DE1270723B - Water-in-oil emulsion for lubrication purposes - Google Patents
Water-in-oil emulsion for lubrication purposesInfo
- Publication number
- DE1270723B DE1270723B DEP1270A DE1270723A DE1270723B DE 1270723 B DE1270723 B DE 1270723B DE P1270 A DEP1270 A DE P1270A DE 1270723 A DE1270723 A DE 1270723A DE 1270723 B DE1270723 B DE 1270723B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- water
- alkyl
- oil
- succinic acid
- 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.)
- Pending
Links
Classifications
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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
- C10M173/00—Lubricating compositions containing more than 10% water
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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- 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
- C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
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- C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
- C10M129/95—Esters
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
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- C10M167/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound, a non-macromolecular compound and a compound of unknown or incompletely defined constitution, each of these compounds being essential
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
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Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. Cl.:Int. Cl .:
ClOmClOm
Deutsche KL: 23 c-1/01 German KL: 23 c -1/01
Nummer: 1 270 723Number: 1 270 723
Aktenzeichen: P 12 70 723.2-43File number: P 12 70 723.2-43
Anmeldetag: 30. August 1962Filing date: August 30, 1962
Auslegetag: 20. Juni 1968Opening day: June 20, 1968
Emulsionen, insbesondere Wasser-in-Öl-Emulsionen, werden als Schmiermittel und ganz besonders als nicht brennbare Hydraulikflüssigkeiten verwendet. Zu diesem Zweck müssen die Emulsionen in einem weiten Bereich von Temperatur und Druck beständig sein. Vorzugsweise sollen sie auch nicht korrodierend wirken, reinigende sowie bakleriostatische bzw. bakterizide Eigenschaften besitzen und ferner den Reibungskoeffizienten sowie den Verschieb herabsetzen. Ein weiteres wichtiges Kennzeichen der Emulsionen, die insbesondere als Hydraulikflüssigkeiten verwendet werden, ist ihre Unbrennbarkeit. Es ist schwierig. Wasser-in-Öl-Emulsionen herzustellen, die den vorgenannten Anforderungen genügen. Emulsions, especially water-in-oil emulsions, are used as lubricants and are very special used as non-flammable hydraulic fluids. For this purpose, the emulsions must be in one be resistant to a wide range of temperature and pressure. They should also preferably not be corrosive act, have cleaning and bakleriostatic or bactericidal properties and also the Reduce the coefficient of friction and the displacement. Another important feature of the Emulsions, which are used in particular as hydraulic fluids, is their incombustibility. It's tough. To produce water-in-oil emulsions that meet the aforementioned requirements.
Ein Ziel der vorliegenden Erfindung ist es. beständige Wasser-in-Öl-Emulsionen zu schaffen, die als Schmiermittel und feuerbeständige Hydraulikflüssigkeiten geeignet sind.It is an object of the present invention. create persistent water-in-oil emulsions that act as Lubricants and fire-resistant hydraulic fluids are suitable.
Gegenstand der Erfindung ist somit eine Wasserin-öl-Emtilsion, bestehend aus 1 bis 80 Teilen Wasser. 20 bis 99 Teilen Mineralöl und 0,2 bis 10 Teilen entwederThe subject of the invention is thus a water-in-oil emtilsion, consisting of 1 to 80 parts of water. 20 to 99 parts of mineral oil and 0.2 to 10 parts of either
a) eines Alkali- oder Erdalkalimetallsalzes mit Ammoniak, einem Hydroxyalkylamin, Alkylen- 2S amin oder einem technischen Gemisch von Alkylenaminen einer Alkyl- oder Alkenylbernsteinsäure mit mindestens 50 Kohlenstoffatomen im Alkyl- bzw. Alkenylrest bzw. deren Chlorsulfonierungsprodukt odera) an alkali or alkaline earth metal salt with ammonia, a hydroxyalkylamine, alkylene 2S amine or a technical mixture of alkylene amines of an alkyl or alkenylsuccinic acid with at least 50 carbon atoms in the alkyl or alkenyl radical or its chlorosulfonation product or
b) eines Esters der Alkyl- oder Alkenylbernsteinsäure mit einem Hydroxyalkylamin oder einem teilweise acylierten, mehrwertigen Alkohol oderb) an ester of alkyl or alkenyl succinic acid with a hydroxyalkylamine or a partially acylated, polyhydric alcohol or
c) dem Amid. Imid oder Amidin der Alkyl- oder Alkenylbernsteinsäure.c) the amide. Imide or amidine of the alkyl or Alkenyl succinic acid.
Die Alkyl- bzw. Alkenylreste leiten sich ab von Erdölfraktionen mit hohem Molekulargewicht und Olefin-Polymeren, insbesondere Polymeren von Monoolefinen mit 2 bis etwa 30 Kohlenstoffatomen im Molekül. Besonders brauchbare Polymere sind diejenigen der ^-Olefine, wie Äthylen, Propylen. Biitylen-1, Isobutylen, Hexen-1. Octen-1, 2-Metliylhepten-1. 3-Cyclohexylbuten-l und 2-Methyl-5-propylhexen-1. Auch Polymere von Olefinen mit nicht endsländiger Doppelbindung sind geeignet. Beispiele für diese Olefine sind Buten-2, Penten-3 und Octen-4.The alkyl or alkenyl radicals are derived from petroleum fractions with a high molecular weight and Olefin polymers, particularly polymers of monoolefins having 2 to about 30 carbon atoms in the molecule. Particularly useful polymers are those of the ^ -olefins, such as ethylene, propylene. Biitylene-1, isobutylene, hexene-1. Octene-1,2-methylheptene-1. 3-cyclohexylbutene-1 and 2-methyl-5-propylhexene-1. Polymers of olefins with non-terminal double bonds are also suitable. Examples for these olefins are butene-2, pentene-3 and octene-4.
Zu den Polymeren gehören auch die Mischpolymerisate der Olefine, ζ. B. die vorgenannten, zusammen mit anderen copolymerisierbaren olefinisch ungesättigten Verbindungen, wie aromatische Olefine, cyclische Olefine und Polyolefine. Die relativen Wasser-in-öl-Emulsion für SchmierzweckeThe polymers also include the copolymers of olefins, ζ. B. the aforementioned together with other copolymerizable olefinically unsaturated compounds, such as aromatic olefins, cyclic olefins and polyolefins. The relative water-in-oil emulsion for lubrication purposes
Anmelder:Applicant:
The Lubrizol Corporation,The Lubrizol Corporation,
Cleveland, Ohio (V. St. A.)Cleveland, Ohio (V. St. A.)
Vertreter:Representative:
Dr. E. Jung und Dr. V. Vossius, Patentanwälte,Dr. E. Jung and Dr. V. Vossius, patent attorneys,
8000 München 23, Siegesstr. 268000 Munich 23, Siegesstr. 26th
Beanspruchte Priorität:Claimed priority:
V. St. v. Amerika vom 30. August 1961 (134 860), vom 20. April 1962 (188 947)V. St. v. America dated August 30, 1961 (134 860), April 20, 1962 (188 947)
Anteile der Monoolefine zu den anderen olefinischen Monomeren in den Mischpolymerisaten beeinflussen die Beständigkeit und die Wirksamkeit der davon abgeleiteten Bernsteinsäurederivate in den Emulsionen der Erfindung. So sollen die Mischpolymerisate im wesentlichen aliphatisch und im wesentlichen gesättigt sein, d. h.. sie sollen mindestens etwa 80"/«. vorzugsweise mindestens etwa 951Vo, auf das Gewicht bezogen, Einheiten aus den aliphatischen Monoolefinen und nicht mehr als etwa 50Zo ungesättigte Bindungen, bezogen auf die Gesamtzahl der Kohlenstoff-Kohlenstoff-Bindungen, enthalten.Proportions of the monoolefins to the other olefinic monomers in the copolymers influence the stability and the effectiveness of the succinic acid derivatives derived therefrom in the emulsions of the invention. The copolymers should be essentially aliphatic and essentially saturated, ie. they should contain at least about 80 "/". preferably at least about 95 1 L, based on the weight, units from the aliphatic monoolefins and no more unsaturated than about 5 0 Zo bonds based on the total number of carbon-carbon bonds.
Beispiele für deraitige Mischpolymerisate sind das Copolymerisat aus - auf das Gewicht bezogen — 95% Isobutylen und 5% Styrol, ein Terpolymerisat aus 98% Isobutylen. 1% Piperylen und 1% Chloiopren, ein Terpolymerisat aus 95% Isobutylen, 2% Buten-1 und 31Vn Hexen-1, ein Terpolymerisat aus 60% Isobutylen, 2011A, Penten-1 und 200A, Octan-1. ein Copolymerisat aus 80% Hexen-1 und 20'Vo Hepten-1. ein Terpolymerisat aus 90% Isobutylen, 2"/o Cyclohexen und 8" » Propylen sowie ein Copolymerisat aus SO"/» Äthylen und 20% Propylen.Examples of such copolymers are the copolymer of - based on weight - 95% isobutylene and 5% styrene, a terpolymer made of 98% isobutylene. 1% piperylene and 1% chloioprene, a terpolymer composed of 95% isobutylene, 2% butene-1 and 3 1 Vn hexene-1, a terpolymer composed of 60% isobutylene, 20 11 A, pentene-1 and 20 0 A, octane-1 . a copolymer of 80% hexene-1 and 20% heptene-1. a terpolymer of 90% isobutylene, 2 "/ o cyclohexene and 8" propylene and a copolymer of SO "/" ethylene and 20% propylene.
Bernsleinsäurederivate, bei denen sich der Alkyl- oder Alkenylrest von einem Olefin-Polymerisat mit einem Molekulargewicht von etwa 750 bis 5000 ableitet, werden bevorzugt; aber auch diejenigen aus Polymeren höheren Molekulargewichts, d. h. von etwa 10 000 bis etwa 100 000 oder darüber, sind ebenfalls brauchbar.Bernsleic acid derivatives, in which the alkyl or alkenyl radical derived from an olefin polymer with a molecular weight of about 750 to 5000, are preferred; but also those made from polymers of higher molecular weight, i.e. H. from about 10,000 to about 100,000 or more are also useful.
Die Alkyl- bzw. Alkenylreste können sich auch von Erdölfraktionen, z. B. Weißölen mit hohem Molekulargewicht und synthetischen Alkalien, wieThe alkyl or alkenyl radicals can also be derived from petroleum fractions, e.g. B. white oils with high Molecular weight and synthetic alkalis, such as
3 43 4
man sie durch Hydrieren von Olefinen hohen Mole- Sorbitandidecanoat, Sorbitantristearat, Sorbitandi-they are made by hydrogenating olefins of high mole- sorbitandidecanoate, sorbitan tristearate,
kulargewichts oder von Fetten erhält, ableiten. behenat, Erythritmonooleat, 1,1,1-Trimethylolpro-derived from gross weight or from fats. behenat, erythritol monooleate, 1,1,1-trimethylolpro-
Die Verfahren zur Herstellung der Polymerisate panmonomyristat, Pentaerythritdilinoleat, Ribit-The process for the preparation of the polymers panmonomyristat, pentaerythritol dilinoleate, ribitol
und der Mischpolymerisate, von denen sich die mono-(9,10-dichlorstearat) und Sorbitanmonooleat. Alkyl- bzw. Alkenylreste der Bernsteinsäurederivate 5 Die Ätherbindungen enthaltenden teilweise acy-and the copolymers, of which the mono- (9,10-dichlorostearate) and sorbitan monooleate. Alkyl or alkenyl radicals of the succinic acid derivatives 5 Some of the ether bonds contain acy-
ableiten, sind bekannt. lierten mehrwertigen Alkohole werden hergestellt.derive are known. Lated polyhydric alcohols are produced.
Die Alkyl- bzw. Alkenylbernsteinsäuren können indem man zunächst einen mehrwertigen AlkoholThe alkyl or alkenyl succinic acids can by first adding a polyhydric alcohol
nach bekannten Verfahren hergestellt werden, z. B. dehydratisiert und dann eine alkoholische Hydroxyl-be prepared by known methods, e.g. B. dehydrated and then an alcoholic hydroxyl
durch Umsetzen von Maleinsäureanhydrid mit einem gruppe acyliert oder indem man zuerst eine alko-Olefin hohen Molekulargewichts oder einem chlo- 10 holische Hydroxylgruppe acyliert und dann dieacylated by reacting maleic anhydride with a group or by first adding an alcohol-olefin high molecular weight or a chlo- 10 holic hydroxyl group and then the
rierten Kohlenwasserstoff, z. B. aus dem vorge- anderen Alkoholfunktionen dehydratisiert. Dierated hydrocarbon, e.g. B. dehydrated from the previous other alcohol function. the
nannten Olefin-Polymerisat. Die Reaktion wird Äthergruppen enthaltenden, teilweise acyliertencalled olefin polymer. The reaction is ether-containing, partially acylated
vorzugsweise bei etwa 100 bis 200 C durchgeführt, mehrwertigen Alkohole können auch durch Um-preferably carried out at about 100 to 200 C, polyhydric alcohols can also be converted
wobei man ein Alkenylbernsteinsäureanhydrid erhält. Setzung mit Epoxyden erhalten werden. Beispiele Die Alkenylgruppe kann zur Alkylgruppe hydriert 15 für diese Verbindungen sind Polyoxyäthylensorbitan-whereby an alkenyl succinic anhydride is obtained. Settlement can be obtained with epoxies. Examples The alkenyl group can be hydrogenated to the alkyl group 15 for these compounds are polyoxyethylene sorbitan
werden. Das Anhydrid kann durch Behandlung mit monooleat, Polyoxyäthylensorbitantristearat undwill. The anhydride can be treated with monooleate, polyoxyethylene sorbitan tristearate and
Wasser oder Wasserdampf zur entsprechenden freien Polyoxypropylensorbitandilinooleat.Water or steam to the corresponding free polyoxypropylene sorbitan dilinooleate.
Säure verseift werden. Die Amide, Imide und Amidine und die stickstoff-Acid saponified. The amides, imides and amidines and the nitrogenous
An Stelle der Olefine oder chlorierten Kohlen- haltigen Salze der Bernsteinsäuren leiten sich ab von Wasserstoffe können auch andere Kohlenwasserstoffe 20 Ammoniak, von den Hydroxyalkylaminen und denInstead of olefins or chlorinated carbon-containing salts of succinic acids are derived from Hydrocarbons can also include other hydrocarbons, including the hydroxyalkylamines and ammonia
verwendet werden, die einen aktivierenden polaren Alkylenaminen. Die Alkylenamine haben die allge-can be used, which have an activating polar alkyleneamine. The alkyleneamines have the general
Substituenten enthalten, d. h. einen Substituenten, meine FormelContain substituents, d. H. a substituent, my formula
der fähig ist, das Kohlenwasserstoffmolekül zur H MiAiWW isn Hwho is able to convert the hydrocarbon molecule to H MiAiWW isn H
Umsetzung mit Maleinsäure oder Maleinsäure- iNiAiKyien in,„πImplementation with maleic acid or maleic acid iNiAiKyien in, “π
anhydrid zu aktivieren. Zu solchen polaren Substi- 25 AA tuen ten gehören Sulfid-, Disulfid-, Nitro-, Mercapto-,to activate anhydride. To such polar substitutes 25 AA types include sulfide, disulfide, nitro, mercapto,
Brom-. Keton- und Aldehydreste. Beispiele für der- in der /; eine ganze Zahl vorzugsweise von unter 10 artige substituierte Kohlenwasserstoffe sind Poly- ist und A ein Wasserstoffatom oder einen Kohlenpropylensulfid, Di-polyisobutylendisulfid, nitriertes wasserstoffrest bedeutet und die Alkylengruppe vorMineralöl, Di-polyäthylensulfid und bromiertes Poly- 30 zugsweise eine niedere Alkylengruppe mit weniger äthylen. als etwa 8 Kohlenstoffatomen ist. Beispiele für dieBromine-. Ketone and aldehyde residues. Examples of the- in the /; an integer, preferably less than 10 like substituted hydrocarbons are poly and A is a hydrogen atom or a carbon propylene sulfide, Di-polyisobutylene disulfide, nitrated hydrogen radical means and the alkylene group before mineral oil, Di-polyethylene sulfide and brominated poly- 30 preferably have a lower alkylene group with less ethylene. than about 8 carbon atoms. Examples of the
Ein weiteres Verfahren zur Herstellung der Bern- Alkylenamine sind Methylenamine, Äthyienamine.Another process for the production of the amber alkylenamines are methylenamines, ethyienamines.
steinsäuren besteht in der Umsetzung von Itacon- Butylenamine. Propylenamine, Pentylenamine. Hexy-stinic acids consists in the conversion of itacon-butyleneamines. Propylene amines, pentylene amines. Hexy
säure mit einem Olefin oder einem polar-substi- lenamine. Heptylenamine, Octylenamine. sonstigeacid with an olefin or a polar-substituted amine. Heptyleneamines, octyleneamines. other
tuierten Kohlenwasserstoff in der Regel bei einer 35 Polymethylenamine und auch die cyclischen und dieusually used hydrocarbons in a 35 polymethylene amine and also the cyclic and the
Temperatur von etwa 100 bis 200 C. höheren Homologen dieser Amine, wie PiperazineTemperature of about 100 to 200 C. higher homologues of these amines, such as piperazines
Zu den Alkalimetall- und Erdalkalimetallsalzen und aminoalkylsubstituierte Piperazine. SpezielleTo the alkali metal and alkaline earth metal salts and aminoalkyl-substituted piperazines. Specific
der Bernsteinsäuren gehören vor allem die Natrium-, Beispiele sind Äthylendiamin. Triäthylentetramin.The succinic acids are mainly sodium, examples are ethylenediamine. Triethylenetetramine.
