WO2003004476A1 - Benzotriazoles et triazoles aminoalkyle substitues utiles en tant que desactivateurs de metaux - Google Patents

Benzotriazoles et triazoles aminoalkyle substitues utiles en tant que desactivateurs de metaux Download PDF

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WO2003004476A1
WO2003004476A1 PCT/EP2002/007015 EP0207015W WO03004476A1 WO 2003004476 A1 WO2003004476 A1 WO 2003004476A1 EP 0207015 W EP0207015 W EP 0207015W WO 03004476 A1 WO03004476 A1 WO 03004476A1
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alkyl
cycloalkyl
phenyl
alkylphenyl
hydrogen
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PCT/EP2002/007015
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Samuel Evans
Jean-Pierre Wolf
Stefan Laeuger
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Ciba Specialty Chemicals Holding Inc.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • 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

Definitions

  • the invention relates to novel triazole compounds which can be prepared from readily obtainable starting materials and can be used as metal deactivators, compositions comprising such compounds and functional liquids, e.g. mineral oil, a process for stabilizing functional liquids by adding the novel triazole compounds and a process for protecting metals which are in contact with functional liquids.
  • compositions comprising such compounds and functional liquids, e.g. mineral oil, a process for stabilizing functional liquids by adding the novel triazole compounds and a process for protecting metals which are in contact with functional liquids.
  • Additives which can be used as metal deactivators display their protective action in functional 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.
  • metal deactivators of the triazole type are problematic. Because of high temperatures, in particular in internal combustion engines and turbines, which are exposed to oils and fuels, the deactivator concentration can rapidly decrease with a corresponding reduction in the protective action.
  • the invention relates to compounds of the formula in which a) X, Y and Z, together with the other substituents, are 1 ,2,3-benzotriazole compounds
  • R is C r C 12 alkyl, phenyl-CrC ⁇ lkyl or CrC 4 alkylphenyl-CrC 4 alkyl;
  • R T is C 2 -C 12 alkyl, phenyl, phenyl-C C alkyl, C r C 4 alkylphenyl, CrC 4 alkylphenyl-C C alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-C C 4 alkyl, CrC 4 alkyl-C 4 -C 8 cycloalkyl or C C 4 alk- yl-C 4 -C 8 cycloalkyl-CrC 4 alkyl;
  • R 2 and R 3) independently of one another, are hydrogen, CrC ⁇ alkyi, phenyl, phenyl-C C 4 alkyl, C r C alkylphenyl, C C 4 alkylphenyl-CrC 4 alkyl, C -C 8 cycloalkyl, CrOtalkyl-OrCscycloalkyl or C r C 4 alkyl-C 4 -C 8 cyclo- alkyl-C C 4 alkyl; or
  • R 2 and R 3 together are C 2 -C 6 alkylene; or in which
  • R 2 is hydrogen, C ⁇ -C 12 alkyl, phenyl, phenyl-C r C 4 alkyl, C C alkylphenyl, C ⁇ -C 4 alkyl- phenyl-C C 4 alkyl, C -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-CrC 4 alkyl, C C ⁇ alkyl-OrCscyclo- alkyl or C ⁇ -C 4 aikyl-C 4 -C 8 cycloalkyl-CrC 4 alkyl; and
  • R 3 is a group or
  • R', Ri' and R 2 ' have the stated meanings of R, and R 2 , and n is an integer from 2 to 8; or in which b) X, Y and Z, together with the other substituents, are bridged 1 ,2,3-benzotriazole compounds
  • A is oxygen, sulphur or methylene
  • R T is C 2 -C 12 alkyl, phenyl, phenyl-C C 4 alkyl, d-dalkylphenyl, C ⁇ -C alkylphenyl-
  • R 2 and R 3 independently of one another, are hydrogen, d-C ⁇ alkyl, phenyl, phenyl-C ⁇ -C 4 alkyl, d-C 4 alkylphenyl, d-C 4 alkylphenyl-C r C 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-C r C aIkyl, C ⁇ -C 4 alkyl-C -C 8 cycloalkyl or CrC 4 alkyl-C 4 -C 8 cyclo- alkyl-d-C 4 alkyl; or
  • R 2 and R 3 together are C 2 -C 6 alkylene
  • R', R and R 2 ' have the stated meanings of R, Ri and R 2 ; or in which X, Y and Z, together with the other substituents, are bicyclic 1 ,2,3-triazole compounds
  • R is hydrogen, C C 12 alkyl, phenyl-C C 4 alkyl or d-dalkylphenyl-d-dalkyl;
  • Ri is C 2 -C 12 alkyl, phenyl, phenyl-d-C 4 alkyl, d-C alkylphenyl, C C 4 alkylphenyl- d-C 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-C C 4 alkyl, C C 4 alkyl-C 4 -C 8 cycloalkyl or C ⁇ -C 4 alkyl-C 4 -C 8 cycloalkyl-C C 4 alkyl;
  • R 2 and R 3 independently of one another, are hydrogen, d-C 12 alkyl, phenyl, phenyl-C C alkyl, C C 4 alkylphenyl, CrC 4 alkylphenyl-d-C 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-C C 4 alkyl, C r C 4 alkyl-C 4 -C 8 cycIoalkyl or C r C 4 alkyl-C 4 -C 8 cyclo- alkyl-C C 4 alkyl; or
  • R 2 and R 3 together are C 2 -C 6 alkylene; or in which
  • R 2 is hydrogen, CrC 12 alkyl, phenyl, phenyl-d-C 4 alkyl, C ⁇ -C 4 alkylphenyl, C C 4 alkyl- phenyl-C C 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-C C 4 aIkyl, C r C alkyl-C 4 -C 8 cyclo- alkyl or C 1 -C 4 alkyl-C 4 -C 8 cycloalkyl-C 1 -C 4 alkyl; and
  • R 3 is a group or
  • R', Ri' and R 2 ' have the stated meanings of R, Ri and R 2 , and n is an integer from 2 to 8; or in which d) X, Y and Z, together with the other substituents, are monocyclic 1 ,2,4-triazole compounds
  • R a and R b independently of one another, are hydrogen, d-C ⁇ 2 alkyl, phenyl-d-C 4 alkyl, C r C 4 alkylphenyl or C C 4 alkylphenyl-C ⁇ -C 4 alkyl;
  • R is C ⁇ -C ⁇ 2 alkyl or phenyl-C C 4 alkyl
  • Ri is C 2 -C 12 alkyl, phenyl, phenyl-C C 4 alkyl, C C 4 alkylphenyl, C ⁇ -C 4 alkylphenyl- C r C 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycIoalkyl-C C 4 alkyl, CrC 4 alkyl-C 4 -C 8 cycloalkyl or d-C 4 alkyl-C 4 -C 8 cycloalkyl-C ⁇ -C 4 alkyl;
  • R 2 and R 3 independently of one another, are hydrogen, d-C 12 alkyl, phenyl, phenyl-C ⁇ -C 4 alkyl, C ⁇ -C 4 alkylphenyl, d-C 4 alkylphenyl-C ⁇ -C alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycloalkyl-C -C 4 alkyl, d-C 4 alkyl-C 4 -C 8 cycloalkyl or C r C 4 alkyl-C 4 -C 8 cyclo- alkyl-C ⁇ -C 4 alkyl; or
  • R 2 and R 3 together are C 2 -C 6 alkylene, and isomers of these compounds.
  • the compounds (I) are suitable as metal deactivators in non-aqueous, partially aqueous or aqueous functional liquids.
  • R is C ⁇ -C ⁇ 2 alkyl, e.g. C ⁇ -C 6 alkyl, e.g. methyl, ethyl, n-propyl or isopropyl or n-butyl, sec-butyl or tert-butyl or straight-chain or branched pentyl or hexyl, and C 7 -C 12 alkyl, e.g. straight-chain or branched heptyl, octyl, isooctyl, nonyl, tert-nonyl, decyl, undecyl or do- decyl.
  • C ⁇ -C ⁇ 2 alkyl e.g. C ⁇ -C 6 alkyl, e.g. methyl, ethyl, n-propyl or isopropyl or n-butyl, sec-butyl or tert-butyl or straight-chain or branched pentyl or hex
  • PhenyI-C C alkyl and d-C 4 alkylphenyl-CrC 4 alkyl radicals R and R' are, for example, benzyl, 1 - or 2-phenethyl or 4-methyIbenzyl.
  • C 2 -C ⁇ 2 alkyl radicals Ri and Ri' are, for example, ethyl, n-propyl or isopropyl or n-butyl, sec- butyl or tert-butyl or straight-chain or branched pentyl or hexyl, and C 7 -C ⁇ 2 alkyl radicals Ri and Ri' are, for example, straight-chain or branched heptyl, octyl, isooctyl, nonyl, tert-nonyl, decyl, undecyl or dodecyl.
  • Phenyl-C ⁇ -C alkyl, d-C 4 alkylphenyl and C C 4 alkylphenyl-CrC 4 alkyl radicals R und Ri' are, for example, benzyl, 1- or 2-phenethyl, 4-methyl- or 4-ethylphenyl, cumyl or 4-methylbenzyl.
  • C 4 -C 8 cycloalkyl, C 4 -C 8 cycloaIkyl-C r C 4 alkyl, CrC 4 alkyl-C 4 -C 8 cycloalkyl or C ⁇ -C 4 alkyl-C -C 8 cycloalkyl-C C 4 aIkyl radicals Ri und R ⁇ are, for example, cyclopentyl, cyclo- hexyl, cyclopentylmethyl or cyclohexylmethyl, cyclopentyl-1 ,1 -ethyl, cyclohexyl-1,1 -ethyl, cyclopentyl-1 ,2-ethyl, cyclohexyl-1 ,2-ethyI, cyclopentyl-1 ,2-propyl or cyclohexyl-1 ,2-propyl, which can be substituted on the C 4 -C 8 cycloalkyl groups by Crdalkyl, e.
  • R 2 and R 2 ' and R 3 and R 3 ' are hydrogen, C r C 12 alkyl, phenyl, phenyl-C C 4 alkyl, C ⁇ -C 4 alkylphenyl, CrC alkylphenyl-C r C aIkyl, C 4 -C 8 cycloalkyl, C -C 8 cycloalkyl-C ⁇ -C alkyl, C C 4 alkyl-C 4 -C 8 cycloalkyl or d-C alkyl-C 4 -C 8 cyclo- alkyl-d-C alkyl, which are defined further above.
  • C ⁇ -C ⁇ 2 alkyl radicals R, R 2 and R 2 ' and R 3 and R 3 ' are methyl, or they are as defined further above for C 2 -C 12 alkyl radicals R ⁇ and R ⁇ .
  • R 2 and R 3 or R 2 ' and R 3 ' may furthermore be linked to one another and may together be C 2 - C 6 alkylene, preferably linear C 2 -C 6 alkylene, e.g. 1 ,2-ethylene, 1 ,3-propylene, 1,4-butyiene or 1 ,5-pentylene.
  • R 2 and R 3 or R 2 ' and R 3 ⁇ together with the -(C O)-N ⁇ group, form an N-substituted lactam radical.
  • R 3 and R 3 ' groups A, A', B and B' are each defined with the appropriate substituents under the compounds (IA) and (I'A) and (IC) and (I'C).
  • isomers includes structural and positional isomers, tautomeric forms, cis-trans isomers and stereoisomers, e.g. enantiomeric forms and racemic mixtures.
  • the compounds (I) according to embodiments a) - d) can be prepared in a manner known per se, as follows: a) Compounds (IA) and (I'A) can be prepared in a manner known per se by reaction of R- substituted benzotriazoles
  • Suitable acidic catalysts are proton donors (so-called Br ⁇ nsted acids), electron acceptor compounds (so-called Lewis acids), cation exchange resins, aluminosilicates or naturally occurring or modified sheet silicates.
  • Suitable proton donors are, for example, salt-forming inorganic or organic acids, e.g. mineral acids, such as hydrochloric acid, sulphuric acid or phosphoric acid, carboxylic acids, e.g. acetic acid, or sulphonic acids, e.g. methanesulphonic acid, benzenesulphonic acid or p-toluenesulphonic acid.
  • p-Toluenesulphonic acid is particularly suitable.
  • Suitable electron acceptor compounds are, for example, tin tetra- chloride, zinc chloride, aluminium chloride or boron trifluoride etherate. Tin tetrachloride and aluminium chloride are particularly suitable.
  • Suitable cation exchange resins are, for example, styrene-divinylbenzene copolymers having sulpho groups as an ion exchange function, e.g. the known products Amberlite® and Amberlyst® from Rohm and Haas, e.g. AMBERLITE 200, or Dowex® 50 from Dow Chemicals, perfluorinated ion exchange resins, e.g. National® H from DuPont, or other su- peracidic ion exchange resins, e.g. those described by 7 " . Yamaguchi in Applied Catalysis ⁇ 1, 1-25 (1990), or M.Hino etal. in J. Chem. Soc. Chemical Comm. 1980. 851-852.
  • Suitable aminosilicates are, for example, amorphous aluminium silicates which comprise about 10-30% of silica and about 70-90% of alumina and are used in the petrochemical industry, e.g. aluminium silicate HA-HPV® from Ketjen (Akzo), or crystalline aluminium silicates, e.g. so-called zeolites, which are used as inorganic cation exchangers, as so-called molecular sieves or in the petrochemical industry as so-called cracking catalysts, e.g. fau- jasite from Union Carbide, Zeolith® R and Y and ultra stable ZEOLITH; ZEOLITH Beta® and ZSM-12® from Mobil Oil; or the zeolite Mordenit® from Norton.
  • zeolites which are used as inorganic cation exchangers, as so-called molecular sieves or in the petrochemical industry as so-called cracking catalysts, e.g.
