US3629115A - Fluorosilicone lubricants containing tris (pentafluorophenyl) phosphine - Google Patents
Fluorosilicone lubricants containing tris (pentafluorophenyl) phosphine Download PDFInfo
- Publication number
- US3629115A US3629115A US846934A US3629115DA US3629115A US 3629115 A US3629115 A US 3629115A US 846934 A US846934 A US 846934A US 3629115D A US3629115D A US 3629115DA US 3629115 A US3629115 A US 3629115A
- Authority
- US
- United States
- Prior art keywords
- phosphine
- pentafluorophenyl
- fluorosilicone
- tris
- containing tris
- 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 - Lifetime
Links
- 239000000314 lubricant Substances 0.000 title abstract description 10
- FQLSDFNKTNBQLC-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)phosphane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1P(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F FQLSDFNKTNBQLC-UHFFFAOYSA-N 0.000 title abstract description 9
- 239000007866 anti-wear additive Substances 0.000 abstract description 3
- 239000003963 antioxidant agent Substances 0.000 abstract description 3
- -1 for example Chemical group 0.000 description 12
- 239000012530 fluid Substances 0.000 description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- 239000000654 additive Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 239000010802 sludge Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241001656634 Scardia Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 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
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
- 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 description 1
- 239000004615 ingredient Substances 0.000 description 1
- AMQDBUIQKQUCKY-UHFFFAOYSA-M magnesium;1,2,3,4,5-pentafluorobenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].FC1=[C-]C(F)=C(F)C(F)=C1F AMQDBUIQKQUCKY-UHFFFAOYSA-M 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
- C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
-
- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
Definitions
- This invention relates to improved fiuoroalkylpolysiloxane lubricants which contain a minor amount of tris(pentafluorophenyl)phosphine. Addition of the phosphine inhibits oxidation of the fluids and enhances the anti-wear characteristics of metal on metal lubrication.
- Organicphosphorus compounds are known lubricity additives for organopolysiloxanes in general-see U.S. Pat. 2,684,336.
- the use of phosphates and phosphites as antiwear additives in fluorosilicone lubricants is discussed in US. Pat. 3,386,917.
- the invention provides a composition consisting essentially of (1) 100 parts by weight of an organopolysiloxane fluid containing at least 70 mol percent of units, any remaining units being of the formula (RSiO (R' SiO) or (R' SiO in which R, is a perfluoroalkyl radical of no more than 12 carbon atoms, R is a lower alkyl radical of no more than 6 carbon atoms or a phenyl radical; R is a monovalent hydrocarbon or monovalent halohydrocarbon radical; and
- R can be any perfluoroalkyl radical of no more than 12 carbon atoms, for example, heptafluoropropyl, perfluorobutyl, perfluoroisohexyl, prefluorooctyl, perfiuorododecyl or, preferably, trifluoromethyl.
- R can be the phenyl radical or any of the lower alkyl radicals such as methyl, isopropyl, t-butyl or hexyl.
- the same or different R substituent can be bonded to the same silicon atom.
- R can be any monovalent hydrocarbon radical, for example, alkyl radicals such as methyl, ethyl, isopropyl, 2-ethylhexyl or octadecyl; aliphatically unsaturated radicals such as vinyl, allyl, ethynyl, butadienyl or 4-hexenyl; or aryl-containing radicals such as phenyl, tolyl, Xenyl, naphthyl, benzyl, or 2-phenylpropyl.
- alkyl radicals such as methyl, ethyl, isopropyl, 2-ethylhexyl or octadecyl
- aliphatically unsaturated radicals such as vinyl, allyl, ethynyl, butadienyl or 4-hexenyl
- aryl-containing radicals such as phenyl, tolyl, Xenyl, naphthy
- R can also be any monovalent halohydrocarbon radical, for example, 3,3,3-trifluoropropyl, chloropropyl, bromohexyl, chloroallyl, dibromophenyl, chlorophenyl, a,a,u-trifluorotoyl or chloroxenyl.
- monovalent halohydrocarbon radical for example, 3,3,3-trifluoropropyl, chloropropyl, bromohexyl, chloroallyl, dibromophenyl, chlorophenyl, a,a,u-trifluorotoyl or chloroxenyl.
- the tris(pentafiuorophenyl)phosphine additive is a known compound and can be prepared by the reaction of pentafluorophenyl magnesium bromide and phosphorus trrchloride. Only minor amounts, from 0.1 to 8 parts per 100 parts of lubricant, are necessary to obtain the desired oxidative stability. Greater amounts can be used if desired but are generally uneconomical. Depending upon the specific composition of the fluid, insolubility of the phosphine at greater concentrations may present problems.
- the additive-containing fluid also gave improved lubrication at high loadings in the four-ball test.
- test conditions 1200 r.p.m. at 167 F. for 30 minutes at a loading of 10 kilograms of steel on aluminum
- the addition of 1% tris(pentafluorophenyl)phosphine to the lubricant reduced the scar diameter from 4.9 millimeters to 0.49 millimeter.
- R is a monovalent hydrocarbon or monovalent halohydrocarbon radical; and (2) from 0.1 to 8 parts by weight of tris(pentafiuoropheny1)phosphine.
- WYMAN Primary Examlner R, is a perfiuoroalkyl radical of no more than 12 20 w CANNON, Assistant Examiner carbon atoms,
- R is a lower alkyl radical of no more than 6 US. Cl. X.R.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84693469A | 1969-08-01 | 1969-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3629115A true US3629115A (en) | 1971-12-21 |
Family
ID=25299347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US846934A Expired - Lifetime US3629115A (en) | 1969-08-01 | 1969-08-01 | Fluorosilicone lubricants containing tris (pentafluorophenyl) phosphine |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3629115A (enrdf_load_stackoverflow) |
| JP (1) | JPS4824985B1 (enrdf_load_stackoverflow) |
| BE (1) | BE754229A (enrdf_load_stackoverflow) |
| DE (1) | DE2038239A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2056928B3 (enrdf_load_stackoverflow) |
| GB (1) | GB1259579A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5595962A (en) * | 1995-06-29 | 1997-01-21 | Dow Corning Corporation | Fluorosilicone lubricant compositions |
-
0
- BE BE754229D patent/BE754229A/xx unknown
-
1969
- 1969-08-01 US US846934A patent/US3629115A/en not_active Expired - Lifetime
-
1970
- 1970-05-11 JP JP45040018A patent/JPS4824985B1/ja active Pending
- 1970-06-08 GB GB1259579D patent/GB1259579A/en not_active Expired
- 1970-07-30 FR FR707028168A patent/FR2056928B3/fr not_active Expired
- 1970-07-31 DE DE19702038239 patent/DE2038239A1/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5595962A (en) * | 1995-06-29 | 1997-01-21 | Dow Corning Corporation | Fluorosilicone lubricant compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| BE754229A (fr) | 1971-02-01 |
| DE2038239A1 (de) | 1971-02-18 |
| GB1259579A (enrdf_load_stackoverflow) | 1972-01-05 |
| FR2056928B3 (enrdf_load_stackoverflow) | 1973-04-27 |
| JPS4824985B1 (enrdf_load_stackoverflow) | 1973-07-25 |
| FR2056928A7 (enrdf_load_stackoverflow) | 1971-05-07 |
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