Improvements in or relating to organic compounds

Abstract

The present invention provides a microcapsule composition comprising at least one core-shell microcapsule, wherein the at least one core-shell microcapsule comprises a core comprising at least one benefit agent and a shell surrounding the core, wherein the shell comprises a resin formed by the reaction of: 5 - a Michael acceptor which is the reaction product of a biodegradable polyester polyol with an α,β-unsaturated acid chloride; and - a Michael donor comprising at least two nucleophilic moieties selected from the group consisting of a nitrogen nucleophile, a sulfur nucleophile, an oxygen nucleophile, a carbon nucleophile, a phosphorus nucleophile, and mixtures thereof, which are capable to react with the 10 acrylic double bond of the Michael acceptor. The invention also relates to consumer products comprising the microcapsule composition, a method for preparing the microcapsule composition and to the use of the microcapsule composition to enhance the performance of a benefit agent in a consumer product.

Description

[0001] Improvements in or Relating to Organic Compounds

[0002] The present invention relates to a microcapsule composition comprising at least one core-shell microcapsule, to a method for preparing such a microcapsule composition, to a consumer product comprising the microcapsule composition, as well as to the use of such a microcapsule composition to enhance the performance of a benefit agent in a consumer product.

[0003] It is known to incorporate encapsulated benefit agents in consumer products, such as household care, personal care and fabric care products. Benefit agents include for example fragrances, cosmetic agents, food ingredients, nutraceuticals, drugs and substrate enhancers.

[0004] Encapsulated benefit agents are known in the art. They may be formed by a process of coating small solid particles or liquid droplets in a thin film of shell material. Although virtually any coating material, conceptually at least, is a candidate capsule shell material, in practice for commercial and regulatory reasons, to-date, there are relatively few materials that have been used in commercial products. Capsule shell material selection is determined by a number of factors including final application, cost, availability, processing ease, and inherent barrier properties. Defining an optimal shell material for a given application can be complex since many interacting parameters determine success of a given capsule shell material.

[0005] Microcapsules that are particularly suitable for delivery of benefit agents are core-shell microcapsules, wherein the core usually comprises the benefit agent and the shell is impervious or at least partially impervious to the benefit agent. Generally, these microcapsules are employed in aqueous media and the encapsulated benefit agents are hydrophobic. A broad selection of shell materials can be used, provided the shell material is impervious or at least partially impervious to the encapsulated benefit agent.

[0006] Benefit agents are encapsulated for a variety of reasons. Microcapsules can isolate and protect such materials from external suspending media, such as consumer product bases, in which they may be incompatible or unstable. They are also used to assist in the deposition of benefit agents onto substrates, such as skin or hair, or also fabrics or hard household surfaces. They can also act as a means of controlling the spatio-temporal release of a benefit agent.

[0007] A wide variety of encapsulating media as well as benefit agents suitable for the preparation of encapsulated compositions has been proposed in the prior art. Such encapsulating media include synthetic resins made from polyamides, polyureas, polyurethanes, polyacrylates, melamine-

[0008] 31455 PCT derived resins, or mixtures thereof. Encapsulated benefit agent compositions are typically prepared in the form of aqueous slurries.

[0009] Consumers are increasingly concerned about using materials obtained from non-renewable sources, such as synthetic petrochemicals, as well as about the processes for manufacturing the consumer products. The “clean label” concept is one of the biggest trends of the decade. The term itself has many definitions including sustainable, naturally sourced or bio-based and biodegradable ingredients as well as minimal processing and impact on the environment. Nevertheless, it is generally difficult to use natural materials or materials derived from nature to satisfy the requirements for suitable encapsulation compositions. Bio-based and biodegradable ingredients for customer formulations must provide a unique combination of performance and sustainability, so consumers feel confident in the safety and efficacy of these ingredients.

[0010] WO 2019 / 121738 A1 discloses core-shell microcapsules comprising a core containing a functional ingredient and a shell surrounding said core, the shell comprising a thermosetting resin formed by the reaction of shell-forming monomers comprising a polyamine and a polyfunctional acrylate, however the document was not concerned with the biodegradability of the microcapsule composition.

[0011] There is still a need to provide core-shell microcapsule compositions, wherein the shell comprises a resin formed by the conjugate addition of a Michael donor to a Michael acceptor, which are sustainable, comprise increased levels of natural materials and have good predicted biodegradability.

[0012] SUMMARY OF THE INVENTION

[0013] In a first aspect, the invention provides a microcapsule composition comprising at least one coreshell microcapsule, wherein the at least one core-shell microcapsule comprises a core comprising at least one benefit agent and a shell surrounding the core, wherein the shell comprises a resin formed by the reaction of: a Michael acceptor which is the reaction product of a biodegradable polyester polyol with an a,[3-unsaturated acid chloride; and a Michael donor comprising at least two nucleophilic moieties selected from the group consisting of a nitrogen nucleophile, a sulfur nucleophile, an oxygen nucleophile, a carbon nucleophile, a phosphorus nucleophile, and mixtures thereof, which are capable to react with the acrylic double bond of the Michael acceptor.

[0014] 31455 PCT In a second aspect, a method for preparing the microcapsule composition as described herein is provided.

[0015] In a further aspect, it is provided the use of a microcapsule composition as described herein to enhance the performance of a benefit agent in a consumer product.

[0016] The invention further provides a consumer product comprising a microcapsule composition as described herein.

[0017] BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figure 1 shows a comparison between the1H NMR (CDCI3) spectra of poly(caprolactone) triol and poly(caprolactone) triacrylate.

[0019] Figure 2 shows a comparison between the1H NMR (CDCI3) spectra of a polycarbonate diol and a polycarbonate diacrylate.

[0020] Figure 3 shows a comparison between the1H NMR (CDCI3) spectra of castor oil and acrylated castor oil.

[0021] Figure 4 shows an example of a microscope image of a microcapsule composition prepared according to Example 4.

[0022] Figure 5 shows examples of microscope images of microcapsule compositions prepared according to Example 5.

[0023] DEFINITIONS

[0024] The term “benefit agent” refers to any substance which, when added to a product, may improve the perception of this product by a consumer or may enhance the action of this product in an application. Examples of benefit agents include perfume / fragrance ingredients, flavor ingredients, cosmetic ingredients, bioactive agents (such as bactericides, insect repellents and pheromones), substrate enhancers (such as silicones and brighteners), enzymes, dyes, pigments and nutraceuticals.

[0025] The term “microcapsules” refers to capsules of sizes ranging from 0.1 pm to 500 pm, preferably from 10 pm to 150 pm.

[0026] Polyols are alcohols with more than one hydroxyl group.

[0027] 31455 PCT An ester residue is an organic moiety that comprises at least one ester functionality.

[0028] A carbonate residue is an organic moiety comprising at least one organic carbonate functionality.

[0029] The term “bio-based” relates to the origin of a material and refers to materials intentionally made from substances derived from living (or once-living) organisms, as opposed to petroleum-derived materials. The definition includes both natural materials, such as naturally-extracted proteins and polysaccharides, and materials that have undergone some degree of processing, such as cellulose fibers.

[0030] “Biodegradable” materials are defined as materials whose physical and chemical properties undergo deterioration and completely degrade when exposed to the environment. This property, therefore, relates to the end-of-life of the material. Bio-based materials can be biodegradable or non-degradable. Similarly, while many bio-based materials are biodegradable (e.g., starch), not all biodegradable materials are bio-based.

[0031] In context of the present invention, a “biodegradable” ingredient, or a “biodegradable" material in general, for instance a shell material, is a material which meets the pass criteria for “inherently biodegradable” and / or “readily biodegradable” in at least one OECD biodegradation study. In order to avoid any ambiguity, this means that if an ingredient passes one test but fails one or more other ones, the pass result overrules the other test results.

[0032] In the context of the present invention, the pass criteria for “readily biodegradable” are assessed according to OECD Method 301 F, which refers to manometric respirometry. In this method the pass level for “ready biodegradability” is to reach 60 % of theoretical oxygen demand and / or chemical oxygen demand. This pass value has to be reached in a 10-day window within the 28- day period of the test. The 10-day window begins when the degree of biodegradation has reached 10% of theoretical oxygen demand and / or chemical oxygen demand and must end before day 28 of the test. Given a positive result in a test of ready biodegradability, it may be assumed that the chemical will undergo rapid and ultimate biodegradation in the environment (Introduction to the OECD Guidelines for the Testing of Chemicals, Section 3, Part 1 : Principles and Strategies Related to the Testing of Degradation of Organic Chemicals; Adopted: July 2003).

[0033] A Michael donor is a nucleophilic compound that donates an electron pair to an a,[3-unsaturated carbonyl compound (an electrophile, Michael acceptor) to form a chemical bond at the [3-carbon of the Michael acceptor. The nucleophile compound may be a nitrogen nucleophile, sulfur

[0034] 31455 PCT nucleophile, oxygen nucleophile, carbon nucleophile, phosphorus nucleophile, and mixtures thereof.

[0035] DETAILED DESCRIPTION

[0036] Preferred and / or optional features of the invention will now be set out. Any aspect of the invention may be combined with any other aspect of the invention unless the context demands otherwise. Any of the preferred or optional features of any aspect may be combined, singly or in combination, with any aspect of the invention, as well as with any other preferred or optional features, unless the context demands otherwise.

[0037] The addition reaction between a Michael donor and an a,[3-unsaturated carbonyl compound (a Michael acceptor) has been employed for the generation of microcapsule shells comprising poly [3-amino-ester (Aza-Michael reaction) or poly [3-thio-ester (Thio-Michael reaction) moieties. However, the reagents used were generally not bio-based and the resulting resins do not show biodegradability as expected.

[0038] The applicant has surprisingly and unexpectedly found that core-shell microcapsules comprising a core comprising at least one benefit agent and a shell surrounding the core, wherein the shell comprises a resin formed by the reaction of: a Michael acceptor which is the reaction product of a biodegradable polyester polyol with an a,[3-unsaturated acid chloride; and a Michael donor comprising at least two nucleophilic moieties selected from the group consisting of a nitrogen nucleophile, a sulfur nucleophile, an oxygen nucleophile, a carbon nucleophile, a phosphorus nucleophile, and mixtures thereof, which are capable to react with the acrylic double bond of the Michael acceptor can be prepared. The microcapsules show good encapsulation efficiency. Due to the structure of the shell involving ester moieties, the microcapsule composition has a high predicted biodegradability.

