CA2650246A1 - Corrosion inhibiting composition for non-ferrous metals - Google Patents
Corrosion inhibiting composition for non-ferrous metals Download PDFInfo
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- CA2650246A1 CA2650246A1 CA002650246A CA2650246A CA2650246A1 CA 2650246 A1 CA2650246 A1 CA 2650246A1 CA 002650246 A CA002650246 A CA 002650246A CA 2650246 A CA2650246 A CA 2650246A CA 2650246 A1 CA2650246 A1 CA 2650246A1
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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
- 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
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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
- 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
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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
- 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
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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
- 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
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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
- 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
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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
- 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
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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
- 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
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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
- 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
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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
- 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
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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
- 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
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- 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
Abstract
The invention relates an additive composition for use as a metal working fluid and a process for protection of metals, particularly zinc or aluminum, against corrosion or oxidative degradation. The composition comprises an additive mixture of an alkenyl succinic half ester, a substituted imidazoline compound and amine phosphate partial ester in a functional fluid.
Description
CORROSION INHIBITING COMPOSITION FOR NON-FERROUS METALS
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 deactivat-ing 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. Ana-logue to metal deactivators, corrosion inhibitors, are forming also film-like layers on the sur-face of metals. In addition some corrosion inhibitors can prevent the corrosion, by emulsify-ing water and minimizing therefore the direct contact of water with the metal surface.
Presently metal protection methods focus primarily on iron and copper surfaces. However, other metals, such as zinc and aluminium and their related alloys, have become very impor-tant in many technical applications. Zinc and aluminium are, for example, widely used in the manufacture of automobiles. Zinc is widely used as corrosion protection coating of steels, e.g. zinc coated steel coils. Corrosion problems often occur during transport, handling and working of semi-finished metal products. Unfortunately, presently used metal deactivator compositions are less satisfactory or even unsatisfactory to protect these metal surfaces.
Therefore, there is a clear need for improved metal working fluids to prevent corrosion of these metals British Patent Specification No. 795,491 discloses the preparation of alkenyl succinic half esters and their applicability as steam turbine lubricant additives.
British Patent Specification No. 1,043,488 lubricating oil compositions comprising substituted imidazoline compounds and phosphate partial esters.
U.S. Patent Application Publication No. 2005/0272614 discloses corrosion inhibiting compo-sitions, wherein substituted imidazolines and neutral metal sulfonate corrosion inhibitors are present.
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 deactivat-ing 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. Ana-logue to metal deactivators, corrosion inhibitors, are forming also film-like layers on the sur-face of metals. In addition some corrosion inhibitors can prevent the corrosion, by emulsify-ing water and minimizing therefore the direct contact of water with the metal surface.
Presently metal protection methods focus primarily on iron and copper surfaces. However, other metals, such as zinc and aluminium and their related alloys, have become very impor-tant in many technical applications. Zinc and aluminium are, for example, widely used in the manufacture of automobiles. Zinc is widely used as corrosion protection coating of steels, e.g. zinc coated steel coils. Corrosion problems often occur during transport, handling and working of semi-finished metal products. Unfortunately, presently used metal deactivator compositions are less satisfactory or even unsatisfactory to protect these metal surfaces.
Therefore, there is a clear need for improved metal working fluids to prevent corrosion of these metals British Patent Specification No. 795,491 discloses the preparation of alkenyl succinic half esters and their applicability as steam turbine lubricant additives.
British Patent Specification No. 1,043,488 lubricating oil compositions comprising substituted imidazoline compounds and phosphate partial esters.
U.S. Patent Application Publication No. 2005/0272614 discloses corrosion inhibiting compo-sitions, wherein substituted imidazolines and neutral metal sulfonate corrosion inhibitors are present.
It has surprisingly been found that mixtures of alkenyl succinic half esters, substituted imida-zoline compounds and amine phosphate partial esters in functional fluids, such as oils, pre-vent the corrosion of zinc, zinc coated steel and aluminum metal samples. This anticorrosive effect can be increased by the further admixture of additional anti-corrosive agents, such as substituted imidazolines and amine phosphate partial esters.
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 H
R-C- CO -OH
CH2 CO-O+CH2 C-OH (I), n Wherein R, represents C6-C,$alkenyl, R2 represents hydrogen or methyl and n is a numeral from 1 to 100;
b) At least one imidazoline compound of the formula F__\
NN-R2 (II), IRi Wherein one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl; or Wherein both of R, and R2 represent substituents selected from the group con-sisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl;
and c) At least one amine phosphate partial ester of the formula Ra ~ +
~N (III), I ~
P ~ Rb Rd (RO)m (O )n Rc n Wherein m represents 1 or 2;
n represents 2, if m represents 1, or represents 1, if m represents 2;
The present invention relates to a composition, which comprises A) An additive mixture that essentially consists of a) At least one alkenyl succinic half ester of the formula H
R-C- CO -OH
CH2 CO-O+CH2 C-OH (I), n Wherein R, represents C6-C,$alkenyl, R2 represents hydrogen or methyl and n is a numeral from 1 to 100;
b) At least one imidazoline compound of the formula F__\
NN-R2 (II), IRi Wherein one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl; or Wherein both of R, and R2 represent substituents selected from the group con-sisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl;
and c) At least one amine phosphate partial ester of the formula Ra ~ +
~N (III), I ~
P ~ Rb Rd (RO)m (O )n Rc n 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 C,-C,2alkyl, hy-droxy-C2-C,2alkyl, amino-C2-C,2alkyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl, C,-C4alkylphenyl-C,-C4alkyl, C4-C$cycloalkyl, C4-C$cyclo-alkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cyclo-alkyl-C,-C4alkyl; and Ra, Rb, Rc and Rd independently of one another represent hydrogen or a substitu-ent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl, C,-C4alkylphenyl-C,-C4alkyl, C4-C$cycloalkyl, C4-C$cycloalkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cycloalkyl-C,-C4alkyl; and B) A functional fluid.
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 R, represents C10-C,6alkenyl, R2 represents methyl and n is a numeral from 1 to 20;
b) At least one imidazoline compound (II), Wherein one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl and C12-C,$alkenyl; or Wherein both of R, and R2 represent substituents selected from the group consist-ing of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl and C12-C,$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 C,-C,2alkyl, hy-droxy-C2-C,2alkyl and amino-C2-C,2alkyl; and Ra, Rb, Rc and Rd independently of one another represent hydrogen or a substituent selected from the group consisting of C,-C,2alkyl and hydroxy-C2-C,2alkyl; and B) A functional fluid.
A particularly preferred embodiment of the invention relates to composition, which comprises A) An additive mixture that essentially consists of a) At least one alkenyl succinic half ester (I), wherein R, represents C12-C,6alkenyl, R2 represents methyl and n is a numeral from 1 to 20;
b) At least one imidazoline compound (II), Wherein one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl and C12-C,$alkenyl;
or Wherein both of R, and R2 represent substituents selected from the group con-sisting of C,-C,2alkyl and C12-C,$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 C,-C,2alkyl and hydroxy-Cz-Clzalkyl; and Ra, Rb, Rc and Rd independently of one another represent hydrogen or a substitu-ent selected from the group consisting of C,-C,2alkyl and hydroxy-C2-C,2alkyl;
and B) A functional fluid.
A highly preferred embodiment of the invention relates to a composition, which comprises a) At least one alkenyl succinic half ester (I), Wherein R, represents C6-C,$alkenyl, R2 represents methyl and n is a nu-meral from 1 to 100;
b) At least one imidazoline compound (II), Wherein one of R, and R2 represents hydrogen and the other one repre-sents a substituent selected from the group consisting of C,-C,2alkyl, hy-droxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl; or Wherein both of R, and R2 represent substituents selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C1-C4alkylphenyl-Cj-C4aIkyI;
c) At least one amine phosphate partial ester (III), Wherein m represents 1 or 2;
n represents 2 if m represents 1; or represents 1 if m represents 2; and R represents a substituent selected from the group consisting of Cl-Cl2alkyl, hydroxy-C2-Cl2alkyl, amino-C2-Cl2alkyl, phenyl, phenyl-Cl-C4alkyl, Cl-C4alkylphenyl, Cl-C4alkylphenyl-Cl-C4alkyl, C4-C$cycloalkyl, C4-C$cycloalkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cycloalkyl-C,-C4alkyl; and Ra, Rb, Rc and Rd independently of one another represent hydrogen or a substituent selected from the group consisting of C,-C,2alkyl, hy-droxy-C2-Cl2alkyl, amino-C2-Cl2alkyl, phenyl, phenyl-Cl-C4alkyl, C,-C4alkylphenyl, C,-C4alkylphenyl-C,-C4alkyl, C4-C$cycloalkyl, C4-C$cyclo-alkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cyclo-alkyl-C,-C4alkyl; and d) Additional customary additives.
The compositions as described above are suitable as corrosion inhibitor in non-aqueous, partially aqueous or aqueous functional fluids or liquids.
The expressions and terms used above and below are preferably defined as follows in the description of the present invention:
In a compound (I) R, defined C6-Cl$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 H
RCH=C-C-H I, R
Wherein 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. Preferably R' and R" are C3-Cl5alkyl or C3-Cl5alkenyl groups. In a particu-larly advantageous embodiment, R has from about 16 to about 18 C-atoms, R' is hydrogen or C,-C7alkyl or C2-C7alkenyl and R" is C5-C,5alkyl or C5-C,5alkenyl.
R2 is hydrogen or preferably methyl.
In a compound (I) the index 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 obtain-able by reacting the R-substituted succinic acid with ethylene oxide or ethylene glycol of de-sired chain length, if R2 represents hydrogen, or with propylene oxide or polypropylene glycol of desired chain length, if R2 represents methyl.
Compounds (I) are known and at least some of them are commercially available.
The prepa-ration of compounds (I) is described in British Patent Specification No.
795,491.
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.
In a compound (II) one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl; or Both of R, and R2 represent substituents selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl.
R, and R2 defined as C,-C,2alkyl is, for example, C,-C6alkyl, 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 C7-C,2alkyl, e.g. straight-chain or branched heptyl, octyl, isooctyl, nonyl, tert-nonyl, decyl, un-decyl or dodecyl.
R, and R2 defined as hydroxy-C2-C,2alkyl, is e.g. 2-hydroxyethyl, dihydroxyethyl, 2- or 3-hydroxypropyl, 2-, 3-dihydroxypropyl, glyceryl or any of the above-mentioned C4-Clzalkyl groups substituted by 1-3 hydroxy groups.
R, and R2 defined as amino-C2-C,2alkyl is e.g. 2-aminoethyl, diaminoethyl or 2-or 3-aminopropyl or any of the above-mentioned C4-C,2alkyl groups substituted by 1-3 amino groups.
R, and R2 defined as C2-C20alkenyl 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.
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 R, represents C10-C,6alkenyl, R2 represents methyl and n is a numeral from 1 to 20;
b) At least one imidazoline compound (II), Wherein one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl and C12-C,$alkenyl; or Wherein both of R, and R2 represent substituents selected from the group consist-ing of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl and C12-C,$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 C,-C,2alkyl, hy-droxy-C2-C,2alkyl and amino-C2-C,2alkyl; and Ra, Rb, Rc and Rd independently of one another represent hydrogen or a substituent selected from the group consisting of C,-C,2alkyl and hydroxy-C2-C,2alkyl; and B) A functional fluid.
A particularly preferred embodiment of the invention relates to composition, which comprises A) An additive mixture that essentially consists of a) At least one alkenyl succinic half ester (I), wherein R, represents C12-C,6alkenyl, R2 represents methyl and n is a numeral from 1 to 20;
b) At least one imidazoline compound (II), Wherein one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl and C12-C,$alkenyl;
or Wherein both of R, and R2 represent substituents selected from the group con-sisting of C,-C,2alkyl and C12-C,$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 C,-C,2alkyl and hydroxy-Cz-Clzalkyl; and Ra, Rb, Rc and Rd independently of one another represent hydrogen or a substitu-ent selected from the group consisting of C,-C,2alkyl and hydroxy-C2-C,2alkyl;
and B) A functional fluid.
A highly preferred embodiment of the invention relates to a composition, which comprises a) At least one alkenyl succinic half ester (I), Wherein R, represents C6-C,$alkenyl, R2 represents methyl and n is a nu-meral from 1 to 100;
b) At least one imidazoline compound (II), Wherein one of R, and R2 represents hydrogen and the other one repre-sents a substituent selected from the group consisting of C,-C,2alkyl, hy-droxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl; or Wherein both of R, and R2 represent substituents selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C1-C4alkylphenyl-Cj-C4aIkyI;
c) At least one amine phosphate partial ester (III), Wherein m represents 1 or 2;
n represents 2 if m represents 1; or represents 1 if m represents 2; and R represents a substituent selected from the group consisting of Cl-Cl2alkyl, hydroxy-C2-Cl2alkyl, amino-C2-Cl2alkyl, phenyl, phenyl-Cl-C4alkyl, Cl-C4alkylphenyl, Cl-C4alkylphenyl-Cl-C4alkyl, C4-C$cycloalkyl, C4-C$cycloalkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cycloalkyl-C,-C4alkyl; and Ra, Rb, Rc and Rd independently of one another represent hydrogen or a substituent selected from the group consisting of C,-C,2alkyl, hy-droxy-C2-Cl2alkyl, amino-C2-Cl2alkyl, phenyl, phenyl-Cl-C4alkyl, C,-C4alkylphenyl, C,-C4alkylphenyl-C,-C4alkyl, C4-C$cycloalkyl, C4-C$cyclo-alkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cyclo-alkyl-C,-C4alkyl; and d) Additional customary additives.
The compositions as described above are suitable as corrosion inhibitor in non-aqueous, partially aqueous or aqueous functional fluids or liquids.
The expressions and terms used above and below are preferably defined as follows in the description of the present invention:
In a compound (I) R, defined C6-Cl$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 H
RCH=C-C-H I, R
Wherein 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. Preferably R' and R" are C3-Cl5alkyl or C3-Cl5alkenyl groups. In a particu-larly advantageous embodiment, R has from about 16 to about 18 C-atoms, R' is hydrogen or C,-C7alkyl or C2-C7alkenyl and R" is C5-C,5alkyl or C5-C,5alkenyl.
R2 is hydrogen or preferably methyl.
In a compound (I) the index 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 obtain-able by reacting the R-substituted succinic acid with ethylene oxide or ethylene glycol of de-sired chain length, if R2 represents hydrogen, or with propylene oxide or polypropylene glycol of desired chain length, if R2 represents methyl.
Compounds (I) are known and at least some of them are commercially available.
The prepa-ration of compounds (I) is described in British Patent Specification No.
