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
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
  • C10M105/54—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen, halogen and oxygen
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09G—POLISHING COMPOSITIONS; SKI WAXES
  • C09G3/00—Ski waxes
• • 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
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
  • C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen 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
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
  • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
  • C10M2211/0225—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic used as base material
• • 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
  • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
  • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
  • C10M2211/0245—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic used as base material
• • 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
  • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
  • C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
  • C10M2211/0425—Alcohols; Ethers; Aldehydes; Ketones used as base material

Definitions

• the invention relates to the use of partially fluorinated compounds as ski lubricants.
• Ski waxes are used in order to enhance the sliding properties of skis.
• Conventional ski waxes generally include relatively high molecular mass hydrocarbons such as paraffins, fatty acids, fatty acid esters, and fatty alcohols or mixtures of these and similar compounds.
• Certain fluorinated compounds have proven extremely effective ski waxes and are employed particularly in the high-performance sport.
• the reason for the great effectiveness of fluorinated waxes is the coating of the ski with a fluorinated surface possessing very low surface tension, thereby greatly reducing the friction.
• fluorochemicals it is possible to lower the surface tension of, say, polyethylene (31 dyn/cm) to levels of 6-18 dyn/cm. The value of 6 dyn/cm is achieved for a surface composed of perfectly oriented CF3 groups.
• WO 89/10950 describes the addition of PTFE micropowder to unfluorinated ski waxes.
• the molar weight of the PTFE is preferably 50 000-400 000 g/mol and the particle size is less than 15 ⁇ m.
• EP 0 132 879 describes the synthesis of relatively long-chain perfluoroalkanes of the formula F(CF 2 ) n F and also their use as lubricants for surfaces.
• DE 4 139 765 describes oligomers of fluorinated olefins of the formula F(CF 2 ) n —CH ⁇ CH 2 .
• the product can be prepared by free-radical oligomerization of said olefins and is suitable as a lubricant for a variety of surfaces.
• U.S. Pat. No. 5,502,225 and DE 100 29 623 describe fluorinated oligomeric urethanes which are obtained by addition reaction of fluorine-free isocyanates and fluorinated alcohols as essential components.
• EP 0 421 303 describes the use of partially fluorinated polyacrylates.
• the preparation takes place by free-radical copolymerization of fluorinated acrylates such as 2-perfluoroalkylethyl acrylate, for example, with nonfluorinated monomers such as long-chain fatty alcohol acrylates, for example.
• Ski waxes may also be provided with a variety of additives in order to prevent the friction-induced electrostatic charging, which can lead to the adherence of a water film.
• CH 660 018 describes the use of graphite for the purpose of increasing the conductivity.
• certain partially fluorinated compounds can surprisingly likewise be used as ski waxes.
• These compounds are coupling products of one or more perfluoroalkyl radicals with a fluorine-free alkyl or aryl radical. Apart from oxygen atoms in the form of ether bonds, the coupling product must be composed exclusively of the elements fluorine, carbon, and hydrogen. Absent an ether bond, the fluorine-free alkyl or aryl radical must have at least one monocyclic or polycyclic structural element, which may be saturated, unsaturated, aromatic, possibly branched, and monofunctional or bifunctional.
• the invention provides lubricants intended for solid surfaces and comprising a partially fluorinated compound of formula 1 RF—(A) a —(O) b —(B) c —(D) d —(RF) e (1) where
• RF is a perfluorinated radical of formula F(CF 2 ) n -,
• n is a number from 1 to 20,
• A is C 1 -C 30 , preferably C 1 -C 18 , alkylene.
• B is arylene having 6 to 14 carbon atoms or is a saturated or unsaturated monocyclic or polycyclic hydrocarbon having 3 to 30, preferably 3 to 18 carbon atoms,
• D is hydrogen or C 1 -C 30 , preferably C 1 -C 18 , alkyl,
• a is zero or 1
• b, c, and d are zero, 1 or 2 and e is zero or 1, with the proviso that b and c are not simultaneously zero.
