AT243960B - Als Schmiermittel und hydraulische Flüssigkeit geeignete Stoffzusammenstellung - Google Patents
Als Schmiermittel und hydraulische Flüssigkeit geeignete StoffzusammenstellungInfo
- Publication number
- AT243960B AT243960B AT735363A AT735363A AT243960B AT 243960 B AT243960 B AT 243960B AT 735363 A AT735363 A AT 735363A AT 735363 A AT735363 A AT 735363A AT 243960 B AT243960 B AT 243960B
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Description
<Desc/Clms Page number 1> Als Schmiermittel und hydraulische Flüssigkeit geeignete Stoffzusammenstellung EMI1.1 <Desc/Clms Page number 2> sehrsche Gruppen aufweisenden organischen Polyamin durch Substitution dieser Aminogruppen mit 4-und 6-se- kundär-Amino- und/oder tertiär-Amino-l. 3, 5-triazinyl- (2) -Gruppen ableiten, wobei gegebenenfalls inert substituierte aliphatische und cycloaliphatische Gruppen, die Stickstoffsubstituenten bilden und die Stickstoffsubstituenten tertiärer Aminogruppen auch, gegebenenfalls unter Einschluss von Heteroatomen, ringförmig verbunden sein können. Als zwei oder mehr acylierbare Aminogruppen aufweisende organische Amine verwendet man bei der Herstellung der erfindungsgemäss verwendbaren Melaminderivate mit Vorteil Polyamine gesättigter oder doch teilweise gesättigter Kohlenwasserstoffe, die inerte Substituenten und Heteroatome als Ketten-, Brücken- oder Ringglieder enthalten können. Sie können jedoch auch aromatische Ringe enthalten, u. zw. einen oder mehrere vorzugsweise unkondensierte aromatische Ringe. Sie können ferner Heteroringe enthalten oder aus Heteroringen bestehen ; es handelt sich dabei vorteilhaft um gesättigte oder zumindest um teilweise gesättigte Heteroringe. Als nur eine acylierbare Aminogruppe aufweisende Aminoverbindungen verwendet man bei der Herstellung der Melaminderivate primäre oder sekundäre Aminoverbindungen mit aliphatischen, alicyclischen, araliphatischen, aromatischen, in diesem Fall mit vorzugsweise ein-oder mehrkernigen, jedoch nicht kondensierten aromatischen Gruppen, oder gesättigte oder doch teilweise gesättigte Stickstoffringe, wie Pyrrolidin, Piperidin, Hexamethylenimin, Morpholin und N-Monoalkyl-oder N-Monoaralkyl-piper- azine usw. Auch in diesen Aminen können die organischen Stickstoffsubstituenten noch inert weitersub- stituiert sein, beispielsweise können aliphatische Reste Alkoxy-, Alkylmercapto-, Phenoxy- oder Phenylmercaptogruppen, alicyclische und aromatische Gruppen Alkylsubstituenten und aromatische Ringe überdies Halogen, wie Fluor, Chlor oder Brom enthalten. Vorzugsweise sind die Stickstoffsubstituenten primärer und sekundärer Amine gesättigte oder doch teilweise gesättigte Reste, beispielsweise normale oder EMI2.1 Die erfindungsgemässverwendbaren, mehrere 1,3, 5-Triazinringe aufweisenden Melaminderivate entsprechen der allgemeinen Formel EMI2.2 In dieser Formel bedeutet A den Rest eines n-acylierbare Aminogruppen enthaltenden, vorzugsweise EMI2.3 genannten und in aromatischen Ringen überdies noch beispielsweiseAlkylgruppen mit 1-18 Kohlenstoffatomen und Halogen, wie Fluor, Chlor oder Brom enthalten kann, wobei die zwei Stickstoffsubstituenten einer Aminogruppe auch, gegebenenfalls unter Einschluss von Heteroatomen, wie Sauerstoff, Schwefel oder weiterem Stickstoff, ringförmig verbunden sein können ; entsprechende Substituenten