DE2601719C2 - - Google Patents
Info
- Publication number
- DE2601719C2 DE2601719C2 DE2601719A DE2601719A DE2601719C2 DE 2601719 C2 DE2601719 C2 DE 2601719C2 DE 2601719 A DE2601719 A DE 2601719A DE 2601719 A DE2601719 A DE 2601719A DE 2601719 C2 DE2601719 C2 DE 2601719C2
- Authority
- DE
- Germany
- Prior art keywords
- examples
- benzotriazole
- alkylene
- formula
- additives
- 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.)
- Expired
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
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- 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
- 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
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/08—Inorganic acids or salts thereof
- C10M2201/082—Inorganic acids or salts thereof containing nitrogen
- C10M2201/083—Inorganic acids or salts thereof containing nitrogen nitrites
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/085—Phosphorus oxides, acids or salts
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/087—Boron oxides, acids or salts
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- 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
- C10M2205/026—Butene
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
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- C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/16—Naphthenic acids
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/22—Acids obtained from polymerised unsaturated acids
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- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- 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
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- C10M2215/066—Arylene diamines
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Description
Die Erfindung betrifft Additive für hydraulische Flüssigkeiten.
Benzotriazol und Derivate davon sind seit vielen Jahren als
wirksame Metallpassivatoren bekannt, insbesondere für Kupfer,
und zwar zur Anwendung zahlreicher Substrate. Benzotriazol
selbst und viele seiner Derivate sind jedoch in ihrer Anwendung
wegen ihrer schlechten Löslichkeit, insbesondere in
Mineralölen, beschränkt. So ist zum Beispiel aus DE-OS 15 21 762
5,5′-Methylen-bisbenzotriazol als Metallpassivator mit guter
Wirksamkeit bekannt.
Wir haben nun bestimmte, bisher unbekannte Benzotriazolderivate
gefunden, die eine verbesserte Löslichkeit in
vielerlei Hydraulikflüssigkeitsmedien, einschließlich
wäßrige Medien und welche auf Ölbasis, haben und zugleich
gute Metallpassivation besitzen.
Die Erfindung betrifft demgemäß neue Benzotriazole der
allgemeinen Formel I
worin R Wasserstoff oder C₁-C₄-Alkyl bedeutet, R₁ und R₂ gleich
sind und HO-(alkylen)- bedeuten, wobei (alkylen) Alkylen mit
2 oder 3 C-Atomen ist.
Ist R C₁-C₄-Alkyl, so handelt es sich um geradkettiges oder
verzweigtes Alkyl wie beispielsweise Methyl, Aethyl, n-Propyl,
Isopropyl, n-Butyl, Isobutyl, sec.-Butyl oder tert.-Butyl.
Sind R₁ und R₂ HO-(alkylen)-, so handelt es sich beispielsweise
um Hydroxyäthyl, Hydroxypropyl oder Hydroxyisopropyl.
Beispiele für erfindungsgemäße Verbindungen sind:
1-Diäthanolaminomethyl-benzotriazol,
1-Diäthanolaminomethyl-tolutriazol,
1-Diisopropanolaminomethyl-benzotriazol.
1-Diäthanolaminomethyl-benzotriazol,
1-Diäthanolaminomethyl-tolutriazol,
1-Diisopropanolaminomethyl-benzotriazol.
Die Erfindung betrifft ein Verfahren zur Herstellung von
Verbindungen der Formel I, dadurch gekennzeichnet, daß in an
sich bekannter Weise eine Verbindung der allgemeinen Formel II,
worin R die vorstehende Bedeutung hat, mit Formaldehyd und
einem Amin der allgemeinen Formel III
umgesetzt wird, worin R₁ und R₂ obige Bedeutung haben.
Verbindungen der Formel II, die als Ausgangsmaterial in obiger
Reaktion geeignet sind, sind z. B. Benzotriazol
und die Verbindungen gemäß GB-PS 10 65 995 (5-Alkyl-benzotriazole).
Bevorzugt ist die Verbindung II Benzotriazol.
Der Formaldehyd-Reaktant wird bevorzugt in der Handelsform
verwendet, z. B. als Formalin oder Paraformaldehyd.
Beispiele geeigneter Amine der Formel III sind sekundäre
Amine der Formel
worin R₁ und R₂ obige Bedeutung haben.
Das Molverhältnis Verbindung II : Formaldehyd : Amin III ist
insbesondere etwa 1,0 : 1,0 : 1,0.
Das erfindungsgemäße Verfahren wird insbesondere ausgeführt,
indem man alle Reaktanten zusammen auf erhöhte Temperatur
erhitzt, z. B. auf 50°-120°C. Wenn erwünscht können die Verbindung
der Formel II und Formaldehyd zunächst miteinander
umgesetzt werden zu dem entsprechen N-Methylol, bevor mit
dem Amin der Formel III reagiert wird.
Die Mannich-Basen der Formel I sind hervorragende
Metallpassivatoren mit hoher Löslichkeit in vielen hydraulischen
Flüssigkeiten.
Die Erfindung betrifft auch eine Zusammensetzung enthaltend
eine hydraulische Flüssigkeit und als Metallpassivator eine
passivierende Menge einer Verbindung der Formel I
gemäß oben.
Insbesondere enthält die Zusammensetzung 0,001%-5% (Gewicht)
der Verbindung der Formel I bezogen auf das Gesamtgewicht
der Zusammensetzung.
Beispiele für hydraulische Flüssigkeiten, für die die erfindungsgemäßen
Stoffe nützlich sind, sind Schmiermittel auf Mineralöl-
oder Synthese-Carbonsäureester-Basis, hydraulische Flüssigkeiten
auf Mineralöl-Basis. Phosphatester, wäßrige Polyglykol/
Polyglykoläther-Mischungen, Glykol-Systeme, Öl-in-Wasser- und
andere Wasser-in-Öl-Emulsionen und Metall-Bearbeitungsflüssigkeiten
auf Mineralöl- oder wäßriger Basis, sowie wäßrige
Glykol-Anti-Frost-Zusammensetzungen.
Von besonderem Interesse sind Flüssigkeiten auf Wasserbasis,
z. B. Frostschutzmittel auf Wasserbasis, hydraulische und
Metall-Bearbeitungs-Flüssigkeiten. Für solche wäßrigen
Flüssigkeiten sind solche Verbindungen der Formel I bevorzugt,
die einen polaren Substituenten an dem N-Atom des heterocyclischen
Rings tragen.
Je nach der Art der Flüssigkeit enthält die Zusammensetzung
insbesondere ein oder mehrere Co-Additive.
Beispiele für Co-Additive für nicht-wäßrige Flüssigkeiten
sind Antioxidantien, Metallpassivatoren, Rostschutzmittel,
Viskositätsverbesserer, Fließpunktsenker, Dispergiermittel,
Detergentien, Extremdruck- und Anti-wear-Additive.
Beispiele für Antioxidantien sind:
- a) Alkylierte und nicht-alkylierte aromatische Amine und Mischungen davon, z. B. Dioctyldiphenylamin, Mono-tert.-octyl- phenyl-a- und -β-naphthylamine, Dioctylphenothiazin, Phenyl-α-naphthylamin, N,N′-Di-sec.-butyl-p-phenylendiamin.
- b) Behinderte Phenole, z. B. 2,6-Di-tert.-butyl-p-cresol, 4,4′-Bis-(2,6-diisopropylphenol), 2,4,6-Triisopropylphenol, 2,2′-Thio-bis-(4-methyl-6-tert.-butylphenol).
- c) Alkyl-, Aryl- oder Alkaryl-phosphite, z. B. Triphenylphosphit, Trinonylphosphit, Diphenyldecylphosphit.
- d) Ester von Thiodipropionsäure, z. B. Dilaurylthiodipropionat.
- e) Salze von Carbamin- und Dithiophosphorsäuren, z. B. Antimon- diamyldithiocarbamat, Zink-diamyldithiophosphat.
- f) Metallsalze, Komplexe von organischen Chelatisierungsmitteln, z. B. Kupfer-bis-(trifluoracetonate), Kupfer- phthalocyanid, Tributyl-ester von EDTA-mono-Natriumsalz.
- g) Free-Radical-Antioxidantien und ihre Vorstufen, z. B. Nitroxide etc.
- h) Kombinationen von zwei oder mehr obiger Antioxidantien, z. B. ein alkyliertes Amin und ein gehindertes Phenol.
Beispiele für Metallpassivatoren sind:
- a) für Kupfer z. B. Benzotriazol, 5,5′-Methylen-bisbenzotriazol, 4,5,6,7-Tetrahydrobenzotriazol, 2,5-Di-mercapto- thiadiazol, Salicylidenpropylendiamin, Salze von Salicylalaminoguanidin, Quinizarin etc.
