US20050220981A1 - Aroma particles - Google Patents

Aroma particles Download PDF

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Publication number
US20050220981A1
US20050220981A1 US10/512,841 US51284105A US2005220981A1 US 20050220981 A1 US20050220981 A1 US 20050220981A1 US 51284105 A US51284105 A US 51284105A US 2005220981 A1 US2005220981 A1 US 2005220981A1
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Prior art keywords
oil
aroma
particles
methyl
matrix
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Abandoned
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US10/512,841
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English (en)
Inventor
Karl-Heinz Renz
Birgit Schleifenbaum
Jens Uhlemann
Fouad Saleeb
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Symrise AG
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Symrise AG
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Application filed by Symrise AG filed Critical Symrise AG
Assigned to SYMRISE GMBH & CO. KG reassignment SYMRISE GMBH & CO. KG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SALEEB, FOUAD, UHLEMANN, JENS, RENZ, KARL-HEINZ, SCHLEIFENBAUM, BIRGIT
Publication of US20050220981A1 publication Critical patent/US20050220981A1/en
Priority to US12/561,798 priority Critical patent/US8641945B2/en
Assigned to SYMRISE AG reassignment SYMRISE AG MERGER (SEE DOCUMENT FOR DETAILS). Assignors: SYMRISE GMBH & CO. KG
Priority to US14/154,511 priority patent/US9706791B2/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • A23L27/88—Taste or flavour enhancing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/40—Tea flavour; Tea oil; Flavouring of tea or tea extract
    • A23F3/405—Flavouring with flavours other than natural tea flavour or tea oil
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/18—Chewing gum characterised by shape, structure or physical form, e.g. aerated products
    • A23G4/20—Composite products, e.g. centre-filled, multi-layer, laminated
    • 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
    • A23L2/385—Concentrates of non-alcoholic beverages
    • A23L2/39—Dry compositions
    • 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
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring 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
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/72—Encapsulation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
    • C08L3/02—Starch; Degradation products thereof, e.g. dextrin
    • 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
    • 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
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
    • 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
    • C11D9/442—Perfumes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the invention relates to vitreous aroma particles and the preparation thereof, as well as to the use thereof in food products, consumer articles and pharmaceuticals.
  • an aroma is understood to be a substance which brings about odour impressions and/or flavour impressions. It can be constituted here by individual substances or individual materials, or by mixtures.
  • An aroma is also understood to be olfactory substances, aroma substances, flavour substances, perfume oils, fragrances, olfactory substance compositions, fragrance mixtures and the like.
  • Aroma particles are understood in the present invention to be encapsulations which comprise the encapsulating material (the matrix) and an aroma.
  • the matrices mentioned hereinbelow are vitreous and are also described as glasses.
  • Aromas are generally highly complex mixtures, that is to say combinations of many chemical substances having different chemical and physical properties. As the need for stable products in a very wide variety of applications such as food products, consumer articles and pharmaceuticals increases, there is a growing need for encapsulation of such aromas.
  • Aroma losses during encapsulation should be minimised and aroma retention during storage maximised. Above and beyond this, for aroma utilisation to be cost-effective for the user a high payload plus high retention of the volatile aromas are important. Retrieval in the encapsulated product of those aroma substances utilised by way of the recipe is described as “retention”.
  • a further aim is a freely adjustable particle size within the range 0.1 to 5 mm, with a narrow size distribution.
  • a virtually spherical product or a cylindrical product having a diameter:length ratio close to 1 is sought.
  • Encapsulated aromas having particularly good stability in storage are generally prepared in the aroma industry by emulsification of the aroma in molten carbohydrate mixtures, followed by forming or comminution.
  • Older processes for example U.S. Pat. No. 4,707,367, U.S. Pat. No. 4,499,112
  • Older processes operate in batch-wise manner with stirred tanks.
  • More recently, a continuous procedure in twin-screw extruders has proved to be particularly advantageous (for example U.S. Pat. No. 5,603,971, WO 94/06308, U.S. Pat. No. 5,009,900).
  • the comminution step destroys the surface structure of the particles.
  • a disadvantage associated with this is an elevated loading with an oily layer of the aroma which is utilised.
  • the oily layer of the aroma which is utilised, which is on the surface causes the particles to adhere, as well as greatly impairing the stability of the particles in storage.
  • An undesirably high proportion of fine dust is, moreover, formed.
  • U.S. Pat. No. 4,820,534 discloses a method for fixing labile substances such as, for example, essential oils in an extruded glass, characterised in that the quantitatively more important component present in a proportion by weight of at least 70% is a maltodextrin having a DE (dextrose equivalent) of up to 20.
  • the resulting matrix is a hard, non-hygroscopic glass from which encapsulated essential oils or other aromas can be prepared without the addition of emulsifiers and flow promoting agents.
  • coarse strands must first be prepared which are subsequently comminuted and sieved in a labour-intensive process, as a result of which undesirable dusty fines arise.
  • a direct processing of this glass by way of perforated disks having small openings (smaller than 1 mm) is not possible because, at the necessary temperatures, undesirable aroma losses and aroma reactions, as well as carbonisation and blockages in the extruder, would result.
