DETAILED DESCRIPTION OF THE INVENTION It has been discovered that acetylene-substituted Schiff's bases can be prepared from the reaction of acetylene-substituted amines and dicarboxaldehydes or from the reaction of acetylene-substituted aldehydes and diamines.
The molecular structures of these products can be illustrated as follow: H--C.
tbd.
C--Ar--R--Ar--C.
tbd.
CH (1) where R may be --N.
dbd.
N--Ar'--CH.
dbd.
N--, or --CH.
dbd.
N--Ar'--N.
dbd.
CH-- and Ar is phenylene, biphenylene, naphthylene, anthracene, phenanthrene, pyrene, alkyl or aryl substituted phenylene, alkyl or aryl substituted biphenylene, alkyl or aryl substituted naphthylene, and heterocyclic analogues of the above wherein one or more of the aromatic carbon atoms is replaced by a nitrogen or sulphur atom.
The advantages of this invention lie in the fact that acetylene-substituted Schiff's bases can be made very easily, they usually have low melting points prior to cure, they can polymerize through a tacky viscous state, and they can produce partially and fully conjugated polymeric products.
Acetylene-substituted amines suitable for use in preparing the prepolymers of this invention have the formula: HC.
tbd.
C--Ar--NH.
sub.
2 ( 2) where Ar is as defined above.
However Ar may also be a compound whose general structure is: ##STR1## Aromatic dicarboxaldehydes suitable for use in preparing the prepolymers of this invention have the general formula OHC--Ar'--CHO (4) where Ar'may be phenylene, diphenylene, terphenylene, naphthalene, anthracene, phenanthrene, or a compound whose structure is .
phi.
--X'--.
phi.
wherein .
phi.
is phenylene and X' is O, S, CH.
sub.
2, --CH.
sub.
2 --.
sub.
n, --CO--, --CF.
sub.
2 --.
sub.
n, >C(CH.
sub.
3).
sub.
2, or --SO.
sub.
2 --.
A typical reaction sequence leading to the production of one species of oligomers in accordance with this invention is as follows: ##STR2## The preferred compounds of this invention are synthesized from ortho or para substituted amino-phenyl acetylenes which yield fully conjugated oligomers.
The term "fully conjugated" is understood to imply that each double or triple bond is attached to a single bond which in turn is attached to another double or triple bond as shown below: ##STR3## In a similar manner, conjugated Schiff's bases can be made by the reaction of a diamine with ethynylphenyl ketone or ethynylphenyl aldehyde
|
Manufacturing Materials 
