DE2120868C2 - Fluorierte sulfoxylierte Ampholyte und Verfahren zu ihrer Herstellung - Google Patents
Fluorierte sulfoxylierte Ampholyte und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2120868C2 DE2120868C2 DE19712120868 DE2120868A DE2120868C2 DE 2120868 C2 DE2120868 C2 DE 2120868C2 DE 19712120868 DE19712120868 DE 19712120868 DE 2120868 A DE2120868 A DE 2120868A DE 2120868 C2 DE2120868 C2 DE 2120868C2
- Authority
- DE
- Germany
- Prior art keywords
- fluorinated
- ampholytes
- sulfoxylated
- preparation
- ppm
- 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
- 239000000872 buffer Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 230000008569 process Effects 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 12
- -1 alkyl radical Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960000380 propiolactone Drugs 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000006957 Michael reaction Methods 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- GVGCUCJTUSOZKP-UHFFFAOYSA-N nitrogen trifluoride Chemical class FN(F)F GVGCUCJTUSOZKP-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7015836A FR2088941A5 (enrdf_load_stackoverflow) | 1970-04-30 | 1970-04-30 | |
| FR7106914A FR2128028B2 (enrdf_load_stackoverflow) | 1970-04-30 | 1971-03-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2120868A1 DE2120868A1 (de) | 1971-11-18 |
| DE2120868C2 true DE2120868C2 (de) | 1984-05-17 |
Family
ID=26215715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712120868 Expired DE2120868C2 (de) | 1970-04-30 | 1971-04-28 | Fluorierte sulfoxylierte Ampholyte und Verfahren zu ihrer Herstellung |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5029450B1 (enrdf_load_stackoverflow) |
| BE (1) | BE765256A (enrdf_load_stackoverflow) |
| CA (1) | CA939381A (enrdf_load_stackoverflow) |
| CH (1) | CH541546A (enrdf_load_stackoverflow) |
| DE (1) | DE2120868C2 (enrdf_load_stackoverflow) |
| FR (2) | FR2088941A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1343990A (enrdf_load_stackoverflow) |
| NL (1) | NL171890C (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2523402A1 (de) * | 1974-05-30 | 1975-12-11 | Montedison Spa | Polyoxapolyfluoralkansulfonate und verfahren zu deren herstellung |
| US7943567B2 (en) | 2004-01-30 | 2011-05-17 | E.I. Du Pont De Nemours And Company | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| US8318656B2 (en) | 2007-07-03 | 2012-11-27 | E. I. Du Pont De Nemours And Company | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2453145B1 (enrdf_load_stackoverflow) | 1979-04-06 | 1981-03-27 | Ugine Kuhlmann | |
| FR2609751B1 (fr) * | 1987-01-20 | 1996-02-02 | Inst Francais Du Petrole | Utilisation de mousses a base de tensioactifs a groupement perfluore pour ameliorer le balayage au gaz d'une formation petroliere |
| FR2647112A1 (fr) * | 1989-05-22 | 1990-11-23 | Atochem | Composes polyfluoralkyle azotes, leurs procedes de preparation et leurs applications |
| US5144069A (en) * | 1990-12-13 | 1992-09-01 | Minnesota Mining And Manufacturing Company | Process for the preparation of fluoroaliphatic aminocarboxylate surfactants |
| FR2893629B1 (fr) | 2005-11-23 | 2009-10-16 | Stephane Szonyi | Nouveaux polyamides perfluoroalkyles lipophobes et leur obtention et leur utilisation |
| CN102491923A (zh) * | 2011-11-15 | 2012-06-13 | 上海威腾化工科技发展有限公司 | 一种以水为溶剂连续法化学合成全氟表面活性剂方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2759019A (en) * | 1954-08-09 | 1956-08-14 | Minnesota Mining & Mfg | Perfluoro amine compounds and quaternary derivatives |
| FR1600425A (enrdf_load_stackoverflow) * | 1968-08-21 | 1970-07-27 | ||
| DE1935991A1 (de) * | 1968-08-28 | 1970-03-05 | Nat Starch Chem Corp | Segmentierte Fluorcarbonsulfonsaeuren,deren Derivate und Gemische daraus |
-
1970
- 1970-04-30 FR FR7015836A patent/FR2088941A5/fr not_active Expired
-
1971
- 1971-03-01 FR FR7106914A patent/FR2128028B2/fr not_active Expired
- 1971-04-05 BE BE765256A patent/BE765256A/xx not_active IP Right Cessation
- 1971-04-19 GB GB2634371A patent/GB1343990A/en not_active Expired
- 1971-04-23 CH CH599971A patent/CH541546A/fr not_active IP Right Cessation
- 1971-04-28 DE DE19712120868 patent/DE2120868C2/de not_active Expired
- 1971-04-29 CA CA111793A patent/CA939381A/en not_active Expired
- 1971-04-29 NL NL7105884A patent/NL171890C/xx not_active IP Right Cessation
- 1971-04-30 JP JP46028154A patent/JPS5029450B1/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2523402A1 (de) * | 1974-05-30 | 1975-12-11 | Montedison Spa | Polyoxapolyfluoralkansulfonate und verfahren zu deren herstellung |
| US7943567B2 (en) | 2004-01-30 | 2011-05-17 | E.I. Du Pont De Nemours And Company | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| US8318656B2 (en) | 2007-07-03 | 2012-11-27 | E. I. Du Pont De Nemours And Company | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
Also Published As
| Publication number | Publication date |
|---|---|
| CA939381A (en) | 1974-01-01 |
| BE765256A (fr) | 1971-08-30 |
| CH541546A (fr) | 1973-09-15 |
| FR2128028A2 (enrdf_load_stackoverflow) | 1972-10-20 |
| DE2120868A1 (de) | 1971-11-18 |
| NL7105884A (enrdf_load_stackoverflow) | 1971-11-02 |
| NL171890B (nl) | 1983-01-03 |
| JPS5029450B1 (enrdf_load_stackoverflow) | 1975-09-23 |
| NL171890C (nl) | 1983-06-01 |
| GB1343990A (en) | 1974-01-16 |
| FR2088941A5 (enrdf_load_stackoverflow) | 1972-01-07 |
| FR2128028B2 (enrdf_load_stackoverflow) | 1973-05-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |