GB1561420A - Azo dyestuffs containing a phthalimido - alkyl group - Google Patents
Azo dyestuffs containing a phthalimido - alkyl group Download PDFInfo
- Publication number
- GB1561420A GB1561420A GB3695077A GB3695077A GB1561420A GB 1561420 A GB1561420 A GB 1561420A GB 3695077 A GB3695077 A GB 3695077A GB 3695077 A GB3695077 A GB 3695077A GB 1561420 A GB1561420 A GB 1561420A
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- Prior art keywords
- denotes
- group
- amino
- methyl
- phenyl
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/51—Monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0801—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
(54) AZO DYESTUFFS CONTAINING A PHTHALIMIDO
ALKYL GROUP
(71) We, BAYER AKTIENGESELLSCHAFT, a body corporate organised under the laws of Germany, of Leverkusen, Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement::
The invention relates to dyestuffs which, in the form of the free acid, correspond to he formula
in which
D denotes the radical of an aromatic-carboxylic or aromatic-heterocyclic diazo
component,
X denotes OH, NH-SO2-R5, N(R6)-alkylene-OSO3H, N(R6)-alkylene-SO3H,
N(R6)-arylene-SO3H, N(R6)-arylene-CH2-SO3H or N(R6)-arylene-SO2
NH-SO2-R5, the arylene group being optionally substituted, R, denotes hydrogen, C1-C4-al1lyl, C1--alkoxy, chlorine or bromine,
R1 denotes hydrogen, alkyl, optionally substituted alkoxy or acylamino,
R2 denotes hydrogen or alkyl,
R3 denotes hydrogen, optionally substituted aralkyl, or alkyl optionally substituted
other than by aryl,
R4 denotes alkylene,
R3 denotes optionally substituted alkyl, aryl or dialkylamino,
R, denotes hydrogen or alkyl and
m denotes 1 or 2.
Suitable aromatic-heterocyclic diazo components are those of the thiazole, benzthiazole, thiadiazole, benzisothiazole, triazole, pyrazole or thiophene series, which optionally can be substituted by C1--alkyl, aryl, halogen, cyano, C1-C4-alkoxy or C144-alkoxycarbonyl.
Suitable aromatic-carbocyclic diazo components are those of the benzene or naphthalene series, which can be substituted by halogen, cyano, carboC1-C4-alkoxy, niuo, optionally substituted alkyl, optionally substituted alkoxy, hydroxyl, thiocyanato, optionally substituted alkylsulphonyl, arylsulphonyl, aralkylsulphonyl, optionally monosubstituted or disubstituted carbatnoyl or optionally monosubstituted or disubstituted sulphatnoyl.
Possible substituents of the carbamoyl and sulphamoyl groups are optionally substituted alkyl, cycloallyl, aryl or aralkyl as well as heterocyclic radicals.
The alkyl groups can also be joined, with the inclusion of the N atom of the carbamoyl or sulphamoyl group and optionally with the inclusion of a further hetero-atom, such as N, O or S, to form a 5-membered or 6-membered ring.
Radicals of such heterocyclic structures are, for example, piperidinyl, pyrrolidinyl
and morpholinyl.
Dialkylamino suitable as R5 is, for example, di-C1-C4-alkylamino.
Cyclopentyl and cyclohexyl, for example, are cycloalkyl which is suitable as a
substituent of the carbamoyl or sulphamoyl groups.
Alkyl sultable as R1, R2 and R6 is, for example, C1-C4-alkyl.
Optionally substituted alkyl suitable as R3 and R5, in the alkylsulphonyl groups, as
a substituent of the carbamoyl and sulphamoyl radicals and in the aromatic-carbo- cyclic diazo component is, for example, C1-C4-alkyl which can be substituted by
halogen, cyano, hydroxyl or C1-C4-alkoxy, such as methyl, ethyl, butyl, methoxy
methyl, hydroxyethyl, cyanoethyl or chloroethyl.
Aryl suitable as R5, in the arylsulphonyl radicals, in the heterocyclic diazo com
ponent and as a substituent of the carbamoyl and sulphamoyl groups is, in particular, phenyl which is optionally further substituted by phenyl, C1-C4-alkyl, halogen, nitro or C1-C4-alkoxy, or naphthyl, for example, phenyl, 1-naphthyl, 2-naphthyl, p
biphenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4-ethoxyphenyl, o-, m- and p-tolyl, 4-nitrophenyl, 2,5-dimethoxyphenyl, 2,5-dimethylphenyl or 4-ethylphenyl.
Aralkyl suitable as R,, in the aralkylsulphonyl groups and as a substituent of the carbamoyl or sulphamoyl groups is, in particular, benzyl or 2-phenylethyl, it being possible for the phenyl radical in these groups optionally to be further substituted by C1-C4-alkyl, C1-C4-alkoxy, halogen or cyano, for example benzyl, 2phenylethyl, p-methylbenzyl, p-methoxybenzyl, 2,4-dichlorobenzyl, 4-cyanobenzyl or p-bromophenylethyl.
Alkoxy suitable as R1 or as a substituent of D is, in particular, C1-C4-alkoxy which optionally can be substituted by OH, halogen or cyano, such as methoxy, ethoxy, propoxy, butoxy, 2-hydroxythoxy, 2-cyano-ethoxy or 2-chloro-ethoxy.
Suitable halogen atoms are fluorine, chlorine and bromine, especially chlorine and bromine.
Alkylene suitable as R4 or in (N(R6)-alkylene-OSO3H and N(R6)-alkylene-SO3H is, in particular, C2-C4-alkylene, for example
-CH2-CH2-, -CH(CH3)-CH2-CH2-, -CH2-CH(CH3)CH2- or
-CH2-CH2-CH2-CH2-.
Arylene suitable in N(R6)-arylene-SO2-NH-SO2-R5, N(R6)-arylene-SO3H or
N(R6)-arylene-CH2-SO3H is, in particular, 1,2-, 1,3- or 1,4-phenylene, it being possible for phenylene to be substituted by C1-C4-alkyl, C1-C4-alkoxy, chlorine, bromine, cyano, nitro of benzyloxy.
A suitable heterocyclic substituent of the sulphamoyl or carbamoyl radicals is, for example, 2-sulpholanyl. Acyl suitable in the acylamino group is, in particular, C1-C4-alkylcarbonyl, C1-C4-aIkoxycarbonyl, phenoxycarbonyl or benzoyl.
Preferred dyestuffs are those which, in the form of the free acid, correspond to the formula
wherein
X has the abovementioned meaning,
R1' denotes hydrogen, C1-C3-alkyl, acetylamino, methoxy or ethoxy,
R2, denotes hydrogen or methyl, R,' denotes methyl, ethyl, benzyl or cyanoethyl,
R4' denotes C2H4 or C3H6,
R7 and R8 denote hydrogen, chlorine, bromine, cyano, nitro, C1-C4-alkyl,
C1-C4-alkoxy, carbo-C1-C4-alkoxy, hydroxyl, trifluoromethyl, C1-C4-alkyl
sulphonyl, phenylsulphonyl or benzylsulphonyl, or carbam@yl or sulphamoyl
which are optionally monosubstituted or disubstituted by C1-C4-alkyl, phenyl, benzyl or phenethyl and
R9 denotes hydrogen, chlorine, bromine, C4-C4-alkyl, trifluoromethyl, sul
phamoyl, C1-C4-alkylsulphonyl, phenylsulphonyl or benzylsulphonyl.
Particularly preferred dyestuffs are those which, in the form of the free acid, correspond to the formula
wherein R1,, R2, and R,' have the abovementioned meaning,
R1, denotes hydrogen, chlorine, bromine, trifluoromethyl, methyl, ethyl, cyano,
methylsulphonyl, ethyl sulphonyl or phenylsulphonyl, or sulphamoyl which
is optionally monosubstituted or disubstituted by C1C4-alkyl, phenyl or
benzyl, Rs' denotes hydrogen, chlorine, bromine, cyano, carbo-C1-C4-alkoxy, Cl-c4- alkylsulphonyl, phenylsulphonyl or benzylsulphonyl, or sulphamoyl which is
optionally monosubstituted or disubstituted by C1-c4-alkyl, benzyl,
phenethyl or phenyl and
R9, denotes methyl, chlorine, bromine or hydrogen.
Very particularly preferred dyestuffs are those which, in the form of the free acid, correspond to the formula
in which
R8, has the meaning indicated above,
R1" denotes hydrogen or methyl,
R3" denotes methyl, ethyl or benzyl,
R7" denotes chlorine or trifluoromethyl and
R9" denotes hydrogen or chlorine.
Further dyestuffs which are particularly preferred are those which, in the form of the free acid, correspond to the formula
in which
R1', R2', R3', R7' and R9' have the meaning indicated above and
X' denotes OH, NH-SO2-R5', N(R6')-C2-C4-alkylene-O-SO3H,
N(R6')-C2-C4-alkylene-SO3H or N(R6')-phenylene-SO3H, in which
R3' denotes C1-C4-alkyl or phenyl which is optionally substituted by methyl,
ethyl, chlorine, bromine or methoxy and
R6' denotes hydrogen or C1-C4-alkyl.
Dyestuffs which, in the form of the free acid, correspond to the formula
in which
R1", R3", R7" and R9" have the meaning indicated above and
X" denotes OH, -NH-SO2-R5", N(R6")-CH2-CH2-OSO3 or
N(R6")-CH2-CH2-SO3H, in which
R5" denotes C1-C4-alkyl or phenyl which is optionally substituted by chlorine,
methyl, methoxy or ethyl and
R6" denotes hydrogen, methyl or ethyl, are very particularly preferred.
Dyestuffs of the formula I can be prepared in the customary manner by diazotising an amine of the formula
[D-NH2-]-(SO2X)n (VII) in which
D and X have the abovementioned meaning and
n denotes 0 or 1, and subjecting the diazo compound to a coupling reaction with an amme or the formula
wherein
Ro, R1, R2, R,, Rs and X have the abovementioned meaning and
p denotes 0 or 1,
with the proviso that n and p cannot at the same time be 0.
The coupling components VIII are prepared by heating amines of the formula
wherein
R1,R2,R3 and R4 have the abovementioned meaning, together with phthalic acids of the formula
wherein R, X and n have the abovementioned meaning,
or with corresponding phthalic anhydrides, to 1502500C.
Examples of suitable amines VII are aniline, 2-, 3-, and 4-chloroaniline 2,5
dichloroaniline, 2,4-dichloroaniline, 3-bromoaniline, 2-bromoaniline, 2-trifluoromethylaniline, 2-, 3- and 4-toluidine, 2-, 3- and 4-anisidine, 2-ethylaniline, 4-propoxyaniline, 4-benzylsulphonylaniline, 2-chloro-4-ethylsulphonylaniline, 2,5-dichloro-4-propylsulphonylaniline, aniline-4-N,N-dimethylsulphonamide, 2-chloroaniline-4-(2-methyl)sulphoanilide, aniline-2-trifluoromethyl-4-sulphonamide, aniline-2-trifluoromethyl-4-Nmethyl-sulphonamide, aniline-2-trifluoromethyl-4-N,N-dimethyl-sulphonamide, aniline-2-trifluoromethyl-4-N-ethyl-sulphonamide, aniline-2-trifluoromethyl-4-N,Ndiethylsulphonamide, aniline-2-trifluoromethyl-4-N-propyl-sulphonamide, aniline-2trifluoromethyl-4-N-butyl-sulphonamide, aniline-2-trifluoromethyl-4-N-phenyl-sulphonamide, aniline-2-trifluoromethyl-4-N-methyl-N-phenyl-sulphonamide, aniline-2-trifluoromethyl-4-N-benzyl-sulphonamide, aniline-2-trifluoromethyl-4-N-(m-tolyl)-sulphonamide, aniline-2-trifluoromethyl-4-N-ss-hydroxyethyl-sulphonamide, aniline-2 trifluoromethyl-4-N-γ-hydroxypropyl-sulphonamide, aniline-2-trifluoromethyl-4-N ss-chloroethyl-sulphonamide, aniline-2-trifluoromethyl-4-N-cyclohexyl-sulphonamide, aniline-2-trifluoromethyl-4-N,N-tetramethylene-sulphonamide, aniline-2-trifluoromethyl-5-N,N-tetramethylene-sulphonamide, aniline-3-trifluoromethyl-4-sulphonamide, aniline-3-trifluoromethyl-4-N,N-dimethylsulphonamide, aniline-2-trifluoromethyl-5chloro-4-sulphonamide, aniline-2-trifluoromethyl-5-chloro-4-N,N-dimethylsulphonamide, aniline-4,54ichloro-2-N,N-dimethyl-sulphonamide, aniline-4,5-dichloro-2- diethyl-sulphonamide, aniline-4,5-dichloro-2-N-ethyl-sulphonamide, aniline-2,5-dichloro-4-sulphonamide, aniline-2,5-dichloro-4-N-methyl-sulphonamide, aniline-2,5dichloro-4-N-ethyl-sulphonamide, aniline-2,5-dichloro-4-N-propyl-sulphonamide, aniline-2,5-dichloro-4-N-butyl-sulphonamide, aniline-2,5-dichloro-4-N-benzyl-sulphonamide, aniline-2,5-dichloro-4-N-phenyl-sulphonamide, aniline-2,5-dichloro-4-N-(mtolyl)-sulphonamide, aniline-2,5-dichloro-4-N-γ-chloropropyl-sulphonamide, aniline2,5-dichloro-4-ss-hydroxyethyl-sulphonamide, aniline-2,5-dichloro-4-N-γ;-hydroxy- propyl-sulphonamide, aniline-2,5-dichloro-4-N-y-hydroxybutyl-suIphonamide, aniline2,5-dichloro-4-N-cyclohexyl-sulphonamide, aniline-2,5-dichloro-4-N,N-dimethyl-sulphonamide, aniline-2,5-dichloro-4-N,N-diethyl-sulphonamide, aniline-2,5-dichloro-4
