WO2006053858A1 - Benzotriazole compositions - Google Patents

Benzotriazole compositions Download PDF

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Publication number
WO2006053858A1
WO2006053858A1 PCT/EP2005/055934 EP2005055934W WO2006053858A1 WO 2006053858 A1 WO2006053858 A1 WO 2006053858A1 EP 2005055934 W EP2005055934 W EP 2005055934W WO 2006053858 A1 WO2006053858 A1 WO 2006053858A1
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WIPO (PCT)
Prior art keywords
alkyl
cycloalkyl
phenyl
represents hydrogen
group
Prior art date
Application number
PCT/EP2005/055934
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English (en)
French (fr)
Inventor
Isabelle Rapenne-Jacob
Samuel Evans
Peter Rohrbach
Martin VON BÜREN
Original Assignee
Ciba Specialty Chemicals Holding Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Specialty Chemicals Holding Inc. filed Critical Ciba Specialty Chemicals Holding Inc.
Priority to US11/667,779 priority Critical patent/US20090105102A1/en
Priority to BRPI0518001-5A priority patent/BRPI0518001A/pt
Priority to EP05808166A priority patent/EP1833953A1/en
Priority to CA002586083A priority patent/CA2586083A1/en
Priority to JP2007541934A priority patent/JP2008520784A/ja
Publication of WO2006053858A1 publication Critical patent/WO2006053858A1/en
Priority to US13/019,567 priority patent/US20110212864A1/en

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M141/06—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 nitrogen-containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/44—Five-membered ring containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • 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
    • C10N2030/14—Metal deactivation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/023—Multi-layer lubricant coatings

Definitions

  • the invention relates to novel benzotriazole compositions comprising mixtures of benzotria- zoles and N-substituted benzotriazoles, the process for preparing N-substituted benzotria- zoles and a method for improving the functional properties of lubricants, hydraulic or metal- working fluids or coating compositions.
  • Additives which can be used as metal deactivators display their protective action in func ⁇ tional liquids, such as mineral oil or fuels, by deactivating the metal ions, such as copper or iron, 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.
  • EP-A-365476 discloses benzotriazole compounds:
  • R 1 represents C 1 -C 12 straight or branched chain alkyl
  • R 2 represents C 1 -C 12 straight or branched chain alkyl interrupted by one or more O-atoms or represents C 5 -Ci 2 cycloalkyl; and lubricant compositions comprising these benzotriazole compounds.
  • metal deactivators of the triazole type are problematic. Because of high temperatures, in particular in internal combus ⁇ tion engines and turbines, which are exposed to oils and fuels, the deactivator concentration can rapidly decrease with a corresponding reduction in the protective action.
  • TTA tolutriazole
  • alkyl aldehydes and cycloalkanols additive components which can be used in lubricant compositions as metal deactivators, possess improved solubility and, in functional liquids, have lower volatility than tolutriazole itself.
  • present invention which relates to novel benzotriazole compo ⁇ sitions comprising mixtures of benzotriazoles and N-substituted benzotriazoles.
  • the invention relates to a composition
  • a composition comprising A) A mixture consisting essentially of: a) A benzotriazole compound:
  • R 1 represents hydrogen or d-C 4 alkyl
  • R 2 represents a substituent selected from the group consisting of Ci-Ci 2 alkyl, C 5 - Cycycloalkyl, (Ci-C 4 alkyl)i -3 C 5 -C 7 cycloalkyl, C 5 -C 7 cycloalkyl-Ci-C 4 alkyl,
  • R 1 1 is as defined as Ri;
  • the index a represents a numeral from 1 to 10; and
  • the index n represents a numeral from 2 to 8;
  • R 3 represents hydrogen or a substituent selected from the group consisting of C 1 - Ci 2 alkyl, C 5 -C 7 cycloalkyl, (Ci-C 4 alkyl)i -3 C 5 -C 7 cycloalkyl, C 5 -C 7 cycloalkyl-Ci- C 4 alkyl, phenyl, phenyl-CrC 4 alkyl, (Ci-C 4 alkyl) 1-3 phenyl and (Ci-C 4 alkyl) 1-3 phen- yl-Ci-C 4 alkyl; b) A benzotriazole compound:
  • R 1 represents hydrogen or CrC 4 alkyl; and, optionally, c) A triazole compound:
  • R 1 represents hydrogen or d-C 4 alkyl
  • R 2 represents a substituent selected from the group consisting of Ci-Ci 2 alkyl, C 5 - Cycycloalkyl, (Ci-C 4 alkyl)i -3 C 5 -C 7 cycloalkyl, C 5 -C 7 cycloalkyl-Ci-C 4 alkyl,
  • R 1 1 is as defined as R 1 ;
  • the index a represents a numeral from 1 to 10;
  • the index n represents a numeral from 2 to 8;
  • R 3 represents hydrogen or a substituent selected from the group consisting of C 1 - C 12 alkyl, C 5 -C 7 cycloalkyl, (C 1 -C 4 alkyl) 1-3 C 5 -C 7 cycloalkyl J C 5 -C 7 cycloalkyl-C r
  • a functional fluid selected from the group consisting of lubricants, hydraulic agents, metal working fluids and coating agents.
  • a more specific embodiment of the invention relates to a composition
  • a composition comprising A) A mixture consisting essentially of: a) A benzotriazole compound:
  • R 1 represents hydrogen or C r C 4 alkyl
  • R 2 represents a substituent selected from the group consisting of CrC 12 alkyl, C 5 -
  • R 3 represents hydrogen or a substituent selected from the group consisting of C 1 - C 12 alkyl, C 5 -C 7 cycloalkyl, (CrC 4 alkyl) 1-3 C 5 -C 7 cycloalkyl, C 5 -C 7 cycloalkyl-CrC 4 alkyl, phenyl, phenyl-CrC 4 alkyl, (d-C 4 alkyl) 1-3 phenyl and (Ci-C 4 alkyl) 1-3 phenyl-Cr C 4 alkyl; b) A benzotriazole compound:
  • R 1 represents hydrogen or C r C 4 alkyl; and, optionally, c) A triazole compound:
  • R 1 represents hydrogen or CrC 4 alkyl
  • R 2 represents a substituent selected from the group consisting of CrC 12 alkyl, C 5 - Cycycloalkyl, (C 1 -C 4 BIkVl) 1-3 C 5 -C 7 CyClOaIkVl and C 5 -C 7 cycloalkyl-CrC 4 alkyl; and
  • R 3 represents hydrogen or a substituent selected from the group consisting of C 1 - C 12 alkyl, C 5 -C 7 cycloalkyl, (CrC 4 alkyl) 1-3 C 5 -C 7 cycloalkyl, C 5 -C 7 cycloalkyl-CrC 4 alkyl, phenyl, phenyl-CrC 4 alkyl, (C r C 4 alkyl) 1-3 phenyl and (CrC ⁇ lkyl ⁇ sphenyl-Cr C 4 alkyl; and B) A functional fluid selected from the group consisting of lubricants, hydraulic agents, metal working fluids and coating agents.
  • compositions defined above are prepared by conventional mixing procedures and are suitable as metal deactivators in functional liquids.
  • compositions according to the invention are defined by the following isomeric structures:
  • R 1 , R 2 and R 3 are as defined above.
  • Ri and Ri 1 defined as CrC 4 alkyl represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobu- tyl or tert-butyl. According to a preferred embodiment, Ri represents methyl.
  • R 2 represents a substituent selected from the group consisting of C r Ci 2 alkyl, C 5 -C 7 cyclo- alkyl, (Ci-C 4 alkyl)i -3 C 5 -C 7 cycloalkyl or C 5 -C 7 cycloalkyl-Ci-C 4 alkyl.
  • R 2 defined as Ci-d 2 alkyl represents C r C 4 alkyl as defined above with regard to Ri and Ri 1 and additionally represents straight chain or branched C 5 -Ci 2 alkyl, e.g. pentyl, hexyl, heptyl, octyl, nonyl, undecyl or dodecyl.
  • R 2 defined as C 5 -C 7 cycloalkyl is preferably cyclopentyl or cyclohexyl.
  • R 2 defined as (Ci-C 4 alkyl) 1-3 C 5 -C 7 cycloalkyl is preferably cyclopentyl or cyclohexyl substituted with CrC 4 alkyl, e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl.
  • R 2 defined as C 5 -C 7 cycloalkyl-Ci-C 4 alkyl is e.g.
  • cyclopentylmethyl cyclohexyl methyl, cyclopentyl-1 ,1 -ethyl, cyclohexyl-1 ,1 -ethyl, cyclopentyl-1,2-ethyl or cyclohexyl-1,2-ethyl.
  • the index a represents a numeral from 1 to 10
  • the index a represents a numeral from 1 to 6
  • the index n represents a numeral from 2 to 6.
  • the index a represents a numeral from 1 to 4
  • the index n represents a numeral from 2 to 4.
  • R 3 represents a substituent a substituent selected from the group consisting of C r Ci 2 alkyl, C 5 -C 7 CyClOaI kyl, (CrC 4 alkyl)i -3 C 5 -C 7 cycloalkyl, C 5 -C 7 cycloalkyl-CrC 4 alkyl, phenyl, phenyl-Ci- C 4 alkyl, (C r C 4 alkyl)i -3 phenyl and (Ci-C 4 alkyl)i -3 phenyl-C r C 4 alkyl.
  • R 3 defined as C r Ci 2 alkyl, C 5 -C 7 cycloalkyl, (Ci-C 4 alkyl) 1-3 C 5 -C 7 cycloalkyl and C 5 -C 7 cycloalkyl- Ci-C 4 alkyl has the same meanings as defined above with regard to R 2 .
  • R 3 defined as phenyl, phenyl-CrC 4 alkyl, (d-C 4 alkyl) 1-3 phenyl and (Ci-C 4 alkyl) 1-3 phenyl-Cr C 4 alkyl is, for example, phenyl, benzyl, 1- or 2-phenylethyl, 4-methyl or 4-ethyl, cumyl or 4-methyl benzyl.
  • Suitable acid catalysts include mineral acids, e.g. sulphuric acid, acid clays, e.g. bentonite, montmorillonite, Bleicherde Tonsil® (Supreme 110 FF, 126 FF) or Fuller's earth, acid ion- exchange resins, e.g. Amberlyst® 15, and sulphonic acids, e.g. p-toluene sulphonic acid.
  • the inert solvent may be cyclohexane, benzene, toluene, xylene or carbon tetrachloride.
  • Ri defined as Ci-C 4 alkyl represents methyl, ethyl, n-propyl, isopropyl, n- butyl, isobutyl or tert-butyl. According to a preferred embodiment, Ri represents methyl.
  • Compounds (II) are known and are commercially available, e.g. Irgamet® (Ciba Specialty Chemicals) TTA.
  • compositions according to the invention are preferably defined by the following isomeric structure:
  • R 1 , R 2 and R 3 are as defined above.
  • Compounds (III), according to the optional component c), can be prepared in a manner analogous to EP O 365476, e.g. by the acid catalysed reaction of a Ri -substituted triazole, e.g. triazole or methyltriazole, with the aldehyde R 3 -C ⁇ O)-H and the alcohol R 2 -OH.
  • Compounds (III), wherein R 2 represents a group of the partial formula (A) or (B) can be pre ⁇ pared in an analogous manner by the acid catalysed reaction of the Ri -substituted triazole, e.g.
  • the term functional liquid selected from the group consisting of lubricants, hydraulic agents, metal working fluids and coating agents includes non-aqueous, partially aqueous and aque ⁇ ous liquids which are in contact with metals to be deactivated, in particular copper or iron.
  • 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 fuel, and lubricants, hydraulic fluid, metal working fluid, en- gine coolants, transformer oil and switch gear oil.
  • 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
  • Suitable partially aqueous functional liquids are hydraulic fluids based on aque ⁇ ous polyglycol/ polyglycol ether mixtures or glycol systems, water-in-oil or oil-in-water sys ⁇ tems and engine cooling systems based on aqueous glycol.
  • aqueous functional liquids are industrial cooling water, filling compositions of a water conditioning plant, steam generation systems, sea water evaporation systems, sugar evaporation systems, irrigation systems, hydrostatic boilers and heating systems or cooling systems having a closed circulation.
