DE2110767C3 - Perfluoralkyl-Phosphorverbindungen - Google Patents
Perfluoralkyl-PhosphorverbindungenInfo
- Publication number
- DE2110767C3 DE2110767C3 DE19712110767 DE2110767A DE2110767C3 DE 2110767 C3 DE2110767 C3 DE 2110767C3 DE 19712110767 DE19712110767 DE 19712110767 DE 2110767 A DE2110767 A DE 2110767A DE 2110767 C3 DE2110767 C3 DE 2110767C3
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- acid
- acids
- perfluoroalkyl
- water
- 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
- -1 Perfluoroalkyl phosphorus compounds Chemical class 0.000 title claims description 29
- 239000000203 mixture Substances 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 16
- 150000007513 acids Chemical class 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- 230000008018 melting Effects 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CPRNWMZKNOIIML-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctylphosphonic acid Chemical compound OP(O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CPRNWMZKNOIIML-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HZBFKCNFYXVCHE-UHFFFAOYSA-N FC(C(C(C(C(F)(F)P(I)I)(F)F)(F)F)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)F Chemical compound FC(C(C(C(C(F)(F)P(I)I)(F)F)(F)F)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)F HZBFKCNFYXVCHE-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- AGCUFKNHQDVTAD-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexylphosphonic acid Chemical compound OP(O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AGCUFKNHQDVTAD-UHFFFAOYSA-N 0.000 description 1
- BWGUYVSJNOGULH-UHFFFAOYSA-N FC(C(C(C(C(C(F)(F)P(I)I)(F)F)(F)F)(F)F)(F)F)(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)F Chemical compound FC(C(C(C(C(C(F)(F)P(I)I)(F)F)(F)F)(F)F)(F)F)(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)F BWGUYVSJNOGULH-UHFFFAOYSA-N 0.000 description 1
- BHXWWUIRGZYFAC-UHFFFAOYSA-N FC(C(C(C(F)(F)P(I)I)(F)F)(F)F)(C(C(F)(F)F)(F)F)F Chemical compound FC(C(C(C(F)(F)P(I)I)(F)F)(F)F)(C(C(F)(F)F)(F)F)F BHXWWUIRGZYFAC-UHFFFAOYSA-N 0.000 description 1
- BVISHIZBEHSFHW-UHFFFAOYSA-N FC(C(C(F)(F)P(I)I)(F)F)(C(F)(F)F)F Chemical compound FC(C(C(F)(F)P(I)I)(F)F)(C(F)(F)F)F BVISHIZBEHSFHW-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- GYGSKBLPPAHJEG-UHFFFAOYSA-N OP(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)F Chemical compound OP(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)F GYGSKBLPPAHJEG-UHFFFAOYSA-N 0.000 description 1
- OVUCOOMPFXIWIS-UHFFFAOYSA-N OP(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O Chemical compound OP(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O OVUCOOMPFXIWIS-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UWETVEYENGVTQS-UHFFFAOYSA-N difluorophosphinous acid Chemical class OP(F)F UWETVEYENGVTQS-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- XHTJLMYQJHCUPE-UHFFFAOYSA-N phosphanylphosphonic acid Chemical class OP(O)(P)=O XHTJLMYQJHCUPE-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- RYIOLWQRQXDECZ-UHFFFAOYSA-N phosphinous acid Chemical class PO RYIOLWQRQXDECZ-UHFFFAOYSA-N 0.000 description 1
- PZHNNJXWQYFUTD-UHFFFAOYSA-N phosphorus triiodide Chemical class IP(I)I PZHNNJXWQYFUTD-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/004—Surface-active compounds containing F
- C11D1/006—Surface-active compounds containing fluorine and phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4816—Acyclic saturated acids or derivatices which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712110767 DE2110767C3 (de) | 1971-03-06 | 1971-03-06 | Perfluoralkyl-Phosphorverbindungen |
| NL7202696A NL172546C (nl) | 1971-03-06 | 1972-03-01 | Werkwijze voor het bereiden van oppervlakte actieve perfluoralkylfosforverbindingen. |
| CH306872A CH565808A5 (enExample) | 1971-03-06 | 1972-03-02 | |
| JP2162572A JPS5616198B1 (enExample) | 1971-03-06 | 1972-03-03 | |
| CA136,164A CA977345A (en) | 1971-03-06 | 1972-03-03 | Perfluoroalkyl-phosphorus compounds |
| GB999072A GB1388924A (en) | 1971-03-06 | 1972-03-03 | Perfluoroalkyl-phosphorus compounds and process for their manufacture |
| IT2145472A IT953469B (it) | 1971-03-06 | 1972-03-04 | Composti perfluorcalchilfosforici |
| FR7207677A FR2128653B1 (enExample) | 1971-03-06 | 1972-03-06 | |
| SU721758808A SU593670A3 (ru) | 1971-03-06 | 1972-03-06 | Способ получени кислот фосфора или их солей |
| BE780266A BE780266A (fr) | 1971-03-06 | 1972-03-06 | Compose de perfluoro-alkyl-phosphores |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712110767 DE2110767C3 (de) | 1971-03-06 | 1971-03-06 | Perfluoralkyl-Phosphorverbindungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2110767A1 DE2110767A1 (de) | 1972-09-28 |
| DE2110767B2 DE2110767B2 (de) | 1973-07-12 |
| DE2110767C3 true DE2110767C3 (de) | 1974-02-14 |
Family
ID=5800731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712110767 Expired DE2110767C3 (de) | 1971-03-06 | 1971-03-06 | Perfluoralkyl-Phosphorverbindungen |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5616198B1 (enExample) |
| BE (1) | BE780266A (enExample) |
| CA (1) | CA977345A (enExample) |
| CH (1) | CH565808A5 (enExample) |
| DE (1) | DE2110767C3 (enExample) |
| FR (1) | FR2128653B1 (enExample) |
| GB (1) | GB1388924A (enExample) |
| IT (1) | IT953469B (enExample) |
| NL (1) | NL172546C (enExample) |
| SU (1) | SU593670A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2656384A1 (de) | 1976-12-13 | 1978-06-22 | Kreussler Chem Fab | Verfahren zur reinigung fester stoffe in organischen loesungsmittelbaedern |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE117168T1 (de) * | 1989-07-08 | 1995-02-15 | Hoechst Schering Agrevo Gmbh | Entschäumer für flüssige netzmittel und schaumarme flüssige pflanzenschutzmittel. |
| JPH03188707A (ja) * | 1989-12-19 | 1991-08-16 | Pioneer Electron Corp | 音響再生装置 |
| JPH0553583A (ja) * | 1991-08-23 | 1993-03-05 | Kawai Musical Instr Mfg Co Ltd | 音量制御ペダルを備えた電子楽器 |
| EP0878128A1 (en) * | 1997-05-07 | 1998-11-18 | American Cyanamid Company | Solid formulations |
| US6030924A (en) * | 1997-05-07 | 2000-02-29 | American Cyanamid Company | Solid formulations |
| DE102006025847A1 (de) | 2006-06-02 | 2007-12-06 | Merck Patent Gmbh | Verwendung von Phosphinsäure in der Galvanotechnik |
| CN102105477B (zh) * | 2008-07-25 | 2014-10-01 | 默克专利股份公司 | 双(全氟烷基)三价膦酸及其衍生物和用途 |
| WO2013037707A1 (en) | 2011-09-14 | 2013-03-21 | Solvay Specialty Polymers Italy S.P.A. | Polymerization process |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3047619A (en) * | 1960-03-14 | 1962-07-31 | Du Pont | Beta-hydroperfluoroalkyl compounds of phosphorus |
| NL6509545A (enExample) * | 1964-07-31 | 1966-02-01 | Bloechl W |
-
1971
- 1971-03-06 DE DE19712110767 patent/DE2110767C3/de not_active Expired
-
1972
- 1972-03-01 NL NL7202696A patent/NL172546C/xx not_active IP Right Cessation
- 1972-03-02 CH CH306872A patent/CH565808A5/xx not_active IP Right Cessation
- 1972-03-03 JP JP2162572A patent/JPS5616198B1/ja active Pending
- 1972-03-03 CA CA136,164A patent/CA977345A/en not_active Expired
- 1972-03-03 GB GB999072A patent/GB1388924A/en not_active Expired
- 1972-03-04 IT IT2145472A patent/IT953469B/it active
- 1972-03-06 FR FR7207677A patent/FR2128653B1/fr not_active Expired
- 1972-03-06 SU SU721758808A patent/SU593670A3/ru active
- 1972-03-06 BE BE780266A patent/BE780266A/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2656384A1 (de) | 1976-12-13 | 1978-06-22 | Kreussler Chem Fab | Verfahren zur reinigung fester stoffe in organischen loesungsmittelbaedern |
Also Published As
| Publication number | Publication date |
|---|---|
| CA977345A (en) | 1975-11-04 |
| JPS5616198B1 (enExample) | 1981-04-15 |
| GB1388924A (en) | 1975-03-26 |
| DE2110767B2 (de) | 1973-07-12 |
| DE2110767A1 (de) | 1972-09-28 |
| SU593670A3 (ru) | 1978-02-15 |
| NL172546C (nl) | 1983-09-16 |
| NL7202696A (enExample) | 1972-09-08 |
| FR2128653A1 (enExample) | 1972-10-20 |
| IT953469B (it) | 1973-08-10 |
| CH565808A5 (enExample) | 1975-08-29 |
| BE780266A (fr) | 1972-09-06 |
| FR2128653B1 (enExample) | 1977-12-23 |
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