[0039] Therefore, the present invention relates to a microcapsule composition comprising at least one core-shell microcapsule, wherein the at least one core-shell microcapsule comprises a core comprising at least one benefit agent and a shell surrounding the core, wherein the shell comprises a resin formed by the reaction of:

[0040] 31455 PCT a Michael acceptor which is the reaction product of a biodegradable polyester polyol with an a,[3-unsaturated acid chloride; and a Michael donor comprising at least two nucleophilic moieties selected from the group consisting of a nitrogen nucleophile, a sulfur nucleophile, an oxygen nucleophile, a carbon nucleophile, a phosphorus nucleophile, and mixtures thereof, which are capable to react with the acrylic double bond of the Michael acceptor.

[0041] Michael acceptor

[0042] Michael acceptors which have been employed so far in core-shell microencapsulation are of the general Formula I,

[0043] R{0-C(=0)C(=CH2)RI]

[0044] Formula I wherein Ri is H or acetyl; and the polyalcohol R(OH)nis trimethylolpropane, pentaerythritol, dipentaerythritol, 1 ,4-butanediol, ethylene glycol, hexane 1 ,6-diol, 1 ,4-phenylenedimethanol, phloroglucinol; or they are polyacrylates such as ((2,4,6-trioxocyclohexane-1 ,3,5-triyl)tris(oxy))tris(ethane-2,1-diyl) triacrylate (TOCTA), tris(2-acryloyloxyethyl) isocyanurate, 1 ,3,5-triacryloylhexahydro-1 ,3,5- triazine (TAHHT) or POSS@octa(acrylate).

[0045] These compounds are generally not bio-based and / or biodegradable.

[0046] The applicant has surprisingly and unexpectedly found that Michael acceptors which are the reaction product of a biodegradable polyester polyol with an a,[3-unsaturated acid chloride are suitable to generate core-shell microcapsules with good predicted biodegradability.

[0047] Such Michael acceptors may have the general Formula II or general Formula III residue-C(=O)C(=CR3R4)R2]

[0048] Formula II

[0049] R2(R3R4C=)C(O=)C-carbonate residue-C(=O)C(=CR3R4)R2

[0050] 31455 PCT Formula III wherein R(OH)nis a polyalcohol, n = 2 to 10, preferably 2 to 8, more preferably, 2 to 6, such as 2, 3, 4, 5 or 6; and

[0051] R2, R3 and R4are each independently H, C1-C5 alkyl or C1-C3 acyl residues, preferably R2, R3 and R4are each independently H;

[0052] Such compounds are either commercially available or are the reaction product of a biodegradable polyester polyol with an a,[3-unsaturated acid chloride. In one embodiment, R2is H.

[0053] Polyester polyol

[0054] Polyester or polycarbonate-based polymeric materials are known to be generally biodegradable. Therefore, use of such materials in the shell of core-shell microcapsules is very desirable in order to improve the overall biodegradability of the microcapsule compositions.

[0055] Polyester polyols are compounds comprising a plurality of both carboxylic acid ester / carbonate groups and hydroxyl groups. Their backbone may comprise aromatic, aliphatic or mixed aliphatic- aromatic moieties.

[0056] In one embodiment, the polyester polyols are aliphatic. These polyester polyols have the advantage of being highly biodegradable.

[0057] The polyester polyols used in the present invention may be selected form the group consisting of polylactone polyols, polycarbonate polyols, triglycerides of hydroxycarboxylic acids, preferably fatty acids, and mixtures thereof.

[0058] The polyester polyols used in the present invention may be commercially available or they may be generated by synthesis. Generation of suitable polyester polyols may involve the following processes: (i) ring-opening polymerization of cyclic monomers such as lactones, cyclic diesters, cyclic carbonates or cyclic ketene acetals; and / or (ii) condensation of hydroxycarboxylic acid / anhydride moieties with polyols, or self-condensation of polyhydroxyacids.

[0059] The polyols from which the polyester polyols of the present invention are derived may be aliphatic or aromatic.

[0060] 31455 PCT In one embodiment, the polyols have a relatively low molecular weight of below about 200 Da, optionally below about 155 Da, optionally below about 140 Da.

[0061] Examples of such polyols include ethylene glycol, diethyleneglycol, propylene glycol, butylene glycol, 2-methyl-1 ,3-propane diol, trimethylolmethane (TMM), neopentyl glycol, trimethylolpropane (TMP), phloroglucinol, pentaerythritol, dipentaetrythritol, sugar alcohols of formula (CH2OH)n, wherein n = 3 to 7, such as glycerol, erythritol, xylitol, sorbitol, or mixtures thereof. In one embodiment, the polyol is trimethylolpropane (TMP) or glycerol.

[0062] Examples of polylactones from which the polyester polyols of the present invention may be derived include propiolactone, poly(dioxanone), poly(butyrolactone)s (11- and y-), poly(valerolactone)s (5- and y-), poly(caprolactone)s (E-, 5- and y-), poly(decalactone)s (5- and y-), ambretollide, ethylene brassylate, and mixtures or copolymers thereof. In one embodiment, the polylactone is poly(E- caprolactone) or poly(5-decalactone).

[0063] The polyester polyol derived from the polyols and polylactones described hereinabove (polylactone polyols) can be produced with narrow molecular weight distributions, which is an advantage, for example in terms of mechanical properties of the resulting core-shell microcapsules.

[0064] In one embodiment, the polylactone polyols include polycaprolactone polyol, such as polycaprolactone diol, polycaprolactone triol, which are both commercially available and polydecalactone polyol, such as polydecalactone triol.

[0065] In one embodiment, the polylactone polyol is polycaprolactone triol. In one embodiment, the polycaprolactone triol has a general formula of C2H5C[CH2O[CO(CH2)5O]nH]3, optionally with molecular weight of about 300 Da.

[0066] Ring opening polymerization of cyclic ketene acetals may also lead to polylactones. Examples of cyclic ketene acetals from which the polyester polyols of the present invention may be derived include 2-methylene-1 ,3-dioxepane, 2,5-methylene-1 ,3-dioxane, 4,7-dimethyl-2-methylene-1 ,3- dioxepane, 2-methylene-4-hexyl / decyl-1 ,3-dioalane and 2-methylene-1,3-dioxalane.

[0067] Likewise, ring opening polymerization of cyclic diesters may lead to polyester polyols. Examples of cyclic diesters from which the polyester polyols of the present invention may be derived include poly(glycolide)s, poly(lactide)s, poly(dioxanone)s and mixtures or copolymers thereof.

[0068] 31455 PCT Polyester polyols may also be obtained by self-polymerization of polyhydroxyacids. Examples of polyhydroxyacids from which the polyester polyols of the present invention may be derived include a-hydroxy acids such as poly(lactic acid) (PLA), poly(glycolic acid) (PGA), poly(lactic-co-mandelic acid), poly(lactic-co-phenyllactic acid), poly (lactic-co-glycolic acid) and mixtures or copolymers thereof; [3-hydroxy acids such as poly (3-hydroxybutyrate), poly(3-hydroxybutyrate-co-3- hydroxyvalerate) and poly(3-hydroxybutyrate-co-4-hydroxybutyrate) copolymers; and co-hydroxy acids.

[0069] Examples of polyester polyol derived from the polyols and polylactones, the cyclic diesters and / or the polyhydroxacids described hereinabove include block copolymers such as poly(decalactone)- poly(L-lactide) copolymers.

[0070] Examples of cyclic carbonates from which the polyester polyols of the present invention may be derived include ethylene carbonate, propylene carbonate and trimethylene carbonate. Ring opening polymerization of these compounds leads to polycarbonates. Therefore, examples of suitable poly(carbonates) include polyethylene carbonate, poly(trimethylene carbonate) (TMC) and polypropylene carbonate. Advantageously, poly(trimethylene carbonate) (TMC) is biodegradable and is produced with low polydispersity.

[0071] In one embodiment, the polycarbonate polyols suitable for the present invention include poly carbonate diols such as 1 ,6-hexanediol polycarbonate diol, or the commercially available Converge diol, which is derived from polypropylene carbonate; or polycarbonate triols such as poly(trimethylene carbonate) triol.

[0072] In one embodiment, the poly carbonate polyol is sold under the tradename Converge Polyol and optionally has a molecular weight of about 2000 Da.

[0073] Polyester polyols may also be obtained by condensation of hydroxycarboxylic acids with polyols. Examples of hydroxycarboxylic acids from which the polyester polyols of the present invention may be derived include hydroxy- or epoxy-functionalized fatty acids, such as ricinoleic acid, 9,10- dihydroxystearic acid; glycolic acid, lactic acid, tartaric acid or citric acid.

[0074] In one embodiment, the polyester polyols are triglycerides of hydroxycarboxylic acids, such as triester of glycerol and ricinoleic acid or epoxidized linolein. In one embodiment, the polyester polyols are commercially available as castor oil or soybean oil. a, / 3-Unsaturated Acid Chloride

[0075] 31455 PCT a,[3-unsaturated acid chlorides have the general formula CI-C(=O)C(=CR3R4)R2, wherein R2-R4 are each independently H or an alkyl.

[0076] The reaction of a,[3-unsaturated acid chloride with alcohols, optionally in the presence of tertiary amines, is known to lead to acrylate derivatives, wherein the hydroxyl functionality of the alcohols is acylated with the a,[3-unsaturated acyl group.

[0077] The Michael acceptors of the present invention may be the reaction product of biodegradable polyester polyol as described hereinabove with an a,[3-unsaturated acid chloride.

[0078] Therefore, the Michael acceptors of the present invention may have the general Formula II or general Formula III

[0079] Formula II

[0080] R2(R3R4C=)C(O=)C-carbonate residue-C(=O)C(=CR3R4)R2

[0081] Formula III wherein R(OH)nis a polyalcohol, n = 2 to 10, preferably 2 to 8, more preferably, 2 to 6, such as 2, 3, 4, 5 or 6; and

[0082] R2, R3and R4 are each independently H, C1-C5 alkyl or Ci-C3acyl residues; the ester residue and carbonate residue are derived from the polyester polyol as described hereinabove.