  • compositions according to the invention preferably comprise 0.01 to 5.0% by weight, in particular 0.02 to 1.0% by weight, of a compound (I), 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- pie, 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.
  • the lubricants are in particular oils and greases, for example based on mineral oil or vegeta ⁇ ble 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, Nn- seed 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, forms or forms prepared by genetic engineering, for example soy bean oil prepared by ge ⁇ netic engineering.
  • Examples of synthetic lubricants include lubricants based on aliphatic or aromatic carboxylic esters, polymeric esters, polyalkylene oxides, phosphoric acid esters, poly- ⁇ -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 ca pry lie and sebacic acid or of a mixture thereof.
  • Particularly suitable in addition to mineral oils are, for example, poly- ⁇ -olefins, ester-based lubricants, phosphates, glycols, polyglycols and polyalkylene 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.
  • a further embodiment of the invention relates to a composition, which comprises additional additives selected from the group consisting of metal deactivators, antioxidants, rust inhibi ⁇ tors, viscosity index improvers, pour-point depressants, dispersants, surfactants, extreme- pressure additives, and antiwear additives.
  • additional additives selected from the group consisting of metal deactivators, antioxidants, rust inhibi ⁇ tors, viscosity index improvers, pour-point depressants, dispersants, surfactants, extreme- pressure additives, and antiwear additives.
  • Such additives are added in the amounts customary in each case for the purpose, each in the range from 0.01 to 10.0% by weight. Examples of further additives are listed below:
  • Alkylated monophenols 2,6-di-tert-butyl-4-methylphenol, 2-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-iso- butylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-( ⁇ -methylcyclohexyl)-4,6-dimethyl- phenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4- methoxymethyl phenol, linear nonylphenols or nonylphenols which are branched in the side chain, e.g.
  • Alkylthiomethylphenols 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl- 6-methyl phenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonyl- phenol U3.
  • Hydroxylated thiodiphenyl ethers 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thio- bis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis-(6-tert-butyl-2- methylphenol), 4,4 1 -thiobis(3,6-di-sec-amylphenol), 4,4 1 -bis(2,6-dimethyl-4-hydroxy- phenyl) disulphide 1.6.
  • Alkylidene bisphenols 2,2 1 -methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methyl- enebis(6-tert-butyl-4-ethylphenol), 2,2 1 -methylenebis[4-methyl-6-( ⁇ -methylcyclohexyl)- phenol], 2,2 1 -methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylenebis(6-nonyl- 4-methylphenol), 2,2 1 -methylenebis(4,6-di-tert-butylphenol) J 2,2 1 -ethylidenebis(4,6-di- tert-butylphenol), 2,2 1 -ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2'-methylene- bis[6-( ⁇ -methylbenzyl)-4-nonylphenol], 2,2 1 -methylenebis[6-( ⁇ , ⁇ -di
  • 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 J 4 J 6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol 1.10.
  • Triazine compounds 2,4-bisoctylmercapto-6-(3 J 5-di-tert-butyl-4-hydroxyanilino)-1 J 3 J 5- triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1 ,3,5-triazine, 2- octylmercapto-4 J 6-bis(3 J 5-di-tert-butyl-4-hydroxyphenoxy)-1 J 3 J 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- hydroxybenzyl) isocyanurate, 1 ,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6-tris(
  • esters of beta-(5-tert-butyl-4-hvdroxy-3-methylphenyl)propionic acid with monohydric or polyhydric alcohols, e.g. the alcohols with methanol, ethanol, n-octanol, isooctanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neo- pentylglycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl) isocyanurate, N,N 1 -bis(hydroxyethyl)-oxalamide, 3-thiaundecanol,
  • Amine antioxidants N.N'-diisopropyl-p-phenylenediamine, N,N'-di-sec-butyl-p-phenyl- enediamine, N,N l -bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N'-bis(1-ethyl-3-me- thylpentyl)-p-phenylenediamine, N,N l -bis(1-methyl-heptyl)-p-phenylenediamine, N 1 N 1 - dicyclohexyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, N,N'-di-(naph- th-2-yl)-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(1 ,3- di
