AU663679B1 - Glycidal azide polymer azide - Google Patents
Glycidal azide polymer azide Download PDFInfo
- Publication number
- AU663679B1 AU663679B1 AU28729/89A AU2872989A AU663679B1 AU 663679 B1 AU663679 B1 AU 663679B1 AU 28729/89 A AU28729/89 A AU 28729/89A AU 2872989 A AU2872989 A AU 2872989A AU 663679 B1 AU663679 B1 AU 663679B1
- Authority
- AU
- Australia
- Prior art keywords
- azide
- polymer
- glycidal
- glycidyl
- energetic
- 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.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B45/00—Compositions or products which are defined by structure or arrangement of component of product
- C06B45/04—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive
- C06B45/06—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component
- C06B45/10—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component the organic component containing a resin
- C06B45/105—The resin being a polymer bearing energetic groups or containing a soluble organic explosive
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
- C07C247/04—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being saturated
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Dispersion Chemistry (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
66 FORM 3 79 S F Ref: 81599 COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952 COMPLETE SPECIFICATION
(ORIGINAL)
FOR OFFICE USE: Class Int Class Complete Specification Lodged: Accepted: Published: Priority: Related Art: Name and Address of Applicant: Address for Service: Rockwell International Corporation 2230 East Imperial Highway El Segundo California 90245 UNITED STATES OF AMERICA Spruson Ferguson, Patent Attorneys Level 33 St Martins Tower, 31 Market Street Sydney, New South Wales, 2000, Australia
SI
Complete Specification for the invention entitled: Glycidal Azide Polymer Azide The following sta:ement is a full description of this invention, including the besc method of pe-forming it known to me/us 5845/5 87R050 GLYCIDYL AZIDE POLYMER AZIOE Milton B. Frankel Michael A. Cunningham Edgar R. Wilson Background of the Invention 1. Field of the Invention This invention relates to a composition of matter, and is particularly directed to an energetic azide terminated glycidyl azide 0 polymer and a method for producing this compound.
S2. Description of the Prior Art Solid propellants are generally formulated to include an oxidizer and fuel together with suitable binders and plasticizers to enhance the S physical and chemical characteristics of-the propellants. Most propellant systems utilize binders and plasticizers containing energetic groups such as nitro (-NO 2 fluorodinitro (FC(NO 2 2 difluoroamino (-NF 2 and others.
These azido plasticizers impart additional energy to propellant systems since each azido group present provides approximately 85 kcal/mole of energy to the system.
One functionally terminated azido polymer is taught by Wilson et al No. 177 1V&c.
in U. S. Patent-iii N .f Another energetic azido polymer is described in U. S. Patent 4,268,450, i ncorporated herein by reference. In contrast to the present invention, Sboth f the aforementioned polymers nd the method of making same, may be both of the aforementioned polymers and the method of making same, may be 87R050 -2distinguished in part by the initiator groups and the repeating units present in the starting materials and final products. Applicants' invention provides a one-step synthesis in high yield of a glycidyl azide polymer azide which fulfills the needs of many propellant systems and is particularly useful as an energetic plasticizer for propellants and explosives.
Summary of the Invention Accordingly there is provided by the present invention an energetic polymer comprising an azide-terminated aliphatic polymer.
Objects of the Invention Therefore it is an object of the present invention to provide a composition of matter useful in formulating solid propellants, explosives, and the like.
Another object of the present invention is to provide an energetic azide-terminated azido plasticizer.
Yet another object of the present invention is to provide a single step process for producing the azide-terminated azido plasticizer.
Detailed Description of the Invention The glycidyl azide polymer azide of this invention is characterized in Table 1 as follows: 87R050 -3- TABLE 1
NAME:
STRUCTURE:
FORMULA:
MOLECULAR WEIGHT: ELEMENTAL ANALYSES: Calculated: Found: INFRARED SPECTRUM:
APPEARANCE:
REFRACTIVE INDEX:
DENSITY:
FREEZING POINT:,
DSC:
WEIGHT LOSS: IMPACT SENSITIVITY: ELECTROSTATIC SENSITIVITY: FRICTION SENSITIVITY: allf (estimated): SHIPPING CLASSIFICATION: GLYCIDYL AZIDE POLYMER A.ZIDE N 3 CH 2 CH 2 OCH 2 H OCH 2 FHN 3 CH 2 N 3 CH 2
N
3
C
1 4 H2 4 N1 804 3 508 C H N 33.07. 4.72 49.61 34.38 5.14 49.30
N
3 (4.7pi) Light Yellow Liquid 1.5138 at 1.27 g/cc at -56C 205C (Onset of Exotherm) 0.48% after 48 hrs. at 74C 40 in-lb 12.5 Joules 36 Kg cm 335 Kcal/mole Class B Explosive (25-35% Solution in CH 2
CL
2 87R050 -4- The glycidyl polymer azide of the general formula:
SN
3
CH
2
CH
2 OCH OCH2HN 3
CH
2
N
3 CH 2
N
3 n-1 can be produced by the. one-step process of reacting a (2-chloroethyl)-w-benzenesulfonyl polyepichlorohydrin of the general formula: C1CH 2
CH
2
O---CH
2 CH S0 3 C 6 H
CH
2
N
3 with sodium azide in a polar solvent such as dimethylsulfoxide (DMSO), and wherein n of formulas and is an integer from 2 to The following example illustrates the invention.