in verschiedenen 1, 3,5-Triazinringen können gleich oder voneinander verschieden sein. Die erfindungsgemäss verwendbaren Melaminderivate können Gemische von primären, sekundären und tertiären AmiDen enthalten. Sie lassen sich dank ihrer grossen Wärmestabilität leicht durch Destilla- <Desc/Clms Page number 3> tion im Hochvakuum in reiner Form gewinnen. Die Reinigung der Melaminderivate kann auch durch Extraktion mit einem selektiven Lösungsmittel wie Essigsäure, durch Behandlung mit einer Bleicherde wie Tonsil AC oder einer Absorptionserde wie Celite FC oder mit einem Ionen-Austauscher wieAmberlite IR 120 durchgeführt werden. Die erfindungsgemäss verwendbaren Melaminderivate sind bei Raumtemperatur entweder flüssige, halbfeste fettähnliche oder wachsartige feste, nichtkristalline Stoffe, die hervorragend thermostabil und wenig flüchtig sind. Dank ihrer Eigenschaft, auf den verschiedensten Materialien Schmierfilme und bei extremer Beanspruchung keine sauren Zersetzungsprodukte zu bilden, sind sie als Schmiermittel für schwer arbeitende Maschinenteile und als hydraulische Flüssigkeiten für starke Beanspruchungen geeignet, beispielsweise als Turbinenöle oder als Schmieröle für Gasturbinen. Auch zeichnen sich erfindungsgemäss verwendbare Melamine durch einen hohen Entzündungspunkt aus. Er wurde nach ASTM-Designation : D 93 - 58 T (The American Society For Testing Materials, [1951] Race St. Philadelphia 3, PA) bestimmt. Er beträgt beispielsweise für die Verbindung No. 37 der Tabelle I 3500C und liegt somit bedeutend höher als derjenige der Sebacate von Alkanolen. Ferner ist die Dichte der erfindungsgemäss verwendbaren Melamine günstig. Vor bisher bekanntgewordenen und als Turbinenschmieröle empfohlenen Stoffen, wie beispielsweise den ortho-Phosphorsäureestern organischer Hydroxylverbindungen, zeichnen sich die erfindungsgemässver- wendbaren Melaminderivate durch viel geringere Korrosionswirkung, vor Estern höherer Polycarbonsäuren mit Polyalkoholen durch geringere Quellwirkung auf Kunststoffe, wie beispielsweise auf hochmolekulare Copolymere aus Butadien und Acrylnitril (z. B. HYCAR 38 der Firma Goodrich in Arkon, Ohio, USA), vor Estern aus Pentaerythrit und Monocarbonsäuren mittlerer Kettenlänge durch erheblich geringereAusscheidung von Verharzungs- und Verkohlungsprodukten aus. Bemerkenswert ist auch die sehr gute Säure- und Alkalibeständigkeit der erfindungsgemäss verwendbaren Melaminderivate. In flüssigem Zustand zeigen sie eine mittlere bis hohe Viskosität ; ihr grosser Vorteil besteht darin, dass diese Viskosität wenig temperaturabhängig ist. Die erfindungsgemäss verwendbaren Melamine können als Mehrzweckschmiermittel verwendet werden. Für einen gegebenen Zweck erwünschte Eigenschaften kann man auch durch Herstellung geeigneter Gemische dieser Melamine unter sich oder mit andern synthetischen oder mineralischen Schmiermitteln erhalten. Die erfindungsgemäss verwendbaren Melamine eignen sich darum zum Schmieren von harten Oberflächen, weil sie bei der Berührung mit diesen Oberflächen festhaftende Oberflächenfilme bilden, beispielsweise zum Schmieren der Oberfläche von Metallen sowie deren Legierungen, der Oberflächen von Silikaten, wie z. B. von Gläsern, sowie von andern schmierbedürftigen Materialien, wie z. B. von Dichtungsringen aus Gummi. Die erfindungsgemäss