• the compounds of formula above can be synthesized in principle in a number of ways. The most common is the addition reaction of perfluoroalkyl iodides with olefinic double bonds, free-radically or metal-catalyzed, for example, and substitution reaction of perfluoroalkyl iodides on aromatic systems, which are carried out with metal catalysis, for example. It will be appreciated that other methods, not specified here but sufficiently well known to the skilled worker, of linking perfluoroalkyl radicals to fluorine-free compounds are also possible.
• the compounds described can be applied in conventional manner to the sliding surface of the ski, by means for example of the melting of these compounds, where present in solid form, with a hot iron and their application to the ski.
• the compounds described can be applied in the form of a solution in one or more organic solvents, preferably in a concentration of 0.5%-5%, or in the form of a solid, to the ski.
• the wax is used in the form of a solution it is necessary to select a suitable solvent, depending on the fluorine content. At high fluorine content it may be necessary to use fluorinated solvents such as perfluorohexane, 1H-perfluorohexane or Frigen products, for example.
• nonfluorinated solvents are suitable as well, such as ethyl acetate, butyl acetate or THF, for example. It is also possible to use mixtures of two or more solvents. A further possibility is to employ the active compound in the form of a suspension or dispersion.
• the fluorinated compounds described can be combined, alone or in a mixture, with other fluorinated or nonfluorinated ski waxes.
• the fluorinated active compounds described are suitable not only as ski waxes but also for coating surfaces of a wide variety of kinds such as metal, plastic, and glass, for example.
• the coating applies a hydrophobic and oleophobic film to the surface in question, and said film greatly reduces the friction.
• Perfluoroalkyl iodide and olefin component are reacted in a molar ratio of 1:1 with 5 mol % of percarbonate and/or peroxide free-radical initiator (e.g., dilauryl peroxide) at 100-110° C. for 2 h. Then a further 5 mol % of free-radical initiator are added and reaction continues at 100-110° C. for 2 h. After the reaction mixture has cooled to room temperature, 1.5 times the mass of isopropanol, 0.5 times the mass of acetic acid, and 150 mol % of zinc powder are added and the mixture is stirred for 1 h. Reaction then takes place under reflux conditions for a further 3 h. Following filtration to remove insoluble fractions, the solvent is stripped off and the residue is freed under a high vacuum from unreacted starting materials and byproducts. The purity of the product is between 85% and 95%.
• percarbonate and/or peroxide free-radical initiator
• Compound 7 was prepared in accordance with a set of instructions from J. Org. Chem. 6, (2002), 7185-7192 by coupling 2 mol of RFI and one mole of biphenyl with copper in DMSO as solvent.
• Compound 8 was prepared by a set of instructions from Organikum, Wiley-VCH, 21 st edition, 2001, p. 375 by Friedel-Crafts alkylation of perfluoroalkylpropyl chloride (prepared by reacting 3-perfluoroalkyl-1-propanol and thionyl chloride) and decylbenzene, with catalysis by aluminum chloride.
• Compound 9 was prepared by a set of instructions following the general procedure of Organikum, Wiley-VCH, 21 st edition, 2001, p. 239 by reacting perfluoroalkylpropyl tosylate (prepared by reacting 3-perfluoroalkyl-1-propanol with p-toluenesulfonyl chloride) and dodecylphenol in acetone with potassium carbonate.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Lubricants (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Moulds For Moulding Plastics Or The Like (AREA)

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• 2003
  • 2003-04-15 DE DE10317198A patent/DE10317198A1/de not_active Withdrawn
• 2004
  • 2004-04-08 JP JP2006505061A patent/JP2006523738A/ja not_active Withdrawn
  • 2004-04-08 DE DE502004005433T patent/DE502004005433D1/de not_active Expired - Fee Related
  • 2004-04-08 ES ES04726455T patent/ES2294491T3/es not_active Expired - Lifetime
  • 2004-04-08 WO PCT/EP2004/003755 patent/WO2004092291A1/de active IP Right Grant
  • 2004-04-08 US US10/553,217 patent/US20060270570A1/en not_active Abandoned
  • 2004-04-08 EP EP04726455A patent/EP1615976B1/de not_active Expired - Lifetime
  • 2004-04-08 CN CN200480009967.0A patent/CN1809621A/zh active Pending
  • 2004-04-08 AT AT04726455T patent/ATE377637T1/de not_active IP Right Cessation
• 2005
  • 2005-11-03 NO NO20055169A patent/NO20055169L/no not_active Application Discontinuation

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