Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2000-09-13
2001-08-28
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S618000, C534S619000, C534S636000, C534S638000, C534S643000, C540S130000, C544S077000, C544S189000, C552S230000
Reexamination Certificate
active
06281339
ABSTRACT:
The present invention relates to new dyes that can be obtained from reactive dyes having at least one acryloylamino radical by the addition of particular nitrogen-, oxygen- or sulfur-containing nucleophilic compounds.
The dyes of the present invention are suitable especially for printing textile fibre materials, paper, plastics films or aluminium foils, preferably using the ink-jet printing method, and for dyeing textile fibre materials, paper, aluminium sheets or foils using traditional dyeing and printing methods, and yield dyeings and prints having good fastness to light and high colour brilliance.
The present invention accordingly relates to monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine dyes comprising at least one structural unit of formula (1)
wherein
Z is C
1
-C
24
alkoxy unsubstituted or substituted in the alkyl moiety, or uninterrupted or interrupted in the alkyl moiety by oxygen; phenoxy unsubstituted or substituted in the phenyl ring; C
1
-C
4
alkylthio unsubstituted or substituted in the alkyl moiety; phenylthio unsubstituted or substituted in the phenyl ring; amino; N-mono- or N,N-di-C
1
-C
24
alkylamino, unsubstituted or substituted in the alkyl moiety, or uninterrupted or interrupted in the alkyl moiety by oxygen or by a radical —NR
1
— in which R
1
is hydrogen or C
1
-C
4
alkyl; C
10
-C
20
terpeneamino; C
5
-C
7
cycloalkylamino unsubstituted or substituted in the cycloalkyl ring; phenyl- or naphthyl-amino or N—C
1
-C
4
alkyl-N-phenyl- or N—C
1
-C
4
alkyl-N-naphthyl-amino, each unsubstituted or substituted in the aryl moiety; morpholino; piperazin-1-yl or piperidin-1-yl, and X is hydrogen, hydroxy, chlorine or bromine, or X has the meanings given for Z.
Z as C
1
-C
24
alkoxy, preferably as C
1
-C
12
alkoxy and especially as C
1
-C
4
alkoxy, is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy. The mentioned radicals are unsubstituted or substituted in the alkyl moiety, for example by C
1
-C
4
alkoxy, e.g. methoxy or ethoxy; hydroxy; sulfo; sulfato or by carboxy. Radicals interrupted in the alkyl moiety by oxygen and unsubstituted or further substituted in the alkyl moiety are, for example, polyalkylene oxides having from 4 to 24 carbon atoms, for example polyethylene oxide of formula —(O—CH
2
—CH
2
)
2-12
—OH, polypropylene oxide of formula
and mixed polyethylene oxide/polypropylene oxide. The hydroxy group of the mentioned polyalkylene oxide radicals may be etherified, for example by C
1
-C
4
alkyl, e.g. methyl or ethyl.
Z as C
1
-C
4
alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio or n-butylthio. The mentioned radicals are unsubstituted or substituted in the alkyl moiety, for example by C
1
-C
4
alkoxy, e.g. methoxy or ethoxy; hydroxy; sulfo or by carboxy. Preference is given to those radicals substituted by one or two radicals from the group hydroxy, sulfo and carboxy.
Z as phenoxy or phenylthio can include both the unsubstituted radicals and radicals substituted in the phenyl ring, for example by C
1
-C
4
alkyl, e.g. methyl or ethyl, unsubstituted or further substituted, for example by carboxy; C
1
-C
4
alkoxy, for example methoxy or ethoxy; carboxy; C
2
-C
4
alkanoylamino, for example acetylamino or propionylamino; carbamoyl; N—C
1
-C
4
alkylcarbamoyl unsubstituted or further substituted in the alkyl moiety, for example by carboxy, for example N-carboxymethylcarbamoyl; sulfamoyl; N—C
1
-C
4
alkylsulfamoyl; sulfo or by halogen, for example chlorine or bromine. Preference is given to the substituted radicals, preferably to those radicals substituted by carboxy, carboxymethyl, N-carboxymethylcarbamoyl or by sulfo, especially to those substituted by carboxy or sulfo.
Z as N-mono- or N,N-di-C
1
-C
24
alkylamino is, for example, methylamino, ethylamino, N,N-di-methylamino, N,N-diethylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino or tert-butylamino, linear or branched pentylamino, hexylamino, heptylamino, octylamino, nonylamino, decylamino, undecylamino, dodecylamino, tridecylamino or tetradecylamino. The mentioned radicals are unsubstituted or substituted in the alkyl moiety, for example by phenyl, which may itself be substituted by carboxy, carbamoyl, sulfo or by sulfamoyl; amino; C
2
-C
4
alkanoylamino, for example acetylamino or propionylamino; C
1
-C
4
alkoxy, for example methoxy or ethoxy; hydroxy; sulfo; sulfato; carboxy; carbamoyl or by sulfamoyl. The mentioned radicals are uninterrupted or interrupted in the alkyl moiety by oxygen or by —NR
1
— in which R
1
is hydrogen or, for example, methyl or ethyl, preferably hydrogen.
As examples of radicals substituted in the alkyl moiety, and/or interrupted in the alkyl moiety by oxygen or by —NH—, the following radicals may be mentioned: N-&bgr;-aminoethylamino, N-&bgr;-aminopropylamino, N-&bgr;-hydroxyethylamino, N,N-di-&bgr;-hydroxyethylamino, N-2-(&bgr;-hydroxyethoxy)ethylamino, N-2-[2-(&bgr;-hydroxyethoxy)ethoxy]ethylamino, N-2-(&bgr;-hydroxyethylamino)ethylamino, N-2-(&bgr;-aminoethylamino)ethylamino, polyethyleneimines of formula —(NH—CH
2
—CH
2
)
3
—NH
2
or —(NH—CH
2
—CH
2
)
4
—NH
2
, N-&bgr;sulfatoethylamnino, N-&bgr;-sulfoethylamino, N-carboxymethylamino, N-&bgr;-carboxyethylamino, N-&agr;&bgr;-dicarboxethylamino, N-&agr;,&ggr;-dicarboxypropylamino, N-ethyl-N-&bgr;-hydroxyethylamino and N-methyl-N-&bgr;-hydroxyethylamino.
Suitable unsubstituted and uninterrupted radicals that are branched in the alkyl moiety correspond, for example, to formula
wherein the sum of the carbon atoms
R
a
+R
b
+R
c
is from 11 to 14. As an example of the amines forming the basis of the radical of the formula above there may be mentioned ®Primene 81 R (Rohm & Haas).
Z as N-mono- or N,N-di-C
1
-C
24
alkylamino substituted in the alkyl moiety, and/or interrupted in the alkyl moiety by oxygen or by —NR
1
— in which R
1
has the meanings and preferred meaning given above is preferably N-mono- or N,N-di-C
1
-C
6
alkylamino and especially N-mono- or N,N-di-C
1
-C
4
alkylamino.
For Z as N-mono- or N,N-di-C
1
-C
24
alkylamino preference is given to those radicals substituted in the alkyl moiety by phenyl, amino, hydroxy, sulfo, sulfato, carboxy or by carbamoyl, especially by phenyl, amino, sulfo, sulfato, carboxy or by carbamoyl, and uninterrupted or interrupted in the alkyl moiety by —NH—.
Z as C
10
-C
20
terpeneamino, preferably C
20
diterpeneamino, is an amino group mono- substituted on the nitrogen by a terpene hydrocarbon radical. There come into consideration as terpene hydrocarbon radical, for example, acyclic, monocyclic or bicyclic C
10
terpenes, acyclic, monocyclic, bicyclic or tricyclic C
15
sesquiterpenes, acyclic, monocyclic or tricyclic C
20
terpenes, especially tricyclic C
20
diterpenes and, more especially, dehydrogenated tricyclic C
20
diterpenes, such as those derived from dehydroabietic acid. As an example of such a dehydrogenated tricyclic C
20
diterpeneamino radical there may be mentioned the radical of formula
Z as C
5
-C
7
cycloalkylamino can include both the unsubstituted radicals and radicals substituted in the cycloalkyl ring, for example by C
1
-C
4
alkyl, e.g. methyl or ethyl, especially methyl, or by carboxy. Preferred as such radicals are the corresponding cyclohexyl radicals.
Z as phenylamino or N—C
1
-C
4
alkyl-N-phenylamino, preferably phenylamino, can include both the unsubstituted radicals and radicals substituted in the phenyl ring, for example by C
1
-C
4
-alkyl, e.g. methyl or ethyl, unsubsbtuted or further substituted, for example by carboxy; C
1
-C
4
alkoxy, for example methoxy or ethoxy; carboxy; carbamoyl; N—C
1
-C
4
alkylcarbamoyl unsubstituted or further substituted in the alkyl moiety, for example by carboxy, for example N-carboxymethylcarbamoyl; sulfo or by halogen, for example chlorine or bromine. Preference is given to the substituted radicals, preferably to those radicals substituted by carboxy, carboxymethyl, N-carboxymethylcarbamoyl or by sulfo, especially to those substituted by sulfo.
Z as naphthylamino or N—C
1
-C
4
Frick Marcel
Lehmann Urs
Ciba Specialty Chemicals Corporation
Mansfield Kevin T.
Powers Fiona T.
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