EP0333548A1 - Stable aqueous emulsions of essential oils - Google Patents

Stable aqueous emulsions of essential oils Download PDF

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Publication number
EP0333548A1
EP0333548A1 EP89400593A EP89400593A EP0333548A1 EP 0333548 A1 EP0333548 A1 EP 0333548A1 EP 89400593 A EP89400593 A EP 89400593A EP 89400593 A EP89400593 A EP 89400593A EP 0333548 A1 EP0333548 A1 EP 0333548A1
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weight
parts
xanthan gum
essential oils
essential oil
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EP89400593A
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German (de)
French (fr)
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EP0333548B1 (en
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Antoine Coutant
Cécile Mercieux
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Rhodia Chimie SAS
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Rhone Poulenc Chimie SA
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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
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials

Definitions

  • the present invention relates to stable aqueous emulsions of essential oils which can be used in particular for the preparation of flavoring concentrates for food products, in particular non-alcoholic drinks and confectionery or concentrates for cosmetics.
  • sucroglycerides or sucroesters it is known to use sucroglycerides or sucroesters to prepare aqueous emulsions of essential oils.
  • aqueous emulsions which may contain up to 15 to 20% of essential oils and a fluid mixture of sucroglycerides and of a fluid rapeseed oil for example ( sucroglyceride / fluid oil weight ratio of 30/70 to 50/50) in an amount expressed as sucroglycerides representing from 40 to 60% of the weight of the essential oil; sufficient water is present to complete the emulsion to 100% by weight.
  • Czech patent n ° 188.576 relates to food perfume powders prepared from an aqueous emulsion of lemon oil for example, obtained using a sucroester or a monoglyceride and carboxymethylcellulose as stabilizer.
  • the amount of monoglyceride or sucroester used corresponds to approximately 50% of the weight of oil.
  • Such emulsions have the major drawback of requiring the presence of too large a quantity of sucroglycerides or of sucroesters.
  • the stable aqueous emulsions of essential oils which are the subject of the invention are characterized in that they consist of: - 1 to 45 parts by weight, preferably from 1 to 20 parts by weight of an essential oil - 0.01 to 1 part by weight, preferably from 0.015 to 0.5 part by weight and more particularly from 0.03 to 0.3 part by weight of a nonionic emulsifier chosen from sucroglycerides and sucroesters - 0.2 to 1.5 parts by weight, preferably 0.25 to 1 parts by weight and very particularly 0.3 to 0.5 parts of xanthan gum - and the complement to 100 parts by weight of water.
  • essential oils means mixtures of various more or less volatile products derived from plant species by an appropriate physical process such as distillation carried out in a stream of water vapor, enfleurage, maceration, solvent extraction and expression. They are also called “essences”.
  • essential oils we can cite: the essence of angelica roots, the essence of anise, the essence of cinnamon, the essence of lemongrass, the essence of coriander, the essence of garlic, onion essence, bitter almond essence, juniper essence, ginger essence and all citrus essences like lemons, tangerines, oranges, grapefruits, etc. ..
  • sucrose denotes the mixture of products obtained by transesterification of sucrose and natural or synthetic triglycerides; this mixture contains monoglycerides, diglycerides, unaltered triglycerides (in small quantities), monoesters and diesters of sucrose.
  • triglyceride means one or more triglycerides of saturated or unsaturated aliphatic fatty acids having at least 12 atoms, preferably 14 to 20 carbon atoms.
  • triglyceride obtained by reaction of glycerol and fatty acids but it is more advantageous for economic reasons to use natural triglycerides which are mixtures.
  • triglycerides suitable for the invention examples that may be mentioned include lard, tallow, peanut oil, butter oil, cotton seed oil, linseed oil, coconut oil, olive oil, palm oil, grape seed oil, fish oil, soybean oil, castor oil, oil copra.
  • fatty acid triglycerides containing no more than one double bond are used and if necessary, they are subjected to hydrogenation in order to reduce the number of unsaturations.
  • palm sugar, lard, coconut oil, tallow sugar are preferably used. They are in the form of more or less consistent pasta and differ commercially by their melting point: - lard sucroglycerides ... 47 to 50 ° C - tallow sucroglycerides ... 50 to 55 ° C - palm oil sucroglycerides ... 55 to 58 ° C - coconut oil sucroglycerides ... 60 to 62 ° C
  • palm oil sucroglycerides are chosen.
  • sucroglycerides can also be in powdered form by placing on a support such as skim milk, whey, sucrose, maltodextrin, starch, polysaccharides ...
  • sucrose monoesters and diesters obtained by the action of sucrose on a fatty acid which may contain from 12 to 20 carbon atoms (of the same type as that used to prepare sucroglycerides) or else by separation with within the mixture (called “sucroglycerides”) resulting from the transterification of sucrose and natural or synthetic triglycerides.
  • the sucroesters can be in pasty form or in pulverulent form by placing on a support of the same type as those mentioned above concerning the sucroglycerides.
  • the stable emulsions of essential oils which are the subject of the invention can be prepared by various methods.
  • a first method of preparation consists in dispersing the sucroglyceride or the sucroester in water at a temperature of the order of 20 to 60 ° C., adding the xanthan gum with stirring until a solution is obtained and then dispersing the essential oil in the aqueous mixture by homogenization.
  • a second mode considered to be preferential consists on the one hand to disperse the sucroglyceride or the sucroester in water at a temperature of the order of 20 to 60 ° C. and then to disperse the essential oil therein by homogenization - on the other hand, to prepare an aqueous solution of xanthan gum at a temperature of the order of 20 to 60 ° C. - to introduce the xanthan gum solution obtained in the dispersion of sucroglyceride or sucroester and essential oil - then homogenize.
  • Stable aqueous emulsions of essential oils can be used for the preparation of food flavoring concentrates (soft drinks, confectionery) or concentrates for cosmetics.
  • sucroglyceride or the sucroester is dissolved in water at 80 ° C. with stirring at 700 rpm.
  • the xanthan gum is then poured in rain; stirring is left for 15 minutes at 700 revolutions / minute.
  • the solution obtained is kept for at least 2 hours at room temperature.
  • sucroglyceride or the sucroester is dissolved in water, at 80 ° C. with stirring at 700 rpm; stirring is still maintained for 15 minutes at 700 revolutions / minute.
  • the solution formed is left to stand at room temperature for at least 2 hours.
  • Orange essential oil is added to the sucroglyceride or sucroester solution with shaking with ULTRA TURRAX T45N.
  • the xanthan gum solution is introduced into the mixture of essential oil and sucroglyceride or sucroester, then the whole is homogenized for 40 seconds with ULTRA TURRAX T45N at maximum speed.
  • the prepared emulsions are stored at different temperatures (ambient, 4 ° C and 50 ° C) in 100 ml graduated cylinders.
  • Emulsions are considered stable when the code assigned to them is 1 or 2.
  • the raw materials used to carry out Examples 1 to 21 are as follows: . orange essential oil . xanthan gum: RHODIGEL marketed by Rhône-Poulenc . palm oil sucroglyceride with the following specifications: - combined sugar 19 ⁇ 2% - free sugar ⁇ 1.5% - acid number ⁇ 8 - saponification index 150 ⁇ 10 - density 0.97 at 66 ° C - melting zone 50 to 60 ° C . palmitic acid sucroester of the following specifications: - stearic acid / palmitic acid: 30/70 - monoester / di and triesters: 70/30 - melting zone 46 at 52 ° C
  • Orange essential oil emulsions are prepared according to procedure No. 1 or No. 2.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Colloid Chemistry (AREA)
  • Cosmetics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Fats And Perfumes (AREA)
  • Seasonings (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

Stable aqueous emulsions of essential oils consisting of - 1 to 45 parts by weight of an essential oil - 0.01 to 1 part by weight of a nonionic emulsifier chosen from sugar glycerides and sugar esters - 0.2 to 1.5 parts by weight of xanthan gum - and the residue to 100 parts by weight of water. They are prepared by dissolving xanthan gum in the nonionic emulsifier and dispersion of the essential oil before or after the addition of xanthan gum. Use for the preparation of aromatising concentrates.

Description

La présente invention a pour objet des émulsions aqueuses stables d'huiles essentielles pouvant être utilisées notamment pour la préparation de concentrats d'aromatisation de produits alimentaires, en particulier de boissons sans alcools et de confiseries ou de concentrats pour cosmétiques.The present invention relates to stable aqueous emulsions of essential oils which can be used in particular for the preparation of flavoring concentrates for food products, in particular non-alcoholic drinks and confectionery or concentrates for cosmetics.

Il est connu d'utiliser des sucroglycérides ou des sucroesters pour préparer des émulsions aqueuses d'huiles essentielles.It is known to use sucroglycerides or sucroesters to prepare aqueous emulsions of essential oils.

On peut citer par exemple le brevet français publié sous le numéro 2.523.134 décrivant des émulsions aqueuses stables pouvant contenir jusqu'à 15 à 20 % d'huiles essentielles et un mélange fluide de sucroglycérides et d'une huile fluide de colza par exemple (rapport pondéral sucroglycéride / huile fluide de 30/70 à 50/50) en une quantité exprimée en sucroglycérides représentant de 40 à 60 % du poids de l'huile essentielle ; l'eau est présente en quantité suffisante pour compléter l'émulsion à 100 % en poids.Mention may be made, for example, of the French patent published under the number 2.523.134 describing stable aqueous emulsions which may contain up to 15 to 20% of essential oils and a fluid mixture of sucroglycerides and of a fluid rapeseed oil for example ( sucroglyceride / fluid oil weight ratio of 30/70 to 50/50) in an amount expressed as sucroglycerides representing from 40 to 60% of the weight of the essential oil; sufficient water is present to complete the emulsion to 100% by weight.

Le brevet tchèque n° 188.576 vise des poudres de parfums alimentaires préparées à partir d'une émulsion aqueuse d'huile de citron par exemple, obtenue à l'aide d'un sucroester ou d'un monoglycéride et de carboxyméthylcellulose comme stabilisant. La quantité de monoglycéride ou sucroester mise en oeuvre correspond à environ 50 % du poids d'huile.Czech patent n ° 188.576 relates to food perfume powders prepared from an aqueous emulsion of lemon oil for example, obtained using a sucroester or a monoglyceride and carboxymethylcellulose as stabilizer. The amount of monoglyceride or sucroester used corresponds to approximately 50% of the weight of oil.

De telles émulsions présentent l'inconvénient majeur de nécessiter la présence d'une quantité trop importante de sucroglycérides ou de sucroesters.Such emulsions have the major drawback of requiring the presence of too large a quantity of sucroglycerides or of sucroesters.

Les émulsions aqueuses stables d'huiles essentielles faisant l'objet de l'invention sont caractérisées en ce qu'elles sont constituées de :
- 1 à 45 parties en poids, de préférence de 1 à 20 parties en poids d'une huile essentielle
- 0,01 à 1 partie en poids, de préférence de 0,015 à 0,5 partie en poids et tout particulièrement de 0,03 à 0,3 partie en poids d'un émulsifiant non-ionique choisi parmi les sucroglycérides et les sucroesters
- 0,2 à 1,5 partie en poids, de préférence de 0,25 à 1 partie en poids et tout particulièrement de 0,3 à 0,5 partie de gomme xanthane
- et du complément à 100 parties en poids d'eau.The stable aqueous emulsions of essential oils which are the subject of the invention are characterized in that they consist of:
- 1 to 45 parts by weight, preferably from 1 to 20 parts by weight of an essential oil
- 0.01 to 1 part by weight, preferably from 0.015 to 0.5 part by weight and more particularly from 0.03 to 0.3 part by weight of a nonionic emulsifier chosen from sucroglycerides and sucroesters
- 0.2 to 1.5 parts by weight, preferably 0.25 to 1 parts by weight and very particularly 0.3 to 0.5 parts of xanthan gum
- and the complement to 100 parts by weight of water.

