Triphendioxazine compounds

Details Triphendioxazine compounds Triphendioxazine compounds

1996-05-08

1998-05-12

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

544 76, 8543, 8549, C07D26538

Patent

active

057506892

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/GB94/02348, filed Oct. 26, 1994.
This invention relates to organic chemicals, and in particular to triphenodioxazine dyes which are free from cellulose-reactive groups, their preparation and uses.
According to the present invention there is provided a compound of Formula (1) and salts thereof: ##STR2## wherein: W is Cl or Br; substituted alkyl; groups.
A is preferably methyl or, more preferably, a group of the Formula (2): ##STR3## wherein: R.sup.2 is H, OH or CH.sub.3 ; and O--(C.sub.1-4 -alkyl).
Preferably R.sup.2 is H or methyl, especially H. R.sup.3 is preferably C.sub.1-3 -alkyl, especially methyl. In a preferred embodiment R.sup.2 is H and R.sup.3 is methyl.
As Examples of groups of Formula (2) there may be mentioned --CH.sub.2 CH.sub.3, --CH.sub.2 CH.sub.2 CH.sub.3, --(CH.sub.2).sub.3 --CH.sub.3, --CH.sub.2 CH(CH.sub.3).sub.2, --CH(CH.sub.3).sub.2, --CH.sub.2 CH.sub.2 --O--CH.sub.3, --CH.sub.2 CH.sub.2 --OCH.sub.2 CH.sub.3, --CH(OH)CH.sub.3 and --CH.sub.2 CH.sub.2 OH, the latter two exemplifying hydroxy-C.sub.1-3 -alkyl groups.
When R is alkyl it is preferably C.sub.1-4 -alkyl, especially methyl or ethyl. When R is alkoxy it is preferably C.sub.1-4 -alkoxy, especially methoxy. R.sup.1 is preferably H or C.sub.1-4 -alkyl.
The groups represented by Z--X--B--X-- in Formula (1) may be the same as each other or different from one another.
Each X independently is preferably NR.sup.1 as hereinbefore defined, especially NH or N(CH.sub.3).
The divalent organic linking group represented by B is preferably alkylene, especially C.sub.1-6 -alkylene, more especially C.sub.2-4 -alkylene; aralkylene, preferably C.sub.7-11 -aralkylene, especially phenyl-C.sub.1-4 alkylene; or arylene, preferably arylene having up to six carbon atoms, especially phenylene; and B may be substituted or unsubstituted.
As examples of alkylene and aralkylene radicals represented by B, there may be mentioned: --(CH.sub.2).sub.3 --) ##STR4##
As examples of arylene radicals represented by B there may be mentioned 1,2-, 1,3- and 1,4-phenylene and 1,4-naphthylene which optionally are sulphonated.
Suitable aromatic nitrogen ring heterocycles (Z) devoid of cellulose-reactive groups include quinoxaline, pyrimidine, pyridine and especially triazine groups. The group Z may be unsubstituted, but preferably contains one or more non-labile substituents.
A particularly preferred group represented by Z is of Formula (3): ##STR5## wherein Y.sup.1 and Y.sup.2 are each independently hydrogen or a non-labile substituent. Y.sup.1 and Y.sup.2 are the same or different. Y.sup.1 and Y.sup.2 are preferably each independently OH, NH.sub.2, C.sub.1-4 -alkyl, H or optionally substituted alkylamino including dialkylamino and cycloaliphatic amino), arylamino, alkylthio, arylthio, alkoxy or aryloxy.
In one embodiment Y.sup.1 and Y.sup.2 are each independently an optionally substituted arylamino group.
In a second embodiment one of Y.sup.1 and Y.sup.2 is optionally substituted arylamino and that the other is a non-aryl group, especially OH, NH.sub.2 or optionally substituted alkylamino, alkylthio or alkoxy.
When Y.sup.1 or Y.sup.2 is an optionally substituted alkylamino group it is preferably of the formula --NR.sup.4 R.sup.5 wherein R.sup.4 is optionally substituted alkyl (especially optionally substituted C.sub.1-4 -alkyl), R.sup.5 is H or an optionally substituted alkyl group, or R.sup.4 and R.sup.5 taken together with the N atom to which they are attached form a 5- or 6-membered ring, especially a morphilino or piperidino ring. Examples of such groups include C.sub.1-4 -alkylamino, e.g. methylamino, ethylamino, butylamino; di(C.sub.1-4 -alkyl)amino, e.g. dimethylamino, diethylamino, methylamino; and C.sub.1-4 -alkylamino and di(C.sub.1-4 -alkyl)amino groups having an OH, CN or SO.sub.3 H group, such as .beta.-hydroxyethylamino, di(.beta.-hydroxyethyl)amino, .beta.-cyanoethylamino, .beta.-sulphoethylamino, .beta.-hydroxypropylamino and (.beta.-hydroxethyl)methylamino.
When Y.sup.1 or Y.sup.2 is an arylamino group it is preferably of

REFERENCES:
patent: 4472575 (1984-09-01), Renfrew
patent: 4785098 (1988-11-01), Fuchs et al.
patent: 5498712 (1996-03-01), Thomson

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