Improvements in or relating to organic compounds

Abstract

The present invention provides microcapsule compositions comprising at least one core-shell microcapsule wherein the at least one core-shell microcapsule comprises a hydrophobic core and a shell surrounding the core wherein the shell comprises a polymer or oligomer generated in situ by an enzymatic process.

Description

[0001] The present invention relates to a microcapsule composition comprising at least one core - shell microcapsule, a method for preparing such a microcapsule composition, and the use of such a microcapsule composition for enhancing the performance of a beneficial agent in a consumer product.

[0002] It is known to incorporate encapsulated beneficial agents into consumer products such as home care, personal care and fabric care products. Beneficial agents include, for example, fragrances, cosmetic agents, food ingredients, nutraceuticals, drugs and substrate enhancers.

[0003] Encapsulated beneficial agents are known in the art. They can be formed by coating small solid particles or droplets in a thin film of a shell material. Although virtually any coating material (at least conceptually) is a candidate for the capsule shell material, in practice, relatively few materials have been used in commercial products to date for commercial and regulatory reasons. The choice of capsule shell material is determined by many factors, including the end - use application, cost, availability, ease of processing and inherent barrier properties. Defining the optimal shell material for a given application can be complex because many interacting parameters determine the success of a given capsule shell material.

[0004] Particularly suitable microcapsules for delivering beneficial agents are core - shell microcapsules, where the core typically contains the beneficial agent and the shell is impermeable or at least partially impermeable to the beneficial agent. Generally, these microcapsules are used in an aqueous medium and the encapsulated beneficial agent is hydrophobic. A wide selection of shell materials can be used provided that the shell material is impermeable or at least partially impermeable to the encapsulated beneficial agent.

[0005] Beneficial agents are encapsulated for a variety of reasons. Microcapsules can isolate and protect these materials from the external suspending medium such as the consumer product base, in which they may be incompatible or unstable. They are also used to assist in depositing the beneficial agent on a substrate such as skin or hair, or in the case of fragrance ingredients, also on fabrics or hard household surfaces. They can also serve as a means of controlling the spatial and temporal release of the beneficial agent.

[0006] A variety of encapsulation media and beneficial agents suitable for preparing encapsulated compositions have been proposed in the prior art. Such encapsulation media include synthetic resins made from polyamides, polyureas, polyurethanes, polyacrylates, melamine - derived resins or mixtures thereof. Encapsulated beneficial agent compositions are typically prepared in the form of an aqueous slurry.

[0007] Consumers are increasingly concerned about the materials used and the methods of manufacturing consumer goods that are obtained from non-renewable sources (such as synthetic petrochemicals). The "clean label" concept is one of the biggest trends in the decade. The term itself has many definitions, including sustainable, natural-source or bio-based and biodegradable ingredients, as well as minimal processing and environmental impact. However, it is often difficult to use natural materials or materials derived from nature to meet the requirements of a suitable encapsulation composition. The bio-based and biodegradable ingredients for customer formulations must provide a unique combination of performance and sustainability, so that consumers can feel confident about the safety and efficacy of these ingredients.

[0008] Naturally derived polymers such as proteins and polysaccharides are attractive chemical structural units for encapsulating reagents and have been explored by the industry in recent years. Many of these materials are also biodegradable. However, there is a continuing need to provide new biodegradable materials for encapsulating beneficial agents.

[0009] The use of enzymes as catalysts to generate macromolecular (oligomeric or polymeric) materials has attracted increasing attention (Nikulin et al, Molecules 2021, 26, 2750), however, the application of such enzymatically produced oligomers or polymers in encapsulating beneficial agents has not been reported. Summary of the Invention

[0011] In a first aspect, the present invention provides a microcapsule composition comprising at least one core-shell microcapsule, wherein the at least one core-shell microcapsule comprises a hydrophobic core and a shell surrounding the core, and wherein the shell comprises a polymer or oligomer generated in situ by enzymatic oligomerization / polymerization of a substrate.

[0012] In a second aspect, there is provided a method for preparing the microcapsule composition as described herein.

[0013] In another aspect, there is provided the use of the microcapsule composition as described herein for enhancing the performance of beneficial agents in consumer goods.

[0014] The present invention also provides a consumer good comprising the microcapsule composition as described herein.

[0015] Brief Description of the Drawings

[0016] Figure 1a An example showing the reaction kinetics of the formation of oligopeptides and / or polypeptides catalyzed by esterase.

[0017] Figure 1b An example showing the comparison between the 1 1H NMR (H2O) spectra of (1bi) monomer L-alanine ethyl ester and (1bii) reaction product polyalanine.

[0018] Figure 2a Examples showing the overlapping IR spectra of monomeric tyrosine methyl ester and the reaction product polytyrosine are provided.

[0019] Figure 2b Examples showing the 1 comparison between the 1H NMR (H2O) spectra of (2bi) monomeric L-tyrosine methyl ester and (2bii) the reaction product polytyrosine are provided.

[0020] Figure 3 Examples showing the microscopic images of microcapsule compositions encapsulating Mygliol obtained by a protease-catalyzed method using an ethyl alaninate substrate are provided.

[0021] Figures 4 to 7 Examples showing the microscopic images of microcapsule compositions encapsulating various fragrances obtained by a protease-catalyzed method using tyrosine methyl ester and N-benzoyl-N-tyrosine ethyl ester (BTEE) substrates are provided.

[0022] Figure 8 Examples showing the microscopic images of microcapsule compositions encapsulating fragrances obtained by a redox enzyme-catalyzed method using tyrosine methyl ester and N-benzoyl-N-tyrosine ethyl ester (BTEE) substrates are provided.

[0023] Figure 9a and 10a Examples showing the microscopic images of microcapsule compositions encapsulating fragrances obtained by a lipase-catalyzed method using a pentadecanolide substrate are provided.

[0024] Figure 9b and 10b Examples showing the SEM (scanning electron microscope) images of microcapsule compositions encapsulating fragrances obtained by a lipase-catalyzed method using a pentadecanolide substrate are provided.

[0025] Definition

[0026] The term "beneficial agent" refers to any substance that, when added to a product, can improve the consumer's perception of the product or enhance the product's performance in its application. Examples of beneficial agents include fragrance / flavor ingredients, flavoring ingredients, cosmetic ingredients, bioactive agents (such as bactericides, insect repellents, and pheromones), substrate enhancers (such as silicones and brighteners), enzymes (such as lipases and proteases), dyes, pigments, and nutraceuticals.

[0027] The term "microcapsule" refers to capsules with a size range from 0.1 μm to 500 μm.

[0028] The term "bio-based" relates to the source of a material and refers to a material intentionally made from substances derived from living (or once-living) organisms, rather than petroleum-derived materials. This definition includes natural materials such as naturally extracted proteins and polysaccharides, as well as materials that have been processed to some extent, such as cellulose fibers.

[0029] A "biodegradable" material is defined as a material whose physical and chemical properties deteriorate and completely degrade when exposed to the environment. Thus, this property is related to the end-of-life of the material. Bio-based materials can be biodegradable or non-biodegradable. Similarly, while many bio-based materials are biodegradable (such as starch), not all biodegradable materials are bio-based.

[0030] In the context of the present invention, a "biodegradable" component or "biodegradable" material in general, such as a shell material, is a material that meets the passing criteria of "inherently biodegradable" and / or "readily biodegradable" in at least one OECD biodegradation study. To avoid any ambiguity, this means that if a component passes one test but fails one or more other tests, the passing result overrides the other test results.

[0031] Enzymes are proteins that act as biological catalysts by accelerating chemical reactions.

[0032] Enzyme immobilization can be defined as the confinement of enzyme molecules on / in a carrier in a physical or chemical or both ways such that it retains all or most of its activity.

[0033] The molecule on which an enzyme acts is called a substrate.

[0034] The prefix "poly" (as in "polycarboxylic acid", "polyol", etc.) indicates a functionality ≥2.

[0035] The term "amino acid ester derivative" refers to any derivative of an amino acid ester produced by reaction at the amino group, ester group, side-chain functional group, or by replacement of any hydrogen by a heteroatom.

[0036] The term "amino acid derivative" refers to any derivative of an amino acid produced by reaction at the amino group, carboxyl group, side-chain functional group, or by replacement of any hydrogen by a heteroatom. Detailed Description

[0037] The preferred and / or optional features of the present invention will now be set forth. Unless the context otherwise requires, any aspect of the present invention can be combined with any other aspect of the present invention. Unless the context otherwise requires, any preferred or optional feature of any aspect can be combined, singly or in combination, with any aspect of the present invention and with any other preferred or optional feature.

[0038] The Applicant has surprisingly and unexpectedly found that microcapsules can be obtained by an in-situ enzymatic polymerization method starting from various substrates. In particular, the Applicant has found that the polymerization reaction can occur in an oil-in-water emulsion medium, where the oil droplets are encapsulated by the reaction product of the enzymatic polymerization of the substrate. The encapsulating material obtained in this way is novel and suitable for use as an encapsulating medium.

[0039] Enzymatic reactions generally occur under mild conditions and, compared to conventional production schemes, they reduce resource consumption and waste generation. Enzymatic catalyzed polymerization (enzymatic polymerization) in particular provides novel polymeric materials that are usually difficult or even impossible to synthesize by conventional polymerization methods.

[0040] Accordingly, the present invention provides a microcapsule composition comprising at least one core-shell microcapsule, wherein the at least one core-shell microcapsule comprises a hydrophobic core and a shell surrounding the core, and wherein the shell comprises a polymer or oligomer formed in-situ by the enzymatic catalyzed oligomerization / polymerization of a substrate.

[0041] It is advantageous if the substrate is derived from natural (bio-based), sustainable and / or renewable sources to produce a bio-based encapsulating material.

[0042] Most of these substrates, as well as the resulting oligomers and polymers, are also biodegradable, thus providing an additional benefit.

[0043] Hydrophobic core

[0044] The hydrophobic core comprises a solvent material, at least one beneficial agent or a mixture thereof.

[0045] Beneficial agent

[0046] Suitable beneficial agents to be incorporated into the core of the core-shell microcapsules of the present invention include fragrance / flavor components, flavoring components, cosmetic components, bioactive agents (such as fungicides, insect repellents and pheromones), substrate enhancers (such as siloxanes and brighteners), enzymes (such as esterases, proteases and redox enzymes), dyes, pigments and nutraceuticals.

[0047] In one embodiment, the at least one beneficial agent can be at least one fragrance ingredient. A comprehensive list of fragrance ingredients that can be encapsulated according to the present invention can be found in fragrance literature such as "Perfume & Flavor Chemicals", S. Arctander (Allured Publishing, 1994). The fragrance ingredients encapsulated according to the present invention preferably comprise fragrance ingredients selected from the following: acetyl isoeugenol ((E)-2-methoxy-4-(prop-1-en-1-yl)phenyl acetate); adoxal (2,6,10-trimethylundec-9-enal); AGRUMEX (2-(tert-butyl)cyclohexyl acetate); C10 decanal (decanal); C11 MOA aldehyde (2-methyldecanal); C11 undecenal (undec-10-enal); C110 undecanal (undecanal); C12 lauraldehyde (dodecanal); C12MNA aldehyde (2-methylundecanal); C8 octanal (octanal); C9 isononanal (3,5,5-trimethylhexanal); food grade C9 nonanal (nonanal); C90 nonenal ((E)-non-2-enal); ISOC11 aldehyde ((E)-undec-9-enal); red mandarin aldehyde ((E)-dodec-2-enal); allyl amyl glycolate (2-(3-methylbutoxy)acetic acid prop-2-enyl ester); allyl hexanoate (hexanoic acid prop-2-enyl ester); allyl cyclohexanepropionate (3-cyclohexanepropionic acid prop-2-enyl ester); allyl heptanoate (heptanoic acid prop-2-enyl ester); amber core (1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-ol); ambroxan (3,8,8,11a-tetramethyldodecahydro-1H-3,5a-epoxynaphtho[2,1-c]oxepine); ambroxol (1,3,4,5,6,7-hexahydro-β,1,1,5,5-pentamethyl-2H-2,4a-methano naphthalen-8-ethanol); gamma-decalactone ((Z)-oxacycloheptadec-10-en-2-one); ambroxane ((3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran); amyl butyrate (amyl butyrate); amyl cinnamic aldehyde ((Z)-2-benzylideneheptanal); amyl salicylate (2-hydroxybenzoic acid pentyl ester); synthetic anethole ((E)-1-methoxy-4-(prop-1-en-1-yl)benzene); anisyl acetate (4-methoxybenzyl acetate); avermectin ester (formic acid 1-(3,3-dimethylcyclohexyl)ethyl ester); anisaldehyde p-cresol (4-methoxybenzaldehyde); aurantiin ((E)-2-((7-hydroxy-3,7-dimethyloctylidene)amino)benzoic acid methyl ester); BELAMBRE ((1R,2S,4R)-2'-isopropyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane]); benzaldehyde (benzaldehyde);Benzyl acetate (benzyl acetate); Benzyl acetone (4-phenylbutan-2-one); Benzyl benzoate (benzyl benzoate); Benzyl salicylate (benzyl 2-hydroxybenzoate); Breviflorin (ethyl 6-acetoxyhexanoate); Bicyclononanolide (octahydro-2H-chromen-2-one); Ethoxycyclododecyloxymethane ((ethoxymethoxy)cyclododecane); Burchellin ((1S,2R,5R)-2-ethoxy-2,6,6-trimethyl-9-methylenebicyclo[3.3.1]nonane); Borneol crystal ((1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol); Bornyl acetate (acetic acid (2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl ester); Bourgeonal (3-(4-(tert-butyl)phenyl)propanal); Butyl butyryllactate (butyric acid 1-butoxy-1-oxopropan-2-yl ester); p-tert-Butylcyclohexyl acetate (acetic acid 4-(tert-butyl)cyclohexyl ester); sec-Butylquinoline (2-(2-methylpropyl)quinoline); Synthetic camphor ((1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one); Carvacrol (5-isopropyl-2-methylphenol); (-)-Carvone ((5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one); Cashmeran (1,1,2,3,3-pentamethyl-2,3,6,7-tetrahydro-1H-inden-4(5H)-one); CASSYRANE (5-tert-butyl-2-methyl-5-propyl-2H-furan); Cedrene ((1S,8aR)-1,4,4,6-tetramethyl-2,3,3a,4,5,8-hexahydro-1H-5,8a-methylenecyclopropa[a]naphthalene); Cedryl acetate (acetic acid (1S,6R,8aR)-1,4,4,6-tetramethyloctahydro-1H-5,8a-methylenecyclopropa[a]naphthalen-6-yl ester); Cedryl methyl ether ((1R,6S,8aS)-6-methoxy-1,4,4,6-tetramethyloctahydro-1H-5,8a-methylenecyclopropa[a]naphthalene); Allyl ionone ((E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)hepta-1,6-dien-3-one); Synthetic cinnamyl alcohol ((E)-3-phenylprop-2-en-1-ol); Cinnamaldehyde ((2E)-3-phenylprop-2-enal); Cinnamyl acetate (acetic acid (E)-3-phenylprop-2-en-1-yl ester); cis-Jasmone ((Z)-3-methyl-2-(pent-2-en-1-yl)cyclopent-2-enone); cis-3-Hexenol ((Z)-hex-3-en-1-ol); Citral ((E)-3,7-dimethylocta-2,6-dienal); Citral diethyl acetal ((Z)-1,1-diethoxy-3,7-dimethylocta-2,6-diene); Citronellal (3,7-dimethyloct-6-enal); Citronellol (3,7-dimethyloct-6-en-1-ol); Citronellyl acetate (acetic acid 3,7-dimethyloct-6-en-1-yl ester);Citronellyl formate (3,7-dimethyloct-6-en-1-yl formate); citronellyl nitrile (3,7-dimethyloct-6-enenitrile); cinnamonitrile (dodecanonitrile); corolla alcohol (4-cyclohexyl-2-methylbutan-2-ol); celestial musk ((Z)-3-methylcyclotetradec-5-enone); coumarin crystal (2H-chromen-2-one); p-cresol acetate (acetic acid (4-methylphenyl) ester); p-cresol methyl ether (1-methoxy-4-methylbenzene); cuminonitrile (4-isopropylbenzonitrile); privet aldehyde (2,4-dimethylcyclohex-3-ene-1-carboxaldehyde); cyperamide (3-(4-isopropylphenyl)-2-methylpropanal); cyclopentane ester (2-(cyclohexyloxy) acetate allyl ester); cyclopentane ester (cyclopentane ester); Hexyl ethyl acetate (2-cyclohexylethyl acetate); cyclohexyl salicylate (2-hydroxybenzoic acid cyclohexyl ester); cyclocitron (8,8-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-carboxaldehyde); p-cymene (1-methyl-4-prop-2-ylbenzene); damascenone ((E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one); methyl damascenone ((E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one); butyl damascenone (1-(2,6,6-trimethyl-1-cyclohex-3-enyl)but-2-en-1-one); propyl decalactone (5-hexyloxacyclopentane) alkane-2-one); trans-4-decenal ((E)-dec-4-enal); DELPHONE (2-pentylcyclopentanone); δ-3-carene ((1S,6S)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene); dihexyl fumarate (dihexyl-but-2-enedioate); dihydroanethole (1-methoxy-4-propylbenzene); dihydrojasmone (3-methyl-2-pentylcyclopent-2-enone); dihydromyrcenol (2,6-dimethyloct-7-en-2-ol); dimethyl anthranilate (methyl 2-(methylamino)benzoate); dimethylbenzylmethanol (2-methyl-1-phenylpropan-2-ol); dimethylbenzyl acetate (acetic acid 2-methyl-1 1-phenylpropan-2-yl ester); dimethyl benzyl butyrate (2-methyl-1-phenylpropan-2-yl butyrate); dimethyl octenone (4,7-dimethyloct-6-en-3-one); dimethyl heptol (2,6-dimethyl hept-2-ol); limonene (1-methyl-4-(prop-1-en-2-yl) cyclohex-1-ene); diphenyl ether (oxydiphenyl); butyl dodecalactone (6-heptyltetrahydro-2H-pyran-2-one); propyl dodecalactone (5-octyloxacyclopentane-2-one); dodecenal ((E)-dodec-2-enal); dobicarb ((E)-4-((3aS,7aS)-hexahydro-1H-4,7-methyleneinden-5(6H)-ylidene)butyraldehyde);Ebanol ((E)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)penta-4-en-2-ol); ESTERLY (ethyl cyclohexyl carboxylate); ethyl acetate (ethyl acetate); ethyl acetoacetate (ethyl 3-oxobutanoate); ethyl cinnamate (ethyl 3-phenylprop-2-enoate); ethyl caproate (ethyl hexanoate); ethyl linalool ((E)-3,7-dimethylnona-1,6-dien-3-ol); ethyl linalyl acetate (ethyl (Z)-3,7-dimethylnona-1,6-dien-3-yl acetate); ethyl maltol (2-ethyl-3-hydroxy-4H-pyran-4-one); ethyl methyl-2-butyrate (ethyl 2-methylbutyrate); ethyl octanoate (ethyl octanoate); ethyl heptanoate (ethyl heptanoate); ethyl phenylglycidate (ethyl 3-phenyloxirane-2-carboxylate); ethyl crocinate (ethyl 2,6,6-trimethylcyclohexa-1,3-diene-1-carboxylate); ethyl vanillin (3-ethoxy-4-hydroxybenzaldehyde); ethyl phthalate (1,4-dioxacycloheptadecane-5,17-dione); eucalyptol ((1S,4S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane); eugenol (4-allyl-2-methoxyphenol); synthetic oakmoss (methyl 2,4-dihydroxy-3,6-dimethylbenzoate); fenchyl acetate (ethyl (2S)-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl acetate); fenchol ((1S,2R,4R)-1,3,3-trimethylbicyclo[2.2.1]hept-2-ol); anisaldehyde (3-(4-methoxyphenyl)-2-methylpropanal); FIXAMBRENE (3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan); tonalide (1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone); marine aldehyde (3-(4-ethylphenyl)-2,2-dimethylpropanal); cyclamen aldehyde (3-(3-isopropylphenyl)butanal); FLORIDILE ((E)-undec-9-enenitrile); tricyclodecenyl propionate (ethyl (3aR,6S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl propionate); floropai (2,4,6-trimethyl-4-phenyl-1,3-dioxane); lily of the valley pyran HC (tetrahydro-4-methyl-2-(2-methylpropyl)-2H-pyran-4-ol); fresh menthone (2-(sec-butyl)cyclohexanone); apple ester (ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate); fructone ester (ethyl (3aS,4S,7R,7aS)-octahydro-1H-4,7-methanoinden-3a-carboxylate); fruit nitrile (2-methyldecanenitrile);Gerponone (1-(5,5-dimethylcyclohex-1-en-1-yl)pent-4-en-1-one); Styralyl acetate (1-phenylethyl acetate); Tricyclodecenyl isobutyrate ((3aR,6S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl 2-methylpropanoate); Geraniol ((E)-3,7-dimethylocta-2,6-dien-1-ol); Geranyl acetate ((E)-3,7-dimethylocta-2,6-dien-1-yl acetate); Geranyl crotonate ((E)-3,7-dimethylocta-2,6-dien-1-yl but-2-enoate); Geranyl isobutyrate ((E)-3,7-dimethylocta-2,6-dien-1-yl 2-methylpropanoate); Kepone (Ethyl 2-ethyl-6,6-dimethylcyclohex-2-ene-1-carboxylate); Exaltolide ((E)-oxacyclohexadec-12-en-2-one); Methyl dihydrojasmonate (Methyl 3-oxo-2-pentylcyclopentaneacetate); Piperonal crystals (Benzod[d][1,3]dioxole-5-carbaldehyde); Shampoo ester ((2S)-Ethyl 3-isopropylbicyclo[2.2.1]hept-5-ene-2-carboxylate); trans-2-Hexenal ((E)-hex-2-enal); cis-3-Hexenol ((Z)-hex-3-en-1-ol); cis-3-Hexenyl acetate ((Z)-hex-3-en-1-yl acetate); cis-3-Hexenyl butyrate ((Z)-hex-3-en-1-yl butyrate); cis-3-Hexenyl isobutyrate ((Z)-hex-3-en-1-yl 2-methylpropanoate); cis-3-Hexenyl salicylate ((Z)-hex-3-en-1-yl 2-hydroxybenzoate); Hexyl acetate (Hexyl acetate); Hexyl benzoate (Hexyl benzoate); Hexyl butyrate (Hexyl butyrate); Hexyl cinnamaldehyde ((E)-2-benzylideneoctanal); Hexyl isobutyrate (Hexyl 2-methylpropanoate); Hexyl salicylate (Hexyl 2-hydroxybenzoate); Hydroxycitronellal (7-Hydroxy-3,7-dimethyloctanal); Indolein (4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin); Indole (1H-Indole); Indolenine liquid (8,8-bis(1H-indol-3-yl)-2,6-dimethyloctan-2-ol); beta-Ionone ((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one); Tonalide ((E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one); alpha-Ionone ((E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one); alpha-Irone ((E)-4-(2,5,6,6-tetramethylcyclohex-2-en-1-yl)but-3-en-2-one); Ambroxan (1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethanone);Isoamyl acetate (3-methylbutyl acetate); Isoamyl butyrate (3-methylbutyl butyrate); Isobutyl methoxypyrazine (2-methylpropyl 3-methoxypyrazine); Isocyclocitral (2,4,6-trimethylcyclohex-3-ene-1-carbaldehyde); Isoeugenol ((E)-2-methoxy-4-(prop-1-en-1-yl)phenol); Isojasmone B11 (2-hexylcyclopent-2-en-1-one); Isomenthone DL (2-isopropyl-5-methylcyclohexanone); Iso-nonyl acetate (3,5,5-trimethylhexyl acetate); Isopropyl 2-methylbutyrate (isopropyl 2-methylbutanoate); Iso-propyl quinoline (6-isopropylquinoline); Isomethyl ionone ((E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one); Tricyclodecenyl acetate ((3aR,6S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl acetate); Cis-jasmone ((Z)-3-methyl-2-(pent-2-en-1-yl)cyclopent-2-enone); Jasmyl acetate (3-butyl-5-methyltetrahydro-2H-pyran-4-yl acetate); Jasmopyran (3-pentyltetrahydro-2H-pyran-4-yl acetate); Javanese sandalwood ((1-methyl-2-((1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)methyl)cyclopropyl)methanol); Homofarnesene ((Z)-3,4,5,6,6-pentamethylhept-3-en-2-one); Lactone (8-isopropyl-1-oxaspiro[4.5]dec-2-one); Leaf alcohol acetal ((Z)-1-(1-ethoxyethoxy)hex-3-ene); Citronitrile ((2E,6Z)-3,7-dimethylnona-2,6-dienenitrile); Green flower fragrance (methyl (Z)-hex-3-enoate); Lyral (3-(4-(tert-butyl)phenyl)-2-methylpropanal); #N / A Linalool (3,7-dimethylocta-1,6-dien-3-ol); Linalool oxide (2-(5-methyl-5-vinyltetrahydrofuran-2-yl)propan-2-ol); Linalyl acetate (3,7-dimethylocta-1,6-dien-3-yl acetate); MAHONIAL ((4E)-9-hydroxy-5,9-dimethyl-4-decenal); Maltol (3-hydroxy-2-methyl-4H-pyran-4-one); Isobutyrate maltol ester (2-methylpropanoic acid 2-methyl-4-oxo-4H-pyran-3-yl ester); Matricin (ethyl 2-methylvalerate); May lily alcohol ((4-isopropylcyclohexyl)methanol); Rose alcohol (3-methyl-5-phenylpent-1-ol); Melonal (2,6-dimethylhept-5-enal); #N / A#N / A Mercapto-8-menthan-3-one (mercapto-p-menthan-3-one); Methyl anthranilate (methyl 2-aminobenzoate); Methyl benzoate (methyl benzoate);Methyl cedryl ketone (1 - ((1S,8aS)-1,4,4,6 - tetramethyl - 2,3,3a,4,5,8 - hexahydro - 1H - 5,8a - methyleneazulene - 7 - yl)ethanone); Methyl cinnamate (methyl 3 - phenylprop - 2 - enoate); Methyl dantilis (2 - ethoxy - 4 - (methoxymethyl)phenol); Methyl dihydrojasmonate (methyl 2 - hexyl - 3 - oxocyclopentane - 1 - carboxylate); Methyl heptenone (6 - methylhept - 5 - en - 2 - one); Methyl lactone (8 - methyl - 1 - oxaspiro[4.5]dec - 2 - one); Methyl nonyl ketone (undecan - 2 - one); Methyl octynoate (methyl non - 2 - ynoate); Pomelo methane (6,6 - dimethoxy - 2,5,5 - trimethylhex - 2 - ene); Methyl salicylate (methyl 2 - hydroxybenzoate); Musk enone ((Z)-3 - methylcyclopentadecen - 5 - one); Citronellal (4 - (4 - methylpent - 3 - en - 1 - yl)cyclohex - 3 - enecarbaldehyde); Myrcene (7 - methyl - 3 - methyleneocta - 1,6 - diene); MYSTIKAL (2 - methylundecanoic acid); Ambroxan (2 - (2 - (4 - methylcyclohex - 3 - en - 1 - yl)propyl)cyclopentanone); Neo - bergamot ester (2 - methyl - 6 - methyleneoct - 7 - en - 2 - yl acetate); NEOCASPIRENE EXTRA (10 - isopropyl - 2,7 - dimethyl - 1 - oxaspiro[4.5]dec - 3,6 - diene); Neo - forcelate ((E)-methyl non - 2 - enoate); NEROLEX ((2Z)-3,7 - dimethylocta - 2,6 - diene - 1 - ol); Nerolidol ((Z)-3,7,11 - trimethyldodeca - 1,6,10 - trien - 3 - ol); NEROLIDYLE ((Z)-3,7,11 - trimethyldodeca - 1,6,10 - trien - 3 - yl acetate); β - naphthyl ethyl ether crystal (2 - ethoxynaphthalene); Neo - neral (1 - (3 - methylbenzofuran - 2 - yl)ethanone); Neryl acetate ((Z)-3,7 - dimethylocta - 2,6 - diene - 1 - yl acetate); NIRVANOLIDE ((E)-13 - methyloxacyclopentadecen - 10 - en - 2 - one); Nonadienal ((2E,6Z)-non - 2,6 - dienal); 2,6 - Nonadienol ((2Z,6E)-2,6 - nonadien - 1 - ol); Nonade (6,8 - dimethylnonan - 2 - ol); γ - Nonalactone (5 - pentyloxolane - 2 - one); cis - 6 - Nonenal ((Z)-non - 6 - enal); cis - 6 - Nonenol ((Z)-non - 6 - en - 1 - ol); Nopol acetate (2 - (6,6 - dimethylbicyclo[3.1.1]hept - 2 - en - 2 - yl)ethyl acetate); NYMPHEAL (3 - (4 - (2 - methylpropyl)-2 - methylphenyl)propanal); δ - Octalactone (6 - propyltetrahydro - 2H - pyran - 2 - one); Methyl hexyl ketone (octan - 2 - one);Sweet Orange Crystal (1-(2-Naphthyl)-Ethanone); Irisone (4-(tert-Amyl) Cyclohexanone); β-Phenylethyl Methyl Ether ((2-Methoxyethyl) Benzene); p-tert-Butylcyclohexyl Acetate (Acetic Acid 4-(tert-Butyl) Cyclohexyl Ester); Fruit Amide (2-Ethyl-N-Methyl-N-(m-Tolyl) Butyramide); Peach Aldehyde (5-Heptyldihydrofuran-2(3H)-One); Geranyl Pyran (2-Methyl-4-Methylene-6-Phenyltetrahydro-2H-Pyran); Tetrahydrogeraniol (3,7-Dimethyloctan-1-Ol); Peony Nitrile (2-Cyclohexylidene-2-Phenylacetonitrile); PETALIA (2-Cyclohexylidene-2-(o-Tolyl) Acetonitrile); Pharaoh's Ketone (2-Cyclohexylhepta-1,6-Dien-3-One); Phenoxyethyl Isobutyrate (2-Methylpropanoic Acid 2-(Phenoxy) Ethyl Ester); Phenylacetaldehyde (2-Phenyl-Acetaldehyde); Phenylethyl Acetate (Acetic Acid 2-Phenylethyl Ester); Phenylethyl Alcohol (2-Phenylethyl Alcohol); Phenylethyl Isobutyrate (2-Methylpropanoic Acid 2-Phenylethyl Ester); Phenylethyl Phenylacetate (2-Phenylacetic Acid 2-Phenylethyl Ester); Phenylpropanol (3-Phenylpropan-1-Ol); α-Pinene (2,6,6-Trimethylbicyclo[3.1.1]Hept-2-Ene); β-Pinene (6,6-Dimethyl-2-Methylenebicyclo[3.1.1]Heptane); Pinonaldehyde (3-(6,6-Dimethylbicyclo[3.1.1]Hept-2-Ene-2-Yl) Propanal); Neo-Rose Ester (Propanoic Acid 2,2-Dimethyl-2-Phenylethyl Ester); POMAROSE ((2E,5E)-5,6,7-Trimethyloct-2,5-Dien-4-One); POMELOL (2,4,7-Trimethyl-6-Octen-1-Ol); Methyl Nerylaldehyde B (1-Methyl-4-(4-Methylpent-3-Ene-1-Yl) Cyclohex-3-Enecarbaldehyde); Isopentenyl Acetate (Acetic Acid 3-Methylbut-2-Ene-1-Yl Ester); Coconut Aldehyde (5-Pentyldihydrofuran-2(3H)-One); Sandalwood Alcohol ((E)-2-Ethyl-4-(2,2,3-Trimethylcyclopent-3-Ene-1-Yl) But-2-Ene-1-Ol); Raspberry Ketone (4-(4-Hydroxyphenyl) Butan-2-One); Cyclic Ether (2,4-Dimethyl-4-Phenyltetrahydrofuran); Crystal Rose (Acetic Acid 2,2,2-Trichloro-1-Phenylethyl Ester); 9-Decenol (Dec-9-Ene-1-Ol); Rose Oxide (4-Methyl-2-(2-Methylprop-1-Ene-1-Yl) Tetrahydro-2H-Pyran); Rose Oxide CO (4-Methyl-2-(2-Methylprop-1-Ene-1-Yl) Tetrahydro-2H-Pyran); ROSYFOLIA (1-Methyl-2-(5-Methylhex-4-Ene-2-Yl) Cyclopropylmethanol); Aromatic Rose Oxide (4-Methyl-2-Phenyl-3,6-Dihydro-2H-Pyran); Crocin Indene (2,3,3-Trimethyl-1-Indanone); Crocin Aldehyde (2,6,6-Trimethylcyclohex-1,3-Dienecarbaldehyde);SCENTAURUS CLEAN ((Z)-2-acetyl-4-methyltridec-2-enoic acid ethyl ester); SCENTAURUS JUICY (4-(dodecylthio)-4-methylpentan-2-one); WHITE MUSK (2-(1-(3,3-dimethylcyclohexyl)ethoxy)-2-methylpropyl cyclohexanecarboxylate); CYCLOPENTADECOLIDE (cyclopentadecanone, hexadecanolide); AGRANDEHYDE (2-methyl-3-[4-(2-methylpropyl)phenyl]propanal); SPIROPENTONE (1-(spiro[4.5]dec-6-en-7-yl)pent-4-en-1-one); OLEFANTONE ((E)-5-methylheptan-3-one oxime); STRYRANYL ACETATE (1-phenylethyl acetate); SUPER MUGUET ((E)-6-ethyl-3-methyloct-6-en-1-ol); Yucca musk (cyclohexanecarboxylic acid (E)-2-((3,5-dimethylhex-3-en-2-yl)oxy)-2-methylpropyl ester); terpinene methyl (1-methyl-4-prop-2-ylcyclohexa-1,3-diene); terpinene propyl (1-methyl-4-prop-2-ylcyclohexa-1,4-diene); terpineol (2-(4-methylcyclohex-3-en-1-yl)propan-2-ol); terpineol methyl (2-(4- methyl-1-cyclohex-3-enyl)propan-2-ol); terpineol (2-(4-methylcyclohex-3-en-1-yl)propan-2-ol); terpinol (1-methyl-4-(propan-2-ylidene)cyclohex-1-ene); terpineol acetate (acetic acid 2-(4-methyl-1-cyclohex-3-enyl)propan-2-yl ester); tetrahydrolinalool (3,7-dimethyloctan-3-ol); tetrahydromyrcenol (2,6-dimethyloctan-2-ol); Tibetan musk (oxacyclohexadecane-2-one); thymol (2-isopropyl ether) propyl-5-methylphenol); cyclopropylanisole (1-(cyclopropylmethyl)-4-methoxybenzene); tricyclic terpene aldehyde (2,4-dimethylcyclohex-3-enecarboxaldehyde); tridecene-2-carbonitrile ((E)-trideca-2-enenitrile); neoprivet aldehyde (3-phenylbutyraldehyde); neoheliotrope aldehyde (3-(benzo[d][1,3]dioxol-5-yl)-2-methylpropanal); neoheliotrope aldehyde (3-(benzo[d][1,3]dioxol-5-yl)-2-methylpropanal); 11-12-carbon-3-ol ene ((3E,5Z)-undec-1,3,5-triene); methyldecenol ((E)-4-methyldec-3-en-5-ol); vanillin (4-hydroxy-3-methoxybenzaldehyde); vanillone (2,2,5-trimethyl-5-pentylcyclopentanone); cyclohexadecenone ((Z)-cyclohexadecan-5-enone); violet nitrile ((2E,6Z)-nona-2,6-dienenitrile); ethyl naphthyl methyl ether (2-methoxynaphthalene); zinarine (2-(2,4-dimethylcyclohexyl)pyridine);BOIS CEDRE ESS CHINE (Cedarwood oil); EUCALYPTUS GLOBULUS ESS CHINA (Eucalyptus oil); GALBANUM ESS (Galbanum oil); GIROFLE FEUILLESESS RECT MADAGASCAR (Clove oil); LAVANDIN GROSSO OIL FRANCE ORPUR (Lavandin oil); MANDARIN OIL WASHED COSMOS (Tangerine oil); ORANGE TERPENES (Orange terpenes); PATCHOULI ESSINDONESIE (Patchouli oil); and YLANG ECO ESSENCE (Ylang-ylang oil). These perfume ingredients are particularly suitable for obtaining stable and well-performing microcapsules due to their favorable lipophilicity and olfactory properties.;

[0048] In a particularly preferred embodiment of the present invention, in a particularly preferred embodiment of the present invention, more than 75%, preferably more than 80%, even more preferably more than 85%, even still more preferably more than 90%, and even yet more preferably more than 95% of the perfume components are biodegradable and are selected from acetyl isoeugenol ((E)-2-methoxy-4-(prop-1-en-1-yl)phenyl acetate); adoxal (2,6,10-trimethylundec-9-enal); AGRUMEX (2-(tert-butyl)cyclohexyl acetate); C10 decanal (decanal); C11 undecenal (undec-10-enal); C110 undecanal (undecanal); C12 lauryl aldehyde (dodecanal); C12 MNA aldehyde (2-methylundecanal); C8 octanal (octanal); cyclamen aldehyde (3-(4-isopropylphenyl)-2-methylpropanal); ISOC11 aldehyde ((E)-undec-9-enal); allyl amyl glycolate (allyl 2-(3-methylbutoxy)acetate); allyl cyclohexanepropionate (allyl 3-cyclohexanepropionate); allyl heptanoate (allyl heptanoate); ambrettolide ((Z)-oxacycloheptadec-10-en-2-one); ambrox ((3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran); amyl salicylate (amyl 2-hydroxybenzoate); anisaldehyde p-cresol (4-methoxybenzaldehyde); benzyl acetate (benzyl acetate); benzyl salicylate (benzyl 2-hydroxybenzoate); bornyl acetate (acetic acid (2S,4S)-1,7,7-trimethylbicyclo[2.2.1] hept-2-yl ester); carvacrol (5-isopropyl-2-methylphenol); cedrene ((1S,8aR)-1,4,4,6-tetramethyl-2,3,3a,4,5,8-hexahydro-1H-5,8a-methanoazulene); cedryl acetate (acetic acid (1S,6R,8aR)-1,4,4,6-tetramethyloctahydro-1H-5,8a-methanoazulen-6-yl ester); cedryl methyl ether ((1R,6S,8aS)-6-methoxy-1,4,4,6-tetramethyloctahydro-1H-5,8a-methanoazulene); citral ((E)-3,7-dimethylocta-2,6-dienal); citronellol (3,7-dimethyloct-6-en-1-ol); citronellyl acetate (acetic acid 3,7-dimethyloct-6-en-1-yl ester); galaxolide ((Z)-3-methylcyclotetradec-5-enone); p-cresyl methyl ether (1-methoxy-4-methylbenzene); cyclohexyl ethyl acetate (acetic acid 2-cyclohexylethyl ester); cyclohexyl salicylate (2-hydroxybenzoic acid cyclohexyl ester); damascenone ((E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one); alpha-damascenone ((E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one); gamma-decalactone (5-hexyloxolane-2-one); trans-4-decenal ((E)-dec-4-enal); dihydromyrcenol (2,6-dimethyloct-7-en-2-ol); diphenyl ether (oxydibenzene); dihydroanethole (1-methoxy-4-propylbenzene); dihydrojasmone (3-methyl-2-pentylcyclopent-2-enone); dimethyl phthalate (methyl 2-(methylamino)benzoate); dimethyl benzyl carbinyl acetate (acetic acid 2-methyl-1-phenylpropan-2-yl ester); dimethyl benzyl carbinyl butyrate (butyric acid 2-methyl-1-phenylpropan-2-yl ester); dimethylheptanol (2,6-dimethylhept-2-ol); delta-dodecalactone (6-heptyltetrahydro-2H-pyran-2-one); gamma-dodecalactone (5-octyloxolane-2-one); dodecenal ((E)-dodec-2-enal); ebony alcohol ((E)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol); ethyl hexanoate (ethyl hexanoate); ethyl 2-methylbutyrate (ethyl 2-methylbutyrate); ethyl maltol (2-ethyl-3-hydroxy-4H-pyran-4-one); ethyl heptanoate (ethyl heptanoate); ethyl vanillin (3-ethoxy-4-hydroxybenzaldehyde); ethyl phthalate (1,4-dioxacycloheptadecane-5,17-dione); eucalyptol ((1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2] Octane); Eugenol (4 - allyl - 2 - methoxyphenol); Synthetic oakmoss (methyl 2,4 - dihydroxy - 3,6 - dimethylbenzoate); FIXAMBRENE (3a,6,6,9a - tetramethyldodecahydronaphtho[2,1 - b]furan); Florhydral (3 - (3 - isopropylphenyl)butanal); FLORIDILE ((E) - undec - 9 - enenitrile); Gerponone (1 - (5,5 - dimethylcyclohex - 1 - en - 1 - yl)penta - 4 - en - 1 - one); Styralyl acetate (1 - phenylethyl acetate); Geraniol ((E) - 3,7 - dimethylocta - 2,6 - dien - 1 - ol); Geranyl acetate ((E) - 3,7 - dimethylocta - 2,6 - dien - 1 - yl acetate); Exaltolide ((E) - oxacyclohexadec - 12 - en - 2 - one); Methyl dihydrojasmonate (methyl 3 - oxo - 2 - pentylcyclopentaneacetate); trans - 2 - Hexenal ((E) - hex - 2 - enal); cis - 3 - Hexenol ((Z) - hex - 3 - en - 1 - ol); cis - 3 - Hexenyl acetate ((Z) - hex - 3 - en - 1 - yl acetate); cis - 3 - Hexenyl salicylate ((Z) - hex - 3 - en - 1 - yl 2 - hydroxybenzoate); Hexyl acetate (hexyl acetate); Indolenine liquid (8,8 - bis(1H - indol - 3 - yl) - 2,6 - dimethyloctan - 2 - ol); beta - Ionone ((E) - 4 - (2,6,6 - trimethylcyclohex - 1 - en - 1 - yl)but - 3 - en - 2 - one); Isoraldein ((E) - 3 - methyl - 4 - (2,6,6 - trimethylcyclohex - 2 - en - 1 - yl)but - 3 - en - 2 - one); alpha - Ionone ((E) - 4 - (2,6,6 - trimethylcyclohex - 2 - en - 1 - yl)but - 3 - en - 2 - one); Isoamyl acetate (3 - methylbutyl acetate); Isoamyl butyrate (3 - methylbutyl butyrate); Isoeugenol ((E) - 2 - methoxy - 4 - (prop - 1 - en - 1 - yl)phenol); Isojasmone B11 (2 - hexylcyclopent - 2 - en - 1 - one); Isomethylionone ((E) - 3 - methyl - 4 - (2,6,6 - trimethylcyclohex - 2 - en - 1 - yl)but - 3 - en - 2 - one); Jasmolide (3 - butyl - 5 - methyltetrahydro - 2H - pyran - 4 - yl acetate); Lactone (8 - isopropyl - 1 - oxaspiro[4.5] Decan - 2 - one); Citronitrile ((2E,6Z)-3,7 - dimethylnona - 2,6 - dienitrile); Linalool (3,7 - dimethylocta - 1,6 - dien - 3 - ol); Linalool oxide (2-(5 - methyl - 5 - vinyltetrahydrofuran - 2 - yl)propan - 2 - ol); Linalyl acetate (3,7 - dimethylocta - 1,6 - dien - 3 - yl acetate); Chrysanthemum ester (ethyl 2 - methylvalerate); May lily alcohol ((4 - isopropylcyclohexyl)methanol); Rose alcohol (3 - methyl - 5 - phenylpent - 1 - ol); Melonal (2,6 - dimethylhept - 5 - enal); Mercapto - 8 - menthan - 3 - one (mercapto - p - menthan - 3 - one); Methyl anthranilate (methyl 2 - aminobenzoate); Methyl benzoate (methyl benzoate); Methyl dantilis (2 - ethoxy - 4-(methoxymethyl)phenol); Methyl heptenone (6 - methylhept - 5 - en - 2 - one); Methyl lactone (8 - methyl - 1 - oxaspiro[4.5]dec - 2 - one); Methyl octynoate (methyl non - 2 - ynoate); Methyl salicylate (methyl 2 - hydroxybenzoate); Ambrosone (2-(2-(4 - methylcyclohex - 3 - en - 1 - yl)propyl)cyclopentanone); Nefrol (methyl (E)-non - 2 - enoate); NEROLEX ((2Z)-3,7 - dimethylocta - 2,6 - dien - 1 - ol); Nerolidol ((Z)-3,7,11 - trimethyldodeca - 1,6,10 - trien - 3 - ol); β - naphthyl ethyl ether crystal (2 - ethoxynaphthalene); Neo - neral (1-(3 - methylbenzofuran - 2 - yl)ethanone); Neryl acetate (acetate of (Z)-3,7 - dimethylocta - 2,6 - dien - 1 - yl); Nonadienal ((2E,6Z)-nona - 2,6 - dienal); cis - 6 - Nonenal ((Z)-nona - 6 - enal); cis - 6 - Nonenol ((Z)-nona - 6 - en - 1 - ol); NYMPHEAL (3-(4-(2 - methylpropyl)-2 - methylphenyl)propanal); δ - Octalactone (6 - propyltetrahydro - 2H - pyran - 2 - one); Sweet orange crystal (1-(2 - naphthyl) - ethanone); p - tert - Butylcyclohexyl acetate (4-(tert - butyl)cyclohexyl acetate); Peach aldehyde (5 - heptyldihydrofuran - 2(3H)-one); Tetrahydrogeraniol (3,7 - dimethyloctan - 1 - ol); Phenethyl acetate (2 - phenylethyl acetate); α - Pinene (2,6,6 - trimethylbicyclo[3.1.1]hept - 2 - ene); β - Pinene (6,6 - dimethyl - 2 - methylenebicyclo[3.1.1]heptane); POMAROSE ((2E,5E)-5,6,7-trimethyloct-2,5-dien-4-one); POMELOL FF (2,4,7-trimethyl-6-octen-1-ol); isopentenyl acetate (3-methylbut-2-en-1-yl acetate); coconut aldehyde (5-pentyldihydrofuran-2(3H)-one); raspberry ketone (4-(4-hydroxyphenyl)butan-2-one); 9-decenol (dec-9-en-1-ol); rose oxide CO (4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran); aromatic rose oxide (4-methyl-2-phenyl-3,6-dihydro-2H-pyran); safranal (2,6,6-trimethylcyclohexa-1,3-diene carboxaldehyde); SCENTAURUS JUICY (4-(dodecylthio)-4-methylpentan-2-one); silver aldehyde (2-methyl-3-[4-(2-methylpropyl)phenyl]propanal); styroyl acetate (1-phenylethyl acetate); yucca musk (cyclohexanecarboxylic acid (E)-2-((3,5-dimethylhex-3-en-2-yl)oxy)-2-methylpropyl ester); propyl terpinene (1-methyl-4-propan-2-ylcyclohexa-1,4-diene); terpineol (2-(4-methylcyclohex-3-en-1-yl)propan-2-ol); terpinolene (1 -methyl-4-(prop-2-ylidene)cyclohex-1-ene); tetrahydrolinalool (3,7-dimethyloctan-3-ol); cyclopropylanisole (1-(cyclopropylmethyl)-4-methoxybenzene); tridecene-2-carbonitrile ((E)-tridecene-2-carbonitrile); neoprivetaldehyde (3-phenylbutyraldehyde); neoheliotropin (3-(benzo[d][1,3]dioxol-5-yl)-2-methylpropanal); methyldecenol ((E)-4-methyldec-3-en-5-ol); ethylnaphthyl ether (2-methoxynaphthalene); BOIS CEDRE ESS CHINE (CEDRE WOOD OIL); EUCALYPTUS GLOBULUS ESS CHINA (Eucalyptus Oil); GALBANUM ESS (Galbanum Oil); GIROFLE FEUILLESESS RECT MADAGASCAR (Clove Oil); LAVANDIN GROSSO OIL FRANCE ORPUR (Lavender Oil); MANDARIN OIL WASHED COSMOS (Mandarin Oil); ORANGE TERPENES (Orange Terpenes); PATCHOULI ESSINDONESIE (Patchouli Oil); and YLANG ECO ESSENCE (Ylang-Ylang Oil). These ingredients have the advantage of providing a particularly sustainable microcapsule. .

[0049] The at least one beneficial agent may comprise at least one fragrance precursor, i.e., a material capable of releasing fragrance components by means of stimuli such as a change in temperature, the presence of an oxidizing agent, the action of an enzyme, or the action of light. Such fragrance precursors are well known in the art.

[0050] The at least one beneficial agent may further comprise at least one functional cosmetic ingredient. The functional cosmetic ingredient in the composition for encapsulation is preferably hydrophobic. Preferably, the cosmetic ingredient has a calculated octanol / water partition coefficient (ClogP) of 1.5 or greater, more preferably 3 or greater. Alternatively, preferably, the ClogP of the cosmetic ingredient is from 2 to 7.

[0051] Particularly useful functional cosmetic ingredients may be selected from emollients, smoothing ingredients, water-absorbing ingredients, soothing and relaxing ingredients, decorative ingredients, deodorants, anti-aging ingredients, cell-regenerating ingredients, draining ingredients, reshaping ingredients, skin-smoothing ingredients, preservatives, antioxidants, antibacterial or bacteriostatic ingredients, cleansing ingredients, lubricating ingredients, structuring ingredients, hair-conditioning ingredients, whitening ingredients, texturing ingredients, softening ingredients, anti-dandruff ingredients, and exfoliating ingredients.

[0052] Particularly useful functional cosmetic ingredients include, but are not limited to, hydrophobic polymers such as alkyl dimethicone, polymethylsilsesquioxane, polyethylene, polyisobutene, styrene-ethylene-styrene and styrene-butene-styrene block copolymers, etc.; mineral oils such as hydrogenated isoparaffin, silicone oil, etc.; vegetable oils such as argan oil, jojoba oil, aloe oil, etc.; fatty acids and fatty alcohols and their esters; glycolipids; phospholipids; sphingolipids such as ceramides; sterols and steroids; terpenes, sesquiterpenes, triterpenes and their derivatives; essential oils such as arnica oil, wormwood oil, bark oil, birch leaf oil, calendula oil, cinnamon oil, echinacea oil, eucalyptus oil, ginseng oil, jujube oil, sunflower oil, jasmine oil, hybrid lavender oil, lotus seed oil, perilla oil, rosemary oil, sandalwood oil, tea tree oil, thyme oil, valerian oil, wormwood oil, ylang-ylang oil and yucca oil.

[0053] In particular, the at least one functional cosmetic ingredient may be selected from sandalwood oil such as Santalum album kernel oil; panthenol triacetate; tocopheryl acetate; tocopherol; naringin; ethyl linoleate; farnesyl acetate; farnesol; citronellyl tiglate; and ceramide-2 (1-stearoyl-C18-sphingosine, CAS-No: 100403-19-8).

[0054] The at least one beneficial agent may include a reagent for suppressing or reducing malodor and its perception by adsorbing odor, a reagent for providing a warming or cooling effect, a repellent, or a UV absorber.

[0055] Solvent material

[0056] The present invention also contemplates incorporating a solvent material in place of or in addition to the beneficial agent. The solvent material is a hydrophobic material that is miscible with the beneficial agent used in the present invention. Suitable solvent materials are those that have a reasonable affinity for the beneficial agent and a Clog P greater than 2.5, preferably greater than 6, and most preferably greater than 10. Suitable solvent materials include, but are not limited to, triglyceride oils, glycerol monoesters and glycerol diesters, mineral oils, silicone oils, diethyl phthalate, polyalphaolefins, castor oil, and isopropyl myristate.

[0057] Examples of suitable solvent materials are mono-, di-, and triesters of fatty acids and glycerol and mixtures thereof, optionally wherein the fatty acid chain is in the range C4-C26, optionally wherein the fatty acid chain has any level of unsaturation; isopropyl myristate; fatty acid esters of polyglycerol oligomers: R 2 CO-[OCH2-CH(OCOR 1 )-CH2O-] n , wherein R 1 and R 2 can be H or a C4-C26 aliphatic chain, or a mixture thereof, and n ranges from 2-50, preferably 2-30; nonionic fatty alcohol alkoxylates, optionally wherein the alkoxyl is ethoxyl, propoxyl, butoxyl, or a mixture thereof; nonionic, anionic, and cationic surfactants containing di- and tri-fatty acid chains, and mixtures thereof; fatty acid esters of polyethylene glycol, polypropylene glycol, and polybutylene glycol, or mixtures thereof; polyalphaolefins; mineral oils; silicone oils such as polydimethylsiloxane and polydimethylcyclosiloxane; diethyl phthalate or diisodecyl adipate.

[0058] In one embodiment, the core comprises a solvent material in combination with at least one beneficial agent. In one embodiment, the beneficial agent is a fragrance material.

[0059] In one embodiment, the beneficial agent is biodegradable.

[0060] Polymer or oligomer

[0061] A polymer or oligomer contained in the shell of the core-shell microcapsules of the present invention is generated in situ by an enzyme-catalyzed method.

[0062] Oligomers and polymers produced from renewable carbon sources and containing components extracted from plant biomass (such as starch, cellulose, vegetable oils, lignin from plants or wood pulp, obtained from atmospheric carbon dioxide by photosynthesis) as well as products of microbial and animal origin are all bio-based. Most of these materials are also expected to be biodegradable.

[0063] In one embodiment, the macromolecular materials (oligomers or polymers) generated by in-situ enzymatic polymerization include low polyesters or polyesters, low polyamides or polyamides, low poly(amino acids) or poly(amino acids), low polyaromatics or polyaromatics, or mixtures thereof.

[0064] Enzyme

[0065] Enzymes have been applied in many industrial (organic) processes. According to the Enzyme Commission (EC), all enzymes are classified into six main groups:

[0066] EC1: Oxidoreductases, which catalyze redox reactions by electron transfer.

[0067] EC2: Transferases, which catalyze the transfer of a functional group (such as a methyl or glycosyl group) from one compound (donor) to another compound (acceptor).

[0068] EC3: Hydrolases, which catalyze the hydrolysis of various bonds in order to transfer a functional group to water.

[0069] EC4: Lyases, which catalyze the cleavage of C-C, C-O, C-N, and other bonds by means other than hydrolysis or oxidation.

[0070] EC5: Isomerases, which catalyze the racemization or epimerization of chiral centers; isomerases are subdivided according to their substrates.

[0071] EC6: Ligases, which catalyze the coupling of two molecules, accompanied by the hydrolysis of a diphosphate bond in ATP or a similar triphosphate.

[0072] The mechanisms of enzyme catalysis are different, but in principle are similar to other types of chemical catalysis, because the key factor is to reduce the energy barrier separating the reactants (or substrates) from the products. The reduction of the activation energy (E a ) increases the fraction of reactant molecules that can overcome this energy barrier and form products. An important principle is that, since they only lower the energy barrier between products and reactants, enzymes always catalyze reactions in both directions and cannot drive the reaction forward or affect the equilibrium position ─ only the rate at which it is achieved. Like other catalysts, enzymes are not consumed or altered by the reaction (as are substrates), but are recycled, such that a single enzyme can perform multiple rounds of catalysis.

[0073] Enzymatic polymerization has been increasingly applied in the past few years, providing many successful examples of functional polymer materials. The application of enzymes in polymer chemistry has many advantages: polymerization can be carried out under mild conditions regarding pressure, temperature, and pH, which makes enzymatic reactions very energy-efficient. Enzymes can be highly selective: chemo-selectivity, regio-selectivity, and enantioselectivity can all be enzymatically induced, thus opening up new directions for precise polymer synthesis. Enzymes are considered "green" non-toxic catalysts, which can meet the growing demands regarding commercial, ecological, and biomedical requirements.

[0074] Redox enzymes

[0075] Most redox enzymes contain low-valent metals as catalytic centers. It is believed that the polymerization process involves enzyme-initiated radical polymerization of aromatic or vinyl monomers. Therefore, the enzyme does not catalyze the polymerization reaction itself but rather the reaction that forms the active form of the monomer.

[0076] For example, laccase (EC1.10.3.2) catalyzes the oxidation of organic substrates (mainly derivatives of phenol and aniline) with molecular oxygen. The catalytic center of laccase consists of four copper atoms, which form complexes with the imidazole groups of histidine and constitute an electron transfer chain. It is believed that one copper atom is directly involved in the oxidation of the organic reductant, while the other three form the center where oxygen is reduced to water.

[0077] Peroxidase (EC1.11.1) catalyzes the oxidation of various organic substrates with hydrogen peroxide. The catalytic site of peroxidase includes a heme with an iron atom, which has variable oxidation states. In the catalytic cycle, it is believed that the Fe(IV) species forms at the active site and oxidizes the organic substrate into a polymerization-active radical. For example, in the presence of hydrogen peroxide, horseradish peroxidase (HRP) effectively catalyzes the polymerization of phenol to obtain a medium-molecular-weight phenol polymer composed of a mixture of phenylene and oxyphenylene units.

[0078] Redox enzymes have been used in the polymerization of phenyl-containing compounds to obtain poly(phenol) or poly(aniline).

[0079] Hydrolases

[0080] Hydrolases are the most studied enzymes for oligomer / polymer synthesis, and among these studies, esterases (EC3.1) and proteases (EC3.4) are the most widely used.

[0081] For example, carboxylester hydrolases (EC 3.1.1.) in the esterase category act on ester bonds and have been applied in several biotechnological methods. Examples of carboxylester hydrolases that act on ester bonds are triacylglycerol lipase (EC 3.1.1.3), carboxylesterase (EC 3.1.1.1.), and cutinase (EC3.1.1.74).

[0082] Lipase (EC 3.1.1.3) can catalyze a very wide range of reactions, including not only the formation and hydrolysis of ester bonds, but also amidation, ammonolysis, aldol condensation, Michael addition, lactone ring opening, and epoxidation. Lipases have been successfully used to obtain many types of biodegradable polymers, most notably polyesters, polyamides, and polyesteramides. There are two main types of polymerization reactions using lipases: ring-opening polymerization and polycondensation. Ring-opening polymerization uses cyclic esters, such as lactones or lactides, to open them and carry out chain growth reactions. Polycondensation uses hydroxy acids as monomers or diacids (diesters) and diols to link them through ester bonds.

[0083] Cutinase (EC 3.1.1.74) is capable of catalyzing ester hydrolysis, esterification, and transesterification reactions. In this regard, cutinase is considered an alternative to lipase in the case of obtaining biodegradable polymers, especially polyesters.

[0084] Proteolytic enzymes such as proteases (EC 3.4) can be used as enzyme catalysts in the synthesis of oligopeptides and oligopeptide mimetics with various functions and physical properties. Among proteases, papain is the most widely used in enzymatic polymerization, probably due to its broad substrate specificity, stability, and ease of production. Proteases have been shown to catalyze the polymerization of amino acid esters and the copolymerization of amino acids with polyamides.

[0085] Hydrolases have been applied to the synthesis of polyesters, polycarbonates, polyamides, polyamino acids, oligopeptides, and polyesteramides.

[0086] Thus, in one embodiment, the enzyme is:

[0087] a) A hydrolase (EC 3), such as an esterase (EC 3.1) or a protease / peptidase (EC 3.4); or

[0088] b) An oxidoreductase (EC 1), such as an oxidoreductase acting on diphenols as donors (EC 1.10) or an oxidoreductase acting on peroxides as acceptors (EC 1.11).

[0089] In one embodiment,

[0090] a1) The esterase is a carboxylester hydrolase (EC 3.1.1), such as a carboxylesterase (EC 3.1.1.1), a triacylglycerol lipase (EC 3.1.1.3), or a cutinase (EC 3.1.1.74), preferably a triacylglycerol lipase (EC 3.1.1.3), such as Amano Lipase PS;

[0091] a2) The protease / peptidase is a serine endopeptidase (EC 3.4.21) or a cysteine endopeptidase (EC 3.4.22), such as papain;

[0092] b) The oxidoreductase is a peroxidase (EC 1.11.1), preferably peroxidase EC 1.11.1.7, such as peroxidase from horseradish (horseradish peroxidase, HRP).

[0093] In one embodiment, the enzyme is immobilized on a solid support by covalent binding and / or physical adsorption to produce a heterogeneous immobilized enzyme system. The heterogeneity of the immobilized enzyme system allows for easy recovery of both the enzyme and the product, multiple reuse of the enzyme, continuous operation of the enzymatic method, rapid termination of the reaction, and a greater variety of bioreactor designs.

[0094] Substrates and oligomers / polymers

[0095] For an enzymatic polymerization reaction, suitable monomers are required.

[0096] As described above, a series of oligomers or polymers have been obtained by enzymatic polymerization, including polyesters, polyamides, amino acid-based polymers including oligopeptides and polypeptides, and oligomers or polymers containing polyphenylene / oxyphenylene.

[0097] In one embodiment, the monomers are derived from nature (bio-based), are sustainable and / or renewable, thereby producing bio-based oligomers / polymers.

[0098] Most of these substrates, as well as the resulting oligomers and polymers, are also biodegradable, thereby providing additional benefits.

[0099] Polyesters are a class of polymers with ester functional groups as the bonds between individual monomers. Methods for synthesizing polyesters require two different routes: (i) ring-opening polymerization of cyclic monomers (lactones, cyclic diesters, cyclic carbonates, and cyclic ketene acetals), and (ii) step-growth polycondensation of diacids or diesters with diols or polyols (polyhydric alcohols), or self-condensation of hydroxyacids or hydroxyesters.

[0100] Generally, lactones, diacids and their ester and anhydride derivatives, diols, polyols, cyclic carbonates, and hydroxyacids and their esters are suitable structural units for polyester synthesis.

[0101] Polyamides are polymers in which monomer units are linked together by amide bonds. Lactams, ω-amino acids and their esters, diacids and their derivatives, and diamines are suitable monomers for polyamide synthesis.

[0102] Polyamino acids are polymers based on amino acids and are composed of amino acids as monomer units. When the amino group of one amino acid forms an amide (peptide) bond with the carboxyl group of another amino acid, a peptide is formed. Oligopeptides consist of 2 to about 20 amino acids and may include di-, tri-, tetra-aso peptides. Suitable substrates for obtaining polyamino acids and / or oligopeptides are amino acid esters and their derivatives. Amino acids used in chemoenzymatic polymerization can be classified into hydrophobic amino acids and hydrophilic amino acids. Proteases have a relatively high affinity for hydrophobic amino acid derivatives. The hydrophobic nature of these amino acids renders the resulting polypeptides insoluble in water, leading to precipitation during the polymerization process. In contrast, hydrophilic amino acid derivatives with or without protecting groups on the reactive side groups can also be used in chemoenzymatic polymerization. Reactive groups on the side chain, such as alcohol and amine groups, can be used for various types of functionalization of the resulting polypeptides. However, due to their water solubility, additional methods are required to separate the product from the protease used in the synthesis reaction.

[0103] There exists a large number of structurally diverse phenols, anilines, and other aromatic monomers that have undergone enzyme-initiated radical polymerization, resulting in poly(phenol) and poly(aniline).

[0104] Therefore, monomers suitable for carrying out the enzymatic polymerization according to the present invention are selected from:

[0105] - lactones, cyclic carbonates, diacids and their ester and anhydride derivatives, diols, polyols, and hydroxy acids and their esters;

[0106] - lactams, ω - amino acids and their esters, diacids and their derivatives, and diamines;

[0107] - hydrophobic and hydrophilic amino acid esters and their derivatives;

[0108] - phenyl-containing amino acids and peptides.

[0109] In one embodiment, the substrate is selected from lactones, cyclic carbonates, polycarboxylic compounds, polyols, cyclic amides / lactams, ω - amino acids and their esters, amino acid alkyl esters and their derivatives, oligopeptide alkyl esters, phenyl-containing peptides, phenyl-containing amino acids, or a combination thereof.

[0110] In one embodiment,

[0111] a1) When the enzyme is lipase, the substrate is selected from lactones, cyclic carbonates, polycarboxylic compounds, polyols, cyclic amides / lactams, ω - amino acids and their esters, amino acid alkyl esters and their derivatives, and combinations thereof;

[0112] a2) When the enzyme is protease, the substrate is selected from amino acid alkyl esters and their derivatives, oligopeptide alkyl esters, and combinations thereof;

[0113] b) When the enzyme is an oxidoreductase, the substrate is a phenyl-containing amino acid or amino acid derivative, a phenyl-containing peptide, or a combination thereof.

[0114] In one embodiment,

[0115] - The lactone is a macrocyclic lactone having more than a 12-membered ring, such as pentadecanolide, ambrettolide, cyclopentadecenolide, or a combination thereof;

[0116] - The cyclic carbonate is a cyclic carbonate having more than an 8-membered ring;

[0117] - The polycarboxylic acid compound is a polycarboxylic acid compound having more than 8 carbon atoms;

[0118] - The polyol is a polyol having more than 8 carbon atoms;

[0119] - The cyclic amide / lactam is a lactam having more than an 8-membered ring;

[0120] - The amino acid alkyl ester and its derivative are hydrophobic amino acid alkyl esters, such as alkyl esters of alanine, valine, isoleucine, leucine, methionine, phenylalanine, tyrosine, tryptophan, or a combination thereof;

[0121] - The oligopeptide alkyl ester is an oligopeptide alkyl ester in which the peptide contains 2 to 9 amino acids;

[0122] - The phenyl-containing amino acid is tyrosine, phenylalanine, or a combination thereof;

[0123] - The phenyl-containing peptide is a phenyl-containing peptide in which the peptide contains 2 to 9 amino acids.

[0124] In one embodiment, the alkyl is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and benzyl.

[0125] In one embodiment, the enzyme is Amano lipase PS, and the substrate is a macrocyclic lactone having more than a 12-membered ring, preferably ω-pentadecanolide.

[0126] In one embodiment, the enzyme is papain, and the substrate is methyl tyrosine or methyl tyrosine and ethyl N-benzoyl-N-tyrosinate.

[0127] In one embodiment, the enzyme is horseradish peroxidase, and the substrate is methyl tyrosine or methyl tyrosine and ethyl N-benzoyl-N-tyrosinate.

[0128] In one embodiment, the microcapsule composition is in the form of an aqueous slurry.

[0129] In one embodiment, the volume average size (Dv(50)) of the microcapsules can be from 1 to 500 μm, optionally from 1 to 100 μm, preferably from 5 to 80 μm, and even more preferably from 10 to 70 μm.

[0130] In one embodiment, the slurry can be dried to present an encapsulated composition in dry powder form.

[0131] The enzymatic polymerization reaction of the present invention results in the formation of oligomeric or polymeric products that are capable of forming a shell around the oil droplets containing the beneficial agent. However, some of the oligomeric or polymeric products produced by the enzymatic method do not assemble to form a shell around the oil droplets. Thus, in one embodiment, in addition to the core-shell microcapsules encapsulating the beneficial agent, the microcapsule composition further comprises oligomers or polymer residues that do not assemble to form a shell around the oil droplets. When drying such a microcapsule composition, the composition comprises microcapsules encapsulating the beneficial agent and a matrix in which the beneficial agent is embedded.

[0132] Method

[0133] In one aspect, there is provided a method for preparing a microcapsule composition as described herein, the method comprising the steps of:

[0134] a) providing a substrate and an enzyme in an aqueous phase under conditions suitable for providing enzyme activity;

[0135] b) providing a hydrophobic phase;

[0136] c) emulsifying the hydrophobic phase in the aqueous phase to form a microcapsule composition.

[0137] The substrate, enzyme and hydrophobic material are as described above.

[0138] In one embodiment, a method for preparing a microcapsule composition comprising at least one core-shell microcapsule, wherein the at least one core-shell microcapsule comprises a hydrophobic core and a shell surrounding the core, the method comprising the steps of:

[0139] a) providing a substrate and an enzyme in an aqueous phase under conditions suitable for providing enzyme activity to generate a polymer or oligomer,

[0140] b) providing a hydrophobic phase;

[0141] c) emulsifying the hydrophobic phase in the aqueous phase to form a microcapsule composition.

[0142] In one embodiment, the substrate is selected from lactones, cyclic carbonates, polycarboxylic acid compounds, polyols, cyclic amides / lactams, ω-amino acids and their esters, amino acid alkyl esters and their derivatives, oligopeptide alkyl esters, phenyl-containing peptides, phenyl-containing amino acids or combinations thereof.

[0143] In one embodiment, the enzyme is

[0144] a) a hydrolase (EC3), such as an esterase (EC3.1) or a protease / peptidase (EC3.4); or

[0145] b) an oxidoreductase (EC1), such as an oxidoreductase acting on diphenols as donors (EC1.10) or an oxidoreductase acting on peroxides as acceptors (EC1.11).

[0146] In one embodiment,

[0147] a1) the esterase is a carboxylester hydrolase (EC3.1.1), such as a carboxylesterase (EC3.1.1.1), a triacylglycerol lipase (EC3.1.1.3) or a cutinase (EC3.1.1.74), preferably a triacylglycerol lipase (EC3.1.1.3), such as Amano lipase PS;

[0148] a2) the protease / peptidase is a serine endopeptidase (EC3.4.21) or a cysteine endopeptidase (EC3.4.22), such as papain;

[0149] b) the oxidoreductase is a peroxidase (EC1.11.1), preferably peroxidase EC1.11.1.7, such as peroxidase from horseradish (HRP).

[0150] In one embodiment,

[0151] a1) when the enzyme is a lipase, the substrate is selected from lactones, cyclic carbonates, polycarboxylic compounds, polyols, cyclic amides / lactams, ω-amino acids and their esters, amino acid alkyl esters and their derivatives or combinations thereof;

[0152] a2) when the enzyme is a protease, the substrate is selected from amino acid alkyl esters and their derivatives, oligopeptide alkyl esters;

[0153] b) when the enzyme is an oxidoreductase, the substrate is a phenyl-containing amino acid or amino acid derivative or a phenyl-containing peptide or a combination thereof.

[0154] In one embodiment, the hydrophobic phase comprises at least one beneficial agent as defined above. In one embodiment, the at least one beneficial agent is at least one fragrance ingredient. In one embodiment, optionally in the presence of a buffer, the enzyme is dissolved in water and incubated at a temperature of about 20 °C to about 50 °C, preferably about 40 °C, for a period of 5 to 20 min, preferably about 10 min, to activate the enzyme.

[0155] Optionally, in the presence of a buffer, the substrate is dissolved in water and incubated for a period of 30 s to 2 min, preferably about 1 min, at a temperature of about 20 °C to about 50 °C, preferably about 40 °C.

[0156] An activated enzyme solution is added to the substrate solution to initiate the reaction.

[0157] An oil (hydrophobic) phase is added to the aqueous phase and emulsified for a period of 12 h to 36 h, preferably about 20 h, at a temperature of about 20 °C to about 50 °C, preferably about 40 °C, to obtain a microcapsule composition in the form of a slurry.

[0158] In one embodiment, when the enzyme is immobilized on a solid substrate, the method includes the step of separating the reaction mixture from the immobilized enzyme on the solid substrate.

[0159] The method according to the invention may include an additional step of drying the microcapsule slurry to obtain a microcapsule powder.

[0160] The drying of the microcapsule slurry is conventional and can be carried out according to techniques known in the art, such as spray drying, evaporation, freeze drying or using desiccants. Generally, as is conventional in the art, the dried microcapsules will be dispersed or suspended in a suitable powder, such as powdered silica, which can be used as a filler or glidant. Such a suitable powder can be added to the encapsulated composition before, during or after the drying step.

[0161] In particular, the drying process may be accompanied by an additional encapsulation process, in which an additional beneficial agent is encapsulated in the encapsulating material. For example, in addition to the core-shell microcapsules obtained by the method according to the invention, the slurry to be dried may also contain at least one unencapsulated beneficial agent and at least one encapsulating material, such that the beneficial agent not encapsulated in the core-shell microcapsules is encapsulated in the encapsulating material during drying. Thus, at the time of drying, a matrix is formed around the core-shell microcapsules or coexists with the core-shell microcapsules.

[0162] Consumer products

[0163] The invention also relates to consumer products comprising the microcapsule composition as described above. The consumer products may be selected from household (home) care, personal care, fabric care and pet care products.

[0164] Suitable household care products include hard surface cleaners, heavy duty detergents and detergent powders, air care compositions.

[0165] Suitable personal care products include cleansing compositions (such as shampoos, bath and shower gels, liquid soaps, soap bars), conditioning compositions (such as hair care conditioners), bath and shower lotions, oral care compositions, deodorant compositions, antiperspirant compositions, skin care products.

[0166] Suitable fabric care compositions include laundry detergents, laundry conditioners, fabric fresheners, and fragrance boosters.

[0167] The microcapsule composition of the present invention in the form of a microcapsule slurry suspended in an aqueous suspension medium can be incorporated into a consumer product matrix as it is, or can be incorporated in the form of a dry powder.

[0168] Another aspect of the present invention relates to the use of the microcapsule composition as described above for improving the perception of a beneficial agent in a consumer product or enhancing the performance of a beneficial agent.

[0169] The present invention is further illustrated by the following non-limiting examples.

[0170] The solid content of the microparticles was measured by a Halogen Moisture Analyzer Mettler Toledo instrument. This test measures the encapsulation efficacy, i.e., the percentage of the theoretical fragrance encapsulated.

[0171] Dv(50) represents the maximum particle size below which 50% of the sample volume is present, also known as the volume median diameter. It is also known as the Malvern volume-weighted particle size distribution, which is measured using light scattering techniques.

[0172] Microscopic images were recorded using an Olympus BX51 microscope.

[0173] SEM images were recorded using a Jeol JSM_6010PLUS / LV scanning electron microscope.

[0174] Table 1 shows the composition of fragrance 1 used in the examples:

[0175]

[0176]

[0177] Table 2 shows the composition of fragrances 2 - 4 used in the examples:

[0178]

[0179]

[0180] Example 1: Synthesis of poly(alanine) (poly(Ala)) using papain

[0181] In a 15 ml glass bottle, lyophilized papain (10 mg) was dissolved and activated at a concentration of 10 mg / ml in 1 ml of 1 M phosphate buffer (pH 7.0) containing 5 mM cysteine and 1 mM EDTA, and then incubated at 40 °C for 10 min.

[0182] The polymerization reaction was carried out in a final volume of 7 mL. 0.75 g (0.7 M) L-alanine ethyl ester (L-Ala-Et), 1 mL of papain (10 mg / mL), and 6 mL of 1 M phosphate buffer were added to a glass reaction tube. The reaction was gently stirred at 40 °C at 250 rpm for 24 h. The product was purified by centrifugation at 7830 rpm at 25 °C for 15 min. The precipitate (culot) PolyAla was washed once with dilute HCl (2% v / v) and twice with distilled water. The precipitate was lyophilized for yield calculation (yield = 71.0%).

[0183] The yield was calculated based on the amount of starting material (monomer), the amount of by-product released (ethanol in this case), and the amount of precipitated product:

[0184]

[0185] m = mass; M = molecular weight; n = number of moles

[0186] Figure 1a The evolution of the peak intensities of the relevant IR wavelengths of amine, ester, and amide functional groups in the reaction medium during the reaction process (i.e., reaction kinetics) was shown, demonstrating the total consumption of the starting material L-alanine ethyl ester (containing amine and ester functional groups) and the formation of amide bonds in the reaction product, thus indicating the formation of oligopeptides or polypeptides.

[0187] Figure 1b The 1 1H NMR (H2O) spectra of (1bi) L-alanine ethyl ester and (1bii) poly(Ala) were compared, thus confirming the consumption of the substrate and the formation of polyalanine.

[0188] Example 2: Synthesis of poly(tyrosine) (poly(Tyr)) using papain

[0189] In a 15 mL glass bottle, lyophilized papain was dissolved and activated in 1 mL of 1 M phosphate buffer (pH 7.0) with 5 mM cysteine and 1 mM EDTA at a concentration of 10 mg / mL, and then incubated at 40 °C for 10 min.

[0190] The polymerization reaction was carried out in a final volume of 7 ml. 0.13 g (0.1 M) L-tyrosine methyl ester, 1 mL papain (10 mg / mL) and 6 mL 1 M phosphate buffer were added to a glass reaction tube. The reaction was gently stirred at 40 °C at 250 rpm for 24 h. The product was purified by centrifugation at 7830 rpm at 25 °C for 15 min. The precipitate was washed once with dilute HCl (2% v / v) and twice with distilled water. Then the precipitate was lyophilized for yield calculation (yield = 86.8%).

[0191] Figure 2a The overlapping IR spectra of tyrosine methyl ester and poly(Tyr) are shown, confirming the conversion of the starting monomer to the reaction product. In particular, the peak at 1730 cm -1 disappears, which is characteristic of the ester bond in the monomer. The ester peak is replaced by the characteristic peak of the amide functional group in the product.

[0192] Figure 2b The comparison between the 1 1H NMR (H2O) spectra of (2bi) L-tyrosine methyl ester and (2bii) the reaction product is shown, confirming the consumption of the substrate and the formation of polytyrosine.

[0193] Example 3: Synthesis of microcapsules - Mygliol using ethyl alaninate and papain

[0194] In a flask, 30 mg of papain was dissolved in 2 ml of phosphate buffer containing 1 mM EDTA + 5 mM cysteine. The solution was incubated at 40 °C for 10 min.

[0195] In another flask equipped with a mechanical stirrer and a reflux condenser, 0.96 g of ethyl alaninate was dispersed in 12 ml of 1 M phosphate buffer. The substrate solution was pre-incubated at 40 °C for 1 min, and then the activated enzyme solution was added to initiate the reaction. The medium was homogenized at 40 °C at 250 rpm for 4 h. Then, the stirring was increased to 800 rpm. 3.5 g of Mygliol (medium-chain triglyceride oil) was added to the reaction mixture. The aqueous and oil phases were combined and homogenized at 40 °C at 800 rpm. The reaction was stopped after 20 h.

[0196] Figure 3 The microscopic image of the microcapsule composition encapsulating Mygliol obtained by the papain-catalyzed polymerization of ethyl alaninate is shown.

[0197] Example 4: Synthesis of microcapsules - fragrance 1 using tyrosine methyl ester, N-benzoyl-N-tyrosine ethyl ester (BTEE) and papain

[0198] In a flask, dissolve 20 mg of papain in 2 ml of phosphate buffer containing 1 mM EDTA + 5 mM cysteine. Incubate the solution at 40 °C for 10 min.

[0199] In another flask equipped with a mechanical stirrer and a reflux condenser, disperse 0.26 g of methyl tyrosine and 0.1 g of BTEE in 12 ml of 1 M phosphate buffer. Pre-incubate the substrate solution at 40 °C for 1 min, then add the activated enzyme solution to initiate the reaction. Homogenize the medium at 40 °C at 250 rpm for 4 h. Then, increase the stirring to 800 rpm. Add 3.5 g of flavor 1 as the oil phase to the reaction. Combine the aqueous and oil phases and homogenize at 800 rpm at 40 °C. Stop the reaction after 20 h.

[0200] Figure 4 The micrograph of the microcapsule composition encapsulating flavor 1 obtained by papain-catalyzed polymerization of methyl tyrosine and BTEE is shown.

[0201] Example 5: Synthesis of microcapsules - flavor 2 using methyl tyrosine, BTEE and papain

[0202] In a flask, dissolve 20 mg of papain in 2 ml of phosphate buffer containing 1 mM EDTA + 5 mM cysteine. Incubate the solution at 40 °C for 10 min.

[0203] In another flask equipped with a mechanical stirrer and a reflux condenser, disperse 0.26 g of methyl tyrosine and 0.1 g of BTEE in 12 ml of 1 M phosphate buffer. Pre-incubate the substrate solution at 40 °C for 1 min, then add the activated enzyme solution to initiate the reaction. Homogenize the medium at 40 °C at 250 rpm for 4 h. Then, increase the stirring to 800 rpm. Add 3.5 g of flavor 2 as the oil phase to the reaction. Combine the aqueous and oil phases and homogenize at 800 rpm at 40 °C. Stop the reaction after 20 h.

[0204] Figure 5 The micrograph of the microcapsule composition encapsulating flavor 2 obtained by papain-catalyzed polymerization of methyl tyrosine and BTEE is shown.

[0205] Example 6: Synthesis of microcapsules - flavor 3 using methyl tyrosine, BTEE and papain

[0206] In a flask, dissolve 20 mg of papain in 2 ml of phosphate buffer containing 1 mM EDTA + 5 mM cysteine. Incubate the solution at 40 °C for 10 min.

[0207] In another flask equipped with a mechanical stirrer and a reflux condenser, 0.26 g of methyl tyrosine and 0.1 g of BTEE were dispersed in 12 ml of 1 M phosphate buffer. The substrate solution was pre-incubated at 40 °C for 1 min, and then the activated enzyme solution was added to initiate the reaction. The medium was homogenized at 40 °C at 250 rpm for 4 h. Then, the stirring was increased to 800 rpm. 3.5 g of flavor 3 as the oil phase was added to the reaction. The aqueous and oil phases were combined and homogenized at 40 °C at 800 rpm. The reaction was stopped after 20 h.

[0208] Figure 6 The micrograph of the microcapsule composition encapsulating flavor 3 obtained by papain-catalyzed polymerization of methyl tyrosine and BTEE is shown.

[0209] Example 7: Synthesis of microcapsule - flavor 4 using methyl tyrosine, BTEE, and papain

[0210] In a flask, 20 mg of papain was dissolved in 2 ml of phosphate buffer containing 1 mM EDTA + 5 mM cysteine. The solution was incubated at 40 °C for 10 min.

[0211] In another flask equipped with a mechanical stirrer and a reflux condenser, 0.26 g of methyl tyrosine and 0.1 g of BTEE were dispersed in 12 ml of 1 M phosphate buffer. The substrate solution was pre-incubated at 40 °C for 1 min, and then the activated enzyme solution was added to initiate the reaction. The medium was homogenized at 40 °C at 250 rpm for 4 h. Then, the stirring was increased to 800 rpm. 3.5 g of flavor 4 as the oil phase was added to the reaction. The aqueous and oil phases were combined and homogenized at 40 °C at 800 rpm. The reaction was stopped after 20 h.

[0212] Figure 7 The micrograph of the microcapsule composition encapsulating flavor 4 obtained by papain-catalyzed polymerization of methyl tyrosine and BTEE is shown.

[0213] Example 8: Synthesis of microcapsule - flavor 2 using methyl tyrosine, BTEE, and peroxidase

[0214] In a flask, 1.4 mg of HRP was dissolved in 2 ml of phosphate buffer containing 1 mM EDTA + 5 mM cysteine. The solution was incubated at 40 °C for 10 min.

[0215] In another flask equipped with a mechanical stirrer and a reflux condenser, 0.26 g of methyl tyrosine and 0.1 g of BTEE were dispersed in 12 ml of 1 M phosphate buffer. The substrate solution was pre-incubated at 40 °C for 1 min, and then the activated enzyme solution was added to initiate the reaction. The medium was homogenized at 40 °C at 250 rpm for 4 h. Then, the stirring was increased to 800 rpm. 3.5 g of flavor 2 as the oil phase was added to the reaction. The aqueous and oil phases were combined and homogenized at 800 rpm at 40 °C for 5 min. 1.5 ml of H2O2 was added dropwise to the mixture over 2 h. The reaction was stopped after 1 h.

[0216] Figure 8 The micrograph of the microcapsule composition encapsulating flavor 2 obtained by peroxidase-catalyzed polymerization of methyl tyrosine and BTEE is shown.

[0217] Example 9: Synthesis of microcapsules - flavor 1 (18.75% ω-pentadecanolide) using ω-pentadecanolide (poly(PDL)) and lipase

[0218] In a flask, 5 g of ω-pentadecanolide and 6 g of flavor 1 were stirred at 45 °C to obtain a homogeneous solution. The solution was added to 40 g of a 1% pectin A104 solution. The mixture was vigorously stirred (800 rpm) at 45 °C for 1 h to form a stable emulsion. The pH was adjusted to 6.2.

[0219] A suspension of 200 mg of lipase from Pseudomonas cepacia in 20 g of a 1% pectin A104 solution was added to the emulsion, and the mixture was stirred at 800 rpm at 60 °C for 2 h. Then the temperature was raised from 60 °C to 70 °C and the emulsion was stirred for 24 h.

[0220] The volume median particle size was measured to be 64.9 μm.

[0221] Figure 9a The micrograph of the microcapsule composition encapsulating flavor 1 obtained by lipase-catalyzed polymerization of ω-pentadecanolide (at 18.75 wt% monomer concentration) is shown.

[0222] Figure 9b The SEM (scanning electron microscope) image of the microcapsule composition encapsulating flavor 1 obtained by catalytic polymerization of ω-pentadecanolide with lipase (at 18.75 wt% monomer concentration) is shown.

[0223] Example 10: Synthesis of microcapsules - flavor 1 (3.75% ω-pentadecanolide) using ω-pentadecanolide (poly(PDL)) and lipase

[0224] In a flask, 1.8 g of ω-pentadecanolide and 16.2 g of fragrance 1 were stirred at 45 °C to obtain a homogeneous solution. This solution was added to 30 g of a 1% pectin A104 solution. The mixture was vigorously stirred (800 rpm) at 45 °C for 1 h to form a stable emulsion. The pH was adjusted to 5.2.

[0225] A suspension of 300 mg of lipase from Pseudomonas cepacia in 30 g of a 1% pectin A104 solution was added to this emulsion, and the mixture was stirred at 60 °C for 7 h while maintaining the stirring speed at 800 rpm.

[0226] The volume median particle size was measured to be 44 μm.

[0227] Figure 10a A micrograph of the microcapsule composition encapsulating fragrance 1 obtained by lipase-catalyzed polymerization of ω-pentadecanolide (at a monomer concentration of 3.75 wt%) is shown.

[0228] Figure 10b An SEM (scanning electron microscope) image of the microcapsule composition encapsulating fragrance 1 obtained by the catalytic polymerization of lipase of ω-pentadecanolide (at a monomer concentration of 3.75 wt%) is shown.

Claims

1. A microcapsule composition comprising at least one core - shell microcapsule, wherein the at least one core - shell microcapsule comprises a hydrophobic core and a shell surrounding the core, and wherein the shell comprises a polymer or oligomer formed in situ by enzymatic oligomerization / polymerization of a substrate.

2. The microcapsule composition according to claim 1, wherein the core comprises a solvent material, at least one beneficial agent or a mixture thereof, preferably wherein the core comprises at least one beneficial agent, and most preferably wherein the beneficial agent is a fragrance ingredient.

3. The microcapsule composition according to claim 2, wherein the microcapsule composition comprises a water - soluble matrix in which the beneficial agent is encapsulated.

4. The microcapsule composition according to any one of the preceding claims, wherein at least one of the shell surrounding the core and the water - soluble matrix in which the beneficial agent is encapsulated is bio - based.

5. The microcapsule composition according to any one of the preceding claims, wherein at least one of the shell surrounding the core, the beneficial agent and the water - soluble matrix in which the beneficial agent is encapsulated is biodegradable.

6. The microcapsule composition according to any one of the preceding claims, wherein the enzyme is a) a hydrolase (EC3), such as an esterase (EC3.1) or a protease / peptidase (EC3.4); or b) an oxidoreductase (EC1), such as an oxidoreductase acting on a diphenol as a donor (EC1.10) or an oxidoreductase acting on a peroxide as an acceptor (EC1.11).

7. The microcapsule composition according to claim 6, wherein a1) the esterase is a carboxylester hydrolase (EC3.1.1), such as a carboxylesterase (EC3.1.1.1), a triacylglycerol lipase (EC3.1.1.3) or a cutinase (EC3.1.1.74), preferably a triacylglycerol lipase (EC3.1.1.3), such as Amano lipase PS; a2) the protease / peptidase is a serine endopeptidase (EC3.4.21) or a cysteine endopeptidase (EC3.4.22), such as papain; b) the oxidoreductase is a peroxidase (EC1.11.1), preferably peroxidase EC1.11.1.7, such as peroxidase from horseradish (HRP).

8. The microcapsule composition according to any one of the preceding claims, wherein the enzyme is immobilized on a carrier by covalent binding and / or physical adsorption.

9. The microcapsule composition according to any one of the preceding claims, wherein the substrate is selected from lactones, cyclic carbonates, polycarboxylic compounds, polyols, cyclic amides / lactams, ω - amino acids and their esters, amino acid alkyl esters and their derivatives, oligopeptide alkyl esters, phenyl - containing peptides, phenyl - containing amino acids or combinations thereof.

10. The microcapsule composition according to any one of the preceding claims, wherein a1) when the enzyme is a lipase, the substrate is selected from lactones, cyclic carbonates, polycarboxylic compounds, polyols, cyclic amides / lactams, ω - amino acids and their esters, amino acid alkyl esters and their derivatives or combinations thereof; a2) When the enzyme is a protease, the substrate is selected from amino acid alkyl esters and their derivatives, and oligopeptide alkyl esters; b) When the enzyme is an oxidoreductase, the substrate is a phenyl-containing amino acid or amino acid derivative, or a phenyl-containing peptide, or a combination thereof.

11. The microcapsule composition according to claim 10, wherein a) the lactone is a macrocyclic lactone having more than 12-membered rings, such as pentadecanolide, ambrettolide, and cyclopentadecenolide; b) the cyclic carbonate is a cyclic carbonate having more than 8-membered rings; c) the cyclic amide / lactam is a lactam having more than 8-membered rings; d) the polycarboxylic acid compound is a polycarboxylic acid compound having more than 8 carbon atoms; e) the polyol is a polyol having more than 8 carbon atoms; f) the amino acid alkyl esters and their derivatives are hydrophobic amino acid alkyl esters, such as alkyl esters of alanine, valine, isoleucine, leucine, methionine, phenylalanine, tyrosine, and tryptophan; g) the oligopeptide alkyl esters are oligopeptide alkyl esters in which the peptide contains 2 to 9 amino acids; h) the phenyl-containing amino acid is tyrosine or phenylalanine; i) the phenyl-containing peptide is a phenyl-containing peptide in which the peptide contains 2 to 9 amino acids, optionally wherein the alkyl is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and benzyl.

12. A method for preparing the microcapsule composition according to any one of claims 1 to 11, the method comprising the following steps: a) providing a substrate and an enzyme in an aqueous phase under conditions suitable for providing enzyme activity; b) providing a hydrophobic phase; c) emulsifying the hydrophobic phase in the aqueous phase to form a microcapsule composition.

13. The method according to claim 12, further comprising the step of spray-drying the emulsion obtained in step c).

14. A consumer product comprising the microcapsule composition according to any one of claims 2 to 11, optionally wherein the consumer product is a fabric care product, a household care product, or a personal care product.

15. Use of the microcapsule composition according to any one of claims 2 to 11 for enhancing the performance of a beneficial agent in a consumer product.

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