  • U.S. Pat. No. 5,972,395 discloses the use of a quantitatively subordinate proportion by weight, of from 15 to 30%, of the maltodextrin having a dextrose equivalent of up to 20.
  • the encapsulation of water-insoluble lipophilic fish oil or of solid labile components such as carotene and maltol is described. These materials have only a slight plasticising effect on the matrix.
  • This method cannot, however, be applied to the encapsulation of commercial aromas because practically all natural, nature-identical or artificial aromas contain components which act as highly effective plasticisers of the carbohydrate matrix according to U.S. Pat. No. 5,972,395, as a result of which the glass becomes sticky and difficult to process.
  • Carbohydrate matrices and processes for the preparation thereof are therefore sought which enable aromas to be encapsulated in a stable manner by means of melt extrusion and die-face pelletisation, while not having the disadvantages of the prior art which have been described.
  • die-face pelletisation is understood to be a comminution, directly at the extruder exit, of the melt discharged from the extruder. The still soft surface structure is sealed by the action of the die-face pelletisation.
  • the present invention provides vitreous aroma particles prepared by extrusion of an aromatised melt, followed by die-face pelletisation, characterised in that the matrix of the particles contains from 20 to 80 wt. %, preferably 30 to 70 wt. %, particularly preferably 40 to 60 wt. %, carbohydrate polymers having an average molecular weight greater than 1000, the aromatised melt is discharged from the extruder by way of an opening and is comminuted in the still unsolidified state.
  • the present invention also provides a process for the preparation of the aroma particles according to the invention, as well as the use thereof in foods, pharmaceuticals and consumer articles.
  • the carbohydrate polymers used are prepared by acid or enzymatic hydrolysis of starch.
  • Starch is a long-chain glucose polymer. Complete acid hydrolysis of starch results in glucose. In enzymatic hydrolysis of starch the glucose dimer, maltose, can also be produced.
  • the characteristic value by which the degree of decomposition of the starch is measured is the “dextrose equivalent” (DE), which can take the limit values 0 for the long-chain glucose polymer and 100 for the pure glucose.
  • DE dehydride equivalent
  • the water-solubility of the starch degradation products increases as the DE value increases. Starch degradation products having a DE of less than 10 are sparingly soluble in water.
  • Maltodextrins substantially comprise polymers having a degree of polymerisation (degree of polymerisation DP) of the glucose starting at 4 (maltotetraose, molecular weight 720) and above. They contain only smaller quantities of monomeric sugars such as glucose (DP 1, molecular weight 180.2), maltose (DP 2, molecular weight 360.4) and maltotriose (DP 3, molecular weight 540.6).
  • maltodextrins having dextrose equivalents within the range 10 to 20 may be used.
  • Maltodextrins having a DE of 15 to 19 are particularly preferred.
  • the plant which originally supplied the starch for the preparation of the starch hydrolysates is immaterial.
  • Maize-based raw materials are suitable and readily available, in order to guarantee a product that is free from genetically modified constituents raw materials from tapioca, rice, wheat, potatoes can, for example, also be utilised.
  • the carbohydrate polymers have melting points greater than 190° C., preferably greater than 200° C.
  • the carbohydrate polymers used have glass transition temperatures of over 70° C., preferably over 80° C., in particular preferably over 90° C.
  • the proportion of from 70 to 30 wt. % which is complementary to the carbohydrate polymer content of 30 to 70 wt. %, embraces water-soluble, low molecular weight compounds having molecular weights within the range 90 to 950 and a melting point within the range 80° C. to 180° C.
  • Suitable water-soluble, low molecular weight compounds are, for example, monosaccharides, disaccharides and trisaccharides, sugar alcohols, solid food acids or mixtures thereof.
  • Particularly suitable monosaccharides, disaccharides and trisaccharides are, for example, arabinose, xylose, fructose, galactose, glucose, mannose, sorbose, lactose, maltose, saccharose, maltotriose.
  • sugar alcohols are, for example, mannitol, sorbitol, xylitol, arabinol, arabitol, adonitol, alditol, ducitol, iditol.
  • Particularly suitable food acids are, for example, citric acid, adipic acid, malic acid, fumaric acid, succinic acid, lactic acid, benzoic acid.
  • the matrix of the particles preferably additionally contains an emulsifier.
  • the additional incorporation of a small quantity, from 0.5 to 3 wt. %, of monoglycerides (a specific class of emulsifiers) into the matrix is advantageous in order to facilitate flow of the melt through openings (for example of a pelletising die) less than 1.0 mm in size.
  • Decaglycerol dipalmitate, hexaglycerol distearate, polyglycerol esters, sulfoacetates, lecithin are also suitable as emulsifiers.
  • glucose in the matrix enables die-face pelletisation to take place without the undesirable formation of fines and without adhesion of the freshly formed particles.
  • a glucose content of from 0.5 to 5 wt. % in the matrix is particularly preferred.
  • maltotriose which can improve holding-back of the aroma, thus making possible a higher aroma payload, is furthermore advantageous. If, with a higher aroma payload, a greater proportion of the undesirable oily layer of the aroma utilised, which arises during comminution, should occur, a convective treatment with inert gas (for example nitrogen, noble gases, air) can be effected in order to remove this oily layer.
