Способ получения водорастворимых азокрасителей

Способ получения водно-нерастворимого азокрасителя

Способ получения водорастворимого азокрасителя

Azoverbindungen,deren Herstellung und Verwendung

SALTS OF SULPHONATED AZO DYES AND THEIR USE

BASIC AZO DYES FREE FROM SULPHONIC ACID GROUPS THEIR PRODUCTION AND USE

... 1332477 Substituted dihydropyridine derivatives SANDOZ Ltd 2 Nov 1970 [7 Nov 1969 23 Dec 1969 13 Aug 1970 18 Aug 1970] 52077/70 Addition to 1273748 Heading C2C [Also in Division C4] Compounds of formula wherein R is H or an organic radical, R 1 is H or a hydrocarbon radical, a heterocyclic radical or an amino group, which radical or group may be substituted, A is an anion and Z represents the atoms needed to complete a ring of aromatic character which may contain one or more further hetero atoms and may be substituted and on which one or more further rings may be condensed are used in the preparation of azo dyes (see Divisions C4-C5) and are prepared by condensing a salt of an acetamide bearing a group of formula with an acylacetic acid ester in an organic solvent in the presence of a basic catalyst. In Examples: (1) N-carbamoylmethyl-pyridinium chloride is reacted with methyl acetoacetate in methanolic NaOH to give 2-keto-3-pyridinium chloride - 4 - methyl - 6 - hydroxy - 1,2 - dihydropyridine ...

AZO PYRIDONES

... 1377614 Azo-pyridone dyestuffs IMPERIAL CHEMICAL INDUSTRIES Ltd 20 Dec 1971 [4 Jan 1971] 39947/72 Divided out of 1377612 Heading C4P Novel dyestuffs, free from sulphonic and carboxylic acid groups, of the formula wherein A is an aromatic (including heterocyclic) radical, Y is H, alkenyl or optionally substituted alkyl, aralkyl, cycloalkyl or aryl, T is C 1-6 alkyl, Hal is Cl or Br, and n is 1 or 2 are prepared by halomethylation of the corresponding 3- unsubstituted pyridones. They may be applied from aqueous dispersion to polyamide, cellulose acetate and triacetate and polyester fibres.

NEW AZO DYESTUFFS AND PROCESSES FOR THEIR MANUFACTURE AND USE

... 1277090 Basic azo dyestuffs CIBA-GEIGY AG 30 May 1969 [31 May 1968] 27444/69 Heading C4P The invention comprises basic azo dyestuffs of general formula and their tantomers, wherein D is a diazo component residue which may contain an azo group and contains at least one amino, hydrazino, or etherified hydroxylamino group that may be quaternated, the dyes being free from acidic groups imparting solubility in water. D is preferably a benze, naphthalene or at most bicyclic heterocyclic radical, the amino, hydrazino or etherified hydroxylamino group being linked thereto via a carbon chain optionally interrupted by a hetero-atom or which forms part of a ring. They are prepared by (a) reacting an azo compound with an amine, hydrazine or etherified hydroxylamine, (b) diazotizing an amine D-NH 2 and coupling to 2,6-dihydroxy- 3-cyano-4-methyl pyridine, or (c) quaternizing an unquaternated azo compound. The dyes dye wool, mordanted cotton and synthetic materials in yellow, orange and red shades.

NEW AZO DYESTUFFS AND PROCESSES FOR THEIR MANUFACTURE AND USE

... 1278312 Azo dyes CIBA-GEIGY AG 9 July 1969 [15 July 1968] 34592/69 Heading C4P New azo dyes containing at least one acidic group which imparts solubility in water, not in a vicinal position to the azo bridge, and a residue of formula are prepared by azo coupling using 2,6- dihydroxy - 3 - cyano - 4 - methyl - pyridine as coupling components. The preferred dyes contain fibre-reactive groups which are present in the diazo component or subsequently introduced into the dye by a condensation reaction. The preparation of mono- and dis-azo, metallized azo and phthalocyanine-azo dyes which dye cellulose and wool fibres in yellow, red, green and brown shades is described in examples.

Process of colouring of textile matters, and coloured textile matters.

Process of dyeing and impressions of organic matters with dyes of development.

Textile matter absorbent coloured and its process of colouring.

PROCEDURE FOR COLORS OF SYNTHETIC SYNTHETIC MATERIALS

PROCEDURE FOR the PRODUCTION OF NEW ONE 3-SULFOALKYL-6-HYDROXY-PYRIDONEN (2)

PROCEDURE FOR COLORS OR PRINTING ON TEXTILE MATERIAL OR LEATHER

Procedure for the production of new Azoverbindungen

Procedures for the production of new Hydroxypyridon monosulfonsäuren

PROCEDURE FOR COLORS OF SYNTHETIC SYNTHETIC MATERIALS

Procedure for the production of water-insoluble Azofarbstoffe

3-SULPHOALKYL-6-HYDROXY-PYRID-%2</ONES

AZO DYESTUFF SULFONIC ACID SALTS, PROCESS FOR THEIR MANUFACTURE AND THEIR USE

Abstract for the Disclosure Azo dyestuff sulfonic acid salts of the formula wherein A represents a carbocyclic or heterocyclic aromatic radical, B represents an aliphatic, cycloaliphatic or araliphatic amine, X represents a hydrogen atom or a substituted or unsubstituted alkyl group, a cycloalkyl, aralkyl or aryl group, Y represents a hydrogen or halogen atom, a nitro, cyano, acyl, sulfonic acid, arylsulfonyl, alkoxycarbonyl group or a substituted or unsubstituted alkyl, sulfa-moyl or carbamoyl group, Z represents a substituted or unsubstituted alkyl group or an aryl radical, m and n are 1 or 2.

