DE1026025B - Heavy-duty lubricating oils - Google Patents

Heavy-duty lubricating oils

Info

Publication number
DE1026025B
DE1026025B DEB41628A DEB0041628A DE1026025B DE 1026025 B DE1026025 B DE 1026025B DE B41628 A DEB41628 A DE B41628A DE B0041628 A DEB0041628 A DE B0041628A DE 1026025 B DE1026025 B DE 1026025B
Authority
DE
Germany
Prior art keywords
thioacetophenone
lubricating oils
heavy
weight
sulfur
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
Application number
DEB41628A
Other languages
German (de)
Inventor
Dr Adolf Hrubesch
Dr Walter Franke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DEB41628A priority Critical patent/DE1026025B/en
Priority to FR1181685D priority patent/FR1181685A/en
Publication of DE1026025B publication Critical patent/DE1026025B/en
Pending legal-status Critical Current

Links

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
    • 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
    • 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
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • 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
    • C10M2215/26—Amines
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

DEUTSCHESGERMAN

Es wurde bereits vorgeschlagen, aromatische Nitroverbindungen als Zusatzstoffe für die Verbesserung von Schmierölen zu verwenden. Die verbessernde Wirkung dieser Stoffe ist jedoch verhältnismäßig gering, sie reicht im allgemeinen nicht aus, um hochdruckfeste Schmieröle zu gewinnen. Durch die weitere Zugabe von elementarem Schwefel konnte die Wirkung der aromatischen Nitroverbindungen zwar so weit gesteigert werden, daß hochdruckfeste Schmieröle erhalten· wurden, jedoch trat mit der Zugabe von Schwefel der Nachteil auf, daß die mit diesen Zusätzen gewonnenen Hodhdruckschmieröle einen positiven Kupferstreifentest gaben und Lagermetalle, oft auch Lager aus weichem Eisen, schwarz färbten. Auch die Verwendung aromatischer Nitroverbindungen mit Umsetzungsprodukten von Olefinen und Schwefel war bekannt.It has already been suggested to use aromatic nitro compounds as additives for the improvement of Use lubricating oils. The improving effect of these substances is relatively small, however, it is sufficient generally not enough to obtain high-pressure-resistant lubricating oils. By further adding elemental With sulfur, the effect of the aromatic nitro compounds could be increased to such an extent that they are highly pressure-resistant Lubricating oils were obtained, but there was a disadvantage with the addition of sulfur that those with these High pressure lubricating oils have a positive effect on additives Copper strip tests gave and colored bearing metals, often also bearings made of soft iron, black. Even the use of aromatic nitro compounds with reaction products of olefins and sulfur was known.

Es wurde nun gefunden, daß man sehr gute hochbelastbare Schmieröle erhält, wenn man Schmierölen Nitrosamine, Sulfnitrosamide und/oder Chloraniline zusammen mit Umsetzungsprodukten von Schwefel mit Olefinen zugibt. Durch die Zugabe der Umsetzungsprodukte von Schwefel mit Olefinen wird die an sich nur verhältnismäßig geringe ~ Wirkung der Nitrosamine, Sulfnitrosamide und Chloraniline aktiviert, und es -werden hochbelastbare Schmieröle mit negativem Kupferstreifentest erhalten. Die erfindungsgemäß verwendeten Produkte zeigen im allgemeinen um 100 bis 200 höhere AWM-Werte und um 50 bis 100 höhere VKA-Werte als die aromatischen Nitroverbindungen mit Umsetzungsprodukten von Olefinen und Schwefel.It has now been found that very good heavy-duty lubricating oils are obtained if lubricating oils are used Nitrosamines, sulfnitrosamides and / or chloranilines together with reaction products of sulfur with Admits olefins. By adding the reaction products of sulfur with olefins, the only relatively little ~ action of nitrosamines, sulfnitrosamides and chloranilines activated, and it -will Heavy-duty lubricating oils obtained with a negative copper strip test. The products used according to the invention generally show 100 to 200 higher AWM values and 50 to 100 higher VKA values than the aromatic ones Nitro compounds with reaction products of olefins and sulfur.

Als Nitrosamine kommen z. B. folgende Verbindungen in Betracht: Nitrosodiphenylamin, Diisoctylnitrosamin, Nitrosomethylanilin, N-Nitrosomethyl-p-Anisidin, Dichlornitrosomethylanilin. As nitrosamines z. B. the following compounds into consideration: nitrosodiphenylamine, diisoctylnitrosamine, Nitrosomethylaniline, N-nitrosomethyl-p-anisidine, dichloronitrosomethylaniline.

Als Sulfnitrosamide können z. B. angewandt werden: Diactin (p-Toluol-N-Nitrösosulfmethylamid) oder Benzsulf-N-nitrosobutylsulfamid. As sulfnitrosamides, for. B. can be used: Diactin (p-toluene-N-Nitrösosulfmethylamid) or Benzsulf-N-nitrosobutylsulfamid.

Als Chloraniline eignen sich z. B. Chlor-N-CH3-AnUm und Monochlor-N-Methylanilin.Suitable chloranilines are, for. B. Chlor-N-CH 3 -AnUm and monochloro-N-methylaniline.

Als Olefine für die Umsetzung mit Schwefel kommen in Frage z. B. Styrol, Stilben, N-Vinylcarbazol, N-Vinylpyrrolidon. As olefins for the reaction with sulfur come in Question z. B. styrene, stilbene, N-vinyl carbazole, N-vinyl pyrrolidone.

Die Umsetzung wird im allgemeinen bei 150 bis 2500C, Hochbelastbare SchmieröleThe reaction is generally conducted at 150 to 250 0 C, Heavy-duty lubricating oils

Anmelder:Applicant:

Badische Anilin- & Soda-Fabrik
Aktiengesellschaft, Ludwigshafen/RheinAniline & Soda Factory in Baden
Aktiengesellschaft, Ludwigshafen / Rhein

Dr. Adolf Hrabesch und Dr. Walter Franke,Dr. Adolf Hrabesch and Dr. Walter Franke,

Ludwigshafen/Rhein,
sind als Erfinder genannt wordenLudwigshafen / Rhine,
have been named as inventors

vorteilhaft unter 2000C, z. B. bei 160 bis 18O0C, durchgeführt. advantageously below 200 0 C, z. As at 160 to 18O 0 C is performed.

Die Nitrosamine, Sulfnitrosamide und Chloraniline werden den Schmierölen zweckmäßig in einer Menge von etwa 0,5 bis 5 Gewichtsprozent, bezogen auf Grundöl, zugesetzt.The nitrosamines, sulfnitrosamides and chloranilines are useful in lubricating oils in an amount of about 0.5 to 5 percent by weight, based on the base oil, added.

An Umsetzungsprodukten von Schwefel mit Olefinen genügt meist die Hälfte dieser Menge, in vielen Fällen sogar noch weniger, d.h. etwa 0,05 bis 2 Gewichtsprozent, bezogenHalf of this amount of reaction products of sulfur with olefins is usually sufficient, in many cases even even less, i.e. about 0.05 to 2 percent by weight

auf Grundöl. „ . . , .on base oil. ". . ,.

Beispiel 1example 1

1550 Gewichtsteile Schwefel erhitzt man in einem Dreihalskolben auf etwa 160° C und tropft im Zeitraum von 1I2, Stunde 5000 Gewichtsteile stabilisiertes Styrol zu. Nach 2 bis 3 Stunden filtriert man das Umsetzungsgemisch bei etwa 8O0C. Es ist in diesem Zustand bereits verwendbar, man kann es aber auch bei 10^2mmHg zwischen 100 und 15O0C destillieren und erhält eine hellgelbe, nicht unangenehm riechende ölige Flüssigkeit, deren Zusammensetzung der des dimeren Thioacetophenons entspricht.1550 parts by weight of sulfur are heated in a three-necked flask to about 160 ° C. and 5000 parts by weight of stabilized styrene are added dropwise over a period of 1 1/2 hours. After 2 to 3 hours, filter the reaction mixture at about 8O 0 C. It is already used in this state, it can be also at 10 ^ 2 mmHg between 100 and 15O 0 C distilled and gives a pale yellow, non malodorous oily liquid whose composition corresponds to that of the dimeric thioacetophenone.

Bei einem Zusatz von 2 Gewichtsprozent dieses Produktes und 4 Gewichtsprozent eines in der folgenden Tabelle genannten Nitrosamines zu einem Grundöl mitWith an addition of 2 percent by weight of this product and 4 percent by weight of one of the following Table mentioned nitrosamines to a base oil with

dem AWM-Wert 160 kg und dem VK A-Wert 160 kg werden folgende Werte erhalten:the AWM value 160 kg and the VK A value 160 kg the following values are obtained:

AWMAWM VKAVKA Nitrosodiphenylamin ohne Thioacetophenon
Nitrosodiphenylamin -f- Thioacetophenon Nitrosodiphenylamine without thioacetophenone
Nitrosodiphenylamine -f- thioacetophenone 700
1900700
1900 180
400180
400 Diisoctylnitrosamin ohne Thioacetophenon
Diisoctylnitrosamin + Thioacetophenon Diisoctylnitrosamine without thioacetophenone
Diisoctylnitrosamine + thioacetophenone 800
1400800
1400 280
700280
700 Nitrosomethylanilin ohne Thioacetophenon
Nitrosomethylanilin + Thioacetophenon Nitrosomethylaniline without thioacetophenone
Nitrosomethylaniline + thioacetophenone 1300
19001300
1900 260
600260
600

709 909/367709 909/367

33 AWMAWM 44th VKAVKA 1800
18501800
1850 190
600190
600 N-Nitrosomethyl-p-Anisidin ohne Thioacetophenon
N-Nitrosomethyl-p-Anisidin + Thioacetophenon N-nitrosomethyl-p-anisidine without thioacetophenone
N-nitrosomethyl-p-anisidine + thioacetophenone 1600
16501600
1650 200
700200
700 Dichlomitrosomethylanilin ohne Thioacetophenon
Dichlornitrosomethylanilin + Thioacetophenon Dichlomitrosomethylaniline without thioacetophenone
Dichloronitrosomethylaniline + thioacetophenone 1400
18501400
1850 200
600200
600 2,5-DicUor-N-nitrosomethylanilin ohne Thioacetophenon ..
2,5-Dichlor-N-nitrosomethylanilin + Thioacetophenon....2,5-DicUor-N-nitrosomethylaniline without thioacetophenone ..
2,5-dichloro-N-nitrosomethylaniline + thioacetophenone .... 1650
17001650
1700 200
600200
600 2,4-Dichlor-N-nitrosomethylanilin ohne Thioacetophenon ..
2,4-Dichlor-N-nitrosomethylanilin + Thioacetophenon ...2,4-dichloro-N-nitrosomethylaniline without thioacetophenone ..
2,4-dichloro-N-nitrosomethylaniline + thioacetophenone ... 1850
20001850
2000 200
800200
800 3,4-Dichlor-N-nitrosoinethylanilin ohne Thioacetophenon ..
3,4-Dichlor-N-nitrosomethylanilin + Thioacetophenon....3,4-dichloro-N-nitrosoinethylaniline without thioacetophenone ..
3,4-dichloro-N-nitrosomethylaniline + thioacetophenone .... 1650
17001650
1700 500
750500
750 2,4,5-Trichlor-N-nitrosomethylanilin ohne Thioacetophenon
2,4,5-Trichlor-N-nitrosomethylanüin -f- Thioacetophenon ..2,4,5-trichloro-N-nitrosomethylaniline without thioacetophenone
2,4,5-trichloro-N-nitrosomethylanüin -f- thioacetophenone .. 1350
19001350
1900 280
800280
800 3,4-Dichlormethylanilin ohne Thioacetophenon
3,4-Dichlormethylanilin + Thioacetophenon 3,4-dichloromethylaniline without thioacetophenone
3,4-dichloromethylaniline + thioacetophenone

Setzt man 2 Gewichtsprozent des genannten Umsetzungsproduktes und 4 Gewichtsprozent eines in derIf 2 percent by weight of the reaction product mentioned is used and 4 percent by weight of one in the

nachstehenden Tabelle genannten Sulfnitrosamids zu dem gleichen Grundöl zu, so ergeben sich folgende Zahlen:Add the sulfnitrosamides mentioned in the table below to the same base oil, the following figures result:

AWMAWM

VKAVKA

Diactin (p-Toluol-N-Nitrososulfmethylamid) ohne Thioacetophenon Diactin (p-toluene-N-nitrososulfmethylamide) without thioacetophenone

Diactin (p-Toluol-N-Nitrososulfmethylamid) + Thioacetophenon Diactin (p-toluene-N-nitrososulfmethylamide) + Thioacetophenone

Benzsulf N-nitrosobutylsulfamid ohne Thioacetophenon . Benzsulf N-nitrosobutylsulfamid + Thioacetophenon ...Benzsulf N-nitrosobutylsulfamide without thioacetophenone. Benzsulf N-nitrosobutylsulfamide + thioacetophenone ...

Benzsulf-(N-mtroso-N-butyl)-amid ohne Thioacetophenon Benzsulf-(N-nitroso-N-butyl)-amid -+- Thioacetophenon ..Benzsulf- (N-mtroso-N-butyl) -amide without thioacetophenone Benzsulf- (N-nitroso-N-butyl) -amid - + - thioacetophenone ..

14001400

15001500

1600
19001600
1900

1600
17001600
1700

280280

700700

260 500260 500

260 600260 600

Bei Zugabe von 2 Gewichtsprozent des genannten Um- anilins wird das oben angeführte Grundöl folgendersetzungsproduktes und 4 Gewichtsprozent eines Chlor- 40 maßen verbessert:When adding 2 percent by weight of the umaniline mentioned, the base oil listed above becomes the following decomposition product and 4 percent by weight of a chlorine mass improved:

AWMAWM

VKAVKA

Chlor-N-C H3-AnUm ohne Thioacetophenon Chlor-NC H 3 -AnUm without thioacetophenone

Chlor-N-CHg-Anilin + Thioacetophenon Chlorine-N-CHg-aniline + thioacetophenone

Monochlor-N-Methylanilin ohne Thioacetophenon. Monochlor-N-Methylanüin + Thioacetophenon ..Monochloro-N-methylaniline without thioacetophenone. Monochloro-N-methylanuine + thioacetophenone ..

1550
16001550
1600

1550
16001550
1600

220 600220 600

220 600220 600

Beispiel 2Example 2

120 Gewichtsteile Stilben und 23 Gewichtsteile Schwefel erhitzt man 4 bis 6 Stunden auf 160 bis 17O0C und kristallisiert das erhaltene Gemisch aus n-Butanol um. Man erhält in einer Ausbeute von über 90 Gewichtsprozent eine Verbindung C14H12S mit dem Schmelzpunkt 116 bis 117° C, die die gleichen aktivierenden Eigenschaften wie das im Beispiel 1 genannte dimere Thioacetophenon zeigt.120 parts by weight of stilbene, and 23 parts by weight of sulfur is heated for 4 to 6 hours to 160 to 17O 0 C and the resulting mixture was crystallized from n-butanol to. A compound C 14 H 12 S with a melting point of 116 ° to 117 ° C., which shows the same activating properties as the dimeric thioacetophenone mentioned in Example 1, is obtained in a yield of over 90 percent by weight.

Claims (1)

Patentanspruch:Claim: Hochbelastbare Schmieröle, gekennzeichnet durch einen Gehalt an Nitrosaminen, Sulfnitrosamiden und/oder Chloranilinen zusammen mit Umsetzungsprodukten von Schwefel mit Olefinen. Heavy-duty lubricating oils, characterized by a content of nitrosamines, sulfnitrosamides and / or chloroanilines together with reaction products of sulfur with olefins. In Betracht gezogene Druckschriften: DeutschePatentschriften Nr. 925 192, 926 680,927820; britische Patentschrift Nr. 455 305.Considered publications: German Patent Nos. 925 192, 926 680,927820; British Patent No. 455 305.
DEB41628A 1956-09-04 1956-09-04 Heavy-duty lubricating oils Pending DE1026025B (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DEB41628A DE1026025B (en) 1956-09-04 1956-09-04 Heavy-duty lubricating oils
FR1181685D FR1181685A (en) 1956-09-04 1957-08-27 Lubricants for high pressures

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB41628A DE1026025B (en) 1956-09-04 1956-09-04 Heavy-duty lubricating oils

Publications (1)

Publication Number Publication Date
DE1026025B true DE1026025B (en) 1958-03-13

Family

ID=6966457

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB41628A Pending DE1026025B (en) 1956-09-04 1956-09-04 Heavy-duty lubricating oils

Country Status (2)

Country Link
DE (1) DE1026025B (en)
FR (1) FR1181685A (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB455305A (en) * 1934-04-24 1936-10-19 Du Pont Improvements in or relating to lubricants
DE925192C (en) * 1952-08-25 1955-03-14 Huels Chemische Werke Ag Additives for lubricants
DE926680C (en) * 1952-08-25 1955-04-21 Huels Chemische Werke Ag Additives for lubricants
DE927820C (en) * 1952-08-25 1955-05-16 Huels Chemische Werke Ag Additives for lubricants

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB455305A (en) * 1934-04-24 1936-10-19 Du Pont Improvements in or relating to lubricants
DE925192C (en) * 1952-08-25 1955-03-14 Huels Chemische Werke Ag Additives for lubricants
DE926680C (en) * 1952-08-25 1955-04-21 Huels Chemische Werke Ag Additives for lubricants
DE927820C (en) * 1952-08-25 1955-05-16 Huels Chemische Werke Ag Additives for lubricants

Also Published As

Publication number Publication date
FR1181685A (en) 1959-06-17

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