1:2 Iron azo-dyestuff complexes

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8685, 8639, 534684, 534688, 534692, 534713, 534723, 534693, 534696, C09D 700, C09B 4512, C09B 6722, C09B 6904






Solvent dyes are used for a great variety of purposes although principally they are used in the mass coloration of plastics materials or in various lacquers and varnishes.
While solvent dyes may, in some cases, be incorporated directly into the product to be colored, as their name suggests, they are usually applied from solutions in organic solvents or mixtures of such solvents.
It has been normal practice to dissolve solvent dyestuffs in solvents such as ethers, esters, ketones, chlorinated hydrocarbons and alcoholic solvents e.g. ethanol. Of these solvents, the alcoholic solvents have become increasingly important because of environmental considerations. Unfortunately, however, dyestuffs having desirably high solubility in alcoholic solvents have not until now been available. There is a need for solvent dyestuffs which are highly soluble in alcoholic solvents, in particular ethanol.


This invention is concerned with 1:2 iron azo-dyestuff complexes. It has now been found that certain new 1:2 iron azo-dyestuff complexes exhibit desirably high solibilities in ethanol The invention provides in one of its aspects a compound of the formula (I) ##STR2## or a mixture thereof wherein ##STR3## R.sub.2 and R.sub.3 independently of each other are hydrogen, alkyl, alkoxyalkyl, cycloalkyl and aryl a naphthyl group, ##STR4## R.sub.7.sup.+ is a protoncled aliphatic or cycloaliphatic amine with the proviso that attached form a naphthyl group then R.sub.4 is hydrogen and R.sub.6 is hydrogen and ##STR5## R.sub.5 is hydrogen, alkyl, alkoxyalkyl and cycloalkyl.


Preferred alkyl groups are C.sub.1-4 alkyl, which may be linear or branched, e.g. methyl, ethyl or n-propyl, iso-propyl and n- and t-butyl. Preferred alkoxyalkyl groups have 1 to 8 carbon atoms and may be, for example, methoxyalkyl or ethoxyalkyl, more particularly methoxypropyl.
Preferred cycloalkyl groups are those forming a 5 or 6 membered ring.
As aryl groups one can mention the phenyl group or fused rings, for example naphthyl groups. Aryl groups may be unsubstituted or they may be substituted with substituents selected from halogen (preferably Cl and Br), OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, cyano, --NO.sub.2, C.sub.1-4 alkylcarbonyl, SCN, C.sub.1-4 alkoxycarbonyl, benzoyl, phenoxycarbonyl, C.sub.1-4 alkylcarbonyloxy, aminocarbonyl, mono(C.sub.1-4 alkyl)aminocarbonyl, di(C.sub.1-4 alkyl)aminocarbonyl, mono(C.sub.1-4 alkoxy-C.sub.2-4 alkyl)-aminocarbonyl, di(C.sub.1-4 alkoxy-C.sub.2-4 alkyl)aminocarbonyl, aminosulphonyl, mono(C.sub.1-4 alkyl)-aminosulphonyl, di(C.sub.1-4 alkyl)aminosulphonyl, mono(C.sub.1-4 alkoxy-C.sub.2-4 alkyl)amino sulphonyl, di(C.sub.1-4 alkoxy C.sub.2-4 alkyl) amino sulphonyl and phenylaminosulphonyl.
The group R.sub.7 + may be selected from ammonium, mono C.sub.5-20 alkyl ammonium, di(C.sub.5-20 alkyl)-ammonium, tri(C.sub.5-20 alkyl)ammonium, preferably mono C.sub.8-16 alkyl ammonium, di(C.sub.8-16 alkyl)-ammonium, tri(C.sub.8-16 alkyl)ammonium and more preferably 4-amino-2,2,6,6-tetra-alkylpiperidinium, 4-hydroxy-2,2,6,6-tetraalkylpiperidinium and 4-keto-2,2,6,6-tetraalkyl-piperidinium. Particularly preferred groups R.sub.7.sup.+ are mono-octyl ammonium, 2-ethylhexyl-ammonium, 4-amino-2,2,6,6-tetramethyl-piperidinium, 4-hydroxy-2,2,6,6-tetramethyl-piperidinium or 4-keto-2,2,6,6-tetramethylpiperidinium.
In a preferred compound according to the invention the sulphamoyl group on a phenyl ring is in the 4- or 5-position whereas the sulfamoyl group on a naphthyl ring is in the 4- or 6-position.
More preferred compounds according to the invention have the following formulae ##STR6## or mixtures thereof wherein R.sub.2, R.sub.3 and R.sub.6 are as hereinabove defined and the group --SO.sub.2 NR.sub.2 R.sub.3 is in the 4- or 5-position when the ring is a phenyl ring and in the 4- or 6-position when the ring is a naphthyl ring. ##STR7## wherein R.sub.3 is methoxypropyl and the group --SO.sub.2 NR.sub.2 R.sub.3 is in the 4- or 5-position, more prefe

patent: 5376151 (1994-12-01), Freeman et al.
Chemical Abstracts, vol. 123, Abstract No. 202030 & JP070097530, Abstract and Compound RN 167768-55-0 Apr. 1995.
Chemical Abstracts, vol. 108, Abstract No. 29373 & JP620129358, Abstract and Compound RN 112210-23-8 & 111920-63-9 Jun. 1987.


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