US2832742A - Corrosion inhibitor composition - Google Patents

Corrosion inhibitor composition Download PDF

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US2832742A
US2832742A US435626A US43562654A US2832742A US 2832742 A US2832742 A US 2832742A US 435626 A US435626 A US 435626A US 43562654 A US43562654 A US 43562654A US 2832742 A US2832742 A US 2832742A
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water
carbon chain
carboxylic acids
corrosion
acids
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US435626A
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Clarence A Weltman
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Alox Corp
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Alox Corp
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    • 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
    • C23F11/14—Nitrogen-containing compounds
    • C23F11/141—Amines; Quaternary ammonium compounds
    • C23F11/143—Salts of amines

Definitions

  • This invention relates to water-soluble corrosion-inhibiting compositions and is more particularly concerned with inhibitors for use primarily in water circulating systems such as automobile radiators, certain industrial heat exchangers, cooling towers and the like.
  • the inhibitor provide some residual protection of the metal after it is removed from contact with the inhibited water.
  • the exposed metal should be protected for a short time. Uninhibited water will cause corrosion While in contact with the steel and will accelerate further corrosion as it evaporates.
  • a corrosion inhibiting composition having outstanding properties may be prepared by blending about equal parts of para tertiary butyl benzoic acid, hereinafter referred to as ptBBA, with relatively high molecular weight aliphatic carboxylic acids derived from a petroleum fraction, e. g., from a normally liquid petroleum fraction such, for instance, as 36-40, distillate, by liquid-phase, controlled partial oxidation of the same according to the process disclosed in U. S. Patents Nos. 1,690,768 and 1,690,769 to Arthur W.
  • ptBBA para tertiary butyl benzoic acid
  • Burwell and completely neutralizing the tree acids present in the resulting mixture by treating the latter, at an elevated temperature not substantially higher than 100 C., with a suitable organic amine such for example as diethanolamine,, triethanolamine, mixtures of these amines, morpholine, and the like.
  • a suitable organic amine such for example as diethanolamine,, triethanolamine, mixtures of these amines, morpholine, and the like.
  • the acids content of the oxidate is removed from the latter by saponification and subsequent acidification.
  • Said acids are, in major portion, aliphatic carboxylic acids ranging in carbon chain length from C to C with a mean length of C
  • the acids content may, and usually does, include in minor proportion straight and branched chain aliphatic hydroxy carboxylic acids having substantially the same carbon chain length.
  • the neutralization reaction being exothermic, must be so conducted that the temperature of the reaction mixture does not rise more than a few-e. g., two or three-degrees above 100 C. Control of the rate at which the organic amine is added to the hot mixture affords a suitable mode of control of temperature rise. Also, the pres ence in the mixture, to which the organic amine is being added, of a substantial but minor proportion of water aids i 2,832,742 Patented Apr. 29, 1958 in maintaining the temperature at approximately 100 C. during the neutralization. The presence of water efiects the further advantage that the reaction mixturewhich, in the absence of water, is or may be viscous and which may tend to crystallize on standing at room temperaturethereby is given a desirable fluidity for ease of handling.
  • the resulting completely neutralized reaction mixture is soluble in Water in practically all proportions, and is soluble also in methanol, ethanol, ethylene glycols and other commonly employed alcoholic anti-freeze agents. It can be added directly to the water of the system to be protected; or it may be dissolved in an alcoholic antifreeze agent and added to the water circulating systems in the dissolved form.
  • the additive of the present invention whether added directly or as a solution in anti-freeze--normal1y is used in an amount to yield a concentration of from 0.1 to 1.0% by weight of the system to be protected.
  • oxidized petroleum acids Alox 425 as used above applicant means the mixture of aliphatic carboxylic acids, ranging in carbon chain length between C, and C and having a mean carbon chain length of C derivable from an oxidate of 3640 petroleum distillate.
  • the product, prepared as above described, is completely soluble in water and in commonly employed alcoholic anti-freeze agents.