verwendbaren N, N', N"-substituierten Melamine können für sich allein verwendet werden; sie können aber auch Zusätze enthalten. So werden sie, wenn sie zwecks Ausnutzung ihrer günstigen Hitzestabilität oberhalb 1500C angewendet werden sollen, zweckmässig mit Antioxydantien vermischt,. um die ab dieser Temperatur einsetzende Autoxydation zu verhindern. Der Anteil an Antioxydantien beträgt hiebei etwa 0, 01-5% der Melamine. Als Antioxydantien kommen homo-oder heterocyclische aromatische Amine, hydroxylsubstituierte Aromate, Aminohydroxyarylverbindungen sowie gewisse heterocyclische Verbindungen in Frage. Unter den Aminen sind im allgemeinen die sekundären Monoamine, besonders die Diarylamine mit homo- und heterocyclischen aromatischen Resten, sowie die aromatischen Diamine, deren vorzugsweise sekundäre Aminsubstituenten entweder ortho- oder vorzugsweise para-Stellungen einnehmen, besonders wertvoll. Beispiele von Antioxydantien aus der Klasse der homo-und heterocyclischen aromatischen Diarylamine sind Diphenylamine, Phenylnaphthylamine, Phenylacenaphthenyl-amine ; 4, 4'-Dinaphthylamino- dipheny1ï Thiazolyl- (2) -naphthylamin8i als aromatische Diamine kommen beispielsweise in Betracht : EMI3.1 Unter den Antioxydantien aus der Klasse der hydroxylsubstituierten Aromaten, die besonders bei nicht zu hohen Arbeitstemperaturen (d. h. unterhalb 200 - 3000C je nach Typ und Substrat) eingesetzt werden, sind diejenigen mit einer sterisch gehinderten Hydroxylgruppe sowie die Derivate von Dihydroxyarylverbindungen, deren Hydroxylgruppen in 0- oder p-Stellung zueinander stehen, geeignet. Besonders wertvolle Beispiele brauchbarer Verbindungen sind die Monophenolderivate, wie 2, 4-Dimethyl-6-tert.-butyl- phenol, 2, 6-Di-tert.-butyl-4-äthylphenol, 2, 6-Bis- (l'-methylcyclohexyl)-4-methylphenol, 2, 6-Di- <Desc/Clms Page number 4> EMI4.1 gallat, Hydrochinon, Butylhydroxy-anisol, Hydrochinonmonobenzyläther. Unter den Aminohydroxyarylverbindungen sind als Antioxydantien diejenigen Derivate, in denen Amino- und Hydroxylgruppen in p-Stellung zueinander stehen, besonders geeignet. Beispiele sind : p-Hydroxydiphenylamin, p-Hydroxyoctylanilin, p-Hydroxy-N-y-aminopropylanilin. Unter den heterocyclischen Antioxydantien sind cyclische Imide am bekanntesten ; daneben kommen aber auch stickstofffreie Heterocyclen in Frage, soweit sie nicht in die Klasse der heterocyclischen Amine fallen. Beispiele sind : Phenothiazin, Iminodibenzyl, 5-Äthyl-10, 10-diphenyl-phenosilazin, 6-Methoxy- EMI4.2 Ferner können erfindungsgemäss verwendbare N, N', N"-substituierte Melamine auch Hochdruckadditive, wie Phosphite, Phosphate, geschwefeltes Spermöl usw., Barium-oder Calcium-mahagonisulfonate, Korrosionsschutzmittel, wie Sarkosine oder Benztriazole, den Stockpunkt erniedrigende Mittel und möglicherweise auch Antischaummittel auf Siliconbasis'enthalten. Ferner umfasst die Erfindung aus erfindungsgemäss verwendbaren Melaminderivaten durch Beifügung von üblichen Verdickungsmitteln hergestellte Schmierfette. Als solche Verdickungsmittel kommen beispielsweise Metallseifen, Bentonite, Phthalocyanine, Violanthrone, Indanthrene, Flavanthrene, Pyranthrone, Isatine, Indigo in Frage. Die folgenden Beispiele veranschaulichen die Herstellung und die Brauchbarkeit der erfindungsgemäss verwendbaren Melaminderivate mit mehr als einem 1, 3, 5-Triazinring. Darin sind die Teile, sofern etwas anderes nicht ausdrücklich vermerkt ist, als Gewichtsteile verstanden. Die Temperaturen sind, soweit nicht anders gekennzeichnet, in Celsiusgraden angegeben. Gewichtsteile stehen zu Volumsteilen im Verhältnis von Gramm zu Milliliter. Beispiel 1 : Man verrührt 50 Teile 1,6-Bis-[2'=diäthylamino-4'-dibutylamino-s-triazinyl-(6')- - amino]-hexan, das eine Viskosität von 12'160 Centistokes bei 37, 8 und 120, 9 Centistokes bei 98, 8 aufweist, mit 50 Teilen eines Polypropylenglykolsebazinsäureesters (im Handel als Reoplex 100 der Fa. Geigy Company Ltd. Manchester, England). Die Mischung zeigt die guten Schmiereigenschaften der Komponenten. und die Viskosität der Mischung beträt bei 37,8 6'263 Gentistokes und bei 98, 80265 Cen- EMI4.3 apparat (der Fa. Janke & Kunkel, Stauffen, Baden, Westdeutschland) verrührt. Zu dieser Mischung werden langsam 9 Teile 1, 6-Bis-[2'-diäthylamino-4'-dibutylamino-s-trizazinyl-(6')-amino]-hexan zugegeben und das Ganze 45 min gerührt. Die so erhaltene homogene Masse wird auf der Glasoberfläche mit dem Spachtel durchgearbeitet, bis das überschüssige Benzol verdunstet ist. Die erhaltene Masse wird während 45 min auf 1500 geheizt und nach dem Abkühlen nochmals verspachtelt. Es entsteht ein weiches, gut verarbeitbares Schmierfett. Beuispiel3 :99Teile1,6-Bis-[2',4'-bis-dibutylamino-s-triazinyl-(6')-amino]-hexanund1Teil Iminodibenzyl werden zusammen verrührt, bis sich das letztere vollständig gelöst hat. Die erhaltene Mischung zeigt gegenüber der reinen Triazinverbindung eine verbesserte Oxydationsstabilität. Ähnliche Resultate werden erhalten, wenn an Stelle der obigen Verbindung die übrigen in diesem Dokument erwähnten, synthetisieren Verbindungen mit den in der Technik üblichen zweckentsprechen- den Antioxydantien in Mengen von 0, 01 bis 5% versetzt werden. Die folgende Tabelle I enthält Beispiele von erfindungsgemäss verwendbaren N, N', N"-substituierten Melaminderivaten der allgemeinen Formel <Desc/Clms Page number 5> EMI5.1 EMI5.2 EMI5.3 <Desc/Clms Page number 6> EMI6.1 EMI6.2 <Desc/Clms Page number 7> EMI7.1 EMI7.2 <Desc/Clms Page number 8> EMI8.1 EMI8.2 EMI8.3 <Desc/Clms Page number 9> A. S. T. M. ist die Abkürzung für American Society for Testing Materials. Kolonnen 5 und 6 geben den Gewichtsverlust innerhalb 6 h in Prozent an, den eine Probe von 25 cm3 beim Erhitzen auf 380 bzw. 4000C in einem Reaktionsrohr aus Glas von zirka 25 mm Durchmesser unter gleichzeitigem Durchleitenvon Stickstoff (2 l/h) erleidet. Kolonne 7 gibt die Änderung der bei 210 F gemessenen Viskosität in Prozent an, welche die Probe bei der oben beschriebenen 6stündigen Hitzealterung erlitten hat. Tabelle II EMI9.1 <tb> <tb> Viskosität <SEP> in <tb> Centistokes <SEP> bei <SEP> Gewichtsverlust <SEP> Viskositätsänderung <SEP> nach <tb> 1000F <SEP> 210 F <SEP> A. <SEP> S. <SEP> T. <SEP> M. <SEP> nach <SEP> 6 <SEP> h <SEP> 6 <SEP> h <SEP> in <SEP> Centistokes <tb> Nr. <SEP> (37, <SEP> 8 C) <SEP> (98, <SEP> 8OC) <SEP> Slope <SEP> C <SEP> % <SEP> in <SEP> % <SEP> gemessen <SEP> bei <SEP> 210 F <tb> 1 <SEP> 12'160 <SEP> 120, <SEP> 9 <SEP> 0,740 <SEP> " <SEP> 380 <SEP> 2, <SEP> 34.. <SEP> 5, <SEP> 4 <SEP> <tb> 400 <SEP> 7, <SEP> 42-4, <SEP> 6 <SEP> <tb> 2 <SEP> 2794 <SEP> 380 <SEP> 4, <SEP> 41-81, <SEP> 3 <SEP> <tb> 400 <SEP> 15, <SEP> 97 <SEP> - <SEP> 91, <SEP> "9 <SEP> <tb> 3 <SEP> 129, <SEP> 5 <SEP> 380 <SEP> 2,61 <SEP> + <SEP> 21, <SEP> 3 <SEP> <tb> 400 <SEP> 8,74 <SEP> +118, <SEP> 0 <SEP> <tb> 4 <SEP> 101, <SEP> 7 <SEP> 380 <SEP> 6, <SEP> 00 <SEP> + <SEP> 1, <SEP> 89 <SEP> <tb> 400 <SEP> 18, <SEP> 05 <SEP> + <SEP> 8, <SEP> 95 <SEP> <tb> 5 <SEP> 1847 <SEP> 58, <SEP> 76 <SEP> 0, <SEP> 675 <SEP> 380 <SEP> 14, <SEP> 80-43, <SEP> 0 <SEP> <tb> 400 <SEP> 30,80 <SEP> + <SEP> 12, <SEP> 36 <SEP> <tb> 6 <SEP> 290,7 <SEP> 380 <SEP> 3, <SEP> 42 <SEP> +18, <SEP> 6 <SEP> <tb> 400 <SEP> 10. <SEP> 94-6, <SEP> 1 <SEP> <tb> 7 <SEP> 347, <SEP> 9 <SEP> 380 <SEP> 3, <SEP> 96 <SEP> + <SEP> 3, <SEP> 4 <SEP> <tb> 400 <SEP> 11, <SEP> 76-23, <SEP> 8 <SEP> <tb> 8 <SEP> 115, <SEP> 5. <SEP> 380 <SEP> 2, <SEP> 69 <SEP> - <SEP> 5, <SEP> 62 <SEP> <tb> 400 <SEP> 9, <SEP> 84 <SEP> + <SEP> 3, <SEP> 03 <SEP> <tb> 9 <SEP> 93, <SEP> 28 <SEP> 380 <SEP> 2, <SEP> 54.. <SEP> 2, <SEP> 34 <SEP> <tb> 400 <SEP> 8,32 <SEP> + <SEP> 1,23 <tb> 10 <SEP> 380 <SEP> 1,81 <tb> 400 <SEP> 5, <SEP> 50 <SEP> <tb> 11 <SEP> 306, <SEP> 4 <SEP> 380 <SEP> 1, <SEP> 92 <SEP> - <SEP> 4, <SEP> 28 <tb> 400 <SEP> 5, <SEP> 84 <SEP> + <SEP> 30, <SEP> 10 <SEP> <tb> 12 <SEP> 253, <SEP> 0 <SEP> 380 <SEP> 6, <SEP> 00-67, <SEP> 4 <SEP> <tb> 400 <SEP> 18, <SEP> 19 <SEP> -70, <SEP> 7 <tb> 13, <SEP> 380 <SEP> 7, <SEP> 15 <tb> 400 <SEP> 22, <SEP> 15 <tb> 14 <SEP> 380 <SEP> 3, <SEP> 68 <SEP> <tb> - <SEP> 400 <SEP> 22,54 <tb> 16 <SEP> 380 <SEP> 2, <SEP> 51 <SEP> <tb> 400 <SEP> 7, <SEP> 04 <SEP> <tb> <Desc/Clms Page number 10> Tabelle II (Fortsetzung) EMI10.1 <tb> <tb> Viskosität <SEP> in <SEP> Viskositätsänderung <SEP> nach <tb> Centistokes <SEP> bei <SEP> Gewichtsverlust <SEP> 6 <SEP> h <SEP> in <SEP> Centistokes <tb> 1000 <SEP> F <SEP> 2100F <SEP> A. <SEP> S. <SEP> T. <SEP> M. <SEP> nach <SEP> 6 <SEP> h <SEP> in <SEP> % <SEP> gemessen <SEP> bei <SEP> 2100 <SEP> F <SEP> <tb> Nr. <SEP> (37,8 C) <SEP> (98,8 C) <SEP> Slope <SEP> C <SEP> % <tb> 24 <SEP> 16'860 <SEP> 129, <SEP> 5 <SEP> 0,781 <SEP> 380 <SEP> 1, <SEP> 43-4, <SEP> 5 <SEP> <tb> 400 <SEP> 5, <SEP> 51-5, <SEP> 8 <SEP> <tb> 27 <SEP> 3'910 <SEP> 101,2 <SEP> 0, <SEP> 644 <SEP> 380 <SEP> 3, <SEP> 00-1, <SEP> 1 <SEP> <tb> 400 <SEP> 10, <SEP> 80-7, <SEP> 3 <SEP> <tb> 28 <SEP> 24'480 <SEP> 1226 <SEP> 0, <SEP> 822 <SEP> 380 <SEP> 2, <SEP> 02 <SEP> + <SEP> 15,4 <tb> 400 <SEP> 6, <SEP> 80 <SEP> + <SEP> 48, <SEP> 7 <SEP> <tb> 29 <SEP> 3'664 <SEP> 95,5 <SEP> 0, <SEP> 650 <SEP> 380 <SEP> 2, <SEP> 64 <SEP> + <SEP> 11, <SEP> 1 <SEP> <tb> 400 <SEP> 11, <SEP> 10 <SEP> + <SEP> 14, <SEP> 6 <SEP> <tb> 30 <SEP> 189,7 <SEP> 380 <SEP> 3, <SEP> 53 <SEP> - <SEP> 10,8 <tb> 400 <SEP> 6, <SEP> 94 <SEP> + <SEP> 5, <SEP> 5 <SEP> <tb> 31 <SEP> 2'183 <SEP> 683 <SEP> 0, <SEP> 657 <SEP> 380 <SEP> 15, <SEP> 42 <SEP> - <SEP> 36,15 <tb> 400 <SEP> 29, <SEP> 55 <SEP> +115,3 <tb> 32 <SEP> 1851, <SEP> 0 <SEP> 380 <SEP> 3,11 <SEP> oF <SEP> 10,1 <SEP> <tb> 400 <SEP> 7, <SEP> 88-21, <SEP> 34 <SEP> <tb> 33 <SEP> 84, <SEP> 82 <SEP> 380 <SEP> 5, <SEP> 83-27, <SEP> 5 <SEP> <tb> 400 <SEP> 16, <SEP> 44-49, <SEP> 9 <SEP> <tb> 34 <SEP> 46, <SEP> 35 <SEP> 380 <SEP> 3, <SEP> 92-12, <SEP> 9 <SEP> <tb> 400 <SEP> 14, <SEP> 72 <SEP> <tb> 35 <SEP> 118, <SEP> 8 <SEP> 380 <SEP> 3, <SEP> 8 <SEP> + <SEP> 6, <SEP> 24 <SEP> <tb> 400 <SEP> 17, <SEP> 0 <SEP> <tb> 36 <SEP> 306, <SEP> 4 <SEP> 380 <SEP> 1, <SEP> 92... <SEP> 4, <SEP> 28 <SEP> <tb> 400 <SEP> 5, <SEP> 86 <SEP> + <SEP> 30, <SEP> 1 <SEP> <tb> 37 <SEP> 380 <SEP> 5, <SEP> 42 <SEP> <tb> 400 <SEP> 16, <SEP> 67 <SEP> <tb> 38 <SEP> 380 <SEP> 6, <SEP> 07 <SEP> <tb> 400 <SEP> 17, <SEP> 95 <SEP> <tb> PATENTANSPRÜCHE : 1. Als Schmiermittel und als hydraulische Flüssigkeit geeignete Stoffzusammenstellung, dadurch gekennzeichnet, dass sie mindestens eine N, N', N"-substituierte Melaminverbindung, die mehr als einen 1, 3, 5-Triazinring aufweist, und die sich von einem mehr als eine acylierbare Aminogruppe aufweisenden, organischen Polyamin durch Substitution dieser Aminogruppen mit 4-und 6-sekundär-Amino- und/oder tertiär-Amino-1,3,5-triazinyl-(2)-Gruppen ableitet, wobei gegebenenfalls inert substituierte aliphatische, cycloaliphatische, araliphatische und-jedoch nur einmal in einer Melamingruppeauch ein-oder mehrkernige, jedoch nicht kondensierte aromatische Gruppen, die Stickstoffsubstituenten bilden, und die Stickstoffsubstituenten tertiärer Aminogruppen auch, gegebenenfalls unter Einschluss von Heteroatomen, ringförmig verbunden sein können und mindestens einen Zusatzstoff enthält.
Claims (1)
- 2. Stoffzusammenstellung gemäss Anspruch 1, dadurch gekennzeichnet, dass sie mindestens ein im Anspruch 1 verwendetes Melaminderivat und einen weiteren Stoff aus der Reihe der hochge- <Desc/Clms Page number 11> reinigten Mineralöle, der synthetischen Schmieröle auf Esterbasis, der Siliconöle, der Antioxydantien, derVerdickungsmittel, der stockpunkterniedrigenden Mittel, der Hochdruckadditive und Korrosionsschutzmittel enthält.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH813061A CH420456A (de) | 1961-07-07 | 1961-07-07 | Verwendung von bei den Anwendungsbedingungen flüssigen bis fettartigen N,N',N''-substituierten Melaminen als hitzebeständige, synthetische Schmiermittel und hydraulische Flüssigkeiten |
CH813161A CH420178A (de) | 1961-07-07 | 1961-07-07 | Verfahren zur Herstellung von Triazinverbindungen |
Publications (1)
Publication Number | Publication Date |
---|---|
AT243960B true AT243960B (de) | 1965-12-10 |
Family
ID=25702838
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT735363A AT243960B (de) | 1961-07-07 | 1962-07-06 | Als Schmiermittel und hydraulische Flüssigkeit geeignete Stoffzusammenstellung |
AT543862A AT247354B (de) | 1961-07-07 | 1962-07-06 | Verfahren zur Herstellung von neuen, mindestens zwei 1,3,5-Triazinringe aufweisenden N,N',N"-substituierten Melaminderivaten |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT543862A AT247354B (de) | 1961-07-07 | 1962-07-06 | Verfahren zur Herstellung von neuen, mindestens zwei 1,3,5-Triazinringe aufweisenden N,N',N"-substituierten Melaminderivaten |
Country Status (10)
Country | Link |
---|---|
US (3) | US3290307A (de) |
AT (2) | AT243960B (de) |
BE (2) | BE619876A (de) |
CS (1) | CS167214B2 (de) |
DE (2) | DE1444843A1 (de) |
DK (2) | DK115860B (de) |
FR (2) | FR1328169A (de) |
GB (3) | GB999614A (de) |
NL (2) | NL280661A (de) |
SE (1) | SE319774B (de) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL274218A (de) * | 1961-02-01 | |||
US3505322A (en) * | 1962-11-28 | 1970-04-07 | American Cyanamid Co | O-substituted oxyamino-s-triazines |
US3374235A (en) * | 1963-12-31 | 1968-03-19 | Geigy Chem Corp | S-triazines |
US3378490A (en) * | 1965-10-08 | 1968-04-16 | Chevron Res | Lubricant compositions and antioxidants therefor |
CH476098A (de) * | 1965-10-12 | 1969-07-31 | Geigy Ag J R | Als Schmiermittel geeignete Mischung |
US3912518A (en) * | 1966-10-27 | 1975-10-14 | Ciba Geigy Corp | 2-Guanidino-4,6-bis-amino-s-triazines |
BE791173A (fr) * | 1971-11-10 | 1973-05-09 | Degussa | Derives de s-triazines contenant des groupes naphtylamino et leur utilisation |
US3888773A (en) * | 1972-04-27 | 1975-06-10 | Mobil Oil Corp | Nitrogen compounds linked to a heterocyclic ring as multifunctional additives in fuel and lubricant compositions |
US3969253A (en) * | 1974-01-02 | 1976-07-13 | Borg-Warner Corporation | Method for lowering the minimum pour temperature of fatty acids |
US4116875A (en) * | 1975-05-09 | 1978-09-26 | Mobil Oil Corporation | Multifunctional substituted triazine functional fluid additives and compositions containing same |
JPS5618626A (en) * | 1979-07-25 | 1981-02-21 | Oji Yuka Gouseishi Kk | Synthetic paper having excellent luster and slip |
DE3006803A1 (de) * | 1980-02-23 | 1981-09-03 | Bayer Ag, 5090 Leverkusen | Vulkanisationsbeschleuniger auf basis von melaminderivaten, melaminderivate enthaltende kautschukmassen sowie ein verfahren zur vulkanisation von kautschuken |
DE3279346D1 (en) * | 1981-07-20 | 1989-02-16 | American Cyanamid Co | Novel light stabilizers for polymers |
US4786672A (en) * | 1986-07-31 | 1988-11-22 | Ciba-Geigy Corporation | Anilinotriazines and the use thereof |
GB8728675D0 (en) * | 1987-12-08 | 1988-01-13 | Ciba Geigy Ag | Compounds & compositions |
DE3927623A1 (de) * | 1989-08-22 | 1991-02-28 | Hoechst Ag | N,n'-bis-1,3,5-triazin-6-yl-piperazine und verfahren zu ihrer herstellung |
US5507963A (en) * | 1994-05-10 | 1996-04-16 | Ciba-Geigy Corporation | Condensation products of melamine, (benzo) triazoles and aldehydes |
US5730906A (en) * | 1996-07-12 | 1998-03-24 | Exxon Research And Engineering Company | Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils (Law406) |
US5714441A (en) * | 1996-07-12 | 1998-02-03 | Exxon Research And Engineering Company | Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils |
US5750475A (en) * | 1996-07-12 | 1998-05-12 | Exxon Research And Engineering Company | Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils |
US7018960B2 (en) * | 2001-06-11 | 2006-03-28 | Fuji Photo Film Co., Ltd. | Lubricant composition, method for using and preparing thereof and molecular complex compound used for the same |
BRPI0611811A2 (pt) | 2005-06-10 | 2008-12-09 | Prometic Biosciences Ltd | ligantes de ligaÇço À proteÍna |
ES2699585T3 (es) * | 2006-12-15 | 2019-02-11 | Nantbio Inc | Derivados de triazina y sus aplicaciones terapéuticas |
GB0703831D0 (en) * | 2007-02-28 | 2007-04-11 | Croda Int Plc | Engine lubricants |
EP3263560A1 (de) | 2016-06-29 | 2018-01-03 | Borealis Agrolinz Melamine GmbH | Neuartige triazin-vorkondensierte aldehydkondensationsprodukte und verfahren zur herstellung davon |
EP3263561A1 (de) | 2016-06-29 | 2018-01-03 | Borealis Agrolinz Melamine GmbH | Neuartiges triazin-vorkondensat und verfahren zur herstellung davon |
WO2018057364A1 (en) * | 2016-09-20 | 2018-03-29 | Lanxess Solutions Us Inc. | Lubricant compositions stabilized by mixtures of diarylamine and hydroxydiarylamine antioxidants |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA552928A (en) * | 1958-02-11 | G. Boatright Leslie | Preparation of substituted melamines from urea, amines, silica gel, etc. | |
US2544071A (en) * | 1951-03-06 | Diethylenetrimelamine and method | ||
US2279561A (en) * | 1940-05-15 | 1942-04-14 | Du Pont | Stabilization of viscous petroleum oils |
US2276162A (en) * | 1940-12-17 | 1942-03-10 | Tide Water Associated Oil Comp | Stabilized mineral oil |
US2714057A (en) * | 1951-07-21 | 1955-07-26 | Universal Oil Prod Co | Stabilization of organic compounds |
US2909421A (en) * | 1955-01-14 | 1959-10-20 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
US2980637A (en) * | 1957-12-04 | 1961-04-18 | Monsanto Chemicals | Coating compositions containing aminoplast resins |
GB919267A (en) * | 1958-07-15 | 1963-02-20 | Albright & Wilson Mfg Ltd | Improvements in or relating to the manufacture of substituted organic phosphine derivatives |
US2984624A (en) * | 1959-07-31 | 1961-05-16 | Gulf Research Development Co | Lubricating oil thickened to a grease with a mixture of a 1, 3, 5-triazine compound and an organophilic siliceous compound |
US3055897A (en) * | 1959-08-08 | 1962-09-25 | Therachemie Chem Therapeut | Process for the production of triazineperhydrate compounds |
US3206407A (en) * | 1961-11-20 | 1965-09-14 | Shell Oil Co | Organic functional fluids and lubricants containing polymeric s-triazines |
-
0
- BE BE619875D patent/BE619875A/xx unknown
- NL NL280662D patent/NL280662A/xx unknown
- DE DENDAT1302636D patent/DE1302636B/de active Pending
- NL NL280661D patent/NL280661A/xx unknown
- BE BE619876D patent/BE619876A/xx unknown
-
1962
- 1962-07-02 GB GB25311/62A patent/GB999614A/en not_active Expired
- 1962-07-05 GB GB2330/65A patent/GB1013223A/en not_active Expired
- 1962-07-05 GB GB25910/62A patent/GB1013222A/en not_active Expired
- 1962-07-06 DE DE19621444843 patent/DE1444843A1/de active Pending
- 1962-07-06 AT AT735363A patent/AT243960B/de active
- 1962-07-06 FR FR903250A patent/FR1328169A/fr not_active Expired
- 1962-07-06 DK DK301762AA patent/DK115860B/da unknown
- 1962-07-06 AT AT543862A patent/AT247354B/de active
- 1962-07-06 CS CS4077A patent/CS167214B2/cs unknown
- 1962-07-06 SE SE7625/62A patent/SE319774B/xx unknown
- 1962-07-06 DK DK260463AA patent/DK102689C/da active
- 1962-07-06 FR FR903249A patent/FR1328168A/fr not_active Expired
-
1963
- 1963-01-03 US US249120A patent/US3290307A/en not_active Expired - Lifetime
-
1964
- 1964-10-21 US US405618A patent/US3250708A/en not_active Expired - Lifetime
-
1965
- 1965-10-12 US US495302A patent/US3322763A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
NL280662A (de) | 1900-01-01 |
GB1013223A (en) | 1965-12-15 |
GB1013222A (en) | 1965-12-15 |
FR1328169A (fr) | 1963-05-24 |
FR1328168A (fr) | 1963-05-24 |
DE1444843A1 (de) | 1969-10-09 |
BE619875A (de) | 1900-01-01 |
GB999614A (en) | 1965-07-28 |
SE319774B (de) | 1970-01-26 |
BE619876A (de) | 1900-01-01 |
DK102689C (da) | 1965-09-27 |
US3250708A (en) | 1966-05-10 |
CS167214B2 (de) | 1976-04-29 |
US3322763A (en) | 1967-05-30 |
NL280661A (de) | 1900-01-01 |
US3290307A (en) | 1966-12-06 |
DK115860B (da) | 1969-11-17 |
DE1302636B (de) | 1971-09-16 |
AT247354B (de) | 1966-06-10 |
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