FR2466435A1 - Nouveaux polychlorophosphazenes et leur procede de preparation - Google Patents
Nouveaux polychlorophosphazenes et leur procede de preparation Download PDFInfo
- Publication number
- FR2466435A1 FR2466435A1 FR7924037A FR7924037A FR2466435A1 FR 2466435 A1 FR2466435 A1 FR 2466435A1 FR 7924037 A FR7924037 A FR 7924037A FR 7924037 A FR7924037 A FR 7924037A FR 2466435 A1 FR2466435 A1 FR 2466435A1
- Authority
- FR
- France
- Prior art keywords
- reaction
- controlled
- polychlorophosphazenes
- polycondensation
- atmospheric pressure
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 43
- 230000008569 process Effects 0.000 title claims description 28
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 25
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- 238000013270 controlled release Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 11
- -1 dichlorophosphoryl Chemical group 0.000 claims description 7
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 101150035983 str1 gene Proteins 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract description 10
- 229910019213 POCl3 Inorganic materials 0.000 abstract description 5
- 238000000576 coating method Methods 0.000 abstract description 3
- 239000003337 fertilizer Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003063 flame retardant Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 7
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000009102 absorption Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000001923 cyclic compounds Chemical class 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000000280 densification Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- LOZAIRWAADCOHQ-UHFFFAOYSA-N triphosphazene Chemical compound PNP=NP LOZAIRWAADCOHQ-UHFFFAOYSA-N 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- MAXUIBVITJKGMP-UHFFFAOYSA-N diphosphazene Chemical compound PN=P MAXUIBVITJKGMP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical class ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- BVIDQAVCCRUFGU-UHFFFAOYSA-M methyl sulfate;trimethyl(1-phenothiazin-10-ylpropan-2-yl)azanium Chemical compound COS([O-])(=O)=O.C1=CC=C2N(CC(C)[N+](C)(C)C)C3=CC=CC=C3SC2=C1 BVIDQAVCCRUFGU-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- NHTMYQCWNYVABS-UHFFFAOYSA-N trichloro(dichlorophosphanylimino)-$l^{5}-phosphane Chemical compound ClP(Cl)N=P(Cl)(Cl)Cl NHTMYQCWNYVABS-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/025—Polyphosphazenes
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/097—Compounds containing nitrogen and non-metals and optionally metals containing phosphorus atoms
- C01B21/098—Phosphonitrilic dihalides; Polymers thereof
- C01B21/0986—Phosphonitrilic dichlorides; Polymers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7924037A FR2466435A1 (fr) | 1979-09-27 | 1979-09-27 | Nouveaux polychlorophosphazenes et leur procede de preparation |
| EP80401248A EP0026685B1 (fr) | 1979-09-27 | 1980-09-02 | Polychlorophosphazènes linéaires, procédé pour leur préparation et leur utilisation |
| DE8080401248T DE3071484D1 (en) | 1979-09-27 | 1980-09-02 | Linear polychlorophosphazenes, process for their preparation and their use |
| US06/187,184 US4377558A (en) | 1979-09-27 | 1980-09-15 | Novel polychlorophosphazenes and process for their preparation |
| SU802985051A SU1131471A3 (ru) | 1979-09-27 | 1980-09-23 | Способ получени полихлорфосфазенов |
| US06/477,397 US4544536A (en) | 1979-09-27 | 1983-03-21 | Polychlorophosphazenes and process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7924037A FR2466435A1 (fr) | 1979-09-27 | 1979-09-27 | Nouveaux polychlorophosphazenes et leur procede de preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2466435A1 true FR2466435A1 (fr) | 1981-04-10 |
| FR2466435B1 FR2466435B1 (enExample) | 1983-01-07 |
Family
ID=9230065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7924037A Granted FR2466435A1 (fr) | 1979-09-27 | 1979-09-27 | Nouveaux polychlorophosphazenes et leur procede de preparation |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US4377558A (enExample) |
| EP (1) | EP0026685B1 (enExample) |
| DE (1) | DE3071484D1 (enExample) |
| FR (1) | FR2466435A1 (enExample) |
| SU (1) | SU1131471A3 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2466435A1 (fr) * | 1979-09-27 | 1981-04-10 | Inst Mondial Phosphate | Nouveaux polychlorophosphazenes et leur procede de preparation |
| FR2548652B1 (fr) * | 1983-07-06 | 1985-11-22 | Elf Aquitaine | Polychlorophosphazenes lineaires possedant un groupement terminal dichlorothiophosphoryle, procede de preparation de ces composes, et leur utilisation |
| FR2571710B1 (fr) * | 1984-10-17 | 1986-12-26 | Elf Aquitaine | Procede de preparation de polychlorophosphazenes lineaires possedant un groupement terminal pxcl2, x designant o ou s, par polycondensation en solution des monomeres p2nxcl5 |
| US4524052A (en) * | 1984-12-24 | 1985-06-18 | The Firestone Tire & Rubber Company | Borate chloride polymerization catalysts |
| FR2606396B1 (fr) * | 1986-11-12 | 1989-02-10 | Atochem | Procede d'obtention de n(dichlorophosphoryl) trichlorophosphazene a partir de pentachlorure de phosphore et de chlorure d'ammonium |
| FR2612172B1 (fr) * | 1987-03-10 | 1989-06-16 | Atochem | Procede de preparation de polychlorophosphazene |
| FR2612169B1 (fr) * | 1987-03-10 | 1989-06-16 | Atochem | Procede de preparation de n(dichlorophosphoryl)trichlorophosphazene |
| FR2612170B1 (fr) * | 1987-03-10 | 1989-06-16 | Atochem | Procede de preparation de polychlorophosphazene en presence de bis(dichlorophosphoryl)imide |
| ATE79835T1 (de) * | 1987-07-02 | 1992-09-15 | Atochem Elf Sa | Verfahren zur regulierung des molekulargewichts von polychlorphosphazenen und davon abgeleiteten polyorganophosphazenen und die in diesem verfahren angewandten regulierungsmittel. |
| US4806322A (en) * | 1987-11-16 | 1989-02-21 | The Firestone Tire & Rubber Company | Process for the production of linear polyphosphazenes |
| FR2629442B1 (fr) * | 1988-03-29 | 1990-11-23 | Atochem | Procede de preparation de compositions de polydichlorophosphazenes a taux controle d'oligomeres cycliques et les compositions resultant de la mise en oeuvre de ce procede |
| FR2647100A1 (fr) * | 1989-05-19 | 1990-11-23 | Atochem | Procede de polycondensation en masse du n-dichlorophosphoryl- ou n-dichlorothiophosphoryl-p-trichlorophosphazene |
| FR2653423A1 (fr) * | 1989-10-20 | 1991-04-26 | Atochem | Procede de regulation des masses moleculaires de polydichlorophosphazenes. |
| FR2682391A1 (fr) * | 1991-10-11 | 1993-04-16 | Atochem | Procede de preparation de polyalkyl ou arylchlorophosphazenes. |
| DE4317909A1 (de) * | 1993-05-28 | 1994-12-01 | Wacker Chemie Gmbh | Verfahren zum Kondensieren und/oder Äquilibrieren von Organosiliciumverbindungen |
| DE4317978A1 (de) * | 1993-05-28 | 1994-12-01 | Wacker Chemie Gmbh | Organosiliciumreste aufweisende Phosphazene, Verfahren zu deren Herstellung und deren Verwendung |
| FR2709256B1 (fr) * | 1993-07-15 | 1997-05-30 | Gen Electric | Procédé de préparation d'une composition catalytique de phosphazène utile pour la polycondensation et la redistribution de polymères d'organosiloxane. |
| US5403909A (en) * | 1993-07-15 | 1995-04-04 | General Electric Company | Catalysts for polycondensation and redistribution of organosiloxane polymers |
| US6309619B1 (en) * | 1998-07-14 | 2001-10-30 | Bechtel Bwxt Idaho, Llc | Solid state synthesis of poly(dichlorophosphazene) |
| RU2645682C1 (ru) * | 2017-05-25 | 2018-02-27 | Михаил Владимирович Горлов | Способ получения олигогалогенфосфазенов и полигалогенфосфазенов с регулируемой молекулярной массой взаимодействием галогенфосфоранов с гексаалкилдисилазанами |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA572951A (en) * | 1959-03-24 | Barth-Wehrenalp Gerhard | Phosphorus compounds and process for making | |
| US2925320A (en) * | 1956-02-16 | 1960-02-16 | Pennsalt Chemicals Corp | Compounds of the class p2x5no and process for producing same |
| US2980506A (en) * | 1956-09-27 | 1961-04-18 | Henkel & Compagnie G M B H | Nitrogen-phosphoric acid compounds containing active chlorine |
| GB1321102A (en) * | 1970-04-09 | 1973-06-20 | Castrol Ltd | Method for preparing trihalophosphazine phosphoryl dihalides |
| FR2466435A1 (fr) * | 1979-09-27 | 1981-04-10 | Inst Mondial Phosphate | Nouveaux polychlorophosphazenes et leur procede de preparation |
-
1979
- 1979-09-27 FR FR7924037A patent/FR2466435A1/fr active Granted
-
1980
- 1980-09-02 DE DE8080401248T patent/DE3071484D1/de not_active Expired
- 1980-09-02 EP EP80401248A patent/EP0026685B1/fr not_active Expired
- 1980-09-15 US US06/187,184 patent/US4377558A/en not_active Expired - Lifetime
- 1980-09-23 SU SU802985051A patent/SU1131471A3/ru active
-
1983
- 1983-03-21 US US06/477,397 patent/US4544536A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4544536A (en) | 1985-10-01 |
| DE3071484D1 (en) | 1986-04-17 |
| US4377558A (en) | 1983-03-22 |
| EP0026685B1 (fr) | 1986-03-12 |
| SU1131471A3 (ru) | 1984-12-23 |
| EP0026685A1 (fr) | 1981-04-08 |
| FR2466435B1 (enExample) | 1983-01-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse | ||
| TP | Transmission of property |