DE2910794C2 - - Google Patents
Info
- Publication number
- DE2910794C2 DE2910794C2 DE2910794A DE2910794A DE2910794C2 DE 2910794 C2 DE2910794 C2 DE 2910794C2 DE 2910794 A DE2910794 A DE 2910794A DE 2910794 A DE2910794 A DE 2910794A DE 2910794 C2 DE2910794 C2 DE 2910794C2
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- carried out
- catalyst
- groups
- amine
- 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
- 239000003054 catalyst Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 9
- -1 β- trichloromethyl- β - propiosultone Chemical compound 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims 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 description 6
- 238000012719 thermal polymerization Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000001923 cyclic compounds Chemical class 0.000 claims description 5
- 239000000155 melt Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 229920005601 base polymer Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
- 229940031826 phenolate Drugs 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229920002627 poly(phosphazenes) Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyethers (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792910794 DE2910794A1 (de) | 1979-03-19 | 1979-03-19 | Verfahren zur thermischen polymerisation von phosphazen-polymeren |
| CH158980A CH644878A5 (de) | 1979-03-19 | 1980-02-28 | Verfahren zur herstellung von phosphazen-polymeren durch thermische polymerisation. |
| IT48093/80A IT1145360B (it) | 1979-03-19 | 1980-03-06 | Procedimento per la polimerizzazione termica di polimeri fosfazenioi |
| CA000347406A CA1150479A (en) | 1979-03-19 | 1980-03-11 | Process for thermal polymerization of phosphorus polymers |
| GB8008962A GB2044742B (en) | 1979-03-19 | 1980-03-17 | Thermal polymerisation of phosphazene polymers |
| FR8006063A FR2451925B1 (fr) | 1979-03-19 | 1980-03-18 | Procede pour la preparation de polymeres phosphazenes par polymerisation thermique |
| SE8002086A SE449366B (sv) | 1979-03-19 | 1980-03-18 | Forfarande for framstellning av fosfazenpolymerer |
| JP3569680A JPS55136107A (en) | 1979-03-19 | 1980-03-19 | Preparation of phosphagen polymer |
| US06/433,803 US4431619A (en) | 1979-03-19 | 1982-10-08 | Process for the thermal polymerization of phosphazene polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792910794 DE2910794A1 (de) | 1979-03-19 | 1979-03-19 | Verfahren zur thermischen polymerisation von phosphazen-polymeren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2910794A1 DE2910794A1 (de) | 1980-10-02 |
| DE2910794C2 true DE2910794C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-11-30 |
Family
ID=6065836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792910794 Granted DE2910794A1 (de) | 1979-03-19 | 1979-03-19 | Verfahren zur thermischen polymerisation von phosphazen-polymeren |
Country Status (9)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5845230A (ja) * | 1981-09-11 | 1983-03-16 | Teikoku Chem Ind Corp Ltd | ホスフアゼン重合物の製造方法 |
| JPS58164619A (ja) * | 1982-03-25 | 1983-09-29 | Teikoku Chem Ind Corp Ltd | ポリジクロロホスフアゼン直鎖ポリマ−の製造方法 |
| JPS60224230A (ja) * | 1984-04-20 | 1985-11-08 | Nec Corp | 半導体表面保護膜及びその製造方法 |
| JPH0647448B2 (ja) * | 1986-08-08 | 1994-06-22 | 丸善石油化学株式会社 | ホスフアゼン重合体の製造法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE790016A (fr) * | 1971-10-13 | 1973-04-12 | Horizons Research Inc | Preparation de polyphosphazenes |
| US4005171A (en) * | 1974-05-28 | 1977-01-25 | Horizons Incorporated, A Division Of Horizons Research Incorporated | Catalytic preparation of soluble poly(dichlorophosphazenes) |
| US4110421A (en) * | 1976-10-12 | 1978-08-29 | Armstrong Cork Company | Catalytic process for the preparation of phosphazene polymers |
| US4116891A (en) * | 1976-12-06 | 1978-09-26 | Armstrong Cork Company | Catalytic process for the preparation of phosphazene polymers |
| BE866783A (fr) * | 1978-05-08 | 1978-11-08 | Firestone Tire & Rubber Co | Polymerisation en solution de chlorophosphazene avec du soufre comme agent de modification |
-
1979
- 1979-03-19 DE DE19792910794 patent/DE2910794A1/de active Granted
-
1980
- 1980-02-28 CH CH158980A patent/CH644878A5/de not_active IP Right Cessation
- 1980-03-06 IT IT48093/80A patent/IT1145360B/it active
- 1980-03-11 CA CA000347406A patent/CA1150479A/en not_active Expired
- 1980-03-17 GB GB8008962A patent/GB2044742B/en not_active Expired
- 1980-03-18 SE SE8002086A patent/SE449366B/sv not_active IP Right Cessation
- 1980-03-18 FR FR8006063A patent/FR2451925B1/fr not_active Expired
- 1980-03-19 JP JP3569680A patent/JPS55136107A/ja active Granted
-
1982
- 1982-10-08 US US06/433,803 patent/US4431619A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2044742B (en) | 1982-11-17 |
| FR2451925A1 (fr) | 1980-10-17 |
| JPS6351963B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-10-17 |
| SE449366B (sv) | 1987-04-27 |
| SE8002086L (sv) | 1980-09-20 |
| CA1150479A (en) | 1983-07-26 |
| US4431619A (en) | 1984-02-14 |
| DE2910794A1 (de) | 1980-10-02 |
| GB2044742A (en) | 1980-10-22 |
| IT1145360B (it) | 1986-11-05 |
| FR2451925B1 (fr) | 1985-06-21 |
| IT8048093A0 (it) | 1980-03-06 |
| CH644878A5 (de) | 1984-08-31 |
| JPS55136107A (en) | 1980-10-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAM | Search report available | ||
| OC | Search report available | ||
| 8110 | Request for examination paragraph 44 | ||
| 8127 | New person/name/address of the applicant |
Owner name: AKZO PATENTE GMBH, 5600 WUPPERTAL, DE |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |