WO2022189047A1 - Low viscosity functional fluid composition - Google Patents

Low viscosity functional fluid composition Download PDF

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Publication number
WO2022189047A1
WO2022189047A1 PCT/EP2022/050757 EP2022050757W WO2022189047A1 WO 2022189047 A1 WO2022189047 A1 WO 2022189047A1 EP 2022050757 W EP2022050757 W EP 2022050757W WO 2022189047 A1 WO2022189047 A1 WO 2022189047A1
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Prior art keywords
fluid
formula
fluid according
alkyl
weight
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PCT/EP2022/050757
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English (en)
French (fr)
Inventor
Felix HÖVELMANN
Andreas Endres
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Clariant International Ltd
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Priority to EP22701202.8A priority Critical patent/EP4305131A1/de
Publication of WO2022189047A1 publication Critical patent/WO2022189047A1/en

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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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
    • 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
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • 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
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/046—Hydroxy ethers
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/124—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers 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
    • 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
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C10M2209/1045—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only 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
    • 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
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • C10M2209/1085—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/26—Waterproofing or water resistance
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • the present invention relates to a low viscosity functional fluid composition
  • a low viscosity functional fluid composition comprising a mixture of alkyl polyglycols, polyglycols and additives, the fluid being virtually free of boric acid esters of glycols or alkyl polyglycols.
  • the fluid exhibits a low temperature kinematic viscosity of less than 900 centistokes, determined at -40°C, exhibits an equilibrium reflux boiling point (ERBP) of at least 250°C and a wet equilibrium reflux boiling point (WERBP) of at least 165°C, according to the methods described in the Federal Motor Vehicle Safety Standards (FMVSS)
  • FMVSS Federal Motor Vehicle Safety Standards
  • the low viscosity functional fluid composition according to the present invention is useful in a variety of applications and in particular as a brake fluid, especially for new electronic or automated anti-lock brake systems which require lower viscosity fluids for satisfactory operation at low temperatures.
  • borate esters are well known in the art.
  • these borate ester based compositions must meet stringent physical properties and performance requirements particularly with respect to minimum dry equilibrium reflux boiling point (“ERBP”), minimum wet equilibrium reflux boiling point (“WERBP”) and maximum low temperature kinematic viscosity (e.g. determined at -40°C) while maintaining adequate resistance to corrosion, stability and meeting other physical property requirements such as pH, reserve alkalinity, corrosion protection and rubber swelling.
  • ERBP dry equilibrium reflux boiling point
  • WERBP minimum wet equilibrium reflux boiling point
  • maximum low temperature kinematic viscosity e.g. determined at -40°C
  • Borate-esters of alkyl glycols are more hygroscopic compared to the sole alkyl glycols, resulting in an elevated water uptake from moisture of borate- containing brake fluids, which is undesired during storage and use.
  • the content of boron in the brake fluids is associated with a certain risk of gel formation or precipitation due to salt formation of the inorganic character of boron salts, especially upon ageing of the brake fluids As a result, particles may occur in the brake fluid and limit its performance in critical situations.
  • WO-00/65001 describes hydraulic fluids comprising alkoxy glycol borate esters, alkoxy glycols and corrosion inhibitors, additionally containing cyclic carboxylic acid derivatives.
  • WO-02/38711 describes low viscosity functional fluid compositions comprising alkoxy glycol borate esters, alkoxy glycol components and additives such as corrosion inhibitors, wherein the alkoxylation degrees of the alkoxy glycol borate esters and the alkoxy glycols are restricted to a certain narrow pattern.
  • US-4371448A teaches a hydraulic fluid which formally fulfils the specification DOT 5.
  • This hydraulic fluid essentially consists of (A) about 20 to 40% by weight of at least one boric acid ester obtained from orthoboric acid, diethylene glycol and an ethylene glycol monoalkyl ether; (B) 30 to 60% by weight of at least one ethylene glycol monoalkyl ether; (C) 10 to 40% by weight of at least one bis-(ethylene glycol monoalkyl ether)-formal; (D) 0.1 to 5% by weight of at least one alkylamine; and (E) 0.05 to 5% by weight of at least one stabilizer and/or inhibitor; the percentages by weight in each case being relative to the total weight of the fluid.
  • EP-0750033A1 teaches a hydraulic fluid composition, especially a brake fluid composition, based on a boric ester of a glycol ether and comprising a corrosion- inhibiting system which includes: (1) at least one constituent (A) chosen from fatty amines or the salts of one or more carboxylic acids with the said amines, and (2) at least one constituent (B) chosen from the products resulting from the reaction of 10 one or more carboxylic fatty acids with a polyoxyalkylene glycol, or from the transesterification reaction of one or more esters of carboxylic fatty acids with a polyoxyalkylene glycol.
  • A fatty amines or the salts of one or more carboxylic acids with the said amines
  • B at least one constituent chosen from the products resulting from the reaction of 10 one or more carboxylic fatty acids with a polyoxyalkylene glycol, or from the transesterification reaction of one or more esters of carboxylic fatty acids with a polyoxyalkylene glycol.
  • EP-0617116A1 teaches a hydraulic fluid composition having a high boiling point, in 15 particular a high equilibrium reflux boiling point and a low viscosity.
  • the composition contains, as additive, at least one ether amine having a molecular weight between 120 and 300 and having the formula in which
  • R 3 is linear or branched radical having at least one ether functional group and no alcohol functional group
  • R is a methyl radical or a hydrogen atom
  • p is an integer from 1 to 3
  • q is an integer from 0 to 2.
  • WO-201 2/003117A1 discloses a functional fluid composition comprising
  • alkoxy glycol mixture in an amount of about 38% to 47% by weight of the functional fluid composition, where the alkoxy glycol mixture is comprised alkoxy glycols having the formula
  • EP-A-0129240 teaches hydraulic fluids with a boron content of from 0 to 1 % by weight, and consisting essentially of a) 2 - 40% by weight, of an alkylene glycol of general formula (I):
  • R a is an alkylene radical having from 2 to 3 carbon atoms, and x is an integer between 1 and 3; b) 15 - 65% by weight, referred to the total weight of the fluid, of an alkylene glycol mono alkylether of general formula (II); R - (RaO) x - OH (II) wherein
  • R a and x have the above indicated meanings, and R is a Ci -C4 alkyl; c) 15 - 55% by weight, referred to the total weight of the fluid, of at least one poly alkylene glycol mono alkylether of general formula (III)
  • R is a Ci -C 4 alkyl
  • R' is H or CH3 and n is an integer whereby the molecular weight of the compound will be between 208 and 1000; d) 0 - 54% by weight, referred to the total weight of the fluid, of the reaction product of H3 BO3 with the alkylene glycols of formula (I), in a molar ratio of 1 : 15 - 3; e) 0 - 10% by weight, referred to the total weight of the fluid, of at least one inhibitor.
  • DE-3627432 teaches a brake fluid based on glycols and glycol ethers, consisting essentially of
  • a glycol ether component consisting of a) 10 to 100% by weight-% of at least one glycol dialkyl ether of the following formula R- (OAIki) x-OR1 , in which R and R1 are an alkyl group with 1 to 4 C atoms, Alki is the ethylene or a propylene group and x is an integer from 3 to 6, and b) 0 to 90 wt.
  • R2- (OAIk2) y-OH a glycol monoalkyl ether of the following formula R2- (OAIk2) y-OH, in which R2 is an alkyl group with 1 to 4 carbon atoms, Alk2 is the ethylene or a propylene group and y is an integer from 2 to 4, percent by weight based on the mixture of these glycol ethers, and
  • GB-1330468 describes brake fluid compositions containing orthoesters of the formulae A and B in combination with polyoxyalkyleneglycol esters of dicarboxylic acids and/or alkyl esters of glycols or polyglycols
  • Such compounds were applied in 10 wt.-% in base fluid, consisting of mainly conventional esters, such as propionates and nylonates and minor amounts of alkyl glycols.
  • base fluid consisting of mainly conventional esters, such as propionates and nylonates and minor amounts of alkyl glycols.
  • the addition of 10% of various ortho esters resulted in a less pronounced reduction of boiling point in the presence of 1 wt.-% water (minus 69°C and less, compared to -100°C reduction in the absence of ortho esters).
  • borate-free brake fluids are described in the literature
  • DOT3/class 3 fluids which are in general of a lower ERBP, lower wERBP and higher viscosity at -40°C), according to FMVSS.
  • GB-1330468 discloses borate-free brake fluids, containing ortho esters in combinations with poly oxyalkylene glycol ether-ester of dicarboxylic acids and/or alkyl ester of glycols or polyglycols and minor amounts of alkylglycols. Such combinations suffer from elevated viscosity at -40°C and the WERBP was not investigated.
  • DE-3627432C2 Hoechst
  • US-2006/0264337 BASF disclose diethylene/triethylene glycol and dipropylene glycol based brake fluids, fulfilling just the minimum requirement of DOT 4 and ISO 4925 class 4 norm.
  • WO-2007/005593A2 describes compositions of brake fluids containing 0-10 wt.-% of borate ester and the use of larger quantities of butoxy-glycols, mainly butoxy-triglycol.
  • EP-0129240A1 (Montedison S.p.A.) discloses borate-free brake fluid formulations consisting of min. 30 wt.-% diethylene glycol or higher glycols but suffering from elevated viscosity at -40°C.
  • the problem to be solved by the instant invention is to provide a hydraulic fluid having the properties mentioned below and being essentially or entirely borate free.
  • a functional fluid composition being essentially free from borates which exhibits superior values of ERBP and of WERBP and for low temperature kinematic viscosity, while maintaining excellent resistance to corrosion, high stability and meeting other physical property requirements such as pH, reserve alkalinity and rubber swell.
  • WERBP values are achieved by using ortho esters as a replacement for borate esters.
  • this invention relates to a functional fluid, comprising (A) from 8 to 80% by weight, based on the total composition, of one or more ortho-ester according to formula (I) wherein
  • Ri, R 2 , R3 are independently selected from H or Ci to Cs alkyl groups, preferably methyl or butyl,
  • R 4 means H or Ci to Cs alkyl, preferably H or methyl, a, b, c are independently numbers from 0 to 6, preferably 3 or 4, with the proviso that a+b+c is at least 1 , (B) from 10 to 87% by weight, based on the total composition, of one or more alkoxy glycol according to formula (II)
  • R5 is a C 1 to Ce alkyl residue, preferably methyl or butyl, m is a number from 2 to 6, preferably 3 or 4,
  • this invention provides the use of the functional fluid of the first aspect as a brake fluid for vehicular brakes.
  • this invention provides for a method of operating a vehicular brake that transmits braking force through a hydraulic system, the method comprising filling the hydraulic system with a functional fluid according to the first aspect.
  • the functional fluid will be referred to as fluid in the following.
  • the orthoester used as component (A) corresponds to one or more components according to formula (I).
  • R1 , R2, R3 are independently selected from H or Ci to Cs alkyl groups preferably from H or Ci to C4 alkyl groups.
  • R1 , R2, R3 are independently selected from methyl or butyl.
  • R1, R2, R3 mean methyl.
  • only one out of R1 , R2, R3 takes the meaning of H.
  • the amount of orthoester according to formula (I) wherein at least one of R1 , R2, R3 takes the meaning H is less than 30 wt.-%, more preferably less than 15 wt.-%, particularly less than 10 wt.-%, on a basis of 100 wt.-% being the total amount of all orthoester according to formula (I).
  • the orthoester used as component (A) corresponds to two or more components according to formula (I).
  • the two or more orthoesters of formula (I) differ in one out of R1 , R2, R3. This may mean e.g. that one out of R1 , R2, R3 is methyl in one of the orthoesters, and one out of R1 , R2, R3 is butyl in the other of the orthoesters.
  • R4 means H or Ci to Cs alkyl. In a preferred embodiment, R4 means H or methyl.
  • a, b, c are independently numbers from 0 to 6, with the proviso that a+b+c is at least 1 , i.e. not all of a, b, c may equal zero.
  • a, b, c are independently 3 or 4.
  • a+b+c is at least 3, more preferably at least 6.
  • the orthoester used as component (A) corresponds to two or more components according to formula (I). It is preferred, that the two or more orthoesters of formula (I) differ in one out of a, b, c., meaning that a, b, c are not all the same in the two or more orthoesters. For example, one out of a, b, c may be 3 in one of the orthoesters, and one out of a, b, c may be 4 in the other of the orthoesters.
  • the orthoester should be clear, homogeneous, and substantially free of salt or suspended components, e.g. such as residues of insoluble catalysts, to render a clear, homogenous functional fluid.
  • the orthoester used as component (A) is not a single compound, but a mixture of at least two orthoesters according to formula (I) and (la).
  • the fluid according to the first aspect not only comprises an orthoester according to formula (I), but in addition a bridged orthoester according to formula (la) wherein R1, R2, R4, a and b have the same meaning as provided for formula (I), and d is a number from 0 to 6, preferably 2 or 3.
