CA1038545A - Process for the preparation of poly (haloaryloxyphosphazene) homopolymers - Google Patents
Process for the preparation of poly (haloaryloxyphosphazene) homopolymersInfo
- Publication number
- CA1038545A CA1038545A CA201,737A CA201737A CA1038545A CA 1038545 A CA1038545 A CA 1038545A CA 201737 A CA201737 A CA 201737A CA 1038545 A CA1038545 A CA 1038545A
- Authority
- CA
- Canada
- Prior art keywords
- poly
- hours
- sites
- polymer
- group
- 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
- 229920001519 homopolymer Polymers 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- -1 alkali metal salt Chemical class 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- 229920002632 poly(dichlorophosphazene) polymer Polymers 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000000460 chlorine Substances 0.000 abstract description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 4
- 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 description 2
- 239000002131 composite material Substances 0.000 abstract description 2
- 239000000835 fiber Substances 0.000 abstract description 2
- 239000003063 flame retardant Substances 0.000 abstract description 2
- 238000009413 insulation Methods 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 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 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002195 soluble material Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 1
- VQZRLBWPEHFGCD-UHFFFAOYSA-N 3-chloro-4-methylphenol Chemical compound CC1=CC=C(O)C=C1Cl VQZRLBWPEHFGCD-UHFFFAOYSA-N 0.000 description 1
- AQJFATAFTQCRGC-UHFFFAOYSA-N 3-chloro-4-methylphenol Natural products CC1=CC=C(O)C(Cl)=C1 AQJFATAFTQCRGC-UHFFFAOYSA-N 0.000 description 1
- WMUWDPLTTLJNPE-UHFFFAOYSA-N 4-bromo-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Br WMUWDPLTTLJNPE-UHFFFAOYSA-N 0.000 description 1
- GPOQODYGMUTOQL-UHFFFAOYSA-N 4-bromo-3-methylphenol Chemical compound CC1=CC(O)=CC=C1Br GPOQODYGMUTOQL-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001282736 Oriens Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 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
- 238000002103 osmometry Methods 0.000 description 1
- 150000002989 phenols Chemical group 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- GQFIWFPBDXSASA-UHFFFAOYSA-M sodium;2-chlorophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1Cl GQFIWFPBDXSASA-UHFFFAOYSA-M 0.000 description 1
- OTIRLXNYGIORBW-UHFFFAOYSA-M sodium;4-bromophenolate Chemical compound [Na+].[O-]C1=CC=C(Br)C=C1 OTIRLXNYGIORBW-UHFFFAOYSA-M 0.000 description 1
- CFPLEOLETMZLIB-UHFFFAOYSA-M sodium;4-chlorophenolate Chemical compound [Na+].[O-]C1=CC=C(Cl)C=C1 CFPLEOLETMZLIB-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000006379 syphilis Diseases 0.000 description 1
- 239000008096 xylene 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Organic Insulating Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36884673A | 1973-06-11 | 1973-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1038545A true CA1038545A (en) | 1978-09-12 |
Family
ID=23453004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA201,737A Expired CA1038545A (en) | 1973-06-11 | 1974-06-05 | Process for the preparation of poly (haloaryloxyphosphazene) homopolymers |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS548399B2 (enrdf_load_stackoverflow) |
| BE (1) | BE816189A (enrdf_load_stackoverflow) |
| CA (1) | CA1038545A (enrdf_load_stackoverflow) |
| DE (1) | DE2428124A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2234332B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1413785A (enrdf_load_stackoverflow) |
| NL (1) | NL7407713A (enrdf_load_stackoverflow) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5146400A (enrdf_load_stackoverflow) * | 1974-10-18 | 1976-04-20 | Kuraray Co | |
| CA1105477A (en) * | 1976-03-22 | 1981-07-21 | Edwin J. Quinn | Structurally regulated polyphosphazene copolymers |
| US4092278A (en) * | 1976-06-11 | 1978-05-30 | Armstrong Cork Company | Molecular-weight modification of polyphosphazenes |
| US4055523A (en) * | 1976-08-16 | 1977-10-25 | Armstrong Cork Company | Poly(dialkylaminoaryloxyphosphazene) polymers and foams |
| US4110421A (en) * | 1976-10-12 | 1978-08-29 | Armstrong Cork Company | Catalytic process for the preparation of phosphazene polymers |
| JPS53109918A (en) * | 1977-01-29 | 1978-09-26 | Kureha Chem Ind Co Ltd | Preparation of anti-tumor polysaccharides |
| JPS53109915A (en) * | 1977-01-29 | 1978-09-26 | Kureha Chem Ind Co Ltd | Preparation of anti-tumor polysaccharides |
| JPS53109914A (en) * | 1977-01-29 | 1978-09-26 | Kureha Chem Ind Co Ltd | Preparation of anti-tumor polysaccharides |
| JPS53109922A (en) * | 1977-01-29 | 1978-09-26 | Kureha Chem Ind Co Ltd | Preparation of anti-tumor polysaccharides |
| JPS53109921A (en) * | 1977-01-29 | 1978-09-26 | Kureha Chem Ind Co Ltd | Preparation of anti-tumor polysaccharides |
| JPS53109919A (en) * | 1977-01-29 | 1978-09-26 | Kureha Chem Ind Co Ltd | Preparation of anti-tumor polysaccharides |
| JPS53109920A (en) * | 1977-01-29 | 1978-09-26 | Kureha Chem Ind Co Ltd | Preparation of anti-tumor polysaccharides |
| FR2542211A1 (fr) * | 1983-03-11 | 1984-09-14 | Nippon Oil Co Ltd | Membrane permeable selective pour les separations de gaz |
| JPS6038307A (ja) * | 1983-08-11 | 1985-02-27 | Nippon Daigaku | 充填用複合材 |
| TW445276B (en) | 1998-08-13 | 2001-07-11 | Otsuka Chemical Co Ltd | Crosslinked phenoxyphosphazene compounds, process for the preparation thereof, flame retardants, flame-retardant resin compositions, and moldings of flame-retardant resins |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1473887A (fr) * | 1964-09-29 | 1967-03-24 | American Cyanamid Co | Polymères et procédé pour la production de ces polymères de phosphonitrile |
-
1974
- 1974-06-05 CA CA201,737A patent/CA1038545A/en not_active Expired
- 1974-06-10 JP JP6588574A patent/JPS548399B2/ja not_active Expired
- 1974-06-10 FR FR7419961A patent/FR2234332B1/fr not_active Expired
- 1974-06-10 GB GB2571674A patent/GB1413785A/en not_active Expired
- 1974-06-10 NL NL7407713A patent/NL7407713A/xx unknown
- 1974-06-11 BE BE145303A patent/BE816189A/xx unknown
- 1974-06-11 DE DE19742428124 patent/DE2428124A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU6951174A (en) | 1975-12-04 |
| NL7407713A (enrdf_load_stackoverflow) | 1974-12-13 |
| DE2428124A1 (de) | 1975-01-02 |
| GB1413785A (en) | 1975-11-12 |
| FR2234332B1 (enrdf_load_stackoverflow) | 1978-01-13 |
| JPS5034097A (enrdf_load_stackoverflow) | 1975-04-02 |
| BE816189A (fr) | 1974-12-11 |
| FR2234332A1 (enrdf_load_stackoverflow) | 1975-01-17 |
| JPS548399B2 (enrdf_load_stackoverflow) | 1979-04-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1038545A (en) | Process for the preparation of poly (haloaryloxyphosphazene) homopolymers | |
| US3370020A (en) | Process for the production of phosphonitrilic polymers and polymers produced thereby | |
| US2435252A (en) | Aryl phosphorus containing resins and the method of preparing the same | |
| US3856712A (en) | Poly(alkoxyaryloxyphosphazene) elastomers | |
| Ganapathiappan et al. | A new class of cation conductors: polyphosphazene sulfonates | |
| EP0044177A3 (en) | Blend of sulfone polymer and wholly aromatic polyester | |
| NZ204592A (en) | Amorphous aromatic etherketone/sulphone copolymers | |
| CN109762203A (zh) | 一种新型生物基磷氮阻燃添加剂及其制备的阻燃环氧树脂 | |
| DE69018040T2 (de) | Flammhemmende, thermoplastische Pfropfcopolymere die Polylsiloxan- und Polyphenylenäthersegmente enthalten. | |
| US3265640A (en) | Crosslinked polymers from alpha, alpha-dichloro-p-xylene and polysubstituted benzenes | |
| Strukelj et al. | Solvent Effects on the Preparation of Novel Amorphous Poly (aryl ether benzil) s | |
| EP0008795B1 (en) | Polyphosphazene polymers containing monoetheroxy and polyetheroxy substituents | |
| US3325530A (en) | Method for making organosilicon copolymers | |
| US4179553A (en) | Polyphosphazene polymers containing cyclic ketal substituents | |
| US4267311A (en) | Novel method for removal of sodium chloride from phosphazene rubber crumb swollen in water | |
| US4242494A (en) | Polyphosphazene polymers containing alkenyl substituents | |
| EP0014232B1 (en) | Polyphosphazene polymers containing substituents derived from ketoximes and process for producing them | |
| US4242493A (en) | Method of preparing substantially pure polyhalophenoxyphosphazene homopolymers and copolymers | |
| US4182836A (en) | Polyphosphazene copolymers containing substituents from alkylphosphite | |
| EP0003550B1 (en) | Process for converting leathery phosphazene polymer to elastomeric phosphazene polymer | |
| US4258171A (en) | Polyphosphazene polymers containing substituted alkyl/cycloalkyl substituents | |
| Haddon et al. | Thallium in the synthesis of phosphazene derivatives: donor-substituted polyphosphazenes | |
| CA1133919A (en) | Polyphosphazene polymers containing substituents derived from thienyl alcohols | |
| EP0159020B1 (en) | Polyphosphazene process | |
| US4247680A (en) | Polyphosphazene copolymers containing alkyl borate substituents |