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Perfluoroether triazine elastomers having improved properties are prepared from oligomeric imidoylamidines that were in turn, prepared by the process of: (1) reacting a perfluorodinitrile with liquid ammonia to yield a perfluorodiamidine, (2) isolating the perfluorodiamidine, (3) reacting the isolated diamidine with a perfluorodinitrile to yield a perfluoro(imidoylamidine) dinitrile, and then repeating the steps to sequentially grow an oligomer of desired molecular size. The isolated amidine and nitrile intermediates are also disclosed. The elastomers can be fashioned into seals, gaskets, and sealing components and the like.

Composite materials made from unfilled and glass-fiber-reinforced epoxy toughened by copolymerization with elastomeric prepolymers of perfluoroalkyl ether diacyl fluoride (EDAF). Improved properties due to hydrogen bonding between rubber phase and epoxy matrix, plus formation of rubberlike phase domains that molecularly interpenetrate with epoxy matrix. With optimum rubber content, particle size, and particle shape, entire molecular structure reinforced and toughened. Improved composites also show increased failure strength, stiffness, glass-transition temperature, and resistance to water.

Filleting and channel sealants developed for sealing cavities in wings and fusealage of aircraft. Both sealants function well at 177 degrees C, as required in current specifications for supersonic aircraft. Sealants have excellent resistance to fuel and other solvents. They stay flexible, resistant to vibrational, thermal, and mechanical stresses, and adhere well to aluminum. Prove useful in industrial applications requiring resistance to solvents at high temperatures.

A perfluorinated alkyl ether diacyl fluoride prepolymer (molecular weight about 1500) was coreacted with Epon 828 epoxy resin and diamino diphenyl sulfone to obtain an elastomer-toughened, glass-cloth composite. Improvements in flexural toughness, impact resistance, and water resistance, without loss of strength, modulus of elasticity or a lowering of the glass-transition temperature, were realized over those of the unmodified composite. Factors concerning optimization of the process are discussed. Results suggest that a simultaneously interpenetrating polymer network may be formed which gives rise to a measured improvement in composite mechanical properties.

New process yields product that resists heat and action of oxygen and water. Ring closing step, which gives elastomer its stability, imidoylamidine dinitrile reacts with perfluoroether acide, yielding prepolymer. Prepolymer then treated with ammonia and cured by heating to form polymer. Elastomers are highly resistant to heat, oxidation, and hydrolysis.

Perfluoroether triazine elastomers having improved properties and utility in seals, gaskets, sealing components and the like are prepared from oligomeric imidoylamidines that have, in turn, been prepared by the process of (1) reacting a perfluorodinitrile with liquid ammonia to yield a perfluorodiamidine, (2) isolating the perfluorodiamidine, (3) reacting the isolated diamidine with a perfluorodinitrile to yield a perfluoror(imidoylamidine) dinitrile, and then repeating step (1), (2), and (3) to sequentially grow an oligomer of desired molecular size. The isolated amidine and nitrile intermediates are also described.

Addition of controlled amounts of perfluorinated alkyl ether diacyl fluoride to epoxy resin systems prior to cure results in a formulation which, exhibits improved energy absorbing properties.

Perfluorinated imidoylamidoxime polymers with excellent resistance to heat, chemicals and solvents are prepared by condensing a perfluorinated nitrile with a perfluorinated amidoxime in vacuum or inert atmosphere from 20 degrees to 70 degrees C. When both reactants are difunctional, oligomeric or polymeric products are obtained. After cyclization of imidoylamidoxime groups to 1,2,4-oxadiazole linkages, process yields highly resistant elastomers. Competing side reactions are inhibited by low processing temperature.

Long-chain perfluoropolyethers containing functional pendent groups were investigated as possible candidates for new sealants and elastomers that function in extreme environments. Of specific interest was development of materials exhibiting high thermal and oxidative stability at temperatures around 400 degrees C, low-temperature flexibility with glass transition at about 50 degrees C, and hydrolytic stability as well as compatibility with metals and resistance to fuels.

The feasibility of applying the in situ fiberization process to the fabrication of strain isolation pads (SIP) for the Space Shuttle and to the fabrication of graphite-epoxy composites was evaluated. The ISF process involves the formation of interconnected polymer fiber networks by agitation of dilute polymer solutions under controlled conditions. High temperature polymers suitable for SIP use were fiberized and a successful fiberization of polychloro trifluoroethylene, a relatively high melting polymer, was achieved. Attempts to fiberize polymers with greater thermal stability were unsuccessful, apparently due to characteristics caused by the presence of aromaticity in the backbone of such materials. Graphite-epoxy composites were fabricated by interconnecting two dimensional arrays of graphite fiber with polypropylene IS fibers with subsequent epoxy resin impregnation. Mechanical property tests were performed on laminated panels of this material to evaluate intralaminar and interlaminar shear strength, and thus fracture toughness. Test results were generally unpromising.

High performance channel sealant is based on NASA patented cyano and diamidoximine-terminated perfluoroalkylene ether prepolymers that are thermally condensed and cross linked. The sealant contains asbestos and, in its preferred embodiments, Lithofrax, to lower its thermal expansion coefficient and a phenolic metal deactivator. Extensive evaluation shows the sealant is extremely resistant to thermal degradation with an onset point of 280 C. The materials have a volatile content of 0.18%, excellent flexibility, and adherence properties, and fuel resistance. No corrosibility to aluminum or titanium was observed.

Fluorinated alkyl or alkylether 1,2,4 oxadiazole compounds are prepared by cyclizing the corresponding alkyl or alkylether imidoyl amidoximes in vacuo or in an inert atmosphere at a temperature within the range of 40 C to 100 C. for a period of 8 to 144 hours in the presence of an acid compound which can accept ammonia to form a salt. The imidoyl amidoximes usable in this process are either polymeric or nonpolymeric. The products, when polymeric, have excellent heat, chemical and solvent resistance.

New 1,1,1-triaryl-2,2,2-trifluoroethanes in which the aryl radicals carry one or more substituents were prepared by condensation of trifluoroacetophenones with substituted phenyl compounds in the presence of catalytic quantities of trifluoromethylsulfonic acid. The reaction can be carried out under reflux in toluene or, for strikingly better results in certain cases, reactants are simply stirred at room temperature for about 24 to 48 hours.

New crosslinked 1,2,4-oxadiazole elastomers were prepared by thermally condensing a monomer having the formula H2N(HON)C-R-Q, wherein Q is a triazine ring-forming group such as nitrile or amidine or a mixture of such group with amidoxime, or a mixture of said monomer with R C(NOH)NH2 sub 2 with R in these formulas standing for a bivalent organic radical. In the monomer charge, the overall proportions of amidoxime groups to triazine ring-forming groups varies depending on the extent of crosslinking desired in the final polymer.