On entend par "huiles essentielles", des mélanges de divers produits plus ou moins volatils issus d'espèces végétales par un procédé physique approprié tel que la distillation effectuée dans un courant de vapeur d'eau, l'enfleurage, la macération, l'extraction aux solvants et l'expression. On les appelle également "essences".The term "essential oils" means mixtures of various more or less volatile products derived from plant species by an appropriate physical process such as distillation carried out in a stream of water vapor, enfleurage, maceration, solvent extraction and expression. They are also called "essences".

Comme exemples d'huiles essentielles, on peut citer : l'essence de racines d'angélique, l'essence d'anis, l'essence de cannelle, l'essence de citronnelle, l'essence de coriandre, l'essence d'ail, l'essence d'oignon, l'essence d'amande amère, l'essence de genièvre, l'essence de gingembre et toutes les essences d'agrumes comme les citrons, les mandarines, les oranges, les pamplemouses, etc...As examples of essential oils, we can cite: the essence of angelica roots, the essence of anise, the essence of cinnamon, the essence of lemongrass, the essence of coriander, the essence of garlic, onion essence, bitter almond essence, juniper essence, ginger essence and all citrus essences like lemons, tangerines, oranges, grapefruits, etc. ..

Il est connu que par le terme "sucroglycérides", on désigne le mélange de produits obtenus par transesterification du saccharose et de triglycérides naturels ou de synthèse ; ce mélange contient des monoglycérides, des diglycérides, des triglycérides inaltérés (en faibles quantités), des monoesters et des diesters de saccharose.It is known that the term "sucroglycerides" denotes the mixture of products obtained by transesterification of sucrose and natural or synthetic triglycerides; this mixture contains monoglycerides, diglycerides, unaltered triglycerides (in small quantities), monoesters and diesters of sucrose.

Par triglycéride, on entend un ou plusieurs triglycérides d'acides gras aliphatiques saturés ou insaturés ayant au moins 12 atomes de préférence 14 à 20 atomes de carbone. On peut évidemment partir d'un triglycéride de synthèse obtenu par réaction du glycérol et d'acides gras mais il est plus intéressant pour des raisons économiques de faire appel aux triglycérides naturels qui sont des mélanges.The term “triglyceride” means one or more triglycerides of saturated or unsaturated aliphatic fatty acids having at least 12 atoms, preferably 14 to 20 carbon atoms. One can obviously start from a synthetic triglyceride obtained by reaction of glycerol and fatty acids but it is more advantageous for economic reasons to use natural triglycerides which are mixtures.

Comme triglycérides convenant à l'invention, on peut citer à titre d'exemples, le saindoux, le suif, l'huile d'arachide, l'huile de beurre, l'huile de graines de coton, l'huile de lin, l'huile de noix de coco, l'huile d'olive, l'huile de palme, l'huile de pépins de raisin, l'huile de poisson, l'huile de soja, l'huile de ricin, l'huile de coprah.As triglycerides suitable for the invention, examples that may be mentioned include lard, tallow, peanut oil, butter oil, cotton seed oil, linseed oil, coconut oil, olive oil, palm oil, grape seed oil, fish oil, soybean oil, castor oil, oil copra.

D'une manière préférentielle, on utilise des triglycérides d'acides gras ne contenant pas plus d'une double liaison et si nécessaire, on les soumet à une hydrogénation afin de réduire le nombre d'insatura­tions.Preferably, fatty acid triglycerides containing no more than one double bond are used and if necessary, they are subjected to hydrogenation in order to reduce the number of unsaturations.

Ainsi, on emploie préférentiellement les sucroglycérides d'huile de palme, de saindoux, d'huile de coprah, de suif. Ils se présentent sous forme de pâtes plus ou moins consistantes et se différencient commercialement par leur point de fusion : - sucroglycérides de saindoux ... 47 à 50° C - sucroglycérides de suif ... 50 à 55° C - sucroglycérides d'huile de palme ... 55 à 58° C - sucroglycérides d'huile de coprah ... 60 à 62° C Thus, palm sugar, lard, coconut oil, tallow sugar are preferably used. They are in the form of more or less consistent pasta and differ commercially by their melting point: - lard sucroglycerides ... 47 to 50 ° C - tallow sucroglycerides ... 50 to 55 ° C - palm oil sucroglycerides ... 55 to 58 ° C - coconut oil sucroglycerides ... 60 to 62 ° C

Encore plus préférentiellement, on choisit les sucroglycérides d'huile de palme.Even more preferably, the palm oil sucroglycerides are chosen.

Les sucroglycérides peuvent également se présenter sous forme pulvérulente par mise sur un support tel que lait écrémé, lactosérum, saccharose, maltodextrine, amidon, polysaccharides ...The sucroglycerides can also be in powdered form by placing on a support such as skim milk, whey, sucrose, maltodextrin, starch, polysaccharides ...

Par "sucroesters", on entend les monoesters et diesters de saccharose obtenus par action du saccharose sur un acide gras pouvant contenir de 12 à 20 atomes de carbone (du même type que celui mis en oeuvre pour préparer des sucroglycérides) ou bien par séparation au sein du mélange (appelé "sucroglycérides") résultant de la transtérification du saccharose et de triglycérides naturels ou de synthèse.By "sucroesters" is meant the sucrose monoesters and diesters obtained by the action of sucrose on a fatty acid which may contain from 12 to 20 carbon atoms (of the same type as that used to prepare sucroglycerides) or else by separation with within the mixture (called "sucroglycerides") resulting from the transterification of sucrose and natural or synthetic triglycerides.

