WO1991008265A1 - Composes azoiques et leur utilisation comme colorants, 1-sulfo-6-carboxy-2-amino-naphtaline, son utilisation comme constituant diazoique et procede de fabrication de ces composes - Google Patents

Composes azoiques et leur utilisation comme colorants, 1-sulfo-6-carboxy-2-amino-naphtaline, son utilisation comme constituant diazoique et procede de fabrication de ces composes Download PDF

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Publication number
WO1991008265A1
WO1991008265A1 PCT/EP1990/002019 EP9002019W WO9108265A1 WO 1991008265 A1 WO1991008265 A1 WO 1991008265A1 EP 9002019 W EP9002019 W EP 9002019W WO 9108265 A1 WO9108265 A1 WO 9108265A1
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
general formula
hydrogen
sulfo
radical
Prior art date
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PCT/EP1990/002019
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German (de)
English (en)
Inventor
Hartmut Springer
Kurt Hussong
Original Assignee
Hoechst Aktiengesellschaft
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.)
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Publication date
Application filed by Hoechst Aktiengesellschaft filed Critical Hoechst Aktiengesellschaft
Priority to KR1019920701289A priority Critical patent/KR927003733A/ko
Priority to BR909007891A priority patent/BR9007891A/pt
Publication of WO1991008265A1 publication Critical patent/WO1991008265A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C07C309/61—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • 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
    • C09B29/0014—Monoazo dyes prepared by diazotising and coupling from diazotized aminonaphthalene
    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
    • C09B62/507—Azo dyes

Definitions

  • Azo compounds and their use as dyes 1-sulfo-6-carboxy-2-a ino-naphthalene, its use as a diazo component and process for the preparation of these compounds
  • the present invention is in the technical field of fiber-reactive azo dyes.
  • Azo dyes based on di- or trisulfonaphthylamines are well known in the literature, for example from Japanese patent application publications Sho-58-142939, Sho-59-115360 and Sho-59-182859, US Pat. Nos. 3,197,456 , 3 406 163, 3 419 542 and 3 518 245 as well as the British patents 1 341 320 and 1 438 051.
  • the ever increasing demands in the handling of the dyes in the dyeing to achieve brilliant dyeings have made it necessary to use new dyes with improved properties to develop.
  • M is a hydrogen atom or salt-forming metal atom, such as in particular an alkali metal atom, such as sodium, potassium or lithium;
  • M has the meaning given above, D is a benzene or naphthalene radical,
  • R 1 is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and in particular methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and in particular methoxy, fluorine, bromine, chlorine, sulfo, carboxy, carbalkoxy of 2 to 5 C. Atoms, such as carbomethoxy and carbethoxy, trifluoromethyl, carbamoyl or N carbamoyl, preferably hydrogen, methoxy or methyl if D is a benzene ring, or R 1 is hydrogen or sulfo if D is a naphthalene ring,
  • R 2 is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and in particular methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and in particular methoxy, chlorine, nitro or sulfo, preferably hydrogen, methoxy or methyl, if D means a benzene ring,. or
  • R 2 is hydrogen or sulfo, if D is a naphthalene radical, Y is the vinyl group or an ethyl group which contains a substituent which can be eliminated by alkaline means to form the vinyl group, a is the number zero, 1 or 2, k the Number 1 or 2,
  • E is a radical of the general formula (3a), (3b), (3c) or (3d)
  • R is hydrogen, alkyl of 1 to 4 carbon atoms, such as methyl, cyano, carboxy, carbalkoxy of 2 to 5 carbon atoms, such as carbomethoxy and carbethoxy, carbamoyl or phenyl, preferably methyl, carboxy, carbomethoxy or carbethoxy,
  • Q is a benzene or naphthalene residue
  • R 1 has one of the abovementioned meanings as a substituent on a benzene radical or is hydrogen or sulfo if Q is a naphthalene radical,
  • R 3 is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and in particular methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and in particular methoxy, chlorine or sulfo, preferably hydrogen, methoxy, ethoxy or methyl, if one Is benzene, or is hydrogen or sulfo if Q is naphthalene,
  • R 4 is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and in particular methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and in particular methoxy, bromine, chlorine, trifluoromethyl, sulfo, carboxy or cyano, preferably methyl, methoxy or is sulfo, R "is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and in particular methyl, alkoxy of 1 to 4 carbon atoms, such as
  • Alkylamino of 1 to 4 carbon atoms such as ethylamino
  • Alkanoylamino of 2 to 5 carbon atoms such as acetylamino and propionylamino, benzoylamino, ureido, N'-phenyl-ureido, N'- (C ] _-C 4 -alkyl) -ureido, phenylsulfonyl or
  • alkylsulfonyl of 1 to 4 carbon atoms such as ethylsulfonyl and methylsulfonyl, preferably hydrogen or methoxy
  • R c is hydrogen or ß-sulfatoethylsulfonyl
  • M has one of the meanings given above, m denotes the number 1 or 2, n denotes the number zero, 1 or 2 (where n is zero this group represents a hydrogen atom), v is the number zero or 1 and K is the rest is a water-soluble coupling component which contains 1 or 2 groups of the general formula -S0 2 -Y with Y of the above meaning, such as, for example, a radical of the general formula (4a), (4b), (4c),
  • M, m, n, Y, k, R 1 , R 2 , D, R 4 , R 5 , R and a have one of the meanings mentioned above,
  • V is a direct, covalent bond or a radical of the formula -NH-CO-phenylene-, -NH-CO-NH-phenylene-, -N (CH 3 ) -CO-phenylene-, -N (CH 3 ) -CO- NH-phenylene-, -N (C 2 H 5 ) -CO-pheny1en-, -N (C 2 H 5 ) -CO-NH-pheny1en-, -NH-CO-alkylene-, -NH-CO-NH- alkylene-, -N (CH 3 ) -CO-alkylene- or -N (CH 3 ) -CO-NH-alkylene-, -N (C 2 H 5 ) -CO-alkylene- or -N (C 2 H 5 ) -C0-NH-alkylene-, in which "alkylene” means a straight-chain or branched alkylene radical of 2 to 6 carbon atoms, preferably 3 carbon
  • R ' is hydrogen or alkyl of 1 to 4 carbon atoms, such as
  • Is methyl or ethyl or is alkyl of 1 to 4 carbon atoms, such as ethyl, which is substituted by sulfo, carboxy, sulfato, phosphato, hydroxy, methoxy or ethoxy, preferably hydrogen
  • W is a phenylene radical which is substituted by 1 or 2 substituents from the group alkyl of 1 to 4 carbon atoms, such as ethyl and in particular methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and in particular methoxy, chlorine, carboxy and sulfo can be, or an alkylene of
  • 1 to 6 carbon atoms preferably 1 to 4 carbon atoms, such as ethylene, or is an alkylene-phenylene with an alkylene of 2 to 4 carbon atoms, such as methylene-phenylene or ethylene-phenylene, is preferably phenylene or ethylene,
  • R 8 is hydrogen, alkyl of 1 to 4 carbon atoms, such as methyl, alkoxy of 1 to 4 carbon atoms, such as methoxy, phenyl or cyano-substituted alkyl of 1 to 4 carbon atoms, is preferably methyl and R 9 is hydrogen , Sulfo, sulfoalkyl of 1 to 4 carbon atoms, such as sulfomethyl, carboxy, cyano or preferably carbamoyl.
  • the formula radical E is to be understood as the radical of a coupling and diazotizable compound according to the general formula HE-NH 2 .
  • the hydroxyl group and the free bond located in the same aromatic nucleus are in the ortho position to one another.
  • the hydroxyl group is preferably bound to the naphthalene radical in the ⁇ -position.
  • Alkaline eliminable substituents of the ethyl group of the radical Y are, for example, halogen atoms, such as the bromine atom and chlorine atom, ester groups of organic carboxylic and sulfonic acids, such as an alkanoyloxy radical of 2 to 5 carbon atoms, for example the acetyloxy group, or a sulfobenzoyloxy, benzoyloxy, phenylsulfonyloxy or tolylsulfonyloxy radical, furthermore, for example, the acidic ester groups of phosphoric acid, sulfuric acid and thiosulfuric acid (phosphato or sulfato or thiosulfato groups), in each case also with alkyl alkyl groups 1 to 4 carbon atoms, such as the dimethylamino and diethylamino group.
  • Y is preferably the vinyl group and in particular the ⁇ -sulfatoethyl group.
  • sulfo groups are groups corresponding to the general formula -SO3M, carboxy groups groups corresponding to the general formula -COOM, thiosulfato groups corresponding to the general formula -S-SO3M, phosphato groups corresponding to the general formula -OP ⁇ M 2 and sulfato groups corresponding to groups of the general formula -OSO3M , each with M of the meaning given above.
  • the present invention further relates to a process for the preparation of the azo compounds of the general formula (1) according to the invention, which is characterized in that in the case where K ° is a radical of the general formula (2A), the diazonium compound of an amine of the general formula ( 5)
  • the diazotization and coupling reactions of the process according to the invention take place in a customary and well-known manner, so the diazotization is generally preferred at a temperature between -5 ⁇ C and +15 ⁇ C and a pH below 2 by means of a strong acid and alkali nitrite aqueous medium and the coupling reaction usually at a temperature between 0 and 30 ⁇ C and at a pH between 1 and 4.5 in the case of an amino group-containing coupling component and at a pH between 3 and 7.5 in the case of a hydroxy group Coupling component, preferably in an aqueous medium.
  • the starting compounds of the general formula (5) with v equal to 1 are prepared in a known manner for the diazotization and coupling reactions of l-sulfo-6-carboxy-2-aminonaphthalene as the diazo component and the compound of the general formula HE-NH 2 as the coupling component.
  • the azo compounds are synthesized in the same way general formula (6) by coupling the diazonium salt of 1-sulfo-6-carboxy-2-aminonaphthalene with 1-amino-8-naphthol-3,6- or -4,6-disulfonic acid analogously to known procedures in a strongly acidic medium.
  • Starting compounds of the general formula HE-NH are, for example, aniline, 3-methyl-aniline, 3-chloro-aniline, 2,5-dimethyl-aniline, 2,5-di-ethoxy-aniline, 3-methoxy-aniline, 3-methyl 6-methoxy-aniline, 3-ureido-aniline, 3-acetylamino-6-methyl-aniline, 2-amino-4-acetylamino-benzene-1-sulfonic acid, 1-aminonaphthalene, 1-aminonaphthalene-6- or -7- or -8-sulfonic acid, 3-acetylamino-niline, 2-methyl-aniline, 2-methoxy-aniline, 3-benzoylamino-aniline, 2,3-dimethyl-aniline, 3,5-D ' imethyl-aniline, 2- Methoxy-5-acetylamino niline, 2-chloro-6-methylaniline, 5-chloro-2-methylaniline, 2,6-dich
  • 6-sulfo-8-naphthol 3- [N-methyl-N- (ß-sulfatoethylsulfonyl)] - amino-6-sulfo-8-naphthol, 1- (4 * -ß-sulfatoethylsulfonyl-benzoylamino) -3.6 -disulfo-8-naphthol, 1- (4'-ß-sulfatoethyl-sulfonyl-benzoylamino) -4,6-disulfo-8-naphthol, 1- [Y- (ß-chloroethylsulfonyl) propionyl] amino- 3,6-disulfo-8-naphthol,
  • Starting compounds of the general formula (7) are, for example, 2- ( ⁇ -sulfatoethylsulfonyl) aniline, 3- ( ⁇ -sulfatoethylsulfonyl) aniline, 4- ( ⁇ -sulfatoethyl sulfonyl) aniline, 2-carboxy-5- ( ⁇ - sulfatoethylsulfonyl) aniline, 2-chloro-3- (ß-sulfatoethylsulfonyl) aniline,
  • the 1-sulfo-6-carboxy-2- a ino-naphthalene compound used according to the invention for the synthesis of the azo compounds of the general formula (1) is not yet known.
  • the invention thus also relates to this compound, processes for its preparation and its use for the synthesis of dyes, in particular for the synthesis of azo compounds, such as those of the general formula (1).
  • the 1-sulfo-6-carboxy-2-amino-naphthalene according to the invention can be prepared according to the invention by adding 2-naphthol-6-carboxylic acid in a sulfuric acid / sulfur trioxide mixture (oleum) with a sulfur trioxide content of 0 to 35% by weight.
  • the intermediate 1-sulfo-6-carboxy-2-naphthol is isolated from the reaction mixture in a conventional manner by carefully stirring the reaction mixture on ice.
  • the precipitated product is suctioned off, suspended in ice water and any sulfuric acid still present is neutralized by means of sodium carbonate by adjusting the suspension to a pH between 4 and 4.5.
  • the connection can then be isolated by suction and drying.
  • the procedure is generally such that the 1-sulfo-6-carboxy-2-naphthol in a 20 to 30 wt .-% aqueous
  • Ammonium bisulfite solution dissolves and the reaction mixture is reacted in an autoclave under the conditions specified above. After this reaction has ended, the mixture is adjusted to a pH of 1 with hydrochloric acid at room temperature. The mixture is stirred for about 1 hour, during which the sulfo-carboxy-aminonaphthalene compound according to the invention precipitates out as an inner salt and can be isolated.
  • the compounds of the general formula (1) according to the invention - hereinafter referred to as compounds (1) - have fiber-reactive properties and have very valuable dye properties. They “can therefore be used for dyeing (including printing) materials containing hydroxy groups and / or carbonamide groups.
  • the solutions obtained in the synthesis of the compounds (1) optionally after the addition of a buffer substance and optionally also after concentration, can be used directly as a liquid preparation for dyeing.
  • the separation and isolation of the compounds (1) from the aqueous synthesis solutions can be carried out according to generally known methods for water-soluble compounds, for example by precipitation from the reaction medium using an electrolyte, such as sodium chloride or potassium chloride, or by evaporation of the reaction solution itself, for example by Spray drying. If the latter type of insulation is chosen, it is often advisable to remove any sulfate amounts present in the solutions by precipitation as calcium sulfate and separation by filtration before evaporation.
  • the present invention therefore also relates to the use of the compounds (1) for dyeing (including printing) hydroxyl- and / or carbonamide-containing materials and processes for their use on these substrates.
  • the materials are preferably used in the form of fiber materials, in particular in the form of
  • Textile fibers such as yarns, packages and fabrics. This can be done analogously to known procedures.
  • Materials containing hydroxyl groups are of natural or synthetic origin, such as cellulose fiber materials ' or their regenerated products and polyvinyl alcohols.
  • Cellulose fiber materials are preferably cotton, but also other vegetable fibers, such as linen, hemp, jute and ramie fibers; Regenerated cellulose fibers are, for example, cellulose and viscose rayon.
  • Materials containing carbonamide groups are, for example, synthetic and natural polyamides and polyurethanes, in particular in the form of fibers, for example wool and other animal hair, silk, leather, polyamide-6,6, polyamide-6, polyamide-11 and polyamide-4.
  • the compounds (1) can be applied and fixed on the substrates mentioned, in particular on the fiber materials mentioned, by the application techniques known for water-soluble, fiber-reactive dyes, for example by dissolving the compound (1) in solution applies to or brings them into the substrate and fixes them on or in this by the action of heat or by the action of an alkaline agent or by both measures.
  • staining and fixing methods have been described in numerous publications (for example in European Patent Application Publication No. 0 181 585-A2).
  • the compounds (1) are distinguished by high degrees of extraction and fixation. In the exhaust process in particular, they deliver dyeings with a high depth of color and a high degree of fixation, even in wide temperature ranges (40 to 80 ° C).
  • the dyeings according to the invention particularly on cellulose fiber materials, have good lightfastness both in the dry state of the dyeing and in the wet state, for example moistened with a sweat solution as well as good wet fastness properties, such as good wash fastness properties at 60 to 95 ° C, even in the presence of perborates, acidic and alkaline whale, over-dyeing and perspiration fastness properties, good acid and alkaline perspiration fastness properties, high steam resistance, good acid, water and seawater fastness properties , furthermore good pleating fastness, ironing fastness and rubbing fastness. They also have good acid fading resistance when storing moist, colored material which still contains acetic acid.
  • Parts by weight relate to parts by volume such as kilograms to liters.
  • the compounds described by formula in these examples are given in the form of the free acids; in general, they are prepared and isolated in the form of their alkali metal salts, such as lithium, sodium or potassium salts, and used in the form of their salts for dyeing.
  • the starting compounds and components mentioned in the following examples, in particular table examples, in the form of the free acid can be used as such or in the form of their salts, preferably alkali metal salts, in the synthesis.
  • the diazonium salt solution from Example B is used, 36.3 parts of 1- (4'- ⁇ -sulfatoethylsulfonyl) phenyl-3-methyl-5-pyrazolone are added and the coupling reaction is carried out at 10 ° C. and a pH of 4 through.
  • the azo compound according to the invention is salted out and isolated using sodium chloride. A yellow, electrolyte-containing powder of the alkali metal salt (sodium salt) of the compound of the formula is obtained
  • the azo compound according to the invention shows very good fiber-reactive dye properties and, on the fiber materials mentioned in the description, such as in particular cotton, provides brilliant, brilliant yellow dyeings and prints with good fastness properties, of which in particular those, according to the application and fixing methods customary in the art for fiber-reactive dyes Lightfastness can be highlighted.
  • the known coupling component 2- (4 * -ß-sulfatoethylsulfonylphenyl) -azo-3,6-disulfo-l-amino-8-naphthol is obtained in a conventional manner by coupling the diazonium salt from 26 parts of 4- ( ⁇ -sulfatoethylsulfonyl) - aniline with 33.2 parts of 1-amino-8-naphthol-3,6-disulfonic acid. The solution obtained is then mixed with the diazonium salt solution of 27 parts of 1-sulfo-6-carboxy-2-amino-naphthalene according to Example B and at a pH of 4 to 5 and a temperature of 15 to 20 ° C. Azo connection coupled. The disazo compound according to the invention obtained is salted out with sodium chloride and isolated. A deep blue electrolyte-containing powder of the alkali metal salt (sodium salt) of the compound of the formula is obtained
  • the azo compound according to the invention shows very good fiber-reactive dye properties and, on the fiber materials mentioned in the description, such as in particular cotton, provides vivid, lively navy-blue dyeings and prints with good fastness properties in the application and fixing methods customary in the art for fiber-reactive dyes.
  • Dye properties provide strong dyeings and prints on the materials mentioned in the description, such as in particular cellulose fiber materials, using the application and fixing methods customary for fiber-reactive dyes, with the hue specified in the respective table example (here on cotton) with good fastness properties; the values given in brackets are the absorption maxima ( ⁇ max ) in nm.
  • the azo compound according to the invention shows very good fiber-reactive dye properties and, on the fiber materials mentioned in the description, such as, in particular, cotton, gives bright, brilliant navy-blue dyeings and prints in accordance with the application and fixing methods customary in the art for fiber-reactive dyes.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention décrit des composés azoïques qui correspondent à la formule générale (1) mentionnée ci-après, possèdent des qualités fibroréactives et représentent des colorants appréciables. Ils colorent une matière synthétique et naturelle contenant des groupes hydroxy- et/ou carbonamide, particulièrement des matières fibreuses comme la laine et particulièrement des matières de fibres cellulosiques, en des tons intenses. La formule (1) où: M est hydrogène ou un métal salifiant tel qu'un métal alcalin; K° est un résidu de formules générales (2A) ou (2B) dans lesquelles E est le résidu d'un agent usuel dans les colorants disazoïques pouvant servir aussi bien de composant de copulation que de composant diazoïque, comme par exemple le résidu d'un composé 1-(aminophényle -ou- aminonaphtyle) -pyrazolone-, aminonaphtol-, aniline- ou 1-aminonaphtaline, v est zéro ou 1, K est le résidu d'un composant de copulation soluble à l'eau, de préférence à partir de la série naphtol-, aminonaphtol, aniline-, pyrazolone, hydroxypyridone- et acétoacétyl- arylide, ce composant de copulation contenant 1 ou 2 groupes fibroréactifs de la série sulfone de vinyle, D est un résidu de benzol ou naphtaline, ses substituants R1 et R2 étant des substituants usuels dans les colorants azoïques comme, par exemple (outre l'hydrogène) alkyle inférieur, alcoxy inférieur, halogène, sulfo et carboxy, le groupe -SO¿2?-Y est un groupe fibroréactif de la série sulfone de vinyle, a est zéro, 1 ou 2 et k est 1 ou 2. On décrit de plus le composé 2-amino-naphthaline-1-acide sulfonique-6-acide carbonique, qui peut servir de pré-produit pour la fabrication de colorants, comme, à titre d'exemple, constituant diazoïque pour la synthèse des colorants de la formule générale (1).
PCT/EP1990/002019 1989-12-02 1990-11-26 Composes azoiques et leur utilisation comme colorants, 1-sulfo-6-carboxy-2-amino-naphtaline, son utilisation comme constituant diazoique et procede de fabrication de ces composes WO1991008265A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1019920701289A KR927003733A (ko) 1989-12-02 1990-11-26 아조 화합물 및 염료로서의 그의 용도, 1-설포-6-카복시-2-아미노 나프탈렌, 디아조 성분으로서의 그의 용도, 및 이 화합물들의 제조방법
BR909007891A BR9007891A (pt) 1989-12-02 1990-11-26 Compostos azo e seu emprego como corantes,1-sulfo-6-carboxi-2-amino-naftalen o,seu emprego como componente diazo e processo para a preparacao destes compostos

