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
  • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
  • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
  • C10M129/04—Hydroxy compounds
  • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
• • 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
  • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
  • C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
  • C10M129/88—Hydroxy compounds
  • C10M129/91—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
• • 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
  • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
  • C10M135/20—Thiols; Sulfides; Polysulfides
  • C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
  • C10M135/30—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups; Derivatives thereof
• • 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
  • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
  • C10M159/12—Reaction products
  • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
  • C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
• • 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
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/027—Neutral salts thereof
• • 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
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/028—Overbased salts thereof
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
  • C10M2219/088—Neutral 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
  • C10M2219/089—Overbased salts

Definitions

• This invention relates to a friction modifier comprising a chain-hydrocarbon-group-substituted metal phenate and a lubricating oil composition containing the same, and more specifically to a friction modifier comprising a specific chain-hydrocarbon-group-substituted metal phenate having excellent friction reducing ability and a lubricating oil composition containing the same.
• an automatic transmission fluid which had been obtained by adding magnesium sulfonate used as a metallic detergent, especially over-based magnesium sulfonate having a base number of 300 mg-KOH/g or greater in a base stock in order to improve its friction characteristics (see JP Kokai 62-84190). Further, it has also been proposed to use calcium salicylate as a friction coefficient modifiers for automatic transmission fluids (see JP Kokai 5-163496).
• the present invention has as objects thereof the provision of a novel friction modifier having friction reducing ability and also the provision of a lubricating oil composition containing the friction modifier.
• the present invention relates in a first aspect thereof to a friction modifier comprising at least one chain-hydrocarbon-group-substituted metal phenate substituted by at least one chain hydrocarbon group, characterized in that said chain hydrocarbon group has an alkyl chain linearity of 20% or higher as determined by a carbon nuclear magnetic resonance measurement ( 13 C-NMR measurement).
• the present invention also relates in a second aspect thereof to a lubricating oil composition characterized in that said lubricating oil composition comprises:
• the chain-hydrocarbon-group-substituted metal phenate which is used as an effective component of the friction modifier according to the present invention, is formed basically of a phenol component, which carries at least one chain hydrocarbon group bonded thereto, and a metal component.
• the above metal phenate may be subjected to sulfurization to contain compounds with two or more aromatic groups bonded together by one or more sulfur atoms, respectively, and the above metal phenate may also contain one obtained by subjecting it to an over-basing treatment as needed.
• chain hydrocarbon group in the chain-hydrocarbon-group-substituted metal phenate according to the present invention those capable of meeting the following requirements are suitable.
• the chain hydrocarbon group of the chain-hydrocarbon-group-substituted metal phenate according to the present invention is an alkyl group having an average carbon number of 12 or more per hydroxyl group.
• an alkyl group having an average carbon number of from 12 to 40 is preferred.
• An average carbon number smaller than 12 involves a potential problem that sufficient friction reducing effects may not be obtained.
• chain-hydrocarbon-group-substituted metal phenate according to the present invention, one containing at least one or more alkyl groups having 12 to 30 carbon atoms is particularly preferred.
• hydroxyl group as used herein means an - OH group existing in a chain-hydrocarbon-group-substituted metal phenate in a form as converted under 13 C-NMR measuring conditions.
• average carbon number per hydroxyl group indicates an average carbon number of an alkyl group as calculated by a 13 C-NMR measurement by supposing that an aromatic carbon bonded to a hydroxyl group is 1.
• alkyl group can include dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, pentatriacontyl, and octatriacontyl.
• the above alkyl group has a specific linearity as determined by a 13 C-NMR measurement as indicated above under the requirement (ii), and is a requirement indispensable for the unique chain-hydrocarbon-group-substituted metal phenate according to the present invention.
• the chain-hydrocarbon-group-substituted metal phenate according to the present invention is one having an alkyl chain linearity of 20% or higher, preferably 30% or higher as determined by a 13 C-NMR measurement.
• the 13 C-NMR measurement was conducted by converting the metal phenate into its corresponding alkyl phenol.
