Nitramine oxetanes and polyethers formed therefrom

• US 4,707,540 A
• Filed: 10/29/1986
• Issued: 11/17/1987
• Est. Priority Date: 10/29/1986
• Status: Expired due to Fees

• Current Assignee: Morton-Thiokol, Inc. (Howmet Aerospace, Inc.)
• Original Assignee: Morton-Thiokol, Inc. (Howmet Aerospace, Inc.)
• Inventors: Manser, Gerald E., Fletcher, Richard W.
• Primary Examiner(s): Nielsen, Earl
• Application Number:
  US06/825,658
• Time in Patent Office: 384 Days
• Field of Search: 528/417, 528/362, 528/361, 549/510
• US Class Current: 528/417
• CPC Class Codes: C06B 45/105 The resin being a polymer bearing energetic groups or containing a soluble organic explosive
• CPC Class Codes: C08G 65/18 Oxetanes
• CPC Class Codes: C08G 65/22 Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
• CPC Class Codes: C08G 65/223 containing halogens epihalohydrins C08G65/24

Abstract

Nitramine oxetanes, specifically 3-methyl nitraminomethyl-3-methyl oxetane and 3,3-Bis (methyl nitraminomethyl) oxetane are synthesized. Polyethers are formed incorporating the nitramine oxetanes, which polyethers are curable with isocyanates to form elastomers suitable for use as binders in propellants or the like.

Claims

1. A nitramine oxetane having the formula:

##STR9## wherein at least one of R¹ and R² have the formula (CH₂)₄ --N(NO)₂ --A, wherein n is at least 1 and A is --H or an alkyl group, and R² is (CH₂)_n --Y wherein Y is ##STR10##

2. An oxetane according to claim 1 wherein said oxetane is selected from the group consisting of 3-methyl nitraminomethyl-3-methyl oxetane and 3,3-Bis(methylnitraminomethyl) oxetane.

3. A polyether having mer units derived from cyclic ethers having the general formula:

##STR11## wherein C_p represents saturated ring carbons and p is between 2 and 4, from about 10 molar percent to 100 percent of the mer units being derived from a nitramine oxetane having the formula;

##STR12## wherein at least one of R¹ and R² have the formula (CH₂)_n --N(NO)₂ --A, wherein n is at least 1 and A is --H or an alkyl group, and R² is (CH₂)_n --Y wherein Y is ##STR13##

4. a polyether according to claim 3, wherein said nitramine oxetane is selected from the group consisting of 3-methyl nitraminomethyl-3-methyl oxetane and 3,3-Bis(methyl nitraminomethyl) oxetane and mixtures thereof.

5. A elastomer comprising a polyether having mer units derived from cyclic ethers, having the general formula:

##STR14## wherein C_p represents saturated ring carbons and p is between 2 and 4, from about 10 molar percent to 100 percent of the mer units being derived from a nitramine oxetane having the formula;

##STR15## wherein at least one of R¹ and R² have the formula (CH₂)_n --N(NO)₂ --A, wherein n is at least 1 and A is --H or an alkyl group, and R² is (CH₂)_n --Y wherein Y is --H, alkyl, ##STR16## an isocyanate having a functionality of 2 or greater curing said polyether.

6. A propellant composition comprising between about 70 and about 90 wt. % solids, including fuel material particulates and/or oxidizer particulates, balance consisting essentially of a binder system comprising an elastomer and optionally a plasticizer with a plasticizer to elastomer ratio of up to about 2.5:

1, said elastomer elastomer comprising a polyether having mer units derived from cyclic ethers, having the general formula;

##STR17## wherein C_p represents saturated ring carbons and p is between 2 and 4, from about 10 molar percent to 100 percent of the mer units being derived from a nitramine oxetane having the formula;

##STR18## wherein at least one of R¹ and R² have the formula (CH₂)_n --N(NO)₂ --A, wherein n is at least 1 and A is --H or an alkyl group, and R² is (CH₂)_n --Y wherein Y is --H, alkyl, ##STR19## an isocyanate having a functionality of 2 or greater curing said polyether.

7. A method of synthesizing a nitramine oxetane comprising providing an oxetane having the general formula:

##STR20## wherein at least one of R¹ and R² have the formula (CH₂)_n --N(NO)₂ --A, wherein n is at least 1 and A is --H or an alkyl group, and R² is (CH₂)_n --Y wherein Y is --H, alkyl, ##STR21## providing a nitramine salt having the general formula;

M(N(NO₂)A)_z (z=1-3) wherein M is a cation and A is --H or an alkyl group, and

reacting said oxetane and said nitramine salt to produce the corresponding nitramine.

8. A method according to claim 7 where z=1.