US3714044A - Fluorosilicone lubricants containing nitrophenyl substituted organopolysiloxanes - Google Patents
Fluorosilicone lubricants containing nitrophenyl substituted organopolysiloxanes Download PDFInfo
- Publication number
- US3714044A US3714044A US00173274A US3714044DA US3714044A US 3714044 A US3714044 A US 3714044A US 00173274 A US00173274 A US 00173274A US 3714044D A US3714044D A US 3714044DA US 3714044 A US3714044 A US 3714044A
- Authority
- US
- United States
- Prior art keywords
- steel
- fluorosilicone
- radicals
- lubricants containing
- lubricants
- 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
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- 239000000314 lubricant Substances 0.000 title abstract description 12
- 229920001296 polysiloxane Polymers 0.000 title description 13
- 125000006501 nitrophenyl group Chemical group 0.000 title 1
- 229910001369 Brass Inorganic materials 0.000 abstract description 5
- 239000010951 brass Substances 0.000 abstract description 5
- 229910052782 aluminium Inorganic materials 0.000 abstract description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 3
- -1 siloxanes Chemical class 0.000 description 60
- 229910000831 Steel Inorganic materials 0.000 description 18
- 239000010959 steel Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- 239000012530 fluid Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000005461 lubrication Methods 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 231100000241 scar Toxicity 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 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 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 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
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000005070 decynyl group Chemical group [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#C* 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229920005560 fluorosilicone rubber Polymers 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930192878 garvin Natural products 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001802 myricyl 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])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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical class [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 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
- 239000000126 substance Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
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- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
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- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon
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- C10M155/00—Lubricating compositions characterised by the additive being a macromolecular compound containing atoms of elements not provided for in groups C10M143/00 - C10M153/00
- C10M155/02—Monomer containing silicon
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- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/041—Carbon; Graphite; Carbon black
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- C10M2201/103—Clays; Mica; Zeolites
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/10—Compounds containing silicon
- C10M2201/105—Silica
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
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- C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
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- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/06—Perfluoro polymers
- C10M2213/062—Polytetrafluoroethylene [PTFE]
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- C10M2229/02—Unspecified siloxanes; Silicones
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- C10M2229/02—Unspecified siloxanes; Silicones
- C10M2229/025—Unspecified siloxanes; Silicones used as base material
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- C10M2229/04—Siloxanes with specific structure
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- 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
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
- C10M2229/0415—Siloxanes with specific structure containing aliphatic substituents used as base material
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- C10M2229/04—Siloxanes with specific structure
- C10M2229/042—Siloxanes with specific structure containing aromatic substituents
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- C10M2229/042—Siloxanes with specific structure containing aromatic substituents
- C10M2229/0425—Siloxanes with specific structure containing aromatic substituents used as base material
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- C10M2229/04—Siloxanes with specific structure
- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
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- 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
- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
- C10M2229/0435—Siloxanes with specific structure containing carbon-to-carbon double bonds used as base material
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- 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
- C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
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Definitions
- This invention relates to improved fluoroalkylpolysiloxanes which contain minor amounts of nitrophenyl-substituted organopolysiloxanes.
- the invention relates to fluorosilicone fluids exhibiting enhanced antiwear characteristics and superior thermal stability.
- Organopolysiloxane fluids are known lubricants.
- Dimethylpolysiloxanes are general lubricants but have poor antiwear characteristics when used to lubricate steel on steel sliding surfaces.
- Fluorosilicones, such as trifluoropropylmethylpolysiloxanes are much better lubricants for steel on steel but exhibit poor lubrication for steel on brass and steel on aluminum.
- the fiuorosilicone fluids find only limited use in environments requiring lubrication of metal surfaces other than or in addition to steel on steel.
- organosilicon compositions comprising of (a) 98 to 99.9 weight percent of an organopolysiloxane fluid containing at least 70 mol percent units in which R is a perfiuoroalkylethyl radical of from 3 to 12 carbon atoms, and R is selected from the group consisting of lower alkyl radicals and the phenyl radical; any remaining units being of the formula R' SiO or which R is selected from the group consisting of monovalent hydrocarbon radicals and monovalent halohydrocarbon radicals; and (b) 0.1 to 2 weight percent of liquid polysiloxane consisting essentially of units wherein R is as defined above, any remaining units being of the formula R Si wherein R is as defined above.