Kalium-, Magnesium-, Barium-, Calcium- und Stron- Propylendiamin, Dekamethylendiamin. Octamethy-Potassium, magnesium, barium, calcium and stron propylenediamine, decamethylenediamine. Octamethy-
tiumsalze. Man erhält sie z. B. durch Neutralisation 40 lendiamin. Di-(heptamethylen)-triamin. Tripropylen-tium salts. You get them z. B. by neutralization 40 lenediamine. Di (heptamethylene) triamine. Tripropylene
der Bernsteinsäure mit dem entsprechenden Metall- tetramin. Tetraäthylenpentamin. Trimethylendiamin.succinic acid with the corresponding metal tetramine. Tetraethylene pentamine. Trimethylenediamine.
oxyd. -hydroxyd, -carbonat, -bicarbonat. -mercaptid. Pentaäthylenhexamin. Di - (trimethylen) - triamin.oxide. hydroxide, carbonate, bicarbonate. -mercaptid. Pentaethylene hexamine. Di (trimethylene) triamine.
-alkoholat oder-phenolat. 2-Heptyl-3-(2-aminopropyl)-imidazolin, 4-Methyl-alcoholate or phenolate. 2-heptyl-3- (2-aminopropyl) -imidazoline, 4-methyl-
Die Alkyl- bzw. Alkenylbernsteinsäureester der imidazolin. 1.3-Bis-(2-Aminoäthyl)-imidazolin. Pyri-The alkyl or alkenyl succinic acid esters of imidazoline. 1.3-bis (2-aminoethyl) imidazoline. Pyri-
Hydroxylalkylamine und teilweise acylierten mehr-45 midin. 1 - (2 - Aminopropyl) - piperazin. 1.4 - Bis-Hydroxylalkylamines and partially acylated more-45 midin. 1 - (2 - aminopropyl) piperazine. 1.4 - to
wertigen Alkohole werden in üblicher Weise durch (2-aminoäthyl)-piperazin und 2-Methyl-l-(2-amino-valent alcohols are in the usual way by (2-aminoethyl) piperazine and 2-methyl-l- (2-amino-
Veresterung der Bernsteinsäure oder ihres Anhydrids butyD-piperazin. Auch höhere Homologe, wie manEsterification of succinic acid or its anhydride butyD-piperazine. Even higher homologues, how to
mit der entsprechenden Hydroxyverbindung her- sie durch die Kondensation von zwei oder mehrerenwith the corresponding hydroxy compound produced by the condensation of two or more
gestellt. Man kann auch einen Bernsteinsäureester der vorgenannten Alkylenamine erhält, sind brauch-posed. You can also obtain a succinic acid ester of the aforementioned alkyleneamines, are useful
eines verhältnismäßig flüchtigen Alkohols oder 50 bar.a relatively volatile alcohol or 50 bar.
Phenols mit dem Hydroxyalkylamin oder teilweise Die Äthyienamine sind ganz besonders geeignet,Phenol with the hydroxyalkylamine or partially The Ethyienamines are particularly suitable,
acylierten mehrwertigen Alkohol umestern. Sie sind in dem Kapitel »Ethylene Amines« in dertransesterify acylated polyhydric alcohol. They are in the chapter "Ethylene Amines" in the
Zu den Hydroxyalkylaminen gehören die Mono-. »Encyclopedia of Chemical Technology« von K i r k Di- und Trihydroxyalkylamine. insbesondere die- und Othmer. Bd. 5, S. 898 bis 905. Verlag jenigen mit einem niederen Alkylrest mit weniger 55 Interscience Publishers, New York (1950). beschrieals etwa 6 Kohlenstoffatomen, z. B. Äthanolamin, ben. Derartige Verbindungen werden durch Um-Diäthanolamin, Triäthanolamin, N-(2-Oxy-l-butyl)- setzen eines Alkylendichlorids mit Ammoniak herdodecylamin, N - (3 - Oxy - 1 - propyl) - octylamin, gestellt, wobei man komplexe Gemische von Alky-N,N-Bis-(2-oxy-l-propyl)-oleylamin. N-(2-Oxy- lenaminen einschließlich cyclischer Kondensationsäthyl)-cyclohexylamin und N,N-Bis-(2-oxyäthyD- 60 produkte, z. B. der Piperazine, erhält. Diese Gebehenylamin. Die teilweise acylierten mehrwertigen mische werden zur Herstellung der Bernsteinsäure-Alkohole enthalten vorzugsweise 3 bis 6 alkoholische derivate verwendet. Andererseits kann man auch Hydroxylgruppen, von denen mindestens eine, aber bei Verwendung reiner Alkylenamine brauchbare nicht alle, mit einer aliphatischen Carbonsäure mit Produkte erhalten. Ein besonders geeignetes Alkyetwa 8 bis 30 Kohlenstoffatomen acyliert ist. Diese 65 lenamin ist ein Gemisch von Äthylenaminen. das Verbindungen können in ihrem Molekül auch Äther- durch Umsetzen von Äthylendichlorid mit Ammobindungen aufweisen. Beispiele sind Glycerin- niak erhalten wird; es hat eine Zusammensetzung, monooleat, Giyeerindistearat, Sorbitanmonostearat, die derjenigen von Tetraäthylenpentamin entspricht.The hydroxyalkylamines include the mono-. "Encyclopedia of Chemical Technology" by K irk Di- and Trihydroxyalkylamine. especially die- and othmer. Vol. 5, pp. 898 to 905. Publisher those with a lower alkyl radical with less 55 Interscience Publishers, New York (1950). described as about 6 carbon atoms, e.g. B. ethanolamine, ben. Such compounds are made by Um-diethanolamine, triethanolamine, N- (2-oxy-l-butyl) - put an alkylene dichloride with ammonia herdodecylamine, N - (3 - oxy - 1 - propyl) - octylamine, with complex mixtures of Alky-N, N-bis (2-oxy-1-propyl) oleylamine. N- (2-oxylenamines including cyclic condensation ethyl) -cyclohexylamine and N, N-bis- (2-oxyäthyD- 60 products, for example the piperazines, are obtained. These behenylamine. The partially acylated polyvalent mixtures are used to produce the Succinic acid alcohols preferably contain 3 to 6 alcoholic derivatives.On the other hand, hydroxyl groups, of which at least one, but not all of which are useful when using pure alkylene amines, can be obtained with an aliphatic carboxylic acid with products. A particularly suitable alkyl is acylated with about 8 to 30 carbon atoms . This lenamin is a mixture of ethylene amines. The compounds can also have ether in their molecule by reacting ethylene dichloride with ammo bonds. Examples are glycerin niac is obtained; it has a composition monooleate, giyeerindistearate, sorbitan monostearate, that of tetraethylene pentamine is equivalent to.
Hydroxyalkylsubstituierte Alkylenamine, d. h. Alkylenamine mit einem oder mehreren Hydroxyalkylresten an den Stickstoffatomen, sind ebenfalls geeignet. Die hydroxyalkylsubstituierten Alkylenamine enthalten vorzugsweise eine niedere Alkylgruppe mit weniger als etwa 6 Kohlenstoffatomen. Spezielle Beispiele sind N-(2-Oxyäthyl)-äthylendiamin. N.N'-Bis-(2-oxyäthyl)-äthylenamin, l-(2-OxyäthyD-piperazin. mono-oxypropyl-siibstituiertes Diäthylentriamin, 1.4 - Bis - (2 - oxypropyl) - piperazin. dioxypropyl-substituiertes Tetraäthylenpentamin. N-(3-Oxypropyl)-tetramethylen-diamin und 2-Heptadecyl-l-(2-oxyäthyl)-imidazolin. Hydroxyalkyl substituted alkyleneamines, d. H. Alkylenamines with one or more hydroxyalkyl radicals on the nitrogen atoms are also suitable. The hydroxyalkyl-substituted alkylene amines preferably contain a lower alkyl group having less than about 6 carbon atoms. Specific examples are N- (2-oxyethyl) ethylenediamine. N.N'-bis (2-oxyethyl) -ethylenamine, l- (2-oxyäthyD-piperazine. mono-oxypropyl-substituted diethylenetriamine, 1.4 - bis (2 - oxypropyl) piperazine. dioxypropyl-substituted tetraethylene pentamine. N- (3-oxypropyl) -tetramethylene-diamine and 2-heptadecyl-1- (2-oxyethyl) -imidazoline.
Höhere Homologe, wie man sie durch Kondensation der vorgenannten Alkylenamine oder hydroxyalkyl-substituierten Alkylenamine über Aminogruppen oder Hydroxylgruppen erhält, sind ebenfalls brauchbar. Die Kondensation über Aminogruppen führt zu einem höheren Amin unter Abspaltung von Ammoniak, die Kondensation über Hydroxylgruppen zu Produkten mit Ätherbindungen unter Abspaltung von Wasser.Higher homologs, such as those obtained by condensation of the aforementioned alkyleneamines or hydroxyalkyl-substituted ones Alkylenamines obtained via amino groups or hydroxyl groups are also available useful. The condensation via amino groups leads to a higher amine with elimination of Ammonia, the condensation via hydroxyl groups to products with ether bonds with splitting off of water.
Die Amide, Imide, Amidine und die entsprechenden stickstoffhaltigen Salze der Bernsteinsäuren werden hergestellt durch Umsetzen z. B. eines Bernsteinsäureanhydrids mit Ammoniak oder einem der obenerwähnten Amine. Je nach der Reaktionstemperatiir und der Art des verwendeten Amins können als Produkte Amide, Imide, Imidazoline, Salze oder auch ein Gemisch solcher Verbindungen erhalten werden. Auch können die von einem Alkylenamin abgeleiteten Amidine cyclische Amidine sein, wie die Imidazoline. Die Bildung einiger dieser Bernsteinsäurederivate wird durch die folgenden Gleichungen erläutert.The amides, imides, amidines and the corresponding nitrogenous salts of succinic acids are made by converting z. B. a succinic anhydride with ammonia or one of the the amines mentioned above. Depending on the reaction temperature and the type of amine used, obtained as products amides, imides, imidazolines, salts or a mixture of such compounds will. The amidines derived from an alkyleneamine can also be cyclic amidines, such as the imidazolines. The formation of some of these succinic acid derivatives is given by the following equations explained.
R-CH — CR-CH - C
CH, — CCH, - C
IlIl
R — CH CH, R - CH CH,
O CO C.
O OO O
j!j!
R-CH — C
CH, — CR-CH - C
CH, - C
■ι■ ι
R-CH-CH, R-CH-CH,
O -CO -C
O + H,N —GH, —NH,O + H, N —GH, —NH,
O + H2N — C2H4 — NH2 -O + H 2 N - C 2 H 4 - NH 2 -
-> R-CH — C — N — C2H4NH2 -> R-CH-C-N-C 2 H 4 NH 2
CH, — C — N — GH4 — NH,CH, - C - N - GH 4 - NH,
ii Iii I
O HO H
N-GH4-NH,N-GH 4 -NH,
O + H2N-C2H4-NH2 O + H 2 NC 2 H 4 -NH 2
R-CH — C — Ο"— HN; — GH4 — NH,R-CH - C - Ο "- HN ; - GH 4 - NH,
CH, — C — N — C2H4 — NH2 CH, - C - N - C 2 H 4 - NH 2
: j: j
O HO H
; N-CH2 ; N-CH 2
O + H2N-C2H4-NH,O + H 2 NC 2 H 4 -NH,
— H, ♦ R-CH — C -H, ♦ R-CH -C
C rl? C_-C rl? C_-
R ist der Alkyl- bzw: Alkenylrest. R is the alkyl or alkenyl radical.
Wenn ein tertiäres Amin verwendet wird, ist das Produkt ein Salz. Ferner wird das Produkt bei niedriger Reaktionstemperatur, beispielsweise unter etwa 60 C, vorwiegend das Salz enthalten. Solche Salze können durch Erhitzen auf über 80 C in Produkte mit vorwiegend Amid-, Imid- und Amidinbindungen umgewandelt werden. Die Verwendung eines Lösungsmittels, wie Benzol, Toluol, Benzin, Mineralöl, Xylol oder η-Hexan ist bei der Umsetzung oft erwünscht, um die Reaktionstemperatur leichter regeln zu können.If a tertiary amine is used, the product is a salt. Furthermore, the product is at low reaction temperature, for example below about 60 C, predominantly contain the salt. Such When heated to over 80 C, salts can be converted into products with predominantly amide, imide and amidine bonds being transformed. The use of a solvent such as benzene, toluene, gasoline, Mineral oil, xylene or η-hexane is often desirable in the reaction to make the reaction temperature easier to be able to regulate.
Das Mengenverhältnis von Bernsteinsäure zu Amin wird in der Regel so bemessen, daß mindestens etwa die Hälfte der stöchiometrisch äquivalenten Menge des Amins je Äquivalent Bernsteinsäure verwendet wird. Das Äquivalentgewicht des Amins berechnet sich aus der Anzahl der Aminogruppen, das Äquivalentgewicht der Bernsteinsäure ist gleich dem halben Molekulargewicht.The quantitative ratio of succinic acid to amine is usually calculated so that at least about half of the stoichiometrically equivalent amount of the amine per equivalent of succinic acid is used will. The equivalent weight of the amine is calculated from the number of amino groups, the equivalent weight of succinic acid is equal to half the molecular weight.
In den meisten Fällen beträgt die bevorzugte Menge des Amins etwa 1 bis 2 Äquivalente je Äquivalent Bernsteinsäure, obwohl anscheinend die obere Grenze für die gewünschte Reaktion allein durch das stöchiometrische Mengenverhältnis bestimmt wird.In most cases the preferred amount of the amine is about 1 to 2 equivalents per equivalent Succinic acid, although apparently the upper limit for the desired reaction by itself the stoichiometric quantity ratio is determined.
Man kann die Ester, Amide, Imide oder Amidine der Alkyl- bzw. Alkenylbernsteinsäure auch aus Bernsteinsäurehalogeniden, -imiden oder -estern erhalten. Zum Beispiel wird das Amid von Äthylendiamin auch durch Erhitzen eines Gemisches von Äthylendiamin mit dem Dimethylester der entsprechenden Bernsteinsäure oder dem Dihalogenid erhalten.The esters, amides, imides or amidines of alkyl or alkenyl succinic acid can also be selected from Obtain succinic acid halides, imides or esters. For example, the amide is made from ethylenediamine also by heating a mixture of ethylenediamine with the dimethyl ester of the corresponding Obtained succinic acid or the dihalide.
Nachstehend werden Vorschriften zur Herstellung der Bernsteinsäurederivate angegeben, die für die Wasser-in-Öl-Emulsionen der Erfindung verwendet werden können. Teile beziehen sich auf das Gewicht, wenn nichts anderes angegeben ist.Instructions for the preparation of the succinic acid derivatives are given below, which are used for the Water-in-oil emulsions of the invention can be used. Parts are by weight, unless otherwise stated.
A. Ein Polyisobutenylbernsteinsäureanhydrid wird durch Umsetzen eines chlorierten Polyisobutylene mit Maleinsäureanhydrid bei 200 C hergestellt. Das chlorierte Polyisobutylen wurde erhalten durch Behandeln eines Polyisobutylene mit einem durchschnittlichen Molekulargewicht von 1000 mit Chlor bei 104 bis 110 C, bis der Chlorgehalt 4,3% erreicht hat. Das Polyisobutenylbernsteinsäureanhydrid hat eine Säurezahl von 109; das Äquivalentgewicht beträgt 514.A. A polyisobutenyl succinic anhydride is made by reacting a chlorinated polyisobutylene made with maleic anhydride at 200 C. The chlorinated polyisobutylene was obtained by Treating a polyisobutylene having an average molecular weight of 1000 with chlorine at 104 to 110 C until the chlorine content has reached 4.3%. The polyisobutenyl succinic anhydride has an acid number of 109; the equivalent weight is 514.
Im Verlauf von 2 Stunden versetzt man ein Gemisch aus 1028 Teilen (2 Äquivalente) dieses Polyisobutenylbernsteinsäureanhydrids und 815 Teilen Mineralöl bei 80 C mit 210 Teilen (2 Äquivalente) Diäthanolamin. Das Gemisch wird dann auf 150 bis 155 C erhitzt und 7 Stunden mit Stickstoff geblasen. Das Produkt hat einen Stickstoffgehalt von 1.4%.A mixture of 1028 parts (2 equivalents) of this polyisobutenylsuccinic anhydride is added over a period of 2 hours and 815 parts of mineral oil at 80 C with 210 parts (2 equivalents) of diethanolamine. The mixture is then set to 150 Heated to 155 C and blown with nitrogen for 7 hours. The product has a nitrogen content of 1.4%.
