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  • C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
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  • C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
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  • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
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  • C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
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  • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/084—Acrylate; Methacrylate
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
  • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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  • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
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  • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
  • C10N2050/10—Semi-solids; greasy

Definitions

• This invention relates to lubricants, particularly those useful for lubrication under severe operating conditions, such as under extreme high speed and at high temperatures.
• the number of -S(CH ),,X units or groups in the final polymeric compound can vary from 10 to 1000 or more
• Oil-soluble mercapto-modified [poly(thioether)]' polymers of the above type can be prepared by reacting a mercapto compound, such as mercapto acid, ester, ether, alcohol, amine, or mixtures thereof, with an oil-soluble unsaturated essentially linear hydrocarbon polymer having a plurality of oil-solubilizing alkyl radicals of from 8 to 20 carbon atoms attached directly or indirectly to a linear hydrocarbon backbone chain prepared by reacting a lower polyene hydrocarbon with a polymerizable monomer having an oil-soluble alkyl group.
• a mercapto compound such as mercapto acid, ester, ether, alcohol, amine, or mixtures thereof
• an oil-soluble unsaturated essentially linear hydrocarbon polymer having a plurality of oil-solubilizing alkyl radicals of from 8 to 20 carbon atoms attached directly or indirectly to a linear hydrocarbon backbone chain prepared by reacting a lower polyene hydrocarbon with a polymeriz
• the unsaturated polymers which are reacted with the above mercaptocompounds are long chain oil-soluble polymers prepared by polymerizing a lower (4 to 8 carbon atoms per molecule) polyene hydrocarbon with a monoolefinically polymerizable monomer having a higher hydrocarbon moiety (10- carbon atoms) such as long chain alkyl esters of alpha,beta-unsaturated acids, such as acrylic and methacrylic acids, esters of lower unsaturated alcohols, such as vinyl and allyl alcohols and long chain fatty acids, long-chain N-alkyl unsaturated fatty acid amides, such as N-alkyl acrylamides.
• long chain alkyl esters of alpha,beta-unsaturated acids such as acrylic and methacrylic acids
• esters of lower unsaturated alcohols such as vinyl and allyl alcohols and long chain fatty acids
• long-chain N-alkyl unsaturated fatty acid amides such as N-alky
• Suitable polyene hydrocarbons for forming the copolymers are, for example, 1,3- and 1,4-pentadiene, isoprene, 1,3 hexadiene, 1,3,5 heptatriene, 1,3 cyclopentadiene, methylcyclopentadiene, 1,3- and 1,4 cyclohexa-diene, methylcyclohexadiene, and mixtures thereof.
• Representative oil-solubilizing monomer compounds which are used to form the copolymers with the polyene hydrocarbons include alpha-unsaturated long chain hydrocarbons, unsaturated esters, unsaturated amides, etc., such as decene-l, dodecene-l, tridecene-l, tetradeceriel, hexadecene-l, heptadecene-l, octadecene-l, tritriacontene- 1, tetratriacontene-l, heptacontene-l, 4-methyl-decene-1, 4,4-dimethyl-decene-l, 5,5-dimethylhexene-1, 5,5,7,7-tetramethyl-decene-l, 4,4,6,G-tetramethylheptene-1, etc., vinyl decanoate, vinyl laurate, vinyl tridecanoate, vinyl myristate, vinyl pentade
• vinyl acetylstearate vinyl dodecyl ether, vinyl tridecyl ether, vinyl tetracosyl ether, vinyl hexacosyl ether, allyl stearate, allyl dodecyl ether, N-lauryl methacrylamide, N-stearyl methacrylamide, and N,N- distearyl methacrylarnide.
• the mol ratio of the polyene hydrocarbons to the oilsolubilizing monomer compounds can be varied within relatively wide limits, e.g., from 1/ 10 to 10/1, preferably from 1/5 to 5/1, respectively.
• the polymer (prior to treatment with mercapto compound) should have a substantial amount of unsaturation and have a molecular weight of at least 500 and may be up to or over 2 million, but preferably from about 2,000 to about 800,000 and still more preferred molecular weight range is from 100,000 to 600,000.
• the polymers can be prepared thermally or in the presence of a suitable catalyst.
• a suitable catalyst such as butadienes or isoprene and long chain alpha-olefins such as alpha-docene or alpha-octadecene
• the so-called Ziegler catalysts are preferred, such as combinations of aluminum trialkyls and a variable valence metal compound, e.g., titanium tetrachloride.
• oxygen-yielding catalysts are preferred such as, for example, various organic peroxides, including aliphatic, aromatic, heterocyclic and acyl peroxides, such as diethyl peroxide, tertiary butyl hydroperoxide, dibenzoyl peroxide, dimethylthienyl peroxide, dicyclohexyl peroxide, dilauroyl peroxide and urea peroxide.
• catalysts include sodium bisulfite, diethyl sulfoxide, ammonium persulfate, alkali metal perborates, azo compounds, such as alpha, alpha-azodiisobutyronitrile; etc.
• the sulfur content of the resulting polymer is in the range of 1% to 30% and usually is about 6 to 12% by weight.
• Example 1 The copolymer of Example I was mixed with about 20% excess of merca-ptoacetic acid and the mixture was reacted in the presence of tert-butyl hydroperoxide for 2-4 hours at about 40 C. The reaction mixture was diluted with diethyl ether, water washed, filtered and dried. The final average polymer molecule contained over 600 units of -S-CH COOH groups distributed in the molecule.
• Example B The procedure of Example A was followed using the polymer of Example 11 and Z-mercaptoethanol as the mercapto compound.
• the final average polymer molecule contained over 500 units of --S-CH CH 0H groups distributed in the molecule.
• the mercapto-modified [poly(thioether)] polymers in general are oil-soluble and can be used in amounts of from about 0.5% to about 20%, preferably from about I Example Catalyst Tempeature, Polyeue/oil-soluble menoolefins ratio M01 Bromine 7 wt. No.
• the final oil-soluble polymeric additive was prepared by reacting the unsaturated copolymers, such as those of Examples I-X, with one or more of the merca-pto compounds by suitable means, such as described in I our. Am. Chem. Soc., 79, 362 (1957) or Ir. Org. Chem., 22, 197 (1957), preferably between room temperature and about 100 C. and in the presence of a free radical catalyst such as an azo or a peroxide catalyst or ultraviolet light and in a non-reactive solvent such as benzene, toluene, xylene or the like.
• suitable means such as described in I our. Am. Chem. Soc., 79, 362 (1957) or Ir. Org. Chem., 22, 197 (1957), preferably between room temperature and about 100 C. and in the presence of a free radical catalyst such as an azo or a peroxide catalyst or ultraviolet light and in a non-reactive solvent such as benzene, toluen
• Suitable initiators include peroxides such as tert-butyl peroxide and azo compounds such as alpha,alpha-azodiisobutyronitrile or emulsion redox systems such as a mixture of sodium bisulfite and persul-fate, ammonium persulfate, alkali metal (Na) perborates, etc. s
• oil compositions containing these polymers a small amount (01-10%) of an oil-soluble branched-chain aliphatic monohydric alcohol. These alcohols can efiectrvely stabilize such compositions without destroying the extreme pressure properties of such oil compositions.
• the oil-soluble alkanols particularly useful for this purpose are the so-called OX0 alcohols derived from branched-chain olefins, such as polymers of lower alkenes of 3 to 5 carbon atoms, and copolymers of mixtures of such alkenes, by catalyzed reaction with carbon monoxide and hydrogen in accordance with the conditions of the .OXO process, as is well known in the art.
• OX0 alcohols derived from branched-chain olefins, such as polymers of lower alkenes of 3 to 5 carbon atoms, and copolymers of mixtures of such alkenes, by catalyzed reaction with carbon monoxide and hydrogen in accordance with the conditions of the .OXO process, as is well known in the art.
• alkanols include 6-methyl-lheptanol, Z-n-propyl-l-pentanol, 3-n-propyl-1 hexanol, 2,2-dimethyl-1-octanol, 10,10-dimethyl-1undecanol, 3- isopropyl-l-heptanol and mixtures thereof.
• the lubricating oil base is suitably selected from various synthetic oils or natural hydrocarbon oils having a viscosity range of from 50 SUS at 100 F. to 250 SUS at 210 F. (SAE viscosity number ranging from SAE 5 to SAE 90).
• the natural hydrocarbon oils are obtainable from paraifinic, naphthenic, asphaltic or mixed base crudes, and/or mixtures thereof.
• Useful synthetic oils include polymerized oletins, alkylated aromatics, isomerized waxes, copolymers of alkylene glycols and alkyleneoxide (Ucon fluid, US.
• organic polyesters such as esters of an aliphatic dibasic acid and a monohydric alcohol, such as di- 2-ethyl hexyl sebacate or di-2-ethyl hexyl adipate esters of polyhydric alcohols and monocarboxylic acids, such as pentaerythritol tetracaproate, and the like.
• Useful Ucon fluids are Ucon 50HB170, Ucon 50HB660 or Ucon LBSSOX, which are copolymers of ethylene and 1,2- propylene oxides; the diols as well as their monoand dialkyl ethers are useful.
• the hydrocarbon oils may be blended with fixed oils such as castor oil, lard oil and the like and/or synthetic oils as mentioned or silicone polymers and the like. Typical oils of this type are petroleum motor oils (A) and (B), characterized below,
• Petroleum Oil (A) B) (SAE 10W) (SAE 30) Pour point, F 10 5 390 415 Viscosity, SUS at 210 F 44 50 Viscosity Index .s 90 65
• Other suitable oils are specification gas turbine lube oils having the following properties:
• Composition A Example A additive 2%.
• Composition D Example A additive 2%. C H OH(OXO- alcohol) 6%. 1010 Mineral oil Balance.
• Composition E Example D additive 1%. 1010 Mineral oil Balance.
• Composition F Example B additive 2%. C13H2'7OH(OXO alcohol) 4%. a 1010 Mineral oil Balance.
• Composition G Example E additive 3%. SAE Mineral oil Balance. Composition H Example F additive 2%.
• Ucon 5'0HB660 polyethylene-propylene glycol having a SUS viscosity at F.
• Composition J Example A additive 5%. Di-Z-ethylhexyl sebacate Balance.
• Compositions of this invention were evaluated for their extreme pressure properties on a Spur-Gear machine.
• the machine consists essentially of two geometrically similar pairs of gears connected by twoparallel shafts.
• the gear pairs are placed in separate gear boxes, which also contain the supporting ball bearings.
• One of the shafts consists of two sections connected by a coupling. Loading is accomplished by locking one side of the coupling and applying torque to the other.
• the conditions of the test were:
• Compositions A, B, D and F carried score loads of from 3,000 to 12,000 lbs./in.
• Compositions I and J are equally eifective and Compositions C, E, G and H carried score loads of over 1,500 lbs'./in.
• 1010 mineral oil containing separately 2% of the polymers of Ex I to X carried score loads of about 700 draulic fluids of the oil, water-in-oil emulsion or synthetic .type with respect to wear inhibition and the like.
• a lubricating oil composition comprising a major amount of mineral lubricating oil and from about 0.5% to about 20%, of an oil-soluble high molecular weight polymer containing C C alkyl groups and S-(CH X groups attached to different carbon atoms of a linear hydrocarbon chain wherein n is an integer of l to 4 and X is a polar group selected from the group consisting of COOR, selected from the group consisting of hydrogen and C alkyl radicals said polymer having a sulfur content OR and NR and R is] of from 1% to 30%, and a molecular weight from 2,000 7 2.
• a lubricting oil composition comprising a major amount of mineral lubricating oil and from about 0.5% to about 20%, of an oil-soluble linear hydrocarbon polymer containing C -C alkyl groups and groups attached to different carbon atoms of the linear amount of mineral lubricating oil and from about 0.5%
• an oil-soluble linear hydrocarbon polymer containing -C -C alkyl groups and groups attached to difierent carbon atoms of the linear hydrocarbon chain said polymer having a sulfur content of from 1% to 30% and a molecular weight of from 2,000 to 800,000.
• a lubricating oil composition comprising a major amount of mineral lubricating oil and from about 0.5
• composition of claim 4 wherein the --C C alkyl groups are attached to different carbon atoms in the linear hydrocarbon chain through carboxyl, groups.
• a lubricating oil composition comprising a major amount of mineral lubricating oil and from about 1% to about 5% of an oil-soluble linear hydrocarbon polymer containing C C alkyl groups and -SCH CH OH groups attached to different carbon atoms of the linear hydrocarbon chain, said polymer having a sulfur content of from 6% to 12% and a molecular weight of from 100,000 to 600,000.
• composition of claim 1 containing from 0.1% to 10% of an oil-soluble branched-chain alkanol containing 8 to 13 carbon atoms.
• composition of claim 3 containing from 0.1% to 10% of an oil-soluble branched-chain alkanol containing 8 to 13 carbon atoms.
• composition of claim 4 containing from 0.1%
• composition of claim 5 containing from 0.1% to 10% of an oil-soluble branched-chain alkanol containing 8 to 13. carbon atoms. g '14.
• composition of claim 6 containing from 0.1% to 10% of an oil-soluble branched-chain alkanol containing 8 to 13 carbon atoms;

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• 0
  • BE BE578775D patent/BE578775A/xx unknown
  • NL NL239215D patent/NL239215A/xx unknown
• 1958
  • 1958-05-19 US US735960A patent/US3041283A/en not_active Expired - Lifetime
• 1959
  • 1959-05-15 GB GB16680/59A patent/GB846856A/en not_active Expired
  • 1959-05-19 DE DEN16732A patent/DE1148680B/de active Pending
  • 1959-05-19 FR FR794936A patent/FR1233702A/fr not_active Expired

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