Process for preparing powdered microcapsules

Abstract

The present invention relates to a new process for the preparation of powdered microcapsules encapsulating active volatile active ingredients, in particular a perfume or a flavour, said process being performed at room temperature. A powdered microcapsule is an object of the invention. Powdered microcapsules obtainable by said process are also an object of the invention. A multiple-microcapsule delivery system, perfuming and flavouring compositions as well as consumer products comprising said microcapsules are also part of the invention.

Description

[0001] PROCESS FOR PREPARING POWDERED MICROCAPSULES

[0002] Technical Field

[0003] The present invention relates to a field of delivery systems. More particularly, the invention pertains to a process for the preparation of powdered microcapsules encapsulating small and volatile active ingredients, in particular a perfume or a flavour. The process of the invention provides an advantageous sustainable alternative to spraydrying as it takes place at room temperature. A powdered microcapsule is an object of the invention. Powdered microcapsules obtainable by said process are also an object of the invention. A multiple-microcapsule delivery system, perfuming and flavouring compositions as well as consumer products comprising said microcapsules are also part of the invention.

[0004] Background of the Invention

[0005] One of the problems faced by the perfume and flavour industry lies in the relatively rapid loss of olfactive benefit provided by active compounds due to their volatility, particularly that of “top-notes”, especially smaller, volatile compounds. The encapsulation of those active substances provides at the same time a protection of the ingredients there- encapsulated against “aggressions” such as oxidation or moisture and allows, on the other hand, a certain control of the kinetics of flavour or fragrance release to induce sensory effects through sequential release.

[0006] Spray-drying is part of the most common techniques used to stabilise volatile substances such as flavours and fragrances by encapsulating them in a solid form, suited to many applications. Spray-drying can be used to transform a simple emulsion into a powder, therefore providing an encapsulated system in the form of a matrix but has also been described as a suitable technique to dry microencapsulated actives in the form of aqueous slurries, in particular core-shell systems. Spray-dried powders are commonly made by spraying liquid emulsions or slurries into a stream of hot air. Spray-drying is usually done by means of a rotating disc or of multicomponent nozzles. Detailed techniques are described for instance in K. Masters, Spray-drying Handbook, Longman Scientific and Technical 1991. This drying technique suffers from several drawbacks, the main one being the temperature at which the process is performed, which necessarily leads to volatile losses during the process. Another related problem is that of technical safety, the above-described encapsulation equipment suffering from explosions of particles suspended in the air. The problem of reducing the violence of possible explosion has therefore to be addressed, e.g. by using particular fireproofing agents in formulations.

[0007] Solutions to address the problem of reducing volatile losses during spray-drying have been described, among which spray-drying at lower temperatures. W02012 / 122010 describes in particular a solution based on a modification of the equipment to have an inlet temperature of less than 100°C and an air inlet dew point comprised between -10°C and +5°C in order to preserve volatiles during the process. However, besides the costs generated by the equipment, this process still generates volatile losses.

[0008] On the other hand, plating is a known technique that is performed at room temperature. It refers to the immobilisation of a liquid active onto a porous carrier. The liquid is either absorbed in the particle pores and / or capillary adsorbed in-between the particles thus leading to agglomeration. This technique is processed by mixing of both liquid and powder phases into a blender which makes it the most cost-effective granulation method for oil delivery. However, plated flavours or perfumes are not properly encapsulated into a shell are therefore prone to evaporation and oxidation over storage, which limits the range of liquids that can be turned into powders by this technique to nonvolatile and non-oxy gen-sensitive compounds.

[0009] There is a need to find an alternative solution to existing drying techniques with the purpose of drying simple emulsions or slurries to form free-flowing powders while preserving the small active volatiles to be encapsulated. The present invention solves this problem by providing a new process taking place at room temperature which allows to efficiently encapsulate an oil phase into a solidified carrier by powder blending with materials meeting certain criteria. Said process is producing unique microcapsules with a better encapsulation performance than spray-dried powders.

[0010] Summary of the Invention

[0011] It has been unexpectedly found that the process of drying emulsions at room temperature, using a well-chosen desiccant powder in order to provide a delivery system for active volatile ingredients, allows to encapsulate more efficiently a larger range of active ingredients. The process of the invention performed at room temperature therefore constitutes a solution to the above-mentioned problems as it allows preparing powdered microencapsulated systems while preserving the volatile ingredients there-encapsulated. In a first aspect, the present invention relates to a process for preparing a powdered microencapsulated composition comprising the steps of: a) Preparing an oil-in-water suspension containing

[0012] (i) an oil phase comprising an active ingredient, preferably a perfume or a flavour oil, characterised in that it comprises at least one compound having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C, said oil phase being dispersed in

[0013] (ii) an aqueous phase including water and a water-soluble carbohydrate carrier; wherein weight ratio between the oil phase and the water is preferably above 1, more preferably above 1.5; b) Blending at room temperature the suspension obtained under step a) with a desiccant powder to form a free-flowing microcapsule powder; c) Optionally sifting the obtained powder to remove the excess desiccant.

[0014] In a second aspect, the invention concerns a powdered microcapsule comprising an active ingredient as defined above, a water-soluble carbohydrate carrier, and a desiccant, wherein the desiccant has a dextrose equivalent (DE) of 10 or less.

[0015] In a third aspect, the invention relates to non-spherical powdered microcapsules, preferably perfuming or flavouring powdered microcapsules, obtainable by a process as described in any of the above-described embodiments.

[0016] In a fourth aspect, the invention concerns a delivery system comprising non- spherical powdered microcapsules according to the invention, preferably perfuming or flavouring powdered microcapsules, and a second type of particles, preferably perfuming or flavouring powdered particles, encapsulating at least one compound having a molecular weight greater than 100 g / mol and / or a vapour pressure less than 500 Pa at 25°C.

[0017] In a fifth aspect, the invention concerns a perfuming or flavouring composition comprising

[0018] (i) non-spherical powdered microcapsules as defined above;

[0019] (ii) at least one perfuming or flavouring co-ingredient. In a sixth and seventh aspects, the invention relates to a perfumed consumer products and flavoured edible products comprising the powdered microcapsules defined above.

[0020] Brief Description of the Figures

[0021] Figure 1 illustrates a comparison of the flavour retention of microcapsules obtainable by the process described in the invention using a desiccant with microcapsules obtained by spray-drying.

[0022] Figure 2 illustrates a comparison of the flavour retention of microcapsules obtainable by the process described in the invention using a desiccant with microcapsules obtained by spray-drying after 14 days of storage in open containers at 23°C and 20% RH.

[0023] Figure 3 illustrates a comparison of the flavour retention of microcapsules obtainable by the process described in the invention using a second desiccant with microcapsules obtained by spray-drying.

[0024] Figure 4 illustrates a comparison of the flavour retention of microcapsules obtainable by the process described in the invention using a second desiccant with microcapsules obtained by spray-drying after 14 days of storage in open containers at 23 °C and 20% RH.

[0025] Figure 5 illustrates a comparison of the flavour retention of microcapsules obtainable by the process described in the invention using a third desiccant with microcapsules obtained by spray-drying.

[0026] Figure 6 illustrates a comparison of the flavour retention of microcapsules obtainable by the process described in the invention using a third desiccant with microcapsules obtained by spray-drying after 14 days of storage in open containers at 23 °C and 20% RH.

[0027] Figure 7 illustrates a comparison of the flavour retention of microcapsules obtainable by the process described in the invention using another water-soluble carrier with microcapsules obtained by spray-drying.

[0028] Figure 8 illustrates a comparison of the flavour retention of microcapsules obtainable by the process described in the invention using two water-soluble carriers with microcapsules obtained by spray-drying. Detailed Description of the Invention

[0029] Unless stated otherwise, percentages (%) are meant to designate a percentage by weight of a composition.

[0030] By “room temperature” it is meant a temperature typically comprised between 15 and 30 °C, typically 20°C and 30°C.

[0031] By “perfume or flavour oil,” it is meant a single perfuming or flavouring compound or a mixture of several perfuming or flavouring compounds.

[0032] For the sake of clarity, the expression “suspension” in the present invention is meant to designate a system in which “particles” are dispersed in a continuous phase of a different composition and specifically includes a dispersion or an emulsion. For avoidance of doubt, a capsules slurry dispersed in a water phase falls under the definition of suspension, as well as “free” i.e. non-encapsulated oil dispersed in a water phase, but also a mixture thereof.