  • Suitable naturally occurring sheet silicates are also referred to as "acid earths" and are, for example, montmorillonites which are activated, for example, with mineral acids, such as sulphuric acid and/or hydrochloric acid, and preferably have a moisture content of less than 10%, in particular less than 5%, e.g. so-called earths of the Fuller type, e.g. types commercially available under the names Fulcat®, e.g. the types 20, 22 A, 22 B and 40 (clays activated with sulphuric acid), Fulmont® (Laporte Industries), e.g.
  • Modified sheet silicates are also referred to as "pillared clays" and are derived from the naturally occurring sheet silicates described further above, in that they also contain oxides of, for example, zirconium, iron, zinc, nickel, chromium, cobalt or magnesium or rare earth elements between the silicate layers. Modified sheet silicates are described, for example, by J. Clark et al. in J. Chem. Soc. Chem. Comm. 1989, 1353-1354. Particularly preferred modified sheet silicates are, for example, the products Envirocat® EPZ-10, EPZG or EPIC produced by Contract Chemicals.
  • the acidic catalyst can be added, for example, in an amount of 1.0-50.0, in particular 5.0- 25.0, very particularly 5.0-20.0, % by weight or, if it is a so-called Br ⁇ nsted acid or Lewis acid, in an amount of 0.002 to 10.0 mol %, preferably 0.1 to 5.0 mol %.
  • the reaction temperature is from about 60° to 250°C, preferably from 110° to 200°C, particularly preferably from 160° to 195°C.
  • reaction in both reaction steps can be carried out with or preferably without solvents or diluents. If a solvent is used, it should be inert under the given reaction conditions and have a suitably high boiling point. Suitable solvents are, for example, free or halogenated hydrocarbons, polar aprotic solvents, liquid amides and alcohols.
  • Examples are petroleum ether fractions, preferably relatively high-boiling ones, toluene, mesitylene, dichlorobenzene, tet- rahydrofuran (THF), dimethylformamide (DMF), dimethylacetamide (DMA), hexamethyl- phosphorotriamide (HMPTA), glyme and diglyme, dimethyl sulphoxide (DMSO) or tetramethylurea (TMU).
  • petroleum ether fractions preferably relatively high-boiling ones, toluene, mesitylene, dichlorobenzene, tet- rahydrofuran (THF), dimethylformamide (DMF), dimethylacetamide (DMA), hexamethyl- phosphorotriamide (HMPTA), glyme and diglyme, dimethyl sulphoxide (DMSO) or tetramethylurea (TMU).
  • R 2 is hydrogen, C C ⁇ 2 alkyl, phenyl, phenyl-C ⁇ -C alkyI, C ⁇ -C alkylphenyl, C ⁇ -C 4 alkylphenylC r C 4 alkyl, C 4 -C 8 cycloalkyl, C 4 -C 8 cycloaIkyl-C ⁇ -C 4 alkyl, C C 4 alkyl-C 4 -C 8 cycloalkyl or C ⁇ -C 4 alkyl-C 4 -C 8 cycloalkyl-d-C 4 alkyl; and R 3 is a group
  • R', Ri' and R 2 ' have the stated meanings of R, R 1 and R 2 , and n is an integer from 2 to 8.
  • Such compounds have, for example, the following structures:
  • the diamides are known, e.g. N,N'-dipentyldecanediamide (Beilstein Registry No.
  • aldehyde Rr(C O)-H or a reactive, functional derivative, e.g. a hemiacetal or acetal, with the use of an acidic catalyst and elimination of water.
  • R, R 1( R 2 and R 3 have the meanings stated further above.
  • aldehyde R ⁇ -(C O)-H or a reactive, functional derivative, e.g. a hemiacetal or acetal, with the use of an acidic catalyst and elimination of water.
  • a reactive, functional derivative e.g. a hemiacetal or acetal
  • the process is analogous to the process, described further above, for the preparation of compounds (I) and (I'A).
  • the preparation of R-substituted bicyclic triazoles can be effected by catalytic hydrogenation of R-substituted benzotriazoles.
  • R 2 is hydrogen, C ⁇ -C ⁇ 2 alkyl, phenyl, phenyl-C C 4 alkyl, d-C 4 alkylphenyl, d-daikylphenyl-d-dalkyl, C -C 8 cycloalkyl, C -C 8 cycloalkyl-C C 4 alkyl, d-C 4 alkyl-C -C 8 cycloalkyl or C C 4 alkyI-C -C 8 cycloalkyl-CrC 4 alkyl; and
  • R 3 is a group or
  • R', Ri' and R 2 ' have the stated meanings of R, Ri and R 2 and n is an integer from 2 to 8.
  • Such compounds have, for example, the structures:
  • R a , R b , R, Ri, R 2 and R 3 have the meanings stated further above.