  • R1 , R2 are independently selected from H or Ci to Cs alkyl groups preferably from H or Ci to C4 alkyl groups.
  • R1 , R2 are independently selected from methyl or butyl.
  • R1 , R2 mean methyl.
  • only one out of R1 , R2 takes the meaning of H.
  • the amount of orthoester according to formula (la) wherein at least one of R1, R2 takes the meaning H is less than 30 wt.-%, more preferably less than 15 wt.-%, particularly less than 10 wt.-%, on a basis of 100 wt.-% being the total amount of all orthoester according to formula (la).
  • the orthoester used as component (A) corresponds to two or more components according to formula (la).
  • the two or more orthoesters of formula (la) differ in one out of R1 , R2. This may mean e.g. that one out of R1 , R2 is methyl in one of the orthoesters, and one out of R1 , R2 is butyl in the other of the orthoesters.
  • R4 means H or Ci to Cs alkyl. In a preferred embodiment, R4 means H or methyl.
  • a, b are independently numbers from 0 to 6, with the proviso that a+b is at least 1 , i.e. not all of a, b, c may equal zero.
  • a, b are independently 3 or 4.
  • a+b is at least 3, more preferably at least 6.
  • the orthoester used as component (A) corresponds to two or more components according to formula (la).
  • the two or more orthoesters of formula (la) differ in one out of a, b, meaning that a, b are not all the same in the two or more orthoesters according to formula (la).
  • one out of a, b may be 3 in one of the orthoesters, and one out of a, b may be 4 in the other of the orthoesters.
  • a bridged orthoester according to formula (la) is present, its amount is preferably at most 30 wt.-%, more preferably less than 15 wt.-%, particularly less than 10 wt.-%, on a basis of 100 wt.-% being the total amount of all orthoester according to formula (I).
  • the bridged orthoester according to formula (la) is to be regarded as part of component A).
  • the amount of orthoester according to formula (la) is to be counted within the amount of component (A).
  • the bridging of orthoester by polyalkylene glycols has the technical effect of increasing the viscosity of the orthoester component, and therefore increasing the viscosity of the fluid of the first aspect.
  • a larger proportion of bridged orthoesters of the formula (la) provides a higher viscosity of the fluid.
  • Orthoesters according to formula (I) and (la) can be synthesized according to procedures known in the art from alkyl glycols and commercially available alkyl ortho esters, according to
  • Useful alkyl ortho esters are selected from R4 being a H or C-i- to Cs-akyl residues and Rx being C-i- bis C 6 -alkyl residues.
  • Radicals R1 , R2 and R3 are preferably C 1 - to C 4 -alkyl groups and may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, preferably n-butyl or methyl.
  • Examples of useful alkoxy glycols as starting material for component (A) of the present invention wherein R1 , R2 or R3 is not H include methyldiglycol, methyltriglycol, methyltetraglycol, methylpentaglycol, methylhexaglycol, ethyldiglycol, ethyltriglycol, ethyltetraglycol, ethylpentaglycol, ethylhexaglycol, n-propyl-diglycol, n-propyltriglycol, n-propyltetraglycol, n-propylpentaglycol, n-propylhexaglycol, n-butyldiglycol, n-butyltriglycol, n-butyltetraglycol, n-butylpentaglycol, n-butylhexaglycol, n-pentyldiglycol, n-
  • Example for useful glycols as starting material for component (A) of the present invention wherein R1 , R2 or R3 is H include preferably diethyleneglycol, triethyleneglycol and tetraethylene glycol and mixtures thereof.
  • hydraulic fluids require the presence of agents providing reserve alkalinity.
  • agents e.g. amines.
  • the required amount of the amine component is dependent on the required reserve alkalinity and the required pH value of the final functional fluids. Both reserve alkalinity and pH contribute to corrosion inhibition.
  • Borate-ester containing brake fluids require higher amounts of amine, usually above 1 wt.-%, in order to maintain a pH value in the range of 7.0 to 11.5, even upon hydrolysis of borate esters into the triprotic boric acid and the corresponding glycols.
  • ortho-ester based brake fluids require reduced amounts of amine.
  • Hydrolysis of ortho esters results in the formation of two equivalents of the corresponding alcohols, and one equivalent of the corresponding ester.
  • the hydrolysis of an orthoacetate to the corresponding alcohol, and the acetic acid ester follows this reaction path:
  • the ester e.g. acetic acid ester
  • the ester may be cleaved into the corresponding alcohol and one equivalent of the mono protic acid, e.g. acetic acid.
