USA as Represented by Secretary of the Navy

Geo-Centers, Inc.

Jacques G O'Rear

James R Griffith

James R Griffth

A fluoroacrylate ester monomer having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently selected from the group consisting of saturated aliphatic hydrocarbons having from 1 to about 3 carbon atoms and R.sub.3 is selected from the group consisting of hydrogen and methyl. The monomer has a water-repellent 'umbrella' of 3 gem bis trifluoromethyl groups around the acrylate monomer which do not interfere with the acrylate properties. Polymerization of the monomer results in a stable, exceptionally hydrophobic, linear thermoplastic polymer. The invention also includes processes for making the monomer from a diether halide and certain novel intermediates.

Fluoroacrylate ester, polymer thereof, and process of making the same

A diacrylate monomer represented by the formula: ##STR1## wherein R represent CF.sub.3 or C.sub.2 F.sub.5, R' represents --H or --sub.3, R' represents H or --(CF.sub.2).sub.n F, and n is an integer from 1 to 10, and polymer therefrom.

Fluorinated diacrylic esters

Fluorinated diacrylic esters and polymers therefrom

A cis-trans fluoropolyol acrylate prepared by reacting acrylic acid anhyde with a fluoropolyol having the structural formula: ##STR1## where R is selected from the group consisting of --C(CF.sub.3).sub.2 C.sub.6 H.sub.4 C(CF.sub.3).sub.2 -- and --C(CF.sub.3).sub.2 CH.sub.2 CH.dbd.CH(CF.sub.3).sub.2 C--, R' is selected from the group consisting of --H and --CF.sub.2).sub.x F, x is 1 to 8 and n is any integer from 1 to 15, and the crosslinked thermosetting polymer prepared therefrom. The fluoropolyacrylate is useful in fabricating castings, coatings or adhesives.

Cis-trans fluoropolyol polyacrylate

A polphthalocyanine with the structure formula: ##STR1## prepared by mixing SnCl.sub.2.2H.sub.2 O with N, N'-bis(3,4-dicyanophenyecane diamide of which the structural formula is: ##STR2## heating the mixture to a temperature from about 175.degree. C. to about 185.degree. C. for about 15 to 20 minutes to form a resin; and curing the resin at a temperature from about 190.degree. C. to about 230.degree. C. The polyphthalocyanine is useful as an adhesive, as a matrix for glass or carbon-fiber reinforced composites, and as structural material.

Alkanediamide-linked polyphthalocyanines coordinated with SnCl.sub.2

Compounds of the general formula: ##STR1## wherein R.sub.1 is a radical of an isomer of phthalaldehyde; R.sub.2 is a adical of an isomer of an aromatic dialdehyde selected from the class consisting of phthalaldehyde, naphthalene dialdehyde, phenanthrene dialdehyde, anthracene dialdehyde, biphenyl dialdehyde, terphenyl dialdehyde; and mixtures thereof and R.sub.3 is a radical of an isomer of an aromatic diamine selected from the class consisting of benzene diamine, naphthalene diamine, phenanthrene diamine anthracene diamine, biphenyl diamine, and terphenyl diamine, and the cyano-condensation resins thereof which are useful in preparing semiconductors.

Bisorthodinitriles

Compounds of the general formula: ##STR1## wherein R.sub.1 is selected from the class consisting of ##STR2## R.sub.2 is an isomer of an aromatic dialdehyde selected from the class cisting of phthalaldehyde, naphthalene dialdehyde, phenanthrene dialdehyde, anthracene dialdehyde, biphenyl dialdehyde, terphenyl dialdehyde; and mixtures thereof and R.sub.3 is an isomer of an aromatic diamine selected from the class consisting of benzene diamine, naphthalene diamine, phenanthrene diamine, biphenyl diamine, and terphenyl diamine, and the cyano-condensation resins thereof which are useful in preparing semiconductors.

Electrical conducting phthalonitrile polymers

Compounds of the general formula: ##STR1## wherein R.sub.1 is an isomer of phthalaldehyde; R.sub.2 is an isomer of an romatic dialdehyde selected from the class consisting of phthalaldehyde, naphthalene dialdehyde, phenanthrene dialdehyde, anthracene dialdehyde, biphenyl dialdehyde, terphenyl dialdehyde; and mixtures thereof and R.sub.3 is an isomer of an aromatic diamine selected from the class consisting of benzene diamine, naphthalene diamine, phenanthrene diamine, biphenyl diamine, and terphenyl diamine, and the cyano-condensation resins thereof which are useful in preparing semiconductors.

N,N'-bis(3,4-dicyanophenyl) alkanediamides of the general formula: ##STR1## wherein R = (CH.sub.2).sub.n-2 and (CH.sub.2).sub.x CH(CH.sub.3)(CH.sub.2).sub.y ; n = 3 to 20; x = 1 to 8; and y = 1 to 8, prepared by reacting 4-aminophthalonitrile with a saturated aliphatic dicarboxylic acid halide. These dinitriles readily polymerize through heating by themselves or with a metal or with a salt to form polyphthalocyanine resins, of the infinite molecular weight type which are useful as coatings, laminates, adhesives, filament windings, and castings. The general formulas for these polyphthalocyanine resins are: ##STR2## wherein R = (CH.sub.2).sub.n-2 and (CH.sub.2).sub.x CH(CH.sub.3)(CH.sub.2).sub.y ; n = 3 to 20; x = 1 to 8; and y = 1 to 8.

N,N'-bis(3,4-dicyanophenyl) alkanediamide, polyphthalocyanines, and

N,N'-bis(3,4-dicyanophenyl) alkanediamides of the general formula: ##STR1## wherein R = (CH.sub.2).sub.n-2 and (CH.sub.2).sub.x CH(CH.sub.3)(CH.sub.sub.y ; n = 3 to 20; x = 1 to 8; and y = 1 to 8, prepared by reacting 4-aminophthalonitrile with a saturated aliphatic dicarboxylic acid halide. These dinitriles readily polymerize through heating by themselves or with a metal or with a salt to form polyphthalocyanine resins, of the infinite molecular weight type which are useful as coatings, laminates, adhesives, filament windings, and castings. The general formulas for these polyphthalocyanine resins are: ##STR2## wherein R = (CH.sub.2).sub.n-2 and (CH.sub.2).sub.x CH(CH.sub.3)(CH.sub.2).sub.y ; n = 3 to 20; x = 1 to 8; and y = 1 to 8.

N,N'-bis(3,4-dicyanophenyl) alkanediamides

Fluoro-anhydride curing agents for fluorinated epoxy resins, especially for highly fluorinated epoxy resins selected from the class consisting of hydroxyperfluoroalkyl phthalic anhydride, hydroxyperfluoroalkyl pyromellitic dianhydride, and mixtures thereof; a fluoro-anhydride curing agent for fluorinated epoxy resins that is the toluene-soluble mixture prepared by heating a hydroxyperfluoroalkyl benzenepentacarboxylic acid at about 240.degree. C; precursors for all of the curing agents; and the epoxy resins prepared therefrom.

Fluoro-anhydride curing agents and precursors thereof for fluorinated

N,N'-bis(3,4-dicyanophenyl) alkanediamides of the general formula: ##SPC1## Wherein R = (CH.sub.2).sub.n.sub.-2 and (CH.sub.2).sub.x CH(CH.sub.3)(CH.sub. 2).sub.y ; n = 3 to 20; x = 1 to 8; and y = 1 to 8, prepared by reacting 4-aminophthalonitrile with a saturated aliphatic dicarboxylic acid halide. These dinitriles readily polymerize through heating by themselves or with a metal or with a salt to form polyphthalocyanine resins, of the infinite molecular weight type which are useful as coatings, laminates, adhesives, filament windings, and castings. The general formulas for these polyphthalocyanine resins are: ##SPC2## ##SPC3## Wherein R = (CH.sub.2).sub.n.sub.-2 and (CH.sub.2).sub.x CH(CH.sub.3)(CH.sub.2).sub.y ; n = 3 to 20; x = 1 to 8; and y = 1 to 8.

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Temple Hills, MD, United States of America

Jacques G O'Rear