• the present inventors were interested in the existence of a correlation between the linearity of the alkyl group or groups in the chain-hydrocarbon-group-substituted metal phenate and its friction reducing effects, and have ascertained that the metal phenate exhibits better friction reducing effects as the alkyl chain linearity becomes higher and also that an alkyl chain linearity lower than 20% cannot exhibit the effects fully although an alkyl chain linearity of 20% or higher, especially of from 30% to 80% shows particularly marked effects.
• a chain-hydrocarbon-group-substituted metal phenate excellent in friction reducing effects can still be obtained provided that its alkyl chain linearity as determined by a 13 C-NMR measurement is 20% or higher, even when the chain-hydrocarbon-group-substituted metal phenate contains two or more hydrocarbon groups per hydroxyl group or is a mixture of two or more different compounds (metal phenates). That is, the overall alkyl chain linearity is 20% or higher.
• a metal phenate, hydrocarbon groups of which are each a linear alkyl group having 12 or more carbon atoms is preferred from the viewpoint that it can substantially improve friction reducing effects.
• the metal component represented by M in the formula (I) of the chain-hydrocarbon-group-substituted metal phenate according to the present invention can be an alkali metal or an alkaline earth metal. Further, a metal of an atomic number in a range of from 12 to 56 is also suited. Specific examples of suitable metals can include sodium, potassium, lithium, calcium, magnesium and barium. In addition, aluminum, zinc, tin, chromium, copper, cobalt and the like are also effective. Particularly preferred are alkaline earth metals such as calcium, magnesium and barium.
• Typical illustrative compounds of the chain-hydrocarbon-group-substituted metal phenate according to the present invention can be represented by the following formulas (I) to (II):
• R 1 and R 2 are alkyl groups which may be the same or different, the average carbon number of the total carbon number of R 1 and the total carbon number of R 2 , said average total carbon number being equivalent to the number of carbon atoms per hydroxyl group, may preferably be from 12 to 40, and the alkyl chain linearity as determined by a 13 C-NMR measurement is 20% or higher.
• alkyl group can include dodecyl, tridecyl, tetradecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, and triacontyl.
• M is appropriately an alkaline earth metal, although it can be other divalent metals described above.
• n indicates the number of alkyl groups substituted on the aromatic group and is an integer of from 1 to 5, preferably an integer of 1 to 2. In the respective formulas, they can be the same or different. Further, x is an integer of from 1 to 5 in the formula (II).
• the chain-hydrocarbon-group-substituted metal phenate can specifically be a metal salt of an alkylphenol or alkylphenol sulfide, which can be a basic salt or over-based salt in addition to a neutral salt.
• Its salt type can be chosen as desired depending on its application.
• the metal salt of the alkylphenol or alkylphenol sulfide can be prepared by a reaction between the alkyl phenol or alkylphenol sulfide and a metal compound, for example, an oxide, hydroxide, alkoxide or the like.
• the over-based salt can be obtained by a method known per se , in the art.
• the alkylphenol sulfide can be produced by reacting the alkylphenol with sulfur or a sulfur-containing compound such as hydrogen sulfide and is obtained in the form of a mixture that two or more phenol groups are bonded by one or more sulfur atoms, respectively.
• a metal phenate mixture with an alkyl chain linearity controlled within the above-described specific range can also be obtained by mixing various metal phenates of different alkyl chain linearities.
• a friction modifier comprising such a specific chain-hydrocarbon-group-substituted metal phenate as described above can be provided.
• This friction modifier is oil-soluble. It can be used by dissolving it in a hydrocarbon or another solvent and diluting the resultant concentrate as needed or as a component of an additive package in combination with other additives.
• the lubricating oil composition according to the present invention contains the lubricating base stock and the chain-hydrocarbon-group-substituted metal phenate.
• the base stock can be any one of mineral base stocks, synthetic base stocks and vegetable base stocks, or can be a blended base stock of two or more of these base stocks.
• a mineral base stock it is possible to use, for example, a mineral oil obtained by the treatment of a lubricating oil fraction, which is in turn available by vacuum distillation of an atmosphere distillation residue of paraffin-base, neutral or naphthene-base crude oil, through a refining step such as solvent refining, hydrocracking, hydro-refining, catalytic dewaxing, solvent dewaxing or clay treatment; a mineral oil obtained by subjecting a vacuum distillation residue to solvent deasphalting and then treating the resulting deasphalted oil through the above-described refining step; a mineral oil obtained by isomerizing wax components; or a blended oil thereof.
• a refining step such as solvent refining, hydrocracking, hydro-refining, catalytic dewaxing, solvent dewaxing or clay treatment
• an aromatic extraction solvent such as phenol, furfural or N-methylpyrrolidone
• a solvent for the solvent dewaxing liquefied propane, MEK/toluene, MEK/MIBK, or the like
• hydro-refined oil is preferred from the standpoint of quality such as oxidation stability, and one containing, for example, 2 wt% or less of aromatic hydrocarbons and 90 wt% or more of saturated hydrocarbons can be used although the preferred mineral base stock varies depending on the application purpose of the lubricating oil.
• Examples of synthetic base stocks can include poly( ⁇ -olefin) oligomers; polybutene; alkylbenzenes; polyol esters such as trimethylolpropane esters and pentaerythritol esters; polyoxyalkylene glycols; polyoxyalkylene glycol esters; polyoxyalkylene glycol ethers; dibasic acid esters; phosphate esters; and silicone oils.
• These base stocks can be used either singly or in combination.
• vegetable base stocks can include rape seed oil, palm oil, coconut oil, olive oil and sunflower oil.
• a blended base stock obtained by suitably blending plural base stocks so that the blended base stock has a viscosity and other properties desired for the intended application of the lubricating oil composition.
• the kinematic viscosity at 100°C in a range of from 2 mm 2 /s to 30 mm 2 /s, especially from 3 mm 2 /s to 10 mm 2 /s for a lubricating oil for internal combustion engines, the kinematic viscosity at 100°C in a range of from 2 mm 2 /s to 30 mm 2 /s, especially from 3 mm 2 /s to 15 mm 2 /s for an automatic transmission fluid, and the kinematic viscosity at 4°C in a range of from 10 mm 2 /s to 1,000 mm 2 /s, especially from 20 mm 2 /s to 500 mm 2 /s.
• the chain-hydrocarbon-group-substituted metal phenate for use in the lubricating oil composition according to the present invention can be added to the lubricating base stock in a proportion of from 0.01 to 10 wt%, preferably from 0.05 to 5 wt% based on the whole weight of the lubricating oil composition or in a proportion of from 1 ppm to 10,000 ppm, preferably from 50 ppm to 5,000 ppm in terms of the metal, although the proportion varies depending on the application field of the lubricating oil.
• viscosity index improvers ashless dispersants, anti-oxidants, extreme pressure agents, wear inhibitors, metal deactivators, pour-point depressants, rust inhibitors, other friction modifiers and other additives as needed.
• Illustrative usable examples of the viscosity index improvers can include polymethacrylates, polyisobutylenes, ethylene-propylene copolymers, and hydrogenated styrene-butadiene copolymers. These viscosity index improvers are used generally in a proportion of from 3 wt% to 35 wt%.
• Illustrative of the ashless dispersants can be polybutenylsuccinimides, polybutenylsuccinamides, benzylamines, and succinate esters. They can be used generally in a proportion of from 0.05 wt% to 7 wt%.
• anti-oxidants can include amine-type anti-oxidants such as alkylated diphenylamines, phenyl- ⁇ -naphthylamine and alkylated phenyl- ⁇ -naphthylamines; phenolic anti-oxidants such as 2,6-di-t-butylphenol and 4,4'-methylene-bis(2,6-di-t-butylphenol); and zinc dithiophosphate. They can be used generally in a proportion of from 0.05 wt% to 5 wt%.
• extreme pressure agents can be dibenzyl sulfide and dibutyl disulfide. They can be used generally in a proportion of from 0.05 wt% to 3 wt%.
• metal deactivators can include benzotriazole, benzotriazole derivatives, and thiadiazole. They can be used generally in a proportion of from 0.01 wt% to 3 wt%.
• pour-point depressants can be ethylene-vinyl acetate copolymers, chlorinated paraffin-naphthalene condensation products, polymethacrylates, and polyalkylstyrenes. They can be used generally in a proportion of from 0.1 wt% to 10 wt%.
• wear inhibitors can be phosphate esters, zinc thiophosphate, and sulfur compounds. They can be used generally in a proportion of from 0.01 wt% to 5 wt%.
• the friction modifier according to the present invention which comprises the chain-hydrocarbon-group-substituted metal phenate
• the lubricating oil composition according to the present invention which contains the friction modifier
• alkyl chain linearities of metal phenates employed in the following Examples and the like and, as performance evaluation of lubricating oil compositions, friction coefficients were measured by the following methods.
• Each metal phenate was converted into its corresponding alkylphenol, and under the following measuring conditions, its 13 C-NMR spectrum was measured. Further, its alkyl chain linearity was calculated in accordance with the below-described formula.
• Calcium Phenate 1 (total base number: 85 mg-KOH/g), which had an average alkyl carbon number of 19 per hydroxyl group and an alkyl chain linearity of 45.3%.
• a lubricating oil composition was formulated by adding the phenate to a refined mineral oil "100SN" (4.2 mm 2 /s at 100°C) as a lubricating base stock in a proportion of 140 ppm in terms of calcium based on the whole weight of the lubricating oil composition.
• the friction coefficient of the resultant lubricating oil composition was measured by the above-described method. It was found to be 0.10.
• a lubricating oil composition was formulated in exactly the same manner as in Example 1 except that the proportion of Calcium Phenate 1 was increased from 140 ppm to 560 ppm in terms of calcium. When subjected to a performance evaluation, its friction coefficient was found to be 0.09.
• Calcium Phenate 2 (total base number: 260 mg-KOH/g), which had an average alkyl carbon number of 20 per hydroxyl group and an alkyl chain linearity of 28.2%.
• a lubricating oil composition was formulated by adding the phenate to a lubricating base stock, which was the same as that employed in Example 1, in a proportion of 950 ppm in terms of calcium based on the whole weight of the lubricating oil composition.
• the resultant lubricating oil composition was subjected to the above-described performance evaluation. Its friction coefficient was found to be 0.09.
• a lubricating oil composition was formulated in exactly the same manner as in Example 3 except that the proportion of Calcium Phenate 2 was increased from 950 ppm to 1,900 ppm in terms of calcium.
• the resultant lubricating oil composition was subjected to a performance evaluation. Its friction coefficient was found to be 0.09.
• a lubricating oil composition was formulated in exactly the same manner as in Example 3 except that the proportion of Calcium Phenate 2 was increased to 5,700 ppm in terms of calcium.
• the resultant lubricating oil composition was subjected to a performance evaluation. Its friction coefficient was found to be 0.09.
• the lubricating base stock i.e., the purified mineral oil alone was subjected to a performance evaluation. Its friction coefficient was found to be 0.14.
• Calcium Phenate 3 (total base number: 250 mg-KOH/g), which had an average alkyl carbon number of 20 per hydroxyl group and an alkyl chain linearity of 15.5%.
• a lubricating oil composition was formulated by adding the phenate to a refined mineral oil, which was the same as that employed in Example 1, in a proportion of 950 ppm in terms of calcium based on the whole weight of the lubricating oil composition. As a result of a performance evaluation, its friction coefficient was found to be 0.14. No advantageous effect was available from the addition of Calcium Phenate 3 the alkyl chain linearity of which is lower than 20%.
• a lubricating oil composition was formulated in exactly the same manner as in Comparative Example 2 except that the proportion of Calcium Phenate 3 was increased to 5,700 ppm in terms of calcium.
• the resultant lubricating oil composition was subjected to a performance evaluation. Its friction coefficient was found to be 0.13.
• a in-hydrocarbon-group-substituted metal phenate having an alkyl chain linearity of 20% or higher has high friction reducing effects, is useful as a friction modifier especially for lubricating oils, and can improve the friction characteristics of lubricating oil compositions.

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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)

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• 1998
  • 1998-03-31 JP JP10409498A patent/JPH1161164A/ja active Pending
  • 1998-05-22 CA CA 2235446 patent/CA2235446A1/en not_active Abandoned
  • 1998-06-12 DE DE1998600723 patent/DE69800723T2/de not_active Expired - Fee Related
  • 1998-06-12 EP EP98110773A patent/EP0884379B1/de not_active Expired - Lifetime

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