DD297443A5 - LUBRICANT COMPOSITIONS - Google Patents
LUBRICANT COMPOSITIONS Download PDFInfo
- Publication number
- DD297443A5 DD297443A5 DD90342534A DD34253490A DD297443A5 DD 297443 A5 DD297443 A5 DD 297443A5 DD 90342534 A DD90342534 A DD 90342534A DD 34253490 A DD34253490 A DD 34253490A DD 297443 A5 DD297443 A5 DD 297443A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkyl
- formula
- hydrogen
- group
- composition according
- Prior art date
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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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
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- 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
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- 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
- 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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- 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
- 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
- C10M129/68—Esters
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- 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
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- 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
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
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- 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
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/40—Six-membered ring containing nitrogen and carbon only
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- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/40—Six-membered ring containing nitrogen and carbon only
- C10M133/42—Triazines
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- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M135/24—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M135/26—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
- C10M135/30—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups; Derivatives thereof
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/041—Carbon; Graphite; Carbon black
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- C10M2201/041—Carbon; Graphite; Carbon black
- C10M2201/042—Carbon; Graphite; Carbon black halogenated, i.e. graphite fluoride
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- C10M2201/066—Molybdenum sulfide
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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- C10M2205/026—Butene
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- C10M2207/027—Neutral salts thereof
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Abstract
Schmierstoffe können gegen Oxidation stabilisiert werden durch Zusatz von a) einem sterisch gehinderten Amin und b) einem Phenol der Formel I, worin A, B und X die in Anspruch 1 gegebenen Bedeutungen haben. Vorzugsweise verwendet man Phenole der Formel I, die eine Thioethergruppe enthalten. Formel I{Schmierstoffzusammensetzung; Stabilisierung gegen Oxidation; sterisch gehindertes Amin; Phenol; Phenol mit Thioethergruppe}Lubricants can be stabilized against oxidation by addition of a) a sterically hindered amine and b) a phenol of the formula I in which A, B and X have the meanings given in claim 1. Preference is given to using phenols of the formula I which contain a thioether group. Formula I {lubricant composition; Stabilization against oxidation; sterically hindered amine; Phenol; Phenol with thioether group}
Description
Die vorliegende Erfindung betrifft Schmierstoffzusammensetzungen, die gegen oxidativen Abbau stabilisiert sind. Die Stabilisierung erfolgt durch Zusatz von mindestens zwei spezifischen Zusatzstoffen.The present invention relates to lubricant compositions stabilized against oxidative degradation. The stabilization takes place by adding at least two specific additives.
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.It is known and customary to add to lubricants based on mineral oils or synthetic oils additives to improve their performance properties. Of particular importance are additives against oxidative degradation of the lubricants, so-called antioxidants. The oxidative degradation of lubricants plays a major role, especially in engine oils, since there are high temperatures in the combustion chamber of the engine and, in addition to oxygen, nitrogen oxides (NO x ) are present, which act as oxidation catalysts.
Als Antioxidantien für Schmierstoffe werden vor allem organische Schwefel- und Phosphorverbindungen verwendet, aber auch aromatische Amine und Phenole, insbesondere sterisch gehinderte Phenole (siehez. B. Ulimanns Encyklopädie der technischen Chemie, 4.Auflage, Verlag Chemie, Band 20 [1981]; Seite 541-53).As antioxidants for lubricants, especially organic sulfur and phosphorus compounds are used, but also aromatic amines and phenols, in particular sterically hindered phenols (see, for example, Ulimanns Encyklopadie der technischen Chemie, 4th Edition, Verlag Chemie, Volume 20 [1981]; 541-53).
Es wurden auch schon sterisch gehinderte Amine als Stabilisatoren für Schmieröle vorgeschlagen, z. B. in der US-A-4 069199 oder der JP-A-85/28496.Hindered amines have also been proposed as stabilizers for lubricating oils, e.g. In US-A-4 069199 or JP-A-85/28496.
In der EP-A-356677 wurden Gemische von aromatischen Aminen und sterisch gehinderten Aminen als Antioxidantien für Schmierstoffe vorgeschlagen, wobei diesen Gemischen auch phenolische Antioxidantien zugesetzt werden können.EP-A-356677 has proposed mixtures of aromatic amines and sterically hindered amines as antioxidants for lubricants, phenolic antioxidants also being able to be added to these mixtures.
Es wurde gefunden, daß sich Kombinationen von phenolischen Antioxidantien mit sterisch gehinderten Aminen auch ohne Zusatz von aromatischen Aminen hervorragend zur Stabilisierung von Schmierstoffen eignen.It has been found that combinations of phenolic antioxidants with sterically hindered amines, even without the addition of aromatic amines, are outstandingly suitable for stabilizing lubricants.
Die vorliegende Erfindung betrifft eine Schmierstoffzusammensetzung, enthaltendThe present invention relates to a lubricant composition containing
(A) ein mineralisches oder synthetisches OeI oder ein Gemisch solcher OeIe,(A) a mineral or synthetic oil or a mixture of such oils,
(B) mindestens ein sterisch gehindertes Amin und(B) at least one sterically hindered amine and
(C) mindestens ein Phenol der Formel I,(C) at least one phenol of the formula I,
worin A Wasserstoff, C,-C24-Alkyl, Ce-C^-Cycloalkyl, Cr-C9-Phenylalkyl, Phenyl oder eine Gruppe -CH2-S-R1 oderwherein A is hydrogen, C, -C 24 alkyl, Ce-C ^ cycloalkyl, Cr-C 9 phenylalkyl, phenyl or a group -CH 2 -SR 1 or
-CH2- Nj-B-CH 2 - N jB
B C)-C24-Alkyl, Cs-C^-Cycloalkyl, C7-C9-Phenylalkyl, Phenyl oder eine Gruppe -CH2-S-R1 bedeutet, X Wasserstoff, C,-C,e-Alkyl oder eine der Gruppen -C,H2,-Sq-R2, -C6H20-CO-OR3, -CbH2b-CO-N(R6)(Re), -CH2N(R10J(R") oderBC) -C 24 alkyl, Cs-C ^ cycloalkyl, C7-C9 phenylalkyl, phenyl or a group -CH 2 -SR 1, X is hydrogen, C, -C, e alkyl, or one of the groups - C, H 2 , -S q -R 2 , -C 6 H 20 -CO-OR 3 , -C b H 2 b-CO-N (R 6 ) (R e ), -CH 2 N (R 10 J (R ") or
• — ·• - ·
-CH2-^ ^--0H bedeutet,-CH 2 - ^ ^ - 0H means
R1 C,-Ci8-Alkyl, Phenyl oder eine Gruppe -(CH2)C-CO-OR4 oder-CH2CH2OR9 bedeutet, R2 Wasserstoff, C1-C18-AIkVl, Phenyl, Benzyl, oder eine GruppeR 1 is C 1 -C 8 -alkyl, phenyl or a group - (CH 2 ) C -CO-OR 4 or -CH 2 CH 2 OR 9 , R 2 is hydrogen, C 1 -C 18 -alkyl, phenyl, benzyl , or a group
^-OH oder -(CHz)0-CO-OR" oder -CH2CH2OR9 ^ -OH or - (CHz) 0 -CO-OR "or -CH 2 CH 2 OR 9
bedeutet,means
R3 C1-C6O-AIkYl, oder eine der Gruppen -CH-CH2-S-R8 R 3 C 1 -C 6 O-AIkYl, or one of the groups -CH-CH 2 -SR 8
-CH2-C--CH 2 -C-
-CH2-O-C-C-H0, ( y~ OH-CH 2 -OCCH 0 , (y~ OH
b Zo \ /b Zo \ /
bedeutet, worin Q Cj-Co-Alkylen, C4-Ce-Thiaalkylen oder eine Gruppe -CH2CH2(OCH2CH2Jd- ist, R4 C,-C24-Alkyl bedeutet,is wherein Q Cj-Co-alkylene, C 4 -C e -Thiaalkylen or a group -CH 2 CH 2 (OCH 2 CH 2 JD, R 4 is C, -C 24 alkyl,
R6 Wasserstoff, C,-C18-Alkyl oder Cyclohexyl bedeutet, Re Ci-Cie-Alkyl, Cyclohexyl, Phenyl, durch C,-Ci8-Alkyl substituiertes Phenyl oder eine der GruppenR 6 is hydrogen, C 1 -C 18 -alkyl or cyclohexyl, R e is C 1 -C 6 -alkyl, cyclohexyl, phenyl, C 1 -C 8 -alkyl-substituted phenyl or one of the groups
•-0H• -0H
-C-(-(CH2)-O-e-C,H_,—f-C - (- (CH 2 ) -OeC, H _, - f
D Δ0 \D Δ0 \
J3 J 3
bedeutet,means
oder R5 und Re zusammen C^Cs-Alkylen, das durch -O- oder-NH- unterbrochen sein kann, bedeuten, R7 Wasserstoff, C,-C4-Alkyl oder Phenyl bedeutet, R8 Ci-C18-Alkyl bedeutet,or R 5 and R e together are C 1 -C 5 -alkylene which may be interrupted by -O- or -NH-, R 7 is hydrogen, C 1 -C 4 -alkyl or phenyl, R 8 is C 1 -C 18 - Alkyl means
R9 Wasserstoff, Ci-C24-Alkyl, Phenyl, C2-Ci8-Alkanoyl oder Benzoyl bedeutet, R'0 Q-Cie-Alkyl, Cyclohexyl, Phenyl, durch C1-Ci8-AIkYl substituiertes Phenyl oder eine GruppeR 9 is hydrogen, Ci-C 2 4 alkyl, phenyl, C2-C 8 alkanoyl or benzoyl, R '0 Q-Cie-alkyl, cyclohexyl, phenyl, C 1 -C 8 -alkyl-substituted phenyl or a group
-(CH2) -NH -CH2-- (CH 2 ) -NH -CH 2 -
B bedeutet,B means
R" Wasserstoff, C,-C18-Alkyl, Cyclohexyl, oder eine GruppeR "is hydrogen, C, -C 18 alkyl, cyclohexyl, or a group
R10 und R" zusammen C^CVAIkylen, das durch-O-oder-NH-unterbrochen sein kann, bedeuten a 0,1,2 oder 3 ist,R 10 and R "together denote C 1 -C 4 -alkylene which may be interrupted by -O- or -NH-, a is 0, 1, 2, or 3,
b 0,1,2 oder 3 ist,b is 0,1,2 or 3,
c 1 oder 2 ist,c is 1 or 2,
d 1 bis 5 ist,d is 1 to 5,
f 2 bis 8 ist undf is 2 to 8 and
q 1,2,3 oder 4 ist,q is 1,2,3 or 4,
oder als Komponente (C) ein Gemisch von Polyphenolen, das durch Reaktion von mindestens einem Phenol der Formelor as component (C) a mixture of polyphenols obtained by reaction of at least one phenol of the formula
V11 OHV 11 OH
c-/\ V\/D c - / \ V \ / D
1J j oder Il i 1 J j or Il i
mit mindestens einem Phenol der Formelwith at least one phenol of the formula
OH OHOH OH
und mit Formaldehyd bzw. Paraformaldehyd entsteht, wobei C, D und E unabhängig voneinander Ci-C24-Alkyl, Cyclohexyl oder Phenyl bedeuten, wobei die Zusammensetzung kein aromatisches Amin enthält.and with formaldehyde or paraformaldehyde, where C, D and E independently of one another are C 1 -C 4 -alkyl, cyclohexyl or phenyl, the composition containing no aromatic amine.
In dieser Zusammensetzung beträgt das Gewichtsverhältnis von (B) zu (C) vorzugsweise 1:1 bis 1:100, insbesondere 1:3 bis 1:20.In this composition, the weight ratio of (B) to (C) is preferably 1: 1 to 1: 100, especially 1: 3 to 1:20.
Die Summe von (B) und (C) beträgt vorzugsweise 0,05 bis 5Ge"w.-%, insbssondere 0,1 bis 3Gew.-%, von (A).The sum of (B) and (C) is preferably 0.05 to 5 wt%, especially 0.1 to 3 wt%, of (A).
A und B als C,-C24-Alkyl können lineares oder verzweigtes Alkyl sein, wie z. B. Methyl, Ethyl, i-Propyl, t-Butyl, s-Butyl, s-Pentyl, t-Pentyl, n-Hexyl, i-Hexyl, t-Hexyl, i-Heptyl, n-Octyl, t-Octyl, s-Decyl, s-Dodscyl, n-Dodecyl, s-Tetradecyl, n-Hexadecyl, n-Octadecyl, s-Octadecyl oder n-Eikosyl.A and B as C, -C 24 alkyl may be linear or branched alkyl, such as. Methyl, ethyl, i-propyl, t -butyl, s -butyl, s -pentyl, t -pentyl, n -hexyl, i -hexyl, t -hexyl, i-heptyl, n -octyl, t -octyl, s-decyl, s-dodecyl, n-dodecyl, s-tetradecyl, n-hexadecyl, n-octadecyl, s-octadecyl or n-eicosyl.
A und B als Cycloalkyl können z.B. Cyclopentyl, Cyclohexyl oder Cyclooctyl sein, insbesondere Cyclohexyl. A und B als Phenylalkyl können z. B. Benzyl, Phenylethyl, Phenylpropyl oder α,α-Dimethylbenzyi sein.A and B as cycloalkyl may be e.g. Cyclopentyl, cyclohexyl or cyclooctyl, in particular cyclohexyl. A and B as phenylalkyl may, for. B. benzyl, phenylethyl, phenylpropyl or α, α-dimethylbenzyi be.
Rs und R6 als C|-C12-Alkyl können z. B. Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl, Octyl, Der.yl oder Dodecyl sein. R1, R2, R3 und R8 als C,-C18-AIkVl können darüber hinaus auch z.B. Tetradecyl, Hexadecyl oder Octadecyl seh;. R4 als C|-C24-Alkyl kann darüber hinaus auch z.B. Eikosyl oder Tetraeikosyl sein.R s and R 6 as C | -C 12 alkyl may, for. Methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, deryl or dodecyl. R 1 , R 2 , R 3 and R 8 as C, -C 18 -AlkVl can also see, for example, tetradecyl, hexadecyl or octadecyl seh ;. In addition, R 4 as C 1 -C 2 4-alkyl may also be, for example, eicosyl or tetra-eicosyl.
