Phosphorus Reactant Contains A Nitrogen Atom Patents (Class 528/399)
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Patent number: 4276403Abstract: Polydihalophosphazenes, e.g. --N.dbd.P(Cl).sub.2 ].sub.n, are allowed to react at ambient temperatures for at least one hour with a lithium carborane in a suitable inert solvent. The remaining chlorine substituents of the carboranyl polyphosphazene are then replaced with aryloxy or alkoxy groups to enhance moisture resistance. The polymers give a high char yield when exposed to extreme heat and flame and can be used as insulation.Type: GrantFiled: March 12, 1980Date of Patent: June 30, 1981Inventors: Robert A. Administrator of the National Aeronautics and Space Administration, with respect to an invention of Frosch, Harry R. Allcock, John P. O'Brien, Angelo G. Scopelianos, Larry L. Fewell
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Patent number: 4267311Abstract: A procedure is disclosed for the removal of alkali metal halide from phosphazene rubber crumb swollen in water. The crumb is pressed whereby a large proportion of the alkali halide is discharged from the crumb.Type: GrantFiled: February 22, 1977Date of Patent: May 12, 1981Assignee: The Firestone Tire & Rubber CompanyInventor: Robert A. Elefritz, Jr.
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Patent number: 4264759Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is represented by: ##STR2## wherein R.sub.1, and R.sub.2 and R.sub.3 are independently selected from the group consisting of substituted or unsubstituted alkyl and alkoxy radicals containing from 1 to 12 carbon atoms and aryl radicals; X' is chlorine or a substituted or unsubstituted alkoxy, aryloxy, amino or mercapto radical or mixture thereof, which are compatible with the alkoxy substituent containing a fully substituted carbon in the beta position; and 20.ltoreq.(w+y+x).ltoreq. 50,000 per polymer.The polymers of the invention can be utilized to form protective films, and can also be utilized in applications such as for molding, coatings, foams and the like.Type: GrantFiled: September 8, 1978Date of Patent: April 28, 1981Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4258172Abstract: Alkylated phosphazene oligomers of the general formula (NP(X.sub.2)).sub.n PRH, wherein X represents chlorine or bromine, R represents a linear or branched alkyl, and n represents an integer from 2 to 8, are prepared by reacting, in a nonoxidizing atmosphere, a perhalopolyphosphazene, a Grignard reagent, and a cuprous complex in solution, followed by the addition of a secondary or tertiary alcohol. Polymers useful as high-temperature elastomers, are prepared from the halo-substituted oligomers by heating them at a temperature from about 200.degree. C. to about 300.degree. C., followed by a reaction with an amine, metal alkoxide, or a metal aryloxide at a temperature from 20.degree. to 200.degree. C.Type: GrantFiled: September 25, 1979Date of Patent: March 24, 1981Assignee: The United States of America as represented by the Secretary of the NavyInventors: Harry R. Allcock, Paul J. Harris
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Patent number: 4258173Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is R(OR').sub.n O-- in which R is alkyl containing from 1 to 20 carbon atoms, aryl, alkylaryl or arylalkyl, R' is an alkylene radical and n is an integer from 1 to 70; wherein X' is X or is selected from the group consisting of substituted or unsubstituted alkoxy, alkenyloxy, aryloxy, alkenylaryloxy, amino and mercapto groups and wherein 20.ltoreq.(a+b+c).ltoreq.50,000 per polymer.The polymers of the invention can be utilized to form films and may also be utilized in applications for moldings, coatings, foams and the like.Type: GrantFiled: October 11, 1979Date of Patent: March 24, 1981Assignee: The Firestone Tire & Rubber CompanyInventors: Donald N. Schulz, Tai C. Cheng, Thomas A. Antkowiak
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Patent number: 4258171Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X and X' are the same or different and are represented by: ##STR2## wherein R.sub.1-4 are independently selected from the group consisting of hydrogen, halogen, nitro, cyano, alkylmercapto, arylmercapto, dialkylamine, alkyl, aryl, alkoxy, aryloxy and heterocyclic radicals or R.sub.1 and R.sub.3 when taken together can form a cycloalkyl or heterocyclic ring; X' can also be selected from a group consisting of chloro radicals, substituted or unsubstituted alkoxy, aryloxy, amino and mercapto radicals or mixtures thereof; and 20.ltoreq.(w+y+z).ltoreq.50,000 per polymer.The polymers of the invention can be utilized to form protective films and can also be utilized in applications such as for molding, coatings, foams and the like.Type: GrantFiled: September 4, 1979Date of Patent: March 24, 1981Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4258170Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is represented by one or more of the following structural formulas: ##STR2## wherein R.sub.1-11 are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, and substituted and unsubstituted alkyl, aryl, alkoxy, aryloxy, alkylmercapto, and dialkylamino radicals, and R.sub.1 or 3 and R.sub.2, or R.sub.5 and R.sub.6 taken together can form a substituted or unsubstituted benzene ring structure; X' can represent one or more substituents from the group consisting of a halogen radical, substituted and unsubstituted alkoxy, aryloxy, amino and mercapto radicals which are known in the state of the art in poly(phosphazene) technology and which are compatible with the copolymer substituents. The polymer can contain from 20 to 50,000 of such units such that 20.ltoreq.(w+y+z).ltoreq.50,000.Type: GrantFiled: August 20, 1979Date of Patent: March 24, 1981Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4247679Abstract: Polyphosphazene copolymers are prepared which contain units represented by the formulas: ##STR1## wherein X is --OR'RC--C.uparw.CH in which R and R' are hydrogen or alkyl groups containing from 1 to 6 carbon atoms; wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, amino and mercapto groups and wherein 20.ltoreq.(a+b+c).ltoreq.50,000 per polymer.The copolymers of the invention can be utilized to form protective films and may also be utilized in applications such as moldings, coatings and the like.Type: GrantFiled: September 8, 1978Date of Patent: January 27, 1981Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4247680Abstract: Polyphosphazene copolymers are prepared which contain randomly distributed units represented by the formulas: ##STR1## wherein X is --OB(OR).sub.2 in which R is a branched, straight chain or cyclic alkyl group containing from 1 to 12 carbon atoms or mixtures thereof, and wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, amino and mercapto groups. The alkyl groups may vary in carbon chain length within the borate or all be the same.The copolymers of the invention can be utilized to form protective films and may also be utilized in applications such as for moldings, coatings, and the like. The copolymers of the invention also crosslink at room temperature in the presence of water yielding a solvent resistant film.Type: GrantFiled: September 8, 1978Date of Patent: January 27, 1981Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4243795Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is the same or a mixture of different radicals represented by the following structural formula: ##STR2## wherein R.sub.1 is selected from the group consisting of alkyl and aryl radicals and R.sub.2, R.sub.3 and R.sub.4 are independently selected from the group consisting of hydrogen, alkyl, alkenyl aryl, alkoxy, aryloxy and heterocyclic radical and R.sub.1-4 can be substituted with one or more substituents which are non-reactive with various materials during polymer formation; and X' can be substituted or unsubstituted and is selected from the group consisting of halogen, alkoxy, aryloxy, amino and mercapto radicals or mixtures thereof; and 20 (w+y+z) 50,000 per polymer.The polymers of the present invention can be utilized in applications such as molding, coatings, foams, fibers and the like.Type: GrantFiled: September 4, 1979Date of Patent: January 6, 1981Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4243796Abstract: Polyphosphazene copolymers are prepared which are comprised of repeating units represented by the formulas: ##STR1## wherein X is represented by the formula: ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, substituted and unsubstituted alkyl radicals containing from 1 to 15 carbon atoms, substituted and unsubstituted cycloalkyl, aryl, arylalkyl, and heterocyclic radicals; X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, mercapto and amino radicals, and mixtures thereof; and 20.ltoreq.(w+y+z).ltoreq.50,000 per polymer unit.The polyphosphazene polymers of the present invention are prepared by the reaction of the enol form of an aldehyde or a ketone and an additional reactant such as an alkanol, aryl alcohol, mercaptan, or amine with poly(dichlorophosphazene) in the presence of a tertiary amine. The polymers of this invention may be modified by crosslinking or curing.Type: GrantFiled: September 8, 1978Date of Patent: January 6, 1981Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4242492Abstract: Polyphosphazene polymers are prepared which contain randomly distributed units represented by the formulas: ##STR1## wherein X is selected from the group consisting of substituted and unsubstituted mono, di, and tri nitro substituted phenoxy groups and mixtures thereof and wherein X' is the same as X or is selected from the group consisting of substituted and unsubstituted alkoxy, alkenyloxy, aryloxy, alkenylaryloxy, amino and mercapto groups.The polymers of the invention can be utilized to form protective films and may also be utilized in