AZO COMPOUNDS, THEIR MANUFACTURE AND USE

Verfahren zur Darstellung eines Abkömmlings der Zitrazinsäure.

Verfahren zur Darstellung eines Abkömmlings der Zitrazinsäure.

Matériel sensible du type diazo.

Monoazo dispersion dyes - from 3-cyan 4-methyl 6-hydroxy pyrid-2-one with N-substit. as coupling component

This patent of addition relates to the prepn. of azo dyes from coupling component of formula (I) and diazotised amines of formula D-NH2, (in which D is phenyl opt. substd. with 1-3 Cl, Br, NO2, CN, CF3, CH3, OCH3, OC2H5, phenyl, acetyl, benzoyl, methoxy-, ethoxy-, beta-methoxy- ethoxy- or benzoyloxy-carbonyl, methoxy- or ethoxy-carbonyloxy, methoxy- or ethoxy-carbonylamino, acetoxy, propionyloxy, benzoyloxy, N-morpholyl sulphonyl, methyl- or ethyl-sulphonyloxy gpas. or phenylsulphonyloxy bearing phenyl gp. or a thienyl gp. opt. substd. with acetyl).

Pure yellow azo cpds - contg a 3-sulphoalkyl-6-hydroxy-pyrid -2-one residue, for dyeing/printing cellulosics,wool,silk,leather pol

The azo cpds. esp. contain the gp. of formula (I):- (where R and R1 are each H, alkyl, aryl or a heterocyclic gp; X is a sulphoalkyl gp, pref. a sulphomethyl gp, and esp. a gp. of formula (II):- -CH(V)-SO3H (II), V being lower alkyl, aryl or heterocyclic gp., opt. substd. or pref H). (I) is linked via an azo bridge to the residue of a diazo component which may be heterocyclic or aromatic, from a cpd. of the anthraquinone, nitroaryl, phthalocyanine, stilbene or analogous series; pref. the diazo residue is of the benzene or naphthalane series. Prepd. by coupling a suitably diazo component with a 3-sulphoalkyl-6-hydroxypyrid-2-one, eps. a 3-sulphomethyl-1:4-dialkyl-6-hydroxy pyrid-2-one and opt. metallising.

Verfahren zur Herstellung wasserlöslicher Azofarbstoffe

Verfahren zur Herstellung von Monoazoverbindungen

Verfahren zur Herstellung von basischen Verbindungen der Azoreihe

Verfahren zur Herstellung neuer wasserlöslicher Azofarbstoffe

3-sulphoalkyl-6-hydroxypyrid-2-ones - coupling components for prepn of dyes

Title cpds. pref. of formula (I) : (where R and R' are H or (substd) alkyl or heterocyclic residues, and X is a sulphoalkyl gp). are prepd. by reacting 6-hydroxypyrid-2-ones with bisulphite addn. cpds. of aldehydes.

Azo metal complexes for dyeing nitrogen contg fibres

Blue, red and violet azo dye heavy metal complexes for dyeing/printing silk, leather and esp. wool but also synthetic superpolyamides, superpolyurethanes, polyacrylonitrile, etc. uniform shades fast to acids, alkalis, light and rubbing are derived from azo cpds. contg. as diazotisation component residue a heterocyclic gp. contg. a complexing site and separated from the azo gp. by one or two atoms and as coupling component, the residue of a halo-2:3-dihydroxypyridine. Preferred cpds. are the heavy metal complexes of azo cpds. of formulae (I) and (II): where D is a quinoline gp. linked in pos. 8; Z is halogen, sulphonic acid, acylamino, or arylazo.

Verfahren zur Herstellung von Reaktivfarbstoffen

VERFAHREN ZUR HERSTELLUNG VON AZOVERBINDUNGEN.

Yellowish-green azo dyes for cotton, wool, silk, etc

Yellowish-green azo cpds. for fast dyeing/printing of silk, leather, wool, synthetic superpolyamides and superpolyurethanes, polyesters, polyacrylonitrile and cellulosics such as linen, cellulose, regenerated cellulose, cotton, etc. contain an acid water-solubilising substituent and a gp. of formula: (wherein R is alkyl and R' is alkyl aryl). Also of interest are the azo cpds. not contg. water-solubilising gps. and complexes of these azo cpds. with heavy metals.

VERFAHREN ZUR HERSTELLUNG VON AZOFARBSTOFFEN.

VERFAHREN ZUR HERSTELLUNG VON AZOFARBSTOFFEN.

VERFAHREN ZUR HERSTELLUNG NEUER AZOFARBSTOFFE.

3-sulphoalkyl-6-hydroxypyrid-2-ones - coupling components for prepn of dyes

Title cpds. pref. of formula (I) : (where R and R' are H or (substd) alkyl or heterocyclic residues, and X is a sulphoalkyl gp). are prepd. by reacting 6-hydroxypyrid-2-ones with bisulphite addn. cpds. of aldehydes.

Yellow,organe and red azo cpds - for dyeing/printing acrylonitrile base fibres

Cpds. of formula (I): (where D is the residue of a diazo component, pref. of the benzene or naphthalene series, R1 and R2 can be H) contain >=1 carboxyl gp. not linked directly to the ring in the posn. next to the azo bridge. They are prepd. by coupling diazo derivs. of amines D-NH2 with appropriate hydroxypyridines.

Basic azo dyes contg no sulphonic acid gps

Compds. have the formula: where D is a (substd.) aromatic-carbocyclic or aromatic-heterocyclic residue, R is H or an organic residue, R1 is H or a (substd.) hydrocarbon residue, a (substd) heterocyclic residue or a (substd) amino group, A- is an anion, K+ has the formula where R2 and R3 are (substd) (cyclo)alkyl groups or form, with R2 and the N atom a heterocyclic group, R4 and R5 are H or (substd) (cyclo)alkyl groups, R6 and R7 are (substd) hydrocarbon residues, and R8 is a (substd) (cyclo)alkyl group, and where R4 and/or R3 with R5 and the N atom, R6 and R7, or R6, R7 and R8 with the N atom, may form heterocyclic groups. The dyes are prepared in known way. The dyes can be used on polyacrylonitrile, polyamides, polyesters, compositions contg. natural materials or resins, synthetic compositions, leather or paper. The dyes have good solubility in water and organic solvents, and have good pH stability. The dyeings are stable to washing perspiration, sublimation, pleating, ironing, steaming ...

Verfahren zur Herstellung eines neuen, substituierten 2,3-Pyridindiols

Verfahren zur Herstellung von 2-Amino-3-pyridinol

Verfahren zur Herstellung von Monoazoverbindungen

Verfahren zur Herstellung von Hydroxypyridonen

Verfahren zur Herstellung wasserunlöslicher Monoazofarbstoffe

Verfahren zur Herstellung von basischen Farbstoffen

Verfahren zur Herstellung von Azoverbindungen

Verfahren zur Herstellung von 2,3-Pyridindiol

Verfahren zur Herstellung von 2,3-Pyridindiol

Verfahren zur Herstellung von wasserunlöslichen Monoazofarbstoffen

VERFAHREN ZUR HERSTELLUNG VON BASISCHEN AZOFARBSTOFFEN.

VERFAHREN ZUR HERSTELLUNG WASSERUNLOESLICHER AZOFARBSTOFFE.

COLORING MONOAZOIC IDROSOLUBILI.

AZOFARBSTOFFE.

Water-insoluble azo dyes and preparation thereof

Process for preparing quinazolone azo pigments

Azo dyes - contg dihydroxypyridine residues

Azo dyes (or salts, quat. derivs or metal complexes of these) contg. as residue of coupling component a dihydroxypyridine residue carrying a substituent in the o-position with respect to the azo grp. with >=1 hetero atom but which is not a halogen atom. Preferred dyes are of the form (I) or (II) where D = residue of diazo component and X = OH, alkoxy, phenoxy, naphthoxy, mercapto, amino (opt. carrying fibre-reactive groups) or sulphone grp., or a water-solubilising grp. such as a sulphonic acid residue, and R = the residue of a diamine. the dyes are useful fibre-reactive dyes for cotton, synthetic polyamides and wool and in the form of heavy metal complexes, for dyeing and printing wool, leather, polyamides etc.

Pure yellow azo cpds

Pure yellow azo cpds contg a 3-sulphoalkyl-6-hydroxy-pyrid -2-one residue, for dyeing/printing cellulosics,wool,silk,leather pol ...

MEANS TO THE FAERBEN OF KERATINHALTIGEM MATERIAL.

Pure yellow azo cpds

Pure yellow azo cpds contg a 3-sulphoalkyl-6-hydroxy-pyrid -2-one residue, for dyeing/printing cellulosics,wool,silk,leather pol ...

Undecyl esters and preparation thereof

The invention relates to 11-amino-undecyl esters. They conform to the formula I where R<1> and R<3> are each for example hydrogen and R<2> and R<4> for example methyl, and R<5> and R<6> are each for example methyl. The esters are suitable for preparing anionic dye salts which are very readily soluble in organic solvents.

AZOFARBSTOFFE.

Cationic 5-arylazo-6-hydroxypyridone-2 dyes

AZO DYES, THEIR PREPARATION AND THEIR APPLICATION

0-AMINOALKYL-PYRIDIN-2-ONES

AZO DYES SERIES [...] THE

Ces colorants azoïques de la série pyridonique répondent à la formule I, dans laquelle D représente le radical d'un composant diazoïque de la série benzénique, azobenzénique, thiophénique, thiazolique, benzothiazolique ou benzoisothiazolique et R représente un atome d'hydrogène ou un radical alcoyle éventuellement substitué, cycloalcoyle, aralcoyle ou aryle. Les colorants donnent en particulier sur les polyesters, des teintures franches, d'une couleur intense, qui se caractérisent par de bonnes résistances à la lumière, à l'humidité et à la fixation thermique. These azo dyes of the pyridonic series have the formula I, in which D represents the radical of a diazo component of the benzene, azobenzene, thiophenic, thiazole, benzothiazole or benzoisothiazole series and R represents a hydrogen atom or an alkyl radical optionally substituted, cycloalkyl, aralkyl or aryl. The dyes give in particular on polyesters, clear dyes, of an intense color, which are characterized by good resistance to light, to humidity and to thermal fixation.

AZO DYESTUFFS CONTAINING HYDROXYPYRIDONE RESIDUES THEIR MANUFACTURE AND USE

PROCESS FOR PREPARING WATER-INSOLUBLE AZO DYES CONTAINING 3-CYANO-5-AZO-6-HYDROXY-PYRIDONE-2-RESIDUES

Monoazo compounds derived from 2-hydroxymethyl-amino benzoic acids and 2,6-dihydroxypyridines

PROCESS FOR RESIST PRINTING

NEW AZO DYESTUFFS AND PROCESSES FOR THEIR MANUFACTURE AND USE

AZO DYES SERIES [...] THE

Novel Pyridone Dyes

The invention relates to compounds of the formula (I): 2. A compound as claimed in claim 1 , wherein the compound of the formula (I) contains at least one sulfo group having the countercation M.3. A compound as claimed in claim 1 , wherein the countercation Mis an organic cation selected from the group consisting of the imidazolium cations claim 1 , alkylguanidinium cations claim 1 , phosphonium cations claim 1 , primary claim 1 , secondary claim 1 , tertiary or quaternary ammonium cations claim 1 , benzotriazolyl cations and pyridinium cations.4. A compound as claimed in claim 1 , wherein{'sup': '0', 'sub': 1', '2, 'Ris C-C-alkyl.'}5. A compound as claimed in claim 1 , wherein{'sup': '1', 'sub': 1', '2', '1', '2', '2, 'Ris (C-C-alkylene)sulfo, CONH(C-C-alkyl) or CONH.'}6. A compound as claimed in claim 1 , wherein{'sup': '2', 'sub': 1', '8', '1', '8', '1', '4', 'm, 'Ris C-C-alkyl, hydroxy-C-C-alkyl or —(C-C-alkylene-O—)—R, wherein'}{'sub': 1', '10, 'R is H or C-C-alkyl, and'}m is a number from 1 to 15.7. A compound as claimed in claim 1 , wherein{'sup': '3', 'sub': 1', '4', '1', '4, 'Ris H, a sulfo group, C-C-alkyl or C-C-alkoxy.'}8. A compound as claimed in claim 1 , wherein{'sup': '4', 'sub': 1', '4', '1', '4, 'Ris H, C-C-alkyl or C-C-alkoxy.'}9. A compound as claimed in claim 1 , wherein{'sup': 5', '−', '+, 'sub': 1', '2, 'Ris OH, OM, C-C-alkyl-, halogen- or sulfo-substituted phenyl or unsubstituted phenyl, where wherein'}{'sup': '+', 'Mis an alkali metal cation, a quaternary ammonium cation or a phosphonium cation.'}12. A solution comprising 0.01% to 45% by weight of one or more compounds of the formula (I) as claimed in claim 1 , dissolved in an organic solvent.13. A binder-containing colorant solution comprising 0.01% to 40% by weight of one or more compounds of the formula (I) as claimed in claim 1 , dissolved in at least one organic solvent claim 1 , at least one polymeric binder and claim 1 , optionally claim 1 , further auxiliaries.14. A colored high ...

Pyridone Dye Composition

The invention relates to a colorant composition comprising at least one compound of the formula (I) and at least one pigment, in which the compounds of the formula (I) have the following formula: 2. The colorant composition as claimed in claim 1 , wherein the at least one compound of the formula (I) contains at least one sulfo group having the countercation M.3. The colorant composition as claimed in claim 1 , wherein the countercation M is an organic ammonium cation or an organic phosphonium cation.4. The colorant composition as claimed in claim 3 , wherein the organic ammonium cation is a primary claim 3 , secondary claim 3 , tertiary or quaternary ammonium cation.5. The colorant composition as claimed in claim 3 , wherein the organic ammonium cation is an imidazolium cation claim 3 , alkylguanidinium cation claim 3 , benzotriazolyl cation or pyridinium cation.6. The colorant composition as claimed in claim 1 , wherein the at least one pigment is an organic pigment.7. The colorant composition as claimed in claim 1 , wherein the at least one organic pigment is selected from the group consisting of anthraquinone pigments claim 1 , laked or unlaked azo pigments claim 1 , anthanthrone pigments claim 1 , benzimidazolone pigments claim 1 , quinacridone pigments claim 1 , quinophthalone pigments claim 1 , diketopyrrolopyrrole pigments claim 1 , dioxazine pigments claim 1 , disazo condensation pigments claim 1 , isoindolinone pigments claim 1 , isoindoline pigments claim 1 , metal complex pigments claim 1 , perinone pigments claim 1 , perylene pigments claim 1 , phthalocyanine pigments and triarylcarbonium pigments.8. The colorant composition as claimed in claim 1 , wherein the mixing ratio of the at least one compound of the formula (I) to the at least one pigment is from 1:99 to 99:1 parts by weight.9. The colorant composition as claimed in claim 1 , wherein the at least one compound of the formula (I) is present in an amount of 1% to 20% by weight claim 1 , based on ...

Storage-stable dye solutions

The present invention relates to storage-stable dye salts, solutions and compositions thereof a process for their preparation and their use for dyeing and/or printing substrates.

Yellow toner

To provide a yellow toner that it provides a sharper color than ever before in small amounts and the hue is greener than ever before, whereby the color range can be increased. Disclosed is a yellow toner containing a binder resin and a yellow colorant, wherein, as the yellow colorant, a compound A represented by the following general formula (1) and a compound B represented by the following formula (2) are contained, and wherein, with respect to 100 parts by mass of the binder resin, a content of the compound A is from 0.5 to 7.5 parts by mass, and a content of the compound B is from 0.5 to 8.0 parts by mass:

COLORING COMPOUND AND THERMAL TRANSFER RECORDING SHEET

A thermal transfer recording sheet includes a base material and, on the base material, a yellow-dye layer containing a yellow dye, a magenta-dye layer containing a magenta dye, and a cyan-dye layer containing a cyan dye. The yellow dye and the cyan dye contain compounds having specific structures. 2. The coloring compound according to claim 1 , wherein Rand Rin Formula (1) are the same alkyl groups.3. The coloring compound according to claim 1 , wherein Rand Rin Formula (2) are the same alkyl groups.4. The coloring compound according to claim 1 , wherein Rand Rin Formula (2) are the same alkyl groups having 1 to 8 carbon atoms. The present disclosure relates to a coloring compound and a thermal transfer recording sheet.In recent years, with the widespread use of portable color display devices, the demand for easy color printing of photographs taken and documents prepared with the devices has been increasing. Examples of a color-printing method that meets the demand include an electrophotographic method, an ink-jet method, and a thermal transfer recording method. The thermal transfer recording method enables printing by a dry process and miniaturization of a printer, thereby providing excellent portability. Thus, of the foregoing methods, the thermal transfer recording method is excellent due to easy printing in any environment. In addition, since this method uses a dye as a coloring material, density of an image can be controlled by using a concentration gradient of coloring materials, thereby resulting in clear images and excellent color reproducibility.The thermal transfer recording method is an image forming method that includes placing a thermal transfer recording sheet on an image-receiving sheet and heating the thermal transfer recording sheet to transfer a coloring agent present in the thermal transfer recording sheet onto the image-receiving sheet. The thermal transfer recording sheet includes, on a sheet-shaped base material, a coloring-material layer ...