B. Ein Gemisch aus 1000 Teilen (1,94 Äquivalente) des Polyisobutenylbernsteinsäureanhydrids nach A und 848 Teilen Mineralöl wird auf 60 C erhitzt und im Verlauf von 2 Stunden tropfenweise mit 289 Teilen (1,94 Äquivalente) Triäthanolamin versetzt. Das Gemisch wird auf 150 C erhitzt und 17 Stunden bei dieser Temperatur mit Stickstoff geblasen. Der Rückstand hat einen Stickstoffgehalt von 1,3% und 2,8"A) Hydroxylgruppen.B. A mixture of 1000 parts (1.94 equivalents) of the polyisobutenyl succinic anhydride according to A. and 848 parts of mineral oil are heated to 60 ° C. and added dropwise over the course of 2 hours 289 parts (1.94 equivalents) of triethanolamine are added. The mixture is heated to 150.degree. C. and Blown with nitrogen at this temperature for 17 hours. The residue has a nitrogen content of 1.3% and 2.8 "A) hydroxyl groups.
C. Ein Gemisch aus 300 Teilen des Polyisobutenylbernsteinsäureanhydrids nach A und 160 Teilen Mineralöl wird auf 65 bis 95 C erhitzt und mit einer äquivalenten Menge (25 Teile) eines technischen Äthylenamingemisches mit einer dem Tetraäthylenpentamin entsprechenden durchschnittlichen Zusammensetzung versetzt. Das Gemisch wird dann auf 150 C erhitzt und mit Stickstoff geblasen, um das bei der Reaktion gebildete Wasser abzudampfen. Der Rückstand wird mit 79 Teilen Mineralöl verdünnt; diese Lösung hat einen Stickstoffgehalt von 1,6%.C. A mixture of 300 parts of the polyisobutenyl succinic anhydride according to A and 160 parts of mineral oil is heated to 65 to 95 C and with an equivalent amount (25 parts) of a technical Ethylene amine mixture with an average composition corresponding to that of tetraethylene pentamine offset. The mixture is then heated to 150 ° C. and blown with nitrogen in order to to evaporate the water formed in the reaction. The residue is diluted with 79 parts of mineral oil; this solution has a nitrogen content of 1.6%.
D. Ein Gemisch aus 514 Teilen (1 Äquivalent) des Polyisobutenylbernsteinsäureanhydrids nach A. 354 Teilen Mineralöl und 9 Teilen Wasser wird 1 Stunde auf 100 bis 105 C erhitzt, um die freie Säure zu bilden. Das Gemisch wird dann auf 60 C abgekühlt und wasserfreies Ammoniak eingeleitet, bis 17 Teile (1 Äquivalent) Ammoniak aufgenommen sind. Das Reaktionsgemisch wird schließlich 1 Stunde auf 90 C erhitzt; der Rückstand hat einen Stickstoffgehalt von 1.40I).D. A mixture of 514 parts (1 equivalent) of the polyisobutenylsuccinic anhydride according to A. 354 parts of mineral oil and 9 parts of water is heated to 100 to 105 ° C. for 1 hour in order to form the free acid. The mixture is then cooled to 60 ° C. and anhydrous ammonia is passed in until 17 parts (1 equivalent) of ammonia have been absorbed. The reaction mixture is finally heated to 90 ° C. for 1 hour; the residue has a nitrogen content of 1.4 0 I).
E. Ein Gemisch aus 1188 Teilen (2,12 Äquivalente) des Polyisobutenylbernsteinsäureanhydrids nach A und 338 Teilen Mineralöl wird auf 80 C erhitzt und mit wasserfreiem Ammoniak behandelt, bis 44 Teile (2,6 Äquivalente) Ammoniak aufgenommen sind. Das Gemisch wird dann bei 80 C 4'ί Stunden gerührt und dann im Verlauf von 3 Stunden auf 140 C erhitzt. Danach wird das Gemisch 2 Stunden bei 140 bis 150 C mit Stickstoff geblasen und schließlich filtriert. Das Filtrat hat einen Stickstoffgehalt von 0.98%.E. A mixture of 1188 parts (2.12 equivalents) of the polyisobutenyl succinic anhydride according to A. and 338 parts of mineral oil is heated to 80 C and treated with anhydrous ammonia, up to 44 parts (2.6 equivalents) of ammonia are added. The mixture is then at 80 ° C. for 4 hours stirred and then heated to 140 ° C. over the course of 3 hours. After that, the mixture is 2 hours Blown with nitrogen at 140 to 150 C and finally filtered. The filtrate has a nitrogen content of 0.98%.
F. Ein Gemisch aus 1400 Teilen des Produkts nach E und 1080 Teilen Mineralöl wird auf 160 bis 170 C erhitzt und mit 7 Teilen Natriummethylat versetzt. Anschließend werden 220 Teile (5 Äquivalente) Äthylenoxyd unter die Oberfläche der Flüssigkeit eingeleitet. Das Gemisch wird dann auf 170 C 3 Torr erhitzt; der Rückstand hat einen Stickstoffgehalt von 0,58" ».F. A mixture of 1400 parts of the product according to E and 1080 parts of mineral oil is made to 160 to Heated at 170 ° C. and mixed with 7 parts of sodium methylate. Then 220 parts (5 equivalents) Ethylene oxide introduced under the surface of the liquid. The mixture is then on 170 C 3 torr heated; the residue has a nitrogen content of 0.58 "».
G. Ein Gemisch aus 770 Teilen (1,5 Äquivalente) des Polyisobutenylbernsteinsäureanhydrids nach A. 126 Teilen (1.5 Äquivalente) Sorbitanmonooleat. 588 Teilen Mineralöl, 9 Teilen p-Toluolsulfonsäuremonohydrat und 500 Volumteilen Xylol wird unter Rückfluß 12 Stunden auf 140 C erhitzt und das Reaktionswasser abgetrennt. Nach dem Abkühlen wird das Reaktionsgemisch mit Wasser gewaschen und durch Erhitzen auf 150 C 20 Torr getrocknet; der Rückstand hat eine Säurezahl von 68.G. A mixture of 770 parts (1.5 equivalents) of the polyisobutenyl succinic anhydride according to A. 126 parts (1.5 equivalents) of sorbitan monooleate. 588 parts of mineral oil, 9 parts of p-toluenesulfonic acid monohydrate and 500 parts by volume of xylene is refluxed for 12 hours at 140 C and that Separated water of reaction. After cooling, the reaction mixture is washed with water and dried by heating to 150 C 20 torr; the residue has an acid number of 68.
H. Ein Gemisch aus 514 Teilen (1 Äquivalent) des Polyisobutenylbernsteinsäureanhydrids nach A. 234 Teilen (1 Äquivalent) Polyoxyäthylensorbitanmonooleat, 492 Teilen Mineralöl, 7 Teilen p-Toluolsulfonsäuremonohydrat und 500 Volumteilen Xylol wird 10 Stunden unter Rückfluß erhitzt und das Reaktionswasser abgetrennt. Nach dem Abkühlen wird das Gemisch mit Wasser gewaschen und durch Erhitzen auf 150 C'20 Torr getrocknet; der Rückstand hat eine Verseifungszahl von 53.H. A mixture of 514 parts (1 equivalent) of the polyisobutenylsuccinic anhydride according to A. 234 parts (1 equivalent) of polyoxyethylene sorbitan monooleate, 492 parts of mineral oil, 7 parts of p-toluenesulfonic acid monohydrate and 500 parts by volume of xylene is refluxed for 10 hours and the water of reaction is separated off. After cooling down the mixture is washed with water and dried by heating to 150 C'20 Torr; the residue has a saponification number of 53.
I. Ein Gemisch aus 514 Teilen (1 Äquivalent) des Polyisobutenylbernsteinsäureanhydrids nach A und 390 Teilen Mineralöl wird auf 50 C erhitzt und im Verlauf von 2 Stunden mit 61 Teilen Chlorsulfonsäure versetzt. Bei der exotherm verlaufenden Reaktion wird Chlorwasserstoff entwickelt. Das Gemisch wird 1 Stunde bei 60 C mit Stickstoff geblasen, um restlichen Chlorwasserstoff zu entfernen. Anschließend werden bei 60 bis 80 C im Verlauf von 30 Minuten 120 Teile 5()%ige Natronlauge eingetragen.I. A mixture of 514 parts (1 equivalent) of the polyisobutenylsuccinic anhydride according to A and 390 parts of mineral oil are heated to 50 ° C. and over the course of 2 hours with 61 parts of chlorosulfonic acid offset. During the exothermic reaction, hydrogen chloride is evolved. The mixture is blown with nitrogen for 1 hour at 60 C to remove residual hydrogen chloride. Afterward 120 parts of 5% strength sodium hydroxide solution are introduced at 60 to 80 ° C. in the course of 30 minutes.