[0033] By “vapour pressure”, it is meant a pressure exerted by a vapour when the vapour is in equilibrium with the liquid or solid form, or both, of the same substance. In other words, vapour pressure is a measure of the tendency of a material to change into the gaseous or vapour state, which varies with temperature. The values of the vapour pressure of molecules can be reliably measured using different methods that are well known to the person skilled in the art. Non-limiting examples of such methods include the Static Equilibrium Method or the Dynamic Vapour Pressure Method. Vapour pressure values can also be reliably calculated using computer-based estimation programs for physical and chemical properties, such as the Estimation Programs Interface Suite™ (EPI Suite™). In an embodiment, the vapour pressure values are calculated using the Estimation Programs Interface Suite™ (EPI Suite™).

[0034] When referring to “water sorption” of a material in the context of the invention what is meant is the percentage of absorbed water by said dry material as a function of relative humidity in isothermic condition.

[0035] Herein, the term “water-soluble” when used to describe a material in the context of the present disclosure refers to the ability of the material to dissolve in water. In some embodiments, “water soluble” when used to describe a material in the context of the present disclosure means that at least 1%, typically at least 40%, more typically at least 50%, of the material by weight relative to the total weight of the water, dissolves in water.

[0036] By “powdered” composition, what is meant is a dry composition. By “non-spherical powdered microcapsules,” it should be understood powdered microcapsules having a coefficient of circularity below 0.70, preferably below 0.60. By contrast, particles obtained by spray-drying have a coefficient of circularity greater than 0.7.

[0037] The coefficient of circularity fcircis a well-known shape parameter and is function of the perimeter P and the area A of the particle (the circularity of a circle is 1):

[0038] The present invention provides an advantageous alternative to spray-dried powders with a process involving no heating and performed at room temperature while providing a better oil encapsulation for small compound(s).

[0039] Indeed, the present invention provides an advantage compared to spray-dried powders with a process allowing encapsulation of at least one active ingredient having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C. The molecular weight of a compound is determined using a variety of numerical and analytical methods well known to a person skilled in the art. Non-limiting examples of such methods include Mass Spectroscopy.

[0040] The present invention therefore relates in a first aspect to a process for preparing a powdered microencapsulated composition comprising the steps of: a) Preparing an oil-in-water suspension containing

[0041] (i) an oil phase comprising an active ingredient, preferably a perfume or a flavour oil, characterised in that it comprises at least one compound having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C, said oil phase being dispersed in

[0042] (ii) a water phase including a water-soluble carbohydrate carrier wherein the ratio between the oil phase and the water is preferably above 1, more preferably above 1.5; b) Blending at room temperature the suspension obtained under step a) with a desiccant powder to form a free-flowing microcapsule powder; c) Optionally sifting the obtained powder to remove the excess desiccant.

[0043] According to the invention, the process described above is free of any spray-drying step. Indeed, step b) of the process consists in drying the suspension obtained under step a) by blending at room temperature said suspension with a desiccant powder to form a free- flowing microcapsule powder, i.e. a dry microcapsule powder.

[0044] The process according to the invention provides over traditional spray-drying the advantage of reducing possible volatile losses and respecting the initial liquid olfactory or flavour profile. It also allows to encapsulate at least one compound having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C with better efficiency. It is also a way of reducing the production costs and carbon footprint, and it avoids explosion risks associated with drying liquids in hot air. It has been found that the presence of a water-soluble carrier in the dispersion which can act as a carrier upon drying to achieve a true encapsulation in a glassy matrix, together with specific respective water sorption isotherms of the carrier and the desiccant, were providing conditions such that the water migrates from the suspension to the desiccant during blending, allowing an efficient encapsulation.

[0045] In a first step of the process, an oil-in-water suspension is prepared. The oil phase comprises at least one active ingredient, preferably a hydrophobic active ingredient. According to a preferred embodiment, the active ingredient consists of a perfume or flavour oil. According to the invention, the oil phase comprises at least one active ingredient, said active ingredient comprising at least one compound having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C. According to an embodiment, the at least one compound having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C is selected from the group consisting of dimethyl sulfide, butan-2-one, 3 -methylbutanal, pentane-2, 3-dione, acetaldehyde, methyl mercaptan, trimethylamine, cis-l,3-pentadiene, trans-l,3-pentadiene, methyl formate, 2-methyl-l,3-butadiene, ethyl mercaptan, allyl mercaptan, 2-methy 1-1 -butene, N,N-dimethylethylamine, propanal, ethanethial, ethyl formate, isopropyl mercaptan, 3-buten-2-one, trans- 1 -propenyl mercaptan, tert-butyl methyl ether, tert-butyl mercaptan, 3 -methylfuran, tetrahydrofuran, 2-methylpropanal, 2,3- dihydrofuran, 2-propanone, diethylamine, 2-methyl-2-propenal, methyl ethyl sulfide, 2- methyltetrahydrofuran, methyl acetate, water, isopropyl formate, propyl mercaptan, 2- methylfuran, methanol, 3-methyltetrahydrofuran, 1 -methylpyrrole, methyl 2-propenoate, vinyl acetate, 2-ethylfuran, propyl formate, cyclohexene, butylamine, butanal, thiophene, 1-penten-3-one, sec-butyl mercaptan, pyruvaldehyde, norbomylene, formic acid, methyl propionate, 3-methyl-3-buten-2-one, isobutyl mercaptan, ethyl acetate, trans-2-heptene, 2- butanone, ethanol, 1 -heptene, diethyl sulfide, 2,3 -butanedione, allyl methyl sulfide, butyl mercaptan, 2-propanol, 2,2-dimethylpropanal, 2-butenal, 2-propen-l-ol, 1,1- dimethylethanol, 2-butenenitrile, 1 -methylcyclohexene, 4-pentenal, 5-methylisoxazole, trans-2-pentenal, 2-methylthiophene, 3-methyl-2-butanone, pentanal, 2-methyl-4,5- dihydrofuran, 1 -methylpyrrole, 2-methylbutanal, 3 -methylthiophene, trans-3- pentenenitrile, cis-2-pentenenitrile, 3-butenenitrile, 2,5-dimethyl-2,3-dihydrofuran, thiazole, 2-methyl-2-butenal, 3-methylbutylamine, 3-pentanone, 2-methyl-3-buten-2-ol, 1- hexen-3-one, trans-3-penten-2-one, l-methyl-l,3-cyclohexadiene, 2-pentanone, 2-butanol,

[0046] 2 -methyl- 1-pyrroline, 2-vinylfuran, 2-methyl-2-propen-l-ol, 2-methyl-l-penten-3-one, 2- methyl-l,3-cyclohexadiene, 1 -propanol, pyrazine, tert-amyl alcohol, acetic acid, 1H- pyrrole, 2-methyl-2-pentenal, trans-2-hexenal, cis-2-hexenal, 4-hexen-3-one, 2- cyclopentenone, trans-2-buten-l-ol, 2-buten-l-ol, 2-buten-l-ol, 5-hexen-2-one, 3-methyl-

[0047] 3-penten-2-one, cyclohexene epoxide, 2-methylpyridine, 3-methyl-2-butanol, 3- furaldehyde, methyl thioacetate, 4-methyl-4-penten-2-one, 2-methylbutyronitrile, 5- hexenal, cis-3-hexenal, trans-3-hexenal, 3-methylpyridine, isobutanol, cyclopentanone, 4- methyl-2-pentenal, thiazolidine, 2-ethenyl-2-butenal, 2-ethyl-trans-2-butenal, 3-methyl-2- butenal, 1 -methoxy -2 -propanol, 3-methylbutyronitrile, 4,5 -dimethyloxazole, 2,5- dimethylfuran, 3-pentanol, 2-pentanol, 1 -ethylpyrrole, (methylthio)methyl mercaptan, 4- methyl-3-penten-2-one, pentanenitrile, 3-methyl-3-butenenitrile, 2-furaldehyde, 2- methylthiazole, l-penten-3-ol, 4-methylpyridine, cis-4-hexenal, 2-ethoxy ethanol, hydroxyacetaldehyde, l-mercapto-2 -propanone, 1-butanol, 4-penten-2-ol, cis-2-penten-l- ol, trans-2-penten-l-ol, pyrimidine, 2-methylcyclopentanone, 3-methyl-2-buten-l-ol, 5- methylisothiazole, 2(5H)-thiophenone, propionic acid, 3,5-dimethylisoxazole, methylpyrazine, 2-methyl-2-cyclopenten-l-one, 5-methyl-2(5H)-furanone, cyclohexanone and mixtures thereof. Alternative hydrophobic ingredients which could benefit from being encapsulated could be used either instead of a perfume or flavour, or in combination with a perfume or flavour. Non-limiting examples of such ingredients include a cosmetic, skin caring, malodour counteracting, bactericide, fungicide, pharmaceutical or agrochemical ingredient, a sanitizing agent, an insect repellent, or attractant. By “perfume oil” (or also “perfume”) or “flavour oil” what is meant here is an ingredient or composition that is a liquid at about 25°C. Said perfume or flavour oil can be a perfuming or flavouring ingredient alone or a mixture of ingredients in the form of a perfuming or flavouring composition. As a “perfuming ingredient”, it is meant here a compound, which is used in perfuming preparations or compositions to impart as primary purpose a hedonic effect. In other words, such an ingredient, to be considered as being a perfuming one, must be recognised by a person skilled in the art as being able to at least impart or modify in a positive or pleasant way the odour of a composition, and not just as having an odour. The nature and type of the perfuming ingredients present in the oil phase do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect. In general terms, these perfuming ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are listed in reference texts such as the book by S. Arctander, Perfume and Flavour Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds.

[0048] The perfuming ingredients may be dissolved in a solvent of current use in the perfume industry. The solvent is preferably not an alcohol. Examples of such solvents are diethyl phthalate, isopropyl myristate, Abalyn® (rosin resins, available from Eastman), benzyl benzoate, ethyl citrate, limonene, or other terpenes, or isoparaffins. Preferably, the solvent is very hydrophobic and highly sterically hindered, like for example Abalyn® or benzyl benzoate. Preferably, the perfume comprises less than 30% of solvent. More preferably, the perfume comprises less than 20%, and even more preferably, less than 10% of solvent, all these percentages being defined by weight relative to the total weight of the perfume. Most preferably, the perfume is essentially free of solvent.

[0049] By “flavour ingredient or composition”, it is meant here a flavouring ingredient or a mixture of flavouring ingredients, solvent or adjuvants of current use for the preparation of a flavouring formulation, i.e. a particular mixture of ingredients which is intended to be added to an edible composition or chewable product to impart, improve or modify its organoleptic properties, in particular its flavour and / or taste. Taste modulator is also encompassed in said definition. Flavouring ingredients are well known to a skilled person in the art and their nature does not warrant a detailed description here, which in any case would not be exhaustive, the skilled flavourist being able to select them on the basis of his general knowledge and according to the intended use or application and the organoleptic effect it is desired to achieve. Many of these flavouring ingredients are listed in reference texts such as in the book by S. Arctander, Perfume and Flavour Chemicals, 1969, Montclair, N.J., USA, or its more recent versions, or in other works of similar nature such as Fenaroli’s Handbook of Flavour Ingredients, 1975, CRC Press or Synthetic Food Adjuncts, 1947, by M.B. Jacobs, can Nostrand Co., Inc. Solvents and adjuvants or current use for the preparation of a flavouring formulation are also well known in the art.

[0050] According to any one of the invention’s embodiments, the active ingredient comprises at least one compound having a molecular weight lower than or equal to 100 g / mol, preferably between 40 g / mol and 100 g / mol.

[0051] According to any one of the invention’s embodiments, the active ingredient comprises at least one compound having a vapour pressure greater than or equal to 500 Pa at 25°C, preferably greater than or equal to 1’000 Pa at 25°C, more preferably greater than or equal to 2’000 Pa at 25°C.

[0052] According to any one of the invention’s embodiments, the perfume or flavour oil consists of compounds having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C. According to a particular embodiment, the compounds having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C represent at least 10 wt.% of the active ingredient(s), preferably at least 20 wt.%, 30 wt.%, 40 wt.%, 50 wt.%, 60 wt.%, 70 wt.%, 80 wt.%, 90 wt.% or 100 wt.% of the active ingredient(s).

[0053] In a particular embodiment, the flavour oil is selected from the group consisting of terpenic flavours including citrus and mint flavours, fruity flavours, floral flavours, spicy flavours, woody flavours, nutty flavours, dairy flavours, caramel flavours, savoury flavours, vanilla flavours, and sulfurous flavours. In some embodiments, the flavouring comprises synthetic flavour oils and flavouring aromatics or oils, oleoresins and extracts derived from plants, leaves, flowers, fruits, and so forth, or combinations thereof. Non-limiting examples of flavour oils include spearmint oil, cinnamon oil, oil of wintergreen (methyl salicylate), peppermint oil, Japanese mint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, oil of nutmeg, allspice, oil of sage, mace, and cassia oil. Non-limiting examples of other flavours include natural and synthetic fruit flavours such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, yuzu, sudachi, and fruit essences including apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, pineapple, watermelon, apricot, banana, melon, apricot, ume, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya and so forth. Other potential flavours include a milk flavour, a butter flavour, a cheese flavour, a cream flavour, and a yogurt flavour; a vanilla flavour; tea or coffee flavours, such as a green tea flavour, a oolong tea flavour, a tea flavour, a cocoa flavour, a chocolate flavour, and a coffee flavour; mint flavours, such as a peppermint flavour, a spearmint flavour, and a Japanese mint flavour; spicy flavours, such as an asafetida flavour, an ajowan flavour, an anise flavour, an angelica flavour, a fennel flavour, an allspice flavour, a cinnamon flavour, a chamomile flavour, a mustard flavour, a cardamom flavour, a caraway flavour, a cumin flavour, a clove flavour, a pepper flavour, a coriander flavour, a sassafras flavour, a savoury flavour, a Zanthoxyli Fructus flavour, a perilla flavour, a juniper berry flavour, a ginger flavour, a star anise flavour, a horseradish flavour, a thyme flavour, a tarragon flavour, a dill flavour, a capsicum flavour, a nutmeg flavour, a basil flavour, a maijoram flavour, a rosemary flavour, a bay leaf flavour, and a wasabi (Japanese horseradish) flavour; meaty flavours, such as a grilled steak flavour, a roast beef flavour, a bacon flavour, a chicken broth flavour, a pulled pork flavour, a beef jerky flavour, a sausage flavour, a hamburger flavour, a beef stew flavour, and a lamb chop flavour; alcoholic flavours, such as a wine flavour, a whisky flavour, a brandy flavour, a rum flavour, a gin flavour, and a liqueur flavour; floral flavours; and vegetable flavours, such as an onion flavour, a garlic flavour, a cabbage flavour, a carrot flavour, a celery flavour, mushroom flavour, and a tomato flavour. These flavouring agents may be used in liquid or solid form and may be used individually or in admixture. In the context of dairy or dairy analogue products, the most commonly used flavour agents are agents that impart flavours such as vanilla, French vanilla, chocolate, banana, lemon, hazelnut, coconut, almond, strawberry, mocha, coffee, tea, chai, cinnamon, caramel, cream, brown sugar, toffee, pecan, butter pecan, toffee, Irish creme, white chocolate, raspberry, pumpkin pie spice, peppermint, or any combination thereof.

[0054] According to any one of the invention’s embodiment, the oil phase represents between about 10% and 60% w / w, preferably between 20 and 60 % w / w, more preferably between 20% and 50% w / w, by weight, relative to the total weight of the suspension. Preferably, the weight ratio between the oil phase and the water is above 1, more preferably above 1.5.

[0055] According to one embodiment, the perfume or flavour is in the form of a free oil dispersed in the water phase. What is meant by “free oil” in the context of the invention is an oil that is not encapsulated. According to a second embodiment, the perfume or flavour is in an encapsulated form dispersed in the water phase, i.e. in the form of a slurry. According to a third embodiment, the perfume or flavour is a mixture of free oil and encapsulated oil. When the suspension prepared in the first step of the invention comprises oil in an encapsulated form, the latter preferably consists of water-insoluble microcapsules. Those microcapsules can be obtained by any process known in the art and do not necessitate a more detailed description. As non-limiting examples, those water-insoluble microcapsules can be obtained by a process selected from the group consisting of interfacial polymerisation, polycondensation, simple and complex coacervation or a combination thereof. According to a particular embodiment, the microcapsules have a coreshell structure with a polymeric shell. The nature of the polymeric shell from the microcapsules of the invention can vary. As non-limiting examples, the shell can be aminoplast-based, polyurea-based or polyurethane-based. The shell can also be hybrid, namely organic-inorganic such as a hybrid shell composed of at least two types of inorganic particles that are cross-linked, or yet a shell resulting from the hydrolysis and condensation reaction of a polyalkoxysilane macro-monomeric composition.

[0056] According to a particular embodiment, the shell comprises an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde or cross-linked melamine formaldehyde or melamine glyoxal.