Pyridinone azo dispersion dyes and its synthetic method containing sulfonate group or sulfoamido

本发明公开了一种含磺酸酯基或磺酰胺基的吡啶酮偶氮分散染料及其制备方法，其化合物分子结构如下式所示：

3-hydroxy-pyridine derivatives

Method of dyeing polyamide and wool fibers

NITROGEN PIGMENTS

L'invention concerne des composés de la formule ci-après, dans laquelle : X est un atome de chlore ou de brome, n vaut 0, 1, 2, 3 ou 4, et K est le reste d'un copulant. Les composés conviennent parfaitement comme pigments pour la coloration d'encres d'impression, de matières plastiques et de vernis.

Hydrophilic textiles dyed with azo dyes of hydroxy-pyridone series - coupled in situ on the fibres (NL070377)

Hydrophilic textiles are dyed with azo dyes of formula D-(N=N-A)n (in which D is the gp. of a diazo or tetrazo component; A is a 6-hydroxy pyrid-2-one gp. coupled in 5-position, the N atom carrying an opt. substd. alkyl gp. with >=5C atoms, or an alkenyl, alkinyl or alkeninyl gp.; n is 1 or 2). Dyeing of hydrophilic textiles by applying an alkaline soln. of 6-hydroxy pyrid-2-one substd. as above and coupling with a diazo or teteazo component is also claimed. Esp. used for dyeing cellulose textiles, or polyester/cellulose blends in ratios 50:50, 67:33 or 80:20. A wide range of shades can be obtained. Certain dyes are readily sublimable, with increased affinity for hydrophobic fibres. In an example, mercerised cotton is impregnated with a hot soln. of 1-(2'-ethyl hexyl) 3-cyan 4-methyl 6-hydroxy pyrid-2-one and dried. A printing paste contg. a diazo or tetrazo component is applied and the fabric dried.

NEW BASIC AZOIC DYES EXEMPTED FROM SULFO GROUPS AND THEIR PREPARATION

L'invention a pour objet de nouveaux composés azoïques exempts de groupes sulfo et leur préparation. Les composés de l'invention répondent à la formule : The subject of the invention is novel azo compounds free from sulfo groups and their preparation. The compounds of the invention correspond to the formula:

Patent FR2190972A1

Patent FR2080879A2

WATER INSOLUBLE YELLOW MONOAZO COLORANTS

LA PRESENTE INVENTION A POUR OBJET UNE CLASSE NOUVELLE DE COLORANTS MONOAZO HYDRO-INSOLUBLES DERIVANT DES 6-HYDROXY-2-PYRIDONES. ELLE EST CARACTERISEE EN CE QUE CES COLORANTS PRESENTENT LA FORMULE GENERALE: (CF DESSIN DANS BOPI) (CF DESSIN DANS BOPI) OU:X EST OR OU NHR, NRR (R, R FORMANT EVENTUELLEMENT UN NOYAU COMPORTANT 5 OU 6ATOMES DE CARBONE); NHR;R EST H, UN ALKYLE COMPORTANT 1 A 5ATOMES DE CARBONE, OU (CH)OH, (CH)OR;R EST CN, COOR, CONHR, CONRR (R, R FORMANT EVENTUELLEMENT AVEC N UN NOYAU COMPRENANT 5 OU 6ATOMES DE CARBONE);R, R SONT DES RADICAUX ALKYLES COMPRENANT 1 A 5ATOMES DE CARBONE; ETR EST UN RADICAL CYCLOALKYLE COMPRENANT 5 OU 6ATOMES DE CARBONE. ELLE SE RAPPORTE A UN PROCEDE DE PREPARATION DE CES COLORANTS AINSI QU'A LEUR PREPARATION POUR LA TEINTURE DE FIBRES SYNTHETIQUES. THE SUBJECT OF THE PRESENT INVENTION IS A NEW CLASS OF HYDRO-INSOLUBLE MONOAZO COLORANTS DERIVED FROM 6-HYDROXY-2-PYRIDONES. IT IS CHARACTERIZED IN THAT THESE COLORANTS HAVE THE GENERAL FORMULA: (CF DRAWING IN BOPI) (CF DRAWING IN BOPI) OR: X IS GOLD OR NHR, NRR (R, R POSSIBLY FORMING A CORE WITH 5 OR 6 ATOMS OF CARBON); NHR; R IS H, AN ALKYL CONTAINING 1 TO 5ATOMS OF CARBON, OR (CH) OH, (CH) OR; R IS CN, COOR, CONHR, CONRR (R, R FORMING POSSIBLY WITH N A CORE CONTAINING 5 OR 6ATOMS OF CARBON); R, R ARE ALKYL RADICALS WITH 1 TO 5 ATOMS OF CARBON; ETR IS A CYCLOALKYL RADICAL WITH 5 OR 6 ATOMS OF CARBON. IT RELATES TO A PROCESS FOR THE PREPARATION OF THESE DYES AS WELL AS TO THEIR PREPARATION FOR DYING SYNTHETIC FIBERS.