application such as for moldings, coatings, and the like where heat stability and solvent resistance are important.Type: GrantFiled: September 8, 1978Date of Patent: December 30, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4242493Abstract: A method of producing substantially pure polyhalophenoxyphosphazene homopolymers or copolymers which are free from phenoxy groups formed by reduction of halophenols is provided. The method involves as a first step preparing a substantially pure sodium salt of a halogen-substituted phenol (in the case of homopolymers) or the substantially pure sodium salts of a mixture of a halogen-substituted phenol and an alkyl or alkoxy-substituted phenol, alkanol, or fluoroalkanol (in the case of copolymers) by reacting said halogen-substituted phenol or mixture with sodium hydride. Following this procedure, the resultant sodium salt or salts are reacted with a poly(dichlorophosphazene) of the formula (NPCl.sub.2).sub.n, in which n is from 20 to 50,000, to produce a mixture of polyhalophenoxyphosphazene homopolymer or copolymer and sodium chloride. The sodium chloride is then separated from the mixture to produce a substantially pure polyhalophenoxyphosphazene homopolymer or copolymer which is free from phenoxy groups.Type: GrantFiled: April 19, 1979Date of Patent: December 30, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: Tai C. Cheng, John R. Schreffler
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Patent number: 4242491Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X and X' are the same or different and are represented by: ##STR2## wherein R.sub.1 is selected from the group consisting of hydrogen and a methyl group; R.sub.2 and R.sub.3 are independently selected for each carbon atom from a group consisting of hydrogen and alkyl radical containing from 1 to 6 carbon atoms; 2.ltoreq.m.ltoreq.20; X' can additionally be selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, amino and mercapto radicals, and mixtures thereof, which are compatible with an alkoxy acrylate substituent and are known in the state of the art of polyphosphazene technology; and 20.ltoreq.(w+y+z).ltoreq.50,000 per polymer.The polymers of the invention can be utilized to form protective films and can also be utilized in applications such as for molding, coatings, foams and the like.Type: GrantFiled: September 8, 1978Date of Patent: December 30, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4242495Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is the same or a mixture of different radicals represented by: ##STR2## wherein X.sub.1 is selected from the group consisting of --O-- and --S--; X.sub.2 is selected from the group consisting of --O--, --S--, --NH--, and --N(R)-- where R is a lower alkyl radical; R.sub.1 and R.sub.2 are independently selected from a group consisting of hydrogen, chloro, bromo, cyano, nitro, alkylmercapto, dialkylamino, and substituted and unsubstituted alkyl, aryl, alkoxy and aryloxy radicals; the sum of (q+q') is an integer from 0 to 4; X' can be the same as X or can be selected from a group consisting of halogen and substituted and unsubstituted alkoxy, aryloxy, amino and mercapto radicals and mixtures thereof.The polymers of the invention can be utilized in applications such as coatings, moldings, foams and the like.Type: GrantFiled: September 4, 1979Date of Patent: December 30, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4242499Abstract: Poly(organophosphazenes) with chromphoric substituents and method of preparation. Products are useful to add color to polyphosphazene polymers to produce food colorants, colored films, colored fibers and similar products.Type: GrantFiled: July 27, 1979Date of Patent: December 30, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: Harry R. Allcock, Karen M. Kosydar, Sarah D. Wright
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Patent number: 4242494Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X and X' are the same or different and are represented by: ##STR2## wherein R is selected from the group consisting of hydrogen and unsubstituted and substituted alkyl, aryl, and heterocyclic groups; X' may additionally be selected from the group consisting of chloro- and substituted or unsubstituted alkoxy, aryloxy, amino and mercapto radicals or a mixture thereof; and 20.ltoreq.(w+y+z).ltoreq.50,000.The polymers of the invention can be utilized in applications such as molding, coatings, foams and the like.Type: GrantFiled: August 20, 1979Date of Patent: December 30, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4237263Abstract: Poly(organophosphazenes) containing one alkyl group per each three repeating units are prepared. These polymers are represented by the structure: ##STR1## wherein R is alkyl containing from 1 to 10 carbon atoms; wherein X is selected from the group consisting of chlorine and --OR' radicals in which R' is the same as R or is selected from the group consisting of substituted alkyl radicals and substituted or unsubstituted aryl radicals and wherein n is from 3 to 15,000.Polymers of the above structure in which X is chlorine are prepared by thermally polymerizing a monoalkyl-pentachloro-cyclotriphosphazene having the formula N.sub.3 P.sub.3 Cl.sub.5 R in which R is as defined above. Polymers of the above structure in which X is an --OR' radical as defined above are prepared by thermally polymerizing the monoalkyl-pentachloro-cyclotriphosphazene and then reacting the resultant linear polymer with a suitable alkali metal alkoxide or aryloxide.Type: GrantFiled: May 21, 1979Date of Patent: December 2, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: Harry R. Allcock, Robert J. Ritchie
