EP0000790A1 - Procédé de préparation de polyphosphazènes - Google Patents

Procédé de préparation de polyphosphazènes Download PDF

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Publication number
EP0000790A1
EP0000790A1 EP7878100652A EP78100652A EP0000790A1 EP 0000790 A1 EP0000790 A1 EP 0000790A1 EP 7878100652 A EP7878100652 A EP 7878100652A EP 78100652 A EP78100652 A EP 78100652A EP 0000790 A1 EP0000790 A1 EP 0000790A1
Authority
EP
European Patent Office
Prior art keywords
solution
process according
hal
group
dihalophosphazene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP7878100652A
Other languages
German (de)
English (en)
Other versions
EP0000790B1 (fr
Inventor
John William Fieldhouse
Daniel Frank Graves
William Max Cole
Mark Lutz Stayer, Jr.
Steven Lee Fenske
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bridgestone Firestone Inc
Original Assignee
Firestone Tire and Rubber Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Firestone Tire and Rubber Co filed Critical Firestone Tire and Rubber Co
Publication of EP0000790A1 publication Critical patent/EP0000790A1/fr
Application granted granted Critical
Publication of EP0000790B1 publication Critical patent/EP0000790B1/fr
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
    • C08G79/025—Polyphosphazenes

Definitions

  • This invention relates to an improved process for the production of polyphosphazenes in which the substituents on the phosphorus atoms are those described in any of the following United States Patents: and others of a similar nature in which products having the general formula wherein R and R t are each selected from the group consisting of alkyl, alkylaryl, aryl any of which may be either substituted or unsubstituted as shown in the above noted patents, and need not be the same and n is an integer between about 7 and about 50,000 or more, and in which some of the R or R' groups may contain some unsaturation to facilitate curing the products.
  • a principal object of this invention is to improve the process in which the halogen atoms in the polydihalophosphazene starting material are replaced by alkoxy and/or aryloxy groups, in the derivatization reaction described in any of the above noted patents.
  • a further object of the invention is to effect said improvement by the provision of a single solvent for both the polydihalophosphazene reactant and the alkoxide or aryloxide reactant and which is also a solvent for the desired ester product and which is a non-solvent for the inorganic halide by-product, i.e. the alkali metal halide or alkaline earth halide formed as the other reaction product.
  • a further object of this invention is to provide a stabilized solution of the polydihalophosphazene in the solvent of choice, suitable for carrying out such a reaction.
  • a further object is to provide a procedure for the preparation of phosphazene polymers in which the rate of reaction is faster than in prior art heterogeneous derivatizations and in which complete substitution of the halogen atoms is more readily achieved than in such prior art processes.
  • a further object of the invention is to simplify the separation of the inorganic halide from the solution of the polyphosphazene derivative formed during said reaction.
  • THF tetrahydrofuran
  • THF THF
  • separation and recovery of a plurality of solvents is eliminated, and in which separate recovery of the polyphosphazene derivative and the inorganic halide is simplified.
  • solutions of the poly(dihalophosphazene) in THF are unstable since as reported in United States Patent 3,260,684 the polydihalophosphazene may catalyze polymerization of the THF. In accordance with the present invention this is avoided by the addition of certain amines to the THF.
  • Amines which were found to inhibit the formation of poly-THF in solutions of polydihalophosphazenes in THF included diphenylamine, N-methyldiphenylamine, N-methylpyrrole, pyrrole and 6-dodecyl-1,2-dihydro-2,2,4-trimethyl- quinoline.
  • the amount of amine is between 0.25 and 5.0 parts by weight for each part by weight of poly(dihalophosphazene ).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
EP78100652A 1977-08-12 1978-08-12 Procédé de préparation de polyphosphazènes Expired EP0000790B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US824004 1977-08-12
US05/824,004 US4129529A (en) 1977-08-12 1977-08-12 Process for the production of phosphazene polymers

Publications (2)

Publication Number Publication Date
EP0000790A1 true EP0000790A1 (fr) 1979-02-21
EP0000790B1 EP0000790B1 (fr) 1984-01-04