Patent FR2176040A1

AZOIC COLORANTS, THEIR PREPARATION AND APPLICATION

Nouveaux colorants azoiques de formule :

Pillidonic azo dyestuff

Patent FR2132123A1

PROCESS FOR DYING KERATINIC MATERIALS

Procédé de teinture de matières kératiniques à l'aide de colorants se développant sur la fibre. Le procédé consiste à appliquer dans un ordre quelconque l'un après l'autre le sel diazoïque et le composant de copulation et à les copuler l'un avec l'autre, le composant de copulation étant choisi parmi ceux de formules : Process for dyeing keratin materials using dyes which develop on the fiber. The method comprises applying in any order one after the other the diazo salt and the coupling component and coupling them with each other, the coupling component being selected from those of formulas:

Process for the preparation of 2.3-dihydroxy-pyridine

AZO DYES

Patent FR2381806B1

Basic azo compounds, their preparation and use

Reactive dyestuffs in tautomeric forms - for polyamide and cellulose textiles

Reactive dyestuffs in tautomeric forms for polyamide and cellulose textiles. N2A. Water-sol. azo dyes which contain at least one sulphonic acid grp., at least one cellulose reactive grp. and at least one grp. of formula: (Z = H or opt. substd. alkyl, aralkyl, cycloalkyl, aryl or heterocyclic residue, T1 = H CN, COOR1, CONR1R2, COR1 or OH grp. of an opt. substd. alkyl, aralkyl, cycloalkyl, aryl or heterocyclic residue, and R1 and R2 each = H, an opt. substd. aralkyl, alkyl, cycloalkyl, aryl or heterocyclic residue, or the gp., -NR1R2 grp. or an opt. substd. alkyl, aralkyl, cycloalkyl, aryl or heterocyclic residue and M = H) are prepd. by diazotising an aromatic amine and coupling the resulting diazo cpd. with a coupling component consisting of one of the possible tautomeric forms of formula: The amine and the coupling component together contain at least one fibre reactive grp. and at least one sulphonic acid grp.

Process for dyeing and printing

O-6-hydroxypyridone-2 dyes bearing a cationic group in the 3-position

Azo dyes of the formula WHEREIN D is carbocyclic or heterocyclic aryl, R is hydrogen or an organic radical, R1 is hydrogen, hydrocarbyl, heterocyclyl, amino or substituted amino, K is substituted ammonium or hydrazinium (including compounds wherein the nitrogen(s) is (are) part of a heterocyclic ring), and A is an anion. These azo dyes are useful for the dyeing and printing of fibers (and textiles thereof) of acrylonitrile polymers and copolymers as well as polyamides and polyesters containing acidic groups. They give level dyeings having good fastness to light and water.

Process for the preparation of azo compounds

Patent FR2016776A1

Patent CS166756B2

NITROGEN COMPOUNDS, PROCESS FOR THE PREPARATION AND THEIR USE

Water insoluble monoazo dye

Azo compounds, their manufacture and use

Patent FR2086281A1

Yellow - green, water-sol reactive azo cpds contg - the residue of a 3-sulpho-6-hydroxy-pyridone-(2),for dyeing/printing

The 3-sulpho-6-hydroxypyridone-(2) gp. has the formula : (where R and R1 are each H, alkyl, aryl or heterocyclic gp.) and is linked via an azo bridge to the residue of a diazo component of the heterocyclic or aromatic series, the dyes so formed being opt. metallised. Prepd. by coupling pref. a 3-sulpho-1:4-di-alkyl-6-hydroxypyridone-(2) with a suitable coupling component, esp. of the benzene series, and opt. metallising.

Pyridone azo disperse dye containing sulfonate group and synthesis method thereof

本发明公开了一种含磺酸酯基的吡啶酮类偶氮分散染料及其合成方法，化学结构通式如下：式（Ⅰ） 和式（Ⅱ）

Azo dyes their preparation and use

Patent FR2024762A1

Ink composition and inkjet recording method

Process for resist printing

1360459 A pyridone CIBA-GEIGY AG 21 Oct 1971 [23 Oct 1970 30 Sept 1971] 49003/71 Heading C2C [Also in Divisions C4 and D1] 3 - Cyano - 6 - hydroxy - 4 - carboxymethyl- 2-pyridone is prepared by saponification of its ethyl ester.

Water insoluble metal salts of azo dyes and their use as pigments

Azo Dyestuffs

A process for the manufacture of azo dyestuffs of the formula: A-N=N-B wherein A is the residue of an aromatic carbocyclic or heterocyclic amine and B is the residue of a 6- hydroxy-pyrid-2-one which comprises mixing together in acidic aqueous medium an aromatic carbocyclic or heterocyclic amine ANH2, a 6- hydroxypyrid-2-one and a diazotising agent.

METHOD OF OBTAINING WATER-SOLUBLE NITRES

Patent FR2102371B1

Water-insoluble monoazo dyes

AZO-DYES.

Water soluble monoazo dyes

Water soluble monoazo dyestuffs.. G2A. Suitable as acid dyestuffs for the dyeing of wool, silk and polyamides in mainly golden-yellow to orange shades have general formula:- (where D1 is an aromatic or heterocyclic residue, R is H or lower alkyl, X is the residue of a reactive compound or the residue of an alpha, beta-unsaturated aliphatic carboxylic acid or a vinylsulphone group. The group X- -D1 contains at least one -SO3H or -COOH group. In an example, 173(wt) aniline-o-SO3H were dissolved in 4000 pts water and diazotised in the usual way with sodium nitrite and conc. HCl. The diazo suspension was then added to a suspension of 150 pts. 2,6-di-hydroxy-3-cyano-4-methylpyridine in alkaline solution. After stirring for 4/6 hours the product was filtered off, washed and dried to yield a yellow powder which dyed wool and polyamides in yellow shades from an acid dyebath.

