CA2764427A1 - Polyfluorosulfonamido amides useful as intermediates in the synthesis of polyfluorosulfonamido amines - Google Patents
Polyfluorosulfonamido amides useful as intermediates in the synthesis of polyfluorosulfonamido amines Download PDFInfo
- Publication number
- CA2764427A1 CA2764427A1 CA2764427A CA2764427A CA2764427A1 CA 2764427 A1 CA2764427 A1 CA 2764427A1 CA 2764427 A CA2764427 A CA 2764427A CA 2764427 A CA2764427 A CA 2764427A CA 2764427 A1 CA2764427 A1 CA 2764427A1
- Authority
- CA
- Canada
- Prior art keywords
- polyfluorosulfonamido
- product
- chosen
- amide
- polyfluorosulfonamide
- 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.)
- Abandoned
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 30
- 150000001408 amides Chemical class 0.000 title claims description 22
- 230000015572 biosynthetic process Effects 0.000 title description 11
- 239000000543 intermediate Substances 0.000 title description 11
- 238000003786 synthesis reaction Methods 0.000 title description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 32
- 150000004985 diamines Chemical class 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 150000002148 esters Chemical class 0.000 claims description 17
- 238000005947 deacylation reaction Methods 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 230000020176 deacylation Effects 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000013067 intermediate product Substances 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract description 23
- 239000000047 product Substances 0.000 abstract description 15
- 229940124530 sulfonamide Drugs 0.000 abstract description 12
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 239000000376 reactant Substances 0.000 abstract description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 abstract description 5
- 239000011737 fluorine Substances 0.000 abstract description 5
- 239000007858 starting material Substances 0.000 abstract description 3
- 239000012535 impurity Substances 0.000 abstract description 2
- 238000010348 incorporation Methods 0.000 abstract description 2
- 238000002955 isolation Methods 0.000 abstract description 2
- 230000000704 physical effect Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000203 mixture Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000010926 purge Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- TYKPMMIFXVBTDJ-UHFFFAOYSA-N acetamide;propane-1,3-diamine Chemical compound CC(N)=O.NCCCN TYKPMMIFXVBTDJ-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- -1 (CF3)2CH Chemical compound 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 229940113088 dimethylacetamide Drugs 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZUDDFQJTUVAEGR-UHFFFAOYSA-N acetamide;propane-1,3-diamine Chemical compound CC(N)=O.CC(N)=O.NCCCN ZUDDFQJTUVAEGR-UHFFFAOYSA-N 0.000 description 3
- DLNFICFQUIYVBX-UHFFFAOYSA-N n-(3-aminopropyl)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-sulfonamide Chemical compound NCCCNS(=O)(=O)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DLNFICFQUIYVBX-UHFFFAOYSA-N 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- MTTJUCUTTQQNCG-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-2-sulfonyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)S(Cl)(=O)=O MTTJUCUTTQQNCG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- UDEWPOVQBGFNGE-UHFFFAOYSA-N propyl benzoate Chemical compound CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 1
- 125000005739 1,1,2,2-tetrafluoroethanediyl group Chemical group FC(F)([*:1])C(F)(F)[*:2] 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- KFNNIILCVOLYIR-UHFFFAOYSA-N Propyl formate Chemical compound CCCOC=O KFNNIILCVOLYIR-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BCQSKNWLNHYIFN-UHFFFAOYSA-N acetamide propane-1,3-diamine Chemical compound C(C)(=O)N.NCCCN.C(C)(=O)N.NCCCN BCQSKNWLNHYIFN-UHFFFAOYSA-N 0.000 description 1
- SOHFOIUQOCUZOO-UHFFFAOYSA-N acetamide;propane-1,3-diamine;hydrochloride Chemical compound Cl.CC(N)=O.NCCCN SOHFOIUQOCUZOO-UHFFFAOYSA-N 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- CFNHVUGPXZUTRR-UHFFFAOYSA-N n'-propylethane-1,2-diamine Chemical compound CCCNCCN CFNHVUGPXZUTRR-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- HTUIWRWYYVBCFT-UHFFFAOYSA-N propyl hexanoate Chemical compound CCCCCC(=O)OCCC HTUIWRWYYVBCFT-UHFFFAOYSA-N 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/500,817 | 2009-07-10 | ||