Danach werden 511 Teile Mineralöl zugegeben, und das Guniscli wird auf 110 C erhitzt und das Wasser entfernt. Hierauf wird das Reaktionsgemisch auf 200 C erhitzt und 5 Stunden mit Stickstoff geblasen. Danach wird das Gemisch filtriert. Das Filtrat hat einen Natriumgehalt von 1.99"/i) und einen Schwefelgehalt von 2.14''(].Then 511 parts of mineral oil are added, and the Guniscli is heated to 110 C and the water removed. The reaction mixture is then heated to 200 ° C. and blown with nitrogen for 5 hours. The mixture is then filtered. The filtrate has a sodium content of 1.99 "/ i) and a sulfur content from 2.14 '' (].
J. Das Ve -fahren \on C wird unter Verwendung von 1.5 Äquivalenten (38 Teilen) des technischen Äthylenamingeniisches wiederholt. Das Produkt hat einen Stickstoffgehalt von 2.11Vo.J. The process of C is repeated using 1.5 equivalents (38 parts) of the technical ethylene amine chemical. The product has a nitrogen content of 2.1 1 vol.
Für die Wasser-in-öl-Emuhion der Erfindung kann als öl ein flüssiger Kohlenwasserstoff mit einer Viskosität von 50 SUS (Sayboll-Uiiiversal-Sekunden) bei 38 C bis 200 SUS bei 99 C verwendet werden. Mineralöle mit Schmierviskositäten (z. B. SAE 5-90) sind besonders vorteilhaft. Auch ein Gemisch von ölen aus verschiedenen Quellen ist brauchbar. Ein derartiges Gemisch kann z. B. aus Mineralölen, pflanzlichen ölen, tierischen ölen sowie aus synthetischen ölen z. B. des Silicon-, Polyolefin- und Polyeslertyps hergestellt werden.For the water-in-oil emulsion of the invention can as an oil a liquid hydrocarbon with a Viscosity of 50 SUS (Sayboll Universal Seconds) at 38 C to 200 SUS at 99 C can be used. Mineral oils with lubricating viscosities (e.g. SAE 5-90) are particularly advantageous. Also a mixture of Oil from various sources is useful. Such a mixture can e.g. B. from mineral oils, vegetable oils, animal oils and synthetic oils oil z. B. of the silicone, polyolefin and polyester type.
Die Wasser-in-Öl-Emulsionen der Erfindung mit den günstigsten Eigenschaften enthalten 30 bis 50 Teile Wasser und 50 bis 70 Teile öl. Die Wasserin-ÖI-Fmulsionen. die als nicht brennbare Hydraulikflüssigkeiten bestimmt sind, müssen mindestens etwa 30" ο Wasser enthalten. Die Konzentration des Beinsteinsäurederivats in den Emulsionen beträgt vorzugsweise 1 bis 5 Teile je 100 Teile der Wassei-30 in-öl-Emulsion. Die Hauptfunktion des Bernsteinsäurederivals ist die eines Emulgators, obwohl es der Emulsion auch reinigende Eigenschaften verleiht.The water-in-oil emulsions of the invention with the most favorable properties contain from 30 to 50 parts of water and 50 to 70 parts of oil. The water-in-oil emulsions. which are intended as non-flammable hydraulic fluids must contain at least about 30 "ο water. The concentration of the The succinic acid derivative in the emulsions is preferably 1 to 5 parts per 100 parts of the water content in-oil emulsion. The main function of the succinic acid derivative is that of an emulsifier, although it also gives the emulsion cleaning properties.
Die Emulsionen können einfach durch Vermischen von Wasser mit öl und dem Bernsteinsäurederivat und sonstiger erwünschter Bestandteile in einem Homogenisator oder einer anderen Mischvorrichtung hergestellt werden. Ein Iiliit/en der Emulsion während oder 11; ch ihrer Herstellung ist nicht notwendig Die Reihenfolge des Mischens der Bestand-40 teile isi ohne Bedeutung. Es ist jedoch zweckmäßig, zunächst ein ölkonzentiat mit etwa 50 bis 95 !eilen der öllöslichen Bestandteile und etwa ^ bis 50 Ieilen öl hei zustellen und dann das Konzentrat mit Wassei in den entsprechenden Mengen zu emulgieren. Dies kann vom Verbraucher vorgenommen werden.The emulsions can be made simply by mixing water with oil and the succinic acid derivative and other desired ingredients in a homogenizer or other mixing device getting produced. A part of the emulsion during or 11; ch their preparation is not necessary The order of mixing the stock 40 share isi without meaning. However, it is advisable to first use an oil concentrate of around 50 to 95% of the oil-soluble constituents and about ^ to 50 parts Heat the oil and then add the concentrate with water to emulsify in the appropriate quantities. This can be done by the consumer.
Weiter können den beanspruchten Emulsionen andere übliche Schmierölzusätze. /. B. Stabilisaloren. Hochdruckzusätze. Rostinhibitoren. Emulgatoren. Bakterizide und Antioxydationsmittel zugeselzl wer den.Other customary lubricating oil additives can also be added to the claimed emulsions. /. B. Stabilizers. High pressure additives. Rust inhibitors. Emulsifiers. Bactericides and antioxidants are added.
( ILWK lltslOllo(ILWK lltslOllo
Produkt von B 950Product of B 950
Sojabohnenlecithin ... 190Soybean Lecithin ... 190
terl.-C'ii 1 i-Alkyl-prim.-aminterl-C'ii 1 i-alkyl-prim.-amine
(Molgewicht 191) 63(Molecular weight 191) 63
Zinksalz der Di-isooctyldithio-Zinc salt of the di-isooctyldithio-
phosphorsäure 317 (,υ phosphoric acid 317 (, υ
Mineralschmieröl SAE 5 30160Mineral lubricating oil SAE 5 30160
Schauminhibitor 0.75Foam inhibitor 0.75
Wasser 24000Water 24000
Produkt von C Product of C
Sojabohnenlecithin Soybean lecithin
I aurvl-diälhanolamin I aurvl-dialhanolamine
(icwahlsloilo 360
72
24(icwahlsloilo 360
72
24
Chloriertes Eikosanwachs Gewk-htstcChlorinated eikosan wax Gewk-htstc
(501V,, Chlor) 24(50 1 V ,, chlorine) 24
Mineralschmieröl SAE 5 11520Mineral lubricating oil SAE 5 11520
Schauminhibitor 0.30Foam inhibitor 0.30
Wasser 8000Water 8000
Produkt von .1 Product of .1
Sojabohnenlecitliin Soybean lecithin
Laurvl-diäthanolamin
Chloiiertes EikosanwachsLaurvl diethanolamine
Chlorinated eikosan wax
(50> Chlor) (50> chlorine)
Mineralschmieröl SAE 5 .
Wasser Mineral lubricating oil SAE 5.
water
Produkt von C Product of C
N-tert.-Nonylacrylamid...
Lauryl-diäthanolamin
Chloriertes EikosanwachsN-tert-nonylacrylamide ...
Lauryl diethanolamine
Chlorinated eikosan wax
(501Vo Chlor) (50 1 Vo chlorine)
Mineralschmieröl SAE 20Mineral lubricating oil SAE 20
Schauminhibitor Foam inhibitor
Wasser water
CiewiclilsRik· IH 3.6CiewiclilsRik IH 3.6
1.21.2
5"( 0 4(>05 "(0 4 (> 0
Gewiilit 'viii· 30.0 3 6 1.2Gewiilit 'viii · 30.0 3 6 1.2
1.2 564.01.2 564.0
COl 5 400.0COl 5 400.0
Gewichlstcik 9.0 1.8Weight 9.0 1.8
Produkt von G Product of G
Sojabohnenlecithin Soybean lecithin
tert.-Cii 1 l-Alkyl-prim.-amintert-Cii 1 l-alkyl-primary amine
(Molgewicht 191) 0.6(Molecular weight 191) 0.6
Zinksalz der Di-isooctyldithio-Zinc salt of the di-isooctyldithio-
phosphorsäure . 3,0phosphoric acid . 3.0
Mineralschmieröl SAE 30 285.6Mineral lubricating oil SAE 30 285.6
Schauminhibitor 0.0075Foam inhibitor 0.0075
Wasser 200Water 200
Gew iclilsteileWeight parts
Produkt von Ii 18Product of ii 18
Sojabohnenlei, ithin 3.6Soybeans, ithin 3.6
Das Benzoesäiiiesalz desThe benzoic acid salt of
tert.-Cii 1 i-Alkyl-prim.-aminstert-Cii 1 i-alkyl-primary amines
(Molgewicht 19"l) 1.2(Molecular weight 19 "l) 1.2
Das' durch 2stünd'ges Erhitzen bei 80 C lunieste'lte Addukt von Zink-dicumyl- h l'iophosphinat mit 0.5 Äquivalenten tert.-Cn 11-Alkyl-prini.-amin The 'by 2 hours' heating at 80 C lunieste'lte adduct of Zinc dicumyl- iophosphinate with 0.5 equivalents of tert-Cn 11-alkyl-prini.-amine
(Molgewicht 191) 12.0(Molecular weight 191) 12.0
Mineralschmieri 1 SAE 5 ς6\.'Mineral lubricant 1 SAE 5 ς 6 \. '
Schauminhibil ι ..... 0.015Foam inhibitor ..... 0.015
Wasser 400.0Water 400.0
(jewichtstoilo(jewichtstoilo
18.018.0
3.63.6
Produkt von .1 Product of .1
Sojabohnenlecithin Soybean lecithin
Das salpetrigsaure Salz eines tert.-C'u 1 i-Alkvl-prim.-aminsThe nitrous acid salt of a tert-C'u 1 i-alkyl-primary amine
(Molgewicht 19'l) |.2(Molecular weight 19'l) | .2
Siilfurierte·» SpermölSilfed · »Sperm oil
(mit 10" ι, Schwefel) 18.0(with 10 "ι, sulfur) 18.0
4-Methyl-2,6-di-terl.-butylphenol .. 3.04-methyl-2,6-di-tert-butylphenol .. 3.0
Mineralschmieröl SAE 5 556.2Mineral lubricating oil SAE 5 556.2
Schauminhibitor . 0.015Foam inhibitor. 0.015
Wasser 400.0Water 400.0
11
Beispiel 8 GcwiehlsleileExample 8 Gcwiehlsleile
Produkt von J 18,0Product of J 18.0
Sojabohnenlecithin 3.6Soybean lecithin 3.6
Das Benzoesäuresalz eines tert.-Cit H-Alkyl-prim.-aminsThe benzoic acid salt of a tert-Cit H-alkyl-primary amine
(Molgewicht 191) 1,2(Molecular weight 191) 1.2
Sulfuriertes SpermölSulfurized sperm oil
(mit ΙΟ»/» Schwefel) 6,0(with ΙΟ »/» sulfur) 6.0
Mineralschmieröl SAE 5 571,2 !0 Mineral lubricating oil SAE 5 571.2 ! 0
Schauminhibitor 0,015Foam inhibitor 0.015
Wasser 400,0Water 400.0
Gewichtsteile ^Parts by weight ^
Produkt von E 18,0Product of E 18.0
Sojabohnenlecithin 3.6Soybean lecithin 3.6
Das Benzoesäuresalz einesThe benzoic acid salt one
tert.-Cn 1 i-Alkyl-prim.-aminstert-Cn 1 i-alkyl-primary amines
(Molgewicht 191) 1,2(Molecular weight 191) 1.2
Zinksalz der Di-isooctyldithio-Zinc salt of the di-isooctyldithio-
phosphorsäure 6,0phosphoric acid 6.0
Mineralschmieröl SAE 5 571.2Mineral lubricating oil SAE 5 571.2
Schauminhibitor 0.015Foam inhibitor 0.015
Wasser 400.0Water 400.0
Polytsobutenylbernsteinsäure- GewichtsteiiePolytsobutenylsuccinic acid parts by weight
anhydrid von A 28anhydride of A 28
Natriumhydroxyd 2Sodium hydroxide 2
Mineralschmieröl SAE 5 570Mineral lubricating oil SAE 5 570
Wasser 400Water 400
Beispiel 11Example 11
Polyisobutenylbemsteinsäure- GewichisieüePolyisobutenylsuccinic acid weights
anhydrid von A 28anhydride of A 28
Sojabohnenlecithin 3.6Soybean lecithin 3.6
Lauryl-diäthanolamin 1.2Lauryl diethanolamine 1.2
Chloriertes EikosanwachsChlorinated eikosan wax
(50% Chlor) 1.2(50% chlorine) 1.2
Mineralschmieröl SAE 5 565Mineral lubricating oil SAE 5 565
Natriumhydroxyd 2Sodium hydroxide 2
Schauminhibitor 0.015Foam inhibitor 0.015
Wasser 400Water 400
Polyisobutenyl bernsteinsäure- GewichtsteilePolyisobutenyl succinic acid parts by weight
anhydrid von A 28.5anhydride of A 28.5
Lauryl-diäthanolamin 1.2Lauryl diethanolamine 1.2
Chloriertes EikosanwachsChlorinated eikosan wax
(50» 0 Chlor) 1.2(50 »0 chlorine) 1.2
Mineralschmieröl SAE 5 568Mineral lubricating oil SAE 5 568
Calciumhydroxyd 1.5Calcium hydroxide 1.5
Wasser ". 400Water ". 400
Schauminhibitor 0.015Foam inhibitor 0.015
723723
Beispiel 13Example 13
Polyisobutenylbemsteinsäure- GewichisteilePolyisobutenylsuccinic acid parts by weight
anhydrid von A 28anhydride of A 28
N-tert.-Nonylacrylamid 3.6N-tert-nonylacrylamide 3.6
Lauryl-diäthanolamin 1,2Lauryl diethanolamine 1,2
Chloriertes EikosanwachsChlorinated eikosan wax
(50° ο Chlor) 1.2(50 ° ο chlorine) 1.2
Mineralschmieröl SAE 5 565Mineral lubricating oil SAE 5 565
Calciumhydroxyd 1.8Calcium hydroxide 1.8
Wasser 400Water 400
Schauminhibitor 0.015Foam inhibitor 0.015
Beispiel 14 Gewichtsteilc Example 14 parts by weight c
Produkt von C 30Product of C 30
Mineralschmieröl SAE 20 570Mineral lubricating oil SAE 20 570
Wasser 4(K)Water 4 (K)
Beispiel 15 „ . ,, , .,Example 15 “. ,,,.,
* Gewichtsteile * Parts by weight
Produkt von Beispiel 14 49.5Product of Example 14 49.5
Zinksalz der Di-isooctyldithiophosphorsäure 5Zinc salt of di-isooctyldithiophosphoric acid 5
Beispiel 16 „ -,,,·,Example 16 "- ,,, ·,
' Gewichtsteiie'Weight parts
Produkt von Beispiel 14 495Product of example 14 495
Sojabohnenlecithin 3Soybean lecithin 3
tert.-Cn 1 i-Alkyl-prim.-ainintert-Cn 1 i-alkyl-primary amine
(Molgewicht "191) 2(Molecular weight "191) 2
Beispiel 17 ,, , , .,Example 17 ,,,,.,
' Gewicntsteile'Parts by weight
Produkt von E 150Product of E 150
Mineralschmieröl SAE 20 650Mineral lubricating oil SAE 20 650
Wasser 400Water 400
Die Wasser-in-Öl-Emulsionen der Erfindung können sowohl als Schmiermittel als auch als Hydraulikflüssigkeiten verwendet werden, insbesondere als nicht brennbare Hydraulikflüssigkeiten.The water-in-oil emulsions of the invention can be used as both lubricants and hydraulic fluids can be used, especially as non-flammable hydraulic fluids.
Die Schmiereigenschaften, insbesondere die \erschleiß\ermindernden Eigenschaften der Wasser-in-Öl-Emulsionen /eigen sich aus den Ergebnissen einer ASTM-Verschleißpriifung. Bei diesem Test wird die Emulsion in einer hydraulischen Pumpe (einer Vickers-Flügelpumpe 104E) verwendet, die unter den folgenden Bedingungen arbeitet: Motordrehzahl: 1200 Γ min: ungefähre Durchflußmenge: 7.57 1min: Druck: 70 kg cm2: Sumpftemperatur: C. Die Ergebnisse des Tests sind in Tabelle Ϊ angegeben. Zum Vergleich wurde eine im Handel erhältliche wasserhaltige Emulsion für H\draulikflüssigkeiten geprüft.The lubricating properties, especially the \ wear \ reducing properties of the water-in-oil emulsions / are based on the results of an ASTM wear test. In this test, the emulsion is used in a hydraulic pump (a Vickers vane pump 104E) which operates under the following conditions: engine speed: 1200 Γ min: approximate flow rate: 7.57 1min: pressure: 70 kg cm 2 : sump temperature: C. The Results of the test are given in Table Ϊ. For comparison, a commercially available water-containing emulsion for hydraulic fluids was tested.
Die Feuerbeständigkeit der Wasser-in-Öl-Emulsionen der Erfindung wurde dadurch nachgewiesen, daß die Emulsion nach Beispiel 9 den Feuerbeständigkeitstest für Hydraulikflüssigkeiten nach \ orschrift des l'S-Bureau of Mines bestand. Das Test- \erfahren ist beschrieben im Federal Register \om 17. Dezember 1959. Bd. 24. Nr. 245. Titel 30. Teil 35. Abschnitte 35.1 bis 35.23.The fire resistance of the water-in-oil emulsions of the invention has been demonstrated by that the emulsion according to Example 9 passed the fire resistance test for hydraulic fluids according to regulations of the l'S Bureau of Mines. The test is described in the Federal Register \ om December 17, 1959. Vol. 24. No. 245. Title 30. Part 35. Sections 35.1 to 35.23.
5555
Emulsion nach BeispielEmulsion according to the example
■)
3 ■)
3
Versuchsdauer StundenTest duration hours
354 3(X) 300354 3 (X) 300
Flügelwing
0.45 0.32 0.110.45 0.32 0.11
TotalTotal
0.1830.183
0.140.14
0.0670.067
Die rosthemmenden Eigenschaften der Wasser- 50 ml der Emulsion eingetaucht wird. Nach in-öl-Emulsionen der Erfindung wurden nachge- 15 5 Wochen wird der Streifen auf Rostbildung unterwiesen durch die Ergebnisse eines Rosttests, bei dem sucht. Die Ergebnisse sind in Tabelle II zusammendie eine Hälfte eines Stahlstreifens in eine Probe von gefaßt.The rust-inhibiting properties of the water- 50 ml of the emulsion is immersed. To In-oil emulsions of the invention were used after 5 weeks, the strip is instructed for rust formation by the results of a rust test in which seeks. The results are summarized in Table II one half of a steel strip caught in a sample of.
Emulsionemulsion
Emulsion nach Beispiel 9 Emulsion according to Example 9
Handelsübliche Emulsion für Hydraulikflüssigkeiten (zum Vergleich) Commercial emulsion for hydraulic fluids (for comparison)
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13486061A | 1961-08-30 | 1961-08-30 | |
US18894762A | 1962-04-20 | 1962-04-20 | |
US280453A US3255108A (en) | 1961-08-30 | 1963-05-14 | Water-in-oil emulsions containing succinic esters |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1270723B true DE1270723B (en) | 1968-06-20 |
Family
ID=27384639
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEP1270A Pending DE1270723B (en) | 1961-08-30 | 1962-08-30 | Water-in-oil emulsion for lubrication purposes |
DEL47797A Pending DE1291436B (en) | 1961-08-30 | 1964-05-12 | Water-in-oil emulsion for lubrication purposes |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEL47797A Pending DE1291436B (en) | 1961-08-30 | 1964-05-12 | Water-in-oil emulsion for lubrication purposes |
Country Status (3)
Country | Link |
---|---|
US (1) | US3255108A (en) |
DE (2) | DE1270723B (en) |
GB (2) | GB1009197A (en) |
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EP0360394A3 (en) * | 1988-09-21 | 1992-03-18 | Imperial Chemical Industries Plc | Water-in-oil emulsion explosive |
FI901921A0 (en) * | 1989-04-20 | 1990-04-17 | Lubrizol Corp | FOERFARANDE FOER MINSKNING AV FRIKTIONEN MELLAN JAERNVAEGSHJUL OCH JAERNVAEGSSPAOR GENOM ANVAENDNING AV KOLLOIDALA DISPERGERINGSSYSTEM INNEHAOLLANDE METALL I OEVERSKOTT. |
EP0407124A1 (en) * | 1989-07-07 | 1991-01-09 | Tonen Corporation | Lubricating oil composition |
US5622649A (en) * | 1991-06-27 | 1997-04-22 | Emory University | Multiple emulsions and methods of preparation |
US5518517A (en) * | 1994-11-14 | 1996-05-21 | The Lubrizol Corporation | Water-in-oil emulsion fertilizer compositions |
US5512079A (en) * | 1994-11-14 | 1996-04-30 | The Lubrizol Corporation | Water-in-oil emulsifiers for slow release fertilizers using tertiary alkanol amines |
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US6200398B1 (en) | 1998-12-30 | 2001-03-13 | The Lubrizol Corporation | Emulsion explosive compositions |
US20040111957A1 (en) | 2002-12-13 | 2004-06-17 | Filippini Brian B. | Water blended fuel composition |
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US20070054968A1 (en) * | 2005-08-23 | 2007-03-08 | Bj Services Company | Environmentally friendly defoamer |
GB0622947D0 (en) * | 2006-11-17 | 2006-12-27 | Croda Int Plc | Surfactant compounds |
CN101985577B (en) * | 2010-11-01 | 2012-10-10 | 彭美东 | Linear cutting emulsified oil |
US20120178824A1 (en) * | 2011-01-11 | 2012-07-12 | Henkel Ag & Co. Kgaa | Hydrogels based on esters of polyisobutenesuccinic acid |
CN102676134A (en) * | 2012-05-02 | 2012-09-19 | 陆明富 | Preparation method for vegetable oil anti-jamming lubricant |
US10336954B2 (en) | 2013-02-07 | 2019-07-02 | Bl Technologies, Inc. | Compositions and methods for inhibiting fouling in hydrocarbons or petrochemicals |
DE112016002261T5 (en) | 2015-05-19 | 2018-03-01 | The Mosaic Company | Reverse emulsions for cavity control |
EP3257920A1 (en) * | 2016-06-17 | 2017-12-20 | Total Marketing Services | Lubricant polymers |
RU2652714C1 (en) * | 2017-07-17 | 2018-04-28 | Общество с ограниченной ответственностью "РудХим" | Universal emulsifier of inverted emulsions |
CN109352100A (en) * | 2018-12-07 | 2019-02-19 | 辽宁泰克诺美科技有限公司 | A kind of electric spark processing liquid that low smog is high in machining efficiency |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1265085A (en) * | 1959-08-24 | 1961-06-23 | California Research Corp | Lubricating oil compositions containing n-dialkylaminoalkyl alkenyl succinimides |
FR1265086A (en) * | 1959-08-24 | 1961-06-23 | California Research Corp | Lubricating oil compositions containing alkenyl succinimides of tetraethylene pentamine |
FR1283719A (en) * | 1960-03-15 | 1962-02-02 | California Research Corp | Lubricating oil compositions containing mixtures of metal dithiophosphates and n-dialkylaminoalkenyl succinimides |
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US2221162A (en) * | 1938-08-06 | 1940-11-12 | Texas Co | Lubricating oil |
US3057890A (en) * | 1958-04-17 | 1962-10-09 | Petrolite Corp | Certain polyoxyalkylene glycol esters |
US3070546A (en) * | 1959-01-16 | 1962-12-25 | Lubrizol Corp | Nitrogen-, phosphorus- and sulfurcontaining lubricants |
US3062612A (en) * | 1959-04-25 | 1962-11-06 | Inst Francais Du Petrole | Method of protecting metals against electrochemical corrosion of the acidic type |
-
1962
- 1962-08-30 DE DEP1270A patent/DE1270723B/en active Pending
- 1962-08-30 GB GB33400/62A patent/GB1009197A/en not_active Expired
-
1963
- 1963-05-14 US US280453A patent/US3255108A/en not_active Expired - Lifetime
-
1964
- 1964-05-12 DE DEL47797A patent/DE1291436B/en active Pending
- 1964-05-14 GB GB20156/56A patent/GB1059847A/en not_active Expired
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1265085A (en) * | 1959-08-24 | 1961-06-23 | California Research Corp | Lubricating oil compositions containing n-dialkylaminoalkyl alkenyl succinimides |
FR1265086A (en) * | 1959-08-24 | 1961-06-23 | California Research Corp | Lubricating oil compositions containing alkenyl succinimides of tetraethylene pentamine |
FR1283719A (en) * | 1960-03-15 | 1962-02-02 | California Research Corp | Lubricating oil compositions containing mixtures of metal dithiophosphates and n-dialkylaminoalkenyl succinimides |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2738040A1 (en) * | 1976-09-01 | 1978-03-02 | Nat Res Lab | METALWORKING LIQUID |
EP0156572A2 (en) * | 1984-03-21 | 1985-10-02 | Imperial Chemical Industries Plc | Surfactants for oil/water systems in which the hydrophilic component contains a specified anionic grouping |
EP0156572A3 (en) * | 1984-03-21 | 1986-11-20 | Imperial Chemical Industries Plc | Surfactants for oil/water systems in which the hydrophilic component contains a specified anionic grouping |
Also Published As
Publication number | Publication date |
---|---|
GB1009197A (en) | 1965-11-10 |
GB1059847A (en) | 1967-02-22 |
US3255108A (en) | 1966-06-07 |
DE1291436B (en) | 1969-03-27 |
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