CA1248323A - Procede de preparation de polychlorophosphazenes lineaires possedant un groupement terminal pxc1.sub.2, x designant o ou s - Google Patents
Procede de preparation de polychlorophosphazenes lineaires possedant un groupement terminal pxc1.sub.2, x designant o ou sInfo
- Publication number
- CA1248323A CA1248323A CA000493085A CA493085A CA1248323A CA 1248323 A CA1248323 A CA 1248323A CA 000493085 A CA000493085 A CA 000493085A CA 493085 A CA493085 A CA 493085A CA 1248323 A CA1248323 A CA 1248323A
- Authority
- CA
- Canada
- Prior art keywords
- polycondensation
- solvent
- pxcl3
- monomer
- release
- 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
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 73
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000000178 monomer Substances 0.000 claims abstract description 21
- 238000010438 heat treatment Methods 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000000470 constituent Substances 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 150000004816 dichlorobenzenes Chemical class 0.000 claims description 2
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 claims 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical class C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 5
- 238000004132 cross linking Methods 0.000 abstract description 4
- 239000000460 chlorine Substances 0.000 description 17
- 239000012429 reaction media Substances 0.000 description 13
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- -1 dichlorophosphoryl Chemical group 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- 239000000499 gel Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- MSGMXYUAWZYTFC-UHFFFAOYSA-N sodium;2,2,2-trifluoroethanolate Chemical compound [Na+].[O-]CC(F)(F)F MSGMXYUAWZYTFC-UHFFFAOYSA-N 0.000 description 5
- 235000017168 chlorine Nutrition 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000009529 body temperature measurement Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- IUYHQGMDSZOPDZ-UHFFFAOYSA-N 2,3,4-trichlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=CC=C1C1=CC=CC=C1 IUYHQGMDSZOPDZ-UHFFFAOYSA-N 0.000 description 1
- IVKPBNVMLKJSFG-UHFFFAOYSA-N 2-chloronaphthalene-1-carbaldehyde Chemical compound C1=CC=CC2=C(C=O)C(Cl)=CC=C21 IVKPBNVMLKJSFG-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101001120868 Homo sapiens Meckel syndrome type 1 protein Proteins 0.000 description 1
- 102100026048 Meckel syndrome type 1 protein Human genes 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 101150051409 let-19 gene Proteins 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8415892 | 1984-10-17 | ||
| FR8415892A FR2571710B1 (fr) | 1984-10-17 | 1984-10-17 | Procede de preparation de polychlorophosphazenes lineaires possedant un groupement terminal pxcl2, x designant o ou s, par polycondensation en solution des monomeres p2nxcl5 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1248323A true CA1248323A (fr) | 1989-01-10 |
Family
ID=9308732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000493085A Expired CA1248323A (fr) | 1984-10-17 | 1985-10-16 | Procede de preparation de polychlorophosphazenes lineaires possedant un groupement terminal pxc1.sub.2, x designant o ou s |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4693876A (enExample) |
| EP (1) | EP0178997B1 (enExample) |
| JP (1) | JPS62501144A (enExample) |
| BE (1) | BE903456A (enExample) |
| CA (1) | CA1248323A (enExample) |
| DE (1) | DE3562761D1 (enExample) |
| FR (1) | FR2571710B1 (enExample) |
| IT (1) | IT1201482B (enExample) |
| WO (1) | WO1986002344A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2612170B1 (fr) * | 1987-03-10 | 1989-06-16 | Atochem | Procede de preparation de polychlorophosphazene en presence de bis(dichlorophosphoryl)imide |
| 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 |
| DE3874035T2 (de) * | 1987-07-02 | 1993-03-18 | Atochem Elf Sa | Verfahren zur regulierung des molekulargewichts von polychlorphosphazenen und davon abgeleiteten polyorganophosphazenen und die in diesem verfahren angewandten regulierungsmittel. |
| 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. |
| IL95939A0 (en) * | 1989-10-20 | 1991-07-18 | Atochem | Process for compensating the harmful effects of impurities of n-dichlorophosphoryltrichlorophosphazene and its polycondensation product |
| 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. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4005171A (en) * | 1974-05-28 | 1977-01-25 | Horizons Incorporated, A Division Of Horizons Research Incorporated | Catalytic preparation of soluble poly(dichlorophosphazenes) |
| FR2424876A1 (fr) * | 1978-05-05 | 1979-11-30 | Firestone Tire & Rubber Co | Polymerisation en solution de chlorophosphazene avec du soufre comme agent de modification |
| 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 |
-
1984
- 1984-10-17 FR FR8415892A patent/FR2571710B1/fr not_active Expired
-
1985
- 1985-10-15 US US06/882,958 patent/US4693876A/en not_active Expired - Fee Related
- 1985-10-15 JP JP60504580A patent/JPS62501144A/ja active Granted
- 1985-10-15 WO PCT/FR1985/000294 patent/WO1986002344A1/fr not_active Ceased
- 1985-10-15 DE DE8585402001T patent/DE3562761D1/de not_active Expired
- 1985-10-15 EP EP85402001A patent/EP0178997B1/fr not_active Expired
- 1985-10-16 CA CA000493085A patent/CA1248323A/fr not_active Expired
- 1985-10-16 BE BE0/215733A patent/BE903456A/fr not_active IP Right Cessation
- 1985-10-17 IT IT22530/85A patent/IT1201482B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| BE903456A (fr) | 1986-02-17 |
| FR2571710A1 (fr) | 1986-04-18 |
| JPS62501144A (ja) | 1987-05-07 |
| IT1201482B (it) | 1989-02-02 |
| WO1986002344A1 (fr) | 1986-04-24 |
| US4693876A (en) | 1987-09-15 |
| EP0178997B1 (fr) | 1988-05-18 |
| JPH0458405B2 (enExample) | 1992-09-17 |
| FR2571710B1 (fr) | 1986-12-26 |
| IT8522530A0 (it) | 1985-10-17 |
| EP0178997A1 (fr) | 1986-04-23 |
| DE3562761D1 (en) | 1988-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |