Monoazo disperse dyes from selected (aromatic amino)propionates or selected (aromatic amino)butyrates

Abstract

The disperse dyes of formula I ##STR1## wherein the symbols D, K, R.sub.3-5, R.sub.10, m, z, n and Y possess the significances given in claim 1, are eminently suitable for dyeing or printing hydrophobic, fully or semi-synthetic, organic fiber materials.

Description

The invention relates to the disperse dyes of the general formula I ##STR2## wherein D signifies a diazo component which is usual with disperse dyes,

K signifies an aromatic radical of formula ##STR3## R.sub.1 signifies hydrogen, chlorine, C.sub.1-2 -alkyl, C.sub.1-2 -alkoxy or acylamino, R.sub.2 signifies hydrogen, C.sub.1-4 -alkoxy, C.sub.1-2 -alkoxyethoxy, chlorine, bromine, or together with R.sub.3 signifies a group of formula --*CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2 -- (*bonded to the nucleus), R.sub.3 signifies hydrogen, C.sub.1-6 -alkyl, C.sub.3-4 -alkenyl, chloro- or bromo-C.sub.3-4 -alkenyl, C.sub.3-4 -alkinyl, phenyl-C.sub.1-3 -alkyl, C.sub.1-4 -alkoxycarbonyl-C.sub.1-3 -alkyl, C.sub.3-4 -alkenyloxycarbonyl-C.sub.1-3 -alkyl, C.sub.3-4 -alkinyloxycarbonyl-C.sub.1-3 -alkyl, phenoxy-C.sub.2-4 -alkyl; C.sub.2-4 -alkyl substituted by halogen, cyano, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylcarbonyloxy or C.sub.1-4 -alkoxycarbonyloxy; or a group of formula --CH.sub.2 --CH(R.sub.8)CH.sub.2 --R.sub.9, R.sub.4 signifies hydrogen, phenyl or C.sub.1-2 -alkyl, R.sub.5 signifies a radical of formula ##STR4## R.sub.6 signifies hydrogen or hydroxyl, R.sub.7 signifies hydrogen or C.sub.1-4 -alkyl, R.sub.8 signifies hydroxyl, C.sub.1-4 -alkylcarbonyloxy or C.sub.1-4 -alkoxycarbonyloxy, R.sub.9 signifies chlorine, C.sub.1-4 -alkoxy, phenoxy, allyloxy or C.sub.1-4 -alkylcarbonyloxy, R.sub.10 signifies hydrogen or C.sub.1-4 -alkyl, Y signifies C.sub.2-3 -alkylene, m and z independently signify zero or 1 and n signifies a number from 1 to 5, with the proviso that, if K is a radical of formula b or c, R.sub.3 only signifies hydrogen

One group of preferred dyestuffs of formula I corresponds to the general formula Ia ##STR5## wherein D.sub.1 is 3-phenyl-1,2,4-thiadiazolyl or corresponds to one of the following formulae: ##STR6## wherein a signifies hydrogen, chlorine, bromine, cyano, nitro-, C.sub.1-4 -alkoxycarbonyl, C.sub.1-3 -alkylsulphonyl, preferably hydrogen, chlorine, cyano or nitro,

b signifies chlorine, bromine, nitro, methyl, C.sub.1-2 -alkylsulphonyl, C.sub.1-4 -alkylcarbonyl, aminosulphonyl, mono- or di-C.sub.1-4 -alkylaminosulphonyl, phenylaminosulphonyl, C.sub.1-4 -alkoxycarbonyl, aminocarbonyl, mono- or di-C.sub.1-4 -alkylaminocarbonyl, phenylaminocarbonyl, phenylazo, benzyloxycarbonyl, tetrahydrofurfuryl-2-oxycarbonyl, C.sub.3-4 -alkenyloxycarbonyl, C.sub.3-4 -alkinyloxycarbonyl or phenoxycarbonyl, c signifies hydrogen or chlorine, or if d is hydrogen, also thiocyano, d signifies hydrogen, chlorine, bromine or cyano, e signifies nitro, C.sub.1-4 -alkylcarbonyl, C.sub.1-4 -alkoxycarbonyl, cyano, aminocarbonyl, mono- or di-C.sub.1-4 -alkylaminocarbonyl, f signifies hydrogen, chlorine, bromine, C.sub.1-2 -alkyl or phenyl, g signifies nitro, cyano, formyl, dicyanovinyl or a group of formula --CH.dbd.CH--NO.sub.2, --CH.dbd.C(CN)CO--OC.sub.1-4 -alkyl, H.sub.5 C.sub.6 --N.dbd.N-- or 3- or 4-NO.sub.2 --C.sub.6 H.sub.4 --N.dbd.N--, h signifies cyano or C.sub.1-4 -alkoxycarbonyl, i signifies C.sub.1-4 -alkyl or phenyl, j signifies --CN, --CH.dbd.CH.sub.2 or phenyl, k signifies C.sub.1-4 -alkyl, l signifies hydrogen, chlorine, bromine, cyano, thiocyano, nitro, C.sub.1-4 -alkoxycarbonyl or di-C.sub.1-4 -alkylaminosulphonyl, p signifies hydrogen, chlorine or bromine and q signifies C.sub.1-4 -alkyl, C.sub.1-4 -alkoxycarbonyl-C.sub.1-4 -alkylene or C.sub.1-4 -alkylene-COOCH.sub.2 CF.sub.3, whereby the phenyl nuclei of these substituents may bear one or two substituents from the series chlorine, bromine, methyl or C.sub.1-2 -alkoxy, R.sub.1 ' signifies hydrogen, C.sub.1-2 -akyl, chlorine or acylamino, R.sub.2 ' signifies hydrogen, chlorine, C.sub.1-2 -alkoxy, C.sub.1-2 -alkoxyethoxy, or with R.sub.3, a group of formula --CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2 --, R.sub.3 and R.sub.5 have the significances given above, R.sub.4 ' and R.sub.10 ' independently signify hydrogen or C.sub.1-2 -alkyl and Y.sub.1 signifies a group of formula --CH.sub.2 CH.sub.2 -- or --CH(CH.sub.3)CH.sub.2 -- m and z independently signify zero or 1 and n signifies a number from 1 to 5.

Particularly preferred disperse dyes correspond to formula Ib ##STR7## wherein D.sub.2 signifies the radical of a diazo component from the series 2,6-dicyano-4-chloro-, -4-bromo-, -4-methyl- or -4-nitrophenyl, 2,4-dinitro-6-chloro-, -6-bromo- or -6-cyanophenyl, 2-chloro- or 2-bromo-4-nitro-6-cyanophenyl, 2,4-dinitrophenyl, 2,6-dichloro- or 2,6-dibromo-4-nitrophenyl, 2-chloro-4-nitro-6-bromophenyl, 2-chloro-, 2-bromo- or 2-cyano-4-nitrophenyl, 2,4-dinitro-5-chlorophenyl or -5-thiocyanophenyl, 2,4-dinitro-5,6-dichlorophenyl, 2,5-dichloro-4-nitrophenyl, 4-nitrophenyl, 4-phenylazophenyl, 4-C.sub.3-4 -alkenyloxycarbonylphenyl, 4-C.sub.3-4 -alkinyloxycarbonylphenyl, 4-C.sub.1-4 -alkoxycarbonylphenyl, 2-C.sub.1-4 -alkoxycarbonyl-4-nitrophenyl, 4-phenoxycarbonylphenyl, 4-benzyloxycarbonylphenyl, 4-(tetrahydrofurfuryl-2'-oxycarbonyl)-phenyl, 3,5-dicyano-4-chloro-thienyl-2, 3,5-dicyano-thienyl-2, 3-cyano-5-nitro-thienyl-2, 3-acetyl-5-nitro-thienyl-2, 3,5-dinitro-thienyl-2, 3-(C.sub.1-4 -alkoxycarbonyl)-5-nitro-thienyl-2, 5-phenylazo-3-cyanothienyl-2, 5-phenylazo-3-cyano-4-methyl-thienyl-2, 5-nitro-thiazolyl-2, 5-nitrobenzisothiazolyl-3, 3-methyl-4-cyano-isothiazolyl-5, 3-phenyl-1,2,4-thiadiazolyl-2, 5-(C.sub.1-2 -alkylmercapto)-1,3,4-thiadiazolyl-2, 3-C.sub.1-2 -alkoxycarbonylethylmercapto-1,2,4-thiadiazolyl-5, 1-cyanomethyl-4,5-dicyano-imidazolyl-2, 6-nitrobenzothiazolyl-2, 5-nitrobenzothiazolyl-2, 6-thiocyanobenzothiazolyl-2, 6-chlorobenzothiazolyl-2, (5),6,(7)-dichlorobenzothiazolyl-2, phthalidyl-5 or of formula ##STR8## in which B signifies oxygen or a group of formula ##STR9## and the symbols R.sub.1 ', R.sub.2 ', R.sub.3, R.sub.4 ', R.sub.5, R.sub.10 ', m, n and Y.sub.1 are defined as above.

Furthermore, particular preference is given to the disperse dyes of formula Ib, wherein

D.sub.2 signifies the radical of a diazo component from the series 2,6-dicyano-4-chloro, -4-bromo, -4-methyl or -4-nitro-phenyl, 2,4-dinitro-6-chloro-, -6-bromo- or -6-cyanophenyl, 2-chloro- or 2-bromo-4-nitro-6-cyanophenyl, 2,4-dinitrophenyl, 2,6-dichloro- or 2,6-dibromo-4-nitrophenyl, 2-chloro-4-nitro-6-bromophenyl, 2-chloro-, 2-bromo- or 2-cyano-4-nitrophenyl, 2,4-dinitro-5-chlorophenyl or -5-thiocyanophenyl, 2,4-dinitro-5,6-dichlorophenyl, 2,5-dichloro-4-nitrophenyl, 4-nitrophenyl, phthalidyl-5, or of formula ##STR10## in which B signifies oxygen or a group of formula ##STR11## and the symbols R.sub.1 ', R.sub.2 ', R.sub.3, R.sub.4 ', R.sub.5, R.sub.10 ', m, n and Y.sub.1 are defined as above.

Furthermore, particular preference is given to the disperse dyes of formula Ib, wherein

D.sub.2 signifies a diazo component from the series 2,4-dinitro-6-chloro-, -6-bromo- or -6-cyanophenyl, 2,4-dinitro-5-chloro- or -5-thiocyanophenyl or 2,4-dinitro-5,6-dichlorophenyl, R.sub.1 ' signifies C.sub.1-2 -alkylcarbonylamino, R.sub.2 ' signifies C.sub.1-2 -alkoxy or C.sub.1-2 -alkoxyethoxy, R.sub.3 signifies hydrogen, C.sub.1-4 -alkyl, cyanoethyl, C.sub.1-2 -alkoxyethyl, C.sub.3-4 -alkenyl, chlorallyl, C.sub.3-4 -alkinyl, C.sub.1-2 -alkoxycarbonylmethyl, allyloxycarbonylmethyl or propargyloxycarbonylmethyl, R.sub.4 ' signifies hydrogen or methyl, R.sub.5 signifies a radical of formula ##STR12## R.sub.10 ' signifies hydrogen or methyl, Y.sub.1 signifies a group of formula --CH.sub.2 CH.sub.2 -- or --CH(CH.sub.3)CH.sub.2 -- m signifies nill or 1, and n signifies a number from 1 to 5.

