren zu deren Herstellung sowie deren Verwendung
DE102005005975A1 (de) Feste Pigmentzubereitungen, enthaltend Füllstoffe und wasserlösliche oberflächenaktive Additive
DE102005020741A1 (de) Verwendung von flüssigen Farbmittelzubereitungen zur Einfärbung von Cellulose/Polymer-Verbundwerkstoffen
WO2008012245A2 (fr) Préparations pigmentaires sous forme de comprimés
DE10204583A1 (de) Pigmentzubereitungen
EP1879945B1 (fr) Utilisation de preparations pigmentaires solides pour colorer des materiaux composites a base de cellulose et de polymere
EP2265678B1 (fr) Préparation solide d'acide silicique
WO2007065839A2 (fr) Procede de dispersion de preparations de pigments solides dans des liquides

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

NENP Non-entry into the national phase

Ref country code: RU

122 Ep: pct application non-entry in european phase

Ref document number: 07787667

Country of ref document: EP

Kind code of ref document: A2