N,N-bis-(ss-hydroxyethyl)-sulphonamide, aniline-2,5-dichloro-4-N,N-tetramethylenesulphonamide, aniline-2,5-dichloro-4-N,N-pentamethylene-sulphonamide, aniline-2,6dichloro-4-sulphonamide, aniline-2,6-dichloro-4-N-methyl-sulpnonamide, aniline-2,6dichloro-4-N-ethyl-sulphonamide, aniline-2,6-dichloro-4-N-ss-hydroxyethyl-sulphonamide, aniline-2,6-dichloro-4-N-benzyl-sulphonamide, aniline-2,6-dichloro-4-N-phenylsulphonamide, aniline-2,6-dichloro-4-N-γ;-hydroxybutyl-sulphonamide, aniline-2,6dichloro-4-N,N-diethyl-sulphonamide, aniline-2,6-dichloro-4-methyl-N-phenyl-sulphonamide, ethyl-(3,5-dichloro-4-amino-phenyl)-sulphone, propyl-(3,5-dichloro-4amino-phenyl)sulphone, butyl-(3,5-dichloro-4-amino-phenyl)-sulphone, benzyl-(3,5dichloro-4-amino-phenyl)-sulphone, ss-phenethyl-(2,5-dichloro-4-amino-phenyl)-sulphone, ss-cyanoethyl-(2,5-dichloro-4-amino-phenyl)-sulphone, methyl-(4,5-dichloro-2amino-phenyl)-sulphone, ethyl-(4,5-dichloro-2-amino-phenyl)-sulphone, methyl-(3chloro-5-methyl-4-amino-phenyl)-sulphone, ethyl-(3-chloro-5-methyl-4-amino-phenyl)sulphone, methyl-(3-chloro-5-methyl-6-amino-phenyl-sulphone, ethyl-(3-chloro-5methyl-6-amino-phenyl)-sulphone, methyl-(3-chloro-4-methyl-6-amino-phenyl)-sulphone, ethyl-(3-chloro-4-methyl-6-amino-phenyl)-sulphone, methyl-(3,5-dichloro-2amino-phenyl)-sulphone, ethyl-(3,3-dichloro-2-amino-phenyl)-sulphone, methyl-(2,5 dichloroGamino-phenylksulphone, ethyl-(2,5-dichloro-4-amino-phenvl)-sulphone, benzyl-(2,5-dichloro-4-amino-phenyl)-sulphone, methyl-(2,6-dibromo-4-amino-phenyl)sulphone, methyl-(4-amino-phenyl)-sulphone, ethyl-(4-amino-phenyl)-sulphone, sscyanoethyl-(4-amino-phenyl)-sulphone, ss-phenylethyl-(4-amino-phenyl)-sulphone, methyl-(2-amino-phenyl)-sulphone, ethyl-(2-amino-phenyl)-sulphone, propyl-(2-aminophenyl)-sulphone, butyl-(2-amino-phenyl)-sulphone, methyl-(3-amino-phenyl)-sulphone, ethyl-(3-amino-phenyl)-sulphone, butyl-(3-amino-phenyl)-sulphone, benzyl-(3amino-phenyl)-sulphone, ss-hydroxyethyl-(3-amino-phenyl)-sulphone,ss-cyanoethyl-(3amino-phenyl)-sulphone, methyl-(3-methyl-4-amino-phenyl)-sulphone, ethyl-(3-methyl4-amino-phenyl)-sulphone, methyl-(3-chloro-4-amino-phenyl)-sulphone, methyl-(3bromo-4-amino-phenyl)-sulphone, methyl-(3-fluoro-4-amino-phenyl)-sulphone, methyl (3-trifluoromethyl-4-amino-phenyl)-sulphone, ethyl-(3-chloro-4-amino-phenyl)-sulphone, ethyl-(3-bromo-4-amino-phenyl)-sulphone, ethyl-3-fluoro-4-amino-phenyl)sulphone, ethyl-(3-trifluoromethyl-4-amino-phenyl)-sulphone, n-propyl-(3-chloro-4amino-phenyl)-sulphone, n-propyl-(3-fluoro-4-amino-phenyl)-sulphone, n-propyl-3
trifluoromethyl-4-amino-phenyl)-sulphone, n-butyl-(3-chloro-4-amino-phenyl)-sulphone,
n-butyl-(3-trifluoro-methyl-4-amino-phenyl)-sulphone, ss-cyanoethyl-(3-chloro-4amino-phenyl-sulphone, ss-cyanoethyl-(3-trifluoromethyl-4-amino-phenyl)-sulphone,
benzyl-(3-chloro-4-amino-phenyl)-sulphone, benzyl-(3-fluoro-4-amino-phenyl)
sulphone, benzyl-(3-trifluoromethyl-4-amino-phenyl)-sulphone, 4-chlorobenzyl
(3-trifluoromethyl-4-amino-phenyl)-sulphone, 4-methylbenzyl-(3-chloro-4-amino
phenyl)-sulphone, ss-phenylethyl-(3-chloro-4-amino-phenyl)-sulphone, ss
hydroxyethyl-(3-chloro-4-amino-phenyl)-sulphone, ss-hydroxyethyl-(3-trifluoromethyl4-amino-phenyl)-sulphone, y-hydroxypropyl-(3-chloro-4-amino-phenyl)-sulphone} y- hydroxypropyl-(3-trifluoromethyl-4-amino-phenyl)-sulphone, ss-methoxycarbonylethyl- (3-chloro-4-amino-phenyl)-sulphone, ss-methoxycarbonylethyl-(3-trifluoromethyl-4amino-phenyl)-sulphone, methyl-(4-chloro-3-amino-phenyl)-sulphone, methyl-(4-tri- fluoromethyl-3-amino-phenyl)-sulphone, ethyl-(4-trifluoromethyl-3-amino-phenyl)sulphone, n-propyl-(4-chloro-3-amino-phenyl)-sulphone, n-butyl-(4-trifluoromethyl-3amino-phenyl)-sulphone, ss-cyanoethyl-(4-trifluoromethyl-3-amino-phenyl)-sulphone, ss-hydroxyethyl-(4-trifluoromethyl-3-amino-phenyl)-sulphone, (3-amino-4-chlorobenzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-chloro-benzenesulphonyl)benzenesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-benzenesulphonamide, (3amino-6-methoxy-benzenesulphonyl)-butanesulphonamide, (4-amino-benzenesulphonyl)p-toluenesulphonamide, (4-amino-benzenesulphonyl)-o-toluene-sulphonamide, (4amino-benzenesulphonyl)-methylsulphonamide, (4-amino-benzenesulphonyl)-butanesulphonamide, (4-amino-3-trifluoromethyl-benzenesulphonyl)-benzenesulphonamide, (4amino-3-trifluoromethyl-benzenesulphonyl)-methanesulphonamide, (4-amino-3-trifluoromethyl-benzenesulphonyl)-butanesulphonamide, (4-amino-3-trifluoromethylbenzenesulphonyl)-p-toluenesulphonamide, (4-amino-3-trifluoromethyl-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-trifluoromethyl-benzenesulphonyl)-2naphthaylsulphonamide, (4-amino-3-chloro-benzenesulphonyl)-benzenesulphonamide, (4-amino-3-chloro-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-3-chlorobenzenesulphonyl)-methanesulphonamide, (4-amino-3 -chloro-benzenesulphonyl)-di- methylaminosulphonamide, (4-amino-3-bromo-benzenesulphonyl)-benzenesulphon amide, (4-amino-3-methyl-henzenesulphonyl-benzenesulphonamide, (4-amino-3methyl-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-2,5-dichloro-benzenesulphonyl)benzenesulphonamide, (4-amino-2,5-dichloro-benzenesulphonyl)-propanesulphonamide, (4-amino-2,5-dichloro-benzenesulphonyl)-p-toluenesulphonamide, (4amino-2,5-dichloro-benzenesulphonyl)-dimethylaminosulphonamide, (4-amino-3,5-dichloro-benzenesulphonyl)-benzenesulphonamide, (4-amino-2-chloro-5-trifluoromethyl