  • C r C ⁇ 2 alkyl radicals R a and R are preferably C C 4 alkyl, e.g. methyl, ethyl, n-propyl or isopropyl or n-butyl, sec-butyl or tert-butyl.
  • aldehyde R ⁇ -(C O)-H or a reactive, functional derivative, e.g. a hemiacetal or acetal, with the use of an acidic catalyst and elimination of water.
  • a reactive, functional derivative e.g. a hemiacetal or acetal
  • the invention preferably provides:
  • R is d-dalkyl, phenyl-d-C 4 alkyl or C r C 4 alkylphenyl-d-C 4 alkyl;
  • Ri is C 2 -C ⁇ 2 alkyl; and R 2 and R 3 , independently of one another, are hydrogen or d-C 12 alkyl; or
  • R 2 and R 3 together are C 2 -C 6 alkylene
  • A is methylene
  • Ri is C 2 -C 12 alkyl
  • R 2 and R 3 independently of one another, are hydrogen or d-C 12 alkyl; or
  • R 2 and R 3 together are C 2 -C 6 alkylene
  • Ri', R 2 ' and R 3 ' have the stated meanings of R , R 2 and R 3 ;
  • R is C ⁇ -C 4 alkyl, phenyl-C ⁇ -C 4 alkyl or C ⁇ -C 4 alkylphenyl-C C 4 alkyl;
  • Ri is C 2 -C ⁇ 2 alkyl
  • R 2 and R 3 independently of one another, are hydrogen or C r C 12 alkyl; or
  • R 2 and R 3 together are C 2 -C 6 alkylene.
  • the invention particularly preferably provides:
  • R is CrC 4 alkyl, phenyl-C C 4 alkyl or d-C 4 alkylphenyl-CrC 4 alkyl;
  • R 1 is C 2 -C ⁇ 2 alkyl
  • R 2 is hydrogen and R 3 is C C alkyl
  • R 2 and R 3 together are C 2 -C 6 alkylene
  • A is methylene
  • R T is C 2 -C ⁇ 2 alkyl
  • R 2 and R 3 together are C 2 -C 6 alkylene
  • Ri', R 2 ' and R 3 ' have the stated meanings of R 1 ( R 2 and R 3 ;
  • R is C C 4 alkyl, phenyl-C r C 4 alkyl or C ⁇ -C 4 alkylphenyl-C C 4 alkyl;
  • Ri is C 2 -C ⁇ 2 alkyl; and R 2 and R 3 together are C 2 -C 6 alkylene.
  • the invention very particularly preferably relates to compounds
  • R is d-C 4 alkyl, e.g. methyl or tert-butyl
  • Ri is n-C 3 -C 8 alkyl, e.g. n-propyl, n-hexyl or n-nonyl, and n is an integer from 1 to 3.
  • the invention furthermore preferably relates to compounds (I) from the group consisting of
  • the invention furthermore provides compositions comprising ⁇ ) a functional liquid; and ⁇ ) a compound (I) according to the embodiments a) - d).
  • compositions are those comprising ⁇ ') a non-aqueous functional liquid in contact with metal; and ⁇ ') a compound (I) according to the embodiments a) - d), in which
  • X, Y and Z together are 1 ,2,3-benzotriazole compounds (IA) and (I'A), in which
  • R is hydrogen, C ⁇ -d 2 alkyl, phenyl-C r C 4 alkyl or C C 4 alkylphenyl-C ⁇ -C 4 alkyl, and Ri, R 2 and R 3 have the meanings stated further above; or in which
  • X, Y and Z together are bridged 1 ,2,3-benzotriazole compounds (IB) and (I'B), in which A, Ri, R , R 2 , R 2 ', R 3 and R 3 ' have the meanings stated further above; or in which
  • X, Y and Z together are bicyclic 1 ,2,3-triazole compounds (IC) and (I'C), in which R, R 1( R 2 and R 3 have the meanings stated further above; or in which
  • X, Y and Z together are monocyclic 1 ,2,4-triazole compounds (ID) and (I'D), in which
  • R a . b , i. R 2 and R 3 have the meanings stated further above.
  • the term functional liquid includes non-aqueous, partially aqueous and aqueous 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 internal 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, engine coolants, transformer oil and switchgear 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 internal 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, engine coolants, transformer oil and switchgear oil.
  • Suitable partially aqueous functional liquids are hydraulic fluids based on aqueous polyglycol/ polyglycol ether mixtures or glycol systems, water-in-oil or oil-in-water systems and engine cooling systems based on aqueous glycol.
  • aqueous functional liquids are industrial cooling water, filling compositions of a water conditioning plant, steam generation systems, sea water evaporation systems, sugar evaporation systems, irrigation systems, hydrostatic boilers and heating systems or cooling systems having a closed circulation.
  • the 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 hydraulic fluids.