Patent FR2115154B1

Patent FR2083689B1

8-hydroxyquinoline base heterocycle azo disperse dyes and preparation method thereof

本发明涉及一种8‑羟基喹啉基杂环偶氮分散染料及其制备方法，所述8‑羟基喹啉基杂环偶氮分散染料由重氮组分与偶合组分两部分组成，其中所述的偶合组分为在碱性条件下偶合的杂环活泼亚甲基化合物或杂环酚类化合物，所述的重氮组分弱碱性杂环芳胺或弱碱性苯胺衍生物。所述制备方法是在稳定剂存在下，在有机溶剂中对弱碱性杂环芳胺或弱碱性苯胺衍生物进行重氮化，析出稳定的重氮盐固体，过滤得到固体后，将之应用于碱性偶合，获得目标染料。该染料可应用于聚酯纤维、聚酰胺纤维、聚乳酸纤维、聚丙烯纤维、醋酸纤维染色，具有优异的染色亮度。

Azo dyestuffs

Patent JPS5714779B1

Azo dyes, process for their preparation and their use

Patent FR2091415A5

Patent FR2147281B1

5-Chloro-2,3-Pyridine Diol and a Process for its Production

1,190,228. 5-chloro-2,3-pyridine-diol. J. R. GEIGY A.G. 30 Aug., 1967 [31 Aug., 1966], No. 39657/67. Heading C2C. Novel 5-chloro-2,3-pyridine-diol is prepared by reacting furfural at a temperature of about 0‹ in an aqueous medium with at least double the molar amount of chlorine or the equivalent amount of a substance or system which releases the said amount of chlorine under the conditions of the reaction, the pH being kept between 0 and 2 during the addition of the first half of the chlorine and between 0 and - 1 during the addition of the second half, reacting the so obtained mixture at a temperature of 30-60‹ C., and a pH of below 1, with at least an equimolar amount of sulphamic acid, and separating the product.

Patent CS166672B2

Azo compounds, their manufacture and use

PROCEDURE FOR PREPARING A HYDROXYPYRIDIN RESIDUE CONTAINING MONOAZO DYE.

3-sulphoalkyl-6-hydroxy-pyrid-(2)-ones, their manufacture and use

Patent FR2363323B1

Patent GB1297116A

1297116 Basic mono- and dis-azo dyes IMPERIAL CHEMICAL INDUSTRIES Ltd 24 Nov 1969 [9 Dec 1968] 58277/68 Heading C4P [Also in Division C2] New basic water-soluble azo dyes, free from SO 3 H and COOH groups, of formula wherein A is an aromatic radical which may be azo-substituted, X is a cationic group, Z is an anion, Y is a hydrogen atom or an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical, T<SP>1</SP> is a hydrogen atom or an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical or a -OH, -ON, -COOR<SP>1</SP>, -CONR<SP>1</SP>R<SP>2</SP> or -COR<SP>1</SP> group, T<SP>2</SP> is a hydrogen atom or an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical or a -CN, -COOR<SP>1</SP>, -CONR<SP>1</SP>R<SP>2</SP> or COR<SP>1</SP> group, R<SP>1</SP> and R<SP>2</SP> each independently represent an hydrogen atom or an optionally substituted alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical or R<SP>1</SP> and R<SP>2</SP> together form with the nitrogen atom a 5- or 6- membered nitrogen-containing heterocyclicring, and n and m are each 1 or 2, are prepared by azo coupling using appropriate components or by a quaternation reaction introducing the X+ group into an azo dye. The dyes are used to colour synthetic fibres, in particular acidmodified polyester, polyamide and polyacrylonitrile fibres, in yellow to red shades.

Novel pyridone dyes

The invention relates to compounds of formula (I), wherein R 0 represents C 1 -C 6 -alkyl or CF 3 ; R 1 represents sulfo, carboxy, C 1 -C 4 -alkylene-sulfo, C 1 -C 4 -alkylene-carboxy, CONH 2 , CONH(C 1 -C 4 -alkyl) or CN, R 2 represents C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, hydroxy-C 1 -C 18 -alkyl or -(C 1 -C 6 -alkylene-O-) m -R, wherein R represents H, C 1 -C 16 -alkyl or hydroxy-C 1 -C 16 -alkyl and m is an integer between 1 to 20, R 3 H, sulfo, carboxy, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy, R 4 H, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy, R 5 OH, OM, C 1 -C 6 -alkyl, unsubstituted C 6 -C 10 -aryl or C 6 -C 10 -aryl substituted by C 1 -C 6 -alky|, halogen, e.g., F, Cl, Br, carboxy or sulfo, wherein the compound of formula (I) contains at least one anionic group from the group of sulfo and carboxy with the counter cation M + , wherein M + represents an alkali metal cation or an organic cation. Compounds of formula (I) are especially suited for use in color filters.

Water-soluble monoazo dyes, process for their preparation and their use for dyeing wool or synthetic polyamide textile materials

Water insoluble azo dyes

ABSTRACT OF THE DISCLOSURE: There are disclosed a new class of water-insoluble monoazo dyes derived from 6-hydroxy-2-pyridones, a process for preparing the dyes, and the dyeing of synthetic fibers with them.

