DE4435548A1 - Stabilisierte Schmierstoff-Grundsubstanz - Google Patents
Stabilisierte Schmierstoff-GrundsubstanzInfo
- Publication number
- DE4435548A1 DE4435548A1 DE4435548A DE4435548A DE4435548A1 DE 4435548 A1 DE4435548 A1 DE 4435548A1 DE 4435548 A DE4435548 A DE 4435548A DE 4435548 A DE4435548 A DE 4435548A DE 4435548 A1 DE4435548 A1 DE 4435548A1
- Authority
- DE
- Germany
- Prior art keywords
- lubricant base
- acid
- carbodiimides
- test
- base substance
- 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.)
- Withdrawn
Links
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- C—CHEMISTRY; METALLURGY
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/22—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms containing a carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones
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- C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
- C10M101/04—Fatty oil fractions
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
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Description
Eine Reihe von Schmierstoff-Grundsubstanzen, z. B. natürliche Triglyceride, syn
thetische Carbonsäureester, Phosphorsäuretriester Olefin-Dicarbonsäure-
Copolymere und Silikonöle werden durch Wasser hydrolytisch angegriffen unter
Bildung von sauren Spaltprodukten und Alkoholen. Diese sauren Spaltprodukte
sind ein Maß für den Zersetzungsgrad. Sie können in Form der Säurezahl
quantitativ angegeben werden, so daß diese als Maß für den Alterungszustand der
Schmierstoff-Grundsubstanzen dient (Säurezahl ist die Menge KOH in mg, die zur
Neutralisation von 1 g Substanz erforderlich ist).
Die Anwesenheit von Säuren oder sauren Spaltprodukten beschleunigt die
Hydrolyse autokatalytisch. Da Wasser unter technischen Bedingungen immer min
destens in geringen Mengen anwesend ist, ist also die Nutzungsdauer von
Schmierstoffen auf der Basis von solchen Estergruppen enthaltenden Schmierstoff-
Grundsubstanzen beschränkt.
Bisher ist es nicht gelungen, diesen entscheidenden Nachteil der Estergruppen
enthaltenden Schmierstoff-Grundsubstanzen durch Zusätze zu beheben. Man war
auch der Ansicht, daß dies aufgrund der Natur der Esterbindung gar nicht möglich
ist. Man hat versucht, den anfänglichen Säuregehalt solcher Substanzen durch
besondere Reinigungsverfahren herabzusetzen. Jedoch wird hierdurch der Abbau
lediglich anfänglich verzögert. Ebenso hat man langkettige öllösliche Amine zuge
setzt, die mit denen in den Grundstoffen enthaltenden oder entstandenen Säuren
unter Salzbildung reagieren. Diese Salze dissoziieren aber sehr leicht (sie werden
z. B. bei der Bestimmung der Säurezahl mit erfaßt), so daß die sauren Verunreini
gungen (im wesentlichen Carboxylationen) nicht dauerhaft aus der Zubereitung
entfernt werden.
Der Erfindung liegt die Erkenntnis zugrunde, daß ein Zusatz von 0,05 bis
5 Gew.-%, bevorzugt 0,1 bis 3 Gew.-% eines darin löslichen Carbodiimids zu
einer Estergruppen enthaltenden Schmierstoff-Grundsubstanz die hydrolytische
Zersetzung wirksam verhindert. Carbodiimide reagieren sowohl mit Säuren, z. B.
den Spaltprodukten der Estergruppen enthaltenden Schmierstoff-Grundsubstanz als
auch mit Wasser. In beiden Fällen entstehen stabile Harnstoffderivate. Die Reak
tion mit den sauren Bestandteilen ist schnell, die mit Wasser sehr langsam. Es
werden also sowohl vorhandene oder entstandene saure Bestandteile dauerhaft
entfernt als auch in das Produkt gelangtes Wasser.