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Patent number: 4226972Abstract: Poly(organophosphazenes) containing repeating units of the structure: ##STR1## wherein X and X' represent organic substituents which may be the same or different and n is from 20 to 50,000, are prepared by a process which involves reacting a poly(dichlorophosphazene) having the formula --(NPCl.sub.2).sub.n --, in which n is from 20 to 50,000, with an active hydrogen-containing compound in the presence of a bicyclic amidine represented by the structure: ##STR2## in which m is an integer of from 1 to 10. A unique aspect of the process of the invention is that it can be utilized to prepare such poly(organophosphazenes) utilizing either soluble or gelled (insoluble) poly(dichlorophosphazenes) as starting materials.Type: GrantFiled: November 3, 1978Date of Patent: October 7, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: Donald N. Schulz, Jung W. Kang, John W. Spiewak
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Patent number: 4225697Abstract: Polyphosphazene polymers are prepared which contain units represented by the formulas: ##STR1## wherein X is ##STR2## in which R is an alkyl group of 1 to 8 carbon atoms and a is an integer of 2 to 8 and wherein X' is the same as X for homopolymers and for copolymers X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, amino or mercapto groups.The polymers of the invention can be utilized to form protective films and may also be utilized in applications such as moldings, coatings and the like.Type: GrantFiled: November 3, 1978Date of Patent: September 30, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4223102Abstract: Polyphosphazene polymers are prepared which contain units represented by the formulas: ##STR1## wherein X is --NHNHCOOR in which R is alkyl containing from 1 to 12 carbon atoms, cycloalkyl containing 3 to 12 carbon atoms or aryl; wherein X' is X or is selected from the group consisting of substituted or unsubstituted alkoxy, aryloxy, amino and mercapto groups and wherein 20.ltoreq.(a+b+c).ltoreq.50,000 per polymer.The polymers of the invention can be utilized to form films and may also be utilized in applications for moldings, coatings and the like.Type: GrantFiled: October 20, 1978Date of Patent: September 16, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4223103Abstract: Polyphosphazene polymers are prepared which contain units represented by the formulas: ##STR1## wherein X is ##STR2## in which R is alkylene radical containing from 0 to 10 carbon atoms, R' is hydrogen or alkyl containing from 1 to 10 carbon atoms and n is an integer of from 0 to 10; wherein X' is X or is selected from the group consisting of substituted or unsubstituted alkoxy, aryloxy, amino and mercapto groups and wherein 20.ltoreq. (a+b+c).ltoreq.50,000 per polymer.The polymers of the invention can be utilized to form films and may also be utilized in applications such as moldings, coatings, foams and the like.Type: GrantFiled: February 26, 1979Date of Patent: September 16, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: Donald N. Schulz, Jung W. Kang
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Patent number: 4221898Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formula: ##STR1## wherein X and Y are the same or different and are selected from the group consisting of:--CH.sub.2 O--, --O--, --S--, and --NH--;and R is selected from the group consisting of halogen, cyano, nitro, alkoxy and alkyl radicals containing from 1 to 12 carbon atoms; n'=0 to 4; and 20.ltoreq.w.ltoreq.50,000 per polymer. The polymers of the invention can contain a mixture of different ortho-difunctional phenylene substituents.The polymers of the invention can be utilized to form protective films and can also be utilized in applications such as for molding, coatings, foams, fibers and the like.Type: GrantFiled: September 8, 1978Date of Patent: September 9, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4221904Abstract: Polyphosphazene copolymers are prepared which contain randomly distributed units represented by the formulas: ##STR1## wherein X is ##STR2## in which R is alkyl containing from 1 to 12 carbon atoms or aryl, wherein X' is selected from the group consisting of substituted or unsubstituted alkoxy, aryloxy, amino and mercapto groups and wherein 20.ltoreq.(a+b+c).ltoreq.50,000 per polymer.The copolymers of the invention can be utilized to form solvent resistant films and may also be utilized in applications for moldings, coatings and the like. Additionally, the copolymers may be utilized as crosslinking agents for other reactive monomers or polymers. An especially useful feature of these copolymers is that they can be cured or crosslinked at room temperature.Type: GrantFiled: September 8, 1978Date of Patent: September 9, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4221899Abstract: Polyphosphazene polymers are prepared which contain units represented by the formulas: ##STR1## wherein X is ##STR2##in which R and R.sub.1 are selected from the group consisting of alkyl groups containing from 1 to 12 carbon atoms, cycloalkyl groups containing from 3 to 12 carbon atoms and aryl groups; wherein X' is X or is selected from the group consisting of substituted or unsubstituted alkoxy, aryloxy, amino and mercapto groups and wherein 20.ltoreq.(a+b+c).ltoreq.50,000 per polymer.The polymers of the invention can be utilized to form films and may also be utilized in applications such as complexing agents, moldings, coatings, foams and the like.Type: GrantFiled: October 20, 1978Date of Patent: September 9, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4221900Abstract: Polyphosphazene polymers are prepared which contain units represented by the formulas: ##STR1## wherein X is ##STR2## in which R and R.sub.1 are selected from the group consisting of alkyl groups containing from 1 to 12 carbon atoms, cycloalkyl groups containing from 3 to 12 carbon atoms and aryl groups wherein X' is selected from the group consisting of substituted or unsubstituted alkoxy, aryloxy, amino and mercapto groups and wherein .ltoreq.20(a+b+c).ltoreq.50,000 per polymer.The copolymers of the invention can be utilized to form films and may also be utilized in applications such as moldings, coatings, foams and the like.Type: GrantFiled: February 16, 1979Date of Patent: September 9, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4219637Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formula: ##STR1## wherein X and Y are the same or different and are selected from the group consisting of: --O--, --S--, or --NH--; R.sub.1-6 are independently selected from a group consisting of hydrogen, alkyl containing 1 to 10 carbon atoms, cycloaliphatic compounds containing 3 to 10 carbon atoms, and substituted or unsubstituted aryl; a is 0 to 1, and 20.ltoreq.w.ltoreq.50,000 per polymer.The polymers of the invention can be utilized to form protective films and can also be utilized in applications such as for molding, coatings, foams and the like.Type: GrantFiled: September 8, 1978Date of Patent: August 26, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4218557Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is represented by: ##STR2## wherein Y is selected from the group consisting of ##STR3## and --SO.sub.2 -- and p=0 or 1; when p=0, R.sub.1 and R.sub.2 are independently selected from a group consisting of substituted or unsubstituted aliphatic, aryl, araryl, and alkylaryl radicals or R.sub.1 and R.sub.2 can form a cyclic amide containing radical wherein R.sub.1 and R.sub.2 taken together are selected from a group consisting of --CH.sub.2).sub.n where n=2 to 12, wherein R.sub.3 is a lower alkyl radical or hydrogen; and when p=1, R.sub.1 and R.sub.2 taken together form a linkage in a cyclic imide containing radical selected from a group consisting of --CH.sub.2).sub.n, where n'=2 or 3 and ##STR4## where R.sub.3 is as defined above, R.sub.Type: GrantFiled: October 20, 1978Date of Patent: August 19, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4218556Abstract: Polyphosphazene copolymers are prepared by a novel, simplified process which contain novel, randomly distributed units represented by the formulas: ##STR1## wherein X is --OSi(OR).sub.3 in which R is a branched, straight chain or cyclic alkyl group containing from 1 to 12 carbon atoms and mixtures thereof and wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, amino and mercapto groups. The alkyl groups may vary in carbon chain length or structure within the silicate or all be the same.The copolymers of the invention can be utilized to form protective films and may also be utilized in applications such as for moldings, coatings, and the like. The copolymers of this invention also crosslink at room temperature in the presence of water.Type: GrantFiled: September 8, 1978Date of Patent: August 19, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4200594Abstract: This invention concerns the preparation of dinitrile phosphonates, as well as their hydrolysis into the corresponding diacids, and reduction into the corresponding diamines. These compounds can be used, in particular, to make polyamides, polyurethanes or polyurates fireproof, as well as to increase their adhesive properties.Type: GrantFiled: December 19, 1977Date of Patent: April 29, 1980Inventors: Georges Sturtz, Jean-Claude Clement
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Patent number: 4182835Abstract: Polyphosphazene copolymers are prepared which contain randomly distributed units represented by the formulas: ##STR1## wherein X is --CNO.sub.2 R.sub.1 R.sub.2 in which R.sub.1 and R.sub.2 are H, a branched, straight chain or cyclic alkyl group containing from 1 to 12 carbon atoms or mixtures thereof, and wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, alkenyloxy, aryloxy, alkenylaryloxy, amino and mercapto groups or mixtures thereof.In the copolymer units represented by the above formulas, all X substituent groups may be the same or they may be mixed and all X' substituent groups may be the same or mixed. In the mixtures, the X substituent groups may be mixtures of different --CNO.sub.2 R.sub.1 R.sub.2 groups and the X' substituent groups may be mixtures of alkoxy, alkenyloxy, aryloxy, alkenylaryloxy, amino and mercapto groups.Type: GrantFiled: September 8, 1978Date of Patent: January 8, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4182834Abstract: Polyphosphazene copolymers are prepared which contain randomly distributed units represented by the formulas: ##STR1## wherein X is --OTi(OR).sub.3 in which R is a branched, straight chain or cyclic alkyl group containing from 1 to 12 carbon atoms or mixtures thereof, and wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, amino and mercapto groups. The alkyl groups may vary in carbon chain length or structure within the titanate or all be the same.The copolymers of the invention can be utilized to form protective films and may also be utilized in applications such as for moldings, coatings, and the like. The copolymers of this invention also crosslink at room temperature in the presence of water.Type: GrantFiled: September 8, 1978Date of Patent: January 8, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4182836Abstract: Polyphosphazene copolymers are prepared which contain randomly distributed units represented by the formulas: ##STR1## wherein X is --OP(OR).sub.2 in which R is a branched, straight chain or cyclic alkyl group containing from 1 to 12 carbon atoms or mixtures thereof, and wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, amino and mercapto groups. The alkyl groups may vary in carbon chain length or structure within the phosphite or all be the same.In the copolymer units represented by the above formulas, all X substituent groups may be the same or they may be mixed and all X' substituent groups may be the same or mixed. In the mixtures, the X substituent groups may be mixtures of different alkylphosphite groups and the X' substituent groups may be mixtures of different alkoxy, aryloxy, amino and mercaptan groups.Type: GrantFiled: September 8, 1978Date of Patent: January 8, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4182837Abstract: Polyphosphazene copolymers are prepared which contain units represented by the formulas: ##STR1## wherein X is a sulfone radical selected from the group consisting of --CR.sub.1 R.sub.2 --SO.sub.2 --R and ##STR2## in which R is alkyl containing from 1 to 12 carbon atoms, cycloalkyl containing from 3 to 12 carbon atoms or aryl and R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl radicals containing from 1 to 11 carbon atoms, cycloalkyl radicals containing from 3 to 11 carbon atoms and aryl radicals; wherein X' is an organic radical selected from the group consisting of substituted or unsubstituted alkoxy, aryloxy, amino and mercapto groups and wherein 20.ltoreq.(a+b+c).ltoreq.50,000 per polymer.The copolymers of the invention can be utilized to form films and may also be utilized in applications for moldings, coatings and the like.Type: GrantFiled: October 20, 1978Date of Patent: January 8, 1980Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4182792Abstract: Novel polymers, useful as films or filaments, are prepared as by the reaction of a bispiperazide with a reactive derivative of an acid.Type: GrantFiled: June 23, 1978Date of Patent: January 8, 1980Assignee: s.a. Texaco Belgium n.v.Inventor: Johny C. Hermans
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Patent number: 4180647Abstract: Polyphosphazene copolymers are prepared which certain randomly distributed units represented by the formulas: ##STR1## wherein X is --CR(CN).sub.2 in which R is H, a branched chain, a straight, or cyclic alkyl group containing from 1 to 12 carbon atoms or an aryl group or mixtures thereof, and wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, alkenyloxy, aryloxy, alkenylaryloxy, amino and mercapto groups or mixtures thereof.In the copolymer units represented by the above formulas, all X substituent groups may be the same or they may be mixed and all X' substituent groups may be the same or mixed. In the mixtures, the X substituent groups may be mixtures of different --CR(CN).sub.2 groups and the X' substituent groups may be mixtures of alkoxy, alkenyloxy, aryloxy, alkenylaryloxy, amino and mercapto groups or mixtures within each group.Type: GrantFiled: September 8, 1978Date of Patent: December 25, 1979Assignee: The Firestone Tire & Rubber CompanyInventors: William J. Hergenrother, Adel F. Halasa
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Patent number: 4180653Abstract: Novel polymers, useful as films or filaments, are prepared as by the reaction of a bispiperazide with a reactive derivative of an acid.Type: GrantFiled: June 23, 1978Date of Patent: December 25, 1979Assignee: s.a. Texaco Belgium n.v.Inventor: Johny C. Hermans
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Patent number: 4179553Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is represented by ##STR2## wherein R.sub.1 and R.sub.2 are independently selected from a group consisting of substituted or unsubstituted aliphatic, aryl, araryl, alkylaryl and heterocyclic radicals or R.sub.1 and R.sub.2 can be linked to form a cyclic radical and R.sub.3 is an aliphatic hydrocarbon radical or hydrogen, X' is a substituted or unsubstituted alkoxy, aryloxy, amino or mercapto substituent group or mixtures thereof which are compatible with an N-substituted amino substituent and are known in the state of the art of polyphosphazene technology; and 20.ltoreq.(w+y+z).ltoreq.50,000 per polymer and (y+z)>0.The polymers of the invention can be utilized to form protective films and can also be utilized in applications such as molding, coatings, foams and the like.Type: GrantFiled: November 3, 1978Date of Patent: December 18, 1979Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4179554Abstract: Polyphosphazene copolymers are prepared which contain units represented by the formulas: ##STR1## wherein X is --O--NR.sub.2 in which R is selected from the group consisting of alkyl groups containing from 1 to 8 carbon atoms, and cycloalkyl groups containing from 3 to 12 ring carbon atoms; and wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, amino and mercapto groups.The polymers of the invention can be utilized to form films and may also be utilized in applications such as moldings, coatings and the like.Type: GrantFiled: November 3, 1978Date of Patent: December 18, 1979Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4179556Abstract: Polyphosphazene copolymers are prepared which are comprised of repeating units represented by the formulas: ##STR1## wherein X is represented by the formula: ##STR2## where R.sub.1 and R.sub.2 are independently selected from the group consisting of substituted and unsubstituted alkyl radicals containing from 1 to 15 carbon atoms, substituted and unsubstituted cycloalkyl, aryl, arylalkyl and heterocyclic ring; X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, mercapto, and amino radicals, and mixtures thereof; and 20.ltoreq.(w+y+z).ltoreq.50,000 per polymer unit.The polyphosphazene polymers of the present invention are prepared by the reaction of a ketoxime and an additional reactant such as alkanol, aryl alcohol, mercaptan, or amine with poly(dichlorophosphazene) in the presence of a tertiary amine. The polymers of this invention may be modified by crosslinking or curing.Type: GrantFiled: November 3, 1978Date of Patent: December 18, 1979Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4176225Abstract: This invention concerns the preparation of dinitrile phosphonates, as well as their hydrolysis into the corresponding diacids, and reduction into the corresponding diamines. These compounds can be used, in particular, to make polyamides, polyurethanes or polyurates fireproof, as well as to increase their adhesive properties.Type: GrantFiled: May 31, 1977Date of Patent: November 27, 1979Inventors: Georges Sturtz, Jean-Claude Clement
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Patent number: 4175181Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X and X' are the same or differnt and are represented by: ##STR2## wherein R.sub.1 is selected from a group consisting of hydrogen and--CN; X' may additionally be selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, mercapto and amino groups and 20 .ltoreq.(w +y+z) .ltoreq.50,000 per polymer.The polymers of the invention can be utilized to form protective films and can also be utilized in applications such as for molding, coatings, foams and the like.Type: GrantFiled: September 8, 1978Date of Patent: November 20, 1979Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Adel F. Halasa
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Patent number: 4175180Abstract: Novel polymers, useful as films or filaments, are prepared as by the reaction of a bispiperazide with a reactive derivative of an acid.Type: GrantFiled: June 19, 1978Date of Patent: November 20, 1979Assignee: s.a. Texaco Belgium n.v.Inventor: Johny C. Hermans