  • p.p'-di-tert-octyldiphenylamine 4-n-butylaminophenol, 4-butyryla- minophenol, 4-nonanoylamino-phenol, 4-dodecanoylaminophenol, 4-octadecanoyl- aminophenol, di-(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethyl- phenol, 2,4 1 -diaminodiphenylmethane, 4,4 1 -diaminodiphenylmethane, N.N.N'.N'-tetra- methyl ⁇ '-diaminodiphenylmethane, 1 ,2-di-[(2-methyl-phenyl)-amino]ethane, 1 ,2-di- (phenylamino)-propane, (o-tolyl)biguanide, di-[4-(1 '.S
  • 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-3,7,11-trithiatridecane and 2,2, 15,15-tetramethyl-5, 12-dihydroxy-
  • Benzotriazoles and derivatives thereof 2-mercaptobenzotriazole, 2,5-dimercaptoben- zotriazole, 4- or 5-alkyl benzotriazoles (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; alkoxyalkyl benzotriazoles, such as 1- (nonyloxymethyl)-benzotriazole, 1-(1-butoxyethyl)benzotriazole and 1-(1-cyclohexyl- oxybutyl)tolutriazole
  • 1 ,2,4-Triazoles and derivatives thereof 3-alkvl (or arvl)-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
  • Imidazole derivatives 4,4 1 -methylenebis(2-undecyl-5-methylimidazole), bis[(N- methyl)imidazol-2-yl]carbinol octyl ether
  • 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
  • Organic acids, their esters, metal salts, amine salts and anhydrides e.g. alkyl- and al- kyenylsuccinic acids and partial esters thereof with alcohols, diols or hydroxycarb- oxylic acids, partial amides of alkyl- and alkenylsuccinic acids, 4-nonylphenoxyacetic acid, alkoxy- and alkoxyethoxycarboxylic acids, such as dodecyloxyacetic acid, do- decyloxy(ethoxy)acetic acid and amine salts thereof, and furthermore N-oleoylsar- cosine, sorbitan monooleate, lead naphthenate, alkenylsuccinic anhydrides, e.g. do- decenylsuccinic anhydride, 2-(2-carboxyethyl)-1-dodecyl-3-methylglycerol and salts thereof, in particular sodium salts and triethanol
  • Sulphur-containing compounds barium dinonylnaphthalenesulphonates, calcium petro ⁇ leum sulphonates, alkylthio-substituted aliphatic car boxy lie acids, esters of aliphatic 2- sulphocarboxylic acids and salts thereof
  • Viscosity index improvers polyacrylates, polymethacrylates, vinylpyrroli- done/methacrylate copolymers, polyvinylpyrrolidones, polybutenes, olefin copolymers, styrene/acrylate copolymers, polyethers 7.
  • Pour point depressants poly(meth)acrylates, ethylene-vinyl acetate copolymers, alkyl polystyrenes, fumarate copolymers, alkylated naphthalene derivatives
  • Dispersants/Surfactants polybutenylsuccinamides or polybutenylsuccinimides, polybu- tenylphosphonic acid derivatives, basic magnesium, calcium and barium sulphonates and phenolates
  • High pressure and antiwear additives sulphur- and halogen-containing compounds, e.g. chlorinated paraffins, sulphonated olefins or vegetable oils (soy bean oil, rapeseed oil), alkyl or aryl di- or trisulphides, benzotriazoles or derivatives thereof, such as bis (2-ethyl- hexyl)aminomethyl tolutriazoles, dithiocarbamates, such as methylenebisdibutyl 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-dimer- capto-1,3,4-thiadiazole, such as 2,5-bis(tert-nonyldithio)-1,3,4-thiadiazole
  • chlorinated paraffins s
  • Emulsifiers petroleum sulphonates, amines, such as polyoxyethylated fatty amines, non-ionic surface-active substances
  • Biocides triazines, thiazolinones, trisnitromethane, morpholine, sodium pyridinethiol
  • Processing speed improvers calcium sulphonates and barium sulphonates.
  • 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 packet, which can be diluted to the con ⁇ centrations of use for the corresponding lubricant according to consumption.
  • a preferred embodiment of the invention relates to a composition
  • a composition comprising A) A mixture consisting essentially of a) A benzotriazole compound:
  • R 1 represents hydrogen or methyl
  • R 2 represents a substituent selected from the group consisting of CrC 8 alkyl, C 5 - Cycycloalkyl,
  • R 1 1 is as defined as R 1 ;
  • the index a represents a numeral from 1 to 10;
  • the index n represents a numeral from 2 to 8;
  • R 3 represents hydrogen or a substituent selected from the group consisting of C 1 - C 8 alkyl, C 5 -C 7 cycloalkyl and phenyl or an isomer of the compound (I 1 ); and b) A benzotriazole compound:
  • R 1 represents hydrogen or methyl
  • a functional fluid selected from the group consisting of lubricants, hydraulic agents, metal working fluids and coating agents.
  • a highly preferred embodiment of the invention relates to a composition