Les sucroesters peuvent se présenter sous forme pâteuse ou sous forme pulvérulente par mise sur support du même type que ceux cités plus haut concernant les sucroglycérides.The sucroesters can be in pasty form or in pulverulent form by placing on a support of the same type as those mentioned above concerning the sucroglycerides.

Les émulsions stables d'huiles essentielles faisant l'objet de l'invention peuvent être préparées par différents procédés.The stable emulsions of essential oils which are the subject of the invention can be prepared by various methods.

Un premier mode de préparation consiste à disperser le sucroglycéride ou le sucroester dans de l'eau à une température de l'ordre de 20 à 60° C, à ajouter la gomme xanthane sous agitation jusqu'à obtenir une solution puis à disperser l'huile essentielle dans le mélange aqueux par homogénéisation.A first method of preparation consists in dispersing the sucroglyceride or the sucroester in water at a temperature of the order of 20 to 60 ° C., adding the xanthan gum with stirring until a solution is obtained and then dispersing the essential oil in the aqueous mixture by homogenization.

Un deuxième mode considéré comme préférentiel consiste
- d'une part à disperser le sucroglycéride ou le sucroester dans de l'eau à une température de l'ordre de 20 à 60° C puis à y disperser l'huile essentielle par homogénéisation
- d'autre part, à préparer une solution aqueuse de gomme xanthane à une température de l'ordre de 20 à 60° C
- à introduire la solution de gomme xanthane obtenue dans la dispersion de sucroglycéride ou sucroester et d'huile essentielle
- puis à homogénéiser.A second mode considered to be preferential consists
on the one hand to disperse the sucroglyceride or the sucroester in water at a temperature of the order of 20 to 60 ° C. and then to disperse the essential oil therein by homogenization
- on the other hand, to prepare an aqueous solution of xanthan gum at a temperature of the order of 20 to 60 ° C.
- to introduce the xanthan gum solution obtained in the dispersion of sucroglyceride or sucroester and essential oil
- then homogenize.

Les émulsions aqueuses stables d'huiles essentielles peuvent être utilisées pour la préparation de concentrats d'aromatisation de produits alimentaires (boissons sans alcools, confiserie) ou de concentrats pour cosmétiques.Stable aqueous emulsions of essential oils can be used for the preparation of food flavoring concentrates (soft drinks, confectionery) or concentrates for cosmetics.

Les exemples suivants sont donnés à titre indicatif et ne peuvent être considérés comme une limite du domaine et de l'esprit de l'invention.The following examples are given for information only and cannot be considered as limiting the scope and spirit of the invention.

Mode opératoire n° 1Procedure n ° 1

Dans un bécher de 800 ml, on dissout le sucroglycéride ou le sucroester dans de l'eau, à 80° C sous agitation à 700 tours / minute.In a 800 ml beaker, the sucroglyceride or the sucroester is dissolved in water at 80 ° C. with stirring at 700 rpm.

La gomme xanthane est ensuite versée en pluie ; l'agitation est laissée pendant 15 minutes à 700 tours / minute. La solution obtenue est conservée pendant au moins 2 heures à température ambiante.The xanthan gum is then poured in rain; stirring is left for 15 minutes at 700 revolutions / minute. The solution obtained is kept for at least 2 hours at room temperature.

On ajoute de l'huile essentielle d'orange à la solution obtenue, sous agitation à l'ULTRA TURRAX T45N (distribué par LABO-MODERNE) puis l'ensemble est homogénéisé pendant 40 secondes à la vitesse maximale.Orange essential oil is added to the solution obtained, with stirring with ULTRA TURRAX T45N (distributed by LABO-MODERNE) then the whole is homogenized for 40 seconds at maximum speed.

Mode opératoire n° 2Procedure n ° 2

Dans un bécher de 800 ml, on dissout le sucroglycéride ou le sucroester dans de l'eau, à 80° C sous agitation à 700 tours / minute ; l'agitation est encore maintenue pendant 15 minutes à 700 tours / minutes.In a 800 ml beaker, the sucroglyceride or the sucroester is dissolved in water, at 80 ° C. with stirring at 700 rpm; stirring is still maintained for 15 minutes at 700 revolutions / minute.

Dans un bécher de 500 ml, on verse en pluie de la gomme xanthane dans de l'eau à 80° C sous agitation à 700 tours minute ; l'agitation est encore maintenue pendant 15 minutes à 700 tours / minute.In a 500 ml beaker, poured rain xanthan gum in water at 80 ° C with stirring at 700 rpm; stirring is still maintained for 15 minutes at 700 revolutions / minute.

La solution formée est laissée reposer à température ambiante pendant au moins 2 heures.The solution formed is left to stand at room temperature for at least 2 hours.

L'huile essentielle d'orange est ajoutée à la solution de sucroglycéride ou de sucroester sous agitation à l'ULTRA TURRAX T45N.Orange essential oil is added to the sucroglyceride or sucroester solution with shaking with ULTRA TURRAX T45N.

Après réhomogénéisation, la solution de gomme xanthane est introduite dans le mélange d'huile essentielle et de sucroglycéride ou sucroester, puis l'ensemble est homogénéisé pendant 40 secondes à l'ULTRA TURRAX T45N à la vitesse maximale.After rehomogenization, the xanthan gum solution is introduced into the mixture of essential oil and sucroglyceride or sucroester, then the whole is homogenized for 40 seconds with ULTRA TURRAX T45N at maximum speed.

Test de stabilitéStability test

Les émulsions préparées sont stockées à différentes températures (ambiante, 4° C et 50° C) dans des éprouvettes graduées de 100 ml.The prepared emulsions are stored at different temperatures (ambient, 4 ° C and 50 ° C) in 100 ml graduated cylinders.

Leur aspect est examiné après 1 jour, 6 jours et 14 jours de stockage (J + 1 ; J + 6 ; J + 14).Their appearance is examined after 1 day, 6 days and 14 days of storage (D + 1; D + 6; D + 14).