Der Index a ist bevorzugt 0,1 oder 2, insbesondere 0 oder 1; b ist bevorzugt 0,1 odsr 2, insbesondere 1 oder 2; q ist bevorzugt 1 oder 2, insbesondere 1.The index a is preferably 0.1 or 2, in particular 0 or 1; b is preferably 0.1 or 2, in particular 1 or 2; q is preferably 1 or 2, in particular 1.
Die Komponente (A) ist ein mineralisches oder synthetisches Basisöl, wie es zur Bereitung von Schmierstoffen üblich ist.The component (A) is a mineral or synthetic base oil, as is customary for the preparation of lubricants.
Synthetische OeIe können z. B. Ester von Polycarbonsäuren oder von Polyolen sein, sie können aliphatische Polyester sein oder Poly-a-olefine, Silicone, Phosphorsäureester oder Polyalkylenglykole. Der Schmierstoff kann auch ein Fett auf Basis eines Oeles und eines Verdickungsmittel sein. Solche Schmierstoffe sind z. B. in D. Klamann „Schmierstoffe und artverwandte Produkte", Verlag Chemie, Weinheim 1982, beschrieben.Synthetic oils may e.g. As esters of polycarboxylic acids or polyols, they may be aliphatic polyesters or poly-α-olefins, silicones, phosphoric acid esters or polyalkylene glycols. The lubricant may also be a grease based on an oil and a thickening agent. Such lubricants are z. B. in D. Klamann "lubricants and related products", Verlag Chemie, Weinheim 1982 described.
Die Komponente (8) kann irgendein cyclisches oder nichtcyclisches, vorzugsweise cyclisches, sterisch gehindertes Amin sein.Component (8) may be any cyclic or noncyclic, preferably cyclic, hindered amine.
Bevorzugt ist (B) eine Verbindung, die mindestens eine Gruppe der Formel Il enthält,(B) is preferably a compound which contains at least one group of the formula II,
RCH2 P^* RCH 2 P ^ *
—N1 -N 1
RCH2 CH3 RCH 2 CH 3
worin R Wasserstoff oder Methyl bedeutet. Bevorzugt ist R Wasserstoff. Es handelt sich dabei um Derivate von Polyalkylpiperidinen, insbesondere von 2,2,6,6-Ttiiramethylpiperidin. Bevorzugt tragen diese Verbindungen in 4-Stellung des Piperidinringes einen oder zwei polare Substituenten oder ein polares Spiro-Ringsystem. Es kann sich bei diesen Verbindungen um niedermolekulare oder oligomere oder polymere Verbindungen handeln.where R is hydrogen or methyl. Preferably, R is hydrogen. These are derivatives of polyalkylpiperidines, in particular 2,2,6,6-tiramethylpiperidine. Preferably, these compounds carry in the 4-position of the piperidine ring one or two polar substituents or a polar spiro ring system. These compounds may be low molecular weight or oligomeric or polymeric compounds.
Von Bedeutung sind insbesondere die folgenden Klasson von Polyalkylpiperidinen. a) Verbindungen der Formel III,Of particular importance are the following Klasson of polyalkylpiperidines. a) compounds of the formula III,
)— () - (
worin η eine Zahl von 1 bis 4, vorzugsweise 1 oder 2 bedeutet, R Wasserstoff oder Methyl bedeutet, R11 Wasserstoff, Oxyl, Hydroxyl, C,-C,rAlkyl, C1-C8 Alkenyl, Cj-Ce-Alkinyl, Cj-Cu-Aralkyl, C,-C18-Alkoxy, C5-C8-CyClOaIkOXy, Cz-CrPhenylalkoxy, Ci-Ce-Alkanoy^Ca-Ce-Alkenoyl, Ci-Cis-Alkanoyloxy, Benzyloxy, Glycidyl oder eine Gruppe -CHjCH(OH)-Z, worin Z Wasserstoff, Methyl oder Phenyl ist, bedeutet, wobei R" vorzugsweise H, Ci-C^-AlkyI, Allyl, Benzyl, Acetyl oder Acryloyl ist und R12, wenn η ist. Wasserstoff, gegebenenfalls durch ein oder mehrere Sauerstoffatome unterbrochenes C,-C)8-Alkyl, Cyanethyl, Benzyl, Glycidyl, einen einwertigen Rest einer aliphatischen, cycloaliphatische^ araliphatischen, ungesättigten oder aromatischen Carbonsäure, Carbaminsäure oder Phosphor enthaltenden Säure oder einen einwertigen Silylrest, vorzugsweise einen Rest einer aliphatischen Carbonsäure mit 2 bis 18 C-Atomen, einer cycloaliphatische!! Carbonsäure mit 7 bis 15 C-Atomen, einer α,β-ungesättigten Carbonsäure mit 3 bis 5 C-Atomen oder einer aromatischen Carbonsäure mit 7 bis 15 C-Atomen bedeutet, wenn η 2 ist, C,-C12-Alkylen, C^-CirAlkenylen, Xylylen, einen zweiwertigen Rest einer aliphatischen, cycloaliphatische^ araliphatischen oder aromatischen Dicarbonsäure, Dicarbaminsäureoder Phosphor enthaltenden Säure oder einen zweiwertigen Silylrest, vorzugsweise einen Rest einer aliphatischen Dicarbonsäure mit 2 bis 36 C-Atomen, einer cycloaliphatischen oder aromatischen Dicarbonsäure mit 8-14 C-Atomen oder einer aliphatischen, cycloaliphatische oder aromatischen Dicarbaminsäure mit 8-14 C-Atomen bedeutet, wenn η 3 ist, einen dreiwertigen Rest einer aliphatischen, cycloaliphatischen oder aromatischen Tricarbonsäure, einer aromatischen Tricarbaminsäure oder einer Phosphor enthaltenden Säure oder einen dreiwertigen Silylrest bedeutet und wenn η 4 ist, einen vierwertigen Rest einer aliphatischen, cycloaliphatischen oder aromatischen Tetracarbonsäure bedeutet.wherein η is a number from 1 to 4, preferably 1 or 2, R is hydrogen or methyl, R 11 is hydrogen, oxyl, hydroxyl, C, -C, r alkyl, C 1 -C 8 alkenyl, Cj-Ce-alkynyl, C 1 -C 6 aralkyl, C 1 -C 18 alkoxy, C 5 -C 8 cycloalkyl, Cz-C 1 -C 4 phenylalkoxy, C 1 -C 6 alkanoyloCaCe-alkenoyl, C 1 -Cis alkanoyloxy, benzyloxy, glycidyl or a group -CHjCH (OH) -Z, where Z is hydrogen, methyl or phenyl, where R "is preferably H, C 1 -C 4 -alkyl, allyl, benzyl, acetyl or acryloyl and R 12 , if η is hydrogen, optionally interrupted by one or more oxygen atoms C, -C ) 8 alkyl, cyanoethyl, benzyl, glycidyl, a monovalent radical of an aliphatic, cycloaliphatic ^ araliphatic, unsaturated or aromatic carboxylic acid, carbamic acid or phosphorus-containing acid or a monovalent silyl radical, preferably a radical an aliphatic carboxylic acid having 2 to 18 C atoms, a cycloaliphatic carboxylic acid having 7 to 15 C atoms, a , β-unsaturated carboxylic acid having 3 to 5 carbon atoms or of an aromatic carboxylic acid having 7 to 15 carbon atoms, when η is 2, C, -C 12 alkylene, C ^ -CirAlkenylen, xylylene, a divalent radical of an aliphatic , cycloaliphatic ^ araliphatic or aromatic dicarboxylic acid, dicarbamic acid or phosphorus-containing acid or a divalent silyl radical, preferably a radical of an aliphatic dicarboxylic acid having 2 to 36 carbon atoms, a cycloaliphatic or aromatic dicarboxylic acid having 8-14 C-atoms or an aliphatic, cycloaliphatic or aromatic Dicarbamic acid having 8-14 C atoms, when η is 3, is a trivalent radical of an aliphatic, cycloaliphatic or aromatic tricarboxylic acid, an aromatic tricarbamic acid or a phosphorus-containing acid or a trivalent silyl radical and when η is 4, a tetravalent radical of an aliphatic , cycloaliphatic or aromatic tetracarboxylic acid b edeutet.
Badeuten etwaige Substituenten Ci-C^-Alkyl, so stellen sie z. B. Methyl, Ethyl, n-Propyl, η-Butyl, sek.-Butyl, tert.-Butyl, n-Hexyl, n-Octyl, 2-Ethyl-hexyl, h Nonyl, n-Decyl, n-Undecyl oder n-Dodecyl dar.Badeuten any substituents Ci-C ^ alkyl, they provide z. For example, methyl, ethyl, n-propyl, η-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethyl-hexyl, h nonyl, n-decyl, n-undecyl or n -Dodecyl is.
In der Bedeutung von C,-C]8-Alkyl kann R" oder R'2 z. B. die oben angeführten Gruppen und dazu noch beispielsweise n-Tridecyl, n-Tetradecyl, n-Hexadecyl oder n-Octadecyl darstellen.In the meaning of C 1 -C 8 -alkyl, R 1 'or R' 2 may, for example, represent the abovementioned groups and additionally, for example, n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl.
Wenn R" C)-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.If R "is C) -C 8 -alkenyl, it may be, for example, 1-propenyl, allyl, methallyl, 2-butenyl, 2-pentenyl, 2-hexenyl, 2-octenyl, 4-tert-butyl-2 -butenyl act.
R" ist als Cj-C8-Alkinyl bevorzugt Propargyl.R "as Cj-C 8 -alkynyl is preferably propargyl.
Als Cr-C,2-Aralkyl ist R" insbesondere Phenethyl und vor allem Benzyl.As Cr-C, 2-aralkyl, R "is in particular phenethyl and especially benzyl.
R" ist als Cp-Cs-Alkanoyl beispielsweise Formyl, Propionyl, Butyryl, Octanoyl, aber bevorzugt Acetyl und als C3-C6-AlkenoyI insbesondere Acryloyl.R "is as Cp-Cs-alkanoyl, for example, formyl, propionyl, butyryl, octanoyl, but preferably acetyl and as C 3 -C 6 -AlkenoyI especially acryloyl.
Bedeutet R'2 einen einwertigen Rest einer Carbonsäure, so stellt es beispielsweise einen Essigsäure-, Capronsäure-, Stearinsäure-, Acrylsäure-, Methaciylsäure-, Benzoe- oder ß-fc3,5-Di-tert.-butyl-4-hydroxyphenyl)-prc.pionsäurerest dar.If R ' 2 denotes a monovalent radical of a carboxylic acid, it represents, for example, an acetic acid, caproic acid, stearic acid, acrylic acid, methacylic acid, benzoic acid or β-fc3,5-di-tert-butyl-4-hydroxyphenyl. -prc.pione acid residue.
Bedeutet R'2 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.If R ' 2 denotes a bivalent radical of a dicarboxylic acid, it represents, for example, a malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, sebacic acid, maleic acid, itaconic acid, phthalic acid, dibutylmalonic acid, dibenzylmalonic acid, butyl (3,5-di-tert-butyl-4-hydroxybenzyl) -malonic acid or BicycloheptendicarbonsÄureeste.
Stellt R'2 einen dreiwertigen Rest einer Tricarbonsäure dar, so bedeutet es z. B. einen Trimellitsäure-, Citronensäure- oder Nitrilotriessigsäurerest.If R ' 2 represents a trivalent radical of a tricarboxylic acid, it means z. B. a Trimellitsäure-, citric acid or nitrilotriacetic acid residue.
Stellt R12 einen vierwertigen Rest einer Tetracarbonsäure dar, so bedeutet es z. B. den vierwertigen Rest von Butan-1,2,3,4-tetracarbonsäure oder von Pyromellitsäure.R 12 represents a tetravalent radical of a tetracarboxylic acid, it means z. As the tetravalent radical of butane-1,2,3,4-tetracarboxylic acid or pyromellitic acid.
Bedeutet R'2 einen zweiwertigen Rest einer Dicarbaminsäure, so stellt es beispielsweise einen Hexamethylendicarbaminsäure- oder einen 2,4-Toluylen-dicarbaminsäurerest dar.If R ' 2 is a bivalent radical of a dicarbamic acid, it represents, for example, a hexamethylenedicarbamic acid or a 2,4-tolylene-dicarbamic acid radical.
Bevorzugt sind Verbindungen der Formel III, worin R Wasserstoff ist, R1' Wasserstoff oder Methyl ist, η 1 ist und R12 C)-C|8-Alkyl ist oder η 2 ist und R12 der Diacylrest einer aliphatischen Dicarbonsäure mit 4-12 C-Atomen ist.Preference is given to compounds of the formula III in which R is hydrogen, R 1 'is hydrogen or methyl, η is 1 and R 12 is C) -C | 8 -alkyl or η is 2 and R 12 is the diacyl radical of an aliphatic dicarboxylic acid having 4-12 C atoms.
