Microcapsules

Abstract

The present invention relates to microcapsules comprising a hydrophobic core within a polymeric shell wherein a) the polymeric shell is formed from a shell component comprising: i) a polyisocyanate wherein the polyisocyanate is selected from the group consisting of xylylene diisocyanates (XDI) and oligomers, adducts and derivatives thereof; ii) a polycaprolactone polyol comprising from 2 to 4 free hydroxyl groups; iii) a polyethyleneimine; iv) optionally, other shell components; and b) the hydrophobic core comprises an active material. The invention also relates to a slurry comprising said microcapsules, a home care formulation comprising said microcapsules, a personal care formulation comprising said microcapsules and a process for preparing said microcapsules.

Description

Technical Field

[0001] The present invention relates to microcapsules comprising an active core material within a polymer shell, home care formulations or personal care formulations comprising the microcapsules, and methods of forming the microcapsules. Background Art

[0002] Microencapsulation systems are known for encapsulating active core materials such as fragrances. The encapsulation process produces microcapsules containing a core of active material surrounded by a polymer shell. Typically, the active material is hydrophobic, which allows the shell to polymerize around particles (e.g., droplets) of the hydrophobic core dispersed and / or emulsified in an aqueous medium and / or solvent.

[0003] Various methods for preparing core-shell microcapsules have been proposed in the literature. For example, it is known to encapsulate a hydrophobic core material by dispersing the core material into an aqueous medium containing a melamine formaldehyde (MF) precondensate and then lowering the pH to produce microcapsules comprising an aminoplast resin shell wall surrounding the core material. EP2794839B discloses aminoplast microcapsules stabilized by polyisocyanates. Such aminoplast microcapsules are generally not considered to be biodegradable.

[0004] There is a need to provide improved microcapsules or to address one or more disadvantages of the prior art. SUMMARY OF THE INVENTION

[0006] The present invention is based in part on the surprising recognition by the inventors that the combination of shell components in microcapsules according to the present invention may contribute to improving the biodegradability and / or performance of the capsules when compared to other microcapsules.

[0007] Viewed from a first aspect, the invention provides a microcapsule comprising a hydrophobic core within a polymeric shell, wherein:

[0008] a) the polymer shell is formed from a shell component, the shell component comprising:

[0009] i) a polyisocyanate, wherein the polyisocyanate is selected from xylylene diisocyanate (XDI) and its oligomers, adducts and derivatives;

[0010] ii) polycaprolactone polyols containing 2 to 4 free hydroxyl groups;

[0011] iii) polyethyleneimine; and

[0012] iv) optionally, other shell components; and

[0013] b) The hydrophobic core comprises an active material.

[0014] Viewed from a second aspect, the invention provides a slurry comprising the microcapsules of the first aspect, water and at least one surfactant.

[0015] Viewed from a third aspect, the present invention provides a home care formulation or a personal care formulation comprising the slurry of the second aspect or the microcapsules of the first aspect.

[0016] From a fourth aspect, the present invention provides a method for preparing a microcapsule according to the first aspect, wherein the method comprises the following steps:

[0017] a) forming a polymerization system comprising an aqueous phase and a dispersed oil phase, wherein the oil phase comprises the active material, the polyisocyanate shell component and the polycaprolactone polyol shell component;

[0018] b) reacting the polyethyleneimine shell component by adding it to the aqueous phase to form microcapsules comprising a core of the oil phase within the polymer shell;

[0019] c) optionally, adding a deposition additive to the surface of the microcapsules; and

[0020] d) Optionally, neutralizing the microcapsules using a metal hydroxide or an inorganic acid.

[0021] Viewed from a fifth aspect, the invention provides microcapsules obtainable by a method according to the fourth aspect.

[0022] Any aspect of the invention may include any feature described herein in relation to that aspect of the invention or any other aspect of the invention. DETAILED DESCRIPTION OF THE INVENTION

[0024] In the context of the present invention, microcapsules are understood to be microparticles containing at least one or more active materials as core materials within the capsule and enclosed by a polymer capsule shell or capsule wall. The active materials are preferably hydrophobic or lipophilic ingredients. These ingredients are preferably insoluble or poorly soluble in water, but soluble in fats and oils.