Les codes suivants sont affectés :

  • 1 émulsions stables ou présentant un léger anneau crémeux en surface dù à une faible agrégation des globules gras.
  • 2 Apparition de quelques gouttes d'huile à la surface des émulsions, remontée des globules huileux et début de coalescence des globules
  • 3 Anneau d'huile à la surface des émulsions
  • 4 Présence d'une phase aqueuse au fond de l'éprouvette
  • 5 Début de rupture d'émulsion
  • 6 Rupture d' émulsion.
The following codes are affected:
  • 1 emulsions stable or having a slight creamy ring on the surface due to poor aggregation of fatty globules.
  • 2 Appearance of a few drops of oil on the surface of the emulsions, rise of the oily globules and beginning of coalescence of the globules
  • 3 Oil ring on the surface of the emulsions
  • 4 Presence of an aqueous phase at the bottom of the test piece
  • 5 Beginning of emulsion rupture
  • 6 Break in emulsion.

On considère les émulsions comme stables lorsque le code qui leur est affecté est 1 ou 2.Emulsions are considered stable when the code assigned to them is 1 or 2.

Les matières premières mises en oeuvre pour réaliser les exemples 1 à 21 sont les suivantes :
. huile essentielle d'orange
. gomme xanthane : RHODIGEL commercialisé par Rhône-Poulenc
. sucroglycéride d'huile de palme de spécifications suivantes :
- sucre combiné 19 ± 2 %
- sucre libre ≦ 1,5 %
- indice d'acide ≦ 8
- indice de saponification 150 ± 10
- densité 0,97 à 66° C
- zone de fusion 50 à 60° C
. sucroester d'acide palmitique de spécifications suivantes :
- acide stearique / acide palmitique : 30/70
- monoester / di et triesters : 70/30
- zone de fusion 46 à 52°CThe raw materials used to carry out Examples 1 to 21 are as follows:
. orange essential oil
. xanthan gum: RHODIGEL marketed by Rhône-Poulenc
. palm oil sucroglyceride with the following specifications:
- combined sugar 19 ± 2%
- free sugar ≦ 1.5%
- acid number ≦ 8
- saponification index 150 ± 10
- density 0.97 at 66 ° C
- melting zone 50 to 60 ° C
. palmitic acid sucroester of the following specifications:
- stearic acid / palmitic acid: 30/70
- monoester / di and triesters: 70/30
- melting zone 46 at 52 ° C

Exemples 1 - 21Examples 1 - 21

On prépare selon le mode opératoire n° 1 ou n° 2 des émulsions d'huile essentielle d'orange.Orange essential oil emulsions are prepared according to procedure No. 1 or No. 2.

Les quantités des différents constituants ainsi que la stabilité des émulsions obtenues figurent aux tableaux I et II.The amounts of the various constituents and the stability of the emulsions obtained are shown in Tables I and II.

