DE1271879B - Schmieroel - Google Patents
SchmieroelInfo
- Publication number
- DE1271879B DE1271879B DEP1271A DE1271879A DE1271879B DE 1271879 B DE1271879 B DE 1271879B DE P1271 A DEP1271 A DE P1271A DE 1271879 A DE1271879 A DE 1271879A DE 1271879 B DE1271879 B DE 1271879B
- Authority
- DE
- Germany
- Prior art keywords
- butyl
- lubricating oil
- phenol
- oil
- benzal
- 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.)
- Pending
Links
- 239000010687 lubricating oil Substances 0.000 title claims description 7
- QKSQEJXIILKPDX-UHFFFAOYSA-N n-cyclohexyl-1-phenylmethanimine Chemical compound C1CCCCC1N=CC1=CC=CC=C1 QKSQEJXIILKPDX-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003921 oil Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- ZDXGQHXSMPGQRI-UHFFFAOYSA-N 2,6-ditert-butyl-3-[(2,4-ditert-butyl-3-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC=C1CC1=CC=C(C(C)(C)C)C(O)=C1C(C)(C)C ZDXGQHXSMPGQRI-UHFFFAOYSA-N 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- WYSSJDOPILWQDC-UHFFFAOYSA-N 2,4-ditert-butyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1C(C)(C)C WYSSJDOPILWQDC-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- -1 Alkyl radical Chemical class 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000011436 cob Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000010727 cylinder oil Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
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
BUNDESREPUBLIK DEUTSCHLAND
DEUTSCHES
PATENTAMT
Int. CL:
. ClOm
Deutsche Kl.: 23 c-1/01
Nummer: 1271 879
Aktenzeichen: P 12 71 879.5-43 (C 27169)
Anmeldetag: 5. Juni 1962
Auslegetag: 4. Juli 1968
Es ist bereits bekannt, Alkylphenole mit wenig- Schmieröl
stens einem sek. oder tert. Alkylrest in o-Stellung zur Hydroxylgruppe als Antioxydationsmittel in
Schmierölen zu verwenden.
Es wurde nun gefunden, daß die Antioxydationswirkung wesentlich verbessert werden kann, wenn
man einem Schmieröl, enthaltend ein Alkylphenol, zusätzlich 0,3 bis 2,0 Gewichtsprozent Benzal-cyclohexylamin
beimischt.
Das Benzal-cyclohexylamin-Additiv wirkt in dem Schmieröl nicht nur als Korrosionsinhibitor, sondern
auch als Schlämmdispergiermittel. Es wird mit Vorteil in Zylinderölen von Schiffsmaschinen
verwendet, wo es als Dispergiermittel und/oder als Inhibitor von überzugsbildung an Kolben als auch
als verschleißverhinderndes Mittel wirksam ist.
Das Alkylphenol besitzt die allgemeine Formel:
OH
20
worin Ri eine verzweigte Cs-Cs-Alkylgruppe ohne
Wasserstoffatome an dem Kohlenstoffatom mit dem Benzolkern ist, R2, R3 und R4 Wasserstoff
oder Methylgruppen oder Ri sind, und X Wasserstoff oder R2 oder eine der beiden Gruppen
R3 R4
• CH2 —\~~V~ 0H
• CH2 —\~~V~ 0H
Anmelder:
Castrol Limited, London
Vertreter:
Dipl.-Chem. Dr. W. J. Berg
und Dipl.-Ing. O. Stapf, Patentanwälte,
8000 München 2, Hilblestr. 20
Als Erfinder benannt:
John Scotchford Elliott, London
Beanspruchte Priorität:
Großbritannien vom 8. Juni 1961 (20 819), vom 15. Mai 1962
Großbritannien vom 8. Juni 1961 (20 819), vom 15. Mai 1962
o-Isopropyl-phenol,
2,4-Dimethyl-6-t-butyl-phenol, 2,6-Di-t-butyl-4-methyl-phenol, 2,6-Di-t-butyl-phenol,
2,4-Dimethyl-6-t-butyl-phenol, 2,6-Di-t-butyl-4-methyl-phenol, 2,6-Di-t-butyl-phenol,
l,l-bis-(3,5-Di-t-butyl-4-hydroxyphenyl)-methan,
3,3',5,5'-tetra-t-Butyl-4,4'-dihydroxydiphenyl, 3-Methyl-4,6-di-t-butyl-phenol,
4-Methyl-2-t-butyl-phenol,
4,4'-bis-(2,6-Di-t-butyl-phenol).
4,4'-bis-(2,6-Di-t-butyl-phenol).
OH
R2 R1
Bevorzugt sind Verbindungen, worin Ri = Ri.
