Claims
- 1. A process for dyeing and printing water-swellable cellulosic materials and blends thereof with synthetic materials in the presence of water and a solvent that is capable of maintaining cellulose in the swollen state, wherein the dye used is a compound of the general formula I: ##STR175## where K is the radical of a coupling component of the pyridone series, one of the radicals X, Y and Z is a carboxylic acid ester group of a total of 2 to 19 carbon atoms; and,
- the remaining substituents X, Y and Z are hydrogen, methyl, chlorine, bromine or nitro, with the proviso that the number of carbon atoms of the N-substituent in the pyridone moiety plus that of the carboxylic ester group is equal to or above 14.
- 2. A process as claimed in claim 1, wherein K in the dye used is a radical of the formula ##STR176## where; R is hydrogen, C.sub.1 -C.sub.10 -alkyl, allyl, C.sub.1 -C.sub.4 -alkyl which is substituted by C.sub.1 -C.sub.4 -alkoxy, by phenoxy, by phenoxyethoxy or by phenyl (which is itself unsubstituted or substituted), C.sub.6 -C.sub.12 -polyalkoxyalkyl, phenyl, cyclohexyl or norbornyl.
Priority Claims (1)
| Number |
Date |
Country |
Kind |
| 2929763 |
Jul 1979 |
DEX |
|
Parent Case Info
This is a continuation of application Ser. No. 164,005, filed June 30, 1980, now U.S. Pat. No. 4,305,718.
The present invention relates to a process for dyeing and printing cellulose-containing textile material, wherein the dye used is a compound of the general formula I ##STR2## where K is the radical of a coupling component of the pyridone, pyrazole or indole series,
The coupling component of the general formula KH preferably has the formula ##STR3## where R is hydrogen, C.sub.1 -C.sub.10 -alkyl, allyl, C.sub.1 -C.sub.4 -alkyl which is substituted by C.sub.1 -C.sub.4 -alkoxy, by phenoxy, by phenoxyethoxy or by phenyl (which is itself unsubstituted or substituted), C.sub.6 -C.sub.12 -polyalkoxyalkyl, phenyl, cyclohexyl or norbornyl,
Examples of N-substituents of the carboxamide or sulfonamide groups of the diazo component are methyl, ethyl, propyl, butyl, n-hexyl, phenyl, benzyl, phenylethyl, 2-phenylpropyl, 2-ethylhexyl, 1,5-dimethylhexyl, n-octyl, n-dodecyl, n-tridecyl, 6-methylheptyl, 3-(2-ethyl-hexoxy)-propyl, stearyl, cyclohexyl, .beta.-methoxyethyl, .beta.-butoxyethyl, .gamma.-methoxypropyl, .gamma.-butoxypropyl or .gamma.-ethoxypropyl; furthermore, the N-substituted carboxamide or sulfonamide can be the pyrrolidide, piperidide or morpholide.
Examples of O-substituents of sulfonic acid ester groups are phenyl, o-, m- and p-tolyl, o-, m- and p-chlorophenyl and 2,5-dichlorophenyl.
Examples of suitable carboxylic acid ester groups are: ##STR4##
The carbamyl and carboxylic acid ester groups listed as possible substituents of the diazo component are also possible meanings of the radical B in the coupling component.
Specific examples of radicals R, in addition to those already mentioned, are: ##STR5##
The dyes of the general formula I, to be used according to the invention, are obtained if an amine of the general formula III ##STR6## which is free from ionic groups is diazotized and coupled in a conventional manner with a component KH of the general formula II, X, Y, Z, R, R.sup.1, A, B, E and T having the stated meanings.
Examples of suitable amines of the formula II are: the methyl, ethyl, n-butyl, i-butyl, n-hexyl, cyclohexyl, .beta.-ethylhexyl, n-decyl, i-decyl, octadecyl, phenyl, 4'-tert.-butylphenyl, benzyl, phenylethyl, phenoxyethyl, .beta.-ethoxy-ethyl, .beta.-butoxy-ethyl, .beta.-(.beta.'-butoxy-ethoxy)-ethyl and .gamma.-(.gamma.'-methoxy-propoxy)-propyl esters of 2-aminobenzoic acid and of 4-aminobenzoic acid, and of the monohalo, dihalo, nitro and nitrohalo derivatives of these acids, eg. decyl 2-amino-3,5-dibromobenzoate, .beta.-phenoxy-ethyl 2-amino-5-chloro-benzoate, decyl 2-amino-5-nitro-benzoate and decyl 2-amino-3-bromo-5-nitro-benzoate, as well as 2- and 4-aminobenzoic acid dimethylamide, diethylamide, iso-propylamide, di-n-butylamide, piperidide, morpholide, n-hexylamide, cyclohexylamide, ethylhexylamide, n- and i-decylamide, anilide, N-methylanilide, .beta.-phenylethylamide and .gamma.-(.beta.'-phenoxy-ethoxy)-propylamide, as well as the corresponding amides of the monohalo, dihalo, nitro and nitrohalo derivatives of the acids, eg. 2-amino-3,5-dibromobenzoic acid .beta.-ethylhexylamide, 2-amino-5-nitro-benzoic acid cyclohexylamide and 2-amino-3-bromo-5-nitro-benzoic acid .beta.-ethylhexylamide.
Further suitable amides are 4-aminobenzenesulfonic acid 2-ethylhexyl-amide, tridecylamide, piperidide, .beta.-phenylethyl-amide, 2-phenylpropyl-amide, n- and i-octylamide, 6-methylhept-2-ylamide, n-hexylamide, .gamma.-(.beta.-phenoxyethoxy)-propylamide, n-dodecylamide, diisooctylamide, 2-ethylhexoxy-propylamide, octadecylamide, anilide, toluidide, N-methylanilide, N-ethylanilide, N-ethylcyclohexylamide, N-methylcyclohexylamide, cyclohexylamide, .beta.-cyclohexylethylamide, benzylamide, di-n-butylamide and dibenzylamide, and the corresponding compounds derived from 4-amino-3-chloro-, -3-bromo-, -3,5-dichloro- and -3,5-dibromo-benzenesulfonic acid; 4-aminobenzoic acid tridecylamide, 2-phenylpropyl-amide, n- and i-octylamide, n-dodecylamide, diisooctylamide, 2-ethylhexoxy-propylamide, octadecylamide, N-ethylcyclohexylamide, N-methylcyclohexylamide, .beta.-cyclohexylethyl-amide and benzylamide, and the corresponding amides of 4-amino-3-chloro-, -3-bromo-, -3,5-dichloro- and -3,5-dibromo-benzoic acid; phenyl, tolyl, chlorophenyl and 2,5-dichlorophenyl 2-aminobenzenesulfonate; 2-aminobenzenesulfonic acid N-methylanilide, N-ethylanilide, N-methylcyclohexylamide, N-ethylcyclohexylamide, di-n-butylamide, dibenzylamide and di-(2-ethylhexyl)-amide, and the corresponding esters and amides of the monohalo, dihalo, nitro and nitrohalo derivatives of 2-aminobenzenesulfonic acid, eg. 2-amino-5-nitro-benzenesulfonic acid N-ethylanilide, phenyl 2-amino-3,5-dibromobenzenesulfonate, phenyl 2-amino-5-nitrobenzenesulfonate, phenyl 2-amino-3-bromo-5-nitro-benzenesulfonate and 2-amino-3,5-dibromobenzenesulfonic acid N-methylanilide; phenyl 4-aminobenzenesulfonate, phenyl 4-amino-3,5-dibromobenzenesulfonate and tolyl 4-aminobenzenesulfonate; 4-amino-2,5-dichlorobenzenesulfonic acid 2-ethylhexoxy-propylamide, 2-phenylethylamide, 2-phenoxy-ethoxy-propylamide, n-octylamide and 2-ethylhexyl-amide.
Preferred dyes for use in the process according to the invention are those of the formula ##STR7## where A, E, R, R.sup.1 and T have the stated meanings and R.sup.2 is methyl or phenyl, and where one of X.sup.1 and Y.sup.1, one of X.sup.2 and Y.sup.2, and one of X.sup.3 and Y.sup.3 is a carboxylic acid ester group or carboxamide group of a total of 2 to 13 carbon atoms, or a sulfonamide group or unsubstituted or substituted sulfonic acid phenyl ester group of a total of 6 to 18 carbon atoms, and of the remaining substituents, either X.sup.1 or Y.sup.1, and Z.sup.1, are hydrogen, either X.sup.2 or Y.sup.2, and Z.sup.2, are hydrogen, chlorine or bromine and either X.sup.3 or Y.sup.3, and Z.sup.3, are hydrogen, chlorine, bromine or nitro.
Suitable processes for applying the dyes of the formula I are, in particular, those described in German Pat. No. 1,811,796, German Laid-Open Applications DOS Nos. 2,524,243 and DOS No. 2,528,743 and German Patent Application P No. 2,855,188.4. Details of the methods of application may be found in the Examples, where parts and percentages are by weight, unless stated otherwise.
US Referenced Citations (3)
| Number |
Name |
Date |
Kind |
| 3706525 |
Blackwell et al. |
Dec 1972 |
|
| 4224026 |
Reinhardt |
Sep 1980 |
|
| 4305718 |
Loffler et al. |
Dec 1981 |
|
Foreign Referenced Citations (2)
| Number |
Date |
Country |
| 1559001 |
Jan 1980 |
GBX |
| 1584212 |
Feb 1981 |
GBX |
Continuations (1)
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Number |
Date |
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| Parent |
164005 |
Jun 1980 |
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Patent Grant
4380452
