NO153302B - Hydroksyavsluttet alifatisk polyeter, samt anvendelse av en slik. - Google Patents
Hydroksyavsluttet alifatisk polyeter, samt anvendelse av en slik. Download PDFInfo
- Publication number
- NO153302B NO153302B NO793718A NO793718A NO153302B NO 153302 B NO153302 B NO 153302B NO 793718 A NO793718 A NO 793718A NO 793718 A NO793718 A NO 793718A NO 153302 B NO153302 B NO 153302B
- Authority
- NO
- Norway
- Prior art keywords
- integer
- hydroxy
- groups
- aliphatic polyether
- polyets
- Prior art date
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- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical class [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 title 1
- 229920000570 polyether Polymers 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 6
- 239000003380 propellant Substances 0.000 claims description 6
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- -1 difluoroamino Chemical group 0.000 description 3
- 150000004820 halides Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000005335 azido alkyl group Chemical group 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910017051 nitrogen difluoride Inorganic materials 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002755 poly(epichlorohydrin) Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000004449 solid propellant Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- BUYPQDYFXPMKTD-UHFFFAOYSA-N 2-(2,3-dichloropropyl)oxirane Chemical compound ClCC(Cl)CC1CO1 BUYPQDYFXPMKTD-UHFFFAOYSA-N 0.000 description 1
- NKWKILGNDJEIOC-UHFFFAOYSA-N 2-(2-chloroethyl)oxirane Chemical compound ClCCC1CO1 NKWKILGNDJEIOC-UHFFFAOYSA-N 0.000 description 1
- LSOXTBBDZHIHDE-UHFFFAOYSA-N 2-(3-chloropropyl)oxirane Chemical compound ClCCCC1CO1 LSOXTBBDZHIHDE-UHFFFAOYSA-N 0.000 description 1
- VOUIEAZSNLLDLK-UHFFFAOYSA-N 2-(4-chlorobutyl)oxirane Chemical compound ClCCCCC1CO1 VOUIEAZSNLLDLK-UHFFFAOYSA-N 0.000 description 1
- IQFAHALNMCMFFA-UHFFFAOYSA-N 2-(5-chloropentyl)oxirane Chemical compound ClCCCCCC1CO1 IQFAHALNMCMFFA-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyethers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Oppfinnelsen vedrører en hydroksyavsluttet alifatisk polyeter som har side-vedhengende alkylazidgrupper, og dens anvendelse som energirikt bindemiddel i drivmidler.
Faste drivmidler settes vanligvis sammen av et ok-sydasjonsmiddel og et brennstoff, hvorved egnede bindemidler og myknere tilsettes. De mest energirike systemer anvender bindemidler og myknere som inneholder energirike grupper, f.eks. nitro (-N02) , fluordinitro [FC(N02)2-], difluoramino (-NF2)
og en rekke andre lignende grupper.
I den senere tid anvendes azidomyknere. Disse gir drivmidlene ytterligere energi, da hver azidogruppe forhøyer energi-innholdet i systemet med ca. 85 kcal/mol. Dessverre oppviser dog de få hittil syntetiserte azidopolymerer ingen egnede endestående funksjonelle grupper. Nærvær av slike endestående grupper er imidlertid forutsetning for god formbarhet og gode fysikalske egenskaper hos drivmidlene.
Fra us-patent 3.453.108 er det kjent en azidopolymer med endestående funksjonelle grupper og azidosulfonyl-substituenter som er bundet til polymerkjeden OY^r en aromatisk ring.
Det karakteristiske ved den hydroksyavsluttede alifatiske polyeter i henhold til oppfinnelsen er at den har den generelle strukturformel:
hvor x er et helt tall fra 10 til 60, og hvor R er valgt fra gruppen som består av -(Ct^^IS^, og -CH2CHN3CH2N3, og hvor n er et helt tall fra 1 til 5.
Fortrinnsvis har den hydroksyavsluttede alifatiske polyeter i henhold til oppfinnelsen følgende strukturformel:
hvor x er et helt tall fra 10 til 60,
fortrinnsvis 20-40.
I U.S.-patentskrift nr. 3 645 913 beskrives polyetere som er fremstilt ved omsetning av poly — epiklorhydrin med natriumazid i polart løsningsmiddel, hvor man imidlertid går ut fra et materiale med meget høyere molekylvekt, og også oppnår et produkt med høyere molekylvekt enn i henhold til foreliggénde oppfinnelse. Ved reaksjonen omdannes halogenidgrupper til azid-grupper, i henhold til nevnte patent dog i så liten grad at det fører til et produkt som er svært forskjellig fra den hydroksyavsluttede alifatiske polyeter i henhold til foreliggende oppfinnelse, hvor så å si alle kloridgrupper er omdannet til azid-grupper, slik det skal forklares i det følgende.
De alifatiske polyetere i henhold til foreliggende oppfinnelse kan fremstilles i henhold til følgende reaksjonsskjerna:
hvor n betyr et helt tall fra 1 til 5 og x et helt tall fra 10
til 60. Egnede halogensubstituerte epoksyforbindelser omsettes i et polart organisk løsningsmiddel med et alkaliazid, slik at under avspaltning av alkalihalogenid oppnås den tilsvarende azido-substituerte epoksyforbindelse. I tilknytning til dette polymeres epoksyforbindelsen under anvendelse av en egnet katalysator, hvorved den ønskede azidopolymer oppnås.
Egnede halogen-substituerte epoksyforbindelser omfatter 1-epiklorhydrin, 1,2-epoksy-4-klorbutan, 1,2-epoksy-5-klorpentan, 1,2-epoksy-6-klorheksan og 1,2-epoksy-7-klorheptan. Fortrinnsvis anvendes det kommersielt tilgjengelige 1-epiklorhydrin.
Egnede alkaliazider omfatter f.eks. natrium- og kalium-azid, hvorved natriumazid foretrekkes.
Reaksjonen utføres fortrinnsvis i nærvær av et polart organisk løsningsmiddel. Egnede polare løsningsmidler omfatter eksempelvis dimetylformamid, metylenklorid, kloroform, tetra-hydrofuran, metanol og andre polare løsningsmidler som tradisjonelt anvendes ved denne reaksjon. Fortrinnsvis anvendes dimetylformamid.
Som katalysator ved polymeriseringen av den azido-"substituerte epoksyforbindelse kan det anvendes en starter som er vanlig på dette fagområde. En typisk katalysator for dette system er f.eks. BF^-
på ganske analog måte kan man under anvendelse av en diklorforbindelse, f.eks.
hvor n står for 1-5, oppnå polymerer med sidevedhengende diazido-alkylgrupper. En slik utgangsforbindelse som er tilgjengelig i handelen, er 1,2-epoksy-4,5-diklorpentan.
En alternativ fremstillingsmulighet forde beskrevne alifatiske polyetere med sidestående azidoalkylgrupper består i at man går ut fra polyepiklorhydrin eller annen alifatisk polyeter med halogenfunksjoner. Det utføres igjen en reaksjon mellom et alkaliazid i et polart organisk løsningsmiddel, hvorved halogenfunksjonen substitueres med en azidogruppe. under avspaltning av alkalihalogenid får man den til-strebede polymer med sidestående azidoalkylgrupper.
Ved begge fremgangsmåtevarianter er så vel reaksjons-temperatur som reaksjonstid for innføringstrinnet av azidogruppen ikke særlig kritisk. Reaksjonstemperaturen ligger fortrinnsvis i et område på 20-150°C, særlig foretrukket mellom 80 og 120°C. Reaksjonstiden kan ligge i et område fra noen timer og opp til noen dager. Under reaksjonen omrøres reaksjonsblandingen med egnede innretninger, eksempelvis med en rører.
I det følgende forklares oppfinnelsen ved hjelp av et eksempel mer i detaljer.
Eksempel
En blanding av 100 g polyepiklorhydrin, 130 g (2,0 mol) natriumazid og 600 ml dimetylformamid oppvarmes til l00°c og omrøres i 72 timer ved denne temperatur. Så avkjøler man blandingen og fortynner den med 500 ml metylenklorid. Reaksjonsblandingen vaskes deretter med vann for fjerning av natriumklorid som har dannet seg og ureagert natriumazid, sammen med dimetylformamidet. Metylenkloridløsningen tørkes over magnesiumsulfat og inndampes,
og man får 78 g (72,9%) av en viskøs, brun væske. Væsken karak-teriseres, hvorved man iakttar følgende egenskaper:
Elementæranalyse: C: 36,21 vekt% H: 5,05 vekt%
N: 40,56 vekt%
Molekylvekt: 2500
Valens: 2
infrarødt-
spektrum: 4,75^u(s) for N3
Tetthet: 1,30 g/cm3
Den oppnådde væske anvendes som bindemiddel ved frem-stilling av et fast drivmiddel eller en drivladning.
Claims (4)
1. Hydroksyavsluttet alifatisk polyeter som har side-vedhengende alkylazidgrupper, for anvendelse som energirikt bindemiddel i drivmidler, karakterisert ved at den har den generelle strukturformel:
hvor x er et helt tall fra 10 til 60, og hvor R er valgt fra gruppen som består av -(CH2)nN3, og -CH2CHN3CH2N3, og hvor n er et helt tall fra 1 til 5.
2. Hydroksyavsluttet alifatisk polyeter som angitt i krav 1, karakterisert ved at den har strukturformelen:
hvor x er et helt tall fra 10 til 60.
3. Hydroksyavsluttet alifatisk polyeter som angitt i krav 1 eller 2, karakterisert ved at x er ét helt tall fra 20 til 40.