Das Alkylphenol wird in Mengen von 0,25 bis bis 2,0, bevorzugt 0,3 bis 1,0 Gewichtsprozent
und Benzal-cyclohexylamin in Mengen von 0,3 bis 2,0, bevorzugt 0,5 bis 1,0 Gewichtsprozent, bezogen
jeweils auf das Gewicht des Schmieröls, zugesetzt.
Ein bevorzugtes Gemisch besteht aus 0,5 Gewichtsprozent
Benzal-cyclohexylamin und 0,3 bis 0,5 Gewichtsprozent Methylen-bis-(2,6-di-t-butylphenol).
809 568/504
Vergleichsbeispiele
Institute of Petroleum Standard Method 114/56 T (abgeändert)
Trockene Luft wird 300 Stunden lang in einen Reaktionskolben eingeleitet, welche öl und einen
Kupferkatalysator enthält. Der Kolben und sein Inhalt werden in ein geeignetes ölbad getaucht,
welches auf 1100C gehalten wird. Die Acidität und der Demulgierungswert des oxidierten Öles wurden
nach Abkühlen bestimmt.
Institute of Petroleum Standard Method 19/61,
Demulgierungszahl
20 ml des Öls werden mit Dampf bei ungefähr 900C emulgiert. Die Emulsion wird dann in ein
Bad mit ungefähr 94°C gebracht, und die Zeit der Abtrennung von 20 ml öl wurde aufgezeichnet.
Institute of Petroleum Standard Method 177/62 T
Gesamtsäurezahl
Gesamtsäurezahl
Die ölprobe wird in einem Gemisch von Toluol und Isopropylalkohol, welcher Wasser enthält,
gelöst und wird in potentiometrischer Weise mit alkoholischer Pottasche bis pH 11 titriert.
Das Mineralöl A ist ein Gemisch, welches aus 88% eines lösungsmittelgereinigten Mineralöls der
Viskosität von ungefähr 164,6 SUS bei 6O0C mit 12% eines lösungsmittelgereinigten Brightstocks der
Viskosität von ungefähr 684 SUS bei 6O0C besteht.
Die Tabellen I und II zeigen, daß eine synergistische Wirkung bei gemeinsamer Verwendung von Alkylphenol
und Benzal-cyclohexylamin innerhalb der beanspruchten Zusatzmengen eintritt.
Abgeänderter IP | 114/56 T Oxydationsversuch, | Additive vorhanden (%) | Benzal-cyclohexylamin | 300 Stunden be | ι HO0C | |
Mineralöl A | Methylen-bis-(2,6-di-t-butyl- phenol) |
0,5 | ||||
Gemisch | nichts | 1,0 | Versuche an | oxydierten ölen | ||
Nr. | nichts | 0,5 | Acidität | Demulgierungswert | ||
1 | 0,2 | 0,25 | 1,39 | 1200 + | ||
2 | 0,25 | 0,5 | > 3,0 | 1200 + | ||
3 | 0,25 | nichts | 0,24 | 1200 + | ||
4 | 0,3 | 0,1 | 1,12 | 1200 | ||
• 5 | 0,3 | 0,2 | 0,08 | 780 | ||
6 | 0,3 | 0,5 | 0,73 | 1200 | ||
7 | 0,3 | 0,7 | 0,89 | 1200 | ||
8 | 0,3 | nichts | 0,67 | 1200 | ||
9 | 0,5 | 0,3 | 0,39 | 750, 630 | ||
10 | 0,5 | 0,5 | 0,34 | 660 | ||
11 | 0,5 | nichts | 0,86 | 1200 | ||
12 | 1,0 | 0,5 | 0,13 | 540 | ||
13 | 1,0 | 1,0 | 0,39 | 600 | ||
14 | 2,0 | 0,45 | 1200 | |||
15 | 0,17 | 840 | ||||
16 . | 0,15 | 1200 | ||||
Abgeänderter IP 114/56 T Oxydationsversuch, 300 Stunden bei HO0C
Mineralöl A
Gemisch | Vorhandene Additive | Benzal-cyclohexylamin | Versuche an oxydierten 01en | Demulgierungswert |
Nr. | Phenolische Additive | 1,0 | Acidität | 1200 |
1 | nichts | 0,5 | 3,0 | 420 |
2 | 0,5% 2,6-Di-t-butyl- | 0,44 | ||
4-methyl-phenol | nichts | 1200 | ||
3- | l,0"/o desgl. | 0,5 | 0,55 | 720 |
4- | 0,5% 4,4'-Bis-(2,6-di-t-butyl- ohenoD |
nichts | 0,48 | 1200 |
5 | 1,0% desgl. | .0,5 | 0,33 | 600 |
6 | 0,5% 2,6-Di-t-butyl-phenol | 0,45 |
Claims (1)
- 5 6τ, . u gruppe,dadurchgekennzeichnet,daßPatentanspruch: es zusätziich Benzal-cyclohexylamin enthält.Schmieröl, enthaltend ein Alkylphenol mit In Betracht gezogene Druckschriften:wenigstens einem sekundären oder tertiären 5 Britische Patentschrift Nr. 824 405;Alkylrest in ortho-Stellung zu der Hydroxyl- USA.-Patentschrift Nr. 3 018 248.X» 561/504 6.68 © Bundesdruckerei Berlin
