CA1140296A - Energetic hydroxy-terminated azido polymer - Google Patents
Energetic hydroxy-terminated azido polymerInfo
- Publication number
- CA1140296A CA1140296A CA000335332A CA335332A CA1140296A CA 1140296 A CA1140296 A CA 1140296A CA 000335332 A CA000335332 A CA 000335332A CA 335332 A CA335332 A CA 335332A CA 1140296 A CA1140296 A CA 1140296A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- integer
- terminated
- terminated aliphatic
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- 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
- 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
- C08G65/04—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 from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
-
- 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
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/325—Polymers modified by chemical after-treatment with inorganic compounds containing nitrogen
Abstract
Abstract of the Disclosure An energetic binder comprises a hydroxy-terminated aliphatic polymer having dependent alkyl azide groups and method for producing same.
Description
1~4('29~i Background of the Invention -l. Field of the Invention This invention relates to composition of matter, and is particularly directed to the disclosure of an ener-getic binder comprising hydroxy-terminated aliphatic poly-ethers having dependent alkyl azide groups, together with a method for producing this compound.
2. Description of the Prior Art Solid propellants are formulated from an oxidizer and fuel together with suitable binders and plasticizers to ; impart physical integrity. Most highly energetic systems utilize binders and plasticizers containing energetic groups such as nitro (-NO2), fluorodinitro (FC(NO2)2-), difluoro-; amino (-NF2), and many others.
Utilization of azido plasticizers has become a reality during the last several years. These azido plasti-cizers impart additional energy to propellants since each azido group present adds approximately 85 kcal/mole of energy to the system. It follows that utilization of an azido polymer would impart additional energy to the system.
Unfortunately, the few azido polymers synthesized to date - are not functionally terminated which is a necessity for good propellant castability and physical properties.
One functionally terminated azido polymer is taught by Delzenne et al, U. S. Patent #3,453,108. In contrast to the presently claimed hydroxy-terminated ali-phatic polyether having directly dependent alkyl azide groups, Delzenne et al teach azidosulphonyl substituents connected through an aromatic ring structured to the poly-mer backbone. In that this polymer has a completely differ-ent structural formula, completely different chemical and physical properties, as well as a completely different use, its teaching would not render obvious the presently claimed invention.
Summary of the Invention 114(~29~
Accordingly there is provided by the present invention ` an energetic polymer comprising a hydroxy-terminated aliphatic `~ polyether having pendant alkyl azide groups having a structural formula of:
' : H~)CH2CH~OH
l l lx R
:' wherein x is an integer from 10 to 60 and wherein R is selected :"
from the group consisting of -(CH2)nN3, and -CE12CHN3CH2N3, and wherein n is an integer from 1 to 5.
There is further provided a process for producing hydroxy-terminated aliphatic polyethers of the general formula .
CH2CH~OH
L I ~x . `.
wherein x is an integer from 10 to 60 and wherein R is selected from the group consisting of -(CH2)nN3 and -C~2CHN3CH2N3' wherein n is an integer from 1 to 5, by reacting a compound of the - general formula C ~ H [CH~ Cl, wherein n is an integer from I to 5 with sodium azide in an appropriate polar organic solvent.
Objects of the Invention _ .
Therefore, it is an object of the present invention to provide improved materials for formulating solid propellants.
Another object of the present invention is to provide a new composition of matter.
An additional object of the present invention is to provide an energetic azido polymer.
A specific object of the present invention is to provide a hydroxy-terminated aliphatic polyetner having de-pendent alkyl azide groups.
These and other objects and features of the present invention will be apparent from the following detailed des-cription.
Description of the Preferred Embodiments In accordance with the present invention there is provided a hydroxy-terminated or carboxy-terminated aliphatic polymer having dependent alkyl azide groups. Although almost
Utilization of azido plasticizers has become a reality during the last several years. These azido plasti-cizers impart additional energy to propellants since each azido group present adds approximately 85 kcal/mole of energy to the system. It follows that utilization of an azido polymer would impart additional energy to the system.
Unfortunately, the few azido polymers synthesized to date - are not functionally terminated which is a necessity for good propellant castability and physical properties.
One functionally terminated azido polymer is taught by Delzenne et al, U. S. Patent #3,453,108. In contrast to the presently claimed hydroxy-terminated ali-phatic polyether having directly dependent alkyl azide groups, Delzenne et al teach azidosulphonyl substituents connected through an aromatic ring structured to the poly-mer backbone. In that this polymer has a completely differ-ent structural formula, completely different chemical and physical properties, as well as a completely different use, its teaching would not render obvious the presently claimed invention.
Summary of the Invention 114(~29~
Accordingly there is provided by the present invention ` an energetic polymer comprising a hydroxy-terminated aliphatic `~ polyether having pendant alkyl azide groups having a structural formula of:
' : H~)CH2CH~OH
l l lx R
:' wherein x is an integer from 10 to 60 and wherein R is selected :"
from the group consisting of -(CH2)nN3, and -CE12CHN3CH2N3, and wherein n is an integer from 1 to 5.
There is further provided a process for producing hydroxy-terminated aliphatic polyethers of the general formula .
CH2CH~OH
L I ~x . `.
wherein x is an integer from 10 to 60 and wherein R is selected from the group consisting of -(CH2)nN3 and -C~2CHN3CH2N3' wherein n is an integer from 1 to 5, by reacting a compound of the - general formula C ~ H [CH~ Cl, wherein n is an integer from I to 5 with sodium azide in an appropriate polar organic solvent.
Objects of the Invention _ .
Therefore, it is an object of the present invention to provide improved materials for formulating solid propellants.
Another object of the present invention is to provide a new composition of matter.
An additional object of the present invention is to provide an energetic azido polymer.
A specific object of the present invention is to provide a hydroxy-terminated aliphatic polyetner having de-pendent alkyl azide groups.
These and other objects and features of the present invention will be apparent from the following detailed des-cription.
Description of the Preferred Embodiments In accordance with the present invention there is provided a hydroxy-terminated or carboxy-terminated aliphatic polymer having dependent alkyl azide groups. Although almost
- 3 -11~()2916 ~ y polymer will work, polyethers and polyesters are preferred, and polyether is most preferred. Basically the hydroxy-termina-ted aliphatic polyethers having dependent alkyl azide groups has the following structural formula:
H~)CH2CH~OH
I ~x R
: wherein R is represented by alkyl a~ides such as -(CH2)nN3, and -CH2CHN3CH2N3 wherein n is an integer from 1 to 5 and . wherein x is an integer from 10 to 60. In its preferred ~; configuration, the hydroxy-terminated aliphatic polyether of ~ .
1~` _3a --``` 114~2916 76R74-A C.I.P. of S.N. 822,490 ,:
the present invention will have the following structural formula:
H - ~OCH2CH ~ OH
'; CH2N3 x wherein x is an integer from 20 to 40.
In ~eneral, the desired hydroxyl-terminated aliphatic polyether having * dependent alkyl azide groups is prepared as follows:
., \0/ [ ]
~¦ NaN3 C\2JCH [CH2 ]nN3 ¦~ Catal Yzed H- OCH2CH ~ x OH
2 n 3 wherein n is an integer from 1-5 and x is an integer from 10 to 60. A typicalcatalyst for this system would be BF3. Similarly, the alkyi diazido polymer can be prepared by starting with a dichloro compound such as C~2~CH (CH2)n ICH CH2Cl O Cl One such commercially available compound is 1,2-diepoxy-4, 5-dichloropentane.
By way of example and not limitation, the azido polymer of the present invention can be prepared as follows:
A mixture of lOOq (1.0 mole) of polyepichlorohydrin, 1309 (2.0 moles) of sodium azide, and 600 ml of dimethyl formamide was heated at 100C and a~itated for 72 hours. The mixture was cooled and diluted with 500 ml of methylene chloride. The reaction mixture was then washed with water to remove sodium azide and dimethylformamide. The methylene chloride solution was dried over magnesium sulfate and concentrated to give 789 (72.9~) of viscous amber liquid.
114029~i 76R74-A C.I.P. of S.~l. 822,490 ;~ The liquid was characterized and the following properties were obtained:
Elemental Analysis: C(36.21); H(5.n5); N(40.56) wt.X
Molecular Weight: 2500 Funct;onality: 2 ` 5 Infrared Spectrum: 4.75~ (s) for N3 Density: 1.30.gm/cc Obviously, numerous variations and modifications may be made without departing from the present invention. Accordingly, it should be clearly understood that the form of the present invention described above is illustra-tive only and is not intended to limit the scope of the present invent;on.
.
H~)CH2CH~OH
I ~x R
: wherein R is represented by alkyl a~ides such as -(CH2)nN3, and -CH2CHN3CH2N3 wherein n is an integer from 1 to 5 and . wherein x is an integer from 10 to 60. In its preferred ~; configuration, the hydroxy-terminated aliphatic polyether of ~ .
1~` _3a --``` 114~2916 76R74-A C.I.P. of S.N. 822,490 ,:
the present invention will have the following structural formula:
H - ~OCH2CH ~ OH
'; CH2N3 x wherein x is an integer from 20 to 40.
In ~eneral, the desired hydroxyl-terminated aliphatic polyether having * dependent alkyl azide groups is prepared as follows:
., \0/ [ ]
~¦ NaN3 C\2JCH [CH2 ]nN3 ¦~ Catal Yzed H- OCH2CH ~ x OH
2 n 3 wherein n is an integer from 1-5 and x is an integer from 10 to 60. A typicalcatalyst for this system would be BF3. Similarly, the alkyi diazido polymer can be prepared by starting with a dichloro compound such as C~2~CH (CH2)n ICH CH2Cl O Cl One such commercially available compound is 1,2-diepoxy-4, 5-dichloropentane.
By way of example and not limitation, the azido polymer of the present invention can be prepared as follows:
A mixture of lOOq (1.0 mole) of polyepichlorohydrin, 1309 (2.0 moles) of sodium azide, and 600 ml of dimethyl formamide was heated at 100C and a~itated for 72 hours. The mixture was cooled and diluted with 500 ml of methylene chloride. The reaction mixture was then washed with water to remove sodium azide and dimethylformamide. The methylene chloride solution was dried over magnesium sulfate and concentrated to give 789 (72.9~) of viscous amber liquid.
114029~i 76R74-A C.I.P. of S.~l. 822,490 ;~ The liquid was characterized and the following properties were obtained:
Elemental Analysis: C(36.21); H(5.n5); N(40.56) wt.X
Molecular Weight: 2500 Funct;onality: 2 ` 5 Infrared Spectrum: 4.75~ (s) for N3 Density: 1.30.gm/cc Obviously, numerous variations and modifications may be made without departing from the present invention. Accordingly, it should be clearly understood that the form of the present invention described above is illustra-tive only and is not intended to limit the scope of the present invent;on.
.
Claims (5)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A hydroxy-terminated aliphatic polyether having pendant alkyl azide groups having a structural formula of:
wherein x is an integer from 10 to 60 and wherein R is selected from the group consisting of -(CH2)nN3, and -CH2CHN3CH2N3, and wherein n is an integer from 1 to 5.
wherein x is an integer from 10 to 60 and wherein R is selected from the group consisting of -(CH2)nN3, and -CH2CHN3CH2N3, and wherein n is an integer from 1 to 5.
2. The hydroxy-terminated aliphatic polyether of Claim 1 wherein said alkyl azide group is -CH2N3.
3. The hydroxy-terminated aliphatic polyether of Claim 1 having a structural formula of:
wherein x is an integer from 10 to 60.
wherein x is an integer from 10 to 60.
4. The hydroxy-terminated aliphatic polyether of Claim 1 or 3 wherein x is an integer from 20 to 40.
5. A process for producing hydroxy-terminated aliphatic polyethers of the general formula wherein x is an integer from 10 to 60 and wherein R is selec-ted from the group consisting of -(CH2)nN3 and -CH2CHN3CH2N3, wherein n is an integer from 1 to 5, by reacting a compound of the general formula , wherein n is an integer from 1 to 5 with sodium azide in an appropriate polar organic solvent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4,978 | 1979-01-08 | ||
| US06/004,978 US4268450A (en) | 1977-08-08 | 1979-01-08 | Energetic hydroxy-terminated azido polymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1140296A true CA1140296A (en) | 1983-01-25 |
Family
ID=21713505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000335332A Expired CA1140296A (en) | 1979-01-08 | 1979-09-10 | Energetic hydroxy-terminated azido polymer |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4268450A (en) |
| BE (1) | BE879858A (en) |
| CA (1) | CA1140296A (en) |
| CH (1) | CH644877A5 (en) |
| DE (1) | DE2945383A1 (en) |
| IT (1) | IT1164732B (en) |
| NO (1) | NO153302C (en) |
| SE (1) | SE446269B (en) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4655859A (en) * | 1980-05-21 | 1987-04-07 | The United States Of America As Represented By The Secretary Of The Army | Azido-based propellants |
| US4303414A (en) * | 1980-12-15 | 1981-12-01 | Rockwell International Corporation | Azido additives for liquid hydrocarbon motor fuels |
| US4483978A (en) * | 1981-05-12 | 1984-11-20 | S R I International | Energetic copolymers and method of making same |
| DE3120310A1 (en) * | 1981-05-21 | 1982-12-09 | Rockwell International Corp., 90245 El Segundo, Calif. | Propellant charges containing a polyglycidyl azide polymer |
| US4406718A (en) * | 1981-07-16 | 1983-09-27 | The United States Of America As Represented By The Secretary Of The Navy | Tetraazido polyesters and methods of preparation |
| US4405762A (en) * | 1981-12-07 | 1983-09-20 | Hercules Incorporated | Preparation of hydroxy-terminated poly(3,3-bisazidomethyloxetanes) |
| US4379894A (en) * | 1981-12-14 | 1983-04-12 | Rockwell International Corporation | Aqueous process for the quantitative conversion of polyepichlorohydrin to glycidyl azide polymer |
| US4379903A (en) * | 1982-03-01 | 1983-04-12 | The United States Of America As Represented By The Secretary Of The Navy | Propellant binders cure catalyst |
| US5092945A (en) * | 1982-03-01 | 1992-03-03 | The United States Of America As Represented By The Secretary Of The Navy | Glycidyl azide propellant with antigassing additives |
| US4432817A (en) * | 1982-03-25 | 1984-02-21 | The United States Of America As Represented By The Secretary Of The Air Force | Propellant containing an azidonitrocarbamate plasticizer |
| US4432814A (en) * | 1982-04-21 | 1984-02-21 | The United States Of America As Represented By The Secretary Of The Air Force | Azido esters |
| US4414384A (en) * | 1982-06-14 | 1983-11-08 | The United States Of America As Represented By The Secretary Of The Navy | Synthesis and polymerization of 3-azidooxetane |
| US4522756A (en) * | 1983-03-28 | 1985-06-11 | Rockwell International Corporation | Alkyl, azido, nitro ethers and method of preparation |
| US4486351A (en) * | 1983-12-14 | 1984-12-04 | Hercules Incorporated | Use of polymeric ethylene oxides in the preparation of glycidyl azide polymer |
| US5597978A (en) * | 1984-12-27 | 1997-01-28 | Aerojet-General Corporation | High energy hydroxy-terminated polyazido polymers |
| US5867981A (en) * | 1985-01-28 | 1999-02-09 | The United States Of America As Represented By The Secretary Of The Air Force | Solid rocket motor |
| US4879419A (en) * | 1985-07-01 | 1989-11-07 | Minnesota Mining And Manufacturing Company | Hydroxyl-terminated polyepichlorohydrin polymers |
| CA1339576C (en) * | 1985-08-30 | 1997-12-09 | Minnesota Mining And Manufacturing Company | Hydroxyl-termitated polyepichlorohydrin and derivatives |
| US4741742A (en) * | 1986-07-03 | 1988-05-03 | The United States Of America As Represented By The Secretary Of The Navy | Diazido alkanes and diazido alkanols as combustion modifiers for liquid hydrocarbon ramjet fuels |
| US4707540A (en) * | 1986-10-29 | 1987-11-17 | Morton Thiokol, Inc. | Nitramine oxetanes and polyethers formed therefrom |
| CA1262918A (en) * | 1986-12-01 | 1989-11-14 | Elie Ahad | Direct conversion of epichlorohydrin to glycidyl azide polymer |
| US5747603A (en) * | 1987-05-19 | 1998-05-05 | Thiokol Corporation | Polymers used in elastomeric binders for high-energy compositions |
| US4781861A (en) * | 1987-06-01 | 1988-11-01 | Rockwell International Corporation | Azide-terminated azido compound |
| US4962213A (en) * | 1987-06-22 | 1990-10-09 | Rockwell International Corporation | Energetic azido curing agents |
| AU663679B1 (en) * | 1988-02-01 | 1995-10-19 | Rockwell International Corporation | Glycidal azide polymer azide |
| US5032653A (en) * | 1988-06-28 | 1991-07-16 | Exxon Chemical Patents, Inc. | Direct synthesis by cationic polymerization of nitrogen-containing polymers |
| NL8801739A (en) * | 1988-07-08 | 1990-02-01 | Europ Agence Spatiale | HIGH PERFORMANCE PROPELLER COMBINATIONS FOR A ROCKET ENGINE. |
| US4937361A (en) * | 1989-02-02 | 1990-06-26 | Rockwell International Corporation | Glycidyl azide polymer and method of preparation |
| US4938812A (en) * | 1989-06-12 | 1990-07-03 | Rockwell International Corporation | Glycidyl azide polymer esters |
| US4970326A (en) * | 1989-06-12 | 1990-11-13 | Rockwell International Corporation | Glycidyl azide polymer diacetate |
| FR2648809B1 (en) * | 1989-06-21 | 1991-09-13 | Livbag Snc | SOLID GAS GENERATOR COMPOSITION AND ITS USE IN GAS GENERATORS FOR AIR BAGS FOR PROTECTING PASSENGERS OF A MOTOR VEHICLE |
| US5214110A (en) * | 1989-10-02 | 1993-05-25 | Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence Of Her Majesty's Canadian Government | Branched azido copolymers |
| US4997497A (en) * | 1990-04-05 | 1991-03-05 | Rockwell International Corporation | Castable smoke-producing pyrotechnic compositions |
| US5055600A (en) * | 1990-04-24 | 1991-10-08 | Rockwell International Corporation | Glycidyl azide polymer (gap) synthesis by molten salt method |
| DE4019322C2 (en) * | 1990-06-16 | 1995-01-19 | Fraunhofer Ges Forschung | Process for the production of high-energy, azide-containing polyester as a binder for solid fuels or explosives |
| US5045132A (en) * | 1990-09-06 | 1991-09-03 | Rockwell International Corporation | High-energy explosive or propellant |
| ES2038538B1 (en) * | 1991-08-01 | 1994-02-16 | Ercros Sa | "PROCEDURE FOR THE OBTAINING OF A HYDROXYTERMINATED GLYCIDYL AZIDE POLYMER" |
| US5223056A (en) * | 1992-01-21 | 1993-06-29 | Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence Of Her Majesty's Canadian Government | Azido thermoplastic elastomers |
| US5278023A (en) * | 1992-11-16 | 1994-01-11 | Minnesota Mining And Manufacturing Company | Propellant-containing thermal transfer donor elements |
| US5444135A (en) * | 1992-12-17 | 1995-08-22 | Exxon Chemical Patents Inc. | Direct synthesis by living cationic polymerization of nitrogen-containing polymers |
| US5380777A (en) * | 1993-01-08 | 1995-01-10 | Thiokol Corporation | Polyglycidyl nitrate plasticizers |
| US5483007A (en) * | 1993-04-22 | 1996-01-09 | Minnesota Mining And Manufacturing Company | Cyclic process for activation, use and recovery of phase-transfer catalysts |
