DK144311B - Smoeremiddel inhiberet mod oxidation - Google Patents

Smoeremiddel inhiberet mod oxidation Download PDF

Info

Publication number
DK144311B
DK144311B DK660774AA DK660774A DK144311B DK 144311 B DK144311 B DK 144311B DK 660774A A DK660774A A DK 660774AA DK 660774 A DK660774 A DK 660774A DK 144311 B DK144311 B DK 144311B
Authority
DK
Denmark
Prior art keywords
thio
thiophene
aza
diaza
phenyl
Prior art date
Application number
DK660774AA
Other languages
English (en)
Other versions
DK144311C (da
DK660774A (da
Inventor
E Rossi
S Fattori
L Imparato
Original Assignee
Snam Progetti
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 Snam Progetti filed Critical Snam Progetti
Publication of DK660774A publication Critical patent/DK660774A/da
Publication of DK144311B publication Critical patent/DK144311B/da
Application granted granted Critical
Publication of DK144311C publication Critical patent/DK144311C/da

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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • 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
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • 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
    • C10N2040/02—Bearings
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

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

(19) DANMARK pf?) fVRR/
i«) FREMUEGGELSESSKRIFT m) 144311 B
DIREKTORATET FOR PATENT- OG VAREMÆRKEVÆSENET
(21) Ansøgning nr. 6607/74 (51) lnt.CI.3 C 10 Μ 1/38 (22) Indleveringsdag 18. dec. 1974 0 ^0 Μ 3/32 (24) Løbedag 1 8. dec. 1974 (41) Aim. tilgængelig 21. jun. 1975 (44) Fremlagt 15- feb. 1982 (86) International ansøgning nr. - (86) International indleveringsdag (85) Videreførelsesdag - (62) Stamansøgning nr. - (30) Prioritet 20. dec. 1975, 54482/73* IT (71) Ansøger _SNAMPROGETTI S.P.A., Milano, IT.
(72) Opfinder Enzo Pose i, IT: Silvano Fattori, IT: Luigi Imparato, IT.
(74) Fuldmægtig Internationalt Patent-Bur eau.
(54) Smøremiddel inhiberet med oxidation.
Opfindelsen angår et smøremiddel, der er inhiberet mod oxidation, og som er tilvejebragt ved hjælp af specielle additiver, der har vist sig yderst fordelagtige i forhold til de, der normalt anvendes i teknikken.
Det er velkendt, at de høje temperaturer, der dannes i de moderne maskiner, fremmer oxidationen af smøremidlerne, idet der også dannes sure produkter, som forårsager korrosion af de metaloverflader, med hvilke de kommer i kontakt.
Endvidere aflejres disse oxidationsprodukter såvel som begagtige produkter eller fernisser eller lak på metaloverfladerne i maskinerne, hvilket så- ffi ledes forårsager en effektivitetsnedgang for selve maskinen.
' Med det formål i så høj grad som muligt at eliminere disse uønskede virk- 00 J· * Ω 2 1443 1 1 ninger tilsættes smøremidlerne sædvanligvis de såkaldte antioxidant-additiver, såsom sterisk hindrede phenoler, aromatiske aminer, alkylphenolsulfider, dialkyl-phosphonater af Ca, Ba og Al og mange andre.
Oxidationsgenerne fjernes imidlertid ikke på tilfredsstillende måde.
Af denne grund tilsigtes det med opfindelsen at tilvejebringe en ny klasse additiver til smøremidler, hvilke additiver er i stand til at inhibere oxidationen af smøremidlet på en mere effektiv måde end den, der opnås med de kendte oxidationsinhibitorer, specielt ved høje temperaturer.
Det tilsigtes endvidere med opfindelsen at tilvejebringe additiver, der in-hiberer oxidation i en bredere klasse af produkter, såsom smøremidler indeholdende mineralolier opnået ud fra de mest forskellige råstoffer raffineret ved hjælp af syrer eller opløsningsmidler eller kommende fra hydrocrackning, hvilke additiver endvidere er egnede til oxidationsinhibering af smøremidler indeholdende stoffer på syntetisk basis, såsom syntetiske carbonhydrider,syntetiske estere, sili-coner, hydrogenerede polyolefiner, polyalkylenoxider, alkylbenzener, phosphorsy-reestere og andre.
Det har nu ifølge opfindelsen vist sig, at man opnår det tilsigtede ved brug af derivaterne af 3-aza-6a-thio-thiophten og af 3,4-diaza-6a~thio-thiophten, som er i stand til at give smøremidlerne en resistens over for oxidation, som er væsentligt bedre end den, der opnås med kendte oxidationsinhibitorer.
Disse antioxiderende additiver kan ved hjælp af varme opløses i det flydende smøremiddel ved en temperatur på ikke over 70-80°C.
I overensstemmelse med ovenstående angår opfindelsen et smøremiddel på basis af mineralolier og/eller syntetiske olier, der er ejendommeligt ved, at man ved en temperatur på ikke over 80°C i olien har opløst et eller flere derivater af 3-aza-6a-thio-thiophten og/eller af 3,4-diaza-6a-thio-thiophten med følgende almene formler !!-s-S S S-s i2 12 .
hvor R, R og R er ens eller forskellige og hver især betegner hydrogen, alkyl, cycloalkyl, aryl, alkylaryl, arylalkyl, aminoaryl, alkoxyaryl eller aminoalkoxyaryl.
Mængden af den anvendte aza-thio-thiophten eller diaza-thio-thiophten afhænger af mange faktorer, såsom naturen af basisolien og tilstedeværelsen af andre additiver.
Anvendelsen af disse additiver frembyder den særlige fordel, at de er effektive selv i meget lave koncentrationer, i området 0,01% og derunder.
3 14431 1
Almindeligvis anvendes aza-thio-thiophteneme eller diaza-thio-thiophte-nerne i koncentrationer i området 0,001-10 vægt7o, fortrinsvis 0,01-5 vægt%.
De antioxidantholdige smøremidler ifølge opfindelsen kan endvidere indeholde forskellige andre typer additiver, der normalt anvendes, såsom detergenter, dispergeringsmidler, korrosionsinhibitorer, midler mod rust, midler til forbedring af viskositetsindekset, slaminhibitorer, midler til nedsættelse af størkningspunktet og også andre antioxidanter, i tilfælde af, at det er ønsket at forbedre egenskaberne med hensyn til oxidationsinhiberingen af midler, der allerede indeholder antioxidanter.
Fremstillingen af aza-thio-thiophten- eller af diaza-thio-thiophtenderiva-terne som omhandlet i opfindelsen er i almindelighed kendt for fagmanden på området.
F.eks. kan den af Hans Behringer et al i Chem. Ber. 97, 2567 (196$-) og Chem. Ber. 100 , 4027 (1967) beskrevne metode anvendes.
De efterfølgende eksempler forklarer opfindelsen og dens fordele nærmere.
Eksempel 1 I en beholder forsynet med en køler blev der anbragt 1,3 g 3-amino-5-phe-nyl-l,2-dithioliumchlorid, 2 ml phenylisothiocyanat og 200 ml toluen. Der blev kogt under tilbagesvaling i ca. 12 timer, hvorpå der blev filtreret, og en del af opløsningsmidlet blev afdampet, hvorefter der atter blev afkølet. På denne måde udkrystalliserede 1,7 g 2-anilin-5-phenyl-3-aza-6a-thio-thiophten. Smp.: 168-169°C (lit. 169-171°C).
Eksempel 2
Ved at gå frem under samme betingelser som i eksempel 1 ud fra 3-amino-5-phenyl-l,2-dithioliumchlorid og p-methoxyphenylisothiocyanat fremstilledes 2-£p-methaxyanili£7-5-phenyl-3-aza-6a-thio-thiophten. Smp.: 210-213°C (lit. 212-214 C).
Eksempel 3
Ved at gå frem under samme betingelser som i eksempel 1 ud fra 3-amino-5-p-tolyl-l,2-dithioliumchlorid og phenylisothiocyanat fremstilledes 2-anilin-5-Zp-tolyl7-3-aza-6a-thio-thiophten. Smp.: 206°G (lit. 206-207°C).
Eksempel 4 8 g phenylthiouret og 8 ml phenylisothiocyanat i 25 ml xylen blev opvarmet i en kolbe ved 150°C i ca. 2 timer. Derefter blev der afkølet, bundfaldet blev frafiltreret, vasket med ether og tørret. På denne måde opnåedes 2,5-dianilin- 3,4-diaza-6a-thio-thiophten. Smp.: 197-212°C (lit. 193-211°C).
4 144311
Eksempel 5
Under samme betingelser som i eksempel 4 blev der ud fra p-methoxyphenyl-thiouret og p.-metoxyphenylisothiocyanat fremstillet 2,5-bisZp-methoxyaniliri7- 3,4-diaza-6a-thio-thiophten. Smp.: 218-223°G (lit. omkrystalliseret af iseddikesyre, 226,5-227°C).
Eksempel 6
Til bedømmelse af deantioxiderende egenskaber af derivaterne af diaza-thio-thiophteneme og aza-thio-thiophteneme i smøremidler blev der udført nogle forsøg med oxygenabsorption.
Der blev udført forsøg i et apparat af den type, der er beskrevet af G. Mi-liotis et al (Bull. Soc. Chim. France 1969; 847), hvilke forsøg består i, at man bestemmer oxidationinduktionsperioden af et produkt holdt under kraftig omrøring i en reaktor med termostat.
Reaktoren, der var fyldt med oxygen, var forbundet med en inddelt burette til gas, også fyldt med gas.
Et differensmanometer indikerede oxygenabsorptionen.
Forsøgene blev udført ved 160^0,2°G på prøver af 10 ml under anvendelse af pulverformigt kobber som katalysator i en mængde på 50 mg.
• Tilsætningsmidlerne blev opløst i paraffinsk mineralolie med en viskositet på SAE 30.
Resultaterne fremgår af tabel 1.
Tabel 1
Forsøg nr. Additiv Koncentration Induktions-
Mol/liter periode.
’ _______________Minutter.
1 Intefe - 14 _2 2 2,6-di-t.butyl-4-methylphenol 10 270 3 2-anilin-5-phenyl-3-aza-6a-thio- - thiophten 10 396 4 2-/p-methQxyanilin7-5-phenyl- _2 3-aza-6a-thio-thiophten 10 415 5 2-anilin-5-/p-tolyi7-3-aza-6a- 2 thio-thiophten 10 372 6 2,5-di-anilin-3,4-diaza-6a-thio- 2 thiophten 10 ' 505 7 2,5-bisZp-me&osyaniliii7-3,4- _2 diaza-6a-thio-thiophten 10 490

Claims (3)

14431 1 5 Eksempel 7 Med det i eksempel 6 beskrevne apparatur og de dér beskrevne trin gav de ifølge opfindelsen benyttede additiver, opløst i trimethyladipat af octyl, de i tabel 2 angivne resultater. Tabel 2 Forsøg nr. Additiv Koncentration Induktionsperiode __Mol/liter_Minutter.
1 Intet - 4 -3 2 phenyl-a-naphthylamin 3,5 x 10 124 3 2-anilin-5-phenyl-3-aza- _3 6a-thio-thiophten 3,5 x 10 216 4 2-/p-methoxyanilin7-5- _3 phenyl-3-aza-6a-thio-thiophten 3,5 x 10 235 5 2-anilin-5Zp-tolyl7-3-aza-6a- _o thio-thiophten 3,5 x 10 207 6 2,5-di-anilin-3,4-diaza-6a- _3 thio-thiophten 3,5 x 10 365 7 2,5-bisZ"p-methoxyanili^7- _3 3,4-diaza-6a-thio-thiophten 3,5 x 10 320 Derivaterne af diaza-thio-thiophten og aza-thio-thiophtenerne kan med fordel anvendes i olier til motorer og til gear og i forskellige hydrauliske væsker. Det fremgår af tabel 1 og tabel 2, at de ifølge opfindelsen anvendte additiver er langt mere aktive som antioxidanter end de velkendte i handelen tilgængelige antioxidanter 2,6-di-t.-butyl-4-methylphenol og phenyl-a-naphthylamin.
1. Smøremiddel inhiberet mod oxidation på basis af mineralolier og/eller syntetiske olier, kendetegnet ved, at man ved en temperatur på ikke over 80°C i olien har opløst et eller flere derivater af 3-aza-6a-thio-thiophten og/eller af 3,4-diaza-6a-thio-thiophten med følgende almene formler S-S-S S-S-S
DK660774A 1973-12-20 1974-12-18 Smoeremiddel inhiberet mod oxidation DK144311C (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT54483/73A IT1000734B (it) 1973-12-20 1973-12-20 Composizioni lubrificanti inibite all ossidazione
IT5448373 1973-12-20

Publications (3)

Publication Number Publication Date
DK660774A DK660774A (da) 1975-09-01
DK144311B true DK144311B (da) 1982-02-15
DK144311C DK144311C (da) 1982-07-05

Family

ID=11287331

Family Applications (1)