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB20819/61A GB976970A (en) | 1961-06-08 | 1961-06-08 | Improvements in or relating to lubricating oils having anticorrosive properties |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1271879B true DE1271879B (de) | 1968-07-04 |
Family
ID=10152229
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEP1271A Pending DE1271879B (de) | 1961-06-08 | 1962-06-05 | Schmieroel |
Country Status (5)
Country | Link |
---|---|
US (1) | US3173871A (de) |
BE (1) | BE618661A (de) |
DE (1) | DE1271879B (de) |
GB (1) | GB976970A (de) |
NL (2) | NL132017C (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3250713A (en) * | 1964-05-29 | 1966-05-10 | Shell Oil Co | Lubricant composition |
US3839210A (en) * | 1971-12-01 | 1974-10-01 | Gaf Corp | Antioxidant composition comprising a synergistic mixture of a phenol, amine and sulfone |
US3900410A (en) * | 1973-04-23 | 1975-08-19 | Ethyl Corp | Lubricating oil compositions containing trialkyl-substituted phenols and benzotriazole |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB824405A (en) * | 1957-03-19 | 1959-12-02 | Exxon Research Engineering Co | Improved oil compositions |
US3018248A (en) * | 1960-01-20 | 1962-01-23 | California Research Corp | Oxidation inhibited mineral oil compositions |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2060138A (en) * | 1935-09-16 | 1936-11-10 | Merrimac Chemical Co | Corrosion inhibitor |
US2308282A (en) * | 1937-12-28 | 1943-01-12 | Us Rubber Co | Corrosion inhibitor |
US2225533A (en) * | 1938-07-26 | 1940-12-17 | Gulf Research Development Co | Transformer oil composition |
US2303819A (en) * | 1940-01-31 | 1942-12-01 | Gulf Oil Corp | Stabilizing solution of tetra-alkyl lead compounds |
GB618083A (en) * | 1946-10-17 | 1949-02-16 | Elliott Alfred Evans | Improvements in or relating to lubricating and protective oil compositions |
US2900417A (en) * | 1955-03-21 | 1959-08-18 | Ethyl Corp | 3,3' - diisopropyl - 5,5' - di - tert - butyl-4,4'-dihydroxydiphenyl, its preparation and use |
US2809164A (en) * | 1955-04-21 | 1957-10-08 | American Cyanamid Co | Oxidation inhibitors for lubricating oil |
US2944086A (en) * | 1955-09-23 | 1960-07-05 | Ethyl Corp | 1, 1-bis(3, 5-dialkyl-4-hydroxyphenyl) methanes |
US2923745A (en) * | 1957-10-21 | 1960-02-02 | Shell Dev | Ortho alkylation of phenols |
US3043775A (en) * | 1959-07-24 | 1962-07-10 | Thomas H Coffield | Organic material containing a 4, 4'-methylenebis phenol |
US3032502A (en) * | 1959-08-17 | 1962-05-01 | Standard Oil Co | Lubricant compositions |
-
0
- BE BE618661D patent/BE618661A/xx unknown
- NL NL279407D patent/NL279407A/xx unknown
- NL NL132017D patent/NL132017C/xx active
-
1961
- 1961-06-08 GB GB20819/61A patent/GB976970A/en not_active Expired
-
1962
- 1962-05-25 US US197571A patent/US3173871A/en not_active Expired - Lifetime
- 1962-06-05 DE DEP1271A patent/DE1271879B/de active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB824405A (en) * | 1957-03-19 | 1959-12-02 | Exxon Research Engineering Co | Improved oil compositions |
US3018248A (en) * | 1960-01-20 | 1962-01-23 | California Research Corp | Oxidation inhibited mineral oil compositions |
Also Published As
Publication number | Publication date |
---|---|
NL132017C (de) | |
BE618661A (de) | |
US3173871A (en) | 1965-03-16 |
GB976970A (en) | 1964-12-02 |
NL279407A (de) |
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