Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
2000-09-25
2003-02-18
Klemanski, Helene (Department: 1755)
Compositions: coating or plastic
Coating or plastic compositions
Marking
C106S031840, C534S693000, C534S701000, C534S713000, C534S720000, C534S724000, C008S641000, C008S682000, C008S685000, C428S195100
Reexamination Certificate
active
06521032
ABSTRACT:
The present invention relates to inks comprising certain copper complex azo dyes based on 1-naphthol-3,6,8-trisulfonic acid or 1-naphthol-3,8-disulfonic acid as coupling component and to dye mixtures comprising the said dyes. The present invention relates also to the novel copper complex azo dyes contained in the inks or dye mixtures according to the invention.
The inks underlying the present invention are especially suitable for the printing of paper, textile fibre materials, plastics films or aluminium foils, especially using the ink-jet printing method, and yield magenta dyeings and prints having good fastness to light and a high colour brilliance.
The dyes and dye mixtures underlying the present invention are suitable for the preparation of the inks according to the invention and for the dyeing of paper, wood, textile fibre materials and aluminium sheets or foils using traditional dyeing and printing methods and yield magenta dyeings and prints having good fastness to light and a high colour brilliance.
Inks are subject to high demands in terms of their fastness to light and their colour brilliance. The known magenta inks do not fulfil all of those demands at the same time. For example, although the known inks produce recordings having good fastness to light, the colour shades in such cases are dull and have a low degree of brilliance, as, for example, in the case of inks that contain C.I. Reactive Red 23. On the other hand, other known inks yield recordings having a high degree of brilliance but do not provide the desired quality in terms of the fastness to light of the recordings.
The present invention is therefore based on the problem of providing improved inks for the dyeing and printing of paper, textile fibre materials, plastics films or aluminium foils that possess the qualities described above to a high degree. The new inks should produce brilliant colour shades and at the same time be distinguished by good fastness to light.
It has now been found, surprisingly, that inks comprising a copper complex structurally similar to C.I. Reactive Red 23 produce a brilliant, bluish magenta having good fastness to light.
The present invention accordingly relates to inks comprising a dye of formula (1)
wherein
X is hydroxy, unsubstituted or hydroxy-substituted C
1
-C
4
alkyl, vinyl or a radical —CH
2
—CH
2
—Z, wherein Z is a group removable under alkaline conditions or is C
1
-C
24
alkoxy unsubstituted or substituted in the alkyl moiety, which may further be 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, which may further be interrupted in the alkyl moiety by oxygen or by a radical —NR
1
— in which R
1
is hydrogen or unsubstituted or further substituted 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 unsubstituted or substituted in the aryl moiety; morpholino; piperidin-1-yl; or piperazin-1-yl unsubstituted or substituted at the nitrogen atom;
or X has the same definitions as Z with the exception of a group removable under alkaline conditions;
R is C
1
-C
4
alkyl, C
1
-C
4
alkoxy or halogen; and
m and n are each independently of the other the number 0, 1 or 2; and
an organic solvent.
Z as C
1
-C
24
alkoxy, especially C
1
-C
12
alkoxy and more especially C
1
-C
4
alkoxy is straight-chain or branched and 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 have been 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-butyl-thio. 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 the 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 the radicals substituted in the phenyl ring, for example by C
1
-C
4
alkyl, e.g. methyl or ethyl, which is unsubstituted or further substituted, e.g. by carboxy; C
1
-C
4
alkoxy, e.g. methoxy or ethoxy; carboxy; C
2
-C
4
alkanoylamino, e.g. acetylamino or propionylamino; carbamoyl; N—C
1
-C
4
alkyl-carbamoyl, which is unsubstituted or further substituted in the alkyl moiety, e.g. by carboxy, for example N-carboxymethylcarbamoyl; sulfamoyl; N—C
1
-C
4
alkylsulfamoyl; sulfo or by halogen, e.g. chlorine or bromine. Preference is given to the substituted radicals, especially the radicals substituted by carboxy, carboxymethyl, N-carboxymethylcarbamoyl or by sulfo, more especially 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, e.g. by phenyl (which may itself be substituted by carboxy, carbamoyl, sulfo or by sulfamoyl); amino; C
2
-C
4
alkanoylamino, e.g. acetylamino or propionylamino; C
1
-C
4
alkoxy, e.g. 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 C
1
-C
4
alkyl, e.g. methyl or ethyl, unsubstituted or substituted, for example by amino or by hydroxy, but is preferably hydrogen.
Examples of radicals that are substituted in the alkyl moiety and/or are interrupted in the alkyl moiety by oxygen or by —NR
1
— include
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, polyethylene imines of formula —(NH—CH
2
—CH
2
)
3
—NH
2
or —(NH—CH
2
—CH
2
)
4
—NH
2
,
N-&bgr;-sulfatoethylamino, N-&bgr;-sulfoethylamino, N-carboxymethylamino, N-&bgr;-carboxyethylamino, N-&agr;,&bgr;-dicarboxyethylamino, N-&agr;,&ggr;-di-carboxypropylamino, 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 the formula
wherein the sum of the carbon atoms R
a
+R
b
+R
c
is from 11 to 14. An example of an amine forming the basis of the radical of the formula given above is ®Primene 81 R (Rohm & Haas).
Z as N-mono- or N,N-di-C
1
-C
24
alkylamino that is substituted in the alkyl moiety and/or is interrupted in the alkyl moiety by oxygen or by —NR
1
— in which R
1
has the definitions and preferred meanings 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.
Preferred for Z as N-mono- or N,N-di-C
1
-C
24
alkylamino are the radicals substituted in the alkyl moiety by phenyl, amino
Frick Marcel
Lehmann Urs
Ciba Specialty Chemicals Corporation
Klemanski Helene
Mansfield Kevin T.
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