US2905644A - Anticorrosion agent - Google Patents
Anticorrosion agent Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- composition
- corrosion
- oxazoline
- test
- anticorrosion agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims description 19
- 238000005260 corrosion Methods 0.000 claims description 12
- 230000007797 corrosion Effects 0.000 claims description 12
- 150000002918 oxazolines Chemical class 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 239000002480 mineral oil Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 235000010446 mineral oil Nutrition 0.000 claims description 3
- 238000000034 method Methods 0.000 description 7
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 ferrous metals Chemical class 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- PMKWOEMFPKQBRI-UHFFFAOYSA-N [2-heptadec-8-enyl-4-(hydroxymethyl)-5h-1,3-oxazol-4-yl]methanol Chemical compound CCCCCCCCC=CCCCCCCCC1=NC(CO)(CO)CO1 PMKWOEMFPKQBRI-UHFFFAOYSA-N 0.000 description 1
- FFJWPXULECNYBC-UHFFFAOYSA-N [2-heptadecyl-4-(hydroxymethyl)-5h-1,3-oxazol-4-yl]methanol Chemical compound CCCCCCCCCCCCCCCCCC1=NC(CO)(CO)CO1 FFJWPXULECNYBC-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US599681A US2905644A (en) | 1956-07-24 | 1956-07-24 | Anticorrosion agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US599681A US2905644A (en) | 1956-07-24 | 1956-07-24 | Anticorrosion agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2905644A true US2905644A (en) | 1959-09-22 |
Family
ID=24400627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US599681A Expired - Lifetime US2905644A (en) | 1956-07-24 | 1956-07-24 | Anticorrosion agent |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2905644A (en) |
Cited By (30)
| 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 |
| US9499762B2 (en) | 2012-12-21 | 2016-11-22 | Afton Chemical Corporation | Additive compositions with a friction modifier and a detergent |
| 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 |
Citations (4)
| 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 |
-
1956
- 1956-07-24 US US599681A patent/US2905644A/en not_active Expired - Lifetime
Patent Citations (4)
| 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)
| 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 |
| US9499762B2 (en) | 2012-12-21 | 2016-11-22 | Afton Chemical Corporation | Additive compositions with a friction modifier and a detergent |
| US9499763B2 (en) | 2012-12-21 | 2016-11-22 | Afton Chemical Corporation | Additive compositions with plural friction modifiers |
| US9499764B2 (en) | 2012-12-21 | 2016-11-22 | Afton Chemical Corporation | Additive compositions with a friction modifier and a dispersant |
| US9499761B2 (en) | 2012-12-21 | 2016-11-22 | Afton Chemical Corporation | Additive compositions with a friction modifier and a metal dialkyl dithio phosphate salt |
| US9550955B2 (en) | 2012-12-21 | 2017-01-24 | Afton Chemical Corporation | Friction modifiers for lubricating oils |
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