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Patent number: 4175178Abstract: Novel polymers, useful as films or filaments, are prepared as by the reaction of a bispiperazide with a reactive derivative of an acid.Type: GrantFiled: June 16, 1978Date of Patent: November 20, 1979Assignee: s.a. Texaco Belgium n.v.Inventor: Johny C. Hermans
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Patent number: 4139598Abstract: High molecular weight poly(dihalophosphazenes) which exhibit solubility in benzene and in substituted benzenes are prepared in solution or in bulk from dihalophosphazenes such as (Cl.sub.2 PN).sub.3-7 at moderate temperatures by the use of novel polymerization catalysts.Type: GrantFiled: January 12, 1977Date of Patent: February 13, 1979Assignee: Horizons Research IncorporatedInventors: Kennard A. Reynard, Arthur H. Gerber
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Patent number: 4129529Abstract: The production of phosphazene polymers represented by the general formula ##STR1## WHEREIN N IS AN INTEGER FROM 7 TO UPWARDS OF 50,000 WHEREIN ONE OR MORE KINDS OF OR or OR' groups is attached to the phosphorus atoms in a substantially linear chain of alternating P and N atoms, the groups when more than one group is present being randomly distributed along the PN backbone, is enhanced by employing a single solvent for both each of the reactants (polydihalophosphazene and either aryloxide and/or alkoxide) and for the product (phosphazene polymer). By this expedient, the formation of the desired product is achieved in a homogeneous system rather than in a heterogeneous system as in the prior art where different solvents were employed for each of the reactants and for the reaction products.Type: GrantFiled: August 12, 1977Date of Patent: December 12, 1978Assignee: The Firestone Tire & Rubber CompanyInventors: John W. Fieldhouse, Daniel F. Graves, William M. Cole, Mark L. Stayer, Steven L. Fenske
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Patent number: 4128710Abstract: The production of phosphazene polymers represented by the general formula ##STR1## WHEREIN R and R' are organic radicals hereinafter defined, and wherein n is an integer from 20 to upwards of 50,000 wherein one or more kinds of OR or OR' groups is attached to the phosphorus atoms in a substantially linear chain of alternating P and N atoms, the groups when more than one group is present being randomly distributed along the PN backbone, as described in copending United States Patent Application Ser. No. 824,004 filed Aug. 12, 1977, is enhanced by an improved procedure for the separation of the sodium chloride by-product from the derivatized phosphazene polymer. By treating the reaction mixture with carbon dioxide, in the presence of water and preferably with an additional alkali metal salt, agglomeration of the sodium chloride is accomplished, and a clean separation of the NaCl from the polyphosphazene ester is more readily achieved.Type: GrantFiled: October 25, 1977Date of Patent: December 5, 1978Assignee: The Firestone Tire & Rubber CompanyInventors: John W. Fieldhouse, Daniel F. Graves, William M. Cole, Mark L. Stayer, Steven L. Fenske
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Patent number: 4124567Abstract: A process is disclosed for the catalytically-induced preparation of phosphazene polymers. Cyclic halophosphazenes are polymerized in the presence of a catalytically sufficient amount of a compound having the formula M(OR').sub.x where M is an alkali metal or alkaline earth metal, x is equal to the valence of the metal and R' is C.sub.1 to C.sub.10 linear or branched alkyl, C.sub.1 to C.sub.10 substituted linear or branched alkyl, the substituent selected from the group consisting of nitro, C.sub.1 to C.sub.10 alkyl, C.sub.1 to C.sub.10 alkoxy, C.sub.6 to C.sub.10 aryl and C.sub.6 to C.sub.10 aryloxy, or N.sub.3 P.sub.3 Cl.sub.z (OR').sub.6-z wherein R' is as defined above and z equals 0 to 5.Type: GrantFiled: April 10, 1978Date of Patent: November 7, 1978Assignee: Armstrong Cork CompanyInventors: Ronald L. Dieck, Alan B. Magnusson
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Patent number: 4124557Abstract: Flame-retardant and low-smoke plasticized polyphosphazenes are disclosed. The plasticizers are substituted cyclotriphosphazenes and cyclotetraphosphazenes.Type: GrantFiled: March 23, 1978Date of Patent: November 7, 1978Assignee: Armstrong Cork CompanyInventors: Ronald L. Dieck, Edwin J. Quinn
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Patent number: 4116891Abstract: A process is disclosed for the catalytically-induced preparation of phosphazene polymers. Cyclic halophosphazenes are polymerized in the presence of a catalytically sufficient amount of a Lewis acid catalyst.Type: GrantFiled: December 6, 1976Date of Patent: September 26, 1978Assignee: Armstrong Cork CompanyInventors: Ronald L. Dieck, Thomas B. Garrett, Alan B. Magnusson