DE1165574B - Process for the production of mixed esters used as emulsifiers for ointment bases - Google Patents

Process for the production of mixed esters used as emulsifiers for ointment bases

Info

Publication number
DE1165574B
DE1165574B DED33979A DED0033979A DE1165574B DE 1165574 B DE1165574 B DE 1165574B DE D33979 A DED33979 A DE D33979A DE D0033979 A DED0033979 A DE D0033979A DE 1165574 B DE1165574 B DE 1165574B
Authority
DE
Germany
Prior art keywords
ester
citric acid
pentaerythritol
weight
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
Application number
DED33979A
Other languages
German (de)
Inventor
Karl Hennig
Dr Gustav Lietz
Dr Guenter Meinhard
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DEHYDAG GmbH
Dehydag Deutsche Hydrierwerke GmbH
Original Assignee
DEHYDAG GmbH
Dehydag Deutsche Hydrierwerke GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by DEHYDAG GmbH, Dehydag Deutsche Hydrierwerke GmbH filed Critical DEHYDAG GmbH
Priority to DED33979A priority Critical patent/DE1165574B/en
Priority to CH651761A priority patent/CH397633A/en
Priority to GB2833061A priority patent/GB962919A/en
Publication of DE1165574B publication Critical patent/DE1165574B/en
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10—Ester interchange

Description

Verfahren zur Herstellung von als Emulgiermittel für Salbengrundlagen dienenden Mischestern Gegenstand der Erfindung ist die Herstellung von als Emulgatoren für Salbengrundlagen zu verwendenden Mischestern, die Kondensationsprodukte aus einem Pentaerythrit-di-fettsäureester und einem Zitronensäure-di-fettalkoholester im Molverhältnis 1:1 darstellen, wobei die Veresterung der Zitronensäure mit dem Fettalkohol zu dem als Zwischenprodukt dienenden Zitronensäure-di-fettalkoholester unter Verwendung wäßriger Zitronensäure erfolgt. Die Mischester zeichnen sich durch Geruchlosigkeit und hohes Wasserbindungsvermögen aus.Process for the preparation of as an emulsifier for ointment bases serving mixed esters The invention relates to the production of emulsifiers mixed esters to be used for ointment bases, the condensation products a pentaerythritol di-fatty acid ester and a citric acid di-fatty alcohol ester represent in a molar ratio of 1: 1, the esterification of citric acid with the Fatty alcohol to the citric acid di-fatty alcohol ester serving as an intermediate takes place using aqueous citric acid. The mixed esters are characterized by Odorless and high water binding capacity.

Es wurde gefunden, daß man zu besonders wertvollen Produkten gelangt, wenn die Kondensationsprodukte höhermolekulare lipophile Reste gleichzeitig sowohl am Zitronensäure- als auch am Pentaerythritrest enthalten. Für die Kondensationsprodukte läßt sich die folgende Konstitutionsformel angeben, wobei die Bindung des Pentaerythritesters an die Zitronensäure auch an die mittelständige Carboxylgruppe erfolgen kann. Im allgemeinen liegen Gemische von Verbindungen der verschiedenen möglichen Varianten der folgenden allgemeinen Konstitutionsformel vor. It has been found that particularly valuable products are obtained if the condensation products contain high molecular weight lipophilic residues at the same time on both the citric acid and pentaerythritol residues. The following constitutional formula can be given for the condensation products, it being possible for the pentaerythritol ester to bond to the citric acid also to the central carboxyl group. In general, there are mixtures of compounds of the various possible variants of the following general constitutional formula.

Dabei bedeuten R1 und R2 gesättigte oder ungesättigte Fettalkoholreste der Kettenlängen C12 bis C20 oder Reste von Dimerisierungsprodukten dieser Fettalkohole. Here, R1 and R2 denote saturated or unsaturated fatty alcohol radicals of chain lengths C12 to C20 or residues of dimerization products of these fatty alcohols.

Der besondere technische Wert der erfindungsgemäß hergestellten Produkte beruht nicht allein auf ihrem strukturellen Aufbau und den sich daraus ergebenden Vorteilen, sondern auch auf der besonderen Art des Herstellungsverfahrens der Mischkondensate und der Zwischenprodukte. The particular technical value of the products manufactured according to the invention is not based solely on their structural design and the resulting from it Advantages, but also on the special type of manufacturing process for the mixed condensates and the intermediates.