benzenesulphonyl)-henzenesuiphonamide, (4-amino-2-chloro-5-trifluoromethyl-benzene- sulphonyl)-methanesulphonamide, (4-amino-2-chloro-5-trifluoromethyl-benzenesul phonyl)-2-naphthylsulphonamide, (4-amino-2-trifluoromethyl-5-chloro-benzenesulphonyl)-benzenesulphonamide, (4-amino-2-trifluoromethyl-5-chlorobenzenesulphonyl)- 2-naphthylsulphonamide, (4-amino-2-trifluoromethyl-5-bromo-benzenesulphonyl)butanesulphonamide, (4-amino-2-trifluoromethyl-benzenesulphonyl)-methanesulphor- amide, (4-amino-2-trifluoromethyl-benzenesulphonyl)-butanesulphonamide, (4-amino-2- methyl-5-chloro-henzenesulphonyl)-p-toluenesulphonamide, (4-amino-2-methyt-5- chloro-benzenesulphonyl)-o-toluenesuiphonamide, (4-amino-2,5-dibromobenzene-sulphonyl)-benzenesulphonamide, (4-amino-2,5-dimethyl-benzene-sulphonyl)-butanesul- phonamide, N-4-amino-phenyl-sulphonyl)-2-amino-ethane-sulphonic acid, N-methyl
N-(4-amino-phenyl-sulphonyl)-2-amino-ethane-sulphonic acid, N-propyl-N-(4-amino phenyl-sulphonyl)-2-arnino-ethane-sulphonic acid, N-(4-amino-2-chlorophenyl-sulphonyl)-2-amino-ethane-sulphonic acid, N-methyl-N-(4-amino-3-chloro-phenyl-sulphonyl)-2-amino-ethane-sulphonic acid, N-(4-amino-3-chloro-phenyl-sulphonyl)-2amino-ethane-sulphonic acid, N-methyl-N-(4-amino-3-chloro-phenyl-sulphonyl)-2amino ethanesulphonic acid, N-ethyl-N-(4-amino-3 -chloro-phenyl-sulphonyl)-2-aminoethanesulphonic acid, N-(4-amino-2,5-dichloro-phenyl-sulphonyl)-2-amino-ethanesulphonic acid, N-methyl-N-(4-amino-2,5-dichloro-phenyl-sulphonyl)-2-amino-ethanesulphonic acid, N-ethyl-N-(4-amino-2,5-dichloro-phenyl-sulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-3,5-dichloro-phenyl-sulphonyl)-2-amino-ethanesulphonic acid, N-methyl-N-(4-amino-3,5-dichloro-phenyl-sulphonyl)-2-amino-ethane-sulphonic acid, N- (4-amino -phenyl.salphonyl)-2-amino-ethane.sulphonic add, N-methyl-N-(4 amino-phenylsulphonyl)-2-amino-ethane-sulphonic acid, N-(4-amino-2-chloro-phenylsulphonyl)-2-amino-ethane-sulphonic acid, N-ethyl-N-(4-amino-2-chloro-phenyl-sulphonyl)-2-amino-ethane-sulphonic acid, N-methyl-N-(4-amino-3-chloro-phenyl-sulphonyl)-2-amino-ethane-sulphonic acid, N-ethyl-N-(4-amino-3-chloro-phenyl-sulphonyl)-2-amino-ethane-sulphonic acid, N-(4-amino-2,5-dichloro-phenyl-sulphonyl)-2amino-ethane-sulphonic acid, N-methyl-N-(4amino-2,3-dichlorophenyl-sulphonyl).2- amino-ethane-sulphonic acid, N-(4-amino-3,5-dichloro-phenyl-sulphonyl)-2-aminoethane-sulphonic acid, N-methyl-N-(4-amino-3,5-dichloro-phenyl-sulphonyl)-2-aminosulphonyl - add, N - methyl - N - (4 - amino - phenyl - sulphonyl) - 3 - amino ethane-sulphonic acid, N-(4-amino3-methyl-phenyl-suiphonyl)-2-aminocthane-sul phonic acid, N-(4-amino-3 -methoxy.phenyl-sulphonyi)-2-amino-ethane-sulphonic add,
N-methyl-N-(4-amino-3-methoxy-phenyl-sulphonyl)-2-amino-ethane-sulphonic acid,
N-(4-amino-3-trifluoromethyl-phenyl-sulphonyl)-2-amino-ethane-sulphonic acid, Nmethyl-N-(4-amino-3-trifluoromethyl-phenyl-sulphonyl)-2-amino-ethane-sulphonic acid,
N - propyl- N -(4 - amino - 3 - trifluoromethyl - phenyl - sulphonyl) - 2 - amino ethane - sulphonic add, N - (4 - amino - phenyl - sulphonyl) - 3 - amino - propyl sulphonic - acid, N - methyl - N - (4 - amino - phenyl - sulphonyl) - 3 - amino propyl - sulphonic acid, N - (4 - amino - 2 - chioro - phenyl - sulphonyl) - 3 - amino propyl - sulphonic add, N - (4 - amino - 2,5 - dichloro - phenyl - sulphonyl) - 3 amino - propyl - sulphonic acid, N - (4 - amino - 3,5 - dichloro - phenyl - sulphonyl) 3 - amino - propyl - sulphonic acid, N - propyl - N - (4 - amino - 3,5 - dichloro phenyl - sulphonyl) - 3 - amino - propyl - sulphonic acid, N - (4 - amino - 3 - trifluoromethyl - phenylsulphonyl) - 3 - amino - propyl - sulphonic acid, N - methyl N - (4 - amino - 2,3 - dichloro phenyl - suiphonyl) - 3 - amino - butyl - sulphonic acid, N - (4 - amino - 2,5 - dichloro - phenyl - sulphonyl) - 3 - amino - phenyl sulphonic acid, N - (4 - amino - 3 - trifluoromethyl - phenyl - sulphonyl) - 3 - amino phenyl - sulphonic acid, N - (4 - amino - 2,5 - dichloro - phenyl - sulphonyl) - 4 amino - phenyl - sulphonic acid, N - methyl - N - (4 - amino - 2,5 - dichloro phenyl) - sulphonyl) - 4 - amino - phenyl - sulphonic acid, aniline - 4 - sulphonic acid, 2 - chloroaniline - 4 - sulphonic acid, 2,5 - dichloroaniline - 4 - sulphonic acid, 2,5 - dibromoaniline - 4 - sulphonic acid, 2 - trifluoro - methylaniline - 5 - sulphonic acid, 2 - bromoaniline - 4 - sulphonic acid, 2,6 - dibromoaniline - 4 - sulphonic acid, 2,6 - dicyanoaniline - 4 - sulphonic acid, 2 - trifluoromethyl - 5 - chloroaniline - 4 sulphonic acid, 2 - methyl - aniline - 4 - sulphonic acid, 3 - methylaniline - 4 sulphonic acid, 3 - chloroaniline - 5 - sulphonic acid, 2,5 - dimethoxyaniline - 4 sulphonic acid, 1 - aminonaphthalene - 4 - sulphonic acid, (3 - amino - 4 - chloro benzenesulphonyl) - methanesulphonamide and (3 - amino - 4 - chloro - benzenesulphonyl) - butanesulphonamide.
Examples of amines suitable as coupling components (VIII) are: N - methyl N - (ss - phthalyliminoethyl) - aniline, N - ethyl - N - (p - phthalyliminoethyl) aniline, N - propyl - N - (ss - phthalyliminoethyl) - aniline, N - benzyl - N - (ss phthalylaminoethyl) - aniline, N - phenylethyl - N - (ss - phthalyliminoethyl) - aniline,
N - ss - cyanoethyl - N - (ss - phthalyliminoethyl) - aniline, N - methyl - N - (ss phthalyliminoethyl) - m - toluidine, N - ethyl - N - (ss - phthalyliminoethyl) - m toluidine, N - propyl - N - (p - phthalyliminoethyl) - m - toluidine, N - benzyl - N (ss - phthalyliminoethyl) - m - toluidine, N - phenylethyl - N - (ss - phthalyliminoethyl) - m - toluidine, N - ss - cyanoethyl - N - (ss - phthalyliminoethyl) - m toluidine, N - methyl - N - (p - phthalyliminoethyl) - 3 - acetylaminoaniline, N ethyl - N - (p - phthalyliminoethyl) - 3 - acetylaminoaniline, N - propyl - N - (p - phthalyliminoethyl) - 3 - acetylaminoaniline, N - benzyl - N - (p - phthalyliminoethyl) - 3 - acetylaminoaniline, N - ss - phenylethyl - N - (ss - phthalyliminoethyl) 3 - acetylaminoaniline, N - ss - cyanoethyl - N - (ss - phthalyliminoethyl) - 3 acetylaminoaniline,, N - methyl - N - (p - sulphophthalyliminoethyl) - aniline, N ethyl - N - (ss - sulphophthalyliminoethyl) - aniline, N - propyl - N - (ss - sulphophthalyliminoethyl) - aniline, N - benzyl - N - (ss - sulphophthalyliminoethyl) aniline, N - ss - phenylethyl - N - (ss - sulphophthalyliminoethyl) - aniline, N - ss cyanoethyl - N - (ss - sulphophthalyliminoethyl) - aniline, N - methyl - N - (ss sulphophthalyliminoethyl) - m - toluidine, N - ethyl - N - ((3 - sulphophthalyliminoethyl) - m - toluidine, N - propyl - N - (ss - sulphophthalyliminoethyl) - m - toluidine,
N - benzyl - N - (ss - sulphophthalyliminoethyl) - m - toluidine, N - ss - phenylethyl N - (ss - sulphophthalyliminoethyl) - m - toluidine, N - p - cyanoethyl - N - (p - sulphophthalyliminoethyl) - m - toluidine, N - methyl - N - (p - sulphophthalyliminoethyl) - 3 - acetylaminoaniline, N - ethyl - N - (p - sulphophthalyliminoethyl) - 3 acetylaminoaniline, N - propyl - N - (ss - sulphophthalyliminoethyl) - 3 - acetylaminoaniline, N - benzyl - N - (ss - sulphophthalyliminoethyl) - 3 - acetylaminoaniline, N ss - phenylethyl - N - (ss - sulphophthalyliminoethyl) - 3 - acetylaminoaniline and
N - ss - cyanoethyl - N - (ss - sulphophthalyliminoethyl) - 3 - acetylaminoaniline.
The dyestuffs according to the invention are suitable for dyeing natural and synthetic fibre materials, especially for dyeing polyamide fibres in level, orange to red shades which are of good tinctorial strength and have very good fastness to wet processing and light. They are already taken up well by polyamide fibres in a neutral to weakly acid dyebath. Polyamide fibres are understood, in particular, as those made of synthetic polyamides, such as e-polycaprolactam or condensation products of adipic acid and hexamethylenediamine.
Example 1
4 g of 4-N,N-diethylaminosulphonyl-2,5-dichloroaniline are diazotised in 100 ml of glacial acetic add and 30 ml of concentrated hydrochloric acid at 0 C with 10 ml of an aqueous 10% strength NaNO, solution. The mixture is stirred for a further two hours at 0 C.
5.4 g of N-ethyl-N-(ss-sulphophthalyliminoethyl)-m-toluidine are dissolved in 100 ml of H20 and 20 ml of glacial acetic acid. This solution is allowed to run into the diazonium salt solution described above. The pH is adjusted to about 4 using a saturated solution of sodium acetate. The dyestuff of the formula
which has precipitated is then filtered off and dried at 400C.
N-Ethyl-N-(ss-sulphophthalyliminoethyl)-m-toluidine, which is employed as the coupling component, was obtained as follows.
17.8 g of N-ethyl-N-(ss-aminoethyl)-m-toluidine are heated together with 32 g of sulphophthalic acid to 200 C in the course of 3 hours. After a further hous, the mixture is allowed to cool, the solidified melt is ground and the finely ground product is stirred thoroughly in 200 ml of methanol.
Dyeing Example
0.1 g of the dyestuff obtained according to Example 1 are dissolved in 100 ml of hot water. 5 ml of ammonium acetate solution are added and the mixture is diluted with water to a volume of 500 ml. 10 g of polyamide fibre material is introduced into the dyebath, the bath is heated to the boil in the course of 20 minutes, 4 ml of 10% strength acetic add are added and the bath is kept at the boiling point for 1 hour. The material is then rinsed and dried at 70--800C. A scarlet dyeing is obtained.
Example 2 4.6 g of 2,5-dichloro-+methylsulphonylaminosulphonvlaniline are diazotised in
100 ml of glacial acetic acid and 30 ml of concentrated hydrochloric acid at OC with 10 ml of a 10% strength NaNO2 solution. The mixture is stirred for a further 2 hours.
4.5 g of N-ethyl-N-Gss-phthalyliminoethyl)-m-toluidine are dissolved in 50 ml of glacial acetic acid. This solution is added to the diazonium salt solution described above. The pH is adjusted to about 4 with a saturated solution of sodium acetate. The dyestuff of the formula
which has precipitated is filtered off and dried at about 40 CC.
The dyestuff leads polyamide in a reddish-tinged orange colour shade.
If the procedure of Example 1 or 2 is followed and the compounds listed in the table which follows are employed as the diazo components and as the coupling components, valuable water-soluble dyestuffs which dye polyamide from a weakly acid or neutral bath in the indicated shades are obtained.
