CA1215211A - Borate chloride polymerization catalysts - Google Patents
Borate chloride polymerization catalystsInfo
- Publication number
- CA1215211A CA1215211A CA000493426A CA493426A CA1215211A CA 1215211 A CA1215211 A CA 1215211A CA 000493426 A CA000493426 A CA 000493426A CA 493426 A CA493426 A CA 493426A CA 1215211 A CA1215211 A CA 1215211A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- polymerization
- catalyst
- mixtures
- 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
- 239000002685 polymerization catalyst Substances 0.000 title abstract description 6
- HITBOAGYESUOFH-UHFFFAOYSA-N boric acid hydrochloride Chemical compound Cl.OB(O)O HITBOAGYESUOFH-UHFFFAOYSA-N 0.000 title abstract description 3
- 239000013638 trimer Substances 0.000 claims abstract description 16
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 2
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 229920002627 poly(phosphazenes) Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- -1 substituted Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 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
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical class [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B35/00—Boron; Compounds thereof
- C01B35/06—Boron halogen compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| US06/685,582 US4524052A (en) | 1984-12-24 | 1984-12-24 | Borate chloride polymerization catalysts |
| US685,582 | 1984-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1215211A true CA1215211A (en) | 1986-12-16 |
Family
ID=24752825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000493426A Expired CA1215211A (en) | 1984-12-24 | 1985-10-21 | Borate chloride polymerization catalysts |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4524052A (enExample) |
| EP (1) | EP0187207B1 (enExample) |
| JP (1) | JPS61155218A (enExample) |
| CA (1) | CA1215211A (enExample) |
| DE (1) | DE3568765D1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4661233A (en) * | 1985-07-05 | 1987-04-28 | Westinghouse Electric Corp. | Cathode/ground shield arrangement in a sputter coating apparatus |
| FR2612172B1 (fr) * | 1987-03-10 | 1989-06-16 | Atochem | Procede de preparation de polychlorophosphazene |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4226840A (en) * | 1979-09-19 | 1980-10-07 | The Firestone Tire & Rubber Company | Process for the polymerization of cyclic polyhalophosphazenes using a catalyst composition of boron trihalide and oxygenated phosphorus compounds |
| FR2466435A1 (fr) * | 1979-09-27 | 1981-04-10 | Inst Mondial Phosphate | Nouveaux polychlorophosphazenes et leur procede de preparation |
| US4327064A (en) * | 1980-08-04 | 1982-04-27 | The Firestone Tire & Rubber Company | Solution polymerization of cyclic dichlorophosphazene oligomers in cycloaliphatic solvents |
-
1984
- 1984-12-24 US US06/685,582 patent/US4524052A/en not_active Expired - Lifetime
-
1985
- 1985-10-17 EP EP85113186A patent/EP0187207B1/en not_active Expired
- 1985-10-17 DE DE8585113186T patent/DE3568765D1/de not_active Expired
- 1985-10-21 CA CA000493426A patent/CA1215211A/en not_active Expired
- 1985-12-17 JP JP60282158A patent/JPS61155218A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0187207A1 (en) | 1986-07-16 |
| JPH0544409B2 (enExample) | 1993-07-06 |
| DE3568765D1 (en) | 1989-04-20 |
| EP0187207B1 (en) | 1989-03-15 |
| US4524052A (en) | 1985-06-18 |
| JPS61155218A (ja) | 1986-07-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4946938A (en) | A process for the catalytic synthesis of polyphosphazenes | |
| US4139598A (en) | Catalytic preparation of soluble poly(dichlorophosphazenes) | |
| US4226840A (en) | Process for the polymerization of cyclic polyhalophosphazenes using a catalyst composition of boron trihalide and oxygenated phosphorus compounds | |
| US4382914A (en) | Process for preparing cyclic phosphonitrilic chloride oligomers | |
| CA1215211A (en) | Borate chloride polymerization catalysts | |
| US4374815A (en) | Phosphonitrilic chloride polymers | |
| US4327063A (en) | Method of purifying cyclic dichlorophosphazenes containing trace amounts of protic impurities | |
| US4080432A (en) | Dissolution of polydihalophosphazenes | |
| US4327064A (en) | Solution polymerization of cyclic dichlorophosphazene oligomers in cycloaliphatic solvents | |
| US4522798A (en) | Halophosphazene polymers | |
| US3272776A (en) | Preparation of poly | |
| US4551317A (en) | Phosphonitrilic halide polymers | |
| US3869540A (en) | Montmorillonite clay catalysts for the production of phosphonitrilic chloride | |
| US4242316A (en) | Sulfamic acid as a catalyst for the polymerization of chlorocyclophosphazenes | |
| US3939228A (en) | Process for producing phosphazene compound | |
| US4522795A (en) | Phosphonitrilic chloride polymers | |
| CA1044438A (en) | Water as a catalyst for the polymerization of chlorocyclophosphazenes | |
| US4522796A (en) | Phosphonitrilic chloride polymers | |
| Tani et al. | Polymerization of α‐piperidone with M–AlEt3, MAlEt4, or KAlEt3 (piperidone) as catalysts and N‐acetyl‐α‐piperidone as initiator | |
| JPS5850924B2 (ja) | 環状ホスホニトリルクロライドオリゴマ−の製造方法 | |
| US4447408A (en) | Phosphonitrilic chloride polymers | |
| US3211753A (en) | Preparation of diphenylphosphinous azide | |
| KR950008966B1 (ko) | 폴리디클로로포스파젠의 제조방법 | |
| US5006324A (en) | Polymerization of phosphonitrilic chloride | |
| US3375084A (en) | Method for the preparation of complex fluoronitrosonium salts |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |