WO2013037665A1 - Vanillin compositions in liquid form - Google Patents

Vanillin compositions in liquid form Download PDF

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Publication number
WO2013037665A1
WO2013037665A1 PCT/EP2012/067181 EP2012067181W WO2013037665A1 WO 2013037665 A1 WO2013037665 A1 WO 2013037665A1 EP 2012067181 W EP2012067181 W EP 2012067181W WO 2013037665 A1 WO2013037665 A1 WO 2013037665A1
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WO
WIPO (PCT)
Prior art keywords
vanillin
solvent
composition
composition according
ether
Prior art date
Application number
PCT/EP2012/067181
Other languages
French (fr)
Inventor
Corine COCHENNEC
Sandrine Rochat
Jean-Claude Le Thiesse
Fabienne HENRY
Original Assignee
Rhodia Operations
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
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Publication of WO2013037665A1 publication Critical patent/WO2013037665A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
    • A23C9/156—Flavoured milk preparations ; Addition of fruits, vegetables, sugars, sugar alcohols or sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/111—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/204—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • 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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/44—Perfumes; Colouring materials; Brightening agents ; Bleaching agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/30—Feeding-stuffs specially adapted for particular animals for swines
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/60—Feeding-stuffs specially adapted for particular animals for weanlings

Definitions

  • the present invention relates to vanillin compositions in liquid form and to their process of preparation.
  • the present invention also relates to the uses of said compositions, in particular in the pharmaceutical or food field.
  • Vanillin is a widely used product in many fields of application as aroma and / or fragrance.
  • vanillin is widely consumed in the food and feed industry but it also has applications in other areas such as for example, pharmacy or perfumery. It follows that it is a consumer product.
  • Vanillin is currently available on the market in the form of a crystalline powder.
  • the disadvantages that result are the presence of fines that cause problems of dusting and flowability, during storage and handling of said powder.
  • - be in the form of a liquid product may be poured or pumped at room temperature of the order of 15 ° C to 25 ° C; and or
  • the present invention aims to provide a new liquid formulation of vanillin meeting the above requirements.
  • the present invention therefore aims to provide a stable liquid vanillin composition over time at room temperature.
  • the present invention therefore aims to provide a liquid vanillin composition having no crystallization or demixing over time.
  • the present invention also aims to provide a liquid composition having good organoleptic properties and having a high aromatic power.
  • the present invention aims to provide a liquid composition having an aromatic power greater than that of vanillin.
  • the present invention relates to a vanillin composition in liquid form comprising vanillin, ethyl vanillin and at least one solvent other than methanol, wherein the amount of solvent is at least 40% by weight with respect to total weight of said composition and vanillin / ethylvanillin mass ratio is from 75/25 to 40/60.
  • the amount of solvent is calculated by weight relative to the total weight of the composition, namely relative to the total weight of vanillin, ethyl vanillin and solvent.
  • compositions of the invention have the advantage of being sufficiently concentrated and therefore of presenting an appropriate aroma force, without the appearance of crystallization phenomena generating instability.
  • the amount of solvent is at least 50%, preferably at least 60%, by weight relative to the total weight of said composition.
  • An advantageous composition according to the present invention is characterized in that the amount of solvent represents from 40% to 90% by weight relative to the total weight of said composition.
  • Another advantageous composition according to the present invention is characterized in that the amount of solvent represents from 60% to 80% by weight relative to the total weight of said composition.
  • the mass ratio vanillin / ethyl vanillin is from 75/25 to 45/55, more preferably from 70/30 to 45/55 and even more preferably from 70/30 to 60/40.
  • the amount of vanillin is from 40% to 75% by weight relative to the total weight of solids and the amount of ethylvanillin is from 25% to 60% by weight relative to the total weight of dry matter.
  • total weight of solids means the total weight of ethylvanillin and vanillin. It is therefore the weight of the composition without the solvent.
  • the amount of vanillin is from 45% to 75% by weight relative to the total weight of solids and the amount of ethylvanillin is from 25% to 55% by weight. % by weight relative to the total weight of dry matter.
  • the amount of vanillin is from 60% to 75% by weight relative to the total weight of solids and the amount of ethylvanillin is from 25% to 40% by weight. % by weight relative to the total weight of dry matter.
  • An advantageous composition according to the present invention preferably comprises from 20 to 60% by weight, very preferably from 20 to 50% by weight of vanillin and ethyl vanillin relative to the total weight of said composition.
  • the solvent present in the vanillin composition according to the invention is liquid at ambient temperature, that is to say generally in a temperature zone varying between 10 ° C. and 30 ° C., preferentially varying between 10 ° C and 25 ° C, very preferably between 16 ° C and 22 ° C.
  • said solvent does not comprise or consists of methanol.
  • the solvent used is an aqueous or organic solvent, or a mixture of solvents.
  • a polar, apolar, protic or aprotic organic solvent is preferably chosen.
  • solvents that can be used in the compositions of the invention it is preferable to use a polar, apolar, protic or aprotic organic solvent or a mixture of said solvents.
  • solvents mention may be made in particular of the following solvents:
  • alcohols or diols preferably aliphatic or arylaliphatic and more preferentially, ethanol, propanol, isopropanol, butanol, beta-phenylethyl alcohol, ethylene glycol, diethylene glycol, monopropylene glycol, glycerol ;
  • ether-oxides preferably aliphatic ether-oxides and, more particularly, diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, methyl tert-butyl ether, ethyl tert-butyl ether, di-tert-butyl ether, ethylene glycol dimethyl ether and diethylene glycol dimethyl ether;
  • the solvent is selected from the group consisting of water, glyceryl triacetate (or triacetin), ethanol, monopropylene glycol, glycerol and mixtures thereof.
  • a solvent that can be used in the food industry is used.
  • the solvent when it is water, it is preferably used in a mixture with another solvent advantageously chosen from the solvents described above.
  • the water / ethanol and water / monopropylene glycol solvent mixtures are preferred.
  • the amount of water present in a solvent mixture is such that it represents from 2% to 30% by weight relative to the total weight of the composition.
  • compositions of the invention may also comprise an antioxidant, in particular ascorbic acid.
  • the present invention relates to a composition as defined above comprising ascorbic acid at, for example, from 0.01% to 1%, preferably from 0.01% to 0.5% by weight. weight relative to the total weight of said composition.
  • solutions of vanillin and ethyl vanillin mixtures in a solvent develop a yellow coloration.
  • This coloration may be limited by the use of a food antioxidant such as ascorbic acid.
  • compositions of the invention may also comprise a food coloring, in particular a caramel.
  • a food coloring such as caramel also allows the color to be stabilized at a higher brown level.
  • the additives advantageously present in the composition according to the invention represent a total amount less than the amount of vanillin and ethyl vanillin.
  • the present invention also relates to a process for preparing the compositions as defined above, comprising mixing vanillin, ethyl vanillin and the solvent with stirring.
  • vanillin and ethyl vanillin are preferably introduced into the solvent which is kept stirring.
  • the process of the invention is carried out at ambient temperature of between 15 ° C. and 30 ° C., but it may also comprise a step of heating the mixture obtained in order to obtain a liquid that is recovered.
  • the mixture is brought to a temperature preferably lower than or equal to 50 ° C, preferably between 20 ° C and 50 ° C, and even more preferably between 20 ° C and 30 ° C.
  • the mixture is stirred with stirring until a homogeneous solution is obtained. Generally, the duration varies between 10 minutes and 3 hours. Then, the composition is obtained in liquid form that is conditioned according to the needs of use.
  • the present invention also relates to a food composition comprising a vanillin composition according to the present invention.
  • the present invention also relates to the use of the vanillin composition according to the present invention as a flavor, as a perfume, as an odor-masking agent or as a perfume base.
  • compositions of the invention can be used in many fields of application, inter alia, in the food and pharmaceutical field, and in the perfume industry.
  • the present invention relates to the use of the vanillin composition as defined above as aroma in the field of food and feed, pharmacy, and as perfume, in the cosmetics industry, the perfumery and detergency.
  • the vanillin composition as defined above can be used as odor masking agent, in particular in the pharmaceutical industry.
  • the vanillin composition as defined above can be used in the field of cosmetics for the preparation of creams, milks and blushes and other products, as perfume base in perfumery and in the field of cosmetics. detergency, especially in soap.
  • compositions of the invention are that of biscuit and pastry, and more particularly:
  • the basic elements present in the mixtures intended for the aforementioned industries are the proteins (gluten) and the starch which are most often brought by the wheat flour.
  • ingredients such as sucrose, salt, eggs, milk, fatty substances, possibly chemical yeasts (sodium bicarbonate or other artificial yeasts) or organic yeasts and flours are added to the flour.
  • the incorporation of the vanillin composition according to the invention is carried out during manufacture, according to the desired product and is carried out according to the classical techniques of the field considered (see in particular JL KIGER and JC KIGER - Modern Techniques of Biscuit, Pastry-bakery industrial and artisanal, DUNOD, Paris, 1968, Volume 2, pp. 231 and following).
  • the composition of the invention is introduced into the fatty substances that are involved in the preparation of the dough.
  • composition of the invention is introduced in an amount of 0.05 to 1.5 g per kg of dough.
  • compositions of the invention are quite suitable for use in the field of chocolate and whatever the form of implementation: chocolate plates, formulation chocolates, filling for chocolates.
  • cocoa paste can be introduced during conching, that is to say the mixing of the cocoa paste with the various ingredients, including flavorings, or after conching, by use in cocoa butter.
  • the vanillin compositions of the invention are used according to the type of chocolate, at a rate of 0.05 g to 1 g per 1 kg of finished product, the highest contents being found in chocolate. for cover.
  • compositions of the invention are the manufacture of sweets of all kinds: sugared almonds, caramels, nougats, boiled sweets, melting sweets and others.
  • compositions of the invention may vary between 0.001% and 0.2%.
  • compositions of the invention are well suited for uses in the dairy industry and more particularly in flavored and gelled milks, desserts, yogurts, ice creams and ice creams.
  • the aromatization is by simple addition of the compositions of the invention, in one of the mixing stages required during the preparation of the product.
  • compositions to be used are generally low, of the order of 0.2 g per 1 kg of finished product.
  • compositions of the invention in the food field is the preparation of vanillin sugar, that is to say the impregnation of the sugar with these, in a content of about 7 g expressed relative to to 1 kg of finished product.
  • compositions of the invention may also be used in various drinks and include, among others, grenadine and chocolate drinks. It is common to use vanillin for the denaturation of butter. For this purpose, the vanillin compositions of the invention may be used at a rate of 6 g per tonne of butter.
  • compositions of the invention are animal feed, especially for the preparation of feed meal for calves and pigs.
  • the recommended content is about 0.2 g per kg of flour to be flavored.
  • compositions of the invention may find other applications as a masking agent, for the pharmaceutical industry (masking the drug odor) or for other industrial products (of the rubber, plastic, rubber, etc. type). .
  • compositions are meant mixtures of various ingredients such as solvents, solid or liquid carriers, fixatives, various odorous compounds, etc., in which are incorporated the compositions of the invention, which are used to provide various types of of finished products, the sought-after fragrance.
  • Fragrance bases are preferred examples of perfume compositions in which the compositions of the invention may be advantageously used at a level of from 0.1% to 2.5% by weight.
  • the bases for perfume can be used for the preparation of many scented products such as, for example, toilet waters, perfumes, aftershave lotions; toilet and hygiene products such as bath or shower gels, deodorant or antiperspirant products, whether in the form of sticks or lotions, talcs or powders of any kind; hair products such as shampoos and hair products of all types.
  • scented products such as, for example, toilet waters, perfumes, aftershave lotions
  • toilet and hygiene products such as bath or shower gels, deodorant or antiperspirant products, whether in the form of sticks or lotions, talcs or powders of any kind
  • hair products such as shampoos and hair products of all types.
  • compositions of the invention is the field of soap. They can be used at a content of 0.3% to 0.75% of the total mass to be perfumed.
  • vanillin is combined in this application with benzoin resinoid and sodium hyposulphite (2%).
  • the vanillin compositions according to the invention can find many other applications, in particular in air fresheners or any maintenance product.
  • MPG monopropyleneglycol (or 1, 2-propanediol)
  • the preparation is carried out at ambient temperature by mixing the various constituents.
  • a vanillin / ethyl vanillin / MPG mixture consisting of 20% by weight of vanillin, 20% by weight of ethyl vanillin and 60% by weight of MPG (mixture according to the 20/20/60 mass ratio) is prepared according to the following procedure:
  • Vanillin and ethyl vanillin are poured in 5 minutes with stirring.
  • a liquid vanillin composition according to the invention is thus obtained.
  • compositions 4 to 8 in Table 1 The same protocol is applied for the preparation of liquid vanillin compositions according to the invention (compositions 4 to 8 in Table 1) and for the preparation of vanillin compositions not in accordance with the invention (compositions 1, 2 and 3 in Table 1), adapting only the amounts of solvent, vanillin and ethyl vanillin.
  • the vanillin / ethyl vanillin / solvent mass proportions for each of compositions 1 to 8 are shown in Table 1.
  • Example 2 Stability of the Vanillin Compositions of the Invention
  • Several liquid compositions of vanillin according to the invention were prepared and the stability of these solutions was evaluated, in particular in order to control the absence of crystallization or demixing over a period of 3 months.
  • liquid compositions are all prepared by mixing the solvent, ethyl vanillin and vanillin according to the protocol of Example 1.
  • compositions according to the invention (4 to 8) are stable over time, both at room temperature and at 4 ° C.
  • compositions comprising only 20% by weight of solvent are not stable over time and crystallizes at room temperature and at 4 ° C.
  • a composition containing a single compound selected from vanillin and ethyl vanillin is also not stable over time and crystallizes at room temperature and at 4 ° C although said composition contains a quantity of dry matter (vanillin or ethyl vanillin) identical to that of the compositions according to the invention (cf. compositions 2 and 3 against composition 4 which contain 40% by weight of dry material (s)).
  • the color number of the vanillin / ethyl vanillin / MPG composition was measured according to the 20/20/60 mass ratio (prepared in Example 1), stored in a transparent bottle at room temperature, in the light during time. Ascorbic acid (antioxidant) was added to the composition. The results are collated in Table 2 below.
  • Table 2 Evolution of the color index of a vanillin / ethyl vanillin composition as a function of time and the presence of antioxidant
  • the color number is determined on a Minolta colorimeter by the so-called "yellow index” test according to the standard method DI No. 6167 (measurement of yellow index according to the standard method DI No. 6167).
  • the color number is lower as the composition is insensitive to light.
  • composition 4 of the invention 0.6 g of the liquid flavor which is the subject of the invention (composition 4 of the invention) are added.
  • composition 4 of the invention 0.6 g of the liquid flavor which is the subject of the invention.
  • Example 1 After homogenization, the preparation is assessed by olfaction by the retro-nasal route by a panel of evaluators.
  • the flavored milk 0.06% by weight of the composition of the invention has a vanilla flavor similar to vanillin.
  • composition 4 of Example 1 250 parts of fat and 0.5 parts of liquid flavor of the invention (composition 4 of Example 1) are mixed with 250 parts of sugar until an ointment.
  • 250 parts of egg are added to the mixture.
  • the mixture is beaten until a homogeneous mixture.
  • 250 parts of flour and 2 parts of salt are also added.
  • the mixture is beaten until a homogeneous paste.
  • the cake is baked for 30 minutes at 150 ° C.
  • the cake is evaluated after one day at room temperature by olfaction by the retro-nasal route by a panel of evaluators.
  • the cake flavored to 0.05% by weight of the composition of the invention has a vanilla flavor, similar to vanillin.

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  • Oil, Petroleum & Natural Gas (AREA)
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Abstract

The invention relates to a vanillin composition in liquid form, which contains vanillin, ethylvanillin, and at least one solvent other than methanol, wherein the solvent is present in an amount of at least 40 wt % relative to the total weight of said composition, while the weight ratio of vanillin/ethylvanillin is 75/25 to 40/60.

Description

COMPOSITIONS DE VANILLINE SOUS FORME LIQUIDE  VANILLIN COMPOSITIONS IN LIQUID FORM
La présente invention a pour objet des compositions de vanilline sous forme liquide ainsi que leur procédé de préparation. La présente invention a également pour objet les utilisations desdites compositions, notamment dans le domaine pharmaceutique ou alimentaire. The present invention relates to vanillin compositions in liquid form and to their process of preparation. The present invention also relates to the uses of said compositions, in particular in the pharmaceutical or food field.
