Improvements in or related to organic compounds

Abstract

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

Description

[Technical Field]

[0001] Field of the present invention The present invention relates to a composition comprising a core-shell microcapsule containing at least one beneficial agent, a method for forming the composition, the use of a composition to enhance the performance of the beneficial agent, and a consumer product comprising the composition.

[0002] Background of the Invention Consumer products, such as household care products, personal care products, and fabric care products, are known to incorporate encapsulated beneficial agents. Beneficial agents include, for example, fragrances, cosmetic agents, food ingredients, nutritional supplements, drugs, and substrate enhancers.

[0003] Encapsulated beneficial agents are typically presented in the form of multiple microcapsules. A specific example of microcapsules is the so-called "core-shell microcapsule," which typically consists of a core containing a beneficial agent encapsulated in a polymer shell that is impermeable to the beneficial agent, or at least partially impermeable to it. Typically, these microcapsules are suspended in an aqueous medium, and the encapsulated beneficial agent is hydrophobic. A wide selection of materials can be used to form the polymer shell material, as long as the shell is impermeable to the encapsulated beneficial agent, or at least partially impermeable to it.

[0004] Beneficial agents are encapsulated for various reasons related to the improved performance of the beneficial agents in consumer product applications. Microcapsules can isolate and protect beneficial agents from external suspension media that may be incompatible or unstable, such as consumer product bases. They are also used to aid in the deposition of beneficial agents onto substrates, such as skin or hair, or, in the case of fragrance components, fabrics or hard household product surfaces. They can also act as a means of controlling the spatiotemporal release of beneficial agents from consumer products.

[0005] A wide variety of encapsulation media suitable for the preparation of 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.

[0006] However, consumers are becoming increasingly concerned about using materials derived from non-renewable sources such as synthetic petrochemicals. In other words, consumers tend to prefer materials with more sustainable origins from an environmental and resource conservation perspective. Nevertheless, using natural and naturally derived materials to address all aspects of encapsulation and performance of beneficial agents is generally challenging.

[0007] In response, the consumer products industry has proposed microcapsules that utilize more bio-based components and exhibit improvements in terms of biodegradability. One example of such an approach is presented in WO 2020 / 233887 A1, which discloses core-shell microcapsules containing pectin and hydroxyethylcellulose. These microcapsules are bio-based and exhibit good biodegradability, while also showing good performance in terms of stability and fragrance release. However, the microencapsulation process is somewhat sensitive to the properties of the oil phase being encapsulated. This sensitivity can lead to incomplete encapsulation or the appearance of shell residue in the microcapsule slurry, as well as the formation of microcapsules that suffer from poor storage stability due to leakage of the encapsulated core material over time. [Overview of the Initiative]

[0008] Summary of the present invention Therefore, overcoming the aforementioned shortcomings of the prior art is a fundamental issue of the present invention. In particular, a fundamental issue of the present invention relates to how to provide a robust process for preparing core-shell microcapsule compositions that exhibit improved biodegradability, high levels of sustainable components, especially those formed from natural or naturally derived materials, while maintaining the release characteristics of the desired beneficial agent during manufacturing, storage, and application, and that are less sensitive to the properties of the encapsulated oil phase. Furthermore, the compositions should be operationally safe, robust, and can be manufactured by cost-effective means.

[0009] These problems are solved by the present invention, which is described in more detail below this specification.

[0010] Therefore, in a first aspect, the present invention provides a method for preparing a composition comprising a plurality of core-shell microcapsules, wherein the method comprises the following steps: a) To provide an oil phase comprising an encapsulated beneficial agent and a macromer formed by the reaction of one or more reactive building blocks; b) Providing an aqueous phase; c) Emulsifying the oil phase and the aqueous phase to form a dispersed phase consisting of multiple oil cores in a continuous aqueous phase; d) Polymerizing the macromer to form a polymer stabilizer at the interface between the oil core and the aqueous phase; e) subjecting the positively charged and negatively charged polymer electrolytes, which were independently added to the aqueous phase during steps b), c), or d), to a coacervation process, thereby forming a hydrated polymer shell around the oil core; and f) Crosslinking a hydrated polymer shell with a polymer stabilizer to cure the shell around the oil core, thereby forming a composition containing multiple core-shell microcapsules.

[0011] In a second aspect, the present invention provides a composition comprising a plurality of core-shell microcapsules obtained by the method described in the first aspect of the present invention.

[0012] In a third aspect, the present invention provides a consumer product comprising a composition comprising a plurality of core-shell microcapsules.

[0013] The details, aspects, examples and preferences provided with respect to one or more aspects described in the present invention are further described herein and will apply equally to all aspects of the present invention. Any combination in any possible variation of the aspects, examples, and preferences described below, unless indicated herein or clearly inconsistent with the context, is encompassed by the present invention.

[0014] Detailed description of the present invention The composition prepared according to the present invention comprises a plurality of core-shell microcapsules, the microcapsules being characterized by comprising a core containing a beneficial agent and a polymer shell surrounding the core. The shell is a cross-linked polymer material formed from both a hydrated polymer and a polymer stabilizer. The shell thus formed provides an impermeable encapsulating material that deposits on the substrate during use and adheres well around the oil core. Furthermore, without being bound by any theory, the hydrated polymer is also thought to provide an optimal point of attack for microbial degradation, thereby leading to enhanced biodegradation in nature.

[0015] The polymer stabilizer can be in the form of a wide range of film-forming materials and resins, the exact nature of which depends on the macromer and in turn on the selection of the reactive building blocks. Preferably, the polymer stabilizer is highly cross-linked in order to significantly reduce the diffusion of the core contents through the shell. Preferably, the impermeability of the shell is high enough to significantly prevent the leakage of the beneficial agent to an extraction-based consumer product containing a surfactant.

[0016] In the context of the present invention, leakage can be considered to be significantly prevented if the amount of the beneficial agent leached into the consumer product base within a period of 3 months at 40 °C is less than 75% by weight, preferably less than 50% by weight, more preferably less than 25% by weight, and even more preferably less than 10% by weight of the total amount of the beneficial agent initially encapsulated.

[0017] In step a) of the method according to the present invention, the macromer can be pre-formed and added to the oil phase. Alternatively, preferably for economic reasons, the reactive building block is added to the oil phase and the macromer is formed in situ in the oil phase.

[0018] The polymer stabilizer is formed at the interface between the dispersed oil core and the continuous aqueous phase by polymerizing the macromer. The emulsification step c) and the step d) of forming the polymer stabilizer can occur simultaneously or sequentially. However, without being bound by any theory, the applicant believes that the formation of the polymer stabilizer is slower than the time required to complete the emulsification step and is completed only after step c) is completed.

[0019] The macromer is a reaction product of the same or different reactive building blocks. The macromer can be formed by a radical reaction; it can be a pre-condensate formed by condensation; or it can be an adduct formed by addition. Chemical substances that may be suitable for the formation of the macromer include, but are not limited to, (i) radical reactions of alpha-beta unsaturated reactive building blocks, such as (meth)acrylic acid and (meth)acrylic acid esters, styrene, divinylbenzene, vinyl esters; (ii) condensation reactions, such as condensation of reactive building blocks, such as condensation of carboxylic acids or carboxylic acid chlorides with alcohols or amines, condensation of phenols or amines with aldehydes, and condensation of silanols; (iii) addition reactions, such as addition of reactive building blocks, such as nucleophilic functional groups having activated olefin double bonds, epoxides having alcohols, and isocyanates having alcohols or amines.

[0020] In embodiments of the present invention in which macromers are formed in sit in the oil phase, preferred chemicals are those specified above in (i) and (iii).

[0021] As defined herein, macromers may be added to the oil phase if they are already formed, or they may be formed from reactive building blocks in the oil phase. When macromers are pre-formed, they may be prepared in an organic solvent or a water-soluble aprotic solvent.

[0022] When macromers are formed in situ in the oil phase, it is preferable that the oil phase does not contain, or substantially contains, any components that could react with the reactive building block to prevent the formation of a core-shell capsule, provided that such components are not the reactive building block itself.

[0023] "Substantially free" means that any reactive building blocks and any readily reactive components are present in amounts of less than 1% by weight, and more specifically less than 0.1% by weight, based on the total weight of the oil phase.

[0024] Furthermore, when the aforementioned components are present, it is preferable that the components have solubility parameters that are compatible with the reactive building block, where the term "compatible" has the meaning defined herein.

[0025] Consequently, in specific embodiments, the present invention relates to a method as defined in the first aspect of the present invention, wherein the macromer is formed in situ in an oil phase, the oil phase is divided into a first part and a second part, and during the formation of the macromer, the reactive building block is in contact only with the first part of the oil phase, and the reactive building block does not include, or substantially does not include, any components that are reactive with the reactive building block.

[0026] The solubility parameters indicated above are Hansen solubility parameters. Hansen solubility parameters are well known in the art and can be calculated by the Yamamoto-Molecular Break (Y-MB) method implemented in the 4th edition of the HSPiP software. Those skilled in the art are familiar with the use of both Hansen solubility parameters and the HSPiP software, including the Yamamoto-Molecular Break (Y-MB) method implemented in this software.

[0027] The "Yamamoto-Molecular Break (Y-MB) method" refers to solubility parameters following the Hansen standard, calculated using a group contribution method developed by Hiroshi Yamamoto (https: / / www.pirika.com / ENG / HSP / E-Book / Chap30.html (updated 2013); HSP Application note #26: Yamamoto-Molecular Break (Y-MB) in HSPiP, https: / / www.pirika.com / NewHP / Y-MB / Functional_Groups.html, 2010). The Y-MB Hansen parameters are automatically and clearly calculated using the Y-MB subroutine in the HSPiP calculation software. The calculation is based on two-dimensional canonical SMILES molecular encoding and does not rely on any detailed knowledge of the three-dimensional structure of the molecule under consideration. The Hansen parameters quantify the interactions that a molecule may experience when it comes into contact with the environment, more specifically with the solvent. These interactions may result from dispersion forces reflected by parameter δD, dipole-dipole electrostatic forces reflected by parameter δP, and hydrogen bonds reflected by parameter δH. Hansen's parameters are well known to those skilled in the art.

[0028] Regarding determining whether a component is compatible with a reactive building block based on the solubility parameter, it is naturally preferred that the component is compatible with all reactive building blocks. However, when various building blocks are used and the compatibility of a certain component is not satisfied by all reactive building blocks, any component contained in the oil phase is preferably compatible with the reactive building block having the highest molecular weight.

[0029] In the context of the present invention, two substances A and B are considered to be compatible when their individual Hansen solubility parameters satisfy the conditions defined by the following Equation 1:

Equation

[0030] When the reactive building block and the medium in which the macromer is formed are incompatible, then phase separation of the reactive building block and the medium may occur, and the formation of the macromer may be inhibited.

[0031] In an embodiment of the present invention, the macromer is formed in situ in the oil phase, and the oil phase, based on the total weight of the oil phase, includes: I. Components that are less reactive with the reactive building block, less than 1% by weight, more specifically less than 0.1% by weight, and even more specifically 0.0% by weight; II. Components having Hansen solubility parameters that satisfy Equation 1, 40% by weight or more, more specifically 60% by weight or more, even more specifically 75% by weight or more, even more specifically 90% by weight or more, and even more specifically 95% by weight or more:

number

number

number

[0032] In embodiments of the present invention in which the macromer is formed in situ in the oil phase, the components may be beneficial agents, or when they contain multiple components, for example, in the case where the beneficial agent is a fragrance formulation containing multiple fragrance components, the components may be any part of the beneficial agent.

[0033] In an embodiment of the present invention, when it is desired to form a macromer in situ in an oil phase, and the sum of the oil phase composition does not satisfy the suitability conditions I) to IV) described above, the oil phase is divided into a first part and a second part, such that the first part satisfies suitability conditions I) to IV). The first part of the oil phase is then combined with the reactive building block in step a). The second part of the oil phase combines with the first part only after the macromer has been formed. In this way, components of the oil phase that could hinder macromer formation are separated from the reactive building block during macromer formation and can only combine with the first part when the macromer is formed. This can be a particularly important precaution when the oil phase contains multiple fragrance components, many of which may be somewhat reactive with the reactive building block.

[0034] In an embodiment of the present invention in which the oil phase is divided into a first part and a second part, the weight ratio of the second part to the first part is between 4.5 and 0.5 and 0.5 and 4.5, more specifically between 4 and 1 and 1 and 4, and more specifically between 3 and 2 and 2 and 3. If the first part is too small compared to the second part, the amount of macromer formed may be too small to form a sufficient polymer stabilizer to adequately cover the entire surface area of ​​the oil / water.

[0035] In specific embodiments of the present invention, the macromer is an adduct formed by the reaction of a reactive building block comprising an aminosilane and a polyfunctional isocyanate. In such cases, the adduct macromer can polymerize (in step d) by a polycondensation process at the oil / water interface to form a polymer stabilizer. Such building blocks are described later in this specification.

[0036] In a specific embodiment of the present invention, the formation of the addition macromer in step a) is carried out under stirring at a temperature of 10°C to 50°C, more specifically 20°C to 45°C, and even more specifically 25°C to 40°C for 15 minutes to 120 minutes, more specifically 30 minutes to 90 minutes.

[0037] The applicant has no intention of being bound by any theory and believes that addition macromers are formed when the amine group of an aminosilane is added to the isocyanate functional group of a polyfunctional isocyanate, forming a urea bond.

[0038] Once a macromer is formed, it can polymerize by forming siloxane bonds through polycondensation of silane functional groups in contact with water, thereby forming a polymer stabilizer at the oil / water interface.

[0039] The polymer stabilizers thus formed are highly crosslinkable and readily provide reactive functional groups on their surface, and can be used to immobilize additional shell-forming material around the polymer stabilizer according to step e), thereby completing the shell formation. These reactive surface groups are isocyanate groups, amine groups, and silane groups that did not react during the formation of the polymer stabilizer. These additional shell-forming materials are described in further detail later in this specification and include hydrogels, e.g., simple coacervates and complex coacervates.

[0040] In a more specific embodiment of the present invention, the aqueous phase provided in step b) comprises water, more specifically deionized water, and an emulsifier, such as a surfactant, more specifically a polymer surfactant. The term polymer surfactant refers to a polymer that, when dissolved in one or both of the oil and aqueous phases, has the property of reducing the interfacial tension between the oil and aqueous phases. Polymer surfactants are useful in promoting the formation of dispersed oil droplets having a desired droplet size.

[0041] Polymer surfactants that can be used in the process according to the present invention are well known to those skilled in the art and include a wide range of hydrophilic colloids, such as copolymers of acrylamide, benzenesulfonates, (meth)acrylic acid, maleic anhydride, polyvinyl alcohol, and polyvinylpyrrolidone, and modified biopolymer-derived components, such as proteins, lignin, polysaccharides, and salts thereof.