[0083] In one embodiment, R2 is H.

[0084] In one embodiment, R2, R3and R4 are each independently H, therefore the a,[3-unsaturated acid chloride is acryloyl chloride.

[0085] In one embodiment, R2= R3= H and R4= C(O)CI, therefore the a,[3-unsaturated acid chloride is fumaryl chloride or maleoyl chloride.

[0086] 31455 PCT In one embodiment, R2= methyl and R3= R4 = H, therefore the a,[3-unsaturated acid chloride is methacryloyl chloride.

[0087] Michael acceptors as described hereinabove may be commercially available or they may be synthesized by the reaction of the polyester polyol as described hereinabove with a,[3-unsaturated acid chlorides as described hereinabove.

[0088] In one embodiment, the Michael acceptor is commercially available poly(caprolactone) trimethacrylate.

[0089] In one embodiment, the Michael acceptor is poly(caprolactone) triacrylate. In one embodiment, the poly(caprolactone) triacrylate is obtained by the reaction of poly(caprolactone) triol as described herein above with acryloyl chloride. In one embodiment, the poly(caprolactone) triol is commercially available and it optionally has a molecular weight of about 300 Da.

[0090] In one embodiment, the Michael acceptor is Converge diacrylate. In one embodiment, the Converge diacrylate is obtained by the reaction of Converge diol as described herein above with acryloyl chloride. In one embodiment, the Converge diol is commercially available and it optionally has a molecular weight of about 2000 Da.

[0091] In one embodiment, the Michael acceptor is acrylated triricinolein. In one embodiment, the Michael acceptor is acrylated castor oil. In one embodiment, the acrylated castor oil is obtained by the reaction of castor oil as described herein above with acryloyl chloride. In one embodiment, the castor oil is commercially available and it optionally has a molecular weight of about 925 Da.

[0092] Michael donor

[0093] Any Michael donor comprising at least two nucleophilic moieties can be used in the present invention. A nucleophilic moiety form bonds by donating an electron pair to an electrophilic moiety such as the acrylic double bone of the Michael acceptor. The nucleophilic groups of the Michael donor must be capable to react with the acrylic double bond of the Michael acceptor as described hereinabove.

[0094] In one embodiment, the Michael donor comprises at least two nucleophilic moieties selected from the group consisting of a nitrogen nucleophile, a sulfur nucleophile, an oxygen nucleophile, a carbon nucleophile, a phosphorus nucleophile, and mixtures thereof.

[0095] 31455 PCT Nitrogen nucleophiles may have at least one functional group selected from the group consisting of ammonia, azides, amines, nitrites, hydroxylamine, hydrazine, carbazide, phenylhydrazine, semicarbazide, amide, and mixtures thereof.

[0096] Sulfur nucleophiles may have at least one functional group selected from the group consisting of hydrogen sulfide and its salts, thiols, thiolate anions, anions of thiolcarboxylic acids, anions of dithiocarbonates and dithiocarbamates and mixtures thereof.

[0097] Oxygen nucleophiles may have at least one functional group selected from the group consisting of water, hydroxide anion, alcohols, alkoxide anions, carboxylate anions, carbonates, sulfonate, sulfate, sodium phosphates, sodium silicates, borax, sodium tetraborate, and mixtures thereof.

[0098] Carbon nucleophiles may have at least one functional group selected from the group consisting of enols carbon nucleophiles, malonate and acetoacetate.

[0099] Phosphorus nucleophiles may have at least one functional group selected from the group consisting of phosphine, phosphite anions and mixtures thereof.

[0100] In one embodiment, the Michael donor is biodegradable, thereby increasing the predicted biodegradability of the core-shell microcapsule composition.

[0101] In one embodiment, the Michael donor is a polyamine, optionally a biodegradable polyamine.

[0102] In one embodiment, the polyamine is aliphatic, cyclic or aromatic.

[0103] In one embodiment, the polyamine is commercially available, such as ethylene diamine, butane- 1 ,4-diamine, hexamethylenediamine (HMDA), dimethyl hexane diamine, diethylene triamine, diaminooctane, tris(2-aminoethyl)amine (TREN), pentaethylenehexamine (PEHA), polyethyleneimine, 4,4’-trimetylene piperidine (TMPP), isophorondiamine (I PDA), meta- xylylenediamine, 1 ,3-phenylenediamine, polypropylene glycol) bis(2-aminopropyl ether), poly(ethylene glycol) bis(3-aminopropyl) terminated, Jeffamines such as Jeffamine diamine or triamines.

[0104] In one embodiment, the polyamine is generated by synthesis, such as trimethylolpropane tri-beta hydroxylamine.

[0105] In one embodiment, the Michael donor is an aminoacid-containing reagent, which is generally biosourced and is believed to lead to increased biodegradability of the resulting core-shell

[0106] 31455 PCT microcapsule composition. In one embodiment, the Michael donor is an aminoacid or a homopolypeptide.

[0107] In one embodiment, the aminoacid is selected from the group consisting of cysteine, serine, arginine, lysine, histidine and mixtures thereof.

[0108] In one embodiment, the Michael donor is lysine, poly-lysine or mixtures thereof.

[0109] Microcapsule composition

[0110] The microcapsule composition of the present invention comprises core-shell microcapsules, wherein the core comprises at least one benefit agent and the shell comprises a resin formed by the reaction of: a Michael acceptor which is the reaction product of a biodegradable polyester polyol with an a,[3-unsaturated acid chloride as described hereinabove; and a Michael donor comprising at least two nucleophilic moieties selected from the group consisting of a nitrogen nucleophile, a sulfur nucleophile, an oxygen nucleophile, a carbon nucleophile, a phosphorus nucleophile, and mixtures thereof, which are capable to react with the acrylic double bond of the Michael acceptor, as described hereinabove.

[0111] The Michael polymerization reactions of the present invention result in formation of networks of oligo- or polymeric products which are capable of forming a shell surrounding benefit-agent containing oil droplets.

[0112] In one embodiment, the microcapsule composition is in the form of an aqueous slurry.

[0113] In one embodiment, the volume average size (Dv(50)) of the microcapsules can be from 1 to 500 pm, optionally from 1 to 100 pm, preferably from 5 to 80 pm, even more preferably from 10 to 70 pm.

[0114] In one embodiment, the slurry may be dried to yield the encapsulated composition in a dry powder form.

[0115] Benefit Agent

[0116] 31455 PCT Suitable benefit agents to be incorporated into the core of the core-shell microcapsules of the present invention include perfume / fragrance ingredients, flavor ingredients, cosmetic ingredients, bioactive agents (such as bactericides, insect repellents and pheromones), substrate enhancers (such as silicones and brighteners), enzymes, dyes, pigments and nutraceuticals.

[0117] In one embodiment, the at least one benefit agent may be at least one fragrance ingredient. A comprehensive list of fragrance ingredients that may be encapsulated in accordance with the present invention may be found in the perfumery literature, for example “Perfume & Flavor Chemicals”, S. Arctander (Allured Publishing, 1994). Encapsulated fragrance ingredients according to the present invention preferably comprise fragrance ingredients selected from the group consisting of 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); ALDEHYDE C 10 DECYLIC (decanal); ALDEHYDE C 11 MOA (2-methyldecanal); ALDEHYDE C 11 UNDECYLENIC (undec-10-enal); ALDEHYDE C 110 UNDECYLIC (undecanal); ALDEHYDE C 12 LAURIC (dodecanal); ALDEHYDE C 12 MNA PURE (2-methylundecanal); ALDEHYDE C 8 OCTYLIC (octanal); ALDEHYDE C 9 ISONONYLIC (3,5,5-trimethylhexanal); ALDEHYDE C 9 NONYLIC FOOD GRADE (nonanal); ALDEHYDE C 90 NONENYLIC ((E)-non-2-enal); ALDEHYDE ISO C 11 ((E)-undec-9-enal); ALDEHYDE MANDARINE ((E)-dodec-2-enal); ALLYL AMYL GLYCOLATE (prop-2-enyl 2-(3-methylbutoxy)acetate); ALLYL CAPROATE (prop-2-enyl hexanoate); ALLYL CYCLOHEXYL PROPIONATE (prop-2-enyl 3-cyclohexylpropanoate); ALLYL OENANTHATE (prop-2-enyl heptanoate); AMBER CORE1-((2-(tert-butyl)cyclohexyl)oxy)butan-2- olAMBERKETAL (3,8,8, 11a-tetramethyldodecahydro-1 H-3,5a-epoxynaphtho[2,1-c]oxepine); AMBERMAX (1 , 3, 4,5,6, 7-hexahydro-. beta. ,1 ,1 ,5, 5-pentamethyl-2H-2,4a-Methanonaphthalene-8- ethanol); AMBRETTOLIDE ((Z)-oxacycloheptadec-10-en-2-one); AMBROFIX ((3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1 H- benzo[e][1]benzofuran); AMYL BUTYRATE (pentyl butanoate); AMYL CINNAMIC ALDEHYDE ((Z)-2-benzylideneheptanal); AMYL SALICYLATE (pentyl 2-hydroxybenzoate); ANETHOLE SYNTHETIC ((E)-1-methoxy-4-(prop-1-en-1-yl)benzene); ANISYL ACETATE (4-methoxybenzyl acetate); APHERMATE (1-(3,3-dimethylcyclohexyl)ethyl formate); AUBEPINE PARA CRESOL (4- methoxybenzaldehyde); AURANTIOL ((E)-methyl 2-((7-hydroxy-3,7- dimethyloctylidene)amino)benzoate); BELAMBRE ((1 R,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); BERRYFLOR (ethyl 6-acetoxyhexanoate); BICYCLO NONALACTONE (octahydro-2H-chromen-