EXAMPLE
In a suitable reaction vessel, 2,750 ml of dimethylsulfoxide was S heated under a nitrogen purge to 70 0 C. To this was added over a 15 minute per id 2,090 grams (32.15 moles) of sodium azide. This mixture was then heat. to 95*C and 2,511.2 grams (26.79 moles) of a-(2-chloroethyl)--benzenesulfonyl polyepichlorohydrin was added over four hours., No additional heat was required during the addition to maintain the temperature at from about 95 to about 1000C.
*6 After the addition was complete, the reaction mixture was heated an additional 12 hours at a temperature of from about 95 to about 100 0 C. The reaction mixture was then quenched with 6.5 liters of water. The resulting organic phase was separated, washed four times with ten liters of hot water, diluted to 20% solution in methylene chloride, dried over anhydrous sodium sulfate, and passed through a column of 2,000 grams of i ?9%7050 silica gel. Concentration of the solution gave 1,896.5 grams of the glycidyl polymer azide, the properties of which are set forth in Table 1 above.
It should be noted that the precise amounts, temperatures, times, solutions, means of addition, drowning procedures, number of washes, extraction and stripping procedures which were used or may be used may all be varied to meet specific requirements and specific reactions. These parameters delineated herein are merely representative.
Obviously, many modifications and variations of the present invention are possible in light of the above teachings. It is therefore to be understood that, within the scope of the appended claims, the invention may be practiced otherwise than as specifically described.
What is ceaimed -d 4^d-to be iseco ed by t-.t1c -1 1 Ak S, I AfC
Claims (1)
- 2. The composition of matter of the general formula: N 3 CH 2 CH 2 OC 2 ?CH OCH 2 FHN 3 CH 2 N 3 CH N 3 DATED this TWELFTH day of JANUARY, 1989 Rockwell International Corporation Patent Attorneys for the Applicant SPRUSON FERGUSON &i 43~
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15059088A | 1988-02-01 | 1988-02-01 | |
| US150590 | 1988-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU663679B1 true AU663679B1 (en) | 1995-10-19 |
Family
ID=22535204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU28729/89A Expired - Fee Related AU663679B1 (en) | 1988-02-01 | 1989-01-12 | Glycidal azide polymer azide |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU663679B1 (en) |
| FR (1) | FR2707979A1 (en) |
| GB (1) | GB2285624B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2039928C (en) * | 1990-05-25 | 2004-07-20 | Birger Johannessen | Non-detonable poly(glycidyl azide) product |
| FR2799762B3 (en) * | 1999-10-15 | 2002-05-17 | Poudres & Explosifs Ste Nale | GLYCIDYL POLYAZOTURES COMPRISING AN ACYLOXY TERMINATION AND AN AZIDE TERMINATION |
| CN111474258B (en) * | 2020-04-17 | 2022-09-06 | 湖北航天化学技术研究所 | Method for measuring branching degree of azido glycidyl polyether |
| CN115028829B (en) * | 2022-06-21 | 2023-06-09 | 西安近代化学研究所 | 1,2, 3-triazole-4-methylene nitrate modified azide adhesive, synthesis method and application |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4268450A (en) * | 1977-08-08 | 1981-05-19 | Rockwell International Corporation | Energetic hydroxy-terminated azido polymer |
-
1989
- 1989-01-12 AU AU28729/89A patent/AU663679B1/en not_active Expired - Fee Related
- 1989-01-31 FR FR8901204A patent/FR2707979A1/en active Pending
- 1989-02-01 GB GB8902163A patent/GB2285624B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2285624A (en) | 1995-07-19 |
| GB8902163D0 (en) | 1995-04-12 |
| GB2285624B (en) | 1996-03-20 |
| FR2707979A1 (en) | 1995-01-27 |
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