DE1275060B - Stabilisatorgemisch fuer mono- oder polymere Kohlenwasserstoffe - Google Patents
Stabilisatorgemisch fuer mono- oder polymere KohlenwasserstoffeInfo
- Publication number
- DE1275060B DE1275060B DEG43802A DEG0043802A DE1275060B DE 1275060 B DE1275060 B DE 1275060B DE G43802 A DEG43802 A DE G43802A DE G0043802 A DEG0043802 A DE G0043802A DE 1275060 B DE1275060 B DE 1275060B
- Authority
- DE
- Germany
- Prior art keywords
- hours
- acid
- stabilized
- polypropylene
- butyl
- 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
Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0092—Mixtures
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
- C09K15/14—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen containing a phenol or quinone moiety
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- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0071—Preserving by using additives, e.g. anti-oxidants containing halogens, sulfur or phosphorus
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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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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/088—Neutral salts
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
-
- 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
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2221/043—Polyoxyalkylene ethers with a thioether group
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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Description
deutsches ^mmmt Patentamt
C07c;C08 f;C101; ClOm
Deutsche KL: 12 ο - 27; 1^9/01, 23/03,
26/01; 12 ρ -10/05; 12 q - U\(hJ 31/02; 23 c-1/01 '
Nummer: 1275 060
Aktenzeichen: P 12 75 060.6-42 (G 43802)
J 275 060 Anmeldetag: 4.Juni 1965
Auslegetag: 14. August 1968
Wie aus der belgischen Patentschrift 637 443 bekannt ist, werden organische Stoffe durch Mischungen
phenolischer Verbindungen und Thio-dipropionsäuredilaurylester stabilisiert. Es wurde nun überraschend
gefunden, daß Alkylmercaptomethylbernsteinsäurediester als Costabilisatoren für phenolische
Antioxydantien den Thio - dipropionsäuredilaurylestern bei der Stabilisierung von mono- und polymeren
aliphatischen Kohlenwasserstoffen überlegen sind.
Gegenstand der Erfindung ist deshalb die Verwendung von Diestern der Alkylmercaptomethylbernsteinsäure
der allgemeinen Formel I
II
R1-S-CH2-CH C-O-R2 (I)
CH2-C-O-R3
worin Ri eine Alkylgruppe mit 8 bis 18 und vorzugsweise 12 bis 18 Kohlenstoffatomen und R2 und R3
jeweils eine Alkylgruppe mit 12 bis 18 Kohlenstoffatomen bedeuten, im Gemisch mit bekannten pheno-
lischen Antioxydantien, zum Stabilisieren von monooder -polymeren aliphatischen Kohlenwasserstoffen.
Ri, Ra und R3 können identisch oder untereinander verschieden sein und im Rahmen der vorstehenden
Definition beispielsweise gerade oder verzweigte Alkylgruppen, wie Octyl-, Nonyl-, Decyl-, Undecyl-,
Dodecyl-, Tridecyl-, Tetradecyl-, Pentadecyl-, Hexadecyl-, Heptadecyl- oder Octadecylgruppen, bedeuten.
Erfindungsgemäß verwendbare Verbindungen der Formel I sind z. B. Dodecylthiomethylbernsteinsäüre-di-dodecylester,
Octadecylthiomethylbernsteinsäure-di-dodecylester, Dodecylthiomethylbernsteinsäure-di-octadecylester,
Octadecylthiomethylbernsteinsäure-di-octadecylester und Octylthiomethylbernsteinsäure-di-dodecylester.
Die erfindungsgemäß verwendeten Verbindungen besitzen die Eigenschaft, die Wirkung zahlreicher
anderer Stabilisatoren, die die Zersetzung mono- oder polymerer aliphatischer Kohlenwasserstoffe verlangsamen,
sehr stark zu erhöhen. In Verbindung mit bekannten phenolischen Stabilisatoren steht die
Stabilisier.ungswirkung in einem weit höheren Maß, als sich dies nach der Summe der Eigenschaften der
Einzelkomponenten erwarten ließe. ,
Mono- oder polymere aliphatische Kohlenwasserstoffe, die durch Zusatz stabilisierender Verbindungen
Stabilisatorgemisch für mono- oder polymere Kohlenwasserstoffe
Anmelder:
J. R. Geigy A. G., Basel (Schweiz)
Vertreter:
Dr. F. Zumstein,
Dipl.-Chem. Dr. rer. nat. Ε. Assmann, Dipl.-Chem. Dr. R. Koenigsberger und Dipl.-Phys. R. Holzbauer, Patentanwälte,
8000 München 2, Bräuhausstr. 4
Als Erfinder benannt:
Dr. Martin Dexter, Briarcliff, Ν. Y.; Kathleen D. Schafer, Bronx, Ν. Υ. (V. St. A.)