795,491.
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.
In a compound (II) one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl; or Both of R, and R2 represent substituents selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl.
R, and R2 defined as C,-C,2alkyl is, for example, C,-C6alkyl, 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 C7-C,2alkyl, e.g. straight-chain or branched heptyl, octyl, isooctyl, nonyl, tert-nonyl, decyl, un-decyl or dodecyl.
R, and R2 defined as hydroxy-C2-C,2alkyl, is e.g. 2-hydroxyethyl, dihydroxyethyl, 2- or 3-hydroxypropyl, 2-, 3-dihydroxypropyl, glyceryl or any of the above-mentioned C4-Clzalkyl groups substituted by 1-3 hydroxy groups.
R, and R2 defined as amino-C2-C,2alkyl is e.g. 2-aminoethyl, diaminoethyl or 2-or 3-aminopropyl or any of the above-mentioned C4-C,2alkyl groups substituted by 1-3 amino groups.
R, and R2 defined as C2-C20alkenyl 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.
R, and R2 defined as phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl radicals are, for example, benzyl, 1- or 2-phenethyl, 4-methyl- or 4-ethylphenyl, cumyl or 4-methylbenzyl.
According to preferred embodiments one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl, hy-droxy-C2-Cl2alkyl, amino-C2-Cl2alkyl and C12-Cl$alkenyl; or Both of R, and R2 represent substituents selected from the group consisting of Cl-Cl2alkyl, hydroxy-C2-C,2alkyl, amino-C2-Cl2alkyl and C12-Cl$alkenyl.
According to another preferred embodiment one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl and C12-C,$alkenyl; or Both of R, and R2 represent substituents selected from the group consisting of C,-C,2alkyl and C12-C,$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.
In a compound (III) m represents 1 or 2. In the event that m represents 1, n represents 2.
Such compounds are represented by the formula Ra O [R+dJ
In the event that m represents 2, n represents 1. Such compounds are represented by the formula Ra +
RO/ IP \O Rb R \ Rd N
OR c In a compound (III) R represents a substituent selected from the group consisting of Cl-Cl2alkyl, hydroxy-C2-Cl2alkyl, amino-C2-Cl2alkyl, phenyl, phenyl-Cl-C4alkyl, Cl-C4alkylphenyl, Cl-C4alkylphenyl-Cl-C4alkyl, C4-C$cycloalkyl, C4-C$cycloalkyl-Cl-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cycloalkyl-C,-C4alkyl; and Ra, Rb, R. and Rd independently of one another represent hydrogen or a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, phenyl, phenyl-Cl-C4alkyl, Cl-C4alkylphenyl, Cl-C4alkylphenyl-Cl-C4alkyl, C4-C$cycloalkyl, C4-C8CyClOalkyl-C,-C4alkyl, C,-C4alkyl-C4-C8CyClOalkyl and C1-C4alkyl-C4-C8CyClO-alkyl-Cl-C4alkyl.
The definitions of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl, C,-C4alkylphenyl-C,-C4alkyl correspond to the defini-tions given above with regard to compounds (I) and (II).
R as well as Ra, Rb, Rc and Rd defined as C4-C$cycloalkyl, C4-C$cycloalkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cycloalkyl-C,-C4alkyl are, for example, cyclopentyl, cyclohexyl, cyclopentylmethyl or cyclohexylmethyl, cyclopentyl-1, 1 -ethyl, cyclo-hexyl-1, 1 -ethyl, cyclopentyl-1,2-ethyl, cyclohexyl-1,2-ethyl, cyclopentyl-1,2-propyl or cyclohe-xyl-1,2-propyl, which can be substituted on the C4-C$cycloalkyl groups by C,-C4alkyl, e.g.
methyl, ethyl, n- propyl or isopropyl.
According to preferred embodiments R represents a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl and amino-C2-C,2alkyl; and Ra, Rb, Rc and Rd independently of one another represent hydrogen or a substituent selected from the group consisting of C,-C,2alkyl and hydroxy-C2-C,2alkyl.
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.
Other 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.
Examples of 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 inter-nal 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.
Examples of 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.
Examples of 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 exam-ple, 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 Chem-istry 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. 13, page 533 et seq. (Hydraulic Fluids);
Performance Testing of Hydraulic Fluids; R. Tourret and E.P. Wright, Hyden & Son Ltd. GB, on behalf of The Institute of Petroleum London, ISBN 0 85501 317 6; Ullmann's Encyclopedia of Ind.
Chem., Fifth Completely Revised Edition, Verlag Chemie, DE-Weinheim, VCH-Publishers for U.S., Vol. A 15, page 423 et seq. (Lubricants), Vol. A 13, page 165 et seq.
(Hydraulic Fluids).
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 engi-neering, for example soy bean oil prepared by genetic engineering.
According to preferred embodiments one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl, hy-droxy-C2-Cl2alkyl, amino-C2-Cl2alkyl and C12-Cl$alkenyl; or Both of R, and R2 represent substituents selected from the group consisting of Cl-Cl2alkyl, hydroxy-C2-C,2alkyl, amino-C2-Cl2alkyl and C12-Cl$alkenyl.
According to another preferred embodiment one of R, and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C,-C,2alkyl and C12-C,$alkenyl; or Both of R, and R2 represent substituents selected from the group consisting of C,-C,2alkyl and C12-C,$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.
In a compound (III) m represents 1 or 2. In the event that m represents 1, n represents 2.
Such compounds are represented by the formula Ra O [R+dJ
In the event that m represents 2, n represents 1. Such compounds are represented by the formula Ra +
RO/ IP \O Rb R \ Rd N
OR c In a compound (III) R represents a substituent selected from the group consisting of Cl-Cl2alkyl, hydroxy-C2-Cl2alkyl, amino-C2-Cl2alkyl, phenyl, phenyl-Cl-C4alkyl, Cl-C4alkylphenyl, Cl-C4alkylphenyl-Cl-C4alkyl, C4-C$cycloalkyl, C4-C$cycloalkyl-Cl-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cycloalkyl-C,-C4alkyl; and Ra, Rb, R. and Rd independently of one another represent hydrogen or a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, phenyl, phenyl-Cl-C4alkyl, Cl-C4alkylphenyl, Cl-C4alkylphenyl-Cl-C4alkyl, C4-C$cycloalkyl, C4-C8CyClOalkyl-C,-C4alkyl, C,-C4alkyl-C4-C8CyClOalkyl and C1-C4alkyl-C4-C8CyClO-alkyl-Cl-C4alkyl.
The definitions of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl, C,-C4alkylphenyl-C,-C4alkyl correspond to the defini-tions given above with regard to compounds (I) and (II).
R as well as Ra, Rb, Rc and Rd defined as C4-C$cycloalkyl, C4-C$cycloalkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cycloalkyl-C,-C4alkyl are, for example, cyclopentyl, cyclohexyl, cyclopentylmethyl or cyclohexylmethyl, cyclopentyl-1, 1 -ethyl, cyclo-hexyl-1, 1 -ethyl, cyclopentyl-1,2-ethyl, cyclohexyl-1,2-ethyl, cyclopentyl-1,2-propyl or cyclohe-xyl-1,2-propyl, which can be substituted on the C4-C$cycloalkyl groups by C,-C4alkyl, e.g.
methyl, ethyl, n- propyl or isopropyl.
According to preferred embodiments R represents a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl and amino-C2-C,2alkyl; and Ra, Rb, Rc and Rd independently of one another represent hydrogen or a substituent selected from the group consisting of C,-C,2alkyl and hydroxy-C2-C,2alkyl.
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.
Other 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.
Examples of 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 inter-nal 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.
Examples of 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.
Examples of 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 exam-ple, 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 Chem-istry 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. 13, page 533 et seq. (Hydraulic Fluids);
Performance Testing of Hydraulic Fluids; R. Tourret and E.P. Wright, Hyden & Son Ltd. GB, on behalf of The Institute of Petroleum London, ISBN 0 85501 317 6; Ullmann's Encyclopedia of Ind.
Chem., Fifth Completely Revised Edition, Verlag Chemie, DE-Weinheim, VCH-Publishers for U.S., Vol. A 15, page 423 et seq. (Lubricants), Vol. A 13, page 165 et seq.
(Hydraulic Fluids).
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 engi-neering, 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-a-olefins or sili-cones 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 ac-ids, 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-a-olefins, ester-based lubricants, phosphates, glycols, polyglycols and polyalkylene gly-cols and mixtures thereof with water.
Said lubricants or mixtures thereof can also be mixed with an 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, e.g. greases, gear fluids, metal working fluids and hydraulic flu-ids, may additionally contain further additives which are added in order further to improve their fundamental properties. These include: antioxidants, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents, tackyfiers, thixotropic builders, dewatering agents, antifoam agents, demulsifiers, high pressure addi-tives 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:
1. 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-(a-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. 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methyl-undec-1'-yl)-phenol, 2,4-dimethyl-6-(1'-methylheptadec-1'-yl)-phenol, 2,4-dimethyl-6-(1'-methyl-tridec-1'-yl)-phenol and mixtures thereof 1.2. Alkylthiomethylphenols: 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonyl-phenol 1.3. Hydroguinones and alkylated hydroguinones: 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyl-oxyphenol, 2,6-di-tert-butyl-hydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenylstearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate 1.4. Tocopherols: a-, R-, y- or b-tocopherols and mixtures thereof (vitamin E) 1.5. Hydroxylated thiodiphenyl ethers: 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis-(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl) disulphide 1.6. Alkylidene bisphenols: 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-(a-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-(a-methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[6-(a,a-di-methylbenzyl)-4-nonylphenol], 4,4'-methylenebis(2,6-di-tert-butylphenol), 4,4'-methyl-enebis(6-tert-butyl-2-methylphenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-phenyl)butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-phenyl)-3-n-dodecylmercaptobutane, ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-methyl-phenyl)dicyclopenta-diene, bis[2-(3'-tert-butyl-2'-hydroxy-5'-methyl-benzyl)-6-tert-butyl-4-methyl-phenyl]
terephthalate, 1,1-bis(3,5-dimethyl-2-hydroxyphenyl)-butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane, 2,2-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dode-cylmercaptobutane, 1,1,5,5-tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane 1.7. 0-, N- and S-benzyl compounds: 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl 4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis(3,5-di-tert-butyl-4-hy-droxybenzyl) sulphide, isooctyl 3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate 1.8. Hydroxybenzylated malonates: dioctadecyl 2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)-malonate, dioctadecyl 2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate, didodecyl mercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, di-[4-(1,1,3,3-tetramethylbutyl)-phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate 1.9. 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-cyanurate, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexahydro-1,3,5-triazine, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl) isocyanurate 1.11. Acylaminophenols: 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl) carbamate 1.12. Esters of beta-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid with monohydric or polyhydric alcohols, e.g. 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-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane 1.13. Esters of beta-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid (with monohydric or polyhydric alcohols), e.g. the alcohols with methanol, ethanol, n-octanol, isooc-tanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentylglycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentae-rythritol, tris(hydroxyethyl) isocyanurate, N,N'-bis(hydroxyethyl)-oxalamide, thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hy-droxymethyl-1 -phospha-2,6,7-trioxabicyclo[2.2.2]octane 1.14. Esters of beta-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with monohydric or polyhydric alcohols, e.g. the alcohols stated under 13.
1.15. Ester of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid with monohydric or polyhydric alcohols, e.g. the alcohols stated under 13.
1.16. Amides of beta-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, e.g.
N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamine, N,N'-bis(3,5-di-tert-butyl-4-hydroxy-phenylpropionyl)hydrazine 1.17. Ascorbic acid (vitamin C) 1.18. Amine antioxidants: N,N'-diisopropyl-p-phenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N'-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N'-bis(1-methyl-heptyl)-p-phenylenediamine, N,N'-dicyclohexyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, N,N'-di-(naphth-2-yl)-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(1,3-dimethyl-butyl)-N'-phenyl-p-phenylenediamine, N-(1-methylheptyl)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, 4-(p-toluenesulphonamido)diphenylamine, N,N'-dimethyl-N,N'-di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxy-diphenylamine, N-phenyl-l-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, e.g. 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-(1',3'-dimethyl-butyl)phenyl]amine, tert-octylated N-phenyl-l-naphthylamine, mixture of mono- and dialkylated tert-butyl/tert-octyldiphenylamines, mixture of mono-and dialkylated nonyldiphenylamines, mixture of mono- and dialkylated dodecyldiphenyl-amines, mixture of mono- and dialkylated isopropyl/isohexyldiphenylamines, mixtures of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, mixture of mono- and dialkylated tert-butyl tert-octyl-phenothiazines, mixture of mono- and dialkylated tert-octylphenothiazines, N-allyl-phenothiazine, N,N,N',N'-tetraphenyl-1,4-diaminobut-2-ene, N,N-bis-(2,2,6,6-tetrame-thylpiperidin-4-yl)-hexamethylenediamine, bis-(2,2,6,6-tetramethylpiperidin-4-yl) seba-cate, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpiperidin-4-ol 2. Further 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 3. Further metal deactivators:
3.1. 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 3.3. Imidazole derivatives: 4,4'-methylenebis(2-undecyl-5-methylimidazole), bis[(N-methyl)imidazol-2-yl]carbinol octyl ether 3.4. Sulphur-containing heterocyclic compounds: 2-mercaptobenzothiazole, 2,5-dimer-capto-1,3,4-thiadiazole, 2,5-dimercaptobenzothiadiazole and derivatives thereof; 3,5-bis[di-(2-ethylhexyl)aminomethyl]-1,3,4-thiadiazolin-2-one 3.5. Amino compounds: salicylidenepropylenediamine, salicylaminoguanidine and salts thereof 4. Corrosion inhibitors:
Said lubricants or mixtures thereof can also be mixed with an 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, e.g. greases, gear fluids, metal working fluids and hydraulic flu-ids, may additionally contain further additives which are added in order further to improve their fundamental properties. These include: antioxidants, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents, tackyfiers, thixotropic builders, dewatering agents, antifoam agents, demulsifiers, high pressure addi-tives 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:
1. 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-(a-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. 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methyl-undec-1'-yl)-phenol, 2,4-dimethyl-6-(1'-methylheptadec-1'-yl)-phenol, 2,4-dimethyl-6-(1'-methyl-tridec-1'-yl)-phenol and mixtures thereof 1.2. Alkylthiomethylphenols: 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonyl-phenol 1.3. Hydroguinones and alkylated hydroguinones: 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyl-oxyphenol, 2,6-di-tert-butyl-hydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenylstearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate 1.4. Tocopherols: a-, R-, y- or b-tocopherols and mixtures thereof (vitamin E) 1.5. Hydroxylated thiodiphenyl ethers: 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis-(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl) disulphide 1.6. Alkylidene bisphenols: 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-(a-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-(a-methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[6-(a,a-di-methylbenzyl)-4-nonylphenol], 4,4'-methylenebis(2,6-di-tert-butylphenol), 4,4'-methyl-enebis(6-tert-butyl-2-methylphenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-phenyl)butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-phenyl)-3-n-dodecylmercaptobutane, ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-methyl-phenyl)dicyclopenta-diene, bis[2-(3'-tert-butyl-2'-hydroxy-5'-methyl-benzyl)-6-tert-butyl-4-methyl-phenyl]
terephthalate, 1,1-bis(3,5-dimethyl-2-hydroxyphenyl)-butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane, 2,2-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dode-cylmercaptobutane, 1,1,5,5-tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane 1.7. 0-, N- and S-benzyl compounds: 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl 4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis(3,5-di-tert-butyl-4-hy-droxybenzyl) sulphide, isooctyl 3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate 1.8. Hydroxybenzylated malonates: dioctadecyl 2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)-malonate, dioctadecyl 2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate, didodecyl mercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, di-[4-(1,1,3,3-tetramethylbutyl)-phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate 1.9. 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-cyanurate, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexahydro-1,3,5-triazine, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl) isocyanurate 1.11. Acylaminophenols: 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl) carbamate 1.12. Esters of beta-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid with monohydric or polyhydric alcohols, e.g. 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-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane 1.13. Esters of beta-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid (with monohydric or polyhydric alcohols), e.g. the alcohols with methanol, ethanol, n-octanol, isooc-tanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentylglycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentae-rythritol, tris(hydroxyethyl) isocyanurate, N,N'-bis(hydroxyethyl)-oxalamide, thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hy-droxymethyl-1 -phospha-2,6,7-trioxabicyclo[2.2.2]octane 1.14. Esters of beta-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with monohydric or polyhydric alcohols, e.g. the alcohols stated under 13.
1.15. Ester of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid with monohydric or polyhydric alcohols, e.g. the alcohols stated under 13.
1.16. Amides of beta-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, e.g.
N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamine, N,N'-bis(3,5-di-tert-butyl-4-hydroxy-phenylpropionyl)hydrazine 1.17. Ascorbic acid (vitamin C) 1.18. Amine antioxidants: N,N'-diisopropyl-p-phenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N'-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N'-bis(1-methyl-heptyl)-p-phenylenediamine, N,N'-dicyclohexyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, N,N'-di-(naphth-2-yl)-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(1,3-dimethyl-butyl)-N'-phenyl-p-phenylenediamine, N-(1-methylheptyl)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, 4-(p-toluenesulphonamido)diphenylamine, N,N'-dimethyl-N,N'-di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxy-diphenylamine, N-phenyl-l-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, e.g. 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-(1',3'-dimethyl-butyl)phenyl]amine, tert-octylated N-phenyl-l-naphthylamine, mixture of mono- and dialkylated tert-butyl/tert-octyldiphenylamines, mixture of mono-and dialkylated nonyldiphenylamines, mixture of mono- and dialkylated dodecyldiphenyl-amines, mixture of mono- and dialkylated isopropyl/isohexyldiphenylamines, mixtures of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, mixture of mono- and dialkylated tert-butyl tert-octyl-phenothiazines, mixture of mono- and dialkylated tert-octylphenothiazines, N-allyl-phenothiazine, N,N,N',N'-tetraphenyl-1,4-diaminobut-2-ene, N,N-bis-(2,2,6,6-tetrame-thylpiperidin-4-yl)-hexamethylenediamine, bis-(2,2,6,6-tetramethylpiperidin-4-yl) seba-cate, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpiperidin-4-ol 2. Further 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 3. Further metal deactivators:
3.1. 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 3.3. Imidazole derivatives: 4,4'-methylenebis(2-undecyl-5-methylimidazole), bis[(N-methyl)imidazol-2-yl]carbinol octyl ether 3.4. Sulphur-containing heterocyclic compounds: 2-mercaptobenzothiazole, 2,5-dimer-capto-1,3,4-thiadiazole, 2,5-dimercaptobenzothiadiazole and derivatives thereof; 3,5-bis[di-(2-ethylhexyl)aminomethyl]-1,3,4-thiadiazolin-2-one 3.5. Amino compounds: salicylidenepropylenediamine, salicylaminoguanidine and salts thereof 4. 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 triethanolamine salts 4.2. Nitrogen-containing compounds:
4.2.1 Tertiary aliphatic and cycloaliphatic amines and amine salts of organic and inorganic acids, e.g. oil-soluble alkylammonium carboxylates, and furthermore 1-[N,N-bis-(2-hy-droxyethyl)amino]-3-(4-nonylphenoxy)propan-2-ol 4.2.2 Heterocyclic compounds, e.g. substituted imidazolines and oxazolines, e.g. 2-hepta-decenyl-1 -(2-hydroxyethyl)-imidazoline 5. Sulphur-containing compounds: barium dinonylnaphthalenesulphonates, calcium petroleum sulphonates, alkylthio-substituted aliphatic carboxylic acids, esters of ali-phatic 2-sulphocarboxylic acids and salts thereof 6. Viscosity index improvers: polyacrylates, polymethacrylates, vinylpyrroli-done/methacrylate copolymers, polyvinylpyrrolidiones, polybutenes, olefin copoly-mers, styrene/acrylate copolymers, polyethers 7. Pour point depressants: poly(meth)acrylates, ethylene-vinyl acetate copolymers, alkyl polystyrenes, fumarate copolymers, alkylated naphthalene derivatives 8. Dispersants/Surfactants: polybutenylsuccinamides or polybutenylsuccinimides, polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sul-phonates and phenolates 9. 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,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 10. Substances for reducing the coefficient of friction: lard oil, oleic acid, tallow, rapeseed oil, sulphurised fats, amines. Further examples are stated in EP-A-O 565 487 11. Special additives for use in water/oil metal processing and hydraulic fluids:
11.1 Emulsifiers: petroleum sulphonates, amines, such as polyoxyethylated fatty amines, non-ionic surface-active substances 11.2 Buffers: alkanolamines 11.3 Biocides: triazines, thiazolinones, trisnitromethane, morpholine, sodium pyridinethiol 11.4 Processing speed improvers: calcium sulphonates and barium sulphonates 11.5 Tackifiers: acrylamide copolymer, polyisubutene resins.
11.6 Thixotropic builders: microcrystalline waxes, oxidized waxes and oxidized esters 11.7 Dewatering agents: polyglycol ethers, butyldiglycols.
Said components can be mixed with the lubricants in a manner known per se. It is also possi-ble to prepare a concentrate or a so-called additive package, which can be diluted to the con-centrations 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 mix-ture A) may vary within the ranges of approximately from 10 : 10 : 80 and 80 :
10 : 10 to 10 80: 10% by weight.
Although 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.
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 triethanolamine salts 4.2. Nitrogen-containing compounds:
4.2.1 Tertiary aliphatic and cycloaliphatic amines and amine salts of organic and inorganic acids, e.g. oil-soluble alkylammonium carboxylates, and furthermore 1-[N,N-bis-(2-hy-droxyethyl)amino]-3-(4-nonylphenoxy)propan-2-ol 4.2.2 Heterocyclic compounds, e.g. substituted imidazolines and oxazolines, e.g. 2-hepta-decenyl-1 -(2-hydroxyethyl)-imidazoline 5. Sulphur-containing compounds: barium dinonylnaphthalenesulphonates, calcium petroleum sulphonates, alkylthio-substituted aliphatic carboxylic acids, esters of ali-phatic 2-sulphocarboxylic acids and salts thereof 6. Viscosity index improvers: polyacrylates, polymethacrylates, vinylpyrroli-done/methacrylate copolymers, polyvinylpyrrolidiones, polybutenes, olefin copoly-mers, styrene/acrylate copolymers, polyethers 7. Pour point depressants: poly(meth)acrylates, ethylene-vinyl acetate copolymers, alkyl polystyrenes, fumarate copolymers, alkylated naphthalene derivatives 8. Dispersants/Surfactants: polybutenylsuccinamides or polybutenylsuccinimides, polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sul-phonates and phenolates 9. 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,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 10. Substances for reducing the coefficient of friction: lard oil, oleic acid, tallow, rapeseed oil, sulphurised fats, amines. Further examples are stated in EP-A-O 565 487 11. Special additives for use in water/oil metal processing and hydraulic fluids:
11.1 Emulsifiers: petroleum sulphonates, amines, such as polyoxyethylated fatty amines, non-ionic surface-active substances 11.2 Buffers: alkanolamines 11.3 Biocides: triazines, thiazolinones, trisnitromethane, morpholine, sodium pyridinethiol 11.4 Processing speed improvers: calcium sulphonates and barium sulphonates 11.5 Tackifiers: acrylamide copolymer, polyisubutene resins.
11.6 Thixotropic builders: microcrystalline waxes, oxidized waxes and oxidized esters 11.7 Dewatering agents: polyglycol ethers, butyldiglycols.
Said components can be mixed with the lubricants in a manner known per se. It is also possi-ble to prepare a concentrate or a so-called additive package, which can be diluted to the con-centrations 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 mix-ture A) may vary within the ranges of approximately from 10 : 10 : 80 and 80 :
10 : 10 to 10 80: 10% by weight.
Although 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), Wherein R, represents C6-C,$alkenyl, R2 represents hydrogen or methyl and n is a numeral from 0 to 100;
b) At least one imidazoline compound (II), Wherein one of R, and R2 represents hydrogen and the other one repre-sents a substituent selected from the group consisting of C,-C,2alkyl, hy-droxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl; or Wherein both of R, and R2 represent substituents selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl; and c) At least one amine phosphate partial ester (III), Wherein m represents 1 or 2, n represents 2, if m represents 1; or repre-sents 1, if m represents 2;
R represents a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl, C,-C4alkylphenyl-C,-C4alkyl, C4-C$cycloalkyl, C4-C$cycloalkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cycloalkyl-C,-C4alkyl; and Ra, Rb, Rc and Rd independently of one another represent hydrogen or a substituent selected from the group consisting of C,-C,2alkyl, hy-droxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-Cl-C4alkyl, Cl-C4alkylphenyl, Cl-C4alkylphenyl-Cl-C4alkyl, C4-C$cycloalkyl, C4-C$cycloalkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C, -C4a l kyl-C4-C8CyCl oa l kyl-C, -C4a l kyl .
The definitions of 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.
According to a preferred embodiment, the invention relates to the additive mixture, as de-fined above, used as additives in a metal working fluid.
b) At least one imidazoline compound (II), Wherein one of R, and R2 represents hydrogen and the other one repre-sents a substituent selected from the group consisting of C,-C,2alkyl, hy-droxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl; or Wherein both of R, and R2 represent substituents selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl and C,-C4alkylphenyl-C,-C4alkyl; and c) At least one amine phosphate partial ester (III), Wherein m represents 1 or 2, n represents 2, if m represents 1; or repre-sents 1, if m represents 2;
R represents a substituent selected from the group consisting of C,-C,2alkyl, hydroxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-C,-C4alkyl, C,-C4alkylphenyl, C,-C4alkylphenyl-C,-C4alkyl, C4-C$cycloalkyl, C4-C$cycloalkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C,-C4alkyl-C4-C$cycloalkyl-C,-C4alkyl; and Ra, Rb, Rc and Rd independently of one another represent hydrogen or a substituent selected from the group consisting of C,-C,2alkyl, hy-droxy-C2-C,2alkyl, amino-C2-C,2alkyl, C2-C20alkenyl, phenyl, phenyl-Cl-C4alkyl, Cl-C4alkylphenyl, Cl-C4alkylphenyl-Cl-C4alkyl, C4-C$cycloalkyl, C4-C$cycloalkyl-C,-C4alkyl, C,-C4alkyl-C4-C$cycloalkyl and C, -C4a l kyl-C4-C8CyCl oa l kyl-C, -C4a l kyl .
The definitions of components a), b) and c) present in the additive mixture corresponds to the definitions of components a), b) and c) present in the compositions as defined above.
According to a preferred embodiment, the invention relates to the additive mixture, as de-fined above, used as additives in a metal working fluid.
The invention also relates to the process for protection against corrosion or oxidative degra-dation of metals, wherein the metal is exposed to a functional fluid comprising the additive mixture as defined above.
According to a preferred embodiment, the invention relates to the process for protection against corrosion or oxidative degradation of zinc, aluminum or alloys thereof, wherein zinc, aluminum or alloys thereof are exposed to a functional fluid comprising the additive mixture as defined above.
A further embodiment of the invention relates to a process for protection against corrosion or oxidative degradation of zinc, aluminum or alloys thereof, wherein zinc, aluminum or alloys thereof are exposed to a functional fluid comprising at least one alkenyl succinic half ester of the formula I as defined above, wherein R, represents C6-C,$alkenyl, R2 represents hydrogen or methyl and n is a numeral from 1 to 100.
The following Examples illustrate the invention:
Application Examples 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.
According to a preferred embodiment, 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, represents C6-C,$alkenyl, R2 represents hydrogen or methyl and n is a numeral from 1 to 100.
The following Examples illustrate the invention:
Application Examples 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.
Corrosion Inhibitor Test Specimen Passed test cycles Additive treat rate Reference oil Zinc 19 app. 15-20%
Mixture A Zinc > 24 3%
Mixture B Zinc > 24 5%
Mixture C Zinc > 24 3%
Mixture D Zinc 20 3%
Reference oil Aluminum 0 app. 15-20%
Mixture A Aluminum > 15 3%
Mixture B Aluminum > 15 5%
Mixture C Aluminum > 15 3%
Mixture D Aluminum > 15 3%
Reference oil: As mentioned in "VDA-Prufblatt" from May 2003; VDA 230- 201:
Mixture A = 3% Irgacor L12 in a paraffinic base oil Mixture B = 5% Irgalube 349 in a parafinic base oil Mixture C = 0.9% IRGACOR L12; 1.5% Amine 0; 0.6% IRGALUBE 349 in an naphthenic base oil Mixture D = 0.6% IRGACOR L12; 0.9% Amine 0; 1.5% IRGALUBE 349 in a paraffinic base oil.
