EP0356677A1 - Schmierstoffzusammensetzung - Google Patents
Schmierstoffzusammensetzung Download PDFInfo
- Publication number
- EP0356677A1 EP0356677A1 EP89112951A EP89112951A EP0356677A1 EP 0356677 A1 EP0356677 A1 EP 0356677A1 EP 89112951 A EP89112951 A EP 89112951A EP 89112951 A EP89112951 A EP 89112951A EP 0356677 A1 EP0356677 A1 EP 0356677A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- tert
- hydrogen
- butyl
- composition according
- 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.)
- Granted
Links
- BUJFTKPQXSIZFX-UHFFFAOYSA-N CCC(C)(C)NC Chemical compound CCC(C)(C)NC BUJFTKPQXSIZFX-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/04—Hydroxy compounds
- C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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Definitions
- the present invention relates to lubricant compositions that are stabilized against oxidative degradation. Stabilization is achieved by adding at least two specific additives.
- Aromatic amines are used as antioxidants for lubricants, e.g. alkylated diphenylamines or alkylated phenothiazines. Such amines are described for example in EP-A-149 422 or GB-A-1 090 688.
- the use of such aromatic amines in combination with other antioxidants such as e.g. with triaryl phosphites, thiodipropionates or phenolic antioxidants is known. e.g. from EP-A-49 133.
- R3 as C1-C12 alkyl can be linear or branched alkyl and can e.g. Be methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl, decyl or dodecyl.
- R1, R5 and R6 as C1-C18 alkyl can also e.g. Tetradecyl, pentadecyl, hexadecyl or octadecyl.
- R4 as C4-C18 alkyl can e.g. be n-butyl, tert-butyl, n-hexyl, tert-octyl, n-dodecyl or octadecyl.
- R1, R5 and R6 as C7-C9-phenylalkyl can e.g. Benzyl, 2-phenylethyl, ⁇ -methylbenzyl, 2-phenylpropyl or ⁇ , ⁇ -dimethylbenzyl.
- R1 and R2 as C7-C18 alkylphenyl can have linear or branched alkyl groups. Examples are tolyl, ethylphenyl, isopropylphenyl, tert-butylphenyl, sec-pentylphenyl, n-hexylphenyl, tert-octylphenyl, iso-nonylphenyl or n-dodecylphenyl.
- R 1 and R 2 can also be mixtures of alkylphenyl groups, such as those formed in technical alkylations of diphenylamine using olefins.
- the alkyl group is preferably in the para position of the aromatic amine.
- Component B) is preferably a compound of the formula I or II in which R1 is C1-C4-alkyl, C7-C9-phenylalkyl, cyclohexyl, phenyl, C10-C18-alkylphenyl or naphthyl, R2 is C10-C18 alkylphenyl or phenyl, R3 is hydrogen, C1-C8-alkyl, benzyl, allyl or a group -CH2SR4, R4 is C8-C18-alkyl or -CH2COO (C8-C18-alkyl), and R5 and R6 independently of one another are H, C1-C12-alkyl or C7-C9-phenylalkyl.
- R1 and R2 independently of one another are phenyl or C18-C18-alkylphenyl and R3 is hydrogen are particularly preferred.
- R3 is hydrogen and R5 and R6 independently of one another are H or C4-C12-alkyl are particularly preferred.
- Examples of compounds of the formula are: Diphenylamine N-allyl diphenylamine 4-isopropoxydiphenylamine N-phenyl-1-naphthylamine N-phenyl-2-naphthylamine Di-4-methoxyphenylamine Di- [4- (1,3-dimethylbutyl) phenyl] amine Di- [4- (1,1,3,3-tetramethylbutyl) phenyl] amine tert-octylated N-phenyl-1-naphthylamine
- Phenothiazine N-allylphenothiazine 3,7-di-tert-octyl-phenothiazine
- Component (C) can be any cyclic or non-cyclic hindered amine.
- (C) is preferably a compound which has at least one group of the formula III contains, wherein R is hydrogen or methyl. R is preferably hydrogen.
- R is hydrogen or methyl.
- R is preferably hydrogen.
- These are derivatives of polyalkylpiperidines, in particular 2,2,6,6-tetramethylpiperidine. These polyalkylpiperidines preferably carry one or two polar substituents or a polar spiro ring system in the 4-position.
- n is a number from 1 to 4, preferably 1 or 2
- R is hydrogen or methyl
- R11 is hydrogen, oxyl, hydroxyl, C1-C12-alkyl, C3-C8 alkenyl, C3-C8-alkynyl, C7-C12-aralkyl , C1-C18 alkoxy, C5-C8-cycloalkoxy, C7-C9-phenylalkoxy, C1-C8-alkanoyl, C3-C5-alkenoyl, C1-C18-alkanoyloxy, benzyloxy, glycidyl or a group -CH2CH (OH) -Z , wherein Z is hydrogen, methyl or phenyl, where R11 is preferably H, C1-C4-alkyl, allyl, benzyl, acetyl or acryloyl and R12, when n is 1, is hydrogen,
- substituents are C1-C12-alkyl, they represent e.g. Methyl, ethyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethyl-hexyl, n-nonyl, n-decyl, n-undecyl or n- Dodecyl.
- R11 or R12 can e.g. represent the groups listed above and, for example, n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl.
- R11 is C3-C8-alkenyl, it can e.g. are 1-propenyl, allyl, methallyl, 2-butenyl, 2-pentenyl, 2-hexenyl, 2-octenyl, 4-tert-butyl-2-butenyl.
- R11 is preferably as C3-C8 alkynyl propargyl.
- R11 is especially phenethyl and especially benzyl.
- R11 is as C1-C8 alkanoyl, for example formyl, propionyl, butyryl, octanoyl, but preferably acetyl and as C3-C5-alkenoyl in particular acryloyl.
- R12 is a monovalent radical of a carboxylic acid, it is, for example, acetic, caproic, stearic, acrylic, methacrylic, benzoic or ⁇ - (3,5-di-tert-butyl-4-hydroxyphenyl) - propionic acid residue.
- R12 is a divalent radical of a dicarboxylic acid, it is, for example, malonic, succinic, glutaric, adipic, suberic, sebacic, maleic, itaconic, phthalic, dibutylmalonic, dibenzylmalonic, butyl (3 , 5-di-tert.butyl-4-hydroxybenzyl) -malonic acid or bicycloheptenedicarboxylic acid residue.
- R 12 represents a trivalent radical of a tricarboxylic acid, it means e.g. a trimellitic acid, citric acid or nitrilotriacetic acid residue.
- R 12 represents a tetravalent radical of a tetracarboxylic acid, it means e.g. the tetravalent residue of butane-1,2,3,4-tetracarboxylic acid or of pyromellitic acid.
- R12 is a divalent radical of a dicarbamic acid, it represents, for example, a hexamethylene dicarbamic acid or a 2,4-tolylene dicarbamic acid radical.
- Preferred compounds of the formula IV are those in which R is hydrogen, R 11 is hydrogen or methyl, n is 2 and R 12 is the diacyl radical of an aliphatic dicarboxylic acid having 4-12 C atoms.
- any substituents are C5-C7-cycloalkyl, they represent in particular cyclohexyl.
- R13 is especially phenylethyl or especially benzyl.
- R13 is in particular 2-hydroxyethyl or 2-hydroxypropyl.
- R13 is as C2-C18 alkanoyl, for example propionyl, butyryl, octanoyl, dodecanoyl, hexadecanoyl, octadecanoyl, but preferably acetyl and as C3-C5-alkenoyl, in particular acryloyl.
- R14 means C2-C8 alkenyl, then it is, for example, allyl, methallyl, 2-butenyl, 2-pentenyl, 2-hexenyl or 2-octenyl.
- R14 as a C1-C4 alkyl substituted with a hydroxy, cyano, alkoxycarbonyl or carbamide group can e.g. 2-Hydroxyethyl, 2-hydroxypropyl, 2-cyanoethyl, methoxycarbonylmethyl, 2-ethoxycarbonylethyl, 2-aminocarbonylpropyl or 2- (dimethylaminocarbonyl) ethyl.
- substituents are C2-C12 alkylene, they are e.g. around ethylene, propylene, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
- substituents are C6-C15 arylene, they represent e.g. o-, m- or p-phenylene, 1,4-naphthylene or 4,4'-diphenylene.
- D is especially cyclohexylene.
- R15 means C2-C8-alkylene or hydroxyalkylene, it represents, for example, ethylene, 1-methyl-ethylene, propylene, 2-ethyl-propylene or 2-ethyl-2-hydroxymethylpropylene.
- R15 means e.g. 2-ethyl-2-acetoxymethylpropylene.
- R16 is hydrogen, C1-C12-alkyl, allyl, benzyl, glycidyl or C2-C6-alkoxyalkyl and R17, if n is 1, is hydrogen , C1-C12-alkyl, C3-C5-alkenyl, C7-Cq-aralkyl, C5-C7 cycloalkyl, C2-C4-hydroxyalkyl, C2-C6-alkoxyalkyl, C6-C10-aryl, glycidyl or a group of the formula - ( CH2) p -COO-Q or of the formula - (CH2) p -O-CO-Q, where p is 1 or 2 and Q is C1-C4 alkyl or phenyl, if n is 2, C2-C12 alkylene, C4- C
- substituents are C1-C12-alkyl, they represent e.g. Methyl, ethyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethyl-hexyl, n-nonyl, n-decyl, n-undecyl or n- Dodecyl.
- C1-C18-alkyl can represent, for example, the groups mentioned above and, for example, n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl.
- substituents are C2-C6-alkoxyalkyl, they represent e.g. Methoxymethyl, ethoxymethyl, propoxymethyl, tert-butoxymethyl, ethoxyethyl, ethoxypropyl, n-butoxyethyl, tert-butoxyethyl, isopropoxyethyl or propoxypropyl.
- R17 is C3-C5-alkenyl, it means e.g. 1-propenyl, allyl, methallyl, 2-butenyl or 2-pentenyl.
- T1 and T2 are especially phenethyl or especially benzyl. If T1 and T2 form a cycloalkane ring together with the C atom, this can e.g. be a cyclopentane, cyclohexane, cyclooctane or cyclododecane ring.
- R17 is C2-C4-hydroxyalkyl, it is e.g. 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxybutyl or 4-hydroxybutyl.
- R17, T1 and T2 mean in particular phenyl, ⁇ - or ⁇ -naphthyl, which are optionally substituted by halogen or C1-C4-alkyl.
- R17 is C2-C12 alkylene, it is e.g. around ethylene, propylene, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
- R17 means in particular 2-butenylene, 2-pentenylene or 3-hexenylene.
- R17 means C6-C12 arylene, it represents, for example, o-, m- or p-phenylene, 1,4-naphthylene or 4,4'-diphenylene.
- Z 'means C2-C12 alkanoyl, for example propionyl, butyryl, octanoyl, dodecanoyl, but preferably acetyl.
- D as C2-C10 alkylene, C6-C15 arylene or C6-C12 cycloalkylene has the meaning given under b).
- substituents are C1-C12-alkyl, they are, for example, methyl, ethyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethylhexyl, n-nonyl , n-decyl, n-undecyl or n-dodecyl.
- substituents are C1-C4-hydroxyalkyl, they represent e.g. 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl or 4-hydroxybutyl.
- R21 and R22 together represent C4-C5-alkylene or oxaalkylene, this means e.g. Tetramethylene, pentamethylene or 3-oxapentamethylene.
- polyalkylpiperidine compounds of this class are the compounds of the following formulas:
- oligomers or polymeric compounds whose recurring structural unit contains a 2,2,6,6-tetraalkylpiperidine radical of the formula (I), in particular polyesters, polyethers, polyamides, polyamines, polyurethanes, polyureas, polyaminotriazines, poly (meth) acrylates, poly ( meth) acrylamides and their copolymers which contain such radicals.
- 2,2,6,6-polyalkylpiperidine light stabilizers of this class are the compounds of the following formulas, where m is a number from 2 to about 200. wherein R and R11 have the meaning given under a).
- Preferred compounds of formula IX are those in which R is hydrogen or methyl and R 11 is hydrogen or methyl.
- the amount of (B) and (C) added to the base oil (A) depends on the type of base oil and the desired degree of stabilization. In general, the sum of (B) and (C) is 0.1 to 2% by weight, preferably 0.5 to 1% by weight, based on (A).
- the ratio of (B) to (C) can be varied within wide limits; in general, (B) is the predominant component in terms of quantity.
- the ratio (B) :( C) is preferably 3-5: 1.
- Component (A) is a mineral or synthetic base oil, as is common for the preparation of lubricants.
- Synthetic oils can e.g. Esters of polycarboxylic acids or of polyols, they can be aliphatic polyesters or poly- ⁇ -olefins, silicones, phosphoric acid esters or polyalkylene glycols.
- the lubricant can also be a grease based on an oil and a thickener. Such lubricants are e.g. described in D. Klamann "Lubricants and related products", Verlag Chemie, Weinheim 1982.
- the lubricant can also contain other additives such as e.g. further antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, surfactants or wear protection additives.
- additives e.g. further antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, surfactants or wear protection additives.
- 2,6-di-tert-butyl-4-methylphenol 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-iso-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2- ( ⁇ -methylcyclohexyl ) -4,6-dimethylphenol, 2,6-di-octadecyl-4-methylphenol, 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol.
- mono- or polyhydric alcohols e.g. with methanol, diethylene glycol, octadecanol, triethylene glycol, 1,6-hexanediol, pentaerythritol, neopentyl glycol, tris-hydroxyethyl isocyanurate, thiodiethylene glycol, bis-hydroxyethyl oxalic acid diamide.
- mono- or polyhydric alcohols e.g. with methanol, diethylene glycol, octadecanol, triethylene glycol, 1,6-hexanediol, pentaerythritol, neopentyl glycol, tris-hydroxyethyl isocyanurate, thiodiethylene glycol, di-hydroxyethyl oxalic acid diamide.
- Aliphatic or aromatic phosphites esters of thiodipropionic acid or thiodiacetic acid, or salts of dithiocarbamide or dithiophosphoric acid.
- metal deactivators e.g. for copper
- metal deactivators e.g. for copper
- Triazoles benzotriazoles and their derivatives, tolutriazoles and their derivatives, 2-mercaptobenzthiazole, 2-mercaptobenztriazole, 2,5-dimercaptobenztriazole, 2,5-dimercaptobenzthiadiazole, 5,5'-methylenebisbenzotriazole, 4,5,6,7-tetrahydrobenztriazole, salicylides -propylenediamine, salicylaminoguanidine and its salts.
- rust inhibitors are:
- viscosity index improvers examples are:
- Polyacrylates polymethacrylates, vinyl pyrrolidone / methacrylate copolymers, polyvinyl pyrrolidones, polybutenes, olefin copolymers, styrene / acrylate copolymers, polyethers.
- pour point depressants examples are:
- dispersants / surfactants examples are:
- wear protection additives are:
- Compounds containing sulfur and / or phosphorus and / or halogen such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl di- and tri-sulfides, triphenyl phosphorothionates, diethanolaminomethyltolyltriazole, di (2-ethyltylylolyl) aminol.
- Examples of usable phosphites and phosphonites are: Triphenyl phosphite, decyl diphenyl phosphite, phenyl didecyl phosphite, tris- (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl-pentaerythritol diphosphite, tris- (2,4-di-tert.butylphenyl) -phosphite, diisodechritol , 4-di-tert.butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert.butylphenyl) -4, 4′-biphenylene diphosphonite, bis- (2,6-di- ter
- the individual additives are dissolved in the oil.
- the oil can be heated or the additives can be pre-dissolved in a solvent.
- the lubricant can also contain additives to solid lubricants, e.g. Graphite or molybdenum sulfide.
- thermo analyzer 1090 thermo analyzer 1090 from Du Pont
- the induction time of the oxidation of oil samples by air containing 400 ppm NO2 is measured under isothermal conditions. The measurement takes place at 170 ° C under a pressure of 8 bar.
- a standard mineral oil (Aral® 136) is used as the base oil, to which 1% by volume 1-decene is added to increase the sensitivity to oxygen.
- the following amine stabilizers are added to the oil.
- Aromatic amines :
- Table 1 shows the induction times. The longer the induction time, the higher the antioxidant effect of the stabilizer additives.
- Table 1 Aromat. Amine Hindered amine Induction time (min) - - 43 0.55% A-1 - 80 0.45% A-1 0.10% H-1 91.5 0.45% A-1 0.10% H-2 91.5 0.45% A-1 0.10% H-3 90.5 0.45% A-1 0.10% H-4 90 0.45% A-1 0.10% H-5 84.5 0.45% A-1 0.10% H-6 89
- the oxidation of hydrocarbons creates oxygen-containing groups such as hydroxyl, carboxyl or ester groups.
- the amount of such groups can be measured well by infrared spectroscopy and the activity of antioxidants can be determined therefrom.
- samples of a standard mineral oil (Aral® 136) to which 1 vol% 1-decene is added to increase the sensitivity to oxygen, under isothermal conditions in an atmosphere of air to which 400 ppm NO2 is added, under a pressure of 8 bar warmed for 12 h. Then the IR absorption at 1730 cm301 and 1630 ⁇ 1 is measured. The lower these values are, the higher the activity of the stabilizers.
- Tables 2a and 2b show the results at different temperatures.
- oxidation behavior of lubricating oils stabilized according to the invention was also tested according to the TOST method (turbine oxidation stability test) in accordance with ASTM D-943.