Beanspruchte Priorität:
V. St. ν. Amerika vom 5. Juni 1964 (373 078)
gegen die Zersetzung stabilisiert werden und sich daher für die alleinige wie auch für die zusätzliche Einverleibung
von Verbindungen der Formel I eignen, sind beispielsweise Poly-a-olefine, wie Polyäthylen,
Polypropylen, Polybutylen oder Polyisopren, einschließlich Copolymerisaten von Poly-a-olefinen und
Copolymerisate, wie hochschlagfestes Polystyrol, das Copolymerisate von Butadien und Styrol enthält.
Weitere erfindungsgemäß stabilisierbare Stoffe sind z. B. gesättigte und ungesättigte Kohlenwasserstoffe,
wie beispielsweise natürliche und synthetische Benzine, Düsenbrennstoffe, Dieselöle, Mineralöle, Heizöle
oder Paraffinwachse.
Typische bekannte phenolische Antioxydantien, deren stabilisierende Eigenschaften durch Zusatz der
erfindungsgemäßen Verbindungen der Formel I verbessert werden können, sind folgende:
A. Phenolische Stabilisatoren auf Triazinbasis
6-(4-Hydroxy-3,5-di-t-butylanilino)-2,4-bis-
(n-octylthio):l,3,5-triazin;
6-(4-Hydroxy-3,5-di-t-butylanilino)-2,4-bis-
6-(4-Hydroxy-3,5-di-t-butylanilino)-2,4-bis-
phenylthio-l,3,5-triazin;
6-(4-Hydroxy-3,5-di-t-butylanilino)-2,4-bis-
6-(4-Hydroxy-3,5-di-t-butylanilino)-2,4-bis-
octadecylthio)-l ,3,5-triazin; 6-(4-Hydroxy-3,5-di-t-butylanilino)-2,4-biscyclohexylthio-1,3,5-triazin;
809 590/478
6-(2-Hydroxy-3,5-di-t-butyl-6-methylanilino)-
2,4-bis-(n-octyl-thio)-l,3,5-triazin; 6-(4-Hydroxy-3,5-di-t-butylanilino)-2,4-bis-
(carbo-n-Iauryloxyäthylthio)-l,3,5-triazin; 6-(4-Hydroxy-3-methyl-5-t-butylanilino)-2s4-bis- 5
(n-octylthio)-l,3,5-triazin;
6-(4-Hydroxy-3,5-di-t-butylanilino)-2,4-bis-
6-(4-Hydroxy-3,5-di-t-butylanilino)-2,4-bis-
(phenoxy)-l ,3,5-triazin;
2,4-Bis-(4-hydroxy-3,5-di-t-butylphenoxy)-
2,4-Bis-(4-hydroxy-3,5-di-t-butylphenoxy)-
6-amino-l,3,5-triazin; 10 2,4-Bis-(4-hydroxy-3,5-di-t-butylphenoxy)-
6-dibutylamino-l,3,5-triazin; 2,4-Bis-(4-hydroxy-3,5-di-t-butylphenoxy)-
6-(n-octadecylthio)-l, 3,5-triazin; 2,4-Bis-(4-hydroxy-3,5-di-t-butylphenoxy)- 15
6-(n-dodecylthioäthyIthio)-l,3,5-triazin;
2.4- Bis-(4-hydroxy-3,5-di-t-butylphenoxy)-6-(n-octylthio)-1,3,5-iriazin.
B. Phenolische Stabilisatoren auf Phosphonatbasis ^
Zu den vielen Phosphonatstabilisatoren, deren Eigenschaften durch Zusatz der erfindiingsgemäßen
Verbindungen verbessert werden können, zählen auch die Di-nieder?-;:y3phosphonate, die in der
USA.-Patentschrift 3 (ii)6 945 beschrieben sind. Be- 25 sonders wertvolle phenolische Phosphonate sind in
dieser Hinsicht jedoch die Di-iicberalkylphenolphosphonate, d. h. solche, die in jeder Alkylgruppe
bis 30 Kohlenstoffatome aufweisen. Beispiele solcher Verbindungen sind: 30
3-t-Butyl-4-hydroxy-5-methylbenzylphosphon-
säure-di-n-octadecylester;
l-(3,5-Di-t-butyl-4-hydroxyphenyl)-äthanphosphonsäure-di-n-octadecylester;
l-(3,5-Di-t-butyl-4-hydroxyphenyl)-äthanphosphonsäure-di-n-octadecylester;
3.5- Di-t-butyl-4-hydroxybenzylphosphonsä ure- 35 di-n-hexadecylester;
3,5-Di-t-butyl-4-hydroxybenzylphosphonsäuredi-n-octadecylester.
C. Phenolische Stabilisatoren auf Esterbasis
3-(3,5-Di-t-butyl-4-hydroxyphenyl)-propion-
säure-n-octadecylester ;
3,5-Di-t-butyl-4-hydroxyphenyl-essigsäure-
3,5-Di-t-butyl-4-hydroxyphenyl-essigsäure-
n-octadecylester;
3,5-Di-t-butyl-4-hydroxybenzoesäure- 45
3,5-Di-t-butyl-4-hydroxybenzoesäure- 45
n-octadecylester;
3,5-Di-t-butyl-4-hydroxyphenylbenzoesäure-
3,5-Di-t-butyl-4-hydroxyphenylbenzoesäure-
n-dodecylester;
3-(3,5-Di-t-butyl-4-hydroxyphenyl)-propion-
3-(3,5-Di-t-butyl-4-hydroxyphenyl)-propion-
säure-dodecylester; 50 a-(4-Hydroxy-3,5-di-t-butylphenyl)-isobutter-
säure-octadecylester;
3,5-Di-t-butyl-4-hydroxybenzoesäure-2-(n-octyl-
3,5-Di-t-butyl-4-hydroxybenzoesäure-2-(n-octyl-
thio)-äthylester;
/i,/?'-Thiodiäthyl-bis-(3,5-di-t-butyl-4-hydroxy- 55
/i,/?'-Thiodiäthyl-bis-(3,5-di-t-butyl-4-hydroxy- 55
phenylacetat);
N,N-Bis-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-
N,N-Bis-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-
propionyloxyäthyl]-stearinsäureamid; 3,5-Di-t-butyI-4-hydroxybenzoesäure-
2-(2-stearoyloxyäthylthio)-äthylester; 60 l,2-Propylenglykol-bis-[3-(3,5-di-t-butyl-
4-hydroxyphenyl)-propionat]; Äthylenglykol-bis-[3-(3,5-di-t-butyl-4-hydroxy-
phenyl)-propionat];
Tetra-[methylen-3-(3,5-di-t-butyl-4-hydroxy- 65
Tetra-[methylen-3-(3,5-di-t-butyl-4-hydroxy- 65
phenyl)-propionat]-methan;
l,2,3-Butantriol-tris-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propionat].
l,2,3-Butantriol-tris-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propionat].
40
D. Reinphenolische Stabilisatoren
4,4'-Butyliden-bis-(5-t-butyl-4-hydroxy-
2-methylphenyl);
Bis-(5-t-butyl-4-hydroxy-2-methylphenyl)-
Bis-(5-t-butyl-4-hydroxy-2-methylphenyl)-
sulfid;
4,4'-Methylen-bis-(2,6-di-t-butylphenoI);
2,2'-Methylen-bis-[4-hydroxy-6-( 1 -methylcyclo-
2,2'-Methylen-bis-[4-hydroxy-6-( 1 -methylcyclo-
hexyl)-phenol];
2,6-Di-t-butylphenol;
2,6-Di-t-butylphenol;
l,l,3-Tris-(5-t-butyl-4-hydroxy-2-methylphenyl)-butan;
4,4'-Isopropyliden-bis-(2-t-butylphenol).
Es empfiehlt sich oft, die vorstehend genannten phenolischen Stabilisatoren mit noch anderen Zusatzstoffen
zu verwenden, wie UV-Absorbern, z. B. 2-Hydroxy-4-methoxybenzophenon, 2-(2'-Hydroxy-5'-methylDhenyl)-benztriazol
oder wie Phosphitverbindungen, z. B. Trioctylphosphit, Dilaurylphosphit, Tris-(nonylphenyl)-phosphit. Solche Mischungen aus
drei oder vier Komponenten besitzen Eigenschaften, die der Summe der Eigenschaften der Einzelkomponenten
weit überlegen sind.
Je nach der Art der zu stabilisierenden Kohlenwasserstoffe können ihnen häufig auch noch andere
Stoffe zugesetzt werden, so z. B. Mittel zur Herabsetzung des Fließpunktes, Korrosionsschutzmittel,
Metallchelierungsmittel, Antischaummittel, Ruß, Beschleuniger, Weichmacher, Farbstabilisatoren, Wärmestabilisatoren,
Farbstoffe.
DieAlkylmercaptomethylbernsteinsäurediester werden vorzugsweise in einer Konzentration von 0,005
bis etwa 10 Gewichtsprozent des gesamten Stoffgemischs, zusammen mit den vorstehend genannten
phenolischen Antioxydantien, verwendet. Sie sind besonders geeignet, um synthetische organische polymere
Substanzen, wie Polypropylen, Polyäthylen und Polystyrol vor Zersetzung während des Gebrauchs
und während der Herstellung — im Falle von Polypropylen beispielsweise während des Walzens
oder bei Polyäthylen während des Blasformens— zu schützen. Die erfindungsgemäßen Verbindungen
der Formel I besitzen zu den verschiedensten Kohlenwasserstoffen und deren Polymeren ausgezeichnete
Verträglichkeit mit geringer oder ohne Geruchsbildung.
Die Verbindungen der Formel I erhält man durch Umsetzen von Itaconsäure-anhydrid mit einem geeigneten
Alkohol in Gegenwart von p-Toluolsulfonsäure und anschließender überführung des entstandenen
Itaconsäurediesters mit einem Alkylmercaptan in Gegenwart von Natriummethylat in den Diester
einer Alkylmercaptomethylbernsteinsäure. Man kann aber auch Mercaptomethylbernsteinsäure mit einem
Alkohol verestern. Nach einem weiteren Herstellungsverfahren wird die Alkylmercaptomethylbernsteinsäure
mit einem geeigneten Alkohol zum gewünschten Diester umgesetzt.
Die folgenden Beispiele dienen der näheren Erläuterung der Erfindung und schränken diese nicht ein.
Prozente beziehen sich darin auf das Gewicht, und Gewichtsteile verhalten sich zu Volumteilen wie
Gramm zu Kubikzentimetern. Temperaturen sind in Grad Celsius angegeben.
Nicht stabilisiertes, gepulvertes, isotaktisches Polypropylen mit einem Molekulargewicht von ungefähr
Claims (2)
1. Verwendung von Diestern der Alkylmercaptomethylbernsteinsäure der allgemeinen Formel
I
II
R1-S-CH2-CH C-O-R2 (I)
CH2-C-O-R3
O
O
worin Ri eine Alkylgruppe mit 8 bis 18 Kohlenstoffatomen und Ra und R3 jeweils eine Alkylgruppe
mit 12 bis 18 Kohlenstoffatomen bedeuten, im Gemisch mit bekannten phenolischen Antioxydantien
zum Stabilisieren von mono- oder polymeren aliphatischen Kohlenwasserstoffen.
2. Verwendung nach Anspruch 1 zum Stabilisieren von Polypropylen.
In Betracht gezogene Druckschriften:
Belgische Patentschrift Nr. 637 443.
Belgische Patentschrift Nr. 637 443.
ein Versuchsbericht ausgelegt worden.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US37307864A | 1964-06-05 | 1964-06-05 | |
US462467A US3345327A (en) | 1964-06-05 | 1965-05-11 | Stabilization of propylene |
Publications (2)
Publication Number | Publication Date |
---|---|
DE1275060B true DE1275060B (de) | 1968-08-14 |
DE1275060C2 DE1275060C2 (de) | 1975-01-09 |
Family
ID=27006032
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1965G0043802 Expired DE1275060C2 (de) | 1964-06-05 | 1965-06-04 | Stabilisatorgemisch fuer mono- oder polymere kohlenwasserstoffe |
Country Status (7)
Country | Link |
---|---|
US (1) | US3345327A (de) |
BE (1) | BE664958A (de) |
CH (1) | CH449002A (de) |
DE (1) | DE1275060C2 (de) |
FR (1) | FR1437024A (de) |
GB (1) | GB1062804A (de) |
NL (1) | NL126798C (de) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4837335B1 (de) * | 1970-12-30 | 1973-11-10 | ||
JPS5138743B1 (de) * | 1971-04-05 | 1976-10-23 | ||
US3909493A (en) * | 1971-10-21 | 1975-09-30 | Goodrich Co B F | Aliphatic esters of carboxymethene- and carboxyethenethiosuccinic acid |
US4238575A (en) * | 1979-02-12 | 1980-12-09 | Ciba-Geigy Corporation | Stabilized compositions containing polymeric thiosynergists |
US4446264A (en) * | 1982-04-15 | 1984-05-01 | The Goodyear Tire & Rubber Company | Synergistic antioxidant mixtures |
US5523007A (en) * | 1987-07-01 | 1996-06-04 | Ciba-Geigy Corporation | Stabilized diesel engine oil |
EP0713867B1 (de) * | 1994-11-25 | 2000-02-16 | Shell Internationale Researchmaatschappij B.V. | Schmierölzusammensetzungen |
DE102005022845A1 (de) * | 2005-05-18 | 2006-11-23 | Fumapharm Ag | Thiobernsteinsäurederivate und deren Verwendung |
US10316265B2 (en) * | 2015-12-28 | 2019-06-11 | Exxonmobil Research And Engineering Company | Low viscosity low volatility lubricating oil base stocks and methods of use thereof |
US10233403B2 (en) | 2016-11-03 | 2019-03-19 | EXXONMOBiL RESEARCH AND ENGiNEERENG COMPANY | High viscosity index monomethyl ester lubricating oil base stocks and methods of making and use thereof |
US9976099B2 (en) | 2015-12-28 | 2018-05-22 | Exxonmobil Research And Engineering Company | Low viscosity low volatility lubricating oil base stocks and methods of use thereof |
US10077409B2 (en) | 2015-12-28 | 2018-09-18 | Exxonmobil Research And Engineering Company | Low viscosity low volatility lubricating oil base stocks and methods of use thereof |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE637443A (de) * | 1962-09-17 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2703811A (en) * | 1955-03-08 | Dibasic acid esters of glycols | ||
US2496798A (en) * | 1946-05-14 | 1950-02-07 | Texas Co | Rust-inhibiting lubricating composition |
GB699440A (en) * | 1948-12-29 | 1953-11-04 | Standard Oil Dev Co | Synthetic esters suitable as lubricants |
US2581514A (en) * | 1949-11-30 | 1952-01-08 | Standard Oil Co | Production of thiasuccinic acid derivatives |
US2846461A (en) * | 1955-02-21 | 1958-08-05 | Universal Oil Prod Co | Production of esters of dithiocarboxylic acids |
DE1217382B (de) * | 1960-04-11 | 1966-05-26 | Ethyl Corporation, New York, N. Y. (V. St. A.) | Stabilisieren von Motortreibstoffen, Schmierölen, oder -fetten auf Kohlenwasserstoffbasis oder von polymeren Kohlenwasserstoffen |
US3136748A (en) * | 1960-06-22 | 1964-06-09 | Fmc Corp | Sulfurized esters |
US3006945A (en) * | 1960-09-01 | 1961-10-31 | Ethyl Corp | Preparation of organic compounds |
US3247109A (en) * | 1962-04-23 | 1966-04-19 | Chevron Res | Lubricant compositions |
-
1965
- 1965-05-11 US US462467A patent/US3345327A/en not_active Expired - Lifetime
- 1965-05-26 CH CH740965A patent/CH449002A/de unknown
- 1965-06-04 NL NL6507169A patent/NL126798C/xx active
- 1965-06-04 GB GB23959/65A patent/GB1062804A/en not_active Expired
- 1965-06-04 DE DE1965G0043802 patent/DE1275060C2/de not_active Expired
- 1965-06-04 BE BE664958A patent/BE664958A/xx unknown
- 1965-06-05 FR FR19764A patent/FR1437024A/fr not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE637443A (de) * | 1962-09-17 |
Also Published As
Publication number | Publication date |
---|---|
NL6507169A (de) | 1965-12-06 |
DE1275060C2 (de) | 1975-01-09 |
BE664958A (de) | 1965-12-06 |
CH449002A (de) | 1967-12-31 |
US3345327A (en) | 1967-10-03 |
GB1062804A (en) | 1967-03-22 |
FR1437024A (fr) | 1966-04-29 |
NL126798C (de) | 1969-06-18 |
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