Application Number Title Priority Date Filing Date
DK660774A DK144311C (da) 1973-12-20 1974-12-18 Smoeremiddel inhiberet mod oxidation

Country Status (11)

Country Link
US (1) US4029586A (da)
BE (1) BE823391A (da)
DE (1) DE2460692C3 (da)
DK (1) DK144311C (da)
FR (1) FR2255373B1 (da)
GB (1) GB1488139A (da)
IE (1) IE40792B1 (da)
IT (1) IT1000734B (da)
LU (1) LU71507A1 (da)
NL (1) NL7416739A (da)
NO (1) NO140139C (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000040664A1 (en) * 1999-01-08 2000-07-13 Loctite (R & D) Limited Novel curative for anaerobic adhesive compositions

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2612504A (en) * 1950-11-21 1952-09-30 Monsanto Chemicals Thianaphthylthiazolyl disulfides and process for preparing same
US2910439A (en) * 1955-12-22 1959-10-27 Standard Oil Co Corrosion inhibited compositions
US3282951A (en) * 1962-05-09 1966-11-01 Geigy Chem Corp Certain thiazolo-[5, 4-d]-thiazole compounds
BE632033A (da) * 1962-05-09
US3228952A (en) * 1962-06-27 1966-01-11 Dow Chemical Co Thiazole thioethers
US3904537A (en) * 1972-05-03 1975-09-09 Lubrizol Corp Novel disulfides derived from 1,2,4-thiadiazole
US3869395A (en) * 1974-02-25 1975-03-04 Texaco Inc 2-amino-5-hydrocarbyldithio-1,3,4-thiadiazole and compositions thereof
US3896050A (en) * 1974-07-05 1975-07-22 Texaco Inc Lubricating oil additives

Also Published As

Publication number Publication date
IE40792L (en) 1975-06-20
US4029586A (en) 1977-06-14
NO744592L (da) 1975-07-14
BE823391A (fr) 1975-04-16
NO140139C (no) 1979-07-11
NL7416739A (nl) 1975-06-24
FR2255373A1 (da) 1975-07-18
FR2255373B1 (da) 1977-04-08
DK144311C (da) 1982-07-05
IT1000734B (it) 1976-04-10
NO140139B (no) 1979-04-02
DE2460692A1 (de) 1975-06-26
DE2460692B2 (de) 1978-09-14
LU71507A1 (da) 1975-06-17
DK660774A (da) 1975-09-01
GB1488139A (en) 1977-10-05
DE2460692C3 (de) 1979-06-07
IE40792B1 (en) 1979-08-15

Similar Documents

Publication Publication Date Title
US3632566A (en) Sulfur-containing compositions
JPS62501014A (ja) 燐および硫黄の少量を含む潤滑油類
US3031284A (en) Fuel oil compositions containing high barium content complex salts of sulfonic acids
JPS6289796A (ja) 新規な組合せの安定化剤を含む潤滑油組成物
US3102096A (en) Lubricating oil containing zinc carboxylate-coordinated zinc dithiophosphates
US4770802A (en) Lubricating oil compositions
US2691632A (en) Oil compositions resistant to oxidation
JPS59219394A (ja) 潤滑剤組成物
US2652367A (en) Lubricating composition
US3050538A (en) Molybdenum blue complexes
US2786812A (en) Mineral oil compositions containing tincontaining dithiophosphate compounds
JPH08291150A (ja) ベンゾトリアゾール基を持つ化合物
DK144311B (da) Smoeremiddel inhiberet mod oxidation
US4042514A (en) Novel lubricating compositions containing derivatives of 1,2-dithiol-3-thiones or 1,2-dithiol-3-ones
US4198303A (en) Antioxidant lubricant compositions
US4519928A (en) Lubricant compositions containing N-tertiary alkyl benzotriazoles
US4119548A (en) Reaction product of nickel thiobis(alkylphenolate) and thiobis(alkylphenol) and organic compositions containing the same
US4174284A (en) Hydrocarbylpolythiobenzoic acids as anti-oxidation additives
US2676926A (en) Stabilizer for petroleum products
EP0164471B1 (en) Composition containing benzothiazolines as antioxidants
DK144216B (da) Smoeremiddel
US3554945A (en) Lubricating compositions containing alkylated polyhydroxy aromatic compounds
US2750340A (en) Combination additive for petroleum products
US2694045A (en) Stabilizer for petroleum products
JPS62181396A (ja) 潤滑油組成物

Legal Events

Date Code Title Description
PBP Patent lapsed