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
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/0834—Compounds having one or more O-Si linkage
  • C07F7/0838—Compounds with one or more Si-O-Si sequences
• • 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
  • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
  • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes

Definitions

• the present invention relates to novel disiloxanes. More particularly, these disiloxanes are of the formula in which each R is independently selected from the group consisting of alkyl radicals having from 14 to 30 inclusive carbon atoms and each R is independently selected from the group consisting of methyl and phenyl radicals.
• Silicone chemistry has reached a stage of detailed development. Most of the technology is focused on the monomeric silanes and on higher polymeric siloxanes, such as used for lubricants or elastomers. Relatively little effort has been expended in the area of disiloxanes, the polysiloxanes containing the least number of silicon atoms.
• the higher alkyl substituted disiloxane of the invention includes and mixtures thereof.
• An alternate method involves the preparation of RR (CH SiCl by the reaction of HR'(CH )SiCl with the described unsaturated hydrocarbon in the presence of chloroplatinic acid and subsequent hydrolysis of the product chlorosilane to obtain the disiloxane. Conventional hydrolysis techniques are utilized.
• the disiloxanes containing the shorter chain alkyl substituents are low viscosity fluids at room temperatures, while the higher alkyl substituted compounds are solid waxy materials.
• the disiloxanes of the invention exhibit much greater resistance to gelling at elevated temperatures. This high temperature stability is a particular advantage in applications, such as die casting, where buildup of the lubricant or release agent is undesirable.
• the novel disiloxanes function as internal lubricants when used as additives for thermal plastic materials, such as nylon, providing greater ease of extrusion of such materials.
• the (Cgf-Czg)(CH3)2SiOSi(CH3)2(C22-C2g) species is especially preferred in that it not only provides internal lubrication but significantly improves the impact strength of polyamide extrusions at the one weight percent additive level.
• EXAMPLE 1 A 3-liter flask fitted with a mechanical stirrer, thermometer, addition funnel and condenser was charged with 1357 grams (6.92 mols) of l-tetradecene. To this, was added 0.2 milliliter of a chloroplatinic acid solution (0.1 molar chloroplatinic acid in isopropanol). The solution was stirred and heated to C. and 421.8 grams (3.18 mols) of H(CH SiOSi(CH H was added slowly from the addition funnel at a rate suflicient to keep the reaction temperature at C. The reaction was exothermic. When all the disiloxane had been added, the solution temperature was maintained at 120 overnight while stirring to complete the reaction.
• a chloroplatinic acid solution 0.1 molar chloroplatinic acid in isopropanol
• the reaction product was stripped at a temperature of 204 C./0.4 mm. Hg of hydrogen to remove the unreacted olefin.
• the product was cooled, treated with activated carbon and filtered to obtain 1419 grams of C H (CH SiOSi(CH C I-I disiloxane Was a clear water-white fluid having a viscosity of 20.2 cs. at 77 F., a flash point of 475 F. and a freezing point of 18 C.
• EXAMPLE 2 A five-liter flask, fitted with mechanical stirrer, thermometer, reflux condenser and addition funnel was charged with 1855 grams (6.5 mols) of a normal alpha olefin fraction containing species having from 22-28 inclusive carbon atoms and 0.5 milliliter of 0.1 molar chloroplatinic acid in isopropanol. This mixture was heated to C. while stirring moderately and 360 grams of H(CH SiOSi(CH H was added at such a rate that the exotherm from the reaction was maintained at a temperature from 125 to 150 C.
• reaction product was stripped at 260 under vacuum to remove the unreacted olefin. It was then cooled, treated with activated carbon and filtered to obtain a mixture product of the formula 22 45 2s 57) 3 zsiosi 3 2( z2 45 2a 57) which was a white waxy material having a melting point of 35-45 C.
• Disiloxanes of the formula 1a s7( a)2 3)2 1a a'1 and (C16H33"'C20H41) 3 asiosi 3 2 1s a3 20 41) were produced by reacting the corresponding alpha-olefin with the disiloxane utilizing the above described method.
• This chlorosilane adduct can be hydrolyzed by the addition of water to yield a low viscosity fluid of the formula C14H29(C6H5) 3) 3) s) 14 29- EXAMPLE 4
• the lubrication properties and gel times of the various disiloxanes were determined by the 4-ball method in which a /2 inch steel ball is rotated against three stationary /2 inch steel balls at a rate of 1200 r.p.m. at a temperature of 167 F. for 30 minutes under loads of 4, and 40 kilograms. At the end of this time, the length and width of the scar formed on each stationary ball is measured and the average of these six measurements is taken as the wear scar diameter. The smaller the wear scar, the better the lubricant.
• the gel times an indication of stability at high temperatures, were determined by placing 10 grams of the disiloxane contained in a 50 ml. beaker in an air circulating oven at 450 F. and recording the time necessary to eifect gellation of the fluid.
• each R is independently selected from the group consisting of alkyl radicals having from 14 to 30 inclusive carbon atoms; and each R is independently selected from the group consisting of methyl and phenyl radicals.
• each R is a methyl radical and R is selected from the group consisting of alkyl radicals having from 22-28 carbon atoms, and mixtures thereof.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Silicon Polymers (AREA)
• Lubricants (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=21763997

Family Applications (1)

Country Status (6)

Cited By (6)

Families Citing this family (1)

• 1970
  • 1970-02-25 US US14183A patent/US3632619A/en not_active Expired - Lifetime
  • 1970-10-22 JP JP45092462A patent/JPS4832547B1/ja active Pending
• 1971
  • 1971-02-24 FR FR7106301A patent/FR2079015A5/fr not_active Expired
  • 1971-02-24 BE BE763364A patent/BE763364A/xx unknown
  • 1971-02-25 DE DE2109051A patent/DE2109051C3/de not_active Expired
  • 1971-04-19 GB GB20316/71A patent/GB1282839A/en not_active Expired

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