JPS5949237B2 - ペルフルオロアルキルエ−テル置換アリ−ルホスフインおよびその潤滑剤組成物 - Google Patents
ペルフルオロアルキルエ−テル置換アリ−ルホスフインおよびその潤滑剤組成物Info
- Publication number
- JPS5949237B2 JPS5949237B2 JP51133082A JP13308276A JPS5949237B2 JP S5949237 B2 JPS5949237 B2 JP S5949237B2 JP 51133082 A JP51133082 A JP 51133082A JP 13308276 A JP13308276 A JP 13308276A JP S5949237 B2 JPS5949237 B2 JP S5949237B2
- Authority
- JP
- Japan
- Prior art keywords
- phosphine
- formula
- perfluoroalkyl ether
- following structural
- inhibiting corrosion
- 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
- 239000000314 lubricant Substances 0.000 title claims description 26
- 125000005010 perfluoroalkyl group Chemical group 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 title description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 43
- 239000007788 liquid Substances 0.000 claims description 25
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- -1 phosphine compound Chemical class 0.000 claims description 19
- 150000003003 phosphines Chemical class 0.000 claims description 18
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 17
- 238000005260 corrosion Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 230000007797 corrosion Effects 0.000 claims description 14
- 125000001033 ether group Chemical group 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 11
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000654 additive Substances 0.000 description 10
- 150000002576 ketones Chemical class 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 6
- QFTZULJNRAHOIY-UHFFFAOYSA-N 1,4-dibromo-2,3,5,6-tetrafluorobenzene Chemical compound FC1=C(F)C(Br)=C(F)C(F)=C1Br QFTZULJNRAHOIY-UHFFFAOYSA-N 0.000 description 5
- 229910001069 Ti alloy Inorganic materials 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 150000001266 acyl halides Chemical class 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- IPLUWQPTPKNBRD-UHFFFAOYSA-N 1,2-dibromo-3,4,5,6-tetrafluorobenzene Chemical compound FC1=C(F)C(F)=C(Br)C(Br)=C1F IPLUWQPTPKNBRD-UHFFFAOYSA-N 0.000 description 1
- 229910000851 Alloy steel Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910000640 Fe alloy Inorganic materials 0.000 description 1
- 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- 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
- C07F9/50—Organo-phosphines
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/06—Perfluoro polymers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/06—Perfluoro polymers
- C10M2213/062—Polytetrafluoroethylene [PTFE]
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/061—Metal salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/02—Macromolecular compounds from phosphorus-containg monomers, obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US000000629469 | 1975-11-06 | ||
| US05/629,469 US4011267A (en) | 1975-11-06 | 1975-11-06 | Perfluoroalkylether substituted aryl phosphines and their synthesis |
| US05/681,871 US4043926A (en) | 1975-11-06 | 1976-04-30 | Lubricant composition |
| US000000681871 | 1976-04-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5278854A JPS5278854A (en) | 1977-07-02 |
| JPS5949237B2 true JPS5949237B2 (ja) | 1984-12-01 |
Family
ID=27090943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51133082A Expired JPS5949237B2 (ja) | 1975-11-06 | 1976-11-05 | ペルフルオロアルキルエ−テル置換アリ−ルホスフインおよびその潤滑剤組成物 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US4011267A (en:Method) |
| JP (1) | JPS5949237B2 (en:Method) |
| BE (1) | BE848019A (en:Method) |
| CA (1) | CA1072121A (en:Method) |
| CH (1) | CH606398A5 (en:Method) |
| DE (1) | DE2650722C2 (en:Method) |
| ES (1) | ES453073A1 (en:Method) |
| FR (1) | FR2330690A1 (en:Method) |
| GB (1) | GB1551425A (en:Method) |
| IT (1) | IT1063558B (en:Method) |
| NL (1) | NL188474C (en:Method) |
