DE2020350B2 - Dye preparations, their mastery and use - Google Patents

Description

The present invention relates to stable, concentrated, liquid dye preparations of fiber-reactive, disperse dyes free of sulfonic acid groups and a process for their preparation.

Liquid formulations of insoluble in water Pigments are known, for example, from DE-PS 5 83 650, which describes a liquid paste of lacquer dyes which, as adjustment agents, are those in water Contains sparingly soluble to insoluble amides of organic acids, which are easily soluble in alcohol. These formulations are unsuitable for dyeing textile material from aqueous or organic liquor,

In GB-PS 11 Jl 043 aqueous dispersions of fiber-reactive Oispersion dyes are described. These dispersions are n \ m dyeing of organic, water-immiscible solvents unusable.

Finally, in GB-I ¹ S 1045 839 a liquid composition is described, which is used to form Aqueous emulsions are suitable, consisting of at least one Textile dye, preferably a water-soluble fiber-reactive dye mixed with one with This consists of water immiscible organic liquid and a corresponding dispersant Composition is not suitable for dyeing synthetic textile material from an organic one Dye liquor.

It has now surprisingly been found that concentrated, laser-stable dye preparations can be used fiber-reactive disperse dyes free of sulfonic acid groups with a water-miscible one organic solvent and optionally a dispersant can be obtained.

The present invention accordingly relates to liquid stable, concentrated dye preparations, which thereby are marked that they are made from

a) at least 20%, based on the court of Preparations, at least one fiber-reactive disperse dye free from sulfonic groups,

b) a phosphorus-free organic solvent which is miscible in all proportions with water and

c) optionally consist of an anionic or non-ionic dispersant.

The dyes can belong to a wide variety of dye classes, such as the classes of mono-, Dis- and polyazo dyes, anthraquinone, perinone, quinophthalone and nitro dyes, including the Styryl dyes ^

Of the particularly preferred series of disperse dyes, the azo dyes in particular come from Mono and disazo series in question. Examples are the dyes of the formula

DN = NA-NRiR ₂

where D is Re. "of a diazo component, A is an optionally substituted p-arylene radical and Ri and R _{2 are} each optionally substituted alkyl radicals, which can be the same or different from one another, and the dyes of the formula

D-N = N-B

where D is the same as above and B is the residue of a naphthol, phenol, pyrazolone or aminopyrazole, mentioned.

If the coupling component contains a fiber-reactive radical, such as. B. in the following coupling components, the diazo component can be z. B. derive from amines D-NH ₂ , which contain r.dne fiber-reactive groups.

Examples of individual coupling components with fiber-reactive groups are:

-N (CH ₂ CH ₂ OCOCHj) ₂ NH-CO-CHBr-CH ₂ Br

-N (CIICH ₂ OCoCH, Cl); N (CHjCH ₂ CI) ₂

HC C-CH ₃

Il Il

HO-C N

CH ₂ CH ₁ Br

Π O

Γ>

C- (H, CH ₃ , COOAIkyl II or CONH ₂ ) N

Alkylene

or

Arylene

where Z is a fiber-reactive radical 'ind c, d, Ri and R2 die have the meaning given below.

Examples of Diaz components D-NH2 without fiber-reactive groups are /. B.

Aminobenzene, I-amino-4-chlorobenzene, l-Amiiio-4-bromben / ol.

I-aniino-4-methylbene / ol, t-aniino-4 nitrobenzene, 1-amina-4 ~ cya. nbenzene,
1-Amino-W-dioyanbenzene, t -amino-4-metbylsulfonyIbenzal, 1-amino-4-carbalkoxybenzene, 1-amino- ^ dichlorobenzene, 1-amino- ^ dibromobenzene, 1-amino ^ -meAyM-chjorbenzene, 1 -amino -a-trifluoroiethyl- ^ chlorobenzene, l-amino ^ -cyan ^ chlorobenzene, l-amino-Z-carboinelhoxy- ^ chlorobenzene, l-amino-2-carbomethoxy-4-nitrobenzene, 1- amino-2-chloro-4 -cyanbenzene, 1-amino ^ -chloro ^ -nitrobenzene, 1-amino ^ -bromo-A-nitrabenzene, 1-amino-.i-chloro- ^ carbethoxybenzene, l-amino-Z-chloro- ^ methylsulfonylbenzene, l-amino -l-methylsulfonyl- ^ chlorobenzene, 1 - amino-2,4-dinitro-6-methylsulfonylbenzene, l-amino-2,4-dinitro-6- (2'-hydroxyethyI-

sulfonyl) benzene,
i-Amino - ^ - dinitro-e ^ '- chloräthylsc! ionyi) benzo !,

l-Amino ^ -methylsulfonyl-'t-nitrobenzene, l-Amino-4-methylsulfonyl-2-n ^ trobenzene, 1 - Amino-2,4-dinitrobenzene, 1 - Amino - ^ - dicyanobenzene, l-amino ^ -cyan ^ -methylsulfonylbenzene, 1 -amino- ^ e-dichl & M-cyanobenzene, l-amino- ^ e-dichloro ^ -nitrobenzene, l-Amino ^^ - dicyan-ö-chlorobenzene, 4-amino-benzoic acid cyclohexyl ester, l-Amino ^^ - dinitro-e-chlorobenzene and particularly

1 -Amino ^ -cyan ^ -nitrobenzene, also 1-aminobenzene-2-, -3- or -4-sulfonic acid-

amide, like that
N-methyl- or Ν, Ν-dimethyl- or

-Diethylamide,
Ny-Isopropyloxypropyl ^ -amino-naphthalene-

6-sulfonic acid amide,
Ny-isopropyloxypropyl-l-aminobenzene-2-,

-3- or -4-sulfonic acid amide, N-isopropyl-1-aminobenzoI-2-, -3- or

-4-sulfonic acid amide,
N, y-methoxypropyl-1-aminobenzene-2-, -3- or

-4-sulfonic acid amide,
N, N-bis (/? - hydroxyethyl) -1 -aminobenzene-2-,

-3- or -4-sulfonic acid amide, i-amino ^ -chlorobenzene ^ -sulfonic acid amide, and the N-substituted derivatives 2-, 3- or 4-aminophenylsulfamate, 2-amino-4-, -5- or -6-methylphenylsulfamate, i-amino-S-methoxy-phenyl sulfamate, S-Aniino-ö-Chlorphenylsulfamat, 3-amino-2,6-dichlorophenyl sulfamate, 4-amino-2- or -3-methoxyphenyl sulfamate, N, N-Dimethyl-2-aminophenylsulfamat, N.N-Di-n-butyl ^ -aminophenylsulfamat, N.N-Dimethyl ^ -amino ^ -chlorophenylsulfamate, N.n-Propyl-3-aminophenylsulfamat, N.N-Di-n-butyl-S-aminophenylsulfamate, 0 (3-aminophenyl) -N-morpholine-N-sulfonate, O (3-aminophenyl) -N-piperidine-sulfonate, N-Cyclohexyl-O- (J-amine (iphenyl) sulfamate, N (N-methylaniline) -O- (3-aminophenyl) sulfonate, N.N-Diethyl-S-amino-O-methylphenyl-sulfamate. N-Ethylamine-O- (4-aminophenyl) -sulfonate, N.N-Dimethyl ^ -aminophenylsulfamat.

0- (n-Propyl) -0- (3-aminophenyl) sulfonate, C / J-chloroethyl-O - ^ - aminophenyOsulfonat, O-BenzyI-O- (3-aminophenyI) sulfonate and O-Ethyl O- (4-amino-2,6-dimethylphenyl) sulfonate

4-aminoazobenzene,

3,2'-DimeihyI-4-aminoazobenzene, 2-Metli / l-5-methoxy-4-aminoazobenzül, ^ Amino ^ -nitroazobenzene, 24-dimethoxy-4-aminoazobenzene, ^ -Methoxy- ^ aminoazobenzene,

2-methyl-4'-methoxy-4-aminoazobenzene,

3,6,4'-trimethoxy-4-aminoazobenzene, 4'-chloro-4-aminoazobenzene, 2'- or S'-chloro- ^ aminoazobenzene, 3-nitro-4-amino-2 ', 4'-dichlorazobenzene, and 4-aminoazobenzene-4'-sulfonic acid amide

2-aminothiazole,

2-Amino-5-nitrothiazo !,

2-Amino-5-methylsulfonyl-th! Azole _> 2-Amino-5-cyanthiazole,

2-amino-4-methyl-5-nitrothiazole, S-amino-V-dibromo-benzisothiazole, S-amino-S-chlorobenzisothiazole, S-amino ^ -chlorobenzisothiazole, S-amino-S-chloro-T-bromo-benzisothiazole, S-amino-S-nitro-benzisothiazole, 2-amino-4-methylthiazole, 2-Amino-4-phenylthiazoI, 2-Amino-4- (4'-chloro) -phenylthiazole, 2-Amino-4- (4'-nitro) -phenylthiazole, 3-aminopyridine,

3-amino quinoIine,

3-aminopyrazole,

3-amino-1-phenylpyrazole, 3-aminoindazole,

3-amino-1,2,4-triazole,

5- (N '»ethyl-, ethyl-, phenyl- or benzyl) -1,2,4-triazole,

3-Amino-1 - (4'-methoxyphenyl) pyrazole, 2-aminobenzothiazole,
2-amino-6-methylbenzthiazole, 2-amino-6-methoxybenzthiazole, 2-amino-6-chlorobenzth! Azo., 2-amino-6-cyanobenzthiazole, 2-amino-6-rhodanobenzthiazole, 2-amino-6-ni (robenzthiazole, 2-amino-6-carbuethoxybenzthiazole, 2-amino- (4- or -6) -methylsulfonylbenzthiazole,

2-amino-1,3,4-thiadiazole, 2-amino-U ^ -thiadiazole, 2-amino-4-phenyl- or -4-methyl-

1,3,5-thiadiazole,
3-Amino-benzisothiazole, S-Amino-S-nitro-Z-bromo-benzisothiazole, 3,5-diamino-benzisothiazole, 2-amino-5-phenyI-1,3,4-thiadiazole, 2-amino-3-nitro- 5-methylsulfonyl thiophene. 2-amino-3,5-bis (methylsulfonyl) -thiophene, S-amino-S-methyl-isothiazole, 2-amino-4-cyano-pyrazole and 2- (4'-nitrophenyl) -3-amino-4- cyanopyra7ol.

If one uses coupling components which have no fiber-active radical, the diazo components must be derived from fiber-reactive amines which contain fiber-reactive groups Z, such as, B, S-triazinyl radicals which have 1 or 2 chlorine or bromine atoms on the triazine ring, pyrimidyl radicals, the carry one or two chlorine atoms or one or two arylsulfonyl or alkanesulfonyl groups on the pyrimidine ring,
Mono- or bis- ()> - halogen - /? - hydroxypropyl)

-amino groups,
0-Halogenäthylsulfamidreste,
ίο 0-haloethoxy groups,

j3-haloethyl mercapto groups,
2-chloro-benzothiazolyl-6-azo groups,
2-chlorobenzothiazolyl-6-amino groups,
y-halogen-0-hydroxy-propylsulfamide residues,
Chloroacetylamino groups,

ocJJ-dibromopropionylamino groups,
Vinylsulfonyl groups and
2,3-epoxypropylamino or oxy groups.
Suitable fiber-reactive diazo components are

E.g.

N ^ -Chlorethyl-S-chloro-t-amiiiObenzoisulfamid

(Hydrochloride),
N ^ -Cchloroethyl-4-aminobenzene-sulfamide

(Hydrochloride),
S-bromine ^ -amino-cü-chloroacetophenon,

N.y-chlorine - ^ - hydroxypropyl ^ -aminobenzene-

sulfamide,

N.jS-chloroethyl-1-amino-4-naphthylsulfonamide,
N.ß-chloroethyl-1-amino-33-di-chlorobenzenesulfamide and

4- (γ-chloro - /? - hydroxy-propoxy) -aniline.
As coupling component HB without a fiber-reactive radical, z. B. named:
the aniline of the formula

R ₁

in which c and d are hydrogen atoms, lower alkyl, alkoxy or alkyl mercapto radicals or, if appropriate ■ n substituted phenyl, phenoxy or uenzyl radicals.

The group c can, in addition to the groups mentioned above, also a chlorine or bromine atom, a Trifluoromethyl group and one optionally alkylated, preferably methylated, on the nitrogen atom so mean acylamino group in which the acyl radical of Remainder of an organic monocarboxylic acid, an organic monosulfonic acid, such as methane, ethane or p-toluene monosulfonic acid, or the remainder of a carbamic acid or a carbonic acid monoester or monoamide, such as phenoxycarbonyl, M.ethoxycarbonyl and is aminocarbonyl.

The groups Ri and R2 can be hydrogen atoms

or lower, d. H. 1 to 4, preferably 2 to 4, carbon atoms containing alkyl groups, such as

bo thyl, Ä'hyl, n-propyl or n-butyl groups, which are in can usually be substituted, such as /. B.

Benzyl-, j3-phenethyl-, ß-Cyanälh; 1-, alkoxyalkyl-,
like /? - Ethoxyethyl- or (i-methoxybutyl-,
Hydroxyalkyl, such as / i-hydroxyethyl,
ι ¹ '· β.γ- dihydro-'ypropyl-, nitroalkyl-, such as

/ i-nitroethyl. Acylaminoalkyl, such as ^ - (acetyl or
-formvl) -aminoethyl-. l ^: acid yacvloxyalkyl, such as
F ^: ormvloxvalkvl.ii-AcL'tvloxväthvl-.

/J.y- diacetoxypropyl and y-butyryloxypropyl, /? - (alkyl- or -aryl) -sulfonylalkyl-, such as

^ -Metnanesulfonylätnyl-.ß-Äthansulfonvläthyl.

Vinylsulfoalkyl, phenylsulfonylalkyl and

/? - (p-chlorobenzenesulfonyl) -ethyl-, alkyl or ί

Arylcarbamoyloxyalkyl-. how

/ i-methylcarbamyloxyethyl-.

Butylcarbamyloxyethyl,

ß-Phenyl-carbamyloxyäthyl-, (alkyl or

Aryl) -oxycarbonyloxyalkyl- such as / 3- (methoxy-, in Ethoxy -, /? - chloroethoxy, isopropyl) or

p-Toluyl-carbonyloxyäthyl-.y-Acetamidopropyl-, /? - (Nitrophenoxy) ethyl,

ß- (p- hydroxyphenoxy) -ethyl-,

^ - (^ '- acetylethoxycarbonylJ-ethyl-, ^ - [(^' - cyano-, 15

Hydroxy, methoxy or Acetoxy) ethoxycarbonyl] ethyl, cyanoalkoxyalkyl,

/ J-carboxyethyl, ß-acetylethyl,

^ -Cyanacetoxyäthyl- and ^ -Benzoyloxyäthyl- and

0- (p-alkoxy- or 20

Phenoxy-benzoyl) -oxyethyl groups. The groups Rt and R ₂ generally contain no more than 18 carbon atoms.

As coupling components without fiber-reactive groups, for example, benzene or 25 Naphthalene series or from the series of heterocyclic coupling components can be used. from the coupling components of the benzene series are in addition to the phenols, such as m- or p-cresol, resorcinol, I-hydroxy-3-cyanomethylbenzene, especially the aminobenzenes mentioned, for example

Aniline,

3-methylaniline,

2-methoxy-5-methylaniline,

3-acetylamino-i-aminobenzene, r>

N-methylaniline. N-0-hydroxyethylaniline, N - /? - methoxyethylaniline, N ^ -cyanoethylaniline, N-0-chloroethylaniline, ^ ₀ Dimethylaniline, and Diethylaniline, N-methyl-N- (benzyl- or ^ -phenylethyl) aniline. N-n-butyl-N-0-chloroethylamine, N- (methyl, ethyl, propyl or butyl). N - ^ - cyanoethylaniline, N-methyl-N - ^ - hydroxyethylaniline, N-ethyl-N - ^ - chloroethylaniline, N-methyl-N - ^ - acetoxyethylaniline. N-ethyl-N-ß-methoxyethylaniline. N - ^ - cyanoethyl-N-zS-chloroethylaniline,

N-CyanäthyI-N- (acetoxy- or benzoyloxyäthyl) aniline,

Nii-Di - ^ - hydroxyethylaniline, NJJ-Di - ^ - acetoxyethylaniline, 55 N-ethyl-N ^ -hydroxy-3-chIoφropylaniIin, N ^ i-Di-ß-cyanäthy! Aniline, N.N-Di-ß-cyanoethyl-S-methylaniline, N - ^ '- cyanoethyl-N ^ "- hydroxyethyl-3-chloroaniline, N, N-Di - ^ - cyanoethyl-3-methoxyaniline, 60 N.N-Dimethyl-S-acetylaminoaniline, N-EthyI-N - ^ - cyanäthyI-3-acetylaminoaniline,

N.N-Di - ^ - cyanäthyI-2-methoxy-5-acetyI-aminoaniline,

N-methyl-N-phenacylaniline .. ts N - ^ - CyanäthyI-2-ChoraniIin, NJ ^ -DiäthyI-3-trifIuormethyIan'lin, N-ethyl-N-phenylaniline,

Diphenylamine, N-methyldiphenylamine. N-methyl-4-ethoxydiphenylamine. Or N-phenylmorpholine, further z. B. Amines of the formula

NHCOR ₃

where d, Ri and R2 mean the same as above and Rs is a hydrogen atom, an optionally substituted alkyl, cycloalkyl or alkoxy group or a Benzene radical means, and in particular those of the formula

CH ₂ CH ₂ OCH ₂ CH ₂ CN CH ₂ CH ₂ OCH ₂ CH ₂ CN

NHCCR ₃

where d and Rj have the meaning given.

Also particularly valuable results are obtained with coupling components of the formulas

CH ₂ CH ₂ OCH ₂ CH ₂ CN CHjCHjOCO-alkyl

4, <^ \ - NH-CH ₂ CH ₂ -O-CH ₂ CH ₂ Cn

obtained, where c and d have the meaning given * to have.

The following coupling components are such examples:

OCH3

N- (CH ₂ CH ₂ OCH ₃ CH ₂ CN) ₂

NHCOCH3 OC ₂ H ₅

N (CH ₂ CH ₂ OCH ₂ CH ₂ CN) ₂

NHCHO

? ^CHl

CK

CH ₂ CH ₃ OCOCH.,

NHCOCH ₃

-NHCH ₂ CHjOCH ₂ CH ₂ CN NHCOCH,

OCH ₃

NHCH, CH, OCH, CH, CN

20th

NHCOCH ₃

OC ₂ H ₅

NHCH ₂ CH ₂ OCH ₂ CH ₂ Cn

NHCOCH,

OCHj

/ ^ J) -NIICH ₂ CH ₂ OCOCh ₃

NHCOCH ₃ OCH ₃

<\ - NHCh ₂ CH ₂ OCH ₂ CH ₂ CN NHCOOC ₂ H ₅ OCH ₃

<(^ \ - NHCH ₂ CH ₂ OCH ₂ CH ₂ CN NHCOCH ₂ CH ₃

As coupling components of the naphthalene series, apart from the naphthols, for example 1- or 2-naphthylamine and 2-phenylaminonaphthalene, 1-dimethylaminonaphthalene or 2-ethylaminonaphthalene called from the series of heterocyclic couplings Treatment components are, for example, the indoles, such as 2-methyl-indole, 24-dimethylindole, 2,4-dimethyl-7-methoxyindole,

2-PhenyI- or 2-MethyI-5-ethoxyindole, b5

N ^ -CyanäthyI-2-MethyIindoI,

2-methyl-5- or -6-chloroindole, 1,2-dimethylindole, l-methyl-2-phenylindole.

2-methyl-5-nitroindole, 2-methyl-5-cyanoindole, 2-methy! -7-chloroindole, 2-methyl-5-fluoro- or -5-bromoindole, 2-methyl-5,7-dichloroindole or 2-phenylindole.

I cyanoethyl ^ ö-dimethylindole, pyridines like

S-cyano ^ .e-dihydroxy ^ -metriyl-pyridine, also Pyrazoles, e.g. B. that

l-phenyl-5-amino-pyrazole or 3-methyl-pyrazolone or that

I -Phenyl-i-methyl-pyrazolon-S-,

l ^ -Dimethyl-pyrazolon-5, l-butyl-S-methylpyrazolone-S, l-oxyethyl-3-methyl-pyrazolon-5, 1-cyanoethyl-3-methylnyl pyrazolone-5, l- (o-chlorophenyl) -3-methylpyrazolon-5,

Quinolines, like that

8-hydroxyquinoline,

I -MethyM-hydroxyquinolone ^, N-ethyl-S-oxy-T-methyl- or N, j3-cyanoethyl-

1,2,3,4-tetrahydroquinoline or pyrimidene, such as

Barbituric acid, as well

1,3-indanedione, 1,8-naphthindanedione,

Dimedon, Acetesäigsäureanilid,

m-hydroxy-N, N-diethylaniline, 3-hydroxy-4'-methyldiphenylamine,

Hydroquinone monomethyl ether, Acetylacetone, 5-hydroxy-benzothiazole and

1 2- diphenylpyrazoline SS-dione. Furthermore, diazotizable amines, such as. B.

1-amino-3-methylbenzene, 1-amino-3-methylbenzene, 1-amino-2-methox> -5-methylbenzene, 1-aminonaphthalene etc.

be used, so that aminoazo dyes are formed, which in turn are diazotized and with the above mentioned coupling components can be combined to dis- or polyazo dyes.

As fiber-reactive anthraquinone dyes are run:

O NH-CH ₂ CHOH-CH ₂ Ci

0 NH-CH ₂ -CHOH-CH ₂ Ci O NH-CH ₃

/ V MH-C C-Cl

Il I

N N

C Cl

O NH

N-S

! ο

NH-CO-CH ₂ CHj-CI

and

20th

CH ₂ -NHCO-CH ₂ -Cl> s

Dioxane is used as a solvent. Tetrahydrofuran, glycerol formal and glycol formal, as well as acetonitrile and pyridine, diacetone alcohol, also higher-boiling glycol derivatives, such as ethylene glycol monomentyl, ethyl and butyl ethers and diethylene glycol nionomethyl or ethyl ether, thiodiglycol, ethyl carbonate, ethylene glycol, as long as they are liquid at room temperature, polyethylene glycol and especially the group of water-miscible active solvents boiling ^{above 120 ° C. such as}

N ₁ N-dimethylformamide, Ν, Ν-dimethylacetamide,
N-methylpyrrolidone, 1,5-dimethylpyrrolidone,
N ₁ N-dimethyl methoxyacetamide,
Ν, Ν, Ν ', Ν'-tetramethylurea,
Tetramethylene sulfone (salfolane) and
3-methylsulfolane and dimethylsulphoxide
In contrast, the dye preparations according to the invention are free from phosphorus-containing solvents.

The dye preparations according to the invention can contain dispersants. However, it is possible to refrain from using dispersants if water-insoluble dyes are to be dissolved in an organic liquor. In other cases, namely whenever the dyes are at least partly in the dispersed state in the dye liquor, the presence of dispersants is indicated
Important representatives of such dispersants belong in particular to the following non-ionic compound types:

a) Polyglycol compounds, such as polyoxyalkylated fatty alcohols, polyoxyalkylated polyols. polyoxyalkylated Mercaptans and aliphatic amines, polyoxyalkylated alkylphenols and naphthols, polyoxyalkylated Alkylaryl mercaptans and alkylarylamines.

b) fatty acid esters of ethylene and polyethylene glycols, as well as propylene and butylene glycol, des Glycerine, or polyglycerine and pentaerythritol, as well as sugar alcohols such as sorbitol, Sorbitans and sucrose.

c) N-hydroxyalkyl-carbonamides, polyoxalkylated Carbonamides and sulfonamides.

d) Liquid polyalkylene glycols, especially polyethylene glycols.