Mixture A Zinc > 24 3%
Mixture B Zinc > 24 5%
Mixture C Zinc > 24 3%
Mixture D Zinc 20 3%
Reference oil Aluminum 0 app. 15-20%
Mixture A Aluminum > 15 3%
Mixture B Aluminum > 15 5%
Mixture C Aluminum > 15 3%
Mixture D Aluminum > 15 3%
Reference oil: As mentioned in "VDA-Prufblatt" from May 2003; VDA 230- 201:
Mixture A = 3% Irgacor L12 in a paraffinic base oil Mixture B = 5% Irgalube 349 in a parafinic base oil Mixture C = 0.9% IRGACOR L12; 1.5% Amine 0; 0.6% IRGALUBE 349 in an naphthenic base oil Mixture D = 0.6% IRGACOR L12; 0.9% Amine 0; 1.5% IRGALUBE 349 in a paraffinic base oil.
Claims (10)
1. A composition, which comprises A) An additive mixture that essentially consists of a) At least one alkenyl succinic half ester of the formula Wherein R1 represents C6-C18Alkenyl, R2 represents hydrogen or methyl and n is a numeral from 1 to 100;
b) At least one imidazoline compound of the formula Wherein one of R1 and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl; or Wherein both of R1 and R2 represent substituents selected from the group con-sisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl;
and c) At least one amine phosphate partial ester of the formula 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 C1-C12alkyl, hy-droxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cyclo-alkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cyclo-alkyl-C1-C4alkyl; and R a, R b, R c and R d independently of one another represent hydrogen or a substitu-ent selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; and B) A functional fluid.
b) At least one imidazoline compound of the formula Wherein one of R1 and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl; or Wherein both of R1 and R2 represent substituents selected from the group con-sisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl;
and c) At least one amine phosphate partial ester of the formula 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 C1-C12alkyl, hy-droxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cyclo-alkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cyclo-alkyl-C1-C4alkyl; and R a, R b, R c and R d independently of one another represent hydrogen or a substitu-ent selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; and B) A functional fluid.
2. A composition according to claim 1, which comprises A) An additive mixture that essentially consists of a) At least one alkenyl succinic half ester (I), wherein R1 represents C10-C16alkenyl, R2 represents methyl and n is a numeral from 1 to 20;
b) At least one imidazoline compound (II), Wherein one of R1 and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl and C12-C18alkenyl; or Wherein both of R1 and R2 represent substituents selected from the group consist-ing of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl and C12-C18alkenyl;
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 C1-C12alkyl, hy-droxy-C2-C12alkyl and amino-C2-C12alkyl; 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 C1-C12alkyl and hydroxy-C2-C12alkyl; and B) A functional fluid.
b) At least one imidazoline compound (II), Wherein one of R1 and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl and C12-C18alkenyl; or Wherein both of R1 and R2 represent substituents selected from the group consist-ing of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl and C12-C18alkenyl;
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 C1-C12alkyl, hy-droxy-C2-C12alkyl and amino-C2-C12alkyl; 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 C1-C12alkyl and hydroxy-C2-C12alkyl; and B) A functional fluid.
3. A composition according to claim 1, which comprises A) An additive mixture that essentially consists of a) At least one alkenyl succinic half ester (I), wherein R1 represents C12-C16alkenyl, R2 represents methyl and n is a numeral from 1 to 20;
b) At least one imidazoline compound (II), Wherein one of R1 and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C1-C12alkyl and C12-C18alkenyl;
or Wherein both of R1 and R2 represent substituents selected from the group con-sisting of C1-C12alkyl and C12-C18alkenyl; 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; and R represents a substituent selected from the group consisting of C1-C12alkyl and hydroxy-C2-C12alkyl; and R a, R b, R c and R d independently of one another represent hydrogen or a substitu-ent selected from the group consisting of C1-C12alkyl and hydroxy-C2-C12alkyl;
and B) A functional fluid.
b) At least one imidazoline compound (II), Wherein one of R1 and R2 represents hydrogen and the other one represents a substituent selected from the group consisting of C1-C12alkyl and C12-C18alkenyl;
or Wherein both of R1 and R2 represent substituents selected from the group con-sisting of C1-C12alkyl and C12-C18alkenyl; 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; and R represents a substituent selected from the group consisting of C1-C12alkyl and hydroxy-C2-C12alkyl; and R a, R b, R c and R d independently of one another represent hydrogen or a substitu-ent selected from the group consisting of C1-C12alkyl and hydroxy-C2-C12alkyl;
and B) A functional fluid.
4. A composition, which comprises a) At least one alkenyl succinic half ester (I), Wherein R1 represents C6-C18alkenyl, R2 represents methyl and n is a nu-meral from 1 to 100;
b) At least one imidazoline compound (II), Wherein one of R1 and R2 represents hydrogen and the other one repre-sents a substituent selected from the group consisting of C1-C12alkyl, hy-droxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl; or Wherein both of R1 and R2 represent substituents selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl;
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 C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; 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 C1-C12alkyl, hy-droxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cyclo-alkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cyclo-alkyl-C1-C4alkyl; and d) Additional customary additives.
b) At least one imidazoline compound (II), Wherein one of R1 and R2 represents hydrogen and the other one repre-sents a substituent selected from the group consisting of C1-C12alkyl, hy-droxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl; or Wherein both of R1 and R2 represent substituents selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl;
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 C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; 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 C1-C12alkyl, hy-droxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cyclo-alkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cyclo-alkyl-C1-C4alkyl; and d) Additional customary additives.
5. An additive mixture that essentially consists of a) At least one alkenyl succinic half ester (I), Wherein R1 represents C6-C18alkenyl, R2 represents hydrogen or methyl and n is a numeral from 0 to 100;
b) At least one imidazoline compound (II), Wherein one of R1 and R2 represents hydrogen and the other one repre-sents a substituent selected from the group consisting of C1-C12alkyl, hy-droxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl; or Wherein both of R1 and R2 represent substituents selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl; 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; and R represents a substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-Cl-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; 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 C1-C12alkyl, hy-droxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl.
b) At least one imidazoline compound (II), Wherein one of R1 and R2 represents hydrogen and the other one repre-sents a substituent selected from the group consisting of C1-C12alkyl, hy-droxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl; or Wherein both of R1 and R2 represent substituents selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl; 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; and R represents a substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-Cl-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; 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 C1-C12alkyl, hy-droxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl.
6. The additive mixture according to claim 5 for use as a metal working fluid.
7. A composition according to claim 1, wherein the functional fluid B) is a non-aqueous functional liquid selected from the group consisting of lubricants, hydraulic fluids, metal working fluids, engine coolants, transformer oils and switch gear oils.
8. A process for protection against corrosion or oxidative degradation of metals, wherein the metal is exposed to a functional fluid comprising the additive mixture according to claim 5.
9. A process for protection against corrosion or oxidative degradation of zinc, aluminum or alloys thereof, or zinc-coated steels, wherein zinc, aluminum or alloys thereof are ex-posed to a functional fluid comprising the additive mixture according to claim 5.
