US4414384A
Expired / Lapsed
US
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Synthesis and polymerization of 3-azidooxetane
Assignee: United States Department of the Navy
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Filing: 1982-06-14
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Granted: 1983-11-08
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Expires: 2002-06-14
Abstract
Abstract 3-Azidooxetane, ##STR1## is prepared by reacting 3-oxetyl p-toluenesulfonate with an alkali metal azide in a polar solvent. In the presence of a Lewis acid catalyst, 3-azidooxetane polymerizes to form a poly(3-azidotrimethylene ether) of the formula ##STR2## which can be cured with diisocyanates to form energetic, rubbery polyurethanes.
Inventors
- 👤 Phillip T. Berkowitz
- 👤 Kurt Baum
- 👤 Vytautas Grakauskas
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 05:19
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/50; C08G18/5021; C08G65/00; C08G65/02; C08G65/04; C08G65/22
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
26 words
A poly(3-azidotrimethylene ether) of the formula ##STR7## wherein n is selected to provide an average molecular weight of from about 1500 about 5000 for the polymer.
Claim 2
Dependent Claim
26 words
A poly(3-azidotrimethylene ether) of the formula ##STR7## wherein n is selected to provide an average molecular weight of from about 1500 about 5000 for the polymer.
Claim 3
Dependent Claim
16 words
The poly(3-azidotrimethylene ether) of claim 1 having an average molecular weight of from 2000 to 3500.
Claim 4
Independent Claim
50 words
A method for preparing a poly(3-azidotrimethylene ether) of the formula ##STR8## comprising the steps of: (1) dissolving 3-azidooxetane in a polar aprotic organic solvent; (2) adding a Lewis acid to the solution to catalyze the polymerization of 3-azidooxetane to form the poly(3-azidotrimethylene ether); and (3) isolating the product poly(3-azidotrimethylene ether).
Claim 5
Independent Claim
50 words
A method for preparing a poly(3-azidotrimethylene ether) of the formula ##STR8## comprising the steps of: (1) dissolving 3-azidooxetane in a polar aprotic organic solvent; (2) adding a Lewis acid to the solution to catalyze the polymerization of 3-azidooxetane to form the poly(3-azidotrimethylene ether); and (3) isolating the product poly(3-azidotrimethylene ether).
Claim 6
Dependent Claim
25 words
The process of claim 3 wherein the polar aprotic organic solvent is selected from the group consisting of acetonitrile, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, and chloroform.
Claim 7
Dependent Claim
14 words
The process of claim 4 wherein the polar aprotic organic solvent is methylene chloride.
Claim 8
Dependent Claim
21 words
The process of claim 3 wherein the Lewis acid catalyst is selected from the group consisting of boron trifluoride, phosphorus pentafluoride.
Claim 9
Dependent Claim
13 words
The process of claim 6 wherein the Lewis acid catalyst is boron trifluoride.
Claim 10
Dependent Claim
25 words
The process of claim 6 or 7 wherein the molar ratio of Lewis acid catalyst to poly(3-azidotrimethylene ether) is from about 1:100 to about 3:20.
Claim 11
Dependent Claim
23 words
The process of claim 6 or 7 wherein the molar ratio of Lewis acid catalyst to poly(3-azidotrimethylene ether) is from 1:20 to 1:10.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-11-07 | 1987-05-09 | 1987-11-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-11-07 | 1991-05-09 | 1991-11-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-11-07 | 1995-05-09 | 1995-11-08 | $7700.00 | Window Closed / Lapsed |