[0057] According to another embodiment, the shell is polyurea-based made from, for example but not limited to, isocyanate-based monomers and amine-containing crosslinkers such as guanidine carbonate and / or guanazole. Preferred polyurea microcapsules comprise a polyurea wall which is the reaction product of the polymerisation between at least one polyisocyanate comprising at least two isocyanate functional groups and at least one reactant selected from the group consisting of a water-soluble guanidine salt and guanidine; a colloidal stabiliser or emulsifier; and an encapsulated perfume.

[0058] According to another embodiment, the shell is polyurethane-based made from, for example but not limited to, polyisocyanate and polyols, polyamide, polyester, etc.

[0059] According to another embodiment, the microcapsules have a polymeric shell resulting from complex coacervation wherein the shell is possibly cross-linked such as described in W02014044840.

[0060] According to another embodiment, the encapsulated perfume or flavour powder consists of water-insoluble microcapsules preferably comprising a plasmolysed microorganism.

[0061] According to another embodiment, the plasmolysed microorganism is preferably selected from the group consisting of fungi, bacteria, algae, protozoa, or mixtures of two or more thereof, and more preferably comprises a yeast. According to another embodiment, the microcapsules comprise a plasmolysed microorganism, wherein the plasmolysed microorganism is selected from the group consisting of fungi, bacteria, algae, protozoa, or mixtures of two or more of these. In a particular embodiment, the microorganism is a fungus or a bacterium, more particularly it may comprise a yeast.

[0062] According to an embodiment, a yeast is added in the water phase.

[0063] The oil phase is dispersed in a water phase including a water-soluble carbohydrate carrier. Without being bound by theory, it is believed that the water-soluble carrier in the process according to the invention can act as a barrier upon drying to achieve a true encapsulation in a glassy matrix. Said water-soluble carrier is preferably present in an amount comprised between 15 wt.% and 40 wt.% of the suspension, more preferably between 25 wt.% and 40 wt.%. According to one embodiment, the water-soluble carbohydrate carrier material comprises at least one emulsifying polymer with a number average molecular weight (Mn) comprised between 400 and 4,500 g / mol. According to a particular embodiment, the water-soluble carbohydrate carrier material consists of one emulsifying polymer having a molecular weight (Mn) between 400 and 1,500 g / mol. According to another embodiment, the carbohydrate carrier comprises two emulsifying polymers, preferably two modified starches, one having a molecular weight (Mn) comprised between 400 and 1,500 g / mol and the other having a molecular weight (Mn) comprised between 1,500 and 4,500 g / mol.

[0064] As used herein, the term “starch” includes natural and modified starch, typically derived from plant sources, such as com, wheat, rice, potatoes, and the like. The term “modified starch” has the normal meaning understood by a person skilled in the art, i.e, a starch that has been physically modified (physical modification), enzymatically modified (enzymatic modification) or chemically modified (chemical modification). “Physically modified starch” means a starch which has been subjected to a heat treatment in the presence of relatively small amounts of water or moisture. No other reagents are added to the starch during the heat treatment. The heat-treatment processes include heat, moisture, and annealing treatments, both of which cause a physical modification of starch without any gelatinization. “Enzymatically modified starch” means a starch which has been treated with one or more enzymes to modify its properties. “Chemically modified starch” means a starch that has been reacted with reagents which have been added to the starch to form new covalent bonds between those molecules and the starch molecules. Examples of modified starches include, but are not limited to, starches that have been acetylated, oxidized, hydroxypropylated, phosphated, octenylsuccinated, cross-linked, pregelatinized, hydrolyzed, and any combination thereof. Herein, a pregelatinized starch is any starch which has been cooked and then dried, making the starch readily water-soluble. The term “natural starch” refers to unmodified starch and is used interchangeably with the term “native starch”.

[0065] According to another embodiment, the water-soluble carbohydrate carrier material comprises at least one starch hydrolysate with a molecular weight (Mn) lower than 1,500 g / mol, and the suspension further comprises an emulsifier. Typical emulsifiers include lecithin, glycerol esters, fatty acid esters, saponins, proteins, gum Arabic and mixtures thereof.

[0066] According to a particular embodiment, the water-soluble carbohydrate carrier material is a modified starch or octenyl succinate starch having a molecular weight greater than or equal to 400 g / mol.

[0067] According to a particular embodiment, the carrier is not a plasmolysed microorganism.

[0068] According to a particular embodiment, the carrier acts as an emulsifier. According to a particular embodiment, the suspension further comprises an emulsifier, preferably chosen from the group consisting of lecithin, glycerol esters, fatty acid esters, saponins, proteins, gum Arabic and mixtures thereof.

[0069] In a second step of the process of the invention, the suspension obtained under step a) is blended at room temperature with a desiccant powder to form a free-flowing powder.

[0070] Water sorption isotherms can be easily measured by using Dynamic Vapor Sorption equipment (Surface Measurement Systems Ltd, Alperton London, UK). Amorphous biopolymers exhibit a S-shaped water sorption isotherm which follows the model developed by Guggenheim- Anders on-de Boer ( GAB’s model). This technique is very popular and recommended: “H. Bizot, Using the GAB model to construct sorption isotherms, in: R. Jowitt, et al. (Eds.), Physical Properties of Foods (European Project Group COST 90 on physical properties of foods), Applied Science Publishers, London, 1983, p. 43”.

[0071] The sorption isotherm is well described by the GAB empirical model (Anderson 1946; Guggenheim 1966; de Boer 1968; van den Berg 1981), where Xw is the water content on a dry basis and Xm, K and C are temperature dependent empirical constants whereas awis the water activity:

[0072] The desiccant is preferably used in an amount such that the weight ratio between the desiccant and the liquid suspension is comprised between 1 and 20, preferably between 1 and 9.

[0073] According to an embodiment, said desiccant is characterised in that the weight difference A between the water sorption of the desiccant and the water sorption of the carrier, at 50% relative humidity and at 25°C, is positive; preferably A is at least 1%, more preferably A is at least 2%.

[0074] Examples of desiccant suitable for the invention include maltodextrin, starch, polyvinyl acetate, polyvinyl alcohol, dextrines, natural or modified starches, vegetable gums, pectins, xanthanes, alginates, carrageenans, cellulose derivatives, gelatines, and mixtures thereof.

[0075] Exemplary vegetable gums include, but are not limited to, xanthan gum, guar gum, locust bean gum, cellulose gum, gellan gum, gum Arabic, and the like. Exemplary cellulose derivatives include, but are not limited to, hydroxypropyl methyl cellulose, sodium carboxymethylcellulose, methylcellulose, ethyl cellulose, croscarmellose sodium, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose acetate succinate, carboxymethyl hydroxyethyl cellulose, hydroxypropyl methyl cellulose phthalate and the like.

[0076] According to a particular embodiment, the desiccant is selected from the group consisting of maltodextrin DE 1, maltodextrin DE 2, maltodextrin DE 3, maltodextrin DE 4, pre-gelatinised com starch, cellulose, processed flour, and mixtures thereof.

[0077] Those of skill in the art would recognize that certain materials may be suitable for use as both the water-soluble carbohydrate carrier material and the desiccant. However, in certain embodiments, the water-soluble carbohydrate carrier material and the desiccant are different. By “different”, it is meant that the water-soluble carbohydrate carrier material and the desiccant do not belong to the same class of material or, if they do belong to the same class of material, they do not comprise the same chemical structure.

[0078] The person skilled in the art will be able to select a suitable carrier and a suitable desiccant to have a weight difference A between the water sorption of the desiccant and the water sorption of the carrier, at 50% relative humidity and at 25°C that is positive.

[0079] According to one embodiment of the process of the invention, the obtained free flowing powder is then sifted. Different sieves characterised by different mesh sizes can be used. As an example, sieves with mesh size 1’400 / 800 / 500 / 200 pm can be used in the context of the invention.

[0080] According to any of the above-described embodiments, a flowing agent can be used in the process of the invention. The flowing agent can ease the separation between the formed microcapsules and the desiccant used to dry the emulsion when there is a sifting step. It can also be used to improve the flowability of the resulting powders in the absence of sifting step. Typical examples of flowing agent include those selected from the group consisting of silicate, rice hull fibres, tricalcium phosphate and magnesium stearate.

[0081] A second object of the invention consists of a powdered microcapsule comprising an active ingredient, preferably a flavour oil or a perfume oil, characterised in that the active ingredient comprises at least one compound having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C, a water-soluble carbohydrate carrier, and a desiccant, wherein the desiccant has a dextrose equivalent (DE) of 10 or less. In some embodiments, the desiccant has a dextrose equivalent (DE) of 5 to 10, typically 5, 6, 7, 8, 9, or 10. According to an embodiment of the invention, the desiccant comprises, preferably consists of a carbohydrate having a dextrose equivalent (DE) lower than 5. In an embodiment, the desiccant has a dextrose equivalent (DE) of 1 to 4, typically 1, 2, 3, or 4, more typically 1 or 2.

[0082] According to a particular embodiment, the desiccant is selected from the group consisting of maltodextrin DE 1, maltodextrin DE 2, maltodextrin DE 3, maltodextrin DE 4, pre-gelatinised com starch, cellulose, processed flour, and mixtures thereof.

[0083] A third object of the invention consists of non-spherical powdered microcapsules, preferably perfuming or flavouring powdered microcapsules, obtainable by a process as described in any of the above-described embodiments.

[0084] The obtained product has, according to a first embodiment, a matrix structure, when an emulsion of free oil is dried by the process according to the invention. According to a second embodiment, it takes the form of dried core-shell microcapsules. According to a third embodiment, the powder consists of a combination of both in a matrix of carbohydrate material.

[0085] A fourth object of the invention is a delivery system comprising non-spherical powdered microcapsules according to the invention, preferably perfuming or flavouring powdered microcapsules and a second type of particles, preferably perfuming or flavouring powdered particles encapsulating at least one compound having a molecular weight greater than 100 g / mol and / or a vapour pressure less than 500 Pa at 25°C.

[0086] The second type of powdered particles can be prepared by different well-known techniques. One may cite as non-limiting examples, extrusion (hot extrusion or twin-screw extrusion), spray-drying, granulation.

[0087] The microcapsules according to the invention, present an advantageous alternative to spray-dried powder as they ensure an optimal preservation of the profile from the perfume or flavour there-encapsulated.

[0088] Such microcapsules could also be prepared with any other hydrophobic active material as mentioned above.

[0089] The products of the invention can be used for the preparation of perfuming or flavouring compositions which are also an object of the invention. In particular a perfuming composition comprising (i) non-spherical perfuming powdered microcapsules as defined above; (ii) at least one perfuming co-ingredient; and (iii) optionally a perfumery adjuvant, is another object of the invention.

[0090] By “perfuming co-ingredient”, it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect and which is not a microcapsule as defined above. In other words, such a co-ingredient, to be considered as being a perfuming one, must be recognised by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odour of a composition, and not just as having an odour. The nature and type of the perfuming co-ingredients present in the perfuming composition do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect. In general terms, these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co- ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavour Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds.

[0091] By “perfumery adjuvant”, we mean here an ingredient capable of imparting additional added benefit such as a colour, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming bases cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art.

[0092] Preferably, the perfuming composition according to the invention comprises between 0.1 and 30% by weight of microcapsules as defined above.

[0093] The invention’s microcapsules can advantageously be used in all the fields of modem perfumery. Consequently, another object of the present invention is represented by a perfuming consumer product comprising as a perfuming ingredient, the microcapsules defined above, or a perfuming composition as defined above.

[0094] The invention’s microcapsules can therefore be added as such or as part of an invention’s perfuming composition in a perfuming consumer product.

[0095] For the sake of clarity, it has to be mentioned that, by “perfuming consumer product”, it is meant a consumer product which is expected to deliver at least a pleasant perfuming effect to the surface to which it is applied (e.g. skin, hair, textile, or home surface). In other words, a perfuming consumer product according to the invention is a perfumed consumer product which comprises a functional formulation, as well as optionally additional benefit agents, corresponding to the desired consumer product, e.g. a detergent or an air freshener, and an olfactive effective amount of at least one invention’s compound.

[0096] The nature and type of the constituents of the perfumery consumer product do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the nature and the desired effect of said product. Formulations of consumer products in which the microcapsules of the invention can be incorporated can be found in the abundant literature relative to such products. These formulations do not warrant a detailed description here which would in any case not be exhaustive. The person skilled in the art of formulating such consumer products is perfectly able to select the suitable components on the basis of his general knowledge and of the available literature.

[0097] Non-limiting examples of suitable perfumery consumer product can be a perfume, such as a fine perfume, a cologne or an after-shave lotion; a fabric care product, such as a detergent, tablets and pods, a fabric softener, a dryer sheet, a fabric refresher, an ironing water, or a bleach; a body-care product, such as a hair care product (e.g. a shampoo, hair conditioner, a colouring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream, body lotion or a deodorant or antiperspirant), or a skin-care product (e.g. a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product); an air care product, such as an air freshener or a “ready-to-use” powdered air freshener; or a home care product, such as all-purpose cleaners, liquid or power or tablet dishwashing products, toilet cleaners or products for cleaning various surfaces. Preferably, the perfuming consumer product comprises from 0.1 to 15 wt.%, more preferably between 0.2 and 5 wt.% of the microcapsules of the present invention, these percentages being defined by weight relative to the total weight of the consumer product. Of course, the above concentrations may be adapted according to the olfactive effect desired in each product.

[0098] The microcapsules of the invention when encapsulating a flavour, can also be used in a great variety of edible end-products. Consumer products susceptible of being flavoured by the microcapsules of the invention may include foods, beverages, pharmaceutical and the like. For example, foodstuff base that could use the powdered microcapsules of the invention include

[0099] • Baked goods (e.g. bread, dry biscuits, cakes, other baked goods),

[0100] • Non-alcoholic beverages (e.g. carbonated soft drinks, bottled waters , sports / energy drinks, juice drinks, vegetable juices, vegetable juice preparations),

[0101] • Alcoholic beverages (e.g. beer and malt beverages, spirituous beverages),

[0102] • Instant beverages (e.g. instant vegetable drinks, powdered soft drinks, instant coffee, and tea),

[0103] • Cereal products (e.g. breakfast cereals, pre-cooked ready-made rice products, rice flour products, millet, and sorghum products, raw or pre-cooked noodles and pasta products),

[0104] • Milk products (e.g. fresh cheese, soft cheese, hard cheese, milk drinks, whey, butter, partially or wholly hydrolysed milk protein-containing products, fermented milk products, condensed milk, and analogues),

[0105] • Dairy based products (e.g. fruit or flavoured yoghurt, ice cream, fruit ices)

[0106] • Confectionary products (e.g. chewing gum, hard and soft candy)

[0107] • Chocolate and compound coatings

[0108] • Products based on fat and oil or emulsions thereof (e.g. mayonnaise, spreads, margarines, shortenings, remoulade, dressings, spice preparations),

[0109] • Spiced, marinated, or processed fish products (e.g. fish sausage, surimi),

[0110] • Eggs or egg products (dried egg, egg white, egg yolk, custard),

[0111] • Desserts (e.g. gelatines and puddings) • Products made of soya protein or other soya bean fractions (e.g. soya milk and products made therefrom, soya lecithin-containing preparations, fermented products such as tofu or tempeh or products manufactured therefrom, soya sauces),

[0112] • Vegetable preparations (e.g. ketchup, sauces, processed and reconstituted vegetables, dried vegetables, deep frozen vegetables, pre-cooked vegetables, vegetables pickled in vinegar, vegetable concentrates or pastes, cooked vegetables, potato preparations),

[0113] • Vegetarian meat replacer, vegetarian burger

[0114] • Spices or spice preparations (e.g. mustard preparations, horseradish preparations), spice mixtures and, in particular seasonings which are used, for example, in the field of snacks.

[0115] • Snack articles (e.g. baked or fried potato crisps or potato dough products, bread dough products, extrudates based on maize, rice, or ground nuts),

[0116] • Meat products (e.g. processed meat, poultry, beef, pork, ham, fresh sausage, or raw meat preparations, spiced or marinated fresh meat or cured meat products, reformed meat),

[0117] • Ready dishes (e.g. instant noodles, rice, pasta, pizza, tortillas, wraps) and soups and broths (e.g. stock, savoury cube, dried soups, instant soups, pre-cooked soups, retorted soups), sauces (instant sauces, dried sauces, ready-made sauces, gravies, sweet sauces).

[0118] Preferably, the microcapsules according to the invention shall be used in products selected from the group consisting of baked goods, instant beverages, cereal products, milk products, dairy -based products, products based on fat and oil or emulsions thereof, desserts, vegetable preparations, vegetarian meat replacer, spices and seasonings, snacks, meat products, ready dishes, soups and broths and sauces.

[0119] The microcapsules according to the invention shall be used in products selected from the group consisting of a stock, a savoury cube, a powder mix, a beef- or a pork-based product, seafood, surimi, instant noodles, rice, pasta, fried potatoes, potato flakes, noodles, potato / tortilla chip, microwave popcorn, nuts, a pretzel, a rice cake, a rice cracker, a biscuit, baked goods, a sports drink, a protein bar, and powdered drinks. The invention will now be further described by way of examples. It will be appreciated that the invention as claimed is not intended to be limited in any way by these examples.

