WO2003099936A1 - Nouveaux derives du c.i. pigment rouge 170 - Google Patents

Nouveaux derives du c.i. pigment rouge 170 Download PDF

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Publication number
WO2003099936A1
WO2003099936A1 PCT/EP2003/004966 EP0304966W WO03099936A1 WO 2003099936 A1 WO2003099936 A1 WO 2003099936A1 EP 0304966 W EP0304966 W EP 0304966W WO 03099936 A1 WO03099936 A1 WO 03099936A1
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WO
WIPO (PCT)
Prior art keywords
compound
formula
acid
meaning
pigment
Prior art date
Application number
PCT/EP2003/004966
Other languages
German (de)
English (en)
Inventor
Martin U. Schmidt
Andreas Wacker
Hans Joachim Metz
Original Assignee
Clariant 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 Clariant Gmbh filed Critical Clariant Gmbh
Publication of WO2003099936A1 publication Critical patent/WO2003099936A1/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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
    • 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
    • C09B67/0025—Crystal modifications; Special X-ray patterns
    • C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
    • C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds

Definitions

  • the present invention relates to new azo pigments based on C.I. Pigment Red 170 and process for its manufacture.
  • the ⁇ phase is mainly used in automotive paints.
  • the ß phase is much more transparent and bluish than the ⁇ phase.
  • the ⁇ phase has significantly poorer fastness properties and is therefore not suitable as an organic pigment.
  • C.I. Pigment Red 170 is described in DE 1 228 731.
  • the ⁇ , ⁇ and ⁇ phases are described in DE 2 043 482.
  • the aim of the present invention was to provide azo red pigments with good general fastness properties, which are more transparent and at the same time more yellowish than the C.I. Pigment Red 170 in the ⁇ phase.
  • the present invention relates to compounds of the formula (1) wherein
  • X has the meaning F, Cl, Br, methyl or nitro.
  • Formula (1) is to be understood as an idealized representation and also includes the corresponding tautomeric forms and the possible configuration isomers of each tautomeric form.
  • the compound of formula (1) where X is methyl can occur in two different crystal modifications.
  • the compound of formula (1) where X is nitro can occur in three different crystal modifications.
  • the line positions of all phases are usually affected by an inaccuracy of 0.2 ° in 2 ⁇ .
  • the crystal phases of the compound of formula (1) with X equal to nitro are characterized by the following characteristic lines (Cu-K ⁇ radiation, 2 ⁇ values in degrees, d values in A " ⁇ relative intensity in%).
  • the ⁇ -phase of the nitro compound arises, for example, when the pigment is heated at 100 to 110 ° C. in dimethylformamide after the synthesis.
  • the ß phase of the nitro compound arises, for example, if the pigment is heated to 90 to 100 ° C. in water after the synthesis.
  • the ⁇ phase of the nitro compound arises, for example, if the pigment is heated to 130 to 150 ° C. in water after the synthesis.
  • the crystal phases of the compound of formula (1) with X equal to methyl are characterized by the following characteristic lines (Cu-K ⁇ radiation, 2 ⁇ values in degrees, d values in ⁇ "1 , relative intensity in%):
  • the ⁇ -phase of the methyl compound is formed, for example, if the pigment is heated to 90 to 110 ° C after the synthesis in acetic acid or heated to 130 to 140 ° C in water.
  • the ⁇ -phase of the methyl compound arises, for example, if the pigment is heated to 100 to 130 ° C. in chlorobenzene after the synthesis.
  • the pigments according to the invention can be obtained by diazotizing an amine of the formula (2)
  • Alkali metal nitrites or the alkyl nitrites of short-chain alkanes, together with strong mineral acids, are suitable for the diazotization reaction.
  • Sodium nitrite and hydrochloric acid are particularly suitable.
  • the reaction can be carried out in a temperature range from -5 ° C to + 30 ° C, preferably between 0 ° C and 10 ° C.
  • non-ionic, anionic or cationic surface-active substances can be present in the diazotization.