Also preferred are the disperse dyes of formula Ib, wherein

D.sub.2 signifies 2,4-dinitro-6-chloro- or -6-bromophenyl, R.sub.1 ' signifies C.sub.1-2 -alkylcarbonylamino, R.sub.2 ' signifies methoxy or ethoxy, R.sub.3 signifies hydrogen, allyl, chlorallyl or propargyl, R.sub.5 signifies a radical of formula ##STR13## R.sub.10 ' signifies hydrogen or methyl, Y.sub.1 signifies 1,2-ethylene, m signifies zero or 1, and n signifies a number from 1 to 5.

Further preference is also given to the disperse dyes of formula I, wherein

D signifies a diazo component from the series 4-nitrophenyl, 4-nitro-2-ethylsulphonylphenyl, 4-nitro-2-methylsulphonylphenyl, 4-methoxycarbonylphenyl, phthalidyl-5, 4-ethoxycarbonylphenyl, 2-chloro-4-nitrophenyl, 2,6-dichloro-4-nitrophenyl, 2-bromo-4-nitro-6-chlorophenyl or 2-cyano-4-nitrophenyl, K signifies a radical of formula a R.sub.1 signifies hydrogen, methyl, acylamino or chlorine, R.sub.2 signifies hydrogen, R.sub.3 signifies C.sub.1-4 -alkyl, C.sub.3-4 -alkenyl, chlorallyl, benzyl, cyanoethyl, C.sub.1-2 -alkoxyethyl, C.sub.1-4 -alkylcarbonyloxyethyl, C.sub.1-2 -alkoxycarbonylethyl or C.sub.1-4 -alkoxycarbonyloxyethyl, R.sub.4 and R.sub.10 independently signify hydrogen or C.sub.1-2 -alkyl, R.sub.5 signifies a radical of formula ##STR14## Y signifies a group of formula --CH.sub.2 CH.sub.2 -- or --CH(CH.sub.3)CH.sub.2 -- m and z independently signify zero or 1, and n signifies a number from 1 to 5.

One further group of especially preferred disperse dyes corresponds to formula Ib, wherein

D.sub.2 signifies a diazo component from the series 4-nitrophenyl, 2-chloro-4-nitrophenyl, 2-bromo-4-nitrophenyl, 2,6-dichloro-4-nitrophenyl, 2-chloro-4-nitro-6-bromophenyl, 2-cyano-4-nitrophenyl, R.sub.1 ' signifies hydrogen or methyl, R.sub.2 ' signifies hydrogen, R.sub.3 signifies C.sub.1-4 -alkyl, R.sub.4 ' signifies hydrogen or methyl, R.sub.5 signifies a radical of formula ##STR15## R.sub.10 ' signifies hydrogen, Y.sub.1 signifies 1,2-ethylene, m signifies zero or 1, and n signifies the number 1.

The diazo components may be all mono- to bi-nuclear, carbocyclic or heterocyclic organic radicals of aromatic character, which may bear substituents that are conventional in the case of disperse dyes. Water-solubilizing substituents are excluded in particular, that is especially sulphonic acid groups. The diazo components may also be radicals of monoazo compounds. Examples of diazo components are: phenyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrazolyl, imidazolyl, triazolyl, benzothiazolyl or benzisothiazolyl radicals, which preferably bear substituents.

The substituents on these nuclei may be in particular halogen atoms, especially chlorine, bromine or iodine atoms, nitro, cyano, thiocyano, hydroxyl, alkyl, alkoxy, phenyl, phenoxy and acyl groups, as well as especially also on the thienyl or thiazolyl diazo components, formyl and radicals of formulae --CH.dbd.CH--NO.sub.2, --CH.dbd.C(CN).sub.2 and --CH.dbd.C(CN)acyl.

Preferred acyl groups correspond to formula E--Y-- or E'--Z--, in which

E signifies a hydrocarbon radical which may bear the above-mentioned substituents and/or may contain hetero atoms, preferably an optionally substituted alkyl or phenyl radical, Y signifies a radical --O--CO--, --SO.sub.2 -- or --O--SO.sub.2 --, E' signifies a hydrogen atom or E, Z signifies --CO--, --NE"--CO-- or --NE"--SO.sub.2 -- (E" is only bonded to the nitrogen atom), and E" signifies hydrogen or E.

If not otherwise stated, all the said alkyl and alkoxy groups contain 1 to 8, especially 1 to 4 carbon atoms. They may be straight-chain or branched, and bear as substituents e.g. halogen atoms, preferably fluorine or chlorine atoms, hydroxy, alkoxy, phenyl, phenoxy, cyano, thiocyano, acyl, acyloxy or acylamino groups. The intermediate element Y is preferably a group of formula ##STR16## especially --CH.sub.2 CH.sub.2 --.

All the said phenyl radicals (also phenoxy and phenylazo radicals) may be further substituted, e.g. by halogen atoms (preferably chlorine or bromine atoms), alkyl, alkoxy, nitro, cyano, thiocyano, acyl, acyloxy or acylamino groups.

If not indicated to the contrary, all alkyl, alkylene and alkenyl radicals are straight-chain.

Production of the new dyestuffs of formula I is characterized in that a diazotised amine of formula II

D--NH.sub.2 (II) is coupled with a compound of formula III ##STR17##

Diazotisation and coupling are effected according to generally known methods.

The compounds of formulae II and III are known, or may be easily produced from known compounds according to methods known to a person skilled in the art.

Dyestuffs of formula I in which D corresponds to the formula ##STR18## where a and/or d are a cyano radical, can also be prepared by cyano-exchange from the corresponding halogen substituted dyestuffs, such a method is known to the skilled person.

From an aqueous suspension, the new dyestuffs of formula I are absorbed in an excellent manner on textile material consisting of fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic matter. They are especially suitable for dyeing or printing textile material consisting of linear, aromatic polyesters, as well as cellulose-21/2-acetate and cellulose triacetate.

Dyeing or printing are effected in accordance with known processes, e.g. those described in French Patent Specification no. 1.445.371.

The dyeings obtained have good all-round fastnesses; apart from the good fastness to thermomigration, also notable are the light fastness, thermofixation fastness and pleating fastness, as well as the excellent wet fastness, following thermal fixation (especially the M&S C4A Co domestic wash).

They are also especially suitable for thermo transfer printing processes.

In the following examples, the parts and percentages are by weight. The temperatures are given in degrees celsius.

EXAMPLE 1

16.3 parts of 2-amino-5-nitrobenzonitrile are stirred into 100 parts of cold sulphuric acid (93%) and mixed at 0.degree. to 5.degree. over the course of 30 minutes with 32 parts of nitrosylsulphuric acid (40%). Stirring continues for 3 to 4 hours at 0.degree. to 5.degree. and then the diazonium salt solution obtained is poured whilst stirring into a mixture of 35.2 parts of 3-(N-methyl-N-phenylamino)-propionic acid-2'-N-phthalimidoethylester, 100 parts of glacial acetic acid, 2 parts of amidosulphonic acid, 200 parts of water and 500 parts of ice. The precipitated dyestuff is filtered off, washed with water until free from acid and dried in a vacuum at 60.degree.. The resultant dyestuff corresponds to formula ##STR19##

It dyes polyester fibre material in ruby-red shades with excellent fastness, in particular very good wet fastness after thermal fixing, and is eminently suitable for the modern rapid-dyeing processes, for example the .sup.R Foron-RD process.

.lambda..sub.max. =533 nm (DMF).

EXAMPLE 2

The process is as described in example 1, but the 35.2 parts of 3-(N-methyl-N-phenylamino)-propionic acid-2'-N-phthalimidoethylester are replaced by 42.4 parts of 3-(N-ethyl-N-phenylamino)-propionic acid-(2'-N-phthalimidoethoxycarbonyl)methylester. The resultant dyestuff corresponds to formula ##STR20##

It dyes polyester fibre materials in ruby-red shades with excellent fastnesses, in particular very good wet fastness, after thermal fixing.

.lambda..sub.max. =537 nm (DMF).

EXAMPLE 3

The process is as described in example 1, but the 35.2 parts of 3-(N-methyl-N-phenylamino)-propionic acid-2'-N-phthalimidoethylester are replaced by 38.8 parts of 3-(N-methyl-N-phenylamino)-propionic acid-2'-N-o-sulphobenzimidoethylester. The resultant dyestuff corresponds to formula ##STR21##

It dyes polyester fibre materials in ruby-red shades with excellent fastness, in particular very good wet fastness, after thermal fixing, and is eminently suitable for the modern rapid-dyeing processes, for example the .sup.R Foron-RD process.

.lambda..sub.max. =534 nm (DMF).

EXAMPLE 4

20.7 parts of 1-amino-2,6-dichloro-4-nitrobenzene are stirred into 100 parts of sulphuric acid (93%) and mixed at 30.degree. over the course of one hour with 32 parts of nitrosylsulphuric acid (40%). Stirring is effected for 2-3 hours at 30.degree.-32.degree., and then the diazonium salt solution obtained is added in drops whilst stirring to a mixture of 35.2 parts of 3-(N-methyl-N-phenylamino)-propionic acid-2'-N-phthalimidoethylester, 100 parts of glacial acetic acid, 2 parts of amidosulphonic acid, 200 parts of water and 500 parts of ice. The precipitated dyestuff is filtered off, washed with water until free from acid, and dried in a vacuum at 60.degree.. It corresponds to formula ##STR22## and dyes polyester fibre material in yellow-brown shades with excellent fastness, in particular very good wet fastness, after thermal fixing.

.lambda..sub.max. (DMF)=439 nm.

EXAMPLE 5

21.8 parts of 2-chloro-4,6-dinitroaniline are stirred into 150 parts of 93% sulphuric acid at 15.degree.-20.degree., and mixed over the course of 30 minutes with 32 parts of 40% nitrosylsulphuric acid. The mixture is stirred for 2-3 hours in an ice bath, and the diazonium salt solution is continuously poured into a mixture of 46.1 parts of 3-N-(5"-acetylamino-2"-methoxyphenylamino)-propionic acid-2'-N-o-sulphobenzimidoethylester, 100 parts of glacial acetic acid and 300 parts of ice/water. The precipitated dyestuff is filtered off, washed with water until free from acid, and dried in a vacuum at 60.degree.. The dyestuff obtained, with .lambda..sub.max. =598 nm (DMF), corresponds to formula ##STR23## and dyes polyester materials, resp. polyester/cotton mixed fabric, in marine-blue shades with excellent fastness, in particular very good wet fastness, after thermal fixing.