Example Compound VII Compound VIII Colour shade 3 2,5-dichloro-4-phenylaminosulphonylaniline N-ethyl-N-ss-sulphophthalimido- scarlet ethyl-3-methylaniline yellowish-tinged 4 2,5-dichloro-4-piperidinosulphonylaniline " scarlet 5 2,5-dichloro-4-benzylaminosulphonylaniline " scarlet 6 2,5-dichloro-4-ss-phenylethylaminosulphonyl- " yellowish-tinged aniline scarlet 7 2,5-dichloro-4-(3-methoxyphenyl)-amino- " scarlet sulphonylaniline 8 2,5-dichloro-4-(2-methylphenyl)-amino- " scarlet sulphonylaniline 9 2,5-dichloro-4-(2,5-dimethylphenyl)-amino- " scarlet aminosulphonylaniline 10 2,5-dichloro-4-(2-methoxy-4-methyl-phenyl)- " scarlet aminosulphonylaniline 11 2,5-dichloro-4-N-methyl-N-phenylamino- " scarlet sulphonylaniline 12 2,5-dichloro-4-N-ethyl-N-phenylamino- " scarlet sulphonylaniline 13 2,5-dichloro-4-N-methyl-N-benzylamino- " scarlet sulphonylaniline 14 2,5-dichloro-4-(4-chlorophenyl)-amino- " yellowish-tinged sulphonylaniline scarlet 15 2,5-dichloro-4-morpholinosulphonylanine " scarlet 16 2,5-dichloro-4-(2,5-dimethoxyphenyl)- " scarlet aminosulphonylaniline 17 2,5-dichloro-4-dimethylaminosulphonyl- " scarlet aniline 18 2-trifluoromethyl-4-dimethylamino- " yellowish-tinged red sulphonyl-5-chloroaniline 19 2-trifluoromethyl-4-dimethylamino- " yellowish-tinged sulphonylaniline scarlet 20 2-trifluoromethyl-4-phenylamino-sulphonyl- " yellowish-tinged aniline scarlet 21 2-trifluoromethyl-4-benzylamino-sulphonyl- " scarlet aniline 22 2-trifluoromethyl-4-ss-phenylethylamino- " reddish-tinged sulphonylaniline orange Example Compound VII Compound VIII Colour shade 23 2-trifluoromethyl-4-(4-chlorophenyl)- " reddish-tinged aminosulphonylaniline orange 24 2-trifluoromethyl-4-(3-methyl-4-chloro- " reddish-tinged phenyl)-aminosulphonylaniline orange 25 2-trifluoromethyl-4-(4-methoxyphenyl)- " yellowish-tinged aminosulphonylaniline scarlet 26 2-trifluoromethyl-4-piperidinosulphonyl- " yellowish-tinged aniline scarlet 27 2-trifluoromethyl-4-morpholinosulphonyl- " yellowish-tinged aniline scarlet 28 2-trifluoromethyl-4-N-methyl-N-benzylamino- " yellowish-tinged sulphonylaniline scarlet 29 2-trifluoromethyl-4-phenylaminosulphonyl- " yellowish-tinged 5-chloroaniline red 30 2-trifluoromethyl-4-N-methyl-N-phenyl- " yellowish-tinged aminosulphonyl-5-chloroaniline red 31 2-trifluoromethyl-phenylaminosulphonyl- " scarlet 6-bromoaniline 32 2-trifluoromethyl-4-dimethylamino- " scarlet sulphonyl-6-bromoaniline 33 2,6-dichloro-4-diethylaminosulphonyl- " orange aniline 34 2,5-dichloroaniline N-propyl-N-ss-sulphophthalimido- reddish-tinged ethylaniline yellow 35 2-cyano-5-chloroaniline N-butyl-N-ss-sulphophthalimido- orange ethyl-3-methylaniline 36 2,5-dichloro-4-methylsulphonylaniline N-benzyl-N-ss-sulpho- yellowish-tinged phthalimidoethyl-3-methyl- scarlet aniline 37 2,5-dichloro-4-propylsulphonylaniline N-benzyl-N-ss-sulphophthalimido- yellowish-tinged ethylaniline scarlet 38 2,5-dichloro-4-benzylsulphonylaniline N-ethyl-N-ss-sulphophthalimido- reddish-tinged ethylaniline orange 39 2,5-dichloro-4-dipropylaminosulphonyl- N-ethyl-N-ss-sulphophthalimido- red aniline ethyl-3-acetylaminoaniline 40 2-trifluoromethyl-4-dibutylaminosulphonyl- N-ethyl-N-ss-sulphothalimido- yellowish-tinged re aniline ethyl-3-acetylaminoaniline Example Compound VII Compound VIII Colour shade 41 2,5-dichloro-4-ss-hydroxyethylamino- N-ethyl-N-ss-sulphophthalimido- red sulphonylaniline ethyl-3-methoxyaniline 42 2,5-dichloro-4-N-methyl-N-ss-hydroxyethyl- N-ethyl-N-sssulphophthalimido- scarlet aminosulphonylaniline ethyl-2,5-dimethylaniline 43 2,5-dichloro-4-nitroaniline N-ethyl-N-ss-sulphophthalimido- ruby ethyl-3-ethylaniline 44 2-chloro-4-methylsulphonyl-5-methylaniline N-methyl-N-γ-sulphophthalimido- orange propyl-3-methylaniline 45 2-bromo-4-methylsulphonylaniline N-ss-cyanoethyl-N-ss-sulpho- orange phthalimidoethyl-3-methylaniline 46 2-phenylsulphonylaniline N-ethyl-N-ss-sulphophthalimido- yellowish-tinged ethyl-2-methoxy-5-methyl- orange aniline 47 3,4-dicyanoaniline N-methyl-N-ss-sulphophthalimido- red ethyl-3-methylaniline 48 3-benzylaminosulphonyl-4-chloroaniline " reddish-tinged yellow 49 2,4-dichloro-5-methylsulphonylaniline N-ethyl-N-ss-sulphophthalimido- yellowish-tinged ethyl-3-ethoxyaniline scarlet 50 2-chloro-4-methoxy-5-dimethylamino " reddish-tinged sulphonylaniline orange 51 2-chloro-4-dimethylaminocarbonylaniline N-ethyl-N-ss-sulphophthalimido- reddish-tinged ethyl-2,5-dimethylaniline orange 52 4-benzylaminocarbonylaniline " reddish-tinged yellow 53 2-dimethylaminocarbonyl-4-bromoaniline " orange 54 2,6-dichloro-4-pyrrolidinosulphonyl- " orange aniline 55 2,5-dichloro-4-sulphoaniline N-ethyl-N-ss-phthalimidoethyl- orange 3-methylaniline 56 2,5-dichloro-4-N-methyl-N-ss-sulpho- " yellowish-tinged red ethylaminosulphonylaniline 57 " N-ethyl-N-ss-phthalimidooethyl- scarlet aniline 58 2,5-dichloro-4-ss-sulphoethylamino- N-ethyl-N-ss-phthalimidoethyl- yellowish-tinged red sulphonylaniline 3-methylaniline 59 2,5-dichloro-4-sulphobenzylamino- " scarlet sulphonylaniline Example Compound VII Compound VIII Colour shade 60 2,5-dichloro-4-phenylsulphonylamino- " reddish-tinged orange sulphonylaniline 61 2,4-dichloro-5-sulphonaniline " orange 62 2-bromo-4-sulphonaniline N-ethyl-N-ss-phthalimidoethyl- orange 2,5-dimethylaniline 63 2-trifluoromethyl-4-sulphoaniline " orange 64 2-trifluoromethyl-4-sulpho-5-chloro- " yellowish-tinged aniline scarlet 65 2,3,6-trichloro-5-sulphoaniline N-ethyl-N-ss-phthalimidoethyl- orange aniline 66 2,4-dichloro-5-sulphoaniline " reddish-tinged yellow 67 2,5-dichloro-4-(3-sulphophenyl)- " orange aminoaniline 68 2-trifluoromethyl-4-ss-sulphoethylamino- " reddish-tinged sulphonylaniline orange 69 2-trifluoromethyl-4-N-methyl-N-ss-sulpho- " scarlet