A titre comparatif sont données au tableau III les stabilités de dispersions aqueuses d'huile essentielle d'orange préparées à l'aide de gomme arabique (dispersant le plus utilisé actuellement mais posant des problèmes d'approvisionnement) d'une part et de gomme xanthane seule d'autre part. TABLEAU I EX MODE OPERATOIRE COMPOSITION CONSERVATION DES EMULSIONS HUILE ESSENTIELLE % GOMME XANTHANE % SUCRO GLYCERIDE % TEMPERATURE ° C J+1 J+6 J+14 1 1 1 0,35 0,03 ambiante 1 1 1 + 4 1 1 1 + 50 1 5 2 1 5 0,35 0,03 ambiante 1 2 2 + 4 1 1 1 + 50 1 6 3 1 10 0,35 0,03 ambiante 1 1 1 + 4 1 1 1 + 50 1 6 4 2 1 0,35 0,03 ambiante 1 1 1 + 4 1 1 1 + 50 1 6 5 2 5 0,35 0,03 ambiante 1 1 1 + 4 1 1 1 + 50 1 6 6 2 10 0,35 0,03 ambiante 1 1 1 + 4 1 1 1 + 50 1 6 7 2 20 0,35 0,03 ambiante 1 2 2 + 4 1 1 2 + 50 1 6 8 2 40 0,35 0,03 ambiante 2 2 2 + 4 2 2 2 + 50 2 6 9 1 8 0,4 0,03 ambiante 1 1 1 + 4 1 1 1 + 50 1 1 10 1 8 1 0,03 ambiante 1 1 2 + 4 1 1 1 + 50 1 1 TABLEAU II EX MODE OPERATOIRE COMPOSITION CONSERVATION DES EMULSIONS HUILE ESSENTIELLE % GOMME XANTHANE % SUCRO GLYCERIDE % TEMPERATURE ° C J+1 J+6 J+14 11 2 8 0,4 0,03 ambiante 1 1 1 + 4 1 1 1 + 50 1 1 12 2 8 1 0,03 ambiante 1 1 2 + 4 1 1 1 + 50 1 1 13 1 8 0,35 0,02 ambiante 1 1 6 + 4 1 1 6 + 50 1 6 14 1 8 0,35 0,07 ambiante 1 1 1 + 4 1 1 1 + 50 1 6 15 2 8 0,35 0,02 ambiante 1 1 6 + 4 1 2 6 + 50 1 6 16 2 8 0,35 0,07 ambiante 1 1 1 + 4 1 1 1 + 50 1 6 17 2 8 0,35 0,3 ambiante 1 1 1 + 4 1 1 1 + 50 1 2 18 1 8 0,35 0,03 ambiante 1 1 2 + 4 1 1 1 + 50 1 5 19 1 8 0,4 0,07 ambiante 1 1 1 + 4 1 1 1 + 50 1 1 20 2 8 0,4 0,07 ambiante 1 1 1 + 4 1 1 1 + 50 1 2 SUCRO ESTER % 21 2 8 0,35 0,05 ambiante 1 1 1 + 4 1 1 1 + 50 1 5 TABLEAU III EX COMPOSITION CONSERVATION DES EMULSIONS HUILE ESSENTIELLE % GOMME XANTHANE % GOMME ARABIQUE % TEMPERATURE ° C CODE A J+1 J+6 J+14 22 8 / 20 ambiante 1 5 + 4 1 5 23 8 0,2 / ambiante 3 24 8 0,35 / ambiante 3 25 5 0,4 / ambiante 3 By way of comparison are given in Table III the stabilities of aqueous dispersions of orange essential oil prepared using gum arabic (dispersant the most used at present but posing supply problems) on the one hand and xanthan gum alone on the other hand. TABLE I EX OPERATING MODE COMPOSITION STORAGE OF EMULSIONS ESSENTIAL OIL % XANTHAN GUM % SUCRO GLYCERIDE% TEMPERATURE ° C D + 1 D + 6 D + 14 1 1 1 0.35 0.03 ambient 1 1 1 + 4 1 1 1 + 50 1 5 2 1 5 0.35 0.03 ambient 1 2 2 + 4 1 1 1 + 50 1 6 3 1 10 0.35 0.03 ambient 1 1 1 + 4 1 1 1 + 50 1 6 4 2 1 0.35 0.03 ambient 1 1 1 + 4 1 1 1 + 50 1 6 5 2 5 0.35 0.03 ambient 1 1 1 + 4 1 1 1 + 50 1 6 6 2 10 0.35 0.03 ambient 1 1 1 + 4 1 1 1 + 50 1 6 7 2 20 0.35 0.03 ambient 1 2 2 + 4 1 1 2 + 50 1 6 8 2 40 0.35 0.03 ambient 2 2 2 + 4 2 2 2 + 50 2 6 9 1 8 0.4 0.03 ambient 1 1 1 + 4 1 1 1 + 50 1 1 10 1 8 1 0.03 ambient 1 1 2 + 4 1 1 1 + 50 1 1 EX OPERATING MODE COMPOSITION STORAGE OF EMULSIONS ESSENTIAL OIL % XANTHAN GUM % SUCRO GLYCERIDE% TEMPERATURE ° C D + 1 D + 6 D + 14 11 2 8 0.4 0.03 ambient 1 1 1 + 4 1 1 1 + 50 1 1 12 2 8 1 0.03 ambient 1 1 2 + 4 1 1 1 + 50 1 1 13 1 8 0.35 0.02 ambient 1 1 6 + 4 1 1 6 + 50 1 6 14 1 8 0.35 0.07 ambient 1 1 1 + 4 1 1 1 + 50 1 6 15 2 8 0.35 0.02 ambient 1 1 6 + 4 1 2 6 + 50 1 6 16 2 8 0.35 0.07 ambient 1 1 1 + 4 1 1 1 + 50 1 6 17 2 8 0.35 0.3 ambient 1 1 1 + 4 1 1 1 + 50 1 2 18 1 8 0.35 0.03 ambient 1 1 2 + 4 1 1 1 + 50 1 5 19 1 8 0.4 0.07 ambient 1 1 1 + 4 1 1 1 + 50 1 1 20 2 8 0.4 0.07 ambient 1 1 1 + 4 1 1 1 + 50 1 2 SUCRO ESTER% 21 2 8 0.35 0.05 ambient 1 1 1 + 4 1 1 1 + 50 1 5 EX COMPOSITION STORAGE OF EMULSIONS ESSENTIAL OIL % XANTHAN GUM % GUM ARABIC % TEMPERATURE ° C CODE A D + 1 D + 6 D + 14 22 8 / 20 ambient 1 5 + 4 1 5 23 8 0.2 / ambient 3 24 8 0.35 / ambient 3 25 5 0.4 / ambient 3

Claims (15)

1/ Emulsions aqueuses stables d'huiles essentielles caractérisées en ce qu'elles sont constituées de :
- 1 à 45 parties en poids d'une huile essentielle
- 0,01 à 1 partie en poids d'un émulsifiant non-ionique choisi parmi les sucroglycérides et les sucroesters
- 0,2 à 1,5 partie en poids de gomme xanthane
- et du complément à 100 parties en poids d'eau.1 / Stable aqueous emulsions of essential oils characterized in that they consist of:
- 1 to 45 parts by weight of an essential oil
- 0.01 to 1 part by weight of a nonionic emulsifier chosen from sucroglycerides and sucroesters
- 0.2 to 1.5 parts by weight of xanthan gum
- and the complement to 100 parts by weight of water. 2/ Emulsions aqueuses stables d'huiles essentielles caractérisées en ce qu'elles sont constituées de :
- de 1 à 20 parties en poids d'une huile essentielle
- de 0,015 à 0,5 partie en poids d'un émulsifiant non-ionique choisi parmi les sucroglycérides et les sucroesters
- de 0,25 à 1 partie en poids de gomme xanthane
- et du complément à 100 parties en poids d'eau.2 / Stable aqueous emulsions of essential oils characterized in that they consist of:
- from 1 to 20 parts by weight of an essential oil
- from 0.015 to 0.5 parts by weight of a nonionic emulsifier chosen from sucroglycerides and sucroesters
- from 0.25 to 1 part by weight of xanthan gum
- and the complement to 100 parts by weight of water. 3/ Emulsions aqueuses stables d'huiles essentielles selon la revendica­tion 1 ou 2 caractérisées en que la quantité d'émulsifiant non-­ionique va de 0,03 à 0,3 partie en poids et celle de gomme xanthane de 0,3 à 0,5 partie.3 / stable aqueous emulsions of essential oils according to claim 1 or 2, characterized in that the amount of nonionic emulsifier ranges from 0.03 to 0.3 parts by weight and that of xanthan gum from 0.3 to 0, 5 part. 4/ Emulsions aqueuses stables d'huiles essentielles selon l'une quelconque des revendications 1 à 3 caractérisées en ce que l'huile essentielle est une essence d'agrume.4 / stable aqueous emulsions of essential oils according to any one of claims 1 to 3 characterized in that the essential oil is a citrus essence. 5/ Emulsions aqueuses stables d'huiles essentielles selon l'une quelconque des revendications 1 à 4 caractérisées en ce que l'émul­sifiant non-ionique est un sucroglycéride d'huile de palme, de saindoux, de coprah ou de suif.5 / stable aqueous emulsions of essential oils according to any one of claims 1 to 4 characterized in that the nonionic emulsifier is a sucroglyceride of palm oil, lard, copra or tallow. 6/ Emulsions aqueuses stables d'huiles essentielles selon l'une quelconque des revendications 1 à 4 caractérisées en ce que l'émul­sifiant non-ionique est un sucroester d'acide palmitique.6 / stable aqueous emulsions of essential oils according to any one of claims 1 to 4 characterized in that the non-ionic emulsifier is a palmitic acid sucroester. 7/ Procédé de préparation d'émulsions stables d'huiles essentielles par mise en solution de gomme xanthane dans une dispersion aqueuse d'un émulsifiant non-ionique choisi parmi les sucroglycérides et les sucroesters et dispersion d'huiles essentielles dans le milieu avant ou après mise en solution de la gomme xanthane, les quantités des différents constituants mis en oeuvre étant les suivants :
- 1 à 45 parties en poids d'huile essentielle
- 0,01 à 1 partie d'émulsifiant non-ionique - 0,2 à 1,5 partie en poids de gomme xanthane - et le complément à 100 parties d'eau.7 / Process for the preparation of stable emulsions of essential oils by dissolving xanthan gum in an aqueous dispersion of a non-ionic emulsifier chosen from sucroglycerides and sucroesters and dispersion of essential oils in the medium before or after solution of xanthan gum, the amounts of the various constituents used being as follows:
- 1 to 45 parts by weight of essential oil
- 0.01 to 1 part of non-ionic emulsifier - 0.2 to 1.5 parts by weight of xanthan gum - and the balance to 100 parts of water. 8/ Procédé selon la revendication 7 caractérisé en ce qu'il consiste à disperser le sucroglycéride ou le sucroester dans de l'eau à une température de l'ordre de 2à à 60° C, à ajouter la gomme xanthane sous agitation jusqu'à obtenir une solution puis à disperser l'huile essentielle dans le mélange aqueux par homogénéisation.8 / A method according to claim 7 characterized in that it consists in dispersing the sucroglyceride or the sucroester in water at a temperature of the order of 2 to 60 ° C, adding xanthan gum with stirring until obtain a solution and then disperse the essential oil in the aqueous mixture by homogenization. 9/ Procédé selon la revendication 7 caractérisé en ce qu'il consiste :
- d'une part à disperser le sucroglycéride ou le sucroester dans de l'eau à une température de l'ordre de 20 à 60° C puis à y disperser l'huile essentielle par homogénéisation
- d'autre part, à préparer une solution aqueuse de gomme xanthane à une température de l'ordre de 20 à 60° C
- à introduire la solution de gomme xanthane obtenue dans la dispersion de sucroglycéride ou sucroester et d'huile essentielle
- puis à homogénéiser.9 / A method according to claim 7 characterized in that it consists:
on the one hand to disperse the sucroglyceride or the sucroester in water at a temperature of the order of 20 to 60 ° C. and then to disperse the essential oil therein by homogenization
- on the other hand, to prepare an aqueous solution of xanthan gum at a temperature of the order of 20 to 60 ° C.
- to introduce the xanthan gum solution obtained in the dispersion of sucroglyceride or sucroester and essential oil
- then homogenize. 10/Procédé selon l'une quelconque des revendications 7 à 9 caractérisé en ce que les quantités des différents constituants sont les suivantes :
- 1 à 20 parties en poids d'huile essentielle
- 0,015 à 0,5 partie en poids d'émulsifiant non-ionique
- 0,25 à 1 partie en poids de gomme xanthane.10 / A method according to any one of claims 7 to 9 characterized in that the amounts of the various constituents are as follows:
- 1 to 20 parts by weight of essential oil
- 0.015 to 0.5 parts by weight of nonionic emulsifier
- 0.25 to 1 part by weight of xanthan gum. 11/Procédé selon l'une quelconque des revendications 7 à 10 caractérisé en ce que la quantité d'émulsifiant non-ionique va de 0,03 à 0,3 partie en poids et celle de gomme xanthane de 0,3 à 0,5 partie.11 / A method according to any one of claims 7 to 10 characterized in that the amount of nonionic emulsifier ranges from 0.03 to 0.3 parts by weight and that of xanthan gum from 0.3 to 0.5 part. 12/Procédé selon l'une quelconque des revendications 7 à 11 caractérisé en ce que l'huile essentielle est une essence d'agrume.12 / A method according to any one of claims 7 to 11 characterized in that the essential oil is a citrus essence. 13/Procédé selon l'une quelconque des revendications 7 à 12 caractérisé en ce que l'émulsifiant non-ionique est un sucroglycéride d'huile de palme, de saindoux, de coprah ou de suif.13 / A method according to any one of claims 7 to 12 characterized in that the nonionic emulsifier is a sucroglyceride of palm oil, lard, copra or tallow. 14/Procédé selon l'une quelconque des revendications 7 à 13 caractérisé en ce que l'émulsifiant non-ionique est un sucroester d'acide palmitique.14 / A method according to any one of claims 7 to 13 characterized in that the nonionic emulsifier is a palmitic acid sucroester. 15/Utilisation des émulsions aqueuses stables d'huiles essentielles faisant l'objet des revendications 1 à 16 à la préparation de concentrats d'aromatisation.15 / Use of stable aqueous emulsions of essential oils forming the subject of claims 1 to 16 for the preparation of flavoring concentrates.
EP89400593A 1988-03-14 1989-03-03 Stable aqueous emulsions of essential oils Expired - Lifetime EP0333548B1 (en)

Priority Applications (1)

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AT89400593T ATE79897T1 (en) 1988-03-14 1989-03-03 STORABLE AQUEOUS EMULSIONS OF ESSENTIAL OILS.

Applications Claiming Priority (2)

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FR8803264A FR2628339B1 (en) 1988-03-14 1988-03-14 STABLE AQUEOUS EMULSIONS OF ESSENTIAL OILS
FR8803264 1988-03-14

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WO1997010803A1 (en) * 1995-09-18 1997-03-27 Stepan Company Methods and compositions for conditioning skin and hair
EP0701813A3 (en) * 1994-09-14 1997-05-07 Unilever Plc Oil-in-water emulsion containing a fragrance
FR2815865A1 (en) * 2000-10-31 2002-05-03 Innovaderm USE OF A THERAPEUTIC OR COSMETIC COMPOSITION FOR THE TOPICAL TREATMENT OF CELLULITE, AND COMPOSITION COMPRISING THE APPLICATION
EP1911464A1 (en) * 2006-09-14 2008-04-16 Manfred Dr. Helms Gel-type base compound based on essential oil mixtures for dermal and transdermal application
FR2944458A1 (en) * 2009-04-20 2010-10-22 Ecole De Biolog Ind Ebi Preparing oil-in-water emulsion by directly/phase inversion, useful e.g. to treat fungal infections, comprises preparing phase A having e.g. xanthan, stirring phase, preparing aqueous phase B, adding phases and stirring
FR2980121A1 (en) * 2011-09-20 2013-03-22 Oreal EMULSION OIL IN WATER COMPRISING A HIGH RATE OF VEGETABLE OIL

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FR2523134A1 (en) * 1982-03-11 1983-09-16 Rhone Poulenc Spec Chim Liq. compsn. contg. mucro:glyceride and edible oil - useful as emulsifier for food and cosmetic prods.
FR2563415A1 (en) * 1984-04-27 1985-10-31 Fauque Co Sarl Method for stabilising alcoholic flavours in crystallised (candied, glacé) fruits used in food preparations and products obtained
FR2603459A1 (en) * 1986-09-05 1988-03-11 Etude Rech Dev Alcoholic product for flavouring food products and process for preparing it

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FR2523134A1 (en) * 1982-03-11 1983-09-16 Rhone Poulenc Spec Chim Liq. compsn. contg. mucro:glyceride and edible oil - useful as emulsifier for food and cosmetic prods.
FR2563415A1 (en) * 1984-04-27 1985-10-31 Fauque Co Sarl Method for stabilising alcoholic flavours in crystallised (candied, glacé) fruits used in food preparations and products obtained
FR2603459A1 (en) * 1986-09-05 1988-03-11 Etude Rech Dev Alcoholic product for flavouring food products and process for preparing it

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0701813A3 (en) * 1994-09-14 1997-05-07 Unilever Plc Oil-in-water emulsion containing a fragrance
WO1997010803A1 (en) * 1995-09-18 1997-03-27 Stepan Company Methods and compositions for conditioning skin and hair
AU2002214111B2 (en) * 2000-10-31 2006-06-08 Pierre Fabre Dermo-Cosmetique Anti-adiposis composition based on garlic bulb extracts
WO2002036093A2 (en) * 2000-10-31 2002-05-10 Innovaderm Anti-adiposis composition based on garlic bulb extracts
WO2002036093A3 (en) * 2000-10-31 2003-01-09 Innovaderm Anti-adiposis composition based on garlic bulb extracts
US6852343B2 (en) 2000-10-31 2005-02-08 Pierre Fabre Dermo-Cosmetique Antiadipose topical treatment composition based on garlic bulbs extracts, and cosmetic and therapeutic uses
FR2815865A1 (en) * 2000-10-31 2002-05-03 Innovaderm USE OF A THERAPEUTIC OR COSMETIC COMPOSITION FOR THE TOPICAL TREATMENT OF CELLULITE, AND COMPOSITION COMPRISING THE APPLICATION
AU2002214111B9 (en) * 2000-10-31 2006-11-09 Pierre Fabre Dermo-Cosmetique Anti-adiposis composition based on garlic bulb extracts
EP1911464A1 (en) * 2006-09-14 2008-04-16 Manfred Dr. Helms Gel-type base compound based on essential oil mixtures for dermal and transdermal application
FR2944458A1 (en) * 2009-04-20 2010-10-22 Ecole De Biolog Ind Ebi Preparing oil-in-water emulsion by directly/phase inversion, useful e.g. to treat fungal infections, comprises preparing phase A having e.g. xanthan, stirring phase, preparing aqueous phase B, adding phases and stirring
FR2944457A1 (en) * 2009-04-20 2010-10-22 Ecole De Biolog Ind Ebi PROCESS FOR MANUFACTURING DIRECT AND INDIRECT COLD-INDIRECT OIL-IN-WATER EMULSION WITH LOW AGITATION
FR2980121A1 (en) * 2011-09-20 2013-03-22 Oreal EMULSION OIL IN WATER COMPRISING A HIGH RATE OF VEGETABLE OIL
WO2013041553A1 (en) * 2011-09-20 2013-03-28 L'oreal Oil-in-water emulsion including a high plant oil content

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NO891055L (en) 1989-09-15
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AU609587B2 (en) 1991-05-02
AU3125689A (en) 1989-09-14
CA1341316C (en) 2001-11-06
ATE79897T1 (en) 1992-09-15
ES2046498T3 (en) 1994-02-01
DK119389D0 (en) 1989-03-13
IL89589A0 (en) 1989-09-10
NO891055D0 (en) 1989-03-13
PT89989A (en) 1989-11-10
EP0333548B1 (en) 1992-08-26
DE68902557T2 (en) 1993-03-18
JPH0661456B2 (en) 1994-08-17
FR2628339A1 (en) 1989-09-15
DK119389A (en) 1989-09-15
JPH0221939A (en) 1990-01-24
DE68902557D1 (en) 1992-10-01

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