Substituted tetraamino heterocyclic compounds, useful in the preparation of substituted polybenzimidazoles and poly-imidazopyrrolones
AssigneeHorizons Incorporated, a division of Horizons Research Incorporated
InventorArthur H. Gerber
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Abstract
This invention relates to substituted tetraamino pyridines and to methods whereby such compounds are prepared. It also relates to the linear precyclized polymers produced by reaction of substituted tetraaminopyridines, or their acid salts, with a substantially equimolar amount of a suitable bis(acid halide) or dianhydride in a polar aprotic solvent at temperatures between about -10.degree.C and 70.degree.C. The resulting soluble, high molecular weight precyclized intermediates can be cyclodehydrated and may also be crosslinked to yield novel polybenzimidazoles and polyimidazopyrrolones.
Claims6
2,6-Di(substituted amino)-3,5-dinitropyridine compounds represented by a formula selected from the group consisting of ##SPC19##
- wherein R.sub.2 represents a monovalent member selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl and pentyl;
- R.sub.1 represents a monovalent member selected from the group consisting of hydrogen, C.sub.1 -C.sub.5 alkyl, substituted C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl, phenyl, pyridyl, picolyl, quinolyl, substituted benzyl, and substituted phenyl wherein the substituents on said members are selected from the group consisting of methyl, phenyl, pyridyl, -CN, -COOH and its salts, -SO.sub.3 and its salts, -NH.sub.2, ##SPC20##
- Cooc.sub.6 h.sub.5, -sh, thioaryl, thioalkyl, -CH=CHC.sub.6 H.sub.5, and N,N-dimethylamino;
- with the proviso that not all three of the R.sub.1 and R.sub.2 members can be H;
- and both of the R.sub.1 's need not be identical;
- R.sub.3 is a monovalent radical selected from the group consisting of H and alkyl of 1 to 5 carbon atoms;
- and
- x is a covalent bond or a divalent radical selected from the group consisting of alkylene of 1 to 3 carbon atoms, -S-, -O- and ##SPC21##
- where m is equal to 1 or 2;
- and each R.sub.3 NH- group is located ortho to a nitro group and the pyridyl rings containing the amino groups are joined via the 2,2', 3,3', or 2,3' positions with the provisos that when X is a covalent bond both R.sub.3 's cannot be hydrogen when the pyridyl groups are joined 2,2';
- and when X is ##SPC22##
- the pyridyl groups are joined 2,2';
- and further that both of the R.sub.3 's need not be identical.
Substituted tetraamino pyridine compounds represented by one of the formulae from the group consisting of ##SPC25##
- wherein R.sub.2 represents a monovalent member selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl and pentyl;
- R.sub.1 represents a monovalent member selected from the group consisting of hydrogen, C.sub.1 -C.sub.5 alkyl, substituted C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl, phenyl, pyridyl, picolyl, quinolyl, substituted benzyl, and substituted phenyl, wherein the substituents on said members are selected from the group consisting of methyl, phenyl, pyridyl, -CN, -COOH and its salts, ##SPC26##
- --COOC.sub.6 H.sub.5, -SO.sub.3 H and its salts, -SH, thioaryl, thioalkyl, --CH=CHC.sub.6 H.sub.5, and N,N-dimethylamino;
- with the proviso that not all three of the R.sub.1 and R.sub.2 members can be H;
- and both of the R.sub.1 's need not be identical;
- R.sub.3 is a monovalent radical selected from the group consisting of H and alkyl of 1 to 5 carbon atoms;
- and
- X is a covalent bond or a divalent radical selected from the group consisting of alkylene of 1 to 3 carbon atoms, -S-, -O-, and ##SPC27##
- where m is equal to 1 or 2;
- and each R.sub.3 NH- group is located ortho to an amino group and the pyridyl rings containing the amino groups are joined via the 2,2', 3,3', or 2,3' positions with the provisos that when X is a covalent bond both R.sub.3 's cannot be hydrogen when the pyridyl groups are joined 2,2';
- and when X is ##SPC28##
- the pyridyl groups are joined 2,2';
- and further that both of the R.sub.3 's need not be identical;
- and
- the acid salts thereof.
Dependencies are inferred from the claim text.