ethylaminosulphonyl-5-chloroaniline 70 2,5-dichloro-4-N-methyl-N-ss-sulphato- N-ethyl-N-ss-phthalimidoethyl- red ethylaminosulphonylaniline 3-methoxyaniline 71 2-trifluoromethyl-4-N-ethyl-N-ss-sulphato- N-propyl-N-ss-phthalimido- scarlet ethylaminosulphonylaniline ethyl-3-ethoxyaniline 72 2,5-dichloro-4-ss-sulphopropylamino- N-ethyl-N-ss-phthalimidoethyl- bluish-tinged red sulphonylaniline 3-acetylaminoaniline 73 2,5-dichloro-4-(4-phenylsulphonylamino- " red sulphonylphenyl)-aminosulphonylaniline 74 2,5-dichloro-4-(4-sulphomethylphenyl)- " red aminosulphonyl aniline 75 2-chloro-4-ethoxycarbonylaniline N-ethyl-N-ss-sulphophthalimido- orange ethyl-3-methylaniline 76 2-chloro-4-butoxycarbonylaniline " orange 77 2-trifluoromethyl-4-propylsulphonylaniline N-benzyl-N-ss-sulphophthalimido- reddish-tinged ethyl-3-methylaniline orange 78 2-trifluoromethyl-4-benzylsulphonyl-5- N-methyl-N-ss-sulphophthalimido- yellowish-tinged chloroaniline ethyl-3-methylaniline red 79 2,5-dichloro-4-cyanoaniline " bluish-tinged red Example Compound VII Compound VIII Colour shade 80 2-trifluoromethyl-4-benzylaminosulphonyl- " scarlet 6-bromoaniline 81 2,5-dichloro-4-ss-(4-methoxyphenyl)-ethyl- " yellowish-tinged red aminosulphonylaniline 82 2,5-dichloro-4-(4-chlorophenyl)-sulphonyl- N-benzyl-N-ss-phthalimidoethyl- orange aminosulphonylaniline 3-methylaniline 83 2,5-dichloro-4-(4-methoxyphenyl)-sulphonyl- " orange aminosulphonylaniline 84 2,6-dichloro-4-(3-ethoxyphenyl)-sulphonyl- " yellowish-tinged aminosulphonylaniline orange 85 2-trifluoromethyl-4-(4-ethylphenyl)- " yellowish-tinged sulphonylaminosulphonylaniline orange 86 2,5-dichloro-4-(2-methylphenyl)-sulphonyl- " orange aminosulphonylaniline 87 2,5-dichloro-4-butylsulphonylamino- N-ethyl-N-ss-phthalimidoethyl- reddish-tinged sulphonylaniline 3-methylaniline orange 88 2-trifluoromethyl-4-propylsulphonylamino- " orange sulphonylaniline 89 2-trifluoromethyl-4-propylsulphonylamino- N-ethyl-N-ss-phthalimidoethyl- orange sulphonyl-6-bromoaniline 3-methylaniline 90 2,5-dichloro-4-(3-phenylsulphonylamino- " yellowish-tinged sulphonylphenyl)-aminosulphonylaniline scarlet 91 2,5-dichloro-4-ss-sulphatoethylamino- N-ss-cyanoethyl-N-ss-phthalimido- scarlet sulphonylaniline ethyl-3-methylaniline 92 2-trifluoromethyl-4-N-ethyl-N-ss-sulpho- " reddish-tinged ethylaminosulphonylaniline orange 93 2,5-dichloro-4-dimethylaminosulphonyl- " reddish-tinged aminosulphonylaniline scarlet 94 2,5-bromo-4-methylsulphonylaminosulphonyl- " reddish-tinged aniline scarlet 95 2-chloro-5-phenylsulphonylaminosulphonyl- " yellowish-tinged aniline orange 96 2-trifluoromethyl-4-butylsulphonylamino- " scarlet sulphonyl-5-chloroaniline 97 2,5-dichloro-4-N-methyl-N-#-sulphobutyl- " scarlet aminosulphonylaniline 98 2,5-dichloro-4-aminosulphonylaniline N-ethyl-N-ss-sulphophthalimido- scarlet ethyl-3-methylaniline Example Compound VII
Compound VIII Colour shade 99 2-trifluoromethyl-4-chloroaniline " reddish-tinged yellow 100 2,4-dichloroaniline " reddish-tinged yellow 101 2-chloro-4-trifluoromethylaniline " reddish-tinged yellow 102 sulphanilic acid N-ethyl-N-ss-phthalimidooethyl- orange 3-methylaniline 103 1-amino-5-sulphonaphthalene " orange 104 2,5-dichloro-4-nitroaniline N-ethyl-N-ss-sulphophthalimido- bluish-tinged red ethyl-3-methylaniline 105 2-aminobenzthiazole " red 106 2-amino-4-phenylthiazole " yellowish-tinged red
British Patent Specification 1,073,227 described and claims azo compounds con taining an N-dicarboximidoalkyl group having the general formula
wherein R represents a stralght or branched chain alkylene group, preferably a lower alkylene group, and Y represents the atoms necessary to complete a dicarboximido group, preferably containing 4 to 5 carbon atoms in addition to the nitrogen atom.
Claims (18)
1. An azo dyestuff which, in the form of the free acid, corresponds to the general formula
in which
D denotes a radical of an aromatic-carbocyclic or aromatic-heterocyclic diazo
component,
X denotes OH, NH-SO2-R5, N(R6)-alkylene-OSO3H, N(R6)-alkylene-SO3H,
N(R6)-arylene-SO3H, N(R6)-arylene-CH2-SO3H or N(R6)-arylene-SO2
NH-SO2-R5, the arylene group being optionally substituted, Re denotes a hydrogen, chlorine or bromine atom or a C1 to C4 alkyl or C1 to C4
alkoxy group,
R1 denotes a hydrogen atom or an alkyl, optionally substituted alkoxy or
acylamino group, Re denotes a hydrogen or an alkyl group, Re denotes a hydrogen atom, an optionally substituted aralkyl group, or an
alkyl group optionally substituted other than by aryl, Re denotes an alkylene group, Re denotes an optionally substituted alkyl, aryl or dialkylamino group, Re denotes a hydrogen atom or an alkyl group and
m is 1 or 2.
2. An azo dyestuff according to claim 1, in which D is a radical of any of those
aromatic-carbocyclic or aromatic-heterocyclic diazo components hereinbefore specifically mentioned.
3. An azo dyestuff according to claim 1, which, in the form of the free acid,
corresponds to the general formula
in which X has the same meaning as in claim 1, Rl' denotes a hydrogen atom or a C1 to C3 alkyl, acetylamino, methoxy or
ethoxy group, R,' denotes a hydrogen atom or a methyl group, R3' denotes a methyl, ethyl, benzyl or cyanoethyl group,
R4' denotes C2H4 or C3H6.
R7 and R8 denote a hydrogen, chlorine or bromine atom or a cyano, nitro, C1 to C4 alkyl, C1-C4 alkoxy, carbo-C1 to C4 alkoxy, hydroxyl, trifluoromethyl,
C1 to C4 alkylsulphonyl, phenylsulphonyl or benzylsulphonyl group, or a carbamoyl or sulphamoyl group which is optionally monosubstituted or di
substituted by C1 to C4 alkyl, phenyl, benzyl or phenethyl and
R9 denotes a hydrogen, chlorine or bromine atom or a C1 to C4 alkyl, trifluoro
methyl, sulphamoyl, C1 to C4 alkylsulphonyl, phenylsulphonyl or benzyl
sulphonyl group.