- b) für Magnesium z. B. Pyridylamine.
- c) für Blei z. B. Sebacinsäure, Propylgallat und Quinazarin.
- d) Kombinationen von zwei oder mehr obiger Additive.
Beispiele für Rostschutzmittel sind:
- a) Organische Säuren und ihre Ester, Metallsalze, Anhydride, z. B. N-Oleoyl-sarcosin, Sorbitan-mono-oleat, Bleinaphthenat, Dodecylbernsteinsäureanhydrid.
- b) Stickstoffhaltige Stoffe, wie
- i) Primäre, sekundäre oder tertiäre aliphatische oder cycloaliphatische Aminsalze von organischen und anorganischen Säuren, z. B. Morpholin, Stearyl-amin, Triäthanolamin- caprylat.
- ii) heterocyclische Verbindungen, wie Imidazoline, Oxazoline.
- c) Phosphorhaltige Stoffe, z. B. anorganische Phosphate, Phosphorsäuren, Amin-phosphate.
- d) Schwefelhaltige Stoffe, z. B. Barium-dinonylnaphthalin- sulfonate.
- e) Kombinationen von zwei oder mehr obiger Additive.
Beispiele für Viskositäts-Index-Verbesserer/Fließpunktsenker
sind:
z. B. Polyacrylate, Polybutene, Polyvinyl-pyrrolidone.
z. B. Polyacrylate, Polybutene, Polyvinyl-pyrrolidone.
Beispiele für Dispergiermittel/Detergentien sind:
z. B. Metallsulfonate (Ca, Ba, Mg) und Phenate, Polybutenyl- succinimide. Additive, Biocide, Puffermittel und Schaumhemmer.
z. B. Metallsulfonate (Ca, Ba, Mg) und Phenate, Polybutenyl- succinimide. Additive, Biocide, Puffermittel und Schaumhemmer.
Beispiele für Extremdruck/Antiwear-Additive sind:
Schwefel- und/oder Phosphor- und/oder Halogen-haltige Stoffe, z. B. geschwefeltes Samenöl, Tritolylphosphat, chloriertes Paraffin.
Schwefel- und/oder Phosphor- und/oder Halogen-haltige Stoffe, z. B. geschwefeltes Samenöl, Tritolylphosphat, chloriertes Paraffin.
Beispiele für Co-Additive für wäßrige Produkte und/oder
Glykol-glykolähter sind Antioxidantien, Korrosions- und
Rostinhibitoren, Metallpassivatoren, Extremdruck/anti-wear-
Additive, Biocide, Puffermittel und Schaumhemmer.
Beispiele für Antioxidantien sind:
2,6-Di-tert.-butyl-p-cresol und Phenyl-α-naphthylamin.
2,6-Di-tert.-butyl-p-cresol und Phenyl-α-naphthylamin.
Beispiele für Korrosions- und Rost-inhibitoren sind:
Natriumnitrit, Natriumbenzoat, Morpholin, Aminseifen, z. B. Triäthanolamin-sebacat, Triäthanolamin-phosphat, Dinatrium- hydrogen-phosphat, Dinatriumsebacat, Arylsulfonamido- carbonsäureester.
Natriumnitrit, Natriumbenzoat, Morpholin, Aminseifen, z. B. Triäthanolamin-sebacat, Triäthanolamin-phosphat, Dinatrium- hydrogen-phosphat, Dinatriumsebacat, Arylsulfonamido- carbonsäureester.
Beispiele für Metallpassivatoren sind:
Benzotriazol und Natriummercaptobenzothiazol.
Benzotriazol und Natriummercaptobenzothiazol.
Beispiele für Extremdruck/Anti-wear-Additive sind:
chloriertes Paraffin, geschwefeltes Samenöl, geschwefelte Olefine, äthoxylierte Halbester und Polyglycole.
chloriertes Paraffin, geschwefeltes Samenöl, geschwefelte Olefine, äthoxylierte Halbester und Polyglycole.
Beispiele für Puffer sind:
Borax und Triäthanolamin.
Borax und Triäthanolamin.
Beispiele für Biocide sind:
2,4,5-Trichlorphenol, Natriumsalz von 2,2′-Dihydroxy-5,5′-dichlordiphenyl- methan, und Natriumsalz von Orthophenylphenol. Beispiele für Schaumhemmer sind Silicone.