Bisher hat man Carbodiimide zur Stabilisierung thermoplastischer Kunststoffe ver
wendet. Diese liegen aber nach einmaliger Verformung im allgemeinen als feste
unveränderliche Formkörper vor, die lediglich an der Oberfläche mit der Umge
bung in Kontakt treten. Schmierstoffe dagegen werden bei Dauertemperaturen von
z. B. 60 bis 120°C ständig umgewälzt, so daß ständig neue Oberflächen gebildet
werden und mit der Umgebung in Berührung kommen. Die thermische und mecha
nische Belastung ist also ganz entscheidend stärker als in Kunststoffen. Es war
nicht vorhersehbar, daß Carbodiimide auch unter diesen wesentlich stringenteren
Bedingungen die Stabilität von Schmierstoff-Grundsubstanzen dramatisch ver
bessern und daß hierzu nur geringe Mengen erforderlich sind.
Gegenstand der Erfindung sind Estergruppen enthaltende Schmierstoff-Grundsub
stanzen, die als Stabilisatoren 0,05 bis 5 Gew.-%, bevorzugt 0,1 bis 3 Gew.-%
Carbodiimid enthalten.
Schmierstoffgrundsubstanzen im Sinne der Erfindung sind insbesondere langkettige
Carbonsäureester, hergestellt aus ein- und mehrwertigen, gesättigten und unge
sättigten, verzweigten und unverzweigten, offenkettigen und cyclischen aliphati
schen, substituierten und unsubstituierten ein- und mehrwertigen aromatischen
Carbonsäuren mit ein- und mehrwertigen, gesättigten und ungesättigten, ver
zweigten und unverzweigten, offenkettigen und cyclischen aliphatischen, sub
stituierten, sterisch gehinderten und ungehinderten, sowie unsubstituierten ein- und
mehrwertigen aromatischen Alkoholen. Hierzu zählen natürliche Fette, Öle und
Wachse, d. h. Triglyceride von Fettsäuren und ebenso künstlich hergestellte Ester,
z. B. von Methanol, 2-Ethylhexanol, Glykol, Glycerin, Trimethylolpropan (im
folgenden kurz TMP) Pentaerythritol, Neopentylglykol mit Carbonsäuren wie z. B.
Sterinsäure, Ölsäure, Adipinsäure, Terephthalsäure und Trimellitsäure. Alkohol
komponenten und Carbonsäuren enthalten 1 bis 100, bevorzugt 1 bis 36 Kohlenstoff
atome.
Beispiele für geeignete Schmierstoffgrundsubstanzen auf Basis organischer Säuren
und Alkohole sind: Rapsölmethylester (im folgenden kurz: RME genannt),
Rapsölraffinat, Trimethylolpropantrioleat (im folgenden kurz TMP-Oleat genannt),
Diisotridecyladipat.
Ebenfalls geeignet als Schmierstoff-Grundsubstanzen im Sinne der Erfindung sind
Ester von anorganischen Säuren mit Alkoholen. Beispiele für anorganische Säuren
sind Phosphorige Säure (H₂PO₃), Phosphorsäure (H₃PO₄), Phosphonsäure (RP(OH)₃),
Borsäure (B(OH)₃), Kieselsäure (Si(OH)₄), "Silikonsäure" (R₂Si(OH)₂) (R = Kohlen
wasserstoff) und deren oligomeren und polymeren Anhydride. Alkohole können sein
ein- und mehrwertig, gesättigt und ungesättigt, verzweigt und unverzweigt,
offenkettig und cyclisch aliphatisch sowie substituiert und unsubstituiert ein- und
mehrwertig aromatisch. Beispiele für Alkohole sind Methanol, Ethanol, Dodecanol,
2-Ethylhexanol, Isotridecylalkohol, Oleylalkohol, Isopropylphenol, Nonylphenol und
2,4-Dimethylphenol.
Beispiele für Vertreter von Schmierstoff-Grundsubstanzen auf Basis anorganischer
Ester sind z. B. Triisopropylphenylphosphat, Trinonylphenylphosphat, Tetraethylsili
kat, Diethylpolysilikat, Dimethylpolysiloxan, Silikone.