| US12/500,817 US8258341B2 (en) | 2009-07-10 | 2009-07-10 | Polyfluorosulfonamido amine and intermediate |
| PCT/US2010/040728 WO2011005642A1 (en) | 2009-07-10 | 2010-07-01 | Polyfluorosulfonamido amides useful as intermediates in the synthesis of polyfluorosulfonamido amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2764427A1 true CA2764427A1 (en) | 2011-01-13 |
Family
ID=42793397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2764427A Abandoned CA2764427A1 (en) | 2009-07-10 | 2010-07-01 | Polyfluorosulfonamido amides useful as intermediates in the synthesis of polyfluorosulfonamido amines |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8258341B2 (enExample) |
| EP (1) | EP2451777A1 (enExample) |
| JP (1) | JP2012532870A (enExample) |
| KR (1) | KR20120034227A (enExample) |
| CN (1) | CN102482206A (enExample) |
| CA (1) | CA2764427A1 (enExample) |
| WO (1) | WO2011005642A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130067093A1 (en) * | 2010-03-16 | 2013-03-14 | Optimi Corporation | Determining Essential Resources in a Wireless Network |
| US9168408B2 (en) * | 2010-03-25 | 2015-10-27 | The Chemours Company Fc, Llc | Surfactant composition from polyfluoroalkylsulfonamido alkyl amines |
| US8729138B2 (en) * | 2010-03-25 | 2014-05-20 | E I Du Pont De Nemours And Company | Mixture of polyfluoroalkylsulfonamido alkyl amines |
| JP5522501B2 (ja) * | 2012-05-18 | 2014-06-18 | Ｄｉｃ株式会社 | フッ素化脂肪族基を含むスルホニルアミド化合物の製造方法及びアニオン性親水基含有界面活性剤の製造方法 |
| JP5920024B2 (ja) * | 2012-05-25 | 2016-05-18 | Dic株式会社 | フッ素化脂肪族基を含むスルホニルアミド化合物の製造方法及びアニオン性親水基含有界面活性剤の製造方法 |
| CN105519067B (zh) * | 2013-09-18 | 2020-04-03 | 华为技术有限公司 | 传输信令的方法、装置和计算机可读介质 |
| EP4175310A1 (en) | 2021-10-28 | 2023-05-03 | Koninklijke Philips N.V. | Checking locality of devices |
| WO2023036523A1 (en) | 2021-09-09 | 2023-03-16 | Koninklijke Philips N.V. | Checking locality of devices |
Family Cites Families (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1259333B (de) * | 1964-03-09 | 1968-01-25 | Minnesota Mining & Mfg | Verfahren zur Herstellung von N-Alkyl-perfluoralkansulfon-amidoalkyl-arylsulfonsaeureestern |
| FR2029262A5 (enExample) | 1969-01-22 | 1970-10-16 | Ugine Kuhlmann | |
| FR2034142B1 (enExample) | 1969-02-11 | 1975-07-04 | Ugine Kuhlmann | |
| NL7103340A (enExample) | 1970-03-19 | 1971-09-21 | ||
| FR2088594A5 (enExample) | 1970-04-17 | 1972-01-07 | Ugine Kuhlmann | |
| US3708538A (en) | 1970-07-29 | 1973-01-02 | Hoechst Ag | N-fluoroalkyl-sulfonamides and process for preparing them |
| US4043923A (en) | 1974-02-26 | 1977-08-23 | Minnesota Mining And Manufacturing Company | Textile treatment composition |
| FR2308674A1 (fr) | 1975-04-25 | 1976-11-19 | Ugine Kuhlmann | Nouvelles compositions extinctrices |
| US4163754A (en) | 1977-02-28 | 1979-08-07 | Ici Americas Inc. | Fluorinated sulfonamides |
| AU3692278A (en) | 1977-07-05 | 1979-12-13 | Ici Ltd | Fluorochemical surfactants |
| DE2744044A1 (de) | 1977-09-30 | 1979-04-12 | Akzo Gmbh | Verfahren zur herstellung von fluorsulfonamiden |
| EP0004919B1 (de) | 1978-04-14 | 1981-06-10 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von N,N,N',N'-Tetraacetyl-ethylendiamin |
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| US8858813B2 (en) | 2008-12-11 | 2014-10-14 | 3M Innovative Properties Company | Patterning process |
-
2009
- 2009-07-10 US US12/500,817 patent/US8258341B2/en not_active Expired - Fee Related
-
2010
- 2010-07-01 CA CA2764427A patent/CA2764427A1/en not_active Abandoned
- 2010-07-01 KR KR1020127003468A patent/KR20120034227A/ko not_active Withdrawn
- 2010-07-01 JP JP2012519594A patent/JP2012532870A/ja not_active Withdrawn
- 2010-07-01 WO PCT/US2010/040728 patent/WO2011005642A1/en not_active Ceased
- 2010-07-01 EP EP10730955A patent/EP2451777A1/en not_active Withdrawn
- 2010-07-01 CN CN201080030765XA patent/CN102482206A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US8258341B2 (en) | 2012-09-04 |
| CN102482206A (zh) | 2012-05-30 |
| WO2011005642A1 (en) | 2011-01-13 |
| KR20120034227A (ko) | 2012-04-10 |
| EP2451777A1 (en) | 2012-05-16 |
| US20110009668A1 (en) | 2011-01-13 |
| JP2012532870A (ja) | 2012-12-20 |
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