For example, the following can be mentioned as advantageously usable L ^ ispcrgotorcn oüs uicscn oruppcn: AniSgC tion products of 8 moles of ethylene oxide to 1 mole of p'-tert-octylphenol, of 15 or 6 moles of ethylene oxide to castor oil, of 20 moles of ethylene oxide to the alcohol CieH33OH, ethylene oxide Adducts of di - («- phenylethyl) phenols, Polyäthylenoxj d-tert.dodecylthioäther, polyamine, polyglycol ethers or adducts of 15 or 30 mol of ethylene oxide with 1 mol of amine Ci ₂ HmNH ₂ or Ci ₈ H ₃₇ NH ₂ .

Useful anionic dispersing agents are alkyl aryl sulfonates Cg_ I _2, QM-alkyl succinic acid, C ₈ -M fatty alcohol Schwefelsäureester, sulfation of unsaturated oils and fats, and C ₈ -2O-alkyl phosphoric acid esters. Particularly valuable dispersants are fatty acid esters of sorbites, ethoxylated alkanolamides, ethoxylated phenols and ethoxylated phosphate esters.

The dye preparations according to the invention are generally produced in a simple manner Mixing, stirring as appropriate, or by grinding the components, e.g. B. in a Kugelmüh-Ie.

The dye preparations described above are suitable for the production of conventional aqueous dye baths and, above all, for production of dyebaths based on organic solvents in which the dyes are dispersed or are preferably solved.

In the examples below, the parts, unless otherwise specified, mean parts by weight, the Percentages by weight and temperatures are given in degrees Celsius.

example 1

In a mixture of 2 parts of tetrachlorethylene and 1 part of dimethylacetamide one carries 1 part at 20 to 25 ° of a fiber-reactive monoazo dye of the formula

BrCH ₂ -CHBr-CO-NH

-N = N

and stir until a clear solution is obtained. A storage-stable liquid preparation is obtained

13th

H c i s ρ i c I 2

Parts of the fiber-reactive dye of the formula

CI-CH ₂ CH ₂ -NH-SO ₂ -

-N =

H ₁ C

14th

CH ₂ CH ₂ OH

CH ₂ CH ₂ OH

are stirred into a mixture of 2 parts of dimethylformamide dilution with a padding liquor made of perchlorethylene and 1 part of coconut fatty acid ethanolamide. That one clear orange solution
created «liquid dye preparation gives at 15

Example 3

A C * mixture of 20 parts of diacetone alcohol, 10 parts of ethylene carbonate, 20 parts of the monoazo dye the formula

-N

N C-N = N

N (C ₂ H ₄ Cl) ₂

C ₂ H ₅

and 5 parts of sodium dodecylbenzenesulfonate are in The following table contains further, according to the

a ball mill until the desired J5 data of Examples 1 to 3 have been reached

Fineness. A stable dye preparation is obtained.
Dye dispersion.

No dye / parts

Solvent dispersant

ClCH ₂ -CH-CH ₂ O
OH

Parts

C-COOC ₂ H ₅ ethylene glycol monobuty lather

5 parts

O NH-CH ₂ CHOHCH ₂ Ci

3
CH ₃ SO ₂

Parts

O NH - CH ₂ CHOHCH ₂ CI
Cl

N = N

C ₆ H _n C Cl

/ / V

N NN

\ Il 1 I.