  • other auxiliaries such as natural or synthetic resins or resin derivatives, can also be used. Coupling is possible by the direct or inverse method, but is preferably carried out indirectly, ie the coupling component is added to the diazonium salt provided.
  • the coupling reaction can be carried out in a temperature range between -5 ° C and 80 ° C, preferably between 5 ° C and 25 ° C, and at a pH between pH 4 and pH 14, in particular between pH 9 and pH 12.
  • Die Azo coupling reaction is preferably carried out in aqueous solution or suspension, but it is also possible to use organic solvents, if appropriate in a mixture with water, for example alcohols having 1 to 10 carbon atoms, such as, for example, methanol, ethanol, n-propanol, isopropanol, butanols, such as n -Butanol, sec-butanol, tert-butanol, pentanols, such as n-pentanol, 2-methyl-2-butanol, hexanols, such as 2-methyl-2-pentanol, 3-methyl-3-pentanol, 2-methyl -2-hexanol, 3-ethyl-3-pentanol
  • Monoethyl ether of ethylene or propylene glycol diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, butyl glycols or methoxybutanol; Ketones such as acetone, diethyl ketone, methyl isobutyl ketone, methyl ethyl ketone or cyclohexanone; aliphatic acid amides such as formamide, dimethylformamide, N-methylacetamide or N, N-dimethylacetamide; Urea derivatives, such as
  • Tetramethylurea Tetramethylurea; or cyclic carboxamides, such as N-methylpyrrolidone, valero- or caprolactam; Esters, such as carboxylic acid C 1 -C 6 -alkyl esters, such as butyl formate, ethyl acetate or propyl propionate; or carboxylic acid -C 6 glycol ester; or glycol ether acetates, such as 1-methoxy-2-propyl acetate; or phthalic or benzoic acid CrC 6 alkyl esters, such as
  • benzoate cyclic esters such as caprolactone; Nitriles such as acetonitrile or benzonitrile; aliphatic or aromatic hydrocarbons, such as cyclohexane or benzene; or by alkyl, alkoxy, nitro or halogen substituted benzene, such as toluene, xylenes, ethylbenzene, anisole, nitrobenzene, chlorobenzene, o-dichlorobenzene, 1, 2,4-trichlorobenzene or bromobenzene; or other substituted aromatics such as benzoic acid or phenol; aromatic heterocycles such as pyridine, morpholine, picoline or quinoline; as well as hexamethylphosphoric triamide, 1, 3-dimetyl-2-imidazolidinone, dimethyl sulfoxide and sulfolane.
  • the solvents mentioned can also be used as mixtures. Water-miscible solvents
  • auxiliaries such as, for example, coupling auxiliaries, surfactants, pigmentary and non-pigmentary dispersants, fillers, adjusting agents, resins, waxes, defoamers, anti-dust agents, extenders, colorants for shading, preservatives, drying retardants, additives for controlling the rheology, wetting agents, antioxidants, UV absorbers, light stabilizers, or a combination thereof can be used.
  • the total amount of auxiliaries added can be 0 to 40% by weight, preferably 1 to 30% by weight, particularly preferably 2.5 to 25% by weight, based on the azo pigment.
  • Suitable surfactants are anionic or anionic, cationic or cationic and nonionic substances or mixtures of these agents.
  • anionic substances are fatty acid taurides, fatty acid N-methyl taurides, fatty acid isethionates, alkylphenyl sulfonates, alkyl naphthalene sulfonates, alkylphenol polyglycol ether sulfates, fatty alcohol polyglycol ether sulfates, fatty acid amide polyglycol ether sulfates, alkyl sulfosuccinamate succinate acid, alkenyl sulfonate urate sulfate, alkenyl sulfonate urate Fatty acids, for example palmitic, stearic and oleic acid; Soaps, for example alkali salts of fatty acids, naphthenic acids and resin acids, for example abietic acid, alkali-soluble resins, for example
  • alkali-soluble resinous auxiliaries or mixtures thereof during or after the coupling, and before or during the lacquering improves the dispersibility of the pigments.
  • the resinous auxiliaries or mixtures thereof are expediently used in the form of their aqueous-alkaline solutions.
  • Natural and synthetic resins are suitable as resinous auxiliaries. Rosin, disproportionated or hydrogenated rosin and rosin derivatives are to be mentioned as advantageous.
  • Natural resin acids such as abietic acid, dihydroabietic acid, tetrahydroabietic acid, laevopimaric acid, dextropimaric acid and isodextropimaric acid, as are present in commercially available types of rosin, are preferred.
