DE2307204A1 - Verfahren zur herstellung von polyfluoralkoholen und deren verwendung - Google Patents
Verfahren zur herstellung von polyfluoralkoholen und deren verwendungInfo
- Publication number
- DE2307204A1 DE2307204A1 DE19732307204 DE2307204A DE2307204A1 DE 2307204 A1 DE2307204 A1 DE 2307204A1 DE 19732307204 DE19732307204 DE 19732307204 DE 2307204 A DE2307204 A DE 2307204A DE 2307204 A1 DE2307204 A1 DE 2307204A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- pocl
- water
- compounds
- phosphorus
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001298 alcohols Chemical class 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- 239000011574 phosphorus Substances 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000000123 paper Substances 0.000 claims description 5
- -1 perfluoro compounds Chemical class 0.000 claims description 5
- 239000004753 textile Substances 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000002657 fibrous material Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 230000002940 repellent Effects 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 18
- 239000007795 chemical reaction product Substances 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000008022 sublimation Effects 0.000 description 9
- 238000000859 sublimation Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical group 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- UWTUEMKLYAGTNQ-UHFFFAOYSA-N 1,2-dibromoethene Chemical group BrC=CBr UWTUEMKLYAGTNQ-UHFFFAOYSA-N 0.000 description 1
- RLFFWWKJSJOYMQ-UHFFFAOYSA-N 1,3-diazepan-2-one Chemical compound O=C1NCCCCN1 RLFFWWKJSJOYMQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N gamma-butyrolactone Natural products O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/40—Halogenated alcohols perhalogenated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Paper (AREA)
- Surface Treatment Of Glass (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH255272A CH565724A5 (enExample) | 1972-02-22 | 1972-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2307204A1 true DE2307204A1 (de) | 1973-08-30 |
Family
ID=4236360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732307204 Pending DE2307204A1 (de) | 1972-02-22 | 1973-02-14 | Verfahren zur herstellung von polyfluoralkoholen und deren verwendung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3927126A (enExample) |
| JP (1) | JPS4896505A (enExample) |
| BE (1) | BE795705A (enExample) |
| CH (1) | CH565724A5 (enExample) |
| DE (1) | DE2307204A1 (enExample) |
| FR (1) | FR2173033B1 (enExample) |
| GB (1) | GB1395454A (enExample) |
| SU (1) | SU460615A3 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4264484A (en) | 1979-01-24 | 1981-04-28 | Minnesota Mining And Manufacturing Company | Carpet treatment |
| DE3051167C3 (de) * | 1979-01-24 | 1994-11-24 | Minnesota Mining & Mfg | Fluorierte Alkohole |
| US4382891A (en) * | 1980-05-09 | 1983-05-10 | E. I. Du Pont De Nemours And Company | Use of fluoroalkoxysulfur fluorides in fluorinations |
| US4517376A (en) * | 1981-06-26 | 1985-05-14 | E. I. Du Pont De Nemours And Company | Manufacture of chloromethyl-substituted polyfluoroalkyl esters |
| US5242487A (en) * | 1988-11-11 | 1993-09-07 | Daikin Industries Ltd. | Water- and oil-repellant composition |
| US7674928B2 (en) * | 2006-11-13 | 2010-03-09 | E.I. Du Pont De Nemours And Company | Polyfluoroether-based phosphates |
| US7470818B2 (en) * | 2006-11-13 | 2008-12-30 | E.I. Du Pont De Nemours & Company | Fluoroalkyl phosphate compositions |
| CN110184847A (zh) * | 2019-05-17 | 2019-08-30 | 华南理工大学 | 一种撕不烂仿皮纸及其制造方法与应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2725394A (en) * | 1950-08-03 | 1955-11-29 | Ici Ltd | Production of esters of orthophosphoric acid and salts thereof |
| US2866807A (en) * | 1954-04-15 | 1958-12-30 | Virginia Carolina Chem Corp | Aliphatic aryl phosphites |
| US2929833A (en) * | 1958-04-23 | 1960-03-22 | Ethyl Corp | Process of preparing phenyl dimethyl phosphates |
| US2960527A (en) * | 1958-08-20 | 1960-11-15 | Akad Wissenschaften Ddr | Process for the preparation of dichloro phosphoric esters |
| US3059016A (en) * | 1959-08-05 | 1962-10-16 | Celanese Corp | Manufacture of aryl phosphate esters |
| NL282705A (enExample) * | 1961-09-01 |
-
0
- BE BE795705D patent/BE795705A/xx unknown
-
1972
- 1972-02-22 CH CH255272A patent/CH565724A5/xx not_active IP Right Cessation
-
1973
- 1973-02-14 DE DE19732307204 patent/DE2307204A1/de active Pending
- 1973-02-15 GB GB748373A patent/GB1395454A/en not_active Expired
- 1973-02-16 US US333246A patent/US3927126A/en not_active Expired - Lifetime
- 1973-02-19 FR FR7305744A patent/FR2173033B1/fr not_active Expired
- 1973-02-21 SU SU1885657A patent/SU460615A3/ru active
- 1973-02-22 JP JP48020753A patent/JPS4896505A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3927126A (en) | 1975-12-16 |
| FR2173033B1 (enExample) | 1976-05-14 |
| CH565724A5 (enExample) | 1975-08-29 |
| FR2173033A1 (enExample) | 1973-10-05 |
| BE795705A (fr) | 1973-08-21 |
| JPS4896505A (enExample) | 1973-12-10 |
| SU460615A3 (ru) | 1975-02-15 |
| GB1395454A (en) | 1975-05-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69901179T3 (de) | Procede et solvant de nettoyage a sec | |
| EP0073364B1 (de) | Verfahren zur Herstellung von Perfluoralkylreste enthaltenden Kondensationsprodukten, die so hergestellten Kondensationsprodukte und deren Verwendung | |
| DE69030564T2 (de) | Stickstoff enthaltende organische Polyfluorverbindungen | |
| DE1018836B (de) | Waessrige Silikonemulsion zum Wasserabstossendmachen von organischen Fasermaterialien | |
| EP0074057A2 (de) | Perfluoralkylester, Verfahren zu deren Herstellung und ihre Verwendung als schmutzabweisendes Mittel | |
| DE2307204A1 (de) | Verfahren zur herstellung von polyfluoralkoholen und deren verwendung | |
| EP0213580A2 (de) | Perfluoralkyl- und Epichlorhydrin-Gruppen enthaltende Urethane, diese Urethane enthaltende wässrige Dispersionen und ihre Verwendung | |
| EP0222334B1 (de) | Perfluoralkylgruppen, von Epichlorhydrin abgeleiteten Gruppen und Dialkoholreste enthaltende Urethane, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2926790C2 (enExample) | ||
| DE1468850C3 (de) | Verfahren zur Herstellung von Fluor enthaltenden Polymerisaten | |
| DE1205097B (de) | Verfahren zur Herstellung neuer Phosphorverbindungen | |
| DE2207183A1 (de) | Phosphorhaltige Perfluorverbindungen, Verfahren zur Herstellung und deren Verwendung | |
| DE2326364A1 (de) | Loesungsmittel-bleichverfahren | |
| DE2652962C3 (de) | Verfahren zur Herstellung von Phospholen-1 -chalcogeniden | |
| DE69301781T2 (de) | Tris-(acetoacetoxy-2-ethyl)-Amin und ihren wasserlöslichen Salzen, Verfahren zu ihrer Herstellung, Verwendung als Formaldehyd-Fänger und Verfahren zur Veredlung von Textilien | |
| EP0170611B1 (de) | Verfahren zum Schützen von Keratinmaterial vor dem Befall durch keratinfressende Insekten | |
| DE3119071A1 (de) | Verfahren zur herstellung von fluorkohlenstoffverbindungen | |
| DE2409109A1 (de) | Neue perfluoralkylalkylcarbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung | |
| DE1925047A1 (de) | Verfahren zum Chemischreinigen von Fasergut | |
| DE2429400A1 (de) | Perfluoralkylaethandiole, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2064901A1 (de) | Homo oder Copolymerisate des 1,4 Bis (heptafluorisopropoxy) 2,3 epoxybutans Ausscheidung aus 2059013 | |
| DE2238398C3 (de) | Verfahren zum kontinuierlichen Färben von synthetischen Fasermaterialien aus organischen Lösemitteln | |
| DE4135499A1 (de) | Vliesausruestung | |
| CH369441A (de) | Verfahren zur Herstellung neuer Aminobenzoesäure-Derivate | |
| AT283555B (de) | Reinigungsmittelmischungen |