10. A process for protection against corrosion or oxidative degradation of zinc, aluminum or alloys thereof, or zinc-coated steels, wherein zinc, aluminum or alloys thereof are ex-posed to a functional fluid comprising at least one alkenyl succinic half ester of the for-mula Wherein R1 represents C6-C18alkenyl, R2 represents hydrogen or methyl and n is a nu-meral from 1 to 100.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06114370 | 2006-05-23 | ||
| EP06114370.7 | 2006-05-23 | ||
| PCT/EP2007/054674 WO2007135017A1 (en) | 2006-05-23 | 2007-05-15 | Corrosion inhibiting composition for non-ferrous metals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2650246A1 true CA2650246A1 (en) | 2007-11-29 |
| CA2650246C CA2650246C (en) | 2014-12-23 |
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|---|---|---|---|
| CA2650246A Expired - Fee Related CA2650246C (en) | 2006-05-23 | 2007-05-15 | Corrosion inhibiting composition for non-ferrous metals |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20100022425A1 (en) |
| EP (1) | EP2027235A1 (en) |
| JP (1) | JP5395658B2 (en) |
| KR (1) | KR20090010041A (en) |
| CN (1) | CN101454429B (en) |
| AU (1) | AU2007253453B2 (en) |
| CA (1) | CA2650246C (en) |
| RU (1) | RU2483099C2 (en) |
| TW (1) | TW200815586A (en) |
| WO (1) | WO2007135017A1 (en) |
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| JP5328185B2 (en) * | 2008-03-19 | 2013-10-30 | 本田技研工業株式会社 | Rust prevention composition and rust prevention treatment method using the same |
| JP5537912B2 (en) * | 2009-11-27 | 2014-07-02 | Ｊｘ日鉱日石エネルギー株式会社 | Surface treatment agent and surface treatment method |
| US8236205B1 (en) | 2011-03-11 | 2012-08-07 | Wincom, Inc. | Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles and other triazoles and methods for using same |
| US8236204B1 (en) | 2011-03-11 | 2012-08-07 | Wincom, Inc. | Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same |
| JP6113268B2 (en) * | 2012-04-26 | 2017-04-12 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | New composition with corrosion resistance in vapor space |
| ES2590979T3 (en) * | 2012-08-22 | 2016-11-24 | Basf Se | Corrosion protective agent formulation for the protection of zinc and cadmium against corrosion |
| RU2539129C1 (en) * | 2013-08-19 | 2015-01-10 | Федеральное государственное бюджетное учреждение науки Институт физической химии и электрохимии им. А.Н. Фрумкина Российской академии наук (ИФХЭ РАН) | Inhibitor of acid metal corrosion |
| US9309205B2 (en) | 2013-10-28 | 2016-04-12 | Wincom, Inc. | Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures |
| ES2843830T3 (en) * | 2014-12-29 | 2021-07-20 | Lubrizol Corp | Synergistic rust inhibitor combination for lubricating grease |
| KR102401413B1 (en) * | 2015-12-23 | 2022-05-24 | 헨켈 아게 운트 코. 카게아아 | metalworking fluid |
| DE112016006190T5 (en) | 2016-01-07 | 2018-10-04 | Autonetworks Technologies, Ltd. | Anti-corrosive agent and connected electrical wire |
| CN108884575A (en) * | 2016-03-30 | 2018-11-23 | 出光兴产株式会社 | Rust preventive oil composition |
| CN105937036A (en) * | 2016-06-28 | 2016-09-14 | 常州大学 | Rust prevention method for outdoor current transformer |
| CN107731492B (en) * | 2016-07-30 | 2019-01-18 | 宁波甬嘉变压器有限公司 | A kind of power transformer |
| WO2019068831A1 (en) | 2017-10-06 | 2019-04-11 | Castrol Limited | Metal working fluid additive composition |
| FR3097874B1 (en) * | 2019-06-28 | 2022-01-21 | Total Marketing Services | Lubricating composition for preventing corrosion and/or tribocorrosion of metal parts in an engine |
| CN110273159A (en) * | 2019-07-02 | 2019-09-24 | 宜兴市中大凯水处理有限公司 | A kind of new type high temperature corrosion inhibiter and preparation method thereof |
| CN113106457A (en) * | 2021-04-08 | 2021-07-13 | 四川瑞冬科技有限公司 | Corrosion inhibitor and preparation method thereof |
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| US2962443A (en) * | 1955-08-31 | 1960-11-29 | Lubrizol Corp | Steam turbine lubricant |
| DE1271877B (en) * | 1963-04-23 | 1968-07-04 | Lubrizol Corp | Lubricating oil |
| GB1043488A (en) * | 1963-12-27 | 1966-09-21 | Shell Int Research | Lubricating oil compositions containing organo phosphorus complexes, the preparation thereof and the complexes thus prepared |
| US4234435A (en) * | 1979-02-23 | 1980-11-18 | The Lubrizol Corporation | Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation |
| US5334329A (en) * | 1988-10-07 | 1994-08-02 | The Lubrizol Corporation | Lubricant and functional fluid compositions exhibiting improved demulsibility |
| ATE140982T1 (en) * | 1992-04-22 | 1996-08-15 | Hoechst Ag | CORROSION PROTECTION AGENTS |
| US5578557A (en) * | 1996-04-01 | 1996-11-26 | Lyondell Petrochemical Company | Food grade compressor oil |
| JP2002363592A (en) * | 2000-08-03 | 2002-12-18 | Nippon Oil Corp | Rust-preventive oil composition |
| JP2002114989A (en) * | 2000-08-03 | 2002-04-16 | Nippon Mitsubishi Oil Corp | Rust-proof oil |
| EP1394289B1 (en) * | 2001-04-06 | 2012-05-09 | Nippon Oil Corporation | Rust-preventive oil composition |
| US6624124B2 (en) * | 2001-07-13 | 2003-09-23 | Renewable Lubricants, Inc. | Biodegradable penetrating lubricant |
| US20040038835A1 (en) * | 2002-08-06 | 2004-02-26 | Chasan David E. | Engine oils that are non-aggressive towards lead |
| US20050272614A1 (en) * | 2004-06-07 | 2005-12-08 | Walker Johnny B | Novel multi-purpose rust preventative and penetrant |
| JP5078614B2 (en) * | 2004-08-18 | 2012-11-21 | チバ ホールディング インコーポレーテッド | Lubricating oil composition having improved performance |
-
2007
- 2007-05-15 EP EP07729126A patent/EP2027235A1/en not_active Withdrawn
- 2007-05-15 JP JP2009511461A patent/JP5395658B2/en not_active Expired - Fee Related
- 2007-05-15 CN CN2007800190983A patent/CN101454429B/en not_active Expired - Fee Related
- 2007-05-15 AU AU2007253453A patent/AU2007253453B2/en not_active Ceased
- 2007-05-15 CA CA2650246A patent/CA2650246C/en not_active Expired - Fee Related
- 2007-05-15 WO PCT/EP2007/054674 patent/WO2007135017A1/en active Application Filing
- 2007-05-15 RU RU2008150626/04A patent/RU2483099C2/en not_active IP Right Cessation
- 2007-05-15 US US12/227,548 patent/US20100022425A1/en not_active Abandoned
- 2007-05-15 KR KR1020087026615A patent/KR20090010041A/en not_active IP Right Cessation
- 2007-05-21 TW TW096118050A patent/TW200815586A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN101454429B (en) | 2012-08-08 |
| JP2009537681A (en) | 2009-10-29 |
| JP5395658B2 (en) | 2014-01-22 |
| TW200815586A (en) | 2008-04-01 |
| CN101454429A (en) | 2009-06-10 |
| CA2650246C (en) | 2014-12-23 |
| US20100022425A1 (en) | 2010-01-28 |
| WO2007135017A1 (en) | 2007-11-29 |
| RU2008150626A (en) | 2010-06-27 |
| AU2007253453B2 (en) | 2012-01-19 |
| KR20090010041A (en) | 2009-01-28 |
| AU2007253453A1 (en) | 2007-11-29 |
| EP2027235A1 (en) | 2009-02-25 |
| RU2483099C2 (en) | 2013-05-27 |
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