US2905644A - Anticorrosion agent - Google Patents

Anticorrosion agent Download PDF

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Publication number
US2905644A
US2905644A US599681A US59968156A US2905644A US 2905644 A US2905644 A US 2905644A US 599681 A US599681 A US 599681A US 59968156 A US59968156 A US 59968156A US 2905644 A US2905644 A US 2905644A
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composition
corrosion
oxazoline
test
anticorrosion agent
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US599681A
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George N Butter
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Commercial Solvents Corp
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Commercial Solvents 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
    • C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom

Definitions

  • My invention relates to corrosion inhibiting compositions and more particularly it is concerned with an anticorrosion composition containing as an essential active ingredient a substituted oxazoline having the formula where R is one of the group consisting of C1'7H35 and C1'7H33, and to a process for preventing corrosion therewith.
  • ferrous used in this application is to be interpreted as iron containing and does not mean iron in the bivalent state.
  • My new compositions utilize as the essential active ingredient 2 (8-heptadecenyl) 4,4 bis(hydroxymethyl)-2-oxazoline or 2-heptadecyl-4,4-bis(hydroxymethyl)- 2-oxazoline dissolved in an oil base.
  • the oxazolines employed in my invention are conveniently produced by reacting tris(hydroxymethyl)amino methane with oleic or stearic acid in approximately equimolar quantities. The temperature employed in carrying out the reaction is preferably maintained between 160 and 185 C. The initial stage of this reaction yields an amide corresponding to the desired product, after which the temperature is increased to approximately 215 C., or higher, thereby resulting in the thermal elimination of one equivalent of Water to give the desired oxazoline.
  • the oxazolines can be produced according to the process described in US. Patent 2,402,791.
  • I can employ either crude or refined mineral or vegetable oils as the inert base of my corrosion inhibiting composition.
  • I can incorporate from 0.04 to 10% by weight of the active ingredient in the inert oil base by any convenient means.
  • EXAMPLE 1 A series of static water drop tests were conducted employing a procedure described by Baker, Jones, and Zisman in Industrial and Engineering Chemistry, vol. 41, pages 137-144 (1949). Generally, the test consisted of submerging a test specimen; prepared by depressing the center portion of a triangular piece of inch S.A.E. 1020 cold rolled steel, polishing the depression to a mirror finish, andbending the corners of the triangle down to form legs; in a beaker containing the composition of my invention and injecting 0.2 ml. of water into the depres sion. The containers were covered and placed in a constant temperature oven at 160 F. and visually'inspected at intervals.
  • EXAMPLE II The results of a test utilizing a procedure described in Corrosion, vol. 11, No. 3, pages 143t-146t (1955), demonstrate the efficacy of my new composition in the presence of hydrosulfuric acid.
  • the test described is a static oil and water test wherein mild steel coupons are contacted with a brine containing hydrosulfuric acid.
  • the weight loss of a coupon coated with my new composition is compared with the weight loss of a coupon coated with the inert oil base of my new composition.
  • a corrosion inhibiting composition comprising a mineral oil solvent in a major amount, based on the weight of the composition, and from about 0.04% to 10% of a substituted oxazoline having the structural formula where R is a radical selected from the group consisting Of C17H35 and C17H33.
  • a corrosion inhibiting composition comprising a vegetable oil solvent in a major amount based on the weight of the composition, and from about 0.04% to 10% of a substituted oxazoline having the structural formula where R is a radical selected from the group consisting of 17 s5 n CHI-I332 v t t.
  • a process for the prevention of corrosion to ferrous metal surfaces which comprises applying to the ferrous metal surfaces a composition comprising a mineral oil containing from 0.04% to 10% of a substituted 'oxazoline having the structural formula OH H (EH, H-l-G-CHaOH where R is a radical selected from the group consisting of C17H35 and C17H33- 4.
  • a process for the prevention of corrosion to ferrous A metal surfaces which comprises applying to the ferrous metal surfaces 21 Vegetable oil containing from 0.04% to 10% of a substituted oxazoline having the structural formula where R is a radical selected from the group consisting Of C I I 5 and C17H3 References Cited in the.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)

