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Publication numberUS2905644 A
Publication typeGrant
Publication dateSep 22, 1959
Filing dateJul 24, 1956
Priority dateJul 24, 1956
Publication numberUS 2905644 A, US 2905644A, US-A-2905644, US2905644 A, US2905644A
InventorsButter George N
Original AssigneeCommercial Solvents Corp
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Anticorrosion agent
US 2905644 A
Abstract  available in
Previous page
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Claims  available in
Description  (OCR text may contain errors)

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

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2402791 *May 11, 1944Jun 25, 1946Commercial Solvents CorpReaction product of oxazolines
US2566793 *Jul 5, 1949Sep 4, 1951Shell DevGrease compositions
US2652363 *Dec 29, 1951Sep 15, 1953Shell DevGrease compositions
US2737491 *Jun 13, 1952Mar 6, 1956Cities Service Res & Dev CoMethod of inhibiting corrosion of metals
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2948597 *Dec 30, 1958Aug 9, 1960Standard Oil CoNovel boron compounds and gasoline containing the same
US2987519 *Nov 9, 1959Jun 6, 1961Sterling Drug Inc3-alkyl-4, 4-bis (hydroxymethyl)-oxazolidines and process for the preparation thereof
US3152187 *Apr 13, 1960Oct 6, 1964Continental Oil CoCondensation product of unsaturated diols and polyalkylene polyamines and method of preparation thereof
US3203935 *May 7, 1962Aug 31, 1965O Brien CorpPolymeric compositions of terpolymers reacted with aminohydroxy compounds
US3208981 *May 7, 1962Sep 28, 1965O Brien CorpProcess for preparing terpolymers containing oxazoline units
US3217802 *Mar 16, 1961Nov 16, 1965Magnet Cove Barium CorpFreeing stuck pipe
US3423349 *Jun 7, 1966Jan 21, 1969Commercial Solvents CorpOxazoline water repellant composition
US3438943 *Aug 17, 1966Apr 15, 1969Brien Corp OPolyesters from oxazoline polyols
US4035309 *Mar 24, 1975Jul 12, 1977Exxon Research And Engineering CompanyMetal-containing oxazoline additives and lubricating oils containing said additives
US4102798 *Jul 27, 1976Jul 25, 1978Exxon Research & Engineering Co.Oxazoline additives useful in oleaginous compositions
US4113639 *Nov 11, 1976Sep 12, 1978Exxon Research & Engineering Co.Lubricating oil composition containing a dispersing-varnish inhibiting combination of an oxazoline compound and an acyl nitrogen compound
US4153566 *Jul 30, 1976May 8, 1979Exxon Research & Engineering Co.Oxazoline additives useful in oleaginous compositions
US4157243 *Jun 19, 1978Jun 5, 1979Exxon Research & Engineering Co.Additive useful in oleaginous compositions
US4169836 *Jul 5, 1977Oct 2, 1979Exxon Research & Engineering Co.Oxazoline containing additive
US4174322 *Jul 20, 1977Nov 13, 1979Exxon Research & Engineering Co.Thiobis(oxazolines)
US4253973 *Nov 20, 1979Mar 3, 1981Mobil Oil CorporationPhosphorus-containing compounds and lubricants containing same
US4255271 *Nov 20, 1979Mar 10, 1981Mobil Oil CorporationPhosphorus-containing compounds and lubricants containing same
US4277354 *Jan 7, 1980Jul 7, 1981Exxon 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
US4374032 *Mar 28, 1980Feb 15, 1983Mobil Oil CorporationLubricant composition containing borated oxazoline friction reducer
US4702854 *May 2, 1983Oct 27, 1987The Dow Chemical CompanyWater-based hydraulic fluids comprising poly-oxazines or poly-oxazolines
US4780227 *May 4, 1987Oct 25, 1988Mobil Oil CorporationGrease composition containing borated alkoxylated alcohols
US4828734 *May 14, 1987May 9, 1989Mobil Oil CorporationGrease compositions containing borated oxazoline compounds and hydroxy-containing soap thickeners
US5084194 *Nov 14, 1990Jan 28, 1992Mobil Oil CorporationGrease composition
US5334329 *Oct 7, 1988Aug 2, 1994The Lubrizol CorporationLubricant and functional fluid compositions exhibiting improved demulsibility
EP2746370A1 *Dec 20, 2013Jun 25, 2014Afton Chemical CorporationFriction modifiers for lubricating oils
U.S. Classification252/392, 548/239, 508/278
International ClassificationC23F11/10, C23F11/14
Cooperative ClassificationC23F11/149
European ClassificationC23F11/14H