  • the requirement of orthoester based fluids for reserve alkalinity is therefore reduced when compared to borate based fluids.
  • Component (B) may be a single species or a mixture of different species with regards to the ethoxylation degree, and/or to R5.
  • R5 is a C-i- to Cs-alkyl group and may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl and 2-ethylhexyl, ethyl. More preferably, R5 is ethyl, n-butyl or methyl, most preferably n-butyl or methyl.
  • Examples of useful alkoxy glycols for component (B) of the present invention include methyldiglycol, methyltriglycol, methyltetraglycol, methylpentaglycol, methylhexaglycol, ethyldiglycol, ethyltriglycol, ethyltetraglycol, ethylpentaglycol, ethylhexaglycol, n-propyl-diglycol, n-propyltriglycol, n-propyltetraglycol, n-propylpentaglycol, n-propylhexaglycol, n-butyldiglycol, n-butyltriglycol, n-butyltetraglycol, n-butylpentaglycol, n-butylhexaglycol, n-pentyldiglycol, n-pentyltriglycol, n-pentylt
  • glycol always means “ethylene glycol”.
  • methyltriglycol, methyltetraglycol, methylpentaglycol, ethyldiglycol, ethyltriglycol, ethyltetraglycol, n-butyldiglycol, n-butyltriglycol, n-butyltetraglycol, n-butylpentaglycol are preferred for component (B).
  • Percentages of species of component (B) are given in wt.-% with the total amount of component (B) being 100 wt.-%.
  • the proportion of component (B) is 40 - 80 wt.-% of the total fluid weight.
  • Component (C) is a polyethylene glycol according to formula (III).
  • k is a number of 2, or higher. It is preferred, that k is a number from 2 - 4. More preferably, k is 2 or 3.
  • component (C) is a mixture of compounds according to formula (III) wherein k is 2 or 3.
  • component (C) it is required that in at least 80 wt.-% of all compounds according to formula (III) k is 2 or 3, the wt.-% being relative to the total weight of all compounds according to formula (III).
  • k is 2 or 3 make up to 18 wt.-%, preferably 3 to 15 wt.-% of the fluid, the total fluid weight being 100 wt.-%.
  • the total amount of species according to formula (III) wherein k is 4 or higher than 4 is at most 10 wt.-%, more preferably at most 6 wt.-%.
  • Said weight percentages provided for species according to formula (III) are provided as weight percentages of the fluid, i.e. the total weight of the fluid is 100 wt.-%. They are not provided as weight percentages of the total weight of component (C).
  • Component (D) is an additive that is required to impart particular properties to the functional fluid for performing on specifications to be fulfilled for brake fluids according to the current norms and standards FMVSS, SAE J 1703 and ISO 4925.
  • the total amount of all components (D) in the fluid is from 0.2 to 6 wt.-%, preferably from 0.5 to 5 wt.-%.
  • Component (D) comprises one or more additives selected from the group consisting of corrosion inhibitors, amines as reserve alkalinity agents, stabilizing antioxidants, defoamers, lubricants and dyes.
  • Component (D) may comprise an amine or mixtures of amines as alkalinity agent.
  • Amines are preferably alkyl or cycloalkyl amines, alkanol amines, alkyl amine ethoxylates and their mixtures.
  • Preferred alkyl amines are mono- and di-(C4- to C2o-alkyl)amines.
  • alkyl or cycloalkyl amines examples include n- butylamine, n-hexylamine, n-octylamine, 2-ethylhexylamine, isononylamine, n- decylamine, n-dodecylamine, oleylamine, d-n-propylamine, di-isopropylamine, di- n-butylamine, tri-n-butylamine, di-n-amylamine, cyclohexylamine, and salts of such amines.
  • alkanolamines are mono-, di- and trimethanolamine, mono-, di- and triethanolamine, mono-, di- and tri-n-propanolamine and mono-, di- and tri-isopropanolamine.
  • suitable alkyl amine ethoxylates are such linear, cyclic or branched alkylamine ethoxylates carrying 1.5 to 5 EO moieties and an alkyl chain having 4 to 18 carbon atoms.
  • Component (D) of the present functional fluid composition may comprise, besides the Amine, at least one additive with corrosion inhibition action, although the alkylamine ethoxylates exhibit corrosion inhibition properties themselves.
  • suitable customary additives with corrosion inhibition properties include fatty acids such as lauric, palmitic, stearic or oleic acid; esters of phosphorus or phosphoric acid with aliphatic alcohols or aliphatic alcohol ethoxylates; such as ethyl phosphate, dimethyl phosphate, isopropyl phosphate, n-butyl phosphate, 2-ethylhexyl phosphate, triphenyl phosphite and diisopropyl phosphite; heterocyclic nitrogen containing organic compounds such as benzotriazole, tolyltriazole, 1 ,2,4-triazole, benzoimidazole, purine, adenine and derivatives of such heterocyclic organic compounds.
  • fatty acids such as lauri
  • Defoamers may be selected from groups of oil based defoamers, such as natural oils, glycerides, waxes, powdered silica, alkoxylates such es EO/PO block copolymers, silicone based defoamers, preferably modified polyether or silicone derivatives and mixtures thereof.
  • oil based defoamers such as natural oils, glycerides, waxes, powdered silica, alkoxylates such es EO/PO block copolymers, silicone based defoamers, preferably modified polyether or silicone derivatives and mixtures thereof.
  • the fluid may include from 0 to 5% by weight, based on the total weight of the fluid, of a lubricant.
  • Suitable lubricants are for example, propylene oxide containing alkylene oxide polymers that are optionally substituted with a Ci to C4 alkyl group, triglycerides, castor oil, ricinoleic acid, and ethoxylates of castor oil or ricinoleic acid and mixtures thereof.
  • the lubricants are homopolymers of propylene oxide, copolymers of propylene oxide with ethylene oxide and/or butylene oxide, mono Ci to C4 alkyl substituted homopolymers of propylene oxide, mono Ci to C4 alkyl substituted copolymers of propylene oxide with ethylene oxide and/or butylene oxide, triglycerides, castor oil, ricinoleic acid, and ethoxylates of castor oil or ricinoleic acid and mixtures thereof. In case of such ethoxylates, 1 to 50 ethoxy units are preferred.
  • the propylene oxide containing alkylene oxide polymers that are optionally substituted with a Ci to C4 alkyl group have a number average molecular weight in the range of 150 to 3000 g/mol.
  • Suitable age protecting agents or antioxidants are phenolic stabilizers like Bisphenols (e,g. Bisphenol A or Bisphenol M), butyl hydroxytoluene, methoxy phenols, butylated hydroxy anisole, hydroquinone derivatives; sterically hindered amines such as benzylated, alkylated or styrenated diphenylamine, styrenated phenylamine, substituted piperidine derivatives, phenothiazine derivatives or quinoline derivatives and mixtures thereof.
  • any literature known glycol stabilizing or age protecting agents could be used herein.
  • the % values (A) - (D) add up to 100% by weight.
  • the total content of the fluid in boric acid esters is at most 3 wt.-%, preferably less than 0.3 wt.-%. Most preferably, the fluid is free of boric acid esters.
  • the combined amount of components (A) and (B) adds up to at least 70% of the fluid weight.
  • the functional fluid composition of the present invention exhibits superior behavior in ERBP and WERBP temperature and simultaneously in low temperature viscosity performance. It exhibits an ERBP of at least 250°C, more preferably of at least 260°C and a WERBP of at least 165°C, more preferably at least 170°C.
  • the low viscosity functional fluid composition of the present invention is especially useful as a brake fluid, for example for vehicles such as passenger cars and trucks, especially for new electronic or automated anti-lock brake systems which require lower viscosity fluids for satisfactory operation at low temperatures.
  • the functional fluid composition of the present invention exhibits a good corrosion protection, a good water compatibility, a mild pH value, a good stability with regard to low and high temperatures, a good oxidation stability, a good chemical stability, a good behavior towards rubber and elastomers, a good lubrication performance and good foaming behavior.
  • OE-A (MTG-Ortho acetate) Trimethylorthoacetate + Methyltriglycol
  • a mixture of 160.3 g (1.33 mol) trimethyl orthoacetate and 420 ml_ (2.66 mol) methyl triglycol is placed under nitrogen in a 1 liter four-necked flask equipped with a stirrer and a distillation attachment including a Vigreux column and heated to 165°C within 40 min. After the constant reaction temperature had been reached, a first portion of methanol was distilled off over the course of 60 minutes.
