Low risk synthesis of energetic poly(3-azidomethyl-3-methyl oxetane) from tosylated precursors

Propellants, Explosives, Pyrotechnics

Volumn 31, Issue 5, 2006, Pages 369-375

  Barbieri, Ugo ^a   Polacco, Giovanni ^a   Paesano, Emanuele ^a   Massimi, Roberto ^b  

^a UNIVERSITY OF PISA   (Italy)

^b AVIO S P A   (Italy)

Author keywords

Azidation; Energetic binder; Poly(3 azidomethyl 3 methyl oxetane) (pAMMO); Solid propellant

Indexed keywords

ACTIVATION ENERGY; MONOMERS; POLYBUTADIENES; RATE CONSTANTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AZIDATION; ENERGETIC BINDERS; POLY(3-AZIDOMETHYL-3-METHYL OXETANE) (PAMMO);

ORGANIC POLYMERS;

EID: 33750435882     PISSN: 07213115     EISSN: 15214087     Source Type: Journal    
DOI: 10.1002/prep.200600050     Document Type: Article

References (15)

1. G. E. Manser, Cationic Polymerization. U.S. Patent 4393199, 1983, SRI International, USA.
2. H. Cheradame, J. P. Andreolety, E. Rousset, Synthesis of Polymers Containing Pseudohalide Groups by Cationic Polymerization 1: Homopolymerization of 3,3-Bis(azidome-thyl)oxetane and its Copolymerization with 3-Chloromethyl 3-(2.5,8-trioxadecyl)oxetane, Makromol. Chem. 1991, 192, 901.
3. M. A. H. Talukder, Ring Opening Polymerization of Oxetanes by Cationic Initiators: Polymerization of 3-Azidomethyl-3-methyloxetane with Bis(chlorodimethylsilyl)benzene/silver hexafluoroantimonate Initiating System, Macromol.-Symp. 1991, 42/43, 501.
4. B. Xu, C. P. Lillya, J. C. W. Chen. Spiro(benzoxasilole) Catalyzed Polymerization of Oxetane Derivatives, J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 1899.
5. n Thermoplastic Elastomers, J. Appl. Polym. Sci. 1992, 46, 1603.
6. G. H. Hsiue, Y. L. Liu. Y. S. Chiu, Triblock Copolymers based on Cyclic Ethers: Preparation and Properties of Tetrahydrofuran and 3,3-Bis(azidomethyl) oxetane Triblock Copolymers, J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 2155.
7. R. B. Wardle, W. W. Edwards, Methods for Controlled Polymerization of Energetic Cyclic Ethers using Alkylating Salts, U.S. Patent 6100375, 2000, Cordant Technologies, Inc., USA.
8. T. W. Campbell, Some Reactions of 3,3-Bis(chloromethyl)oxetane, J. Org. Chem. 1957, 22, 1029.
9. M. B. Frankel, J. E. Flanagan, Energetic Hydroxy-Terminated Azido Polymer, U.S. Patent 4268450, 1981, Rockwell International Corporation. USA.
10. J. J. Jutier, A. De Gunzbourg, R. E. Proud'Homme, Synthesis and Characterization of Poly(3,3-bis(azidomethyl)oxetaneco-ε-caprolactone. J. Polym. Sci., Part A: Polym. Chem., 1999, 37, 1027.
11. U. Barbieri, G. Polacco, R. Massimi, Synthesis of Energetic Polyethers from Halogenated Precursors, Macromol. Symp. 2006, 234(1), 51.
12. A. A. Malik, G. E. Manser, R. P. Carson, T. G. Archibald, Solvent free Process for the Synthesis of Energetic Oxetane Monomers, U.S. Patent 5523424, 1996, Aerojet-General Corporation, USA.
13. E. R. Wilson, M. B. Frankel, Synthesis of Novel Energetic Compounds. Azido Derivatives of Pentaerythritol. J. Org. Chem. 1985, 50, 3211.
14. A. J. Parker, Protic Dipolar Aprotic Solvent Effects on Rates of Bimolecular Reactions, Chem. Rev. 1969, 69, 1.
15. Y. Oyumi, T. B. Brill, Thermal Decomposition of Energetic Materials 12. Infrared Spectral and Rapid Thermolysis Studies of Azide-containing Monomers and Polymers, Combust. Flame 1986, 65, 127.