4. Anvendelse av en hydroksyavsluttet alifatisk polyeter i henhold til ett av kravene 1 og 2, som energirikt bindemiddel i drivmidler.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/004,978 US4268450A (en) | 1977-08-08 | 1979-01-08 | Energetic hydroxy-terminated azido polymer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO793718L NO793718L (no) | 1980-07-09 |
| NO153302B true NO153302B (no) | 1985-11-11 |
| NO153302C NO153302C (no) | 1986-02-19 |
Family
ID=21713505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO793718A NO153302C (no) | 1979-01-08 | 1979-11-16 | Hydroksyavsluttet alifatisk polyeter, samt anvendelse av en slik. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4268450A (no) |
| BE (1) | BE879858A (no) |
| CA (1) | CA1140296A (no) |
| CH (1) | CH644877A5 (no) |
| DE (1) | DE2945383A1 (no) |
| IT (1) | IT1164732B (no) |
| NO (1) | NO153302C (no) |
| SE (1) | SE446269B (no) |
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 (de) * | 1981-05-21 | 1982-12-09 | Rockwell International Corp., 90245 El Segundo, Calif. | Treibladungen mit einem gehalt an einem polyglycidylazid-polymeren |
| 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 (nl) * | 1988-07-08 | 1990-02-01 | Europ Agence Spatiale | Stuwstofcombinaties met hoge prestatie voor een raketmotor. |
| US4937361A (en) * | 1989-02-02 | 1990-06-26 | Rockwell International Corporation | Glycidyl azide polymer and method of preparation |
| US4970326A (en) * | 1989-06-12 | 1990-11-13 | Rockwell International Corporation | Glycidyl azide polymer diacetate |
| US4938812A (en) * | 1989-06-12 | 1990-07-03 | Rockwell International Corporation | Glycidyl azide polymer esters |
| FR2648809B1 (fr) * | 1989-06-21 | 1991-09-13 | Livbag Snc | Composition solide generatrice de gaz et son utilisation dans les generateurs de gaz pour coussins gonflables destines a proteger les passagers d'un vehicule automobile |
| 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 (de) * | 1990-06-16 | 1995-01-19 | Fraunhofer Ges Forschung | Verfahren zur Herstellung energiereicher, azidgruppenhaltiger Polyester als Binder für feste Treib- oder Explosivstoffe |
| US5045132A (en) * | 1990-09-06 | 1991-09-03 | Rockwell International Corporation | High-energy explosive or propellant |
| ES2038538B1 (es) * | 1991-08-01 | 1994-02-16 | Ercros Sa | "procedimiento para la obtencion de un polimero glicidil azida hidroxiterminado" |
| 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 (de) * | 1998-05-11 | 1999-10-28 | Bayern Chemie Gmbh Flugchemie | Gasgenerator-Festtreibstoff und dessen Verwendung |
| US7521492B2 (en) * | 2005-06-01 | 2009-04-21 | 3M Innovative Properties Company | Self-extinguishing polymer composition |
| WO2009003930A1 (en) | 2007-06-29 | 2009-01-08 | 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 (ru) * | 2011-12-22 | 2013-07-10 | Ильгиз Хазиевич Гараев | Способ получения поли-3,3-бис(азидометил)оксетана |
| RU2529188C1 (ru) * | 2013-06-26 | 2014-09-27 | Федеральное государственное бюджетное учреждение науки Институт химической физики им. Н.Н. Семенова Российской академии наук (ИХФ РАН) | Способ получения олигоглицидилазидов |
| FR3027597B1 (fr) * | 2014-10-28 | 2016-12-09 | Herakles | Produit pyrotechnique composite performant sans pb dans sa composition et sa preparation |
| FR3027598B1 (fr) * | 2014-10-28 | 2018-05-04 | Arianegroup Sas | Produit pyrotechnique composite avec charges d'adn et de rdx dans un liant de type pag et sa preparation |
| WO2019043559A1 (en) | 2017-08-30 | 2019-03-07 | King Abdullah University Of Science And Technology | DIRECT SYNTHESIS OF GLYCIDYL NITROGEN POLYMERS |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE549814A (no) * | 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/it active
- 1979-10-31 SE SE7909027A patent/SE446269B/sv not_active IP Right Cessation
- 1979-11-06 BE BE0/197993A patent/BE879858A/fr not_active IP Right Cessation
- 1979-11-09 DE DE19792945383 patent/DE2945383A1/de active Granted
- 1979-11-16 NO NO793718A patent/NO153302C/no unknown
-
1980
- 1980-01-07 CH CH7380A patent/CH644877A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1164732B (it) | 1987-04-15 |
| DE2945383A1 (de) | 1980-07-24 |
| US4268450A (en) | 1981-05-19 |
| CA1140296A (en) | 1983-01-25 |
| SE446269B (sv) | 1986-08-25 |
| DE2945383C2 (no) | 1989-07-06 |
| BE879858A (fr) | 1980-03-03 |
| IT7950579A0 (it) | 1979-10-16 |
| SE7909027L (sv) | 1980-07-09 |
| NO153302C (no) | 1986-02-19 |
| CH644877A5 (en) | 1984-08-31 |
| NO793718L (no) | 1980-07-09 |
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