  • a concentration of 0.1 to 0.1% (a 0.2% concentration being usual, it protects steel, or iron, from the normally corrosive action of water containing a normal amount of dissolved oxygen or air; moreover, it provides residual protection of the metal after the latter has been removed from contact with the inhibited water. It has no significantly detrimental effect on copper, brass, alumi num, lead or solder. It is efiective at from room temperature to at least 160 F., and in water having a pH of from 6 to 10.
  • VARIABLES IN PREPARATION or INHIBITOR Effect of components glycols; and, the amine-neutralized ptBBA per se is a" less etiective corrosion inhibitor at elevated temperatures, besides being expensive.
  • the amine-neutralized, approximately 50-50, mixture of ptBBA and oxidized petroleum acids combines the advantages of full range of solubilities, performance at elevated as well as low temperatures, limited attack on lead, copper and brass, and desirably low cost. Where alcohol solubility is not required, the proportion of ptBBA to petroleum acids may be lowered, e. g., to -80 or to a ratio intermediate these extremes.
  • red oil (oleic acid) has been found to be an operable although not preferred component.
  • a 50 50 blend of red oil and ptBBA when 100% neutralized with diethanolamine was found to be elfective, in water, at concentrations above 0.5 This suggests that other relatively high molecular weight organic acids may have at least limited effectiveness.
  • the neutralization of the mixture of ptBBA and oxidized petroleum acids may be carried out at any temperature between about and 100 C. If the temperature is permitted to rise appreciably above 100 C., amides rather than amine complexes or salts tend to 'be produced, which amides are insoluble or only poorly soluble in water. As to the observance of temperatures substantially below 100 C., it is to be noted that effective inhibitors have been prepared at 25 C., C., C., and C. However, because the temperature rise, due to the exothermicity of the reaction, is difi'icultly controllable when the reaction is started, at lower temperature, it seems preferable to control the temperature during neutralization at about C.
  • the ASTM acid number of the blend of oxidized petroleum acids e. g., Alox 425, and ptBBA is calculated as follows:
  • Products have also been prepared in which only 75 of the theoretical amount of amine has been used. Such products are effective protective agents, butshow mild corrosion of lead, copper and brass.
  • the optimum range of neutralization is 95-103 Complete, or 100% neutralization is preferred. 7
  • a wide range of degress of neutralization is possible to yield products which protect steel.
  • increased attack of non-ferrous metals occurs at less than 100% neutralization, and a loss of clarity of product occurs when an excess of amine is used.
  • the steel panels are tested in solutions of the inhibitor in tap water.
  • panels are tested at a range of solution pH values.
  • HCl is added to adjust the pH (4 or 6 in the tests).
  • Other solutions are adjusted with concentrated NH OH to pH values of 8 and 10.
  • test metals are copper, brass, brass with a /2" diameter solder spot, lead, magnesium, steel and cast iron.
  • the brass rod and test metals are immersed in the test solution at 160 F. and rotated at 500 R. P. M. for two weeks. At the end of that period each metal is cleaned, examined for staining, etc., and then re-weighed. The weight loss per square centimeter of surface is calculated.
  • Residual protection test This test is designed to determine whether steel will be protected after removal from contact with inhibited water. A sand-blasted panel is immersed in the test solution, removed and allowed to drain for one hour. It is then stored in a static humidity cabinet which is essentially a 4. Test results Selected test data are summarized in the following tables, in which Table 1' compares corrosion protection versus degree of neutralization, and Table II compares temperatures at which the product was prepared.
  • pH refers to the pH resulting from dissolving the inhibitor in tap water without addition of H01 or NHAOH.
  • the pH of such solutions is approximately 7.6.
  • a water-soluble corrosion inhibiting composition for mixture derived from an oxidized petroleum fraction said use in aqueous liquid systems, in contact with ferrous and aliphatic carboxylic acids having carbon chain lengths non-ferrous metals, consisting essentially of substantially between C and C and a mean carbon chain length completely neutral diethanolamine salts of about equal of C parts by weight of para tertiary butyl benzoic acid and 3.
  • aliphatic carboxylic acids having carbon chain lengths 4.
  • a liquid coolant composition for use in contact with e c s ted in the file of this patent ferrous and non-ferrous metals characterized in that the UNITED STATES PATENTS same 1s a solution in aqueous medium of from about 0.1% to about 1.0% by weight of a water-soluble corrosion 2:330:524 sPlelds p 1943 inhibiting composition consisting essentially of substan- ,949 Lleber June 27, 1950 tially completely neutral diethanolamine salts of about 2,578,654 Hearne et a1. Dec. 18, 1951 equal parts by weight of para tertiary butyl benzoic acid 2,629,649 Wachter et al. Feb. 24, 1953

Description

CORRGQGN ENEEEBIT R COMPOSITION Clarence A. Weltrnan, Niagara Falls, N. Y., assignor to Aiox Corporation, Niagara Falls, N. Y., a corporation of New York No Drawing. Application June 9, 1954 Serial No. 435,626
4 Claims. (Cl. 252-77) This invention relates to water-soluble corrosion-inhibiting compositions and is more particularly concerned with inhibitors for use primarily in water circulating systems such as automobile radiators, certain industrial heat exchangers, cooling towers and the like.
The requirements of a good water-soluble corrosion inhibitor can be summarized as follows:
(a) It shall protect steel or iron from the normally corrosive action of hard or soft water containing normal amounts of dissolved oxygen or air.
(b) It shall not attack or corrode other metal normal- 1y used in circulating systems, such as copper, brass, aluminum, lead or sloder.
(c) It shall be completely water-soluble.
(d) It is desirable, also, that it besoluble in alcohols (methanol, ethanol) and ethylene glycols in the required concentrations.
(e) It is desirable that the inhibitor provide some residual protection of the metal after it is removed from contact with the inhibited water. Thus, if some water evaporates from a cooling bath or system; the exposed metal should be protected for a short time. Uninhibited water will cause corrosion While in contact with the steel and will accelerate further corrosion as it evaporates.
It has been found that a corrosion inhibiting composition having outstanding properties may be prepared by blending about equal parts of para tertiary butyl benzoic acid, hereinafter referred to as ptBBA, with relatively high molecular weight aliphatic carboxylic acids derived from a petroleum fraction, e. g., from a normally liquid petroleum fraction such, for instance, as 36-40, distillate, by liquid-phase, controlled partial oxidation of the same according to the process disclosed in U. S. Patents Nos. 1,690,768 and 1,690,769 to Arthur W. Burwell, and completely neutralizing the tree acids present in the resulting mixture by treating the latter, at an elevated temperature not substantially higher than 100 C., with a suitable organic amine such for example as diethanolamine,, triethanolamine, mixtures of these amines, morpholine, and the like.
As disclosed in the aforesaid Patents Nos. 1,690,768
and 1,690,769, the acids content of the oxidate is removed from the latter by saponification and subsequent acidification. Said acids are, in major portion, aliphatic carboxylic acids ranging in carbon chain length from C to C with a mean length of C The acids content may, and usually does, include in minor proportion straight and branched chain aliphatic hydroxy carboxylic acids having substantially the same carbon chain length.
The neutralization reaction, being exothermic, must be so conducted that the temperature of the reaction mixture does not rise more than a few-e. g., two or three-degrees above 100 C. Control of the rate at which the organic amine is added to the hot mixture affords a suitable mode of control of temperature rise. Also, the pres ence in the mixture, to which the organic amine is being added, of a substantial but minor proportion of water aids i 2,832,742 Patented Apr. 29, 1958 in maintaining the temperature at approximately 100 C. during the neutralization. The presence of water efiects the further advantage that the reaction mixturewhich, in the absence of water, is or may be viscous and which may tend to crystallize on standing at room temperaturethereby is given a desirable fluidity for ease of handling.
The resulting completely neutralized reaction mixture is soluble in Water in practically all proportions, and is soluble also in methanol, ethanol, ethylene glycols and other commonly employed alcoholic anti-freeze agents. It can be added directly to the water of the system to be protected; or it may be dissolved in an alcoholic antifreeze agent and added to the water circulating systems in the dissolved form. In industrial water circulating systems the additive of the present inventionwhether added directly or as a solution in anti-freeze--normal1y is used in an amount to yield a concentration of from 0.1 to 1.0% by weight of the system to be protected.
SPECIFIC EXAMPLE A typical preparation illustrative of the present invention is prepared as follows, all percentages being by weight:
a. Blend: Alox 37.5% oxidized petroleum acids 425=375 g. 37.5%.ptBBA=375 g.
25.0% water=250 g.
0. Stir until cool (not essential) The final composition is, then, a reaction mixture of:
27.1% Alox 425 27.1% ptBBA 27.7% diethanolamine 18.1% water By the expression oxidized petroleum acids Alox 425 as used above applicant means the mixture of aliphatic carboxylic acids, ranging in carbon chain length between C, and C and having a mean carbon chain length of C derivable from an oxidate of 3640 petroleum distillate.
The product, prepared as above described, is completely soluble in water and in commonly employed alcoholic anti-freeze agents. When dissolved in water in an amount to give a concentration of 0.1 to 0.1% (a 0.2% concentration being usual, it protects steel, or iron, from the normally corrosive action of water containing a normal amount of dissolved oxygen or air; moreover, it provides residual protection of the metal after the latter has been removed from contact with the inhibited water. It has no significantly detrimental effect on copper, brass, alumi num, lead or solder. It is efiective at from room temperature to at least 160 F., and in water having a pH of from 6 to 10.
VARIABLES IN PREPARATION or INHIBITOR 1. Effect of components glycols; and, the amine-neutralized ptBBA per se is a" less etiective corrosion inhibitor at elevated temperatures, besides being expensive. The amine-neutralized, approximately 50-50, mixture of ptBBA and oxidized petroleum acids combines the advantages of full range of solubilities, performance at elevated as well as low temperatures, limited attack on lead, copper and brass, and desirably low cost. Where alcohol solubility is not required, the proportion of ptBBA to petroleum acids may be lowered, e. g., to -80 or to a ratio intermediate these extremes.
In lieu of the oxidized petroleum acids referred to above red oil (oleic acid) has been found to be an operable although not preferred component. A 50 50 blend of red oil and ptBBA when 100% neutralized with diethanolamine was found to be elfective, in water, at concentrations above 0.5 This suggests that other relatively high molecular weight organic acids may have at least limited effectiveness.
It does not appear that the ptBBA can be replaced with Worthwhile results; Thus, benzoic acid substituted for the ptBBA yielded a greatly inferior .product.
As was suggested above, either triethanolamine or morpholine can be substituted for diethanolamine with fair effectiveness.
2. Efiects of temperature The neutralization of the mixture of ptBBA and oxidized petroleum acids may be carried out at any temperature between about and 100 C. If the temperature is permitted to rise appreciably above 100 C., amides rather than amine complexes or salts tend to 'be produced, which amides are insoluble or only poorly soluble in water. As to the observance of temperatures substantially below 100 C., it is to be noted that effective inhibitors have been prepared at 25 C., C., C., and C. However, because the temperature rise, due to the exothermicity of the reaction, is difi'icultly controllable when the reaction is started, at lower temperature, it seems preferable to control the temperature during neutralization at about C.
3. Effect of degree of neutralization The degree of neutralization of the acids is critical in terms of meeting all of the requirements set forth for a good inhibitor.
The amount of amine to use for complete neutralization (called 100%) is as follows:
The ASTM acid number of the blend of oxidized petroleum acids, e. g., Alox 425, and ptBBA is calculated as follows:
Acid No. ptBBA=3l5 (calculated from molecular weight or determined) Acid No. Alox 425=l80 (determined) Therefore, a 50- 50 blend has an acid number of 50% of 3l5=l57.5 50% of 180: 90.0'
Combined acid No.=247.5
When 1000 g. of this is neutralized directly, the calculation for diethanolamine is:
Mol. wt. KOH= 56.1 Mol. wt. DEAL-105.1 x=464 g. DEA per 1000 g. mixed acids calculated from any other combination of ptBBA and ill Te's't's have been performed in which as much as 13% excess of diethanolamine has been added. The resulting product is hazy and tends to separate a slight clear layer. The product containing an excess of amine is essentially as efiective a corrosion inhibitor as the normal product, but is wasteful of amine and yields a. physically unstable product.
Products have also been prepared in which only 75 of the theoretical amount of amine has been used. Such products are effective protective agents, butshow mild corrosion of lead, copper and brass.
Thus, the optimum range of neutralization is 95-103 Complete, or 100% neutralization is preferred. 7 To repeat, a wide range of degress of neutralization is possible to yield products which protect steel. However, increased attack of non-ferrous metals occurs at less than 100% neutralization, and a loss of clarity of product occurs when an excess of amine is used.
