CA1084520A - Polymerization and ring equilibration of trifluoroethyoxy-chloro-cyclotriphosphazenes - Google Patents
Polymerization and ring equilibration of trifluoroethyoxy-chloro-cyclotriphosphazenesInfo
- Publication number
- CA1084520A CA1084520A CA278,480A CA278480A CA1084520A CA 1084520 A CA1084520 A CA 1084520A CA 278480 A CA278480 A CA 278480A CA 1084520 A CA1084520 A CA 1084520A
- Authority
- CA
- Canada
- Prior art keywords
- sodium
- compound
- reaction
- products produced
- chlorine atoms
- 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
- 238000006116 polymerization reaction Methods 0.000 title abstract description 8
- 238000011067 equilibration Methods 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 16
- 229920001577 copolymer Polymers 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 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 abstract description 4
- 239000011734 sodium Substances 0.000 claims description 13
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- 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 claims description 10
- MSGMXYUAWZYTFC-UHFFFAOYSA-N sodium;2,2,2-trifluoroethanolate Chemical group [Na+].[O-]CC(F)(F)F MSGMXYUAWZYTFC-UHFFFAOYSA-N 0.000 claims description 6
- -1 sodium alkoxide Chemical class 0.000 claims description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- NYYLKNDBZDKKAV-UHFFFAOYSA-N ClP1N=PN=P[N]1 Chemical class ClP1N=PN=P[N]1 NYYLKNDBZDKKAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 claims 6
- 239000007795 chemical reaction product Substances 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical group [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 2
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000007944 thiolates Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 abstract description 6
- 125000001424 substituent group Chemical group 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000006260 foam Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- NXDBMYTZSNQBEW-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,3,5,2,4,6-triazatriphosphinine Chemical class N1=PNPNP1 NXDBMYTZSNQBEW-UHFFFAOYSA-N 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 238000012719 thermal polymerization Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000001212 derivatisation Methods 0.000 description 3
- 229920002627 poly(phosphazenes) Polymers 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000004452 microanalysis Methods 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 1
- COLOHWPRNRVWPI-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound [CH2]C(F)(F)F COLOHWPRNRVWPI-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 238000004679 31P NMR spectroscopy Methods 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920002632 poly(dichlorophosphazene) polymer Polymers 0.000 description 1
- 229920003221 poly(phosphazene) elastomer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68706976A | 1976-05-17 | 1976-05-17 | |
| US687,069 | 1976-05-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1084520A true CA1084520A (en) | 1980-08-26 |
Family
ID=24758918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA278,480A Expired CA1084520A (en) | 1976-05-17 | 1977-05-16 | Polymerization and ring equilibration of trifluoroethyoxy-chloro-cyclotriphosphazenes |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS534100A (enrdf_load_stackoverflow) |
| AU (1) | AU511328B2 (enrdf_load_stackoverflow) |
| BE (1) | BE854757A (enrdf_load_stackoverflow) |
| CA (1) | CA1084520A (enrdf_load_stackoverflow) |
| DE (2) | DE2721826A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1543544A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111574676A (zh) * | 2020-05-21 | 2020-08-25 | 上海工程技术大学 | 阻燃水性聚氨酯乳液 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116917383A (zh) * | 2021-03-02 | 2023-10-20 | 株式会社日本触媒 | 含磷腈键的聚合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3370020A (en) * | 1964-09-29 | 1968-02-20 | American Cyanamid Co | Process for the production of phosphonitrilic polymers and polymers produced thereby |
| US3515688A (en) | 1967-08-30 | 1970-06-02 | Horizons Research Inc | Extreme service phosphonitrile elastomers |
| US3732175A (en) | 1971-09-27 | 1973-05-08 | Firestone Tire & Rubber Co | Crosslinking of phosphazene polymers |
| JPS4912570A (enrdf_load_stackoverflow) * | 1972-05-15 | 1974-02-04 | ||
| SE374377B (enrdf_load_stackoverflow) * | 1972-07-17 | 1975-03-03 | Mo Och Domsjoe Ab | |
| US3836608A (en) * | 1972-08-17 | 1974-09-17 | Fmc Corp | Process for self condensing phosphonitrilic chloroesters and product |
| US3838073A (en) | 1972-08-28 | 1974-09-24 | Horizons Research Inc | Poly(fluoroalkoxyphosphazene)homopolymers |
| CA1028339A (en) * | 1973-06-12 | 1978-03-21 | Carroll W. Lanier | Process for producing phosphazene fire retardant |
-
1977
- 1977-05-13 DE DE2721826A patent/DE2721826A1/de active Granted
- 1977-05-13 DE DE2759712A patent/DE2759712C2/de not_active Expired - Lifetime
- 1977-05-16 JP JP5625077A patent/JPS534100A/ja active Granted
- 1977-05-16 CA CA278,480A patent/CA1084520A/en not_active Expired
- 1977-05-16 AU AU25156/77A patent/AU511328B2/en not_active Expired
- 1977-05-17 GB GB20682/77A patent/GB1543544A/en not_active Expired
- 1977-05-17 BE BE177681A patent/BE854757A/xx not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111574676A (zh) * | 2020-05-21 | 2020-08-25 | 上海工程技术大学 | 阻燃水性聚氨酯乳液 |
| CN111574676B (zh) * | 2020-05-21 | 2022-02-08 | 上海工程技术大学 | 阻燃水性聚氨酯乳液的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2721826C2 (enrdf_load_stackoverflow) | 1987-10-22 |
| AU2515677A (en) | 1978-11-23 |
| DE2759712C2 (enrdf_load_stackoverflow) | 1990-01-11 |
| AU511328B2 (en) | 1980-08-14 |
| BE854757A (fr) | 1977-11-17 |
| DE2721826A1 (de) | 1977-12-08 |
| JPS534100A (en) | 1978-01-14 |
| GB1543544A (en) | 1979-04-04 |
| JPS5432840B2 (enrdf_load_stackoverflow) | 1979-10-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |