Hoechst Aktiengesellschaft

Cassella Aktiengesellschaft

Rudolf Schickfluss

Manfred Schneider

Walter Birke

Franz Schon

Willi Steckelberg

Reinhard Hahnle

Wolfgang Teige

Karl Sommer

Claus Schuster

Ulrich Buhler

Manfred Hahnke

Konrad Opitz

Ernst Hoyer

Reinhard Kuhn

Rudolf Lowenfeld

Walter Deucker

Uwe Kosubek

Dieter Cornelius

Disperse Blue 56 is an important blue dyestuff for dyeing PES fibers at the boil or under high-temperature conditions. This anthraquinonoid compound Disperse Blue 56, in addition to its advantages (high light fastness, pH/reduction insensitivity, purity of hue), has some technical disadvantages (poor leveling properties, pronounced staining of adjacent fiber, metameric red shift). By combining a plurality of blue disperse azo dyestuffs having selected structural features in the form of mixtures or mix-crystals it is possible to match the advantages of Disperse Blue 56 while substantially avoiding its disadvantages at the same time. These azo dyestuffs are based on coupling products of diazotized 2,6-substituted 4-nitroanilines with substituted N,N-dialkylanilines.

Mixtures of blue disperse azo dyestuffs for dyeing synthetic fibers

Process for preparing ring-substituted N-alkylanilines of the formula (1) ##STR1## in which R.sub.1 and R.sub.2 each denote methyl or ethyl, in a single vessel, which comprises acylating m-nitroaniline in an excess of an aliphatic carbonyl compound of the formula (2) ##STR2## in which R.sub.1 is as defined above, with an acylating agent which contains the --CO--R.sub.2 acyl radical--which is transferred-- and reductively alkylating the resulting compound of the formula (3) ##STR3## in which R.sub.2 is as defined above, at temperatures of 120.degree.-160.degree. C. under a hydrogen pressure of 20-150 bar without intermediate isolation through the presence of an acid reaction promoter and of a nickel catalyst.

Single-vessel process for preparing ring-substituted n-alkylanilines

A dyeing-stable modification (.beta.-modification) of the dyestuff of the formula (I) ##STR1## which has the X-ray diffraction diagram shown in FIG. 1 and having the characteristic reflections at the following glancing angles and relative intensities:

Dyeing-stable monoazo dyestuff, a process for its preparation, and its

Transfer printing supports impregnated or printed with a formulation containing a dyestuff of the formula I ##STR1## in which R.sup.1 is alkyl having from 1 to 4 carbon atoms, R.sup.2 is hydrogen or has the meaning of R.sup.1, R.sup.3 is methyl, methoxy or ethoxy, and R.sup.4 is hydrogen, methyl, methoxy or ethoxy, or containing mixtures of such dyestuffs, a process for the manufacture of these supports, which comprises impregnating or printing the support material with formulations containing a dyestuff of the formula I or mixtures of such dyestuffs, and the use of these supports for the dyeing and printing of flat web or sheet structures of synthetic or natural materials according to the heat transfer printing process.

Transfer printing support, process for the manufacture thereof, with

Transfer-printing supports, which are impregnated or printed with a formulation containing a mixture of a blue disperse dyestuff which sublimes readily and has the formula ##STR1## in which X is hydrogen or halogen, R, R.sup.1 and R.sup.2 denote alkyl with 1 to 4 carbon atoms and R.sup.3 denotes hydrogen or alkyl with 1 to 4 carbon atoms, and yellow to red disperse dyestuffs which sublime readily, give deep and fast black dyeings on polyester materials and polyester mixed materials by the heat transfer-printing process.

Transfer-printing support

An azo dyestuff of the formula ##STR1## wherein R is linear alkyl having 2 to 4 carbon atoms and R' is linear alkyl having 3 to 5 carbon atoms and isopropyl.

Water-insoluble azo dyestuffs, their manufacture and their use

The invention relates to a novel crystallographic modification ('.beta.-modification') being stable under dyeing conditions of the dyestuff of the formula ##STR1## which is characterized by an X-ray diffraction pattern as shown in FIG. 1 with characteristic reflexes at the following glance angles .theta. (CuK.sub..alpha. radiation) with the relative intensities:

Monoazo dyestuff being stable under dyeing conditions; its manufacture

Water-insoluble azlactone dyestuffs of the formula ##STR1## wherein A represents phenyl, chlorophenyl, bromophenyl, lower alkyl-phenylene, lower alkoxy-phenylene or pyridyl, B represents phenyl, chlorophenyl, lower alkyl-phenylene, lower alkoxy-phenyl, di(lower alkyl) amino-phenylene, cyano-phenyl, ##STR2## acetylamino-phenylene, nitro-phenyl, methylenedioxyphenyl, naphthyl, furyl, thienyl, pyrollyl, N-lower alkyl-pyrollyl, pyridyl or indolyl, and n stands for the integer 0 or 1, said dyestuffs being suitable--alone or in mixture with one another or in mixture with other dyestuffs--for the dyeing or printing of synthetic fibrous materials, such as fibers of cellulose di, 21/2- or triacetate, polyamides or particularly of polyesters, such as polyethylene terephthalate.

Water-insoluble azlactone dyestuffs, processes for their preparation and

A process for the dyeing or printing of a hydrophobic organic fibrous material containing or consisting of polyester, wherein

Process for the dyeing and printing of hydrophobic synthetic organic

Process for the dyeing of a water-insoluble thermoplastic polymer or polycondensate in mass, which comprises adding to the said thermoplastic material before the final molding thereof, an azlactone dyestuff of the formula (1) ##STR1## in which A and B each represents phenyl, lower alkyl-phenyl, lower alkoxy-phenyl, chlorophenyl, nitrophenyl, cyanophenyl, ##STR2## METHYLENE-DIOXY-PHENYLENE OR NAPHTHYL, A and B being identical or different, D represents phenylene, lower alkyl-phenylene, di-lower alkoxy-phenylene, monochlorophenylene, dichlorophenylene, biphenylene or naphthylene, and n represents the integer 0 or 1, or a mixture of dyestuffs of the said formula (1), the dyeings so obtained representing brilliant yellow dyeings of high tinctorial strength being distinguished by very good fastness to light, rubbing and ironing, and, particularly, by an outstanding stability toward heat.

Process for the dyeing of water-insoluble thermoplastic polymers and

Process for the dyeing of a water-insoluble thermoplastic polymer or polycondensate in mass, which comprises adding to the said thermoplastic material before the final molding thereof an azlactone dyestuff of the formula (1) ##STR1## in which A and B each represents naphthyl, phenyl, chlorophenyl, bromophenyl, lower alkyl-phenyl, lower alkoxyphenyl, nitrophenyl, ##STR2## CYANOPHENYL, DICHLOROPHENYL, CHLORO-LOWER ALKYL-PHENYL, NITRO-LOWER ALKYL-PHENYL, CHLORO-NITROPHENYL, A and B being identical or different, D represents naphthylene, phenylene, monochlorophenylene, dichlorophenylene or di-lower alkoxyphenylene, or with a mixture of dyestuffs of the said formula (1), the dyeings so obtained representing brilliant yellow dyeings of high tinctorial strength being distinguished by very good fastness to light, rubbing and ironing and, particularly, an outstanding stability toward heat.

Process for the manufacture of 1-(N-.beta.-cyanethylamino)-3-acylaminobenzenes of the formula (1) ##STR1## in which R.sub.1 represents hydrogen, methyl or alkoxy of 1 to 4 carbon atoms, R.sub.2 represents hydrogen, alkyl from 1 to 3 carbon atoms or phenyl, R.sub.3 represents hydrogen or alkyl from 1 to 3 carbon atoms, and n represents the integer 0 or 1, which comprises reacting 1 mole of an amino of the formula (2) ##STR2## in which R.sub.1, R.sub.2 and R.sub.3 are defined as above, with 1 to 1.75 moles of acrylonitrile between 70.degree. and 150.degree. C in water with the addition of 1 to 30% by weight of an organic carboxylic acid or carbonic acid, and oxethylating the compound at the said formula (1) obtained, if n stands for the integer 0, without or after isolation, with 1 to 10 moles of ethylene oxide between 50.degree. and 100.degree. C.

Process for preparing 1-(N-.beta.-cyanethylaminol-3-acylaminobenzenes

A process for the continuous dyeing of synthetic fibrous materials from organic solvents, which comprises impregnating the said fibrous materials with organic dyebaths containing at least one dyestuff of the formula (1) ##SPC1## In which R represents a secondary or tertiary amino group of the formula (2) ##EQU1## in which R.sub.4, R.sub.5 each represents, straight chain or branched alkyl, hydroxyalkyl, lower alkyl --COO-- lower alkylene, and R.sub.4 additionally represents hydrogen lower alkyl --o-- lower alkylene, or R.sub.4 and R.sub.5 represent together with the nitrogen atom the heterocyclic ring ##EQU2## R.sub.1 and R.sub.1 ' each represents hydrogen, chlorine, bromine, lower alkyl, lower alkoxy, nitro or --SO.sub.2 -- lower alkyl, R.sub.2 and R.sub.3 each represents hydrogen, lower alkyl, cyano-lower alkylene, hydroxy- lower alkylene, lower alkylene ##EQU3## lower alkyl, lower alkylene LOWER ALKYL, ##EQU4## lower alkylene-phenyl or phenyl, X represents hydrogen, chlorine, bromine, lower alkyl or lower alkoxy, Y represents hydrogen, chlorine, bromine, lower alkyl, lower alkoxy or acylamino, and subsequently fixing the applied dyestuffs by a heat treatment.

Process for dyeing synthetic fiber materials

A process for the continuous dyeing of textile material containing or consisting of synthetic fibers from organic solvents, which comprises impregnating the said textile materials with an organic dyebath containing at least one dyestuff of the formula

Process for the dyeing of synthetic fiber materials from organic solvents

A process for the continuous dyeing of textile materials containing or consisting of synthetic fibrous materials from organic solvents, which comprises impregnating the said textile materials with an organic dyebath containing at least one dyestuff of the formula ##SPC1## In which the phenyl radical A is unsubstituted or substituted by 1 to 3 substituents of the group consisting of halogen, nitro, cyano, trifluoromethyl, lower alkyl, lower alkoxy and lower alkoxy-lower alkylene--O--, B represents naphthylene or ##SPC2## R.sub.2, r.sub.3, r.sub.4 and R.sub.5 each represent hydrogen, halogen, lower alkyl, lower alkoxy or lower alkoxy-lower alkylene--O--, and R.sub.1 stands for a linear or branched alkylcarbonyl of at most 18 carbon atoms, ##SPC3## ##SPC4## ##SPC5## ##SPC6## And an organic solvent, and fixing the dyestuffs by submitting the impregnated materials to a heat treatment.

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Kelkheim, Germany

Rudolf Schickfluss