  • Suitable greases, metal working fluids, gear fluids and hydraulic fluids are based, for example, on mineral or synthetic oils or mixtures thereof.
  • the lubricants are familiar to a person skilled in the art and are described in the relevant literature, such as, for example, in Chemistry and Technology of Lubricants; Mortier, R.M. and Orszulik, S.T. (Editors); 1992 Blackie and Son Ltd. for GB, VCH-Publishers N.Y. for U.S., ISBN 0-216-92921-0, cf. pages 208 et seq. and 269 et seq.; in Kirk-Othmer Encyclopedia of Chemical Technology, Fourth Edition 1969, J. Wiley & Sons, New York, Vol. 13, page 533 et seq.
  • the lubricants are in particular oils and greases, for example based on mineral oil 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, forms or forms prepared by genetic engineering, for example soy bean oil prepared by genetic engineering.
  • Examples of synthetic lubricants include lubricants based on aliphatic or aromatic carboxylic esters, polymeric esters, polyalkylene oxides, phosphoric acid esters, poly- ⁇ -olefins or silicones of the diester of a dibasic acid with a monohydric alcohol, e.g. dioctyl sebacate or di- nonyl adipate, of a triester of trimethylolpropane with a monobasic acid or with a mixture of such acids, e.g.
  • trimethylolpropane tripelargonate trimethylolpropane tricaprylate or mixtures thereof, of a tetra ester of pentaerythritol with a monobasic acid or with a mixture of such acids, e.g. pentaerythrityl tetracaprylate, or of a complex ester of monobasic and dibasic acids with polyhydric alcohols, e.g. a complex ester of trimethylolpropane with caprylic and sebacic acid or of a mixture thereof.
  • Particularly suitable in addition to mineral oils are, for example, poly- ⁇ -olefins, ester-based lubricants, phosphates, glycols, polyglycols and polyalkylene 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 may additionally contain further additives which are added in order further to improve their fundamental properties.
  • additives include: antioxidants, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents, high pressure additives and antiwear additives.
  • Such additives are added in the amounts customary in each case for the purpose, each in the range from 0.01 to 10.0% by weight. Examples of further additives follow:
  • Alkylated monophenols 2,6-di-tert-butyl-4-methylphenol, 2-butyl-4,6-dimethylphenol, 2,6-di-tert-butyI-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-methyIphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4- methoxymethylphenol, linear nonylphenols or nonylphenols which are branched in the side chain, e.g.
  • Alkylthiomethylphenols 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl- 6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonyl- phenol
  • Hvdroquinones and alkylated hvdroquinones 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di- tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyloxy- phenol, 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
  • Tocopherols ⁇ -, ⁇ -, ⁇ - or ⁇ -tocopherols and mixtures thereof (vitamin E)
  • Hydroxylated thiodiphenyl ethers 2,2 , -thiobis(6-tert-butyl-4-methyIphenol), 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-hy- droxyphenyl) disulphide 1.6.
  • Alkylidene bis p henols 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylene- bis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-( ⁇ -methylcyclohexyl)-phe- nol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylenebis(6-nonyl-4-me- thylphenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(4,6-di-tert- butylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2'-methylenebis[6-( ⁇ - methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[6-( ⁇ , ⁇ -
  • Hvdroxybenzylated 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-butyi-4-hydroxybenzyl)malonate, di-[4-(1 ,1 ,3,3- tetramethylbutyl)-phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate
  • Hvdroxybenzyl 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
  • Triazine com p ounds 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-oc- tylmercapto-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-hydroxybenzyl) isocyanurate, 1 ,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)
  • esters of beta-(3,5-di-tert-butyl-4-hvdroxyphenvh-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 -phos- pha-2,6,7-trioxabicyclo[2.2.2]octane
  • esters of beta-(5-tert-butyl-4-hvdroxy-3-methylphenyl)propionic acid (with monohydric or polyhydric alcohols), e.g. the alcohols with methanol, ethanol, n-octanol, isooctanol, octadecanol, 1 ,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentylglycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl) isocyanurate, N,N'-bis(hydroxyethyl)-oxalamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl- 1-phospha-2
  • 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-buty -N'-pheny
  • p.p'-di-tert-octyldiphenylamine 4-n-butyiaminophenol, 4- butyrylaminophenol, 4-nonanoylamino-phenol, 4-dodecanoylaminophenol, 4-octa- decanoylaminophenol, di-(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylami- nomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N,N,N',N'-tetramethyl-4,4'-diaminodiphenyImethane, 1 ,2-di-[(2-methyl-phenyl)- amino]ethane, 1 ,2-di-(phenylamino)-propane, (o-tolyl)biguanide, di-[4-(1',3'-dimethyl-
  • 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- 3,7,10,14-tetrathiahexadecane
  • Benzotriazoles and derivatives thereof 2-mercaptobenzotriazole, 2,5-dimercaptobenz- otriazole, 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 -(nony- loxymethyl)-benzotriazole, 1-(1-butoxyethyl)benzotriazole and 1-(1-cyclohexyloxybu- tyl)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-
  • 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 hydroxycarboxylic acids, partial amides of alkyl- and alkenylsuccinic acids, 4-nonylphenoxyacetic acid, alkoxy- and alkoxyethoxycarboxylic acids, such as dodecyloxyacetic acid, dodecy- loxy(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
  • Heterocyclic compounds e.g. substituted imidazolines and oxazolines, e.g. 2-heptade- cenyl-1-(2-hydroxyethyl)-imidazoiine 5.
