US2682489A - Rust preventing compositions and process - Google Patents

Rust preventing compositions and process Download PDF

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Publication number
US2682489A
US2682489A US198483A US19848350A US2682489A US 2682489 A US2682489 A US 2682489A US 198483 A US198483 A US 198483A US 19848350 A US19848350 A US 19848350A US 2682489 A US2682489 A US 2682489A
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Prior art keywords
rust
mono
succinic acid
oil
preventive
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US198483A
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Fuchs George Hugo Von
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Priority to NL82067D priority Critical patent/NL82067C/xx
Priority to BE507482D priority patent/BE507482A/xx
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Priority to US198483A priority patent/US2682489A/en
Priority to GB27430/51A priority patent/GB712431A/en
Priority to FR1049577D priority patent/FR1049577A/fr
Priority to DEF7763A priority patent/DE923153C/de
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    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
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    • 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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • 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
    • C23F11/12—Oxygen-containing compounds
    • C23F11/128—Esters of carboxylic acids
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/022—Ethene
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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
    • C10M2207/02—Hydroxy compounds
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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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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
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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
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Definitions

  • the present invention relates to chemical compounds which have rust-preventive properties, to lubricating and other compositions containing such compounds, and to processes for preventing the rusting of ferrous metal surfaces.
  • the problem of preventing rusting of machinery, apparatus and the like is a serious one to the solving of which much effort has been devoted.
  • the problem is complicated by the fact that, other factors being equal, the formation of rust on ferrous metal surfaces is promoted by an increase in temperature.
  • Such surfaces can be prevented from rusting even under conditions which would otherwise favor rusting by establishing thereon a firmly attached hydrophobic film.
  • a film prevents access of water to the metal surface and therefore no rust can form.
  • materials which will provide hydrophobic films cannot be applied in water solution.
  • a hydrophobic film may be provided by supplying a suitable material in an organic solvent or by flowing such a material in molten condition over the metal surface. Neither of these methods is, however, satisfactory in the case of apparatus or machinery in which there is movement of contacting parts.
  • a hydrophobic or water-repellant film is most conveniently established on the ferrous metal surfaces in such apparatus or machinery with a rust-preventive material dissolved in the lubricant employed in the machinery.
  • a rust-preventive material dissolved in the lubricant employed in the machinery.
  • a number of compositions have been suggested for use in this manner as rust preventives.
  • rust preventives are harmful to the stability of the lubricant in which they are used.
  • the rust preventive employed attacks and dissolves to a considerable extent the ferrous metal and/or other catalytic metals, such as copper, present in the system.
  • the metal reaction products thus formed tend to promote decomposition of the lubricant and thereby materially reduce the useful life thereof.
  • alkyl and alkylene succinic acids which have carbon chain lengths of 12 or more carbon atoms in the substituent group are in general not satisfactory for one reason or another.
  • alkylene succinic acids are usually quickly broken down and removed by oxidation at temperatures above atmospheric, thus losing their effectiveness.
  • Branched chain alkyl-substituted acids such, for example, as iso-octadecyl succinic acid, while stable and sufficiently soluble for use, are quite corrosive to copper and other metals commonly employed in apparatus such as engines, pumps, turbines and the like.
  • Mono-esters such as, for example, octadecyl succinic acid mono-methyl ester and tetradecyl succinic acid mono-propyl ester, having the general formula 1-1 X-c-oooY H-o-oooY alkyl radical containing not more than three carbon atoms in a straight chain, and the other Y is hydrogen, have been found very effective as rust-preventive agents.
  • the efiectiveness of such esters as rust preventives is surprising since previously it has been believed that the rustpreventive action of alkyl and alkylene succinic acids results from the reaction of both of the proximate carboxyl groups of the acids with the surface of the protected metal. Such a conclusion appeared reasonable when it is considered that mono-carboxylic acids are of slight or no value as rust preventives in the small percentages normally used, and are actually corrosive.
  • Alkyl and alkylene succinic acids are conveniently prepared by the reaction of olefins with maleic anhydride.
  • the resultant product is an alkylene succinic acid anhydride which may be converted into the corresponding alkyl succinic anhydride by hydrogenation.
  • the general process is disclosed in Patent No. 2,055,456, issued September 22, 1936, to Egon Eichwald, and Patent No. 2,411,215, issued November 19, 1946, to Mearl A. Kise et al.
  • Esters of the alkyl succinic acid may be conveniently formed by merely heating together stoichiometric amounts of the desired alcohol and the anhydride of the desired acid. The extent of esterification may be determined by determination of the acid number of the resultant product.
  • the mono-esters of alkyl succinic acids in which the alcohol has no more than three carbon atoms in a straight chain which for convenience will be referred to hereinafter merely as rust inhibitive mono-esters, are shown to be lacking in harmful effect.
  • Table B shows the results of tests in which the copper wire coil was immersed in oil which was of the same type as that used before but which contained 0.25 per cent of ditertbutyl-p-cresol as an inhibitor of oil oxidation.
  • the ability of a material suggested for use as a rust-preventive to establish an adherent waterrepellant film on a ferrous metal surface immersed in an oil solution of the material is preferably determined by the A. S. T. M. Steam- Turbine Oil Rusting Test (D665-49T).
  • the procedure involves suspending a polished steel rod in a bath of oil which contains a definite percentage of the proposed rust preventive and which is maintained at 140 F. and constantly stirred, and subsequently, after a water-repellant film has had an opportunity to form, adding distilled water While continuing the stirring. From time to time the steel specimen is examined for rust spots.
  • the adherence or tenacity of the water-repellant film on the steel specimens used in the A. S. T. M. rusting test was determined by the supplement to that test described in The Texas Company publication, Lubrication in the issue of May 1944, pages 49 and 50.
  • the specimens were removed from the oil and immersed in distilled Water for 24 hours during which period the water was agitated and maintained at a temperature of 140 F. At the end of the 24. hour test period no sign of rusting was observed on any of the specimens treated with the rust-preventive mono-esters described herein.
  • the resistance of steel specimens coated With water-repellant films. of various mono-esters of the present invention to attack by an aqueous salt solution was determined by the so-called static water drop corrosion test described'by Baker et al. in Industrial and Engineering Chemistry, vol. 41, January 1949, at page 137, using a medium viscosity white oil as a carrier, a test temperature of F., and a concentration of rust-preventing agent of 0.1 per cent.
  • the test was, however, modified, as suggested elsewhere by one of the authors, by placing a drop of synthetic sea water in the cup of each specimen instead of a drop of distilled water. This modification greatly increases the severity of the test.
  • the synthetic sea water used was prepared according to the method described in A. S. T. M. designation: D665-49T, Tentative Method of Test for Rust-Preventive Characteristics of Steam-Turbine Oil in the Presence of Water, by dissolving the specified amounts of the following salts in 1000 ml. of distilled water.
  • oils comprising derivatives of polyalkylene glycols, which are now known, and available commercially, as Ucon brand fluids and lubricants.
  • These fluids can be formed by the reaction of alkylene oxides with aliphatic monohydric alcohols, and they are essentially addition products comprising complex mixtures of molecules having polyoxyalkylene chains of different lengths and varying internal arrangements. Further description of typical fluids of this nature can be found in Patent 2,448,664, issued to Harvey R. Fife and Frederick H. Roberts on September 7, 1948.
  • Test I A standard Studebaker automobile engine was run at full throttle-4500 R. P. M.for 50 hours using the synthetic oil mentioned above with the addition of 2.0 per cent of the mono-methyl ester of octadecyl succinic acid. The lubricant temperature was maintained at 195 F. and the coolant temperature at 170 F. After completion of the test the engine was dismantled. Upon inspection, it was then found to be in excellent condition. Cleanliness, bearing weight losses and wear measurements showed no more than normal differences between results obtained with LB-300X alone and the same lubricant to which the mono-ester had been added.
  • crankcase lubricant consisting of the polyalkylene glycol synthetic oil mentioned above plus 2.0 per cent of the mono-methyl ester of octadecyl succinic acid was run in a Chevrolet automobile engine under the standard Coordinating Research Council L-4 Procedure for determining oxidation characteristics of heavy-duty crankcase oils.
  • the engine operated at 3150 R. P. M., 30 B. H. P., for 36 hours with a lubricant temperature of 280 F. and a coolant temperature of 200 F.
  • synthetic oil #1 was a medium viscosity polyalkylene glycol oil identified as Uncon brand fluid LB-270
  • synthetic oil #2 was a low viscosity, low pour point oil produced by the polymerization of ethylene to give an average molecular weight of about 250
  • synthetic oil #3 was di(2-ethylhexyl) sebacate, sold under the name Plexol- 01.
  • the last mentioned oil is representative of the diester type synthetic lubricants which are formed by reacting branched chain aliphatic alcohols such as Z-ethyl hexanol with straight chain dibasic acids such as sebacic and adipic acids.
  • the diester synthetic oils are expensive but have very low viscosities and are used for the lubrication of instruments and similar purposes Where corrosion is very undesirable.
  • the rust preventive compounds identified and listed in Table E by the letters A, B, C, and D are respectively the mono-methyl ester of octadecyl succinic acid, the mono-methyl ester of dodecyl succinic acid, the mono-methyl ester of tetradecyl succinic acid, and the mono-methyl ester of hexadecyl succinic acid.
  • the rust-preventive mono-esters of the present invention may also be employed with good results in other types of compositions.
  • slushing oil Or compound formed of a low viscosity mineral oil containing 1 per cent of a rust preventive mono-ester is easily applied by dipping, painting or spraying.
  • the water repellant film formed by the mono-ester provides substantially permanent rust protection for the coated ferrous metal surface even after the oil has been wiped 01f.
  • the viscous oils or greases formerly required to give even temporary protection from rust are difficult to remove whereas the low viscosit oil may be easily wiped from the metal surface.
  • Rust resistance can be imparted to fresh ferrous metal surfaces by the incorporation of the rust-preventive mono-esters of the present invention in the cutting oils or coolants used in -machining, grinding and similar operations on the metal.
  • Temporary rust inhibitors are now frequently used in such fluids but no lasting water-repellant film is left on the metal surfaces.
  • Ordinary cutting oils or coolants containing a small amount, in the order of 1-2 per cent, of a rust-preventive mono-esmr of an alkyl-substituted succinic acid leave the metal surfaces wtih a durable long-lasting film which prevents rusting thereof.
  • organic fluids used for many other purposes which may come into contact with iron or steel surfaces may be compounded with the rust-preventive mono-esters to prevent the rusting of such surfaces.
  • transformer oils, fluids used in hydraulic systems and torque converters, and fluids employed for heat transfer if mixed with (Jill-0.1 per cent of one of the rust-preventive monoesters will prevent rusting in the systems in which they are used.
  • Rust-preventive monoesters may also be used effectively in small amount in antifreeze fluids, flushing oils, and gasoline, fuel oils and other liquid petroleum products with or Without other materials added for other purposes.
  • Water-repellant, rust-preventing films may also be provided on ferrous metal surfaces by deposition of rust-preventive mono-esters from solutions of organic solvents.
  • the mono-esters readily dissolve in a number of organic solvents such, for example, as carbon tetrachloride, benzene, kerosene, naphtha, and the mixtures of alcohols and benzene commonly used as cleaners for metal parts.
  • the alkylsubstitute-d succinic acid mono-esters of the present invention are highly effective in preventing the rusting of ferrous metals. They are, moreover, capable of being used widely and conveniently since they are readily soluble in liquid petroleum products and in a large variety of other organic fluids although substantially insoluble in water. Mixtures of different rustpreventive mono-esters may, of course, be used where desired as may also mixtures of one or more rust-preventive mono-esters and one or more alkyl or alkylene succinic acids.
  • an oxidation inhibitor in oils or other organic rust-preventing fluids containing a rust-preventive mono-ester is not a necessity, it will usually be desirable since in many cases the stability of the oil or fluid will thereby be considerably improved.
  • the amount of such inhibitor will vary with the organic material used, but generally will be within a range of from 0.0025 to 5.0 per cent.
  • oxidation inhibitors of other types such as phe'nyl-alphanapthylamine and phenothiazine may be used.
  • the rust-preventive monoesters are compatible with many of the other additives which are widely used in lubricants and hence may be used in oils containing pour point depressants, extreme pressure additives and the like.
  • ester is a mono-tert-butyl ester of octadecyl succinic acid.
  • a rust-preventive composition comprising a major proportion of an organic medium having in solution therein a minor proportion of an ester of an alkyl succinic acid having the general formula in which X is a straight chain alkyl radical containing at least 12 carbon atoms, one Y is an alkyl radical containing not more than 3 carbon atoms in a straight chain, and the other Y is hydrogen.
  • a rust-preventive composition as set forth in claim 8 which also contains a minor amount of an oxidation inhibitor for said organic medium.
  • a rust-preventive lubricating composition comprising a major proportion of an organic lubricant having in solution therein a minor proportion of an ester of an alkyl succinic acid having the general formula i XC-COO'Y H(
  • a rust-preventive cutting oil comprising in solution in a mineral oil a minor proportion of an ester of an alkyl succinic acid having the general formula in which X is a straight chain alkyl radical containing at least 12 carbon atoms, one Y is an alkyl radical containing not more than 3 carbon atoms in a straight chain, and the other Y is hydrogen.
  • a rust preventive composition comprising a major proportion of an organic medium having in solution therein a minor proportion of a monotert-butyl ester of octadecyl succinic acid.
  • a ferrous metal article having a surface coating thereon which comprises the reaction product of said metal and an ester of an alkyl succinic acid having the general formula in which X is a straight chain alkyl radical containing at least 12 carbon atoms, one Y is an alkyl radical containing not more than 3 carbon atoms in a straight chain, and the other Y is hydrogen.
  • a ferrous metal article having a surface coating thereon which comprises the reaction product of said metal and a mono-tert-butyl ester of octadecyl succinic acid.

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  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
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US198483A US2682489A (en) 1950-11-30 1950-11-30 Rust preventing compositions and process
GB27430/51A GB712431A (en) 1950-11-30 1951-11-22 Improvements in or relating to rust preventing compositions and process
FR1049577D FR1049577A (fr) 1950-11-30 1951-11-27 Perfectionnements apportés aux produits antirouille et aux procédés pour leur utilisation
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2962443A (en) * 1955-08-31 1960-11-29 Lubrizol Corp Steam turbine lubricant
US3032502A (en) * 1959-08-17 1962-05-01 Standard Oil Co Lubricant compositions
US3223636A (en) * 1961-05-23 1965-12-14 Exxon Research Engineering Co Lead corrosion inhibitor
US3291736A (en) * 1964-11-20 1966-12-13 Mobil Oil Corp Grease compositions containing alkyl succinic partial esters
US3381022A (en) * 1963-04-23 1968-04-30 Lubrizol Corp Polymerized olefin substituted succinic acid esters
US3720615A (en) * 1969-08-11 1973-03-13 Kao Corp Oil-soluble rust preventive composition
US3730485A (en) * 1969-09-10 1973-05-01 Shell Oil Co Ashless anti-rust additives
US4128403A (en) * 1974-09-06 1978-12-05 Chevron Research Company Fuel additive for distillate fuels
US5021174A (en) * 1986-05-27 1991-06-04 Euron S.P.A. Compounds useful as detergent additives for lubricants and lubricating compositions
US20070284412A1 (en) * 2006-05-31 2007-12-13 Prakash Anna M Solder flux composition
US20080156852A1 (en) * 2006-12-29 2008-07-03 Prakash Anna M Solder flux composition and process of using same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9818323D0 (en) * 1998-08-21 1998-10-14 Ass Octel Fuel additives
WO2004024850A1 (en) 2002-09-13 2004-03-25 Octel Starreon Llc Process for the production of a fuel composition

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2284241A (en) * 1939-05-13 1942-05-26 Du Pont Corrosion inhibition
GB580603A (en) * 1943-04-13 1946-09-13 Standard Oil Co California Turbine lubricating oil compositions
US2442672A (en) * 1941-02-18 1948-06-01 Shell Dev Rust-preventive hydrocarbon compositions
US2459717A (en) * 1946-01-23 1949-01-18 Shell Dev Organic lubricant composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2284241A (en) * 1939-05-13 1942-05-26 Du Pont Corrosion inhibition
US2442672A (en) * 1941-02-18 1948-06-01 Shell Dev Rust-preventive hydrocarbon compositions
GB580603A (en) * 1943-04-13 1946-09-13 Standard Oil Co California Turbine lubricating oil compositions
US2459717A (en) * 1946-01-23 1949-01-18 Shell Dev Organic lubricant composition

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2962443A (en) * 1955-08-31 1960-11-29 Lubrizol Corp Steam turbine lubricant
US3032502A (en) * 1959-08-17 1962-05-01 Standard Oil Co Lubricant compositions
US3223636A (en) * 1961-05-23 1965-12-14 Exxon Research Engineering Co Lead corrosion inhibitor
US3381022A (en) * 1963-04-23 1968-04-30 Lubrizol Corp Polymerized olefin substituted succinic acid esters
US3291736A (en) * 1964-11-20 1966-12-13 Mobil Oil Corp Grease compositions containing alkyl succinic partial esters
US3720615A (en) * 1969-08-11 1973-03-13 Kao Corp Oil-soluble rust preventive composition
US3730485A (en) * 1969-09-10 1973-05-01 Shell Oil Co Ashless anti-rust additives
US4128403A (en) * 1974-09-06 1978-12-05 Chevron Research Company Fuel additive for distillate fuels
US5021174A (en) * 1986-05-27 1991-06-04 Euron S.P.A. Compounds useful as detergent additives for lubricants and lubricating compositions
US20070284412A1 (en) * 2006-05-31 2007-12-13 Prakash Anna M Solder flux composition
US20080156852A1 (en) * 2006-12-29 2008-07-03 Prakash Anna M Solder flux composition and process of using same

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FR1049577A (fr) 1953-12-30
GB712431A (en) 1954-07-21
DE923153C (de) 1955-02-03
NL82067C (de)

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