EXAMPLE 6

20.8 parts of 2-cyano-4,6-dinitroaniline are stirred into 150 parts of sulphuric acid (93%) at 0.degree. to 5.degree. and mixed over the course of 30 minutes with 32 parts of nitrosylsulphuric acid (40%). Stirring continues for 2 to 3 hours at 0.degree. to 5.degree. and then the diazonium salt solution obtained is poured whilst stirring into a mixture of 39.6 parts of 3-[N-methyl-N-(5"-methyl-2"-methoxyphenyl)amino]-propionic acid-2'-N-phthalimidoethylester, 100 parts of glacial acetic acid and 300 parts of ice/water. The precipitated dyestuff is filtered off, washed with water until free from acid and dried in a vacuum at 60.degree.. The resultant dyestuff having a .lambda..sub.max =613 nm (DMF) corresponds to formula ##STR24##

It dyes polyester fibre material in blue shades with excellent fastness, in particular very good wet fastness after thermal fixing, and is eminently suitable for the modern rapid-dyeing processes, for example the .sup.R Foron-RD process.

EXAMPLE 7

20.8 parts of 2-cyano4,6-dinitroaniline are stirred into 150 parts of sulphuric acid (93%) at 0.degree. to 5.degree. and mixed over the course of 30 minutes with 32 parts of nitrosylsulphuric acid (40%). Stirring continues for 2 to 3 hours at 0.degree. to 5.degree. and then the diazonium salt solution obtained is poured whilst stirring into a mixture of 45.2 parts of 3-[N-ethyl-N-(3'-methylphenyl)amino]-propionic acid-(3"-N-phthalimido-n-propoxycarbonyl)-methylester, 100 parts of glacial acetic acid, and 300 parts of ice/water. The precipitated dyestuff is filtered off, washed with water until free from acid and dried in a vacuum at 60.degree.. The resultant dyestuff having a .lambda..sub.max =590 nm (DMF) corresponds to formula ##STR25##

It dyes polyester fibre material in ruby-red shades with excellent fastness, in particular very good wet fastness after thermal fixing, and is eminently suitable for the modern rapid-dyeing processes, for example the .sup.R Foron-RD process.

Analogously to the method of Example 1 by using the corresponding starting materials further compounds of formula I may be obtained.

These compounds correspond to the formulae given hereinbelow, for which the particular variants are listed in the following tables. They dye polyester fibers in the indicated shades with excellent fastnesses, in particular very good wet fastness after thermal fixing. In the following tables "do." signifies ditto, i.e. same as the previous entry, PES stands for polyester fibres and DK stands for diazo component radical.

The dyestuffs of the following Table I correspond to formula ##STR26##

TABLE 1__________________________________________________________________________exp. Shadeno. DK R.sub.1 R.sub.2 R.sub.3 on__________________________________________________________________________ PES 8 H H C.sub.2 H.sub.5 ruby 9 " H H CH.sub.3 "10 " H H CH.sub.2 CH.sub.2 CN red11 ##STR27## H H CH.sub.3 "12 ##STR28## H H C.sub.2 H.sub.4 CN scarlet13 ##STR29## H H " "14 ##STR30## NHCOCH.sub.3 H " red15 " " Cl H scarlet16 ##STR31## " " H ruby17 ##STR32## H H CH.sub.3 "18 ##STR33## H H CH.sub.2 CHCH.sub.2 yellow-brown19 ##STR34## H H C.sub.4 H.sub.9 "20 ##STR35## H H CH.sub.2 CHCH.sub.2 yellow-brown21 ##STR36## H H " "22 ##STR37## NHCOCH.sub.3 H C.sub.2 H.sub.5 bluish-violet23 ##STR38## CH.sub.3 H C.sub.4 H.sub.9 reddish blue24 " NHCOCH.sub.3 H C.sub.3 H.sub.7 blue25 " NHCOC.sub.2 H.sub.5 H " "26 " NHCOCH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) "27 ##STR39## CH.sub.3 H C.sub.2 H.sub.5 scarlet28 ##STR40## NHCOC.sub.2 H.sub.5 H C.sub.2 H.sub.5 bluish red29 " NHSO.sub.2 CH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) red30 ##STR41## NHCOC.sub.2 H.sub.5 H " ruby31 ##STR42## CH.sub.3 H C.sub.4 H.sub.9 bluish violet32 ##STR43## H H CH.sub.3 bluish red33 " CH.sub.3 H C.sub.2 H.sub.5 violet34 ##STR44## NHCOCH.sub.3 H C.sub.2 H.sub.4 CN bluish red35 ##STR45## CH.sub.3 H C.sub.2 H.sub.5 scarlet36 " NHCOC.sub.2 H.sub.5 H " red37 ##STR46## H H C.sub.2 H.sub.5 scarlet38 " CH.sub.3 H " red39 " NHCOCH.sub.3 H " ruby40 " " H C.sub.2 H.sub.4 CN red41 ##STR47## CH.sub.3 H C.sub.4 H.sub.9 bluish red42 ##STR48## " H C.sub.2 H.sub.5 dark blue43 ##STR49## NHCOCH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) greenish blue44 ##STR50## H H C.sub.2 H.sub.5 blue45 " CH.sub.3 H " greenish blue46 " H H C.sub.2 H.sub.4 OCOCH.sub.3 reddish blue47 " NHCOCH.sub.3 H C.sub.2 H.sub.5 bluish green48 ##STR51## CH.sub.3 H C.sub.4 H.sub.9 reddish blue49 ##STR52## " H C.sub.2 H.sub.5 reddish navy blue50 ##STR53## H H " dark blue51 ##STR54## H H C.sub.2 H.sub.5 dark blue52 ##STR55## H H C.sub.2 H.sub.5 greenish navy blue53 ##STR56## NHCOCH.sub.3 H ##STR57## red54 " " H C.sub.2 H.sub.5 bluish red55 ##STR58## H H C.sub.2 H.sub.5 violet56 ##STR59## H H C.sub.2 H.sub.4 CN red57 ##STR60## CH.sub.3 H C.sub.2 H.sub.5 violet58 ##STR61## " H CH.sub.3 violet59 ##STR62## CH.sub.3 H " ruby60 " H H C.sub.2 H.sub.5 red61 ##STR63## NHCOC.sub.2 H.sub.5 H " blue62 " NHCOCH.sub.3 H " "63 " " H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) "64 ##STR64## CH.sub.3 OCH.sub.3 CH.sub.3 bluish violet65 ##STR65## NHCOCH.sub.3 H C.sub.2 H.sub.5 "66 ##STR66## NHCOCH.sub.3 H C.sub.2 H.sub.5 red67 ##STR67## H H CH.sub.3 yellow68 " H H C.sub.2 H.sub.5 "69 ##STR68## H H CH.sub.3 "70 " CH.sub.3 H " "71 ##STR69## " H " "72 " H H " "73 ##STR70## H H " orange74 " H H C.sub.2 H.sub.5 "75 ##STR71## H H CH.sub.2 CH.sub.2 OCOOCH.sub.3 orange76 " CH.sub.3 H CH.sub.3 red77 ##STR72## H H " "78 ##STR73## H H CH.sub.2 CHCH.sub.2 "79 ##STR74## H H CH.sub.2 CH.sub.2 OCOCH.sub.3 ruby80 " H H CH.sub.2 CH.sub.2 OCOOCH.sub.3 "81 ##STR75## H H C.sub.2 H.sub.5 "82 ##STR76## H H C.sub.2 H.sub.5 ruby83 ##STR77## H H " yellow-brown__________________________________________________________________________

The dyestuffs of the following Table 2 correspond to the formula

TABLE 2__________________________________________________________________________ ##STR78## Shadeexp. no. DK R.sub.1 R.sub.2 R.sub.3 on PES__________________________________________________________________________84 ##STR79## H H C.sub.2 H.sub.5 ruby85 ##STR80## H H C.sub.4 H.sub.9 "86 " H H CH.sub.2 CH.sub.2 CN red87 ##STR81## H H CH.sub.3 "88 ##STR82## H H C.sub.2 H.sub.4 CN scarlet89 ##STR83## H H C.sub.2 H.sub.4 CN scarlet90 ##STR84## NHCOCH.sub.3 H " red91 " " Cl H scarlet92 ##STR85## " " H ruby93 ##STR86## H H C.sub.2 H.sub.5 "94 ##STR87## H H CH.sub.2 CHCH.sub.2 yellow-brown95 ##STR88## H H C.sub.4 H.sub.9 yellow-brown96 ##STR89## H H CH.sub.2 CHCH.sub.2 "97 ##STR90## H H " "98 ##STR91## NHCOCH.sub.3 H C.sub.2 H.sub.5 bluish violet99 ##STR92## CH.sub.3 H C.sub.4 H.sub.9 reddish blue100 ##STR93## NHCOCH.sub.3 H C.sub.3 H.sub.7 blue101 " NHCOC.sub.2 H.sub.5 " "102 " NHCOCH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) "103 ##STR94## CH.sub.3 H C.sub.2 H.sub.5 scarlet104 ##STR95## NHCOC.sub.2 H.sub.5 H C.sub.2 H.sub.5 bluish red105 " NHSO.sub.2 CH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) red106 ##STR96## NHCOC.sub.2 H.sub.5 H " ruby107 ##STR97## CH.sub.3 H C.sub.4 H.sub.9 bluish violet108 ##STR98## H H CH.sub.3 bluish red109 " CH.sub.3 H C.sub.2 H.sub.5 violet110 " NHCOCH.sub.3 H C.sub.2 H.sub.4 CN bluish red111 ##STR99## CH.sub.3 H C.sub.2 H.sub.5 scarlet112 " NHCOC.sub.2 H.sub.5 H " red113 ##STR100## H H C.sub.2 H.sub.5 scarlet114 " CH.sub.3 H " red115 " NHCOCH.sub.3 H " ruby116 " " H C.sub.2 H.sub.4 CN red117 ##STR101## CH.sub.3 H C.sub.4 H.sub.9 bluish red118 ##STR102## CH.sub.3 H C.sub.2 H.sub.5 dark blue119 " NHCOCH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) greenish blue120 ##STR103## H H C.sub.2 H.sub.5 blue121 " CH.sub.3 H " greenish blue122 " H H C.sub.2 H.sub.4 OCOCH.sub.3 reddish blue123 " NHCOCH.sub.3 H C.sub.2 H.sub.5 bluish green124 ##STR104## CH.sub.3 H C.sub.4 H.sub.9 reddish blue125 ##STR105## " H C.sub.2 H.sub.5 reddish navy blue126 ##STR106## H H " dark blue127 ##STR107## H H C.sub.2 H.sub.5 dark blue128 ##STR108## H H C.sub.2 H.sub.5 greenish navy blue129 ##STR109## NHCOCH.sub.3 H ##STR110## red130 " " H C.sub.2 H.sub.5 bluish red131 ##STR111## H H C.sub.2 H.sub.5 violet132 ##STR112## H H C.sub.2 H.sub.4 CN red133 ##STR113## CH.sub.3 H C.sub.2 H.sub.5 violet134 ##STR114## CH.sub.3 H CH.sub.3 violet135 ##STR115## CH H " ruby136 " H H C.sub.2 H.sub.5 red137 ##STR116## NHCOC.sub.2 H.sub.5 H " blue138 ##STR117## NHCOCH.sub.3 H " "139 " " H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) "140 ##STR118## " H " bluish violet141 ##STR119## NHCOCH.sub.3 H C.sub.2 H.sub.5 bluish violet142 ##STR120## " H " red143 ##STR121## H H CH.sub.3 yellow144 " H H C.sub.2 H.sub.5 "145 ##STR122## H H CH.sub.3 "146 " CH.sub.3 H " "147 ##STR123## H H " "148 " H H " "149 ##STR124## H H CH.sub.3 orange150 " H H C.sub.2 H.sub.5 "151 " H H CH.sub.2 CH.sub.2 OCOOCH.sub.3 "152 " CH.sub.3 H CH.sub.3 red153 ##STR125## H H " "154 ##STR126## H H CH.sub.2 CHCH.sub.2 "155 ##STR127## H H CH.sub.2 CH.sub.2 OCOCH.sub.3 ruby156 " H H CH.sub.2 CH.sub.2 OCOOCH.sub.3 "157 ##STR128## H H CH.sub.3 ruby158 ##STR129## H H " "159 ##STR130## H H " yellow brown160 " H H CH.sub.3 "__________________________________________________________________________

The dyestuffs of the following Table 3 correspond to formula

TABLE 3__________________________________________________________________________ ##STR131##exp. Shadeno. DK R.sub.1 R.sub.2 R.sub.3 on PES__________________________________________________________________________161 ##STR132## H H CH.sub.3 ruby162 ##STR133## H H C.sub.4 H.sub.9 "163 " H H CH.sub.2 CH.sub.2 CN red164 ##STR134## H H CH.sub.3 "165 ##STR135## H H C.sub.2 H.sub.4 CN scarlet166 ##STR136## H H C.sub.2 H.sub.4 CN scarlet167 ##STR137## NHCOCH.sub.3 H " red168 " " Cl H scarlet169 ##STR138## " " H ruby170 ##STR139## H H CH.sub.3 "171 ##STR140## H H CH.sub.2 CHCH.sub.2 yellow-brown172 ##STR141## H H C.sub.4 H.sub.9 yellow-brown173 ##STR142## H H CH.sub.2 CHCH.sub.2 "174 ##STR143## H H " "175 ##STR144## NHCOCH.sub.3 H C.sub.2 H.sub.5 bluish violet176 ##STR145## CH.sub.3 H C.sub.4 H.sub.9 reddish blue177 ##STR146## NHCOCH.sub.3 H C.sub.3 H.sub.7 blue178 " NHCOC.sub.2 H.sub.5 H " "179 " NHCOCH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) "180 ##STR147## CH.sub.3 H C.sub.2 H.sub.5 scarlet181 " NHCOC.sub.2 H.sub.5 H " bluish red182 " NHSO.sub.2 CH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) red183 ##STR148## NHCOC.sub.2 H.sub.5 H " ruby184 ##STR149## CH.sub.3 H C.sub.4 H.sub.9 bluish violet185 ##STR150## H H CH.sub.3 bluish red186 " CH.sub.3 H C.sub.2 H.sub.5 violet187 " NHCOCH.sub.3 H C.sub.2 H.sub.4 CN bluish red188 ##STR151## CH.sub.3 H C.sub.2 H.sub.5 scarlet189 " NHCOC.sub.2 H.sub.5 H " red190 ##STR152## H H C.sub.2 H.sub.5 scarlet191 " CH.sub.3 H " red192 " NHCOCH.sub.3 H " ruby193 " " H C.sub.2 H.sub.4 CN red194 ##STR153## CH.sub.3 H C.sub.4 H.sub.9 bluish red195 ##STR154## CH.sub.3 H C.sub.2 H.sub.5 dark blue196 " NHCOCH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) greenish blue197 ##STR155## H H C.sub.2 H.sub.5 blue198 " CH.sub.3 H " greenish blue199 " H H C.sub.2 H.sub.4 OCOCH.sub.3 reddish blue200 " NHCOCH.sub.3 H C.sub.2 H.sub.5 bluish green201 ##STR156## CH.sub.3 H C.sub.4 H.sub.9 reddish blue202 ##STR157## " H C.sub.2 H.sub.5 reddish navy blue203 ##STR158## H H " dark blue204 ##STR159## H H C.sub.2 H.sub.5 dark blue205 ##STR160## H H C.sub.2 H.sub.5 greenish navy blue206 ##STR161## NHCOCH.sub.3 H ##STR162## red207 " " H C.sub.2 H.sub.5 bluish red208 ##STR163## H H C.sub.2 H.sub.5 violet209 ##STR164## H H C.sub.2 H.sub.4 CN red210 ##STR165## CH.sub.3 H C.sub.2 H.sub.5 violet211 ##STR166## CH.sub.3 H CH.sub.3 violet212 ##STR167## CH.sub.3 H " ruby213 " H H C.sub.2 H.sub.5 red214 ##STR168## NHCOC.sub.2 H.sub.5 H " blue215 " NHCOCH.sub.3 H " "216 " " H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) "217 ##STR169## " H " bluish violet218 ##STR170## NHCOCH.sub.3 H C.sub.2 H.sub.5 bluish violet219 ##STR171## " H " red220 ##STR172## H H CH.sub.3 yellow221 " H H C.sub.2 H.sub.5 "222 ##STR173## H H CH.sub.3 "223 " CH.sub.3 H " "224 ##STR174## " H " "225 " H H " "226 ##STR175## H H " orange227 " H H C.sub.2 H.sub.5 "228 " H H CH.sub.2 CH.sub.2 OCOOCH.sub.3 "229 " CH.sub.3 H CH.sub.3 red230 ##STR176## H H " "231 ##STR177## H H CH.sub.2 CHCH.sub.2 "232 ##STR178## H H CH.sub.2 CH.sub.2 OCOCH.sub.3 ruby233 " H H CH.sub.2 CH.sub.2 OCOOCH.sub.3 "234 ##STR179## H H C.sub.2 H.sub.5 ruby235 ##STR180## H H C.sub.3 H.sub.7 "236 ##STR181## H H " yellow-brown237 " H H CH.sub.3 "__________________________________________________________________________