[0042] In a specific embodiment, the polymer surfactant is a negatively charged polysaccharide.

[0043] The emulsification step c) is preferably carried out at a temperature of 10°C to 50°C, more specifically 20°C to 45°C, and even more specifically 25°C to 40°C, for 15 minutes to 120 minutes, and more specifically 30 minutes to 90 minutes.

[0044] The emulsification step c) generates multiple droplets, which act as molds, causing shell formation around them. The droplet size distribution can be controlled by means commonly known in the art, by controlling the emulsification conditions, e.g., the stirring speed and the shape of the stirrer. As a result, multiple microcapsules with controlled average size and size distribution can be obtained, where the oil phase is encapsulated, thereby forming the core element of the core-shell microcapsule. The appropriate stirring speed and shape of the mixer can be selected by standard means to obtain the desired average droplet size and droplet size distribution.

[0045] In specific embodiments of the present invention, emulsification step c) may be carried out in a vessel equipped with a turbine or a cross-beam stirrer having a pitched beam, such as a MIG stirrer, and having a stirrer diameter to reactor diameter of 0.6 to 0.8. Microcapsules may be formed in a reactor having a volume-average size (d50) of 30 μm or less, more specifically 20 μm or less, at a stirring speed of about 100 to about 1200 rpm, more specifically about 600 rpm to 1000 rpm. Preferably, a MIG stirrer operating at a speed of 850 + / - 50 rpm is used. However, those skilled in the art will readily understand that such stirring conditions may vary depending on the size of the reactor, the batch size, the exact shape of the stirrer, and the ratio of the stirrer diameter to the reactor diameter. For example, for a MIG stirrer with a stirrer diameter ratio of 0.5 to 0.9 relative to the reactor, and a slurry volume in the range of 0.5 to 8 tons, the preferred stirring speed in the context of the present invention is 150 rpm to 50 rpm. Adjusting the emulsification conditions considering the variables indicated above is within the scope of those skilled in the art.

[0046] In specific embodiments of the present invention, the reactive building block may include an aminosilane. A suitable aminosilane reactive building block to be used in the formation of a polymer stabilizer may be selected from compounds represented by formula (I). [ka]

[0047] In equation (I) above, R 1 , R 2 and R 3 Each is independently a linear or branched alkyl or alkenyl residue of C1-C4, particularly methyl or ethyl, and R 4 C1-C2 containing an amino functional group 12 Preferably, these are linear or branched alkyl or alkenyl residues of C1 to C4, particularly primary, secondary, or tertiary amines.

[0048] When the functional group is a primary amine, the functional group can be a terminal primary amine. Then, R 4 is a linear terminal primary aminoalkyl residue of C1 - C8, more preferably C1 - C4. Specific amino silanes in this category are selected from the group consisting of aminomethyltriethoxysilane, 2-aminoethyltriethoxysilane, 3-aminopropyltriethoxysilane, 4-aminobutyltriethoxysilane, 5-aminopentyltriethoxysilane, 6-aminohexyltriethoxysilane, 7-aminoheptyltriethoxysilane, and 8-aminooctyltriethoxysilane.

[0049] Without being bound by any theory, it is speculated that silane groups polycondense with each other to form a silica network at the oil-water interface, further stabilizing this interface.

[0050] In a specific embodiment of the present invention, the amino silane is a bipolar amino silane, which means a molecule containing at least 1 amino group and 2 residues, each of these residues having at least 1 alkoxysilane moiety.

[0051] At least 1 bipolar amino silane can have the formula (II).

Chemical formula

[0052] In the above formula (II), X is -NR 1 -, -NR 1 -CH2-NR 1 -, -NR 1 -CH2-CH2-NR 1 -, -NR 1 -CO-NR 1 -, or

Chemical formula

[0053] In the above formula (II), R 1Each of these independently represents H, CH3, or C2H5. R 2 Each of these independently represents a linear or branched alkylene group having 1 to 6 carbon atoms. 3 Each of these independently represents a linear or branched alkyl group having 1 to 4 carbon atoms. 4 Each of these independently represents a linear or branched alkyl group having H or 1 to 4 carbon atoms. f represents 0, 1, or 2.

[0054] Bipodal aminosilanes are particularly advantageous for forming stable oil-water interfaces.

[0055] Examples of bipodal aminosilanes include, but are not limited to, bis(3-(triethoxysilyl)propyl)amine, N,N'-bis(3-(trimethoxysilyl)propyl)urea, bis(3-(methyldiethoxysilyl)propyl)amine, N,N'-bis(3-(triethoxysilyl)propyl)methoxysilyl)propyl)ethane-1,2-diamine, bis(3-(methyldimethoxysilyl)propyl)-N-methylamine, and N,N'-bis-(3--(triethoxysilyl)propyl)piperazine.

[0056] Bipodal aminosilanes can be secondary bipodal aminosilanes. Using secondary bipodal aminosilanes instead of primary aminosilanes reduces the reactivity of polymer stabilizers with respect to electrophilic species, particularly aldehydes. Therefore, beneficial agents containing high levels of aldehydes, such as fragrance components with aldehyde functionality, can be encapsulated with less tendency towards harmful interactions between the components in the oil phase and the shell-forming material.

[0057] The secondary bipodal aminosilane may be a bis(3-(triethoxysilyl)propyl)amine. This particular secondary aminosilane has the advantage of releasing ethanol instead of methanol, which is more toxic and undesirable, during the polycondensation of the ethoxysilane group, for example.

[0058] Other aminosilanes may also be used in combination with the aforementioned bipodal aminosilanes, in particular any aminosilanes listed herein.

[0059] In specific embodiments of the present invention, the reactive building block may include a polyfunctional isocyanate. A suitable polyfunctional isocyanate building block may be selected from organic isocyanates in which the isocyanate group is bonded to an organic residue (RN=C=O or R-NCO). In the context of the present invention, the polyfunctional isocyanate may be selected from alkyl, alicyclic, aromatic, alkyl-aromatic, and anionically modified polyfunctional isocyanates having two or more (e.g., three, four, five, etc.) isocyanate groups in the molecule.

[0060] Preferably, the polyfunctional isocyanate is an aromatic or alkyl aromatic isocyanate, and more preferably, an alkyl aromatic polyfunctional isocyanate having a methyl isocyanate group attached to the aromatic ring. Both aromatic and methyl isocyanate-substituted aromatic polyfunctional isocyanates have superior reactivity compared to alkyl and alicyclic polyfunctional isocyanates. Of these, 2-ethylpropane-1,2,3-tritris((3-(isocyanatemethyl)phenyl)carbamate) is particularly preferred due to its trifunctionality, which is favorable for the formation of intermolecular crosslinks, and its intermediate reactivity, which is favorable for the uniformity of the network. This alkyl aromatic polyfunctional isocyanate is commercially available under the trademark Takenate D-100 N, sold by Mitsui, or under the trademark Desmodur® Quix175, sold by Covestro.

[0061] As an alternative to aromatic or alkyl-aromatic polyfunctional isocyanates, it may also be advantageous to employ anionically modified polyfunctional isocyanates due to their ability to react at the oil / water interface, and even in the aqueous phase close to the oil / water interface. Particularly preferred anionically modified polyfunctional isocyanates have formula (III). [ka]

[0062] Formula (III) represents a commercially available anionic polyisocyanate, which is a modified isocyanate of hexamethylene diisocyanate sold by Covestro under the trademark Bayhydur® XP2547.

[0063] In a specific embodiment of the present invention, step d) is carried out using a macromer which is an adduct of an aminosilane and a polyfunctional isocyanate as indicated herein, and the polymer stabilizer is formed by polycondensation of the silane groups of the adduct at the oil-water interface.

[0064] Such polycondensation can be catalyzed by either an acidic or alkaline pH. For example, the pH of the aqueous phase is lower than 7, more specifically 2.5–6, and even more specifically 3.5–5, or higher than 7, more specifically 8–12, and even more specifically 9–11. If the aqueous phase is too acidic or alkaline, undesirable hydrolysis of the siloxane bond may occur.

[0065] The polycondensation step is preferably carried out within a temperature range of 10°C to 95°C, more specifically 25°C to 90°C. If the temperature is too low, the polycondensation may be too slow, but if the temperature is too high, the polycondensation may be too fast and uncontrollable, for example, leading to the formation of microcapsule aggregates.

[0066] In a specific embodiment of the present invention, step d) employs an adduct of aminosilane and a polyfunctional isocyanate, wherein the pH of the aqueous phase is lower than 7, more specifically 2.5 to 6, and even more specifically 3.5 to 5; and the temperature of the emulsion is raised to 10°C to 95°C, more specifically 25°C to 90°C, over a period of 2 to 6 hours, more specifically 3 to 5 hours.

[0067] In a specific embodiment of the present invention, the hydrated polymer phase in step e) is a coacervate, more specifically a composite coacervate formed from a positively charged polymer electrolyte and a negatively charged polymer electrolyte.

[0068] As used herein, the term “coacervate” refers to a phase of polymer electrolyte-rich droplets coexisting with an aqueous, polymer electrolyte-poor continuous phase. The droplets may aggregate at the interface to form an interfacial layer. In this context, coacervate droplets aggregate at the interface between the polymer stabilizer and the aqueous phase. As a result, a composition encapsulated in water is formed, containing multiple core droplets stabilized by the polymer stabilizer, each droplet surrounded by coacervate droplets.

[0069] "Composite coacervation" refers to the formation of an interfacial layer containing a mixture of polymer electrolytes.

[0070] The phenomenon of coacervation can also be observed with an optical microscope and is indicated by the appearance of a ring around the core droplet. This ring consists of the aforementioned polymer electrolyte-rich phase, which has a different refractive index from the surrounding aqueous phase.

[0071] Coacervation of polymer electrolytes is generally induced by bringing the polymer electrolyte to its isoelectric point, which means the point at which its net charge is zero or near zero. This can be achieved by changing the salt concentration or pH of the aqueous phase. In the process of complex coacervation, complexation occurs at a pH where one polymer electrolyte has an overall positive charge and the other polymer electrolyte has an overall negative charge, resulting in the overall charge of the complex becoming neutral.

[0072] As is known in the art, pH control can be used as a means to induce coacervation. Therefore, positively charged polymeric electrolytes preferably have a pH-dependent charge. This is the case for polymers with primary, secondary, and tertiary amino groups, such as polyamines like chitosan, and most proteins, such as gelatin. Proteins have the additional advantage of being prone to temperature-dependent structural transitions, which can also be used to control the morphology of coacervates. In particular, varying the temperature of some proteins induces the formation of secondary, tertiary, or quaternary structures of the proteins, which can also be used to control the properties of coacervates.

[0073] Similarly, negatively charged polymer electrolytes containing carboxyl groups have a pH-dependent charge.

[0074] Particularly suitable coacervates are described in WO2023020883A1.

[0075] In a specific embodiment of the present invention, in the formation of a composite coacervate, a negatively charged polysaccharide is used as a negatively charged polymer electrolyte. By using one component for two purposes, the overall complexity and cost of the encapsulated composition can be reduced. Furthermore, because fewer components are required for manufacturing, the environmental impact of the product can be improved.

[0076] In a specific embodiment of the present invention, in step f), the composite coacervate and polymer stabilizer are crosslinked. Crosslinking in this means immobilizes the coacervate on the polymer stabilizer present at the core interface, providing a shell consisting of a polymer complex rather than a simple blend of individual polymers. Crosslinking can be achieved using a polyfunctional aldehyde, a polyfunctional epoxidized compound, a polyfunctional succinimidyl compound, or an enzyme, particularly transglutaminase.

[0077] Polyfunctional aldehydes can be selected from the group consisting of succinaldehyde, glutaraldehyde, glyoxal, benzene-1,2-dialdehyde, benzene-1,3-dialdehyde, benzene-1,4-dialdehyde, piperazine-N,N-dialdehyde, and 2,2'-bipyridyl-5,5'-dialdehyde.

[0078] Epoxidized compounds or resins, more specifically polyfunctional glycidyl compounds, are described in joint application GB2203193.4. Epoxidized compounds include, but are not limited to, epoxidized unsaturated oils, e.g., epoxidized soybean oil, epoxidized vegetable oil, etc.; epoxidized alcohols, e.g., isosorbide glycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, glycerol polyglycidyl ether, diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, polyglycerol-3-glycidyl ether, trimethylolpropane polyglycidyl This includes diglycidyl ethers, neopentyl glycol diglycidyl ethers, 1,6-hexanediol diglycidyl ethers, pentaerythritol polyglycidyl ethers; castor oil glycidyl ethers; epoxidized polysaccharides, such as sorbitol polyglycidyl ethers; epoxidized phenols, such as resorcinol diglycidyl ethers, hydrogenated bisphenol A diglycidyl ethers, diglycidyl terephthalate; diglycidyl o-phthalate; N-glycidyl phthalimide; epoxy cresol novolac resins; hexahydrophthalate diglycidyl esters; epoxidized terpenes, etc.

[0079] In the context of the present invention, coacervates, and in particular composite coacervates crosslinked by covalent bonds, are considered hydrogels. A "hydrogel" is a three-dimensional network of hydrophilic polymers that can swell in water while maintaining its structure, due to chemical or physical crosslinking of individual polymer chains.

[0080] The applicant found that the use of hydrogels particularly enhances both the deposition and adhesion of microcapsules to the substrate and, separately, to the fabric.

[0081] Such hydrogels can also be formed by several methods at the interface, particularly by the self-assembly of polymer electrolytes around an existing interface, covalent grafting of pre-formed hydrogel particles in solution, polymerization of water-soluble monomers initiated at the interface, and phase separation of water-soluble macromolecules at the interface.

[0082] The shell may further contain one or more polyfunctional carboxylic acids selected from the group consisting of citric acid, benzene-1,3,5-tricarboxylic acid, benzene-1,2,4-tricarboxylic acid, 2,5-franzicarboxylic acid, itaconic acid, poly(itaconic acid), and combinations thereof. These polyfunctional carboxylic acids improve the retention of beneficial agents in the microcapsules during drying, for example, when the microcapsules are deposited on a substrate and the substrate is dried in a line or dryer.

[0083] After core-shell microcapsules are formed, the resulting composition is typically cooled to room temperature. The composition may be further processed before, during, or after cooling. Further processing may include treatment of the composition with an antimicrobial preservative, which is well known in the art. Further processing may also include the addition of suspension aids, such as hydrophilic colloidal suspension aids, to help stabilize the physical dispersion of the microcapsules and prevent creaming or coalescence. Any additional adjuvants conventional in the art may also be added during further processing.

[0084] A method according to the present invention may include an additional step of drying the microcapsules to obtain a powder form of the composition.

[0085] Optionally, additional materials including carrier materials such as salts, silicates, clays, and carbohydrates; refractory materials; additional functional materials such as fragrance components, cosmetic components, bioactive components, and substrate enhancers; additional materials such as polysaccharides, proteins, alkoxysilanes, synthetic polymers, and copolymers; surfactants; and waxes may be added to the powdered composition.