TEST PROCEDURES AND RESULTS 1. Immersion test-Corrosion of steel This is a static test in which a 2" x 4" cold rolled steel panel, with a sand-blasted surface, is immersedih the. test solution. The panel is examined daily for evidence of rusting, staining or other visible signs of corrosion.
The steel panels are tested in solutions of the inhibitor in tap water. In addition panels are tested at a range of solution pH values. Thus, to'the solution of inhibitor in tap water, HCl is added to adjust the pH (4 or 6 in the tests). Other solutions are adjusted with concentrated NH OH to pH values of 8 and 10.
In addition to static tests at pH 4, 6, 7.6 (pH of inhibi tor in tap water), 8, 10 at temperature (77 F.), a'similar series is run, at F. Thus protection tests were run a at varying pH and at two temperatures.
2. Rotating metals test This test Wasdesigned to determine the eifect of moving water over various metals. It is hoped that this test will simulate actual conditions in a circulating system.
One inch squares of metal with holes drilled through their centers are weighed and then suspended on a brass rod. 'Each metal square is separated from the others by a As'fthick brass washer. The test metals are copper, brass, brass with a /2" diameter solder spot, lead, magnesium, steel and cast iron.
The brass rod and test metals are immersed in the test solution at 160 F. and rotated at 500 R. P. M. for two weeks. At the end of that period each metal is cleaned, examined for staining, etc., and then re-weighed. The weight loss per square centimeter of surface is calculated.
3. Residual protection test This test is designed to determine whether steel will be protected after removal from contact with inhibited water. A sand-blasted panel is immersed in the test solution, removed and allowed to drain for one hour. It is then stored in a static humidity cabinet which is essentially a 4. Test results Selected test data are summarized in the following tables, in which Table 1' compares corrosion protection versus degree of neutralization, and Table II compares temperatures at which the product was prepared.
TABLE I {Corrosion protection versus degree of neutralization] Composition Corrosion tests (Days to fail) React Percent of Percent Std. Residual Code Designation Temp, theory additive pH,* Protec- Percent Percent Percent C. Ncutralized in Water R.- l. Std. pH 4 pH 6, pH 8, pH 10, tion ptBBA 425 Water pH,* @160" 160 F. 160 F. 160 F. (Days) OP-l-lll 37. 5 37. 5 25. 100 13 XS OP-l-lll 37. 5 37. 5 25. 0 100 75 999992-9999999999 DIN l-OoOlmMHOmwMl-Q oo coon-cocoon Standard pH refers to the pH resulting from dissolving the inhibitor in tap water without addition of H01 or NHAOH. The pH of such solutions is approximately 7.6.
TABLE II [Preparation temperature versus corrosion protection] Percent Corrosion tests (Days to Fail) Code of theory React Percent Std. %H,
Designation Neutrai- Temp., inWater R ized 0. Std. pH, p114, pH 6, pH 3, pH 10, 100 F. 160 F. 160 F. 160 F. 100 F.
3'22 1 01 00+ 17 1 1 24+ 0. 30 60+ 30+ 0.05 1 2 0r-1-119A-- 100 so 0. 10 60+ 4 0.20 60+ 0.05 1 OP-l-ilQB.-. 100 0. 10 60+ 4 Iclaim: and a high molecular weight aliphatic carboxylic acids 1. A water-soluble corrosion inhibiting composition for mixture derived from an oxidized petroleum fraction, said use in aqueous liquid systems, in contact with ferrous and aliphatic carboxylic acids having carbon chain lengths non-ferrous metals, consisting essentially of substantially between C and C and a mean carbon chain length completely neutral diethanolamine salts of about equal of C parts by weight of para tertiary butyl benzoic acid and 3. The composition defined in claim 1, in which the oxa high molecular weight aliphatic carboxylic acids mixidized petroleum fraction is an oxidized 36-40 distillate ture derived from an oxidized petroleum fraction, said of petroleum origin.
aliphatic carboxylic acids having carbon chain lengths 4. The coolant composition defined in claim 2 in which between G; and C and a mean carbon chain length said medium is a solution of alcohol in water. Of C14.
2. A liquid coolant composition for use in contact with e c s ted in the file of this patent ferrous and non-ferrous metals, characterized in that the UNITED STATES PATENTS same 1s a solution in aqueous medium of from about 0.1% to about 1.0% by weight of a water-soluble corrosion 2:330:524 sPlelds p 1943 inhibiting composition consisting essentially of substan- ,949 Lleber June 27, 1950 tially completely neutral diethanolamine salts of about 2,578,654 Hearne et a1. Dec. 18, 1951 equal parts by weight of para tertiary butyl benzoic acid 2,629,649 Wachter et al. Feb. 24, 1953

Claims (1)

1. A WATER-SOLUBLE CORROSION INHIBITING COMPOSITION FOR USE IN AQUEOUS LIQUID SYSTEMS, IN CONTACT WITH FERROUS AND NON-FERROUS METALS, CONSISTING ESSENTIALLY OF SUBSTANTIALLY COMPLETELY NEUTRAL DIETHANOLAMINE SALTS OF ABOUT EQUAL PARTS BY WEIGHT OF PARA TERTIARY BUTYL BENZOIC ACID AND A HIGH MOLECULAR WEIGHT ALIPHATIC CARBOXYLIC ACIDS MIXTURE DERIVED FROM AN OXIDIZED PETROLEUM FRACTION, SAID ALIPHATIC CARBOXYLIC ACIDS HAVING CARBON CHAIN LENGTHS BETWEEN C7 AND C18 AND A MEAN CARBON CHAIN LENGTH OF C14.
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3425954A (en) * 1966-01-24 1969-02-04 Cromwell Paper Co Four component multipurpose corrosion inhibitor
JPS5029440A (en) * 1974-04-22 1975-03-25
US3897349A (en) * 1973-05-29 1975-07-29 Exxon Research Engineering Co Anti-rust additive composition
FR2346465A1 (en) * 1976-04-02 1977-10-28 Parker Ste Continentale ANTI-CORROSION AGENT FOR METAL SURFACES
EP0126069A1 (en) * 1982-11-22 1984-11-28 Ford Motor Co Coatings comprising alkanolamine-carboxylic acid salts for friction material.
EP0251480A1 (en) * 1986-06-30 1988-01-07 S.A. Texaco Belgium N.V. Corrosion-inhibited antifreeze/coolant composition
US4759864A (en) * 1987-09-04 1988-07-26 Texaco Inc. & S.A. Texaco Petro, N.V. Corrosion-inhibited antifreeze formulation
US5741436A (en) * 1995-12-05 1998-04-21 Prestone Products Corp. Antifreeze concentrates and compositions comprising neodecanoic acid corrosion inhibitors

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2330524A (en) * 1941-06-16 1943-09-28 Alox Corp Corrosion inhibitor
US2512949A (en) * 1945-12-22 1950-06-27 Nox Rust Chemical Corp Corrosion inhibitor for metals
US2578654A (en) * 1950-01-28 1951-12-18 Shell Dev Preparation of tertiary-alkyl-substituted benzene carboxylic acids
US2629649A (en) * 1949-10-31 1953-02-24 Shell Dev Vapor-phase corrosion inhibitor

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2330524A (en) * 1941-06-16 1943-09-28 Alox Corp Corrosion inhibitor
US2512949A (en) * 1945-12-22 1950-06-27 Nox Rust Chemical Corp Corrosion inhibitor for metals
US2629649A (en) * 1949-10-31 1953-02-24 Shell Dev Vapor-phase corrosion inhibitor
US2578654A (en) * 1950-01-28 1951-12-18 Shell Dev Preparation of tertiary-alkyl-substituted benzene carboxylic acids

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3425954A (en) * 1966-01-24 1969-02-04 Cromwell Paper Co Four component multipurpose corrosion inhibitor
US3897349A (en) * 1973-05-29 1975-07-29 Exxon Research Engineering Co Anti-rust additive composition
JPS5029440A (en) * 1974-04-22 1975-03-25
JPS5910996B2 (en) * 1974-04-22 1984-03-13 株式会社ネオス anti-rust
FR2346465A1 (en) * 1976-04-02 1977-10-28 Parker Ste Continentale ANTI-CORROSION AGENT FOR METAL SURFACES
EP0126069A4 (en) * 1982-11-22 1986-11-26 Ford Motor Co Coatings comprising alkanolamine-carboxylic acid salts for friction material.
EP0126069A1 (en) * 1982-11-22 1984-11-28 Ford Motor Co Coatings comprising alkanolamine-carboxylic acid salts for friction material.
EP0251480A1 (en) * 1986-06-30 1988-01-07 S.A. Texaco Belgium N.V. Corrosion-inhibited antifreeze/coolant composition
JPS6326388A (en) * 1986-06-30 1988-02-03 ソシエテ・アノニム・テキサコ・ベルジャン・エヌ・ヴィ Corrosion suppressing antifreeze liquid/cooling composition
US4851145A (en) * 1986-06-30 1989-07-25 S.A. Texaco Petroleum Nv Corrosion-inhibited antifreeze/coolant composition
JPH0442477B2 (en) * 1986-06-30 1992-07-13 Texaco Belgium Nv Sa
US4759864A (en) * 1987-09-04 1988-07-26 Texaco Inc. & S.A. Texaco Petro, N.V. Corrosion-inhibited antifreeze formulation
US5741436A (en) * 1995-12-05 1998-04-21 Prestone Products Corp. Antifreeze concentrates and compositions comprising neodecanoic acid corrosion inhibitors

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