Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1992-03-09
1995-11-14
Geist, Gary L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546 10, 546 37, C09B 562, C07D47106
Patent
active
054668077
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel, useful perylene compounds which contain sulfonic acid groups and correspond to the general formula I ##STR1## and in which A is a bivalent radical --O--, >NR.sup.1 or >N--R.sup.2 --SO.sub.3.sup.- X.sup.+ and thereof, and C.sub.1 -C.sub.18 -alkyl and in particular C.sub.1 -C.sub.4 -alkyl, or an aryl group, preferably phenyl, which can be unsubstituted or mono- or polysubstituted by halogen, such as chlorine or bromine, sulfo, C.sub.1 -C.sub.4 -alkyl, such as methyl or ethyl, C.sub.1 -C.sub.4 -alkoxy, such as methoxy or ethoxy, or phenylazo, in particular ethylene or propylene, and metal cation from main group 1 to 5 or from subgroup 1 or 2 or 4 to 8 of the periodic system of the chemical elements, in which m is one of the numbers 1, 2 or 3, such as, for example, Li.sup.1+, Na.sup.1+, K.sup.1+, Mg.sup.2+, Ca.sup.2+, Sr.sup.2+, Ba.sup.2+, Mn.sup.2+, Cu.sup.2 +, Ni.sup.2+, Cd.sup.2+, Co.sup.2+, Zn.sup.2+, Fe.sup.2+, Al.sup.3+, Cr.sup.3+, or Fe.sup.3+ ; or an ammonia ion N.sup.+ R.sup.3 R.sup.4 R.sup.5 R.sup.6, in which the substituents R.sup.3, R.sup.4, R.sup.5 and R.sup.6 on the quaternary N atom independently of one another are each a hydrogen atom or a group from the series comprising C.sub.1 -C.sub.30 -alkyl, C.sub.1 -C.sub.30 -alkenyl and C.sub.1 -C.sub. 30 -cycloalkyl, unsubstituted or by [sic] C.sub.1 -C.sub.8 -alkylated phenyl or a (poly)alkyleneoxy group ##STR2## in which R.sup.7 is hydrogen or C.sub.1 -C.sub.4 -alkyl and k is a number from 1 to 30, and in which alkyl, alkenyl, cycloalkyl, phenyl or alkylphenyl identified as R.sup.3, R.sup.4, R.sup.5 and/or R.sup.6 can moreover optionally be substituted by amino, hydroxyl and/or carboxyl; or in which the substituents R.sup.3 and R.sup.4, together with the quaternary N atom, can form a five- to seven-membered saturated ring system, which optionally also contains further hetero atoms, such as an O, S and/or N atom, for example of the pyrrolidone, imidazolidine, hexamethyleneimine, piperidine, piperazine or morpholine type; or in which the substituents R.sup.3, R.sup.4 and R.sup.5, together with the quaternary N atom, c an form a five- to seven-membered aromatic ring system, which Optionally also contains further hetero atoms, such as an O, S and/or N atom, and onto which additional rings are optionally fused, for example of the pyrrole, imidazole, pyridine, picoline, pyrazine, quinoline or isoquinoline type.
Compounds of the general formula I which have found particular interest according to the invention are, those in which --SO.sub.3.sup.- X.sup.+ and metal cation of the chemical elements described individually above, or an ammonium ion N.sup.+ R.sup.3 R.sup.4 R.sup.5 R.sup.6, in which the substituents R.sup.3, R.sup.4 and R.sup.5 on the quaternary N atom independently of one another are each a hydrogen atom or the group C.sub.2 -C.sub.3 -hydroxyalkyl, and R.sup.6 is one of the groups from the series comprising C.sub.1 -C.sub.30 -alkyl, C.sub.1 -C.sub.30 -alkenyl, C.sub.2 -C.sub.3 -hydroxyalkyl and C.sub.5 -C.sub.6 -cycloalkyl.
Perylene compounds of the general formula I which contain sulfonic acid groups and are classified as exceptionally useful according to the invention are those in which --SO.sub.3.sup.- X.sup.+ and and H.sub.3 R.sup.6, in which R.sup.6 is to be considered as being of the type described immediately above.
The invention in question also relates to a process for the preparation of the above-described perylene compounds containing sulfonic acid groups and having the chemical structure according to formula I. These novel compounds can be obtained by reacting perylene-3,4,9,10-tetracarboxylic acid monoanhydride mono-alkali metal salts, in particular the monopotassium salt, perylene-3,4,9,10-tetracarboxylic acid monoanhydride monoimide, N-monoalkyl- or N-monoarylimides or perylene-3,4,9,10-tetracarboxylic acid dianhydride with primary aliphatic amines containing sulfonic acid groups, of the general formula II aminoalkanesulfonic acids or salts thereof, such as, in particular, taurine (2-ami
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Dietz Erwin
Urban Manfred
Geist Gary L.
Hoechst Aktiengesellschaft
Kilby Scalzo Catherine S.
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