Family

ID=25240354

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100652A Expired EP0000790B1 (fr) 1977-08-12 1978-08-12 Procédé de préparation de polyphosphazènes

Country Status (4)

Country Link
US (1) US4129529A (fr)
EP (1) EP0000790B1 (fr)
CA (1) CA1098534A (fr)
DE (1) DE2862358D1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0312435A1 (fr) * 1987-10-14 1989-04-19 Elf Atochem S.A. Procédé de purification des polyorganophosphazènes bruts obtenus par co-substitution de polydichlorophosphazènes

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU530988B2 (en) * 1978-09-08 1983-08-04 Firestone Tire And Rubber Co., The Polyphosphazenes
US4609724A (en) * 1985-04-29 1986-09-02 The Firestone Tire & Rubber Company Process for preparing and purifying alkoxyphosphazene polymer
US4665152A (en) * 1985-09-09 1987-05-12 The Firestone Tire & Rubber Company Curable poly(aryloxyphosphazene) copolymers
US4663420A (en) * 1986-01-21 1987-05-05 Ethyl Corporation Polyetheroxy-substituted polyphosphazene purification
US4870113A (en) * 1988-12-23 1989-09-26 Ethyl Corporation Rigid polyphosphazene foam and process for making same
US5286469A (en) * 1991-12-17 1994-02-15 Northeastern University Metal-phosphorus-nitrogen polymers, metal-phosphorus compounds and methods of preparation thereof
JP4184158B2 (ja) * 2003-06-05 2008-11-19 旭化成ケミカルズ株式会社 ホスホニトリル酸エステルの製造法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB991201A (en) * 1962-03-27 1965-05-05 Albright & Wilson Mfg Ltd Polymeric phosphonitrilic derivatives
FR1473887A (fr) * 1964-09-29 1967-03-24 American Cyanamid Co Polymères et procédé pour la production de ces polymères de phosphonitrile
US3344087A (en) * 1960-04-01 1967-09-26 Olin Mathieson Polymeric phosphorus-nitrogen compounds and the production thereof
FR2074147A5 (fr) * 1969-12-24 1971-10-01 Sandoz Sa
FR2156306A1 (fr) * 1971-10-13 1973-05-25 Horizons Research Inc
DE2708319A1 (de) * 1976-02-27 1977-09-08 Armstrong Cork Co Elastomeres copolymeres von poly(aryloxyphosphazen)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271330A (en) * 1962-01-29 1966-09-06 Minnesota Mining & Mfg High molecular weight phosphonitrile fluoroesters
US3443913A (en) * 1967-10-12 1969-05-13 Grace W R & Co Process for preparing high molecular weight linear phosphonitrilic polymers

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3344087A (en) * 1960-04-01 1967-09-26 Olin Mathieson Polymeric phosphorus-nitrogen compounds and the production thereof
GB991201A (en) * 1962-03-27 1965-05-05 Albright & Wilson Mfg Ltd Polymeric phosphonitrilic derivatives
FR1473887A (fr) * 1964-09-29 1967-03-24 American Cyanamid Co Polymères et procédé pour la production de ces polymères de phosphonitrile
FR2074147A5 (fr) * 1969-12-24 1971-10-01 Sandoz Sa
FR2156306A1 (fr) * 1971-10-13 1973-05-25 Horizons Research Inc
DE2708319A1 (de) * 1976-02-27 1977-09-08 Armstrong Cork Co Elastomeres copolymeres von poly(aryloxyphosphazen)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 84, 1976, 136925x *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0312435A1 (fr) * 1987-10-14 1989-04-19 Elf Atochem S.A. Procédé de purification des polyorganophosphazènes bruts obtenus par co-substitution de polydichlorophosphazènes

Also Published As

Publication number Publication date
US4129529A (en) 1978-12-12
EP0000790B1 (fr) 1984-01-04
DE2862358D1 (en) 1984-02-09
CA1098534A (fr) 1981-03-31

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