La vanilline est un produit largement utilisé dans de nombreux domaines d'application en tant qu'arôme et/ou parfum.  Vanillin is a widely used product in many fields of application as aroma and / or fragrance.
Ainsi, la vanilline se trouve abondamment consommée dans l'industrie alimentaire et animale mais elle a aussi des applications dans d'autres domaines tels que par exemple, la pharmacie ou la parfumerie. Il s'ensuit que c'est un produit de grande consommation.  Thus, vanillin is widely consumed in the food and feed industry but it also has applications in other areas such as for example, pharmacy or perfumery. It follows that it is a consumer product.
La vanilline est actuellement disponible sur le marché sous la forme d'une poudre cristallisée. Les inconvénients qui en résultent sont la présence de fines qui entraînent des problèmes de poussiérage et de coulabilité, lors du stockage et de la manipulation de ladite poudre.  Vanillin is currently available on the market in the form of a crystalline powder. The disadvantages that result are the presence of fines that cause problems of dusting and flowability, during storage and handling of said powder.
Actuellement, on souhaite disposer dans de multiples applications, des ingrédients sous une forme liquide. En effet, outre que cette forme résolve le problème du poussiérage et de coulabilité, une présentation liquide présente beaucoup d'avantages, en particulier une facilité de dosage et une manipulation plus aisée.  Currently, it is desired to have in many applications, ingredients in a liquid form. Indeed, besides this form solves the problem of dusting and flowability, a liquid presentation has many advantages, particularly ease of dosing and easier handling.
Par ailleurs, il est connu qu'il est difficile de mettre au point des compositions liquides de vanilline suffisamment concentrées et présentant en outre une bonne stabilité au cours du temps, à savoir des compositions liquides stables au cours du temps, notamment à température ambiante, sans cristallisation.  Moreover, it is known that it is difficult to develop liquid compositions of sufficiently concentrated vanillin and further having good stability over time, namely stable liquid compositions over time, especially at room temperature, without crystallization.
Le problème qui se pose est donc de trouver une nouvelle formulation de la vanilline qui satisfasse aux impératifs suivants :  The problem is therefore to find a new formulation of vanillin which satisfies the following requirements:
- se présenter sous la forme d'un produit liquide susceptible d'être versé ou pompé à température ambiante de l'ordre de 15°C à 25°C ; et/ou  - be in the form of a liquid product may be poured or pumped at room temperature of the order of 15 ° C to 25 ° C; and or
- être mécaniquement stable c'est-à-dire, ne pas se séparer en phases lors d'une variation de températures dans une zone se situant entre 0°C et 50°C, ni cristalliser lors d'un stockage prolongé ; et/ou  - be mechanically stable, that is to say, not separate in phases during a temperature variation in an area between 0 ° C and 50 ° C, or crystallize during prolonged storage; and or
- être chimiquement stable ; et/ou  - be chemically stable; and or
- posséder une facilité de mise en oeuvre se traduisant par une simple dilution lors de l'emploi ; et/ou - se présenter sous la forme d'une solution transparente ; et/ou - have an ease of implementation resulting in a simple dilution during use; and or - be in the form of a transparent solution; and or
- présenter une coloration qui n'évolue pas ou peu ; et/ou  - have a color that does not evolve or little; and or
- posséder une stabilité bactérienne et ne pas constituer un terrain favorable à un développement de bactéries dans les conditions de températures optimales ; et/ou  - to possess a bacterial stability and not to constitute a ground favorable to a development of bacteria under the conditions of optimal temperatures; and or
- répondre aux exigences organoleptiques dans le cas d'un emploi alimentaire ; et/ou  - meet the organoleptic requirements in the case of a food use; and or
- être en conformité avec la législation du domaine d'application considéré ; et/ou  - to be in conformity with the legislation of the field of application considered; and or
- être facile à fabriquer afin de ne pas grever le prix de vente.  - be easy to manufacture so as not to burden the selling price.
La présente invention a pour but de fournir une nouvelle formulation liquide de la vanilline répondant aux exigences précitées.  The present invention aims to provide a new liquid formulation of vanillin meeting the above requirements.
La présente invention a donc pour but de fournir une composition de vanilline liquide stable au cours du temps à température ambiante.  The present invention therefore aims to provide a stable liquid vanillin composition over time at room temperature.
La présente invention a donc pour but de fournir une composition de vanilline liquide ne présentant pas de cristallisation ou de démixtion au cours du temps.  The present invention therefore aims to provide a liquid vanillin composition having no crystallization or demixing over time.
La présente invention a également pour but de fournir une composition liquide présentant de bonnes propriétés organoleptiques et possédant une puissance aromatique élevée. En particulier, la présente invention vise à mettre à disposition une composition liquide possédant une puissance aromatique supérieure à celle de la vanilline.  The present invention also aims to provide a liquid composition having good organoleptic properties and having a high aromatic power. In particular, the present invention aims to provide a liquid composition having an aromatic power greater than that of vanillin.
Ainsi, la présente invention concerne une composition de vanilline sous forme liquide comprenant de la vanilline, de l'éthylvanilline et au moins un solvant autre que le méthanol, dans laquelle la quantité de solvant est d'au moins 40% en poids par rapport au poids total de ladite composition et le ratio massique vanilline / éthylvanilline est compris de 75/25 à 40/60.  Thus, the present invention relates to a vanillin composition in liquid form comprising vanillin, ethyl vanillin and at least one solvent other than methanol, wherein the amount of solvent is at least 40% by weight with respect to total weight of said composition and vanillin / ethylvanillin mass ratio is from 75/25 to 40/60.
Dans le cadre de la présente invention, la quantité de solvant est calculée en poids par rapport au poids total de la composition, à savoir par rapport au poids total de la vanilline, de l'éthylvanilline et du solvant.  In the context of the present invention, the amount of solvent is calculated by weight relative to the total weight of the composition, namely relative to the total weight of vanillin, ethyl vanillin and solvent.
Les compositions de l'invention présentent l'avantage d'être suffisamment concentrées et donc de présenter une force d'arôme appropriée, sans l'apparition des phénomènes de cristallisation engendrant une instabilité.  The compositions of the invention have the advantage of being sufficiently concentrated and therefore of presenting an appropriate aroma force, without the appearance of crystallization phenomena generating instability.
Selon un mode de réalisation, la quantité de solvant est d'au moins 50%, de préférence d'au moins 60%, en poids par rapport au poids total de ladite composition. Une composition avantageuse selon la présente invention est caractérisée en ce que la quantité de solvant représente de 40% à 90% en poids par rapport au poids total de ladite composition. According to one embodiment, the amount of solvent is at least 50%, preferably at least 60%, by weight relative to the total weight of said composition. An advantageous composition according to the present invention is characterized in that the amount of solvent represents from 40% to 90% by weight relative to the total weight of said composition.
Une autre composition avantageuse selon la présente invention est caractérisée en ce que la quantité de solvant représente de 60% à 80% en poids par rapport au poids total de ladite composition.  Another advantageous composition according to the present invention is characterized in that the amount of solvent represents from 60% to 80% by weight relative to the total weight of said composition.
Selon un mode de réalisation, dans les compositions de l'invention, le ratio massique vanilline / éthylvanilline est compris de 75/25 à 45/55, de manière plus préférée de 70/30 à 45/55 et de manière encore plus préférée de 70/30 à 60/40.  According to one embodiment, in the compositions of the invention, the mass ratio vanillin / ethyl vanillin is from 75/25 to 45/55, more preferably from 70/30 to 45/55 and even more preferably from 70/30 to 60/40.
Ainsi, selon un mode de réalisation, dans les compositions de l'invention, la quantité de vanilline est comprise de 40% à 75% en poids par rapport au poids total de matières sèches et la quantité d'éthylvanilline est comprise de 25% à 60% en poids par rapport au poids total de matières sèches.  Thus, according to one embodiment, in the compositions of the invention, the amount of vanillin is from 40% to 75% by weight relative to the total weight of solids and the amount of ethylvanillin is from 25% to 60% by weight relative to the total weight of dry matter.
Dans le cadre de la présente invention, on entend par "poids total de matières sèches" le poids total de l'éthylvanilline et de la vanilline. Il s'agit donc du poids de la composition sans le solvant.  In the context of the present invention, the term "total weight of solids" means the total weight of ethylvanillin and vanillin. It is therefore the weight of the composition without the solvent.
