DE2721826A1 - Verfahren zur polymerisation und ringgleichgewichtseinstellung von trifluoraethoxy-chlorcyclotriphosphazenen - Google Patents
Verfahren zur polymerisation und ringgleichgewichtseinstellung von trifluoraethoxy-chlorcyclotriphosphazenenInfo
- Publication number
- DE2721826A1 DE2721826A1 DE2721826A DE2721826A DE2721826A1 DE 2721826 A1 DE2721826 A1 DE 2721826A1 DE 2721826 A DE2721826 A DE 2721826A DE 2721826 A DE2721826 A DE 2721826A DE 2721826 A1 DE2721826 A1 DE 2721826A1
- Authority
- DE
- Germany
- Prior art keywords
- sodium
- npcl
- copolymer
- product obtained
- compound
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 30
- 238000006116 polymerization reaction Methods 0.000 title claims description 11
- 229920000642 polymer Polymers 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- 229920001577 copolymer Polymers 0.000 claims description 18
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000012719 thermal polymerization Methods 0.000 claims description 8
- 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 7
- MSGMXYUAWZYTFC-UHFFFAOYSA-N sodium;2,2,2-trifluoroethanolate Chemical compound [Na+].[O-]CC(F)(F)F MSGMXYUAWZYTFC-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- -1 sodium alkoxide Chemical class 0.000 claims description 6
- 229920002627 poly(phosphazenes) Polymers 0.000 claims description 5
- 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 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 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
- 125000003118 aryl group Chemical group 0.000 claims description 2
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 claims description 2
- 239000000047 product Substances 0.000 claims 8
- 150000004703 alkoxides Chemical class 0.000 claims 3
- 239000007795 chemical reaction product Substances 0.000 claims 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 2
- 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
- 230000001105 regulatory effect Effects 0.000 claims 1
- 150000007944 thiolates Chemical class 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 239000013256 coordination polymer Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 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
- 238000004458 analytical method Methods 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 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 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000003063 flame retardant Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000006049 ring expansion reaction Methods 0.000 description 2
- 239000002904 solvent 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
- DZKXDEWNLDOXQH-UHFFFAOYSA-N 1,3,5,2,4,6-triazatriphosphinine Chemical class N1=PN=PN=P1 DZKXDEWNLDOXQH-UHFFFAOYSA-N 0.000 description 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
- 101100462138 Brassica napus OlnB1 gene Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 101150048735 POL3 gene Proteins 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical group N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000009826 distribution Methods 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
- 239000012530 fluid Substances 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000000269 nucleophilic effect Effects 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
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003221 poly(phosphazene) elastomer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical class [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68706976A | 1976-05-17 | 1976-05-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2721826A1 true DE2721826A1 (de) | 1977-12-08 |
| DE2721826C2 DE2721826C2 (xx) | 1987-10-22 |
Family
ID=24758918
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2759712A Expired - Lifetime DE2759712C2 (xx) | 1976-05-17 | 1977-05-13 | |
| DE2721826A Granted DE2721826A1 (de) | 1976-05-17 | 1977-05-13 | Verfahren zur polymerisation und ringgleichgewichtseinstellung von trifluoraethoxy-chlorcyclotriphosphazenen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2759712A Expired - Lifetime DE2759712C2 (xx) | 1976-05-17 | 1977-05-13 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS534100A (xx) |
| AU (1) | AU511328B2 (xx) |
| BE (1) | BE854757A (xx) |
| CA (1) | CA1084520A (xx) |
| DE (2) | DE2759712C2 (xx) |
| GB (1) | GB1543544A (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS584017Y2 (ja) * | 1977-11-04 | 1983-01-24 | シャープ株式会社 | 液体燃料燃焼装置 |
| 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 |
Citations (6)
| 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 |
| DE2334402A1 (de) * | 1972-07-17 | 1974-01-31 | Mo Och Domsjoe Ab | Verfahren zur herstellung von phosphornitrilatpolymerisaten |
| US3838073A (en) | 1972-08-28 | 1974-09-24 | Horizons Research Inc | Poly(fluoroalkoxyphosphazene)homopolymers |
| DE2427879A1 (de) * | 1973-06-12 | 1975-01-09 | Ethyl Corp | Verfahren zur herstellung von phosphornitrilatpolymerisaten und ihre verwendung als feuerhemmende mittel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4912570A (xx) * | 1972-05-15 | 1974-02-04 | ||
| US3836608A (en) * | 1972-08-17 | 1974-09-17 | Fmc Corp | Process for self condensing phosphonitrilic chloroesters and product |
-
1977
- 1977-05-13 DE DE2759712A patent/DE2759712C2/de not_active Expired - Lifetime
- 1977-05-13 DE DE2721826A patent/DE2721826A1/de active Granted
- 1977-05-16 JP JP5625077A patent/JPS534100A/ja active Granted
- 1977-05-16 AU AU25156/77A patent/AU511328B2/en not_active Expired
- 1977-05-16 CA CA278,480A patent/CA1084520A/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
Patent Citations (6)
| 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 |
| DE2334402A1 (de) * | 1972-07-17 | 1974-01-31 | Mo Och Domsjoe Ab | Verfahren zur herstellung von phosphornitrilatpolymerisaten |
| US3838073A (en) | 1972-08-28 | 1974-09-24 | Horizons Research Inc | Poly(fluoroalkoxyphosphazene)homopolymers |
| DE2427879A1 (de) * | 1973-06-12 | 1975-01-09 | Ethyl Corp | Verfahren zur herstellung von phosphornitrilatpolymerisaten und ihre verwendung als feuerhemmende mittel |
Non-Patent Citations (1)
| Title |
|---|
| Polymer Science USSR, Bd. 16, S. 1878-1882, 1974 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2759712C2 (xx) | 1990-01-11 |
| JPS5432840B2 (xx) | 1979-10-17 |
| GB1543544A (en) | 1979-04-04 |
| DE2721826C2 (xx) | 1987-10-22 |
| AU2515677A (en) | 1978-11-23 |
| AU511328B2 (en) | 1980-08-14 |
| JPS534100A (en) | 1978-01-14 |
| BE854757A (fr) | 1977-11-17 |
| CA1084520A (en) | 1980-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: KOHLER, M., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 80 |
|
| 8128 | New person/name/address of the agent |
Representative=s name: GLAESER, J., DIPL.-ING., 2000 HAMBURG KRESSIN, H., |
|
| AH | Division in |
Ref country code: DE Ref document number: 2759712 Format of ref document f/p: P |
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
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| 8339 | Ceased/non-payment of the annual fee |