US2285752A - Anticorrosive - Google Patents
Anticorrosive Download PDFInfo
- Publication number
- US2285752A US2285752A US366148A US36614840A US2285752A US 2285752 A US2285752 A US 2285752A US 366148 A US366148 A US 366148A US 36614840 A US36614840 A US 36614840A US 2285752 A US2285752 A US 2285752A
- Authority
- US
- United States
- Prior art keywords
- phenyl
- corrosiveness
- alpha
- ethers
- naphthyl
- 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
- -1 alkyl phenyl alpha naphthyl ethers Chemical class 0.000 description 15
- 239000010687 lubricating oil Substances 0.000 description 13
- ARNKHYQYAZLEEP-UHFFFAOYSA-N 1-naphthalen-1-yloxynaphthalene Chemical class C1=CC=C2C(OC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ARNKHYQYAZLEEP-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000009972 noncorrosive effect Effects 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- DZRLNYVDCIYXPG-UHFFFAOYSA-N 2-naphthalen-2-yloxynaphthalene Chemical class C1=CC=CC2=CC(OC=3C=C4C=CC=CC4=CC=3)=CC=C21 DZRLNYVDCIYXPG-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 229910000760 Hardened steel Inorganic materials 0.000 description 1
- 241000158728 Meliaceae Species 0.000 description 1
- 229910000978 Pb alloy Inorganic materials 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 240000004460 Tanacetum coccineum Species 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical compound [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- OJIJEKBXJYRIBZ-UHFFFAOYSA-N cadmium nickel Chemical compound [Ni].[Cd] OJIJEKBXJYRIBZ-UHFFFAOYSA-N 0.000 description 1
- NSAODVHAXBZWGW-UHFFFAOYSA-N cadmium silver Chemical compound [Ag].[Cd] NSAODVHAXBZWGW-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 229940073532 candelilla wax Drugs 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- 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
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/18—Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
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- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/16—Naphthenic acids
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- C10M2207/18—Tall oil acids
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- C10M2207/40—Fatty vegetable or animal oils
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- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/16—Dielectric; Insulating oil or insulators
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/17—Electric or magnetic purposes for electric contacts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
- C10N2060/04—Oxidation, e.g. ozonisation
Definitions
- This invention deals with the use of alpha naphthyl ethers as addition agents to hydrocarbon oils and other organic substances. I have discovered that the presence of these compounds in suitable amounts reduces or inhibits the corrosiveness toward metallic surfaces of such hydrocarbon oils and other organic substances as possess this objectionable property.
- corrosiveness of organic substances may be inherent in their chemical structure or composition, or may be induced by oxidation. Either type of corrosiveness may be reduced, and in many instances be completely inhibited.
- Suitable alpha naphthyl ethers are particularly the symmetrical dialpha naphthyl ether, the phenyl and alkyl phenyl alpha naphthyl ethers, such as tolyl, xylyl, trimethyl phenyl, tetramethyl phenyl, methyl ethyl phenyl, n-propyl phenyl, isopropyl phenyl, primary, secondary and tertiary butyl or amyl phenyl, ditertiary butyl phenyl, methyl ditertiary butyl phenyl, tritertiary butyl phenyl, ditertiary amyl phenyl, methyl ditertiary amyl phenyl, tritertiary amyl phenyl, etc., alpha naphthyl ethers; and alkyl or aralkyl alpha naphthyl ethers, such as
- beta naphthyl ethers and particularly the dibeta naphthyl ether, have very little inhibiting properties, and in some instances have been found to aggravate corrosiveness of substances to which they are added.
- the alpha naphthyl ethers of this invention are thermally quite stable, and therefore are useful as addition agent -to a large number of substances which are in need of improvement with regard to reduction of corrosiveness. may be added to gasolines, kerosenes, diesel fuels, lubricants, electrical oils, or to non-hydrocarbon substances such as fats, fatty acids. soaps, naphthenate driers, essential oils. extracts of pyrethrum, or other insecticides which lose their potency on exposure to air. etc. Of particular interest is the use of the alpha naphthyl ethers in lubricating oils containing corrosion-inducing amounts, e.
- oil-soluble detergents such as salts of polyvalent metals, more particularly of Mg, Ca, Sr, Ba, Zn, Cd, Al, Sn, Pb, Cr, Mn, Fe, Ni, Co, Cu.
- organic acids such as fatty acids, fatty acids having attached aromatic radicals as phenyl, hydroxy phenyl, benzyl, benzal, etc., radicals; naphthenic acids, acids obtained from natural waxes as montan wax, carnauba wax. candelilla wax, etc., acids obtained by oxidation of paraflin wax, acids obtained by hydrolysis of rosin oil or tall oil, alkyl- Thus they.
- the amounts of the ethers to be added varies somewhat depending upon the original corrosiveness or upon the tendency of the substance to increase in corrosiveness during storage or use or both. Thus, while lubricating oils and the like may require the use of amounts in excess of .2%
- the alpha-naphthyl ethers As against alpha-naphthol, beta-naphthol, and many phenolic inhibitors, the alpha-naphthyl ethers have the advantage of being color stable in the presence of alkali.
- Many compounded lubricating oils for internal combustion engines contain alkaline detergents, and in the presence of free alkali the naphthols in particular turn to weird hues, as purple, green or blue.
- Mineral oil 0. 20 Mineral nil+2. 5% calcium petroleum sulfonate 5. 7 Mineral oil+2.5% calcium petroleum sulfonato+l% (ii-alpha naphthyl ether O. ()9 Mineral oil+2.5% calcium petroleum sulfonate+1% di-beta naphthyl other l0. 0
- a non-corrosive lubricating oil composition 4. The composition of claim 3 wherein said small amount is between .1 96-5% 5.
- a non-corrosive lubricating oil composition comprising a lubricating oil which normally causes corrosion containing dissolved a small amount 01' phenyl alpha naphthyl ether.
- a non-corroslve-lubricating oil composition comprising a lubricating oil which normally causes corrosion containing dissolved a small amount of (ii-alpha naphthyl ether.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
Patented June 9, 1942 ANTICORROSIVE Paul R. Van Ess, Berkeley, Calif., assignor to Shell Development Company, San Francisco, Calif., a corporation of Delaware No Drawing. Application November 18, 1940,
Serial No. 366,148
7 Claims.
This invention deals with the use of alpha naphthyl ethers as addition agents to hydrocarbon oils and other organic substances. I have discovered that the presence of these compounds in suitable amounts reduces or inhibits the corrosiveness toward metallic surfaces of such hydrocarbon oils and other organic substances as possess this objectionable property.
corrosiveness of organic substances may be inherent in their chemical structure or composition, or may be induced by oxidation. Either type of corrosiveness may be reduced, and in many instances be completely inhibited.
Suitable alpha naphthyl ethers are particularly the symmetrical dialpha naphthyl ether, the phenyl and alkyl phenyl alpha naphthyl ethers, such as tolyl, xylyl, trimethyl phenyl, tetramethyl phenyl, methyl ethyl phenyl, n-propyl phenyl, isopropyl phenyl, primary, secondary and tertiary butyl or amyl phenyl, ditertiary butyl phenyl, methyl ditertiary butyl phenyl, tritertiary butyl phenyl, ditertiary amyl phenyl, methyl ditertiary amyl phenyl, tritertiary amyl phenyl, etc., alpha naphthyl ethers; and alkyl or aralkyl alpha naphthyl ethers, such as methyl, ethyl, n-propyl, isopropyl, primary, secondary or tertiary butyl, primary, secondary or tertiary amyl, hexyl, benzyl, etc., alpha naphthyl ethers. If desired, the aromatic nucleus or nuclei, e. g., the naphthyl radical, may contain one or several alkyl radicals.
, It is of interest to note that the corresponding beta naphthyl ethers, and particularly the dibeta naphthyl ether, have very little inhibiting properties, and in some instances have been found to aggravate corrosiveness of substances to which they are added.
The alpha naphthyl ethers of this invention are thermally quite stable, and therefore are useful as addition agent -to a large number of substances which are in need of improvement with regard to reduction of corrosiveness. may be added to gasolines, kerosenes, diesel fuels, lubricants, electrical oils, or to non-hydrocarbon substances such as fats, fatty acids. soaps, naphthenate driers, essential oils. extracts of pyrethrum, or other insecticides which lose their potency on exposure to air. etc. Of particular interest is the use of the alpha naphthyl ethers in lubricating oils containing corrosion-inducing amounts, e. g., from about .1 of oil-soluble detergents such as salts of polyvalent metals, more particularly of Mg, Ca, Sr, Ba, Zn, Cd, Al, Sn, Pb, Cr, Mn, Fe, Ni, Co, Cu. with organic acids such as fatty acids, fatty acids having attached aromatic radicals as phenyl, hydroxy phenyl, benzyl, benzal, etc., radicals; naphthenic acids, acids obtained from natural waxes as montan wax, carnauba wax. candelilla wax, etc., acids obtained by oxidation of paraflin wax, acids obtained by hydrolysis of rosin oil or tall oil, alkyl- Thus they.
ated benzoic, hydroxy benzoic, naphthoic, etc., acids, sulfonic acids, such as so-called mahogany acids, etc. It is known that these soaps cause lubricating oils to become more or less corrosive, particularly to alloy bearings, such as copperlead, cadmium-silver, cadmium-nickel, etc.
The amounts of the ethers to be added varies somewhat depending upon the original corrosiveness or upon the tendency of the substance to increase in corrosiveness during storage or use or both. Thus, while lubricating oils and the like may require the use of amounts in excess of .2%
and up to 5 to 10% to insure continued non-corrosiveness, particularly if such lubricating oils should contain corrosive addition compounds, smaller amounts usually are suflicient to inhibit cases of slight corrosiveness as is normal for example in gasolines, kerosenes, etc. in which amounts varying from .001% to 1% are normally sufilcient.
As against alpha-naphthol, beta-naphthol, and many phenolic inhibitors, the alpha-naphthyl ethers have the advantage of being color stable in the presence of alkali. Many compounded lubricating oils for internal combustion engines contain alkaline detergents, and in the presence of free alkali the naphthols in particular turn to weird hues, as purple, green or blue.
The following example further illustrates my invention:
Samples of lubricating oils were subjected to a thrust-bearing corrosion test to determine their corrosiveness. In this test, a hardened steel disc The bearings reported below consisted of copper-lead alloy. The oils tested were of the type of anti-ringsticking diesel lubricating oil consisting of a 55 V. I. mineral lubricating oil S. A. E. 30 and containing a detergent soap which caused the oil to be quite corrosive. For comparison, the corrosiveness of the straight mineral oil is also shown:
Bearing loss, on mgJsq. cm.
Mineral oil 0. 20 Mineral nil+2. 5% calcium petroleum sulfonate 5. 7 Mineral oil+2.5% calcium petroleum sulfonato+l% (ii-alpha naphthyl ether O. ()9 Mineral oil+2.5% calcium petroleum sulfonate+1% di-beta naphthyl other l0. 0
I claim as my invention: 1. A non-corrosive lubricating oil composition 4. The composition of claim 3 wherein said small amount is between .1 96-5% 5. A non-corrosive lubricating oil composition comprising a lubricating oil which normally causes corrosion containing dissolved a small amount 01' phenyl alpha naphthyl ether.
6. A non-corrosive lubricating oil composition of claim 3 in which the ethers are present in amounts ranging from .001% to 10%.
7. A non-corroslve-lubricating oil composition comprising a lubricating oil which normally causes corrosion containing dissolved a small amount of (ii-alpha naphthyl ether.
PAUL R. VAN ESS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US366148A US2285752A (en) | 1940-11-18 | 1940-11-18 | Anticorrosive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US366148A US2285752A (en) | 1940-11-18 | 1940-11-18 | Anticorrosive |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2285752A true US2285752A (en) | 1942-06-09 |
Family
ID=23441841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US366148A Expired - Lifetime US2285752A (en) | 1940-11-18 | 1940-11-18 | Anticorrosive |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2285752A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2438468A (en) * | 1942-12-31 | 1948-03-23 | Standard Oil Dev Co | Oil composition |
| US2449025A (en) * | 1943-07-21 | 1948-09-07 | Atlantic Refining Co | Rust-inhibiting lubricant |
| US2453690A (en) * | 1944-10-23 | 1948-11-16 | Ulrie B Bray | Process of producing polyvalentmetal hydrocarbon sulfonate |
| US2485861A (en) * | 1945-10-01 | 1949-10-25 | Sumner E Campbell | Lubricating oil |
| US2501731A (en) * | 1946-10-14 | 1950-03-28 | Union Oil Co | Modified lubricating oil |
| US2677618A (en) * | 1950-10-21 | 1954-05-04 | Standard Oil Co | Rust preventive compositions |
| US4304707A (en) * | 1979-03-12 | 1981-12-08 | Ici Americas Inc. | Rust inhibiting coating compositions |
| US4889614A (en) * | 1989-05-09 | 1989-12-26 | Betz Laboratories, Inc. | Methods for retarding coke formation during pyrolytic hydrocarbon processing |
-
1940
- 1940-11-18 US US366148A patent/US2285752A/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2438468A (en) * | 1942-12-31 | 1948-03-23 | Standard Oil Dev Co | Oil composition |
| US2449025A (en) * | 1943-07-21 | 1948-09-07 | Atlantic Refining Co | Rust-inhibiting lubricant |
| US2453690A (en) * | 1944-10-23 | 1948-11-16 | Ulrie B Bray | Process of producing polyvalentmetal hydrocarbon sulfonate |
| US2485861A (en) * | 1945-10-01 | 1949-10-25 | Sumner E Campbell | Lubricating oil |
| US2501731A (en) * | 1946-10-14 | 1950-03-28 | Union Oil Co | Modified lubricating oil |
| US2677618A (en) * | 1950-10-21 | 1954-05-04 | Standard Oil Co | Rust preventive compositions |
| US4304707A (en) * | 1979-03-12 | 1981-12-08 | Ici Americas Inc. | Rust inhibiting coating compositions |
| US4889614A (en) * | 1989-05-09 | 1989-12-26 | Betz Laboratories, Inc. | Methods for retarding coke formation during pyrolytic hydrocarbon processing |
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