[0118] 31455 PCT 2-one); BOISAMBRENE FORTE ((ethoxymethoxy)cyclododecane); BOISIRIS ((1S,2R,5R)-2- ethoxy-2,6,6-trimethyl-9-methylenebicyclo[3.3.1]nonane); BORNEOL CRYSTALS ((1S,2S,4S)- 1 ,7,7-trimethylbicyclo[2.2.1]heptan-2-ol); BORNYL ACETATE ((2S,4S)-1 ,7,7- trimethylbicyclo[2.2.1]heptan-2-yl acetate); BOURGEONAL (3-(4-(tert-butyl)phenyl)propanal); BUTYL BUTYRO LACTATE (1 -butoxy- 1-oxopropan-2-yl butanoate); BUTYL CYCLOHEXYL ACETATE PARA (4-(tert-butyl)cyclohexyl acetate); BUTYL QUINOLINE SECONDARY (2-(2- methylpropyl)quinoline); CAMPHOR SYNTHETIC ((1S,4S)-1 ,7,7-trimethylbicyclo[2.2.1]heptan-2- one); CARVACROL (5-isopropyl-2-methylphenol); CARVONE LAEVO ((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-1 H-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-1 H-5,8a-methanoazulene); CEDRYL ACETATE ((1S,6R,8aR)-1 ,4,4,6-tetramethyloctahydro-1 H-5,8a-methanoazulen-6-yl acetate); CEDRYL METHYL ETHER ((1 R,6S,8aS)-6-methoxy-1 ,4,4,6-tetramethyloctahydro-1 H-5,8a- methanoazulene); CETONE V ((E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)hepta-1 ,6-dien-3-one); CINNAMIC ALCOHOL SYNTHETIC ((E)-3-phenylprop-2-en-1-ol); CINNAMIC ALDEHYDE ((2E)-

[0119] 3-phenylprop-2-enal); CINNAMYL ACETATE ((E)-3-phenylprop-2-en-1-yl acetate); CIS

[0120] JASMONE ((Z)-3-methyl-2-(pent-2-en-1-yl)cyclopent-2-enone); CIS-3-HEXENOL ((Z)-hex-3-en- 1-ol); CITRAL TECH ((E)-3,7-dimethylocta-2,6-dienal); CITRATHAL R ((Z)-1 ,1-diethoxy-3,7- dimethylocta-2,6-diene); CITRONELLAL (3,7-dimethyloct-6-enal); CITRONELLOL EXTRA (3,7- dimethyloct-6-en-1-ol); CITRONELLYL ACETATE (3,7-dimethyloct-6-en-1-yl acetate); CITRONELLYL FORMATE (3,7-dimethyloct-6-en-1-yl formate); CITRONELLYL NITRILE (3,7- dimethyloct-6-enenitrile); CLONAL (dodecanenitrile); CORANOL (4-cyclohexyl-2-methylbutan-2- ol); COSMONE ((Z)-3-methylcyclotetradec-5-enone); COUMARIN PURE CRYSTALS (2H- chromen-2-one); CRESYL ACETATE PARA ((4-methylphenyl) acetate); CRESYL METHYL ETHER PARA (1-methoxy-4-methylbenzene); CUMIN NITRILE (4-isopropylbenzonitrile); CYCLAL C (2,4-dimethylcyclohex-3-ene-1-carbaldehyde); CYCLAMEN ALDEHYDE EXTRA (3- (4-isopropylphenyl)-2-methylpropanal); CYCLOGALBANATE (allyl 2-(cyclohexyloxy)acetate); CYCLOHEXYL ETHYL ACETATE (2-cyclohexylethyl acetate); CYCLOHEXYL SALICYLATE (cyclohexyl 2-hydroxybenzoate); CYCLOMYRAL (8,8-dimethyl-1 , 2, 3, 4, 5, 6,7,8- octahydronaphthalene-2-carbaldehyde); CYMENE PARA (1-methyl-4-propan-2-ylbenzene); DAMASCENONE ((E)-1-(2,6,6-trimethylcyclohexa-1 ,3-dien-1-yl)but-2-en-1-one); DAMASCONE ALPHA ((E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one); DAMASCONE DELTA (1- (2,6,6-trimethyl-1-cyclohex-3-enyl)but-2-en-1-one); DECALACTONE GAMMA (5-hexyloxolan-2- one); DECENAL-4-TRANS ((E)-dec-4-enal); DELPHONE (2-pentylcyclopentanone); DELTA-3

[0121] 31455 PCT CARENE ((1S,6S)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene); DI HEXYL FUMARATE (dihexyl-but- 2-enedioate); DIHYDRO ANETHOLE (1-methoxy-4-propylbenzene); DIHYDRO JASMONE (3- methyl-2-pentylcyclopent-2-enone); DI HYDRO MYRCENOL (2,6-dimethyloct-7-en-2-ol); DIMETHYL ANTHRANILATE (methyl 2-(methylamino)benzoate); DIMETHYL BENZYL CARBINOL (2-methyl-1-phenylpropan-2-ol); DIMETHYL BENZYL CARBINYL ACETATE (2- methyl-1-phenylpropan-2-yl acetate); DIMETHYL BENZYL CARBINYL BUTYRATE (2-methyl-1- phenylpropan-2-yl butanoate); DIMETHYL OCTENONE (4,7-dimethyloct-6-en-3-one); DIMETOL (2,6-dimethylheptan-2-ol); DI PENTENE (1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene); DIPHENYL OXIDE (oxydi benzene); DODECALACTONE DELTA (6-heptyltetrahydro-2H-pyran-2-one); DODECALACTONE GAMMA (5-octyloxolan-2-one); DODECENAL ((E)-dodec-2-enal); DUPICAL ((E)-4-((3aS,7aS)-hexahydro-1 H-4,7-methanoinden-5(6H)-ylidene)butanal); EBANOL ((E)-3- methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-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 HEXANOATE (ethyl hexanoate); ETHYL LINALOOL ((E)-3,7-dimethylnona-1 ,6-dien-3-ol); ETHYL LINALYL ACETATE ((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-methylbutanoate); ETHYL OCTANOATE (ethyl octanoate); ETHYL OENANTHATE (ethyl heptanoate); ETHYL PHENYL GLYCIDATE (ethyl 3- phenyloxirane-2-carboxylate); ETHYL SAFRANATE (ethyl 2,6,6-trimethylcyclohexa-1 ,3-diene-1- carboxylate); ETHYL VANILLIN (3-ethoxy-4-hydroxybenzaldehyde); ETHYLENE BRASSYLATE (1 ,4-dioxacycloheptadecane-5, 17-dione); EUCALYPTOL ((1 s,4s)-1 ,3,3-trimethyl-2- oxabicyclo[2.2.2]octane); EUGENOL (4-allyl-2-methoxyphenol); EVERNYL (methyl 2,4- dihydroxy-3,6-dimethylbenzoate); FENCHYL ACETATE ((2S)-1,3,3-trimethylbicyclo[2.2.1]heptan- 2-yl acetate); FENCHYL ALCOHOL ((1S,2R,4R)-1 ,3,3-trimethylbicyclo[2.2.1]heptan-2-ol); FENNALDEHYDE (3-(4-methoxyphenyl)-2-methylpropanal); FIXAMBRENE (3a, 6, 6,9a- tetramethyldodecahydronaphtho[2,1-b]furan); FIXOLIDE (1-(3, 5, 5,6,8, 8-hexamethyl-5, 6,7,8- tetrahydronaphthalen-2-yl)ethanone); FLORALOZONE (3-(4-ethylphenyl)-2,2-dimethylpropanal); FLORHYDRAL (3-(3-isopropylphenyl)butanal); FLORIDILE ((E)-undec-9-enenitrile); FLOROCYCLENE ((3aR,6S,7aS)-3a,4,5,6,7,7a-hexahydro-1 H-4,7-methanoinden-6-yl propanoate); FLOROPAL (2,4,6-trimethyl-4-phenyl-1 ,3-dioxane); FLOROSA HC (tetra hydro-4- methyl-2-(2-methylpropyl)-2H-pyran-4-ol); FRESKOMENTHE (2-(sec-butyl)cyclohexanone); FRUCTONE (ethyl 2-(2-methyl-1 ,3-dioxolan-2-yl)acetate); FRUITATE ((3aS,4S,7R,7aS)-ethyl octahydro-1 H-4,7-methanoindene-3a-carboxylate); FRUTONILE (2-methyldecanenitrile); GALBANONE PURE (1-(5,5-dimethylcyclohex-1-en-1-yl)pent-4-en-1-one); GARDENOL (1-

