Thiokol Corporation

Alfred G Stern

Rodney L Willer

Robert S Day

Dennis J Park

This invention is first, a difunctional poly(glycidyl nitrate) oligomer (PGN oligomer), second, nitrated PGN oligomer and third, the use of the nitrated PGN oligomer as a plasticizer, particularly as a plasticizer for binders used in and/or as energetic formulations. Examples of energetic formulations are propellants, pyrotechnics and explosives and other such compositions. More particularly, this invention is a difunctional poly(glycidyl nitrate) oligomer of the formula ##STR1## where n is 0 to 3, having a M.sub.n of from about 304 to about 994. Another embodiment is the nitrated difunctional poly(glycidyl nitrate) oligomer of the formula ##STR2## where n is 0 to 3, having a M.sub.n of from about 394 to about 1084. This invention also comprises a plasticizer for binder compounds, namely, the nitrated PGN oligomer above; preferably the plasticizer above is used wherein the binder compound is used in energetic formulations; and preferably the binder compound is an energetic compound; more preferably the energetic formulation is selected from the group consisting of propellants, pyrotechnics and explosives.

Polyglycidyl nitrate plasticizers

Isotactic poly(glycidyl nitrate) useful in solid propellants is produced by polymerizing chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate. Chiral (R) glycidyl nitrate or its enantiomer is prepared by sequential treatment of chiral (S) glycidyl tosylate or its enantiomer with nitric acid and sodium hydroxide. Chiral (S) glycidyl tosylate or its enantiomer, (R) glycidyl tosylate, can be produced by Sharpless epoxidation of allyl alcohol or by direct tosylation or commercially available chiral glycidol. Likewise, chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate, can be prepared directly via nitration of (S) or (R) glycidol, respectively.

Isotactic poly(glycidyl nitrate) and synthesis thereof

This invention is for new compounds, namely, diethanolammoniummethylcubane nitrates, a composition of diethanolammonium methylcubyl nitrates - hydroxylammonium nitrate (HAN) solutions and their method of use as aqueous liquid gun propellant ingredients.

Diethanolammoniummethylcubane nitrates hydroxylammonium nitrate (HAN)

Isotactic poly(glycidyl nitrate) useful in solid propellants is produced by polymerizing chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate. Chiral (R) glycidyl nitrate or its enantiomer is prepared by sequential treatment of chiral (S) glycidyl tosylate or its enantiomer with nitric acid and sodium hydroxide. Chiral (S) glycidyl tosylate or its enantiomer, (R) glycidyl tosylate, can be produced by Sharpless epoxidation of allyl alcohol or by direct tosylation of commercially available chiral glycidol. Likewise, chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate, can be prepared direcly via nitration of (S) or (R) glycidol, respectively.

Isotactic poly(glydicyl nitrate) and synthesis thereof

An improved process for producing poly(glycidyl nitrate) having a functionality substantially equivalent to the hydroxy functionality of the initiator employed in which a catalyst-initiator complex is reacted with glycidyl nitrate and wherein the ratio of mols catalyst/mols hydroxyls in the initiator is &lt;1:1, the gylcidyl nitrate monomer is added to the catalyst-initiator complex reaction mixture at a rate in which the monomer is used up (reacted) essentially as fast as it is added, and the reaction temperature is maintained at a temperature within the range of from about 10.degree. to 25.degree. C.

Process for producing improved poly(glycidyl nitrate)

Cyanogen is prepared from glyoxime by reaction with acetic anhydride to form N,N'-diacetoxyglyoxime which is then pyrolyzed to cyanogen.

Growing community of inventors

Elkton, MD, United States of America

Alfred G Stern