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3939909.5 1989-12-02
DE3939909A DE3939909A1 (de) 1989-12-02 1989-12-02 Azoverbindungen und ihre verwendung als farbstoffe, 1-sulfo-6-carboxy-2-amino-naphthalin, dessen verwendung als vorprodukt der azoverbindungen und verfahren zur herstellung dieser verbindungen

Publications (1)

Publication Number Publication Date
WO1991008265A1 true WO1991008265A1 (fr) 1991-06-13

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PCT/EP1990/002019 WO1991008265A1 (fr) 1989-12-02 1990-11-26 Composes azoiques et leur utilisation comme colorants, 1-sulfo-6-carboxy-2-amino-naphtaline, son utilisation comme constituant diazoique et procede de fabrication de ces composes

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EP (1) EP0502893A1 (fr)
JP (1) JPH05501278A (fr)
KR (1) KR927003733A (fr)
BR (1) BR9007891A (fr)
DE (1) DE3939909A1 (fr)
WO (1) WO1991008265A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0827984A1 (fr) * 1996-09-09 1998-03-11 Bayer Ag Colorants dérivés de l'acide amino-alkyl-inférieur naphtalènecarboxylique
CN103030994A (zh) * 2010-08-27 2013-04-10 天津德凯化工股份有限公司 一种用于染色纯棉的染料活性兰

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR738680A (fr) * 1931-06-15 1932-12-28 Ig Farbenindustrie Ag Procédé de préparation de dérivés chlorés ou bromés de l'acide 2-amino-naphtalène-1-sulfonique
BE663540A (fr) * 1964-05-06 1965-11-08
BE670089A (fr) * 1964-09-24 1966-03-24
FR2229742A1 (fr) * 1973-05-17 1974-12-13 Hoechst Ag

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR738680A (fr) * 1931-06-15 1932-12-28 Ig Farbenindustrie Ag Procédé de préparation de dérivés chlorés ou bromés de l'acide 2-amino-naphtalène-1-sulfonique
BE663540A (fr) * 1964-05-06 1965-11-08
BE670089A (fr) * 1964-09-24 1966-03-24
US3518245A (en) * 1964-09-24 1970-06-30 Hoechst Ag Azo dyestuffs and their metal complex compounds
FR2229742A1 (fr) * 1973-05-17 1974-12-13 Hoechst Ag

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0827984A1 (fr) * 1996-09-09 1998-03-11 Bayer Ag Colorants dérivés de l'acide amino-alkyl-inférieur naphtalènecarboxylique
US5795971A (en) * 1996-09-09 1998-08-18 Bayer Aktiengesellschaft Aminomethylnaphthalenecarboxlic acid dyestuffs
CN103030994A (zh) * 2010-08-27 2013-04-10 天津德凯化工股份有限公司 一种用于染色纯棉的染料活性兰

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BR9007891A (pt) 1992-09-29
KR927003733A (ko) 1992-12-18
DE3939909A1 (de) 1991-06-06
JPH05501278A (ja) 1993-03-11
EP0502893A1 (fr) 1992-09-16

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