[0122] 31455 PCT phenylethyl acetate); GARDOCYCLENE ((3aR,6S,7aS)-3a,4,5,6,7,7a-hexahydro-1 H-4,7- methanoinden-6-yl 2-methyl propanoate); 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); GIVESCONE (ethyl 2-ethyl-6,6- dimethylcyclohex-2-enecarboxylate); HABANOLIDE ((E)-oxacyclohexadec-12-en-2-one); HEDIONE (methyl 3-oxo-2-pentylcyclopentaneacetate); HELIOTROPINE CRYSTALS (benzo[d][1 ,3]dioxole-5-carbaldehyde); HERBANATE ((2S)-ethyl 3-isopropylbicyclo[2.2.1]hept-5- ene-2-carboxylate); HEXENAL-2-TRANS ((E)-hex-2-enal); HEXENOL-3-CIS ((Z)-hex-3-en-1-ol); HEXENYL-3-CIS ACETATE ((Z)-hex-3-en-1-yl acetate); HEXENYL-3-CIS BUTYRATE ((Z)-hex- 3-en-1-yl butanoate); HEXENYL-3-CIS ISOBUTYRATE ((Z)-hex-3-en-1-yl 2-methylpropanoate); HEXENYL-3-CIS SALICYLATE ((Z)-hex-3-en-1-yl 2-hydroxybenzoate); HEXYL ACETATE (hexyl acetate); HEXYL BENZOATE (hexyl benzoate); HEXYL BUTYRATE (hexyl butanoate); HEXYL CINNAMIC ALDEHYDE ((E)-2-benzylideneoctanal); HEXYL ISOBUTYRATE (hexyl 2- methylpropanoate); HEXYL SALICYLATE (hexyl 2-hydroxybenzoate); HYDROXYCITRON ELLAL (7-hydroxy-3,7-dimethyloctanal); INDOFLOR (4,4a,5,9b-tetrahydroindeno[1 ,2-d][1 ,3]dioxine); INDOLE PURE (1 H-indole); INDOLENE (8,8-di(1 H-indol-3-yl)-2,6-dimethyloctan-2-ol); IONONE BETA ((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one); IRISANTHEME ((E)-3-methyl-4- (2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one); IRISONE ALPHA ((E)-4-(2,6,6- trimethylcyclohex-2-en-1-yl)but-3-en-2-one); IRONE ALPHA ((E)-4-(2,5,6,6-tetramethylcyclohex- 2-en-1-yl)but-3-en-2-one); ISO E SUPER (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 butanoate); ISOBUTYL METHOXY PYRAZINE (2-methylpropyl 3- methoxypyrazine); ISOCYCLOCITRAL (2,4,6-trimethylcyclohex-3-enecarbaldehyde); ISOEUGENOL ((E)-2-methoxy-4-(prop-1-en-1-yl)phenol); ISOJASMONE B 11 (2-hexylcyclopent- 2-en-1-one); ISOMENTHONE DL (2-isopropyl-5-methylcyclohexanone); ISONONYL ACETATE (3,5,5-trimethylhexyl acetate); ISOPROPYL METHYL-2- BUTYRATE (isopropyl 2- methylbutanoate); ISOPROPYL QUINOLINE (6-isopropylquinoline); ISORALDEINE ((E)-3- methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one); JASMACYCLENE ((3aR,6S,7aS)- 3a,4,5,6,7,7a-hexahydro-1 H-4,7-methanoinden-6-yl acetate); JASMONE CIS ((Z)-3-methyl-2- (pent-2-en-1-yl)cyclopent-2-enone); JASMONYL (3-butyl-5-methyltetrahydro-2H-pyran-4-yl acetate); JASMOPYRANE FORTE (3-pentyltetrahydro-2H-pyran-4-yl acetate); JAVANOL ((1- methyl-2-((1 ,2,2-trimethylbicyclo[3.1 ,0]hexan-3-yl)methyl)cyclopropyl)methanol); KOAVONE ((Z)- 3,4,5,6,6-pentamethylhept-3-en-2-one); LAITONE (8-isopropyl-1-oxaspiro[4.5]decan-2-one);

[0123] 31455 PCT LEAF ACETAL ((Z)-1-(1-ethoxyethoxy)hex-3-ene); LEMONILE ((2E,6Z)-3,7-dimethylnona-2,6- dienenitrile); LIFFAROME ((Z)-hex-3-en-1-yl methyl carbonate); LILIAL (3-(4-(tert-butyl)phenyl)-2- methylpropanal); 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); MALTYL ISOBUTYRATE (2-methyl-4-oxo-4H-pyran-3-yl 2-methylpropanoate); MANZANATE (ethyl 2-methylpentanoate); MAYOL ((4-isopropylcyclohexyl)methanol); MEFROSOL (3-methyl-5-phenylpentan-1-ol); MELONAL (2,6-dimethylhept-5-enal); MERCAPTO- 8-METHANE-3-ONE (mercapto-para-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-1 H-5,8a-methanoazulen-7-yl)ethanone);

[0124] METHYL CINNAMATE (methyl 3-phenylprop-2-enoate); METHYL DIANTILIS (2-ethoxy-4- (methoxymethyl)phenol); METHYL DI HYDRO ISOJASMONATE (methyl 2-hexyl-3- oxocyclopentane-1 -carboxylate); METHYL HEPTENONE PURE (6-methylhept-5-en-2-one); METHYL LAITONE (8-methyl-1-oxaspiro[4.5]decan-2-one); METHYL NONYL KETONE (undecan-2-one); METHYL OCTYNE CARBONATE (methyl non-2-ynoate); METHYL PAMPLEMOUSSE (6,6-dimethoxy-2,5,5-trimethylhex-2-ene); METHYL SALICYLATE (methyl 2- hydroxybenzoate); MUSCENONE ((Z)-3-methylcyclopentadec-5-enone); MYRALDENE (4-(4- methylpent-3-en-1-yl)cyclohex-3-enecarbaldehyde); MYRCENE (7-methyl-3-methyleneocta-1 ,6- diene); MYSTIKAL (2-methylundecanoic acid); NECTARYL (2-(2-(4-methylcyclohex-3-en-1- yl)propyl)cyclopentanone); NEOBERGAMATE FORTE (2-methyl-6-methyleneoct-7-en-2-yl acetate); NEOCASPIRENE EXTRA (10-isopropyl-2,7-dimethyl-1-oxaspiro[4.5]deca-3,6-diene); NEOFOLIONE ((E)-methyl 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); NEROLIDYLE ((Z)-3,7,11- trimethyldodeca-1 ,6,10-trien-3-yl acetate); NEROLINE CRYSTALS (2-ethoxynaphthalene); NEROLIONE (1-(3-methylbenzofuran-2-yl)ethanone); NERYL ACETATE ((Z)-3,7-dimethylocta- 2,6-dien-1-yl acetate); NIRVANOLIDE ((E)-13-methyloxacyclopentadec-10-en-2-one); NONADIENAL ((2E,6Z)-nona-2,6-dienal); NONADIENOL-2,6 ((2Z,6E)-2,6-nonadien-1-ol); NONADYL (6,8-dimethylnonan-2-ol); NONALACTONE GAMMA (5-pentyloxolan-2-one); NONENAL-6-CIS ((Z)-non-6-enal); NONENOL-6-CIS ((Z)-non-6-en-1-ol); NOPYL ACETATE (2- (6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl acetate); NYMPHEAL (3-(4-(2-methylpropyl)-2- methylphenyl)propanal); OCTALACTONE DELTA (6-propyltetrahydro-2H-pyran-2-one); METHYL HEXYL KETONE (octan-2-one); GRANGER CRYSTALS (1-(2-naphtalenyl)-ethanone); ORIVONE (4-(tert-pentyl)cyclohexanone); PANDANOL ((2-methoxyethyl)benzene); PARA TERT

[0125] 31455 PCT BUTYL CYCLOHEXYL ACETATE (4-(tert-butyl)cyclohexyl acetate); PARADISAMIDE (2-ethyl-N- methyl-N-(m-tolyl)butanamide); PEACH PURE (5-heptyldihydrofuran-2(3H)-one); PELARGENE (2-methyl-4-methylene-6-phenyltetrahydro-2H-pyran); PELARGOL (3,7-dimethyloctan-1-ol); PEONILE (2-cyclohexylidene-2-phenylacetonitrile); PETALIA (2-cyclohexylidene-2-(o- tolyl)acetonitrile); PHARAONE (2-cyclohexylhepta-1 ,6-dien-3-one); PHENOXY ETHYL ISOBUTYRATE (2-(phenoxy)ethyl 2-methylpropanoate); PHENYL ACETALDEHYDE (2-phenyl- ethanal); PHENYL ETHYL ACETATE (2-phenylethyl acetate); PHENYL ETHYL ALCOHOL (2- phenylethanol); PHENYL ETHYL ISOBUTYRATE (2-phenylethyl 2-methylpropanoate); PHENYL ETHYL PHENYL ACETATE (2-phenylethyl 2-phenylacetate); PHENYL PROPYL ALCOHOL (3- phenylpropan-1-ol); PINENE ALPHA (2,6,6-trimethylbicyclo[3.1.1]hept-2-ene); PINENE BETA (6,6-dimethyl-2-methylenebicyclo[3.1 .1]heptane); PINOACETALDEHYDE (3-(6,6- dimethylbicyclo[3.1.1]hept-2-en-2-yl)propanal); PIVAROSE (2,2-dimethyl-2-pheylethyl propanoate); POMAROSE ((2E,5E)-5,6,7-trimethylocta-2,5-dien-4-one); POMELOL (2,4,7- Trimethyl-6-octen-1-ol); PRECYCLEMONE B (1-methyl-4-(4-methylpent-3-en-1-yl)cyclohex-3- enecarbaldehyde); PRENYL ACETATE (3-methylbut-2-en-1-yl acetate); PRUNOLIDE (5- pentyldihydrofuran-2(3H)-one); RADJANOL SUPER ((E)-2-ethyl-4-(2,2,3-trimethylcyclopent-3- en-1-yl)but-2-en-1-ol); RASPBERRY KETONE (4-(4-hydroxyphenyl)butan-2-one); RHUBAFURAN (2,4-dimethyl-4-phenyltetrahydrofuran); ROSACETOL (2,2,2-trichloro-1- phenylethyl acetate); ROSALVA (dec-9-en-1-ol); ROSE OXIDE (4-methyl-2-(2-methylprop-1-en- 1-yl)tetrahydro-2H-pyran); ROSE OXIDE CO (4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H- pyran); ROSYFOLIA (1-methyl-2-(5-methylhex-4-en-2-yl)cyclopropylmethanol); ROSYRANE SUPER (4-methyl-2-phenyl-3,6-dihydro-2H-pyran); SAFRALEINE (2,3,3-trimethyl-1-indanone); SAFRANAL (2,6,6-trimethylcyclohexa-1 ,3-dienecarbaldehyde); SANDALORE EXTRA (3-methyl- 5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol); SCENTAURUS CLEAN (ethyl (Z)-2-acetyl-4- methyltridec-2-enoate); SCENTAURUS JUICY (4-(dodecylthio)-4-methylpentan-2-one); SERENOLIDE (2-(1-(3,3-dimethylcyclohexyl)ethoxy)-2-methylpropyl cyclopropanecarboxylate); SILVANONE SUPRA (cyclopentadecanone, hexadecanolide); SILVIAL (2-methyl-3-[4-(2- methylpropyl)phenyl]propanal); SPIROGALBANONE (1-(spiro[4.5]dec-6-en-7-yl)pent-4-en-1- one); STEMONE ((E)-5-methylheptan-3-one oxime); STYRALLYL ACETATE (1 -phenylethyl acetate); SUPER MUGUET ((E)-6-ethyl-3-methyloct-6-en-1-ol); SYLKOLIDE ((E)-2-((3,5- dimethylhex-3-en-2-yl)oxy)-2-methylpropyl cyclopropanecarboxylate); TERPINENE ALPHA (1- methyl-4-propan-2-ylcyclohexa-1 ,3-diene); TERPINENE GAMMA (1-methyl-4-propan-2- ylcyclohexa-1 ,4-diene); TERPINEOL (2-(4-methylcyclohex-3-en-1-yl)propan-2-ol); TERPINEOL ALPHA (2-(4-methyl-1-cyclohex-3-enyl)propan-2-ol); TERPINEOL PURE (2-(4-methylcyclohex-3-

[0126] 31455 PCT en-1-yl)propan-2-ol); TERPINOLENE (1-methyl-4-(propan-2-ylidene)cyclohex-1-ene); TERPINYL ACETATE (2-(4-methyl-1-cyclohex-3-enyl)propan-2-yl acetate); TETRAHYDRO LINALOOL (3,7- dimethyloctan-3-ol); TETRAHYDRO MYRCENOL (2,6-dimethyloctan-2-ol); THIBETOLIDE (oxacyclohexadecan-2-one); THYMOL (2-isopropyl-5-methylphenol); TOSCANOL (1- (cyclopropylmethyl)-4-methoxybenzene); TRICYCLAL (2,4-dimethylcyclohex-3- enecarbaldehyde); TRIDECENE-2-NITRILE ((E)-tridec-2-enenitrile); TRIFERNAL (3- phenylbutanal); TROPIONAL (3-(benzo[d][1 ,3]dioxol-5-yl)-2-methylpropanal); TROPIONAL (3- (benzo[d][1 ,3]dioxol-5-yl)-2-methylpropanal); UNDECATRIENE ((3E,5Z)-undeca-1 ,3,5-triene); UNDECAVERTOL ((E)-4-methyldec-3-en-5-ol); VANILLIN (4-hydroxy-3-methoxybenzaldehyde); VELOUTONE (2,2,5-trimethyl-5-pentylcyclopentanone); VELVIONE ((Z)-cyclohexadec-5-enone); VIOLET NITRILE ((2E,6Z)-nona-2,6-dienenitrile); YARA YARA (2-methoxynaphtalene); ZINARINE (2-(2,4-dimethylcyclohexyl)pyridine; BOIS CEDRE ESS CHINE (cedar wood oil); EUCALYPTUS GLOBULUS ESS CHINA (eucalyptus oil); GALBANUM ESS (galbanum oil); GIROFLE FEUILLES ESS RECT MADAGASCAR (clove oil); LAVANDIN GROSSO OIL FRANCE ORPUR (lavandin oil); MANDARIN OIL WASHED COSMOS (mandarin oil); ORANGE TERPENES (orange terpenes); PATCHOULI ESS INDONESIE (patchouli oil); and YLANG ECO ESSENCE (ylang oil). These fragrance ingredients are particularly suitable for obtaining stable and performing microcapsules, owing to their favorable lipophilicity and olfactive performance.

[0127] In particularly preferred embodiments of the present invention, more than 75 %, preferably more than 80 %, even more preferably more than 85 %, even still more preferably more than 90 %, even yet still more preferably more than 95 %, of the fragrance ingredients are biodegradable and 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); ALDEHYDE C 10 DECYLIC (decanal); ALDEHYDE C 11 UNDECYLENIC (undec-10-enal); ALDEHYDE C 110 UNDECYLIC (undecanal); ALDEHYDE C 12 LAURIC (dodecanal); ALDEHYDE C 12 MNA (2-methylundecanal); ALDEHYDE C 8 OCTYLIC (octanal); CYCLAMEN ALDEHYDE EXTRA (3-(4-isopropylphenyl)-2-methylpropanal); ALDEHYDE ISO C 11 ((E)-undec- 9-enal); ALLYL AMYL GLYCOLATE (prop-2-enyl 2-(3-methylbutoxy)acetate); ALLYL CYCLOHEXYL PROPIONATE (prop-2-enyl 3-cyclohexylpropanoate); ALLYL OENANTHATE (prop-2-enyl heptanoate); AMBRETTOLIDE ((Z)-oxacycloheptadec-10-en-2-one); AMBROFIX ((3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1 H- benzo[e][1]benzofuran); AMYL SALICYLATE (pentyl 2-hydroxybenzoate); AUBEPINE PARA CRESOL (4-methoxybenzaldehyde); BENZYL ACETATE (benzyl acetate); BENZYL SALICYLATE (benzyl 2-hydroxybenzoate); BORNYL ACETATE ((2S,4S)-1 ,7,7-

[0128] 31455 PCT trimethylbicyclo[2.2.1]heptan-2-yl acetate); CARVACROL (5-isopropyl-2-methylphenol); CEDRENE ((1 S,8aR)-1 ,4,4,6-tetramethyl-2,3,3a,4,5,8-hexahydro-1 H-5,8a-methanoazulene); CEDRYL ACETATE ((1S,6R,8aR)-1 ,4,4,6-tetramethyloctahydro-1 H-5,8a-methanoazulen-6-yl acetate); CEDRYL METHYL ETHER ((1 R,6S,8aS)-6-methoxy-1 ,4,4,6-tetramethyloctahydro-1 H- 5,8a-methanoazulene); CITRAL ((E)-3,7-dimethylocta-2,6-dienal); CITRONELLOL (3,7- dimethyloct-6-en-1-ol); CITRONELLYL ACETATE (3,7-dimethyloct-6-en-1-yl acetate); COSMONE ((Z)-3-methylcyclotetradec-5-enone); CRESYL METHYL ETHER PARA (1-methoxy- 4-methylbenzene); CYCLOHEXYL ETHYL ACETATE (2-cyclohexylethyl acetate); CYCLOHEXYL SALICYLATE (cyclohexyl 2-hydroxybenzoate); DAMASCENONE ((E)-1-(2,6,6- trimethylcyclohexa-1 ,3-dien-1-yl)but-2-en-1-one); DAMASCONE ALPHA ((E)-1-(2,6,6- trimethylcyclohex-2-en-1-yl)but-2-en-1-one); DECALACTONE GAMMA (5-hexyloxolan-2-one); DECENAL-4-TRANS ((E)-dec-4-enal); DIHYDRO MYRCENOL (2,6-dimethyloct-7-en-2-ol); DIPHENYL OXIDE (oxydibenzene); DIHYDRO ANETHOLE (1-methoxy-4-propylbenzene); DIHYDRO JASMONE (3-methyl-2-pentylcyclopent-2-enone); DIMETHYL ANTHRANILATE (methyl 2-(methylamino)benzoate); DIMETHYL BENZYL CARBINYL ACETATE (2-methyl-1- phenylpropan-2-yl acetate); DIMETHYL BENZYL CARBINYL BUTYRATE (2-methyl-1- phenylpropan-2-yl butanoate); DIMETOL (2,6-dimethylheptan-2-ol); DODECALACTONE DELTA (6-heptyltetrahydro-2H-pyran-2-one); DODECALACTONE GAMMA (5-octyloxolan-2-one); DODECENAL ((E)-dodec-2-enal); EBANOL ((E)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1- yl)pent-4-en-2-ol); ETHYL HEXANOATE (ethyl hexanoate); ETHYL METHYL-2-BUTYRATE (ethyl 2-methyl butyrate); ETHYL MALTOL (2-ethyl-3-hydroxy-4H-pyran-4-one); ETHYL OENANTHATE (ethyl heptanoate); ETHYL VANILLIN (3-ethoxy-4-hydroxybenzaldehyde); ETHYLENE BRASSYLATE (1 ,4-dioxacycloheptadecane-5, 17-dione); EUCALYPTOL ((1s,4s)-1 ,3,3-trimethyl- 2-oxabicyclo[2.2.2]octane); EUGENOL (4-allyl-2-methoxyphenol); EVERNYL (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); GALBANONE PURE (1-(5,5-dimethylcyclohex-1-en-1- yl)pent-4-en-1-one); GARDENOL (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); HABANOLIDE ((E)- oxacyclohexadec-12-en-2-one); HEDIONE (methyl 3-oxo-2-pentylcyclopentaneacetate); HEXENAL-2-TRANS ((E)-hex-2-enal); HEXENOL-3-CIS ((Z)-hex-3-en-1-ol); HEXENYL-3-CIS ACETATE ((Z)-hex-3-en-1-yl acetate); HEXENYL-3-CIS SALICYLATE ((Z)-hex-3-en-1-yl 2- hydroxybenzoate); HEXYL ACETATE (hexyl acetate); INDOLENE (8,8-di(1 H-indol-3-yl)-2,6- dimethyloctan-2-ol); IONONE BETA ((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one);

[0129] 31455 PCT IRISANTHEME ((E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one); IRISONE ALPHA ((E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one); ISOAMYL ACETATE (3- methylbutyl acetate); ISOAMYL BUTYRATE (3-methylbutyl butanoate); ISOEUGENOL ((E)-2- methoxy-4-(prop-1-en-1-yl)phenol); ISOJASMONE B 11 (2-hexylcyclopent-2-en-1-one); ISORALDEINE ((E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one); JASMONYL (3-butyl-5-methyltetrahydro-2H-pyran-4-yl acetate); LAITONE (8-isopropyl-1-oxaspiro[4.5]decan- 2-one); LEMONILE ((2E,6Z)-3,7-dimethylnona-2,6-dienenitrile); 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); MANZANATE (ethyl 2-methylpentanoate); MAYOL ((4-isopropylcyclohexyl)methanol); MEFROSOL (3-methyl-5-phenylpentan-1-ol); MELONAL (2,6-dimethylhept-5-enal); MERCAPTO-8-METHANE-3-ONE (mercapto-para- menthan-3-one); METHYL ANTHRANILATE (methyl 2-aminobenzoate); METHYL BENZOATE (methyl benzoate); METHYL DIANTILIS (2-ethoxy-4-(methoxymethyl)phenol); METHYL HEPTENONE PURE (6-methylhept-5-en-2-one); METHYL LAITONE (8-methyl-1- oxaspiro[4.5]decan-2-one); METHYL OCTYNE CARBONATE (methyl non-2-y noate); METHYL SALICYLATE (methyl 2-hydroxybenzoate); NECTARYL (2-(2-(4-methylcyclohex-3-en-1- yl)propyl)cyclopentanone); NEOFOLIONE ((E)-methyl 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); NEROLINE CRYSTALS (2-ethoxynaphthalene); NEROLIONE (1-(3-methylbenzofuran-2- yl)ethanone); NERYL ACETATE ((Z)-3,7-dimethylocta-2,6-dien-1-yl acetate); NONADIENAL ((2E,6Z)-nona-2,6-dienal); NONENAL-6-CIS ((Z)-non-6-enal); NONENOL-6-CIS ((Z)-non-6-en-1- ol); NYMPHEAL (3-(4-(2-methylpropyl)-2-methylphenyl)propanal); OCTALACTONE DELTA (6- propyltetrahydro-2H-pyran-2-one); GRANGER CRYSTALS (1-(2-naphtalenyl)-ethanone); PARA TERT BUTYL CYCLOHEXYL ACETATE (4-(tert-butyl)cyclohexyl acetate); PEACH PURE (5- heptyldihydrofuran-2(3H)-one); PELARGOL (3,7-dimethyloctan-1-ol); PHENYL ETHYL ACETATE (2-phenylethyl acetate); PINENE ALPHA (2,6, 6-trimethylbicyclo[3.1.1]hept-2-ene); PINENE BETA (6,6-dimethyl-2-methylenebicyclo[3.1 .1]heptane); POMAROSE ((2E,5E)-5,6,7-trimethylocta-2,5- dien-4-one); POMELOL FF (2,4,7-Trimethyl-6-octen-1-ol); PRENYL ACETATE (3-methylbut-2- en-1-yl acetate); PRUNOLIDE (5-pentyldihydrofuran-2(3H)-one); RASPBERRY KETONE (4-(4- hydroxyphenyl)butan-2-one); ROSALVA (dec-9-en-1-ol); ROSE OXIDE CO (4-methyl-2-(2- methylprop-1-en-1-yl)tetrahydro-2H-pyran); ROSYRANE SUPER (4-methyl-2-phenyl-3,6-dihydro- 2H-pyran); SAFRANAL (2,6,6-trimethylcyclohexa-1 ,3-dienecarbaldehyde); SCENTAURUS JUICY (4-(dodecylthio)-4-methylpentan-2-one); SILVIAL (2-methyl-3-[4-(2- methylpropyl)phenyl]propanal); STYRALLYL ACETATE (1-phenylethyl acetate); SYLKOLIDE

[0130] 31455 PCT ((E)-2-((3,5-dimethylhex-3-en-2-yl)oxy)-2-methylpropyl cyclopropanecarboxylate); TERPINENE GAMMA (1-methyl-4-propan-2-ylcyclohexa-1 ,4-diene); TERPINEOL (2-(4-methylcyclohex-3-en- 1-yl)propan-2-ol); TERPINOLENE (1-methyl-4-(propan-2-ylidene)cyclohex-1-ene); TETRAHYDRO LINALOOL (3,7-dimethyloctan-3-ol); TOSCANOL (1-(cyclopropylmethyl)-4- methoxybenzene); TRIDECENE-2-NITRILE ((E)-tridec-2-enenitrile); TRIFERNAL (3- phenylbutanal); TROPIONAL (3-(benzo[d][1 ,3]dioxol-5-yl)-2-methylpropanal); UNDECAVERTOL ((E)-4-methyldec-3-en-5-ol); YARA YARA (2-methoxynaphtalene); BOIS CEDRE ESS CHINE (cedar wood oil); EUCALYPTUS GLOBULUS ESS CHINA (eucalyptus oil); GALBANUM ESS (galbanum oil); GIROFLE FEUILLES ESS RECT MADAGASCAR (clove oil); LAVANDIN GROSSO OIL FRANCE ORPUR (lavandin oil); MANDARIN OIL WASHED COSMOS (mandarin oil); ORANGE TERPENES (orange terpenes); PATCHOULI ESS INDONESIE (patchouli oil); and YLANG ECO ESSENCE (ylang oil). These ingredients have the advantage of providing microcapsules which are particularly sustainable.

[0131] The at least one benefit agent may comprise at least one fragrance precursor, meaning a material that is capable of releasing a fragrance ingredient by the means of a stimulus, such as a change of temperature, the presence of oxidants, the action of enzymes or the action of light. Such fragrance precursors are well-known to the art.

[0132] The at least one benefit agent may also comprise at least one functional cosmetic ingredient. The functional cosmetic ingredients for use in the encapsulated composition are preferably hydrophobic. Preferably, the cosmetic ingredients have a calculated octanol / water partition coefficient (ClogP) of 1.5 or more, more preferably 3 or more. Alternatively preferred, the ClogP of the cosmetic ingredient is from 2 to 7.

[0133] Particularly useful functional cosmetic ingredients may be selected from the group consisting of emollients, smoothening ingredients, hydrating ingredients, soothing and relaxing ingredients, decorative ingredients, deodorants, anti-aging ingredients, cell rejuvenating ingredients, draining ingredients, remodeling ingredients, skin levelling ingredients, preservatives, anti-oxidants, 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.

[0134] Particularly useful functional cosmetic ingredients include, but are not limited to hydrophobic polymers, such as alkyldimethylsiloxanes, polymethylsil-sesquioxanes, polyethylene, polyisobutylene, styrene-ethylene-styrene and styrene-butylene-styrene block copolymers, and

[0135] 31455 PCT the like; mineral oils, such as hydrogenated isoparaffins, silicone oils and the like; vegetable oils, such as argan oil, jojoba oil, aloe vera oil, and the like; fatty acids and fatty alcohols and their esters; glycolipides; phospholipides; sphingolipides, such as ceramides; sterols and steroids; terpenes, sesquiterpenes, triterpenes and their derivatives; essential oils, such as Arnica oil, Artemisia oil, Bark tree oil, Birch leaf oil, Calendula oil, Cinnamon oil, Echinacea oil, Eucalyptus oil, Ginseng oil, Jujube oil, Helianthus oil, Jasmine oil, Lavender oil, Lotus seed oil, Perilla oil, Rosmary oil, Sandal wood oil, Tea tree oil, Thyme oil, Valerian oil, Wormwood oil, Ylang Ylang oil, and Yucca oil.

[0136] In particular, the at least one functional cosmetic ingredient may be selected from the group consisting of Sandal wood oil, such as Fusanus Spicatus kernel oil; Panthenyl triacetate; Tocopheryl acetate; Tocopherol; Naringinin; Ethyl linoleate; Farnesyl acetate; Farnesol; Citronellyl methyl crotonate; and Ceramide-2 (1-Stearoiyl-C18-Sphingosine, CAS-No: 100403-19-8).

[0137] The at least one benefit agent may comprise agents which suppress or reduce malodour and its perception by adsorbing odour, agents which provide a warming or cooling effect, insect repellents or UV absorbers.

[0138] In one embodiment, the benefit agent is bio-degradable.

[0139] In one embodiment, the microcapsule composition of the present invention comprises a core comprising at least one fragrance ingredient and a shell surrounding the core, wherein the shell comprises a resin formed by the reaction of: a Michael acceptor which is poly(caprolactone) triacrylate, polycarbonate diacrylate or acrylated triricinolein; and a Michael donor which is lysine, polylysine or mixtures thereof.

[0140] Polymeric stabilizer

[0141] The encapsulated composition of the present invention may be generated via the formation of an oil-in-water emulsion. The oil-in-water emulsion may be stabilized using a polymeric stabilizer.

[0142] The polymeric stabilizers that are suitable for the purpose of the present invention include water soluble polymers of natural origin, such as cellulose derivatives, degraded or modified starch, gums, pectin, gelatin, and the like; water-soluble polymers of synthetic origin, such poly(vinyl alcohol), poly(vinyl pyrrolidone), poly(acrylic-co-acrylate) copolymers, poly(acrylamide),

[0143] 31455 PCT sulfonated poly(acrylate), copolymers of maleic anhydride with styrene, isobutylene, butadiene and ethylene, poly(styrene sulfonic acid), and the like, and mixtures thereof.

[0144] In one embodiment, the microcapsule composition comprises between about 0.1 % and 5% w / w of a polymeric stabilizer, relative to the total weight of the composition.

[0145] Methods

[0146] In one aspect, a method for preparing a microcapsule composition as described herein is provided.

[0147] The method comprises the steps of: a) Providing an oil phase comprising the benefit agent and a Michael acceptor; b) Providing an aqueous phase, optionally comprising a stabilizer; c) Emulsifying the oil phase of step a) into the aqueous phase of step b) to obtain an oil in water emulsion; d) Adding to the emulsion obtained in step c) a Michael donor; e) Providing conditions for condensation between the Michael donor and the Michael acceptor to obtain a microcapsule composition.

[0148] The benefit agent, Michael acceptor, stabilizer and Michel donor are as described hereinabove.

[0149] In one embodiment, the Michael acceptor is generated by synthesis as described hereinabove, prior to step a).

[0150] The microcapsule composition prepared according to the method hereinabove are in the form of a microcapsule slurry.

[0151] The method according to the present invention may comprise the additional step of drying the microcapsule slurry, in order to obtain a microcapsule powder.

[0152] Drying of a slurry of microcapsules is conventional, and may be carried out according techniques known in the art, such as spray-drying, evaporation, lyophilization or use of a desiccant. Typically, as is conventional in the art, dried microcapsules will be dispersed or suspended in a suitable powder, such as powdered silica, which can act as a bulking agent or flow aid. Such suitable powder may be added to the encapsulated composition before, during or after the drying step.

[0153] 31455 PCT In particular, the drying process may be accompanied by an additional entrapping process, wherein additional benefit agent is entrapped in an entrapping material. For example, the slurry to be dried may comprise, in addition to the core-shell microcapsules obtained in the methods according to the present invention, at least one non-encapsulated benefit agent and at least one entrapping material, so that the benefit agent that is not encapsulated in the core-shell microcapsule is entrapped in the entrapping material during drying. Therefore, upon drying, a matrix is formed around or coexisting with the core-shell microcapsules.

[0154] Consumer Product

[0155] The present invention also relates to a consumer product comprising a microcapsule composition as described hereinabove. The consumer product may be selected from the group consisting of household (home) care, personal care, fabric care and pet care products.

[0156] Suitable home care products include hard surface cleaners, heavy duty detergents and detergent powders, air care compositions.

[0157] 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. In one embodiment, the consumer product is a cosmetic product.