Monoazo pyridone dyes - of low water-solubility for use on hydrophobic synthetic fibres

Basic azo dyes free from sulphonic acid groups, their production and use

NITROGEN AND NITROGEN COMPOUNDS, THEIR PREPARATION PROCESS AND THEIR USE DYE

Basic azo dyes free from sulphonic acid groups, their production and use

Patent IN139896B

Patent FR2132123B1

Diazotype prints with hydroxy pyridone couplers

METHOD KRA1M1SH and PRESS TZHSTYLNYL iViATEPHAJiOB

Patent SU415886A3

AZOIC COLORANTS

CES COLORANTS SONT REPRESENTES PAR LA FORMULE I CI-APRES; POUR LES PREPARER, ON COPULE UN COMPOSE DIAZOIQUE D'AMINES DE FORMULE II AVEC UN COMPOSE DE FORMULE III. ON LES UTILISE POUR LA TEINTURE DE FIBRES SYNTHETIQUES, EN PARTICULIER DE FIBRES POLYESTER (POLYETHYLENE TEREPHTALATE). (CF DESSIN DANS BOPI) X H, CL, BR, NO, CH, CH, CHO, CHO, CF, ESTER D'ACIDE SULFONIQUE, SULFAMOYLE EVENTUELLEMENT SUBSTITUE. YH, CL, BR; ZH, CH-CO, CN OU CARBAMOYLE EVENTUELLEMENT SUBSTITUE; RH, ALKYLE EN C-C RENFERMANT O ET EVENTUELLEMENT SUBSTITUE PAR ARYLE, PHENYL-(C-C-ALKYLE), ARYLVINYLE OU RESTE DE FORMULE (CH) COOR; RH, ALKYLE EN C-C, OH OU AMINO, RH, ALKYLE EN C-C EVENTUELLEMENT SUBSTITUE PAR ALCOXY EN C-C OU PHENYLE; M0 A 5; RH, ALKYLE EN C-C, ARALKYLE, CYCLOALKYLE OU ARYLE. THESE COLORANTS ARE REPRESENTED BY FORMULA I BELOW; TO PREPARE THEM, A DIAZOIC COMPOUND OF AMINES OF FORMULA II IS COPULATED WITH A COMPOUND OF FORMULA III. THEY ARE USED FOR DYING SYNTHETIC FIBERS, IN PARTICULAR POLYESTER FIBERS (POLYETHYLENE TEREPHTHALATE). (CF DRAWING IN BOPI) X H, CL, BR, NO, CH, CH, CHO, CHO, CF, SULPHONIC ACID ESTER, SULFAMOYL POSSIBLE SUBSTITUTED. YH, CL, BR; ZH, CH-CO, CN OR POSSIBLE SUBSTITUTE CARBAMOYL; RH, C-C ALKYL CONTAINING O AND POSSIBLY SUBSTITUTED BY ARYL, PHENYL- (C-C-ALKYL), ARYLVINYL OR REMAINDER OF FORMULA (CH) COOR; RH, C-C ALKYL, OH OR AMINO, RH, C-C ALKYL POSSIBLY SUBSTITUTED BY C-C ALCOXY OR PHENYL; M0 A 5; RH, C-C ALKYL, ARALKYL, CYCLOALKYL OR ARYL.

Hair dye composition

PROCESS FOR THE MANUFACTURE OF HALOGEN 2 HYDROXY PYRIDONE - (2)

BASIC AZOIC COLORANTS AND THEIR

Water-insoluble monoazo dyestuffs containing hydroxypyridone residues

1384090 Disperse monoazo dyes BAYER AG 14 Dec 1972 [15 Dec 1971] 57713/72 Heading C4P New monoazo dyes, free from SO 3 H and COOH groups, of formula wherein D is a diazo component radical, R is H or an alkyl, aralkyl, cycloalkyl or aryl group X is CN or an optionally substituted carbamoyl or carboxylic ester group and A is H or an alkyl, aralkyl or acyl group are prepared by azo coupling with optional alkylation, aralkylation or cylation when A is H. The dyes are used to dye and print polyolefin, polyvinyl, cellulose ester and, in particular, polyester fabrics in yellow shades.

Basic azo compounds, their production and use

Reactive monoazo dyestuffs containing 3-azo-2-hydroxy-pyrid-6- -one residues

1348641 Reactive monoazo dyes IMPERIAL CHEMICAL INDUSTRIES Ltd 30 June 1971 [27 July 1970] 36199/70 Addition to 1271226 Heading C4P Reactive monoazo dyes of formula wherein Z is H or C 1-4 alkyl, R is a monosulphonaphthyl radical and n is 1 or 2 are prepared by successive condensation reactions of an appropriate amino-azo dye, with cyanuric chloride and a mono-sulpho-naphthylamine. They are used to colour cellulose materials by reactive dyeing processes in greenish-yellow shades.

MONOAZO DYES

Patent FR2083689A1

Process for the preparation of 2,3-pyridinediol.

Patent FR2163674B1

Preparation of dispersible azo dyestuff compositions by azo coupling

1426053 Azo dyes IMPERIAL CHEMICAL INDUSTRIES Ltd 27 Feb 1973 [15 March 1972 21 Nov 1972] 12084/72 and 53694/72 Heading C4P [Also in Division D1] Dispensible azo dyestuff compositions are prepared by coupling, in the presence of 20 to 500% of the theoretical weight of the dyestuff of an anionic dispensing agent, an aqueous solution of a diazonium salt obtained by diazotisation of an amine free from water-solubilizing groups with an aqueous solution, suspension or emulsion of a coupling component free from water-solubilizing groups, if necessary adding further anionic dispensing agent until the amount is at least 100% of the theoretical weight of dyestuff and drying the suspension obtained. The suspension is preferably milled before drying. Diethylene glycol, glycol or urea may be added as humectants or antifreeze agents. The granular products are dispersed in water and the dispersions used to dye cellulose acetate, polyester and synthetic polyamide fibres.