  • Sulphur-containing compounds barium dinonylnaphthalenesulphonat.es, calcium petroleum sulphonates, alkylthio-substituted aliphatic carboxylic acids, esters of aliphatic 2-sulphocarboxylic acids and salts thereof
  • Viscosity index improvers polyacrylates, polymethacrylates, vinylpyrroli- done/methacrylate copolymers, polyvinylpyrrolidiones, polybutenes, olefin copolymers, styrene/acrylate copolymers, polyethers
  • 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-ethylhexyl)aminomethyl tolutriazoles, dithiocarbamates, such as methylenebisdibu- tyl dithiocarbamate, derivatives of 2-mercaptobenzothiazole, such as 1-[N,N-bis(2- ethylhexyl)aminomethyl]-2-mercapto-1 H-1 ,3-benzothiazoIe, derivatives of 2,5-dimer- capto-1 ,3,4-thiadiazole, such as 2,5-bis(tert.nonyldithio)-1 ,3,4-thiadiazole
  • 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 possible to prepare a concentrate or a so-called additive packet, which can be diluted to the concentrations of use for the corresponding lubricant according to consumption.
  • the invention likewise relates to a process for protection against corrosion or oxidative degradation of metals which are in contact with functional liquids, or of functional liquids or fuel, wherein one of the compounds (I) defined further above is added to the functional liquid.
  • 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 immersed in the prepared solution, which is kept at 100°C for two hours. The strip is then removed, washed with isooctane and dried and its colour is compared with the standardized colour samples of the tarnish chart which is applicable for the corrosion test of copper strips according to ASTM D130.
  • a 0.05% solution of the test compound in a mineral oil of turbine quality is prepared, which oil has a viscosity of 26.2 mm 2 /sec (40°C) and 4.8 mm 2 /sec (100°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. Table 3

Abstract

L'invention concerne de nouveaux composés de (benzo)triazoles pouvant être préparés à partir de matières premières qui peuvent être obtenues facilement, ces composés comportant des substituants aminoalkyle et pouvant être utilisés en tant que désactivateurs de métaux. L'invention concerne également des compositions contenant lesdits composés et des liquides fonctionnels, de l'huile minérale par exemple. L'invention concerne encore un procédé permettant de stabiliser les liquides fonctionnels par l'ajout de ces nouveaux composés de (benzo)triazoles, ainsi qu'un procédé permettant de protéger des métaux en contact avec des liquides fonctionnels.
PCT/EP2002/007015 2001-07-02 2002-06-25 Benzotriazoles et triazoles aminoalkyle substitues utiles en tant que desactivateurs de metaux WO2003004476A1 (fr)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005117031A2 (fr) * 2004-04-30 2005-12-08 Abb Technology Ltd. Procede et appareil destines a administrer un passivateur a un conducteur
EP1854867A1 (fr) 2006-05-12 2007-11-14 Repsol Ypf S.A. Nouvelle composition stabilisée de carburant
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
US9309205B2 (en) 2013-10-28 2016-04-12 Wincom, Inc. Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures
WO2020083837A1 (fr) 2018-10-24 2020-04-30 Total Marketing Services Association d'additifs pour carburant

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3707477A (en) * 1969-09-11 1972-12-26 Boehringer Sohn Ingelheim 1,1,1-trichloro-2-amido-2-amino-ethanes
US4177155A (en) * 1975-01-23 1979-12-04 Ciba-Geigy Corporation Additives for water-based functional fluids
GB2156813A (en) * 1984-04-04 1985-10-16 Ciba Geigy Ag Substituted aminomethyl triazole compounds useful as metal deactivators
EP0462061A1 (fr) * 1990-06-13 1991-12-18 Ciba-Geigy Ag Composés de triazole utiles comme désactivateurs de métaux
DE4217534A1 (de) * 1992-05-27 1993-12-02 Henkel Kgaa 1-(þ-Amidoalkyl)-diazole, -triazole oder -tetrazole, Verfahren zu deren Herstellung und deren Verwendung
US5441563A (en) * 1993-07-06 1995-08-15 Armstrong World Industries, Inc. Highly insoluble azole embossing inhibitor and the use thereof
FR2722205A1 (fr) * 1995-04-11 1996-01-12 Armstrong World Ind Inc Encre d'imprimerie contenant un inhibiteur de gaufrage azolique, derive de benzotriazole et de benzimidazole
EP0737684A1 (fr) * 1995-04-11 1996-10-16 Ciba-Geigy Ag Composés contenant des groupes (benzo)triazole, leur préparation et leur utilisation comme désactivateurs de métaux et inhibiteurs de corrosion

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3707477A (en) * 1969-09-11 1972-12-26 Boehringer Sohn Ingelheim 1,1,1-trichloro-2-amido-2-amino-ethanes
US4177155A (en) * 1975-01-23 1979-12-04 Ciba-Geigy Corporation Additives for water-based functional fluids
GB2156813A (en) * 1984-04-04 1985-10-16 Ciba Geigy Ag Substituted aminomethyl triazole compounds useful as metal deactivators
EP0462061A1 (fr) * 1990-06-13 1991-12-18 Ciba-Geigy Ag Composés de triazole utiles comme désactivateurs de métaux
DE4217534A1 (de) * 1992-05-27 1993-12-02 Henkel Kgaa 1-(þ-Amidoalkyl)-diazole, -triazole oder -tetrazole, Verfahren zu deren Herstellung und deren Verwendung
US5441563A (en) * 1993-07-06 1995-08-15 Armstrong World Industries, Inc. Highly insoluble azole embossing inhibitor and the use thereof
FR2722205A1 (fr) * 1995-04-11 1996-01-12 Armstrong World Ind Inc Encre d'imprimerie contenant un inhibiteur de gaufrage azolique, derive de benzotriazole et de benzimidazole
EP0737684A1 (fr) * 1995-04-11 1996-10-16 Ciba-Geigy Ag Composés contenant des groupes (benzo)triazole, leur préparation et leur utilisation comme désactivateurs de métaux et inhibiteurs de corrosion

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
A. KATRITZKY ET AL.: "the conversion of secondary into tertiary amides using benzotriazole methodology.", J.ORG.CHEM., vol. 58, no. 8, 1993, pages 2086 - 2093, XP001096184 *
KATRITZKY ET AL: "Benzotriazole-assisted synthesis of.alpha.-(acylamino) nitriles and a conceptually novel method for peptide elongation", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, CHEMICAL SOCIETY. LETCHWORTH, GB, no. 7, 1990, pages 1853 - 1857, XP002140042, ISSN: 0300-922X *
KATRITZKY, ALAN R. ET AL: "New synthesis of amines and amides mediated by additions of benzotriazole to enamines and enamides and transformations of the adducts", SYNTHESIS (1992), (12), 1295-8, XP001094043 *
KATRITZKY, ALAN R. ET AL: "The chemistry of benzotriazole part 8.", J.CHEM.SOC., PERKIN TRANS. I, no. 8, 1988, pages 2339 - 2344, XP001096360 *
KOBAYASHI S ET AL: "A Novel Mannich-type Reaction: Reactions of N-(alpha-Aminoalkyl)benzotriazoles with Silyl Enolates", TETRAHEDRON LETTERS, vol. 37, no. 21, 2 May 1996 (1996-05-02), pages 3731 - 3734, XP004029245, ISSN: 0040-4039 *
S. OHTA ET AL.: "Reaction of 1-(1-alkoxyalkyl)-1H-1,2,4-triazole with amides", HETEROCYCLES, vol. 31, no. 11, 1990, pages 2029 - 2032, XP001096277 *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005117031A2 (fr) * 2004-04-30 2005-12-08 Abb Technology Ltd. Procede et appareil destines a administrer un passivateur a un conducteur
WO2005117031A3 (fr) * 2004-04-30 2006-04-13 Abb Technology Ltd Procede et appareil destines a administrer un passivateur a un conducteur
US7989019B2 (en) 2004-04-30 2011-08-02 Abb Technology Ltd. Method and apparatus for administering passivator to a conductor
EP1854867A1 (fr) 2006-05-12 2007-11-14 Repsol Ypf S.A. Nouvelle composition stabilisée de carburant
US8535569B2 (en) 2011-03-11 2013-09-17 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
US8236205B1 (en) 2011-03-11 2012-08-07 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles and other triazoles 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
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
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
WO2020083837A1 (fr) 2018-10-24 2020-04-30 Total Marketing Services Association d'additifs pour carburant
FR3087788A1 (fr) * 2018-10-24 2020-05-01 Total Marketing Services Association d'additifs pour carburant

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