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WO2024153727A1 - Microcapsules obtenues à partir d'un prépolymère à base de polylactone - Google Patents

Microcapsules obtenues à partir d'un prépolymère à base de polylactone Download PDF

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Publication number
WO2024153727A1
WO2024153727A1 PCT/EP2024/051100 EP2024051100W WO2024153727A1 WO 2024153727 A1 WO2024153727 A1 WO 2024153727A1 EP 2024051100 W EP2024051100 W EP 2024051100W WO 2024153727 A1 WO2024153727 A1 WO 2024153727A1
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WO
WIPO (PCT)
Prior art keywords
core
polylactone
polyisocyanate
origin
perfume
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2024/051100
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English (en)
Inventor
Yongtao WU
Jia-jun SHEN
Damien Berthier
Nicolas Paret
Lahoussine Ouali
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Firmenich SA
Original Assignee
Firmenich SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Firmenich SA filed Critical Firmenich SA
Priority to EP24701346.9A priority Critical patent/EP4651987A1/fr
Priority to CN202480017550.6A priority patent/CN120957806A/zh
Publication of WO2024153727A1 publication Critical patent/WO2024153727A1/fr
Priority to MX2025008292A priority patent/MX2025008292A/es
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking
    • B01J13/18—In situ polymerisation with all reactants being present in the same phase
    • B01J13/185—In situ polymerisation with all reactants being present in the same phase in an organic phase
    • 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

Definitions

  • the present invention relates to a process of preparing a core-shell microcapsule and a core-shell microcapsule slurry comprising a polylactone-based polyisocyanate prepolymer obtained by reacting a polylactone polyol and a polyisocyanate, the core-shell microcapsule and core-shell microcapsule slurry as well as perfuming compositions and consumer products comprising the same.
  • Polyurea and polyurethane-based microcapsule slurries are widely used for example in perfumery industry as they provide a long lasting pleasant olfactory effect after their applications on different substrates.
  • Those microcapsules have been widely disclosed in the prior art (see for example W02007/004166 or EP 2300146 from the Applicant).
  • the main disadvantage of polyurea and polyurethane-based microcapsule is their weak or non-existing biodegradability.
  • the present invention is proposing a solution to the above-mentioned problem by providing new microcapsules and a process for preparing said microcapsules.
  • active ingredient it is meant a single compound or a combination of ingredients.
  • perfume or flavor oil it is meant a single perfuming or flavoring compound or a mixture of several perfuming or flavoring compounds.
  • consumer product or “end-product” it is meant a manufactured product ready to be distributed, sold and used by a consumer.
  • a “microcapsule”, or the similar, in the present invention has a morphology that can vary from a core-shell to a matrix type. According to one embodiment, it is of the core-shell type.
  • the microcapsules comprise a core based on a hydrophobic material, typically a perfume, and a shell surrounding the core.
  • Microcapsules have a particle size distribution in the micron range (e.g. a mean diameter) comprised between about 1 and 3000 microns, preferably comprised between 1 and 1000 microns, more preferably between 1 and 500 microns, and even more preferably between 5 and 50 microns.
  • the polymeric shell of the microcapsule according to the present invention is formed by interfacial polymerization and/or interfacial reaction.
  • particle size it is meant an average diameter of particles based on size distribution measured by dynamic light scattering (DLS) using Zetasizer Nano ZS equipment from Malvern Instruments Ltd., UK when particles are dispersed into a water phase.
  • DLS dynamic light scattering
  • microcapsules size it is meant the volume mean diameter (D[4,3]) of the relevant capsules, capsules suspension as obtained by laser light scattering of a diluted sample in a Malvern Mastersizer 3000.
  • the present invention relates to a process for preparing a core-shell microcapsule or core-shell microcapsule slurry, wherein the process comprises the steps of: a. Admixing a hydrophobic material, preferably a perfume oil, and a polylactone- based polyisocyanate prepolymer, obtained by reacting a polylactone polyol and a polyisocyanate, to form an oil phase; b. Dispersing the oil phase in a dispersing phase comprising an emulsifier or a stabilizer and, optionally, a cross-linker to form an emulsion; c. Optionally, adding into the emulsion a cross-linker; d. Applying conditions sufficient to induce cross-linking of the polylactone-based polyisocyanate prepolymer to form the core-shell microcapsule or core-shell microcapsule slurry.
  • a hydrophobic material preferably a perfume oil
  • a hydrophobic material and a polylactone-based polyisocyanate prepolymer, obtained by reacting a polylactone polyol and polyisocyanate, are admixed to form an oil phase.
  • a polylactone-based polyisocyanate prepolymer is optionally dissolved in a solvent (e.g., ethyl acetate) before admixing with a hydrophobic material to form an oil phase.
  • a solvent e.g., ethyl acetate
  • the solvent may be chloroform, dichloromethane, carbon tetrachloride, benzene, toluene, xylene, cyclohexanone and 2- nitropropane, acetone, 2-butanone, ethyl acetate, butyl acetate, such as n-butyl acetate, dimethylformamide and/or acetonitrile.
  • the hydrophobic material is preferably an oil.
  • the hydrophobic material according to the invention can be “inert” material like solvents or active ingredients.
  • hydrophobic material any hydrophobic material which forms a two-phase dispersion when mixed with water.
  • the hydrophobic material is typically liquid at about 20°C.
  • the hydrophobic material is a hydrophobic active ingredient.
  • hydrophobic materials When the hydrophobic materials is an active ingredient, it is preferably chosen from the group consisting of flavors, flavor ingredients, perfumes, perfume ingredients, nutraceuticals, cosmetics, pest control agents, biocide actives and mixtures thereof.
  • the hydrophobic material comprises a phase change material (PCM).
  • PCM phase change material
  • the hydrophobic material comprises a mixture of a perfume with another ingredient selected from the group consisting of nutraceuticals, cosmetics, pest control agents and biocide actives.
  • the hydrophobic material comprises a mixture of biocide actives with another ingredient selected from the group consisting of perfumes, nutraceuticals, cosmetics, pest control agents.
  • the hydrophobic material comprises a mixture of pest control agents with another ingredient selected from the group consisting of perfumes, nutraceuticals, cosmetics, biocide actives.
  • the hydrophobic material comprises a perfume.
  • the hydrophobic material consists of a perfume.
  • the hydrophobic material consists of biocide actives.
  • the hydrophobic material consists of pest control agents.
  • perfume an ingredient or a composition that is a liquid at about 20°C.
  • said perfume oil can be a perfuming ingredient alone or a mixture of ingredients in the form of a perfuming composition.
  • a perfuming ingredient it is meant here a compound, which is used for the primary purpose of conferring or modulating an odor.
  • such an ingredient, to be considered as being a perfuming one must be recognized by a person skilled in the art as being able to at least impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
  • perfume oil also includes a combination of perfuming ingredients with substances which together improve, enhance or modify the delivery of the perfuming ingredients, such as perfume precursors, modulators, emulsions or dispersions, as well as combinations which impart an additional benefit beyond that of modifying or imparting an odor, such as long- lastingness, blooming, malodor counteraction, antimicrobial effect, microbial stability, pest control.
  • perfuming ingredients such as perfume precursors, modulators, emulsions or dispersions, as well as combinations which impart an additional benefit beyond that of modifying or imparting an odor, such as long- lastingness, blooming, malodor counteraction, antimicrobial effect, microbial stability, pest control.
  • 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.
  • these perfuming ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfurous heterocyclic compounds and essential oils (for example Thyme oil), 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.
  • Aromatic-herbal ingredients eucalyptus oil, camphor, eucalyptol, 5- methyltricyclo[6.2.1 ,0 2 ’ 7 ]undecan-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4- dimethyl-1 ,3-oxathiane, 2,2,7/8,9/10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and/or alpha-pinene;
  • Citrus ingredients dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and/or 1,4(8)-p-menthadiene;
  • ingredients e.g. amber, powdery spicy or watery: dodecahydro-3a,6,6,9a- tetramethyl-naphtho[2,1-b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, eugenol, cinnamic aldehyde, clove oil, 3-(1 ,3-benzodioxol-5-yl)-2- methylpropanal, 7-methyl-2H-1 ,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl- 1 ,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1- thia-4-azaspiro[4.4]nonane and/or 3-(3-isopropyl-1-phenyl)butanal.
  • ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds also known as properfume or profragrance.
  • suitable properfumes may include 4-(dodecylthio)-4- (2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1- cyclohexen-1-yl)-2-butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1- butanone, 2-(dodecylthio)octan-4-one, 2-phenylethyl oxo(phenyl)acetate, 3,7-dimethylocta- 2,6-dien-1-yl oxo(phenyl)acetate, (Z)-hex-3-en-1-yl oxo(
  • the perfuming ingredients may be dissolved in a solvent of current use in the perfume industry.
  • the solvent is preferably not an alcohol.
  • solvents are diethyl phthalate, isopropyl myristate, Abalyn® (rosin resins, available from Eastman), benzyl benzoate, ethyl citrate, triethyl citrate, limonene or other terpenes, or isoparaffins.
  • the solvent is very hydrophobic and highly sterically hindered, like for example Abalyn® or benzyl benzoate.
  • 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.
  • Preferred perfuming ingredients are those having a high steric hindrance and in particular those from one of the following groups:
  • Group 1 perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched Ci to C4 alkyl or alkenyl substituent;
  • Group 2 perfuming ingredients comprising a cyclopentane, cyclopentene, cyclopentanone or cyclopentenone ring substituted with at least one linear or branched C4 to Cs alkyl or alkenyl substituent;
  • Group 3 perfuming ingredients comprising a phenyl ring or perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched C5 to Cs alkyl or alkenyl substituent or with at least one phenyl substituent and optionally one or more linear or branched Ci to C3 alkyl or alkenyl substituents;
  • Group 4 perfuming ingredients comprising at least two fused or linked Cs and/or Ge rings;
  • Group 5 perfuming ingredients comprising a camphor-like ring structure
  • Group 6 perfuming ingredients comprising at least one C? to C20 ring structure
  • Group 7 perfuming ingredients having a logP value above 3.5 and comprising at least one tert-butyl or at least one trichloromethyl substituent;
  • Group 1 2,4-dimethyl-3-cyclohexene-1-carbaldehyde (origin: Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, methyl 2,2-dimethyl-6-methylene- 1 -cyclohexanecarboxylate (origin: Firmenich SA, Geneva, Switzerland), nerone, terpineol, dihydroterpineol, terpenyl acetate, dihydroterpenyl acetate, dipentene, eucalyptol, hexylate, rose oxide, (S)-1 ,8-p-menthadiene-7-ol (origin: Firmenich SA, Geneva, Switzerland), 1-p-menthene-4-ol, (1RS,3RS,4SR)-3-p-mentanyl acetate, (1 R,2S,4R)-4,6,6-trimethyl-bicyclo[3,1,1]heptan-2-ol, tetrahydr
  • Group 3 damascenes, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one (origin: Firmenich SA, Geneva, Switzerland), (1'R)-2-[2-(4'-methyl-3'-cyclohexen-T- yl)propyl]cyclopentanone, alpha-ionone, beta-ionone, damascenone, mixture of 1-(5,5- dimethyl-1-cyclohexen-1-yl)-4-penten-1-one and 1-(3,3-dimethyl-1-cyclohexen-1-yl)-4- penten-1-one (origin: Firmenich SA, Geneva, Switzerland), 1-(2,6,6-trimethyl-1- cyclohexen-1-yl)-2-buten-1-one (origin: Firmenich SA, Geneva, Switzerland), (1S,1'R)- [1-(3',3'-Dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl
  • Group 4 Methyl cedryl ketone (origin: International Flavors and Fragrances, USA), a mixture of (1 RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1.0 2 ’ 6 ]dec-3-en-8-yl 2-methylpropanoate and (1 RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1 ,0 2 ’ 6 ]dec-4-en-8-yl 2-methylpropanoate, vetyverol, vetyverone, 1 -(octahydro-2, 3, 8, 8-tetramethyl-2-naphtalenyl)-1 -ethanone (origin: International Flavors and Fragrances, USA), (5RS,9RS,10SR)-2,6,9,10- tetramethyl-1-oxaspiro[4.5]deca-3,6-diene and the (5RS,9SR,10RS) isomer, 6-ethyl- 2,10,10
  • Group 5 camphor, borneol, isobornyl acetate, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5- ene-2-carbaldehyde, pinene, camphene, 8-methoxycedrane, (8- meth oxy-2, 6, 6, 8- tetramethyl-tricyclo[5.3.1.0(1 ,5)]undecane (origin: Firmenich SA, Geneva, Switzerland), cedrene, cedrenol, cedrol, mixture of 9-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecan-4- one and 10-ethylidene-3-oxatricyclo[6.2.1.0 2 ’ 7 ]undecan-4-one (origin: Firmenich SA, Geneva, Switzerland), 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (origin: Firmenich SA, Geneva, Switzerland);
  • the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients selected from Groups 1 to 7, as defined above. More preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3 to 7, as defined above. Most preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3, 4, 6 or 7, as defined above.
  • the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients having a logP above 3, preferably above 3.5 and even more preferably above 3.75.
  • the perfume used in the invention contains less than 10% of its own weight of primary alcohols, less than 15% of its own weight of secondary alcohols and less than 20% of its own weight of tertiary alcohols.
  • the perfume used in the invention does not contain any primary alcohols and contains less than 15% of secondary and tertiary alcohols.
  • the oil phase (or the oil-based core) comprises:
  • “High impact perfume raw materials” should be understood as perfume raw materials having a LogT ⁇ -4.
  • the odor threshold concentration of a chemical compound is determined in part by its shape, polarity, partial charges and molecular mass. For convenience, the odor threshold concentration is presented as the common logarithm of the threshold concentration, i.e., Log [Threshold] (“LogT”).
  • LogT Log [Threshold]
  • a “density balancing material” should be understood as a material having a density greater than 1.07 g/cm 3 and having preferably low or no odor.
  • the odor threshold concentration of a perfuming compound is determined by using a gas chromatograph (“GC”). Specifically, the gas chromatograph is calibrated to determine the exact volume of the perfume oil ingredient injected by the syringe, the precise split ratio, and the hydrocarbon response using a hydrocarbon standard of known concentration and chain-length distribution. The air flow rate is accurately measured and, assuming the duration of a human inhalation to last 12 seconds, the sampled volume is calculated. Since the precise concentration at the detector at any point in time is known, the mass per volume inhaled is known and hence the concentration of the perfuming compound. To determine the threshold concentration, solutions are delivered to the sniff port at the back-calculated concentration.
  • GC gas chromatograph
  • a panelist sniffs the GC effluent and identifies the retention time when odor is noticed. The average across all panelists determines the odor threshold concentration of the perfuming compound. The determination of odor threshold is described in more detail in C. Vuilleumier et al., Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development, Perfume & Flavorist, Vol. 33, September,, 2008, pages 54-61.
  • the high impact perfume raw materials having a Log T ⁇ -4 are selected from the group consisting of (+-)-1-methoxy-3-hexanethiol, 4-(4-hydroxy-1- phenyl)-2-butanone, 2-methoxy-4-(1-propenyl)-1 -phenyl acetate, pyrazobutyle, 3- propylphenol, 1-(3-methyl-1-benzofuran-2-yl)ethanone, 2-(3-phenylpropyl)pyridine, 1- (3,3/5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one , 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4- penten-1-one, a mixture comprising (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl- benzo[b]furan-2-one and (3SR,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl
  • perfume raw materials having a Log T ⁇ -4 comprise at least one compound chosen in the group consisting of alcohols, phenols, esters lactones, ethers, epoxydes, nitriles and mixtures thereof, preferably in amount comprised between 20 and 70% by weight based on the total weight of the perfume raw materials having a Log T ⁇ - 4.
  • perfume raw materials having a Log T ⁇ -4 comprise between 20 and 70% by weight of aldehydes, ketones, and mixtures thereof based on the total weight of the perfume raw materials having a Log T ⁇ -4.
  • the remaining perfume raw materials contained in the oil-based core may have therefore a Log T>-4.
  • the perfume raw materials having a Log T>-4 are chosen in the group consisting of ethyl 2-methylbutyrate, (E)-3-phenyl-2-propenyl acetate, (+- )-6/8-sec-butylquinoline, (+-)-3-(1 ,3-benzodioxol-5-yl)-2-methylpropanal, verdyl propionate, 1- (octahydro-2, 3, 8, 8-tetramethyl-2-naphtalenyl)-1 -ethanone, methyl 2-((1 RS,2RS)-3-oxo-2- pentylcyclopentyl)acetate, (+-)-(E)-4-methyl-3-decen-5-ol, 2,4-dimethyl-3-cyclohexene-1- carbaldehyde, 1 ,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, tetrahydro-4-methyl-2-(
  • the core comprises a perfume formulation comprising: 0 to 60 wt.% of a hydrophobic solvent (based on the total weight of the perfume formulation),
  • a perfume oil (based on the total weight of the perfume formulation), wherein the perfume oil has at least two, preferably all of the following characteristics: o at least 35%, preferably at least 40%, preferably at least 50%, more preferably at least 60% of perfuming ingredients having a log P above 3, preferably above 3.5, o at least 20%, preferably at least 25%, preferably at least 30%, more preferably at least 40% of Bulky materials of groups 1 to 6, preferably 3 to 6 as herein defined and o at least 15%, preferably at least 20%, more preferably at least 25%, even more preferably at least 30% of high impact perfume materials having a Log T ⁇ -4, optionally, further hydrophobic active ingredients.
  • the perfume comprises 0 to 60 wt.% of a hydrophobic solvent.
  • the hydrophobic solvent is a density balancing material preferably chosen in the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylate, benzyl cinnamate, and mixtures thereof.
  • the hydrophobic solvent has Hansen Solubility Parameters compatible with entrapped perfume oil.
  • Hansen solubility parameter refers to a solubility parameter approach proposed by Charles Hansen used to predict polymer solubility and was developed around the basis that the total energy of vaporization of a liquid consists of several individual parts. To calculate the "weighted Hansen solubility parameter” one must combine the effects of (atomic) dispersion forces, (molecular) permanent dipole-permanent dipole forces, and (molecular) hydrogen bonding (electron exchange).
  • the weighted Hansen solubility parameter is calculated as (5D 2 + 5P 2 + 6H 2 ) 05 , wherein 5D is the Hansen dispersion value (also referred to in the following as the atomic dispersion fore), ⁇ 5P is the Hansen polarizability value (also referred to in the following as the dipole moment), and ⁇ 5H is the Hansen Hydrogen-bonding ("h-bonding") value (also referred to in the following as hydrogen bonding).
  • 5D is the Hansen dispersion value (also referred to in the following as the atomic dispersion fore)
  • ⁇ 5P is the Hansen polarizability value (also referred to in the following as the dipole moment)
  • ⁇ 5H is the Hansen Hydrogen-bonding (“h-bonding”) value (also referred to in the following as hydrogen bonding).
  • Euclidean difference in solubility parameter between a fragrance and a solvent is Calculated as (4 (bDsolvent-bDfragrance) ⁇ + (bP solvent-QPfragrance) ⁇ + (bHsolvent-bHfragrance) ⁇ ) ⁇ in which GDsassemble, GPsassemble, and 5H S rete, are the Hansen dispersion value, Hansen polarizability value, and Hansen h-bonding values of the solvent, respectively; and bDf ra grance, GPfragrance, and GHfragrance are the Hansen dispersion value, Hansen polarizability value, and Hansen I bonding values of the fragrance, respectively.
  • the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force (bD) from 12 to 20, a dipole moment (bP) from 1 to 8, and a hydrogen bonding (bH) from 2.5 to 11.
  • the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force (bD) from 12 to 20, preferably from 14 to 20, a dipole moment (bP) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (bH) from 2.5 to 11, preferably from 4 to 11.
  • At least 90% of the perfume oil, preferably at least 95% of the perfume oil, most preferably at least of 98% of the perfume oil has at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force (bD) from 12 to 20, a dipole moment (bP) from 1 to 8, and a hydrogen bonding (bH) from 2.5 to 11.
  • the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force (bD) from 12 to 20, preferably from 14 to 20, a dipole moment (bP) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (bH) from 2.5 to 11 , preferably from 4 to 11.
  • the perfuming formulation comprises a fragrance modulator (that can be used in addition to the hydrophobic solvent when present or as substitution of the hydrophobic solvent when there is no hydrophobic solvent).
  • the fragrance modulator is defined as a fragrance material with i. a vapor pressure of less than 0.0008 Torr at 22°C; ii. a clogP of 3.5 and higher, preferable 4.0 and higher and more preferable 4.5 iii. at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force from 12 to 20, a dipole moment from 1 to 7, and a hydrogen bonding from 2.5 to 11, iv.
  • Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force from 14 to 20, a dipole moment from 1 to 8, and a hydrogen bonding from 4 to 11, when in solution with a compound having a vapor pressure range of 0.0008 to 0.08 Torr at 22°C.
  • ingredients can be listed as modulators but the list in not limited to the following materials: alcohol C12, oxacyclohexadec-12/13-en-2-one, 3- [(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)methoxy]-2-butanol, cyclohexadecanone, (Z)-4- cyclopentadecen-1-one, cyclopentadecanone, (8Z)-oxacycloheptadec-8-en-2-one, 2-[5- (tetrahydro-5-methyl-5-vinyl-2-furyl)-tetrahydro-5-methyl-2-furyl]-2-propanol, muguet aldehyde, 1 ,5,8-trimethyl-13-oxabicyclo[10.1 ,0]trideca-4,8-diene, (+-)-4,6,6,7,8,8-hexamethyl- 1 ,3,4,6,7,
  • the hydrophobic material is free of any active ingredient (such as perfume).
  • it comprises, preferably consists of hydrophobic solvents, preferably chosen in the group consisting of isopropyl myristate, tryglycerides (e.g.
  • hydrophilic solvents preferably chosen in the group consisting of 1,4-butanediol, benzyl alcohol, triethyl citrate, triacetin, benzyl acetate, ethyl acetate, propylene glycol (1 ,2-propanediol), 1 ,3-propanediol, dipropylene glycol, glycerol, glycol
  • biocide refers to a chemical substance capable of killing living organisms (e.g. microorganisms) or reducing or preventing their growth and/or accumulation. Biocides are commonly used in medicine, agriculture, forestry, and in industry where they prevent the fouling of, for example, water, agricultural products including seed, and oil pipelines.
  • a biocide can be a pesticide, including a fungicide, herbicide, insecticide, algicide, molluscicide, miticide and rodenticide; and/or an antimicrobial such as a germicide, antibiotic, antibacterial, antiviral, antifungal, antiprotozoal and/or antiparasite.
  • Pests refer to any living organism, whether animal, plant or fungus, which is invasive or troublesome to plants or animals, pests include insects notably arthropods, mites, spiders, fungi, weeds, bacteria and other microorganisms.
  • flavor oil it is meant here a flavoring ingredient or a mixture of flavoring ingredients, solvents or adjuvants of current use for the preparation of a flavoring 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 flavor and/or taste.
  • flavoring ingredients are well known to a person skilled in the art and their nature does not warrant a detailed description here, which in any case would not be exhaustive, the skilled flavorist 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 flavoring ingredients are listed in reference texts such as in the book by S.
  • the flavor is a mint flavor.
  • the mint is selected from the group consisting of peppermint and spearmint.
  • the flavor is a cooling agent or mixtures thereof.
  • the flavor is a menthol flavor.
  • Flavors that are derived from or based on fruits where citric acid is the predominant, naturally-occurring acid include but are not limited to, for example, citrus fruits (e.g. lemon, lime), limonene, strawberry, orange, and pineapple.
  • the flavors food is lemon, lime or orange juice extracted directly from the fruit.
  • Further embodiments of the flavor comprise the juice or liquid extracted from oranges, lemons, grapefruits, key limes, citrons, clementines, mandarins, tangerines, and any other citrus fruit, or variation or hybrid thereof.
  • the flavor comprises a liquid extracted or distilled from oranges, lemons, grapefruits, key limes, citrons, clementines, mandarins, tangerines, any other citrus fruit or variation or hybrid thereof, pomegranates, kiwifruits, watermelons, apples, bananas, blueberries, melons, ginger, bell peppers, cucumbers, passion fruits, mangos, pears, tomatoes, and strawberries.
  • the flavor comprises a composition that comprises limonene, in a particular embodiment, the composition is a citrus that further comprises limonene. In another particular embodiment, the flavor comprises a flavor selected from the group comprising strawberry, orange, lime, tropical, berry mix, and pineapple.
  • flavor includes not only flavors that impart or modify the smell of foods but include taste imparting or modifying ingredients.
  • the latter do not necessarily have a taste or smell themselves but are capable of modifying the taste that other ingredients provides, for instance, salt enhancing ingredients, sweetness enhancing ingredients, umami enhancing ingredients, bitterness blocking ingredients and so on.
  • suitable sweetening components may be included in the particles described herein.
  • a sweetening component is selected from the group consisting of sugar (e.g., but not limited to sucrose), a stevia component (such as but not limited to stevioside or rebaudioside A), sodium cyclamate, aspartame, sucralose, sodium saccharine, and Acesulfam K or mixtures thereof.
  • the hydrophobic material represents between about 10% and 60% w/w, or even between 15% and 45% w/w, by weight, relative to the total weight of the oil phase.
  • a polylactone-based polyisocyanate prepolymer according to the present invention is obtained by reacting a polylactone polyol and a polyisocyanate. Thereby it is understood that the polylactone-based polyisocyanate prepolymer is obtained in a separate process to the process according to the present invention and then introduced in a separate step to the process according to the present invention.
  • the polylactone-based polyisocyanate prepolymer according to the present invention is not understood as a polymeric structure in the sense that it does not comprise multiple repetitions (i.e. not more than 3, preferably not more than 2, more preferably not more than 1) of monomeric units such as the polylactone polyol or the polyisocyanate.
  • the polylactone-based polyisocyanate prepolymer is capable of entering, through reactive groups, such as terminal reactive isocyanate functional groups, into further polymerization, thereby contributing more than one monomeric unit to at least one chain of the polymeric shell.
  • the polylactone-based polyisocyanate is obtained by reacting only a polylactone polyol and a polyisocyanate.
  • the polylactone-based polyisocyanate is obtained by only one or more (i.e. 2 or 3), preferably one, polylactone polyol(s) and only one or more (i.e. 2 or 3), preferably one polyisocyanate.
  • the polylactone-based polyisocyanate prepolymer is obtained in a separate process to the process according to the present invention and in the presence of excess isocyanate groups to obtain a prepolymer with terminated isocyanate groups.
  • the polylactone-based polyisocyanate prepolymer is obtained by reacting a polylactone polyol and a polyisocyanate in a manner that the polylactone-based polyisocyanate prepolymer comprises at least 2 terminal isocyanate groups.
  • the polylactone-based polyisocyanate prepolymer is obtained by reacting a polylactone polyol and a polyisocyanate in a manner that the polylactone-based polyisocyanate prepolymer comprises at least 3 terminal isocyanate groups.
  • the polylactone-based polyisocyanate prepolymer is obtained by reacting a polylactone polyol and a polyisocyanate in a manner that the polylactone-based polyisocyanate prepolymer comprises not more than 4 terminal isocyanate groups.
  • the polylactone-based polyisocyanate prepolymer is obtained by reacting a polylactone polyol and a polyisocyanate in a manner that the polylactone-based polyisocyanate prepolymer comprises not more than 3 terminal isocyanate groups.
  • the polylactone-based polyisocyanate prepolymer is obtained by a process comprising the following steps: i. Providing a polylactone polyol and optionally a solvent; ii. Adding a polyisocyanate to the mixture of step i. with an excess of isocyanate (NCO) functional groups over hydroxy (OH) groups; iii. Applying conditions to form a reaction between the OH functional groups of the polylactone polyol and the NCO functional groups of the polyisocyanate to form the polylactone-based polyisocyanate prepolymer.
  • NCO isocyanate
  • any suitable solvent may be used in which the polylactone polyol can be dissolved at room temperature.
  • the solvent may be chloroform, dichloromethane, carbon tetrachloride, benzene, toluene, xylene, cyclohexanone and 2-nitropropane, acetone, 2-butanone, ethyl acetate, butyl acetate, such as n-butyl acetate, dimethylformamide and/or acetonitrile.
  • the solvent is xylene or n-butyl acetate.
  • the molar ratio NCO/OH is > 2, preferably the molar ratio of NCO/OH > 2.
  • the molar ratio NCO/OH is > 3, preferably the molar ratio of NCO/OH > 3.
  • the molar ratio NCO/OH is > 4, preferably the molar ratio NCO/OH is > 4.
  • the molar ratio NCO/OH is > 5, preferably the molar ratio NCO/OH is > 5.
  • the molar ratio NCO/OH is > 6.5, preferably the molar ratio NCO/OH is > 6.5.
  • Any conditions can be applied which are known form a reaction between the OH functional groups of the polylactone polyol and the NCO functional groups of the polyisocyanate.
  • any conditions can be applied which are known to form an addition reaction between the OH functional groups of the polylactone polyol and the NCO functional groups of the polyisocyanate.
  • the reaction temperature can be above 40°C, preferably above 60°C, more preferably above 80°C, more preferably above 100°C and most preferably at 120°C.
  • reaction time can be more than 1 h, preferably more than 1h 30 min, more preferably equal to or more than 2 h.
  • the reaction can be applied in the presence of catalyst, such as bases, preferably amine bases (e.g., tertiary amines) and organometals (e.g., alkyltin carboxylates or organobismuth).
  • bases preferably amine bases (e.g., tertiary amines) and organometals (e.g., alkyltin carboxylates or organobismuth).
  • a polylactone polyol is herein understood as a polyol from a polylactone.
  • a polylactone in turn is herein understood as a (cyclic) polyester polymer whose monomers are aliphatic hydroxy acids.
  • Polylactone polyol can be the reaction product of dicarboxylic acid, preferably azelic acid, and polyol, preferably ethylene glycol.
  • the polylactone polyol is a biodegradable polylactone polyol.
  • the polylactone polyol is polylactide (PLA), polyglycolide (PGA), polycaprolactone (PCL), copolylactones such as poly(lactide-co-glycolide) (PLGA), poly (glycolide-co-lactide-co-caprolactone), tri-component copolymer (PGLC), tri- and multiblock polylactide/poly(ethylene oxide) copolymer (TPLE and BPLE), as well as polycaprolactone/polylactide/poly(ethylene oxide) copolymer (PCEL), or ethylene glycol azelate (being the reaction product of azelic acid and ethylene glycol.
  • PLA polylactide
  • PGA polyglycolide
  • PCL polycaprolactone
  • copolylactones such as poly(lactide-co-glycolide) (PLGA), poly (glycolide-co-lactide-co-caprolactone), tri-component copolymer (PG
  • the polylactone polyol is a polycaprolactone polyol.
  • the polylactone polyol is a polycaprolactone diol or triol.
  • the polylactone polyol has a molecular weight at the range from 200 g/mol to 10000 g/mol, preferably from 220 g/mol to 2000 g/mol, and more preferably from 240 g/mol to 550 g/mol.
  • the polylactone polyol used in the process for preparing the polylactone-based polyisocyanate prepolymer may be present in amounts of more than 60 wt.%, preferably more than 40 wt.%, more preferably more than 20 wt.%, more preferably more than 10 wt.% of the preparing the polylactone-based polyisocyanate prepolymer reaction mixture.
  • the polylactone polyol moiety of the polylactone-based polyisocyanate prepolymer may be present in the process according to the present invention amounts representing from 0.1 to 10%, preferably from 0.5 to 7% and more preferably from 1 to 5% by weight of the microcapsule slurry.
  • the polyisocyanate may comprise at least 2 or even at least 3 isocyanate functional groups.
  • the polyisocyanate may comprise up to 6, or even up to 4 isocyanate functional groups.
  • Low volatility polyisocyanates are preferred because of their low toxicity.
  • the at least one polyisocyanate may be aliphatic, aromatic or a mixture of both aromatic and aliphatic polyisocyanates. In the case of mixtures of polyisocyanates, each member of the mixture has at least two isocyanate functional groups. According to one embodiment, the at least one polyisocyanate is an aromatic polyisocyanate.
  • aromatic polyisocyanate is meant here as encompassing any polyisocyanate comprising an aromatic moiety. Preferably, it comprises a phenyl, a toluyl, a xylyl, a naphthyl or a diphenyl moiety, more preferably a toluyl or a xylyl moiety.
  • Preferred aromatic polyisocyanates are biurets and polyisocyanurates, more preferably comprising one of the above-cited specific aromatic moieties.
  • the aromatic polyisocyanate is a polyisocyanurate of toluene diisocyanate (commercially available from Bayer under the tradename Desmodur® RC), a trimethylol propane (TMP)-adduct of toluene diisocyanate (commercially available from Bayer under the tradename Desmodur® L75), a trimethylol propane (TMP)-adduct of xylylene diisocyanate (commercially available from Mitsui Chemicals under the tradename Takenate® D-110N).
  • the aromatic polyisocyanate is a trimethylol propane (TMP)-adduct of xylylene diisocyanate.
  • said polyisocyanate is an aliphatic polyisocyanate.
  • aliphatic polyisocyanate is defined as a polyisocyanate which does not comprise any aromatic moiety.
  • Preferred aliphatic polyisocyanates are a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate, a trimethylol propane (TMP)-adduct of hexamethylene diisocyanate (available from Mitsui Chemicals) or a biuret of hexamethylene diisocyanate (commercially available from Bayer under the tradename Desmodur® N 100), among which a biuret of hexamethylene diisocyanate is even more preferred.
  • TMP trimethylol propane
  • the polyisocyanate comprises an aliphatic polyisocyanate, an aromatic polyisocyanate or a mixture of an aliphatic and aromatic polyisocyanates, preferably comprising an aromatic polyisocyanate.
  • said at least one polyisocyanate is in the form of a mixture of at least one aliphatic polyisocyanate and of at least one aromatic polyisocyanate, both comprising at least two or three isocyanate functional groups, such as a mixture of a biuret of hexamethylene diisocyanate with a trimethylol propane (TMP)-adduct of xylylene diisocyanate, a mixture of a biuret of hexamethylene diisocyanate with a polyisocyanurate of toluene diisocyanate and a mixture of a biuret of hexamethylene diisocyanate with a trimethylol propane (TMP)-adduct of toluene diisocyanate.
  • TMP trimethylol propane
  • TMP trimethylol propane
  • the polyisocyanate is xylylene diisocyanate, toluene diisocyanate, 1,5-pentamethylene diisocyanate, 1,6-hexamethylene diisocyanate, L-Lysine diisocyanate, sophorone diisocyanate, methylene diphenyl diisocyanate, L-Lysine diisocyanate ethyl ester, lysine triisocyanate, aliphatic isocyanate biuret, aliphatic or aromatic isocyanate trimethylol propane (TMP) adduct, aromatic isocyanate trimethylol propane (TMP) adduct, preferably xylylene diisocyanate, toluene diisocyanate, methylene diphenyl diisocyanate and aromatic isocyanate trimethylol propane (TMP) adduct, more preferably xylylene diisocyanate, toluene diisocyanate, to
  • the at least one aliphatic polyisocyanate and the at least one aromatic polyisocyanate are used in a respective molar ratio comprised between 80:20 and 10:90, preferably between 75:25 and 20:80, more preferably between 60:40 and 20:80, even more preferably between 60:40 and 30:70, most preferably between 45:55 and 30:70.
  • the polyisocyanate used in the process for preparing the polylactone-based polyisocyanate prepolymer may be present in amounts of more than 40wt.%, preferably more than 60%, more preferably more than 80 wt.%, more preferably more than 90 wt.% of the preparing the polylactone-based polyisocyanate prepolymer reaction mixture.
  • the polyisocyanate moiety of the polylactone-based polyisocyanate prepolymer may present in the process according to the present invention in amounts representing from 0.1 to 15%, preferably from 0.5 to 8% and more preferably from 1 to 6% by weight of the microcapsule slurry.
  • the oil phase is dispersed in a dispersing phase comprising an emulsifier or colloidal stabilizer and, optionally, a cross-linker to form an emulsion.
  • the dispersing phase comprises, preferably consists of water, i.e. the dispersing phase is an aqueous phase.
  • the content of water is below or equal to 10%, preferably below or equal to 5%, more preferably below or equal to 3% by weight based on the total weight of the aqueous phase.
  • the dispersing phase is free of water.
  • the dispersing phase comprises a solvent chosen in the group consisting of glycerol, 1 ,4-butanediol, ethylene glycol and mixtures thereof.
  • Emulsifier / stabilizer According to the invention, the emulsifier or stabilizer can be ionic or non-ionic.
  • the stabilizer is a colloidal stabilizer.
  • the stabilizer is solid particles (Pickering emulsion).
  • the ionic emulsifier or stabilizer is chosen in the group consisting of gum Arabic, carboxymethyl cellulose, soy protein, sodium caseinate, gelatin, bovine serum albumin, sugar beet pectin, hydrolyzed soy protein, hydrolyzed sericin, Pseudocollagen, Biopolymer SA-N (INCI name : Hyaluronic Acid (and) Serum Albumen (and) Dextran Sulfate), Pentacare-NA PF (Hydrolyzed Wheat Gluten (and) Ceratonia Siliqua (Carob) Gum (and) Aqua (and) Sodium Dextran Sulfate (and) Bis-Hydroxyethyl Tromethamine (and) Phenoxyethanol (and) Ethylhexylglycerin), and mixtures thereof.
  • gum Arabic carboxymethyl cellulose
  • soy protein sodium caseinate
  • gelatin bovine serum albumin
  • sugar beet pectin sugar beet pec
  • the ionic emulsifier or stabilizer is chosen in the group consisting of gum Arabic, carboxymethyl cellulose, sodium caseinate, sugar beet pectin and mixtures thereof.
  • the non-ionic emulsifier or stabilizer is chosen in the group consisting of polyvinyl alcohol, modified polyvinyl alcohol, modified starch, modified cellulose, polysaccharides, and mixtures thereof.
  • the non-ionic emulsifier or stabilizer is chosen in the group consisting of polyvinyl alcohol, modified starch and mixtures thereof.
  • the emulsifier or stabilizer is polymeric stabilizer such as polyvinyl alcohol, a cellulose derivative, polyethylene oxide, a copolymer of polyethylene oxide and polyethylene or polypropylene oxide, a copolymer of acrylamide and acrylic acid, a copolymer of vinylpyrrolidone and of a quaternized vinylimidazol and sodium dodecyl sulfate; inorganic colloidal stabilizer such as hydroxyapatite, calcium carbonate, kaolin, laponite, silica, amine functionalized silica, clays, sericite mica, tri-calcium phosphate; polysaccharides such as Gum Arabic, starch, modified starch, chitosan, sodium alginate, alginic acid, cellulose, chitin, pectin, sugar beet pectin or colloidal stabilizers comprising these polysaccharides; proteins such as silk fibroin, sericin, gelatin, sodium
  • cellulose derivative is herein understood as cellulose which is modified by chemical and/or biotechnological modification, particularly chemical modification.
  • the “cellulose derivative” is characterized by modifications such as esterification, etherification, or other chemical reactions that impart specific changes to the original cellulose molecule.
  • Particular cellulose derivatives include substances like cellulose acetate, cellulose ethers (e.g. methyl cellulose, ethyl cellulose, propyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose and/or hydroxypropyl methyl cellulose), and carboxymethyl cellulose.
  • the emulsion comprises between about 0.1% and 5% w/w of at least an emulsifier or stabilizer, percentage being expressed on a w/w basis relative to the total weight of the dispersion as obtained after step b).
  • the emulsion comprises between about 0.1% and 2% w/w of at least an emulsifier or stabilizer.
  • the emulsion comprises between about 0.1% and 1% w/w of at least an emulsifier or stabilizer.
  • a cross-linker may be added to the dispersing phase.
  • Any compound can be used as a cross-linker which is able to react with the isocyanate functional groups of the polylactone-based polyisocyanate prepolymer to further cross-link the polylactone-based polyisocyanate prepolymer.
  • the cross-linker may be multifunctionalized amines, multifunctionalized alcohols and/or multifunctionalized thiols.
  • the cross-linker is multi-functionalized amines such as ethylenediamine, diethylenetriamine, triethylenetetramine, guanidine, 1,5-pentanediamine, 1 ,8-diaminooctane, 1 ,12-diaminododecane, 3,5-Diamino-1 ,2,4-triazole, urea; amino acids such as l-lysine, l-tryptophan, l-cystine, cystamine, and their hydrochloric acid salts, multifunctionalized polyols such as 1 ,5-petanediol, 1,6-hexanediol, and polylactone-based polyols or multi-functionalized thiols.
  • amines such as ethylenediamine, diethylenetriamine, triethylenetetramine, guanidine, 1,5-pentanediamine, 1 ,8-diaminooctane, 1 ,12-dia
  • the cross-linker may be an amino acid, such as l-lysine, I- tryptophan, l-cystine, cystamine, and their hydrochloric acid salts, more preferably l-lysine.
  • the cross-linker may be present in an amount of more than 0.5 wt.%, preferably more than 1.0 wt.%, even more preferably equal or more than 1.2 wt.% based on the weight of the emulsion.
  • a cross-linker may be optionally added into the emulsion.
  • conditions are applied sufficient to induce cross-linking of the polylactone-based polyisocyanate prepolymer to form the core-shell microcapsule or core-shell microcapsule slurry.
  • any conditions can be applied which induces crosslinking of the polylactone-based polyisocyanate prepolymer to form the core-shell microcapsule.
  • condition sufficient to induce the cross-linking include heating the oil in water emulsion at elevated temperature, preferably at a temperature of at least 30°C, preferably more than 45°C, more preferably more than 60°C, even more preferably more than 70°C, such as for example 80°C.
  • condition sufficient to induce the cross-linking include heating the oil in water emulsion at elevated temperature for at least 30 minutes, preferably at least 1 hours, even more preferably at least 2 hours, such as for example 3 hours.
  • condition sufficient to induce the cross-linking include heating the oil in water emulsion at elevated temperature and at a pH of 4 to 10.
  • a polymer selected from the group consisting of a non-ionic polysaccharide, a cationic polymer, a polysuccinimide derivative (as described for instance in WO2021185724), and mixtures thereof to form an outer coating to the microcapsule.
  • Non-ionic polysaccharide polymers are well known to a person skilled in the art and are described for instance in WO2012/007438 page 29, lines 1 to 25 and in WO2013/026657 page 2, lines 12 to 19 and page 4, lines 3 to 12.
  • Preferred non-ionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar, hydroxypropyl cellulose and hydroxypropyl methyl cellulose.
  • Cationic polymers are well known to a person skilled in the art.
  • Preferred cationic polymers have cationic charge densities of at least 0.5 meq/g, more preferably at least about 1.5 meq/g, but also preferably less than about 7 meq/g, more preferably less than about 6.2 meq/g.
  • the cationic charge density of the cationic polymers may be determined by the Kjeldahl method as described in the US Pharmacopoeia under chemical tests for Nitrogen determination.
  • the preferred cationic polymers are chosen from those that contain units comprising primary, secondary, tertiary and/or quaternary amine groups that can either form part of the main polymer chain or can be borne by a side substituent directly connected thereto.
  • the weight average (Mw) molecular weight of the cationic polymer is preferably between 10,000 and 3.5M Dalton, more preferably between 50,000 and 1.5M Dalton.
  • Mw weight average molecular weight
  • cationic polymers based on acrylamide, methacrylamide, N-vinylpyrrolidone, quaternized N,N-dimethylaminomethacrylate, diallyldimethylammonium chloride, quaternized vinylimidazole (3-methyl-1 -vinyl-1 H-imidazol- 3-ium chloride), vinylpyrrolidone, acrylamidopropyltrimonium chloride, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride or polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride.
  • copolymers shall be selected from the group consisting of polyquaternium-5, polyquaternium- 6, polyquaternium-7, polyquaterniumIO, polyquaternium-11 , polyquaternium-16, polyquaternium-22, polyquaternium-28, polyquaternium-43, polyquaternium-44, polyquaternium-46, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride or polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride.
  • Salcare® SC60 cationic copolymer of acrylamidopropyltrimonium chloride and acrylamide, origin: BASF
  • Luviquat® such as the PQ 11 N, FC 550 or Style (polyquaternium-11 to 68 or quaternized copolymers of vinylpyrrolidone origin: BASF), or also the Jaguar® (C13S or C17, origin Rhodia).
  • an amount of polymer described above comprised between about 0% and 5% w/w, or even between about 0.1% and 2% w/w, percentage being expressed on a w/w basis relative to the total weight of the slurry as obtained after step d). It is clearly understood by a person skilled in the art that only part of said added polymers will be incorporated into/deposited on the microcapsule shell.
  • Another object of the invention is a process for preparing a microcapsule powder comprising the steps as defined above and an additional step consisting of submitting the microcapsule slurry to a drying process, like spray-drying, to provide the microcapsules as such, i.e. in a powdery form.
  • the slurry may be spray-dried preferably in the presence of a polymeric carrier material such as polyvinyl acetate, polyvinyl alcohol, dextrins, natural or modified starch, vegetable gums, pectins, xanthans, alginates, carragenans or cellulose derivatives to provide microcapsules in a powder form.
  • a polymeric carrier material such as polyvinyl acetate, polyvinyl alcohol, dextrins, natural or modified starch, vegetable gums, pectins, xanthans, alginates, carragenans or cellulose derivatives to provide microcapsules in a powder form.
  • drying method such as the extrusion, plating, spray granulation, the fluidized bed, or even a drying at room temperature using materials (carrier, desiccant) that meet specific criteria as disclosed in WO2017/134179.
  • the carrier material contains free perfume oil which can be the same or different from the perfume from the core of the microcapsules.
  • the present invention also relates to a core-shell microcapsule or core-shell microcapsule slurry obtainable by the process according to the present invention.
  • the present invention also relates to the core-shell microcapsule or core-shell microcapsule, wherein the core-shell microcapsule comprises a core, preferably oil core, comprising a hydrophobic material, preferably a perfume oil, a cross-linked polymeric shell surrounding the oil core and wherein the crosslinked polymeric shell is obtained by reacting a polylactone-based polyisocyanate prepolymer obtained by reacting polylactone polyol and a polyisocyanate and, optionally, a cross-linker.
  • a core preferably oil core, comprising a hydrophobic material, preferably a perfume oil
  • a cross-linked polymeric shell surrounding the oil core
  • the crosslinked polymeric shell is obtained by reacting a polylactone-based polyisocyanate prepolymer obtained by reacting polylactone polyol and a polyisocyanate and, optionally, a cross-linker.
  • the polylactone-based polyisocyanate prepolymer is capable of entering, through its reactive groups, such as terminal reactive isocyanate functional groups, into further polymerization, thereby contributing more than one monomeric unit to at least one chain of the polymeric shell.
  • hydrophobic material polylactone-based polyisocyanate prepolymer, polylactone polyol, polyisocyanate and cross-linker are the same as described herein-above.
  • the shell material is a biodegradable material.
  • the shell has a biodegradability of at least 40%, preferably at least 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98%, within 60 days according to OECD301 F.
  • the core-shell microcapsule has a biodegradability of at least 40 %, preferably at least 60 %, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD301F.
  • the core-shell microcapsule including all components, such as the core, shell and optionally coating may have a biodegradability of at least 40 %, preferably at least 60 %, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD301 F.
  • the oil core preferably perfume oil
  • OECD301 F is a standard test method on the biodegradability from the Organization of Economic Co-operation and Development.
  • a typical method for extracting the shell for measuring the biodegradability is disclosed in Gasparini and all in Molecules 2020, 25,718.
  • the present invention also relates to a perfuming composition
  • a perfuming composition comprising a core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above, at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base, and optionally, at least one perfumery adjuvant.
  • the composition comprises:
  • an active ingredient preferably chosen in the group consisting of a cosmetic ingredient, skin caring ingredient, perfume ingredient, flavor ingredient, malodour counteracting ingredient, bactericide ingredient, fungicide ingredient, pharmaceutical or agrochemical ingredient, a sanitizing ingredient, an insect repellent or attractant, and mixtures thereof.
  • a core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described hereinabove can also be added in different perfumed consumer products
  • present invention relates to a perfuming composition
  • a perfuming composition comprising a core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above and optionally, a free perfume oil.
  • the perfuming composition according to the invention comprises between 0.1 and 30 % by weight of a core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above.
  • free perfume it is herein understood a perfume or perfume oil which is comprised in the perfuming composition and not entrapped in the core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above.
  • the total amount of the core-shell microcapsule or coreshell microcapsule slurry obtained by the process according to the present invention or as described herein-above is 0.05 to 5 wt.% (based on the total weight of the perfuming composition) and the total amount of the free perfume oil is 0.05 to 5 wt.% (based on the total weight of the perfuming composition).
  • the total perfume oil of the perfume formulation entrapped in the core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above and total free perfume oil are present in the perfuming composition in a weight ratio of 1:20 to 20:1, preferably 10:1 to 1 :10.
  • the perfuming composition can further comprise at least one perfuming co-ingredient and, optionally a perfumery adjuvant,
  • perfuming co-ingredient it is herein understood a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect and which is not a microcapsule as 20 defined above.
  • a co-ingredient to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
  • 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.
  • these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfur heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.
  • Many of these co-30 ingredients are in any case listed in reference texts such as the book by S.
  • perfumery adjuvant an ingredient capable of imparting additional 5 added benefit such as a color, 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.
  • the core-shell microcapsules or core-shell microcapsules slurries obtained by the process according to the present invention or as described herein-above can be used in combination with a second type of delivery system.
  • the perfuming composition comprises:
  • first type of delivery system and the second type of delivery system differ in their perfuming formulations and/or carrier material (shell or matrix) and/or outer coating.
  • the core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above can advantageously be used in many application fields and used in consumer products.
  • the present invention also relates to a perfumed consumer product comprising a core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above, and a personal care, home care, or fabric care active base.
  • the consumer products of the invention can in particular be of used in perfumed consumer products such as product belonging to fine fragrance or “functional” perfumery.
  • Functional perfumery includes in particular personal-care products including hair-care, body cleansing, skin care, hygiene-care as well as home-care products including laundry care and air care.
  • liquid consumer product comprising:
  • a perfumed consumer product it is meant a consumer product which is expected to deliver among different benefits a perfuming effect to the surface to which it is applied (e.g. skin, hair, textile, paper, or home surface) or in the air (air-freshener, deodorizer etc).
  • a perfumed consumer product according to the invention is a manufactured product which comprises a functional formulation also referred to as “base”, together with benefit agents, among which an effective amount of microcapsules according to the invention.
  • Non-limiting examples of suitable perfumed consumer products can be a fine perfume, a splash or eau de perfume, a cologne, a shave or after-shave lotion, a liquid or solid detergent, a mono or multi chamber unidose detergent , a fabric softener, a fabric refresher, liquid or solid scent-boosters (PEG I urea or salts), a dryer sheet, an ironing water, a paper, a bleach, a carpet cleaners, curtain-care products, a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a hair conditioning product, a vanishing cream, a deodorant or antiperspirant, hair remover, tanning or sun product, nail products, skin cleansing, a makeup, a perfumed soap, shower or bath mousse, oil or gel, or a foot/hand care products, a hygiene product, an air freshener, a “ready to use” powdere
  • the perfumed consumer product is preferably selected from the group consisting of personal care composition, home care composition or fabric care composition, most preferably in form of antiperspirants, hair care products, such as shampoo or hair-conditioner, body care products such as a shower gel, oral care products, laundry care products, preferably a detergent or a fabric softener.
  • Another object of the invention is a consumer product comprising:
  • the personal care composition is preferably chosen in the group consisting of a haircare product (e.g. a shampoo, hair conditioner, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream, body lotion or a deodorant or antiperspirant), a skin-care product (e.g. a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product), oral care product (toothpaste or mouthwash composition) or a fine fragrance product (e.g. Eau de Toilette - EdT).
  • a haircare product e.g. a shampoo, hair conditioner, a coloring preparation or a hair spray
  • a cosmetic preparation e.g. a vanishing cream, body lotion or a deodorant or antiperspirant
  • a skin-care product e.g. a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product
  • oral care product e.g.
  • Another object of the invention is a consumer product comprising:
  • the home or fabric care composition is preferably chosen in the group consisting fabric softener, liquid detergent, powder detergent, liquid scent booster and solid scent booster.
  • An object of the invention is a consumer product in the form of a fabric softener composition comprising:
  • a fabric softener active base preferably chosen in the group consisting of dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (esterquats), Hamburg esterquat (HEQ), TEAQ (triethanolamine quat), silicones, cationic guars and mixtures thereof, preferably in an amount comprised between 85 and 99.95% by weight (excluding water) based on the total weight of the composition, - the core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition.
  • An object of the invention is a consumer product in the form of a liquid detergent composition comprising:
  • liquid detergent active base preferably chosen in the group consisting of anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), methyl ester sulfonate (MES) and nonionic surfactant such as alkyl amines, alkanolamide, fatty alcohol poly(ethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxydes, alkyl polyglucosides, alkyl polyglucosamides, preferably in an amount comprised between 85 and 99.95% by weight (excluding water) based on the total weight of the composition,
  • anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS),
  • the core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition.
  • An object of the invention is a consumer product in the form of a solid detergent composition comprising:
  • a solid detergent active base preferably chosen in the group consisting of anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), methyl ester sulfonate (MES) and nonionic surfactant such as alkyl amines, alkanolamide, fatty alcohol poly(ethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxydes, alkyl polyglucosides, alkyl polyglucosamides, preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition,
  • anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lau
  • the core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition.
  • An object of the invention is a consumer product in the form of a solid scent booster comprising:
  • a solid carrier preferably chosen in the group consisting of urea, sodium chloride, sodium sulphate, sodium acetate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, saccharides such as sucrose, mono-, di-, and polysaccharides and derivatives such as starch, cellulose, methyl cellulose, ethyl cellulose, propyl cellulose, polyols/sugar alcohols such as sorbitol, maltitol, xylitol, erythritol, and isomalt, PEG, PVP, citric acid or any water soluble solid acid, fatty alcohols or fatty acids and mixtures thereof.
  • urea sodium chloride, sodium sulphate, sodium acetate, zeolite, sodium carbonate
  • the core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above in a powdered form, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition.
  • An object of the invention is a consumer product in the form of a liquid scent booster comprising:
  • surfactant system essentially consisting of one or more than one non-ionic surfactant, wherein the surfactant system has a mean HLB between 10 and 14, preferably chosen in the group consisting of ethoxylated aliphatic alcohols, POE/PPG (polyoxyethylene and polyoxypropylene) ethers, mono and polyglyceryl esters, sucrose ester compounds, polyoxyethylene hydroxylesters, alkyl polyglucosides, amine oxides and combinations thereof;
  • POE/PPG polyoxyethylene and polyoxypropylene
  • linker chosen in the group consisting of alcohols, salts and esters of carboxylic acids, salts and esters of hydroxyl carboxylic acids, fatty acids, fatty acid salts, glycerol fatty acids, surfactant having an HLB less than 10 and mixtures thereof, and
  • An object of the invention is a consumer product in the form of a shampoo or a shower gel composition comprising:
  • a shampoo or a shower gel active base preferably chosen in the group consisting of sodium alkylether sulfate, ammonium alkylether sulfates, alkylamphoacetate, cocamidopropyl betaine, cocamide MEA, alkylglucosides and aminoacid based surfactants and mixtures thereof, preferably in an amount comprised between 85 and 99.95% (excluding water) by weight based on the total weight of the composition,
  • the core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition.
  • An object of the invention is a consumer product in the form of a rinse-off conditioner composition
  • a rinse-off conditioner composition comprising:
  • a rinse-off conditioner active base preferably chosen in the group consisting of cetyltrimonium chloride, stearyl trimonium chloride, benzalkonium chloride, behentrimonium chloride and mixture thereof, preferably in an amount comprised between 85 and 99.95% by weight (excluding water) based on the total weight of the composition,
  • the core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition.
  • the consumer product is in the form of a perfuming composition
  • a perfuming composition comprising:
  • PCL polycaprolactone
  • PCL-diol or PCL-triol was dissolved in butyl acetate (5 mL) to obtain solutions, which was then added into the flask of excess m-xylylene diisocyanate with molar ratio of -NCO/-OH>4 dissolved in butyl acetate (10 mL) by a syringe pump dropwise in 1 h with stirring at 120°C. It was then heated for another 1 h to obtain a PCL-based multi-functionalized isocyanate prepolymer solution. The butyl acetate was removed by vacuum first, and the excess m- xylylene diisocyanate was removed by liquid-liquid extraction using hexane. After washing and extraction with hexane, it was removed by vacuum to obtain a transparent viscous product.
  • PCL-based polyisocyanate prepolymers were dissolved in ethyl acetate and mixed with perfume oil, with which colloidal stabilizers suspensions were mixed by an overhead disperser to make emulsion.
  • the emulsion was transferred into a reactor and the interfacial reaction was carried out at 45°C for 15 min, 60°C for 15 min, and 80°C for 2 h.
  • Microcapsules with PCL incorporated in the shell were obtained.
  • Table 3 Composition of microcapsules slurry synthesized with PCL-di-isocyanate prepolymer
  • microcapsules according to Table 4 hereinabove were used for the stability. test: The microcapsules were added in a Fabric Softener base (see Table 6) and stored for 3 days at 37°C with a perfume oil dosage in the base is 0.2%. The microcapsules showed an oil leakage of 18.5%.
  • CAPA3050 (a 540 MW polycaprolactone triol initiated with trimethylol propane (TMP); 2.01 g, 3.64 mmol) was added in ethyl acetate (4.60 mL, 3.64 mmol) in a second 25 mL round- bottomed flask to give a colorless solution. The latter was added dropwise over the period of 5 min to the diisocyanate solution. The reaction mixture was stirred at 50°C for 3 h and then slowly cooled down to room temperature under stirring. Product was recovered by solvent evaporation to afford a white pasty solid.
  • TMP trimethylol propane
  • PCL-based polyisocyanate prepolymer (4.96 g, 2.22 mmol NCO) was dissolved in perfume oil B (see Table A, 20 g) in a 150 mL beaker to give a yellow solution. This solution was stirred for 5 min. A solution of PVOH at 1% in water (46.30 g) was added in the beaker and an emulsion was prepared with an ultra Turrax (S25N 10G) at 20,000 rpm for 2 min. The droplet size was controlled by light microscopy and pH was measured at 5.01. The reaction mixture was transferred in a 250 mL reactor and stirred at 350 r.p.m. at room temperature for 1 h. The temperature was increased to 70°C over the period of 1 h and the reaction mixture was stirred at 70°C for 2h. At the end of process, the dispersion was cooled down to room temperature and pH was measured at 5.71.
  • microcapsule slurry was dried and the shell was recovered by solvent extraction of the perfume by ethyl acetate (5 times), filtration, water washing at 0.5% for 24h, filtration, and a second extraction by ethyl acetate (5 times). A white solid was recovered by filtration and dried.
  • Emerox 14555 linear diol polyol based on ethylene glycol (EG) azelate; 5.03 g, 2.31 mmol, diol from azelic acid and ethylene glycol
  • titanium IV isopropoxyde in ethyl acetate 0.1 mL, 0.04 mmol
  • ethyl acetate 6.5 mL
  • This solution was added into a 50 mL round bottomed three necked flask in the presence of 1,3-bis(isocyanatomethyl)benzene (0.76 mL, 4.85 mmol) to give a colorless solution.
  • the reaction mixture was stirred at 50°C for 3 h and then slowly cooled down to room temperature under stirring to afford a yellow viscous oil.
  • Polylactone polyol based polyisocyanate prepolymer (4.81 g) was dissolved in perfume oil B (Table A, 20 g) in a 150 mL beaker to give a yellow solution. This solution was stirred for 3 min. A solution of PVOH at 1% in water (46.10 g) was added in the beaker and an emulsion was prepared with an ultra Turrax (S25N 10G) at 21,500 rpm for 2 min. The droplet size was controlled by light microscopy and pH was measured at 4.89. The reaction mixture was transferred in a 250 mL reactor and stirred at 350 r.p.m. at room temperature for 1 h.
  • the temperature was increased to 70°C over the period of 1 h and the reaction mixture was stirred at 70°C for 2 h.
  • the dispersion was cooled down to room temperature and pH was measured at 5.68.
  • the microcapsule slurry was dried and the shell was recovered by solvent extraction of the perfume by ethyl acetate (5 times), filtration, water washing at 0.5% for 24h, filtration, and a second extraction by ethyl acetate (5 times). A white solid was recovered by filtration and dried.
  • a sufficient amount of microcapsules of the present invention according to Examples 1 and 3 is dispersed in liquid detergent base described in Table 6 to obtain a concentration of encapsulated perfume oil at 0.22%.
  • a sufficient amount of microcapsule of the present invention according to Examples 1 to 3 is dispersed in liquid detergent base described in Table 7 to obtain a concentration of encapsulated perfume oil at 0.22%.
  • microcapsules of the present invention according to Examples 1 and 3 are incorporated at the required dosage (corresponding to an encapsulated perfume oil at 0.5%) in the rinse-off base (see Table 8).
  • Phase A Ingredients of Phase A are mixed until a uniform mixture was obtained. Tylose is allowed to completely dissolve. Then the mixture is heated up to 70-75°C. Ingredients of Phase B are combined and melted at 70-75°C. Then ingredients of Phase B are added to Phase A with good agitation and the mixing is continued until cooled down to 60°C. Then, ingredients of Phase C are added while agitating and keeping mixing until the mixture cooled down to 40°C. The pH is adjusted with citric acid solution till pH: 3.5 - 4.0.
  • Emulsions 1-5 having the following ingredients are prepared.
  • Table 9 Composition of Emulsions 1-5 and composition of granulated powder 1-5 after spray-drying
  • Components for the polymeric matrix are added in water at 45-50°C until complete dissolution.
  • free perfume C is added to the aqueous phase.
  • Microcapsules according to Examples 1 to 3 are added to the obtained mixture. Then, the resulting mixture is then mixed gently at 25°C (room temperature).
  • Granulated powder 1-5 are prepared by spray-drying Emulsion A-E using a Sodeva Spray Dryer (Origin France), with an air inlet temperature set to 215°C and a throughput set to 500 ml per hour. The air outlet temperature is of 105°C. The emulsion before atomization is at ambient temperature.
  • Liquid scent booster composition Liquid scent booster composition
  • a sufficient amount of microcapsules of the present invention according to Examples 1 and 3 is weighed and mixed in a liquid scent booster to add the equivalent of 0.2% perfume.
  • compositions 1-6 Different ringing gel compositions are prepared (compositions 1-6) according to the following protocol.
  • aqueous phase water
  • solvent propylene glycol
  • surfactants are mixed together at room temperature under agitation with magnetic stirrer at 300 rpm for 5 min.
  • the linker is dissolved in the hydrophobic active ingredient (fragrance) at room temperature under agitation with magnetic stirrer at 300 rpm. The resulting mixture is mixed for 5 min.
  • the aqueous phase and the oil phase are mixed together at room temperature for 5 min leading to the formation of a transparent or opalescent ringing gel.
  • a sufficient amount of granules 1-5 according to Example 7 is weighed and mixed in a powder detergent composition to add the equivalent of 0.2% perfume.
  • a sufficient amount of microcapsules of the present invention according to Examples 1 and 3 is weighed and mixed in a concentrated all-purpose cleaner composition to add the equivalent of 0.2% perfume.
  • Table 12 concentrated all-purpose cleaner composition
  • Neodol 91-8 ® trademark and origin : Shell Chemical
  • Example 7 A sufficient amount of microcapsules in dried form according to Example 7 is weighed and mixed with a solid scent booster composition to add the equivalent of 0.2% perfume.
  • Shampoo composition A sufficient amount of microcapsules of the present invention according to Examples 1 and 3 is weighed and mixed in a shampoo composition to add the equivalent of 0.2% perfume.
  • Polyquaternium-10 is dispersed in water.
  • the remaining ingredients of phase A are mixed separately by addition of one after the other while mixing well after each adjunction.
  • this pre-mix is added to the Polyquaternium-10 dispersion and was mixed for 5 min.
  • Phase B and the premixed Phase C (heat to melt Monomuls 90L-12 in Texapon NSO IS) are added.
  • the mixture is mixed well.
  • Phase D and Phase E are added while agitating.
  • the pH was adjusted with citric acid solution till pH: 5.5 - 6.0.
  • a premix comprising Guar Hydroxypropyltrimonium Chloride and Polyquaternium-10 are added to water and Tetrasodium EDTA while mixing. When the mixture is homogeneous, NaOH is added. Then, Phase C ingredients are added and the mixture was heat to 75 °C. Phase D ingredients are added and mixed till homogeneous. The heating is stopped and temperature of the mixture is decreased to RT. At 45 °C, ingredients of Phase E while mixing final viscosity is adjusted with 25% NaCI solution and pH of 5.5-6 is adjusted with 10% NaOH solution.
  • Antiperspirant spray anhydrous composition A sufficient amount of microcapsules of the present invention according to Examples 1 and 3 is weighed and mixed in an antiperspirant spray anhydrous composition to add the equivalent of 0.2% perfume.
  • Aerosil® 200 trademark and origin : Evonik
  • a sufficient amount of microcapsules of the present invention according to Examples 1 and 3 is weighed and mixed in antiperspirant spray emulsion composition to add the equivalent of 0.2% perfume.
  • Sensiva sc 50 trademark and origin : KRAFT
  • Aerosil R 812 trademark and origin : Evonik
  • Nipagin mna trademark and origin : CLARIANT
  • Part A and Part B are weighted separately. Ingredients of Part A are heated up to 60°C and ingredients of Part B are heated to 55 °C. Ingredients of Part B are poured small parts while continuous stirring into A. Mixture were stirred well until the room temperature was reached. Then, ingredients of part C are added. The emulsion is mixed and is introduced into the aerosol cans. The propellant is crimped and added.
  • Aerosol filling 30% Emulsion: 70% Propane I Butane 2,5 bar
  • Irgasan® DP 300 trademark and origin : BASF
  • Antiperspirant roll-on emulsion composition
  • a sufficient amount of microcapsules of the present invention according to Examples 1 and 3 is weighed and mixed in antiperspirant roll-on emulsion composition to add the equivalent of 0.2% perfume.
  • Part A and B are heated separately to 75°C; Part A is added to part B under stirring and the mixture is homogenized for 10 minutes. Then, the mixture is cooled down under stirring; and part C is slowly added when the mixture reached 45°C and part D when the mixture reached at 35 °C while stirring. Then the mixture is cooled down to RT.
  • a sufficient amount of microcapsules of the present invention according to Examples 1 and 3 is weighed and mixed in antiperspirant roll-on composition to add the equivalent of 0.2% perfume.
  • part B The ingredients of part B are mixed in the vessel then ingredient of part A is added. Then dissolved part C in part A and B. With perfume, 1 part of Cremophor RH40 for 1 part of perfume is added while mixing well
  • a sufficient amount of microcapsules of the present invention according to Examples 1 and 3 is weighed and mixed in antiperspirant roll-on emulsion composition to add the equivalent of 0.2% perfume.
  • Part A is prepared by sprinkling little by little the Hydroxyethylcellulose in the water whilst rapidly stirring with the turbine. Stirring is continued until the Hydroxyethylcellulose is entirely swollen and giving a limpid gel. Then, Part B is poured little by little in Part A whilst continuing stirring until the whole is homogeneous. Part C is added.
  • microcapsules of the present invention according to Examples 1 and 3 are weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • microcapsules of the present invention according to Examples 1 and 3 are weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • Cremophor® RH 40 trademark and origin : BASF
  • Ingredients from Part B are mixed together. Ingredients of Part A are dissolved according to the sequence of the Table and are poured into part B.
  • microcapsules of the present invention according to Examples 1 and 3 are weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • Part A All the components of Part A are weighted and heated up to 70-75°C. Ceteareth-25 is added once the other Part A ingredients are mixed and heated. Once the Ceteareth-25 is dissolved, the Stearic Acid is added.
  • Part B is prepared by dissolving the Triclosan in 1,2 Propylene Glycol. Water which has evaporated is added. Slowly under mixing, Part B is poured into part A. To stock, a plastic bag into the bucket is put in to be sealed after cooling. Moulds was filled at about 70°C.
  • microcapsules of the present invention according to Examples 1 and 3 are weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • Part A All the components of Part A are weighted, heated up to 70-75°C and mixed well.
  • Ingredient of Part B is dispersed in Part A. The mixture is mixed and putted into a tick at 65 °C.
  • microcapsules of the present invention according to Examples 1 and 3 are weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • a sufficient amount of granules 1-5 according to Example 7 is weighed and mixed in introduced in a standard talc base: 100% talc, very slight characteristic odor, white powder, origin: LUZENAC to add the equivalent of 0.2% perfume.
  • microcapsules of the present invention according to Examples 1 and 3 are weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • CARBOPOL AQUA SF-1 POLYMER trademark and origin: NOVEON
  • KATHON CG trademark and origin: ROHM & HASS
  • shower-gel composition A sufficient amount of microcapsules of the present invention according to Examples 1 and 3 is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • MERQUAT 550 trademark and origin: LUBRIZOL Ingredients are mixed, pH is adjusted to 4.5 (Viscosity: 3000cPo +/-1500cPo (Brookfield R I Spindle#4 / 20RPM)).
  • microcapsules of the present invention according to Examples 1 and 3 are weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • EUPERLAN PK 3000 AM trademark and origin: COGNIS
  • microcapsules of the present invention according to Examples 1 and 3 are weighed and mixed with alkaline base A to add the equivalent of 0.2% perfume.
  • Phase B was added to Phase A (both at 70-75°C) with good agitation.
  • Phase C was added while mixing continued until cooled down to room temperature At room temperature Phase D ingredients were added while mixing
  • Phase B was added to Phase A (both at 70-75°C) with good agitation and mixing continued until cooled down to room temperature
  • microcapsules of the present invention according to Examples 1 and 3 are weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • microcapsule slurry R (corresponding to microcapsules of the present invention according to Examples 1 and 3 except that a flavor is encapsulated instead of a perfume) is weighed and mixed in the following composition to add the equivalent of 0.2% flavor.
  • Tixosil 73 trademark and origin :
  • microcapsule slurry R (corresponding to microcapsules of the present invention according to Examples 1 and 3 except that a flavor is encapsulated instead of a perfume) is weighed and mixed in the following composition to add the equivalent of 0.2% flavor.
  • Aerosil®200 trademark and origin:
  • microcapsule slurry R (corresponding to microcapsules of the present invention according to Examples 1 and 3 except that a flavor is encapsulated instead of a perfume) is weighed and mixed in the following composition to add the equivalent of 0.2% flavor.
  • microcapsule slurry R corresponding to microcapsules of the present invention according to Examples 1 and 3 except that a flavor is encapsulated instead of a perfume
  • Table 37 Mouthwash formulation

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Abstract

La présente invention concerne un procédé de préparation d'une microcapsule coeur-écorce et une suspension de microcapsules coeur-écorce comprenant un prépolymère de polyisocyanate à base de polylactone obtenu par réaction d'un polyol de polylactone et d'un polyisocyanate, la microcapsule coeur-écorce et la suspension de microcapsules coeur-écorce ainsi que des compositions parfumantes et des produits de consommation les comprenant.
PCT/EP2024/051100 2023-01-20 2024-01-18 Microcapsules obtenues à partir d'un prépolymère à base de polylactone Ceased WO2024153727A1 (fr)

Priority Applications (3)

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EP24701346.9A EP4651987A1 (fr) 2023-01-20 2024-01-18 Microcapsules obtenues à partir d'un prépolymère à base de polylactone
CN202480017550.6A CN120957806A (zh) 2023-01-20 2024-01-18 由聚内酯基预聚物得到的微胶囊
MX2025008292A MX2025008292A (es) 2023-01-20 2025-07-16 Microcapsulas a partir de prepolimero a base de polilactona

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CNPCT/CN2023/073306 2023-01-20
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EP23156995 2023-02-16

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Publication number Priority date Publication date Assignee Title
CN119350832A (zh) * 2024-10-22 2025-01-24 深圳永昌和科技有限公司 一种含微胶囊结构的双组份3d打印弹性体材料的制备方法
CN119877288A (zh) * 2025-03-31 2025-04-25 宁波博洋家纺集团有限公司 一种天雪棉小提花家纺面料及其制备方法

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