- TOST method turbine oxidation stability test
- 300 ml of a mineral oil Mobil STOC K 305
- 60 ml of water are mixed with 60 ml of water and heated to 95 ° C for 1000 hours in the presence of iron and copper wire while passing oxygen through.
- SLUDGE (mg) 100% - 0.46 30th 95% 5% 0.38 27th 90% 10% 0.30 24th 75% 25% 0.31 27th
- the resistance to oxidation can also be measured by measuring the increase in viscosity when treated with oxygen at elevated temperature.
- an oxygen stream (1 l / h) is passed through the oil at 150 ° C. for 70 hours.
- the oil is previously sensitized with a catalytic amount of a copper naphthenate.
- the viscosity of the oil is measured before and after with an Ubbelode viscometer.
- Table 6 Oil Percentage increase in viscosity Base oil 168% Base oil with the addition of 0.6% A-1 and 0.15% H-8 3.4%
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Abstract
Description
- Die vorliegende Erfindung betrifft Schmierstoffzusammensetzungen, die gegen oxidativen Abbau stabilisiert sind. Die Stabilisierung erfolgt durch Zusatz von mindestens zwei spezifischen Zusatzstoffen.
- Es ist bekannt und üblich, zu Schmierstoffen auf Basis von Mineralölen oder synthetischen Oelen Zusatzstoffe zur Verbesserung ihrer Gebrauchseigenschaften zuzusetzen. Von besonderer Bedeutung sind Zusatzstoffe gegen oxidativen Abbau der Schmierstoffe, sogenannte Antioxidantien. Der oxidative Abbau von Schmierstoffen spielt vor allem bei Motorenölen eine grosse Rolle, da im Verbrennungsraum der Motoren hohe Temperaturen herrschen und neben Sauerstoff Stickoxide (NOx) vorhanden sind, welche als Oxidationskatalysatoren wirken.
- Als Antioxidantien für Schmierstoffe werden unter anderem aromatische Amine verwendet, wie z.B. alkylierte Diphenylamine oder alkylierte Phenothiazine. Solche Amine sind beispielsweise in der EP-A- 149 422 oder der GB-A-1 090 688 beschrieben. Auch die Verwendung solcher aromatischer Amine in Kombination mit anderen Antioxidantien wie z.B. mit Triarylphosphiten, Thiodipropionaten oder phenolischen Antioxidantien ist bekannt. z.B. aus der EP-A-49 133.
- Es wurde gefunden, dass sich eine Kombination von aromatischen Aminen mit sterisch gehinderten Aminen hervorragend als Antioxidans für Schmierstoffe eignet.
- Gegenstand der Erfindung ist eine Schmierstoffzusammensetzung, enthaltend
- (A) ein mineralisches oder synthetisches Basisöl oder ein Gemisch solcher Oele,
- (B) mindestens ein aromatisches Amin der Formel I oder II,
R² Phenyl, C₇-C₁₈-Alkylphenyl, C₇-C₁₈-Alkoxyphenyl oder Naphthyl bedeutet,
R³ Wasserstoff, C₁-C₁₂-Alkyl, Benzyl, Allyl, Methallyl, Phenyl oder eine Gruppe -CH₂SR⁴ bedeutet,
R⁴ C₄-C₁₈-Alkyl, -CH₂COO(C₄-C₁₈-Alkyl) oder -CH₂CH₂COO(C₄-C₁₈-Alkyl) bedeutet, und
R⁵ und R⁶ unabhängig voneinander H, C₁-C₁₈-Alkyl oder C₇-C₉-Phenylalkyl bedeuten und - (C) mindestens ein sterisch gehindertes Amin.
- R³ als C₁-C₁₂-Alkyl kann lineares oder verzweigtes Alkyl sein und kann z.B. Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl, Octyl, Nonyl, Decyl oder Dodecyl sein. R¹, R⁵ und R⁶ als C₁-C₁₈-Alkyl können darüber hinaus auch z.B. Tetradecyl, Pentadecyl, Hexadecyl oder Octadecyl sein. R⁴ als C₄-C₁₈-Alkyl kann z.B. n-Butyl, tert.Butyl, n-Hexyl, tert.Octyl, n-Dodecyl oder Octadecyl sein.
- R¹, R⁵ und R⁶ als C₇-C₉-Phenylalkyl können z.B. Benzyl, 2-Phenylethyl, α-Methylbenzyl, 2-Phenylpropyl oder α,α-Dimethylbenzyl sein.
- R¹ und R² als C₇-C₁₈-Alkylphenyl können lineare oder verzweigte Alkylgruppen haben. Beispiele sind Tolyl, Ethylphenyl, Isopropylphenyl, tert.Butylphenyl, sec.Pentylphenyl, n-Hexylphenyl, tert.Octylphenyl, iso-Nonylphenyl oder n-Dodecylphenyl. Es kann sich bei R¹ und R² auch um Gemische von Alkylphenylgruppen handeln, wie sie bei technischen Alkylierungen von Diphenylamin mittels Olefinen entstehen. Bevorzugt steht die Alkylgruppe in para-Stellung des aromatischen Amins.
- Bevorzugt verwendet man als Komponente B) eine Verbindung der Formel I oder II, worin
R¹ C₁-C₄-Alkyl, C₇-C₉-Phenylalkyl, Cyclohexyl, Phenyl, C₁₀-C₁₈-Alkylphenyl oder Naphthyl bedeutet,
R² C₁₀-C₁₈-Alkylphenyl oder Phenyl bedeutet,
R³ Wasserstoff, C₁-C₈-Alkyl, Benzyl, Allyl oder eine Gruppe -CH₂SR⁴ bedeutet,
R⁴ C₈-C₁₈-Alkyl oder -CH₂COO(C₈-C₁₈-Alkyl) bedeutet, und
R⁵ und R⁶ unabhängig voneinander H, C₁-C₁₂-Alkyl oder C₇-C₉-Phenylalkyl bedeuten. - Unter den Verbindungen der Formel I sind solche besonders bevorzugt, worin R¹ und R² unabhängig voneinander Phenyl oder C₁₀-C₁₈-Alkylphenyl bedeuten und R³ Wasserstoff ist.
- Unter den Verbindungen der Formel II sind solche besonders bevorzugt, worin R³ Wasserstoff ist und R⁵ und R⁶ unabhängig voneinander H oder C₄-C₁₂-Alkyl bedeuten.
- Beispiele für Verbindungen der Formel sind:
Diphenylamin
N-Allyldiphenylamin
4-Isopropoxydiphenylamin
N-Phenyl-1-naphthylamin
N-Phenyl-2-naphthylamin
Di-4-methoxyphenyl-amin
Di-[4-(1,3-dimethylbutyl)-phenyl]-amin
Di-[4-(1,1,3,3-tetramethylbutyl)-phenyl]-amin
tert.octyliertes N-Phenyl-1-naphtylamin
technische Gemische erhalten durch Reaktion von Diphenylamin mit Diisobutylen (mono-, di- und trialkylierte tert.Butyl- und tert.Octyldiphenylamine)
Phenothiazin
N-Allylphenothiazin
3,7-Di-tert.octyl-phenothiazin
technische Gemische erhalten durch Reaktion von Phenothiazin mit Diisobutylen - Besonders bevorzugt verwendet man als Komponente B) 4,4′-Di-tert.octyl-diphenylamin oder 3,7-Di-tert.octyl-phenothiazin oder ein technisches Gemisch erhalten durch Reaktion von Diphenylamin mit Diisobutylen, insbesondere ein solches Gemisch, das folgende Bestandteile enthält:
- a) maximal 5 Gew.-% Diphenylamin,
- b) 8-15 Gew.-% 4-tert.Butyldiphenylamin,
- c) 24-32 Gew. 4-tert.Octyl-diphenylamin, 4,4′-Di-tert.butyl-diphenylamin und 2,4,4′-Tri-tert.butyl-diphenylamin,
- d) 23-34 Gew.-% 4-tert.Butyl-4′-tert.octyl-diphenylamin, 2,2′- und 3,3′-Di-tert.octyl-diphenylamin und 2,4-Di-tert.butyl-4′-tert.octyl-diphenylamin
- e) 21-34 Gew.-% 4,4′-Di-tert.octyl-diphenylamin und 2,4-Di-tert.octyl-4′-tert.butyl-diphenylamin.
- Die Komponente (C) kann irgendein cyclisches oder nicht-cyclisches sterisch gehindertes Amin sein. Bevorzugt ist (C) eine Verbindung, die mindestens eine Gruppe der Formel III
- Von Bedeutung sind insbesondere die folgenden Klassen von Polyalkylpiperidinen.
- a) Verbindungen der Formel 1V
- Bedeuten etwaige Substituenten C₁-C₁₂-Alkyl, so stellen sie z.B. Methyl, Ethyl, n-Propyl, n-Butyl, sek.-Butyl, tert.-Butyl, n-Hexyl, n-Octyl, 2-Ethyl-hexyl, n-Nonyl, n-Decyl, n-Undecyl oder n-Dodecyl dar.
- In der Bedeutung von C₁-C₁₈-Alkyl kann R¹¹ oder R¹² z.B. die oben angeführten Gruppen und dazu noch beispielsweise n-Tridecyl, n-Tetradecyl, n-Hexadecyl oder n-Octadecyl darstellen.
- Wenn R¹¹ C₃-C₈-Alkenyl bedeutet, so kann es sich z.B. um 1-Propenyl, Allyl, Methallyl, 2-Butenyl, 2-Pentenyl, 2-Hexenyl, 2-Octenyl, 4-tert.Butyl-2-butenyl handeln.
- R¹¹ ist als C₃-C₈-Alkinyl bevorzugt Propargyl.
- Als C₇-C₁₂-Aralkyl ist R¹¹ insbesondere Phenethyl und vor allem Benzyl.
- R¹¹ ist als C₁-C₈-Alkanoyl beispielsweise Formyl, Propionyl, Butyryl, Octanoyl, aber bevorzugt Acetyl und als C₃-C₅-Alkenoyl insbesondere Acryloyl.
- Bedeutet R¹² einen einwertigen Rest einer Carbonsäure, so stellt es beispielsweise einen Essigsäure-, Capronsäure-, Stearinsäure-, Acrylsäure-, Methacrylsäure-, Benzoe- oder β-(3,5-Di-tert.-butyl-4-hydroxyphenyl)-propionsäurerest dar.
- Bedeutet R¹² einen zweiwertigen Rest einer Dicarbonsäure, so stellt es beispielsweise einen Malonsäure-, Bernsteinsäure-, Glutarsäure-, Adipinsäure-, Korksäure-, Sebacinsäure-, Maleinsäure-, Itaconsäure-, Phthalsäure-, Dibutylmalonsäure-, Dibenzylmalonsäure-, Butyl-(3,5-di-tert.butyl-4-hydroxybenzyl)-malonsäure- oder Bicycloheptendicarbonsäurerest dar.
- Stellt R¹² einen dreiwertigen Rest einer Tricarbonsäure dar, so bedeutet es z.B. einen Trimellitsäure-, Citronensäure- oder Nitrilotriessigsäurerest.
- Stellt R¹² einen vierwertigen Rest einer Tetracarbonsäure dar, so bedeutet es z.B. den vierwertigen Rest von Butan-1,2,3,4-tetracarbonsaure oder von Pyromellitsäure.
- Bedeutet R¹² einen zweiwertigen Rest einer Dicarbaminsäure, so stellt es beispielsweise einen Hexamethylendicarbaminsäure- oder einen 2,4-Toluylen-dicarbaminsäurerest dar.
- Bevorzugt sind Verbindungen der Formel IV, worin R Wasserstoff ist, R¹¹ Wasserstoff oder Methyl ist, n 2 ist und R¹² der Diacylrest einer aliphatischen Dicarbonsäure mit 4-12 C-Atomen ist.
- Beispiele für Polyalkylpiperidin-Verbindungen dieser Klasse sind folgende Verbindungen:
- 1) 4-Hydroxy-2,2,6,6-tetramethylpiperidin
- 2) 1-Allyl-4-hydroxy-2,2,6,6-tetramethylpiperidin
- 3) 1-Benzyl-4-hydroxy-2,2,6,6-tetramethylpiperidin
- 4) 1-(4-tert.-Butyl-2-butenyl)-4-hydroxy-2,2,6,6-tetramethylpiperidin
- 5) 4-Stearoyloxy-2,2,6,6-tetramethylpiperidin
- 6) 1-Ethyl-4-salicyloyloxy-2,2,6,6-tetramethylpiperidin
- 7) 4-Methacryloyloxy-1,2,2,6,6-pentamethylpiperidin
- 8) 1,2,2,6,6-Pentamethylpiperidin-4-yl-β-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionat
- 9) Di-(1-benzyl-2,2,6,6-tetramethylpiperidin-4-yl)-maleinat
- 10) Di-(2,2,6,6-tetramethylpiperidin-4-yl)-succinat
- 11) Di-(2,2,6,6-tetramethylpiperidin-4-yl)-glutarat
- 12) Di-(2,2,6,6-tetramethylpiperidin-4-yl)-adipat
- 13) Di-(2,2,6,6-tetramethylpiperidin-4-yl)-sebacat
- 14) Di-(1,2,2,6,6-pentamethylpiperidin-4-yl)-sebacat
- 15) Di-(1,2,3,6-tetramethyl-2,6-diethyl-piperidin-4-yl)-sebacat
- 16) Di-(1-allyl-2,2,6,6-tetramethylpiperidin-4-yl)-phthalat
- 17) 1-Hydroxy-4-ß-cyanoethyloxy-2,2,6,6-tetramethylpiperidin
- 18) 1-Acetyl-2,2,6,6-tetramethylpiperidin-4-yl-acetat
- 19) Trimellithsäure-tri-(2,2,6,6-tetramethylpiperidin-4-yl)-ester
- 20) 1-Acryloyl-4-benzyloxy-2,2,6,6-tetramethylpiperidin
- 21) Diethylmalonsäure-di(2,2,6,6-tetramethylpiperidin-4-yl)-ester
- 22) Dibutyl-malonsäure-di-(1,2,2,6,6-pentamethylpiperidin-4-yl)-ester
- 23) Butyl-(3,5-di-tert.-butyl-4-hydroxybenzyl)malonsäure-di-(1,2,2,6,6-pentamethylpiperidin-4-yl)-ester
- 24) Di-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-sebacat
- 25) Di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-sebacat
- 26) Hexan-1′,6′-bis-(4-carbamoyloxy-1-n-butyl-2,2,6,6-tetramethylpiperidin)
- 27) Toluol-2′,4′-bis-(4-carbamoyloxy-1-n-propyl-2,2,6,6-tetramethylpiperidin)
- 28) Dimethyl-bis-(2,2,6,6-tetramethylpiperidin-4-oxy)-silan
- 29) Phenyl-tris-(2,2,6,6-tetramethylpiperidin-4-oxy)-silan
- 30) Tris-(1-propyl-2,2,6,6-tetramethylpiperidin-4-yl)-phosphit
- 31) Tris-(1-propyl-2,2,6,6-tetramethylpiperidin-4-yl)-phosphat
- 32) Phenyl-[bis-(1,2,2,6,6-pentamethylpiperidin-4-yl)]-phosphonat
- 33) 4-Hydroxy-1,2,2,6,6-pentamethylpiperidin
- 34) 4-Hydroxy-N-hydroxyethyl-2,2,6,6-tetramethylpiperidin
- 35) 4-Hydroxy-N-(2-hydroxypropyl)-2,2,6,6-tetramethylpiperidin
- 36) 1-Glycidyl-4-hydroxy-2,2,6,6-tetramethylpiperidin
- b) Verbindungen der Formel (V)
- Stellen etwaige Substituenten C₁-C₁₂- oder C₁-C₁₈-Alkyl dar, so haben sie die bereits unter a) angegebene Bedeutung.
- Bedeuten etwaige Substituenten C₅-C₇-Cycloalkyl, so stellen sie insbesondere Cyclohexyl dar.
- Als C₇-C₈-Aralkyl ist R¹³ insbesondere Phenylethyl oder vor allem Benzyl. Als C₂-C₅-Hydroxyalkyl ist R¹³ insbesondere 2-Hydroxyethyl oder 2-Hydroxypropyl.
- R¹³ ist als C₂-C₁₈-Alkanoyl beispielsweise Propionyl, Butyryl, Octanoyl, Dodecanoyl, Hexadecanoyl, Octadecanoyl, aber bevorzugt Acetyl und als C₃-C₅-Alkenoyl insbesondere Acryloyl.
- Bedeutet R¹⁴ C₂-C₈-Alkenyl, dann handelt es sich z.B. um Allyl, Methallyl, 2-Butenyl, 2-Pentenyl, 2-Hexenyl oder 2-Octenyl.
- R¹⁴ als mit einer Hydroxy-, Cyano-, Alkoxycarbonyl- oder Carbamidgruppe substituiertes C₁-C₄-Alkyl kann z.B. 2-Hydroxyethyl, 2-Hydroxypropyl, 2-Cyanethyl, Methoxycarbonylmethyl, 2-Ethoxycarbonylethyl, 2-Aminocarbonylpropyl oder 2-(Dimethylaminocarbonyl)-ethyl sein.
- Stellen etwaige Substituenten C₂-C₁₂-Alkylen dar, so handelt es sich z.B. um Ethylen, Propylen, 2,2-Dimethylpropylen, Tetramethylen, Hexamethylen, Octamethylen, Decamethylen oder Dodecamethylen.
- Bedeuten etwaige Substituenten C₆-C₁₅-Arylen, so stellen sie z.B. o-, m- oder p-Phenylen, 1,4-Naphthylen oder 4,4′-Diphenylen dar.
- Als C₆-C₁₂-Cycloalkylen ist D insbesondere Cyclohexylen.
-
- Beispiele für Polyalkylpiperidin-Verbindungen dieser Klasse sind folgende Verbindungen:
- 37) N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-hexamethylen-1,6-diamin
- 38) N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-hexamethylen-1,6-di-acetamid
- 39) Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-amin
- 40) 4-Benzoylamino-2,2,6,6-tetramethylpiperidin
- 41) N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-N,N′-dibutyl-adipamid
- 42) N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-N,N′-dicyclohexyl-2-hydroxypropylen-1,3-diamin
- 43) N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-p-xylylen-diamin
- 44) N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-succindiamid
- 45) N-(2,2,6,6-Tetramethylpiperidin-4-yl)-β-aminodipropionsäure-di-(2,2,6,6-tetramethylpiperidin-4-yl)-ester
- 46) Die Verbindung der Formel
- 47) 4-(Bis-2-hydroxyethyl-amino)-1,2,2,6,6-pentamethylpiperidin
- 48) 4-(3-Methyl-4-hydroxy-5-tert.-butyl-benzoesäureamido)-2,2,6,6-tetramethylpiperidin
- 49) 4-Methacrylamido-1,2,2,6,6-pentamethylpiperidin
- Bedeutet R¹⁵ C₂-C₈-Alkylen oder -Hydroxyalkylen, so stellt es beispielsweise Ethylen, 1-Methyl-ethylen, Propylen, 2-Ethyl-propylen oder 2-Ethyl-2-hydroxymethylpropylen dar.
- Als C₄-C₂₂-Acyloxyalkylen bedeutet R¹⁵ z.B. 2-Ethyl-2-acetoxymethylpropylen.
- Beispiele für Polyalkylpiperidin-Verbindungen dieser Klasse sind folgende Verbindungen:
- 50) 9-Aza-8,8,10,10-tetramethyl-1,5-dioxaspiro[5.5]undecan
- 51) 9-Aza-8,8,10,10-tetramethyl-3-ethyl-1,5-dioxaspiro[5.5]undecan
- 52) 8-Aza-2,7,7,8,9,9-hexamethyl-1,4-dioxaspiro[4.5]decan
- 53) 9-Aza-3-hydroxymethyl-3-ethyl-8,8,9,10,10-pentamethyl-1,5-dioxaspiro [5.5]undecan
- 54) 9-Aza-3-ethyl-3-acetoxymethyl-9-acetyl-8,8,10,10-tetramethyl-1,5-dioxaspiro[5.5]undecan
- 55) 2,2,6,6-Tetramethylpiperidin-4-spiro-2′-(1′,3′-dioxan)-5′-spiro-5˝-(1˝,3˝-dioxan)-2˝-spiro-4‴-(2‴,2‴,6‴,6‴,-tetramethylpiperidin).
- d) Verbindungen der Formeln VIIA, VIIB und VIIC
- Bedeuten etwaige Substituenten C₁-C₁₂-Alkyl, so stellen sie z.B. Methyl, Ethyl, n-Propyl, n-Butyl, sek.-Butyl, tert.-Butyl, n-Hexyl, n-Octyl, 2-Ethyl-hexyl, n-Nonyl, n-Decyl, n-Undecyl oder n-Dodecyl dar.
- Etwaige Substituenten in der Bedeutung von C₁-C₁₈-Alkyl können z.B. die oben angeführten Gruppen und dazu noch beispielsweise n-Tridecyl, n-Tetradecyl, n-Hexadecyl oder n-Octadecyl darstellen.
- Bedeuten etwaige Substituenten C₂-C₆-Alkoxyalkyl, so stellen sie z.B. Methoxymethyl, Ethoxymethyl, Propoxymethyl, tert.-Butoxymethyl, Ethoxyethyl, Ethoxypropyl, n-Butoxyethyl, tert.-Butoxyethyl, Isopropoxyethyl oder Propoxypropyl dar.
- Stellt R¹⁷ C₃-C₅-Alkenyl dar, so bedeutet es z.B. 1-Propenyl, Allyl, Methallyl, 2-Butenyl oder 2-Pentenyl.
- Als C₇-C₉-Aralkyl sind R¹⁷, T₁ und T₂ insbesondere Phenethyl oder vor allem Benzyl. Bilden T₁ und T₂ zusammen mit dem C-Atom einen Cycloalkanring, so kann dies z.B. ein Cyclopentan-, Cyclohexan-, Cyclooctan- oder Cyclododecanring sein.
- Bedeutet R¹⁷ C₂-C₄-Hydroxyalkyl, so stellt es z.B. 2-Hydroxyethyl, 2-Hydroxypropyl, 2-Hydroxybutyl oder 4-Hydroxybutyl dar.
- Als C₆-C₁₀-Aryl bedeuten R¹⁷, T₁ und T₂ insbesondere Phenyl, α- oder β-Naphthyl, die gegebenenfalls mit Halogen oder C₁-C₄-Alkyl substituiert sind.
- Stellt R¹⁷ C₂-C₁₂-Alkylen dar, so handelt es sich z.B. um Ethylen, Propylen, 2,2-Dimethylpropylen, Tetramethylen, Hexamethylen, Octamethylen, Decamethylen oder Dodecamethylen.
- Als C₄-C₁₂-Alkenylen bedeutet R¹⁷ insbesondere 2-Butenylen, 2-Pentenylen oder 3-Hexenylen.
- Bedeutet R¹⁷ C₆-C₁₂ Arylen, so stellt es beispielsweise o-, m- oder p-Phenylen, 1,4-Naphthylen oder 4,4′-Diphenylen dar.
- Bedeutet Z′ C₂-C₁₂ Alkanoyl, so stellt es beispielsweise Propionyl, Butyryl, Octanoyl, Dodecanoyl, aber bevorzugt Acetyl dar.
- D hat als C₂-C₁₀ Alkylen, C₆-C₁₅ Arylen oder C₆-C₁₂ Cycloalkylen die unter b) angegebene Bedeutung.
- Beispiele für Polyalkylpiperidin-Verbindungen dieser Klasse sind folgende Verbindungen:
- 56) 3-Benzyl-1,3,8-triaza-7,7,9,9-tetramethylspiro[4.5]decan-2,4-dion
- 57) 3-n-Octyl-1,3,8-triaza-7,7,9,9-tetramethylspiro[4.5]decan-2,4-dion
- 58) 3-Allyl-1,3,8-triaza-1,7,7,9,9-pentamethylspiro[4.5]decan-2,4-dion
- 59) 3-Glycidyl-1,3,8-triaza-7,7,8,9,9-pentamethylspiro[4.5]decan-2,4-dion
- 60) 1,3,7,7,8,9,9-Heptamethyl-1,3,8-triazaspiro[4.5]decan-2,4-dion
- 61) 2-Iso-propyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro-[4.5]decan
- 62) 2,2-Dibutyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro-[4.5]decan
- 63) 2,2,4,4-Tetramethyl-7-oxa-3,20-diaza-21-oxo-dispiro[5.1.11.2]-heneicosan
- 64) 2-Butyl-7,7,9,9-tetramethyl-1-oxa-4,8-diaza-3-oxo-spiro-[4,5]decan
- 65) 8-Acetyl-3-dodecyl-1,3,8-triaza-7,7,9,9-tetramethylspiro[4,5]-decan-2,4-dion
- e) Verbindungen der Formel VIII
- Bedeuten etwaige Substituenten C₁-C₁₂-Alkyl, so stellen sie beispielsweise Methyl, Ethyl, n-Propyl, n-Butyl, sek.-Butyl, tert.-Butyl, n-Hexyl, n-Octyl, 2-Ethylhexyl, n-Nonyl, n-Decyl, n-Undecyl oder n-Dodecyl dar.
- Bedeuten etwaige Substituenten C₁-C₄-Hydroxyalkyl, so stellen sie z.B. 2-Hydroxyethyl, 2-Hydroxypropyl, 3-Hydroxypropyl, 2-Hydroxybutyl oder 4-Hydroxybutyl dar.
- Bedeutet A C₂-C₆ Alkylen, so stellt es beispielsweise Ethylen, Propylen, 2,2-Dimethylpropylen, Tetramethylen oder Hexamethylen dar.
- Stellen R²¹ und R²² zusammen C₄-C₅-Alkylen oder Oxaalkylen dar, so bedeutet dies z.B. Tetramethylen, Pentamethylen oder 3-Oxapentamethylen.
-
- f) Oligomere oder polymere Verbindungen, deren wiederkehrende Struktureinheit einen 2,2,6,6-Tetraalkylpiperidinrest der Formel (I) enthält, insbesondere Polyester, Polyäther, Polyamide, Polyamine, Polyurethane, Polyharnstoffe, Polyaminotriazine, Poly(meth)acrylate, Poly(meth)acrylamide und deren Copolymere, die solche Reste enthalten.
-
- Bevorzugt sind Verbindungen der Formel IX, worin R Wasserstoff oder Methyl ist und R¹¹ Wasserstoff oder Methyl ist.
- Beispiele für solche Verbindungen sind:
- 95) 2,2,6,6-Tetramethyl-4-piperidon (Triacetonamin)
- 96) 1,2,2,6,6-Pentamethyl-4-piperidon
- 97) 2,2,6,6-Tetramethyl-4-piperidon-1-oxyl
- 98) 2,3,6-Trimethyl-2,6-diethyl-4-piperidon
- Die Menge des Zusatzes von (B) und (C) zum Basisöl (A) richtet sich nach der Art des Basisöls und nach dem gewünschten Stabilisierungsgrad. Im allgemeinen beträgt die Summe von (B) und (C) 0,1 bis 2 Gew.-%, vorzugsweise 0,5 bis 1 Gew.-%, bezogen auf (A). Das Verhältnis von (B) zu (C) kann in weiten Grenzen variiert werden, im allgemeinen ist (B) die mengenmässig überwiegende Komponente. Vorzugsweise beträgt das Verhältnis (B):(C) 3-5:1.
- Die Komponente (A) ist ein mineralisches oder synthetisches Basisöl, wie es zur Bereitung von Schmierstoffen üblich ist. Synthetische Oele können z.B. Ester von Polycarbonsäuren oder von Polyolen sein, sie können aliphatische Polyester sein oder Poly-α-olefine, Silicone, Phosphorsäureester oder Polyalkylenglykole. Der Schmierstoff kann auch ein Fett auf Basis eines Oeles und eines Verdickungsmittels sein. Solche Schmierstoffe sind z.B. in D. Klamann "Schmierstoffe und artverwandte Produkte", Verlag Chemie, Weinheim 1982, beschrieben.
- Der Schmierstoff kann zusätzlich andere Additive enthalten wie z.B. weitere Antioxidantien, Metallpassivatoren, Rostinhibitoren, Viskositätsindex-Verbesserer, Stockpunktserniedriger, Dispergiermittel, Tenside oder Verschleissschutz-Additive.
- 2,6-Di-tert-butyl-4-methylphenol, 2,6-Di-tert-butylphenol, 2-tert-Butyl-4,6-dimethylphenol, 2,6-Di-tert-butyl-4-ethylphenol, 2,6-Di-tert-butyl-4-n-butylphenol, 2,6-Di-tert-butyl-4-iso-butylphenol, 2,6-Di-cyclopentyl-4-methylphenol, 2-(α-Methylcyclohexyl)-4,6-dimethylphenol, 2,6-Di-octadecyl-4-methylphenol, 2,4,6-Tri-cyclohexylphenol, 2,6-Di-tert-butyl-4-methoxymethylphenol, o-tert-Butylphenol.
- 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-Di-tert-butyl-hydrochinon, 2,5-Di-tert-amyl-hydrochinon, 2,6-Diphenyl-4-octadecyloxyphenol.
- 2,2′-Thio-bis-(6-tert-butyl-4-methylphenol), 2,2′-Thio-bis-(4-octylphenol), 4,4′-Thio-bis-(6-tert-butyl-3-methylphenol), 4,4′-Thio-bis-(6-tert-butyl-2-methylphenol).
- 2,2′-Methylen-bis-(6-tert-butyl-4-methylphenol), 2,2′-Methylen-bis-(6-tert-butyl-4-ethylphenol), 2,2′-Methylen-bis-[4-methyl-6-(α-methylcyclohexyl)-phenol], 2,2′-Methylen-bis-(4-methyl-6-cyclohexylphenol), 2,2′-Methylen-bis-(6-nonyl-4-methylphenol), 2,2′-Methylen-bis-(4,6-di-tert-butylphenol), 2,2′-Ethyliden-bis-(4,6-di-tert-butylphenol), 2,2′-Ethyliden-bis-(6-tert-butyl-4- oder -5-iso-butylphenol), 2,2′-Methylen-bis-[6-(α-methylbenzyl)-4-nonylphenol], 2,2′-Methylen-bis-[6-(α,α-dimethylbenzyl)-4-nonylphenol], 4,4′-Methylen-bis-(2,6-di-tert-butylphenol), 4,4′-Methylen-bis-(6-tert-butyl-2-methylphenol), 1,1-Bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-butan, 2,6-Di-(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-Tris-(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutan, Ethylenglycol-bis-[3,3-bis-(3′-tert-butyl-4′-hydroxyphenyl)-butyrat], Bis-(3-tert-butyl-4-hydroxy-5-methylphenyl)-dicyclopentadien, Bis-[2-(3′-tert-butyl-2′ -hydroxy-5′-methyl-benzyl)-6-tert-butyl-4-methyl-phenyl-terephthalat.
- 1,3,5-Tri-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzol, Bis-(3,5-di-tert-butyl-4-hydroxybenzyl)-sulfid, 3,5-Di-tert-butyl-4-hydroxybenzyl-mercaptoessigsäure-isooctylester, Bis-(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-dithiol-terephthalat, 1,3,5-Tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurat, 1,3,5-Tris-(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-isocyanurat, 3,5-Di-tert-butyl-4-hydroxybenzyl-phosphonsäure-dioctadecylester, 3,5-Di-tert-butyl-4-hydroxybenzyl-phosphonsäure-monoethylester, Calcium-salz.
- 4-Hydroxy-laurinsäureanilid, 4-Hydroxy-stearinsäureanilid, 2,4-Bis-octylmercapto-6-( 3, 5-di-tert-butyl-4-hydroxyanilino)-s-triazin, N-( 3, 5-di-tert-butyl-4-hydroxyphenyl)-carbaminsäureoctylester.
- mit ein- oder mehrwertigen Alkoholen, wie z.B. mit Methanol, Diethylenglycol, Octadecanol, Triethylenglycol, 1,6-Hexandiol, Pentaerythrit, Neopentylglycol, Tris-hydroxyethyl-isocyanurat, Thiodiethylenglycol, Bis-hydroxyethyl-oxalsäurediamid.
- mit ein- oder mehrwertigen Alkoholen, wie z.B. mit Methanol, Diethylenglycol, Octadecanol, Triethylenglycol, 1,6-Hexandiol, Pentaerythrit, Neopentylglycol, Tris-hydroxyethyl-isocyanurat, Thiodiethylenglycol, Di-hydroxyethyl-oxalsäurediamid.
- wie z.B. N,N′-Bis-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexamethylendiamin, N,N′-Bis-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-trimethylendiamin, N,N′-Bis-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hydrazin.
- Aliphatische oder aromatische Phosphite, Ester der Thiodipropionsäure oder der Thiodiessigsäure, oder Salze der Dithiocarbamid- oder Dithiophosphorsäure.
- Triazole, Benztriazole und deren Derivate, Tolutriazole und deren Derivate, 2-Mercaptobenzthiazol, 2-Mercaptobenztriazol, 2,5-Dimercaptobenztriazol, 2,5-Dimercaptobenzthiadiazol, 5,5′-Methylenbisbenztriazol, 4,5,6,7-Tetrahydrobenztriazol, Salicyliden-propylendiamin, Salicylaminoguanidin und dessen Salze.
-
- a) Organische Säuren, ihre Ester, Metallsalze und Anhydride, z.B.:
N-Oleoyl-sarcosin, Sorbitan-mono-oleat, Blei-naphthenat, Alkenylbernsteinsäureanhydrid, z.B. Dodecenylbernsteinsäure-anhydrid, Alkenylbernsteinsäure-Teilester und -Teilamide, 4-Nonylphenoxyessigsäure. - b) Stickstoffhaltige Verbindungen, z.B.:
- I. Primäre, sekundäre oder tertiäre aliphatische oder cycloaliphatische Amine und Amin-Salze von organischen und anorganischen Säuren, z.B. öllösliche Alkylammoniumcarboxylate.
- II. Heterocyclische Verbindungen, z.B.:
Substituierte Imidazoline und Oxazoline.
- c) Phosphorhaltige Verbindungen, z.B.:
Aminsalze von Phosphorsäurepartialestern oder Phosphonsäurepartialestern, Zinkdialkyldithiophosphate. - d) Schwefelhaltige Verbindungen, z.B.:
Barium-dinonylnaphthalin-sulfonate, Calciumpetroleum-sulfonate. - Polyacrylate, Polymethacrylate, Vinylpyrrolidon/Methacrylat-Copolymere, Polyvinylpyrrolidone, Polybutene, Olefin-Copolymere, Styrol/Acrylat-Copolymere, Polyether.
- Polymethacrylat, alkylierte Naphthalinderivate.
- Polybutenylbernsteinsäureamide oder -imide, Polybutenylphosphonsäurederivate, basische Magnesium-, Calcium-, und Bariumsulfonate und -phenolate.
- Schwefel und/oder Phosphor und/oder Halogen enthaltende Verbindungen, wie geschwefelte pflanzliche Oele, Zinkdialkyldithiophosphate, Tritolyl-phosphat, chlorierte Paraffine, Alkyl- und Aryldi- und tri-sulfide, Triphenylphosphorothionate, Diethanolaminomethyltolyltriazol, Di(2-ethylhexyl)aminomethyltolyltriazol.
- Von besonderer Bedeutung ist der Zusatz von phenolischen Antioxidantien und/oder von aliphatischen und aromatischen Phosphiten oder Phosphoniten, die die Stabilisatorwirkung der Komponenten (B) und (C) erhöhen können.
- Beispiele für verwendbare Phosphite und Phosphonite sind:
Triphenylphosphit, Decyl-diphenylphosphit, Phenyl-didecylphosphit, Tris-(nonylphenyl)-phosphit, Trilaurylphosphit, Trioctadecylphosphit, Distearyl-pentaerythritdiphosphit, Tris-(2,4-di-tert.butylphenyl)-phosphit, Diisodecylpentaerythrit-diphosphit, Bis-(2,4-di-tert.butylphenyl)-pentaerythritdiphosphit, Tristearyl-sorbit-triphosphit, Tetrakis-(2,4-di-tert.butylphenyl)-4, 4′-biphenylen-diphosphonit, Bis-(2,6-di-tert.butyl-4-methyl-phenyl)-pentaerythrit-diphosphit. - Die einzelnen Zusätze werden im Oel gelöst. Zur Beschleunigung des Lösevorganges kann das Oel erwärmt werden oder man löst die Zusätze in einem Lösungsmittel vor.
- Der Schmierstoff kann auch Zusätze an festen Schmierstoffen enthalten, wie z.B. Graphit oder Molybdänsulfid.
- Die nachfolgenden Beispiele erläutern die Erfindung näher. Darin bedeuten Teile Gewichtsteile und Prozente Gewichtsprozente, soweit nicht anders angegeben.
- Mittels eines Differential-Scanning-Calorimeters (Thermoanalysator 1090 der Fa. Du Pont) wird die Induktionszeit der Oxidation von Oelproben durch Luft, die 400 ppm NO₂ enthält, unter isothermen Bedingungen gemessen. Die Messung geschieht bei 170°C unter einem Druck von 8 bar. Als Basisöl wird ein Standard-Mineralöl (Aral® 136) verwendet, dem 1 Vol-% 1-Decen zur Steigerung der Sauerstoffempfindlichkeit zugesetzt wird. Zum Oel werden die folgenden Amin-Stabilisatoren zugesetzt.
-
- A-1 Technisches Gemisch erhalten durch Reaktion von Diphenylamin mit Diisobutylen, enthaltend
- a) 3 % Diphenylamin
- b) 14 % 4-tert.Butyl-diphenylamin,
- c) 30 % 4-tert.Octyl-diphenylamin, 4,4′-Di-tert.butyl-diphenylamin und 2,4,4′-Tri-tert.butyl-diphenylamin,
- d) 29 % 4-tert.Butyl-4′-tert.octyl-diphenylamin, 2,2′- und 3,3′-Ditert.octyl-diphenylamin und 2,4-Di-tert.butyl-4′-tert.octyl-diphenylamin,
- e) 18 % 4,4′-Di-tert.octyl-diphenylamin,
- f) 6 % 2,4-Di-tert.octyl-4′-tert.butyl-diphenylamin.
- A-2 3,7-Di(tert.octyl)-phenothiazin
-
- H-1 Di-(2,2,6,6-tetramethylpiperidin-4-yl)-sebacat
- H-2 2,2,6,6-Tetramethyl-4-piperidon
- H-3 Di-(2,2,6,6-tetramethylpiperidin-4-yl)-succinat
- H-4 Di-(1,2,2,6,6-pentamethylpiperidin-4-yl)-sebacat
- H-5 2,3,6-Trimethyl-2,6-diethyl-4-piperidon
- H-6 2,2,6,6-Tetramethyl-4-butylaminopiperidin
- In Tabelle 1 sind die Induktionszeiten angegeben. Je höher die Induktionszeit ist, desto höher ist die antioxidative Wirkung der Stabilisator-Zusätze.
Tabelle 1 Aromat. Amin Gehindertes Amin Induktionszeit (min) - - 43 0,55 % A-1 - 80 0,45 % A-1 0,10 % H-1 91,5 0,45 % A-1 0,10 % H-2 91,5 0,45 % A-1 0,10 % H-3 90,5 0,45 % A-1 0,10 % H-4 90 0,45 % A-1 0,10 % H-5 84,5 0,45 % A-1 0,10 % H-6 89 - Bei der Oxidation von Kohlenwasserstoffen entstehen sauerstoffhaltige Gruppen wie z.B. Hydroxyl-, Carboxyl- oder Estergruppen. Durch Infrarot-Spektroskopie lässt sich die Menge solcher Gruppen gut messen und daraus die Aktivität von Antioxidantien bestimmen. Hierzu werden Proben eines Standard-Mineralöls (Aral® 136), dem zur Erhöhung der Sauerstoffempfindlichkeit 1 Vol-% 1-Decen beigemischt wird, unter isothermen Bedingungen in einer Atmosphäre von Luft, der 400 ppm NO₂ zugemischt wird, unter einem Druck von 8 bar für 12 h erwärmt. Anschliessend wird die IR-Absorption bei 1730 cm⁻¹ und 1630⁻¹ gemessen. Je niedriger diese Werte sind, desto höher ist die Aktivität der Stabilisatoren. Die Tabellen 2a und 2b zeigen die Ergebnisse bei verschiedenen Temperaturen.
Tabelle 2a Oxidation bei 120°C Stabilisator IR-Absorption bei 1730 cm⁻¹ bei 1630⁻¹ 0,55 % A-1 0,471 1,051 0,45 % A-1 + 0,10 % H-2 0,392 0,839 0,45 % A-1 + 0,10 % H-3 0,424 0,863 0,45 % A-1 + 0,10 % H-5 0,396 0,673 - Das Oxidationsverhalten von erfindungsgemäss stabilisierten Schmierölen wurde auch nach der TOST-Methode (turbine oxidation stability test) gemäss ASTM D-943 geprüft.
Hierzu werden 300 ml eines Mineralöls (Mobil STOC K 305) mit 60 ml Wasser versetzt und in Gegenwart von Eisen- und Kupferdraht unter Durchleiten von Sauerstoff 1000 Stunden auf 95°C erwärmt. Gemessen wird die Bildung von Säuren durch Bestimmung der Neutralisationszahl TAN (mg KOH/g Oel) sowie die gebildete Menge an Schlamm = SLUDGE. - Als Stabilisation wird das Amin A-1 allein und im Gemisch mit dem gehinderten Amin H-7 = 2,2,6,6-Tetramethyl-4-dodecyloxypiperidin verwendet, wobei die Gesamtkonzentration der Stabilisatoren immmer 0,25 %, bezogen auf das Oel, beträgt.
A-1 H-7 TAN (mg KOH/g Oel) SLUDGE (mg) 100 % - 0,46 30 95 % 5 % 0,38 27 90 % 10 % 0,30 24 75 % 25 % 0,31 27 - Analog Beispiel 1 wird die Induktionszeit der Oxidation bei 170°C gemessen. Dabei werden die folgenden gehinderten Amine verwendet:
- H-8 N,N′-Bis(2,2,6,6-tetramethylpiperidin-4-yl)-hexamethylendiamin
- H-9 N,N′-Bis(2,2,6,6-tetramethylpiperidin-4-yl)-pentamethylendiamin
- H-10 4-(3-Methoxypropylamino)-2,2,6,6-tetramethylpiperidin
- Wie in Beispiel 1 beschrieben wird die Induktionszeit der Oxidation bei 170°C gemessen. Hierbei wird als aromatisches Amin verwendet:
- A-3 N-(p-Octylphenyl)-1-naphthylamin
- Die Oxidationsbeständigkeit kann auch durch Messung der Viskositätszunahme bei Behandlung mit Sauerstoff bei erhöhter Temperatur gemessen werden.
- Dazu wird durch das Oel 70 Stunden bei 150°C ein Sauerstoff-Strom (1l/h) durchgeleitet. Das Oel wird vorher mit einer katalytischen Menge eines Kupfernaphthenates sensibilisiert. Die Viskosität des Oeles wird vorher und nachher mit einem Ubbelode-Viskosimeter gemessen.
Tabelle 6 Oel Prozentuale Zunahme der Viskosität Basisöl 168 % Basisöl mit Zusatz von 0,6 % A-1 und 0,15 % H-8 3,4 %
Aromatisches Amin | Gehindertes Amin | Induktionszeit (min) |
- | - | 48 |
0,55 % A-1 | - | 86 |
0,45 % A-1 | 0,10 % H-8 | 95 |
0,45 % A-1 | 0,10 % H-9 | 96 |
0,45 % A-1 | 0,10 % H-10 | 89 |
Aromatisches Amin | Gehindertes Amin | Induktionszeit (min) |
0,55 % A-3 | - | 52,8 |
0,45 % A-3 | 0,10 % H-7 | 66 |
Claims (15)
R² Phenyl, C₇-C₁₀-Alkylphenyl, C₇-C₁₈-Alkoxyphenyl oder Naphthyl bedeutet,
R³ Wasserstoff, C₁-C₁₂-Alkyl, Benzyl, Allyl, Methallyl, Phenyl oder eine Gruppe -CH₂SR⁴ bedeutet,
R⁴ C₄-C₁₈-Alkyl, -CH₂COO(C₄-C₁₈-Alkyl) oder -CH₂CH₂COO(C₄-C₁₈-Alkyl) bedeutet, und
R⁵ und R⁶ unabhängig voneinander H, C₁-C₁₈-Alkyl oder C₇-C₉-Phenylalkyl bedeuten und
R¹ C₁-C₄-Alkyl, C₇-C₉-Phenylalkyl, Cyclohexyl, Phenyl, C₁₀-C₁₈-Alkylphenyl oder Naphthyl bedeutet,
R² C₁₀-C₁₈-Alkylphenyl oder Phenyl bedeutet,
R³ Wasserstoff, C₁-C₈-Alkyl, Benzyl, Allyl oder eine Gruppe -CH₂SR⁴ bedeutet,
R⁴ C₈-C₁₈-Alkyl oder -CH₂COO(C₈-C₁₈-Alkyl) bedeutet, und
R⁵ und R⁶ unabhängig voneinander H, C₁-C₁₂-Alkyl oder C₇-C₉-Phenylalkyl bedeuten.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH273788 | 1988-07-18 | ||
CH2737/88 | 1988-07-18 |
Publications (2)
Publication Number | Publication Date |
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EP0356677A1 true EP0356677A1 (de) | 1990-03-07 |
EP0356677B1 EP0356677B1 (de) | 1993-06-09 |
Family
ID=4240482
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EP89112951A Expired - Lifetime EP0356677B1 (de) | 1988-07-18 | 1989-07-14 | Schmierstoffzusammensetzung |
Country Status (13)
Country | Link |
---|---|
US (1) | US5073278A (de) |
EP (1) | EP0356677B1 (de) |
JP (1) | JP2832541B2 (de) |
KR (1) | KR970007781B1 (de) |
CN (1) | CN1020748C (de) |
AU (1) | AU621910B2 (de) |
BR (1) | BR8903526A (de) |
CA (1) | CA1334532C (de) |
DE (1) | DE58904610D1 (de) |
ES (1) | ES2055762T3 (de) |
MX (1) | MX169536B (de) |
SU (1) | SU1736343A3 (de) |
ZA (1) | ZA895408B (de) |
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EP0432089A1 (de) * | 1989-11-08 | 1991-06-12 | Ciba-Geigy Ag | Schmierstoffzusammensetzungen |
EP0475904A2 (de) * | 1990-09-13 | 1992-03-18 | Ciba-Geigy Ag | Stoffgemische und Zusammensetzungen enthaltend Phenothiazine |
FR2671354A1 (fr) * | 1991-01-08 | 1992-07-10 | Ciba Geigy Ag | Compositions lubrifiantes renfermant une association de stabilisants. |
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Cited By (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0406825A1 (de) * | 1989-07-07 | 1991-01-09 | Ciba-Geigy Ag | Schmierstoffzusammensetzung |
EP0406826A1 (de) * | 1989-07-07 | 1991-01-09 | Ciba-Geigy Ag | Schmierstoffzusammensetzung |
US5268113A (en) * | 1989-07-07 | 1993-12-07 | Ciba-Geigy Corporation | Lubricant composition |
US5167844A (en) * | 1989-11-08 | 1992-12-01 | Ciba-Geigy Corporation | Lubricant formulations |
EP0432089A1 (de) * | 1989-11-08 | 1991-06-12 | Ciba-Geigy Ag | Schmierstoffzusammensetzungen |
EP0475904A2 (de) * | 1990-09-13 | 1992-03-18 | Ciba-Geigy Ag | Stoffgemische und Zusammensetzungen enthaltend Phenothiazine |
EP0475904A3 (en) * | 1990-09-13 | 1993-02-03 | Ciba-Geigy Ag | Mixtures and compositions containing phenothiazines |
GB2253411A (en) * | 1991-01-08 | 1992-09-09 | Ciba Geigy Ag | Lubricant compositions containing antioxidant additives |
BE1004925A5 (fr) * | 1991-01-08 | 1993-02-23 | Ciba Geigy Ag | Compositions lubrifiantes renfermant une association de stabilisants. |
US5198130A (en) * | 1991-01-08 | 1993-03-30 | Ciba-Geigy Corporation | Lubricant compositions |
FR2671354A1 (fr) * | 1991-01-08 | 1992-07-10 | Ciba Geigy Ag | Compositions lubrifiantes renfermant une association de stabilisants. |
GB2253411B (en) * | 1991-01-08 | 1994-12-07 | Ciba Geigy Ag | Lubricant compositions |
US5773393A (en) * | 1991-09-16 | 1998-06-30 | The Lubrizol Corporation | Oil compositions useful in hydraulic fluids |
US6013704A (en) * | 1996-09-13 | 2000-01-11 | Ciba Specialty Chemicals Corporation | Hydroxyphenyltriazines |
WO2008015116A2 (en) * | 2006-07-31 | 2008-02-07 | Ciba Holding Inc. | Lubricant composition |
AU2007280548B2 (en) * | 2006-07-31 | 2012-04-05 | Basf Se | Lubricant composition |
RU2462505C2 (ru) * | 2006-07-31 | 2012-09-27 | Циба Холдинг Инк. | Смазочная композиция |
WO2008015116A3 (en) * | 2006-07-31 | 2008-03-20 | Ciba Sc Holding Ag | Lubricant composition |
US9370764B2 (en) | 2007-05-23 | 2016-06-21 | International Paper Company | Compositions and particles containing cellulosic fibers and stabilized-and/or activated-urease inhibitors, as well as methods of making and using the same |
US20080294132A1 (en) * | 2007-05-23 | 2008-11-27 | Zheng Tan | Cellulosic fiber compositions having odor control and methods of making and using the same |
US8809616B2 (en) * | 2007-05-23 | 2014-08-19 | International Paper Company | Cellulosic fiber compositions having odor control and methods of making and using the same |
EP2671449A1 (de) | 2012-06-06 | 2013-12-11 | Construction Research & Technology GmbH | Verwendung von Vanadiumpentoxidpartikeln als Biozid |
CN104640961A (zh) * | 2012-08-14 | 2015-05-20 | 巴斯夫欧洲公司 | 用于润滑剂组合物的聚合物和形成其的方法 |
EP2885388A4 (de) * | 2012-08-14 | 2016-03-09 | Basf Se | Polymer für schmiermittelzusammensetzungen und verfahren zu ihrer herstellung |
US9688938B2 (en) | 2012-08-14 | 2017-06-27 | Basf Se | Lubrican composition comprising acyclic hindered amines |
US9862909B2 (en) | 2012-08-14 | 2018-01-09 | Basf Se | Polymer for lubricant compositions and method of forming the same |
US9902916B2 (en) | 2012-08-14 | 2018-02-27 | Basf Se | Lubricant composition comprising hindered cyclic amines |
US10081777B2 (en) | 2012-08-14 | 2018-09-25 | Basf Se | Polymer for lubricant compositions and method of forming the same |
US10093879B2 (en) | 2012-08-14 | 2018-10-09 | Basf Se | Lubricant composition comprising hindered cyclic amines |
Also Published As
Publication number | Publication date |
---|---|
KR970007781B1 (en) | 1997-05-16 |
EP0356677B1 (de) | 1993-06-09 |
BR8903526A (pt) | 1990-03-13 |
SU1736343A3 (ru) | 1992-05-23 |
ES2055762T3 (es) | 1994-09-01 |
KR910003078A (ko) | 1991-02-26 |
MX169536B (es) | 1993-07-09 |
AU621910B2 (en) | 1992-03-26 |
ZA895408B (en) | 1990-03-28 |
US5073278A (en) | 1991-12-17 |
AU3817489A (en) | 1990-01-18 |
JPH0273894A (ja) | 1990-03-13 |
CN1041610A (zh) | 1990-04-25 |
JP2832541B2 (ja) | 1998-12-09 |
CA1334532C (en) | 1995-02-21 |
CN1020748C (zh) | 1993-05-19 |
DE58904610D1 (de) | 1993-07-15 |
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