2,4,5-Trichlorphenol, Natriumsalz von 2,2′-Dihydroxy-5,5′-dichlordiphenyl- methan, und Natriumsalz von Orthophenylphenol. Beispiele für Schaumhemmer sind Silicone.
Alle Produkte werden durch das gleiche allgemeine Verfahren
hergestellt, wie es unten für Mannich Basen von sekundären
Aminen beschrieben ist. Mannich Basen hergestellt aus primären
Aminen benötigen die halbe molare Menge Amin.
23,82 Teile Benzotriazol und 21,03 Teile Diäthanolamin werden
mit 75 Teilen Äthanol gemischt. 6,0 Teile Formaldehyd werden
als 36%ige wäßrige Lösung zugegeben. Die Mischung wird zum
Sieden erhitzt und 8 Stunden unter Rückfluß gehalten (Amine mit
höherem Molekulargewicht benötigen eine Reaktionszeit bis zu
16 Stunden, um ausreichende Ausbeute zu liefern). Nach Kühlen
wird das Lösungsmittel am Wasserstrahlvakuum abgezogen. Der
Rückstand wird mit 3 × 50 Teilen Äthanol unter Wasserstrahlvakuum
azeotrop destilliert. Man erhält 1-Diäthanolaminomethyl-benzotriazol
in 80% Ausbeute.
Werden feste Produkte erhalten, wird am besten aus Äthylacetat
umkristallisiert.
Die Produkte sind im wesentlichen 1-N-substituiert, obgleich
aus dem NMR-Spektrum ein Hinweis auf etwas 2-N-Substitution
vorliegt, in Mengen bis zu 20%.
Mit der gleichen Methode werden verschiedene andere Verbindungen
der Formel I hergestellt.
Die folgenden Verbindungen wurden auf ihre Korrosionsschutzwirkung
untersucht.
1. 1-Diäthanolaminomethylbenztriazol
2. 1-Diäthanolaminomethyltolutriazol
3. 5,5′-Methylen-bisbenztriazol (Stand der Technik)
1. 1-Diäthanolaminomethylbenztriazol
2. 1-Diäthanolaminomethyltolutriazol
3. 5,5′-Methylen-bisbenztriazol (Stand der Technik)
Eine Kupferprobe, wie sie in Kühlsystemen von Verbrennungsmaschinen
vorkommt, wird ganz in eine belüftete Testlösung zwei Wochen bei
82°C eingetaucht.
Die Kupferprobe ist vom Typ ETP oder STP der U.S. Standard
Specification für Kupferblech, Platte oder gewalzter Stab ASTM
B 152, SAE 71 kalt gewalzter Stahl.
Die Kupferprobe wird gut mit Bimstein und einem feuchten Pinsel
gerieben, in kaltem Wasser gespült, dann in Aceton und schließlich
getrocknet und gewogen.
Die Kupferprobe (1) (50 mm × 25 mm mit einer 6 mm Zentralbohrung) wird
auf eine Messingmaschinenschraube (12) mit einer Messingmutter (11) und mit einem dünnen Isolationsrohr
gegeben, das durch die Zentralbohrung der Probe paßt. Bei mehreren
Metallproben werden die Proben (1) bis (6) durch Abstandsringe (8), (9) und (10) von
5 mm Länge, 11 mm Außendurchmesser und 6 mm Innendurchmesser
voneinander getrennt. Am Ende der Anordnung befindet sich ein
Messingfuß (7), 50 mm × 25 mm, geschnitten aus 1,5 mm Messingblech
mit einer 6 mm Bohrung, in Richtung der Bohrungen in den Proben.
Eine Frostschutzmischung wird wie folgt bereitet
Monoäthylen-glykol93,0 Teile
Triäthanolamin 2,9 Teile
Phosphorsäure (d 1,75) 1,1 Teile
Borax 3,0 Teile
Ein Gewichtsteil dieser Mischung wird mit 2 Teilen Wasser verdünnt.
Zu dieser Lösung wird soviel Korrosionsschutzmittel zugegeben, daß
dessen Konzentration ca. 10 ppm beträgt.
750 ml dieser verdünnten Lösung (15) werden in ein belüftbares Gefäß (13)
gegeben, das mit einem Kühler (16) versehen ist. Das Gefäß wird in ein
Wasserbad bei 82±2°C getaucht. Die Belüftung (14) wird auf 100±
15 ml pro Minute eingestellt.
Der Test wird 336 Stunden (2 Wochen) durchgeführt. Am Ende wird die
Probe entnommen und unter fließendem Wasser gewaschen und
gepinselt, um leichthaftende Korrosionsprodukte zu entfernen. Fester
haftende Produkte werden durch Tauchen der Kupferprobe in 30%ige
HCl-Lösung während 30 Sekunden entfernt.
Schließlich wird die Probe mit einem feuchten Pinsel gereinigt, mit
Aceton gespült, getrocknet und gewogen.
Claims (3)
1. Benzotriazole der allgemeinen Formel I
worin R Wasserstoff oder C₁-C₄-Alkyl bedeutet, R₁ und
R₂ gleich sind und HO-(alkylen)- bedeuten, wobei
(alkylen) Alkylen mit 2 oder 3 C-Atomen ist.
2. Verfahren zur Herstellung der Verbindungen gemäß Anspruch 1,
dadurch gekennzeichnet, daß in an sich bekannter Weise eine
Verbindung der allgemeinen Formel II
worin R die in Anspruch 1 angegebene Bedeutung hat, mit
Formaldehyd und einem Amin der allgemeinen Formel III
umgesetzt wird, wobei R₁ und R₂ die vorstehenden Bedeutungen haben.
3. Hydraulische Flüssigkeit enthaltend eine Verbindung gemäß
Anspruch 1.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB292975A GB1466558A (en) | 1975-01-23 | 1975-01-23 | Additives for functional fluids |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2601719A1 DE2601719A1 (de) | 1976-07-29 |
DE2601719C2 true DE2601719C2 (de) | 1988-01-07 |
Family
ID=9748727
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19762601719 Granted DE2601719A1 (de) | 1975-01-23 | 1976-01-19 | Additive fuer hydraulische fluessigkeiten |
Country Status (18)
Country | Link |
---|---|
JP (1) | JPS6224427B2 (de) |
AT (1) | AT343655B (de) |
AU (1) | AU502892B2 (de) |
BE (1) | BE837796A (de) |
BR (1) | BR7600385A (de) |
CA (1) | CA1077047A (de) |
CH (1) | CH597198A5 (de) |
DD (1) | DD123745A5 (de) |
DE (1) | DE2601719A1 (de) |
ES (1) | ES444523A1 (de) |
FR (1) | FR2298543A1 (de) |
GB (1) | GB1466558A (de) |
IT (1) | IT1060209B (de) |
NL (1) | NL7600732A (de) |
PL (1) | PL97084B1 (de) |
SE (1) | SE426243B (de) |
SU (1) | SU582759A3 (de) |
ZA (1) | ZA76372B (de) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4268610A (en) * | 1979-11-05 | 1981-05-19 | Hercules Incorporated | Photoresist formulations |
DE3172025D1 (en) * | 1980-07-15 | 1985-10-03 | Ciba Geigy Ag | Printing ink and its use in the manufacture of textured, foamed resinous materials |
EP0088724B1 (de) * | 1982-02-26 | 1988-05-18 | Ciba-Geigy Ag | Benzotriazolgemische, Verfahren zu deren Herstellung und ihre Verwendung als Metallpassivatoren |
GB2152073B (en) * | 1983-12-23 | 1986-10-22 | Ciba Geigy | Lubricant stabilizer additives |
JPS63191514U (de) * | 1987-05-28 | 1988-12-09 | ||
JPH01127127U (de) * | 1988-02-25 | 1989-08-30 | ||
US4880551A (en) * | 1988-06-06 | 1989-11-14 | R. T. Vanderbilt Company, Inc. | Antioxidant synergists for lubricating compositions |
JPH0236132U (de) * | 1988-08-31 | 1990-03-08 | ||
EP0428383A1 (de) * | 1989-11-13 | 1991-05-22 | Shikoku Chemicals Corporation | Verfahren zur Oberflächenbehandlung von Kupfer und Kupferlegierungen |
US4997585A (en) * | 1990-03-30 | 1991-03-05 | Exxon Research And Engineering Company | Aromatic substituted benzotriazole containing lubricants having improved oxidation stability |
GB9013142D0 (en) * | 1990-06-13 | 1990-08-01 | Ciba Geigy Ag | Chemical compounds useful as metal deactivators |
JPH06100881A (ja) * | 1992-09-18 | 1994-04-12 | Kyoseki Seihin Gijutsu Kenkyusho:Kk | 冷凍機油組成物 |
US5441563A (en) * | 1993-07-06 | 1995-08-15 | Armstrong World Industries, Inc. | Highly insoluble azole embossing inhibitor and the use thereof |
TW399094B (en) * | 1995-04-11 | 2000-07-21 | Ciba Sc Holding Ag | Compounds with (benzo)triazole radicals |
US5548003A (en) * | 1995-08-14 | 1996-08-20 | Armstrong World Industries, Inc. | Azole-aldehyde addition product embossing inhibitors and the use thereof |
US5622922A (en) * | 1995-12-27 | 1997-04-22 | Exxon Chemical Patents Inc. | Method of solubilizing a benzotriazole with a thiadiazole |
US5824721A (en) * | 1996-06-10 | 1998-10-20 | Armstrong World Industries, Inc. | Water soluble triazole derivative embossing inhibitor and the use thereof |
JP3702069B2 (ja) * | 1997-05-07 | 2005-10-05 | 東洋アルミニウム株式会社 | アルミニウム顔料組成物 |
GB9924358D0 (en) * | 1999-10-14 | 1999-12-15 | Brad Chem Technology Ltd | Corrosion inhibiting compositions |
CN104649985A (zh) * | 2013-11-25 | 2015-05-27 | 刘现梅 | 一种水溶性的甲基苯骈三氮唑的次甲基衍生物及其制备方法 |
US11788026B2 (en) * | 2021-07-28 | 2023-10-17 | Afton Chemical Corporation | Hydraulic fluid |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1081282A (en) * | 1964-08-14 | 1967-08-31 | Geigy Uk Ltd | Bis-benzotriazoles and compositions containing same |
-
1975
- 1975-01-23 GB GB292975A patent/GB1466558A/en not_active Expired
-
1976
- 1976-01-09 SE SE7600160A patent/SE426243B/xx not_active IP Right Cessation
- 1976-01-19 DE DE19762601719 patent/DE2601719A1/de active Granted
- 1976-01-20 CH CH63376A patent/CH597198A5/xx not_active IP Right Cessation
- 1976-01-20 PL PL1976186652A patent/PL97084B1/pl unknown
- 1976-01-20 SU SU7602314150A patent/SU582759A3/ru active
- 1976-01-21 CA CA244,033A patent/CA1077047A/en not_active Expired
- 1976-01-21 DD DD190901A patent/DD123745A5/xx unknown
- 1976-01-22 BR BR7600385A patent/BR7600385A/pt unknown
- 1976-01-22 AT AT42476A patent/AT343655B/de not_active IP Right Cessation
- 1976-01-22 BE BE163700A patent/BE837796A/xx not_active IP Right Cessation
- 1976-01-22 IT IT19494/76A patent/IT1060209B/it active
- 1976-01-22 ZA ZA372A patent/ZA76372B/xx unknown
- 1976-01-22 AU AU10508/76A patent/AU502892B2/en not_active Expired
- 1976-01-22 ES ES444523A patent/ES444523A1/es not_active Expired
- 1976-01-22 FR FR7601653A patent/FR2298543A1/fr active Granted
- 1976-01-23 NL NL7600732A patent/NL7600732A/xx not_active Application Discontinuation
- 1976-01-23 JP JP51007065A patent/JPS6224427B2/ja not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR2298543A1 (fr) | 1976-08-20 |
DE2601719A1 (de) | 1976-07-29 |
DD123745A5 (de) | 1977-01-12 |
AU502892B2 (en) | 1979-08-09 |
CH597198A5 (de) | 1978-03-31 |
ES444523A1 (es) | 1977-06-16 |
AT343655B (de) | 1978-06-12 |
SE7600160L (sv) | 1976-07-26 |
SE426243B (sv) | 1982-12-20 |
ATA42476A (de) | 1977-10-15 |
BR7600385A (pt) | 1976-08-31 |
CA1077047A (en) | 1980-05-06 |
PL97084B1 (pl) | 1978-02-28 |
JPS5198276A (de) | 1976-08-30 |
BE837796A (fr) | 1976-07-22 |
JPS6224427B2 (de) | 1987-05-28 |
FR2298543B1 (de) | 1979-02-02 |
NL7600732A (nl) | 1976-07-27 |
SU582759A3 (ru) | 1977-11-30 |
IT1060209B (it) | 1982-07-10 |
ZA76372B (en) | 1977-01-26 |
GB1466558A (en) | 1977-03-09 |
AU1050876A (en) | 1977-07-28 |
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