US2908648A - Corrosion-inhibited compositions containing n-(alkylarylsulfonyl) amino acids and salts thereof - Google Patents

Corrosion-inhibited compositions containing n-(alkylarylsulfonyl) amino acids and salts thereof Download PDF

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Publication number
US2908648A
US2908648A US463842A US46384254A US2908648A US 2908648 A US2908648 A US 2908648A US 463842 A US463842 A US 463842A US 46384254 A US46384254 A US 46384254A US 2908648 A US2908648 A US 2908648A
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Prior art keywords
corrosion
dodecylbenzenesulfonyl
water
vehicle
acid
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US463842A
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Inventor
John D Spivack
Janet B Peterson
Kroll Harry
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Novartis Corp
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Geigy Chemical Corp
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Priority to BE542184D priority Critical patent/BE542184A/xx
Application filed by Geigy Chemical Corp filed Critical Geigy Chemical Corp
Priority to US463842A priority patent/US2908648A/en
Priority to CH344886D priority patent/CH344886A/de
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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
    • 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
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/32—Wires, ropes or cables lubricants
    • 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
    • C10N2040/34—Lubricating-sealants
    • 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
    • C10N2040/36—Release agents or mold release agents
    • 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
    • C10N2040/38—Conveyors or chain belts
    • 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
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • 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
    • C10N2040/42—Flashing oils or marking oils
    • 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
    • C10N2040/44—Super vacuum or supercritical use
    • 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
    • C10N2040/46—Textile oils
    • 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
    • C10N2040/50—Medical uses
    • 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
    • C10N2050/10—Semi-solids; greasy
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • compositions having corrosion inhibited, and especially" rust-inhibited properties which contain alkylarylsulfonyl derivatives. More particularly the present invention relates to organic compositions, especially oleag'inous compositions containing an alkyl-arylsul'fonyl derivative, which compositions have the property of preventing or inhibiting corrosion and/0r, rusting; especially in sy'ste'rhsem'ploying water or steam or which may be contaminated with water or steam.
  • V In various equipment in which water and/ or steam is used, or which may become contaminated with water or steam during service orstorag'e, corrosion and/orrustirrg of the metal parts, particularly'the ferrous metalparts, is encountered causing material damage to such equipment.
  • the prevention of rust formation is particularly impore taut in the protection of metal surfaces where such surfaces are to be lubricated in the presenee ofmoisture.
  • Moisture may enter lubricating systems of land or marine turbines, for example, by leakage through steamglands and through water-cooled heat exchangers or :by, condensation fromqthe amesphere.
  • compositions employed for the protection of metals against atmospheric corrosion vand/ or Such compositions are applied to metallic articles, includipg fabricated metallic artieles and finished of semi-fin v ished riiet'al stock to be stored or for shipment by rail or water, to p'r'eveliq r'u'stiiig arid/or corrosion thereo f. r
  • the aim in the use' of protective orslushirig; compositions is tofprot ect fobiec s against Q attack by moisture by coat in'gthem'.
  • Important industrial a'plication's' of the corrosion this invention may be added to awide of vehicles to produce compositions having corrosion-inhibited properties, including acidic. aqueousliquids, suchas used in V amidoalk ue ca y i -a f the. general fopmula' R SO ','-NH --R C O OR (wherein R is a saturated hyd-roca'r bfon of ,C C k is'either aliphatic C H m or aryl or aromatic radicals and R is H or an alkalim'etal; or amn'aoni-u'm') to alcohols, ketones and mixtures thereof.
  • alkanes'ul'fonamidoalkane .carboxylic acids used for that purpose are described in U.S. Patent No. 2,225,960 granted December 24, 1940.
  • a specific example is hexadecanesulfonamidoacetic acid of the formula:
  • R represents one or two alkyl groups of 8-24 carbon atoms inclusiveg
  • Ar representsan aryl group. which may bephehyl, naphtHyL-arithracyl, plienanth'ryl, chrysyl (Beilstein; vol. V,- p.
  • R represents a substituent selected from the group consisting of hydrogen, allgyl; lrjydroxyalkyl, carboxyalkyl and phenyl; R represents a substituent selected from the group consist- 1 ing of hydrogen, alkyl and czirboxyalkyl; n represents l" or 2; Y represents hydrogen or a-salt forming group;
  • the above type compounds are added to a liquid or semi-solid vehicle iii a quantity sufiicient to confer corrosion and/or rust prevention to the composition which otherwise tends to permit corrosion of metal when brought and/or rust preventing compounds of the present invenr-;1
  • Non-limiting examples of the new type of compounds which are useful asrust and/or corrosion preventives are: N-(dodecylbenzenesulfonyl) glycine, N-(dodecylbenzenesulfonyl) sarcosine, N-(dodecylbenzenesulfonyl) irnin'odiacetic acid, N-(dodecylbenzenesulfonyl) glutamic' acid, N-(dodecylbenzenesulfonyl) alanine, N'-(dinonylnapha thalenesulfonyl) glycine, N-(dinonylnaphthalenesulfonyl) sarcosine, N-(dinonylnaphthalenesulfonyl)-iminodiacetic acid, N-(dinonylnaphthalenesulfonyl) glutamic
  • the sulfonylated amino acids of the general type of the corrosion preventative agents of our'invention can be prepared in a number of ways, forexample, as out- Ssponification Saponification 2 Acidification RArSaNR1(CHz),-CHC00H R-Ar- SO2NH+Cl(CH2)n-(i7HGOONa '-v .1 R,” v v R-A'r-s0mr21(o11,)..-on'o ooNa e ifi n .7 n-ar-soirmaomn onooon V ,1 2
  • Thereactants in the process of manufacture maybe re atrvelypure single compounds, for example, pure allgylarylsulfonyl, chloride or :thesulfon yl a'mide (see empir cal: formula of respective first; mentioned reactant 1n .l'Tiq1 lt10l1S'A
  • the reactants may be mixtures resulting in a product consisting of a mixture of compounds, all represented by the formula the symbols in which are defined above.
  • the RA1' grouping set forth above may be derived from straightchain or branched-chain octyl, decyl, dodecyl, tetradecyl, hexadecyl, or octadecyl derivatives of either benzene, naphthalene, anthacene or chrysene or from mixtures thereof.
  • the R-Ar grouping may also be derived from the reduction of fatty acylated or alkenylated aromatic
  • the products obtained by processes (B) and (C) outlined above may also have more or less unsaponified ester or nitrile groupings present therein in addition to free carboxyl groups or salts thereof.
  • One of the major uses of the additives of the present invention is in the industrial field of lubrication of metal surfaces employing both oils and greases. Another use is the protection of metals, such as iron or broader the ferrous type metal, in humid atmospheres by preservative oils and slushing oils or greases.
  • the members of the class of compounds of this invention can be used alone in an oleaginous vehicle or solvent. Used thus these additives which function as corrosion inhibitors, may be used in a variety of physical states, e.g., as a dispersion, emulsion or solution. When employed in an oleaginous vehicle, the compounds should be soluble, miscible or dispersible in said vehicle.
  • oleaginous vehicle is employed in the broader sense and to include hydrocarbon oils, fatty oils, fats, the synthetic lubricants such as those of the polyester, poly siloxane, polyalkylene glycols and polyolefine types, and rustproof bases, etc., which may be used as the medium of application of rust-preventive additive to the metal surface.
  • V I a The N-(alkylarylsulfonyl) amino acids may be incor-' porated in the oleaginous vehicle in varying proportions being governed by specific use to which the rust preven tive compositionis to be put, the degree of rust prevention desired, as well as economic considerations, and on the specific alkylarylsulfonyl amino. acid selected. Generally it is suificient to use an amount between 0.005 and a 10% by weight, although greater or lesser amounts may be used.
  • alkylarylsulfonyl amino acids and their salts which are the corrosion inhibitors of the'present inventors, are believed to have the rust tests and emulsion tests.
  • reaction mixture was'poured into 300 grams of ice, and 300 milliliters of diethyl ether were added, intimately mixed therewith, whereupon after Stratification the water layer was separated from the upper or ether layer. The water layer was extracted with anadditional 300 milliliters of ether.
  • the combined ether extracts were extracted with 300 milliliters of a aqueous solution of sodium bicarbonate also containing 10% by weight of sodium chloride to remove residual inorganic acids.
  • the ether in the purified ether layer was removed by distillation at atmospheric pressure followed by reduced pressure.
  • the residue was taken up in 500 milliliters of acetone and filtered free of inorganic salts. Analysis of the residue (A) from the acetone distillation indicated that product (A) contained about 8.3% of n-dodecylbenzene sulfonyl chloride, the remainder being n-dodecylbenzene sulfonic acid.
  • Phosphorus pentachloride (19.3 grams) was added gradually with occasional shaking to product (A) amounting to 28 grams, in an Erlenmeyer flask fitted with a drying tube. After eifervescence stopped, the reaction mixture was warmed on a water bath for about 30 minutes. The product was then poured into ice, and extracted with 200 milliliters of ether. The ether extract was thereupon washed with water' and then dried over anhydrous sodium sulfate. After being separated, ether was removed by evaporation. The residue, which was product (B), was a viscous, reddish oil, the analysis of which indicated that it consisted of 96%-97% of ndodecylbenzenesulfonyl chloride.
  • the chloroform solution of the reaction product was washed successively with water and 5% aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. It was then decanted from the drying agent. The residue, after evaporation of chloroform was heated on a steam bath with milliliters of 1 N sodium hydroxide solution in water for two hours.' The product was the sodium salt of N-'(n dodecylbenzenesulfonyl) iminocliace'tic acid in solution. The alkaline solution was extracted with 100 milliliters of ether to remove uns'aponified material.
  • Example 3 of corrosion inhibitor-(N-dodecylbenzenesulfonyl) sarcosine technical A PREPARATION OF DODECYLBENZENESULFON'YL CHLORIDE This compound was prepared in the following manner from a commercial grade of dodecylbenzene.
  • aqueous alkali containing 4.7 grams of sodium hydroxide
  • the reaction mixture was stirred at 45 C. for one hour and then let stand at room temperature for about sixteen hours.
  • Example 4 of corrosion inhibitor Reactin product of technical dodecylbenzenesulfonyl chloride with iminodiacetic acid Iminodiacetic acid (2 g.) (0.015 mole) and triethylamine (4.55 g.) (0.045 mole) were mixed in boiling chloroform, and after cooling to room-temperature the 90% dodecylbenzenesulfonyl chloride, prepared by Example 3(A) supra, in an amount of 5.15 grams (0.0105
  • reaction product thus has an analysis which varies quite appreciably from that expected for (N-dodecylbenzenesulfonyl) iminodiacetic acid.
  • Example of corrosion inhibitor Reaction product of dodecylbenzenesulfonyl chloride with dimethyliminodiacetate hydrochloride
  • Dimethyliminodiacetate hydrochloride (20.0 grams) (0.10 mole) was dispersed in 200 milliliters of chloroform, and 24.3 grams of triethylamine (0.24 mole) was added rapidly while the chloroform dispersion was stirred.
  • rust test data and emulsion test data were obtained for a selected mineral oil containing the respective products synthesized in Examples 1, 2, 3, 4 and 5 described above.
  • the oil used in these was a solvent-refined and filtered non-additive turbine-grade lubricating mineral oil of 150 Saybolt Universal Seconds viscosity at F.
  • the rust test which was selected because it'has been widely used was the Static Water Drop Corrosion Test developed by Zisman et al. and described in Industrial and Engineering Chemistry, vol. 41, page 137 it (1949). Briefly, the test consists essentially of observing rusting at 140 F. in the presence of liquid water in the dimple of a triangular cold-rolled steel specimen immersed in the test oil, An effective rust preventive ,oil will prevent rusting for several days while straight mineral oils permit rusting to occur within'2 hours. of test.
  • Solubilization of these 'N-(alkylarylsulfonyl) amino acids of these examples was effected by the addition of a solubilization agent which per se in oil solution had little, if any, rust preventive properties.
  • the specific agent used was a commercially available tertiary alkyl primary'amine, the tertiary alkyl groups having'from 18 to 24 carbon atoms, known as Primene JMR, which is descn'bedmore' exactly in a footnote-in Table I.
  • the test used for determining the demulsibility properties of lubricating oils is to be found in the Federal Standard Stock Catalogue method 320.1.5 dated November 15, 1948, and entitled Emulsion (Lubricating Oils). Briefly, this test involves mixin 40 milliliters of water and 40 milliliters of test oil at 130 F. or Fpunder standard conditions and observing the separation of oil and water phases at the test temperature.
  • the test temperature selected is usually 130 F. for light viscosity turbine oils up' to about 500 SayboltUniversal seconds viscosity at 100 F., andthat'was the temperature which was selected for the tests reported.
  • Thefigures in the table show the number of minutes at which thereis no continuous layer of emulsion between the oil and the emulsant (water).
  • the corrosion test and the emulsion test were run on the base oil as'a check, the tertiaryalkyl primary amine- (2 concentrations) in the oil, stearic acid in the oil, and mixtureof stearic acid with the tertiaryallgyl primary amine in the oil, as well as the oil containingi the investigated N-(alkyl aryls'ulfonyl) amino acids in the compositions given in the appended table.
  • N -(n-dodecylbenzenesulfonyl) sarcosine More than 300 hrs. N-(n-dodecylbenzenesulfonyl)iminodiacetic acid. II Do. (N -dodecylbenzenesulfonyl)sarcosine (technical) III Do.
  • the vehicle can be aqueous which includes aqueous solutions of liquids, such as alcohol-water mixtures, or the like
  • suitable vehicles for the corrosive inhibitor additives of this invention are mineral lubricating oils of all grades; gasolines and otherlight petroleum products, such as fuel oil; water, alcohols, such as ethanol, isopropanoL'butanol; cyclohexanol, methylcyclohexanol, octanol, decanol, dodecanol, hexadecanol, octadecanoh-oleyl alcohol, benzyl alcohol, ctc.; glycols, such as ethylene glycol, propylene glycol, butylene glycol; glycerol, etc.; ketones, such as acetone, methyl ethyl ketone, dipropyl ketone, cyclohexanone, etc.
  • keto alcohols such as benzoin; others, such as diethyl ether, dipropyl ether, dichloro diethyl ether, diphenyl oxide, polyethylene glycols as diethylene glycol and triethylene glycol, ethy1 ene glycol monobutyl ether, etc.; neutral esters, such as ethyl acetate, butyl propionate, cresyl acetate, dodecyl acetate, ethyl maleate, butyl stearate, tridecyl phosphate, tributyl trithiophosphate, triamyl phosphite, dibutyl sebacate and dioctyl sebacate, etc.; petroleumwaxes, such as slack wax and paraffin wax; natural waxes, such as carnauba wax, japan Wax, beeswax, etc.; natural fats and oils, such as sperm oil, tallow, cottonseed oil, cast
  • Acidic aqueous solutions for metal pickling baths cananti-freezes include Water, water-alcoho1, glycols, glycolwater, etc.
  • the corrosion inhibitors of this invention can be added to compositions contemplated herein to impart other desirable properties thereto, such as anti-oxidants, pour point depressants, V.I. improver's, etc.
  • Some members of this class of compounds will be preferred for specific applications While other members will be preferred for other applications whererust prevention is desired.
  • Some members of this class of compounds are particularly applicable for turbine lubrication, because lubricant compositions containing them permit ready separation of entrained water. It is essential that Water be easily separable from turbine lubricants by auxiliary oil purification equipment such as settling tanks, filters, blotter presses, centrifuges, etc., because ,Water in addition to causing rusting accelerates oil breakdown, causes excessive foaming and facilitates the dispersion of other contaminants which accelerate oil breakdown and are injurious to the lubricating system in other ways.
  • a corrosion-inhibiting composition which comprises a liquid vehicle which tends to permit the corrosion of metalin the service to which said vehicle is put, containing a member selected from the group consisting of N-(n-dodecylbenzenesulfonyl) sarcosine and N-(n-dodecylbenzenesulfonyl) iminoacetic acid, said member being present in said liquid vehicle in amounts of as little as a fraction of 1% by Weight but in a sulficient quantity to inhibit corrosion of said vehicle.
  • a corrosion-inhibiting composition which comprises a liquid vehicle which tends to permit the corrosion of metal in the service to Which said vehicle is put, containing N-(n-dodecylbenzenesulfonyl) sarcosine, said latter component being present in said liquid vehicle in amounts of as little as a fraction of 1% by weight but in a sufficient quantity to inhibit corrosion of said metal.
  • a corrosion inhibiting composition which comprises a liquid vehicle which tends to permit the corrosion of metal in the service to which said vehicle is put, containing N-(n-dodccylbenzenesulfonyl) iminodiacetic acid, said latter component being present in said liquid vehicle in amounts of as little as a fraction of 1% by weight but in a suflicient quantity to inhibit corrosion of said metal.
  • a rust-inhibited oleaginous composition adapted for use in the presence of water in systems containing metal susceptible to corrosion by said water, comprising an oleaginous vehicle and a member selected from the group consisting of N-(n-dodecylbenzenesulfonyl) sarcosine and N-(n-dodecylbenzenesulfonyl) iminoacetic acid, said member being present in said oleaginous vehicle in amounts of as little as a fraction of 1% by weight but in a sufiicient quantity to inhibit corrosion of said vehicle.
  • a rust-inhibited oleaginous composition adapted foruse in the presence of water in systems containing metal susceptible to corrosion by said water comprising an oleaginous vehicle and N-(n-dedocylbenzenesulfonyl) sarcosine, said latter component being present in said oleaginous vehicle in amounts of as little as a fraction of 1% by weight but in a sufficient quantity to inhibit corrosion of said metal.
  • a rust-inhibited oleaginous composition adapted for use in the presence of water in systems containing metal susceptible to corrosion by said water comprising an oleaginous vehicle and N-(n-dodecylbenzenesulfonyl) iminodiacetic acid, said latter component being present in said oleaginous vehicle in amounts of as little as a fraction of 1% by Weight but in a suflicient quantity to inhibit corrosion of said metal.
  • a rust-inhibited oleaginous composition adapted for use in the presence of water in systems containing metal susceptible to corrosion by said water comprising an oleaginous vehicle, a member selected from the group consisting of N-(n-dodecylbenzenesulfonyl) sarcosine and N--(n-dodecylbenzenesulfony1) iminoacetic acid in amounts of as little as a fraction of 1% but in suflicient quantity'to inhibit corrosion of said metal, and an alkyl primary amine having 18-24 carbon atoms in sufiicient amount to solubilize said member in the oleaginous vehicle.
  • a rust-inhibited oleaginous composition adapted for use in the presence of water in systems containing metal susceptible to corrosion by said water, comprising an oleaginous vehicle, N-(n-dodecylbenzenesulfonyl) sarcosine in amounts of as little as a fraction of 1% but in sufiicient quantity to inhibit corrosion of said metal,
  • a rust-inhibited oleaginous composition adapted for use in the presence of water in systems containing metal susceptible to corrosion by said water, comprising an oleaginous vehicle, N-(n'dodecylbenzenesulfonyl) iminodiacetic acid in amounts of as little as a fraction of 1% but in suificient quantity to inhibit corrosion of said 12 metal, and an alkyl primary amine having 18-24 carbon atoms in suflicient amount to solubilize said N-(n-dodecylbenzenesulfonyl) iminodiacetic acid.
  • a rust-inhibited oleaginous composition adapted for use in the presence of water in systems containing metal susceptible to corrosion bysaid Water comprising an oleaginous vehicle, a member selected from the group consisting of N-(n-dodecylbenzenesulfonyl) sarcosine and N-(n-dodecylbenzenesulfonyl) iminoacetic acid in amounts to between substantially 0.005 to about 10% by weight, and an alkyl primary amine having 18-24 carbon atoms in suflicient amount to solubilize said member in the oleaginous vehicle.
  • a rust-inhibited oleaginous composition adapted for use in the presence of water in systems containing metal susceptible to corrosion by said Water, comprising an oleaginous vehicle, N-(n-dodecylbenzenesulfonyl) sar cosine in amounts between substantially 0.005% to about 10% by weight, and an alkyl primary amine having 18-24 carbon atoms in suflicient amount to solubilize said N-(n-dodecylbenzenesulfonyl) sarcosine in the oleaginous vehicle.
  • N-(n-dodecylbenzenesulfonyl) sar cosine in amounts between substantially 0.005% to about 10% by weight
  • an alkyl primary amine having 18-24 carbon atoms in suflicient amount to solubilize said N-(n-dodecylbenzenesulfonyl) sarcosine in the oleaginous vehicle.
  • a rust-inhibited oleaginous composition adapted for use in the presence of water in systems containing metal susceptible to corrosion by said water, comprising an oleaginous vehicle, N-(n-dodecylbenzenesulfonyl) iminodiacetic'acid in amounts between substantially 0.005% to about 10% by weight, and an alkyl primary amine having 18-24 carbon atoms insufficient amount to solubilize said N-(n-dodecylbenzenesulfonyl) iminodiacetic acid.

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US463842A 1954-10-21 1954-10-21 Corrosion-inhibited compositions containing n-(alkylarylsulfonyl) amino acids and salts thereof Expired - Lifetime US2908648A (en)

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CH344886D CH344886A (de) 1954-10-21 1955-10-18 Verwendung von neuen Alkylarylsulfonylaminosäuren als korrosions- und rostverhindernde Zusatzstoffe

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US3027405A (en) * 1959-07-29 1962-03-27 Geigy Chem Corp Nu-(alkylarylsulfonyl)-amino acids and salts thereof
US3291645A (en) * 1964-09-10 1966-12-13 Allied Chem Corrosion inhibitor in dry cell battery
US3625894A (en) * 1967-05-13 1971-12-07 Hoechst Ag Anticorrosive for lubricants
US3992306A (en) * 1973-06-18 1976-11-16 Hoechst Aktiengesellschaft Metal-working and corrosion protection agent
US4344862A (en) * 1979-11-24 1982-08-17 Basf Aktiengesellschaft Reaction products of sulfonamido-carboxylic acids or carboxamido-carboxylic acids with alkanolamines, and their use as low-foaming corrosion inhibitors
US4443477A (en) * 1980-01-07 1984-04-17 Boehringer Mannheim Gmbh Sulphonamidophenylcarboxylic acid compounds and pharmaceutical compositions containing them
US4970026A (en) * 1988-09-21 1990-11-13 Drew Chemical Corporation Corrosion inhibitor
US4999134A (en) * 1987-09-25 1991-03-12 Basf Aktiengesellschaft Zinc salts, lead salts and/or calcium salts of carboxylic acids and their use as corrosion inhibitors
US11492569B2 (en) * 2020-02-03 2022-11-08 Kepco Nuclear Fuel Co., Ltd. Composition of external lubricant for cold pilgering
US11492568B2 (en) * 2020-02-03 2022-11-08 Kepco Nuclear Fuel Co., Ltd. Composition of internal lubricant for cold pilgering

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US2225960A (en) * 1939-01-27 1940-12-24 Gen Aniline & Film Corp Condensation products and a process of preparing them
DE900041C (de) * 1943-04-22 1953-12-17 Hoechst Ag Korrosionsschutzmittel
US2578725A (en) * 1949-10-20 1951-12-18 Josef M Michel Process of protecting metals against corrosion
US2602760A (en) * 1950-07-18 1952-07-08 Josef M Michel Process of protecting metals against corrosion
US2656381A (en) * 1950-10-21 1953-10-20 Merck & Co Inc Secondary alkylsulfonamido benzoic acids
US2692857A (en) * 1951-01-19 1954-10-26 Josef M Michel Noncorrosive graphite emulsions
US2660562A (en) * 1951-03-26 1953-11-24 Phillips Petroleum Co Lubricants
US2704264A (en) * 1951-07-16 1955-03-15 Josef M Michel Process of protecting surfaces of metals against corrosion
US2694045A (en) * 1951-12-14 1954-11-09 Standard Oil Dev Co Stabilizer for petroleum products

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3027405A (en) * 1959-07-29 1962-03-27 Geigy Chem Corp Nu-(alkylarylsulfonyl)-amino acids and salts thereof
US3291645A (en) * 1964-09-10 1966-12-13 Allied Chem Corrosion inhibitor in dry cell battery
US3625894A (en) * 1967-05-13 1971-12-07 Hoechst Ag Anticorrosive for lubricants
US3992306A (en) * 1973-06-18 1976-11-16 Hoechst Aktiengesellschaft Metal-working and corrosion protection agent
US4344862A (en) * 1979-11-24 1982-08-17 Basf Aktiengesellschaft Reaction products of sulfonamido-carboxylic acids or carboxamido-carboxylic acids with alkanolamines, and their use as low-foaming corrosion inhibitors
US4443477A (en) * 1980-01-07 1984-04-17 Boehringer Mannheim Gmbh Sulphonamidophenylcarboxylic acid compounds and pharmaceutical compositions containing them
US4999134A (en) * 1987-09-25 1991-03-12 Basf Aktiengesellschaft Zinc salts, lead salts and/or calcium salts of carboxylic acids and their use as corrosion inhibitors
US4970026A (en) * 1988-09-21 1990-11-13 Drew Chemical Corporation Corrosion inhibitor
US11492569B2 (en) * 2020-02-03 2022-11-08 Kepco Nuclear Fuel Co., Ltd. Composition of external lubricant for cold pilgering
US11492568B2 (en) * 2020-02-03 2022-11-08 Kepco Nuclear Fuel Co., Ltd. Composition of internal lubricant for cold pilgering

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Publication number Publication date
CH344886A (de) 1960-02-29
BE542184A (fr)

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