  • inert gas for example nitrogen, noble gases, air
  • the water-soluble low molecular weight compounds reduce the softening point of the matrix: the higher the proportion thereof in the mixture, the more readily the matrix can be melted.
  • the processing temperature is reduced thereby.
  • the product strands are, however, more difficult to cut, and the pellets are less stable to humidity and temperature.
  • the low molecular weight compounds additionally facilitate pelletisation at the pelletising dies. The product becomes glass-hard more rapidly. If, however, excessive quantities of low molecular weight compounds are utilised the product already adheres at the pelletising die. In storage too, increased sticking occurs.
  • the aroma particles according to the invention typically have a glass transition temperature within the range 30 to 100° C., preferably within the range 45 to 75° C., particularly preferably within the range 50 to 60° C.
  • the glass transition temperatures were obtained by means of differential scanning calorimetry (DSC, heating rate 20 K/min).
  • the aroma particles preferably have a cylindrical or spherical geometry and a narrow particle size profile. They have a diameter of from 0.1 to 5 mm, preferably 0.2 to 2.5 mm, in particular preferably 0.3 to 1.5 mm, and a length of from 0.1 to 10 mm, preferably 0.2 to 3.0 mm, in particular preferably 0.3 to 1.5 mm.
  • the aroma particles according to the invention are highly stable in storage.
  • the aroma particles according to the invention are on the surface practically free from any oily layer of the aroma which is utilised.
  • the aroma is practically exclusively in the interior of the particles. If necessary, flow promoting agents may be added to the aroma particles in order to reduce still further the stickiness of the matrix.
  • the aroma particles according to the invention have an aroma content of from 0.5 to 25 wt. %, preferably 1 to 20 wt. %, in particular preferably 3 to 15 wt. %, in relation to the total weight of aroma particles.
  • olfactory substances which may be a constituent of the aroma, are found, for example, in S. Arctander, Perfume and Flavor Materials, Vols. I and II, Montclair, N.J., 1969, published by the author, or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 3 rd Edition, Wiley-VCH, Weinheim 1997.
  • extracts from natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures such as, for example, ambergris tincture; amyris oil, angelica seed oil; angelica root oil; aniseed oil; valerian oil, basil oil; tree moss absolute; bay oil; mugwort oil; benzoin resin; bergamot oil; beeswax absolute; birch tar oil; bitter almond oil; savory oil; buchu leaf oil; cabreuva oil; cade oil; calmus oil; camphor oil; cananga oil; cardamom oil; cascarilla oil; cassia oil; cassia absolute; castoreum absolute; cedar leaf oil; cedar wood oil; cistus oil; citronella oil; lemon oil; copaiba balsam; copaiba balsam oil; coriander oil: costus root oil; cumin oil; cypress oil; davana oil; dill herb oil;
  • olfactory substances from the group of hydrocarbons such as, for example, 3-carene; ⁇ -pinene; ⁇ -pinene; ⁇ -terpinene, ⁇ -terpinene, p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1,3,5-undecatriene;
  • the aroma particles may contain substances or substance mixtures, which are active in nutritional physiology (neutriceuticals).
  • the following might be named by way of example: panthenol, pantothenic acid, essential fatty acids, vitamin A and derivatives, carotenes, vitamin C (ascorbic acid), vitamin E (tocopherol) and derivatives, vitamins of the B and D series, such as vitamin B 6 (nicotinamide), vitamin B 12 , vitamin D 1 , vitamin D 3 , vitamin F, folic acid, biotin, amino acids, compounds of the elements magnesium, silicon, phosphorus, calcium, manganese, iron or copper, coenzyme Q10, unsaturated fatty acids, ⁇ -3-fatty acids, polyunsaturated fatty acids, ⁇ -linolenic acid, oleic acid, eicosapentaenoic acid, docosahexaenoic acid and derivatives thereof, bisabolene, chloramphenicol, caffeine, capsaicin, prostaglandins
  • Oils such as apricot kernel oil, avocado oil, babassu oil, cottonseed oil, borage oil, thistle oil, groundnut oil, gamma-oryzanol, rose-hip seed oil, hemp oil, hazelnut oil, blackcurrant seed oil, jojoba oil, cherry kernel oil, salmon oil, linseed oil, maize germ oil, macadamia nut oil, almond oil, evening primrose oil, mink fat, olive oil, pecan nut oil, peach kernel oil, pistachio nut oil, rape-seed oil, rice germ oil, castor oil, safflower seed oil, sesame seed oil, soybean oil, sunflower seed oil, tea tree oil, grape-seed oil or wheat germ oil.
  • avocado oil babassu oil, cottonseed oil, borage oil, thistle oil, groundnut oil, gamma-oryzanol, rose-hip seed oil, hemp oil, hazelnut oil, blackcurrant seed oil, jojoba oil,
  • the aroma particles according to the invention may contain additionally other substances such as, for example, emulsifiers, colorants, antioxidants, stabilisers, UV-filters, vitamins and other ingredients which are conventional in the food, cosmetics or olfactory substance industries.
  • substances such as, for example, emulsifiers, colorants, antioxidants, stabilisers, UV-filters, vitamins and other ingredients which are conventional in the food, cosmetics or olfactory substance industries.