[0086] Drying methods such as spray drying, spray coating, belt drying, and drum drying may be employed. These methods are well known to the technicians. In particular, the drying process may involve an additional encapsulation process in which additional functional materials are encapsulated in additional encapsulating materials. For example, a composition in the form of a drying slurry obtained according to the present invention may, in addition to the core-shell microcapsules obtained in the process according to the present invention, include at least one unencapsulated functional material and at least one water-soluble encapsulating material, so that the functional material not encapsulated in the core-shell microcapsules is encapsulated in the water-soluble encapsulating material during drying. Typically, the at least one water-soluble encapsulating material includes at least one hydrophilic colloid, such as starch octenyl succinic acid and gum acacia. The hydrophilic colloid promotes and stabilizes the dispersion of the unencapsulated material in the aqueous phase of the slurry, and upon drying, causes a matrix to form around or coexist with the core-shell microcapsules.

[0087] A method for obtaining the encapsulated composition described herein in a dry powder form represents an additional aspect of the present invention.

[0088] The beneficial agent encapsulated in a core-shell microcapsule may contain a first fragrance, while the functional material enclosed in a water-soluble encapsulating material may contain a second fragrance, and the first and second fragrances may be the same or different.

[0089] Combining at least two encapsulation processes has the advantage of providing different mechanisms for releasing functional materials and beneficial agents, such as a combination of moisture-induced release and mechanical pressure-induced release.

[0090] The drying step may be followed by mechanical or thermal treatments, such as spheroidizing, granulation, and extrusion.

[0091] In specific embodiments, the polymer stabilizer is formed by the polycondensation of an adduct formed by the reaction of bis(3-(triethoxysilyl)propyl)amine with 2-ethylpropane-1,2,3-triyltris((3-(isocyana-tomethyl)phenyl)carbamate). Under such conditions, the oil phase or portion of the oil phase in which the adduct is formed preferably does not contain amines, aldehydes, and alpha-beta unsaturated alcohols. More specifically, the oil phase contains less than 5% by weight, more specifically less than 1% by weight, and even more specifically less than 0.1% by weight of amines, aldehydes, enols, and halogenated components. Without being bound by any theory, the applicant believes that avoiding amines, aldehydes, and alpha-beta unsaturated alcohols may help mitigate undesirable side reactions that may interfere with the formation of core-shell microcapsules.

[0092] In these specific embodiments, the Hansen solubility parameter of 2-ethylpropane-1,2,3-triyltris((3-(isocyanate-methyl)phenyl)carbamate) is used in equations 1-4: δD B =19.077, δP B =10.76 and δH B = 4.81.

[0093] In specific embodiments of the present invention, the beneficial agent is a fragrance composition comprising one or more fragrance components. A wide range of fragrance components that may be used in the present invention are listed below herein.

[0094] In aspects of the present invention, the fragrance component has a calculated logarithm of an octanol / water partition coefficient (ClogP) of 2.8 or higher, more specifically 3.2 or higher, and 150 cm 3 More than / mol, or more specifically 170cm³ 3 It has a molar volume of 1 / mol or more. Components that meet these conditions are less likely to leach from the oil core into the aqueous phase during the encapsulation process and after the core-shell microcapsules have been formed.

[0095] The ClogP value provides a convenient estimate of the affinity of fragrance components to the encapsulated oil phase. A higher ClogP indicates a higher affinity of the component to the oil phase. In the context of this invention, the ClogP of a component is preferably calculated using the calculation software incorporated in ChemDraw professional software version 18.1.0.535. ChemDraw is part of the ChemOffice software platform commercialized by Perkin Elmer.

[0096] Molar volume provides a convenient estimate of the tendency of encapsulated components to diffuse through the shell of a core-shell microcapsule. A larger molar volume indicates a lower tendency of components to diffuse through the microcapsule shell. In the context of this invention, molar volume can be calculated using the ACD / Labs Percepta Platform - ChemSketch Module version 2020.1.2, commercialized by ACD / Labs. In all cases, the average value is used. Those skilled in the art are familiar with calculating physicochemical properties using the PhySchem module of ACD / Labs ChemSketch.

[0097] As referred to above in this specification, in specific embodiments, in particular, when the macromer is formed in situ in the oil phase, the fragrance component may be divided into a first and second portion of the oil phase, and the macromer may be formed in the first portion of the oil phase. Under such conditions, the first portion of the oil phase contains the fragrance component which is compatible with both the reactive building blocks that form the macromer and the macromer itself.

[0098] In a specific embodiment, the first portion of the oil phase includes, based on the total weight of the first portion of the oil phase: a) Amines, aldehydes, enols, and halogenated components in amounts less than 5% by weight, more specifically less than 1% by weight, and even more specifically less than 0.1% by weight; b) Components that have a Hansen solubility parameter of 40% by weight or more, more specifically 60% by weight or more, even more specifically 75% by weight or more, even more specifically 90% by weight or more, and even more specifically 95% by weight or more, and are referred to as Group 1 components:

number

number

number

[0099] Components that meet these conditions are less likely to leach from the microcapsule core into the aqueous phase during the encapsulation process and after the microcapsules have been formed.

[0100] In a specific embodiment of the present invention, the first portion of the oil phase contains a Group 1 component which is a fragrance component selected from the group consisting of: (2-(1-propoxyethoxy)ethyl)benzene (Acetal R); (Z)-Oxacycloheptadeca-10-en-2-one (Ambrettolide); Pentyl 2-phenyl acetate (Amyl Phenyl Acetate); 3,5-Diethyl-2,5-dimethylcyclohexa-2-enone (Azarbre); 7-Isopentyl-2H-benzo[b][1,4]dioxepin-3(4H)-one (Azurone); Benzyl Benzoate; Benzyl 3-phenylpropanoate (Benzyl Cinnamate); Benzyl 2-methylpropanoate (Benzyl Isobutyrate); Benzyl 3-methylbutanoate (Benzyl Isovalerate); Benzyl 2-phenyl acetate (Benzyl Phenyl Acetate; Benzyl 2-hydroxybenzoate; Butyl Butyro Lactate;

[0101] ((1S,8aR)-1,4,4-trimethyl-2,3,3a,4,5,8-hexahydro-1H-5,8a-methanoazulene-6-yl)methanol (Cedrenol); (1S,6R,8aR)-1,4,4,6-tetramethyloctahydro-1H-5,8a-methanoazulene-6-ol (Cedrol Crystals Extra); (4Z,8Z)-1,5,9-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene (Cedroxyde); methyl 2-(3-oxo-2-pentylcyclopentyl)acetate (Cepionate); 3-phenylpropa-2-enyl 3-phenylpropa-2-enoate (Cinnamyl Cinnamate Distilled); (E)-1,1-Dimethoxy-3,7-dimethylocta-2,6-diene (Citral Dimethyl Acetal); (Z)-1,1-Diethoxy-3,7-dimethylocta-2,6-diene (Citrathal R); 3,7-Dimethylocta-6-en-1-ylethyloxalate (Citronellyl Ethoxalate); 3,7-Dimethylocta-6-en-1-ylformate (Citronellyl Formate); 3,7-Dimethylocta-6-ennitrile (Citronellyl Nitrile); (Z)-3-Methylcyclotetradeca-5-enone (Cosmone); (4-Methylphenyl)octanoate (Cresyl Caprylate Para); (4-Methylphenyl)2-phenylacetate (Cresyl Caprylate Para; 2-(4-methylphenoxy)acetaldehyde (Curgix); Allyl 2-(cyclohexyloxy)acetate (Cyclogalbanate); 2-cyclohexyl ethyl acetate (Cyclohexyl Ethyl Acetate); Cyclohexyl 2-hydroxybenzoate (Cyclohexyl Salicylate); 3-(4-methylcyclohexa-3-en-1-yl)butan-1-ol (Cyclomethylene Citronellol);

[0102] (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)buta-2-en-1-one (Damascenone); (E)-1-(2,6,6-trimethylcyclohexa-2-en-1-yl)buta-2-en-1-one (Damascone Alpha); (E)-1-(2,6,6-trimethyl-1-cyclohexenyl)buta-2-en-1-one (Damascone Beta); 1-(2,6,6-trimethyl-1-cyclohexa-3-enyl)buta-2-en-1-one (Damascone Delta); Decanonitrile; (oxybis(methylene))dibenzene; 3-methyl-2-pentylcyclopenta-2-enone (Dihydro Jasmone); 6-Heptyltetrahydro-2H-pyran-2-one (Dodecalactone Delta); 5-Octyloxolan-2-one (Dodecalactone Gamma); 1,4-Dioxacycloheptadecane-5,17-dione (Ethylene Brassylate; 3-(4-ethylphenyl)-2,2-dimethylpropanenitrile (Fleuranil); (E)-undeca-9-ennitrile (Floridile); (3aR,6S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoindene-6-ylpropanoate (Florocyclene); 2,4,6-trimethyl-4-phenyl-1,3-dioxane (Floropal); (3aS,4S,7R,7aS)-ethyloctahydro-1H-4,7-methanoindene-3a-carboxylate (Fruitate); 2-methyldecanonitrile (Frutonile);

[0103] 1-(1,2,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-yl)ethanone (Georgywood); (E)-6,10-dimethylundeca-5,9-dien-2-one (Geranyl Acetone); (E)-oxacyclohexadeca-12-en-2-one (Habanolide); methyl 3-oxo-2-pentylcyclopentaneacetate (Hedione); heptane-2-one (Heptone); (Z)-hexa-3-en-1-ylbenzoate (Hexenyl-3-Cis Benzoate); (Z)-hexa-3-en-1-yl(Z)-hexa-3-enoate (Hexenyl-3-Cis Hexenoate; (Z)-Hexenyl-3-Cis Salicylate; (Z)-Hexenyl-3-Enyl](E)-2-Methylbuta-2-enoate; Hexyl Salicylate;

[0104] (E)-4-(2,6,6-trimethylcyclohexa-1-en-1-yl)buta-3-en-2-one (Ionone Beta); (E)-3-methyl-4-(2,6,6-trimethylcyclohexa-2-en-1-yl)buta-3-en-2-one (Irisantheme); (E)-4-(2,6,6-trimethylcyclohexa-2-en-1-yl)buta-3-en-2-one (Irisone Alpha); 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-yl)ethanone (Iso E Super); 2-methylpropyl 2-phenylacetate (Isobutyl Phenyl Acetate); 2-methylpropyl 2-hydroxybenzoate (Isobutyl Salicylate; 2-Hexylcyclopenta-2-en-1-one (Isojasmone B 11); 2-Hexylcyclopenta-2-enone (Isojasmone T); (E)-3-methyl-4-(2,6,6-trimethylcyclohexa-2-en-1-yl)buta-3-en-2-one (Isoraldeine 70); (3aR,6S,7aS)-3a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoindene-6-yl acetate (Jasmacyclene); 2-Hexylcyclopentanone (Jasmatone); (E)-6-(penta-3-en-1-yl)tetrahydro-2H-pyran-2-one (Jasmolactone); 3-Butyl-5-methyltetrahydro-2H-pyran-4-yl acetate (Jasmonyl); 3-Pentyltetrahydro-2H-pyran-4-yl acetate (Jasmopyrane);

[0105] (4Z)-Hepta-4-en-2-yl 2-hydroxybenzoate (Karmaflor); (2E,6Z)-3,7-dimethylnonano-2,6-diennitrile (Lemonile); 3-methyl-5-phenylpentan-1-ol (Mefrosol); 5-methyl-2-propan-2-ylcyclohexyl]2-hydroxypropanoate (Menthyl Lactate); methylnonano-2-inoate (Methyl Octyne Carbonate); (E)-3-methyl-4-(2,6,6-trimethylcyclohexa-1-en-1-yl)buta-3-en-2-one (Methylionantheme); (Z)-3-methylcyclopentadeca-5-enone (Muscenone); 1,4-dioxacyclohexadecane-5,16-dione (Musk C14); 1,7-dioxacycloheptadecane-8-one (Musk R1); (4-(4-methylpenta-3-en-1-yl)cyclohexa-3-en-1-yl)methylacetate; 2-(2-(4-methylcyclohexa-3-en-1-yl)propyl)cyclopentan-1-one (Nectaryl); (E)-methylnona-2-enoate (Neofolione); (E)-13-methyloxacyclopentadeca-10-en-2-one (Nirvanolide); 4,4a-dimethyl-6-(propa-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalene-2(3H)-one (Nootkatone Crystals);

[0106] 4-(tert-pentyl)cyclohexanone (Orivone); 2-ethyl-N-methyl-N-(m-tolyl)butanamide (Paradisamide); 1,1-dimethoxynonana-2-yin (Parmavert); 5-heptyldihydrofuran-2(3H)-one (Peach Pure); 2-cyclohexyllidene-2-phenylacetonitrile (Peonile); 3,7-dimethylocta-1,6-diene-3-yldimethylcarbamate (Pepperwood); 2-cyclohexyllidene-2-(o-tolyl)acetonitrile (Petalia); 2-(phenoxy)ethyl 2-methylpropanoate (Phenoxy Ethyl Isobutyrate); 2-phenylethyl 3-phenylpropanoate (Phenyl Ethyl Cinnamate); 2-phenylethyl 2-methylpropanoate (Phenyl Ethyl Isobutyrate; 2-Phenyl Ethyl Phenyl Acetate; 2-Phenyl Ethyl Salicylate Crystals; (2E,5E)-5,6,7-Trimethylocta-2,5-dien-4-one (Pomarose);

[0107] (4aR,8aS,E)-6-ethylideneoctahydro-2H-5,8-methanochromene (Rhuboflor); 3-(2-methylpropyl)-1-methylcyclohexanol (Rossitol); 2,3,3-trimethyl-1-indanone (Safraleine); 4,5,6,7,8,9,10,11,12,13-decahydrocyclododeca[d]oxazole (Sclarene 50% / Tec); 1-(spiro[4.5]deca-6-en-7-yl)penta-4-en-1-one (Spirogalbanone Pure); (E)-tridecene-2-ennitrile (Tridecene-2-Nitrile); 6-hexyltetrahydro-2H-pyran-2-one (Undecalactone Delta); (Z)-cyclohexadeca-5-enone (Velvione); or mixtures thereof.