- R can be any perfluoroalkylethyl radical of no more than 12 carbon atoms, such as CF CH CH C F CH CH C F CH CH C F CH CH C10F21CH2CH2 and the like.
- R can be any lower alkyl radical containing from 1 to 6 inclusive carbon atoms, such as methyl, propyl, isopropyl, butyl and hexyl. R can also be a phenyl radical.
- R can be any monovalent hydrocarbon radical, such as alkyl radicals such as methyl, ethyl, propyl, isopropyl, butyl, pentyl, isopentyl, neopentyl, hexyl, octyl, dodecyl,
- alkenyl radicals such as, vinyl, allyl, hexenyl, butenyl, 3-0ctenyl, 4,9-octadecadienyl and 4-nonenyl
- alkynyl radicals such as propynyl, heptynyl, butynyl, decynyl
- alkenylnyl radicals such as l-penten-3-ynyl, 2-ethyl-1-buten-3-ynyl
- cycloaliphatic radicals such as, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, propylcyclohexyl, 2,4-dimethylcyclopentyl, cyclohexenyl,
- R monovalent halohydrocarbon radicals, such as aliphatic groups such as chloromethyl, 3-chloropropyl, 3,3,3-trichloropropyl, perfiuorovinyl, chlorooctadecyl or radicals of the formula R CH CH Where R can be any perfiuoroalkyl group such as trifiuoromethyl, perfiuoroethyl, perfluoroisobutyl, perfluoroheptyl or perfluorooctadecyl; aromatic groups such as dichlorophenyl, tetrabromoxenyl, tetrachlorophenyl, alpha,alpha,alpha-trifluorotolyl or iodonaphthyl; cycloaliphatic groups such as chlorocyclohexyl, brornocyclopentyl or chlorocyclohexenyl and aralkyl groups
- the preferred monovalent hydrocarbon and halohydrocarbon radicals are those having no more than 18 carbon atoms.
- R groups are lower alkyl radicals, the phenyl radical and Z-phenylpropyl radicals.
- fiuoroalkylpolysiloxanes are fluids, generally having a viscosity in the range of 20 to 20,000 es. and include copolymers such as and the like.
- Particularly preferred fluids are the triorganosilyl endblocked 3,3,3 trifluoropropylmethylpolysiloxanes having a viscosity in the range of about to 1000 cs. when measured at C.
- the nitrophenyl-substituted polysiloxanes are known polymers-see US Pat. 3,375,218.
- the polymers are prepared by nitration of phenylsilanes followed by hydrolysis and condensation. Monofunctional silanes are added to provide endblocking units (R SiO and thus control viscosity of the additive polymer.
- R SiO endblocking units
- the fluid polymeric additive has a degree of polymerization of from 3 to 15. Only minor amounts of the additive, from 0.1 to 2 weight percent, preferably from 0.5 to 1.5 weight percent, are necessary to obtain the desired degree of lubricity. The optimum amount will depend upon the nature of the fluorosilicone and its application. Amounts greater than two weight percent can be used, but are generally uneconomical.
- the lubricating compositions of the invention may optionally contain corrosion inhibitors, extreme pressure agents, anti-oxidants, dyes and the like.
- the invention also contemplates the use of thickening agents in combination with the compositions to formulate improved greases.
- Thickening agents suitable for use in such a grease formulation include fatty acid soaps, carbon black, silica, clay, polytetrafiuoroethylene and the like.
- the thickener should not be one that is reactive with the nitrophenylsiloxane additive.
- the thickening agent will generally be present in an amount for about 10 to 60 weight percent of the grease compositions.
- the nitrophenylsiloxane increases the thermal stability of the fluid.
- the weight loss at elevated temperatures of additive-containing fluids is significantly decreased. Because of this thermal stability, the compositions of the invention have utility as base stocks in fluorosilicone rubber formulations.
- the lubricity characteristics were determined by means of the 4-Ball test.
- the 4-Ball tests were conducted on a Roxanna wear testing machine wherein a /2 inch diameter steel ball is rotated against three lubricated stationary /2 inch metal balls under various conditions and loads. After testing, the length and width of the scar on each stationary ball is measured and the average of the six measurements is taken as the wear scar diameter. The smaller the wear scar, of course, the better the lubricant.
- a composition consisting essentially of (a) 98 to 99.9 weight percent of an organopolysiloxane fluid containing at least 70 mol percent units in which R is a perfiuoroalkylethyl radical of from 3 to 12 inclusive carbon atoms, and R is selected from the group consisting of alkyl radicals of no more than 6 carbon atoms and the phenyl radical; any remaining units being of the formula R' SiO which R is selected from the group consisting of monovalent hydrocarbon radicals and monovalent halohydrocarbon radicals; and (b) 0.1 to 2 weight percent of polysiloxane fluid consisting essentially of S (R)S
- composition of claim 1 wherein the organopolysiloxane (a) is triorganosilyl-endblocked 3,3,3 tnfiuoropropylmethylpolysiloxane having a viscosity of from 20 to 1000 centistokes at 25 C.
- composition of claim 1 where the organopolysiloxane (a) is trimethylsilyl-endblocked 3,3,3 trifluoropropylmethylpolysiloxane.
- a lubricant comprising the composition of claim 1 containing suflicient thickening agent to form a grease.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
MINOR AMOUNTS OF NITROPHEYL-SUBSTITUTED SILOXANES ARE ADDED TO FLUOROSILICONE LUBRICANTS TO IMPROVE THE STEEL ON BRASS AND STEEL ON ALUMINUM ANTIWEAR CHARACTERISTICS.
Description
United States Patent 3,714,044 FLUOROSILICDNE LUBRICANT CQNTAINHNG NI'I'ROPl-llENYL-SUBSTITUTED ORGANOPOLY- filLOXANES Yung Ki Kim, Midland, Mich, assignor to Dow Chemical Corporation, Midland, Mich. No Drawing. Filed Aug. 19, 1971, Ser. No. 173,274 int. Cl. ClOrn 3/44, 7/48 U5. Cl. 252-49.6 6 Claims ABSTRACT OF THE DISCLOSURE Minor amounts of nitrophenyl-substituted siloxanes are added to fluorosilicone lubricants to improve the steel on brass and steel on aluminum antiwear characteristics.
This invention relates to improved fluoroalkylpolysiloxanes which contain minor amounts of nitrophenyl-substituted organopolysiloxanes. In one aspect the invention relates to fluorosilicone fluids exhibiting enhanced antiwear characteristics and superior thermal stability.
Organopolysiloxane fluids are known lubricants. Dimethylpolysiloxanes are general lubricants but have poor antiwear characteristics when used to lubricate steel on steel sliding surfaces. Fluorosilicones, such as trifluoropropylmethylpolysiloxanes are much better lubricants for steel on steel but exhibit poor lubrication for steel on brass and steel on aluminum. Thus, the fiuorosilicone fluids find only limited use in environments requiring lubrication of metal surfaces other than or in addition to steel on steel.
By the practice of the present invention, the antiwear characteristics of fluorosilicones on steel on brass are greatly enhanced and the thermal stability is increased, thus rendering them suitable for the high temperature lubrication of various metals.
In accordance with the invention, there are provided improved organosilicon compositions comprising of (a) 98 to 99.9 weight percent of an organopolysiloxane fluid containing at least 70 mol percent units in which R is a perfiuoroalkylethyl radical of from 3 to 12 carbon atoms, and R is selected from the group consisting of lower alkyl radicals and the phenyl radical; any remaining units being of the formula R' SiO or which R is selected from the group consisting of monovalent hydrocarbon radicals and monovalent halohydrocarbon radicals; and (b) 0.1 to 2 weight percent of liquid polysiloxane consisting essentially of units wherein R is as defined above, any remaining units being of the formula R Si wherein R is as defined above.
As described above, R, can be any perfluoroalkylethyl radical of no more than 12 carbon atoms, such as CF CH CH C F CH CH C F CH CH C F CH CH C10F21CH2CH2 and the like.
R can be any lower alkyl radical containing from 1 to 6 inclusive carbon atoms, such as methyl, propyl, isopropyl, butyl and hexyl. R can also be a phenyl radical.
R can be any monovalent hydrocarbon radical, such as alkyl radicals such as methyl, ethyl, propyl, isopropyl, butyl, pentyl, isopentyl, neopentyl, hexyl, octyl, dodecyl,
octadecyl, 3-methylheptyl, 6-butyloctadecyl, tertiary butyl, myricyl and 2,2-diethylpentyl; alkenyl radicals such as, vinyl, allyl, hexenyl, butenyl, 3-0ctenyl, 4,9-octadecadienyl and 4-nonenyl; alkynyl radicals such as propynyl, heptynyl, butynyl, decynyl; alkenylnyl radicals such as l-penten-3-ynyl, 2-ethyl-1-buten-3-ynyl; cycloaliphatic radicals such as, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, propylcyclohexyl, 2,4-dimethylcyclopentyl, cyclohexenyl, bicyclloE31101hexyl, tricyclo[3.2.1.1 ]-5-nonenyl, spiro- [4.5]decyl, dispiro[4.1.4.2]-1-tridecenyl, decahydronaphthyl, 2,3-dihydroindyl and 1,2,3,4-tetrahydronaphthyl; aryl radicals such as phenyl, tolyl, Xylyl, 3-ethylphenyl, Xenyl, na hthyl, anthracyl, pentacenyl, 3,4-methylethylphenyl, 9,9-bifiuoryl and 4-m-terphenyl; and aralkyl radicals such as Z-phenyl-octyl, 3-methyl-2-(4-isopropylphenyl)heptyl, benzyl, 2-ethyltolyl, 2-ethyl-p-cymyl, diphenylmethyl, 4,5-diphenylpentyl, 2-phenylethyl and 2- phenylpropyl.
Also included within the scope or" R are monovalent halohydrocarbon radicals, such as aliphatic groups such as chloromethyl, 3-chloropropyl, 3,3,3-trichloropropyl, perfiuorovinyl, chlorooctadecyl or radicals of the formula R CH CH Where R can be any perfiuoroalkyl group such as trifiuoromethyl, perfiuoroethyl, perfluoroisobutyl, perfluoroheptyl or perfluorooctadecyl; aromatic groups such as dichlorophenyl, tetrabromoxenyl, tetrachlorophenyl, alpha,alpha,alpha-trifluorotolyl or iodonaphthyl; cycloaliphatic groups such as chlorocyclohexyl, brornocyclopentyl or chlorocyclohexenyl and aralkyl groups such as chlorobenzyl, beta-(chlorophenyl)ethyl or beta-(iodophenyl)ethyl or beta-(bromophenyl)propyl.
The preferred monovalent hydrocarbon and halohydrocarbon radicals are those having no more than 18 carbon atoms. Especially preferred as R groups are lower alkyl radicals, the phenyl radical and Z-phenylpropyl radicals.
The above-described fiuoroalkylpolysiloxanes are fluids, generally having a viscosity in the range of 20 to 20,000 es. and include copolymers such as and the like.
Particularly preferred fluids are the triorganosilyl endblocked 3,3,3 trifluoropropylmethylpolysiloxanes having a viscosity in the range of about to 1000 cs. when measured at C.
The nitrophenyl-substituted polysiloxanes are known polymers-see US Pat. 3,375,218. The polymers are prepared by nitration of phenylsilanes followed by hydrolysis and condensation. Monofunctional silanes are added to provide endblocking units (R SiO and thus control viscosity of the additive polymer. It is preferred that the fluid polymeric additive has a degree of polymerization of from 3 to 15. Only minor amounts of the additive, from 0.1 to 2 weight percent, preferably from 0.5 to 1.5 weight percent, are necessary to obtain the desired degree of lubricity. The optimum amount will depend upon the nature of the fluorosilicone and its application. Amounts greater than two weight percent can be used, but are generally uneconomical.
Other additives can be utilized in the above compositions without departing from scope of the invention. Thus, the lubricating compositions of the invention may optionally contain corrosion inhibitors, extreme pressure agents, anti-oxidants, dyes and the like. The invention also contemplates the use of thickening agents in combination with the compositions to formulate improved greases. Thickening agents suitable for use in such a grease formulation include fatty acid soaps, carbon black, silica, clay, polytetrafiuoroethylene and the like. The thickener should not be one that is reactive with the nitrophenylsiloxane additive. The thickening agent will generally be present in an amount for about 10 to 60 weight percent of the grease compositions.
In addition to enhancing the antiwear properties of fluorosilicones, the nitrophenylsiloxane increases the thermal stability of the fluid. The weight loss at elevated temperatures of additive-containing fluids is significantly decreased. Because of this thermal stability, the compositions of the invention have utility as base stocks in fluorosilicone rubber formulations.
The following example is illustrative and not intended to be limiting of the present invention which is delineated in the claims. In the example, the lubricity characteristics were determined by means of the 4-Ball test. The 4-Ball tests were conducted on a Roxanna wear testing machine wherein a /2 inch diameter steel ball is rotated against three lubricated stationary /2 inch metal balls under various conditions and loads. After testing, the length and width of the scar on each stationary ball is measured and the average of the six measurements is taken as the wear scar diameter. The smaller the wear scar, of course, the better the lubricant.
EXAMPLE Sufficient trimethylsilyl-endblocked nitrophenylmethylpolysiloxane having a degree of polymerization of about 12 was mixed with trimethylsilyl endblocked 3,3,3 trifluoropropylmethylpolysiloxane (300 cs.) to form a fluorosilicone composition containing 0.2 weight percent of the additive. The antiwear properties and thermal stability of this composition were compared to the properties of the pure polymer. Results are given below:
Fluorosilicone 0.2
Fluorowt. percent silicone nitrophenyl- (scarsiloxane 4-ba1l test conditions min.) (Scar-mm.)
Steel on steel-167 F., 1 hr., 1,200 r.p.m., 40 kg 0. 81 0. 43
Steel on steel-167 F., 1 hr., 1,200 r.p.m., 60 kg. 1. 47 0.50
Steel on brass167 F., hr., 1,200 r.p.m., kg 3. 7 1. 5
Weight loss (percent) as determined on lO-gram sample in 50 ml. open beaker at 450 F.:
After 1 day 11. 3 4. 5 After 7 days 46. 4 17. 4
These data demonstrate the effect of the additive on the steel on brass and steel on steel lubrication properties of fluorosilicones at high loads. The additive also reduces the weight loss of fluorosilicones at elevated temperature. These effects are quite unexpected since they were not observed in other silicone lubricants, such as polydimethylsiloxane.
That which is claimed is:
1. A composition consisting essentially of (a) 98 to 99.9 weight percent of an organopolysiloxane fluid containing at least 70 mol percent units in which R is a perfiuoroalkylethyl radical of from 3 to 12 inclusive carbon atoms, and R is selected from the group consisting of alkyl radicals of no more than 6 carbon atoms and the phenyl radical; any remaining units being of the formula R' SiO which R is selected from the group consisting of monovalent hydrocarbon radicals and monovalent halohydrocarbon radicals; and (b) 0.1 to 2 weight percent of polysiloxane fluid consisting essentially of S (R)S|i0 units wherein R is as defined above any remaining units being of the formula RSiO units wherein R is as defined above.
2. The composition of claim 1 wherein the organopolysiloxane (a) is triorganosilyl-endblocked 3,3,3 tnfiuoropropylmethylpolysiloxane having a viscosity of from 20 to 1000 centistokes at 25 C.
3. The composition of claim 1 wherein the organopolysiloxane (b) has a degree of polymerization in the range of from 3 to 15.
4. The composition of claim 1 where the organopolysiloxane (a) is trimethylsilyl-endblocked 3,3,3 trifluoropropylmethylpolysiloxane.
5. A lubricant comprising the composition of claim 1 containing suflicient thickening agent to form a grease.
6. The lubricant of claim 5 wherein the thickening agent is present in an amount in the range of from 10 to weight percent, based on the total weight of lubricant.
References Cited UNITED STATES PATENTS 3,377,284 4/ 1968 Schiefer et al. 25249.6 3,575,921 4/1971 Lee 25249.6 3,662,765 5/1972 Clark 26046.5 E X PATRICK P. GARVIN, Primary Examiner A. H. METZ, Assistant Examiner US. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17327471A | 1971-08-19 | 1971-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3714044A true US3714044A (en) | 1973-01-30 |
Family
ID=22631273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00173274A Expired - Lifetime US3714044A (en) | 1971-08-19 | 1971-08-19 | Fluorosilicone lubricants containing nitrophenyl substituted organopolysiloxanes |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3714044A (en) |
| JP (1) | JPS5527600B2 (en) |
| CA (1) | CA965405A (en) |
| DE (1) | DE2237835C3 (en) |
| FR (1) | FR2149558B1 (en) |
| GB (1) | GB1346150A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4515702A (en) * | 1983-04-12 | 1985-05-07 | Shin-Etsu Chemical Co., Ltd. | Heat-resistant silicone fluid compositions |
| EP0284268A3 (en) * | 1987-03-24 | 1988-11-23 | Dev Er Fluid Ltd | Improvements in, or relating to electro-rheological fluids/electric field responsive fluids |
| EP0311984A3 (en) * | 1987-10-12 | 1989-10-11 | American Cyanamid Company | Improvements in or relating to electro-rheological fluids |
| US5217633A (en) * | 1988-06-25 | 1993-06-08 | Bayer Aktiengesellschaft | Low-temperature lubricating oil |
| US5384057A (en) * | 1990-08-09 | 1995-01-24 | E. I. Du Pont De Nemours And Company | Compositions and process of using in refrigeration |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2309628A1 (en) * | 1975-01-09 | 1976-11-26 | Cetehor | Polysiloxane lubricants contg. polar cpds. - to reduce the critical wetting tension of lubricated surfaces |
| JP2669993B2 (en) * | 1992-04-16 | 1997-10-29 | 信越化学工業株式会社 | Silicone grease composition |
-
1971
- 1971-08-19 US US00173274A patent/US3714044A/en not_active Expired - Lifetime
-
1972
- 1972-05-26 CA CA143,131A patent/CA965405A/en not_active Expired
- 1972-07-25 JP JP7452972A patent/JPS5527600B2/ja not_active Expired
- 1972-08-01 DE DE2237835A patent/DE2237835C3/en not_active Expired
- 1972-08-15 GB GB3793972A patent/GB1346150A/en not_active Expired
- 1972-08-18 FR FR7229630A patent/FR2149558B1/fr not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4515702A (en) * | 1983-04-12 | 1985-05-07 | Shin-Etsu Chemical Co., Ltd. | Heat-resistant silicone fluid compositions |
| EP0284268A3 (en) * | 1987-03-24 | 1988-11-23 | Dev Er Fluid Ltd | Improvements in, or relating to electro-rheological fluids/electric field responsive fluids |
| EP0311984A3 (en) * | 1987-10-12 | 1989-10-11 | American Cyanamid Company | Improvements in or relating to electro-rheological fluids |
| US5217633A (en) * | 1988-06-25 | 1993-06-08 | Bayer Aktiengesellschaft | Low-temperature lubricating oil |
| US5384057A (en) * | 1990-08-09 | 1995-01-24 | E. I. Du Pont De Nemours And Company | Compositions and process of using in refrigeration |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1346150A (en) | 1974-02-06 |
| DE2237835B2 (en) | 1974-09-26 |
| CA965405A (en) | 1975-04-01 |
| FR2149558B1 (en) | 1975-03-07 |
| DE2237835C3 (en) | 1975-05-22 |
| JPS5527600B2 (en) | 1980-07-22 |
| JPS4829972A (en) | 1973-04-20 |
| FR2149558A1 (en) | 1973-03-30 |
| DE2237835A1 (en) | 1973-03-01 |
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