Es ist bekannt, daß die Herstellung von Zitronensäureestern nach den üblichen Veresterungsmethoden Schwierigkeiten bereitet, da die Zitronensäure bei längerem Erhitzen unter Wasserabspaltung teilweise in die ungesättigte Aconitsäure übergeht, die im weiteren Verlauf der Reaktion zu störenden Harzbildungen führt. It is known that the production of citric acid esters according to Difficulties with the usual esterification methods, since citric acid with prolonged heating with elimination of water partially into the unsaturated aconitic acid passes, which leads to disruptive resin formation in the further course of the reaction.

Es wurde nun gefunden, daß sich diese Schwierigkeiten vermeiden lassen, wenn man zur Veresterung wäßrige Zitronensäure einsetzt. Diesc Feststellung ist außerordentlich überraschend und läuft den üblichen Veresterungsmethoden völlig zuwider, da die Gegenwart von Wasser normalerweise eine Verzögerung des Reaktionsablaufes bewirkt und damit gerade eine Begünstigung von Nebenreaktionen hervorruft. Die Veresterung wird in der Weise durchgeführt, daß zu dem vorgelegten, auf etwa 140 bis 170"C, vorzugsweise 160"C C erhitzten Fettalkohol die wäßrige Zitronensäure unter Rühren portionsweise zugegeben wird. Die Zitronensäure löst sich sofort auf und verestert mit dem Alkohol. Das Reaktionswasser sowie das mit der Zitronensäure eingebrachte Wasser wird bei vermindertem Druck abdestilliert. Durch die schnelle Veresterung wird jegliche Nebenreaktion und damit Verharzung vermieden, und man erhält ein einwandfreies, hellfarbiges Veresterungsprodukt. It has now been found that these difficulties can be avoided if aqueous citric acid is used for the esterification. This is a finding extremely surprising and runs the usual Completely contrary to esterification methods, since the presence of water normally delays the reaction causes and thus just causes side reactions to be favored. The esterification is carried out in such a way that to the submitted, to about 140 to 170 "C, Preferably 160 ° C fatty alcohol heated the aqueous citric acid with stirring is added in portions. The citric acid immediately dissolves and esterifies with the alcohol. The water of reaction as well as that introduced with the citric acid Water is distilled off under reduced pressure. Due to the rapid esterification any side reaction and thus resinification is avoided, and you get a perfect, light-colored esterification product.

Die Herstellung des zweiten Veresterungsproduktes, des Pentaerythrit-fettsäureesters, geschieht nach einem der üblichen Verfahren, wobei der Umesterung eines Fettsäuremethylesters mit dem Polyalkohol der Vorzug zu geben ist, da auf diesem Wege besonders helle Produkte mit einer Säurezahl unter 1 erhalten werden. The production of the second esterification product, the pentaerythritol fatty acid ester, takes place according to one of the customary processes, the transesterification of a fatty acid methyl ester with the polyalcohol is to be given preference, since this way particularly bright Products with an acid number below 1 can be obtained.

Die Kondensation des Zitronensäureesters mit dem Pentaerythritester erfolgt unter Rühren bei etwa 25 mm Unterdruck und 180 bis 1900C im Stickstoffstrom. Wenn die Säurezahl einer aus der Apparatur entnommenen Probe unter 1 liegt, ist die Veresterung beendet. The condensation of the citric acid ester with the pentaerythritol ester takes place with stirring at about 25 mm negative pressure and 180 to 1900C in a nitrogen stream. If the acid number of a sample taken from the apparatus is below 1, is the esterification ended.

Die erfindungsgemäß erhältlichen Kondensationsprodukte zeigen sehr wertvolle Eigenschaften. Sie sind insbesondere als Emulgatoren für pharmazeutische und kosmetische Salben und Linimente interessant. The condensation products obtainable according to the invention show a lot valuable properties. They are particularly useful as emulsifiers for pharmaceutical and cosmetic ointments and liniments interesting.

Die Temperaturstabilität der mit ihrer Hilfe hergestellten Emulsionen ist ebenfalls besonders hoch, und zwar werden nicht nur größere Wassermengen wesentlich schneller aufgenommen, sondern die größere Gesamtwassermenge kann auch in größeren Anteilen eingearbeitet werden. Ferner sind die bei Verwendung üblicher Vaselinequalitäten erhaltenen Salben rein weiß und nicht mehr gelb gefärbt wie bisher, weiterhin praktisch geruchfrei und leicht und dauerhaft parfümierbar. Als weiterer ins Gewicht fallender Vorteil ergibt sich ihre leichte Konservierbarkeit und verbesserte Haltbarkeit bei längerer Lagerung. Die mit den erfindungsgemäßen Kondensationsprodukten hergestellten Salben zeigen ferner eine glattere, weichere Struktur, eine geschmeidigere Konsistenz, d. h., sie kleben nicht, vermitteln einen subjektiv angenehmeren Hauteindruck und werden leichter von der Haut aufgenommen als auf gleicher Basis, jedoch mit üblichen Emulgatoren hergestellte Salben. Die unter Verwendung der erfindungsgemälden Produkte hergestellten Salben sind dermatologisch völlig einwandfrei.The temperature stability of the emulsions produced with their help is also particularly high, and not only do larger amounts of water become essential absorbed faster, but the larger total amount of water can also be larger Shares be incorporated. Furthermore, those are more common when used Ointments obtained from Vaseline qualities are pure white and no longer colored yellow as before, still practically odorless and easily and permanently perfumable. As another A significant advantage is their easy preservability and improved Shelf life with prolonged storage. Those with the condensation products according to the invention Ointments produced also show a smoother, softer structure, a more supple Consistency, d. that is, they do not stick, convey a subjectively more pleasant skin impression and are more easily absorbed by the skin than on the same basis, but with ointments made from conventional emulsifiers. The using the inventive Ointments made in products are completely dermatologically sound.

Beispiel 1 a) 115 Gewichtsteile Octadecylalkohol mit einer Hydroxylzahl 206 und 54 Gewichtsteile wäßrige Zitronensäure (44kg Zitronensäure in 10 kg Wasser gelöst) werden derart miteinander umgesetzt, daß zu dem auf 160 C erhitzten Alkohol innerhalb 30 Minuten portionsweise jeweils so viel wäßrige Zitronensäure zugegeben wird, wie mit dem vorgelegten Alkohol gleichzeitig reagieren kann. Das Reaktionswasser sowie das eingebrachte Wasser wird bei vermindertem Druck (25 bis 50 mm Hg) abdestilliert. Der Verlauf der Veresterung läßt sich am übergehenden Reaktionswasser verfolgen. Der erhaltene Zitronensäure-dioctadecylester ist von heller Farbe, hat eine Veresterungszahl von 241 und eine Säurezahl von 80 bis 85, wie sie für die weitere Herstellung des Mischesters erforderlich ist. Die Ausbeute an Ester beträgt etwa 140 Gewichtsteile. b) 76 Gewichtsteile Pentaerythrit, 260 Gewichtsteile Kokosfettsäuremethylester mit einer Verseifungszahl von 240 und 1 Gewichtsteil Natriummethylat als Veresterungskatalysator werden im Rührkessel auf etwa 70c C erhitzt und der bei dieser Temperatur frei werdende Methylalkohol abdestilliert. Die letzten Reste Methylalkohol werden unter Vakuum entfernt, bis die Säurezahl unter 2 gesunken ist. Der gebildete Pentaerythrit-di-kokosfettsäureester wird mit 1 °/o Bleicherde durchgerührt und so von der anhaftenden Seife befreit. Die Ausbeute an Ester beträgt etwa 93 bis 940/o der Theorie. c) 140 Gewichtsteile Zitronensäure-di-octadecylester aus a) und 115 Gewichtsteile Pentaerythrit-di-Kokosfettsäureester aus b) werden unter Rühren bei 180 bis 190"C und 25 mm Unterdruck im Stickstoffstrom so lange verestert, bis die Säurezahl einer Probe unter 1 liegt, was nach 3 bis 4 Stunden der Fall ist. Nach beendeter Veresterung wird der Mischester auf 60 bis 65"C abgekühlt und mit 0,1 0/0 (bezogen auf die Gesamtmenge) 400/,dem Wasserstoffsuperoxyd gebleicht. Es wird ein Mischester von wachsgelber Farbe und wachsartiger Konsistenz mit einer Säurezahl unter 1, einer Verseifungszahl von 224 und einer Hydroxylzahl von 75 erhalten. Die Ausbeute beträgt 236 Gewichtsteile. Example 1 a) 115 parts by weight of octadecyl alcohol with a hydroxyl number 206 and 54 parts by weight of aqueous citric acid (44 kg of citric acid in 10 kg of water dissolved) are reacted with one another in such a way that the alcohol heated to 160.degree as much aqueous citric acid was added in portions over the course of 30 minutes how can react with the submitted alcohol at the same time. The water of reaction and the water introduced is distilled off under reduced pressure (25 to 50 mm Hg). The course of the esterification can be followed on the water of reaction which passes over. The citric acid dioctadecyl ester obtained is light in color and has an esterification number of 241 and an acid number of 80 to 85, as required for the further preparation of the Mixed ester is required. The yield of ester is about 140 parts by weight. b) 76 parts by weight of pentaerythritol, 260 parts by weight of coconut fatty acid methyl ester with a saponification number of 240 and 1 part by weight of sodium methylate as an esterification catalyst are heated in the stirred kettle to about 70c C and the one released at this temperature Distilled off methyl alcohol. The last residues of methyl alcohol are under vacuum removed until the acid number has dropped below 2. The pentaerythritol di-coconut fatty acid ester formed is stirred with 1% fuller's earth and freed from the adhering soap. The ester yield is about 93 to 940 / o of theory. c) 140 parts by weight Citric acid di-octadecyl ester from a) and 115 parts by weight of pentaerythritol di-coconut fatty acid ester from b) are stirred at 180 to 190 "C and 25 mm negative pressure in a stream of nitrogen Esterified until the acid number of a sample is below 1, which is after 3 to 4 hours is the case. After the esterification has ended, the mixed ester is increased to 60 to 65 "C cooled and with 0.1 0/0 (based on the total amount) 400 /, the hydrogen peroxide bleached. It becomes a mixed ester of waxy yellow color and waxy consistency with an acid number below 1, a saponification number of 224 and a Hydroxyl number received from 75. The yield is 236 parts by weight.

In entsprechender Weise können Kondensationsprodukte aus folgenden Esterpaaren hergestellt werden: Zitronensäure-di-laurylester und Pentaerythritdi-stearinsäureester, Zitronensäure-di-laurylester und Pentaerythrit-di-kokosfettsäureester, Diester aus Zitronensäure mit dem durch sogenannter Guerbetreaktion aus Laurylalkohol erhaltenen dimeren Fettalkohol und Pentaerythrit- di - steari nsäureester, Zitronensäure - dioctadecandiolester und Pentaerythrit-di-kokosfettsäureester, Zitronensäure-di-octadecandiolester und Pentaerythrit-di-stearinsäureester, Zitronensäure-didodecylester und Pentaerythrit-di-kokosfettsäureester. In a corresponding manner, condensation products can be obtained from the following Pairs of esters are produced: citric acid di-lauryl ester and pentaerythritol di-stearic acid ester, Citric acid di-lauryl ester and pentaerythritol di-coconut fatty acid ester, diesters from Citric acid with that obtained from lauryl alcohol by the so-called Guerbet reaction dimeric fatty alcohol and pentaerythritol di-stearic acid esters, citric acid dioctadecanediol ester and pentaerythritol di-coconut fatty acid ester, citric acid di-octadecanediol ester and pentaerythritol di-stearic acid ester, citric acid didodecyl ester and pentaerythritol di-coconut fatty acid ester.

Unter den aufgeführten Kondensationsprodukten eigneten sich diejenigen aus Zitronensäure-di-octadecylester und Pentaerythrit-di-kokosfettsäureester am besten als Emulgatoren für Salbengrundlagen. Among the condensation products listed, those were suitable from citric acid di-octadecyl ester and pentaerythritol di-coconut fatty acid ester am best as emulsifiers for ointment bases.

Beispiel 2 Eine Salbengrundmasse aus 35 Gewichtsprozent Vaseline DAB 6, 30 Gewichtsprozent Ölsäuredecylester, 6 Gewichtsprozent Cetylalkohol, 5 Gewichtsprozent Ozokerit, weiß, 70 bis 72 C, 5 Gewichtsprozent Hartparaffin, 50 bis 52es, 5 Gewichtsprozent Paraffin, dickflüssig, 2 Gewichtsprozent Aluminiumstearat wird unter Zugabe von 12 Gewichtsprozent des gemäß Beispiel 1, c) hergestellten Mischesters auf dem Wasserbad zusammengeschmolzen, homogen gerührt und erkalten gelassen. Man erhält eine Salbengrundlage, die eine hohe Wasseraufnahmefähigkeit besitzt. Example 2 An ointment base made from 35 percent by weight Vaseline DAB 6, 30 percent by weight of oleic acid decyl ester, 6 percent by weight of cetyl alcohol, 5 percent by weight Ozokerite, white, 70 to 72 C, 5 percent by weight hard paraffin, 50 to 52es, 5 percent by weight Paraffin, viscous, 2 percent by weight aluminum stearate is added with 12 percent by weight of the mixed ester prepared according to Example 1, c) on the water bath melted together, stirred homogeneously and allowed to cool. An ointment base is obtained, which has a high water absorption capacity.

In diese Salbengrundlage können Parfüms sowie pharmazeutische und kosmetische Wirkstoffe eingearbeitet werden, wobei gebrauchsfertige Salben oder Cremes erhalten werden. Weiterhin kann in die Salbengrundlage bis zur dreifachen Gewichtsmenge Wasser eingearbeitet werden, wobei salbenartige Emulsionen vom Typ »Wasser in Öl« entstehen. Die Konsistenz richtet sich nach der verwendeten Wassermenge und läßt sich den verschiedenen Verwendungszwecken anpassen. In this ointment base can perfumes as well as pharmaceutical and Cosmetic active ingredients are incorporated, with ready-to-use ointments or Creams are obtained. Furthermore, up to three times as much can be added to the ointment base Weight of water are incorporated, with ointment-like emulsions of the type "Water in oil" is created. The consistency depends on the amount of water used and can be adapted to different uses.

Claims (2)

Patentansprüche: 1. Verfahren zur Herstellung von als Emulgiermittel für Salben grundlagen dienenden Mischestern, dadurch gekennzeichnet, daß man einen Fettalkohol mit wäßriger Zitronensäure zum entsprechenden Zitronensäure-di-fettalkoholester und diesen mit einem in bekannter Weise hergestellten Pentaerythrit-di-fettsäureester im Molverhältnis 1:1 umsetzt. Claims: 1. Process for the production of as an emulsifier mixed esters serving as a basis for ointments, characterized in that one Fatty alcohol with aqueous citric acid to form the corresponding citric acid di-fatty alcohol ester and this with a pentaerythritol di-fatty acid ester prepared in a known manner in a molar ratio of 1: 1. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man Zitronensäure-di-octadecalester mit Pentaerythrit-di-kokosfettsäureester umsetzt. 2. The method according to claim 1, characterized in that citric acid di-octadecal ester with pentaerythritol di-coconut fatty acid ester. In Betracht gezogene Druckschriften: Deutsche Patentschrift Nr. 860 204. Documents considered: German Patent No. 860 204.
DED33979A 1960-08-08 1960-08-08 Process for the production of mixed esters used as emulsifiers for ointment bases Pending DE1165574B (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DED33979A DE1165574B (en) 1960-08-08 1960-08-08 Process for the production of mixed esters used as emulsifiers for ointment bases
CH651761A CH397633A (en) 1960-08-08 1961-06-05 Process for the production of emulsifiers for ointment bases
GB2833061A GB962919A (en) 1960-08-08 1961-08-04 Process for the preparation of emulsifiers for ointment base compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED33979A DE1165574B (en) 1960-08-08 1960-08-08 Process for the production of mixed esters used as emulsifiers for ointment bases

Publications (1)

Publication Number Publication Date
DE1165574B true DE1165574B (en) 1964-03-19

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DED33979A Pending DE1165574B (en) 1960-08-08 1960-08-08 Process for the production of mixed esters used as emulsifiers for ointment bases

Country Status (3)

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CH (1) CH397633A (en)
DE (1) DE1165574B (en)
GB (1) GB962919A (en)

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