[0108] In a specific embodiment of the present invention, the first part of the oil phase contains a group 2 component which is a fragrance component selected from the group consisting of: octyl acetate (Acetate C 8 Octylic); (Z)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene (Acetyl Caryophyllene); 2-methyl-4-(5,6,6-trimethylbicyclo[2.2.1]hepta-2-ylcyclohexanone (Aldrone); propa-2-enyl 2-(3-methylbutoxy)acetate (Allyl Amyl Glycolate); propa-2-enylheptanoate (Allyl Oenanthate); 1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-ol (Amber Core); 1,3,4,5,6,7-Hexahydro--Beta-,1,1,5,5-Pentamethyl-2H-2,4a-Methanonaphthalene-8-ethanol (Ambermax); (2-(Isopentyloxy)ethyl)benzene (Anther); 1-(3,3-Dimethylcyclohexyl)ethyl formate (Aphermate); (E)-2-Ethyl-4-(2,2,3-Trimethylcyclopenta-3-en-1-yl)buta-2-en-1-ol (Bacdanol); (1R,2S,4R)-2'-Isopropyl-1,7,7-Trimethylspiro[Bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] (Belambre); 2-Methyl-6-methyleneocta-7-en-2-yl acetate (Bergamyl Acetate; (Ethoxymethoxy)cyclododecane (Boisambrene Forte); (2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate (Bornyl Acetate); 4-(tert-butyl)cyclohexanol (Butyl Cyclohexanol Para);

[0109] 1,1,2,3,3-Pentamethyl-2,3,6,7-Tetrahydro-1H-Indene-4(5H)-one (Cashmeran); ((3R,3aS,7R,8aS)-3,8,8-Trimethyl-2,3,4,7,8,8a-Hexahydro-1H-3a,7-Methanoazulene-6-yl)methylacetate (Cedrenyl Acetate); (1S,6R,8aR)-1,4,4,6-Tetramethyloctahydro-1H-5,8a-Methanoazulene-6-ylacetate (Cedryl Acetate Crystals); 2-Methyl-4-(2,6,6-Trimethylcyclohexa-2-en-1-yl)butanal (Cetonal); 3,7-Dimethylocta-6-en-1-ol (Citronellol) 750); 3,7-Dimethylocta-6-en-1-ol (Citronellol); 3,7-Dimethylocta-6-en-1-yl acetate (Citronellyl Acetate); 3,7-Dimethylocta-6-en-1-yl propanoate (Citronellyl Propionate); 4-Cyclohexyl-2-methylbutan-2-ol (Coranol); Ethyl 2,6,6-trimethylcyclohexa-1,3-diene-1-carboxylate (Cristalon);

[0110] 3,7-Dihydro Linalool; 2,6-Dihydro Myrcenol; 2-Dimethyl Benzyl Carbinyl Butyrate; (E)-3-Methyl-5-(2,2,3-Trimethylcyclopenta-3-en-1-yl)penta-4-en-2-ol (Ebanol); (2E,4Z)-Ethyl Decadienoate; Ethyl Decadienoate; (E)-3,7-Dimethylnonano-1,6-Dien-3-ol (Ethyl Linalool); Ethyl Octanoate; Ethyl Nonanoate; Ethyl 2,6,6-Trimethylcyclohexa-1,3-Dien-1-Carboxylate (Ethyl Safranate; (2S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl acetate (Fenchyl Acetate); 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalene-2-yl)ethanone (Fixolide); 2,6-dimethylocta-7-en-2-ol (Floralym); (Z)-1-(cycloocta-3-en-1-yl)propan-1-ol (Florymoss); 4,4,8,8-tetramethyloctahydro-4a,7-methanonaphtho[1,8a-b]oxylen (Folenox);

[0111] (3aR,6S,7aS)-3a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoinden-6-yl 2-methylpropanoate (Gardocyclene); (E)-3,7-dimethylocta-2,6-dien-1-yl acetate (Geranyl Acetate) Synthetic); 2-(8-isopropyl-6-methylbicyclo[2.2.2]octa-5-en-2-yl)-1,3-dioxolane (Glycolierral); (Z)-hexa-3-en-1-ylbutanoate; (Z)-hexa-3-en-1-yl2-methylpropanoate; hexylbutanoate; hexyl2-methylpropanoate; (E)-4-(2,5,6,6-tetramethyl-1-cyclohexa-2-enyl)buta-3-en-2-one (Ironal); (E)-4-(2,5,6,6-tetramethylcyclohexa-2-en-1-yl)buta-3-en-2-one (Irone Alpha); 2,2,7,7-Tetramethyltricyclo[6.2.1.01,6]undecane-5-one (Isolongifolanone); (1-Methyl-2-((1,2,2-trimethylbicyclo[3.1.0]hexane-3-yl)methyl)cyclopropyl)methanol (Javanol); 1-(4-Methoxy-2,2,6,6-Tetramethylcyclohexa-3-en-1-yl)ethanone (Kefarene); (Z)-1-(1-Ethoxyethoxy)hexa-3-ene (Leaf Acetal); 3,7-Dimethylocta-1,6-dien-3-ol (Linalool Synthetic); 3,7-Dimethylocta-1,6-dien-3-yl formate (Linalyl Formate);

[0112] 2-(4-methylcyclohexyl)propane-2-yl acetate (Menthanyl Acetate); 2-isopropyl-5-methylcyclohexanol (Menthol); 1-((1S,8aS)-1,4,4,6-tetramethyl-2,3,3a,4,5,8-hexahydro-1H-5,8a-methanoazulene-7-yl) ethane (Methyl Cedryl Ketone); (2-methyl-6-methyllideneocta-7-en-2-yl) acetate (Myrcenyl Acetate); 2-methylundecanoic acid (Mystikal); 2-methyl-6-methyleneocta-7-en-2-yl acetate (Neobergamate) Forte); 10-Isopropyl-2,7-dimethyl-1-oxaspiro[4.5]deca-3,6-diene (Neocaspirene); (E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol (Nerolidol); (Z)-3,7-dimethylocta-2,6-dien-1-yl acetate (Neryl Acetate); 2-(6,6-dimethylbicyclo[3.1.1]hepta-2-en-2-yl)ethyl acetate (Nopyl Acetate);

[0113] 2,4-Dimethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)-1,3-dioxolane (Okoumal); (1-methyl-2-(((1R,3R)-2,2,3-trimethylcyclopentyl)methyl)cyclopropyl)methanol (Pashminol); 2,2-dimethyl-2-phenylethylpropanoate (Pivarose); ethyl 2-cyclohexylpropanoate (Poirenate); (E)-2-ethyl-4-(2,2,3-trimethylcyclopenta-3-en-1-yl)buta-2-en-1-ol (Radjanol); 2-(cyclohexylmethyl)-4,4,6-trimethyl-1,3-dioxane (Resedal); A mixture of 3,7-dimethylocta-6-en-1-ol and 3,7-dimethylocta-7-en-1-ol (Rhodinol); Deca-9-en-1-ol (Rosalva); 3-((1R,2S,4R,6R)-5,5,6-trimethylbicyclo[2.2.1]heptan-2-yl)cyclohexanol (Sandela); (E)-2-methyl-4-(2,2,3-trimethyl-1-cyclopenta-3-enyl)buta-2-en-1-ol (Santacore); 2-(1-(3,3-dimethylcyclohexyl)ethoxy)-2-methylpropylcyclopropanecarboxylate (Serenolide); (E)-6-ethyl-3-methylocta-6-en-1-ol (Super Muguet; (E)-2-((3,5-dimethylhexa-3-en-2-yl)oxy)-2-methylpropylcyclopropanecarboxylate (Sylkolide);

[0114] (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate (Tangerinol); 2-(4-methyl-1-cyclohexa-3-enyl)propane-2-yl acetate (Terpinyl Acetate); oxacyclohexadecan-2-one (Thibetolide); (E)-4-methyldeca-3-en-5-ol (Undecavertol); 2,2,5-trimethyl-5-pentylcyclopentanone (Veloutone); 1-((1S,8aS)-1,4,4,6-tetramethyl-2,3,3a,4,5,8-hexahydro-1H-5,8a-methanoazulene-7-yl) ethanolone (Vertofix Coeur); 4-methyl-4-phenylpentan-2-yl acetate (Vetikol Acetate / Corps Rhubarb; (4,8-dimethyl-2-propane-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulene-6-yl) acetate (Vetiveryl Acetate); (2R,5R,8S)-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecane-1-yl acetate (Vetynal); [(3Z)-4,11,11-trimethyl-8-methylidene-5-bicyclo[7.2.0]undeca-3-enyl] acetate (Vetyvenal); or mixtures thereof.

[0115] A second portion of the oil phase may be added before the adduct is formed and before the formation of the polymer stabilizer is completed by polycondensation of the adduct at the oil-water interface. The selection criteria for the second portion of the oil phase fragrance components are not so restrictive in terms of compatibility with the reactive block and the adduct. However, the adduct should preferably be compatible with the oil phase as a whole so that polycondensation of the adduct occurs at the oil-water interface. Therefore, the second oil phase preferably is substantially free of incompatible fragrance components, such as alpha-beta unsaturated aldehydes that can react with residual unreacted amino groups remaining in the adduct. "Substantially free" means that incompatible components, such as alpha-beta unsaturated aldehydes, should be present in amounts of less than 5% by weight, more specifically less than 1% by weight, and even more specifically less than 0.1% by weight, based on the total weight of the second oil phase.

[0116] In a preferred embodiment of the present invention, the oil phase is divided into a first part and a second part, the first part being as defined herein, and the second part of the oil phase being, based on the total weight of the second oil phase, including: a) Amines and alpha-beta unsaturated aldehydes in amounts less than 5% by weight, more specifically less than 1% by weight, and even more specifically less than 0.1% by weight; b) Aldehydes that are not alpha-beta unsaturated aldehydes, present in an amount of 15% by weight or less. c) Components having a ClogP of 2.5 to 3.0 in less than 40% by weight, and components having a ClogP of less than 2.5 in less than 5% by weight; d) 150cm with less than 30% by weight 3 / mol~170cm 3 Components having a molar volume of / mol, and less than 5% by weight of 150cm³ 3 Components having a molar volume of less than / mol, e) Components having Hansen solubility parameters δD, δp, and δh that satisfy the conditions given by equation 8, with a concentration of 50% by weight or less:

number

[0117] The alpha-beta unsaturated aldehydes particularly desired in the second part of the oil phase include: (E)-dodeca-2-enal (Aldehyde Mandarine); (Z)-2-benzylideneheptanal (Amyl Cinnamic Aldehyde); (2E)-3-phenylpropa-2-enal (Cinnamic Aldehyde); (E)-3,7-dimethylocta-2,6-dienal (Citral); (E)-dodeca-2-enal (Dodecenal); (E)-hexa-2-enal (Hexenal-2-Trans); (E)-2-benzylideneoctanal (Hexyl Cinnamic Aldehyde); nona-2-enal (Iris Aldehyde); methyl 2-aminobenzoate (Methyl Anthranilate); (Z)-2-methyl-3-phenylacrylaldehyde (Methyl Cinnamic Aldehydes; (E)-5-methyl-2-phenylhexa-2-enal and (Z)-5-methyl-2-phenylhexa-2-enal (Methyl Phenyl Hexenal); (2E,6Z)-nona-2,6-dienal (Nonadienal); 2,6,6-trimethylcyclohexa-1,3-diencarbaldehyde (e.g., Safranal); (E)-tridecenal-2-trans); and mixtures thereof, alpha-beta unsaturated aldehydes, e.g., (E)-methyl 2-(((4-(4-hydroxy-4-methylpentyl)cyclohexa Schiff bases that readily release -3-en-1-yl)methylene)amino)benzoate (Lyranthion); methyl 2-((E)-((E)-2-benzylideneheptylidene)-amino)benzoate (Seringone) and (E)-methyl 2-((3-(4-(tert-butyl)phenyl)-2-methylprop-1-en-1-yl)amino)benzoate (Verdantion) are also desired in the second oil phase.

[0118] In a specific embodiment of the present invention, the second portion of the oil phase contains at least one fragrance component. The encapsulated fragrance according to the present invention preferably comprises a fragrance component selected from the group consisting of: (E)-2-methoxy-4-(prop-1-en-1-yl)phenylacetate (Acetyl Isoeugenol); (2-(1-ethoxyethoxy)ethyl)benzene (Acetal E); (2-(1-propoxyethoxy)ethyl)benzene (Acetal R); octylacetate (Acetate C 8 Octylic); (Z)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undeca-4-ene (Acetyl Caryophyllene); 2,6,10-trimethylundeca-9-enal (Adoxal); N-ethyl-N-(m-tolyl)propionamide (Agarbois); 2-(tert-butyl)cyclohexylacetate (Agrumex); decane-1-ol (Alcohol C 10 Decylic); Dodecane-1-ol (Alcohol C 12 Lauric); Tridecane-1-ol (Alcohol C 13 Oxo); Decanal (Aldehyde C 10 Decylic); 2-Methyldecanal (Aldehyde C 11 MOA); Undeca-10-enal (Aldehyde C 11 Undecylenic); Undecal (Aldehyde C 11); Dodecal (Aldehyde C 12 Lauric); 2-Methylundecal (Aldehyde C 12 MNA); (E)-Undeca-9-enal (Aldehyde Iso C 11); (E)-Dodeca-2-enal (Aldehyde Mandarine) 10% / Tec); 2-methyl-4-(5,6,6-trimethylbicyclo[2.2.1]hepta-2-ylcyclohexanone (Aldrone); 2,6-dimethylheptan-4-yl acetate (Alicate); propa-2-enyl 2-(3-methylbutoxy)acetate (Allyl Amyl Glycolate); propa-2-enyl 3-cyclohexylpropanoate (Allyl Cyclohexyl Propionate); propa-2-enylheptanoate (Allyl Oenanthate);1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-ol (Amber Core); 3,8,8,11a-tetramethyldodecahydro-1H-3,5a-epoxynaphtho[2,1-c]oxepene (Amberketal); (Z)-oxacycloheptadeca-10-en-2-one (Ambrettolide); 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene-2-ol (Ambrinol); (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazureno[5,6-d]-1,3-dioxol (Ambrocenide) Crystals); (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran (Ambrofix); (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran (Ambroxan); (Z)-2-benzylideneheptanal (Amyl Cinnamic Aldehyde); pentyl 2-phenylacetate (Amyl Phenyl Acetate); pentyl 2-hydroxybenzoate (Amyl Salicylate; Phenylethyl 2-methylbutanoate (Anatolyl); (2-(isopentyloxy)ethyl)benzene (Anther); 1-(3,3-dimethylcyclohexyl)ethyl formate (Aphermate); (E)-methyl 2-((7-hydroxy-3,7-dimethyloctylidene)amino)benzoate (Aurantiol Pure); 3,5-diethyl-2,5-dimethylcyclohexa-2-enone (Azarbre); 7-isopentyl-2H-benzo[b][1,4]dioxepin-3(4H)-one (Azurone);

[0119] (1R,2S,4R)-2'-isopropyl-1,7,7-trimethylspiro[bicyclo-[2.2.1]heptane-2,4'-[1,3]dioxane](Belambre); benzyl bezoate; benzyl butyrate; benzyl 3-phenylpropanoate-2-enoate; benzyl cinnamate; benzyl 2-methylpropanoate; benzyl isovalerate; benzyl 2-phenyl acetate; benzyl 2-hydroxybenzoate; 2-methyl-6-methyleneocta-7-en-2-yl acetate; (ethoxymethoxy)cyclododecane (Boisambrene) Forte); (1S,2R,5R)-2-ethoxy-2,6,6-trimethyl-9-methylenebicyclo[3.3.1]nonane (Boisiris); (2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ylacetate (Bornyl Acetate); 3-(4-(tert-butyl)phenyl)propanal (Bourgeonal); (1R,5S,E)-1,5-dimethylbicyclo-[3.2.1]octane-8-oneoxime (Buccoxime); 1-Butoxy-1-oxopropane-2-ylbutanoate (Butyl Butyro Lactate); 4-(tert-butyl)cyclohexanol (Butyl Cyclohexanol Para); 4-(tert-butyl)cyclohexylacetate (Butyl Cyclohexyl Acetate) Para; 2-(2-methylpropyl)quinoline (Butyl Quinoline Secondary);

[0120] 1,2,4-Trimethoxy-5-propylbenzene (Calmode); (4Z)-4,11,11-Trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene (Caryophyllene); 1,1,2,3,3-Pentamethyl-2,3,6,7-Tetrahydro-1H-indene-4(5H)-one (Cashmeran); 5-Tert-Butyl-2-methyl-5-propyl-2H-furan (Cassyrane); ((1S,8aR)-1,4,4-Trimethyl-2,3,3a,4,5,8-H Xahydro-1H-5,8a-methanoazulene-6-yl)methanol (Cedrenol); (1S,6R,8aR)-1,4,4,6-tetramethyloctahydro-1H-5,8a-methanoazulene-6-ol (Cedrol); (4Z,8Z)-1,5,9-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene (Cedroxyde); (1S,6R,8aR)-1,4,4,6-tetramethyloctahydro-1H-5,8a-methanoazulene-6-yl acetate (Cedryl Acetate Crystals; (1R,6S,8aS)-6-Methoxy-1,4,4,6-Tetramethyloctahydro-1H-5,8a-Methanoazulene (Cedryl Methyl Ether); Methyl 2-(3-Oxo-2-Pentylcyclopentyl) Acetate (Cepionate); 3a,6,6,9a-Tetramethyl-2,4,5,5a,7,8,9,9b-Octahydro-1H-Benzo[e][1]Benzofran (Cetalox); 2-Methyl-4-(2,6,6-Trimethylcyclohexa-2-en-1-yl) Butanal (Cetonal); (E)-1-(2,6,6-Trimethylcyclohexa-2-en-1-yl)Hepta-1,6-Dien-3-one (Cetone) V); 3-Phenylpropa-2-enyl3-phenylpropa-2-enoate (Cinnamyl Cinnamate); (E)-1,1-Dimethoxy-3,7-Dimethylocta-2,6-diene (Citral Dimethyl Acetal); 3,7-Dimethylocta-6-enal (Citronellal Synthetic); 3,7-Dimethylocta-6-en-1-ol (Citronellol);3,7-Citronellyl Acetate; 3,7-Citronellyl Ethoxalate; 3,7-Citronellyl Formate; 3,7-Citronellyl Isobutyrate; 3,7-Citronellyl Nitrile; 2-((3,7-Citronellyl Oxyacetaldehyde); 3,7-Citronellyl Propionate); (Z)-Cycloheptadeca-9-enone (Civettone); 2,4,4,7-Tetramethylocta-6-en-3-one (Claritone); Dodecanenitrile (Clonal); 2-(tert-pentyl)cyclohexyl acetate (Coniferan); 4-Cyclohexyl-2-methylbutan-2-ol (Coranol); 2-(2-mercaptopropan-2-yl)-5-methylcyclohexanone (Corps Cassis); (4S)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane (Corps Pamplemousse); 2-(3-phenylpropyl)pyridine (Corps Racine Vs 10% / Tec); (Z)-3-methylcyclotetradeca-5-enone (Cosmone); (4-methylphenyl)octanoate (Cresyl Caprylate) Para; (4-methylphenyl)2-methylpropanoate (Cresyl Isobutyrate Para); (4-methylphenyl)2-phenylacetate (Cresyl Caprylate Para); Ethyl 2,6,6-trimethylcyclohexa-1,3-diene-1-carboxylate (Cristalon); 2-(4-methylphenoxy)acetaldehyde (Curgix); 3-(4-isopropylphenyl)-2-methylpropanal (Cyclamen Aldehyde Extra);8,8-Dimethyl-1,2,3,4,5,6,7,8-Octahydronaphthalene-2-carbaldehyde (Cyclemone A); Allyl 2-(cyclohexyloxy)acetate (Cyclogalbanate); 2-Cyclohexyl ethyl acetate (Cyclohexyl Ethyl Acetate); 3-(4-Methylcyclohexa-3-en-1-yl)butan-1-ol (Cyclomethylene Citronellol); 8,8-Dimethyl-1,2,3,4,5,6,7,8-Octahydronaphthalene-2-carbaldehyde (Cyclomyral); Hexyl 2-methylbutanoate (Cydrane); Methyl 1,4-dimethylcyclohexanecarboxylate (Cyprisate);

[0121] (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)buta-2-en-1-one (Damascenone); (E)-1-(2,6,6-trimethylcyclohexa-2-en-1-yl)buta-2-en-1-one (Damascone Alpha); (E)-1-(2,6,6-trimethyl-1-cyclohexenyl)buta-2-en-1-one (Damascone Beta); 1-(2,6,6-trimethyl-1-cyclohexa-3-enyl)buta-2-en-1-one (Damascone Delta); Decanonitrile; 6-Isopropyloctahydronaphthalene-2(1H)-one; (Z)-Decen-1-Al,Cis-4-; (E)-Decenal-2-Trans; (E)-Decenal-4-Trans; 9-Decenal-9; (Oxybis(methylene))dibenzene; 2-(sec-butyl)-1-vinylcyclohexyl acetate; (Z)-3,7,11-trimethyldodeca-6,10-dienal; 4-(2,6,6-trimethylcyclohexa-1-en-1-yl)butan-2-one Beta; 3-methyl-2-pentylcyclopenta-2-enone (Dihydro Jasmone); 3,7-dimethylocta-6-en-3-ol (Dihydro Linalool); 2,6-dimethylocta-7-en-2-ol (Dihydro Myrcenol); 2,6-dimethylocta-7-en-2-yl acetate (Dihydro Myrcenyl Acetate); 2-(4-methylcyclohexyl)propane-2-ol (Dihydro Terpineol); 2-methyl-1-phenylpropane-2-yl acetate (Dimethyl Benzyl Carbinyl Acetate); 2-methyl-1-phenylpropane-2-yl butyrate (Dimethyl Benzyl Carbinyl Butyrate);4,7-Dimethyl Octa-6-en-3-one; 2,6-Dimyrcetol; 2-(2-(3,3,5-trimethylcyclohexyl)acetyl)cyclopentanone (Dione); 6-Heptyltetrahydro-2H-pyran-2-one (Dodecalactone Delta); 5-Octyloxolan-2-one (Dodecalactone Gamma); (E)-Dodecenal 10% / Tec; (E)-4-((3aS,7aS)-Hexahydro-1H-4,7-methanoindene-5(6H)-ylidene)butanal (Dupical);

[0122] (E)-3-methyl-5-(2,2,3-trimethylcyclopenta-3-en-1-yl)penta-4-en-2-ol (Ebanol); 3-(1-ethoxyethoxy)-3,7-dimethylocta-1,6-diene (Elintaal); 3-(1-ethoxyethoxy)-3,7-dimethylocta-1,6-diene (Elintaal Forte); (2E,4Z)-ethyldecadienoate (Ethyl Decadienoate); (E)-3,7-dimethylnonano-1,6-dien-3-ol (Ethyl Linalool); (Z)-3,7-dimethylnonano-1,6-dien-3-yl acetate (Ethyl Linalyl Acetate); ethyloctanoate (Ethyl Octanoate); ethylnonanoate (Ethyl Pelargonate; Ethyl 2,6,6-trimethylcyclohexa-1,3-diene-1-carboxylate; Ethylene Brassylate; Methyl 2,4-dihydroxy-3,6-dimethylbenzoate (Evernyl);

[0123] (3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene (Farnesene); (2E,6Z)-3,7,11-trimethyldodeca-2,6,10-triene-1-ol (Farnesol Synthetic); (2S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl acetate (Fenchyl Acetate); 3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan (Fixambrene); 1-(3,5,5,6,8,8-Hexamethyl-5,6,7,8-Tetrahydronaphthalene-2-yl)ethanone (Fixolide); 3-(4-Ethylphenyl)-2,2-Dimethylpropanenitrile (Fleuranil); 3-(4-Ethylphenyl)-2,2-Dimethylpropanal (Floralozone); 2,6-Dimethylocta-7-en-2-ol (Floralym); 2-(tert-butyl)cyclohexylethylcarbonate (Floramat); 3-(3-Isopropylphenyl)butanal (Florhydral); (E)-Undeca-9-ennitrile (Flori dile); (3aR,6S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoindene-6-ylpropanoate (Florocyclene); 2,4,6-trimethyl-4-phenyl-1,3-dioxane (Floropal); (Z)-1-(cycloocta-3-en-1-yl)propane-1-ol (Florymoss); 4,4,8,8-tetramethyloctahydro-4a,7-methanonaphtho[1,8a-b]oxylen (Folenox); 3-methyldodecanenitrile (Frescile); (3aS,4S,7R,7aS)-ethyloctahydro-1H-4,7-methanoindene-3a-carboxylate (Fruitate); 2-methyldecanenitrile (Frutonile);

[0124] 4,6,6,7,8,8-Hexamethyl-1,3,4,6,7,8-Hexahydrocyclopenta[g]isochromene (Galaxolide); (3aR,6S,7aS)-3a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoinden-6-yl 2-methylpropanoate (Gardocyclene); 1-(1,2,8,8-Tetramethyl-1,2,3,4,5,6,7,8-Octahydronaphthalene-2-yl)ethanone (Georgywood); (E)-3,7-Dimethylocta-2,6-dien-1-ol (Geraniol 980); (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate (Geraniol Acetate; (E)-6,10-dimethylundeca-5,9-dien-2-one (Geranyl Acetone); (E)-3,7-dimethylocta-2,6-dien-1-yl formate (Geranyl Formate); ethyl 2-ethyl-6,6-dimethylcyclohexa-2-enecarboxylate (Givescone); 2-(8-isopropyl-6-methylbicyclo[2.2.2]octa-5-en-2-yl)-1,3-dioxolane (Glycolierral); 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho[1,2-c]furan (Grisalva); 2-(3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulene-5-yl)propan-2-yl acetate (Guaiyl Acetate; 2-butyl-4,6-dimethyl-3,6-dihydro-2H-pyran (Gyrane);

[0125] (E)-Oxacyclohexadeca-12-en-2-one (Habanolide); Methyl 3-oxo-2-pentylcyclopentaneacetate (Hedione); [2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methylpropyl]propanoate (Helvetolide); Heptane-2-one (Heptone); (2S)-Ethyl 3-isopropylbicyclo[2.2.1]hepta-5-en-2-carboxylate (Herbanate); (3R,5R)-3-ethoxy-1,1,5-trimethylcyclohexane (Herbavert); 2-butyl-4,4,6-trimethyl-1,3-dioxane (Herboxane); (Z)-Hexa-3-en-1-ylbenzoate (Hexenyl-3-Cis Benzoate); (Z)-Hexenyl-3-Cis Butyrate; (Z)-Hexenyl-3-Cis Hexenoate; (Z)-Hexenyl-3-Cis Isobutyrate; (Z)-Hexenyl-3-Cis Methyl-2-Butyrate; (Z)-Hexenyl-3-Cis Salicylate; (Z)-Hexenyl-3-Cis Tiglate; Hexyl Butanoate (Hexyl Butyrate; (E)-2-Benzylidene Octanal (Hexyl Cinnamic Aldehyde); Hexyl 2-Methylpropanoate (Hexyl Isobutyrate); Hexyl 2-Hydroxybenzoate (Hexyl Salicylate);

[0126] 8,8-di(1H-indol-3-yl)-2,6-dimethyloctan-2-ol (Indolene); (E)-4-(2,6,6-trimethylcyclohexa-1-en-1-yl)buta-3-en-2-one (Ionone Beta); (E)-3-methyl-4-(2,6,6-trimethylcyclohexa-2-en-1-yl)buta-3-en-2-one (Irisantheme); (E)-4-(2,6,6-trimethylcyclohexa-2-en-1-yl)buta-3-en-2-one (Irisone Alpha); (E)-4-(2,5,6,6-tetramethylcyclohexa-2-en-1-yl)buta-3-en-2-one (Irone Alpha); 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-yl)ethanone (Iso E Super); 2-methylpropyl benzoate (Isobutyl Benzoate); 2-methylpropyl 2-phenylacetate (Isobutyl Phenyl Acetate); 6-butan-2-yl quinoline (Isobutyl Quinoline-2); 2-methylpropyl 2-hydroxybenzoate (Isobutyl Salicylate); 2-methoxy-3-(4-methylpentyl)pyrazine (Isohexylmethoxy Pyrazine); 2-hexylcyclopenta-2-en-1-one (Isojasmone B 11); 2-hexylcyclopenta-2-enone (Isojasmone T); 2,2,7,7-tetramethyltricyclo[6.2.1.[01,6] Undecane-5-one (Isolongifolanone); 3,5,5-Trimethylhexyl Acetate (Isononanyl Acetate Pure); 3-Methylbutyl 3-Methylbutanoate (Isopentyl Isovalerate); 4-Methylpenta-4-en-2-yl 2-methylpropanoate (Isopentyrate); (E)-3-methyl-4-(2,6,6-Trimethylcyclohexa-2-en-1-yl)buta-3-en-2-one (Isoraldeine 70); (E)-3-methyl-4-(2,6,6-Trimethylcyclohexa-2-en-1-yl)buta-3-en-2-one (Isoraldeine Cetone Alpha);

[0127] (3aR,6S,7aS)-3a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoindene-6-ylacetate (Jasmacyclene); 2-Hexylcyclopentanone (Jasmatone); (Z)-3-Methyl-2-(penta-2-en-1-yl)cyclopenta-2-enone (Jasmone) Cis); (1-methyl-2-((1,2,2-trimethylbicyclo[3.1.0]hexane-3-yl)methyl)cyclopropyl)methanol (Javanol); 1-(4-methoxy-2,2,6,6-tetramethylcyclohexa-3-en-1-yl)ethanone (Kefarene); 4-(1-ethoxyethenyl)-3,3,5,5-tetramethylcyclohexane-1-one (Kephalis); (Z)-3,4,5,6,6-pentamethylhepta-3-en-2-one (Koavone); 3,4,5,6,6-pentamethylheptan-2-ol (Kohinool);

[0128] (3E,6E)-2,4,4,7-Tetramethylnonano-6,8-dien-3-one oxime (Labienoxime); 2,8,8-Trimethyloctahydro-1H-4a,2-(epoxymethano)naphthalene-10-one (Lactoscatone); 8-Isopropyl-1-Oxaspiro[4.5]decane-2-one (Laitone); (Z)-1-(1-Ethoxyethoxy)hexa-3-ene (Leaf Acetal); (2E,6Z)-3,7-Dimethylnonano-2,6-diennitrile (Lemonile); 3-(4-(tert-butyl)phenyl)-2-methylpropanal (Lilial); 3,7-Dimethylocta-1,6-dien-3-ol (Linalool Synthetic); 3,7-Dimethylocta-1,6-dien-3-yl acetate (Linalyl Acetate) Synthetic; 3,7-Dimethylocta-1,6-dien-3-yl 3-phenylpropanoate (Linalyl Cinnamate); 3,7-Dimethylocta-1,6-dien-3-yl Formate; 3,7-Dimethylocta-1,6-dien-3-yl 2-methylpropanoate (Linalyl Isobutyrate); 3,7-Dimethylocta-1,6-dien-3-ylpropanoate (Linalyl Propionate); (3R,3aR,8R,8aS)-4,4,8-trimethyl-9-methylenedecahydro-3,8-methanoazulene (Longifolene Std);

[0129] Bicyclo[2.2.2]octa-5-en-2-carboxaldehyde (Maceal); 2,2-dimethyl-3-(m-tolyl)propan-1-ol (Majantol); 2-(4-(tert-butyl)phenyl)acetonitrile (Marenil); 3-methyl-5-phenylpentanal (Mefranal); 3-methyl-5-phenylpentan-1-ol (Mefrosol); 2-(4-methylcyclohexyl)propan-2-yl acetate (Menthanyl Acetate); 2-isopropyl-5-methylcyclohexanol (Menthol Dl); 2-(4-methylcyclohexa-3-en-1-yl)propan-2-thiol (Mercapto-8 Menthene-1 Para); (2-butan-2-yl-1-methylcyclohexyl) acetate (Metambrate); butyl 2-methylpentanoate (Methyl Camomille); 1-((1S,8aS)-1,4,4,6-tetramethyl-2,3,3a,4,5,8-hexahydro-1H-5,8a-methanoazulene-7-yl) ethane (Methyl Cedryl Ketone); 5-hexyl-5-methyloxolan-2-one (Methyl Decalactone Gamma); methyl 2-hexyl-3-oxocyclopentan-1-carboxylate (Methyl Dihydro Isojasmonate); (E)-1,2-dimethoxy-4-(propa-1-en-1-yl)benzene (Methyl Isoeugenol); methylnonano-2-inoate (Methyl Octyne Carbonate); 6,6-dimethoxy-2,5,5-trimethylhexa-2-ene (Methyl Pamplemousse); (E)-3-methyl-4-(2,6,6-trimethylcyclohexa-1-en-1-yl)buta-3-en-2-one (Methylionantheme); 1a,3,3,4,6,6-hexamethyl-1a,2,3,4,5,6,7,7a-octahydronaphtho[2,3-b]oxylen (Moxalone); (Z)-3-methylcyclopentadecane-5-enone (Muscenone); 3-methylcyclopentadecanone (Muscone); 1,7-dioxacycloheptadecane-8-one (Musk R1);4-(4-methylpenta-3-en-1-yl)cyclohexa-3-encarbaldehyde (Myraldene); (4-(4-methylpenta-3-en-1-yl)cyclohexa-3-en-1-yl)methylacetate (Myraldyl Acetate); 7-methyl-3-methyleneocta-1,6-diene (Myrcene 90); (2-methyl-6-methyllideneocta-7-en-2-yl)acetate (Myrcenyl Acetate); 2-methylundecanoic acid (Mystikal); 2-methylundecanoic acid (Mystikal);

[0130] 2-(2-(4-methylcyclohexa-3-en-1-yl)propyl)cyclopentan-1-one (Nectaryl); 2-methyl-6-methyleneocta-7-en-2-yl acetate (Neobergamate Forte); 10-isopropyl-2,7-dimethyl-1-oxaspiro[4.5]deca-3,6-diene (Neocaspirene); (E)-methylnonano-2-enoate (Neofolione); (2Z)-3,7-dimethylocta-2,6-dien-1-ol (Nerolex); (E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol (Nerolidol Synthetic); (Z)-3,7-dimethylocta-2,6-dien-1-yl acetate (Neryl Acetate Hc); 1-(2,2,6-trimethylcyclohexyl)hexane-3-ol (Nimberol); (E)-13-methyloxacyclopentadeca-10-en-2-one (Nirvanolide); (2Z,6E)-2,6-nonadienyl acetate; 6,8-dimethylnonan-2-ol (Nonadyl); 4,4a-dimethyl-6-(propa-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalene-2(3H)-one (Nootkatone Crystals); 2-(6,6-dimethylbicyclo[3.1.1]hepta-2-en-2-yl)ethyl acetate (Nopyl Acetate);

[0131] 2,4-Dimethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)-1,3-dioxolane (Okoumal); 7-Isopropyl-8,8-dimethyl-6,10-dioxaspiro[4.5]decane (Opalal); 4-(2-methoxypropan-2-yl)-1-methylcyclohexene (Orange Flower Ether); 4-(tert-pentyl)cyclohexanone (Orivone); 2,4a,5,8a-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-yl formate (Oxyoctaline Formate);

[0132] 2-Ethyl-N-methyl-N-(m-tolyl)butanamide (Paradisamide); 1,1-dimethoxynonana-2-yin (Parmavert); 5-heptyldihydrofuran-2(3H)-one (Peach Pure); 2-methyl-4-methylene-6-phenyltetrahydro-2H-pyran (Pelargene); 3,7-dimethyloctan-1-ol (Pelargol); 2-cyclohexyllidene-2-phenylacetonitrile (Peonile); 3,7-dimethylocta-1,6-dien-3-yldimethylcarbamate (Pepperwood); 2-methylpentyl 2-methylpentanoate (Peranat); 2-cyclohexylhepta-1,6-dien-3-one (Pharaone); 2-(phenoxy)ethyl 2-methylpropanoate (Phenoxy Ethyl Isobutyrate); 2-phenylethyl 3-phenylpropanoate (Phenyl Ethyl Cinnamate; 2-Phenyl Ethyl 2-Methylpropanoate; 2-Phenyl Ethyl 2-Phenyl Acetate; 2-Phenyl Ethyl 2-Hydroxybenzoate; 3-Phenyl Propyl Acetate; 3-(6,6-Dimethylbicyclo[3.1.1]Hepta-2-en-2-yl)propanal (Pinoace); (3aR,6S,7aS)taldehyde-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl 2,2-dimethylpropanoate (Pivacyclene); 2,2-dimethyl-2-phenylethylpropanoate (Pivarose); (4aS,8aR)-7-methyloctahydro-1,4-methanonaphthalene-6(2H)-one (Plicatone); ethyl 2-cyclohexylpropanoate (Poirenate); (2E,5E)-5,6,7-trimethylocta-2,5-dien-4-one (Pomarose); 1-methyl-4-(4-methylpenta-3-en-1-yl)cyclohexa-3-encarbaldehyde (Precyclemone) B); (E)-2-ethoxy-5-(propenyl guaethol (vanitrope)); 6-(sec-butyl)quinoline (pyralone);

[0133] (E)-2-ethyl-4-(2,2,3-trimethylcyclopenta-3-en-1-yl)buta-2-en-1-ol (Radjanol); 2-(cyclohexylmethyl)-4,4,6-trimethyl-1,3-dioxane (Resedal); mixture of 3,7-dimethylocta-6-en-1-ol and 3,7-dimethylocta-7-en-1-ol (Rhodinol); 2,4-dimethyl-4-phenyltetrahydrofuran (Rhubafuran); (2R,8aS)-3',6-dimethyl-3,4,4a,5,8,8a-hexahydro-1H-spiro[1,4-methanonaphthalene-2,2'-oxirane] (Rhubofix); (4aR ,8aS,E)-6-ethylideneoctahydro-2H-5,8-methanochromene (Rhuboflor); 2,2,2-trichloro-1-phenylethyl acetate (Rosacetol); deca-9-en-1-ol (Rosalva); 3-(2-methylpropyl)-1-methylcyclohexanol (Rossitol); 4-methyl-2-phenyl-3,6-dihydro-2H-pyran (Rosyrane Super);

[0134] 1,1-Diethoxycyclohexane (Rum Acetal); 2,3,3-Trimethyl-1-indanone (Safraleine); 3-((1R,2S,4R,6R)-5,5,6-Trimethylbicyclo[2.2.1]heptan-2-yl)cyclohexanol (Sandela Concentrated); 4,5,6,7,8,9,10,11,12,13-Decahydrocyclododeca[d]oxazole (Sclarene); 2-(1-(3,3-dimethylcyclohexyl)ethoxy)-2-methylpropylcyclopropanecarboxylate (Serenolide); Cyclopentadecanone, Hexadecanol (Silvanone) Supra); 2-methyl-3-[4-(2-methylpropyl)phenyl]propanal (Silvial); 2',2',3,7,7-pentamethylspiro[bicyclo[4.1.0]heptan-2,5'-[1,3]dioxane] (Spirambrene); 1-(spiro[4.5]deca-6-en-7-yl)penta-4-en-1-one (Spirogalbanone); ethylmethylphenylglycidate (Strawberry Pure); 1-phenylethylpropanoate (Styrallyl Propionate); (E)-6-ethyl-3-methylocta-6-en-1-ol (Super Muguet); 2-(heptan-3-yl)-1,3-dioxolane (Syvertal);

[0135] (E)-6,10-dimethylundeca-5,9-diene-2-yl acetate (Tangerinol); 2-(4-methyl-1-cyclohexa-3-enyl)propane-2-yl acetate (Terpinyl Acetate); 3,7-dimethyloctanal (Tetrahydro Citral); 3,7-dimethyloctan-3-ol (Tetrahydro Linalool); 3,7-dimethyloctan-3-yl acetate (Tetrahydro Linalyl Acetate); 2,6-dimethyloctan-2-ol (Tetrahydro Myrcenol; Thibetolide; (E)-3,7-Dimethylocta-2,6-dien-1-thiol; Timberol; (E)-Tridecene-2-Nitrile; Trimofix O; 6-Hexyltetrahydro-2H-pyran-2-one; Methyl Nonyl Ketone; (3E,5Z)-Undecatriene; (E)-4-Methyldeca-3-en-5-ol; (E)-Undecene 2 Nitrile

[0136] 2,2,5-Trimethyl-5-Pentylcyclopentanone (Veloutone); (Z)-Cyclohexadeca-5-enone (Velvione); (E)-Methyl 2-((3-(4-(tert-butyl)phenyl)-2-methylprop-1-en-1-yl)aminobenzoate (Verdantiol); (2-(1-Ethoxyethoxy)ethyl)benzene (Verdilyn); 2-(tert-butyl)cyclohexanol (Verdol); 1-Methyl-4-(4-methylpentyl)cyclohexa-3-encarbaldehyde (Vernaldehyde); 1-((1S,8aS)-1,4,4,6-Tetramethyl-2,3,3a,4,5,8-Hexahydro-1H-5,8a-Methanoazulene-7-yl)Ethanone (Vertofix Coeur); 2,4-diethoxy-5-methylpyrimidine (Vethymine); 4-methyl-4-phenylpentan-2-yl acetate (Vetikol Acetate / Corps Rhubarb); (2R,5R,8S)-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecane-1-yl acetate (Vetynal); [(3Z)-4,11,11-trimethyl-8-methylidene-5-bicyclo[7.2.0]undeca-3-enyl] acetate (Vetyvenal); undeca-10-ennitrile (Violiff); 2-(2,4-dimethylcyclohexyl)pyridine (Zinarine);

[0137] Cedarwood oil; eucalyptus oil; galbanum oil; clove oil; lavandin and lavender oil; mandarin oil; orange terpenes; patchouli oil; ylang-ylang oil; and mixtures thereof. These fragrance components are particularly preferred for obtaining stable and high-performing microcapsules due to their advantageous lipophilicity and olfactory properties.

[0138] Components (group 1 or group 2) that satisfy the requirements defined herein for the first part of the oil phase may be used in both oil phases.

[0139] The second part of the oil phase may contain one or more precursors, which are materials capable of releasing fragrance components upon stimulation, such as changes in temperature, the presence of an oxidizing agent, the action of an enzyme, or the action of light, provided that these precursors are neither alpha-beta unsaturated aldehydes nor do alpha-beta unsaturated aldehydes. Such profragrances are well known to those skilled in the art.

[0140] The oil core may also contain at least one functional cosmetic ingredient. The functional cosmetic ingredient for the encapsulated composition is preferably hydrophobic.

[0141] Particularly useful functional cosmetic ingredients may be selected from the group consisting of softeners, smoothing ingredients, moisturizing ingredients, soothing and relaxing ingredients, decorative ingredients, deodorants, anti-aging ingredients, cell rejuvenation ingredients, draining ingredients, remodeling ingredients, skin leveling ingredients, preservatives, antioxidants, antibacterial or bacteriostatic ingredients, cleansing ingredients, lubricating ingredients, structuring ingredients, hair conditioning ingredients, whitening ingredients, texturizing ingredients, softening ingredients, anti-dandruff ingredients, and exfoliating ingredients.

[0142] Particularly useful functional cosmetic ingredients include, but are not limited to, hydrophobic polymers such as alkyldimethylsiloxane, polymethylsilsesquioxane, polyethylene, polyisobutylene, styrene-ethylene-styrene and styrene-butylene-styrene block copolymers; mineral oils such as hydrogenated isoparaffin and silicone oil; vegetable oils such as argan oil, jojoba oil, and aloe vera oil; fatty acids and fatty alcohols and their esters; glycolipids; phospholipids; sphingolipids, for example. This includes ceramides; sterols and steroids; terpenes, sesquiterpenes, triterpenes and their derivatives; and 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, rosemary oil, sandalwood oil, tea tree oil, thyme oil, valerian oil, wormwood oil, ylang-ylang oil, and yucca oil.

[0143] In particular, at least one functional cosmetic ingredient may be selected from the group consisting of sandalwood oil, e.g., Fusanus spicatus kernel oil; panthenyl triacetate; tocopheryl acetate; tocopherol; naringinine; ethyl linoleate; farnesyl acetate; farnesol; citronellyl methyl crotonate; and ceramide-2(1-stearoy)-C18-sphingosine) (CAS-No: 100403-19-8).

[0144] Regarding step b), the second portion of the oil phase is preferably added after the formation of the macromer is complete.

[0145] In specific embodiments, the complex coacervate comprises a cationic macromolecule selected from gelatin, chitosan, and permanently charged cationic polysaccharides, such as cationic hydroxypropyltrimonium starch or hydroxypropyltrimonium guar gum, and mixtures thereof, and an anionic polysaccharide selected from the group consisting of pectin, gum arabic, and alginates, as well as sodium, potassium, magnesium, or calcium carboxylates thereof, and mixtures thereof. Preferably, the anionic polysaccharide is pectin.

[0146] In a preferred embodiment of the present invention, the negatively charged polymer electrolyte contained in the coacervate is a polymer surfactant contained in the aqueous phase of the composition.

[0147] In a preferred embodiment, the weight ratio of coacervate to polymer stabilizer in the composition obtained according to the present invention is 1 to 3, more specifically 1.5 to 2.0. Such a ratio provides a desired balance between the stability of the microcapsules with respect to the retention of beneficial agents in the microcapsules over time and the biodegradability of the shell.

[0148] In specific embodiments of the present invention, the composite coacervate and polymer stabilizer are crosslinked with a polyfunctional aldehyde, a polyfunctional glycidyl compound, a polyfunctional succinimidyl compound, or an enzyme; and are crosslinked with unreacted isocyanate groups present on the polymer stabilizer.

[0149] A second aspect of the present invention provides a composition comprising a plurality of core-shell microcapsules obtained by the method described herein.

[0150] Beneficial agents, macromers, reactive building blocks, polymer stabilizers, positively charged polymer electrolytes, and negatively charged polymer electrolytes are as defined herein.

[0151] In a specific embodiment, a core-shell microcapsule composition comprising a plurality of core-shell microcapsules obtained by the method described herein is provided.

[0152] The compositions according to the present invention may be in various physical forms, such as slurry, powder, granules, flakes, or extruded products.

[0153] A composition in the form of a liquid slurry according to the present invention may contain 10 to 50% by weight, more specifically 15 to 25% by weight of core-shell microcapsules.

[0154] A solid-state composition according to the present invention may contain 1 to 100% by weight of core-shell microcapsules. However, depending on the application or properties of the beneficial agent, it may be preferable to limit or, conversely, maximize the level of core-shell microcapsules in the solid state. For example, limiting the level of core-shell microcapsules in the solid may be particularly desirable if the encapsulated material is flammable, reactive, irritating, or expensive.

[0155] Therefore, the optimal level of encapsulated fragrance components in a solid composition according to the present invention may be less than 50% by weight, more specifically less than 35% by weight, even more specifically less than 20% by weight, and even less than 15% by weight, depending on the flammability of such fragrance components and the associated explosion risk.

[0156] In yet another aspect, the present invention relates to the use of compositions according to the present invention for enhancing the performance of beneficial agents, particularly fragrance compositions, in consumer products.

[0157] The present invention also relates to consumer products comprising compositions according to the present invention. Consumer products are preferably selected from the group consisting of fabric care detergents and conditioners, hair care conditioners, shampoos, heavy-duty liquid detergents, hard surface cleaners, detergent powders, soaps, shower gels, and skin care products.

[0158] The compositions according to the present invention are particularly useful when employed as fragrance delivery vehicles for consumer goods that require good adhesion to a substrate to which microcapsules are applied in order to provide optimal fragrance benefits. Such consumer goods include hair shampoos and conditioners, as well as textile treatment products, such as laundry detergents and conditioners.

[0159] The specific features and further advantages of the present invention are described more fully in the following examples.

[0160] Example 1 - Fragrance Composition A series of fragrances were prepared, and their compositions are reported in Table 1. Table 1 shows the complete fragrance compositions and how these fragrances were divided into the first and second parts of the oil phase.

[0161] Table 1: Fragrance composition and fragrance division Fragrance 1.1 [Table 1]

[0162] Fragrance 1.2 [Table 2]

[0163] Fragrance 1.3 [Table 3]

[0164] Example 2 - Formation of microcapsules containing a hydrogel formed by a combination of pectin and gelatin (according to the present invention) In Example 2.1, microcapsules were obtained as follows: a) The core composition was prepared by mixing 0.7 g of bipodal aminosilane (bis(3-triethoxysilylpropyl)amine), 0.48 g of Takenate D-110N (ex Mitsui), and 19.25 g of the first portion of the oil phase of Fragrance 1.1, which corresponds to 50% by weight of the total fragrance composition; b) The core composition was heated to 25 ± 2°C and maintained under stirring for 15 minutes; c) After 15 minutes, 19.25 g of the second oil phase of fragrance 1 was added to the emulsion obtained in step c) while maintaining both temperature and stirring; d) The core composition obtained in step b) was emulsified in a mixture of 1.0 g of high-methoxylated grade pectin (APA 104 type, ex Roeper) in 73.3 g of water by using a 300 ml reactor and a cross-beam stirrer with a pitched beam operating at a stirring speed of 600 rpm at a temperature of 25 + / - 2°C for 10 minutes; e) The system temperature was raised to 85 ± 2°C over 4 hours, 0.3 g of trimesic acid (1,3,5-benzenetricarboxylic acid) was added, and the system was maintained at this temperature for 1.3 hours while maintaining stirring as in step b); f) While maintaining stirring as in step b), the system was slowly cooled to 40°C over a period of 2.25 hours; g) At a temperature of 40+ / -2°C, 10 g of 10% gelatin solution in water was added while maintaining stirring as in step b); h) While maintaining stirring as in step b), the system was slowly cooled to 10°C over a period of 2.25 hours; i) Once the system reached a temperature of 10°C, 0.02 g of a 50 wt% glutaraldehyde solution in water was added, and the system was maintained at this temperature for 1 hour while continuing to stir as in step b) to form a slurry of core-shell microcapsules; j) The core-shell capsule slurry obtained in step f) was finally stabilized at room temperature.

[0165] The obtained slurry had a solid content of 33.1% by weight, the median volume size (d50) of the capsules was 32 μm, and the encapsulation efficiency was 99%. In Example 2.2, Fragrance 2 was used, and the weight ratio of the first part to the second part of the fragrance oil was modified, i.e., 12.3 g of the first part was used in step a) and 26.2 g of the second part was used in step d). In Example 2.3, these amounts were 16.5 g and 22 g, respectively.

[0166] Example 3 - Formation of microcapsules containing a hydrogel formed by a combination of pectin and gelatin (Comparative Example) In Example 2.1, microcapsules were obtained as follows: a) The core composition was prepared by mixing 0.7 g of bipodal aminosilane (bis(3-triethoxysilylpropyl)amine), 0.48 g of Takenate D-110N (ex Mitsui), and 38.5 g of fragrance composition 1, which corresponds to 50% by weight of fragrance composition 1; b) The core composition obtained in step a) was emulsified in a mixture of 1.0 g of high-methoxylated grade pectin (APA 104 type, ex Roeper) in 73.3 g of water by using a 300 ml reactor and a cross-beam stirrer with a pitched beam operating at a stirring speed of 600 rpm at a temperature of 25 + / - 2°C for 10 minutes; c) The system temperature was raised to 85 ± 2°C over a period of 4 hours, 0.3 g of trimesic acid (1,3,5-benzenetricarboxylic acid) was added, and the system was maintained at this temperature for 1.3 hours while maintaining stirring as in step b); d) While maintaining stirring as in step b), the system was slowly cooled to 40°C over a period of 2.25 hours; e) At a temperature of 40+ / -2°C, 10 g of 10% gelatin solution in water was added while maintaining stirring as in step b); f) While maintaining stirring as in step b), the system was slowly cooled to 10°C over a period of 2.25 hours; g) Once the system reached a temperature of 10°C, 0.02 g of 50 wt% glutaraldehyde solution in water was added, and the system was maintained at this temperature for 1 hour while continuing to stir as in step b) to form a slurry of core-shell microcapsules; h) The core-shell capsule slurry obtained in step f) was finally stabilized at room temperature.

[0167] The obtained slurry had a solid content of 33.1% by weight, the median volume size (d50) of the capsules was 32 μm, and the encapsulation efficiency was 99%. In Example 3.2, the same procedure was applied, but perfume 1.2 was used in step a), whereas in Example 3.3, perfume 1.3 was used in step a).

[0168] Example 4 - Comparison of Microcapsule Performance The performance of the capsules obtained in Examples 1 and 2 was evaluated from the standpoint of stability. For stability assessment, the base was a commercially available, fragrance-free laundry care conditioner base. For each assessment, a 1% by weight slurry was dispersed in the base while stirring with a paddle mixer. The encapsulated core composition contained 0.02% by weight of Hostasol® Yellow 3G (Clariant) as a fluorescent dye. The samples were then stored at 37°C for 8 weeks. Leakage from the capsules was visually assessed using a fluorescence microscope operating at an excitation wavelength of 488 nm and an emission wavelength of 515 nm, according to the following scale.

[0169] - Poor stability: Disintegrated microcassels and fluorescent droplets are visible; - Average stability: Partially disintegrated microcapsules coexist with fluorescent droplets; - Good stability: All capsules still contain the complete fluorescent core composition, and no fluorescent droplets are visible.

[0170] [Table 4]

Claims

1. A method for preparing a composition comprising multiple core-shell microcapsules, wherein the method comprises the following steps: a) To provide an oil phase comprising an encapsulated beneficial agent and a macromer formed by the reaction of one or more reactive building blocks; b) Providing an aqueous phase; c) Emulsifying the oil phase and the aqueous phase to form a dispersed phase consisting of multiple oil cores in a continuous aqueous phase; d) Polymerizing the macromer to form a polymer stabilizer at the interface between the oil core and the aqueous phase; e) subjecting the positively charged and negatively charged polymer electrolytes, which were independently added to the aqueous phase during steps b), c), or d), to a coacervation process, thereby forming a hydrated polymer shell around the oil core; and f) Crosslinking a hydrated polymer shell with a polymer stabilizer to cure the shell around the oil core, thereby forming a composition containing multiple core-shell microcapsules.

2. The method according to claim 1, wherein a macromer is formed in situ in an oil phase, and the oil phase comprises, based on the total weight of the oil phase: a) Less than 1% by weight, more specifically less than 0.1% by weight, and even more specifically 0.0% by weight of reactive building blocks and readily reactive components; b) Components having a Hansen solubility parameter that satisfies Equation 1 in an amount of 40% by weight or more, more specifically 60% by weight or more, even more specifically 75% by weight or more, even more specifically 90% by weight or more, and even more specifically 95% by weight or more; [Math 1] c) Components having Hansen solubility parameters δD, δp, δh that satisfy the conditions given by equation 2, less than 60% by weight, more specifically less than 40% by weight, even more specifically less than 25% by weight, even more specifically less than 10% by weight, and even more specifically less than 5% by weight, and referred to as Group 2: [Math 2] and d) Components having Hansen solubility parameters δD, δp, and δh that satisfy the condition given by equation 3, less than 1% by weight; [Math 3] Here, the subscript A refers to a component of the oil phase, and B refers to the reactive building block with the highest molecular weight; Here, the Hansen solubility parameter is calculated using the Yamamoto-Molecular Break (Y-MB) method implemented in the 4th edition of the HSPiP software.

3. The method according to claim 1 or 2, wherein an oil phase containing a beneficial agent is divided into a first part and a second part, the first part satisfying the conformance conditions a) to d) of claim 2, wherein a macromer is formed in this first part, and wherein, once the macromer is formed, the second part of the oil phase is added.

4. The method according to any one of claims 1 to 3, wherein the weight ratio of the second part to the first part is between 4.5 and 0.5 and 0.5 and 4.5, specifically between 4 and 1 and 1 and 4, and more specifically between 3 and 2 and 2 and 3.

5. The method according to any one of claims 1 to 4, wherein the macromer is an adduct formed by the reaction of a reactive building block comprising an aminosilane and a polyfunctional isocyanate, and the polymer stabilizer is formed by polycondensation of the adduct at the oil / water interface.

6. The method according to any one of claims 1 to 5, wherein the hydrated polymer shell in step e) is a crosslinked coacervate, more specifically a crosslinked composite coacervate formed from a positively charged polymer electrolyte and a negatively charged polymer electrolyte.

7. The method according to any one of claims 1 to 6, wherein the polymer stabilizer is formed by polycondensation of an adduct formed by the reaction of bis(3-(triethoxysilyl)propyl)amine and 2-ethylpropane-1,2,3-triyltris((3-(isocyanatemethyl)phenyl)carbamate).

8. The method according to claim 7, wherein the first portion of the oil phase includes the following: a) Amines, aldehydes, enols, and halogenated components in amounts less than 5% by weight, more specifically less than 1% by weight, and even more specifically less than 0.1% by weight; b) Components having δD, δP, and δH that satisfy the conditions given by Equation 4, which are 40% or more by weight, more specifically 60% or more by weight, even more specifically 75% or more by weight, even more specifically 90% or more by weight, and even more specifically 95% or more by weight, and are referred to as Group 1 components: [Math 4] c) Components having Hansen solubility parameters δD, δp, and δh that satisfy the conditions given by equation 5, less than 60% by weight, more specifically less than 40% by weight, even more specifically less than 25% by weight, even more specifically less than 10% by weight, and even more specifically less than 5% by weight, and referred to as Group 2: [Math 5] d) Components having Hansen solubility parameters δD, δp, and δh that satisfy the condition given by equation 6 for less than 1% by weight: [Math 6] e) Components having a ClogP of 2.5 to 3.0 in less than 40% by weight, and components having a ClogP of less than 2.5 in less than 5% by weight; and f) 150cm with less than 30% weight 3 / mol~170cm 3 Components having a molar volume of / mol, and less than 5% by weight of 150cm³ 3 Components having a molar volume of less than / mol; Here, the Hansen solubility parameter is calculated using the Yamamoto-Molecular Break (Y-MB) method implemented in the 4th edition of the HSPiP software.