[0158] Suitable fabric care compositions include laundry care detergents, laundry care conditioners, fabric refreshers, scent boosters.

[0159] The microcapsule composition of the present invention, presented in the form of a slurry of microcapsules suspended in an aqueous suspending medium may be incorporated as such in a consumer product base or it may be incorporated in dry powder form.

[0160] Yet another aspect of the present invention relates to the use of a microcapsule composition as described hereinabove to improve the perception or enhance the performance of the benefit agent in a consumer product.

[0161] The solid content of the microparticles has been measured by a Halogen Moisture Analyzer Mettler Toledo instrument. The test measures the encapsulation efficacy, i.e. the percentage of the theoretical fragrance that was encapsulated.

[0162] 31455 PCT Dv(50) represents the maximum particle diameter below which 50% of the sample volume exists, also known as the median particle size by volume. It is also known as the Malvern volume weighted particle size distribution, measured using light scattering techniques.

[0163] The microscopic images were recorded with an Olympus BX51 Microscope.

[0164] The table below shows the composition of the fragrance used in the examples:

[0165] The present invention is further illustrated by means of the following non-limiting examples:

[0166] Example 1 : Poly(caprolactone) triacrylate

[0167] Poly(caprolactone) triol (25.65 g, 0.0855 mol) was introduced in a three-necked 500 mL round bottom flask and dissolved with 120 ml of dichloromethane. 53.66 mL of triethyl amine (38.95 g, 0.385 mol) was added to the solution and the latter was cooled down to 5°C by putting the flask in an ice bath. A solution of 31 mL acryloyl chloride (34.82 g, 0.385 mol) in 40 mL of dichloromethane was added dropwise in the round bottom flask during 1 h. The reaction medium was left stirring overnight. After 18 h, the reaction medium was washed with 200 mL 0.1M HCI solution twice, and once with saturated NaCI solution. The organic phase was dried over anhydrous magnesium sulfate and filtered. The traces of dichloromethane were eliminated through vacuum drying. 23.85 g yellow and slightly viscous poly(caprolactone) triacrylate was obtained (92% yield).

[0168] Figure 1 shows the comparison between the1H NMR (CDCI3) spectra of poly(caprolactone) triol (B) and poly(caprolactone) triacrylate (C), with the peaks in the 5.5-6.5 ppm region clearly showing the formation of the acrylated product.

[0169] 31455 PCT Example 2: Converge diacrylate

[0170] Converge (diol) with molecular weight of 2000 g / mol (41.5 g, 0.0207 mol) was introduced in a three-necked 500 mL round bottom flask and dissolved with 135 ml of dichloromethane. Afterwards, 8.67 mL of triethyl amine (6.3 g, 0.06225 mol) was added to the solution and the latter was cooled down to 5°C by putting the flask in an ice bath. A solution of 5 mL acryloyl chloride (5.63 g, 0.06225 mol) in 15 mL of dichloromethane was added drop wise in the round bottom flask during 30 min. The reaction medium was left stirring overnight. After 18h, the reaction medium was washed with 150 mL 0.1M HCI solution twice, and once with saturated NaCI solution. The organic phase was dried over anhydrous magnesium sulfate and filtered. The traces of dichloromethane were eliminated through vacuum drying. 39.42 g of viscous yellow Converge diacrylate was obtained (95% yield).

[0171] Figure 2 shows the comparison between the1H NMR (CDCI3) spectra of Converge diol (B) and Converge diacrylate (C), with the peaks in the 5.5-6.5 ppm region clearly showing the formation of the acrylated product.

[0172] Example 3: Acrylated Castor Oil

[0173] Castor oil (10 g, 0.0108 mol) was introduced in a two-necked 250 ml round bottom flask and dissolved in 25 mL of dry THF, then mixed with triethyl amine (3.54 g, 0.035 mol). The solution was cooled down to 5°C by putting the flask in an ice bath. A solution of acryloyl chloride (3.17 g, 0.035 mol) in 10 ml of dry THF was added drop-wise in the round bottom flask. The reaction mixture was kept stirring overnight. After complete reaction, the product was vacuum-evaporated and dissolved in 50 ml of DCM. The product was then washed with 50 mL 0.1M HCI solution followed by several washings with 50 mL of brine solution. The organic phase was dried with anhydrous magnesium sulfate then filtered. The traces of DCM solvent were evaporated and 11 .38 g of acrylated castor oil were obtained with a yield of 96 %.

[0174] Figure 3 shows the comparison between the1H NMR (CDCI3) spectra of castor oil and acrylated castor oil, with the peaks in the 5.5-6.5 ppm region clearly showing the formation of the acrylated product.

[0175] Example 4: Synthesis of microcapsules with Acrylated Castor Oil

[0176] (Phase A) In a glass beaker, an oil phase was prepared by dissolving 0.5 g acrylated castor oil in 4.5 g perfume at room temperature.

[0177] 31455 PCT (Phase B) In another beaker, 0.4 g Mowiol 4-88 was added to 39.6 g distilled water and dissolved at 80°C for 1 h.

[0178] The oil phase was then added to the solution PV(OH) 1 % and homogenized at 10000 rpm for 5 min. Once the emulsion was obtained, 0.35 g L-Lysine (Phase C) was added. The emulsion was then gently stirred. The pH was adjusted to pH 8 with HCI 10%. The slurry was stirred at 60°C for 4 h, then at room temperature overnight.

[0179] Figure 4 shows an example of a microscope image of the resulting composition, clearly demonstrating formation of a microcapsule slurry.

[0180] Example 5: Synthesis of microcapsules with Poly(caprolactone) triacrylate

[0181] (Phase A) In a glass beaker, an oil phase was prepared by dissolving 0.5 g acrylated polycaprolactone in 4.5 g perfume at room temperature.

[0182] (Phase B) In another beaker, 0.4 g Mowiol 4-88 was added to 39.6 g distilled water and dissolved at 80°C for 1 h.

[0183] The oil phase was then added to the solution PV(OH) 1 % and homogenized at 10000 rpm for 5 min. Once the emulsion was obtained, Phase C comprising at least one amino compound in the amounts (g) as shown in the table below was added. The emulsion was then gently stirred. The pH was adjusted to pH 8 with HCI 10%. The slurry was stirred at 60°C for 4 h, then at room temperature overnight.

[0184] The values of the solid content and the encapsulation efficiency of the microcapsule compositions are also shown in the table.

[0185] Figure 5 shows examples of microscope images of the resulting compositions, clearly demonstrating formation of microcapsule slurries.

[0186] 31455 PCT

Claims

Claims1 . A microcapsule composition comprising at least one core-shell microcapsule, wherein the at least one core-shell microcapsule comprises a core comprising at least one benefit agent and a shell surrounding the core, wherein the shell comprises a resin formed by the reaction of: a Michael acceptor which is the reaction product of a biodegradable polyester polyol with an a,p-unsaturated acid chloride; and a Michael donor comprising at least two nucleophilic moieties selected from the group consisting of a nitrogen nucleophile, a sulfur nucleophile, an oxygen nucleophile, a carbon nucleophile, a phosphorus nucleophile, and mixtures thereof, which are capable to react with the acrylic double bond of the Michael acceptor; optionally wherein the Michael donor is biodegradable.

2. The composition according to claim 1 , wherein the a,[3-unsaturated acid chloride is an a- unsubstitued a,[3-unsaturated acid chloride, optionally acryloyl chloride.

3. The composition according to claim 1 or claim 2, wherein the biodegradable polyester polyol is an aliphatic polyester polyol.

4. The composition according to claim 3, wherein the biodegradable aliphatic polyester polyol is selected form the group consisting of polylactone polyols, polycarbonate polyols, triglycerides of hydroxycarboxylic acids, preferably fatty acids, and mixtures thereof.

5. The composition according to claim 4, wherein the polylactone polyol is a polycaprolactone polyol, such as a difunctional polycaprolactone (e.g. polycaprolactone diol), trifunctional caprolactone (e.g. polycaprolactone triol), tetrafunctional caprolactone and mixtures thereof.

6. The composition according to claim 4, wherein the polycarbonate polyol is a polycarbonate diol produced from propylene oxide and carbon dioxide (polypropylene carbonate) diol).

7. The composition according to claim 4, wherein the fatty hydroxycarboxylic acid is ricinoleic acid.31455 PCT8. The composition according to any one of the preceding claims, wherein the Michael donor is a polyamine, optionally an aliphatic, a cyclic or an aromatic polyamine.

9. The composition according to any one of the preceding claims, wherein the Michael donor is an aminoacid-containing reagent, optionally wherein the aminoacid is selected from the group consisting of cysteine, serine, arginine, lysine, histidine and mixtures thereof.

10. The composition according to any one of the preceding claims, wherein the Michael donor is lysine, polylysine and mixtures thereof.11 . The composition according to any one of the preceding claims comprising a stabilizer.

12. The composition according to claim 11 , wherein the polymeric stabilizers are water soluble polymers of natural origin, such as cellulose derivatives, degraded or modified starch, gums, pectin and gelatin; water-soluble polymers of synthetic origin, such poly(vinyl alcohol), poly(vinyl pyrrolidone), poly(acrylic-co-acrylate) copolymers, poly(acrylamide), sulfonated poly(acrylate), copolymers of maleic anhydride with styrene, isobutylene, butadiene and ethylene, poly(styrene sulfonic acid), and the like, and mixtures thereof, optionally wherein the stabilizer is polyvinyl alcohol.

13. A method of making the microcapsule composition according to any one of claims 1 to 12, the method comprising the steps of: a) Providing an oil phase comprising the benefit agent and a Michael acceptor; b) Providing an aqueous phase, optionally comprising a stabilizer; c) Emulsifying the oil phase of step a) into the aqueous phase of step b) to obtain an oil in water emulsion; d) Adding to the emulsion obtained in step c) a Michael donor; e) Providing conditions for condensation between the Michael donor and the Michael acceptor to obtain a microcapsule composition.

14. A consumer product comprising a microcapsule composition according to any one of claims 1 to 12, optionally wherein the consumer product is a fabric care product, a home care product or a personal care product.31455 PCT15. Use of a microcapsule composition according to any one of claims 1 to 12 to enhance the performance of a benefit agent in a consumer product.31455 PCT

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