[0025] It should be understood that any upper or lower amount or range limits used herein may be independently combined.

[0026] It should be understood that when describing the number of carbon atoms in a substituent (e.g., "C1 to C6"), this number refers to the total number of carbon atoms present in the substituent, including any number of carbon atoms present in any branching groups. Additionally, when describing the number of carbon atoms in, for example, a fatty acid, this refers to the total number of carbon atoms including the carbon atoms at the carboxylic acid and the carbon atoms present in any branching groups.

[0027] Many chemicals that can be used to produce the present invention are obtained from natural sources. Such chemicals, due to their natural sources, often include mixtures of chemical substances. Due to the presence of such mixtures, the various parameters defined herein may be average values ​​and may be non-integer.

[0028] The term biodegradability refers to the ability of an organic material to degrade into water, carbon dioxide (CO) and / or 2 ) and biomass. According to the standard test method of OECD 301F, if more than 60% of the test material (such as microcapsule shell) is degraded after 28 days, the test material (such as microcapsule shell) is considered to be readily biodegradable.

[0029] As used herein, the term "personal care preparation" refers to a consumer product intended for application to the human body or any part thereof for cleansing, beautification, or improving appearance. Personal care preparations include, but are not limited to, cosmetics; deodorants; bar soaps; liquid soaps; face and body washes; face and body cleansers; shampoos; hair conditioners; toothpastes; shaving creams or gels; and foot care products. Personal care preparations do not include any product requiring a prescription.

[0030] As used herein, the term "home care formulation" refers to consumer products for household cleaning, care or conditioning by household and / or institutional consumers. Home care formulations include, but are not limited to, detergents, including laundry detergents and dishwashing detergents; conditioners, including fabric conditioners; cleaning formulations, including hard surface cleaners; polishes and floor finishes.

[0031] As used herein, the term "polymerization system" refers to the aqueous phase, oil phase, shell component and all other ingredients used to produce the microcapsules.

[0032] Microcapsules

[0033] The microcapsules according to the invention comprise a hydrophobic core within a polymer shell, wherein:

[0034] a) the polymer shell is formed from a shell component, the shell component comprising:

[0035] i) a polyisocyanate, wherein the polyisocyanate is selected from xylylene diisocyanate (XDI) and its oligomers, adducts and derivatives;

[0036] ii) polycaprolactone polyols containing 2 to 4 free hydroxyl groups;

[0037] iii) polyethyleneimine; and

[0038] iv) optionally, other shell components; and

[0039] b) The hydrophobic core comprises an active material.

[0040] The microcapsules can be produced in a polymerization system. The slurry can include the produced microcapsules, water and at least one surfactant. Preferably, the microcapsules do not include an aminoplast resin. As used herein, the aminoplast resin is a urea-formaldehyde (UF) or melamine-formaldehyde (MF) resin. Due to environmental reasons, such as poor biodegradability, two types of aminoplast resins may be undesirable.

[0041] The particle size parameters of the microcapsules (eg D10, D50 or D90 volume average diameter) can be measured by laser diffraction particle size analysis. The measurement can be performed using a Malvern Mastersizer 3000E with a measuring unit Hydro EV.

[0042] The microcapsules may have a D10 volume average diameter (i.e., the point below which 10% of the microcapsules are contained, measured based on volume as described herein) of at least 0.5 μm, preferably at least 1 μm, more preferably at least 1.5 μm. The microcapsules may have a D10 volume average diameter of at most 30 μm, preferably at most 20 μm, more preferably at most 10 μm.

[0043] The microcapsules may have a D50 volume mean diameter of at least 2 μm, preferably at least 4 μm, more preferably at least 5 μm, measured as described herein.The microcapsules may have a D50 volume mean diameter of at most 50 μm, preferably at most 40 μm, more preferably at most 30 μm, yet more preferably at most 20 μm.

[0044] The microcapsules may have a D90 volume mean diameter of at least 7 μm, preferably at least 9 μm, especially at least 11 μm, measured as described herein.The microcapsules may have a D90 volume mean diameter of at most 80 μm, preferably at most 60 μm, especially at most 40 μm.

[0045] Shell component i) - polyisocyanate

[0046] The first component of the polymer shell is a polyisocyanate. The polyisocyanate is selected from xylene diisocyanate (XDI) and its oligomers, adducts and derivatives. Surprisingly, the benefit of using XDI or its oligomers, adducts or derivatives in microcapsule production is that such polyisocyanates have one or more of the following advantages: excellent degree of reactivity, improved pot life, improved heat resistance and / or reduced tendency of polymer yellowing. The polyisocyanate can be selected from xylene diisocyanate (XDI), hydrogenated XDI (H6XDI), XDI-TMP (trimethylolpropane) adduct, XDI trimer and H6XDI-TMP adduct. This polyisocyanate can be obtained from Mitsui Chemicals in the Takenate series of products. Preferably, the polyisocyanate is selected from XDI trimer (e.g., Takenate D131N from Mitsui) or XDI-TMP adduct (e.g., Takenate D110N from Mitsui). Preferably, the polyisocyanate is selected from XDI trimer, XDI-TMP adduct and mixtures thereof. The polyisocyanate may be an XDI trimer. The polymer shell may comprise only one polyisocyanate.

[0047] Preferably, the polymer shell does not contain isophorone diisocyanate (IPDI).

[0048] The polymer shell may comprise 20 to 75% by weight of polyisocyanate, based on the total weight of the shell components in the microcapsule. The polymer shell may comprise at least 25%, preferably at least 30% by weight of polyisocyanate, based on the total weight of the shell components in the microcapsule. The polymer shell may comprise up to 70%, preferably up to 65%, more preferably up to 60% by weight of polyisocyanate, based on the total weight of the shell components in the microcapsule.

[0049] The amount of polyisocyanate in the microcapsules can also be specified by reference to the amount of polyisocyanate contained in the polymerization system, as described in Example 1 below. The polymerization system may contain at least 0.5 wt%, preferably at least 1 wt%, more preferably at least 1.5 wt%, and in particular at least 2 wt% of polyisocyanate, based on the total weight of the polymerization system. The polymerization system may contain up to 8 wt%, preferably up to 6 wt%, and more preferably up to 4 wt% of polyisocyanate, based on the total weight of the polymerization system.

[0050] Shell component ii) - polycaprolactone polyol

[0051] The second component of the polymer shell is a polycaprolactone polyol containing 2 to 4 free hydroxyl groups. The polycaprolactone polyol can be a diol, a triol or a tetraol, preferably a diol or a triol, more preferably a triol. Preferably, the polycaprolactone polyol is formed by a caprolactone monomer and a diol (e.g., diethylene glycol or butanediol) or a triol (e.g., trimethylolpropane) initiator. Without being bound by theory, preferably when measured using the method described in OECD 301F, the presence of the polycaprolactone polyol in the polymer shell can surprisingly increase the biodegradability of the polymer shell or microcapsule.

[0052] The molecular weight (preferably number average molecular weight) of the polycaprolactone polyol may be at least 200 g / mol, preferably at least 300 g / mol, more preferably at least 350 g / mol. The molecular weight (preferably number average molecular weight) of the polycaprolactone polyol may be at most 20,000 g / mol, preferably at most 15,000 g / mol, more preferably at most 10,000 g / mol, still more preferably at most 5,000 g / mol, preferably at most 4,000 g / mol, preferably at most 3,000 g / mol, preferably at most 2,000 g / mol, preferably at most 1,500 g / mol. Preferably, the molecular weight (preferably number average molecular weight) range of the polycaprolactone polyol is 200 to 10,000 g / mol, more preferably 300 to 5,000 g / mol, more preferably 300 to 2,000 g / mol.

[0053] Suitable polycaprolactone polyols include, but are not limited to, the CAPA series available from Perstorp / Ingevity and mixtures thereof. The polycaprolactone polyol may be selected from CAPA 2043, 2101, 2201, 2205, 2209, 2201A, 2203A, 2302, 2402, 7201A, 7203, 3031, 3050, 3091 and 4101 from Perstorp / Ingevity, preferably the polycaprolactone polyol is selected from CAPA 2043, CAPA 2101 and CAPA 3050 from Perstorp / Ingevity. Preferably, the polycaprolactone polyol is a polycaprolactone triol.

[0054] The polymer shell may comprise 0.5% to 50% by weight of polycaprolactone polyol, based on the total weight of the shell components in the microcapsule. The polymer shell may comprise at least 1%, preferably at least 2.5% by weight of polycaprolactone polyol, based on the total weight of the shell components in the microcapsule. The polymer shell may comprise up to 40%, preferably up to 30%, more preferably up to 20% by weight of polycaprolactone polyol, based on the total weight of the shell components in the microcapsule. Preferably, the polymer shell comprises 2.5% to 30% by weight of polycaprolactone polyol, based on the total weight of the shell components in the microcapsule.

[0055] The amount of polycaprolactone polyol in the microcapsule can also be specified by reference to the amount of polycaprolactone polyol contained in the polymerization system, see Example 1 below. Based on the total weight of the polymerization system, the polymerization system may contain at least 0.05 wt%, preferably at least 0.1 wt%, more preferably at least 0.15 wt%, and especially at least 0.2 wt% of polycaprolactone polyol. Based on the total weight of the polymerization system, the polymerization system may contain up to 2 wt%, preferably up to 1 wt%, more preferably up to 0.75 wt%, and especially up to 0.5 wt% of polycaprolactone polyol.

[0056] Shell component iii) - Polyethyleneimine

[0057] Another component of the polymer shell is polyethyleneimine. Any molecular weight and any degree of crosslinking or branching of the polymer can be used in the present invention. Preferably, the polyethyleneimine has a branched structure. Preferably, the polyethyleneimine is not a linear polyethyleneimine. The molecular weight (preferably number average molecular weight) of the polyethyleneimine can be at least 500g / mol, preferably at least 1,000g / mol, more preferably at least 1,500g / mol. The molecular weight (preferably number average molecular weight) of the polyethyleneimine can be at most 10,000g / mol, preferably at most 8,000g / mol, more preferably at most 6,000g / mol, more preferably at most 5,000g / mol, preferably at most 4,000g / mol, preferably at most 3,000g / mol, preferably at most 2,500g / mol. Preferably, the molecular weight (preferably number average molecular weight) of the polyethyleneimine ranges from 500 to 5,000g / mol. Preferably, the polyethyleneimine is cationic. Cationic polyethyleneimines may advantageously promote retention of the microcapsules on fiber surfaces such as fabric or hair.Preferably, the polyethyleneimines are cationic and have a branched structure.

[0058] Suitable polyethyleneimines are available from BASF (Ludwigshafen, Germany) as Lupasol grades (e.g. Lupasol FG, Lupasol G20 anhydrous, Lupasol PR 8515, Lupasol WF, Lupasol FC, Lupasol G20, Lupasol G35, Lupasol G100, Lupasol G500, Lupasol HF, Lupasol PS, Lupasol HEO 1, Lupasol PN50, Lupasol PN60, Lupasol PO100 and Lupasol SK). Preferably, the polyethyleneimine is LUPASOL PR 8515.

[0059] Preferably, the polymer shell comprises at least 0.5%, more preferably at least 1%, still more preferably at least 1.5%, in particular at least 2% by weight of polyethyleneimine, based on the total weight of the shell components in the microcapsule. Preferably, the polymer shell comprises at most 20%, more preferably at most 15%, still more preferably at most 10% by weight of polyethyleneimine, based on the total weight of the shell components in the microcapsule. Preferably, the polymer shell comprises from 1% to 10% by weight of polyethyleneimine, based on the total weight of the shell components in the microcapsule.