9. The Group 1 component of the first oil phase is a fragrance component selected from the following group: (2-(1-propoxyethoxy)ethyl)benzene, (Z)-oxacycloheptadeca-10-en-2-one, pentyl 2-phenylacetate, 3,5-diethyl-2,5-dimethylcyclohexa-2-enone, 7-isopentyl-2H-benzo[b][1,4]dioxepin-3(4H)-one, benzyl benzoate, benzyl 3-phenylpropanoate, benzyl 2-methylpropanoate, benzyl 3-methylbutanoate, benzyl Zyl 2-phenylacetate, benzyl 2-hydroxybenzoate, 1-butoxy-1-oxopropane-2-ylbutanoate, ((1S,8aR)-1,4,4-trimethyl-2,3,3a,4,5,8-hexahydro-1H-5,8a-methanoazulene-6-yl)methanol, (1S,6R,8aR)-1,4,4,6-tetramethyloctahydro-1H-5,8a-methanoazulene-6-ol, (4Z,8Z)-1,5,9-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene, methyl 2-(3-oxo-2 (E)-Pentylcyclopentyl)acetate, 3-phenylpropa-2-enyl3-phenylpropa-2-enoate, (E)-1,1-dimethoxy-3,7-dimethylocta-2,6-diene, (Z)-1,1-diethoxy-3,7-dimethylocta-2,6-diene, 3,7-dimethylocta-6-en-1-ylethyloxalate, 3,7-dimethylocta-6-en-1-ylformate, 3,7-dimethylocta-6-ennitrile, (Z)-3-methylcyclotetradeca-5-enone, (4-methylphenyl)octanoate, (4-methylphenyl) (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-ol, (E)-1-(2,6,6-trimethylcyclohexa-2-en-1-yl)butan-2-en-1-one, (E)-1-(2,6,6-trimethylcyclohexa-2-en-1-yl)butan-2-en-1-one, (E)-1-(2,6,6-Trimethyl-1-cyclohexenyl)buta-2-en-1-one, 1-(2,6,6-trimethyl-1-cyclohexa-3-enyl)buta-2-en-1-one, decanonitrile, (oxybis(methylene))dibenzene, 3-methyl-2-pentylcyclopenta-2-enone, 6-heptyltetrahydro-2H-pyran-2-one, 5-octyloxolan-2-one, 1,4-dioxacycloheptadecane-5,17-dione, 3-(4-ethylphenyl)-2,2-dimethylpropanenitrile, (E)-undeca-9-ennitrile, (3aR, (6S,7aS)-3a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoindene-6-ylpropanoate, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, (3aS,4S,7R,7aS)-ethyloctahydro-1H-4,7-methanoindene-3a-carboxylate, 2-methyldecanonitrile, 1-(1,2,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-yl)ethanone, (E)-6,10-dimethylundeca-5,9-dien-2-one, (E)-oxacyclohex Sadeca-12-en-2-one, methyl 3-oxo-2-pentylcyclopentane acetate, heptan-2-one, (Z)-hexa-3-en-1-yl benzoate, (Z)-hexa-3-en-1-yl (Z)-hexa-3-enoate, (Z)-hexa-3-en-1-yl 2-hydroxybenzoate, (Z)-hexa-3-enyl](E)-2-methylbuta-2-enoate, hexyl 2-hydroxybenzoate, (E)-4-(2,6,6-trimethylcyclohexa-1-en-1-yl)buta-3-en-2-one, (E)-3-methyl -4-(2,6,6-trimethylcyclohexa-2-en-1-yl)buta-3-en-2-one, (E)-4-(2,6,6-trimethylcyclohexa-2-en-1-yl)buta-3-en-2-one, 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-yl)ethanone, 2-methylpropyl 2-phenylacetate, 2-methylpropyl 2-hydroxybenzoate, 2-hexylcyclopenta-2-en-1-one, 2-hexylcyclopenta-2-enone, (E)-3-methyl-4-(2,6,6-Trimethylcyclohexa-2-en-1-yl)buta-3-en-2-one, (3aR,6S,7aS)-3a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoindene-6-yl acetate, 2-Hexylcyclopentanone, (E)-6-(penta-3-en-1-yl)tetrahydro-2H-pyran-2-one, 3-Butyl-5-methyltetrahydro-2H-pyran-4-yl acetate, 3-Pentyltetrahydro-2H-pyran-4-yl acetate, (4Z)-Hepta-4-en-2-yl 2-hydroxybenzoate (2E,6Z)-3,7-dimethylnonano-2,6-diennitrile, 3-methyl-5-phenylpentan-1-ol, 5-methyl-2-propane-2-ylcyclohexyl]2-hydroxypropanoate, methylnonano-2-inoate, (E)-3-methyl-4-(2,6,6-trimethylcyclohexa-1-en-1-yl)buta-3-en-2-one, (Z)-3-methylcyclopentadeca-5-enone, 1,4-dioxacyclohexadecane-5,16-dione, 1,7-dioxacycloheptadecane-8-one, (4-(4-methylpenta (-3-en-1-yl)cyclohexa-3-en-1-yl)methylacetate, 2-(2-(4-methylcyclohexa-3-en-1-yl)propyl)cyclopentan-1-one, (E)-methylnona-2-enoate, (E)-13-methyloxacyclopentadeca-10-en-2-one, 4,4a-dimethyl-6-(propa-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalene-2(3H)-one, 4-(tert-pentyl)cyclohexanone, 2-ethyl-N-methyl-N-(m-tolyl)butanamide, 1,1 -Dimethoxynonana-2-in, 5-heptyldihydrofuran-2(3H)-one, 2-cyclohexylidene-2-phenylacetonitrile, 3,7-dimethylocta-1,6-dien-3-yldimethylcarbamate, 2-cyclohexylidene-2-(o-tolyl)acetonitrile, 2-(phenoxy)ethyl 2-methylpropanoate, 2-phenylethyl 3-phenylpropanoate, 2-phenylethyl 2-methylpropanoate, 2-phenylethyl 2-phenylacetate, 2-phenylethyl 2-hydroxybenzoate, (2E,(5E)-5,6,7-trimethylocta-2,5-dien-4-one, (4aR,8aS,E)-6-ethylideneoctahydro-2H-5,8-methanochromene, 3-(2-methylpropyl)-1-methylcyclohexanol, 2,3,3-trimethyl-1-indanone, 4,5,6,7,8,9,10,11,12,13-decahydrocyclododeca[d]-oxazole, 1-(spiro[4.5]deca-6-en-7-yl)penta-4-en-1-one, (E)-trideca-2-ennitrile, 6-hexyltetrahydro-2H-pyran-2-one, (Z)-cyclohexadeca-5-enone, or mixtures thereof; and, where the Group 2 components of the first oil phase are fragrance components selected from the group consisting of: Octyl acetate, (Z)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undeca-4-ene, 2-methyl-4-(5,6,6-trimethylbicyclo[2.2.1]hepta-2-ylcyclohexanone, propa-2-enyl-2-(3-methylbutoxy)acetate, propa-2-enylheptanoate, 1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-ol, 1,3,4,5,6,7-hexahydro-beta, 1,1,5,5-pentamethyl-2H-2,4a-methanonaphthalene-8-ethanol, (2-(isopentyloxy)ethyl)benzene, 1-(3,3-dimethylcyclohexyl)ethyl formate, (E)-2-ethyl-4-(2,2,3- (Dimethylcyclopenta-3-en-1-yl)buta-2-en-1-ol, (1R,2S,4R)-2'-isopropyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane], 2-methyl-6-methyleneocta-7-en-2-yl acetate, (ethoxymethoxy)cyclododecane, (2S,4S)-1 ,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate, 4-(tert-butyl)cyclohexanol, 1,1,2,3,3-pentamethyl-2,3,6,7-tetrahydro-1H-indene-4(5H)-one, ((3R,3aS,7R,8aS)-3,8,8-trimethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-methanoazulene-6-yl)methylacetate, (1S,6R,8aR)-1,4,4,6-tetramethyloctahydro-1H-5,8a-methanoazulene-6-ylacetate, 2-methyl-4-(2,6,6-trimethylcyclohexa-2-en-1-yl)butanal, 3,7-dimethylocta-6-en-1-ol, 3,7-dimethylocta-6-en-1-ol, 3,7-dimethylocta-6-en-1-ylacetate, 3,7-dimethylocta-6-en-1-ylpro Panoate, 4-cyclohexyl-2-methylbutan-2-ol, ethyl 2,6,6-trimethylcyclohexa-1,3-dien-1-carboxylate, 3,7-dimethylocta-6-en-3-ol, 2,6-dimethylocta-7-en-2-ol, 2-methyl-1-phenylpropane-2-ylbutanoate, (E)-3-methyl-5-(2,2,3-trimethylcyclopenta-3-en-1-yl)penta-4-en-2-ol, (2E,4Z)-ethyldeca-2,4-dienoate Ethyl decanoate, (E)-3,7-dimethylnonanoate-1,6-dien-3-ol, ethyl octanoate, ethyl nonanoate, ethyl 2,6,6-trimethylcyclohexa-1,3-dien-1-carboxylate, (2S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl acetate, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalene-2-yl)ethanolone, 2,6-dimethylocta-7-en-2-ol, (Z) -1-(cycloocta-3-en-1-yl)propan-1-ol, 4,4,8,8-tetramethyloctahydro-4a,7-methanonaphtho[1,8a-b]oxylen, (3aR,6S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl2-methylpropanoate, (E)-3,7-dimethylocta-2,6-dien-1-yl acetate, 2-(8-isopropyl-6-methylbicyclo[2.2.2]octa-5-en-2-yl)-1,3-Dioxolane, (Z)-Hexa-3-en-1-ylbutanoate, (Z)-Hexa-3-en-1-yl2-methylpropanoate, (Z)-Hexa-3-en-1-yl2-methylbutanoate, Hexylbutanoate, Hexyl2-methylpropanoate, (E)-4-(2,5,6,6-tetramethyl-1-cyclohexa-2-enyl)buta-3-en-2-one, (E)-4-(2,5,6,6-tetramethylcyclohexa-2-en-1-yl)buta-3-en-2-one, (E)-4-(2,5,6,6-tetramethylcyclohexa (-2-en-1-yl)buta-3-en-2-one, 2,2,7,7-tetramethyltricyclo[6.2.1.01,6]undecane-5-one, (1-methyl-2-((1,2,2-trimethylbicyclo[3.1.0]hexane-3-yl)methyl)cyclopropyl)methanol, 1-(4-methoxy-2,2,6,6-tetramethylcyclohexa-3-en-1-yl)ethanone, (Z)-1-(1-ethoxyethoxy)hexa-3-ene, 3,7-dimethylocta-1,6-dien-3-ol, 3,7-dimethylocta-1,6-dien-3-yl 10-Isopropyl-2,7-dimethyl-1-oxaspiro[4.5]decane, 10-Isopropyl-2,7-dimethyl-1-oxaspiro[4.5]decane, 10-Isopropyl-2,7-dimethyl-1-oxaspiro[4.5]decane, 10-Isopropyl-2,7-dimethyl-1-oxaspiro[4.5]decane, 10-Isopropyl-2,7-dimethyl-1-oxaspiro[4.5]decane, 10-Isopropyl-2,7-dimethyl-1-oxaspiro[4.5]decane -3,6-diene, (E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol, (Z)-3,7-dimethylocta-2,6-dien-1-yl acetate, 2-(6,6-dimethylbicyclo[3.1.1]hepta-2-en-2-yl)ethyl acetate, 2,4-dimethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)-1,3-dioxolane, (1-methyl-2-(((1R,3R)-2,2,3-trimethylcyclopentyl)methyl)cyclopropyl)methanol, 2,2-dimethyl-2-phenylethylpropanoate, ethyl 2-cyclohexylpropanoate, (E)-2-ethyl-4-(2,2,3-trimethylcyclopenta-3-en-1-yl)buta-2-en-1-ol, 2-(cyclohexylmethyl)-4,4,6-trimethyl-1,3-dioxane, 3,7-dimethylocta-6-en-1-ol and 3,7-dimethylocta- Mixture with 7-en-1-ol, deca-9-en-1-ol, 3-((1R,2S,4R,6R)-5,5,6-trimethylbicyclo[2.2.1]heptan-2-yl)cyclohexanol, 3-((1R,2S,4R,6R)-5,5,6-trimethylbicyclo[2.2.1]heptan-2-yl)cyclohexanol, (E)-2-methyl-4-(2,2,3-trimethyl (E)-1-Cyclopenta-3-enyl)buta-2-en-1-ol, 2-(1-(3,3-dimethylcyclohexyl)ethoxy)-2-methylpropylcyclopropanecarboxylate, (E)-6-ethyl-3-methylocta-6-en-1-ol, (E)-2-((3,5-dimethylhexa-3-en-2-yl)oxy)-2-methylpropylcyclopropanecarboxylate, (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate, 2-(4-methyl-1-cyclohexa-3-enyl)propane-2-yl acetate, oxacyclohexadecan-2-one, (E)-4-methyldeca-3-en-5-ol, 2,2,5-trimethyl-5-pentylcyclopentanone, 1-((1S,8aS)-1,4,4,6-tetramethyl, -2,3,3a,4,5,8-Hexahydro-1H-5,8a-methanoazulene-7-yl)ethanone, 4-methyl-4-phenylpentan-2-yl acetate, (4,8-dimethyl-2-propane-2-ylidene-3,3a,4,5,6,8a-Hexahydro-1H-azulene-6-yl) acetate, (2R,5R,8S)-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecane-1-yl acetate, [(3Z)-4,11,11-trimethyl-8-methylidene-5-bicyclo[7.2.0]undeca-3-enyl] acetate, or mixtures thereof; The method according to claim 7 or 8.

10. The method according to any one of claims 7 to 9, wherein the second oil phase comprises, based on the total weight of the second oil phase: a) Amines and alpha-beta unsaturated aldehydes in amounts less than 5% by weight, more specifically less than 1% by weight, and even more specifically less than 0.1% by weight; b) Aldehydes that are not alpha-beta unsaturated aldehydes, present in an amount of 15% by weight or less. c) Components having a ClogP of 2.5 to 3.0 in less than 40% by weight, and components having a ClogP of less than 2.5 in less than 5% by weight; d) 150cm with less than 30% by weight 3 / mol~170cm 3 Components having a molar volume of / mol, and less than 5% by weight of 150cm³ 3 Components having a molar volume of less than / mol; e) Components having Yamamoto-Molecular Break (Y-MB) Hansen solubility parameters δD, δp, and δh that satisfy the conditions given by equation 7 in amounts of 50% by weight or less: [Number 7]

11. The method according to any one of claims 7 to 10, wherein the composite coacervate comprises: a) Gelatin, chitosan, and positively charged polymer electrolytes selected from permanently charged cationic polysaccharides selected from cationic hydroxypropyltrimonium starch or hydroxypropyltrimonium guar gum, and mixtures thereof; b) A negatively charged polymer electrolyte selected from the group consisting of pectin, gum arabic and alginates, as well as sodium, potassium, magnesium or calcium carboxylate salts thereof, and mixtures thereof, preferably pectin and its salts.

12. The method according to claims 7 to 11, wherein the weight ratio of coacervate to polymer stabilizer is 1 to 3, preferably 1.5 to 2.

5.

13. A composition comprising a core-shell microcapsule obtained by the method of at least one of claims 1 to 12.

14. Use of the encapsulated composition according to claim 13 for enhancing the performance of a beneficial agent in a consumer product.

15. A consumer product comprising the encapsulated composition according to claim 13, wherein the consumer product is selected from the group consisting of fabric care detergents and conditioners, hair care conditioners, shampoos, heavy-duty liquid detergents, hard surface cleaners, detergent powders, soaps, shower gels, and skin care products.

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