EP2027235A1 - Corrosion inhibiting composition for non-ferrous metals - Google Patents

Corrosion inhibiting composition for non-ferrous metals

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Publication number
EP2027235A1
EP2027235A1 EP07729126A EP07729126A EP2027235A1 EP 2027235 A1 EP2027235 A1 EP 2027235A1 EP 07729126 A EP07729126 A EP 07729126A EP 07729126 A EP07729126 A EP 07729126A EP 2027235 A1 EP2027235 A1 EP 2027235A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
phenyl
crc
alkylphenyl
cycloalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07729126A
Other languages
German (de)
English (en)
French (fr)
Inventor
Karl-Heinz Michel
Eric Nehls
Tassilo Habereder
Anja Keller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Mercedes Benz Group AG
Original Assignee
Ciba Holding AG
Daimler AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Holding AG, Daimler AG filed Critical Ciba Holding AG
Priority to EP07729126A priority Critical patent/EP2027235A1/en
Publication of EP2027235A1 publication Critical patent/EP2027235A1/en
Withdrawn legal-status Critical Current

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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
    • C10M161/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
    • 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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • 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
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
    • 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
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • 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
    • 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
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms 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
    • 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
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • C10M2215/224—Imidazoles
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/043—Ammonium or amine salts thereof
    • 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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives

Definitions

  • the invention relates to an additive composition for use as a metal working fluid or corrosion protection oil and a process for the protection of metals, particularly zinc or aluminium alloys, against corrosion or oxidative degradation.
  • Additives which have the purpose to protect metals against corrosion are commonly divided in to two classes:
  • Metal deactivators are used to protect yellow metals or alloys, such as copper or brass, and display their protective action in functional liquids, such as mineral oil or fuels, by deactivating the metal ions contained therein. These metal ions can have catalytic effects in undesired oxidative decomposition processes of mineral oil or fuels.
  • the protective action is explained by the formation of film-like layers on the surface of metals or by complex formation with metal ions.
  • Corrosion inhibitors are primary used to protect ferrous metals such as iron or steel.
  • Analogue to metal deactivators, corrosion inhibitors are forming also film-like layers on the sur- face of metals.
  • some corrosion inhibitors can prevent the corrosion, by emulsifying water and minimizing therefore the direct contact of water with the metal surface.
  • British Patent Specification No. 795,491 discloses the preparation of alkenyl succinic half esters and their applicability as steam turbine lubricant additives.
  • the present invention relates to a composition, which comprises A) An additive mixture that essentially consists of a) At least one alkenyl succinic half ester of the formula
  • R 1 represents C 6 -Ci 8 alkenyl
  • R 2 represents hydrogen or methyl and n is a numeral from 1 to 100
  • Ri and R 2 represents hydrogen and the other one represents a substituent selected from the group consisting of CrCi 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, C 2 -C 20 alkenyl, phenyl, phenyl-CrC 4 alkyl, CrC 4 alkylphenyl and Ci-C 4 alkylphenyl-Ci-C 4 alkyl; or
  • both of Ri and R 2 represent substituents selected from the group consisting of Ci-Ci 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, C 2 -C 20 alkenyl, phenyl, phenyl-Ci-C 4 alkyl, Ci-C 4 alkylphenyl and Ci-C 4 alkylphenyl-Ci-C 4 alkyl; and c) At least one amine phosphate partial ester of the formula
  • n represents 2, if m represents 1 , or represents 1 , if m represents 2;