The dyestuffs of the following Table 4 correspond to formula

TABLE 4__________________________________________________________________________ ##STR182##exp. Shadeno. DK R.sub.1 R.sub.2 R.sub.3 on PES__________________________________________________________________________238 ##STR183## H H C.sub.2 H.sub.5 ruby239 ##STR184## H H CH.sub.3 "240 " H H CH.sub.2 CH.sub.2 CN red241 ##STR185## H H CH.sub.3 "242 ##STR186## H H C.sub.2 H.sub.4 CN scarlet243 ##STR187## H H C.sub.2 H.sub.4 CN scarlet244 ##STR188## NHCOCH.sub.3 H " red245 " " Cl H scarlet246 ##STR189## " " H ruby247 ##STR190## H H CH.sub.3 "248 ##STR191## H H CH.sub.2 CHCH.sub.2 yellow-brown249 ##STR192## H H C.sub.4 H.sub.9 yellow-brown250 ##STR193## H H CH.sub.2 CHCH.sub.2 "251 ##STR194## H H " "252 ##STR195## NHCOCH.sub.3 H C.sub.2 H.sub.5 bluish violet253 ##STR196## CH.sub.3 H C.sub.4 H.sub.9 reddish blue254 ##STR197## NHCOCH.sub.3 H C.sub.3 H.sub.7 blue255 " NHCOC.sub.2 H.sub.5 H " "256 " NHCOCH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) "257 ##STR198## CH.sub.3 H C.sub.2 H.sub.5 scarlet258 " NHCOC.sub.2 H.sub.5 H " bluish red259 " NHSO.sub.2 CH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) red260 ##STR199## NHCOC.sub.2 H.sub.5 H " ruby261 ##STR200## CH.sub.3 H C.sub.4 H.sub.9 bluish violet262 ##STR201## H H CH.sub.3 bluish red263 " CH.sub.3 H C.sub.2 H.sub.5 violet264 " NHCOCH.sub.3 H C.sub.2 H.sub.4 CN bluish red265 ##STR202## CH.sub.3 H C.sub.2 H.sub.5 scarlet266 " NHCOC.sub.2 H.sub.5 H " red267 ##STR203## H H C.sub.2 H.sub.5 scarlet268 " CH.sub.3 H " red269 " NHCOCH.sub.3 H " ruby270 " " H C.sub.2 H.sub.4 CN red271 ##STR204## CH.sub.3 H C.sub.4 H.sub.9 bluish red272 ##STR205## " H C.sub.2 H.sub.5 dark blue273 " NHCOCH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) greenish blue274 ##STR206## H H C.sub.2 H.sub.5 blue275 " CH.sub.3 H " greenish blue276 " H H C.sub.2 H.sub.4 OCOCH.sub.3 reddish blue277 " NHCOCH.sub.3 H C.sub.2 H.sub.5 bluish green278 ##STR207## CH.sub.3 H C.sub.4 H.sub.9 reddish blue279 ##STR208## CH.sub.3 H C.sub.2 H.sub.5 reddish navy blue280 ##STR209## H H " dark blue281 ##STR210## H H " "282 ##STR211## H H C.sub.2 H.sub.5 greenish navy blue283 ##STR212## NHCOCH.sub.3 H ##STR213## red284 " " H C.sub.2 H.sub.5 bluish red285 ##STR214## H H C.sub.2 H.sub.5 violet286 ##STR215## H H C.sub.2 H.sub.4 CN red287 ##STR216## CH.sub.3 H C.sub.2 H.sub.5 violet288 " " H CH.sub.3 violet289 ##STR217## CH.sub.3 H " ruby290 " H H C.sub.2 H.sub.5 red291 ##STR218## CH.sub.3 OCH.sub.3 CH.sub.3 blue292 " NHCOCH.sub.3 H " "293 " " H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) "294 ##STR219## NHCOCH.sub.3 H C.sub.2 H.sub.5 /C.sub.3 H.sub.7 (1:1) bluish violet295 ##STR220## " H C.sub.2 H.sub.5 "296 ##STR221## " H " red297 ##STR222## H H CH.sub.3 yellow298 " H H C.sub.2 H.sub.5 "299 ##STR223## H H CH.sub.3 "300 " CH.sub.3 H " "301 ##STR224## CH.sub.3 H CH.sub.3 yellow302 " H H " "303 ##STR225## H H " orange304 " H H C.sub.2 H.sub.5 "305 " H H CH.sub.2 CH.sub.2 OCOOCH.sub.3 "306 " CH.sub.3 H CH.sub.3 red307 ##STR226## H H " "308 ##STR227## H H CH.sub.2 CHCH.sub.2 "309 ##STR228## H H CH.sub.2 CH.sub.2 OCOCH.sub.3 ruby310 ##STR229## H H CH.sub.2 CH.sub.2 OCOOCH.sub.3 ruby311 ##STR230## H H C.sub.2 H.sub.5 "312 ##STR231## H H " "313 ##STR232## H H " yellow-brown314 " H H CH.sub.3 "__________________________________________________________________________ TABLE 5__________________________________________________________________________The dyestuffs of the following Table 5 correspond to the formula ##STR233##exp. no. R.sub.11 R.sub.12 R.sub.3 R.sub.4 R.sub.10 Shade on PES__________________________________________________________________________315 Cl Cl CH.sub.3 H CH.sub.3 yellow-brown316 Cl Cl " CH.sub.3 H "317 Br Br " H CH.sub.3 "318 CN H CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H ruby-red319 " H CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H CH.sub.3 "320 " H CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 CH.sub.3 H "321 " H CH.sub.2 CH.sub.2 OCOOCH.sub.3 H CH.sub.3 bluish red322 " H CH.sub.2 CHCH.sub.2 H " "323 Cl Cl CH.sub.2 CH.sub.3 H " yellow-brown324 CN H ##STR234## CH.sub.3 H ruby-red325 " H CH.sub.3 H CH.sub.3 "326 " H CH.sub.2 CH.sub.2 OCOOC.sub.2 H.sub.5 H " "327 Br Cl CH.sub.3 H " yellow-brown__________________________________________________________________________ TABLE 6__________________________________________________________________________The dyestuffs of the following Table 6 correspond to the formula ##STR235##exp. no. R.sub.11 R.sub.12 R.sub.3 R.sub.4 R.sub.10 Shade on PES__________________________________________________________________________328 Cl Cl CH.sub.3 H CH.sub.3 yellow-brown329 Cl Cl " CH.sub.3 H "330 Br Br " H CH.sub.3 "331 CN H CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H ruby-red332 " H CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H CH.sub.3 "333 " H CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 CH.sub.3 H "334 " H CH.sub.2 CH.sub.2 OCOOCH.sub.3 H CH.sub.3 bluish red335 " H CH.sub.2 CHCH.sub.2 H " "336 Cl Cl CH.sub.2 CH.sub.3 H " yellow-brown337 CN H ##STR236## CH.sub.3 H ruby-red338 " H CH.sub.3 H CH.sub.3 "339 " H CH.sub.2 CH.sub.2 OCOOC.sub.2 H.sub.5 H " "340 Br Cl CH.sub.3 H " yellow-brown__________________________________________________________________________ TABLE 7__________________________________________________________________________The dyestuffs of the following Table 7 correspond to the formula ##STR237##exp. Shade onno. DK R.sub.1 R.sub.2 Y R.sub.3 PES__________________________________________________________________________341 ##STR238## H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 ruby342 ##STR239## H H " " "343 ##STR240## NHCOCH.sub.3 OCH.sub.3 " H navy blue344 ##STR241## " OC.sub.2 H.sub.5 " H "345 ##STR242## CH.sub.3 H CH.sub.2 CH.sub.2 CH.sub.2 C.sub.2 H.sub.5 scarlet-red__________________________________________________________________________ TABLE 8__________________________________________________________________________exp. no. 346 ##STR243## navy blueexp. no. 347 ##STR244## "__________________________________________________________________________ TABLE 9__________________________________________________________________________The dyestuffs of the following Table 9 correspond to the formula ##STR245##exp. Shade onno. DK R.sub.1 R.sub.2 Y R.sub.3 PES__________________________________________________________________________348 ##STR246## H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 ruby349 ##STR247## H H " " "350 ##STR248## NHCOCH.sub.3 OCH.sub.3 " H navy blue351 ##STR249## " OC.sub.2 H.sub.5 " H "352 ##STR250## CH.sub.3 H " C.sub.2 H.sub.5 scarlet-red__________________________________________________________________________ TABLE 10__________________________________________________________________________exp. no. 353 ##STR251## navy blueexp. no. 354 ##STR252## navy blue__________________________________________________________________________ TABLE 11__________________________________________________________________________The dyestuffs of the following Table 11 correspond to formula ##STR253##exp.no. DK R.sub.1 R.sub.2 Y R.sub.3 Shade on PES__________________________________________________________________________355 ##STR254## H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 ruby356 ##STR255## H H ##STR256## CH.sub.3 ruby357 ##STR257## NHCOCH.sub.3 OCH.sub.3 C.sub.3 H.sub.6 H navy blue358 ##STR258## " OC.sub.2 H.sub.5 " H "359 ##STR259## CH.sub.3 H " C.sub.2 H.sub.5 scarlet-red__________________________________________________________________________ TABLE 12__________________________________________________________________________exp. no. 360 ##STR260## navy blueexp. no. 361 ##STR261## navy__________________________________________________________________________ blue TABLE 13__________________________________________________________________________The dyestuffs of Table 13 correspond to formula ##STR262##exp.no. DK R.sub.1 R.sub.2 Y R.sub.3 Shade on PES__________________________________________________________________________362 ##STR263## H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 ruby363 " H H ##STR264## " "364 ##STR265## NHCOCH.sub.3 OCH.sub.3 C.sub.3 H.sub.6 H navy blue365 ##STR266## NHCOCH.sub.3 OC.sub.2 H.sub.5 C.sub.3 H.sub.6 H navy blue366 ##STR267## CH.sub.3 H " C.sub.2 H.sub.5 scarlet-red__________________________________________________________________________ TABLE 14__________________________________________________________________________exp. no. 367 ##STR268## navy blueexp. no. 368 ##STR269## navy blue__________________________________________________________________________ TABLE 15__________________________________________________________________________The dyestuffs of following Table 15 correspond to formula ##STR270##exp.no. M R.sub.12 R.sub.8 R.sub.3 Shade on PES__________________________________________________________________________369 H Br CH.sub.3 H navy blue370 H " C.sub.2 H.sub.5 H "371 H " C.sub.2 H.sub.4 OCH.sub.3 H "372 Cl Cl " H "373 H " C.sub.2 H.sub.4 OCH.sub.3 H "374 H " C.sub.2 H.sub.5 H "375 H " CH.sub.3 C.sub.2 H.sub.5 greenish navy blue376 H " " CH.sub.2 CHCH.sub.2 navy blue377 H Br " CH.sub.2 CHCHCl reddish navy blue378 H Cl " ##STR271## "379 H " " CH.sub.2 C.sub.6 H.sub.5 navy blue380 H " C.sub.2 H.sub.5 CH.sub.2 CHCH.sub.2 "381 H " " CH.sub.2 CHCHCl "382 H " " ##STR272## reddish navy blue383 H Cl CH.sub.3 C.sub.2 H.sub.4 C.sub.6 H.sub.5 greenish navy blue384 H " " C.sub.3 H.sub.6 OC.sub.6 H.sub.5 "385 H H " CHCHCHCl reddish navy blue386 HJ " CH.sub.2 CHCH.sub.2 "387 H CN " " greenish blue388 H " " C.sub.2 H.sub.5 bluish green__________________________________________________________________________ TABLE 16__________________________________________________________________________The dyestuffs of following Table 16 correspond to formula ##STR273##exp.no. M R.sub.12 R.sub.8 R.sub.3 Shade on PES__________________________________________________________________________389 H Br CH.sub.3 H navy blue390 H " C.sub.2 H.sub.5 H "391 H " C.sub.2 H.sub.4 OCH.sub.3 H "392 H Cl CH.sub.3 H "393 Cl Cl " H "394 H " C.sub.2 H.sub.4 OCH.sub.3 H "395 H " C.sub.2 H.sub.5 H "396 H " CH.sub.3 C.sub.2 H.sub.5 greenish navy blue397 H " " CH.sub.2 CHCH.sub.2 navy blue398 H Br " CH.sub.2 CHCHCl reddish navy blue399 H Cl " ##STR274## "400 H " " CH.sub.2 C.sub.6 H.sub.5 navy blue401 H " C.sub.2 H.sub.5 CH.sub.2 CHCH.sub.2 "402 H " " CH.sub.2 CHCHCl "403 H " " ##STR275## reddish navy blue404 H Cl CH.sub.3 C.sub.2 H.sub.4 C.sub.6 H.sub.5 greenish navy blue405 H " " C.sub.3 H.sub.6 OC.sub.6 H.sub.5 "406 H H " CHCHCHCl reddish navy blue407 HJ " CH.sub.2 CHCH.sub.2 "408 H CN " " greenish blue409 H " " C.sub.2 H.sub.5 bluish green__________________________________________________________________________ TABLE 17__________________________________________________________________________The dyestuffs of following Table 17 correspond to formula ##STR276##exp.no. M R.sub.12 R.sub.8 R.sub.3 Shade on PES__________________________________________________________________________410 H Br CH.sub.3 H navy blue411 H " C.sub.2 H.sub.5 H "412 H " C.sub.2 H.sub.4 OCH.sub.3 H "413 H Cl CH.sub.3 H "414 Cl Cl " H "415 H " C.sub.2 H.sub.4 OCH.sub.3 H "416 H " C.sub.2 H.sub.5 H "417 H " CH.sub.3 C.sub.2 H.sub.5 greenish navy blue418 H " " CH.sub.2 CHCH.sub.2 navy blue419 H Br " CH.sub.2 CHCHCl reddish navy blue420 H Cl " ##STR277## "421 H " " CH.sub.2 C.sub.6 H.sub.5 navy blue422 H " C.sub.2 H.sub.5 CH.sub.2 CHCH.sub.2 "423 H " " CH.sub.2 CHCHCl "424 H " " ##STR278## reddish navy blue425 H Cl CH.sub.3 C.sub.2 H.sub.4 C.sub.6 H.sub.5 greenish navy blue426 H " " C.sub.3 H.sub.6 OC.sub.6 H.sub.5 "427 H H " CHCHCHCl reddish navy blue428 HJ " CH.sub.2 CHCH.sub.2 "429 H CN " " greenish blue430 H " " C.sub.2 H.sub.5 bluish green__________________________________________________________________________ TABLE 18__________________________________________________________________________The dyestuffs of following Table 18 correspond to formula ##STR279##exp.no. M R.sub.12 R.sub.8 R.sub.3 Shade on PES__________________________________________________________________________431 H Br CH.sub.3 H navy blue432 H " C.sub.2 H.sub.5 H "433 H " C.sub.2 H.sub.4 OCH.sub.3 H "434 H Cl CH.sub.3 H "435 Cl Cl " H "436 H " C.sub.2 H.sub.4 OCH.sub.3 H "437 H " C.sub.2 H.sub.5 H "438 H " CH.sub.3 C.sub.2 H.sub.5 greenish navy blue439 H " " CH.sub.2 CHCH.sub.2 navy blue440 H Br " CH.sub.2 CHCHCl reddish navy blue441 H Cl " ##STR280## "442 H " " CH.sub.2 C.sub.6 H.sub.5 navy blue443 H " C.sub.2 H.sub.5 CH.sub.2 CHCH.sub.2 "444 H " " CH.sub.2 CHCHCl "445 H " " ##STR281## reddish navy blue446 H Cl CH.sub.3 C.sub.2 H.sub.4 C.sub.6 H.sub.5 greenish navy blue447 H " " C.sub.3 H.sub.6 OC.sub.6 H.sub.5 "448 H H " CHCHCHCl reddish navy blue449 HJ " CH.sub.2 CHCH.sub.2 "450 H CN " " greenish blue451 H " " C.sub.2 H.sub.5 bluish green__________________________________________________________________________ TABLE 19__________________________________________________________________________The dyestuffs of the following Table 19 correspond to formula ##STR282##exp.no. B Z R.sub.1 R.sub.2 R.sub.3 Shade on__________________________________________________________________________ PES452 O ##STR283## CH.sub.3 H C.sub.2 H.sub.5 blue453 O " " H C.sub.4 H.sub.9 "454 CHNO.sub.2 " " H C.sub.2 H.sub.5 greenish blue455 ##STR284## " " H " "456 O " NHCOCH.sub.3 H " reddish blue457 O N CH.sub.3 H " violet458 O " NHCOCH.sub.3 OCH.sub.3 H navy blue459 O " " " CH.sub.2 CHCH.sub.2 "460 O " " " CH.sub.2 HCCHCl "461 O " " OC.sub.2 H.sub.5 " "462 O " " " CH.sub.2 CHCH.sub.2 "463 O " " OC.sub.2 H.sub.4 OCH.sub.3 " "464 O " " OC.sub.2 H.sub.5 H "465 O.sub.2 NCH " CH.sub.3 H C.sub.2 H.sub.5 blue466 ##STR285## " " OCH.sub.3 " "__________________________________________________________________________ TABLE 20__________________________________________________________________________The dyestuffs of the following Table 20 correspond to formula ##STR286##exp.no. B Z R.sub.1 R.sub.2 R.sub.3 Shade on__________________________________________________________________________ PES467 O ##STR287## CH.sub.3 H C.sub.2 H.sub.5 blue468 O " " H C.sub.4 H.sub.9 "469 CHNO.sub.2 " " H C.sub.2 H.sub.5 greenish blue470 ##STR288## " " H " "471 O " NHCOCH.sub.3 H " reddish blue472 O N CH.sub.3 H " violet473 O " NHCOCH.sub.3 OCH.sub.3 H navy blue474 O " " " CH.sub.2 CHCH.sub.2 "475 O " " " CH.sub.2 HCCHCl "476 O " " OC.sub.2 H.sub.5 " "477 O " " " CH.sub.2 CHCH.sub.2 "478 O " " OC.sub.2 H.sub.4 OCH.sub.3 " "479 O " " OC.sub.2 H.sub.5 H "480 O.sub.2 NCH " CH.sub.3 H C.sub.2 H.sub.5 blue481 ##STR289## " " OCH.sub.3 " "__________________________________________________________________________ TABLE 21__________________________________________________________________________The dyestuffs of the following Table 21 correspond to formula ##STR290##exp.no. B Z R.sub.1 R.sub.2 R.sub.3 Shade on__________________________________________________________________________ PES482 O ##STR291## CH.sub.3 H C.sub.2 H.sub.5 blue483 O " " H C.sub.4 H.sub.9 "484 CHNO.sub.2 " " H C.sub.2 H.sub.5 greenish blue485 ##STR292## " " H " "486 O " NHCOCH.sub.3 H " reddish blue487 O N CH.sub.3 H " violet488 O " NHCOCH.sub.3 OCH.sub.3 H navy blue489 O " " " CH.sub.2 CHCH.sub.2 "490 O " " " CH.sub.2 HCCHCl "491 O " " OC.sub.2 H.sub.5 " "492 O " " " CH.sub.2 CHCH.sub.2 "493 O " " OC.sub.2 H.sub.4 OCH.sub.3 " "494 O " " OC.sub.2 H.sub.5 H "495 O.sub.2 NCH " CH.sub.3 H C.sub.2 H.sub.5 blue497 ##STR293## " " OCH.sub.3 " "__________________________________________________________________________ TABLE 22__________________________________________________________________________The dyestuffs of the following Table 22 correspond to formula ##STR294##exp.no. B Z R.sub.1 R.sub.2 R.sub.3 Shade on__________________________________________________________________________ PES498 O ##STR295## CH.sub.3 H C.sub.2 H.sub.5 blue499 O " " H C.sub.4 H.sub.9 "500 CHNO.sub.2 " " H C.sub.2 H.sub.5 greenish blue501 ##STR296## " " H " "502 O " NHCOCH.sub.3 H " reddish blue503 O N CH.sub.3 H " violet504 O " NHCOCH.sub.3 OCH.sub.3 H navy blue505 O " " " CH.sub.2 CHCH.sub.2 "506 O " " " CH.sub.2 HCCHCl "507 O " " OC.sub.2 H.sub.5 " "508 O " " " CH.sub.2 CHCH.sub.2 "509 O " " OC.sub.2 H.sub.4 OCH.sub.3 " "510 O " " OC.sub.2 H.sub.5 H "511 O.sub.2 NCH " CH.sub.3 H C.sub.2 H.sub.5 blue512 ##STR297## " " OCH.sub.3 " "__________________________________________________________________________ TABLE 23__________________________________________________________________________The dyestuffs of the following Table 23 correspond to formula ##STR298##exp.no. R.sub.11 R.sub.12 R.sub.13 R.sub.1 R.sub.2 R.sub.3 R.sub.10 Shade on PES__________________________________________________________________________513 CN H NO.sub.2 H H CH.sub.3 CH.sub.3 1 ruby514 " H " H H " H 2 ruby515 " H " H H " H 3 ruby516 " H " H H " H 4 ruby517 " H " H H " H 5 ruby518 Cl Cl " H H " CH.sub.3 1 yellow-brown519 Cl Cl " H H " H 2 yellow-brown520 NO.sub.2 Cl " NHCOCH.sub.3 OCH.sub.3 H CH.sub.3 1 navy blue521 " Cl " " " H H 2 navy blue522 " Cl " " " CH.sub.2 CHCH.sub.2 H 2 navy blue523 " CN " CH.sub.3 " CH.sub.3 H 2 blue524 " CN " " H " H 2 reddish blue__________________________________________________________________________ TABLE 24__________________________________________________________________________The dyestuffs of the following Table 25 correspond to formula ##STR299##exp.no. R.sub.11 R.sub.12 R.sub.13 R.sub.1 R.sub.2 R.sub.3 R.sub.10 n Shade on PES__________________________________________________________________________525 CN H NO.sub.2 H H CH.sub.3 CH.sub.3 1 ruby526 " H " H H " H 2 "527 Cl Cl " H H " H 2 yellow-brown528 NO.sub.2 Cl " NHCOCH.sub.3 OCH.sub.3 H H 2 navy blue529 " Br " " " H CH.sub.3 1 "530 " CN " CH.sub.3 " CH.sub.3 H 2 blue531 " " " " H C.sub.2 H.sub.5 H 2 reddish blue532 " " " CH.sub.3 OCH.sub.3 CH.sub.3 H 1 blue533 " " " CH.sub.3 " C.sub.2 H.sub.5 H 1 "534 Cl H NO.sub.2 H H CH.sub.2 CH.sub.2 OCOCH.sub.3 H 2 scarlet535 CN CN " CH.sub.3 H C.sub.2 H.sub.5 H 2 blue__________________________________________________________________________ TABLE 25__________________________________________________________________________The dyestuffs of following Table 25 correspond to formula ##STR300##exp.no. R.sub.11 R.sub.12 R.sub.1 R.sub.2 R.sub.3 m n Q Shade on PES__________________________________________________________________________536 NO.sub.2 CN CH.sub.3 OCH.sub.3 CH.sub.3 1 3 ##STR301## blue537 " " " H " 1 3 " reddish blue538 " Br " H C.sub.2 H.sub.5 1 3 ' violet539 " Cl NHCOCH.sub.3 OCH.sub.3 CH.sub.2 CHCH.sub.2 0 3 " navy blue540 CN H H H CH.sub.3 1 3 " ruby541 Cl Cl H H " 1 3 " yellow-brown542 NO.sub.2 CN CH.sub.3 H " 0 2 " reddish blue543 " " " H C.sub.2 H.sub.5 0 2 " "544 " " " OCH.sub.3 CH.sub.3 0 3 ##STR302## blue545 " " " H C.sub.2 H.sub.5 1 3 " reddish blue546 " " " H CH.sub.3 1 3 " "547 CN H H H " 1 3 " ruby548 NO.sub.2 Cl NHCOCH.sub.3 OCH.sub.3 H 1 3 " navy blue__________________________________________________________________________