  • the commercially available resin Rosin N which contains the resin acids abietic acid, dehydroabetic acid, neoabietic acid, palustric acid, isopimaric acid, pimaric acid and sandaracopimaric acid, or a commercial product equivalent to Rosin N, is particularly preferred.
  • alkyd resins or synthetic hydrocarbon resins with a high acid number can also be used.
  • the resins mentioned are preferably added to the reaction mixture following the coupling reaction.
  • Suitable cationic substances are quaternary ammonium salts, fatty amine oxyalkylates, oxyalkylated polyamines, fatty amine polyglycol ethers, fatty amines, di- and polyamines derived from fatty amines or fatty alcohols and their oxyalkylates, imidazolines derived from fatty acids, and salts of these cationic substances, such as acetates.
  • nonionic substances include amine oxides, fatty alcohol polyglycol ethers, fatty acid polyglycol esters, betaines such as fatty acid amide-N-propyl-betaine, phosphoric acid esters of aliphatic and aromatic alcohols, fatty alcohols or fatty alcohol polyglycol ethers, fatty acid amide ethoxylates, fatty alcohol-alkylene oxide adducts and alkylphenol adducts and alkylphenol in consideration.
  • Nonpigmentary dispersants mean substances that are not derived from organic pigments by chemical modification. They are used as dispersants either in the manufacture of pigments, but often also in the incorporation of the pigments into the application media to be colored, for example in the manufacture of paints or printing inks
  • Dispersion of the pigments in the corresponding binders can be polymeric substances, for example polyolefins, polyesters, polyethers, polyamides, polyimines, polyacrylates, polyisocyanates, block copolymers thereof, copolymers from the corresponding monomers or polymers from one class which have been modified with a few monomers from another class.
  • These polymeric substances carry polar anchor groups such as, for example, hydroxyl, amino, imino and ammonium groups, carboxylic acid and carboxylate groups, sulfonic acid and sulfonate groups or phosphonic acid and phosphonate groups, and can also be modified with aromatic, non-pigmentary substances.
  • Non-pigmentary dispersants can furthermore also be aromatic substances which are chemically modified with functional groups and are not derived from organic pigments.
  • Nonpigmentary dispersants are known in the art and some are available commercially (for example, Solsperse ®, Avecia; Disperbyk ®, Byk, Efka ®, Efka).
  • Pigmentary dispersants mean pigment dispersants which are derived from an organic pigment as the base body and are produced by chemical modification of this base body, for example saccharin-containing pigment dispersants, piperidyl-containing pigment dispersants, naphthalene or perylene-derived pigment dispersants, pigment dispersants with functional groups which have a methylene group with the Basic pigment bodies are linked, chemically modified basic pigment bodies, pigment dispersants containing sulfonic acid groups, pigment dispersants containing sulfonamide groups, pigment dispersants containing ether groups, or pigment dispersants containing carboxylic acid, carboxylic acid ester or carbonamide groups.
  • buffer solutions can be added, preferably of organic acids and their salts, such as, for example, formic acid / formate buffer, acetic acid / acetate buffer, citric acid / citrate buffer; or of inorganic acids and their salts, such as, for example, phosphoric acid / phosphate buffer or carbonic acid / bicarbonate or carbonate buffer.
  • organic acids and their salts such as, for example, formic acid / formate buffer, acetic acid / acetate buffer, citric acid / citrate buffer
  • inorganic acids and their salts such as, for example, phosphoric acid / phosphate buffer or carbonic acid / bicarbonate or carbonate buffer.
  • the coupling component based on the diazonium compound, is used in a slight excess, preferably 1 equivalent of diazo component is reacted with 1,001 to 1,10 equivalents of the coupling component.
  • the compounds according to the invention are preferably subjected to heat treatment in an aqueous, aqueous-organic or organic medium using the solvents described above
  • the compounds of formula (1) can be used for pigmenting high molecular weight organic materials of natural or synthetic origin, for example plastics, resins, lacquers, paints or electrophotographic toners and developers, as well as inks and printing inks.
  • High molecular weight organic materials which can be pigmented with the compounds according to the invention are, for example, cellulose ethers and esters, such as ethyl cellulose, nitrocellulose, cellulose acetate or cellulose butyrate, natural resins or synthetic resins, such as polymerization resins or condensation resins, for example aminoplasts, in particular urea and melamine formaldehyde resins, alkyd resins, Acrylic resins, phenoplasts, polycarbonates, polyolefins, such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, polyacrylic acid esters, polyamides, polyurethanes or polyesters, rubber, casein, silicone and silicone resins, individually or in mixtures.
  • cellulose ethers and esters such as ethyl cellulose, nitrocellulose, cellulose acetate or cellulose butyrate
  • natural resins or synthetic resins such as polymerization resins or condensation resins, for
  • the compounds according to the invention are used in an amount of 0.05 to 30% by weight, preferably 0.1 to 15% by weight.
  • the pigments according to the invention are suitable as colorants in electrophotographic toners and developers, such as, for example, one- or two-component powder toners (also one- or two-component developers called), magnetic toner, liquid toner, latex toner, polymerization toner and special toner.
  • electrophotographic toners and developers such as, for example, one- or two-component powder toners (also one- or two-component developers called), magnetic toner, liquid toner, latex toner, polymerization toner and special toner.
  • Typical toner binders are polymerization, polyaddition and polycondensation resins, such as styrene, styrene-acrylate, styrene-butadiene, acrylate, polyester, phenol-epoxy resins, polysulfones, polyurethanes, individually or in combination, and polyethylene and polypropylene, which also contain other ingredients, such as charge control agents, waxes or flow aids, or can be modified with these additives afterwards.
  • resins such as styrene, styrene-acrylate, styrene-butadiene, acrylate, polyester, phenol-epoxy resins, polysulfones, polyurethanes, individually or in combination, and polyethylene and polypropylene, which also contain other ingredients, such as charge control agents, waxes or flow aids, or can be modified with these additives afterwards.
  • the pigments according to the invention are suitable as colorants in powders and powder coatings, in particular in triboelectrically or electrokinetically sprayable powder coatings which are used for the surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber.
  • Epoxy resins, carboxyl- and hydroxyl-containing polyester resins, polyurethane and acrylic resins are typically used as powder coating resins together with conventional hardeners. Combinations of resins are also used. For example, epoxy resins are often used in combination with carboxyl- and hydroxyl-containing polyester resins.
  • Typical hardener components are, for example, acid anhydrides, imidazoles and dicyandiamide and their derivatives, blocked isocyanates, bisacyl urethanes, phenolic and melamine resins, triglycidyl isocyanurates, oxazolines and dicarboxylic acids.
  • the pigments according to the invention are suitable as colorants in inks, preferably ink-jet inks, such as, for example, on an aqueous or non-aqueous basis, microemulsion inks and in such inks which work according to the hot-melt process.
  • Ink-jet inks generally contain a total of 0.5 to 15% by weight, preferably 1.5 to 8% by weight (calculated on a dry basis) of one or more of the compounds according to the invention.
  • Microemulsion inks are based on organic solvents, water and possibly an additional hydrotropic substance (interface mediator).
  • Microemulsion inks contain 0.5 to 15% by weight, preferably 1.5 to 8% by weight, of one or more of the compounds according to the invention, 5 to 99% by weight of water and 0.5 to 94.5% by weight organic solvent and / or hydrotropic compound.
  • solvent based ink-jet inks preferably contain 0.5 to 15% by weight of one or more compounds according to the invention, 85 to 99.5% by weight of organic solvent and / or hydrotropic compounds.
  • Hot-melt inks are mostly based on waxes, fatty acids, fatty alcohols or sulfonamides, which are solid at room temperature and become liquid when heated, the preferred melting range being between approx. 60 ° C and approx. 140 ° C.
  • Hot melt ink jet inks are e.g. essentially from 20 to 90% by weight of wax and 1 to 10% by weight of one or more of the compounds according to the invention.
  • an additional polymer as a "dye dissolver”
  • dispersing aid 0 to 20% by weight of viscosity modifier
  • plasticizer 0 to 10% by weight % Tack additive
  • the compounds according to the invention are also suitable as colorants for color filters, both for additive and for subtractive color production.
  • the compounds according to the invention are also suitable for coloring seed.
  • the pigments according to the invention are notable for good fastness properties and high transparency. They are essential more yellowish than CI Pigment Red 170. They do not contain any heavy metals that are harmful to the environment.
  • the properties listed qualify the pigments of the invention in particular for use as colorants in paints, preferably automotive paints, and in plastics, and in printing inks.
  • the synthesis takes place as in comparative example 1a, but instead of 4-aminobenzamide 15.4 parts of 4-amino-3-fluoro-benzamide.
  • the press cake is heated in acetic acid at 114 ° C. for 50 minutes, filtered off, washed with water and dried.
  • Example 2a The synthesis is carried out as in Example 2a.
  • the press cake is heated in acetic acid at 100 ° C. for 20 minutes, filtered off, washed with water and dried.
  • Example 4 The synthesis is carried out as in Example 4.
  • the press cake is heated in water at 98 ° C. for 2 hours, filtered off, washed with water and dried.
  • the ⁇ -phase of the nitroderivative is obtained with smaller additions of the ⁇ -phase of the nitroderivative.
  • Example 4 The press cake is used for aftertreatment Heated in water at 140 ° C. for 1 hour, filtered off, washed with water and dried.
  • the ⁇ -phase of the nitroderivative is obtained with smaller additions of the ⁇ - and ß-phase of the nitroderivative.
  • Example 7 The synthesis takes place as in Example 7.
  • the press cake is heated in chlorobenzene for 1 hour at 120 ° C., filtered off, washed with chlorobenzene and dried.
  • an aromatic-containing alkyd melamine resin paint (AM) based on a medium-oil alkyd resin and a butanol-etherified melamine resin was selected from the large number of known paints.
  • AM aromatic-containing alkyd melamine resin paint
  • white lightenings were created with a pigment: TiO 2 ratio of 1:10.
  • ⁇ H is the color difference between the coating of the pigment and the coating of the product of Comparative Example 1.
  • a positive ⁇ H value means that the pigment is more yellow than the comparative example.
  • PVC coloring is made and coloristically compared to a PVC coloring of Comparative Example 1.
  • the PVC colorations of the pigments according to the invention from Examples 7 and 8 are significantly more yellow and more transparent than the PVC coloration of Comparative Example 1.
  • Application example 9a-d light and weather fastness
  • the pigments are dispersed in an aromatic alkyd melamine resin paint (AM) based on a medium oil alkyd resin and a butanol etherified melamine resin and subjected to a light and weather fastness test in a rapid exposure or rapid weathering apparatus.
  • the tests were carried out both in full tone and in brightening.
  • the overall coloristic distance ⁇ E in the CIELAB system
  • the exposures were carried out in synchronism in the Xenotest Beta device.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne des composés de formule (1), (1), ou des tautomères de ces composés, X signifiant F, Cl, Br, méthyle ou nitro. L'invention est caractérisée en ce que ces composés présentent une dominante jaune, une transparence et une résistance aux intempéries supérieures au pigment non substitué rouge 170.
PCT/EP2003/004966 2002-05-28 2003-05-13 Nouveaux derives du c.i. pigment rouge 170 WO2003099936A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2002124279 DE10224279A1 (de) 2002-05-28 2002-05-28 Neue Derivate von C.I. Pigment Red 170
DE10224279.8 2002-05-28

Publications (1)

Publication Number Publication Date
WO2003099936A1 true WO2003099936A1 (fr) 2003-12-04

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WO (1) WO2003099936A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102816456A (zh) * 2012-08-29 2012-12-12 天津城市建设学院 无机纳米材料改性制备包核颜料红170的方法
WO2016206928A1 (fr) * 2015-06-25 2016-12-29 Clariant International Ltd Utilisation de nouveaux mélanges de pigments de naphtol as dans des matières d'impression

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1658336B1 (fr) * 2003-08-19 2006-11-22 Clariant Produkte (Deutschland) GmbH CRISTAUX MIXTES A BASE DE DERIVES DU PIGMENT ROUGE CI No 170

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB844394A (en) * 1956-03-23 1960-08-10 Hoechst Ag Water-insoluble monoazo-dyestuffs of the benzene-azo-naphthalene series and process for their manufacture
FR1411277A (fr) * 1963-08-22 1965-09-17 Bayer Ag Colorants azoïques insolubles dans l'eau et procédé pour leur fabrication
DE1228731B (de) * 1963-03-13 1966-11-17 Hoechst Ag Verfahren zur Herstellung von wasserunloeslichen Monoazofarbstoffen
US3332932A (en) * 1964-08-14 1967-07-25 Interchem Corp Monoazo pigments of diazotized 3-amino-4-methylbenzamide with naphthols
DE2043482A1 (de) * 1970-09-02 1972-03-16 Farbwerke Hoechst AG, vorm. Meister Lucius & Brüning, 6000 Frankfurt Monoazopigment und Verfahren zu seiner Herstellung

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB844394A (en) * 1956-03-23 1960-08-10 Hoechst Ag Water-insoluble monoazo-dyestuffs of the benzene-azo-naphthalene series and process for their manufacture
DE1228731B (de) * 1963-03-13 1966-11-17 Hoechst Ag Verfahren zur Herstellung von wasserunloeslichen Monoazofarbstoffen
FR1411277A (fr) * 1963-08-22 1965-09-17 Bayer Ag Colorants azoïques insolubles dans l'eau et procédé pour leur fabrication
US3332932A (en) * 1964-08-14 1967-07-25 Interchem Corp Monoazo pigments of diazotized 3-amino-4-methylbenzamide with naphthols
DE2043482A1 (de) * 1970-09-02 1972-03-16 Farbwerke Hoechst AG, vorm. Meister Lucius & Brüning, 6000 Frankfurt Monoazopigment und Verfahren zu seiner Herstellung

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102816456A (zh) * 2012-08-29 2012-12-12 天津城市建设学院 无机纳米材料改性制备包核颜料红170的方法
CN102816456B (zh) * 2012-08-29 2013-10-23 天津城市建设学院 无机纳米材料改性制备包核颜料红170的方法
WO2016206928A1 (fr) * 2015-06-25 2016-12-29 Clariant International Ltd Utilisation de nouveaux mélanges de pigments de naphtol as dans des matières d'impression
US10782625B2 (en) 2015-06-25 2020-09-22 Clariant Plastics & Coatings Ltd Use of novel naphthol AS-pigment-mixtures in printing-materials

Also Published As

Publication number Publication date
DE10224279A1 (de) 2003-12-11

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