  • R represents a substituent selected from the group consisting of d-C ⁇ alkyl, hy- droxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, phenyl, phenyl-Ci-C 4 alkyl, CrC 4 alkylphenyl, Ci-C 4 alkylphenyl-Ci-C 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cyclo- alkyl-CrC 4 alkyl, Ci-C 4 alkyl-C 4 -C 8 cycloalkyl and Ci-C 4 alkyl-C 4 -C 8 cyclo- alkyl-CrC 4 alkyl; and
  • Ra, Rb, Rc and R d independently of one another represent hydrogen or a substituent selected from the group consisting of CrC ⁇ alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, phenyl, phenyl-CrC 4 alkyl, CrC 4 alkylphenyl, Ci-C 4 alkylphenyl-Ci-C 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-Ci-C 4 alkyl, Ci-C 4 alkyl-C 4 -C 8 cycloalkyl and Ci-C 4 alkyl-C 4 -C 8 cycloalkyl-Ci-C 4 alkyl; and
  • a preferred embodiment of the invention relates to a composition, which comprises A) An additive mixture that essentially consists of a) At least one alkenyl succinic half ester (I), wherein Ri represents Cio-Ci6alkenyl, R 2 represents methyl and n is a numeral from 1 to 20; b) At least one imidazoline compound (II),
  • Ri and R 2 represents hydrogen and the other one represents a substituent selected from the group consisting of Ci-Ci 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl and Ci 2 -Ci 8 alkenyl; or Wherein both of Ri and R 2 represent substituents selected from the group consisting of Ci-Ci 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl and Ci 2 -Ci 8 alkenyl; and c) At least one amine phosphate partial ester (III), Wherein m represents 1 or 2; n represents 2, if m represents 1 , or represents 1 , if m represents 2; R represents a substituent selected from the group consisting of Ci-Ci 2 alkyl, hy- droxy-C 2 -Ci 2 alkyl and amino-C 2 -C- ⁇ 2 alkyl; and
  • R a , R b , R c and R d independently of one another represent hydrogen or a substituent selected from the group consisting of Ci-Ci 2 alkyl and hydroxy-C 2 -Ci 2 alkyl;
  • composition which comprises - A -
  • An additive mixture that essentially consists of a) At least one alkenyl succinic half ester (I), wherein
  • Ri represents Ci 2 -Ci 6 alkenyl, R 2 represents methyl and n is a numeral from 1 to 20; b) At least one imidazoline compound (II),
  • Ri and R 2 represents hydrogen and the other one represents a substituent selected from the group consisting of Ci-Ci 2 alkyl and Ci 2 -Ci 8 alkenyl; or
  • Ri and R 2 represent substituents selected from the group con- sisting of Ci-Ci 2 alkyl and Ci 2 -Ci 8 alkenyl; and c) At least one amine phosphate partial ester (III), Wherein m represents 1 or 2; n represents 2, if m represents 1 , or represents 1 , if m represents 2;
  • R represents a substituent selected from the group consisting of Ci-Ci 2 alkyl and hydroxy-C 2 -Ci 2 alkyl;
  • R a , R b , R c and R d independently of one another represent hydrogen or a substituent selected from the group consisting of Ci-Ci 2 alkyl and hydroxy-C 2 -Ci 2 alkyl;
  • a functional fluid relates to a composition, which comprises a) At least one alkenyl succinic half ester (I),
  • R 1 represents Ce-C-i ⁇ alkenyl
  • R 2 represents methyl and n is a numeral from 1 to 100
  • At least one imidazoline compound (II) wherein one of Ri and R 2 represents hydrogen and the other one represents a substituent selected from the group consisting of CrCi 2 alkyl, hy- droxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, C 2 -C 20 alkenyl, phenyl, phenyl-Ci-C 4 alkyl, Ci-C 4 alkylphenyl and Ci-C 4 alkylphenyl-Ci-C 4 alkyl; or
  • both of Ri and R 2 represent substituents selected from the group consisting of Ci-Ci 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, C 2 -C 2 oalkenyl, phenyl, phenyl-Ci-C 4 alkyl, CrC 4 alkylphenyl and Ci-C 4 alkylphenyl-C r C 4 alkyl; c) At least one amine phosphate partial ester (III), Wherein m represents 1 or 2; n represents 2 if m represents 1 ; or represents 1 if m represents 2; and
  • R represents a substituent selected from the group consisting of CrCi 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, phenyl, phenyl-CrC 4 alkyl, Ci-C 4 alkylphenyl, Ci-C 4 alkylphenyl-CrC 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-C r C 4 alkyl, C r C 4 alkyl-C 4 -C 8 cycloalkyl and
  • R a , R b , R c and R d independently of one another represent hydrogen or a substituent selected from the group consisting of Ci-Ci 2 alkyl, hy- droxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, phenyl, phenyl-Ci-C 4 alkyl, Ci-C 4 alkylphenyl, Ci-C 4 alkylphenyl, Ci-C 4 alkylphenyl-CrC 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cyclo- alkyl-CrC 4 alkyl, C r C 4 alkyl-C 4 -C 8 cycloalkyl and C r C 4 alkyl-C 4 -C 8 cyclo- alkyl-Ci-C 4 alkyl; and d) Additional customary additives.
  • compositions as described above are suitable as corrosion inhibitor in non-aqueous, partially aqueous or aqueous functional fluids or liquids.
  • Ri defined C 6 -Ci 8 alkenyl is preferably straight chain or, where possible, branched radical, for example n-2-octenyl, n-2-dodecenyl, iso-dodecenyl, or is preferably a group of the partial formula
  • R' and R" are independently of one another hydrogen or substantially straight chain hydrocarbyl groups, with the proviso that the total number of carbon atoms in R is within the indicated ranges.
  • R' and R" are C3-Cisalkyl or C3-Cisalkenyl groups.
  • R has from about 16 to about 18 C-atoms
  • R' is hydrogen or Ci-C 7 alkyl or C 2 -C 7 alkenyl
  • R" is C 5 -Ci 5 alkyl or C 5 -Ci 5 alkenyl.
  • R 2 is hydrogen or preferably methyl.
  • n represents a numeral from 1 to about 100. According to pre- ferred embodiments n represents a numeral from 1 to about 20.
  • Compounds (I) are obtainable by reacting the R-substituted succinic acid with ethylene oxide or ethylene glycol of desired chain length, if R 2 represents hydrogen, or with propylene oxide or polypropylene glycol of desired chain length, if R 2 represents methyl.
  • Compounds (I) are known oil soluble corrosion inhibitors, which are commercially available as solution in mineral oil, such as the product Ciba® Irgacor® L 12. Other products are Hi- tec® 536 commercially available from Ethyl Corp. Richmond VA, USA.
  • one of Ri and R 2 represents hydrogen and the other one represents a substituent selected from the group consisting of CrCi 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, C 2 -C 20 alkenyl, phenyl, phenyl-CrC 4 alkyl, CrC 4 alkylphenyl and Ci-C 4 alkylphenyl-C"i-C 4 alkyl; or
  • Both of Ri and R 2 represent substituents selected from the group consisting of CrCi 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, C 2 -C 20 alkenyl, phenyl, phenyl-Ci-C 4 alkyl, Ci-C 4 alkylphenyl and Ci-C 4 alkylphenyl-C r C 4 alkyl.
  • R 1 and R 2 defined as CrCi 2 alkyl is, for example, Ci-C ⁇ alkyl, e.g. methyl, ethyl, n-propyl or isopropyl or n-butyl, sec-butyl or tert-butyl or straight-chain or branched pentyl or hexyl, and C 7 -Ci 2 alkyl, e.g. straight-chain or branched heptyl, octyl, isooctyl, nonyl, tert-nonyl, decyl, un- decyl or dodecyl.
  • Ri and R 2 defined as hydroxy-C 2 -Ci 2 alkyl is e.g. 2-hydroxyethyl, dihydroxyethyl, 2- or
  • Ri and R 2 defined as amino-C 2 -Ci 2 alkyl is e.g. 2-aminoethyl, diaminoethyl or 2- or 3-aminopropyl or any of the above-mentioned C 4 -Ci 2 alkyl groups substituted by 1-3 amino groups.
  • Ri and R 2 defined as C 2 -C 20 alkenyl is a straight chain or, where possible, branched radical, for example vinyl, allyl, 2-butenyl, 3-butenyl, isobutenyl, n-2,4-pentadienyl, 3-methyl-2-bu- tenyl, n-2-octenyl, n-2-dodecenyl or iso-dodecenyl.
  • Ri and R 2 defined as phenyl-Ci-C 4 alkyl, Ci-C 4 alkylphenyl and Ci-C 4 alkylphenyl-CrC 4 alkyl radicals are, for example, benzyl, 1- or 2-phenethyl, 4-methyl- or 4-ethylphenyl, cumyl or 4-methylbenzyl.
  • one of Ri and R 2 represents hydrogen and the other one represents a substituent selected from the group consisting of CrCi 2 alkyl, hy- droxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl and Ci 2 -Ci 8 alkenyl; or
  • Ri and R 2 represent substituents selected from the group consisting of Ci-Ci 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl and C-
  • one of Ri and R 2 represents hydrogen and the other one represents a substituent selected from the group consisting of Ci-Ci 2 alkyl and Ci 2 -Ci 8 alkenyl; or
  • Ri and R 2 represent substituents selected from the group consisting of CrCi 2 alkyl and Ci 2 -Ci 8 alkenyl.
  • Compounds (II) are known compounds and applicable oil soluble corrosion inhibitors, which are commercially available as solution in mineral oil, such as the product Ciba® Amine 0.
  • R represents a substituent selected from the group consisting of Ci-C"i 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, phenyl, phenyl-Ci-C 4 alkyl, Ci-C 4 alkylphenyl, Ci-C 4 alkylphenyl-CrC 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-CrC 4 alkyl, Ci-C 4 alkyl-C 4 -C 8 cycloalkyl and Ci-C 4 alkyl-C 4 -C 8 cycloalkyl-C r C 4 alkyl; and Ra, R b , R c and R d independently of one another represent hydrogen or a substituent selected from the group consisting of CrC ⁇ alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl; and Ra,
  • d-C ⁇ alkyl hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, phenyl, phenyl-CrC 4 alkyl, Ci-C 4 alkylphenyl, Ci-C 4 alkylphenyl-Ci-C 4 alkyl correspond to the definitions given above with regard to compounds (I) and (II).
  • R as well as R 3 , Rb, R c and R d defined as C 4 -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-Ci-C 4 alkyl, Ci-C 4 alkyl-C 4 -C 8 cycloalkyl and Ci-C 4 alkyl-C 4 -C 8 cycloalkyl-CrC 4 alkyl are, for example, cyclopentyl, cyclohexyl, cyclopentylmethyl or cyclohexylmethyl, cyclopentyl-1 ,1 -ethyl, cyclo- hexyl-1 ,1 -ethyl, cyclopentyl-1 ,2-ethyl, cyclohexyl-1 ,2-ethyl, cyclopentyl-1 ,2-propyl or cyclohe- xyl-1 ,2-propyl, which can be substituted on the C 4 -C 8
  • R represents a substituent selected from the group consisting of Ci-Ci 2 alkyl, hydroxy-C 2 -Ci 2 alkyl and amino-C 2 -Ci 2 alkyl;
  • Ra, Rb, Rc and R d independently of one another represent hydrogen or a substituent selected from the group consisting of CrC ⁇ alkyl and hydroxy-C 2 -Ci 2 alkyl.
  • Amine phosphate partial ester as represented by the formula III are known compounds that can be prepared by known methods.
  • Compounds (III) are applicable as oil soluble corrosion inhibitors and commercially available, such as the product Ciba® Irgalube® 349.
  • amine phosphate partial ester as represented by the formula III are commercially available from Rheinchemie Rheinau GmbH, Mannheim Germany, such as the products Ad- ditin® RC 3740, RC 3741 or RC 3760 (amine neutralized phosphoric acid ester of aliphatic alcohols).
  • the term functional liquid includes non-aqueous, partially aqueous and aqueous liquids which are in contact with metals to be protected, in particular aluminium and zinc.
  • non-aqueous functional liquids are fuels, e.g. hydrocarbon mixtures comprising mineral oil fractions which are liquid at room temperature and are suitable for use in internal combustion engines, e.g. internal combustion engines with external (petrol engines) or internal ignition (diesel engines), e.g. petrol having different octane contents (regular grade or premium grade petrol) or diesel fuels, and lubricants, hydraulic fluids, metal working fluids, such as drawing oil, cutting oils, forming oils, drilling oils etc, engine coolants, transformer oils and switchgear oils.
  • fuels e.g. hydrocarbon mixtures comprising mineral oil fractions which are liquid at room temperature and are suitable for use in internal combustion engines, e.g. internal combustion engines with external (petrol engines) or internal ignition (diesel engines), e.g. petrol having different octane contents (regular grade or premium grade petrol) or diesel fuels, and lubricants, hydraulic fluids, metal working fluids, such as drawing oil, cutting oils, forming
  • Suitable partially aqueous functional liquids are water-in-oil or oil-in-water metal working fluids, hydraulic fluids based on aqueous polyglycol/ polyglycol ether mixtures or gly- col systems, and engine cooling systems based on aqueous glycol.
  • aqueous functional liquids are industrial cooling water, filling compositions of a water conditioning plant, steam generation systems, sea water evaporation systems, sugar evaporation systems, irrigation systems, hydrostatic boilers and heating systems or cooling systems having a closed circulation.
  • the composition according to the invention preferably comprise 0.01 to 10.0% by weight, in particular 0.02 to 3.0 % by weight, of the additive mixture, as defined above, based on the weight of the functional liquid.
  • Non-aqueous functional liquids are preferred, in particular base oils of lubricating viscosity, which can be used for the preparation of greases, metal working fluids, gear fluids and hy- draulic fluids.
  • Suitable greases, metal working fluids, gear fluids and hydraulic fluids are based, for example, on mineral or synthetic oils or mixtures thereof.
  • the lubricants are familiar to a person skilled in the art and are described in the relevant literature, such as, for example, in Chemistry and Technology of Lubricants; Mortier, R.M. and Orszulik, S.T. (Editors); 1992 Blackie and Son Ltd. for GB, VCH-Publishers N. Y. for U.S., ISBN 0-216-92921-0, cf. pages 208 et seq. and 269 et seq.; in Kirk-Othmer Encyclopedia of Chemical Technology, Fourth Edition 1969, J. Wiley & Sons, New York, Vol.
  • the lubricants are in particular oils and greases, for example based on mineral oil, synthetic oils, or vegetable and animal oils, fats, tallow and wax or mixtures thereof.
  • Vegetable and animal oils, fats, tallow and wax are, for example, palm kernel oil, palm oil, olive oil, colza oil, rapeseed oil, linseed oil, soy bean oil, cotton wool oil, sunflower oil, coconut oil, maize oil, castor oil, walnut oil and mixtures thereof, fish oils, and chemically modified, e.g. epoxidised or sulphoxidised or alkylated or hydrogenated, forms or forms prepared by genetic engineering, for example soy bean oil prepared by genetic engineering.
  • Examples of synthetic lubricants include lubricants based on aliphatic or aromatic carboxylic esters, polymeric esters, polyalkylene oxides, phosphoric acid esters, poly- ⁇ -olefins or silicones of the diester of a dibasic acid with a monohydric alcohol, e.g. dioctyl sebacate or di- nonyl adipate, of a triester of trimethylolpropane with a monobasic acid or with a mixture of such acids, e.g.
  • trimethylolpropane tripelargonate trimethylolpropane tricaprylate or mixtures thereof, of a tetra ester of pentaerythritol with a monobasic acid or with a mixture of such acids, e.g. pentaerythrityl tetracaprylate, or of a complex ester of monobasic and dibasic acids with polyhydric alcohols, e.g. a complex ester of trimethylolpropane with caprylic and sebacic acid or of a mixture thereof.
  • Particularly suitable in addition to mineral oils are, for example, poly- ⁇ -olefins, ester-based lubricants, phosphates, glycols, polyglycols and polyalkylene glycols and mixtures thereof with water.
  • Said lubricants or mixtures thereof can also be mixed with an organic or inorganic thickener (base fat).
  • Organic or inorganic thickener base fat
  • Metal working fluids and hydraulic fluids can be prepared on the basis of the same substances as described above for the lubricants. These are frequently also emulsions of such substances in water or other liquids.
  • Said lubricant compositions may additionally contain further additives which are added in order further to improve their fundamental properties.
  • additives include: antioxidants, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents, tackyfiers, thixotropic builders, dewatering agents, antifoam agents, demulsifiers, high pressure additives and antiwear additives.