APPLICATION EXAMPLE

The dyestuff obtained according to example 1 is converted by means of sand-grinding in the presence of dispersing agents, e.g. commercial lignin sulphonate, with subsequent fine disintegration, into an ultra-disperse dye preparation having an average particle size of 1 .mu.m and a dilution ratio of 3.5:10.

12 parts of this preparation are made into a dispersion with 1000 parts of water, and added to the circulating liquor (13,000 parts, containing 30 parts of ammonium sulphate and 0.3 parts of formic acid as a buffer and optionally a carrier/levelling agent combination) at 60.degree.. The pre-cleaned, compressed, cross-wound spool (1000 parts of polyester yarn on a plastic sleeve) is introduced, the dyeing autoclave closed, and heated in 35 minutes to 130.degree.. After 90 minutes, cooling is effected to 80.degree., the exhausted liquor is drained, and the substrate thus dyed is washed thoroughly with cold water, and purified by reduction in the usual manner. It is then centrifuged and dried. A level, pure, deep ruby-red dyeing is obtained.

Dyeing of polyester yarn can be carried out analogously with examples 2-548, whereby yielding a level, deep dyeing.

The following table gives the .lambda..sub.max -values of the above examples measured in dimethylformamide (DMF).

______________________________________exp. no. .lambda..sub.max nm exp. no. .lambda..sub.max nm______________________________________ 8 532 26 614 9 527 27 511 10 508 28 530 11 494 29 517 12 490 30 542 13 489 31 600 14 520 32 541 15 510 33 545 16 530 35 517 17 527 36 537 18 435 37 524 19 443 38 534 20 433 39 544 21 432 42 604 22 583 44 645 23 604 45 660 24 615 46 630 25 616 48 625 49 622 70 456 50 625 71 459 51 626 72 446 52 661 73 487 53 529 74 492 54 550 75 488 55 556 76 497 56 510 77 509 57 587 78 502 58 584 79 526 59 558 80 524 60 549 81 532 61 605 82 536 62 605 83 443 63 606 84 532 64 572 85 538 65 561 86 515 66 525 87 495 67 451 88 490 68 457 89 489 69 449 90 521 91 511 113 525 92 531 114 534 93 532 115 544 94 435 118 605 95 443 120 646 96 433 121 661 97 432 122 631 98 584 124 625 99 605 125 622100 616 126 626101 617 127 626102 615 128 661103 512 129 530104 531 130 551105 518 131 557106 543 132 511107 601 133 588108 542 134 585109 545 135 559111 518 136 550112 538 137 606138 606 159 443139 607 160 440140 560 161 527141 562 162 539142 526 163 513143 452 164 493144 458 165 489145 449 166 488146 456 167 519147 459 168 509148 446 169 529149 487 170 526150 492 171 435151 489 172 443152 498 173 433153 509 174 432154 503 175 582155 527 176 603156 525 177 614157 527 178 615158 538 179 613180 510 206 528181 529 207 549182 516 208 555183 514 209 509184 599 210 586185 540 211 583186 544 212 557188 516 213 548189 536 214 604190 523 215 604191 533 216 605192 543 217 558195 603 218 560197 644 219 524198 659 220 450199 629 221 456201 624 222 448202 621 223 455203 624 224 458204 624 225 445205 660 226 486227 491 248 435228 487 249 441229 496 250 432230 508 251 431231 501 252 582232 525 253 603233 523 254 614234 531 255 615235 540 256 613236 442 257 510237 439 258 529238 530 259 516239 532 260 542240 513 261 599241 493 262 540242 487 263 544243 487 265 516244 519 266 536245 509 267 523246 529 268 533247 527 269 544272 603 295 560274 644 296 524275 659 297 445276 629 298 451278 624 299 448279 621 300 455280 624 301 458281 625 302 445282 660 303 486283 528 304 491284 549 305 487285 555 306 496286 509 307 508287 586 308 502288 583 309 525289 557 310 523290 548 311 530291 604 312 536292 604 313 442293 605 314 439294 558 315 440316 441 337 516317 437 338 533318 530 339 524319 534 340 439320 530 341 542321 524 342 537322 530 343 607323 443 344 610324 516 346 583325 533 347 622326 524 348 543327 439 349 537328 440 350 607329 441 351 609330 530 354 621331 530 354 621332 534 355 541333 530 356 540334 524 357 605335 530 358 607336 443 360 602361 628 386 599362 541 387 634363 539 388 637364 605 389 597365 607 390 597367 602 391 594368 629 392 598369 597 393 585370 597 394 593371 594 395 599372 581 396 603373 593 397 599374 600 398 589375 604 399 574376 599 401 600377 589 402 591378 573 403 575380 601 406 564381 592 407 598382 576 408 633385 565 409 635410 596 434 596411 596 435 583412 593 436 592413 597 437 598414 584 438 602415 592 439 598416 598 440 588417 602 441 571418 598 443 600419 588 444 590420 574 445 574422 598 448 564423 590 449 598424 574 450 633427 563 451 636428 596 452 611429 632 453 613430 635 455 638431 595 457 587432 596 458 610433 593 459 624460 613 487 586461 615 488 609462 626 489 623463 625 490 612464 610 491 614466 680 492 625467 612 493 624468 613 494 609470 639 497 679472 587 498 610473 611 499 612474 624 501 637475 613 503 586476 615 504 609477 627 505 623478 626 506 612479 611 507 614481 681 508 625482 610 509 624483 612 510 609485 637 512 679513 534 531 601514 535 532 614515 535 533 619516 536 534 511517 536 535 619518 440 536 613519 440 537 588520 597 538 557521 597 539 599522 599 540 533523 613 541 439524 587 542 587525 535 543 593526 536 544 613527 441 545 590528 598 546 587529 598 547 534530 595 548 598______________________________________ .lambda..sub.max -values

Claims

1. The disperse dye of the general formula I ##STR303## wherein D signifies a diazo component which is usual with disperse dyes,

K signifies an aromatic radical of formula ##STR304## R.sub.1 signifies hydrogen, chlorine, C.sub.1-2 -alkyl, C.sub.1-2 -alkoxy or acylamino,

R.sub.2 signifies hydrogen, C.sub.1-4 -alkoxy, C.sub.1-2 -alkoxyethoxy, chlorine, bromine, or together with R.sub.3 signifies a group of formula --*CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2 -- (*bonded to the nucleus),

R.sub.3 signifies hydrogen, C.sub.1-6 -alkyl, C.sub.3-4 -alkenyl, chloro- or bromo-C.sub.3-4 -alkenyl, C.sub.3-4 -alkinyl, phenyl-C.sub.1-3 -alkyl, C.sub.1-4 -alkoxycarbonyl-C.sub.1-3 -alkyl, C.sub.3-4 -alkenyloxycarbonyl-C.sub.1-3 -alkyl, C.sub.3-4 -alkinyloxycarbonyl-C.sub.1-3 -alkyl, phenoxy-C.sub.2-4 -alkyl; C.sub.2-4 -alkyl substituted by halogen, cyano, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylcarbonyloxy or C.sub.1-4 -alkoxycarbonyloxy; or a group of formula --CH.sub.2 --CH(R.sub.8)CH.sub.2 --R.sub.9,

R.sub.4 signifies hydrogen, phenyl or C.sub.1-2 -alkyl,

R.sub.5 signifies a radical of formula ##STR305## R.sub.7 signifies hydrogen or C.sub.1-4 -alkyl, R.sub.8 signifies hydroxyl, C.sub.1-4 -alkylcarbonyloxy or C.sub.1-4 -alkylcarbonyloxy,

R.sub.9 signifies chlorine, C.sub.1-4 -alkoxy, phenoxy, allyloxy or C.sub.1-4 -alkylcarbonyloxy,

R.sub.10 signifies hydrogen or C.sub.1-4 -alkyl,

Y signifies C.sub.2-3 -alkylene,

m and z independently signify zero or 1 and

n signifies a number from 1 to 5,

whereby, if K is a radical of formula b or c, R.sub.3 only signifies hydrogen, provided that when Y.dbd.--CH(CH.sub.3)CH.sub.2 --, m=1.

2. The disperse dye according to claim 1, of the general formula Ia ##STR306## wherein D.sub.1 is 3-phenyl-1,2,4-thiadiazolyl or corresponds to one of the following formulae: ##STR307## wherein a signifies hydrogen, chlorine, bromine, cyano, nitro-, C.sub.1-4 -alkoxycarbonyl, C.sub.1-3 -alkylsulphonyl, preferably hydrogen, chlorine, cyano or nitro,

b signifies chlorine, bromine, nitro, methyl, C.sub.1-2 -alkylsulphonyl, C.sub.1-4 -alkylcarbonyl, aminosulphonyl, mono- or di-C.sub.1-4 -alkylaminosulphonyl, phenylaminosulphonyl, C.sub.1-4 -alkoxycarbonyl, aminocarbonyl, mono- or di-C.sub.1-4 -alkylaminocarbonyl, phenylaminocarbonyl, phenylazo, benzyloxycarbonyl, tetrahydrofurfuryl-2-oxycarbonyl, C.sub.3-4 -alkenyloxycarbonyl, C.sub.3-4 -alkinyloxycarbonyl or phenoxycarbonyl,

c signifies hydrogen or chlorine, or if d is hydrogen, also thiocyano,

d signifies hydrogen, chlorine, bromine or cyano,

e signifies nitro, C.sub.1-4 -alkylcarbonyl, C.sub.1-4 -alkoxycarbonyl, cyano, aminocarbonyl, mono- or di-C.sub.1-2 -alkylaminocarbonyl,

f signifies hydrogen, chlorine, bromine, C.sub.1-2 -alkyl or phenyl,

g signifies nitro, cyano, formyl, dicyanovinyl or a group of formula --CH.dbd.CH--NO.sub.2, --CH.dbd.C(CN)CO--OC.sub.1-4 -alkyl, H.sub.5 C.sub.6 --N.dbd.N-- or 3- or 4-NO.sub.2 --C.sub.6 H.sub.4 --N.dbd.N--,

h signifies cyano or C.sub.1-4 -alkoxycarbonyl,

i signifies C.sub.1-4 -alkyl or phenyl,

j signifies --CN, --CH.dbd.CH.sub.2 or phenyl,

k signifies C.sub.1-4 -alkyl,

l signifies hydrogen, chlorine, bromine, cyano, thiocyano, nitro, C.sub.1-4 -alkoxycarbonyl or di-C.sub.1-4 -alkylaminosulphonyl,

p signifies hydrogen, chlorine or bromine and

q signifies C.sub.1-4 -alkyl, C.sub.1-4 -alkoxycarbonyl-C.sub.1-4 -alkylene or C.sub.1-4 -alkylene-COOCH.sub.2 CF.sub.3,

whereby the phenyl nuclei of these substituents may bear one or two substituents from the series chlorine, bromine, methyl or C.sub.1-2 -alkoxy,

R.sub.1 ' signifies hydrogen, C.sub.1-2 -akyl, chlorine or acylamino,

R.sub.2 ' signifies hydrogen, chlorine, C.sub.1-2 -alkoxy, C.sub.1-2 -alkoxyethoxy, or with R.sub.3, a group of formula --CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2 --,

R.sub.3 signifies hydrogen, C.sub.1-6 -alkyl, C.sub.3-4 -alkenyl, chloro- or bromo-C.sub.3-4 -alkenyl, C.sub.3-4 -alkinyl, phenyl-C.sub.1-3 -alkyl, C.sub.1-4 -alkoxycarbonyl-C.sub.1-3 -alkyl, C.sub.3-4 -alkenyloxycarbonyl-C.sub.1-3 -alkyl, C.sub.3-4 -alkinyloxycarbonyl-C.sub.1-3 -alkyl, phenoxy-C.sub.2-4 -alkyl; C.sub.2-4 -alkyl substituted by halogen, cyano, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylcarbonyloxy or C.sub.1-4 -alkoxycarbonyloxy; or a group of formula --CH.sub.2 --CH(R.sub.8)CH.sub.2 --R.sub.9,

R.sub.5 signifies a radical of formula ##STR308## R.sub.4 ' and R.sub.10 ' independently signify hydrogen or C.sub.1-2 -alkyl and

Y.sub.1 signifies a group of formula --CH.sub.2 CH.sub.2 -- or --CH(CH.sub.3)CH.sub.2 --

m and z independently signify zero or 1 and

n signifies a number from 1 to 5 provided that when Y=--CH(CH.sub.3)CH.sub.2 --, m=1.

3. The disperse dye according to claim 2, of formula Ib ##STR309## wherein D.sub.2 signifies the radical of a diazo component from the series 2,6-dicyano-4-chloro-, -4-bromo-, -4-methyl- or -4-nitrophenyl, 2,4-dinitro-6-chloro-, -6-bromo- or -6-cyanophenyl, 2-chloro- or 2-bromo-4-nitro-6-cyanophenyl, 2,4-dinitrophenyl, 2,6-dichloro or 2,6-dibromo-4-nitrophenyl, 2-chloro-4-nitro-6-bromophenyl, 2-chloro-, 2-bromo- or 2-cyano-4-nitrophenyl, 2,4-dinitro-5-chlorophenyl or -5-thiocyanophenyl, 2,4-dinitro-5,6-dichlorophenyl, 2,5-dichloro-4-nitrophenyl, 4-nitrophenyl, 4-phenylazophenyl, 4-C.sub.3-4 -alkenyloxycarbonylphenyl, 4-C.sub.3-4 -alkinyloxycarbonylphenyl, 4-C.sub.1-4 -alkoxycarbonylphenyl, 2-C.sub.1-4 -alkoxycarbonyl-4-nitrophenyl, 4-phenoxycarbonylphenyl, 4-benzyloxycarbonylphenyl, 4-(tetrahydrofurfuryl-2'-oxycarbonyl)-phenyl, 3,5-dicyano-4-chloro-thienyl-2, 3,5-dicyano-thienyl-2, 3-cyano-5-nitro-thienyl-2, 3-acetyl-5-nitro-thienyl-2, 3,5-dinitro-thienyl-2, 3-(C.sub.1-4 -alkoxycarbonyl)-5-nitro-thienyl-2, 5-phenylazo-3-cyanothienyl-2, 5-phenylazo-3-cyano-4-methyl-thienyl-2, 5-nitro-thiazolyl-2, 5-nitrobenzisothiazolyl-3, 3-methyl-4-cyano-isothiazolyl-5, 3-phenyl-1,2,4-thiadiazolyl-2, 5-(C.sub.1-2 -alkylmercapto)-1,3,4-thiadiazolyl-2, 3-C.sub.1-2 -alkoxycarbonylethylmercapto-1,2,4-thiadiazolyl-5, 1-cyanomethyl-4,5-dicyanoimidazolyl-2, 6-nitrobenzothiazolyl-2, 5-nitrobenzothiazolyl-2, 6-thiocyanobenzothiazolyl-2, 6-chlorobenzothiazolyl-2, (5),6,(7)-dichlorobenzothiazolyl-2, ##STR310## or of formula ##STR311## and B signifies oxygen or a group of formula ##STR312## R.sub.1 ' signifies hydrogen, C.sub.1-2 -alkyl, chlorine or acylamino, R.sub.2 ' signifies hydrogen, chlorine, C.sub.1-2 -alkoxy, C.sub.1-2 -alkoxyethoxy, or with R.sub.3, a group of formula --CH(CH.sub.3)CH.sub.2 C(CH.sub.3).sub.2 --,

R.sub.3 signifies hydrogen, C.sub.1-6 -alkyl, C.sub.3-4 -alkenyl, chloro- or bromo-C.sub.3-4 -alkenyl, C.sub.3-4 -alkinyl, phenyl-C.sub.1-3 -alkyl, C.sub.1-4 -alkoxycarbonyl-C.sub.1-3 -alkyl, C.sub.3-4 -alkenyloxycarbonyl-C.sub.1-3 -alkyl, C.sub.3-4 -alkinyloxycarbonyl-C.sub.1-3 -alkyl, phenoxy-C.sub.2-4 -alkyl; C.sub.2-4 -alkyl substituted by halogen, cyano, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylcarbonyloxy or C.sub.1-4 -alkoxycarbonyloxy; or a group of formula --CH.sub.2 --CH(R.sub.8)CH.sub.2 --R.sub.9,

R.sub.5 signifies a radical of formula ##STR313## R.sub.4 ' and R.sub.10 ' independently signify hydrogen or C.sub.1-2 -alkyl and

Y.sub.1 signifies a group of formula --CH.sub.2 CH.sub.2 -- or --CH(CH.sub.3)CH.sub.2 --

m and z independently signify zero or 1 and

n signifies a number from 1 to 5.

4. The disperse dye according to claim 3, wherein

D.sub.2 signifies the radical of a diazo component from the series 2,6-dicyano-4-chloro, -4-bromo, -4-methyl or -4-nitrophenyl, 2,4-dinitro-6-chloro-, -6-bromo- or -6-cyanophenyl, 2-chloro- or 2-bromo-4-nitro-6-cyanophenyl, 2,4-dinitrophenyl, 2,6-dichloro- or 2,6-dibromo-4-nitrophenyl, 2-chloro-4-nitro-6-bromophenyl, 2-chloro-, 2-bromo- or 2-cyano-4-nitrophenyl, 2,4-dinitro-5-chlorophenyl or -5-thiocyanophenyl, 2,4-dinitro-5,6-dichlorophenyl, 2,5-dichloro-4-nitrophenyl, 4-nitrophenyl, phthalidyl-5 or of formula ##STR314## and B signifies oxygen or a group of formula ##STR315##

5. The disperse dye of the general formula Ib according to claim 3, wherein

D.sub.2 signifies a diazo component from the series 2,4-dinitro-6-chloro-, -6-bromo- or -6-cyanophenyl, 2,4-dinitro-5-chloro- or -5-thiocyanophenyl or 2,4-dinitro-5,6-dichlorophenyl,

R.sub.1 ' signifies C.sub.1-2 -alkylcarbonylamino,

R.sub.2 ' signifies C.sub.1-2 -alkoxy or C.sub.1-2 -alkoxyethoxy,

R.sub.3 signifies hydrogen, C.sub.1-4 -alkyl, cyanoethyl, C.sub.1-2 -alkoxyethyl, C.sub.3-4 -alkenyl, chlorallyl, C.sub.3-4 -alkinyl, C.sub.1-2 -alkoxycarbonylmethyl, allyloxycarbonylmethyl or propargyloxycarbonylmethyl,

R.sub.4 ' signifies hydrogen or methyl,

R.sub.5 signifies a radical of formula ##STR316## R.sub.10 ' signifies hydrogen or methyl, Y.sub.1 signifies a group of formula --CH.sub.2 CH.sub.2 -- or --CH(CH.sub.3)CH.sub.2 --

m signifies zero or 1 and

n signifies a number from 1 to 5.

6. The disperse dye of formula Ib, according to claim 3, wherein

D.sub.2 signifies a diazo component from the series 2,4-dinitro-6-chloro- or -6-bromophenyl,

R.sub.1 ' signifies C.sub.1-2 -alkylcarbonylamino,

R.sub.2 ' signifies methoxy or ethoxy,

R.sub.3 signifies hydrogen, allyl, chlorallyl or propargyl,

R.sub.5 signifies a radical of formula ##STR317## R.sub.4 ' and R.sub.10 ' independently signify hydrogen or methyl, Y.sub.1 signifies 1,2-ethylene,

m signifies zero or 1, and

n signifies a number from 1 to 5.

7. The disperse dye of formula I, according to claim 1, wherein

D signifies a diazo component from the series 4-nitrophenyl, 4-nitro-2-ethylsulphonylphenyl, 4-nitro-2-methylsulphonylphenyl, 4-methoxycarbonylphenyl, phthalidyl-5, 4-ethoxycarbonylphenyl, 2-chloro-4-nitrophenyl, 2,6-dichloro-4-nitrophenyl, 2-bromo-4-nitro-6-chlorophenyl or 2-cyano-4-nitrophenyl,

K signifies a radical of formula a

R.sub.1 signifies hydrogen, methyl, acylamino or chlorine,

R.sub.2 signifies hydrogen,

R.sub.3 signifies C.sub.1-4 -alkyl, C.sub.3-4 -alkenyl, chlorallyl, benzyl, cyanoethyl, C.sub.1-2 -alkoxyethyl, C.sub.1-4 -alkylcarbonyloxyethyl, C.sub.1-2 -alkoxycarbonylethyl or C.sub.1-4 -alkoxycarbonyloxyethyl,

R.sub.4 and R.sub.10 independently signify hydrogen or C.sub.1-2 -alkyl,

R.sub.5 signifies a radical of formula ##STR318## Y signifies a group of formula --CH.sub.2 CH.sub.2 -- or --CH(CH.sub.3)CH.sub.2 --

m and z independently signify zero or 1, and

n signifies a number from 1 to 5.

8. The disperse dye of formula Ib, according to claim 3, wherein

D.sub.2 signifies a diazo component from the series 4-nitrophenyl, 2-chloro-4-nitrophenyl, 2-bromo-4-nitrophenyl, 2,6-dichloro-4-nitrophenyl, 2-chloro4-nitro-6-bromophenyl, 2-cyano-4-nitrophenyl,

R.sub.1 ' signifies hydrogen or methyl,

R.sub.2 ' signifies hydrogen,

R.sub.3 signifies C.sub.1-4 -alkyl,

R.sub.4 ' signifies hydrogen or methyl,

R.sub.5 signifies a radical of formula ##STR319## R.sub.10 ' signifies hydrogen, Y.sub.1 signifies 1,2-ethylene,

m signifies zero or 1, and

n signifies the number 1.

9. Process for the production of the disperse dyes of formula I, according to claim 1, characterized in that a diazotised amine of formula II

D--NH.sub.2 (II)

is coupled with a compound of formula III ##STR320##

10. A process for dyeing or printing a substrate comprising applying to the substrate a compound according to claim 1.

11. A process according to claim 10 wherein the substrate is a fibre, filament or a material produced therefrom.

12. A process according to claim 11 wherein the substrate is a fully synthetic or semi-synthetic, hydrophobic, high-molecular weight material.

13. A process according to claim 10 wherein the substrate is a textile material consisting of linear, aromatic polyesters, cellulose-2 1/2-acetate, cellulose triacetate or a combination thereof.

14. A process for thermo transfer printing comprising thermo transferring to a substrate a compound according to claim 1.