| SE (1) | SE423553B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH034650A (ja) * | 1989-05-31 | 1991-01-10 | Matsushita Electric Ind Co Ltd | コードレス電話装置 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097388A (en) * | 1976-10-12 | 1978-06-27 | The United States Of America As Represented By The Secretary Of The Air Force | Linear fluorinated polyether lubricant compositions containing perfluoroalkylether substituted phosphines |
| US4194983A (en) * | 1979-02-06 | 1980-03-25 | The United States Of America As Represented By The Secretary Of The Air Force | Perfluorinated polyalkylether based lubricant composition |
| US4438006A (en) | 1981-06-29 | 1984-03-20 | The United States Of America As Represented By The Secretary Of The Air Force | Perfluorinated aliphatic polyalkylether lubricant with an additive composed of an aromatic phosphine substituted with perfluoroalkylether groups |
| IT1152230B (it) * | 1982-05-31 | 1986-12-31 | Montedison Spa | Procedimento per la preparazione di grassi lubrificanti a base di politetrafluoroetilene e perfluoropolieteri |
| US4443349A (en) * | 1982-09-14 | 1984-04-17 | The United States Of America As Represented By The Secretary Of The Air Force | Fluorinated aliphatic polyalkylether lubricant with an additive composed of an aromatic phosphine substituted with perfluoroalkylether groups |
| US4454349A (en) * | 1982-09-14 | 1984-06-12 | The United States Of America As Represented By The Secretary Of The Air Force | Perfluoroalkylether substituted phenyl phosphines |
| US4431556A (en) * | 1982-09-14 | 1984-02-14 | The United States Of America As Represented By The Secretary Of The Air Force | Oxidation stable polyfluoroalkylether grease compositions |
| US4431555A (en) * | 1982-09-14 | 1984-02-14 | The United States Of America As Represented By The Secretary Of The Air Force | Oxidation stable polyfluoroalkylether grease compositions |
| JPS60109028A (ja) * | 1983-11-17 | 1985-06-14 | Hitachi Maxell Ltd | 磁気記録媒体 |
| US4668823A (en) * | 1983-12-30 | 1987-05-26 | Union Carbide Corporation | Process for the preparation of bulky alkyldiarylphosphines and unsymmetrical aryldialkyl phosphines |
| IT1188166B (it) * | 1985-04-24 | 1988-01-07 | Montefluos Spa | Stabilizzanti a struttura arilfosfinica per olii e grassi perfluoropolieterei |
| US5219477A (en) * | 1991-04-15 | 1993-06-15 | The Dow Chemical Company | Antioxidant-containing cyclophosphazene compositions, antioxidants for use therein, and method therefor |
| WO1995013341A1 (fr) * | 1993-11-12 | 1995-05-18 | Aktsionernoe Obschestvo Zakrytogo Tipa 'amtek' | Compose de modification antifriction |
| USH1537H (en) | 1994-12-01 | 1996-06-04 | The United States Of America As Represented By The Secretary Of The Air Force | Perfluorinated polyether lubricant compositions |
| GB0001859D0 (en) * | 2000-01-28 | 2000-03-22 | Univ Liverpool | A method of generating a functionalised arylphosphine |
| US7569527B2 (en) * | 2005-06-27 | 2009-08-04 | E.I. Dupont De Nemours And Company | Fluoro derivative-substituted aryl pnictogens and their oxides |
| JP6227550B2 (ja) * | 2011-12-22 | 2017-11-08 | ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． | 芳香族末端基を有する（パー）フルオロポリエーテルの製造方法 |
| JP7142405B2 (ja) * | 2018-01-24 | 2022-09-27 | 出光興産株式会社 | 潤滑油組成物及び冷凍機用組成物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3201445A (en) * | 1963-05-20 | 1965-08-17 | Du Pont | Cyclic phosphonitrilate esters of polyfluoroether alcohols |
| US3393151A (en) * | 1965-07-28 | 1968-07-16 | Air Force Usa | Perfluorinated aliphatic polyether lubricant with a perfluorinated phenyl compound additive |
| US3481872A (en) * | 1965-07-28 | 1969-12-02 | Us Air Force | Degradation resistant and non-corrosive high-temperature lubricant formulation |
| US3306855A (en) * | 1966-03-24 | 1967-02-28 | Du Pont | Corrosion and rust inhibited poly (hexafluoropropylene oxide) oil compositions |
| US3499041A (en) * | 1968-02-13 | 1970-03-03 | Us Air Force | Perfluoroalkaryl,-araryl and-phenoxyaryl phosphines |