  • Such additives are added in the amounts customary in each case for the purpose, each in the range from 0.01 to 10.0% by weight. Examples of further additives follow:
  • Phenolic antioxidants 1.1. Alkylated monophenols: 2,6-di-tert-butyl-4-methylphenol, 2-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-iso- butylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-( ⁇ -methylcyclohexyl)-4,6-dimethyl- phenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4- methoxymethylphenol, linear nonylphenols or nonylphenols which are branched in the side chain, e.g.
  • Alkylthiomethylphenols 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl- 6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonyl- phenol
  • Tocopherols ⁇ -, ⁇ -, ⁇ - or ⁇ -tocopherols and mixtures thereof (vitamin E)
  • Tocopherols ⁇ -, ⁇ -, ⁇ - or ⁇ -tocopherols and mixtures thereof (vitamin E)
  • Vitamin E ⁇ -, ⁇ -, ⁇ - or ⁇ -tocopherols and mixtures thereof (vitamin E)
  • Hydroxylated thiodiphenyl ethers 2,2'-thiobis(6-tert-butvl-4-methylphenol),
  • Alkylidene bisphenols 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'- methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-( ⁇ -methylcy- clohexyl)-phenol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylene- bis(6-nonyl-4-methylphenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'- ethylidenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2'-methylenebis[6-( ⁇ -methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[6-( ⁇ , ⁇ -di- methylbenzy
  • Hydroxybenzyl aromatics 1 ,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethyl- benzene, 1 ,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol 1.10.
  • Triazine compounds 2,4-bisoctylmercapto-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1 ,3,5- triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1 ,3,5-triazine, 2- octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1 ,3,5-triazine, 2,4,6- tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1 ,2,3-triazine, 1 ,3,5-tris(3,5-di-tert-butyl-4-hy- droxybenzyl) isocyanurate, 1 ,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) iso- cyan
  • esters of beta-(5-tert-butyl-4-hvdroxy-3-methylphenyl)propionic acid (with monohydric or polyhydric alcohols), e.g. the alcohols with methanol, ethanol, n-octanol, isooctanol, octadecanol, 1 ,6-hexanediol, 1 ,9-nonanediol, ethylene glycol, 1 ,2-propanediol, neopentylglycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl) isocyanurate, N,N'-bis(hydroxyethyl)-oxalamide, 3- thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hy--
  • p,p'-di-tert-octyldiphenyl- amine 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylamino-phenol, 4-do- decanoylaminophenol, 4-octadecanoylaminophenol, di-(4-methoxyphenyl)amine, 2,6- di-tert-butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diami- nodiphenylmethane, N,N,N',N'-tetramethyl-4,4'-diaminodiphenylmethane, 1 ,2-di-[(2- methyl-phenyl)-amino]ethane, 1 ,2-di-(phenylamino)-propane, (o-tolyl)biguanide, di-[4-[4-[4-[4
  • antioxidants aliphatic or aromatic phosphites, esters of thiodipropionic acid or thiodiacetic acid or salts of dithiocarbamic or dithiophosphoric acid, 2,2, 12,12-tetra- methyl-5,9-dihydroxy-3,7,1 1-trithiatridecane and 2,2,15,15-tetramethyl-5,12-dihy- droxy-3,7,10,14-tetrathiahexadecane
  • Benzotriazoles and derivatives thereof 2-mercaptobenzotriazole, 2,5-dimercaptoben- zotriazole, 4- or 5-alkylbenzotriazoles (e.g. tolutriazole) and derivatives thereof, 4,5,6,7-tetrahydrobenzotriazole, 5,5'-methylenebisbenzotriazole; Mannich bases of benzotriazole or tolutriazole, such as 1-[di(2-ethylhexylaminomethyl)]tolutriazole and 1-[di(2-ethylhexylaminomethyl)]benzotriazole; alkoxyalkylbenzotriazoles, such as 1- (nonyloxymethyl)-benzotriazole, 1-(1-butoxyethyl)benzotriazole and 1-(1-cyclohexyl- oxybutyl)tolutriazole
  • 3.2. 1 ,2,4-Triazoles and derivatives thereof 3-alkyl (or aryl)-1 ,2,4-triazoles, Mannich bases of 1 ,2,4-triazoles, such as 1-[di(2-ethylhexyl)aminomethyl]-1 ,2,4-triazole; alkoxyalkyl-1 ,2,4-triazoles, such as 1-(1-butoxyethyl)-1 ,2,4-triazole; acylated 3-amino- 1 ,2,4-triazoles
  • Corrosion inhibitors 4.1. Organic acids, their esters, metal salts, amine salts and anhydrides: alkyl- and al- kyenylsuccinic acids and partial esters thereof with alcohols, diols or hydroxycarbox- ylic acids, partial amides of alkyl- and alkenylsuccinic acids, 4-nonylphenoxyacetic acid, alkoxy- and alkoxyethoxycarboxylic acids, such as dodecyloxyacetic acid, dode- cyloxy(ethoxy)acetic acid and amine salts thereof, and furthermore N-oleoylsarcosine, sorbitan monooleate, lead naphthenate, alkenylsuccinic anhydrides, e.g. dodecenyl- succinic anhydride, 2-(2-carboxyethyl)-1-dodecyl-3-methylglycerol and salts thereof, in particular sodium salts and
  • Sulphur-containing compounds barium dinonylnaphthalenesulphonat.es, calcium petroleum sulphonates, alkylthio-substituted aliphatic carboxylic acids, esters of aliphatic 2-sulphocarboxylic acids and salts thereof
  • Viscosity index improvers polyacrylates, polymethacrylates, vinylpyrroli- done/methacrylate copolymers, polyvinylpyrrolidones, polybutenes, olefin copoly- mers, styrene/acrylate copolymers, polyethers
  • Dispersants/Surfactants polybutenylsuccinamides or polybutenylsuccinimides, polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sul- phonates and phenolates
  • High pressure and antiwear additives sulphur- and halogen-containing compounds, e.g. chlorinated paraffins, sulphonated olefins or vegetable oils (soy bean oil, rape- seed oil), alkyl or aryl di- or trisulphides, benzotriazoles or derivatives thereof, such as bis (2-ethylhexyl)aminomethyl tolutriazoles, dithiocarbamates, such as methylenebis- dibutyl dithiocarbamate, derivatives of 2-mercaptobenzothiazole, such as 1-[N 1 N- bis(2-ethylhexyl)aminomethyl]-2-mercapto-1 H-1 ,3-benzothiazole, derivatives of 2,5- dimercapto-1 ,3,4-thiadiazole, such as 2,5-bis(tert.nonyldithio)-1 ,3,4-thiadiazole
  • chlorinated paraffins e.g.
  • Emulsifiers petroleum sulphonates, amines, such as polyoxyethylated fatty amines, non-ionic surface-active substances
  • Biocides triazines, thiazolinones, trisnitromethane, morpholine, sodium pyridinethiol
  • Tackifiers acrylamide copolymer, polyisubutene resins.
  • Thixotropic builders microcrystalline waxes, oxidized waxes and oxidized esters
  • Said components can be mixed with the lubricants in a manner known per se. It is also possible to prepare a concentrate or a so-called additive package, which can be diluted to the concentrations of use for the corresponding lubricant according to the application purposes as intended.
  • the ratio of component a) to component b) to component b) present in the additive mixture A) may vary within the ranges of approximately from 10 : 10 : 80 and 80 : 10 : 10 to 10 : 80 : 10% by weight.
  • the total content of the additive mixture A) in the composition is not critical, the preferred total content of the additive mixture A) in the composition is in the range between 10.0 and 0.01 , preferably 10.0 and 0.1 or 3.0 and 0.1 % by weight, based on the total weight of the composition.
  • a further embodiment of the invention relates to an additive mixture that essentially consists of a) At least one alkenyl succinic half ester (I),
  • R 1 represents C 6 -C- ⁇ 8 alkenyl
  • R 2 represents hydrogen or methyl and n is a numeral from 0 to 100
  • At least one imidazoline compound (II) At least one imidazoline compound (II),
  • one of Ri and R 2 represents hydrogen and the other one represents a substituent selected from the group consisting of CrCi 2 alkyl, hy- droxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, C 2 -C 20 alkenyl, phenyl, phenyl-Ci-C 4 alkyl, Ci-C 4 alkylphenyl and Ci-C 4 alkylphenyl-Ci-C 4 alkyl; or
  • both of Ri and R 2 represent substituents selected from the group consisting of Ci-Ci 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, C 2 -C 2 oalkenyl, phenyl, phenyl-Ci-C 4 alkyl, Ci-C 4 alkylphenyl and Ci-C 4 alkylphenyl-Ci-C 4 alkyl; and c) At least one amine phosphate partial ester (III),
  • n represents 2, if m represents 1 ; or represents 1 , if m represents 2;
  • R represents a substituent selected from the group consisting of Ci-Ci 2 alkyl, hydroxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, C 2 -C 20 alkenyl, phenyl, phenyl-Ci-C 4 alkyl, C r C 4 alkylphenyl, Ci-C 4 alkylphenyl-Ci-C 4 alkyl,
  • R a , R b , R c and R d independently of one another represent hydrogen or a substituent selected from the group consisting of Ci-Ci 2 alkyl, hy- droxy-C 2 -Ci 2 alkyl, amino-C 2 -Ci 2 alkyl, C 2 -C 2 oalkenyl, phenyl, phenyl-CrC 4 alkyl, CrC 4 alkylphenyl, Ci-C 4 alkylphenyl-Ci-C 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-Ci-C 4 alkyl, Ci-C 4 alkyl-C 4 -C 8 cycloalkyl and Ci-C 4 alkyl-C 4 -C 8 cycloalkyl-Ci-C 4 alkyl.
  • components a), b) and c) present in the additive mixture corresponds to the definitions of components a), b) and c) present in the compositions as defined above.
  • the invention relates to the additive mixture, as defined above, used as additives in a metal working fluid.
  • the invention also relates to the process for protection against corrosion or oxidative degradation of metals, wherein the metal is exposed to a functional fluid comprising the additive mixture as defined above.
  • the invention relates to the process for protection against corrosion or oxidative degradation of zinc, aluminum or alloys thereof, wherein zinc, aluminum or alloys thereof are exposed to a functional fluid comprising the additive mixture as defined above.
  • a further embodiment of the invention relates to a process for protection against corrosion or oxidative degradation of zinc, aluminum or alloys thereof, wherein zinc, aluminum or alloys thereof are exposed to a functional fluid comprising at least one alkenyl succinic half ester of the formula I as defined above, wherein R 1 represents C 6 -Ci 8 alkenyl, R 2 represents hydrogen or methyl and n is a numeral from 1 to 100.
  • a typical test procedure to test the corrosion inhibition is the climate chamber test according to DIN EN ISO 6270-2. This test is slightly modified by using several different metal samples and more severe conditions. Each sample is treated in the following test cycle: Exposure for 8 hours in a closed climate chamber at 50 ⁇ 3 °C, humidity ca. 100%, followed by 16 hours in an open climate chamber, cooling at 21 ⁇ 3°C and humidity approaching am- bient. The test cycles are repeated until 100% corrosion is detected visually. In the event that the test sample is not corroded, the test procedure is stopped after 24 cycles.
  • VDA-Pr ⁇ fblatt As mentioned in “VDA-Pr ⁇ fblatt” from May 2003; VDA 230- 201 :
  • Mixture B 5% Irgalube® 349 in a parafinic base oil

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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)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP07729126A 2006-05-23 2007-05-15 Corrosion inhibiting composition for non-ferrous metals Withdrawn EP2027235A1 (en)

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EP06114370 2006-05-23
EP07729126A EP2027235A1 (en) 2006-05-23 2007-05-15 Corrosion inhibiting composition for non-ferrous metals
PCT/EP2007/054674 WO2007135017A1 (en) 2006-05-23 2007-05-15 Corrosion inhibiting composition for non-ferrous metals

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US20100022425A1 (en) 2010-01-28
JP5395658B2 (ja) 2014-01-22
AU2007253453B2 (en) 2012-01-19
KR20090010041A (ko) 2009-01-28
CN101454429B (zh) 2012-08-08
AU2007253453A1 (en) 2007-11-29
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RU2483099C2 (ru) 2013-05-27

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