Diarylacetylenes, enamines and acetylenic polymers and their production
OwnerAllan S. Hay, Martino Paventiinventors
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Abstract
Diarylacetylenes and diarylenamines are synthesized from a Schiff's base and an N-arylmethylheterocycle; these compounds are useful as intermediates for a variety of polymers; in particular an efficient process is provided for producing diaryl acetylenes useful in the efficient production of acetylene group-containing polymers which can be cross-linked to produce high strength polymers free of structural defects such as conventionally arise as a result of liberation of volatiles during the cross-linking.
Claims6
A process for producing an acetylenic group-containing polymer or copolymer of formula (VII):
- ##STR27## wherein Z.sub.1 is fluorine, hydroxyl or mercaptyl, Z.sub.2 is hydrogen or fluorine Z.sub.3 is --O--, --S--, --CH.sub.2 --, --CO--, --CO--Ar.sub.6 --CO-- or --Ar.sub.7 --, in which Ar.sub.6 and Ar.sub.7 are selected from divalent aromatic linkages, Y.sub.1 and Y.sub.2 are each selected from --O-- or --S--, provided that when Z.sub.3 is --O-- or --S--, Y.sub.1 and Y.sub.2 are both single bonds, Ar.sub.4 and Ar.sub.5 are each independently selected from arylene or hetarylene, unsubstituted or substituted one or more times by radicals selected from F;
- Cl,;
- Br;
- alkyl of 1 to 6 carbon atoms;
- alkenyl of 2 to 6 carbon atoms;
- aryl of 6 to 12 carbon atoms;
- aralkyl of 7 to 18 carbon atoms;
- aralkenyl of 8 to 18 carbon atoms;
- alkoxy of 1 to 6 carbon atoms;
- thioalkoxy of 1 to 6 carbon atoms;
- aryloxy of 6 to 12 carbon atoms or thioaryloxy of 6 to 12 carbon atoms;
- X is --Ar.sub.4 --C.tbd.C--Ar.sub.5 or a copolymer unit, n is an integer of 2 to 200, x is an integer of 0 to 199 and n is >x, comprising:
- polymerizing a diarylacetylene of formula (VI):
- X.sub.1 --Ar.sub.4 --C.tbd.C--Ar.sub.5 --X.sub.2 (VI)
- in which X.sub.1 and X.sub.2 are independently selected from F or OH and Ar.sub.4 and Ar.sub.5 are as defined above, or copolymerizing said diarylacetylene of formula (VI) with a comonomer selected from dihydroxy aromatics or dihaloaromatics in which the halogen atoms are activated for displacement, or in the presence of a reactant which provides a divalent linkage for the acetylenic monomer units, selected from --CH.sub.2 --, --O--, --S--, --CO-- or said copolymer unit X.
An acetylenic group-containing polymer or copolymer of formula (VII):
- ##STR32## wherein Z.sub.1 is fluorine, hydroxyl or mercaptyl, Z.sub.2 is hydrogen or fluorine, Z.sub.3 is --O--, --S--, --CH.sub.2 --, --CO--, --CO--Ar.sub.6 --CO-- or --Ar.sub.7 --, in which Ar.sub.6 and Ar.sub.7 are selected from divalent aromatic linkages, Y.sub.1 and Y.sub.2 are each selected from --O-- or --S--, provided that when Z.sub.3 is --O-- or --S--, Y.sub.1 and Y.sub.2 are both single bonds, Ar.sub.4 and Ar.sub.5 are each independently selected from arylene or hetarylene, unsubstituted or substituted one or more times by radicals selected from F;
- Cl,;
- Br;
- alkyl of 1 to 6 carbon atoms;
- alkenyl of 2 to 6 carbon atoms;
- aryl of 6 to 12 carbon atoms;
- aralkyl of 7 to 18 carbon atoms;
- aralkenyl of 8 to 18 carbon atoms;
- alkoxy of 1 to 6 carbon atoms;
- thioalkoxy of 1 to 6 carbon atoms;
- aryloxy of 6 to 12 carbon atoms or thioaryloxy of 6 to 12 carbon atoms;
- X is Ar.sub.4 --C.tbd.C--Ar.sub.5 or a copolymer unit, n is an integer of 2 to 200, x is an integer of 0 to 199 and n is >x, provided that when the polymer or copolymer has acetylenic units --Ar.sub.4 --C.tbd.C--Ar.sub.5 at both terminal positions, n is at least 3.
Dependencies are inferred from the claim text.