JPH0465004B2 - - Google Patents
Info
- Publication number
- JPH0465004B2 JPH0465004B2 JP59138086A JP13808684A JPH0465004B2 JP H0465004 B2 JPH0465004 B2 JP H0465004B2 JP 59138086 A JP59138086 A JP 59138086A JP 13808684 A JP13808684 A JP 13808684A JP H0465004 B2 JPH0465004 B2 JP H0465004B2
- Authority
- JP
- Japan
- Prior art keywords
- polycondensation
- preparation
- carried out
- temperature
- polychlorophosphazene
- 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 - Lifetime
Links
- 238000006068 polycondensation reaction Methods 0.000 claims description 75
- 238000002360 preparation method Methods 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- -1 dichlorothiophosphoryl Chemical group 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 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 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 13
- 239000003208 petroleum Substances 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003085 diluting agent Substances 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
- 239000007788 liquid Substances 0.000 description 2
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 2
- 235000019392 nitrosyl chloride Nutrition 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 125000001863 phosphorothioyl group Chemical group *P(*)(*)=S 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- BOFCBEWFMWULDG-UHFFFAOYSA-N ClP(=S)(Cl)P(Cl)(Cl)N=P(Cl)(Cl)Cl Chemical compound ClP(=S)(Cl)P(Cl)(Cl)N=P(Cl)(Cl)Cl BOFCBEWFMWULDG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003831 antifriction material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- LOZAIRWAADCOHQ-UHFFFAOYSA-N triphosphazene Chemical compound PNP=NP LOZAIRWAADCOHQ-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- 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
-
- 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8311264 | 1983-07-06 | ||
| FR8311264A FR2548652B1 (fr) | 1983-07-06 | 1983-07-06 | Polychlorophosphazenes lineaires possedant un groupement terminal dichlorothiophosphoryle, procede de preparation de ces composes, et leur utilisation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6071504A JPS6071504A (ja) | 1985-04-23 |
| JPH0465004B2 true JPH0465004B2 (enExample) | 1992-10-16 |
Family
ID=9290582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59138086A Granted JPS6071504A (ja) | 1983-07-06 | 1984-07-05 | ジクロロチオホスフオリル端末基を有する線状ポリクロロホスフアゼン及びその調製法並びに用途 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4554113A (enExample) |
| EP (1) | EP0132188B1 (enExample) |
| JP (1) | JPS6071504A (enExample) |
| BE (1) | BE900090A (enExample) |
| CA (1) | CA1251011A (enExample) |
| DE (1) | DE3468009D1 (enExample) |
| FR (1) | FR2548652B1 (enExample) |
| IT (1) | IT1180203B (enExample) |
| SU (1) | SU1426457A3 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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. |
| US5620499A (en) * | 1992-12-14 | 1997-04-15 | Farley; James J. | Chemical dispensing device and method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3193343A (en) * | 1962-07-11 | 1965-07-06 | Olin Mathieson | Composition having the formula p2nscl5 and process for preparing same |
| US3348927A (en) * | 1962-11-29 | 1967-10-24 | Olin Mathieson | Composition and process |
| DE2234373A1 (de) * | 1972-07-13 | 1974-03-28 | Basf Ag | Verfahren zur herstellung von phosphinimino-thiophosphonylverbindungen |
| FR2466435A1 (fr) * | 1979-09-27 | 1981-04-10 | Inst Mondial Phosphate | Nouveaux polychlorophosphazenes et leur procede de preparation |
-
1983
- 1983-07-06 FR FR8311264A patent/FR2548652B1/fr not_active Expired
-
1984
- 1984-07-04 DE DE8484401423T patent/DE3468009D1/de not_active Expired
- 1984-07-04 EP EP84401423A patent/EP0132188B1/fr not_active Expired
- 1984-07-05 BE BE0/213278A patent/BE900090A/fr not_active IP Right Cessation
- 1984-07-05 CA CA000458210A patent/CA1251011A/fr not_active Expired
- 1984-07-05 SU SU843761601A patent/SU1426457A3/ru active
- 1984-07-05 JP JP59138086A patent/JPS6071504A/ja active Granted
- 1984-07-06 US US06/628,403 patent/US4554113A/en not_active Expired - Fee Related
- 1984-07-06 IT IT21773/84A patent/IT1180203B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2548652B1 (fr) | 1985-11-22 |
| US4554113A (en) | 1985-11-19 |
| BE900090A (fr) | 1984-11-05 |
| JPS6071504A (ja) | 1985-04-23 |
| SU1426457A3 (ru) | 1988-09-23 |
| IT8421773A1 (it) | 1986-01-06 |
| FR2548652A1 (fr) | 1985-01-11 |
| IT8421773A0 (it) | 1984-07-06 |
| EP0132188B1 (fr) | 1987-12-09 |
| IT1180203B (it) | 1987-09-23 |
| EP0132188A1 (fr) | 1985-01-23 |
| CA1251011A (fr) | 1989-03-14 |
| DE3468009D1 (en) | 1988-01-21 |
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