Eine weitere Gruppe von Schmierstoff-Grundsubstanzen im Sinne der Erfindung sind
die Olefin-Dicarbonsäure-Copolymere (Handelsname: Ketjenlube; Hersteller AKZO)
Geeignete Carbodiimide sind solche der Formel (I)
Geeignete Carbodiimide sind solche der Formel (I)
(X)m-[-N=C=N-Y-]p-N=C=N-Y (I)
in der
X und Y aromatische oder araliphatische Kohlenwasserstoffreste mit 6 bis 20 C- Atomen bedeuten, die in mindestens einer Orthostellung zur Carbodiimidgruppe aromatische, aliphatische und/oder cycloaliphatische Substituenten mit mindestens 2 C-Atomen, bevorzugt verzweigte oder cyclische aliphatische Reste mit minde stens 3 C-Atomen tragen, und die Carbodiimidgruppe(n) an aromatischen Kohlen stoff gebunden ist (sind), p = 0 bis 100, bevorzugt 0 bis 50 (im Mittel) ist, wobei X noch freie Isocyanat-Gruppen enthalten kann.
X und Y aromatische oder araliphatische Kohlenwasserstoffreste mit 6 bis 20 C- Atomen bedeuten, die in mindestens einer Orthostellung zur Carbodiimidgruppe aromatische, aliphatische und/oder cycloaliphatische Substituenten mit mindestens 2 C-Atomen, bevorzugt verzweigte oder cyclische aliphatische Reste mit minde stens 3 C-Atomen tragen, und die Carbodiimidgruppe(n) an aromatischen Kohlen stoff gebunden ist (sind), p = 0 bis 100, bevorzugt 0 bis 50 (im Mittel) ist, wobei X noch freie Isocyanat-Gruppen enthalten kann.
Bevorzugt sind Carbodiimide der Formel (I), deren aromatische Reste X und Y,
beispielsweise Phenyl, in beiden Orthostellungen und gegebenenfalls in Parastel
lung zur Carbodiimidgruppe durch (cyclo-)aliphatische und/oder aromatische
Reste, beispielsweise C₁-C₆-Alkyl oder Phenyl substituiert sind, wobei einer dieser
orthoständigen Substituenten eine Methylgruppe sein kann. Besonders bevorzugt
sind Verbindungen, deren aromatische Ringe X und Y in beiden Nachbar
stellungen zur Carbodiimidgruppe durch (cyclo)aliphatische Reste substituiert sind,
wobei einer dieser orthoständigen Substituenten eine Methylgruppe sein kann, der
andere mindestens 2 C-Atome enthält.
Ganz besonders bevorzugt sind Carbodiimide, die in Orthostellung bzw. Ortho-
und Parastellung zur Carbodiimidgruppe 2 bzw. 3 Substituenten tragen, von denen
mindestens einer eine verzweigte aliphtische Kette mit mindestens 3 C-Atomen,
oder ein Cycloaliphat mit 5 oder 6 C-Atomen ist. p ist vorzugsweise 0 bis 40.
Die Carbodiimide können als Dimere, oligomere oder polymere Verbindungen
oder aus Gemischen daraus eingesetzt werden. Vorzugsweise werden dimere und
polymere Carbodiimide (p 11) eingesetzt.
Erfindungsgemäß geeignete zur Carbodiimidgruppe benachbarte Substituenten am
aromatischen Ring sind C₂-C₂₀-Alkyl- und/oder Cycloalkylgruppen, wie Ethyl-,
Propyl-, Isopropyl-, sek. Butyl-, tert.-Butyl, Cyclohexyl-, Dodecyl-, oder auch
Aryl- und Aralkylreste mit 6 bis 15 C-Atomen, wie Phenyl-, Tolyl-, Benzyl-,
Naphthylreste usw.
Besonders geeignet sind solche Carbodiimide, die in den Ortho-Stellungen zur
Carbodiimidgruppe durch iso-Propyl substituiert sind, und die gegebenenfalls in
der para-Stellung zur Carbodiimidgruppe ebenfalls durch iso-Propyl substituiert
sind.
Beispielhaft seien die folgenden Carbodiimide genannt:
Die Carbodiimide der Formel (I) können nach an sich bekannten Verfahren herge
stellt werden. Ein mögliches Herstellungsverfahren ist z. B. in der DAS 25 37 685
beschrieben. Nach der Lehre dieser Patentschrift werden organische Polyisocyanate
in Gegenwart einer geeigneten Phosphorverbindung bis zum gewünschten Grad
teilweise umgesetzt und der Katalysator anschließend mit einem geeigneten
Halogenid, z. B. einem Säurehalogenid, desaktiviert.
Polycarbodiimide können außerdem, wenn sie aus Isocyanaten hergestellt worden
sind, noch reaktionsfähige NCO-Gruppen und komplex gebundene monomere Iso
cyanate enthalten. Polycarbodiimide lassen sich beispielsweise nach der französi
schen Patentschrift 1 180 370 aus Polyisocyanaten mit katalytischen Mengen an
Phospholinen, Phospholidinen und deren Oxiden und Sulfiden herstellen. Weitere
geeignete Polycarbodiimide lassen sich herstellen aus aromatischen Di- und Poly
isocyanaten, die in o-Stellung zu allen NCO-Gruppen einen oder zwei Aryl-,
Alkyl- bzw. Aralkylsubstituenten tragen, wobei wenigstens einer der Substituenten
mindestens zwei Kohlenstoffatome aufweisen soll, unter Einwirkung von tertiären
Aminen, basisch reagierenden Metallverbindungen, carbonsauren Metallsalzen und
nicht basischen Organometallverbindungen. NCO-Gruppen-haltige Polycarbodi
imide können in der Weise modifiziert werden, daß die noch vorhandenen Iso
cyanatgruppen mit reaktionsfähigen, Wasserstoff enthaltenden Verbindungen wie
Alkoholen, Phenolen oder Aminen beseitigt werden (vgl. DE-AS 11 56 401 und
DE-OS 24 19 968).
Die erfindungsgemäßen stabilisierten Schmierstoff-Grundsubstanzen können herge
stellt werden durch Vermischen der Grundstoffe mit den Carbodiimiden in übli
chen Mischaggregaten.
Die erfindungsgemäßen Mischungen können beispielsweise eingesetzt werden für
folgende Anwendungen: Prozeßöle, Treibstoffe, Wärmeträgeröle, Motorenöle,
Fette, Metallbearbeitungsflüssigkeiten und Flugturbinenöle. Besonders geeignet
sind die erfindungsgemäßen Mischungen für Kraftübertragungsflüssigkeiten
(Hydrauliköle) und Kältemaschinenöle.
Die erfindungsgemäßen stabilisierten Schmierstoff-Grundsubstanzen können in
Verbindung mit neutralen oder alkalischen Korrosionsschutz-Additiven z. B. Cal
cium-Sulfonat (RC 4220, Rheinchemie Rheinau GmbH), aminischen und phenoli
schen Oxidationsinhibitoren, Buntmetalldesaktivatoren, metallhaltigen und metall
freien Verschleiß- und Hochdruckzusätzen sowie Stockpunktverbesserern, Ent
schäumern und Demulgatoren, Dispersants, Detergentien und Viskositätsindexver
besserern eingesetzt werden.
Durch einfaches Vermischen bei ca. 50°C wurden die erfindungsgemäßen
Mischungen von Carbodiimiden mit Schmierstoff-Grundsubstanzen hergestellt.
Diese Lösungen wurden genormten Schmierstoffprüfungen unterzogen und
hinsichtlich der hydrolytischen Beständigkeit untersucht. Hauptbewertungs
kriterium dieser Hydrolyseprüfungen ist der Anstieg der Säurezahl über den
Versuchszeitraum. Nachfolgend beschrieben sind die Testmethoden und
Ergebnisse.
Der TOST-Test ist Bestandteil vieler verschiedener Industrieölspezifikationen. Es
wird der Säurezahlanstieg als Maßzahl für den Alterungszustand des Öles verfolgt
bis die kritische Zahl von 2 mg KOH/g Öl überschnitten wird.
Einerseits trägt der Sauerstoff über einen radikalischen Sauerstoff-Oxidations
mechanismus und andererseits das Wasser über die Hydrolyse (Spaltung des Esters
in Säure und Alkoholen) zum Anstieg bei. Um die beiden Einflüsse getrennt
bewerten zu können, wurde bei einigen Prüfungen ein Gemisch von Alterungs
stabilisatoren und Korrosionsschutzprodukten (im folgenden abgekürzt AO/CI-
Paket) eingesetzt, die bekanntermaßen die Sauerstoffalterung unterdrücken. Die
Tabelle macht deutlich, daß durch Zugabe eines Carbodiimids (Handelsname:
Stabaxol 1; Hersteller: Rhein Chemie) der Säurezahlanstieg in den Prüfölen bei
Anwesenheit von ca. 17% Wasser zeitlich wesentlich verzögert werden kann.
Prüfbedingungen:
300 ml Öl → Prüfsubstanz
60 ml Wasser (dest.) → Hydrolyse
Cu-Spirale → Oxidationskatalysatoren
Eisen-Spirale → Oxidationskatalysatoren
Sauerstoff 3 l/h → Oxidation
95°C → Temperaturbelastung
Bewertung:
Zeit [h] bis Säurezahl < 2 mg KOWg
300 ml Öl → Prüfsubstanz
60 ml Wasser (dest.) → Hydrolyse
Cu-Spirale → Oxidationskatalysatoren
Eisen-Spirale → Oxidationskatalysatoren
Sauerstoff 3 l/h → Oxidation
95°C → Temperaturbelastung
Bewertung:
Zeit [h] bis Säurezahl < 2 mg KOWg
Dieser Test ist Teil von international anerkannten Hydrauliköl-Spezifikationen und
wird zur Überprüfung der hydrolytischen Beständigkeit von Flüssigkeiten heran
gezogen. Das wichtigste Prüfkriterium im ASTM-D 2619 ist der Anstieg der
Säurezahl in der wäßrigen Phase.
Prüfbedingungen:
75 g Öl → Prüfsubstanz
25 g Wasser → Hydrolyse
Cu-Blech → Katalysator
93°C → Prüftemperatur
48 h → Prüfdauer (rotierende Flaschen)
75 g Öl → Prüfsubstanz
25 g Wasser → Hydrolyse
Cu-Blech → Katalysator
93°C → Prüftemperatur
48 h → Prüfdauer (rotierende Flaschen)
Bewertung:
Anstieg der Acidität der Wasserphase nach Ablauf der Prüfzeit
Anstieg der Acidität der Wasserphase nach Ablauf der Prüfzeit
Die Zugabe von Carbodiimiden zu unterschiedlichen Schmierstoff-Grundsub
stanzen hat jeweils einen deutlich geringen Säurezahlanstieg der wäßrigen Phase
über den Versuchszeitraum zur Folge: Die Schmierstoff-Grundsubstanzen werden
bei Anwesenheit von Carbodiimiden wesentlich langsamer durch Wasser
zersetzt.
Claims (1)
- Estergruppen enthaltende Schmierstoff-Grundsubstanzen, die als Stabilisatoren 0,05 bis 5 Gew.-% Carbodiimid enthalten.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4435548A DE4435548A1 (de) | 1994-10-05 | 1994-10-05 | Stabilisierte Schmierstoff-Grundsubstanz |
EP95114956A EP0705898A3 (de) | 1994-10-05 | 1995-09-22 | Stabilisierte Schmierstoff-Grundsubstanz |
US08/534,703 US5614483A (en) | 1994-10-05 | 1995-09-27 | Stabilized lubricant base material |
CA002159696A CA2159696A1 (en) | 1994-10-05 | 1995-10-02 | Stabilised lubricant base material |
JP7276174A JPH08209169A (ja) | 1994-10-05 | 1995-10-02 | 安定化された潤滑剤ベース材料 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4435548A DE4435548A1 (de) | 1994-10-05 | 1994-10-05 | Stabilisierte Schmierstoff-Grundsubstanz |
Publications (1)
Publication Number | Publication Date |
---|---|
DE4435548A1 true DE4435548A1 (de) | 1996-04-11 |
Family
ID=6529991
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE4435548A Withdrawn DE4435548A1 (de) | 1994-10-05 | 1994-10-05 | Stabilisierte Schmierstoff-Grundsubstanz |
Country Status (5)
Country | Link |
---|---|
US (1) | US5614483A (de) |
EP (1) | EP0705898A3 (de) |
JP (1) | JPH08209169A (de) |
CA (1) | CA2159696A1 (de) |
DE (1) | DE4435548A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014180833A1 (de) | 2013-05-07 | 2014-11-13 | Rhein Chemie Rheinau Gmbh | Verfahren zur herstellung von ölformulierungen mittels bestimmter carbodiimide |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6174999B1 (en) * | 1987-09-18 | 2001-01-16 | Genzyme Corporation | Water insoluble derivatives of polyanionic polysaccharides |
JP3941150B2 (ja) * | 1997-03-07 | 2007-07-04 | 新日本理化株式会社 | エンジン油組成物 |
DE19809634A1 (de) * | 1998-03-06 | 1999-09-09 | Basf Ag | Carbodiimide und Verfahren zu deren Herstellung |
US6750182B1 (en) | 1998-10-09 | 2004-06-15 | Exxonmobil Research And Engineering Company | Polar oil based industrial oils with enhanced sludge performance |
US6235687B1 (en) | 1998-10-09 | 2001-05-22 | Exxon Research And Engineering Company | Method for producing lubrication oils possessing anti rust properties containing acidic anti rust additive and acid scavengers |
US6143702A (en) * | 1998-10-09 | 2000-11-07 | Exxon Research And Engineering Company | Lubricating oils of enhanced oxidation stability containing n-phenyl-naphthyl amines, or substituted derivatives of n-phenyl naphthyl amine and carbodiimide acid scavengers |
US7423000B2 (en) * | 1999-01-19 | 2008-09-09 | International Lubricants, Inc. | Non-phosphorous, non-metallic anti-wear compound and friction modifier |
FR2792325B1 (fr) * | 1999-06-30 | 2006-07-14 | Renault | Fluides fonctionnels de non toxiques et biodegradables a base d'esters a chaines grasses de neopolyols pour vehicules automobiles |
DE10015658A1 (de) * | 2000-03-29 | 2001-10-04 | Rhein Chemie Rheinau Gmbh | Blockcopolymere auf Basis von Polycarbodiimiden, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Hydrolysestabilisatoren |
DE10115829A1 (de) * | 2001-03-29 | 2002-10-10 | Cognis Deutschland Gmbh | Oxidationsstabiles Hydrauliköl |
US7456137B2 (en) * | 2004-12-03 | 2008-11-25 | Afton Chemical Corporation | Compositions comprising at least one carbodiimide |
US20060122077A1 (en) * | 2004-12-03 | 2006-06-08 | Bruce Wilburn | Compositions comprising at least one carbodiimide |
WO2008041492A1 (fr) * | 2006-09-29 | 2008-04-10 | Idemitsu Kosan Co., Ltd. | Lubrifiant pour machine frigorigène à compression et appareil frigorigène utilisant celui-ci |
DE102009001130A1 (de) * | 2009-02-25 | 2010-08-26 | Rhein Chemie Rheinau Gmbh | Transformatorölzusammensetzung, umfassend mindestens einen Säurefänger |
EP2290043B1 (de) * | 2009-08-24 | 2012-08-29 | Infineum International Limited | Schmierölzusammensetzung enthaltend ein Metalldialkyldithiophosphat und ein Carbodiimid |
FR2954346B1 (fr) | 2009-12-18 | 2013-02-08 | Total Raffinage Marketing | Composition additive pour huile moteur |
US20120220697A2 (en) | 2010-03-16 | 2012-08-30 | Andersen Corporation | Sustainable compositions, related methods, and members formed therefrom |
US8829097B2 (en) | 2012-02-17 | 2014-09-09 | Andersen Corporation | PLA-containing material |
US9200230B2 (en) | 2013-03-01 | 2015-12-01 | VORA Inc. | Lubricating compositions and methods of use thereof |
WO2014134506A1 (en) * | 2013-03-01 | 2014-09-04 | VORA Inc. | Lubricating compositions and methods of use thereof |
EP3053992A1 (de) | 2015-02-09 | 2016-08-10 | LANXESS Deutschland GmbH | Biodiesel |
WO2020201928A1 (en) | 2019-03-29 | 2020-10-08 | 3M Innovative Properties Company | Film comprising polylactic acid polymer suitable for graphic articles |
FR3127952A1 (fr) | 2021-10-11 | 2023-04-14 | Totalenergies Marketing Services | Carbodiimide comme additif dans des lubrifiants destinés à des systèmes de motorisation pour améliorer la compatibilité avec les élastomères |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1180370A (fr) | 1957-07-30 | 1959-06-03 | Perfectionnements apportés aux compositions de métallisation de textile | |
US2878181A (en) * | 1957-12-30 | 1959-03-17 | Pure Oil Co | Method of preparing neutral oils |
DE1156401B (de) | 1960-05-24 | 1963-10-31 | Bayer Ag | Verfahren zur Herstellung von Carbodiimiden |
NL272088A (de) * | 1960-12-02 | |||
DE1243811B (de) * | 1964-06-16 | 1967-07-06 | Bayer Ag | Schmierstoffzusatzmittel |
DE2419968A1 (de) | 1974-04-25 | 1975-12-18 | Basf Ag | Zaehe, waermealterungsbestaendige und verarbeitungsstabile polybutylenterephthalat-formmassen |
DE2537685C2 (de) | 1975-08-23 | 1989-04-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur teilweisen Carbodiimidisierung der Isocyanatgruppen von organischen Polyisocyanaten |
DE3221137A1 (de) * | 1982-06-04 | 1983-12-08 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von schwerentflammbaren fluessigkeiten mit hohem viskositaetsindex und deren verwendung |
EP0647701B1 (de) * | 1993-03-25 | 1999-10-06 | Asahi Denka Kogyo Kabushiki Kaisha | Schmiermittel für kühlschrank und dieses enthaltende schmiermittelzusammensetzung |
-
1994
- 1994-10-05 DE DE4435548A patent/DE4435548A1/de not_active Withdrawn
-
1995
- 1995-09-22 EP EP95114956A patent/EP0705898A3/de not_active Withdrawn
- 1995-09-27 US US08/534,703 patent/US5614483A/en not_active Expired - Fee Related
- 1995-10-02 CA CA002159696A patent/CA2159696A1/en not_active Abandoned
- 1995-10-02 JP JP7276174A patent/JPH08209169A/ja active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014180833A1 (de) | 2013-05-07 | 2014-11-13 | Rhein Chemie Rheinau Gmbh | Verfahren zur herstellung von ölformulierungen mittels bestimmter carbodiimide |
Also Published As
Publication number | Publication date |
---|---|
CA2159696A1 (en) | 1996-04-06 |
US5614483A (en) | 1997-03-25 |
EP0705898A3 (de) | 1997-05-21 |
JPH08209169A (ja) | 1996-08-13 |
EP0705898A2 (de) | 1996-04-10 |
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