Selon un mode de réalisation avantageux, dans les compositions selon l'invention, la quantité de vanilline est comprise de 45% à 75% en poids par rapport au poids total de matières sèches et la quantité d'éthylvanilline est comprise de 25% à 55% en poids par rapport au poids total de matières sèches.  According to an advantageous embodiment, in the compositions according to the invention, the amount of vanillin is from 45% to 75% by weight relative to the total weight of solids and the amount of ethylvanillin is from 25% to 55% by weight. % by weight relative to the total weight of dry matter.
Selon un mode de réalisation avantageux, dans les compositions selon l'invention, la quantité de vanilline est comprise de 60% à 75% en poids par rapport au poids total de matières sèches et la quantité d'éthylvanilline est comprise de 25% à 40% en poids par rapport au poids total de matières sèches.  According to an advantageous embodiment, in the compositions according to the invention, the amount of vanillin is from 60% to 75% by weight relative to the total weight of solids and the amount of ethylvanillin is from 25% to 40% by weight. % by weight relative to the total weight of dry matter.
Une composition avantageuse selon la présente invention comprend préférentiellement de 20 à 60% en poids, très préférentiellement de 20 à 50% en poids de vanilline et d'éthylvanilline par rapport au poids total de ladite composition.  An advantageous composition according to the present invention preferably comprises from 20 to 60% by weight, very preferably from 20 to 50% by weight of vanillin and ethyl vanillin relative to the total weight of said composition.
Dans le cadre de la présente invention, le solvant présent dans la composition de vanilline selon l'invention est liquide à température ambiante, c'est-à-dire généralement dans une zone de température variant entre 10°C et 30°C, préférentiellement variant entre 10°C et 25°C, très préférentiellement entre 16°C et 22°C.  In the context of the present invention, the solvent present in the vanillin composition according to the invention is liquid at ambient temperature, that is to say generally in a temperature zone varying between 10 ° C. and 30 ° C., preferentially varying between 10 ° C and 25 ° C, very preferably between 16 ° C and 22 ° C.
Il est choisi pour être chimiquement inerte vis-à-vis de la vanilline et de l'éthylvanilline. Conformément à l'invention, ledit solvant ne comprend ni n'est constitué de méthanol. Selon la présente invention, le solvant utilisé, à l'exception du méthanol, est un solvant aqueux ou organique, ou un mélange de solvants. Parmi les solvants organiques, on choisit préférentiellement un solvant organique polaire, apolaire, protique ou aprotique. It is chosen to be chemically inert to vanillin and ethyl vanillin. According to the invention, said solvent does not comprise or consists of methanol. According to the present invention, the solvent used, with the exception of methanol, is an aqueous or organic solvent, or a mixture of solvents. Among the organic solvents, a polar, apolar, protic or aprotic organic solvent is preferably chosen.
Comme solvants susceptibles d'être mis en oeuvre dans les compositions de l'invention, on peut utiliser, de préférence, un solvant organique polaire, apolaire, protique ou aprotique ou un mélange desdits solvants.  As solvents that can be used in the compositions of the invention, it is preferable to use a polar, apolar, protic or aprotic organic solvent or a mixture of said solvents.
A titre de solvants, on peut citer notamment les solvants suivants :  As solvents, mention may be made in particular of the following solvents:
- de l'eau ou du sirop de glucose ;  - water or glucose syrup;
- des monalcools ou des diols, de préférence, aliphatiques ou arylaliphatiques et plus préférentiellement, l'éthanol, le propanol, l'isopropanol, le butanol, l'alcool beta-phényléthylique, l'éthylèneglycol, le diéthylèneglycol, le monopropylèneglycol, le glycérol ;  alcohols or diols, preferably aliphatic or arylaliphatic and more preferentially, ethanol, propanol, isopropanol, butanol, beta-phenylethyl alcohol, ethylene glycol, diethylene glycol, monopropylene glycol, glycerol ;
- des éther-oxydes de préférence, aliphatiques, et, plus particulièrement, le diéthyléther, le dipropyléther, le diisopropyléther, le dibutyléther, le méthyltertiobutyléther, l'éthyltertiobutyléther, le ditertiobutyléther, le diméthyléther de l'éthylèneglycol, le diméthyléther du diéthylèneglycol ;  preferably aliphatic ether-oxides and, more particularly, diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, methyl tert-butyl ether, ethyl tert-butyl ether, di-tert-butyl ether, ethylene glycol dimethyl ether and diethylene glycol dimethyl ether;
- des esters d'alkyle ou d'arylalkyle d'acides carboxyliques, aliphatiques, cycloaliphatiques ou aromatiques, et plus préférentiellement, l'acétate d'éthyle, l'acétate de butyle, le salicylate de benzyle, le laurate de méthyle, le benzoate de méthyle, le citrate d'éthyle et le triacétate de glycéryle (ou triacétine) ; et  alkyl or arylalkyl esters of carboxylic, aliphatic, cycloaliphatic or aromatic acids, and more preferably, ethyl acetate, butyl acetate, benzyl salicylate, methyl laurate, benzoate methyl, ethyl citrate and glyceryl triacetate (or triacetin); and
- leurs mélanges.  - their mixtures.
Selon un mode de réalisation avantageux, le solvant est choisi dans le groupe constitué de l'eau, du triacétate de glycéryle (ou triacétine), de l'éthanol, du monopropylène glycol, du glycérol et de leurs mélanges. De manière très préférée, on utilise un solvant pouvant être utilisé dans l'industrie alimentaire.  According to an advantageous embodiment, the solvent is selected from the group consisting of water, glyceryl triacetate (or triacetin), ethanol, monopropylene glycol, glycerol and mixtures thereof. Very preferably, a solvent that can be used in the food industry is used.
Selon un mode de réalisation, lorsque le solvant est l'eau, il est de préférence utilisé en mélange avec un autre solvant avantageusement choisi parmi les solvants décrits ci-dessus. Les mélanges de solvants eau/éthanol et eau/ monopropylène glycol sont préférés. La quantité d'eau présente dans un mélange de solvants est telle qu'elle représente de 2% à 30 % en poids par rapport au poids total de la composition.  According to one embodiment, when the solvent is water, it is preferably used in a mixture with another solvent advantageously chosen from the solvents described above. The water / ethanol and water / monopropylene glycol solvent mixtures are preferred. The amount of water present in a solvent mixture is such that it represents from 2% to 30% by weight relative to the total weight of the composition.
Le choix du solvant est effectué en fonction du domaine d'application envisagé. Ainsi, dans le cas de l'utilisation des compositions de l'invention dans le domaine alimentaire, il est impératif que le solvant utilisé ne soit pas toxique et toléré par les législations de ce domaine. Les compositions de l'invention peuvent également comprendre un antioxydant, notamment de l'acide ascorbique. Selon un mode de réalisation, la présente invention concerne une composition telle que définie ci-dessus comprenant de l'acide ascorbique à raison par exemple de 0,01 % à 1 %, de préférence de 0,01 % à 0,5% en poids par rapport au poids total de ladite composition. The choice of the solvent is made according to the intended field of application. Thus, in the case of the use of the compositions of the invention in the food field, it is imperative that the solvent used is not toxic and tolerated by the legislations of this field. The compositions of the invention may also comprise an antioxidant, in particular ascorbic acid. According to one embodiment, the present invention relates to a composition as defined above comprising ascorbic acid at, for example, from 0.01% to 1%, preferably from 0.01% to 0.5% by weight. weight relative to the total weight of said composition.
La présence d'un tel anti-oxydant permet de limiter les phénomènes de colorations parasites.  The presence of such an antioxidant makes it possible to limit the phenomena of parasitic staining.
En effet, les solutions de mélanges vanilline et éthylvanilline dans un solvant, tout comme les solutions de vanilline dans un solvant et les solutions d'éthylvanilline dans un solvant, développent une coloration jaune.  In fact, solutions of vanillin and ethyl vanillin mixtures in a solvent, as well as solutions of vanillin in a solvent and solutions of ethyl vanillin in a solvent, develop a yellow coloration.
Cette coloration peut être limitée par l'utilisation d'un antioxydant alimentaire tel que l'acide ascorbique.  This coloration may be limited by the use of a food antioxidant such as ascorbic acid.
Les compositions de l'invention peuvent également comprendre un colorant alimentaire, notamment un caramel. L'ajout d'un colorant alimentaire tel que du caramel permet également à la coloration d'être stabilisée à un niveau supérieur brun.  The compositions of the invention may also comprise a food coloring, in particular a caramel. The addition of a food coloring such as caramel also allows the color to be stabilized at a higher brown level.