| EP0646614A1 (en) * | 1993-10-04 | 1995-04-05 | Her Majesty The Queen In Right Of Canada As Represented By The Minister Of National Defence | Improved branched energetic azido polymers |
| US5681904A (en) * | 1996-04-01 | 1997-10-28 | Minnesota Mining And Manufacturing Company | Azido polymers having improved burn rate |
| DE19821010C1 (en) * | 1998-05-11 | 1999-10-28 | Bayern Chemie Gmbh Flugchemie | Gas generator solid propellant for submarine emergency surfacing system |
| US7521492B2 (en) * | 2005-06-01 | 2009-04-21 | 3M Innovative Properties Company | Self-extinguishing polymer composition |
| EP2167570A1 (en) | 2007-06-29 | 2010-03-31 | Basell Poliolefine Italia S.R.L. | An irradiated polyolefin composition comprising a non - phenolic stabilizer |
| US7824511B1 (en) | 2007-07-03 | 2010-11-02 | The United States Of America As Represented By The Secretary Of The Navy | Method of making GAP propellants by pre-reacting a metal fuel with isocyanate before mixing with binder and plasticizer |
| RU2487140C1 (en) * | 2011-12-22 | 2013-07-10 | Ильгиз Хазиевич Гараев | Method of producing poly-3,3-bis(azidomethyl)oxetane |
| RU2529188C1 (en) * | 2013-06-26 | 2014-09-27 | Федеральное государственное бюджетное учреждение науки Институт химической физики им. Н.Н. Семенова Российской академии наук (ИХФ РАН) | Method of producing oligoglycidyl azides |
| FR3027597B1 (en) * | 2014-10-28 | 2016-12-09 | Herakles | PERFORMANT COMPOSITE PYROTECHNIC PRODUCT WITHOUT PB IN ITS COMPOSITION AND PREPARATION |
| FR3027598B1 (en) * | 2014-10-28 | 2018-05-04 | Arianegroup Sas | COMPOSITE PYROTECHNIC PRODUCT WITH DNA AND RDX LOADS IN PAG TYPE BINDER AND PREPARATION THEREOF |
| EP3676312B1 (en) | 2017-08-30 | 2021-04-14 | King Abdullah University Of Science And Technology | Direct synthesis of glycidyl azide polymers |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE549814A (en) * | 1955-07-29 | |||
| US3122570A (en) * | 1960-04-29 | 1964-02-25 | Union Carbide Corp | Triazoalkyl ethers |
| US3453108A (en) * | 1965-04-13 | 1969-07-01 | Agfa Gevaert Nv | Photochemical cross-linking of polymers |
| US3849230A (en) * | 1969-07-18 | 1974-11-19 | Hercules Inc | Process of bonding using epoxy-azido adhesives |
| US3645917A (en) * | 1970-02-25 | 1972-02-29 | Hercules Inc | Polyethers containing azidomethyl side chains |
| US4031068A (en) * | 1976-07-26 | 1977-06-21 | Uniroyal Inc. | Non-migratory sulfonyl azide antioxidants |
| US4085123A (en) * | 1976-10-21 | 1978-04-18 | Rockwell International Corporation | 1,3-Diazido-2-nitrazapropane |
| US4141910A (en) * | 1977-02-14 | 1979-02-27 | Rockwell International Corporation | Azido compounds |
-
1979
- 1979-01-08 US US06/004,978 patent/US4268450A/en not_active Expired - Lifetime
- 1979-09-10 CA CA000335332A patent/CA1140296A/en not_active Expired
- 1979-10-16 IT IT7950579A patent/IT1164732B/en active
- 1979-10-31 SE SE7909027A patent/SE446269B/en not_active IP Right Cessation
- 1979-11-06 BE BE0/197993A patent/BE879858A/en not_active IP Right Cessation
- 1979-11-09 DE DE19792945383 patent/DE2945383A1/en active Granted
- 1979-11-16 NO NO793718A patent/NO153302C/en unknown
-
1980
- 1980-01-07 CH CH7380A patent/CH644877A5/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO793718L (en) | 1980-07-09 |
| SE7909027L (en) | 1980-07-09 |
| DE2945383A1 (en) | 1980-07-24 |
| SE446269B (en) | 1986-08-25 |
| NO153302C (en) | 1986-02-19 |
| CH644877A5 (en) | 1984-08-31 |
| IT7950579A0 (en) | 1979-10-16 |
| NO153302B (en) | 1985-11-11 |
| IT1164732B (en) | 1987-04-15 |
| US4268450A (en) | 1981-05-19 |
| BE879858A (en) | 1980-03-03 |
| DE2945383C2 (en) | 1989-07-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
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