DE2409109A1 - Neue perfluoralkylalkylcarbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung - Google Patents
Neue perfluoralkylalkylcarbonsaeuren, verfahren zu ihrer herstellung und ihre verwendungInfo
- Publication number
- DE2409109A1 DE2409109A1 DE2409109A DE2409109A DE2409109A1 DE 2409109 A1 DE2409109 A1 DE 2409109A1 DE 2409109 A DE2409109 A DE 2409109A DE 2409109 A DE2409109 A DE 2409109A DE 2409109 A1 DE2409109 A1 DE 2409109A1
- Authority
- DE
- Germany
- Prior art keywords
- perfluoroalkylalkylcarboxylic
- acids
- integer
- cooh
- formula
- 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
- 239000002253 acid Substances 0.000 title claims description 23
- 150000007513 acids Chemical class 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000000123 paper Substances 0.000 claims description 3
- 239000005871 repellent Substances 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 8
- 230000002940 repellent Effects 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 239000000543 intermediate Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000004744 fabric Substances 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 3
- -1 perfluoroalkyl iodides Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-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
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
- C07C53/21—Acids containing three or more carbon atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH318473 | 1973-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2409109A1 true DE2409109A1 (de) | 1974-09-12 |
Family
ID=4250444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2409109A Pending DE2409109A1 (de) | 1973-03-05 | 1974-02-26 | Neue perfluoralkylalkylcarbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4002657A (enExample) |
| JP (1) | JPS49117421A (enExample) |
| BE (1) | BE811821A (enExample) |
| DE (1) | DE2409109A1 (enExample) |
| FR (1) | FR2220505B1 (enExample) |
| GB (1) | GB1429280A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4124469A (en) * | 1975-12-24 | 1978-11-07 | Hoechst Aktiengesellschaft | Perfluoroalkylacetyl chloride process |
| US4169904A (en) * | 1978-01-05 | 1979-10-02 | International Business Machines Corporation | Preparation of polymer monomolecular films |
| JPS60123442A (ja) * | 1983-12-07 | 1985-07-02 | Okamura Seiyu Kk | 含フッ素カルボン酸エステルの製造法 |
| US5233058A (en) * | 1988-07-25 | 1993-08-03 | E. I. Du Pont De Nemours And Company | Partially fluorinated compounds and polymers |
| US7989568B2 (en) * | 2008-11-13 | 2011-08-02 | E.I. Du Pont De Nemours And Company | Fluorosulfonates |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA696239A (en) * | 1964-10-20 | Hauptschein Murray | Fluorinated halosulfates and method for their preparation | |
| US2951051A (en) * | 1957-06-26 | 1960-08-30 | Minnesota Mining & Mfg | Perfluoro-substituted aliphatic acids and derivatives thereof |
| US3106589A (en) * | 1960-09-06 | 1963-10-08 | Pennsalt Chemicals Corp | Fluorinated olefins |
| US3016406A (en) * | 1960-09-21 | 1962-01-09 | Du Pont | Reactions of perfluoroalkyl iodides and olefins in the presence of esters |
| US3641083A (en) * | 1968-11-01 | 1972-02-08 | Allied Chem | Chromium complexes of fluoroisoalkoxyalkyl carboxylic acids |
| DE1916669B1 (de) * | 1969-04-01 | 1970-03-05 | Hoechst Ag | Verfahren zur Herstellung von geradkettigen Fluorcarbonsaeuren |
| FR2070452A5 (en) * | 1969-12-05 | 1971-09-10 | Ugine Kuhlmann | Fluorocarboxylic acid chromium complexes - oil repellants - for paper,leather, textiles |
| CH182370A4 (enExample) * | 1970-02-09 | 1972-10-13 |
-
1974
- 1974-02-15 US US05/442,953 patent/US4002657A/en not_active Expired - Lifetime
- 1974-02-26 DE DE2409109A patent/DE2409109A1/de active Pending
- 1974-02-26 GB GB864374A patent/GB1429280A/en not_active Expired
- 1974-02-27 FR FR7406692A patent/FR2220505B1/fr not_active Expired
- 1974-03-04 BE BE141598A patent/BE811821A/xx unknown
- 1974-03-05 JP JP49024879A patent/JPS49117421A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2220505A1 (enExample) | 1974-10-04 |
| US4002657A (en) | 1977-01-11 |
| BE811821A (fr) | 1974-09-04 |
| JPS49117421A (enExample) | 1974-11-09 |
| GB1429280A (en) | 1976-03-24 |
| FR2220505B1 (enExample) | 1976-12-10 |
| USB442953I5 (enExample) | 1976-03-23 |
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