| US3483129A (en) * | 1968-02-13 | 1969-12-09 | Us Air Force | Perfluorinated substituted phenyl phosphine lubricant additives |
| US3567802A (en) * | 1968-12-03 | 1971-03-02 | Du Pont | Perfluoropolyoxoalkane substttuted phosphinates |
-
1975
- 1975-11-06 US US05/629,469 patent/US4011267A/en not_active Expired - Lifetime
-
1976
- 1976-04-30 US US05/681,871 patent/US4043926A/en not_active Expired - Lifetime
- 1976-11-02 NL NLAANVRAGE7612135,A patent/NL188474C/xx not_active IP Right Cessation
- 1976-11-02 SE SE7612165A patent/SE423553B/xx not_active IP Right Cessation
- 1976-11-03 CA CA264,801A patent/CA1072121A/en not_active Expired
- 1976-11-03 IT IT29005/76A patent/IT1063558B/it active
- 1976-11-05 BE BE172097A patent/BE848019A/xx not_active IP Right Cessation
- 1976-11-05 FR FR7633406A patent/FR2330690A1/fr active Granted
- 1976-11-05 DE DE2650722A patent/DE2650722C2/de not_active Expired
- 1976-11-05 ES ES453073A patent/ES453073A1/es not_active Expired
- 1976-11-05 JP JP51133082A patent/JPS5949237B2/ja not_active Expired
- 1976-11-05 CH CH1399676A patent/CH606398A5/xx not_active IP Right Cessation
- 1976-11-08 GB GB46342/76A patent/GB1551425A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH034650A (ja) * | 1989-05-31 | 1991-01-10 | Matsushita Electric Ind Co Ltd | コードレス電話装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2330690B1 (en:Method) | 1978-12-22 |
| NL188474C (nl) | 1992-07-01 |
| US4043926A (en) | 1977-08-23 |
| CA1072121A (en) | 1980-02-19 |
| JPS5278854A (en) | 1977-07-02 |
| IT1063558B (it) | 1985-02-11 |
| US4011267A (en) | 1977-03-08 |
| NL188474B (nl) | 1992-02-03 |
| FR2330690A1 (fr) | 1977-06-03 |
| GB1551425A (en) | 1979-08-30 |
| DE2650722A1 (de) | 1977-05-12 |
| ES453073A1 (es) | 1978-03-01 |
| DE2650722C2 (de) | 1986-09-25 |
| CH606398A5 (en:Method) | 1978-10-31 |
| SE7612165L (sv) | 1977-05-07 |
| NL7612135A (nl) | 1977-05-10 |
| BE848019A (fr) | 1977-05-05 |
| SE423553B (sv) | 1982-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5949237B2 (ja) | ペルフルオロアルキルエ−テル置換アリ−ルホスフインおよびその潤滑剤組成物 | |
| US4097388A (en) | Linear fluorinated polyether lubricant compositions containing perfluoroalkylether substituted phosphines | |
| US2671799A (en) | Perhalocarbon compounds and method of preparing them | |
| EP1479753B1 (en) | Perfluoropolyether additives | |
| KR940005343B1 (ko) | 과플루오로폴리에테르 오일 및 그리스용 아릴포스핀 구조를 갖는 안정제 | |
| US4174461A (en) | Stabilized perfluoropolyether fluids | |
| US4454349A (en) | Perfluoroalkylether substituted phenyl phosphines | |
| TW202014396A (zh) | 全氟鏈烷二烯化合物的製造方法 | |
| US4438007A (en) | Perfluorinated aliphatic polyalkylether lubricant with an additive composed of an aromatic phosphine substituted with perfluoroalkylether groups | |
| JP6826694B2 (ja) | グリース組成物 | |
| Tamborski et al. | Synthesis and properties of silahydrocarbons, a class of thermally stable, wide liquid range fluids | |
| US4194983A (en) | Perfluorinated polyalkylether based lubricant composition | |
| US2998453A (en) | Phenoxy diphenyl sulfones and their preparation | |
| US2452944A (en) | Other | |
| US1737203A (en) | Ketone and method of making same | |
| US2998454A (en) | Substituted phenyl biphenylyl sulfones and their preparation | |
| US5326910A (en) | Monophospha-S-triazines of improved hydrolytic and thermal oxidative stability | |
| JP2018535817A (ja) | ペルフルオロアルキル基をルイス酸触媒として含有しているビスマス化合物 | |
| US6326337B1 (en) | Perfluoropolyalkylether lubricant formulation with improved stability | |
| US4393241A (en) | Synthesis of alkoxy and phenoxy substituted aryl sulfides | |
| Brown et al. | Preparation, Retractive Indices, and Boiling Points of Certain Organic Liquids. | |
| Gopal et al. | The synthesis of perfluoro (alkyletherphenyl) phosphines | |
| US2547679A (en) | 3, 3'-bis-(trifluoromethyl) diphenyl ether | |
| US3080429A (en) | Preparation of halocareon having the empirical formula c10cl4f14 | |
| Martin et al. | Synthesis and Fluorination of Phosphorus (III) β-Chloroethoxy Dichloride1 |