US3452038A - Certain bis(benzothiazole) compounds - Google Patents

Certain bis(benzothiazole) compounds Download PDF

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US3452038A
US3452038A US479344A US3452038DA US3452038A US 3452038 A US3452038 A US 3452038A US 479344 A US479344 A US 479344A US 3452038D A US3452038D A US 3452038DA US 3452038 A US3452038 A US 3452038A
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parts
bis
benzotriazole
water
solution
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Donald Richard Randall
Donald Kearey Howard
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Novartis Corp
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Geigy Chemical Corp
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
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    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
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    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/02—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in air or gases by adding vapour phase inhibitors
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    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/14—Nitrogen-containing compounds
    • C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
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    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/16—Sulfur-containing compounds
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/14—Synthetic waxes, e.g. polythene waxes
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • 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
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/30—Heterocyclic compounds
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
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    • 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
    • C10N2030/08—Resistance to extreme temperature
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    • 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
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/922—Static electricity metal bleed-off metallic stock
    • Y10S428/923—Physical dimension

Definitions

  • X is (a) methylene which is substituted with one or two C alkyl groups, or C alkylene which is unsubstituted or substituted with 1 or more C alkyl groups, (b) a lzl-cycloalkyl containing at least five carbon atoms, (c) carbonyl, (d) sulfonyl, (e) oxygen, or (f) sulfur.
  • X is unsubstituted methylene or a chemical bond, are useful for inhibiting the tarnishing or corrosion of metals and the metal-induced deterioration of functional materials.
  • X represents (a) a divalent straight chain alkylene bridging group containing from one to six carbon atoms in the chain and being substituted with from one or two alkyl groups containing each from one to four carbon atoms where the alkylene group contains only one carbon atom, or being unsubstituted or substituted with at least one alkyl group containing from one to four carbon atoms where the alkylene group contains two or more carbon atoms; (b) lzl-cycloalkyl residue containing at least five carbon atoms; (c) a carbonyl group; ((1) a sulfonyl group; or (f) a sulfur atom.
  • X as defined under (a) and being alkyl-substituted, bears as substituents from one to four alkyl groups each containing from one to four carbon atoms.
  • metallic surface is used generically for both metal and metal alloy surfaces; corrosion-inhibiting is used generically for inhibiting corrosion as well as tarnishing.
  • the bridging group X of Formula III represents an alkylene group, it contains from one to six carbon atoms; if one or more alkyl substituents are present in the alkylene group, the substituent may be a methyl, ethyl, npropyl, iso-propyl, n-butyl or iso-butyl group.
  • alkylene bridging groups X include ethylene, n-propylene, n-butylene, n-amylene, n-hexylene, methyl-methylene, dimethyl-methylene, ethyl-methylene, diethyl-methylene, propyl-methylene, dipropyl-methylene-, n-butyl-methylene, di-n-butyl-methylene, 1 methyl-ethylene, 1,2 dimethylethylene, l-ethyl-ethylene, 1,2-ethyl-ethylene, l-npropylethylene, 1,2-n-propyl-ethylene, l-n-butyl-ethylene, 1,2 n-butyl-ethylene, 1,1-dimethyl-ethylene, 1,1-diethylethylene, 1,1 diethyl-ethylene, 1,l-di-n-propyl-ethylene, 1,1-di-n-butyl-ethylene, 1,1,2-trimethyl-ethylene or 1,1,2,2- tetramethyl-ethylene
  • the metallic surface can be treated with a solution containing one or several bis-benzotriazole compounds of Formulas I, II and/or III.
  • a solution containing the bis-benzotriazole compound or compounds in a proportion in the range of from 0.001% by weight to saturation may be used, but a solution containing from 0.01% to 5%, and particularly containing from 0.1% to 1%, by weight of the bis-benzotriazole compound, calculated on the weight of the solution, is preferred.
  • the bis-benzotriazole compounds of Formulas I, II and III are sparingly soluble in water or other aqueous media, and organic solvents, especially oxygenated hydrocarbon compounds, can be used, for example acetone and other dialkyl ketones, isopropanol and other alkanols, 2-methoxy-ethanol and other al'koxy-al- 'kanols, or ethylene glycol or other alkylene-or dial'kyleneglycols, depending on the nature of the bis-benzotriazole compound, the concentration desired and the mode of treatment of the metallic surface with the solution.
  • organic solvents for example, trichlorethylene, can also be used where appropriate.
  • the metallic surface may be treated with the solution in any convenient manner.
  • the surface can be dipped into or passed through the solution containing the bis-benzotriazole compound.
  • the surface can also be treated by padding with absorbent material soaked in the solution, or by spraying the surface with an atomized mist of the solution.
  • Other methods of carrying out the process according to the invention include condensing the vapor of one or several of the bis-benzotriazole compounds of Formulas I, II and/or III on the metallic surface; enclosing or otherwise wrapping the metal object bearing the surface to be protected in wrapping material impregnated with one or several of the bis-benzotriazole compounds of Formulas I, II and/or III; applying one or several of the said hisbenzotriazole compounds in an abrasive or non-abrasive polish composition to the metallic surface; and incorporating one or several of the said bis-benzotriazole compounds in other compositions, for example anti-freeze or coolant formulations, or in functional fluids, for example synthetic lubricants or polymeric formulations, which are normally applied to, or are used in the presence of, a metallic surface.
  • a temperature within the range of from 60 to 100 C., and then allowing the treated metallic surface to dry in air or heating it to remove by evaporation any solvent remaining on the surface.
  • Another mode of carrying out the process of the invention in practice comprises packing the surface of the metallic surface to be protected in wrapping material, for example, tissue paper imregnated with one or several bisbenzotriazole derivatives of Formulas I, II and/ or III.
  • the wrapping material may be impregnated by soaking in a solution containing from 0.1% up to 5% by weight of the said bis-benzotriazole derivative, calculated on the weight of the solution.
  • a third mode of carrying out the process of the invention comprises moving or suspending the surface of the metallic surface in an atmosphere saturated with the vapor of one or several bis-benzotriazole derivatives of the Formulas I, H and/or III so as to expose said surface to the action of said atmosphere.
  • the vapor is conveniently maintained at 85 C. and the metallic object may be chilled prior to being moved into the vapor to facilitate rapid condensation of the latter on the metallic surface to be protected.
  • a further mode of carrying out the process of the invention in practice comprises treating the surface of the metallic surface with a non-abrasive wax or polish containing one or several bis-benzotriazole derivatives of Formulas I, II and/or III.
  • the wax or polish preferably contains between 0.1% and by weight of the said hisbenzotriazole derivative or derivatives. If solid wax is used, the bis-benzotriazole derivatives can be stirred into the molten wax and the mixture subsequently cast into a convenient form; if a liquid wax is used, the bis-benzotriazole derivatives can be added as a solution in a solvent Which is compatible with the liquid base of the wax.
  • a fifth mode of carrying out the process of the invention in practice comprises treating the metallic surface with a suspension of an abrasive material suspended in a liquid or soft solid medium and containng one or several bisbenzotriazole derivatives of Formulas I, II and/or III.
  • the amount of bis-benzotriazole derivatives in such suspension is within the range of from 0.01% to 5% and optimally within the range of from 0.1% to 1.0% by weight, calculated on the weight of the aforesaid medium.
  • the bis-'benzotriazole derivatives of Formulas I, II and III possess useful corrosion-inhibiting properties when applied to metallic surfaces, particularly to surfaces of copper, copper alloys, cadmium, or cadmium alloys.
  • the bisbenzotriazole derivatives of Formulas I, II and III can be used, for example, to inhibit corrosion of a metallic surface exposed to an atmosphere comprising sulfur dioxide, hydrogen sulfide or ammonia or other corrosive gaseous constituent; for example, brass or other copper alloys may be treated with a benzotriazole derivative or derivatives of Formulas I, II and/or III in accordance with the process of the invention, to inhibit stress corrosion cracking due to exposure to sulfur dioxide.
  • bis-benzotriazoles of the formula Nrr ⁇ NH/ 111 appearance of the surfaces are also valuable metal deactivators, particularly copper deactivators, when comprised in functional materials susceptible to deterioration of function in contact with the metal; such materials include functional fluids, and the said bis-benzotriazole derivatives when included in functional fluids for use at high temperatures, for example in high temperature synthetic lubricants.
  • corrosion-inhibiting compositions for application to a metallic surface, and particularly to a copper or copper alloy surface, containing, as corrosion-inhibiting agent a bis-benzotriazole derivative or derivatives of Formulas I, II and/ or III.
  • the concentration of inhibitors in the corrosion-inhibiting compositions according to the invention is preferably within the range of from 0.01% to 5.0% and more preferably within the range of from 0.1% to 1.0% by weight based on the total weight of the composition, the concentration of the inhibitor varying according to the composition containing the inhibitor.
  • the present invention also provides a functional material per se susceptible to deterioration of function in contact with a metal, particularly copper or a copper alloy, which has been rendered less susceptible by comprising, as metal deactivator, a bis-benzotriazole derivative of Formulas I, II and/or III.
  • the conventration of inhibitors in the composition in the functional material is preferably within the range of from 0.001% to 0.5% and more preferably within the range of from 0.001% to 0.01% by weight based on the total weight of the functional material.
  • the compounds of Formulas I, II and III may also be advantageously used in metal or metal alloy protecting compositions or in functional materials in conjunction with other inhibitors, especially with inhibitors effective for the protection of ferrous metals.
  • Bis-benzotriazole, of Formula I is produced by reacting 3:3'z4:4-tetraaminodiphenyl with nitrous acid or with a compound capable of forming nitrous acid under the conditions of the reaction, in the stoichiometric amounts required to diazotize only two of the four amino groups.
  • the 3:3':4:4'-tetraaminodiphenyl may be treated, for example, with a mixture of an alkali metal nitrite and an inorganic acid.
  • the reaction may be carried out under conditions similar to a conventional diazotization method, for example by treatment at a controlled temperature with an aqueous mixture of an alkali metal nitrite and hydrochloric acid, acetic acid or other inorganic or organic acid.
  • the desired bis-triazole of Formula I is then formed by simultaneous elimination of two molecules of water under the diazotization conditions.
  • 3:3:4:4'-tetraaminodiphenyl is produced, for instance, by reduction of 3 3'-dinitro-4:4'-diaminodiphenyl.
  • the reduction can be carried out by treating the 3:3'-dinitro- 4:4'-diaminodiphenyl with molecular hydrogen in the presence of a cataylst; the hydrogenation cataylst can be, for example, Raney nickel.
  • the reduction can be carried out in practice by contacting 3:3-dinitro-4:4'-diaminodiphenyl with a hydrogen-generating mixture, for instance with hydrochloric acid and iron or tin.
  • the 3z3'-dinitro-4:4-diaminodiphenyl is, in turn, produced by nitration of 4:4'-diaminodiphenyl.
  • the nitration is carried out by reaction with nitric acid by a conventional method.
  • the amino groups of the 4:4- diaminodiphenyl are protected during the nitration by conversion, for instance, into acetylamino or other acylamino groups.
  • the conversion of the amino groups may be effected by reacting 4:4-diaminodiphenyl with the corresponding acid anyhdride or acylhalide, and after the nitration has been carried out, the amino group can be regenerated by hydroylsis, for example, with an aqueous solution of an alkali metal hydroxide.
  • 5:5'-methylene-bis-benzotriazole of Formula II is produced by reacting 3 :3':4:4'-tetraaminodiphenylmethanc of the formula with nitrous acid or with a compound capable of forming nitrous acid under the conditions of the reaction in the stoichiometric amounts required to diazotize only two of the four amino groups.
  • the 3:3':4:4-tetraaminodiphenylmethane is treated, for example, with a mixture of an alkali metal nitrite and an inorganic or organic acid.
  • the reaction is carried out under conditions similar to a conventional diazotization method, for example, by treatment at a controlled temperature with an aqueous mixture of an alkali metal nitrite and hydrochloric acid, acetic acid or other inorganic or organic acid.
  • the desired 5:S'-methylene-bis-benzotriazole is then formed by simultaneous elimination of two molecules of water under diazotization conditions.
  • the 3:3:4:4'-tetraaminodiphenylmethane is produced for instance, by reduction of 3:3-dinitro-4:4-diaminodiphenylmethane.
  • the reduction is carried out by treating the 3:3'-dinitro-4:4-diaminodiphenylrnethane with molecular hydrogen in the presence of a catalyst; the hydrogenation catalyst can be, for example, Raney nickel.
  • the reduction is carried out in practice by contacting the 3:3- dinitro-4:4'-diaminodiphenylmethane with a hydrogengenerating mixture, for instance with hydrochloric acid and iron or tin.
  • the 3:3-dinitro-4:4'-diaminodiphenylmethane is, in turn, produced by nitration of 4:4'-diaminodiphenylmethane.
  • the nitration is carried out by reaction with nitric acid by a conventional method.
  • the amino groups of the 4:4'-diaminodiphenylmethane are protected during the nitration by conversion, for example, into acetylamino or other acylamino groups.
  • the conversion of the amino groups can be effected by reacting 4:4'- diaminodiphenylmethane with the corresponding acid anhydride or acyl halide, and after the nitration has been carried out, the amino groups can be regenerated by hydrolysis, for instance with an aqueous solution of an alkali metal hydroxide.
  • 3:3 dinitro-4:4'-diaminodiphenylmethane can be produced by rearrangement of N,N-methylenebis-o-nitroaniline of the formula NO: OzN
  • the rearrangement is preferably carried out initially in the presence of excess concentrated hydrochloric acid at a moderate temperature, for example, a temperature within the range of from 20 to 55 C. and subsequently at a higher temperature, for example, a temperature within the range of from 60 to 100 C. in the presence of gaseous hydrogen chloride.
  • a moderate temperature for example, a temperature within the range of from 20 to 55 C.
  • a higher temperature for example, a temperature within the range of from 60 to 100 C. in the presence of gaseous hydrogen chloride.
  • the 3:3'-dinitro-4:4-diaminodiphenylmethane product is isolated and purified by con ventional methods.
  • the 3:3- dinitro-4:4'-diaminodiphenylmethane is then converted to 5:5'-methylene-bisbenzotriazole by the procedure described above.
  • the N,N'-methylene-bis-o-nitroaniline is, in turn, produced for example, by condensing two molecules of o-nitroaniline with one molecule of formaldehyde in an organic solvent, for instance methylated spirits, at an elevated temperature.
  • the product is isolated by conventional methods such as distillation, and can be further purified, for example by recrystallization techniques.
  • Bis-benzotriazole derivatives of Formula III are produced by reacting a 3z3':4:4'-tetraaminodiphenyl derivative of the formula wherein X has the same meaning as in Formula III, with nitrous acid or with a compound capable of forming nitrous acid under the conditions of the reaction, in the stoichiometric amounts required to diazotize only two of the four amino groups.
  • the 3:3:4:4'-tetraaminodipheny1 derivative can be treated, for example, with a mixture of an alkali metal nitrite and an inorganic or organic acid.
  • the reaction can be carried out under conditions similar to a conventional diazotization method, for example, by treatment at a controlled temperature with an aqueous mixture of an alkali metal nitrite and hydrochloric acid, acetic acid or other inorganic or organic acid.
  • the desired bis-benzotriazole derivative of Formula III is then formed by simultaneous elimination of two molecules of water under the diazotization conditions.
  • the 3:3:4:4'-tetraaminodiphenyl derivative of Formula VI is produced, for instance, by reduction of the corresponding 3:3-dinitro-4:4-diaminodiphenyl derivative of the formula NO: VII
  • the reduction iscarried out by treating the 3:3'-dinitro-4:4'-diaminodiphenyl derivative with molecular hydrogen in the presence of a catalyst; the hydrogenation catalyst can be, for example, Raney nickel.
  • the reduction can also be carried out in practice by contacting the 3:3'-dinitro-4:4'-diaminodiphenyl derivative with a hydrogen-generating mixture, for instance with hydrochloric acid and iron or tin.
  • the 3:3'-dinitro-4:4'-diaminodiphenyl derivative is in turn, produced by nitration of the corresponding 4:4'-diamino-diphenyl derivative with nitric acid by a conventional method.
  • the amino groups of the 4:4- diaminodiphenyl derivatives are protected during the nitration by conversion, for example, to acetylamino or other acylamino groups.
  • the conversion of the amino groups is effected by reacting the 4:4'-diaminodiphenyl derivative with the corresponding acid anhydride or acyl halide, and, after the nitration has been effected, regenerating the amino groups by hydrolysis, for instance with an aqueous solution of an alkali metal hydroxide.
  • bis-benzotriazole derivatives falling under Formula III can also 'be obtained by slightly modified methods.
  • bis-(benzotriazolyl-S) ketone of the formula can be produced by nitrating 4:4'-dichlorobenzophenone using, for instance, fuming nitric acid at a low temperature, for example a temperature Within the range of from -10 to +10 C. and reacting the resulting 4:4'- dichloro-3:3-dinitrobenzophenone with ammonia, preferably in a closed vessel and at an elevated temperature, for example a temperature Within the range of from to 300 C.
  • Bis-(benzotriazolyl-S)ketone can also be produced by the controlled oxidation of the bis-(benzotriazolyl)methane of Formula II.
  • bis-'(benzotriazolyl-5)sulfone can be produced by the controlled oxidation of bis (b enzotriazolyl-S sulfur.
  • EXAMPLE 1 5-methylene-bis-benzotriazole (A) 4:4-diacetamino-3 3-dinitrodiphenylmethane.- 562 parts of acetic anhydride were added to a solution of 496 parts of 4:4'-diaminodiphenylmethane in 496 parts by volume of benzene at 30 to 35 C. over a period of 3 hours. The mixture was then stirred at the same temperature for a further period of 1 /2 hours before being poured into an excess of cold water. The solid product formed was filtered ott, recrystallised from glacial acetic acid and dried in a vacuum oven. 596 parts of 4:4-diacetaminodiphenylmethane, having melting point 236 C. were obtained, representing a yield of 84.5% theoretical.
  • (C) 4:4 diamino 3:3 dinitrodiphenylmethane A mixture of 144 parts of 4:4-diacetamino 3:3'-dinitrodiphenylmethane, 62 parts of sodium hydroxide, 93 parts by volume of water and 1000 parts by volume of 2- methoxyethanol were heated under reflux conditions for 15 minutes and then allowed to cool to room temperature. The orange-red crystalline product which separated was filtered ofl, washed well with water and oven-dried. In this Way 97.7 parts of 4:4-diamino 3:3-dinitrodiphenylmethane were obtained, having melting point 238 C., representing a yield of 87.7% theoretical.
  • EXAMPLE 2 A specimen from the same bright acid dipped copper foil was immersed in one of each of the following solutions: 0.01% w./v. aqueous solution of benzotriazole; 0.01% w./v. aqueous solution of 5 :5'-methylene-bis benzotriazole (as produced in the procedure described in Example l); 0.01% w./v. solution of benzotriazole in industrial methylated spirits; 0.01% w./v. solution of 5:5- methylene-bis benzotriazole in industrial methylated spirits; 0.1% w./v. solution of benzotriazole in industrial methylated spirits; 0.1% w./v. solution of 5 :5-methylenebis-benzotriazole in industrial methylated spirits.
  • the six immersed specimens were maintained at 65 C. for five minutes and they were then washed in distilled water and dried in hot air.
  • the resistance to tarnishing of the copper specimens was compared with that of a seventh specimen of the same acid-dipped, but otherwise untreated, copper foil as a control, by exposing the specimens to an atmosphere containing 10 parts per million by weight of hydrogen sulphide. The time taken for the onset of visible tarnish to occur was recorded as a measure of tarnish resistance.
  • EXAMPLE 3 A specimen from the same sheet of cadmium foil was immersed in one of the following solutions: 0.01% solution of 5:5 methylene-bis-benzotriazole in industrial methylated spirtis; 0.01% solution of 5 :5'-methylene-bisbenzotriazole in water. The two immersed specimens were maintained at 65 C. for five minutes and they were then washed in distilled water and dried in hot air.
  • the resistance to tarnishing of the cadmium specimens was compared with that of an untreated specimen of the same cadmium foil as a control by exposing the four specimens to an atmosphere containing 10 parts per million by weight of hydrogen sulphide. The time taken for the onset of visible tarnish to occur was recorded as a measured of tarnish resistance.
  • EXAMPLE 4 Samples of bright acid dipped copper were polished with an aqueous isopropanol suspension of an abrasive material containing 84 parts of aqueous 40% isopropanol and 15 parts of a-alumina (abrasive) both with and without the addition of 0.3% weight/weight of 5:5'-methylenebis-benzotriazole. A sample of the same copper was also polished with a similar abrasive material containing 1% of benzotriazole. The polished specimens of copper were then tested for tarnish inhibition by exposure to an atmosphere containing 10 parts per million by weight of hydrogen sulphide. The time taken for the onset of visible tarnishing to occur was recorded as a measure of the tarnish resistance imparted to the copper surface by the polish used.
  • EXAMPLE 7 Bis-(benzotriazolyl-S) sulphone (A) 4,4-dichloro-3,3'-dinitrodiphenylsulphone.--60.3 parts of 4,4-dichlorodiphenyl-sulphone were dissolved in 301 parts of concentrated sulphuric acid and then 301 parts of fuming nitric acid (d.1.50) added slowly keeping temperature at 20 to 40 C. initially, then at 80 C. to give a clear yellow solution from which 83 parts (substantially of theoretical yield 100%) of the dinitro compound, having melting point 202 C. separated on pouring on to water.
  • EXAMPLE l0 Bis- (benzotriazolyl-S -1 :2-ethane (A) 4,4-dinitrodibenzyl.274 parts of p-nitrotoluene and 464 parts of isoamyl formate dissolved in 250 parts by volume of toluene were added to a suspension of 272 parts of sodium ethoxide in 500 parts by volume of toluene at 0 to 2 C. over 2 hours. The mixture was then stirred for a further 21 hours at 0 to 5 C. and poured into water. In this way, 136 parts (50% yield) of the dinitro compound, having melting point 176 to 176.5 C. were obtained.
  • EXAMPLE 1 1 Bis(benzotriazolyl-5 )-1 l-cyclohexane (A) 4,4-diaminodiphenyl-l,l-cyclohexane.-To 475 parts of aniline dissolved in 440 parts by volume of concentrated hydrochloric acid was added 250 parts cyclohexanone and 52 parts by volume of alcohol and the mixture was heated on a steam bath for 12 days. By filtering off the solid that separated on cooling, dissolving this in water and treating with excess alkali, 132.3 parts of the diamino compound having melting point 114 C. were obtained.
  • EXAMPLE 13 A specimen from the same bright acid-dipped copper foil was immersed in one of each of the following solutions:
  • the seven immersed specimens were maintained at 65 to 70 C. for two minutes and were then removed and dried in an oven at C., the tarnish so produced being of a uniform golden/ brown colour.
  • the resistance to tarnishing of the copper specimens was compared with that of an eighth specimen of the same acid-dipped but otherwise untreated copper foil as a control.
  • the times indicated in the following Table 4 are the times at which the first sign of tarnish occurred.
  • EXAMPLE 14 Samples of bright acid dipped copper were polished with a water emulsifiable polish containing 0.2% weight/ weight of bis-benzotriazole, 5 :5-methylene bis-benzotriazole, bis-(benzotriazolyl-S)ketone and bis-(benzotriazolyl-S) ether. A sample of the same copper was also polished with the same water emulsifiable polish containing no bis-benzotriazole compound.
  • the water emulsifiable soap consisted of 25 parts of red iron oxide (jewellers rouge), 1 part of hydroxymethyl cellulose, as gelling agent, 13.1 parts of soap consisting of 4.5 parts of triethanolamine and 8.6 parts of stearic acid, 3.2 parts of glycerol and 56.7 parts of water.
  • the polished specimens were then tested for tarnish inhibition by exposing the speci- 10 parts per million by weight of hydrogen sulfide. The time taken for the onset of visible tranish to occur was recorded as a measure of tarnish resistance.
  • the six immersed specimens were maintained at 65 C. for two minutes and then washed in distilled water and dried in hot air.
  • EXAMPLE 18 1 kg. of tissue paper is immersed in a 0.01% w./v. aqueous solution of 5 :5'-methylene-bis-benzotriazole, withdrawn from the solution and air-dried.
  • the resulting materials can be used for wrapping metal 17 articles or articles possessing metallic surfaces which require protection from corrosion and tarnishing.
  • a bis-benzotriazole compound having the formula carbon atom, or being unsubstituted or substituted with 1 at least one alkyl group containing from one to four carbon atoms where the alkylene group contains two or more carbon atoms; (b) a 1: l-cycloalkyl residue containing five or six carbon atoms; (c) a carbonyl group; (d)
  • a sulfonyl group (e) an oxygen atom; or (f) a sulfr atom.

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US3755069A (en) * 1970-12-14 1973-08-28 Eastman Kodak Co Highly stable resin coated paper products and method of making same
US4314809A (en) * 1978-12-02 1982-02-09 Henkel Kommanditgesellschaft Auf Aktien Novel coupler components for oxidation hair dyes, the manufacture thereof, and hair colorants
US4323707A (en) * 1975-10-28 1982-04-06 Eli Lilly And Company Antifertility compounds
US4388215A (en) * 1980-12-12 1983-06-14 Sanyo Mokuzai Bofu Kabushiki Kaisha Wood preservative composition
US4629466A (en) * 1982-09-25 1986-12-16 Henkel Kommanditgesellschaft Auf Aktien Oxidation hair dyes comprising bis-(2,4-diaminophenyl)-alkanes as coupling components
US4636359A (en) * 1983-10-27 1987-01-13 Henkel Kommanditgesellschaft Auf Aktien Method for inhibiting corrosion of zinc using bis-triazoles
US4714779A (en) * 1980-11-20 1987-12-22 Xerox Corporation Aromatic aryl amine polymers
US5190723A (en) * 1988-02-25 1993-03-02 Ciba-Geigy Corporation Process for inhibiting corrosion
US6265667B1 (en) 1998-01-14 2001-07-24 Belden Wire & Cable Company Coaxial cable

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US4060491A (en) * 1975-10-02 1977-11-29 Mobil Oil Corporation Lubricant composition
NL170757C (nl) * 1977-04-12 1982-12-16 Akzo Nv Werkwijze voor het reinigen en tegen roest beschermen van een ijzeren of stalen oppervlak.
US4153563A (en) * 1978-05-24 1979-05-08 Mobil Oil Corporation Lubricant compositions containing benzotriazole-allyl sulfide reaction products
US4153565A (en) * 1978-06-15 1979-05-08 Mobil Oil Corporation Benzotriazole adduct and lubricant compositions containing said adduct
US4508756A (en) * 1980-10-08 1985-04-02 Murata Manufacturing Co., Ltd. Method for inhibiting oxidation of a copper film on ceramic body
US4595523A (en) * 1983-07-01 1986-06-17 Petrolite Corporation Corrosion inhibition in engine fuel systems
US4871644A (en) * 1986-10-01 1989-10-03 Ciba-Geigy Corporation Photoresist compositions with a bis-benzotriazole
US4835085A (en) * 1986-10-17 1989-05-30 Ciba-Geigy Corporation 1,2-Naphthoquinone diazide sulfonyl ester compound with linking benzotriazole groups and light-sensitive composition with compound
US4731128A (en) * 1987-05-21 1988-03-15 International Business Machines Corporation Protection of copper from corrosion
JP3077193B2 (ja) * 1990-11-23 2000-08-14 株式会社デンソー アルミニウム表面に耐食性化成皮膜を形成する方法
GB9425030D0 (en) 1994-12-09 1995-02-08 Alpha Metals Ltd Silver plating
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TW399094B (en) * 1995-04-11 2000-07-21 Ciba Sc Holding Ag Compounds with (benzo)triazole radicals
US5752358A (en) * 1997-01-07 1998-05-19 Chadwick Engineering Limited Stretch wrap dispenser head with coating applicator
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MXPA05002763A (es) * 2002-09-13 2005-09-08 Octel Starreon Llc Procedimiento para la produccion de una composicion de combustible.
JP4313750B2 (ja) * 2004-11-04 2009-08-12 新日本製鐵株式会社 埋設地際部の腐食防御性を有する鋼製柱
US7820068B2 (en) * 2007-02-21 2010-10-26 Houghton Technical Corp. Chemical assisted lapping and polishing of metals
US9051098B2 (en) * 2009-10-19 2015-06-09 Inoflate, Llc Method for pressurizing containers with nitrogen
WO2016194668A1 (ja) * 2015-05-29 2016-12-08 シャープ株式会社 液晶表示装置
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3755069A (en) * 1970-12-14 1973-08-28 Eastman Kodak Co Highly stable resin coated paper products and method of making same
US4323707A (en) * 1975-10-28 1982-04-06 Eli Lilly And Company Antifertility compounds
US4314809A (en) * 1978-12-02 1982-02-09 Henkel Kommanditgesellschaft Auf Aktien Novel coupler components for oxidation hair dyes, the manufacture thereof, and hair colorants
US4714779A (en) * 1980-11-20 1987-12-22 Xerox Corporation Aromatic aryl amine polymers
US4388215A (en) * 1980-12-12 1983-06-14 Sanyo Mokuzai Bofu Kabushiki Kaisha Wood preservative composition
US4629466A (en) * 1982-09-25 1986-12-16 Henkel Kommanditgesellschaft Auf Aktien Oxidation hair dyes comprising bis-(2,4-diaminophenyl)-alkanes as coupling components
US4636359A (en) * 1983-10-27 1987-01-13 Henkel Kommanditgesellschaft Auf Aktien Method for inhibiting corrosion of zinc using bis-triazoles
US5190723A (en) * 1988-02-25 1993-03-02 Ciba-Geigy Corporation Process for inhibiting corrosion
US6265667B1 (en) 1998-01-14 2001-07-24 Belden Wire & Cable Company Coaxial cable

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