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Home Vasodialators Perimidene-and-benzimidazole-derivatives-useful-in-curable-compositions

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Details
Inventors: Moulton, Richard J.; Neuner, John D.;
Assignee: Hexcel Corporation (San Francisco, CA)
Primary Examiner:
Assistant Examiner:
Attorney, Agent or Firm:

A compound prepared by reacting at least one aromatic or aliphatic polyamine compound having at least two amine groups, which are separated by no more than one carbon atom, with at least one carbonyl-containing compound selected from the group consisting of aldehydes and ketones, wherein said polyamine compound is selected from: aliphatic polyamines having 2-20 carbon atoms corresponding to the formula: ##STR1## wherein A is a direct carbon-carbon bond or --CH.sub.2 -- and R.sub.3 and R.sub.4 are independently hydrogen or alkyl which may be branched or unbranched and which may be unsubstituted or substituted with amine groups; wherein said aldehydes correspond to the formula: ##STR2## wherein R represents alkyl of 1-20 carbon atoms, which may be branched or unbranched, and which may be unsubstituted or substituted with --CHO or --COOH; --CHO; --COOH; or phenyl which may be unsubstituted or substituted with --CHO, --OH OR lower alkoxy of 1-5 carbon atoms, and wherein said ketones correspond to the formula: ##STR3## wherein R.sub.1 and R.sub.2 independently represent alkyl of 1-20 carbon atoms, which may be branched or unbranched, and whose chain may be interrupted by one or more ##STR4## groups; phenyl; or R.sub.1 or R.sub.2 may together form a cycloaliphatic ring which may be interrupted by a ##STR5## group; or R.sub.1 and R.sub.2 may together form an O-heterocyclic ring which may be substituted with lower alkyl of 1-5 carbon atoms, --OH or acetyl; curable compositions containing the same; a method of curing; and composite articles are disclosed.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS It is common knowledge that amines react with ketones to form Schiff's bases or ketamines, e.
g.
, ##STR6## It is also know that 1,8-diamino-naphthalene will react with carboxylic acids and esters, in the present of an oxidizing agent to yield perimidines, Balasubramaniyan, Chem.
Revs.
, 66, 6, pp 567.
The novel heterocyclic multifunctional amine adduct of the present invention is the reaction product of at least one aromatic or aliphatic polyamine compound having at least two amine groups, which are separated by no more than one carbon atom, with at least one carbonyl-containing compound selected from the group consisting of aldehydes and ketones.
Suitable aldehydes correspond to the formula: ##STR7## wherein R represents: an alkyl group of one to twenty carbon atoms, which may be branched or unbranched, and which may be unsubstituted or substituted with an aldehyde group (--CHO) or a carboxyl group (--COOH); an aromatic residue, preferably a phenyl group, which may be unsubstituted or substituted with an aldehyde group, a hydroxyl group or a lower alkoxy group of one to five carbon atoms.
Examples of such aldehydes are terephtalaldehyde, glyoxal, glutaraldehyde, glyoxylic acid, salicylaldehyde, vanillin and o-vanillin and heptaldehyde Suitable ketones correspond to the formula: ##STR8## wherein R.
sub.
1 and R.
sub.
2 independently represent: an alkyl group of one to twenty carbon atoms, which may be branched or unbranched, whose chain may be interrupted by one or more carbonyl groups ##STR9## an aromatic residue, preferably phenyl; or R.
sub.
1 and R.
sub.
2 may together form a cycloaliphatic ring may be interrupted by a carbonyl group; or R.
sub.
1 and R.
sub.
2 may together form an O-heterocyclic ring which may be substituted with lower alkyl group of one to five carbon atoms, hydroxyl group or acetyl group.
Examples of such ketones are 2,4-pentanedione; 2,3-butanedione; benzil; 1,3-cyclohexanedione; acetone; 2-butanone; 2-heptanone; dehydroacetic acid and acetophenone



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