[0120] Examples Example 1

[0121] Flavour oil composition

[0122] The flavour oil destined to be used in the flavour emulsion contains 8 aroma compounds, admixed in different amounts, and a solvent NEOBEE® (Stepan Company, Illinois, United States). The mixture’s proportions are described in Table 1. Table 1: Flavour oil containing 8 aroma compounds and a solvent

[0123] N.A. = not available

[0124] Example 2 Preparation of powdered microcapsules according to the invention based on a flavour emulsion A pre-emulsion was made using a simple overhead stirrer. The emulsion, under high shearrate stirring (600 RPM, then 1’000 RPM), was made of 50% of flavour oil (origin: dsm- firmenich), 25% of modified starch (HiCap®100, trademark and origin from Ingredion Ltd, Manchester, UK), and 25% of water. 200 g of desiccant, i.e. maltodextrin, dextrose equivalent 1 (GLUCIDEX® 1, Roquette,

[0125] France), were transferred in a bowl mixer and 50 g of the above emulsion were added evenly on top while blending to obtain powdered flavour microcapsules A. The resulting blend contained 20 wt.% of the emulsion corresponding to 10 wt.% of flavour.

[0126] The final mixture’s contents can be found in Table 2. Table 2: Composition of mixture for preparation of microcapsules A according to the invention

[0127] Example 3

[0128] Preparation of powdered microcapsules according to the invention based on a flavour emulsion

[0129] A pre-emulsion was made using a simple overhead stirrer. The emulsion, under high shearrate stirring (600 RPM, then 1’000 RPM), was made of 50% of flavour oil (origin: dsm- firmenich), 25% of modified starch (HiCap®100, trademark and origin from Ingredion Ltd, Manchester, UK), and 25% of water.

[0130] 200 g of desiccant, i.e. maltodextrin, dextrose equivalent 2 (GLUCIDEX® 2, Roquette, France), were transferred in a bowl mixer and 50 g of the above emulsion were added evenly on top while blending to obtain powdered flavour microcapsules B. The resulting blend contained 20 wt.% of the emulsion corresponding to 10 wt.% of flavour.

[0131] The final mixture’s contents can be found in Table 3.

[0132] Table 3: Composition of mixture for preparation of microcapsules B according to the invention

[0133] Example 4

[0134] Preparation of powdered microcapsules according to the invention based on a flavour emulsion

[0135] A pre-emulsion was made using a simple overhead stirrer. The emulsion, under high shear- rate stirring (600 RPM, then 1’000 RPM), was made of 50% of flavour oil (origin: dsm- firmenich), 25% of modified starch (HiCap®100, trademark and origin from Ingredion Ltd, Manchester, UK), and 25% of water. 200 g of desiccant, i.e. pre-gelatinised com starch (Merigel™300; Tate & Lyle, United Kingdom), were transferred in a bowl mixer and 50 g of the above emulsion were added evenly on top while blending to obtain powdered flavour microcapsules C. The resulting blend contained 20 wt.% of the emulsion corresponding to 10 wt.% of flavour. The final mixture’s contents can be found in Table 4.

[0136] Table 4: Composition of mixture for preparation of microcapsules C according to the invention

[0137] Example 5 Preparation of powdered microcapsules according to the invention based on a flavour emulsion

[0138] A pre-emulsion was made using a simple overhead stirrer. The emulsion, under high shearrate stirring (600 RPM, then 1’000 RPM), was made of 50% of flavour oil (origin: dsm- firmenich), 25% of modified starch (CAPSUL®, trademark and origin from Ingredion Ltd, Manchester, UK), and 25% of water.

[0139] 200 g of desiccant, i.e. maltodextrin, dextrose equivalent 2 (GLUCIDEX® 2, Roquette, France), were transferred in a bowl mixer and 50 g of the above emulsion were added evenly on top while blending to obtain powdered flavour microcapsules D. The resulting blend contained 20 wt.% of the emulsion corresponding to 10 wt.% of flavour.

[0140] The final mixture’s contents can be found in Table 5.

[0141] Table 5: Composition of mixture for preparation of microcapsules D according to the invention

[0142] Example 6

[0143] Preparation of powdered microcapsules according to the invention based on a flavour emulsion A pre-emulsion was made using a simple overhead stirrer. The emulsion, under high shearrate stirring (600 RPM, then 1’000 RPM), was made of 50% of flavour oil (origin: dsm- firmenich), 25% of modified starch (1 : 1 HiCap®100:CAPSUL®, trademark and origin from Ingredion Ltd, Manchester, UK), and 25% of water.

[0144] 200 g of desiccant, i.e. maltodextrin, dextrose equivalent 2 (GLUCIDEX® 2, Roquette, France), were transferred in a bowl mixer and 50 g of the above emulsion were added evenly on top while blending to obtain powdered flavour microcapsules E. The resulting blend contained 20 wt.% of the emulsion corresponding to 10 wt.% of flavour.

[0145] The final mixture’s contents can be found in Table 6. Table 6: Composition of mixture for preparation of microcapsules E according to the invention

[0146] Example 7 Comparative example: preparation of a microencapsulated powder based on a flavour emulsion outside the scope of the invention

[0147] The liquid flavour oil was spray-dried to obtain the powdered microcapsules F. The carrier and emulsifier used were maltodextrin DE 18 and CAPSUL® respectively with 90 / 10 ratio by weight. The spray drying took place at 50 wt.% of solids with 190°C co-current air flow. The theoretical flavour load of SD powder was 10 wt.%, which was equal to the standard GD formulation. The final mixture’s contents can be found in Table 7. The SD powder was stored in a plastic container at 10-20% RH and 23°C.

[0148] Table 7: Composition of mixture for preparation of microcapsules F not according to the invention

[0149] Example 8

[0150] Performance of powdered microcapsules according to the invention.

[0151] Flavour retention of the microencapsulated powder as per invention was evaluated by Atmospheric Pressure Chemical Ionization Mass Spectroscopy (APCI-MS) using SQ Detector 2 (Waters Corporation, Milford, Massachusetts, United States) and compared to spray-dried powder results at “time 0” (5 days after production of flavour powders stored in closed containers at 10-20% RH and 23°C) and after 14 days of storage in open containers at 23°C and 20% relative humidity. The results are shown in Figures 1 to 8. The average flavour retention after production and storage is summarised in Table 8.

[0152] Table 8: Average flavour retention The dried flavour as per invention had a higher retention of compounds having a MW < 100 g / mol and a vapour pressure > 500 Pa, at 25°C after production than the spray-dried flavour powder, regardless of the carrier and desiccant used.

[0153] The same trend is observed after storage for 14 days in open containers at 20% RH and 23°C.

[0154] Example 9A

[0155] Particles obtained by a process according to the invention applied to a suspension of microcapsules obtained by coacervation a) preparation of a suspension containing oil in the form of flavoured microcapsules made by complex coacervation.

[0156] Core-shell microcapsules based on complex coacervation were obtained following state of the art processes described in US 20090253165, example 1, using a model flavour as the microcapsules’ core.

[0157] The obtained slurry is a suspension of microcapsules in water containing 45% flavour oil of Table 1 and 45% water, at that stage the ratio between the encapsulated oil and water was 1. The carrier material (Hi-Cap®) is then added to the capsule suspension to reach a concentration of 50% into the water phase and mix until complete solubilisation. The final system obtained consisted of a stabilised suspension. b) Blending step

[0158] The prepared capsule suspension was recovered and transferred in a cutter blender containing native starch (desiccant) having a water content of 5.1 % and optionally 0. 1 % of a flowing agent (Sipemat®).

[0159] The mixture desiccant + capsules suspension was then mixed during 1 min to allow a complete homogenization. The mixture was then transferred into a sifting tower and sifted for 5 min at maximum amplitude to eliminate agglomerates above 1 ’700 pm and recover the desiccant below 100 pm.

[0160] The resulting product is a free-flowing powder.

[0161] Example 9B

[0162] Particles obtained by a process according to the invention applied to suspension of composite microcapsules. a) preparation of a suspensions containing oil in the form of flavoured composite microcapsules. Composite Core-shell microcapsules were obtained following the process described in (Multilayered core-shell microcapsules - EP2897723, example 4) using a model flavour as the microcapsules’ core.

[0163] The obtained slurry is a suspension of microcapsules in water containing 45% flavour oil of Table 1 and 45% water, at that stage the ratio between the encapsulated oil and water was 1. The carrier material (Hi-Cap®) is then poor into the capsule suspension to reach a concentration of 50% into the water phase and mix until complete solubilisation. The final system obtained consisted of a stabilised suspension. b) Blending step

[0164] The prepared capsule suspension was recovered and transferred in a cutter blender containing native starch (desiccant) having a water content of 5.1 % and optionally 0.1 % of a flowing agent (Sipemat®).

[0165] The mixture desiccant + capsule suspension was then mixed during 1 min to allow a complete homogenization. The mixture was then transferred into a sifting tower and sifted for 5 min at maximum amplitude to eliminate agglomerates above 1’700 pm and recover the desiccant below 100 pm.

[0166] The resulting product is a free-flowing powder.

[0167] Example 9C

[0168] Particles obtained by a process according to the invention applied to suspension of microbial microcapsules. a) preparation of a suspensions containing oil in the form of flavoured microbial microcapsules.

[0169] Microbial core-shell microcapsules were obtained following the process described in Edible products comprising flavouring microcapsules - W02018002331, examples 1-5 using a model flavour oil composition as the microcapsules’ core.

[0170] The obtained slurry is a suspension of microcapsules in water containing 45% flavour oil of Table 1 and 45% water, at that stage the ratio between the encapsulated oil and water was 1. The carrier material (Hi-Cap®) is then poured into the capsule suspension to reach a concentration of 50% into the water phase and mix until complete solubilisation. The final system obtained consisted of a stabilised suspension. b) Blending step The prepared capsule suspension was recovered and transferred in a cutter blender containing native starch (desiccant) having a water content of 5.1 % and optionally 0.1 % of a flowing agent (Sipemat®).

[0171] The mixture desiccant + capsule suspension was then mixed during 1 min to allow a complete homogenization. The mixture was then transferred into a sifting tower and sifted for 5 min at maximum amplitude to eliminate agglomerates above 1’700 pm and recover the desiccant below 100 pm.

[0172] The resulting product is a free-flowing powder

[0173] Example 10

[0174] Food consumer products comprising the flavouring powdered microcapsules according of the invention

[0175] Preparation of the flavouring powdered microcapsules (dried flavour) according to the present invention:

[0176] 50 g of a viscous emulsion containing 12.5 g water, 12.5 g HiCap 100 (modified starch) and 25 g of a liquid flavour (according to the invention) was prepared using a roto-stator homogenizer.

[0177] Then, 20 g of this emulsion was mixed with 79 g of maltodextrin 2DE using a kitchen cutter blender by shearing for 30 seconds. 1 g silicon dioxide was finally added before blending for 30 seconds more. The obtained sample containing 10% flavour is referred to as the dried flavour powder prepared according to the present invention.

[0178] 1. Basic Beef Noodles Seasoning

[0179] Procedure:

[0180] Plate xanthan into sugar, add the rest of powder ingredients and mix. Add palm fat and mix till homogeneous. 2. Beef burger in oven

[0181] Procedure:

[0182] Dilute the flavours in the water together with salt, pepper and add the breadcrumbs. Mix all the ingredients thoroughly. Form the beef burger (70 g) and then freeze.

[0183]

[0184] Procedure

[0185] Mix all ingredients thoroughly.

[0186] Make cubes.

[0187] 4. Chicken Nuggets

[0188] • Meat core

[0189] Procedure

[0190] Combine phosphate with water until dissolved and add to salt.

[0191] Mince chicken meat (10mm grind) and chicken skin (double pass, fine grind).

[0192] Mix chicken meat, skin and solution until liquid is absorbed.

[0193] Chill, form in mould, blast freeze.

[0194] • Predust

[0195] Procedure

[0196] Mix predust.

[0197] Apply to core at 5% weight of meat.

[0198] • Nuggets (meat core + predust)

[0199] Procedure

[0200] Predust core.

[0201] Cook in a steam oven, 90°C, 90% steam for 5 minutes.

[0202] Coat in breader and tempura batter (mix 1 : 1.1 water) Parfry at 190°C for 35 secs.

[0203] Blast freeze. 5. Cocido "HAM"

[0204] • Meat

[0205] Procedure:

[0206] Prepare the good quantity of chicken and put in a water cold bath to defrost. Grind the Turkey meat in the grinder size 10mm plate, keep in fridge.

[0207] • Marinade

[0208] Procedure:

[0209] Dissolve phosphate in Ice water.

[0210] Add salt and cured salt (sodium nitrite). Then add remaining ingredients and mix well with a handmixer until all dissolves.

[0211] Mix well Meat and Marinade together.

[0212] Add to the tumbler program 13 under vacuum for 1 hour.

[0213] Stay 14 hours in the refrigerator. Tumble again 1 hour program 13 under vacuum.

[0214] Stuff into a cooking bag and seal under vacuum if possible.

[0215] Cook in oven 80 °C 100% steam 25 minutes until internal temperature 73°C.

[0216] Cool quickly in ice. Store refrigerated at 4°C.

[0217] 6. Vegetarian Beef burger

[0218] Total 102.48 100.00%

[0219] Procedure:

[0220] Blend water and colourants.

[0221] Hydrate textured pea protein 45 minutes. Blend all ingredients (Thermomix® speed 2 REVERSE SENS), add slowly the oil, and keep speed for 2 minutes. Stop and mix with a spoon. Then continue to mix speed 2 for 3 minutes

[0222] Shape the Burgers (60 g)

[0223] Cook then 10 min in oven at 100°C - 50% RH

[0224] Deep fry 30 sec. at 170°C. Pack and deep freeze. 7. Vegetarian chicken nuggets

[0225] Procedure:

[0226] Hydrate soy protein concentrate in vacuum bag during 15 minutes (Phase 1),

[0227] Pre-mix isolate soy protein and water,

[0228] Mix phase 1 (Stephan®, cooking mixer), add the pre-mix (soy protein and water), when homogenous add oil slowly to form an emulsion.

[0229] Add all other ingredients as per the phases indicated in the recipe, mix between each ingredient during 30 seconds,

[0230] Cut under vacuum for 1.5 minutes at speed 9 to shred the textured soy protein concentrate, Release vacuum, scrape, and check if all the protein soy concentrate pieces have been shredded,

[0231] Let under vacuum 1 bar for 1.5 minutes at speed 3.

[0232] Shap the nuggets and freeze for 1 hour.

[0233] Example 11 Powdered soft drink comprising powdered microcapsules according to the invention

[0234] The dried lime flavour emulsion was prepared according to the present invention as follows:

[0235] A viscous emulsion was prepared by shearing 50 g lime flavour (according to the invention) in an aqueous solution containing 12.5 g HiCap® and 12.5 g water, using a mechanic stirrer equipped with a propeller (flavour / Hicap / water 50 / 25 / 25 w / w / w).

[0236] Then 20 g of this concentrate emulsion was blended 30 seconds within 79 g maltodextrin 2DE using a cutter-blender, followed by the addition of 1 g silicon dioxide, before mixing again for 30 seconds. A nicely free-flowing powder was obtained.

[0237] This sample was then formulated in a powdered soft drink so that the flavour content is 0.01%, according to the following table:

[0238] Example 12

[0239] Biscuits and baked goods comprising powdered microcapsules according to the invention

[0240] Preparation of the flavouring powdered microcapsules (dried flavour) according to the present invention:

[0241] 50 g of a viscous emulsion containing 12.5 g water, 12.5 g HiCap 100 (modified starch) and 25 g of a liquid flavour (according to the invention) was prepared using a roto-stator homogenizer.

[0242] Then, 20 g of this emulsion was mixed with 79 g of maltodextrin 2DE using a kitchen cutter blender by shearing for 30 seconds. 1 g silicon dioxide was finally added before blending for 30 seconds more. The obtained sample containing 10% flavour is referred to as the dried flavour powder prepared according to the present invention. This sample was then formulated in a powdered soft drink so that the flavour content is 0.025%, according to the following table:

[0243] 100.00

[0244] Ready-made biscuits : 1000.00

[0245] Example 13 Sports drinks comprising powdered microcapsules according to the invention Preparation of the flavouring powdered microcapsules (dried flavour) according to the present invention:

[0246] 50 g of a viscous emulsion containing 12.5 g water, 12.5 g HiCap 100 (modified starch) and 25 g of a liquid flavour (according to the invention) was prepared using a roto-stator homogenizer.

[0247] Then, 20 g of this emulsion was mixed with 79 g of maltodextrin 2DE using a kitchen cutter blender by shearing for 30 seconds. 1 g silicon dioxide was finally added before blending for 30 seconds more. The obtained sample containing 10% flavour is referred to as the dried flavour powder prepared according to the present invention. This sample was then formulated in a sports drink according to the following table: 2024P00185WG

[0248] 40

Claims

CLAIMS1. A process for preparing a powdered microencapsulated composition comprising the steps of: a) Preparing an oil-in-water suspension containing(i) An oil phase comprising an active ingredient, preferably a flavour oil or a perfume oil, characterised in that the active ingredient comprises at least one compound having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C, said oil phase being dispersed in(ii) A water phase including a water-soluble carbohydrate carrier, wherein the weight ratio between the oil phase and the water is preferable above 1, more preferably above 1.5; b) Blending at room temperature the suspension obtained under step a) with a desiccant powder to form a dry microcapsule powder; c) Optionally sifting the obtained powder to remove the excess desiccant.

2. The process according to claim 1, characterised in that the suspension comprises the oil phase, preferably a perfume or a flavour oil, freely dispersed in the water phase.

3. The process according to claim 1, characterised in that the suspension comprises the oil phase, preferably a perfume or flavour oil, wherein part of said oil is freely dispersed in the water phase and another part of the oil is dispersed in an encapsulated form in the water phase.

4. The process according to claim 1, characterised in that the suspension comprises the oil phase, preferably a perfume or flavour oil, dispersed in an encapsulated form in the water phase.

5. The process according to any one of claims 1 to 4, characterised in that the at least one compound having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C is selected from the group consisting of dimethyl sulfide, butan-2-one, 3-methylbutanal, pentane-2, 3-dione, acetaldehyde, methyl mercaptan, trimethylamine, cis-l,3-pentadiene, trans-l,3-pentadiene, methyl formate, 2-methyl-l,3-butadiene, ethyl mercaptan, allyl mercaptan, 2-methyl-l -butene, N,N-dimethylethylamine, propanal, ethanethial, ethyl formate, isopropyl mercaptan, 3- buten-2-one, trans- 1 -propenyl mercaptan, tert-butyl methyl ether, tert-butyl mercaptan,3 -methylfuran, tetrahydrofuran, 2-methylpropanal, 2,3-dihydrofuran, 2-propanone, diethylamine, 2-methyl-2-propenal, methyl ethyl sulfide, 2-methyltetrahydrofuran, methyl acetate, water, isopropyl formate, propyl mercaptan, 2-methylfuran, methanol, 3-methyltetrahydrofuran, 1 -methylpyrrole, methyl 2-propenoate, vinyl acetate, 2- ethylfuran, propyl formate, cyclohexene, butylamine, butanal, thiophene, l-penten-3- one, sec-butyl mercaptan, pyruvaldehyde, norbomylene, formic acid, methyl propionate, 3-methyl-3-buten-2-one, isobutyl mercaptan, ethyl acetate, trans-2- heptene, 2-butanone, ethanol, 1 -heptene, diethyl sulfide, 2,3-butanedione, allyl methyl sulfide, butyl mercaptan, 2-propanol, 2,2-dimethylpropanal, 2-butenal, 2-propen-l-ol, 1,1 -dimethylethanol, 2-butenenitrile, 1 -methylcyclohexene, 4-pentenal, 5- methylisoxazole, trans-2-pentenal, 2-methylthiophene, 3-methyl-2-butanone, pentanal, 2-methyl-4,5-dihydrofuran, 1 -methylpyrrole, 2-methylbutanal, 3 -methylthiophene, trans-3-pentenenitrile, cis-2-pentenenitrile, 3-butenenitrile, 2,5-dimethyl-2,3- dihydrofuran, thiazole, 2-methyl-2-butenal, 3 -methylbutylamine, 3-pentanone, 2- methyl-3-buten-2-ol, l-hexen-3-one, trans-3-penten-2-one, l-methyl-1,3- cyclohexadiene, 2-pentanone, 2-butanol, 2-methyl-l-pyrroline, 2-vinylfuran, 2- methyl-2-propen-l-ol, 2-methyl-l-penten-3-one, 2-methyl-l,3-cyclohexadiene, 1- propanol, pyrazine, tert-amyl alcohol, acetic acid, IH-pyrrole, 2-methyl-2-pentenal, trans-2-hexenal, cis-2-hexenal, 4-hexen-3-one, 2-cyclopentenone, trans-2-buten-l-ol,2-buten-l-ol, 2-buten-l-ol, 5-hexen-2-one, 3-methyl-3-penten-2-one, cyclohexene epoxide, 2-methylpyridine, 3-methyl-2 -butanol, 3-furaldehyde, methyl thioacetate, 4- methyl-4-penten-2-one, 2-methylbutyronitrile, 5-hexenal, cis-3-hexenal, trans-3- hexenal, 3 -methylpyridine, isobutanol, cyclopentanone, 4-methyl-2-pentenal, thiazolidine, 2-ethenyl-2-butenal, 2-ethyl-trans-2-butenal, 3-methyl-2-butenal, 1- methoxy-2-propanol, 3 -methylbutyronitrile, 4,5-dimethyloxazole, 2,5 -dimethylfuran,3-pentanol, 2-pentanol, 1 -ethylpyrrole, (methylthio)methyl mercaptan, 4-methyl-3- penten-2-one, pentanenitrile, 3 -methyl-3 -butenenitrile, 2-furaldehyde, 2- methylthiazole, l-penten-3-ol, 4-methylpyridine, cis-4-hexenal, 2-ethoxyethanol, hydroxyacetaldehyde, l-mercapto-2 -propanone, 1 -butanol, 4-penten-2-ol, cis-2- penten-l-ol, trans-2-penten-l-ol, pyrimidine, 2-methylcyclopentanone, 3-methyl-2- buten-l-ol, 5-methylisothiazole, 2(5H)-thiophenone, propionic acid, 3,5-dimethylisoxazole, methylpyrazine, 2-methyl-2-cyclopenten-l-one, 5-methyl-2(5H)- furanone, cyclohexanone and mixtures thereof.

6. The process according to any one of claims 1 to 5, characterised in that the active ingredient consists of compounds having a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C.

7. The process according to any one of claims 1 to 6, characterised in that the oil phase, preferably a perfume or flavour oil, is present in an amount comprised between 10 and 60 wt.% of the suspension.

8. The process according to any one of claims 1 to 7, characterised in that the water- soluble carbohydrate carrier is present in an amount comprised between 15 and 40 wt.%, preferably between 25 and 40 wt.% of the suspension.

9. The process according to any one of claims 1 to 8, characterised in that the desiccant is used in an amount such that the weight ratio between the desiccant and the liquid suspension is comprised between 1 and 20.

10. The process according to any one of claims 1 to 9, characterised in that the water- soluble carbohydrate carrier material comprises at least one emulsifying polymer with a molecular weight (Mn) between 400 and 4,500 g / mol.

11. The process according to any one of claims 1 to 10, characterised in that the water- soluble carbohydrate carrier material consists of one emulsifying polymer having a molecular weight (Mn) between 400 and 1,500 g / mol.

12. The process according to any one of claims 1 to 11, characterised in that the weight difference A between the water sorption of the desiccant and the water sorption of the carrier, at 50% relative humidity and at 25°C, is positive; preferably A is at least 1%, more preferably A is at least 2%.

13. The process according to any one of claims 1 to 12, characterised in that the desiccant is selected from the group consisting of maltodextrin, starch, polyvinyl acetate, polyvinyl alcohol, dextrines, natural or modified starch, vegetable gums, pectins, xanthanes, alginates, carragenans, cellulose derivatives and mixtures thereof.

14. A powdered microcapsule comprising: an active ingredient, wherein the active ingredient is a flavour oil or a perfume oil, characterised in that the active ingredient comprises at least one compoundhaving a molecular weight lower than or equal to 100 g / mol and a vapour pressure greater than or equal to 500 Pa at 25°C, a water-soluble carbohydrate carrier, and a desiccant, wherein the desiccant has a dextrose equivalent (DE) of 10 or less.

15. The powdered microcapsule according to claim 14, wherein the desiccant has a dextrose equivalent (DE) of lower than 5.

16. The powdered microcapsule according to claim 15, characterized in that the desiccant is selected from the group consisting of maltodextrin DE 1, maltodextrin DE 2, maltodextrin DE 3, maltodextrin DE 4, pre-gelatinised com starch, cellulose, processed flour, and mixtures thereof.

17. A food or beverage consumer product comprising the powdered microcapsule as defined in claim 14, said consumer product being selected from the group consisting of a stock, a savoury cube, a powder mix, a beef or pork-based product, a seafood, surimi, instant noodles, rice, pasta, potatoes flakes or fried, noodles, a potato / tortilla chip, a microwave popcorn, nuts, a pretzel, a rice cake, a rice cracker, a biscuit, baked goods, a sports drink, a protein bar, and powdered drinks.

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