Description

United States Patent ANTICORROSION AGENT George N. Butter, Terre Hante, Ind., assignor to Commercial Solvents Corporation, Terre Haute, Ind., a corporation of Maryland No Drawing. Application July 24, 1956 Serial No. 599,681
4 Elaims. (Cl. 252-392) My invention relates to corrosion inhibiting compositions and more particularly it is concerned with an anticorrosion composition containing as an essential active ingredient a substituted oxazoline having the formula where R is one of the group consisting of C1'7H35 and C1'7H33, and to a process for preventing corrosion therewith.
Many difierent agents have been discovered which are efiective corrosion inhibitors under limited conditions. However, since no acceptable theory has been advanced to delineate the mode of operation of corrosion inhibitors, extensive experimentation is required to develop inhibitors having special properties which can be utilized for a particular purpose.
I have now discovered that certain oxazolines impart to ferrous metals resistance to attack by a variety of corrosion agents in both acidic and basic solutions.
The word ferrous used in this application is to be interpreted as iron containing and does not mean iron in the bivalent state.
My new compositions utilize as the essential active ingredient 2 (8-heptadecenyl) 4,4 bis(hydroxymethyl)-2-oxazoline or 2-heptadecyl-4,4-bis(hydroxymethyl)- 2-oxazoline dissolved in an oil base. The oxazolines employed in my invention are conveniently produced by reacting tris(hydroxymethyl)amino methane with oleic or stearic acid in approximately equimolar quantities. The temperature employed in carrying out the reaction is preferably maintained between 160 and 185 C. The initial stage of this reaction yields an amide corresponding to the desired product, after which the temperature is increased to approximately 215 C., or higher, thereby resulting in the thermal elimination of one equivalent of Water to give the desired oxazoline. Generally, the oxazolines can be produced according to the process described in US. Patent 2,402,791.
I have found that I can employ either crude or refined mineral or vegetable oils as the inert base of my corrosion inhibiting composition. In preparing my new composition, I can incorporate from 0.04 to 10% by weight of the active ingredient in the inert oil base by any convenient means. I prefer to employ about 1% by weight of the oxazoline in my new composition.
To illustrate the effectiveness of my invention, the following examples are set out; however, I do not intend to be limited to the particular materials, procedures or amounts set forth but rather I intend for all equivalents obvious to those skilled in the art to be included within the scope of my specification and claims.
EXAMPLE 1 A series of static water drop tests were conducted employing a procedure described by Baker, Jones, and Zisman in Industrial and Engineering Chemistry, vol. 41, pages 137-144 (1949). Generally, the test consisted of submerging a test specimen; prepared by depressing the center portion of a triangular piece of inch S.A.E. 1020 cold rolled steel, polishing the depression to a mirror finish, andbending the corners of the triangle down to form legs; in a beaker containing the composition of my invention and injecting 0.2 ml. of water into the depres sion. The containers were covered and placed in a constant temperature oven at 160 F. and visually'inspected at intervals.
The following table sets out the results of the abovedescribed tests showing the condition of the test specimens while submerged in compositions of my invention containing varying amounts of the active agents at the end of various time periods up to 351 hours when the ATest area of disk bright.
B-Test area bright except for 1 small rust spot. This failure may result from an imperfect disk.
C-Test area of disk completely rusted.
EXAMPLE II The results of a test utilizing a procedure described in Corrosion, vol. 11, No. 3, pages 143t-146t (1955), demonstrate the efficacy of my new composition in the presence of hydrosulfuric acid. The test described is a static oil and water test wherein mild steel coupons are contacted with a brine containing hydrosulfuric acid. The weight loss of a coupon coated with my new composition is compared with the weight loss of a coupon coated with the inert oil base of my new composition.
The per cent protection effected by use of my compositions is set out below.
Table II Concentration Percent of inhibprotec- Compound itor in tion in mineral test oil, p.p.m.
2- (8-heptadecenyl) -4,4-bis (hydroxymethyD-Z-oxaz ine 96.6 2- heptadecyl-4,4-bis (hydroxymethyl)-2-0xazoline. 100 97. 2
Now having described my invention, what I claim is: 1. A corrosion inhibiting composition comprising a mineral oil solvent in a major amount, based on the weight of the composition, and from about 0.04% to 10% of a substituted oxazoline having the structural formula where R is a radical selected from the group consisting Of C17H35 and C17H33.
2. A corrosion inhibiting composition comprising a vegetable oil solvent in a major amount based on the weight of the composition, and from about 0.04% to 10% of a substituted oxazoline having the structural formula where R is a radical selected from the group consisting of 17 s5 n CHI-I332 v t t.
3. A process for the prevention of corrosion to ferrous metal surfaces which comprises applying to the ferrous metal surfaces a composition comprising a mineral oil containing from 0.04% to 10% of a substituted 'oxazoline having the structural formula OH H (EH, H-l-G-CHaOH where R is a radical selected from the group consisting of C17H35 and C17H33- 4. A process for the prevention of corrosion to ferrous A metal surfaces which comprises applying to the ferrous metal surfaces 21 Vegetable oil containing from 0.04% to 10% of a substituted oxazoline having the structural formula where R is a radical selected from the group consisting Of C I I 5 and C17H3 References Cited in the. file of this patent UNITED STATES PATENTS 2,402,791 Wampner June 25, 1946 2,566,793 Davis et a1 Sept. 4, 1951 2,652,363 Woods et al Sept. 15, 1953 2,737,491 Hughes et a1. Mar. 6, 1956

Claims (1)

1. A CORROSION INHIBITING COMPOSITION COMPRISING A MINERAL OIL SOLVENT IN A MAJOR AMOUNT, BASED ON THE WEIGHT OF THE COMPOSITION AND FROM ABOUT 0.04% TO 10% OF A SUBSTITUTED OXAZOLINE HAVING THE STRUCTURAL FORMULA
US599681A 1956-07-24 1956-07-24 Anticorrosion agent Expired - Lifetime US2905644A (en)

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Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2948597A (en) * 1958-12-30 1960-08-09 Standard Oil Co Novel boron compounds and gasoline containing the same
US2987519A (en) * 1959-11-09 1961-06-06 Sterling Drug Inc 3-alkyl-4, 4-bis (hydroxymethyl)-oxazolidines and process for the preparation thereof
US3152187A (en) * 1960-04-13 1964-10-06 Continental Oil Co Condensation product of unsaturated diols and polyalkylene polyamines and method of preparation thereof
US3203935A (en) * 1962-05-07 1965-08-31 O Brien Corp Polymeric compositions of terpolymers reacted with aminohydroxy compounds
US3208981A (en) * 1962-05-07 1965-09-28 O Brien Corp Process for preparing terpolymers containing oxazoline units
US3217802A (en) * 1961-03-16 1965-11-16 Magnet Cove Barium Corp Freeing stuck pipe
US3423349A (en) * 1966-06-07 1969-01-21 Commercial Solvents Corp Oxazoline water repellant composition
US3438943A (en) * 1966-08-17 1969-04-15 Brien Corp O Polyesters from oxazoline polyols
US4035309A (en) * 1975-03-24 1977-07-12 Exxon Research And Engineering Company Metal-containing oxazoline additives and lubricating oils containing said additives
US4102798A (en) * 1974-03-27 1978-07-25 Exxon Research & Engineering Co. Oxazoline additives useful in oleaginous compositions
US4113639A (en) * 1976-11-11 1978-09-12 Exxon Research & Engineering Co. Lubricating oil composition containing a dispersing-varnish inhibiting combination of an oxazoline compound and an acyl nitrogen compound
US4153566A (en) * 1974-03-27 1979-05-08 Exxon Research & Engineering Co. Oxazoline additives useful in oleaginous compositions
US4157243A (en) * 1974-12-06 1979-06-05 Exxon Research & Engineering Co. Additive useful in oleaginous compositions
US4169836A (en) * 1974-03-27 1979-10-02 Exxon Research & Engineering Co. Oxazoline containing additive
US4174322A (en) * 1976-09-24 1979-11-13 Exxon Research & Engineering Co. Thiobis(oxazolines)
US4253973A (en) * 1979-11-20 1981-03-03 Mobil Oil Corporation Phosphorus-containing compounds and lubricants containing same
US4255271A (en) * 1979-11-20 1981-03-10 Mobil Oil Corporation Phosphorus-containing compounds and lubricants containing same
US4277354A (en) * 1975-05-01 1981-07-07 Exxon Research & Engineering Co. Oil-soluble hydrocarbyl substituted 1-aza-3,7-dioxabicyclo[3.3.0]oct-5-yl methyl alcohols, as additives for functional fluids
US4374032A (en) * 1980-03-28 1983-02-15 Mobil Oil Corporation Lubricant composition containing borated oxazoline friction reducer
US4702854A (en) * 1983-05-02 1987-10-27 The Dow Chemical Company Water-based hydraulic fluids comprising poly-oxazines or poly-oxazolines
US4780227A (en) * 1984-08-22 1988-10-25 Mobil Oil Corporation Grease composition containing borated alkoxylated alcohols
US4828734A (en) * 1985-08-27 1989-05-09 Mobil Oil Corporation Grease compositions containing borated oxazoline compounds and hydroxy-containing soap thickeners
US5084194A (en) * 1984-03-07 1992-01-28 Mobil Oil Corporation Grease composition
US5334329A (en) * 1988-10-07 1994-08-02 The Lubrizol Corporation Lubricant and functional fluid compositions exhibiting improved demulsibility
EP2746370A1 (en) * 2012-12-21 2014-06-25 Afton Chemical Corporation Friction modifiers for lubricating oils
US9249371B2 (en) 2012-12-21 2016-02-02 Afton Chemical Corporation Additive compositions with a friction modifier and a dispersant
US9279094B2 (en) 2012-12-21 2016-03-08 Afton Chemical Corporation Friction modifiers for use in lubricating oil compositions
US9499763B2 (en) 2012-12-21 2016-11-22 Afton Chemical Corporation Additive compositions with plural friction modifiers
US9499761B2 (en) 2012-12-21 2016-11-22 Afton Chemical Corporation Additive compositions with a friction modifier and a metal dialkyl dithio phosphate salt
US9499762B2 (en) 2012-12-21 2016-11-22 Afton Chemical Corporation Additive compositions with a friction modifier and a detergent

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2402791A (en) * 1944-05-11 1946-06-25 Commercial Solvents Corp Reaction product of oxazolines
US2566793A (en) * 1940-04-05 1951-09-04 Shell Dev Grease compositions
US2652363A (en) * 1951-12-29 1953-09-15 Shell Dev Grease compositions
US2737491A (en) * 1952-06-13 1956-03-06 Cities Service Res & Dev Co Method of inhibiting corrosion of metals

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2566793A (en) * 1940-04-05 1951-09-04 Shell Dev Grease compositions
US2402791A (en) * 1944-05-11 1946-06-25 Commercial Solvents Corp Reaction product of oxazolines
US2652363A (en) * 1951-12-29 1953-09-15 Shell Dev Grease compositions
US2737491A (en) * 1952-06-13 1956-03-06 Cities Service Res & Dev Co Method of inhibiting corrosion of metals

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2948597A (en) * 1958-12-30 1960-08-09 Standard Oil Co Novel boron compounds and gasoline containing the same
US2987519A (en) * 1959-11-09 1961-06-06 Sterling Drug Inc 3-alkyl-4, 4-bis (hydroxymethyl)-oxazolidines and process for the preparation thereof
US3152187A (en) * 1960-04-13 1964-10-06 Continental Oil Co Condensation product of unsaturated diols and polyalkylene polyamines and method of preparation thereof
US3217802A (en) * 1961-03-16 1965-11-16 Magnet Cove Barium Corp Freeing stuck pipe
US3203935A (en) * 1962-05-07 1965-08-31 O Brien Corp Polymeric compositions of terpolymers reacted with aminohydroxy compounds
US3208981A (en) * 1962-05-07 1965-09-28 O Brien Corp Process for preparing terpolymers containing oxazoline units
US3423349A (en) * 1966-06-07 1969-01-21 Commercial Solvents Corp Oxazoline water repellant composition
US3438943A (en) * 1966-08-17 1969-04-15 Brien Corp O Polyesters from oxazoline polyols
US4153566A (en) * 1974-03-27 1979-05-08 Exxon Research & Engineering Co. Oxazoline additives useful in oleaginous compositions
US4169836A (en) * 1974-03-27 1979-10-02 Exxon Research & Engineering Co. Oxazoline containing additive
US4102798A (en) * 1974-03-27 1978-07-25 Exxon Research & Engineering Co. Oxazoline additives useful in oleaginous compositions
US4157243A (en) * 1974-12-06 1979-06-05 Exxon Research & Engineering Co. Additive useful in oleaginous compositions
US4035309A (en) * 1975-03-24 1977-07-12 Exxon Research And Engineering Company Metal-containing oxazoline additives and lubricating oils containing said additives
US4277354A (en) * 1975-05-01 1981-07-07 Exxon Research & Engineering Co. Oil-soluble hydrocarbyl substituted 1-aza-3,7-dioxabicyclo[3.3.0]oct-5-yl methyl alcohols, as additives for functional fluids
US4174322A (en) * 1976-09-24 1979-11-13 Exxon Research & Engineering Co. Thiobis(oxazolines)
US4113639A (en) * 1976-11-11 1978-09-12 Exxon Research & Engineering Co. Lubricating oil composition containing a dispersing-varnish inhibiting combination of an oxazoline compound and an acyl nitrogen compound
US4255271A (en) * 1979-11-20 1981-03-10 Mobil Oil Corporation Phosphorus-containing compounds and lubricants containing same
US4253973A (en) * 1979-11-20 1981-03-03 Mobil Oil Corporation Phosphorus-containing compounds and lubricants containing same
US4374032A (en) * 1980-03-28 1983-02-15 Mobil Oil Corporation Lubricant composition containing borated oxazoline friction reducer
US4702854A (en) * 1983-05-02 1987-10-27 The Dow Chemical Company Water-based hydraulic fluids comprising poly-oxazines or poly-oxazolines
US5084194A (en) * 1984-03-07 1992-01-28 Mobil Oil Corporation Grease composition
US4780227A (en) * 1984-08-22 1988-10-25 Mobil Oil Corporation Grease composition containing borated alkoxylated alcohols
US4828734A (en) * 1985-08-27 1989-05-09 Mobil Oil Corporation Grease compositions containing borated oxazoline compounds and hydroxy-containing soap thickeners
US5334329A (en) * 1988-10-07 1994-08-02 The Lubrizol Corporation Lubricant and functional fluid compositions exhibiting improved demulsibility
EP2746370A1 (en) * 2012-12-21 2014-06-25 Afton Chemical Corporation Friction modifiers for lubricating oils
US9249371B2 (en) 2012-12-21 2016-02-02 Afton Chemical Corporation Additive compositions with a friction modifier and a dispersant
US9279094B2 (en) 2012-12-21 2016-03-08 Afton Chemical Corporation Friction modifiers for use in lubricating oil compositions
US9499763B2 (en) 2012-12-21 2016-11-22 Afton Chemical Corporation Additive compositions with plural friction modifiers
US9499761B2 (en) 2012-12-21 2016-11-22 Afton Chemical Corporation Additive compositions with a friction modifier and a metal dialkyl dithio phosphate salt
US9499762B2 (en) 2012-12-21 2016-11-22 Afton Chemical Corporation Additive compositions with a friction modifier and a detergent
US9499764B2 (en) 2012-12-21 2016-11-22 Afton Chemical Corporation Additive compositions with a friction modifier and a dispersant
US9550955B2 (en) 2012-12-21 2017-01-24 Afton Chemical Corporation Friction modifiers for lubricating oils

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