  • Suitable antioxidants are, for example, amino acids (for example, glycin, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (for example urocanic acid) and derivatives thereof, peptides such as D,L-carnosine, D-carnosine, L-carnosine and derivatives thereof (for example anserine), carotinoids, carotenes (for example ⁇ -carotene, ⁇ -carotene, lycopene) and derivatives thereof, lipoic acid and derivatives thereof (for example dihydro- ⁇ -lipoic acid), aurothioglucose, propyl thiouracil and other thiols (for example thioredoxin, glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl
  • Suitable light stabilisers are, for example, organic UV absorbers from the class of 4-aminobenzoic acid and derivatives, salicylic acid derivatives, benzophenone derivatives, dibenzoylmethane derivatives, diphenyl acrylates, 3-imidazol-4-yl acrylic acid and esters thereof, benzofurane derivatives, benzylidene malonate derivatives, polymeric UV absorbers, containing one or more organosilicon radicals, cinnamic acid derivatives, camphor derivatives, trianilino-s-triazine derivatives, 2-hydroxyphenyl benzotriazole derivatives, 2-phenylbenzimidazole-5-sulfonic acid and salts thereof, anthranilic acid menthyl esters, benzotriazole derivatives.
  • organic UV absorbers from the class of 4-aminobenzoic acid and derivatives, salicylic acid derivatives, benzophenone derivatives, dibenzoylmethane derivatives, dipheny
  • suitable cooling substances 1-menthol, menthone glycerol acetal, menthyl lactate, substituted menthyl-3-carboxylic acid amides (for example menthyl-3-carboxylic acid-N-ethylamide), 2-isopropyl-N,2,3-trimethylbutanamide, substituted cyclohexane carboxylic acid amides, 3-menthoxypropane-1,2-diol, 2-hydroxyethylmenthyl carbonate, 2-hydroxypropylmenthyl carbonate, N-acetylglycine menthyl ester, menthylhydroxycarboxylic acid esters (for example menthyl-3-hydroxybutyrate), monomenthyl succinate 2-mercaptocyclodecanone, menthyl-2-pyrrolidin-5-one carboxylate.
  • suitable cooling substances 1-menthol, menthone glycerol acetal, menthyl lactate, substituted menthyl-3-carbox
  • the melts obtainable by the process according to the invention are still flowable such that the melt can be discharged through small openings at feasible temperatures and not excessive extrusion pressure, without leading to undesirable aroma losses.
  • the melt discharged from the extruder enables effective die-face pelletisation to be carried out virtually without cutting losses. Cutting losses are understood to be those aroma particles which do not fall within the desired particle size fraction.
  • the preferred type of extruder is a twin-screw extruder.
  • the openings at the extruder exit, through which the melt is delivered may be of any form and size. Round openings having a diameter of from 0.1 to 5 mm, preferably 0.2 to 2.5 mm, in particular preferably 0.3 to 1.5 mm, are preferred. Perforated disks are normally used.
  • the aroma particles obtained have an apparent density of from 0.5 to 1.5 kg/l, preferably 0.7 to 0.9 kg/l.
  • a die-face pelletisation of the melt discharged from the extruder in a flowable, still unsolidified state is carried out in the immediate spatial proximity of the extruder exit.
  • the comminution may thus take place by means of knives, wires or some other cutting tool.
  • the direction of motion of the cutting tools may be designed to be vertical, horizontal or in both directions, as well as rotary.
  • the die-face pelletisation of the melt according to the invention enables a homogeneous product having a narrow, regulated particle size distribution to be prepared and simultaneously to a large extent eliminates the occurrence of the undesirable dusty fines, confining it to less than 2 wt. %.
  • process according to the invention may be carried out in the following stages:
  • the aromas can normally be released from the aroma particles by humidity, water, temperature or combinations thereof.
  • the aroma particles according to the invention can be used, for example, for aromatising foods or oral hygiene products, such as instant beverage powders, teas, soup or sauce powders, confectionery, chewing-gums, toothpastes, oral gels, chewable tablets or chewable sweets.
  • foods or oral hygiene products such as instant beverage powders, teas, soup or sauce powders, confectionery, chewing-gums, toothpastes, oral gels, chewable tablets or chewable sweets.
  • the aroma particles according to the invention can be used, for example, for atomatising pharmaceuticals and pharmaceutical formulations, such as sweets for sucking, tablets for sucking, chewable sweets, chewable tablets, tablets to be dissolved in water or infusion formulations.
  • pharmaceuticals and pharmaceutical formulations such as sweets for sucking, tablets for sucking, chewable sweets, chewable tablets, tablets to be dissolved in water or infusion formulations.
  • the aroma particles according to the invention can be used, for example, for aromatising consumer articles such as cosmetics, soaps, detergents, washing agents, room fragrancers, hygienic or household products.
  • a suitable carbohydrate mixture is melted in a twin-screw, TO-EX 45-type extruder from Togum, having nine housing blocks and a plurality of separately temperature-controllable zones having the following operating conditions: heating temperature 1 st zone 75° C. heating temperature 2 nd zone 90° C. heating temperature 3 rd zone 40° C. heating temperature die 100 to 120° C., depending on pressure and flow rate product temperature entering room temperature 1 st zone product temperature entering 2 nd zone 60° C. product temperature entering 3 rd zone 120° C. product temperature entering die 110° C. product temperature entering l st zone e.g. 96° C. (90 to 110° C.) screw speed 100 rpm dry substance flow rate 30 kg/h lemon aroma flow rate 1.8 kg/h
  • the carbohydrate mixture comprises the raw materials Glucidex IT 47 W from wheat (from Roquette; monosaccharides 0.7%, disaccharides 56.3%, trisaccharides 18.7%, tetrasaccharides 1.8%, oligosaccharides from the pentasaccharides upwards, having a molecular weight of over 1000, 22.5%) as well as Maltodextrin DE 15-19 from wheat (from Cerestar, monosaccharides 0.4%, disaccharides 5.0%, trisaccharides 9.5%, tetrasaccharides 5.0%, pentasaccharides 4.8%, hexasaccharides 11.4%, oligosaccharides from the heptasaccharides upwards 63.9%).
  • a suitable formulation contains 8340 g Glucidex IT 47 W from wheat, 3600 g Maltodextrin DE 15-19 from wheat and 60 g Monomuls (from Grunau-Illertissen, molecularly distilled monoglyceride based on palm oil, E471). It has a calculated 33.50% content of oligosaccharides greater than DP 6.
  • the aroma to which is added 3% of the emulsifier Tween 80 (from ICI, polyoxyethylene-(20)-sorbitan monooleate or polysorbate 80), is introduced continuously into the front region of the extruder at a dose of, for example, 6%, with reference to the dry mixture, by way of a supply by electromechanical reciprocating metering pump at a pressure of approximately 30 to 35 bar.
  • the extrusion dies effect the emulsification of the aroma in the melt.
  • the die-face pelletisation is implemented in gas-tight manner in order to prevent aroma contamination of the environment.
  • 3 knives of 0.5 mm sheet steel and a pelletising plate having 600 drilled holes of nominal diameter ⁇ 1.0 and 1000* ⁇ 0.6 drilled holes on concentric circles are utilised for the preparation of aroma particles of nominal particle size 1 mm.
  • the die-face pelletisation rotation speed, for adjusting the pellet length is infinitely variable dependent on the solids flow rate.
  • the pellets obtained here have an apparent density of approx. 0.8 to 0.9 kg/l. Dust and/or oversized particles are then removed by a doubledeck sieve having 0.8 mm and 1.25 mm sieve sizes. The sieving losses are less than 5% of yield.
  • a further suitable formulation having 4740 g Glucidex maize, 3600 g maltodextrin maize, 1400 g spray-dried glucose from maize, 200 g gum arabic and 60 g Monomuls has a calculated 39.70% content of oligosaccharides greater than DP 6.
  • the Cerestar spray-dried glucose from maize has the trade name C * Dry GL 01934 and comprises 11.5% monosaccharides, 40.1% disaccharides, 21.0% trisaccharides, 8.7% tetrasaccharides, 3.2% pentasaccharides and 1.0% hexasaccharides as well as 24.5% oligosaccharides from the heptasaccharides upwards.
  • the operating conditions of the TO-EX 45 twin-screw extruder are as follows: heating temperature 1 st zone 75° C. heating temperature 2 nd zone 90° C. heating temperature 3 rd zone 40° C. heating temperature die 100 to 120° C., depending on pressure and flow rate product temperature entering room temperature 1 st zone product temperature entering 2 nd zone 60° C. product temperature entering 3 rd zone 120° C. product temperature entering die 110° C. product temperature entering 1 st zone e.g. 96° C. (90 to 110° C.) screw speed 100 rpm dry substance flow rate 30 kg/h passion fruit aroma flow rate 1.8 kg/h
  • the Maltodextrin DE 15-19 should be regarded as carbohydrate polymers having an average molecular weight greater than 1000, while the two glucose syrups are on average markedly below a molecular weight of 1000.
  • the procedure is transferable to any other flavours, but also to fragrance oils. Using the same procedure, it is furthermore possible to prepare larger particle sizes of up to several millimetres as well as smaller particle sizes up to 0.3 mm.
  • Aromatisation of black tea in tea-bags with 3 wt. % lemon aroma particles ( ⁇ 1 mm, length 1 to 2 mm). During storage of the tea, the aroma remains enclosed in the pellet matrix and is not released until, on brewing, the particle matrix is dissolved in hot water.
  • Aromatisation of an instant beverage powder mixture comprising 90 wt. % saccharose, 8 wt. % citric acid, 1 wt. % further ingredients (calcium phosphate, ascorbic acid, modified cellulose, colorant) and 1 wt. % yellow-coloured passion fruit aroma particles ( ⁇ 0.6 mm) which have been prepared by the procedure described.
  • the mixture is distinguished by particularly good stability of the aroma in storage, even at low particle size. Because of the small proportion of oxidation-sensitive passion fruit aroma at the surface of the particles, the occurrence of off-flavours (caused by oxidation) is very greatly minimised.
  • Blue-coloured peppermint aroma particles ( ⁇ 0.6 mm, length 0.4 mm) prepared by the process described are added to chewing-gum mass. The particles create a particular optical effect. The aroma is released in mechanical manner during chewing.
  • Uncoloured perfume oil particles ( ⁇ 0.6 mm, length 0.4 mm) which have been prepared by the process described are added to a heating and cooling plate.
  • the perfume oil is released by heating.
  • the release of the perfume oil can be started and stopped repeatedly by a heating and cooling cycle until the perfume oil is completely consumed.
  • Uncoloured perfume oil particles ( ⁇ 0.6 mm, length 0.4 mm) prepared by the process described are added to a soap.
  • the perfume oil is released by dissolution.
  • the release of the perfume oil can be started and stopped repeatedly by a solubilisation and drying until the soap is completely consumed.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Seasonings (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Surface Treatment Of Glass (AREA)
  • Detergent Compositions (AREA)
  • Confectionery (AREA)
  • Tea And Coffee (AREA)
US10/512,841 2002-04-30 2003-04-26 Aroma particles Abandoned US20050220981A1 (en)

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DE10219228A DE10219228A1 (de) 2002-04-30 2002-04-30 Aromapartikel
DE10219228.6 2002-04-30
PCT/EP2003/004383 WO2003092412A2 (fr) 2002-04-30 2003-04-26 Particules aromatiques

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060182775A1 (en) * 2005-02-16 2006-08-17 Jacqui Everett Insect repellent
US20070142795A1 (en) * 2005-12-15 2007-06-21 Kimberly-Clark Worldwide, Inc. Food scented personal hygiene products
US20080044546A1 (en) * 2006-08-18 2008-02-21 Michael Jensen Product and method for providing texture, aroma, and flavor to microwave popcorn
US20080138492A1 (en) * 2004-08-06 2008-06-12 Juris Union Ltd Comletely-Soluble Solid Particle(s) Based on Dietary Fibre(s)
US20080220140A1 (en) * 2007-01-25 2008-09-11 Symrise Gmbh & Co. Kg Use of propenylphenyl glycosides for enhancing sweet sensory impressions
NL2001320C2 (nl) * 2008-02-25 2009-08-26 Friesland Brands Bv Systeem voor aroma-afgifte.
US20100239716A1 (en) * 2006-01-23 2010-09-23 Symrise Gmbh & Co., Kg Tea aromatization
US20100248962A1 (en) * 2009-03-31 2010-09-30 Smg Brands, Inc. Compositions for the masking of malodor in agricultural compositions and methods of making and using thereof
US20100316760A1 (en) * 2008-02-19 2010-12-16 Jorg Kowalczyk confectionery aroma containing products
EP2415357A1 (fr) * 2010-08-02 2012-02-08 Unilever N.V. Produit alimentaire doté d'une saveur encapsulée
US8695609B2 (en) * 2006-02-10 2014-04-15 R. J. Reynolds Tobacco Company Smokeless tobacco composition
US20140311016A1 (en) * 2011-11-09 2014-10-23 Rutgers, The State University Of New Jersey Beg Bug Lures
FR3007290A1 (fr) * 2013-06-25 2014-12-26 Expressions Aromatiques Procede de fabrication de granules contenant un principe actif, a dluo et charge en principe actif optimisees
US9687010B2 (en) 2012-03-14 2017-06-27 Mccormick & Company, Incorporated Extrusion encapsulation of actives at an increased load, using surface active plant extracts
US10897918B1 (en) * 2013-03-15 2021-01-26 Mccormick & Company, Incorporated Extrusion encapsulation with narrow particle size and shape distribution, high solubility, and low surface oil

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR0313108B1 (pt) * 2002-08-27 2013-11-26 Processo para preparação de lascas de filme com perfume, lasca de filme com perfume, composição granular para limpeza, e, métodos para melhorar a estabilidade na armazenagem de partículas de perfume e para depositar perfume sobre uma superfície
JP2005187431A (ja) * 2003-12-26 2005-07-14 Shiseido Co Ltd 脂肪蓄積促進用組成物
CA2553048A1 (fr) * 2004-01-23 2005-09-01 Firmenich Sa Grosses perles vitreuses
JP2006083071A (ja) * 2004-09-14 2006-03-30 Takasago Internatl Corp 香粧品用固形製剤
WO2006068486A2 (fr) * 2004-12-23 2006-06-29 Dolphys Medical B.V. Detergent ou composition adoucissante comprenant un moyen de liberation de parfum controle
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DE102010001425A1 (de) 2010-02-01 2011-08-04 Martin Bauer GmbH & Co. KG, 91487 Verfahren zur Extrusion von Extrakten, Aromen, Vitaminen und/oder deren Mischungen zur Herstellung von lagerstabilen Granulaten sowie danach hergestellte Granulate für Tee und teeähnliche Erzeugnisse
FR2966700B1 (fr) * 2010-10-29 2013-01-11 Bernard Mompon Procede de fabrication d?articles d?origine vegetale impregnes de substance liquide vegetale
EP2457554A1 (fr) 2010-11-24 2012-05-30 Symrise AG Mélange comprenant du menthol
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US9732305B2 (en) 2014-12-17 2017-08-15 Seyed Mohammad Bagher Marashi Compositions and methods for extracting perfume oil from pistachio hulls
CN107105721B (zh) * 2014-12-24 2021-04-06 弗门尼舍有限公司 前体调味料递送颗粒
CN112745984B (zh) * 2020-12-15 2021-10-22 广州芬豪香精有限公司 持久留香型香精
WO2024054529A1 (fr) * 2022-09-08 2024-03-14 Abstrax Tech Inc. Composés modificateurs d'agrumes dans le cannabis

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3704137A (en) * 1970-06-11 1972-11-28 Eugene E Beck Essential oil composition and method of preparing the same
US4689235A (en) * 1984-01-31 1987-08-25 Scm Corporation Encapsulation matrix composition and encapsulate containing same
US4820534A (en) * 1984-03-19 1989-04-11 General Foods Corporation Fixation of volatiles in extruded glass substrates
US5009900A (en) * 1989-10-02 1991-04-23 Nabisco Brands, Inc. Glassy matrices containing volatile and/or labile components, and processes for preparation and use thereof
US5496574A (en) * 1995-02-01 1996-03-05 Nestec S.A. Encapsulated sensory agents
US5972395A (en) * 1997-04-25 1999-10-26 Kraft Foods, Inc. Method of preparing glass stabilized material
US6190591B1 (en) * 1996-10-28 2001-02-20 General Mills, Inc. Embedding and encapsulation of controlled release particles
US20010036503A1 (en) * 1999-09-06 2001-11-01 Daniel Benczedi Process for the preparation of granules for the controlled release of volatile compounds
US6436453B1 (en) * 2000-06-16 2002-08-20 General Mills, Inc. Production of oil encapsulated minerals and vitamins in a glassy matrix
US20020117769A1 (en) * 2000-12-04 2002-08-29 Arch Paul Edward Foamed cellular particles of an expandable polymer composition
USRE37860E1 (en) * 1994-10-17 2002-09-24 Firmenich Sa Particulate flavor compositions and process to prepare same

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2856291A (en) 1957-03-18 1958-10-14 Thomas H Schultz Preparation of solid flavoring compositions
US4499112A (en) * 1983-03-21 1985-02-12 Sunkist Growers, Inc. Process for forming solid juice composition and product of the process
US4707367A (en) * 1984-07-16 1987-11-17 Sunkist Growers, Inc. Solid essential oil flavor composition
JP2824679B2 (ja) 1989-11-24 1998-11-11 日本電子テクニクス株式会社 荷電粒子線装置
DE69121098T2 (de) * 1990-04-04 1997-01-23 Berwind Pharma Service Wässrige filmbildende überzugszusammensetzungen aus maltodextrin und zellulosederivaten
WO1992019649A1 (fr) 1991-04-26 1992-11-12 Clonatec Antigenes reconnus par des anticorps de la polyarthrite rhumatoide, leur preparation et leurs applications
US5137860A (en) 1991-06-27 1992-08-11 Monsanto Company Process for the transformation of vanadium/phosphorus mixed oxide catalyst precursors into active catalysts for the production of maleic anhydride
WO1994006308A1 (fr) 1992-09-22 1994-03-31 Mccormick & Company, Inc. Encapsulage d'agents aromatiques
AU6701694A (en) * 1993-04-16 1994-11-08 Mccormick & Company, Inc. Encapsulation compositions
GB2281841B (en) 1993-09-20 1997-07-09 Int Flavors & Fragrances Inc Extrusion and agglomeration process for fiber containing food ingredient
TW518251B (en) 1997-09-24 2003-01-21 Mitsubishi Chem Corp Powdered emulsifier composition and process for producing the same
EP1018816A1 (fr) * 1998-10-19 2000-07-12 Lucent Technologies Inc. Procédé et système ARQ cumulatif
EP1124443B1 (fr) * 1998-11-04 2005-02-09 Firmenich Sa Systeme de liberation solide pour ingredients aromatiques
EP1034705A3 (fr) * 1999-03-10 2001-02-28 Haarmann & Reimer Gmbh Matériau d'encapsulation et procédé d'encapsulation des parfums et des arômes
DE19954528A1 (de) * 1999-11-12 2001-05-17 Haarmann & Reimer Gmbh Eingekapseltes Aroma
US6290591B1 (en) * 2000-05-11 2001-09-18 Townsend Engineering Company Method and apparatus for determining the number of looped sausages for deposit on a smokestick
US6413573B1 (en) * 2000-06-27 2002-07-02 Nestac, S.A. Flavor composition
GB0018811D0 (en) * 2000-08-02 2000-09-20 Quest Int Particles
FR2828380B1 (fr) * 2001-08-10 2005-07-29 Fontarome Composition a structure composite contenant des substances aromatiques et/ou des substances non aromatiques volatiles et/ou sensibles aux agents exterieurs, et son procede de fabrication
US6797290B2 (en) * 2001-09-17 2004-09-28 Mcneil-Ppc, Inc. Compositions for appetite control and related methods

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3704137A (en) * 1970-06-11 1972-11-28 Eugene E Beck Essential oil composition and method of preparing the same
US4689235A (en) * 1984-01-31 1987-08-25 Scm Corporation Encapsulation matrix composition and encapsulate containing same
US4820534A (en) * 1984-03-19 1989-04-11 General Foods Corporation Fixation of volatiles in extruded glass substrates
US5009900A (en) * 1989-10-02 1991-04-23 Nabisco Brands, Inc. Glassy matrices containing volatile and/or labile components, and processes for preparation and use thereof
USRE37860E1 (en) * 1994-10-17 2002-09-24 Firmenich Sa Particulate flavor compositions and process to prepare same
US5496574A (en) * 1995-02-01 1996-03-05 Nestec S.A. Encapsulated sensory agents
US6190591B1 (en) * 1996-10-28 2001-02-20 General Mills, Inc. Embedding and encapsulation of controlled release particles
US5972395A (en) * 1997-04-25 1999-10-26 Kraft Foods, Inc. Method of preparing glass stabilized material
US20010036503A1 (en) * 1999-09-06 2001-11-01 Daniel Benczedi Process for the preparation of granules for the controlled release of volatile compounds
US6436453B1 (en) * 2000-06-16 2002-08-20 General Mills, Inc. Production of oil encapsulated minerals and vitamins in a glassy matrix
US20020117769A1 (en) * 2000-12-04 2002-08-29 Arch Paul Edward Foamed cellular particles of an expandable polymer composition

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080138492A1 (en) * 2004-08-06 2008-06-12 Juris Union Ltd Comletely-Soluble Solid Particle(s) Based on Dietary Fibre(s)
US7875306B2 (en) 2004-08-06 2011-01-25 Maya Flowers S.A. Completely-soluble solid particle(s) based on dietary fibre(s)
US20060182775A1 (en) * 2005-02-16 2006-08-17 Jacqui Everett Insect repellent
US20070142795A1 (en) * 2005-12-15 2007-06-21 Kimberly-Clark Worldwide, Inc. Food scented personal hygiene products
US20100239716A1 (en) * 2006-01-23 2010-09-23 Symrise Gmbh & Co., Kg Tea aromatization
US8695609B2 (en) * 2006-02-10 2014-04-15 R. J. Reynolds Tobacco Company Smokeless tobacco composition
US20080044546A1 (en) * 2006-08-18 2008-02-21 Michael Jensen Product and method for providing texture, aroma, and flavor to microwave popcorn
US20080220140A1 (en) * 2007-01-25 2008-09-11 Symrise Gmbh & Co. Kg Use of propenylphenyl glycosides for enhancing sweet sensory impressions
US20100316760A1 (en) * 2008-02-19 2010-12-16 Jorg Kowalczyk confectionery aroma containing products
NL2001320C2 (nl) * 2008-02-25 2009-08-26 Friesland Brands Bv Systeem voor aroma-afgifte.
US20110065791A1 (en) * 2008-02-25 2011-03-17 Albert Thijs Poortinga System for aroma release
WO2009108051A1 (fr) * 2008-02-25 2009-09-03 Friesland Brands B.V. Système de libération d'arôme
US20100248962A1 (en) * 2009-03-31 2010-09-30 Smg Brands, Inc. Compositions for the masking of malodor in agricultural compositions and methods of making and using thereof
EP2415357A1 (fr) * 2010-08-02 2012-02-08 Unilever N.V. Produit alimentaire doté d'une saveur encapsulée
WO2012016764A1 (fr) * 2010-08-02 2012-02-09 Unilever Nv Produit alimentaire contenant un arôme encapsulé
US20140311016A1 (en) * 2011-11-09 2014-10-23 Rutgers, The State University Of New Jersey Beg Bug Lures
US9510581B2 (en) * 2011-11-09 2016-12-06 Rutgers, The State University Of New Jersey Bed bug lures
US9687010B2 (en) 2012-03-14 2017-06-27 Mccormick & Company, Incorporated Extrusion encapsulation of actives at an increased load, using surface active plant extracts
US10897918B1 (en) * 2013-03-15 2021-01-26 Mccormick & Company, Incorporated Extrusion encapsulation with narrow particle size and shape distribution, high solubility, and low surface oil
FR3007290A1 (fr) * 2013-06-25 2014-12-26 Expressions Aromatiques Procede de fabrication de granules contenant un principe actif, a dluo et charge en principe actif optimisees
WO2014207355A1 (fr) * 2013-06-25 2014-12-31 Expressions Aromatiques Procédé de fabrication de granulés contenant un principe actif, à dluo et charge en principe actif optimisées

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DE10219228A1 (de) 2003-11-13
JP2005528482A (ja) 2005-09-22
AU2003232211A1 (en) 2003-11-17
US20140127390A1 (en) 2014-05-08
US20100007040A1 (en) 2010-01-14
US9706791B2 (en) 2017-07-18
EP1501375A2 (fr) 2005-02-02
WO2003092412A3 (fr) 2004-02-05
ATE381893T1 (de) 2008-01-15
BR0309755A (pt) 2005-03-08
WO2003092412A2 (fr) 2003-11-13
EP1501375B1 (fr) 2007-12-26
DE50308884D1 (de) 2008-02-07
AU2003232211A8 (en) 2003-11-17
US8641945B2 (en) 2014-02-04

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