  • the reaction temperature was increased to 185°C and held for a further 45 minutes, a total of about 83% (71 g, 2.22 mol) of the theoretical amount of methanol being distilled off. Thereafter, a further 211 ml (1.34 mol) of methyl triglycol were metered in at constant heating power, and after one hour the reaction temperature was increased to 225°C and held for one hour, further methanol being distilled off. A further 50 ml (0.32 mol) of methyl triglycol were then metered in at constant heating power, and 1.9 g of benzoic acid were added. After 3 hours, a further 0.9 g and finally another 0.4 g of benzoic acid were added after a further hour.
  • OE-B (MTG/MTeG-Ortho acetate) Triethylorthacetate + Methyltriglykol (MTG) and Methyltetraglykol (MTeG)
  • Trimethyl ortho acetate (1.8 mol) was reacted with a mixture of 70% triethyleneglycolmonobutylether and 30% tetraethyleneglycolmonobutylether (combined 6.3 mol), resulting in the corresponding product with 88% conversion according to NMR.
  • Table 1 shows functional fluid compositions and their performance. Percentages are wt.-% with respect to the total fluid weight, unless otherwise noted. Table 1

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PCT/EP2022/050757 2021-03-12 2022-01-14 Low viscosity functional fluid composition WO2022189047A1 (en)

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1330468A (en) 1969-12-16 1973-09-19 Castrol Ltd Hydraulic fluids
US4371448A (en) 1979-11-08 1983-02-01 Hoechst Aktiengesellschaft Hydraulic fluid composition with improved properties based on boric acid esters, glycol mono-ethers and bis-(glycolether) formals
EP0129240A1 (de) 1983-06-21 1984-12-27 Montedison S.p.A. Hydraulische Flüssigkeiten
DE3627432A1 (de) 1986-08-13 1988-02-18 Hoechst Ag Bremsfluessigkeit auf der basis von glykolen und glykolethern
EP0617116A1 (de) 1993-03-17 1994-09-28 BP Chemicals Limited Hydraulische Flüssigkeitszusammensetzung
EP0750033A1 (de) 1995-06-23 1996-12-27 BP Chemicals Limited Hyraulische Flüssigkeitzusammensetzung
WO2000065001A1 (de) 1999-04-22 2000-11-02 Basf Aktiengesellschaft Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate
WO2002038711A1 (en) 2000-11-10 2002-05-16 Union Carbide Chemicals & Plastics Technology Corporation Low viscosity functional fluids compositions
US20060264337A1 (en) 2003-03-12 2006-11-23 Bernd Wenderoth Dot 4 brake fluids
WO2007005593A2 (en) 2005-07-01 2007-01-11 Dow Global Technologies, Inc. Low viscosity functional fluid
WO2012003117A1 (en) 2010-07-01 2012-01-05 Dow Global Technologies Llc Low viscosity functional fluids

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1330468A (en) 1969-12-16 1973-09-19 Castrol Ltd Hydraulic fluids
US4371448A (en) 1979-11-08 1983-02-01 Hoechst Aktiengesellschaft Hydraulic fluid composition with improved properties based on boric acid esters, glycol mono-ethers and bis-(glycolether) formals
EP0129240A1 (de) 1983-06-21 1984-12-27 Montedison S.p.A. Hydraulische Flüssigkeiten
DE3627432A1 (de) 1986-08-13 1988-02-18 Hoechst Ag Bremsfluessigkeit auf der basis von glykolen und glykolethern
DE3627432C2 (de) 1986-08-13 1990-10-31 Hoechst Ag, 6230 Frankfurt, De
EP0617116A1 (de) 1993-03-17 1994-09-28 BP Chemicals Limited Hydraulische Flüssigkeitszusammensetzung
EP0750033A1 (de) 1995-06-23 1996-12-27 BP Chemicals Limited Hyraulische Flüssigkeitzusammensetzung
WO2000065001A1 (de) 1999-04-22 2000-11-02 Basf Aktiengesellschaft Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate
WO2002038711A1 (en) 2000-11-10 2002-05-16 Union Carbide Chemicals & Plastics Technology Corporation Low viscosity functional fluids compositions
US20060264337A1 (en) 2003-03-12 2006-11-23 Bernd Wenderoth Dot 4 brake fluids
WO2007005593A2 (en) 2005-07-01 2007-01-11 Dow Global Technologies, Inc. Low viscosity functional fluid
WO2012003117A1 (en) 2010-07-01 2012-01-05 Dow Global Technologies Llc Low viscosity functional fluids

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