Beispiele für Polyalkyl^-oeridin-Verbindungen dieser Klasse sind folger/de Verbindungen:Examples of polyalkyl ^ -oeridine compounds of this class are the following compounds:
1) 4-Hydroxy-2,2,6,6-tetramethylpiperidin1) 4-hydroxy-2,2,6,6-tetramethylpiperidine
2) 1-Allyl-4-hydroxy-2,2,6,6-tetramethylpiperidin2) 1-allyl-4-hydroxy-2,2,6,6-tetramethylpiperidine
3) 1 -8enzyl-4-hydroxy-2,2,6,6-tetramethylpiperidin3) 1 -8-Cyl-4-hydroxy-2,2,6,6-tetramethylpiperidine
4) 1-(4-tert.-Butyl-2-butenyl)-4-hydroxy-2,2,6,6-tetramethylpiperidin4) 1- (4-tert-butyl-2-butenyl) -4-hydroxy-2,2,6,6-tetramethylpiperidine
5) 4-Stearoyloxy-2,2,6,6-tetramethylpiperidin5) 4-stearoyloxy-2,2,6,6-tetramethylpiperidine
6) 1 -Ethyl^-salicyloyloxy^^e.e-tetramethylpiperidin6) 1-Ethyl ^ -salicyloyloxy ^^ e.e-tetramethylpiperidine
7) 4-Methacryloyloxy-1,2,2,6,6-pentamethylpiperidin7) 4-Methacryloyloxy-1,2,2,6,6-pentamethylpiperidine
8) 1,2,2,6,6-Pentamethylpiperidin-4-yl-ß-(3,5-di-tert.-butyl-4-hydroxyphi3nyl)-propionat8) 1,2,2,6,6-pentamethylpiperidin-4-yl-β- (3,5-di-tert-butyl-4-hydroxyphilyl) propionate
9) Di-(I-benzyl-2,2,6,6-tetramethylpiperidin-4-yl)-maleinat9) di (I-benzyl-2,2,6,6-tetramethylpiperidin-4-yl) maleate
10) Di-te.^e-tetramethylpiperidin^-yU-succinat10) Di-tert-e-tetramethylpiperidine-y-succinate
11) Di-(2,2,6,6-tetramethylpiperidin-4-yl)-glutarat11) di (2,2,6,6-tetramethylpiperidin-4-yl) -glutarate
12) Di-(2,2,6,6-teti .smethylpiperidin-4-yO-adipat12) di- (2,2,6,6-tetra-methylpiperidin-4-y-adipate
13) Di-(2,2,6,6-tetrameihylpiperidin-4-yl)-sebacat13) Di (2,2,6,6-tetramethylpiperidin-4-yl) sebacate
14) Di-(1,2,2,6,6-pentamethylpiperidin-4-yl)-sebacat14) di (1,2,2,6,6-pentamethylpiperidin-4-yl) sebacate
15) Di-(1,2,3,6-tetramethyl-2,6-diethyl-piperidin-4-yl)-sebacat15) di- (1,2,3,6-tetramethyl-2,6-diethyl-piperidin-4-yl) sebacate
16) Di-(I-allyl-2,2,6,6-tetramethylpiperidin-4-yl)-phthalat16) di (I-allyl-2,2,6,6-tetramethylpiperidin-4-yl) phthalate
17) i-Hydroxy^-ß-cyanoethyloxy^.e.e-tetramethylpiperidin17) i-Hydroxy ^ -β-cyanoethyloxy ^ .e.e-tetramethylpiperidine
18) i-Acetyl^^e.e-tetramethylpiperidin^-yl-acetat18) i-Acetyl ^^ e.e-tetramethylpiperidine ^ -yl-acetate
19) Trimellithsäure-tri-(2,2,6,6-tetramethylpiperidin-4-yl)-ester19) Trimellitic acid tri- (2,2,6,6-tetramethylpiperidin-4-yl) ester
20) i-AcryloyM-benzyloxy^AÖ-tetramethylpiperidin20) i-AcryloyM-benzyloxy ^ -α-tetramethylpiperidine
21) Diethylm8lonsäure-di(2,2l6l6-tetramethylpiperidin-4-yl)-ester21) diethylmonic acid di (2.2 l 6 l of 6-tetramethylpiperidin-4-yl) ester
22) Dibutyl-malonsäure-di-d^Ae-pentamethyiplperidin^-yU-ester22) dibutyl malonic acid di-d ^ Ae-pentamethyiplperidin ^ -yU-ester
23) Butyl-(3,5-di-tert.-butyl-4-hydroxybenzyl)-malonsäure-di-(1,2,2,6,6-pentamethylpiperidin-4-yl)-ester23) Butyl- (3,5-di-tert-butyl-4-hydroxybenzyl) -malonic acid di- (1,2,2,6,6-pentamethylpiperidin-4-yl) ester
24) Di-fi-octyloxy^^.e.ö-tetramethylpiperidin^-yD-sebacat24) di-fi-octyloxy ^^. E.-tetramethylpiperidine ^ -d-sebacate
25) Di-(1-cyciohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-sebacat25) Di- (1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate
26) Hexan-1',6'-bis-(4-carbamoyloxy-1-n-butyl-2,2,6/6-tetramethylpiperidin)26) hexane-1 ', 6'-bis (4-carbamoyloxy-1-n-butyl-2,2,6 / 6-tetramethylpiperidine)
27) ToIuol-2',4'-bis-(4-carbamoyloxy-1-n-propyl-2,2,e/e-tetramethylpiperidin)27) toluene-2 ', 4'-bis (4-carbamoyloxy-1-n-propyl-2,2, e / tetramethylpiperidine)
28) Dimethyl-bis-(2,2,6,6-tetramethylpiperidin-4-oxy)-silan28) Dimethyl bis (2,2,6,6-tetramethylpiperidine-4-oxy) silane
29) Phenyl-tr;s-(2,2,6,6-tetramethylpiperidin-4-oxy)-silan29) phenyl-tr ; s- (2,2,6,6-tetramethylpiperidin-4-oxy) silane
30) Tris-(1 -propyl-2,2,6,6-tetramethylpiperidin-4-yl)-phosphit30) Tris (1-propyl-2,2,6,6-tetramethylpiperidin-4-yl) phosphite
31) Tris-(1-propyl-2,2,6,6-tetramethylpiperidin-4-yl)-phosphat31) Tris (1-propyl-2,2,6,6-tetramethylpiperidin-4-yl) phosphate
32) Phenyl-[bis-(1,2,2,6,6-pentamethylpiperidin-4-yl)]-phosphonat32) phenyl [bis (1,2,2,6,6-pentamethylpiperidin-4-yl)] - phosphonate
33) 4-Hydroxy-1,2,2,6,6-pentamethylpiperidin33) 4-hydroxy-1,2,2,6,6-pentamethylpiperidine
34) 4-Hydroxy-N-hydroxyethyl-2,2,6,6-tetramethylpiperidin34) 4-hydroxy-N-hydroxyethyl-2,2,6,6-tetramethylpiperidine
35) 4-Hydroxy-N-(2-hydroxypropyl)-2,2,6,6-tetramethylpiperidin 36! 1-Glycidyl-4-hydroxy-2,2,6,6-tetramethylpip8ridin35) 4-hydroxy-N- (2-hydroxypropyl) -2,2,6,6-tetramethylpiperidine 36! 1-glycidyl-4-hydroxy-2,2,6,6-tetramethylpip8ridin
b) Verbindungen der Formel IV,b) compounds of the formula IV,
RCHzn /CH3/R RCHz n / CH 3 / R
-Rl- IV-Rl- IV
RCH2 κ XCH3 RCH 2 κ X CH 3
Jn Y n
worin η die Zahl 1 oder 2 bedeutet, R und R" die unter a) angegebene Bedeuturg habeii, R13 Wasserstoff, Ct—Ct2-Alkyl, C2-C6- Hydroxyalkyl, Cs-CT-Cycloalkyl, CT-Ce-Aralkyl, Cy-C^-Alkanoyl, Cj-CB-Alkenoyl, Benzoyi oder eine Gruppe der Formelin which η is the number 1 or 2, R and R "are the meanings given under a), R 13 is hydrogen, C t -C t2 -alkyl, C 2 -C 6 -hydroxyalkyl, Cs-CT-cycloalkyl, CT-Ce -Aralkyl, Cy-C ^ alkanoyl, Cj-CB alkenoyl, benzoyi or a group of the formula
RCH -/ NCH3 RCH - / N CH 3
ist und R14 wenn η 1 ist, Wasserstoff, C1-Ci8-AIkVl, Cj-Cg-Alkenyl, C6-C7-CyClOaIkVl, mit einer Hydroxy-, Cyano-, Alkoxycarbonyl- oder Carbamidgruppe substituiertes C,-C4-Alkyl, Glycidyl, eine Gruppe der Formel -CHt-CH(OH)-Z oder der Formel -CONH-Z ist, worin Z Wasserstoff, Methyl oder Phenyl bedeutet; wenn η 2 ist, C2-C12-Alkylen, Ce-C^-Arylen, Xylylen, eine -CHr-CHIOHJ-CHa-Gruppe oder eine GrUpPe-CH2-CH(OH)-CH2-O-D-O- bedeutet, worin D Cr-C10-Alkylen, Ce-C^-Arylen, Cg-C^Cycloalkylen ist, oder vorausgesetzt, daß R13 nicht Alkanoyl, Alkenoyl oder Benzoyl bedeutet, R14 auch einen zweiwertigen Rest einer aliphatischen, cycloaliphatischen oder aromatischen Dicarbonsäure oder Dicarbaminsäure oder auch die Gruppe -CO- bedeuten kann, oder R13 und R'4 zusammen, wenn η 1 ist, den zweiwertigen Rest einer aliphatischen, cycloaliphatischen oder aromatischen 1,2- odor 1,3-Dicarbonsäure bedeuten können.and R 14 is, when η is 1, hydrogen, C 1 -C 8 -alkyl, C 1 -C 6 -alkenyl, C 6 -C 7 -cycloalkyl, C, -C substituted with a hydroxy, cyano, alkoxycarbonyl or carbamide group 4 alkyl, glycidyl, a group of the formula -CHt-CH (OH) -Z or the formula -CONH-Z, wherein Z is hydrogen, methyl or phenyl; when η is 2, C 2 -C 12 -alkylene, C 1 -C 4 -arylene, xylylene, a -CHR-CHIOHJ-CHa group or a GrUpPe-CH 2 -CH (OH) -CH 2 -ODO-, wherein D is C 1 -C 10 -alkylene, C 1 -C 4 -arylene, C 1 -C 4 -cycloalkylene, or provided that R 13 is not alkanoyl, alkenoyl or benzoyl, R 14 is also a bivalent radical of an aliphatic, cycloaliphatic or aromatic dicarboxylic acid or dicarbamic acid or else the group -CO-, or R 13 and R ' 4 together, when η is 1, may denote the divalent radical of an aliphatic, cycloaliphatic or aromatic 1,2-odor 1,3-dicarboxylic acid.
Stellen etwaige Substituenten C)-C12- oder C1-C18-AIkYl dar, so haben sie die bereits unter a) angegebene Bedeutung.If any substituents are C) -C 12 - or C 1 -C 18 -alkyl, then they have the meaning already given under a).
Bedeuten etwaige Substituenten Cs-CT-Cycloalkyl, so stellen sie insbesondere Cyclohexyl dar.If any substituents are Cs-Ct-cycloalkyl, they are in particular cyclohexyl.
Als CT-Ce-Aralkyl ist R13 insbesondere Phenylethyl oder vor allem Benzyl. Als Cz-Cs-Hydroxyalkyl ist R13 insbesondere 2-Hydroxyethyl oder 2-Hydroxypropyl.As CT-Ce-aralkyl R 13 is in particular phenylethyl or especially benzyl. As Cz-Cs-hydroxyalkyl R 13 is in particular 2-hydroxyethyl or 2-hydroxypropyl.
R'3 ist als Cj-C18-Alkanoyl beispielsweise Propionyl, Butyryl, Octanoyl, Dodecanoyl, Hexadecanoyl, Octadecanoyl, aber bevorzugt Acetyl und als Cj-Cs-Alkenoyl, insbesondere Acryloyl.R ' 3 as Cj-C 18 alkanoyl, for example, propionyl, butyryl, octanoyl, dodecanoyl, hexadecanoyl, octadecanoyl, but preferably acetyl and as Cj-Cs-alkenoyl, in particular acryloyl.
Bedeutet R14 CHVAIkenyl, dann handelt es sich z. B. um Allyl, Methallyl, 2-Butenyl, 2-Pentenyl, 2-Hexenyl oder 2-Octenyl.If R 14 is CHVA-alkenyl, then it is z. Allyl, methallyl, 2-butenyl, 2-pentenyl, 2-hexenyl or 2-octenyl.
R14 als mit einer Hydroxy-, Cyano-, Alkoxycarbonyl- oder Carbamidgruppe substituiertes Ci-C4-Alkyl kann z. B. 2-hydroxyethyl, 2-Hydroxypropyl, 2-Cyanethyl, Methoxycarbonylmethyl, 2-Ethoxycarbonylethyl, 2-Aminocarbonylpropyl oder 2-(Dimethylaminocarbonyl)-ethylsein.R 14 as with a hydroxy, cyano, alkoxycarbonyl or carbamide substituted Ci-C 4 -alkyl may, for. 2-hydroxyethyl, 2-hydroxypropyl, 2-cyanoethyl, methoxycarbonylmethyl, 2-ethoxycarbonylethyl, 2-aminocarbonylpropyl or 2- (dimethylaminocarbonyl) -ethyl.
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.If any substituents represent C 2 -C 12 -alkylene, these are, for example, ethylene, propylene, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
Bedeuten etwaige Substituenten Cs-C16-Arylen, so stellen sie z. B. o-, m- oder p-Phenylen, 1,4-Naphthylen oder 4,4'-DiphenylenIf any substituents Cs-C 16 -arylene, they represent z. As o-, m- or p-phenylene, 1,4-naphthylene or 4,4'-diphenylene
Als Ce-C12-Cycloalkylen ist D insbesondere Cyclohexylen.As Ce-C 12 -cycloalkylene D is in particular cyclohexylene.
Bevorzugt sind Verbindungen der Formel IV, worin η 1 oder 2 ist, R Wasserstoff ist, R" Wasserstoff oder Methyl ist, R13 Wasserstoff, C)-C12-Alkyl oder eine Gruppe der FormelPreference is given to compounds of the formula IV in which η is 1 or 2, R is hydrogen, R "is hydrogen or methyl, R 13 is hydrogen, C) -C 12 -alkyl or a group of the formula
RCH2 7 NCH3 ist und Ru im Fall von η = 1 Wasserstoff oder C,-Cj2-Alkyl ist, und im Fall von η = 2 C2-C8-Alkylen ist.RCH 2 7 N CH 3 and R u in the case of η = 1 is hydrogen or C, -Cj 2 alkyl, and in the case of η = 2 C 2 -C 8 -alkylene.
Beispiele für Polyalkylplperldln-Verblndungen dieser Klasse sind folgende Verbindungen:Examples of Polyalkylplperldln-Verblndungen this class are the following compounds:
37) N,N'-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-hexamethvlen-1,6-diamin37) N, N'-bis (2,2,6,6-tetramethylpiperidin-4-yl) hexamethylene-1,6-diamine
38) N,N'-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-hexamethylen-1,6-diacetamid38) N, N'-bis (2,2,6,6-tetramethylpiperidin-4-yl) hexamethylene-1,6-diacetamide
39) Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-amin39) Bis (2,2,6,6-tetramethylpiperidin-4-yl) amine
40) 4-Benzoylamino-2,2,6,6-totramethylpiperidin40) 4-Benzoylamino-2,2,6,6-tetramethylpiperidine
41) N,N'-Bis-(2,2,6,e-tetramethylpiperidin-4-yl)-N,N'-dibutyl-adipamid41) N, N'-bis (2,2,6, e-tetramethylpiperidin-4-yl) -N, N'-dibutyl-adipamide
42) N,. '-Bis-(2,2,6,6-tötramethylplperidin-4-yl)-N,N'-dicyclohexyl-2-hydroxypropylen-1,3-diami!i42) N ,. '-Bis- (2,2,6,6-tötramethylplperidin-4-yl) -N, N'-dicyclohexyl-2-hydroxypropylene-1,3-diamino! I
43) N,N'-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-p-xylylen-diamin43) N, N'-bis (2,2,6,6-tetramethylpiperidin-4-yl) -p-xylylenediamine
44) N,N'-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-succindiamid44) N, N'-bis (2,2,6,6-tetramethyl-piperidin-4-yl) -succin-diamide
45) N-(2,2,6,6-Tetramethylpiperidin-4-yl)-ß-aminodipropionsäure-di-(2,2,6,6-tetramethylpiperidin-4-yl)ester45) N- (2,2,6,6-tetramethylpiperidin-4-yl) -β-aminodipropionic acid di (2,2,6,6-tetramethylpiperidin-4-yl) ester
46) Die Verbindung der Formel46) The compound of the formula
CH3, CH3 CH 3 , CH 3
t r_ y u ι t r_yu ι
CH3-N7 ^'-N-CH2-CH(OH)-CH2—OCH 3 -N 7 ^ '- N-CH 2 -CH (OH) -CH 2 -O
' Nch3 y\ ' N ch 3 y \
CH3-(Jl-CH3 CH 3 - (Jl-CH 3
η ι η ι
CH3 CH3 \ / CH 3 CH 3 /
Nn ^'-N-CK2-CH(OH)-CH2—0N n ^ '- N-CK 2 -CH (OH) -CH 2 -0
47) 4-{Bis-2-hydroxyethyl-amino)-1,2,2,6,6-pentamethylpiperidin47) 4- {bis-2-hydroxyethylamino) -1,2,2,6,6-pentamethylpiperidine
48) 4-(3-Methyl-4-hydroxy-5-tert.-butyl-benzoesäureamido)-2,2,6,6-tetramethylpiperidin48) 4- (3-methyl-4-hydroxy-5-tert-butylbenzoic acid amido) -2,2,6,6-tetramethylpiperidine
49) 4-Methacrylamido-1,2,2,6,6-pentamethylpiperidin49) 4-methacrylamido-1,2,2,6,6-pentamethylpiperidine
c) Verbindungen der Formel V,c) compounds of the formula V,
worin η die Zahl 1 oder 2 bedeutet, R und R" die unter a) angegebene Bedeutung haben und R16, wenn η 1 ist, Cj-Ce-Alkylen oder -Hydroxyalkylen oder C^C^-AcyloxValkylen, wenn π 2 ist, die Gruppe (-CH2J2C(CH2-)? bedeutet.in which η is the number 1 or 2, R and R "are as defined under a) and R 16 , when η is 1, is C 1 -C 6 -alkylene or -hydroxyalkylene or C 1 -C 4 -cycloxalkylene, if π 2 is the group (-CH 2 J 2 C (CH 2 -)? means.
Bedeutet R15 CHVAIkylen oder -Hydroxyalkylen, so stellt es beispielsweise Ethylen, 1-Methyl-ethylen, Propylen, 2-Ethyl-propylen oder 2-Ethyl-2-hydroxymethylpropylen dar.When R 15 is CHA alkylene or hydroxyalkylene, it represents, for example, ethylene, 1-methylethylene, propylene, 2-ethyl-propylene or 2-ethyl-2-hydroxymethylpropylene.
Als C4-C22-Acyloxyalkylen bedeutet R16 z.B. 2-Ethyl-2-acetoxymethylpropylen.As C4-C22 acyloxyalkylene, R 16, for example, 2-ethyl-2-acetoxymethylpropylene.
Beispiele für Polyalkylpiperldin-Verbindungen dieser Klasse sind folgende Verbindungen:Examples of polyalkylpiperidin compounds of this class are the following compounds:
50) 9-A2a-8,8,10,10-tetramethyl-1,5-dioxaspiro[5.5]undecan50) 9-A2a-8,8,10,10-tetramethyl-1,5-dioxaspiro [5.5] undecane
51) 9-Aza-8,8,10,10-tetramethyl-3-ethyl-1,5-dioxaspiroI5.5]undecan51) 9-aza-8,8,10,10-tetramethyl-3-ethyl-1,5-dioxaspiro [5.5] undecane
52) 8-Aza-2,7,7,8,9,9-hexamethyl-1,4-dioxaspiro[4.5jdecan52) 8-aza-2,7,7,8,9,9-hexamethyl-1,4-dioxaspiro [4.5] decane
53) g-Aza-S-hydroxymethyl-S-ethyl-e.e.S.IO.IO-pentamethyl-I.S-dioxaspiroiö.Slundecan53) g-Aza-S-hydroxymethyl-S-ethyl-e.e.S.IO.IO-pentamethyl-I.S-dioxaspiroiö.Slundecan
54) S-Aza-S-ethyl-S-acetoxymethyl-g-acetyl-e.e.iO.IO-tetramethyl-i^-dioxaspirolS.Sjundecan54) S-Aza-S-ethyl-S-acetoxymethyl-g-acetyl-e.e.iO.IO-tetramethyl-i-dioxaspirol S.Sjundecan
55) 2,2,6/6-T3tramethylpiperidin-4-spiro-2'-(1',3'-dioxan)-5'-spiro-5"-(r,3"-dioxan)-2"-spiro-4"'-(2"',2"',6"',6"'-tetramethylpiperidin).55) 2,2,6 / 6-T3-tramethyl-piperidine-4-spiro-2 '- (1', 3'-dioxane) -5'-spiro-5 "- (r, 3" -dioxane) -2 "-spiro -4 "'-(2"', 2 "',6"', 6 "'- tetramethylpiperidine).
d) Verbindungen der Formeln VIA, Vl B und VICd) compounds of the formulas VIA, VI B and VIC
R11-NR 11 -N
X'X '
?=o? = O
VIAVIA
-R17 -R 17
R11 -K R 11 -K
VIBVIB
R11-R 11 -
VICVIC
worin η die Zahl 1 oder 2 bedeutet. R und " die unter a) angegebene Bedeutung haben, R16 Wasserstoff, C1-C12-AIkYl, Allyl, Benzyl, Glycidyl oder Cj-Ce-Alkoxyalkyl ist und R", wenn η 1 ist, Wasserstoff, C1-C12-AIkYl, CHVAIkenyl, Cy-CrAralkyl, C6-C; Cycloalkyl, C2-C4-Hydroxyalkyl, CHVAIkoxyalkyl, C8-C10-ArYl, Glycidyl oder eine Gruppe der Formel -(CH2)p-C00-Q oder der Formel -(CH2Ip-O-CO-Q ist, worin ρ 1 oder 2 und Q C1-C4 Alkyl oder Phenyl sind, wenn η 2 ist, C2 -C12 Alkylen, C^C^-Alkenylen, C6-C12 Arylen, eine GrUpPe-CH2-CH(OHJ-CH2-O-D-O-CH2-CH(OH)-CHr-, worin D C2-C10 Alkylen, Ce-C18-Arylen, C6-C12 Cycloalkylen ist, oder eine Gruppe -CH2CH(OZ')CH2-(OCH2-CH(OZ')CH2)r- bedeutet, worin Z' Wasserstoff, C1-C18-AIkVl, Allyl, Benzyl, C2-C12-Alkanoyl oder Benzoyl ist, T1 und T2 unabhängig voneinander Wasserstoff, Ci-C1e-Alkyl oder gegebenenfalls durch Halogen oder C1-C4-AIkYl substituiertes Ce-C|0-Aryl oder Cr-C^Aralkyl bedeuten oder T1 und T2 zusammen mit dem sie bindenden C-Atom einen Cs-C12-Cycloalkanring bilden.wherein η is the number 1 or 2. R and "have the meaning given under a), R 16 is hydrogen, C 1 -C 12 -alkyl, allyl, benzyl, glycidyl or Cj-C e alkoxyalkyl and R" is, if η 1, is hydrogen, C 1 - C 12 alkyl, CH 2 alkenyl, cy-Cr aralkyl, C 6 -C; Cycloalkyl, C 2 -C 4 hydroxyalkyl, CH 3 alkoxyalkyl, C 8 -C 10 aryl, glycidyl or a group of the formula - (CH 2 ) p -COQ or the formula - (CH 2 Ip-O-CO-Q wherein ρ is 1 or 2 and Q is C 1 -C 4 alkyl or phenyl when η is 2, C 2 -C 12 alkylene, C 1 -C 4 alkenylene, C 6 -C 12 arylene, a GrUpPe CH 2 -CH (OHJ-CH 2 -O-O-CH 2 -CH (OH) -CHR-, wherein DC 2 -C 10 is alkylene, Ce-C 18 -arylene, C 6 -C 12 -cycloalkylene, or a group -CH 2 CH ( OZ ') CH 2 - (OCH 2 -CH (OZ') CH 2 ) r -, wherein Z 'is hydrogen, C 1 -C 18 alkyl, allyl, benzyl, C 2 -C 12 alkanoyl or benzoyl, T is 0 aryl or Cr-C ^ aralkyl, or T 1 and T 2 together with the | 1 and T 2 are independently hydrogen, Ci-C 1e alkyl or optionally halogen or C 1 -C 4 -alkyl substituted Ce-C they form a C s -C 12 cycloalkane ring.
Bedeuten etwaige Substituenten C)-C12-Alkyl, so stellen sie z. B. Methyl, Ethyl, n-Propyl, η-Butyl, sek.-Butyl, tert.-Butyl, n-Hexyl, n-Octyl, 2-Ethyl-hexyl, n-Nonyl, n-Decyl, n-Undecyl oder n-Dodecyl dar.If any substituents C) -C 12 alkyl, so they provide z. For example, methyl, ethyl, n-propyl, η-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethyl-hexyl, n-nonyl, n-decyl, n-undecyl or n-dodecyl.
Etwaige Substituenten in der Bedeutung von C|-C)8-Alkyl können z. B. die oben angeführten Gruppen und dazu noch beispielsweise n-Tridecyl, n-Tetradecyl, n-Hexsdecyl oder n-Octadecyl darstellen.Any substituents in the meaning of C 1 -C 8 -alkyl may, for. As the above-mentioned groups and in addition, for example, n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl represent.
Bedeuten etwaige Substituenten C^Ce-Alkoxyalkyl, so stellen sie z. B. Methoxymethyl, Ethoxymethyl, Propoxymethyl, tert.-Butoxymethyl, Ethoxyethyl, Ethoxypropyl, n-Butoxyethyl, tert.-Butoxyethyl, Isopropoxyethyl oder Propoxypropyl dar.If any substituents C ^ Ce-alkoxyalkyl, so they provide z. For example, methoxymethyl, ethoxymethyl, propoxymethyl, tert-butoxymethyl, ethoxyethyl, ethoxypropyl, n-butoxyethyl, tert-butoxyethyl, isopropoxyethyl or propoxypropyl.
Stellt R17 Ci-Cs-Alkenyl dar, so bedeutet es z. B. 1-Propenyl, Allyl, Methallyl, 2-Butenyl oder 2-Pentenyl.R 17 represents Ci-Cs-alkenyl, it means z. 1-propenyl, allyl, methallyl, 2-butenyl or 2-pentenyl.
Als Cy-Ca-Aralkyl sind R17, T1 und Tj, insbesondere Phenethyl oder vor allem Benzyl. Bilden T1 und T2 zusammen mit dem C-Atom einen Cycloalkanring, so kann dies z. B. ein Cyclopentane Cyclohexan-, Cyclooctan- oder Cyclododecanring sein.As Cy-Ca-aralkyl R 17 , T 1 and Tj, in particular phenethyl or especially benzyl. If T 1 and T 2 together with the C atom form a cycloalkane ring, this can be done, for example, by As a cyclopentane cyclohexane, cyclooctane or cyclododecane be.
Bedeutet R17 C2-C4-Hydroxyalkyl, so stellt es z. B. 2-Hydroxyethyl, 2-Hydroxypropyl, 2-Hydroxybutyl oder 4-Hydroxybutyl dar.If R 17 is C 2 -C 4 -hydroxyalkyl, it is z. For example, 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxybutyl or 4-hydroxybutyl.
Als Cg-C10-Aryl bedeuten R17, T1 und T2, insbesondere Phenyl, α- oder ß-Naphthyl, die gegebenenfalls mit Halogen oder C,-C4-Alkyl substituiert sind.As Cg-C 10 -aryl R 17 , T 1 and T 2 , in particular phenyl, α- or ß-naphthyl, which are optionally substituted by halogen or C, -C 4 alkyl.
Stellt R17 C2-C12-Alkylen dar, so handelt es sich z. B. um Ethylen, Propy'»-, 2,2-Dimethylpropylon, Tetramethylen, Hexamethylen, Octamethylen, Decamethylen oder Dodecamethylen.If R 17 is C 2 -C 12 -alkylene, this is z. For example, ethylene, propylene, 2,2-dimethylpropylon, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
Als C4-Cj2-Alkenylen bedeutet R17 insbesondere 2-Butenylen, 2-Pentenylen od r 3-Hexenylen.As C 4 -C 12 -alkenylene, R 17 is in particular 2-butenylene, 2-pentenylene or 3-hexenylene.
Bedeutet R17 Ce-C^-Arylen, so stellt es beispielsweise o-, m- oder p-Phenylen, 1,4-Naphthylen oder 4,4'-Diphenylen dar.If R 17 is Ce-C 1-4 -arylene, it is, for example, o-, m- or p-phenylene, 1,4-naphthylene or 4,4'-diphenylene.
Bedeutet Z' C2-C12-Alkanoyl, so stellt es beispielsweise Propionyl, Butyryl, Octanoyl, Dodecanoyl, aber bevorzugt Acetyl dar.If Z 'is C 2 -C 12 -alkanoyl, it represents, for example, propionyl, butyryl, octanoyl, dodecanoyl, but preferably acetyl.
D hat als C2-C10-Alkylen, Ce-Cl6-Arylen oder Cg-C12 -Cycloalkylen die unter b) angegebene Bedeutung.D has the meaning given under b) as C 2 -C 10 -alkylene, Ce-C l6 -arylene or Cg-C 12 -cycloalkylene.
Beispiele f Or Polyalkylpiperldln-Verblndungen dieser Klasse sind folgende Verbindungen:Examples of polyalkylpiperidine compounds of this class are the following compounds:
56) 3-Benzyl-1,3,8-triaza-7,7,9,9-tetramethylspiro[4.5ldecan-2,4-dion56) 3-Benzyl-1,3,8-triaza-7,7,9,9-tetramethylspiro [4.5-decane-2,4-dione
57) 3-n-Octyl-1,3,8-triaza-7,7,9,9-tetramethylspiro[4.5ldecan-2,4-dion57) 3-n-octyl-1,3,8-triaza-7,7,9,9-tetramethylspiro [4.5-decane-2,4-dione
58) 3-Allyl-1,3,8-triaza-7,7,9,9-pentamethylspiro[4.5Jdecan-2,4-dion58) 3-allyl-1,3,8-triaza-7,7,9,9-pentamethylspiro [4.5-decane-2,4-dione
59) 3-Glycidyl-1,3,8-triaza-7,7,8,9,9-pentamethylspiro[4.5]decan-2,4-dion59) 3-Glycidyl-1,3,8-triaza-7,7,8,9,9-pentamethylspiro [4.5] decane-2,4-dione
60) 1,3,7,7,8,9,9-HeptamethyM ,3,8-triazaspiro[4.5]decan-2,4-dion60) 1,3,7,7,8,9,9-heptamethyl, 3,8-triazaspiro [4.5] decane-2,4-dione
61) 2-lso-propyl-7,7,9,9-tetramethyl-1 -oxa-3,8-diaza-4-oxo-spiro-[4.5)decan61) 2-iso-propyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro [4.5] decane
62) 2,2-Dibutyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro-[4.5J-decan62) 2,2-dibutyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro [4.5] decane
63) 2,2,4,4-Tetramethyl-7-oxa-3,20-diaza-21-oxo-dispiro|5.1.H.2]-heneicosan63) 2,2,4,4-tetramethyl-7-oxa-3,20-diaza-21-oxo-dispiro | 5.1.H.2] -heneicosane
64) 2-Butyl-7,7,9,9-tetramethyl-1-oxa-4,8-diaza-3-oxo-spiro-[4,5]decan64) 2-Butyl-7,7,9,9-tetramethyl-1-oxa-4,8-diaza-3-oxo-spiro [4,5] decane
65) 8-Acetyl-3-dodecyl-1,3,8-triaza-7,7,9,9-tetramethylspiro[4,5]-decan-2,4-dion oder die Verbindungen der folgenden Formeln:65) 8-acetyl-3-dodecyl-1,3,8-triaza-7,7,9,9-tetramethylspiro [4,5] -decane-2,4-dione or the compounds of the following formulas:
CH3, CH3-N,CH 3 , CH 3 -N,
xHxH
CH3 7 NiH3 CH 3 7 NiH 3
:=o o=c—N: = o o = c-N
N-CH2CH(OH)CH2-[OCH2-CH(OH)CH2 ] 2-liN-CH 2 CH (OH) CH 2 - [OCH 2 -CH (OH) CH 2 ] 2 -li
I r- I r- 7 x7x
N-CH3 CH3 N-CH 3 CH 3
CH3 CH 3
L_ NH-C=OL_ NH-C = O
67) C"3-< X '67) C "3- <X '
O=C-NH · ^-O = C-NH · ^ -
(CH2)(CH 2 )
-CH3 -CH 3
CH3 7 XCH3 CH 3 7 X CH 3
CH3 7 XCH3 CH 3 7 X CH 3
H-C=OH-C = O
O=C—NO = C-N
« ———. % "---. %
CH3 7 NCH3 CH 3 7 N CH 3
I.,- tI, - t
CH3 7 XCH3 CH 3 7 X CH 3
-CH2CH2COOCi2H25 -CH 2 CH 2 COOCi 2 H 25
e) Verbindungen der Formel VII,e) compounds of the formula VII,
_R2 0_ R 2 0
worin η die Zahl 1 oder 2 ist und R'8 eine Gruppe der Formelwherein η is the number 1 or 2 and R ' 8 is a group of the formula
CH3 7 CH 3 7
bedeutet, worin R und R" die unter a) angegebene Bedeutung haben, E-O- oder-NR21- ist, A Cr-Ce-Alkylen oder-(CH2)j-O-undxdieZahlenOoderi bedeuten,R'9gleichR18odereinederGruppen-NR2IR",-OR23,-NHCH2OR23oder-N(CH2OR23)2ist,H20, wenn η = 1 ist, gleich R18 oder R18, und wenn η = 2 ist, eine Gruppe -E-B-E- ist, worin B gegebenenfalls durch -N(R2')-unterbrochenes Cr-Ce-Alkylen bedeutet, R" Ci-Ci2-Alkyl, Cyclohexyl, Benzyl oder C,-C4-Hydroxyalkyl oder eine Gruppe der Formelwhere R and R "are as defined under a), EO- or -NR 21 -, A is Cr-Ce-alkylene or- (CH 2 ) jO- andx are the numbers O ori, R ' 9 is R 18 or one of the group NR 2I R ", - OR 23 , -NHCH 2 OR 23 or -N (CH 2 OR 23 ) 2 , H 20 if η = 1, R 18 or R 18 , and if η = 2, a group - EBE-, wherein B is optionally -N (R 2 ') -interrupted Cr-C e -alkylene, R "is Ci-Ci 2 -alkyl, cyclohexyl, benzyl or C, -C 4 -hydroxyalkyl or a group of the formula
CH2RCH 2 R
CH3 7 NCH2RCH 3 7 N CH 2 R
ist, R" C1-C)2 Alkyl, Cyclohexyl, Benzyl, C1-C4 Hydroxyalkyl und R23 Wasserstoff, Ci-Ci2 Alkyl odsr Phenyl bedeuten oder R21 und R22 zusammen C4-C6-Alkylen oder -Oxaalkylen, beispielsweise, R "is C 1 -C) 2 alkyl, cyclohexyl, benzyl, C 1 -C 4 hydroxyalkyl and R 23 is hydrogen, Ci-Ci 2 alkyl mean ODSR phenyl or R 21 and R 22 together are C 4 -C 6 alkylene or -Oxaalkylen, for example
O, oder eine Gruppe der Formel -CH2CH2 / -CH2CHO, or a group of the formula -CH 2 CH 2 / -CH 2 CH
sind oder aucli R2' und R22 jeweils eine Gruppe der Formelor R 2 'and R 22 are each a group of the formula
CH3. ,CH3 r „ \ /T 9NCH 3 . , CH 3 r "\ / T 9 N
CH3 7 NCH3 CH 3 7 N CH 3
• ·• ·
CH / Y XCH3 CH / Y x CH 3
bedeuten.mean.
Bedeuten etwaige Substituenten C1-C12-AIRyI, so stellen sie beispielsweise Methyl, Ethyl, n-Propyl, η-Butyl, sek.-Butyl, tert.-Butyl, n-Hexyl, n-Octyl, 2-Ethylhexyl, n-Nonyl, n-Decyl, n-Undecyl oder n-Dodecyl dar.If any substituents C 1 -C 12 -AIRyI, they represent, for example, methyl, ethyl, n-propyl, η-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethylhexyl, n Nyl, n-decyl, n-undecyl or n-dodecyl.
Bedeuten etwaige Substituenten CHVHydroxyalkyl, so stellen sie z. B. 2-Hydroxyethyl, 2-Hydroxypropyl, 3-Hydroxypropyl, 2-Hydroxybutyl oder 4-Hydroxybutyl dar.If any substituents CHVHydroxyalkyl, so they provide z. 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl or 4-hydroxybutyl.
Bedeutet A C2-C6 Alkylen, so stellt es beispielsweise Ethylen, Propylen, 2,2-Dimethylpropylen, Tetramethylen oder Hexamethylen dar.If AC 2 -C 6 alkylene, it represents, for example, ethylene, propylene, 2,2-dimethylpropylene, tetramethylene or hexamethylene.
Stellen R21 und R22 zusammen C4-Cs-Alkylen oder -Oxaalkylen dar, so bedeutet dies z. B. Tetramethylen, Pentamethylen oder 3-Oxapentamethylen.R 21 and R 22 together represent C 4 -Cs-alkylene or -oxaalkylene, this means z. As tetramethylene, pentamethylene or 3-oxapentamethylene.
Beispiele für Polyalkylpiperidin-Verbindungen dieser Klasse sind die Verbindungen der folgenden Formeln:Examples of polyalkylpiperidine compounds of this class are the compounds of the following formulas:
H3 /CH3 H 3 / C H 3
(CH3CHz)2N7 \' N(CH2CH3)(CH 3 CHz) 2 N 7 \ ' N (CH 2 CH 3 )
/CH3 \ CH3n /CH3 / CH3 \ CH3n / CH3
c2h5-n( )-f V ΐ ^ — 7 c 2 h 5 -n () -f V ΐ ^ - 7
i ^ ch3 7'\h3 i ^ ch 3 7 '\ h 3
H3Cn H 3 C n
·· 72) N Jf mit R = -NH-CH2CH2CH2-O-N ^N-CH3 ·· 72) N Jf with R = -NH-CH 2 CH 2 CH 2 -O- N ^ N-CH 3
H3C7 H 3 C 7
ro ·ro ·
χ ι χ ι
CJCJ
CJCJ
•=55• 55 =
rcrc
CJCJ
CJCJ
75) R-NH-(CHz)3-N-(CHz)z-N-(CH2)3-NH-R75) R-NH- (CHz) 3 -N- (CHz) z N- (CH 2 ) 3 -NH-R
mit Rwith R
CH3^ —CH 3 ^ -
Λ—ϊ^-·' >Λ-ϊ ^ - · '>
CH9-IjICH 9 -IjI
CH / Y XCH3 CH / Y x CH 3
76) R-NH-(CHz)3-N-(CHz)z-N-(CHz)3-NH-R76) R-NH- (CHz) 3 -N- (CHz) zN- (CHz) 3 -NH-R
mit Rwith R
A.A.
-A.-A.
CH3' Ύ XCH3 CH 3 ' Ύ X CH 3
CH3 CH3 CH 3 CH 3
CH3 CH3 CH 3 CH 3
CH3 R R CH3 CH 3 RR CH 3
7 7) R-N-(CHz)3-N-(CHz)z-N-(CHz)3-N-R7 7) RN- (CHz) 3 -N- (CHz) zN- (CHz) 3 -NR
mit Rwith R
.A..A.
-/ ^N-CH3 - / ^ N-CH 3
• — ·• - ·
cfi3 NCH3 cfi 3 N CH 3
CH / \y NCH3 CH3 CH / \ y N CH 3 CH 3
• ·• ·
C8Hi7-IjI-C 8 Hi 7 -IjI-
—Y Nj7 \h(ch2)3- Y Nj 7 \ h (ch 2 ) 3
J i/ \J i / \
CH,CH,
CH3 CH 3
CH2CH2OHCH 2 CH 2 OH
CH\ Λ CH \ Λ
JJl-CH9 JJl-CH 9
n yCH3 ny CH 3
• — ·• - ·
HO-CH2CH2-l/ /·—fHO-CH 2 CH 2 -l / / · -f
·-· C11H9 · - · C 11 H 9
CH3 CH3 CH 3 CH 3
CH3 CH 3
C \-CH2CH2-OHC \ -CH2CH2-OH
H9 ·-·(H 9 · · · (
CH3 CH3 CH 3 CH 3
CH2-CH=CH2 X /CH3 CH 2 -CH = CH 2 X / C H 3
A Ϊ.H3 /CH3 A Ϊ.H 3 / CH 3
Π 2 Ο—MO—Π 2 »J—W,Π 2 Ο-MO-Π 2 »J-W,
H9 CH 9 C
• t• t
CH3Z NCH3 CH3Z N CH 3
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.f) oligomeric 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 containing such radicals.
Beispiele für 2,2,6,6-Polyalkylpiperidin-Lichtschutzmittel dieser Klasse sind die Verbindungen der folgenden Formeln, wobei m eine Zahl von 2 bis etwa 200 bedeutet.Examples of 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.
81) «" /CH3 81) "" / C H 3
Vo-4Vo-4
m Vm V
-^C-CH2-CH2-C-O-CH2-CH2-N7 ^- O-l·-- ^ C-CH 2 -CH 2 -CO-CH 2 -CH 2 -N 7 ^ - Ol · -
SCH3 S CH 3
CH3 84) PH PHCH 3 84) PH PH
yn3 yn3 yn 3 yn 3
NH-C-CH2-C-CH3 ,' CH3 CH3 NH-C-CH 2 -C-CH 3 , ' CH 3 CH 3
N (CH2 ) 6- N (CH 2 ) 6-6
Ln3. · T ,1.113 Ln3. ' ' .LH3\l I/ \l I/Ln 3 . · T, 1,113 Ln 3 . '' .LH 3 \ l I / \ l I /
CH3 7 N7 NCH3 CH3 7 N7 \h3 CH 3 7 N 7 N CH 3 CH 3 7 N 7 \ h 3
-f N CH 2 -CH (OH ) -CH 2+-fN CH 2 -CH (OH) -CH 2 +
CH3nJ7 \/CH3 CH 3n J 7 \ / C H 3
• ·• ·
CH3 7 Y \h3 CH 3 7 Y \ h 3
CH3 CH 3
-f-0—·7 ^N-CH2-CH=CH-CH2-N-f-O- • 7 ^ N-CH 2 -CH = CH-CH 2 -N
CH3 CH 3
.A..A.
-(CH2),- (CH 2 ),
ι ϊι ϊ
CH3 7 Y NCH3 CH 3 7 Y N CH 3
CH3 CH 3
Ο-·7 N-CH2-Ο- · 7 N-CH 2 -
* —— ·* - ·
CH3 7 XCH3 CH 3 7 X CH 3
CH3 7 XCH3 CH 3 7 X CH 3
-O—CH2-CH2-N7 X—7&A- -O-CH 2 -CH 2 -N 7 X - 7 & A-
CH3 7 XCH3 CH 3 7 X CH 3
?Ha?Ha
O=CO = C
-CH2-^ CH3x /CH3 -CH 2 - ^ CH 3x / CH 3
< >—CH3 <> -CH 3
CH3 7 XCH3 CH 3 7 X CH 3
-CH2--CH 2 -
O=C C6H13-N-' O = C C 6 H 13 -N- '
CH3 CH3 CH 3 CH 3
-CH3 -CH 3
CH3 7 XCH3 CH 3 7 X CH 3
92) A 92) A
• ·• ·
I II i
I I/ CH3 7 Y XCH3 CH3 7 Y XCH3 II / CH 3 7 Y X CH 3 CH 3 7 Y X CH 3
-f IjI (CH2)e IjI CH2-CH2--f IjI (CH 2 ) e IjI CH 2 -CH 2 -
CH3^ '/ N ,CH3 CH3v ;7 X; ,CH3 CH 3 ^ '/ N, CH 3 CH 3v ; 7X ; , CH 3
\l I/ \] I/I / \] I /
-f N ( CH 2 ) 6 ti—-C CH 2- -f N (CH 2) 6 ti - C CH 2-
g) Verbindungen der Formel VIII, RCH2x /CH3/Rg) Compounds of the formula VIII, RCH 2x / CH3 / R
· ·
Rii_N/ \=0 ' V||| R ii_ N / \ = 0 ' V |||
RCH2 7 XCH3 RCH 2 7 X CH 3
worin R und R" die unter a) angegebene Bedeutung haben.wherein R and R "have the meaning given under a).
Bevorzugt sind Verbindungen der Formel VIII, worin R Wasserstoff oder Methyl ist und R" Wasserstoff oder Methyl ist.Preference is given to compounds of the formula VIII in which R is hydrogen or methyl and R "is hydrogen or methyl.
Beispiele for solche Verbindungen sind:Examples of such compounds are:
95) 2,2,6,6-Tetramethyl-4-piperidon (Triacetonamin)95) 2,2,6,6-tetramethyl-4-piperidone (triacetonamine)
96) 1,2,2,6,6-Pentamethyl-4-piperidon96) 1,2,2,6,6-pentamethyl-4-piperidone
97) 2,2,6,6-Tetramethyl-4-piperidon-1-oxyl97) 2,2,6,6-tetramethyl-4-piperidone-1-oxyl
98) 2,3,6-Trimethyl-2,6-diethyl-4-piperidon98) 2,3,6-trimethyl-2,6-diethyl-4-piperidone
Die Polyalkylpiperidine sind bekannte Verbindungen und werden als Lichtschutzmittel für organische Materialien benützt. Einige von ihnen sind im Handel erhältlich.The polyalkylpiperidines are known compounds and are used as light stabilizers for organic materials. Some of them are available in stores.
Die Komponente (C) ist ein phenolisches Antioxidans. Bevorzugt ist (C) eine Verbindung der Formel I, worin A Wasserstoff, Ci-Cg-Alkyl, Cyclohexyl, Phenyl oder eine GruppeComponent (C) is a phenolic antioxidant. Preferably (C) is a compound of formula I, wherein A is hydrogen, Ci-Cg-alkyl, cyclohexyl, phenyl or a group
λ bedeutet,λ means
B Ci-Ce-Alkyl, Cyclohexyl oder Phenyl bedeutet, X C,-Ce-Alkyl oder eine der Gruppen-C,H2,-S-R2,-CbH2b-COOR3 /-CH2N(R10J(R") oderB is C 1 -C 6 -alkyl, cyclohexyl or phenyl, XC, -C e -alkyl or one of the group-C, H 2 , -SR 2 , -CbH 2 b-COOR 3 / -CH 2 N (R 10 J (R ") or
-CH2-^ ^--0H-CH 2 - ^ ^ - 0H
ο bedeutet, o means
R2 C1-C12-AIkYl, Phenyl oder eine Gruppe -(CHj)0-COOR4 bedeutet, R3 C,-C|8-Alkyl oder eine GruppeR 2 is C 1 -C 12 alkyl, phenyl or a group - (CHj) 0 -COOR 4 , R 3 C, -C | 8- alkyl or a group
Έ ist,Έ is,
worin UC2-Ce-AIkYIe^-CHjCH2SCH2CH2-oder-CH2CH2(OCH2CH2),!-bedeutet, R4 C,-C|8-Alkyl bedeutet,wherein UC 2 -Ce-AIkYIe ^ -CHjCH 2 SCH 2 CH 2 -or-CH 2 CH 2 (OCH 2 CH 2 ),! - means R 4 C, -C | 8- alkyl,
R10 und R" unabhängig voneinander Ci-C12-Alkyl sind oder R10 und R" zusammen Pentamethylen oder 3-Oxapentamethylen bedeuten, a 1 oder 2 ist, b 1 oder 2 ist, c 1 oder 2 ist und d 1 bis 3 ist, oder (C) ist ein Reaktionsgemisch aus einem Phenol der FormelR 10 and R "independently of one another are C 1 -C 12 -alkyl or R 10 and R" together are pentamethylene or 3-oxapentamethylene, a is 1 or 2, b is 1 or 2, c is 1 or 2 and d is 1 to 3 or (C) is a reaction mixture of a phenol of the formula
C-HC-H
C-JC-J
Il IIl
mit einem Phenol der Formelwith a phenol of the formula
?H ? H
E-;E;
oderor
oderor
C-C-
?H ? H
/V/ V
-D-D
Il IIl
und (Para)Formaldehyd, worin C, D und E unabhängig voneinander C,-C8-Alkyl bedeuten.and (para) formaldehyde, wherein C, D and E are independently C, -C 8 alkyl.
Eine als Komponente (C) besonders geeignete Klasse sind die Verbindungen der Formel I, worin A und B unabhängig voneinander C,-C4-Alkyl bedeuten, X eine Gruppe -C,H2,-Sq-R2 bedeutet, a O oder 1 ist, q 1 oder 2 ist, R2 C4-C18-AIkYi, PhenylA particularly suitable as component (C) class are the compounds of formula I, wherein A and B are independently C, -C4-alkyl, X is a group -C, H 2 , -S q -R 2 , a O or 1 is, q is 1 or 2, R 2 is C 4 -C 18 alkyl, phenyl
oder-CH2-CO-OR4 bedeutet und R4 Ci-Cie-Alkyl ist, insbesondere die Verbindungen der Formel I, worin A und B unabhängig voneinander C1-C4-AIkYl bedeuten, X -CH2-S-R2 ist, R2 Cg-C12-Älkyl oder -CH2-CO-OR4 ist und R4 Cs-C18-AIkYl bedeutet.or-CH 2 -CO-OR 4 and R 4 Ci-Cie-alkyl, in particular the compounds of formula I, wherein A and B are independently C 1 -C 4 -alkyl, X is -CH 2 -SR 2 , R 2 is Cg-C 12 -alkyl or -CH 2 -CO-OR 4 and R 4 is Cs-C 18 -alkyl.
Besonders bevorzugt in dieser Klasse sind Verbindungen der Formel I, worin A und B tert.Buiyl sind und X-CH2SCH2COO(C8-Ci3-Alkyl) ist.Especially preferred in this class are compounds of the formula I, wherein A and B are tert.Buiyl and X-CH 2 SCH 2 COO (C 8 -C 3 alkyl).
Eine weitere als Komponente (C) besonders geeignete Klasse sind die Verbindungen der Formel I1 worin A und B unabhängig voneinander C1-C4-AIkYl bedeuten, X eine Gruppe -CbH2b-CO-OR3 ist, b 1 oder 2 ist und R3 eine der GruppenAnother class which is particularly suitable as component (C) are the compounds of the formula I 1 in which A and B, independently of one another, denote C 1 -C 4 -alkyl, X is a group -C b H 2 b -CO-OR 3 , b 1 or 2 and R 3 is one of the groups
-(CH2)2-S-(CH2)2-O-C-CbH2b N - (CH 2 ) 2-S- (CH 2 ) 2 -OCC b H 2b N
—OH-OH
-(CH2)6-O-ö-CbH2b ( )-0H- (CH 2 ) 6 -O-ö-C b H 2b () -OH
-CH2-C--CH 2 -C-
•-0H• -0H
bedeutet, , ,means,,
insbesondere die Verbindungen der Formel I, worin X eine Gruppe -(CH2I2-CO-OR ist und R eine Gruppein particular the compounds of the formula I in which X is a group - (CH 2 I 2 -CO-OR and R is a group
-(CH2) Z-S-(CH2) 2-0-C-(CH2)-- (CH 2) ZS (CH2) 2-0-C (CH 2) -
Eine weitere als Komponente (C) besonders geeignete Klasse sind die Methylenbisphenole der Formel (J)H (J)HAnother class which is particularly suitable as component (C) are the methylene bisphenols of the formula (I) H (J) H
CH2CH2
HO-HO
—CH2 -CH 2
< N < N
-OH-OH
worin A, B und X unabhängig voneinander C,-C4-Alkyl bedeuten.wherein A, B and X are independently C, -C 4 alkyl.
Besonders geeignet als Komponente (C) sind ferner Gemische von Polyphenolen, wie man sie durch Reaktion mindestens eines dialkylierten Phenols der FormelAlso particularly suitable as component (C) are mixtures of polyphenols, as obtained by reaction of at least one dialkylated phenol of the formula
(J)H (J)H(J) H (J) H
C /\ C-.'X-DC \ \ C -. 'X-D
υ Il I oder Il I υ Il I or Il I
V VV v
mit mindestens einem monoalkylierten Phenol der Formel VHwith at least one monoalkylated phenol of the formula V H
oderor
y\y \
und Formaldehyd oder Paraformaldehyd erhält, wobei C, D und E unabhängig voneinander C|-C4-Alkyl bedeuten. Die dabei entstehenden Gemische enthalten vorwiegend Diphenole und Triphenole.and formaldehyde or paraformaldehyde, where C, D and E independently of one another are C 1 -C 4 -alkyl. The resulting mixtures contain mainly diphenols and triphenols.
Beispiele für Verbindungen der Formel I sind: Tridecyl-4-(4-hydroxy-3,5-di-tert.butylphenyl)-3-thiabutyrat 3-Thie-1,5-pentadiol-di[3-(4-hydroxy-3,5-di-tert.butylphenyl)]-propionat Di(3-thiap8ntadecyl)-di(4-hydroxy-3,5-di-tert.butylphenyl)-malonat Octadecyl-4-(4-hydroxy-3,5-di-tert.butylphenyl)-3-thiabutyrat 4-(2-Thiapropyl)-2,b-di-tert.butyl-phenol Octadecyl-3-(4-hydroxy-3,5-di-tert.butylphenyl)-propionat 3-Thiapentadecyl-3-(4-hydroxy-3,5-di-tert. butylphenyO-propionat Di(4-hydroxy-3,5-di-tert. butylphenyD-sulfid Di(4-hydroxy-3,5-di-tert. butylphenyll-disulfid 2,4-Di(octylthiomethyl)-6-methylphenolExamples of compounds of the formula I are: tridecyl-4- (4-hydroxy-3,5-di-tert-butylphenyl) -3-thiabutyrate 3-thie-1,5-pentadiol-di [3- (4-hydroxybenzoyl) 3,5-di-tert-butylphenyl)] - propionate di (3-thiap8ntadecyl) -di (4-hydroxy-3,5-di-tert-butylphenyl) -malonate octadecyl-4- (4-hydroxy-3,5 -di-tert-butylphenyl) -3-thiabutyrate 4- (2-Thiapropyl) -2, b-di-tert-butylphenol Octadecyl-3- (4-hydroxy-3,5-di-tert-butylphenyl) - propionate 3-thiapentadecyl-3- (4-hydroxy-3,5-di-tert-butylphenyl-propionate di (4-hydroxy-3,5-di-tert-butylphenyD-sulfide di (4-hydroxy-3,5- di-tert-butylphenyll-disulfide 2,4-di (octylthiomethyl) -6-methylphenol
N-Octadecyl-3-(4-hydroxy-3,5-di-tert. butylphenylj-propionamid N,N'-[3-(4-Hydroxy-3,5-di-tert. butylphenyl)-propionyl]-hexamethylen-diamin 4,4'-Methylen-bis(2,6-di-tert. butylphanol) 2,2'-Methylen-bis(2-tert. butyl-4-methylphenol) 2,4-Di(4-hydroxy-3,5-di-tert. butylbenzyl)-6-tert. butylphenol 4,4'-Methylen-bis[2-tert. butyl-4-(4-hydroxy-3,5-di-tert. butylbenzyl)phenol| 4-Dimethylaminomethyl-2,6-di-tert. butylphenol 4-Dibutyiamino-methyl-2-methyl-6-tert. butylphenol N-Di(4-hydroxy-3,5-di-tert. butylbenzylj-octylaminN-Octadecyl-3- (4-hydroxy-3,5-di-tert-butylphenyl) propionamide N, N '- [3- (4-hydroxy-3,5-di-tert-butylphenyl) -propionyl] hexamethylene -diamine 4,4'-methylenebis (2,6-di-tert-butylphanol) 2,2'-methylenebis (2-tert-butyl-4-methylphenol) 2,4-di (4-hydroxybenzyl) 3,5-di-tert-butylbenzyl) -6-tert-butylphenol 4,4'-Methylenebis [2-tert-butyl-4- (4-hydroxy-3,5-di-tert-butylbenzyl) phenol 4-Dimethylaminomethyl-2,6-di-tert-butylphenol 4-Dibutyiamino-methyl-2-methyl-6-tert-butylphenol N-di (4-hydroxy-3,5-di-tert-butylbenzyl-octylamine
Besonders bevorzugte Schmierstoffzusammensetzungen sind solche, worin (B) eine Verbindung der Formel IX oder X ist,Particularly preferred lubricant compositions are those wherein (B) is a compound of formula IX or X,
CH3/CHjCH 3 / CHj
=0= 0
IXIX
worin η 1 oder 2 ist, R" Wasserstoff oder Methyl ist und Y, wenn η 1 ist,-O(CB-C16-Alkyl) bedeutet, und wonn π 2 ist, eine Gruppe -NH-(CH2)J-NH- oder -0-CO-(CHj)1n-CO-O- bedeutet, worin m 2-8 ist, undwherein η is 1 or 2, R "is hydrogen or methyl and Y when η is 1, -O (CB-C 16 -alkyl), and when π is 2, a group -NH- (CH 2 ) J- NH- or -O-CO- (CHj) 1n -CO-O-, wherein m is 2-8, and
(C) eine Verbindung der Formel I ist, worin A Wasserstoff, C,-C4-Alkyl oder eine Gruppe(C) is a compound of formula I, wherein A is hydrogen, C, -C 4 alkyl or a group
bedeutet,means
B Ct-C4-Alkyl bedeutet,BC t -C 4 alkyl,
X C,-C4-Alkyl oder eine der Gruppen -CH2-S-R2, -CH2CH2COOR3, -CH2N(R10I(R11) oderX is C, -C 4 alkyl or one of the groups -CH 2 -SR 2 , -CH 2 CH 2 COOR 3 , -CH 2 N (R 10 I (R 11 ) or
bedeutet,means
a2 C,-C,8-Alkyl OdOr-(CH2Ir-COOR4 ist,a 2 is C 1 -C 8 -alkyl, OdOR- (CH 2 Ir-COOR 4 ,
R3 C1-C18-AIkVl oderR 3 C 1 -C 18 -AlkVl or
-C-CH2CH2-".7 -C-CH 2 CH 2 - ". 7
-CH2CH2-S-CH2CH2-O-C-Ch2CH2-*^-CH 2 CH 2 -S-CH 2 CH 2 -OC-Ch 2 CH 2 - * ^
bedeutet,means
R4 C,-C18-Alkyl ist undR 4 is C 1 -C 18 -alkyl and
R10 und R11 Ct-Ca-Alkyl sind, oaer (C) ein Reaktionsgemisch aus 2-tert. Butylphenol, 2,6-Di-tert. butylpheno! und (Para)Formaldehyd ist.R 10 and R 11 are Ct-Ca-alkyl, oaer (C) a reaction mixture of 2-tert. Butylphenol, 2,6-di-tert. butylpheno! and (para) formaldehyde.
Die Komponenten (B) und (C) können direkt dem Basisöl zugegeben werden oder man löst zuerst (B) und (C) in einer kleinen Menge Basisöl, gegebenenfalls unter Erwärmen, und mischt die Lösung mit der restlichen Menge des OeIs. Man kann auch ein ι konzentrierte Lösung von (B) und (C) in einem Lösungsmittel dem OeI zumischen.Components (B) and (C) may be added directly to the base oil, or first dissolve (B) and (C) in a small amount of base oil, optionally with heating, and mix the solution with the remaining amount of OeI. One can also mix in a ι concentrated solution of (B) and (C) in a solvent to the oil.
Der Zusatz von (B) und (C) zum Basisöl bewirkt eine Stabilisierung gegen oxidativen Abbau und bewirkt in Motorenölen eine Verminderung der Sc' 'ammbildung.The addition of (B) and (C) to the base oil stabilizes against oxidative degradation and causes a reduction in scum formation in engine oils.
Die Schmiermittelzuoammensetzung kann zusätzlich andere Additive enthalten, wie z. B. Phosphor-lll-ester, Metalldesaktivatoren, Rostinhibitoren, Viskositäisindex-Verbesserer, Stockpunktserniedriger, Dispergiermittel, Tenside oder/ und Verschleißschutz-Additive.The lubricant composition may additionally contain other additives, such as. Phosphorus III esters, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, surfactants or / and anti-wear additives.
Beispiele für Phosphor-lli-estcr sind:Examples of phosphorus esters are:
Triphenylphosphit, Decyl-diphenylphosphit, Phenyl-didecylphosphit, Tris-(nonylphenyl)-phosphit, Trilaurylphosphit, Trioctadecylphosphit, Distearyl-pentaerythritdiphosphit,Tris-(2,4-di-tert.butylphenyl)-phosphit, Diisodecylpentaerythritdiphosphit,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.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, diisodecyl pentaerythritol diphosphite, bis (2,4 -di-tert-butylphenyl) -pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert-butylphenyl) -4,4'-biphenylene diphosphonite, bis (2,6-di-tert. butyl-4-methyl-phenyl) pentaerythritol diphosphite.
Beispiele für Metall-Dosaktivatoren, z. B. für Kupfer, sind:Examples of metal dosifactants, e.g. For copper, are:
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.Triazoles, benzotriazoles and their derivatives, tolutriazoles and their derivatives, 2-mercaptobenzothiazole, 2-mercaptobenzotriazole, 2,5-dimercaptobenztriazole, 2,5-dimercaptobenzothiadiazole, 5,5'-methylenebisbenzotriazole, 4,5,6,7-tetrahydrobenzotriazole, salicylidene propylenediamine, salicylaminoguanidine and its salts.
Beispiele für Rost-Inhibitoren sind:Examples of rust inhibitors are:
a) Organische Säuren, ihre Ester, Metalisalze und Anhydride, z.B.: N-Oleoyl-sarcosin, Sorbitan-mono-oleat, Blei-naphthenat, Alkenylbernsteinsäureanhydrid, z. B. Dodecenylbernsteinsäure-anhydrid, Alkenylbernsteinsäure-Teilester und -Teilamide, 4-Nonylphenoxyessigsäure.a) Organic acids, their esters, metal salts and anhydrides, e.g., N-oleoyl sarcosine, sorbitan mono-oleate, lead naphthenate, alkenyl succinic anhydride, e.g. Dodecenylsuccinic anhydride, alkenylsuccinic acid partial esters and -partamides, 4-nonylphenoxyacetic acid.
b) Stickstoffhaltige Verbindungen, z.B.:b) Nitrogen-containing compounds, for example:
I. Primäre, sekundäre oder tertiäre aliphatische oder cycloaliphatische Amine und Amin-Salze von organischen und anorganischen Säuren, z. B. öllöslicho Alkylammoniumcarboxylate.I. Primary, secondary or tertiary aliphatic or cycloaliphatic amines and amine salts of organic and inorganic acids, eg. B. oil soluble alkyl ammonium carboxylates.
II. Heterocyclische Verbindungen, z. B.: Substituierte Imidazoline und Oxazoline.II. Heterocyclic compounds, eg. B.: Substituted imidazolines and oxazolines.
c) PhosphorhaltigeVerbindungen,z.B.:c) Phosphorus-containing compounds, e.g.
Aminsalze von Phosphorsäurepartialestern odor Phosphonsäurepartialestern, Zinkdialkyldithiophosphate.Amine salts of phosphoric acid partial esters or phosphoric acid partial esters, zinc dialkyldithiophosphates.
d) Schwefelhaltige Verbindungen, z. B.: Barium-dinonylnaphthalin-sulfonate, Calciumpetroleum-suifonate.d) Sulfur-containing compounds, for. B.: Barium dinonylnaphthalenesulfonates, calcium petroleum sulfonates.
Beispiele für Viskositätsindex-Verbesserer sind:Examples of viscosity index improvers are:
Polyacrylate, Polymethacrylate, Vinylpyrrolidon/Methacrylat-Copolymere, Polyvinylpyrrolidone, Polybutene, Olefin-Copolymere, Styrol/Acrylat-Copolymere, Polyether.Polyacrylates, polymethacrylates, vinylpyrrolidone / methacrylate copolymers, polyvinylpyrrolidones, polybutenes, olefin copolymers, styrene / acrylate copolymers, polyethers.
Beispiele für Stockpunktern'ddrlger sind:Examples of pour point depressants are:
Polymethacrylat, alkylierto Naphthalinderivate.Polymethacrylate, alkylated naphthalene derivatives.
Beispiele für Diopergipimittel/Tenside sind:Examples of di-excipients / surfactants are:
Polybutenylbernsieinsäureamide oder -imide, Polybutenylphosphonsäurederivate, basische Magnesium-, Calcium-, und Bariumsulfonate und -phenolate.Polybutenylsuccinic acid amides or imides, polybutenylphosphonic acid derivatives, basic magnesium, calcium, and barium sulfonates and phenates.
Beispiele für Vorschlelßschutz-Add.tlve sind; Schwefel und/oder Phosphor und/oder Halogen enthaltende Verbindungen, wie geschwefelte pflanzliche Öle, Zinkdialkyldithiophosphate, Tritolyl-phosphat, chlorierte Paraffine, Alkyl- und Aryldi- und tri-sulfide, Triphenylphosphorothionate, Diethanolaminomethyltolyltriazol, Di(2-ethylhoxyl)u.Tiinomethyltolyltriazol.Examples of precursors add.tlve are; Sulfur and / or phosphorus and / or halogen-containing compounds, such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl di- and tri-sulfides, triphenyl phosphorothioates, diethanolaminomethyltolyl triazole, di (2-ethylhoxyl) u.Tiinomethyltolyltriazol.
Der Schmierstoff kann auch feste Schmierstoffe enthalten, wie z. B. Graphit oder Molybdänsulfid.The lubricant may also contain solid lubricants, such as. As graphite or molybdenum sulfide.
Die folgenden Beispiele erläutern die Erfindung näher. Darin bedeuten % Gew.-%.The following examples illustrate the invention in more detail. Therein mean% by weight.
Das Oxidationsverhalten von erfindungsgemäß stabilisierten Schmierölen wird nach der TOST-Methode (turbi.o oxidation stability test) gemäß ASTM D-943 geprüft.The oxidation behavior of lubricating oils stabilized according to the invention is tested according to the TOST method (turbi.o oxidation stability test) according to ASTM D-943.
Hierzu werden 300ml eines Mineralöls (Mobil STOCK305), das 0,05% eines Korrosionsinhibitors (Reocor812) enthält, mit 60ml Wasser versetzt und in Gegenwart von Eise·)- und Kupferdraht unter Durchleiten von Sauerstoff 1000 Stunden auf 95°C erwärmt.For this purpose, 300 ml of a mineral oil (Mobil STOCK305) containing 0.05% of a corrosion inhibitor (Reocor 8 12), mixed with 60ml of water and heated in the presence of ice ·) and copper wire while passing oxygen for 1000 hours at 95 ° C.
Gemessen wird die Bildung von Säuren durch Bestimmung der Neutralisationszahl TAN (mg KOH/g Öl) sowie die gebildete Menge an Schlamm = SLUDGE.The formation of acids is measured by determining the neutralization number TAN (mg KOH / g oil) and the amount of sludge = SLUDGE formed.
Als Stabilisatoren werden verwendet;As stabilizers are used;
• — ·• - ·
CH3 CH 3
,CH3 , CH 3
H-1 HN J, OCi2H25 H-1 HN J, OCi 2 H 25
• ·• ·
CH3 CH3 CH 3 CH 3
Die Gesamtmenge an Stabilisatoren beträgt 0,25%, bezogen auf das Öl. Die Zusammensetzung des Stabilisator-Gemisches wird variiert. Die Ergebnisse sind in Tabelle 1 aufgeführt.The total amount of stabilizers is 0.25%, based on the oil. The composition of the stabilizer mixture is varied. The results are shown in Table 1.
Es wird wie in Beispiel 1 getestet. Als Stabilisatoren werden verwendet:It is tested as in Example 1. As stabilizers are used:
(CH3)3C(CH 3) 3 C
P_2 HO-^ ^--CH2CH2COOCH2CH2SCH2CH2OOCCHzCH2-'7 P_2 HO- ^ ^ - CH 2 CH 2 COOCH 2 CH 2 SCH 2 CH 2 OOCchzCH 2 - ' 7
3H3 CH3 CH3 CH3 3H 3 CH 3 CH 3 CH 3
XC(CH3)3 X C (CH 3 ) 3
CH3 CUi \h3 CH 3 CUi \ h 3
Die Gesamtkonzentration beträgt 0,25%, bezogen auf das Öl.The total concentration is 0.25%, based on the oil.
Anteil TOST PJ H-2 JAN SLUDGE Share TOST PJ H-2 JAN SLUDGE
100% - >2 > 1000mg 95% 5% 0,26 219 mg 90% 10% ΓΛ24 190 mg 100% ->2> 1000mg 95% 5% 0.26 219 mg 90% 10% ΓΛ24 190 mg
Es wird wie in Beispiel 1 getestet. Als Stabilisatoren werden verwendet:It is tested as in Example 1. As stabilizers are used:
S /C(CH3)3 S / C (CH 3 ) 3
p.2 HO—N ^'-CH2CH2COOCH2CH2SCH2Ch2OOCCH2CH2-N /'-0Hp.2 HO - N - '- CH 2 CH 2 COOCH 2 CH 2 SCH 2 Ch 2 OOCCH 2 CH 2 - N /' - 0H
C C(CH3) jCC (CH 3 ) j
CH3 CH3 CH3 CH3 CH 3 CH 3 CH 3 CH 3
Ch3 CH3 CH3 CH3 Ch 3 CH 3 CH 3 CH 3
Die Gesamtkonzentration beträgt 0,25%. Die Ergebnisse sind in Tabelle 3 aufgeführt.The total concentration is 0.25%. The results are shown in Table 3.
Anteil TOST P-2 H-3 TAN SLUDGE Share TOST P-2 H-3 TAN SLUDGE
100% - >2 > 1000mg100% -> 2> 1000mg
95% 5% 0,24 180 mg95% 5% 0.24 180 mg
Es wird wie in Beispiel 1 getestet. Als Stabilisatoren werden verwendet:It is tested as in Example 1. As stabilizers are used:
(CH3)3CX P-2 HO—N ^'-CH2CH2COOCH2CH2SCH2CH2OOCCH2Ch2-N /·(CH 3) 3 C X P-2 HO N ^ '- CH 2 CH 2 COOCH 2 CH 2 SCH 2 CH 2 OOCCH 2 Ch 2 - N / ·
NC(CH3)3 N C (CH 3 ) 3
CH3 ,CH3 CH 3 , CH 3
H-1 HN^ OCi2H25 H-1 HN ^ OCi 2 H 25
CH3 CH 3
Die Gesamtkonzentration beträgt 0,25%. Die Ergebnisse sind in Tabelle 4 aufgeführt. Tabelle 4The total concentration is 0.25%. The results are shown in Table 4. Table 4
Es wird wie in Beispiel 1 getestet. Als Stabilisatoren werden verwendet:It is tested as in Example 1. As stabilizers are used:
/ \ P-2 HO—χ ^-CH2CH2COOCH2CH2SCH2CH2OOCCH2Ch2-/ \ P-2 HO- χ ^ -CH 2 CH 2 COOCH 2 CH 2 SCH 2 CH 2 OOCCH 2 Ch 2 -
(CHjhC7 (CHjhC 7
C(CH3)C (CH 3 )
CH3 Die Gesamtkonzentration beträgt 0,25%. Die Ergebnisse sind in Tabelle 5 aufgeführt.CH 3 The total concentration is 0.25%. The results are shown in Table 5.
Anteil P-2Share P-2
H-4H-4
TANTAN
TOSTTOST
SLUDGESLUDGE
5% 10%5% 10%
>2> 2
0,18 0,160.18 0.16
> 1000 mg> 1000mg
91 mg91 mg
161 mg161 mg
Die Oxidationsbeständigkeit der erfindungsgemäß stabilisierten Öle wird in einem Differential-Scanning-Kalorimeter gemessen.The oxidation resistance of the oils stabilized according to the invention is measured in a differential scanning calorimeter.
Dabei wird in einem Al-Schälchen ein Basisöl mit 0,025% Eisen-lll-acetylacetonat (als Oxidationskatalysator) und 0,55% eines Stabilisato· s vermischt und im Kalorimeter unter 10bar Sauerstoff isotherm auf 160 JC erwärmt. Gemessen wird die Zeit bis zum Beginn der exothermen Reaktion Tb (Induktionszeit) und die Zeit bis zum Ende der exothermen Reaktion TE. Je langer die Induktionszeit ist, desto höher ist die Oxidationsbeständigkeit.·Als Stabilisatoren werden die phenolischen Antioxidantien P-1 und P-2 verwendet sowie:Here, in a Al-bowl a base oil with 0.025% ferric acetylacetonate (as an oxidation catalyst) and 0.55% of a Stabilisato · s and is mixed in the calorimeter under 10bar oxygen isothermally heated to 160 C J. The time until the beginning of the exothermic reaction Tb (induction time) and the time until the end of the exothermic reaction T E is measured. The longer the induction time, the higher the oxidation resistance. The stabilizers used are the phenolic antioxidants P-1 and P-2, and:
P-3: Reaktionsprodukt von 160g 2,6-Di-teit. bulylphenol, 40g 2-Tert.-butylphenol, 5,8g KOH, 50ml Ethanol und 24g Paraformaldehyd bei 800C, enthaltend als HauptkomponentenP-3: reaction product of 160g 2,6-di-teit. bulylphenol, 40g of 2-tert-butylphenol, 5.8 g KOH, 50 ml of ethanol and 24 g of paraformaldehyde at 80 0 C, comprising as main components
(CH3)3C(CH 3) 3 C
CH2 CH 2
C(CH3):C (CH 3 ):
C(CH3)3C (CH 3 ) 3
(CH3)(CH 3 )
HO—HO
-CH2--CH 2 -
:h2-: h 2 -
Ύ\)Η C(CH3)3 Ύ \) Η C (CH 3 ) 3
,C(CHj)3 S-OH C(CH3)3, C (CHj) 3 S-OH C (CH 3 ) 3
(CH3)3C.(CH 3 ) 3C .
HO-(CHj)3CHO- (CHj) 3 C
-CH2--CH 2 -
Il IIl
YAYA
-CH2--CH 2 -
Il IIl
0H0H
γ OH C(CH3)3 γ OH C (CH 3 ) 3
C(CH3)C (CH 3 )
-OH-OH
C(CH3):C (CH 3 ):
OH OHOH OH
p.^. ν ^n3 ^3C- j · CH2 jj j—C(TH3 )3 p. ^. ν ^ n 3 ^ 3 C-j · CH 2 jj j-C (TH 3 ) 3
C(CH3)3 C(CH3)3 C (CH 3 ) 3 C (CH 3 ) 3
P-5: Gemisch 1:1 vonP-5: mixture 1: 1 of
OH OHOH OH
(CHs)3C-J7 X'-C(CH3)3 und jX X'-C(CH3)3 (CHs) 3 CJ 7 X '-C (CH 3 ) 3 and J XX ' -C (CH 3 ) 3
C(CHa)3 C(CH3)3 C (CHa) 3 C (CH 3 ) 3
Als sterisch gehindertes Amin wird verwendetAs hindered amine is used
C^3/CH3 CH3 CH3 C ^ 3 / CH 3 CH 3 CH 3
Die Ergebnisse sind in Tabelle 6 aufgeführt.The results are shown in Table 6.
Daran ist zu ersehen, daß bei Verwendung von Stabilisaxorgemischen aus 0,10% der Komponente A und 0,45% der Komponente B die Oxidationsbeständigkeit 'es Öles höher ist, als aus den Daten der einzelnen Komponenten zu erwarten wäreIt can be seen that when using Stabilisaxorgemischen from 0.10% of component A and 0.45% of component B, the oxidation resistance 'it is higher oil than would be expected from the data of the individual components
Die Oxidationsbeständigkeit wird wie in Beispiel 6 in einem Differential-Scanning-Kalorimeter getestet, mit dem Unterschied, daß statt unter Sauerstoff unter 8bar Luft, der 380ppm (NO)x beigemischt sind, gemessen wird und daß die isotherme Temperatur 170°C beträgt. Gemessen wird nur der Beginn der Exotherme.The oxidation resistance is tested as in Example 6 in a differential scanning calorimeter, with the difference that instead of under 8 bar air, the 380ppm (NO) x are mixed, measured and that the isothermal temperature is 170 ° C. Only the beginning of the exotherm is measured.
P-6 HO-'( P-6 HO- '(
Claims (19)
M ι oderOH
M ι or
/X OH
/ X
beträgt.A composition according to claim 1, wherein the weight ratio of (B) to (C) is 1: 3 to 1:20
is.
8. Zusammensetzung gemäß Anspruch 5, worin (B) eine Verbindung der Formel IV ist,wherein R is hydrogen, R 11 is hydrogen or methyl, η is 1 and R 12 is C 1 -C 18 -AIRyI or η is 2 and R 12 is the diacyl radical of an aliphatic dicarboxylic acid having 4-12 C atoms.
8. A composition according to claim 5, wherein (B) is a compound of formula IV,
(C) eine Verbindung der Formel I ist, worin A Wasserstoff, C1-C4-A^yI oder eine Gruppewherein η is 1 or 2, R 11 is hydrogen or methyl and Y, when η is 1, -O (C 8 -C 15 -alkyl), and when η is 2, a group -NH- (CH 2 ) O- NH- or -O-CO- (CH 2 ) m -CO-O-, wherein m is 2-8, and
(C) is a compound of formula I, wherein A is hydrogen, C 1 -C 4 -A ^ yI or a group
2\ Verwendung einer Zusammensetzung gemäß Anspruch 1 als Motorenöl.is.
2 \ Use of a composition according to claim 1 as a motor oil.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CH252889 | 1989-07-07 |
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Publication Number | Publication Date |
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DD297443A5 true DD297443A5 (en) | 1992-01-09 |
Family
ID=4235829
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DD90342534A DD297443A5 (en) | 1989-07-07 | 1990-07-05 | LUBRICANT COMPOSITIONS |
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EP (1) | EP0406826B1 (en) |
JP (1) | JP2943004B2 (en) |
KR (1) | KR0151400B1 (en) |
CN (1) | CN1028243C (en) |
BR (1) | BR9003187A (en) |
CA (1) | CA2020558C (en) |
DD (1) | DD297443A5 (en) |
DE (1) | DE59002284D1 (en) |
ZA (1) | ZA905305B (en) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
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US5486316A (en) * | 1987-06-01 | 1996-01-23 | Henkel Corporation | Aqueous lubricant and surface conditioner for formed metal surfaces |
BE1004925A5 (en) * | 1991-01-08 | 1993-02-23 | Ciba Geigy Ag | LUBRICANT COMPOSITIONS CONTAINING A COMBINATION OF STABILIZERS. |
JP3401349B2 (en) * | 1994-12-07 | 2003-04-28 | 新日本石油株式会社 | Lubricating oil composition |
JP3527555B2 (en) * | 1994-12-09 | 2004-05-17 | 出光興産株式会社 | Heat treated oil composition |
JP3508785B2 (en) * | 1994-12-13 | 2004-03-22 | 出光興産株式会社 | Lubricating oil composition for gears |
JP3527556B2 (en) * | 1994-12-14 | 2004-05-17 | 出光興産株式会社 | Lubricating oil composition for internal combustion engines |
JP4946063B2 (en) * | 2006-01-12 | 2012-06-06 | 日本精工株式会社 | Grease composition and rolling bearing |
MX2009001124A (en) * | 2006-07-31 | 2009-03-05 | Ciba Holding Inc | Lubricant composition. |
US9422501B2 (en) | 2012-07-27 | 2016-08-23 | Jx Nippon Oil & Energy Corporation | Lubricating oil composition and method for lubricating sliding material while preventing elution of copper and lead |
FR3020377B1 (en) * | 2014-04-25 | 2020-11-27 | Total Marketing Services | LUBRICATING COMPOSITION INCLUDING AN ANTI-CLICKING COMPOUND |
WO2016156328A1 (en) * | 2015-03-31 | 2016-10-06 | Shell Internationale Research Maatschappij B.V. | Use of a lubricating composition comprising a hindered amine light stabilizer for improved piston cleanliness in an internal combustion engine |
CN110273159A (en) * | 2019-07-02 | 2019-09-24 | 宜兴市中大凯水处理有限公司 | A kind of new type high temperature corrosion inhibiter and preparation method thereof |
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US3336226A (en) * | 1965-12-28 | 1967-08-15 | Chevron Res | Phenolic pour point depressants |
US3480635A (en) * | 1966-09-28 | 1969-11-25 | Universal Oil Prod Co | N-piperidyl substituted phenylenediamines |
US3939163A (en) * | 1973-12-28 | 1976-02-17 | Ciba-Geigy Corporation | Metal salts of hindered piperidine carboxylic acids and stabilized compositions |
DE3266599D1 (en) * | 1981-02-19 | 1985-11-07 | Ciba Geigy Ag | Organic elastomers and mineral and synthetic lubricating oils containing phenolmercaptocarboxylic esters as stabilizers |
US4362887A (en) * | 1981-04-10 | 1982-12-07 | The Goodyear Tire & Rubber Company | Synergistic antioxidant mixtures |
US4582943A (en) * | 1983-12-23 | 1986-04-15 | Ciba-Geigy Corporation | Stabilization of polyalkylene glycols |
US4607104A (en) * | 1985-07-11 | 1986-08-19 | Uniroyal Chemical Company, Inc. | Process for the production of 2,2,6,6-tetraalkyl-4-piperidylamines |
CA1248516A (en) * | 1985-07-15 | 1989-01-10 | Stephen C. Cohen | Lubricating oil compositions containing novel combination of stabilizers |
DE3671241D1 (en) * | 1985-11-13 | 1990-06-21 | Ciba Geigy Ag | SUBSTITUTED PHENOLES AS STABILIZERS. |
DE3785320D1 (en) * | 1986-12-24 | 1993-05-13 | Ciba-Geigy Ag, Basel, Ch | |
US4836943A (en) * | 1987-07-15 | 1989-06-06 | Texaco Inc. | Anti-oxidant system |
DE58901932D1 (en) * | 1988-06-09 | 1992-09-03 | Ciba Geigy Ag | LUBRICATING OIL COMPOSITION. |
US5073278A (en) * | 1988-07-18 | 1991-12-17 | Ciba-Geigy Corporation | Lubricant composition |
-
1990
- 1990-07-04 DE DE9090112762T patent/DE59002284D1/en not_active Expired - Lifetime
- 1990-07-04 EP EP90112762A patent/EP0406826B1/en not_active Expired - Lifetime
- 1990-07-05 CA CA002020558A patent/CA2020558C/en not_active Expired - Lifetime
- 1990-07-05 DD DD90342534A patent/DD297443A5/en not_active IP Right Cessation
- 1990-07-05 BR BR909003187A patent/BR9003187A/en not_active Application Discontinuation
- 1990-07-06 JP JP2179385A patent/JP2943004B2/en not_active Expired - Lifetime
- 1990-07-06 ZA ZA905305A patent/ZA905305B/en unknown
- 1990-07-07 KR KR1019900010358A patent/KR0151400B1/en not_active IP Right Cessation
- 1990-07-07 CN CN90103183A patent/CN1028243C/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
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EP0406826A1 (en) | 1991-01-09 |
CA2020558A1 (en) | 1991-01-08 |
BR9003187A (en) | 1991-08-27 |
JP2943004B2 (en) | 1999-08-30 |
EP0406826B1 (en) | 1993-08-11 |
KR0151400B1 (en) | 1998-10-01 |
ZA905305B (en) | 1991-05-29 |
KR910003079A (en) | 1991-02-26 |
CN1048560A (en) | 1991-01-16 |
DE59002284D1 (en) | 1993-09-16 |
CN1028243C (en) | 1995-04-19 |
CA2020558C (en) | 2001-11-06 |
JPH0345696A (en) | 1991-02-27 |
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