C ₂ H ₄ -NC C-OCH ₂ CH

CH ₃ I \ / j

C ₂ H ₅ N CH ₃

Tetramethylene adduct of sulfone stearyl

alcohol and

4 parts 20 moles

Ethylene oxide 1 part

y-butyrolactone -

CH ₃ ^{3 Te> le}

15th

continuation

16

No. Dye / Parts Solvent Dispersal

C ₂ H ₄ OCOCH ₃ CH ₂ CH ₃

4 CI-

-N = N

5 parts

5 O ₂ N

N = N

2 parts of 6 HO O NH-C ₂ H ₄ OCOCH ₂ Cl

NC C-OC ₂ H ₄ OC ₂ Hj

N (C ₂ H ₄ O CO C ₃ H ₄ ) Z

NHCOCH = CH-CH-CH ₂

I I

F ₂ C CF ₂

Part 1

7 NC

HO O NH-C ₂ H ₄ OCOCH ₂ CI

CHj

C ₂ H ₄ OCH ₃

NH

NO ₂

8 O ₂ N

5 parts

SO ₂ NHCjH ₄ Cl

= N

N = Ν, Ν, Ν ', Ν'- dibutyl-tetramethyl- naphtha urea sulfonic acid

C ₂ H ₄ OCOCH ₂ CH ₂ CH ₃ 4 parts

!Part

Diethylene

glycol mono-

methyl ether

5 parts

Dimethyl sulfoxide

2 parts

Thiodiglycol 5 parts

N-methylpyrrolidone

5 parts

Sodium oleate

5 parts

N-methyl
pyrrolidone
5 parts CH, Dioctyl
sulfo-
amber and
Tetrachlor
ethylene (Na-SaIz)
Part 1 10 parts Dimethyl
acctamid - OH
Jv 2 parts V? * H ₂ CC-
ι ι
CH,

Dyes / parts 17th O
n O NHCH ₃
COo 20 20 350 OCH ₃ OH 18th Disperser ClCH ₂ CO- <
< O NF Lauryl benzene
imidazole
sulfonate
O ^ parts continuation Ch ₃ \ _y solvent Castor oil
and 40 moles
Ethylene
os.fi No. .J 2 TeU Ethylene
glycol mono-
methyl ether
3.5 teüe 2 parts 10 CICH ₂ CO- < 1 ^ -DimethyI-
pyrrolidone
3 parts 11th I - ^^^> - C ₄ H, ^ VN (C ₂ H ₄ OCOCH ₂ CI) ₂ - CH ₂ NHCOCH ₂ Cl 5 parts CHj Cl
C ₂ H ₅ C
/ / \
N NN
\ Il
C ₂ H ₄ OC CN (C ₂ H ₄ OH) ₂
\ / "
N Dimethyl form
amide HjCO ₂ S- / O ^N - ^N - (
_ ^^ j> --Ν = Ν-γ 2 parts 12th 5 parts N /
Part 1 )H
S. and
Dimethyl sulf
oxide Coconut fat
acid- Cl
2 parts γ 2 parts methyl-
taurid (HOC ₂ H ₁ HN- Cl
i Cl Methylethyl
ketone 2 parts V-N = N- < 5 parts 13th 2 parts Nonyl
phenol and
9 moles
Ethylenic
oxide N = N - <^ Vi Dimethyl
acetamide
4 pieces 2 parts 14th C-Cl
N N
-C C- NH Dimethyl
sulfoxide
4 pieces 15th N

19th

continuation

No. Dye / Part Solvent Dispergator

16 (CIC ₂ Hi) ₂ N

Il c

CH = C

HjC

. C.

Il ο

5 parts

Ν, Ν, Ν ', Ν', - tetramethylurea

5 parts

Claims (7)

Patent claims: 1. Liquid dye preparations containing fiber-reactive dye, organic solvent and optionally dispersant, characterized in that it consists of a) at least 20%, based on the weight of the preparations, of at least one of sulfo groups free fiber-reactive disperse dye, b) a phosphorus-free organic solvent which is miscible with water in any ratio and c) optionally consist of an anionic or nonionic dispersant. 2. Dyestuff preparations according to claim 1, characterized * that one boils over 100 ° C Solvent used 3. Dye preparations according to Claims 1 and 2, characterized in that the dye component is an azo dye or an anthraquinone derivative 4. dye preparations according to claims 1 to 3, characterized in that they contain 25 to 50% Have dye content. 5. Process for the preparation of dye preparations, characterized in that the in the Claims 1 to 4 mentioned components mixed with one another or wet-ground 6. Use of the dye preparations according to claims 1-5 for dyeing fully synthetic Fibers, preferably polyamide fibers and / or hasically modified polyester fibers or polypropylene fibers. 7. Use of the dye preparations according to claims 1-5 for dyeing fully synthetic Fassrn, preferably polyamide fibers and / or base modified polyester fibers or polypropylene fibers, from organic liquors.