4. An azo dyestuff according to claim 1, which, in the form of the free acid, corresponds to the general formula
in which R1', R2' and R3' have the same meanings as in claim 3,
R7' denotes a hydrogen, chlorine or bromine atom or a trifluoromethyl, methyl ethyl, cyano, methylsulphonyl, ethylsulphonyl or phenylsulphonyl group or a
sulphamoyl group which is optionally monosubstituted or disubstituted by
C1 to C4 alkyl, phenyl or benzyl,
R8' denotes a hydrogen, chlorine or bromine atom or a cyano, carbo-C1 to C4
alkoxy, C1 to C4 alkylsulphonyl, phenylsulphonyl or benzylsulphonyl group,
or a sulphamoyl group which is optionally monosubstituted or disubstituted
by C1 to C4 alkyl, benzyl, phenethyl or phenyl group and
R9' denotes a methyl group or a chlorine, bromine or hydrogen atom.
5. An azo dyestuff according to claim 1, which, in the form of the free acid, corresponds to the general formula
in which Rs' has the same meaning as in claim 4,
R1" denotes a hydrogen atom or a methyl group, R3" denotes a methyl, ethyl or benzyl group,
R7'' denotes a chlorine atom or a trifluoromethyl group and Rg' denotes a methyl group or a chlorine, bromine or hydrogen atom.
6. An azo dyestuff according to claim 1, which, in the form of the free acid, corresponds to the general formula
in which
R1', R2', R3', R7' and R9' have the same meanings as in claim 4 and
X' denotes an OH, NH-SO-R5, N(R6')-C2-C4-alkylene-O-SO3H,
N(R6')-C2-C4-alkylene-SO3H or N(R6')-phenylene-SO3H group; in which
R5' denotes a C1 to C4 alkyl group or a phenyl radical which is optionally sub-
stituted by methyl, ethyl, chlorine, bromine or methoxy and B,' denotes a hydrogen atom or a C1 to C, alkyl group.
7. An azo dyestuff according to claim 1, which, in the form of the free add, corresponds to the general formula
in which R,", R3", R7" and B," have the same meanings as in claim S and
X" denotes an OH, -NH-SO2-R5", N(R6")-CH2-CH2-OSO3 or
N(R6")-CH2-CH2-SO3H group, in which
R5" denotes a C1 to C4 alkyl group or a phenyl radical which is optionally
substituted by chlorine, methyl, methoxy or ethyl and Rss" denotes a hydrogen atom or a methyl or ethyl group.
8. An azo dyestuff according to claim 1, as hereinbefore specifically identified.
9. A process for the production of an azo dyestuff of formula I in claim 1 in which an amine of the general formula
[D-NH2-]-(SO2X). (VII) in which
D and X have the same meanings as in claim 1 and
n is 0 or 1, is diazotised and subjected to a coupling reaction with an amine of the general formula
in which
Ro, R1, R2, R3, Ri and X have the same meanings as in claim 1 and
p denotes 0 or 1,
with the proviso that n and p cannot at the same time be 0.
10. A process according to claim 9, in which the amine of formula (VII) is any of those hereinbefore specifically mentioned.
11. A process according to claim 9 or 10, in which the amine of formula (VIII) is any of those hereinbefore specifically mentioned.
12. A process according to claim 9, in which the amine of formula (Vm) is prepared by heating an amine of the general formula
in which R1, R, R3 and R1 have the same meanings as in claim 1, together with a phthalic
acid of the general formula
in which Ro, X and n have the same meanings as in claim 9, or with a corresponding phthalic anhydride, to 150 to 2500 C.
13. A process for the production of an azo dyestuff as claimed in claim 1, when carried out substantially as described in any one of the Examples.
14. An azo dyestuff as claimed in claim 1, when produced by the process of any of claims 9 to 13.
IS. A process for dyeing or printing a natural or synthetic fibre material comprising treating the material with a dyestuff as claimed in any of claims 1 to 8 and 14.
16. A process according to claim 15, in which the fibre material is of a synthetic polyamide.
17. A process according to claim 15, when carried out substantially as described in the "Dyeing Example".
18. A natural or synthetic fibre material when dyed or printed by the process of any of claims 15 to 17.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762640764 DE2640764A1 (en) | 1976-09-10 | 1976-09-10 | AZO DYES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1561420A true GB1561420A (en) | 1980-02-20 |
Family
ID=5987617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3695077A Expired GB1561420A (en) | 1976-09-10 | 1977-09-05 | Azo dyestuffs containing a phthalimido - alkyl group |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5334824A (en) |
| DE (1) | DE2640764A1 (en) |
| FR (1) | FR2364246A1 (en) |
| GB (1) | GB1561420A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4447358A (en) * | 1980-10-16 | 1984-05-08 | Ciba-Geigy Corporation | Monoazo compounds |
| US5532345A (en) * | 1994-05-30 | 1996-07-02 | Ciba-Geigy Corporation | Fiber reactive phthalimidylazo dyes and use thereof |
| US5576445A (en) * | 1994-05-30 | 1996-11-19 | Ciba-Geigy Corporation | Intermediates for reactive dyes |
| CN101755012A (en) * | 2007-07-20 | 2010-06-23 | 亨斯迈先进材料（瑞士）有限公司 | azo dyes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3525733A (en) * | 1967-05-09 | 1970-08-25 | Eastman Kodak Co | Water-insoluble monoazo compounds containing an aniline coupling component substituted by both an acylamido group and a dicarboximido group |
| CH549627A (en) * | 1969-07-17 | 1974-05-31 | Sandoz Ag | Difficultly water-sol azo cpds - of the 2-cyano-4-alkyl-or phenylsulphonyl-2'-acylamino-4'-dialkylamino-1:1'-azobenzene series |
| DE2263295A1 (en) * | 1972-12-23 | 1974-06-27 | Bayer Ag | MONOAZO DYES |
-
1976
- 1976-09-10 DE DE19762640764 patent/DE2640764A1/en not_active Withdrawn
-
1977
- 1977-09-05 GB GB3695077A patent/GB1561420A/en not_active Expired
- 1977-09-08 JP JP10732677A patent/JPS5334824A/en active Pending
- 1977-09-09 FR FR7727395A patent/FR2364246A1/en active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4447358A (en) * | 1980-10-16 | 1984-05-08 | Ciba-Geigy Corporation | Monoazo compounds |
| US5532345A (en) * | 1994-05-30 | 1996-07-02 | Ciba-Geigy Corporation | Fiber reactive phthalimidylazo dyes and use thereof |
| US5576445A (en) * | 1994-05-30 | 1996-11-19 | Ciba-Geigy Corporation | Intermediates for reactive dyes |
| US5665125A (en) * | 1994-05-30 | 1997-09-09 | Ciba-Geigy Corporation | Mixtures of fibre-reactive ring-opened phthalimidylazo dyes |
| CN101755012A (en) * | 2007-07-20 | 2010-06-23 | 亨斯迈先进材料（瑞士）有限公司 | azo dyes |
| CN101755012B (en) * | 2007-07-20 | 2015-04-29 | 亨斯迈先进材料（瑞士）有限公司 | Azo dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2364246A1 (en) | 1978-04-07 |
| FR2364246B1 (en) | 1981-08-28 |
| JPS5334824A (en) | 1978-03-31 |
| DE2640764A1 (en) | 1978-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |