Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2003-09-02
2004-06-29
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C106S031480, C106S031770, C106S196100, C524S087000, C347S106000, C349S106000
Reexamination Certificate
active
06756487
ABSTRACT:
The present invention relates to novel monoazoquinolone pigments, to a process for their preparation, and to their use as colourants, especially for coloring high molecular weight material.
Monoazoquinolone pigments are known. For example, U.S. Pat. No. 3,119,808 discloses monoazoquinolone pigments containing neither sulfonic acid groups nor carboxylic acid groups at the coupling component.
The ever greater demands made of the quality of colourations, for example the fastness properties, or of application-related properties, for example the migration behaviour or the oversprayability, have resulted in there still being a need for new pigments that exhibit improved properties, especially with regard to fastness properties.
Accordingly, the object underlying the present invention is to find novel, improved monoazoquinolone pigments, especially for producing surface coatings, printing inks and colour filters or for the colouring of plastics, which pigments possess the above-characterised qualities to a high degree. The novel pigments should yield colourations having a high purity of shade, high tinctorial strength, and good fastness to overspraying and migration. The resulting colourations should especially exhibit good fastness to heat, light and weathering.
It has been found that the stated object is largely achieved with the novel monoazoquinolone pigments defined hereinbelow.
Accordingly, the present invention relates to monoazoquinolone pigments which, in one of the tautomeric forms thereof, correspond to the formula
wherein
Ar is a radical of the formula
wherein
R
1
is C
1
-C
4
alkyl,
R
2
and R
3
are each independently of the other hydrogen, halogen, C
1
-C
4
alkyl, carboxy, sulfo, cyano, C
1
-C
4
alkoxycarbonyl, C
1
-C
4
alkylcarbonyl, C
1
-C
4
alkanoylamino, benzoylamino that is unsubstituted or substituted in the phenyl ring by halogen, nitro, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy; carbamoyl, N-C
1
-C
4
alkylaminocarbonyl, N-arylaminocarbonyl that is unsubstituted or substituted in the aryl moiety by halogen, nitro, C
1
-C
4
alkyl or by C
1
-C
4
-alkoxy; N,N-di-C
1
-C
4
alkylaminocarbonyl, C
1
-C
4
alkoxysulfonyl, C
1
-C
4
alkylsulfonyl, sulfamoyl, N-C
1
-C
4
alkylaminosulfonyl, N-arylaminosulfonyl that is unsubstituted or substituted in the aryl moiety by halogen, nitro, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy; or N,N-di-C
1
-C
4
alkylaminosulfonyl,
wherein carboxy and sulfo are in the form of the free acid or in salt form,
R
8
and R
9
are each independently of the other hydrogen, halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, carboxy, sulfo, cyano, C
1
-C
4
alkoxycarbonyl, C
1
-C
4
alkylcarbonyl, C
1
-C
4
alkanoylamino, benzoylamino that is unsubstituted or substituted in the phenyl ring by halogen, nitro, C
1
-C
4
-alkyl or by C
1
-C
4
alkoxy; carbamoyl, N-C
1
-C
4
alkylaminocarbonyl, N-arylaminocarbonyl that is unsubstituted or substituted in the aryl moiety by halogen, nitro, C
1
-C
4
alkyl or by C
1
-C
4
-alkoxy; N,N-di-C
1
-C
4
alkylaminocarbonyl, C
1
-C
4
alkoxysulfonyl, C
1
-C
4
alkylsulfonyl, sulfamoyl, N-C
1
-C
4
alkylaminosulfonyl, N-arylaminosulfonyl that is unsubstituted or substituted in the aryl moiety by halogen, nitro, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy; or N,N-di-C
1
-C
4
alkylaminosulfonyl,
wherein carboxy and sulfo are in the form of the free acid or in salt form,
Ar
1
is an aryl radical,
p is a number 0, 1 or 2, and
r is a number 0, 1 or 2, wherein (R
8
)
r
in formula (2f) denotes r identical or different radicals R
8
.
There come into consideration as C
1
-C
4
alkyl for R
1
, R
2
, R
3
, R
8
and R
9
each independently of the others, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl or isobutyl, preferably methyl or ethyl and especially methyl.
There come into consideration as C
1
-C
4
alkoxy for R
8
and R
9
each independently of the other, for example, methoxy, ethoxy, propoxy or butoxy.
There come into consideration as halogen for R
2
, R
3
, R
8
and R
9
each independently of the others, for example, fluorine, chlorine or bromine, preferably chlorine or bromine and especially chlorine.
There come into consideration as C
1
-C
4
alkanoylamino for R
2
, R
3
, R
8
and R
9
each independently of the others, for example, formylamino, acetylamino or propionylamino, especially acetylamino.
R
2
, R
3
, R
8
and R
9
, each independently of the others, as benzoylamino are unsubstituted or substituted in the phenyl ring by halogen, for example chlorine or bromine, preferably chlorine; nitro; C
1
-C
4
alkyl, for example methyl, ethyl, n- or iso-propyl, n-, sec-, tert- or iso-butyl, preferably methyl or ethyl and especially methyl; or by C
1
-C
4
alkoxy, for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, preferably methoxy or ethoxy and especially methoxy.
There come into consideration as C
1
-C
4
alkoxycarbonyl for R
2
, R
3
, R8 and R
9
each independently of the others, for example, methoxy-, ethoxy-, n-propoxy-, isopropoxy- or n-butoxy-carbonyl, preferably methoxy- or ethoxy-carbonyl and especially methoxycarbonyl.
There come into consideration as C
1
-C
4
alkylcarbonyl for R
2
, R
3
, R
8
and R
9
each independently of the others, for example, acetyl, propionyl, butyroyl or valeroyl, preferably acetyl or propionyl and especially acetyl.
There come into consideration as N-C
1
-C
4
alkylaminocarbonyl for R
2
, R
3
, R
8
and R
9
each independently of the others, for example, N-methyl-, N-ethyl-, N-propyl-, N-isopropyl-, N-butyl-, N-sec-butyl- or N-isobutyl-aminocarbonyl, preferably N-methyl- or N-ethyl-amino-carbonyl and especially N-methylaminocarbonyl.
There come into consideration as N-arylaminocarbonyl for R
2
, R
3
, R
8
and R
9
each independently of the others, for example, N-phenyl- or N-naphthyl-aminocarbonyl, preferably N-phenylaminocarbonyl. The mentioned radicals are unsubstituted or substituted in the aryl moiety by halogen, for example chlorine or bromine, preferably chlorine; nitro; C
1
-C
4
alkyl, for example methyl, ethyl, n- or iso-propyl, n-, sec-, tert- or iso-butyl, preferably methyl or ethyl and especially methyl; or by C
1
-C
4
alkoxy, for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, preferably methoxy or ethoxy and especially methoxy.
There come into consideration as N,N-di-C
1
-C
4
alkylaminocarbonyl for R
2
, R
3
, R
8
and R
9
each independently of the others, for example, N,N-di-methyl-, N,N-di-ethyl-, N-methyl-N-ethyl-, N,N-di-propyl-, N,N-di-isopropyl-, N,N-di-butyl-, N,N-di-sec-butyl-, N-methyl-N-sec-butyl- or N,N-di-isobutyl-aminocarbonyl, preferably N,N-di-methyl- or N,N-di-ethyl-aminocarbonyl and especially N,N-di-methylaminocarbonyl.
There come into consideration as C
1
-C
4
alkoxysulfonyl for R
2
, R
3
, R
8
and R
9
each independently of the others, for example, methoxy-, ethoxy-, n-propoxy-, isopropoxy- or n-butoxy-sulfonyl, preferably methoxy- or ethoxy-sulfonyl and especially methoxysulfonyl.
There come into consideration as C
1
-C
4
alkylsulfonyl for R
2
, R
3
, R8 and R
9
each independently of the others, for example, methyl-, ethyl-, n-propyl-, isopropyl-, n-butyl-, sec-butyl-, tert-butyl- or isobutyl-sulfonyl, preferably methyl- or ethyl-sulfonyl and especially methylsulfonyl.
There come into consideration as N-C
1
-C
4
alkylaminosulfonyl for R
2
, R
3
, R8 and R
9
each independently of the others, for example, N-methyl-, N-ethyl-, N-propyl-, N-isopropyl-, N-butyl-, N-sec-butyl-, N-tert-butyl- or N-isobutyl-aminosulfonyl, preferably N-methyl- or N-ethyl-aminosulfonyl and especially N-methylaminosulfonyl.
There come into consideration as N-arylaminosulfonyl for R
2
, R
3
, R
8
and R
9
each independently of the others, for example, N-phenyl- or N-naphthyl-aminosulfonyl, preferably N-phenylaminosulfonyl. The mentioned radicals are unsubstituted or substituted in the aryl moiety by halogen, for example chlorine or bromine, preferably chlorine; nitro; C
1
-C
4
alkyl, for example methyl, ethyl, n- or iso-propyl, n-, sec-, tert- or iso-butyl, preferably methyl or ethyl and especially methyl; or by C
1
-C
4
alkoxy, for exampl
Benkhoff Johannes
De Keyzer Gerardus
Hyuga Tetsuo
Wallquist Olof
Ciba Specialty Chemicals Corporation
Powers Fiona T.
Stevenson Tyler A.
LandOfFree
Monoazoquinolone pigments, process for their preparation and... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Monoazoquinolone pigments, process for their preparation and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Monoazoquinolone pigments, process for their preparation and... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3352144