Conformément à l'invention, les additifs avantageusement présents dans la composition selon l'invention représentent une quantité totale inférieure à la quantité de vanilline et d'éthylvanilline.  According to the invention, the additives advantageously present in the composition according to the invention represent a total amount less than the amount of vanillin and ethyl vanillin.
Le mode d'obtention des compositions à base de vanilline selon l'invention est décrit ci-après.  The method for obtaining the vanillin-based compositions according to the invention is described below.
La présente invention concerne également un procédé de préparation des compositions telles que définies ci-dessus, consistant à mélanger la vanilline, l'éthylvanilline et le solvant sous agitation.  The present invention also relates to a process for preparing the compositions as defined above, comprising mixing vanillin, ethyl vanillin and the solvent with stirring.
Selon un mode de réalisation de l'invention, on introduit de préférence la vanilline et l'éthylvanilline dans le solvant maintenu sous agitation.  According to one embodiment of the invention, vanillin and ethyl vanillin are preferably introduced into the solvent which is kept stirring.
De préférence, le procédé de l'invention est mis en œuvre à température ambiante comprise entre 15°C et 30°C mais il peut également comprendre une étape de chauffage du mélange obtenu afin d'obtenir un liquide que l'on récupère.  Preferably, the process of the invention is carried out at ambient temperature of between 15 ° C. and 30 ° C., but it may also comprise a step of heating the mixture obtained in order to obtain a liquid that is recovered.
Selon un mode de réalisation, on porte le mélange à une température de préférence inférieure ou égale à 50°C, de préférence, comprise entre 20°C et 50°C, et encore plus préférentiellement entre 20°C et 30°C.  According to one embodiment, the mixture is brought to a temperature preferably lower than or equal to 50 ° C, preferably between 20 ° C and 50 ° C, and even more preferably between 20 ° C and 30 ° C.
On maintient le mélange sous agitation jusqu'à obtention d'une solution homogène. Généralement, la durée varie entre 10 min et 3 heures. Ensuite, on obtient la composition sous forme liquide que l'on conditionne selon les besoins d'usage. The mixture is stirred with stirring until a homogeneous solution is obtained. Generally, the duration varies between 10 minutes and 3 hours. Then, the composition is obtained in liquid form that is conditioned according to the needs of use.
La présente invention concerne également une composition alimentaire comprenant une composition de vanilline selon la présente invention.  The present invention also relates to a food composition comprising a vanillin composition according to the present invention.
La présente invention concerne également l'utilisation de la composition de vanilline selon la présente invention comme arôme, comme parfum, comme agent de masquage d'odeur ou comme base parfumante.  The present invention also relates to the use of the vanillin composition according to the present invention as a flavor, as a perfume, as an odor-masking agent or as a perfume base.
Les compositions de l'invention peuvent être utilisées dans de nombreux domaines d'application, entre autres, dans le domaine alimentaire et pharmaceutique, et dans l'industrie de la parfumerie.  The compositions of the invention can be used in many fields of application, inter alia, in the food and pharmaceutical field, and in the perfume industry.
Plus particulièrement, la présente invention concerne l'utilisation de la composition de vanilline telle que définie ci-dessus comme arôme dans le domaine de l'alimentation humaine et animale, la pharmacie, et comme parfum, dans l'industrie des cosmétiques, de la parfumerie et de la détergence.  More particularly, the present invention relates to the use of the vanillin composition as defined above as aroma in the field of food and feed, pharmacy, and as perfume, in the cosmetics industry, the perfumery and detergency.
Selon un autre mode de réalisation, la composition de vanilline telle que définie ci-dessus peut être utilisée comme agent de masquage d'odeur, notamment dans l'industrie pharmaceutique.  According to another embodiment, the vanillin composition as defined above can be used as odor masking agent, in particular in the pharmaceutical industry.
Selon un autre mode de réalisation, la composition de vanilline telle que définie ci-dessus peut être utilisée dans le domaine de la cosmétique pour la préparation de crèmes, laits et fards et autres produits, comme base parfumante dans la parfumerie et dans le domaine de la détergence, notamment en savonnerie.  According to another embodiment, the vanillin composition as defined above can be used in the field of cosmetics for the preparation of creams, milks and blushes and other products, as perfume base in perfumery and in the field of cosmetics. detergency, especially in soap.
Un domaine d'application privilégié de compositions de l'invention est celui de la biscuiterie et pâtisserie, et plus particulièrement :  A preferred field of application of compositions of the invention is that of biscuit and pastry, and more particularly:
- biscuiterie sèche, notamment biscuits sucrés de type classique, petit beurre, galettes, casse-croûte ou sablés ;  - dry biscuits, especially sweet biscuits of the classic type, small butter, cookies, snack foods or shortbread cookies;
- pâtisserie industrielle, notamment boudoirs Champagne, langues de chat, biscuits à la cuillère, pain de gênes, génoise, madeleines, quatre-quarts, cakes, pâtisserie aux amandes, petits fours.  - industrial pastry, including champagne boudoirs, cat tongues, sponge biscuits, genoa bread, sponge cake, madeleines, pound cake, cakes, almond pastry, petits fours.
Les éléments fondamentaux présents dans les mélanges destinés aux industries précitées sont les protéines (gluten) et l'amidon qui sont le plus souvent apportés par la farine de froment. Pour la préparation des divers types de biscuits et gâteaux, on ajoute à la farine, des ingrédients tels que saccharose, sel, oeufs, lait, corps gras, éventuellement levures chimiques (bicarbonate de sodium ou autres levures artificielles) ou levures biologiques et farines de céréales diverses etc..  The basic elements present in the mixtures intended for the aforementioned industries are the proteins (gluten) and the starch which are most often brought by the wheat flour. For the preparation of the various types of biscuits and cakes, ingredients such as sucrose, salt, eggs, milk, fatty substances, possibly chemical yeasts (sodium bicarbonate or other artificial yeasts) or organic yeasts and flours are added to the flour. various cereals etc.
L'incorporation de la composition de vanilline selon l'invention est réalisée au cours de la fabrication, en fonction du produit souhaité et est conduite selon les techniques classiques du domaine considéré (cf. notamment J.L. KIGER et J.C. KIGER - Techniques Modernes de la Biscuiterie, Pâtisserie-Boulangerie industrielles et artisanales, DUNOD, Paris, 1968, Tome 2, pp. 231 et suivantes). The incorporation of the vanillin composition according to the invention is carried out during manufacture, according to the desired product and is carried out according to the classical techniques of the field considered (see in particular JL KIGER and JC KIGER - Modern Techniques of Biscuit, Pastry-bakery industrial and artisanal, DUNOD, Paris, 1968, Volume 2, pp. 231 and following).
D'une manière préférentielle, la composition de l'invention est introduite dans les corps gras qui interviennent dans la préparation de la pâte.  In a preferential manner, the composition of the invention is introduced into the fatty substances that are involved in the preparation of the dough.
A titre indicatif, on précisera que la composition de l'invention est introduite en une quantité de 0,05 à 1 ,5 g par kg de pâte.  As a guide, it will be noted that the composition of the invention is introduced in an amount of 0.05 to 1.5 g per kg of dough.
Les compositions de vanilline de l'invention sont tout à fait adaptées pour être utilisées dans le domaine de la chocolaterie et quelle que soit la forme de mise en oeuvre : chocolats en plaques, chocolats de couverture, fourrage pour chocolats.  The vanillin compositions of the invention are quite suitable for use in the field of chocolate and whatever the form of implementation: chocolate plates, couverture chocolates, filling for chocolates.
Elles peuvent être introduites au cours du conchage c'est-à-dire du malaxage de la pâte de cacao avec les différents ingrédients, notamment les arômes, soit après le conchage, par mise en oeuvre dans le beurre de cacao.  They can be introduced during conching, that is to say the mixing of the cocoa paste with the various ingredients, including flavorings, or after conching, by use in cocoa butter.
Dans ce domaine d'application, les compositions de vanilline de l'invention sont utilisées selon le type de chocolat, à raison de 0,05 g à 1 g pour 1 kg de produit fini, les teneurs les plus fortes se retrouvant dans le chocolat pour couverture.  In this field of application, the vanillin compositions of the invention are used according to the type of chocolate, at a rate of 0.05 g to 1 g per 1 kg of finished product, the highest contents being found in chocolate. for cover.
Une autre utilisation des compositions de l'invention est la fabrication des bonbons de tout genre : dragées, caramels, nougats, sucres cuits, bonbons fondants et autres.  Another use of the compositions of the invention is the manufacture of sweets of all kinds: sugared almonds, caramels, nougats, boiled sweets, melting sweets and others.
Elles sont introduites de préférence en phase liquide.  They are introduced preferably in the liquid phase.
La quantité de vanilline introduite dépend du goût plus ou moins prononcé que l'on recherche. Ainsi, les doses d'utilisation des compositions de l'invention peuvent varier entre 0,001 % et 0,2%.  The amount of vanillin introduced depends on the more or less pronounced taste that is sought. Thus, the use doses of the compositions of the invention may vary between 0.001% and 0.2%.
Les compositions de l'invention conviennent bien à des utilisations dans l'industrie laitière et plus particulièrement dans les laits aromatisés et gélifiés, les entremets, les yaourts, les glaces et les crèmes glacées.  The compositions of the invention are well suited for uses in the dairy industry and more particularly in flavored and gelled milks, desserts, yogurts, ice creams and ice creams.
L'aromatisation se fait par simple addition des compositions de l'invention, dans l'un des stades de mélange requis au cours de l'élaboration du produit.  The aromatization is by simple addition of the compositions of the invention, in one of the mixing stages required during the preparation of the product.
Les teneurs desdites compositions à mettre en oeuvre sont généralement faibles de l'ordre de 0,2 g pour 1 kg de produit fini.  The contents of said compositions to be used are generally low, of the order of 0.2 g per 1 kg of finished product.
Une autre application des compositions de l'invention dans le domaine alimentaire est la préparation du sucre vanilliné, c'est-à-dire l'imprégnation du sucre avec celles-ci, en une teneur de l'ordre de 7 g exprimée par rapport à 1 kg de produit fini.  Another application of the compositions of the invention in the food field is the preparation of vanillin sugar, that is to say the impregnation of the sugar with these, in a content of about 7 g expressed relative to to 1 kg of finished product.
Les compositions de l'invention peuvent également intervenir dans différentes boissons et l'on peut citer, entre autres, la grenadine et les boissons chocolatées. Il est courant d'utiliser la vanilline pour la dénaturation du beurre. A cet effet, les compositions de vanilline de l'invention peuvent être mises en oeuvre à raison de 6 g par tonne de beurre. The compositions of the invention may also be used in various drinks and include, among others, grenadine and chocolate drinks. It is common to use vanillin for the denaturation of butter. For this purpose, the vanillin compositions of the invention may be used at a rate of 6 g per tonne of butter.
Un autre domaine d'application des compositions de l'invention est l'alimentation animale, notamment pour la préparation de farines pour aliments des veaux et des porcs. La teneur préconisée est d'environ 0,2 g par kg de farine à aromatiser.  Another field of application of the compositions of the invention is the animal feed, especially for the preparation of feed meal for calves and pigs. The recommended content is about 0.2 g per kg of flour to be flavored.
Les compositions de l'invention peuvent trouver d'autres applications comme agent de masquage, pour l'industrie pharmaceutique (masquage de l'odeur de médicament) ou pour d'autres produits industriels (de type gomme, plastique, caoutchouc...).  The compositions of the invention may find other applications as a masking agent, for the pharmaceutical industry (masking the drug odor) or for other industrial products (of the rubber, plastic, rubber, etc. type). .
Elles conviennent tout à fait bien dans des domaines totalement différents tels que la cosmétique, l'industrie de la parfumerie ou la détergence.  They are quite suitable in completely different fields such as cosmetics, the perfume industry or detergency.
Elles peuvent être utilisées dans les cosmétiques tels que crèmes, laits, fards et autres produits et aussi, comme ingrédients parfumants, dans les compositions parfumantes, substances et produits parfumés.  They can be used in cosmetics such as creams, milks, blushes and other products and also, as perfume ingredients, in perfume compositions, substances and scented products.
Par "compositions parfumantes", on désigne des mélanges de divers ingrédients tels que solvants, supports solides ou liquides, fixateurs, composés odorants divers, etc., dans lesquels sont incorporées les compositions de l'invention, lesquelles sont utilisées pour procurer à divers types de produits finis, la fragrance recherchée.  By "perfuming compositions" are meant mixtures of various ingredients such as solvents, solid or liquid carriers, fixatives, various odorous compounds, etc., in which are incorporated the compositions of the invention, which are used to provide various types of of finished products, the sought-after fragrance.
Les bases pour parfum constituent des exemples préférés de compositions parfumantes dans lesquelles les compositions de l'invention peuvent être avantageusement utilisées à raison d'une teneur de 0,1 % à 2,5% en poids.  Fragrance bases are preferred examples of perfume compositions in which the compositions of the invention may be advantageously used at a level of from 0.1% to 2.5% by weight.
Les bases pour parfum peuvent servir à la préparation de nombreux produits parfumés tels que, par exemple, les eaux de toilettes, les parfums, les lotions après rasage ; les produits de toilette et d'hygiène tels que les gels de bain ou de douche, les produits déodorants ou anti-transpirants, qu'ils soient sous forme de sticks ou de lotions, les talcs ou poudres de toute nature ; les produits pour les cheveux tels que les shampooings et les produits capillaires de tout type.  The bases for perfume can be used for the preparation of many scented products such as, for example, toilet waters, perfumes, aftershave lotions; toilet and hygiene products such as bath or shower gels, deodorant or antiperspirant products, whether in the form of sticks or lotions, talcs or powders of any kind; hair products such as shampoos and hair products of all types.
Un autre exemple de mise en oeuvre des compositions de l'invention est le domaine de la savonnerie. Elles peuvent être utilisées à une teneur de 0,3% à 0,75% de la masse totale à parfumer. Généralement, la vanilline est associée dans cette application, à du résinoïde de benjoin et de l'hyposulfite de sodium (2%). Les compositions de vanilline selon l'invention peuvent trouver de nombreuses autres applications, notamment dans les désodorisants d'air ambiant ou tout produit d'entretien. Another example of implementation of the compositions of the invention is the field of soap. They can be used at a content of 0.3% to 0.75% of the total mass to be perfumed. Generally, vanillin is combined in this application with benzoin resinoid and sodium hyposulphite (2%). The vanillin compositions according to the invention can find many other applications, in particular in air fresheners or any maintenance product.
On ne sortira pas du cadre de l'invention, à ajouter dans les compositions de l'invention, des additifs requis au niveau de l'application envisagée. It will not be departing from the scope of the invention, to add in the compositions of the invention, additives required at the level of the intended application.
On donne ci-après des exemples illustrant la présente invention, sans caractère limitatif. Examples illustrating the present invention are given below, without being limiting in nature.
EXEMPLES EXAMPLES
Dans les exemples, les pourcentages mentionnés sont exprimés en poids. MPG : monopropylèneglycol (ou 1 ,2-propanediol) In the examples, the percentages mentioned are expressed by weight. MPG: monopropyleneglycol (or 1, 2-propanediol)
Exemple 1 - préparation d'une composition de vanilline selon l'invention Example 1 - Preparation of a Vanillin Composition According to the Invention
La préparation s'opère à température ambiante par mélange des différents constituants. The preparation is carried out at ambient temperature by mixing the various constituents.
Un mélange vanilline/éthylvanilline/MPG constitué de 20% poids de vanilline, de 20 % poids d'éthylvanilline et de 60% poids de MPG (mélange selon les proportions massiques 20/20/60) est préparé selon le mode opératoire suivant :  A vanillin / ethyl vanillin / MPG mixture consisting of 20% by weight of vanillin, 20% by weight of ethyl vanillin and 60% by weight of MPG (mixture according to the 20/20/60 mass ratio) is prepared according to the following procedure:
Dans un réacteur type calorimètre de 2 L on charge 792,45 g de MPG à 22°C. In a 2L calorimeter reactor, 792.45 g of MPG are charged at 22 ° C.
On coule la vanilline et l'éthylvanilline en 5 minutes sous agitation. Vanillin and ethyl vanillin are poured in 5 minutes with stirring.
On agite à 22°C pendant 2h à 300 t/min.  Stirred at 22 ° C for 2h at 300 rpm.
On obtient ainsi une composition liquide de vanilline selon l'invention.  A liquid vanillin composition according to the invention is thus obtained.
Le même protocole est appliqué pour la préparation des compositions de vanilline liquides selon l'invention (compositions 4 à 8 dans le tableau 1 ) et pour la préparation de compositions de vanilline non-conformes à l'invention (compositions 1 , 2 et 3 dans le tableau 1 ), en adaptant uniquement les quantités de solvant, de vanilline et d'éthylvanilline. Les proportions massiques vanilline/éthylvanilline/solvant pour chacune des compositions 1 à 8 figurent dans le tableau 1. The same protocol is applied for the preparation of liquid vanillin compositions according to the invention (compositions 4 to 8 in Table 1) and for the preparation of vanillin compositions not in accordance with the invention (compositions 1, 2 and 3 in Table 1), adapting only the amounts of solvent, vanillin and ethyl vanillin. The vanillin / ethyl vanillin / solvent mass proportions for each of compositions 1 to 8 are shown in Table 1.
Exemple 2 - Stabilité des compositions de vanilline de l'invention Plusieurs compositions liquides de vanilline selon l'invention ont été préparées et la stabilité de ces solutions a été évaluée, notamment afin de contrôler l'absence de cristallisation ou de démixion sur une période de 3 mois. Example 2 - Stability of the Vanillin Compositions of the Invention Several liquid compositions of vanillin according to the invention were prepared and the stability of these solutions was evaluated, in particular in order to control the absence of crystallization or demixing over a period of 3 months.
Ces compositions liquides sont toutes préparées par mélange du solvant, de l'éthylvanilline et de la vanilline selon le protocole de l'exemple 1 .  These liquid compositions are all prepared by mixing the solvent, ethyl vanillin and vanillin according to the protocol of Example 1.
La stabilité de chacune des compositions liquides est évaluée pendant une période de 3 mois, dans les conditions suivantes : The stability of each of the liquid compositions is evaluated for a period of 3 months under the following conditions:
- à température ambiante (conditions normales d'utilisation) ; et - at ambient temperature (normal conditions of use); and
- à 4°C (conditions pouvant être rencontrées lors du transport par exemple en soute) - at 4 ° C (conditions that may be encountered during transport, for example in the hold)
Les résultats obtenus sont indiqués ci-après dans le tableau 1. The results obtained are shown below in Table 1.
Tableau 1 Table 1
Figure imgf000011_0001
Figure imgf000011_0001
Il a donc été constaté que les compositions selon l'invention (4 à 8) sont stables au cours du temps, aussi bien à température ambiante qu'à 4°C. It has thus been found that the compositions according to the invention (4 to 8) are stable over time, both at room temperature and at 4 ° C.
Au contraire, une composition comprenant seulement 20% en poids de solvant n'est pas stable au cours du temps et cristallise à température ambiante et à 4°C. De même une composition contenant un seul composé choisi parmi la vanilline et l'éthylvanilline n'est pas non plus stable au cours du temps et cristallise à température ambiante et à 4°C bien que ladite composition contienne une quantité de matière sèche (vanilline ou éthylvanilline) identique à celle des compositions selon l'invention (cf les compositions 2 et 3 contre la composition 4 qui contiennent 40% poids de matière(s) sèche(s)). In contrast, a composition comprising only 20% by weight of solvent is not stable over time and crystallizes at room temperature and at 4 ° C. Similarly, a composition containing a single compound selected from vanillin and ethyl vanillin is also not stable over time and crystallizes at room temperature and at 4 ° C although said composition contains a quantity of dry matter (vanillin or ethyl vanillin) identical to that of the compositions according to the invention (cf. compositions 2 and 3 against composition 4 which contain 40% by weight of dry material (s)).
Exemple 3 - Coloration Example 3 - Coloring
On a mesuré l'indice de coloration de la composition vanilline/éthylvanilline/MPG selon les proportions massiques 20/20/60 (préparée dans l'exemple 1 ), conservée dans un flacon transparent, à température ambiante, à la lumière, au cours du temps. De l'acide ascorbique (antioxydant) a été ajouté à la composition. Les résultats sont rassemblés dans le tableau 2 ci-dessous. The color number of the vanillin / ethyl vanillin / MPG composition was measured according to the 20/20/60 mass ratio (prepared in Example 1), stored in a transparent bottle at room temperature, in the light during time. Ascorbic acid (antioxidant) was added to the composition. The results are collated in Table 2 below.
Tableau 2 : évolution de l'indice de coloration d'une composition vanilline/éthylvanilline en fonction du temps et de la présence d'antioxydant Table 2: Evolution of the color index of a vanillin / ethyl vanillin composition as a function of time and the presence of antioxidant
Figure imgf000012_0001
Figure imgf000012_0001
L'indice de coloration est déterminé sur un colorimètre Minolta par test dit de « yellow index » selon la méthode normalisée DI N 6167 (mesure d'indice de jaune selon la méthode normalisée DI N 6167). L'indice de coloration est d'autant plus faible que la composition est insensible à la lumière. The color number is determined on a Minolta colorimeter by the so-called "yellow index" test according to the standard method DI No. 6167 (measurement of yellow index according to the standard method DI No. 6167). The color number is lower as the composition is insensitive to light.
Ces résultats démontrent l'effet bénéfique de l'addition d'acide ascorbique sur la coloration : la coloration de la composition de vanilline liquide varie peu en fonction du temps lorsqu'elle contient un antioxydant. These results demonstrate the beneficial effect of ascorbic acid addition on staining: the coloring of the liquid vanillin composition varies little with time when it contains an antioxidant.
Exemple 4 - Applications Example 4 - Applications
Exemple 4.1 . Préparation d'une boisson lactée Example 4.1. Preparation of a milk drink
A un lait demi-écrémé sucré à 5% par addition de 50 g de sucre (saccharose) à 950 g de lait demi-écrémé, on ajoute 0,6 g de l'arôme liquide objet de l'invention (composition 4 de l'exemple 1 ). Après homogénéisation, la préparation est évaluée par olfaction par voie rétronasale par un panel d'évaluateurs. Le lait aromatisé à 0,06% pds de la composition de l'invention présente un arôme vanille, similaire à la vanilline. To a semi-skimmed milk sweetened to 5% by addition of 50 g of sugar (sucrose) to 950 g of semi-skimmed milk, 0.6 g of the liquid flavor which is the subject of the invention (composition 4 of the invention) are added. Example 1). After homogenization, the preparation is assessed by olfaction by the retro-nasal route by a panel of evaluators. The flavored milk 0.06% by weight of the composition of the invention has a vanilla flavor similar to vanillin.
Exemple 4.2. Préparation d'un gâteau Example 4.2. Preparing a cake
250 parties de matière grasse et 0,5 parties d'arôme liquide de l'invention (composition 4 de l'exemple 1 ) sont mélangées avec 250 parties de sucre jusqu'à obtention d'une pommade.  250 parts of fat and 0.5 parts of liquid flavor of the invention (composition 4 of Example 1) are mixed with 250 parts of sugar until an ointment.
250 parties d'œuf sont ajoutées au mélange. Le mélange est battu jusqu'à obtention d'un mélange homogène. On ajoute également 250 parties de farine et 2 parties de sel. Le mélange est battu jusqu'à obtention d'une pâte homogène.  250 parts of egg are added to the mixture. The mixture is beaten until a homogeneous mixture. 250 parts of flour and 2 parts of salt are also added. The mixture is beaten until a homogeneous paste.
Le gâteau est cuit 30 minutes à 150°C.  The cake is baked for 30 minutes at 150 ° C.
Le gâteau est évalué après un jour à température ambiante par olfaction par voie rétronasale par un panel d'évaluateurs.  The cake is evaluated after one day at room temperature by olfaction by the retro-nasal route by a panel of evaluators.
Le gâteau aromatisé à 0,05% pds de la composition de l'invention présente un arôme vanille, similaire à la vanilline.  The cake flavored to 0.05% by weight of the composition of the invention has a vanilla flavor, similar to vanillin.

Claims

REVENDICATIONS
1. Composition de vanilline sous forme liquide comprenant de la vanilline, de l'éthylvanilline et au moins un solvant autre que le méthanol, dans laquelle la quantité de solvant est d'au moins 40% en poids par rapport au poids total de ladite composition et le ratio massique vanilline / éthylvanilline est compris de 75/25 à 40/60. 1. Vanillin composition in liquid form comprising vanillin, ethyl vanillin and at least one solvent other than methanol, wherein the amount of solvent is at least 40% by weight relative to the total weight of said composition and the vanillin / ethylvanillin mass ratio is from 75/25 to 40/60.
2. Composition selon la revendication 1 , dans laquelle la quantité de solvant représente de 40% à 90% en poids par rapport au poids total de ladite composition. 2. Composition according to claim 1, wherein the amount of solvent represents from 40% to 90% by weight relative to the total weight of said composition.
3. Composition selon la revendication 1 ou la revendication 2 dans laquelle la quantité de solvant représente de 60% à 80% en poids par rapport au poids total de ladite composition. 3. Composition according to claim 1 or claim 2 wherein the amount of solvent is from 60% to 80% by weight relative to the total weight of said composition.
4. Composition selon l'une quelconque des revendications 1 à 3, dans laquelle le ratio massique vanilline / éthylvanilline est compris de 75/25 à 45/55. 4. Composition according to any one of claims 1 to 3, wherein the mass ratio vanillin / ethylvanillin is between 75/25 to 45/55.
5. Composition selon l'une quelconque des revendications 1 à 4, dans laquelle le solvant est un solvant aqueux ou un solvant organique polaire, apolaire, protique ou aprotique ou un mélange de solvants. The composition of any one of claims 1 to 4, wherein the solvent is an aqueous solvent or a polar, apolar, protic or aprotic organic solvent or a mixture of solvents.
6. Composition selon l'une quelconque des revendications 1 à 5, dans laquelle le solvant est choisi dans le groupe constitué : 6. Composition according to any one of claims 1 to 5, wherein the solvent is selected from the group consisting of:
- de l'eau ou du sirop de glucose ;  - water or glucose syrup;
- des monalcools ou des diols, de préférence, aliphatiques ou arylaliphatiques et plus préférentiellement, l'éthanol, le propanol, l'isopropanol, le butanol, l'alcool beta-phényléthylique, l'éthylèneglycol, le diéthylèneglycol, le monopropylèneglycol, le glycérol ;  alcohols or diols, preferably aliphatic or arylaliphatic and more preferentially, ethanol, propanol, isopropanol, butanol, beta-phenylethyl alcohol, ethylene glycol, diethylene glycol, monopropylene glycol, glycerol ;
- des éther-oxydes de préférence, aliphatiques, et, plus particulièrement, le diéthyléther, le dipropyléther, le diisopropyléther, le dibutyléther, le méthyltertiobutyléther, l'éthyltertiobutyléther, le ditertiobutyléther, le diméthyléther de l'éthylèneglycol, le diméthyléther du diéthylèneglycol ; - des esters d'alkyle ou d'arylalkyle d'acides carboxyliques, aliphatiques, cycloaliphatiques ou aromatiques, et plus préférentiellement, l'acétate d'éthyle, l'acétate de butyle, le salicylate de benzyle, le laurate de méthyle, le benzoate de méthyle, le citrate d'éthyle et le triacétate de glycéryle ; et preferably aliphatic ether-oxides and, more particularly, diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, methyl tert-butyl ether, ethyl tert-butyl ether, di-tert-butyl ether, ethylene glycol dimethyl ether and diethylene glycol dimethyl ether; alkyl or arylalkyl esters of carboxylic, aliphatic, cycloaliphatic or aromatic acids, and more preferably, ethyl acetate, butyl acetate, benzyl salicylate, methyl laurate, benzoate methyl, ethyl citrate and glyceryl triacetate; and
- leurs mélanges.  - their mixtures.
7. Composition selon l'une quelconque des revendications 1 à 6, dans laquelle le solvant est choisi dans le groupe constitué de l'eau, du triacétate de glycéryle, de l'éthanol, du monopropylène glycol, du glycérol et de leurs mélanges. The composition according to any one of claims 1 to 6, wherein the solvent is selected from the group consisting of water, glyceryl triacetate, ethanol, monopropylene glycol, glycerol and mixtures thereof.
8. Composition selon l'une quelconque des revendications 1 à 7, comprenant en outre un anti-oxydant. 8. Composition according to any one of claims 1 to 7, further comprising an antioxidant.
9. Composition selon l'une quelconque des revendications 1 à 8, comprenant en outre un colorant alimentaire. 9. Composition according to any one of claims 1 to 8, further comprising a food coloring.
10. Procédé de préparation d'une composition de vanilline selon l'une quelconque des revendications 1 à 9, consistant à mélanger la vanilline, l'éthylvanilline et le solvant sous agitation. A process for preparing a vanillin composition according to any one of claims 1 to 9, comprising mixing vanillin, ethyl vanillin and the solvent with stirring.
11. Composition alimentaire comprenant la composition de vanilline selon l'une quelconque des revendications 1 à 9. 11. Food composition comprising the vanillin composition according to any one of claims 1 to 9.
12. Utilisation de la composition de vanilline selon l'une quelconque des revendications 1 à 9, comme arôme dans le domaine de l'alimentation humaine et animale, la pharmacie, et comme parfum, dans l'industrie des cosmétiques, de la parfumerie et de la détergence. 12. Use of the vanillin composition according to any one of claims 1 to 9, as aroma in the field of food and feed, pharmacy, and as perfume, in the cosmetics industry, perfumery and detergency.
13. Utilisation de la composition de vanilline selon l'une quelconque des revendications 1 à 9, comme agent de masquage d'odeur, notamment dans l'industrie pharmaceutique. 13. Use of the vanillin composition according to any one of claims 1 to 9, as odor masking agent, especially in the pharmaceutical industry.
14. Utilisation de la composition de vanilline selon l'une quelconque des revendications 1 à 9, dans le domaine de la cosmétique pour la préparation de crèmes, laits et fards et autres produits, comme base parfumante dans la parfumerie et dans le domaine de la détergence, notamment en savonnerie. 14. Use of the vanillin composition according to any one of claims 1 to 9, in the field of cosmetics for the preparation of creams, milks and blushes and other products, as perfume base in perfumery and in the field of cosmetics. detergency, especially in soap.
PCT/EP2012/067181 2011-09-13 2012-09-04 Vanillin compositions in liquid form WO2013037665A1 (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL54771B1 (en) * 1965-11-06 1968-02-26 Instytut Przemyslu Drobnego I Rzemiosla
US4385073A (en) * 1982-03-26 1983-05-24 International Flavors & Fragrances Inc. Flavoring foodstuffs and chewing gums with 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone
HU206817A (en) * 1991-04-29 1993-01-28 Egal Vegyipari Koezoes Vallala Spice and process for its production
EP0692195A2 (en) * 1994-06-29 1996-01-17 Rhone-Poulenc Chimie S.A. Vanillin compound in liquid form, its preparation and uses
FR2937639A1 (en) * 2008-10-24 2010-04-30 Rhodia Operations NEW COMPOUND BASED ON VANILLIN AND ETHYLVANILLIN, ITS PREPARATION AND APPLICATIONS
FR2956661A1 (en) * 2010-02-24 2011-08-26 Rhodia Operations PROCESS FOR THE PREPARATION OF A COMPOSITION COMPRISING A COMPOUND BASED ON VANILLINE AND ETHYLVANILLIN, COMPOSITION OBTAINED AND APPLICATIONS THEREOF

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL54771B1 (en) * 1965-11-06 1968-02-26 Instytut Przemyslu Drobnego I Rzemiosla
US4385073A (en) * 1982-03-26 1983-05-24 International Flavors & Fragrances Inc. Flavoring foodstuffs and chewing gums with 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone
HU206817A (en) * 1991-04-29 1993-01-28 Egal Vegyipari Koezoes Vallala Spice and process for its production
EP0692195A2 (en) * 1994-06-29 1996-01-17 Rhone-Poulenc Chimie S.A. Vanillin compound in liquid form, its preparation and uses
FR2937639A1 (en) * 2008-10-24 2010-04-30 Rhodia Operations NEW COMPOUND BASED ON VANILLIN AND ETHYLVANILLIN, ITS PREPARATION AND APPLICATIONS
FR2956661A1 (en) * 2010-02-24 2011-08-26 Rhodia Operations PROCESS FOR THE PREPARATION OF A COMPOSITION COMPRISING A COMPOUND BASED ON VANILLINE AND ETHYLVANILLIN, COMPOSITION OBTAINED AND APPLICATIONS THEREOF

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J.L. KIGER; J.C. KIGER: "Techniques Modernes de la Biscuiterie, Pâtisserie-Boulangerie industrielles et artisanales", 1968, pages: 231

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