  • a composition comprising A) A mixture consisting essentially of a) A benzotriazole compound:
  • R 1 represents hydrogen or methyl
  • R 2 represents a substituent selected from the group consisting of CrC 8 alkyl, C 5 - Cycycloalkyl,
  • R 1 1 is as defined as Ri
  • the index a represents a numeral from 1 to 10;
  • the index n represents a numeral from 2 to 8, and
  • R 3 represents hydrogen or a substituent selected from the group consisting of C 1 -
  • R 1 represents hydrogen or methyl
  • R 1 represents hydrogen or methyl
  • R 2 represents a substituent selected from the group consisting of CrC 8 alkyl, C 5 - Cycycloalkyl,
  • R 1 1 is as defined as Ri;
  • the index a represents a numeral from 1 to 10;
  • the index n represents a numeral from 2 to 8;
  • R 3 represents hydrogen or a substituent selected from the group consisting of d- Ci 2 alkyl, C 5 -C 7 cycloalkyl and phenyl; and B) A functional fluid selected from the group consisting of lubricants, hydraulic agents, metal working fluids and coating agents.
  • the invention particularly refers to a composition comprising
  • R 2 represents C 5 -C 7 cycloalkyl or the group (A 1 ), wherein R 1 1 is as defined as Ri;
  • index a represents a numeral from 1 to 8.
  • R 3 represents CrC 8 alkyl or C 5 -C 7 cycloalkyl or an isomer of the compound (I 1 ); and b) A benzotriazole compound (II), wherein Ri represents hydrogen or methyl; and
  • composition comprising A) A mixture consisting essentially of a) A benzotriazole compound (I 1 ), wherein
  • Ri represents hydrogen or methyl
  • R 2 represents C 5 -C 7 cycloalkyl or the group (A), wherein R 1 1 is as defined as Ri;
  • index a represents a numeral from 1 to 8; and R 3 represents CrC 8 alkyl or C 5 -C 7 cycloalkyl or an isomer of the compound (I 1 ); b) A benzotriazole compound (II), wherein Ri represents hydrogen or methyl; and c) A triazole compound (III), wherein
  • Ri represents hydrogen or methyl
  • R 2 represents C 5 -C 7 cycloalkyl or the group (B), wherein R 1 1 is as defined as R 1 ; and The index a represents a numeral from 1 to 8; and R 3 represents C r C 8 alkyl or C 5 -C 7 cycloalkyl or an isomer of the compound (I 1 ); and B) A functional fluid selected from the group consisting of lubricants, hydraulic agents, metal working fluids and coating agents.
  • a further embodiment of the invention relates to a mixture comprising a) A benzotriazole compound (I), wherein Ri represents hydrogen or C r C 4 alkyl; R 2 represents a substituent selected from the group consisting of C r Ci 2 alkyl, C 5 -
  • C 7 cycloalkyl (Ci-C 4 alkyl) 1-3 C 5 -C 7 cycloalkyl and C 5 -C 7 cycloalkyl-Ci-C 4 alkyl or represents the group (A),
  • R 1 1 is as defined as Ri;
  • the index a represents a numeral from 1 to 10; and R 3 represents hydrogen or a substituent selected from the group consisting of d-
  • R 2 represents a substituent selected from the group consisting of Ci-Ci 2 alkyl, C 5 - Cycycloalkyl, (Ci-C 4 alkyl) 1-3 C 5 -C 7 cycloalkyl and C 5 -C 7 cycloalkyl-Ci-C 4 alkyl or represents the group (B), wherein
  • Ri 1 is as defined as R 1 ;
  • the index a represents a numeral from 1 to 10;
  • R 3 represents hydrogen or a substituent selected from the group consisting of C r Ci 2 alkyl, C 5 -C 7 cycloalkyl, (Ci-C 4 alkyl)i -3 C 5 -C 7 cycloalkyl, C 5 -C 7 cycloalkyl-C r
  • the mixtures defined above is particularly useful in method for improving the functional prop ⁇ erties of lubricants, hydraulic or metal-working fluids or coating compositions, which com- prises adding to a functional fluid the mixture defined above and, optionally, further additives.
  • Montmorillonit is replaced with Bleicherde Tonsil® Supreme 110FF.
  • a 0.05% solution of the test composition in a mineral oil of turbine quality is prepared, which oil has a viscosity of 26.2 mm 2 /sec (40 0 C) and 4.8 mm 2 /sec (100 0 C) and a sulphur content of 0.54%.
  • the solution can also contain a phenolic or amine antioxidant. The time required at a temperature of 150°C for a minimum pressure drop of 1.75 bar starting from the maximum pressure of 6.2 bar is measured. 3.1.2 Modified ASTM D-130 copper strip test
  • a copper strip (50 x 10 x 1 mm) is polished with grade 150 silicon carbide, which was absorbed with a wool pad wet with high-boiling petroleum ether. The polished strip is then completely im ⁇ mersed in the prepared solution, which is kept at 100°C for two hours.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
PCT/EP2005/055934 2004-11-22 2005-11-14 Benzotriazole compositions WO2006053858A1 (en)

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BRPI0518001-5A BRPI0518001A (pt) 2004-11-22 2005-11-14 composições de benzotriazol
EP05808166A EP1833953A1 (en) 2004-11-22 2005-11-14 Benzotriazole compositions
CA002586083A CA2586083A1 (en) 2004-11-22 2005-11-14 Benzotriazole compositions
JP2007541934A JP2008520784A (ja) 2004-11-22 2005-11-14 ベンゾトリアゾール組成物
US13/019,567 US20110212864A1 (en) 2004-11-22 2011-02-02 Benzotriazole compositions

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Cited By (7)

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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
CN103450102A (zh) * 2013-05-08 2013-12-18 如皋市金陵化工有限公司 1－正丁基－1h－苯并三氮唑的合成工艺
US9309205B2 (en) 2013-10-28 2016-04-12 Wincom, Inc. Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures
CN107987917A (zh) * 2017-12-11 2018-05-04 国网福建省电力有限公司 一种变压器油中硫腐蚀防护方法
US11788026B2 (en) 2021-07-28 2023-10-17 Afton Chemical Corporation Hydraulic fluid
US12018224B2 (en) 2021-07-28 2024-06-25 Afton Chemical Corporation Hydraulic fluid

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US20110212864A1 (en) * 2004-11-22 2011-09-01 Isabelle Rapenne-Jacob Benzotriazole compositions
SG11201600138XA (en) * 2013-07-11 2016-02-26 Basf Se Chemical-mechanical polishing composition comprising benzotriazole derivatives as corrosion inhibitors
CN104649985A (zh) * 2013-11-25 2015-05-27 刘现梅 一种水溶性的甲基苯骈三氮唑的次甲基衍生物及其制备方法

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EP0365476A1 (en) * 1988-10-18 1990-04-25 Ciba-Geigy Ag Lubricant compositions
US5714442A (en) * 1995-04-11 1998-02-03 Ciba Speciality Chemicals Corporation Compounds with (benzo) triazole radicals

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US8535568B2 (en) 2011-03-11 2013-09-17 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same
US8535569B2 (en) 2011-03-11 2013-09-17 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles and other triazoles and methods for using same
US8535567B2 (en) 2011-03-11 2013-09-17 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same
US9447322B2 (en) 2011-03-11 2016-09-20 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same
CN103450102B (zh) * 2013-05-08 2016-03-09 如皋市金陵化工有限公司 1－正丁基－1h－苯并三氮唑的合成工艺
CN103450102A (zh) * 2013-05-08 2013-12-18 如皋市金陵化工有限公司 1－正丁基－1h－苯并三氮唑的合成工艺
US9309205B2 (en) 2013-10-28 2016-04-12 Wincom, Inc. Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures
US9802905B2 (en) 2013-10-28 2017-10-31 Wincom, Inc. Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures
CN107987917A (zh) * 2017-12-11 2018-05-04 国网福建省电力有限公司 一种变压器油中硫腐蚀防护方法
US11788026B2 (en) 2021-07-28 2023-10-17 Afton Chemical Corporation Hydraulic fluid
US12018224B2 (en) 2021-07-28 2024-06-25 Afton Chemical Corporation Hydraulic fluid

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CA2586083A1 (en) 2006-05-26
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TW200621731A (en) 2006-07-01
BRPI0518001A (pt) 2008-10-21
CN101061206A (zh) 2007-10-24

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