[0060] The amount of polyethyleneimine in the microcapsules can also be specified by reference to the amount of polyethyleneimine contained in the polymerization system, for example see Example 1 below. The polymerization system may contain at least 0.05 wt%, preferably at least 0.1 wt%, more preferably at least 0.15 wt% polyethyleneimine, based on the total weight of the polymerization system. The polymerization system may contain up to 3 wt%, preferably up to 2 wt%, more preferably up to 1 wt%, in particular up to 0.5 wt% polyethyleneimine, based on the total weight of the polymerization system.

[0061] Optional other shell components

[0062] In addition to polyisocyanate, polycaprolactone polyol and polyethyleneimine, the polymer shell may optionally contain one or more other shell components. Preferably, the optional shell component comprises an alkyl silicate. Preferably, the optional shell component comprises a sugar or a sugar alcohol. Preferably, the polymer shell also comprises at least one of an alkyl silicate, a sugar and a sugar alcohol. The polymer shell may further comprise an alkyl silicate. The polymer shell may further comprise a sugar or a sugar alcohol, preferably a monosaccharide, preferably glucose. Preferably, the polymer shell also comprises iv) an alkyl silicate and v) a sugar or a sugar alcohol.

[0063] Preferably, the polymer shell further comprises an alkyl silicate. Preferably, the alkyl silicate is polymeric. Preferably, the alkyl silicate is ethyl silicate, more preferably ethyl silicate polymer. The alkyl silicate may be selected from Wacker TES 40WN and Dynasylan 40. The alkyl silicate may react during the formation of the polymer shell to provide polymeric silicon dioxide (SiO 2) structure. The rapidity of this reaction can provide advantages in the production process of microcapsules. The microcapsules may contain a polymerized silica structure. The polymerized shell may contain a polymerized silica structure. The combination of polyisocyanates and alkyl silicates in the shell component can advantageously provide beneficial properties for the microcapsules. Alkyl silicates can increase the heat resistance of the microcapsules. Alkyl silicates can provide stability for the microcapsule slurry formed during the production of the microcapsules. Without being bound by theory, when alkyl silicates are present in a formulation comprising microcapsules and one or more surfactants, alkyl silicates can provide stability for the microcapsules. The surfactant can be selected from anionic, cationic, nonionic and zwitterionic surfactants, preferably anionic and cationic surfactants. Alkyl silicates can surprisingly improve the tolerance of microcapsules to such surfactants. Many home care and personal care formulations such as fabric detergents and fabric softeners include such surfactants.

[0064] Preferably, the polymer shell comprises at least 1% by weight of alkyl silicate, more preferably at least 2.5%, still more preferably at least 5%, in particular at least 7.5%, based on the total weight of the shell components in the microcapsule. The polymer shell comprises up to 35%, more preferably up to 25% by weight of alkyl silicate, based on the total weight of the shell components in the microcapsule. Preferably, the polymer shell comprises from 7.5% to 25% by weight of alkyl silicate, based on the total weight of the shell components in the microcapsule.

[0065] The amount of alkyl silicate in the microcapsules can also be specified by reference to the amount of alkyl silicate contained in the polymerization system, for example see Example 1 below. The polymerization system may contain at least 0.2 wt%, preferably at least 0.4 wt%, more preferably at least 0.6 wt% of alkyl silicate, based on the total weight of the polymerization system. The polymerization system may contain up to 4 wt%, preferably up to 3 wt%, more preferably up to 2 wt% of alkyl silicate, based on the total weight of the polymerization system.

[0066] Preferably, the polymer shell further comprises a sugar or sugar alcohol (including but not limited to glucose and sorbitol), preferably a monosaccharide, more preferably glucose, and particularly preferably glucose monohydrate. The sugar or sugar alcohol can be reacted with a polyisocyanate to be incorporated into the polymer shell as a shell component.

[0067] Preferably, the polymer shell comprises at least 5% by weight of sugar or sugar alcohol, more preferably at least 10%, still more preferably at least 15%, in particular at least 20%, based on the total weight of the shell components in the microcapsule. Preferably, the polymer shell comprises at most 60%, more preferably at most 50%, even more preferably at most 40% by weight of sugar or sugar alcohol, based on the total weight of the shell components in the microcapsule.

[0068] The amount of sugar or sugar alcohol in the microcapsule can also be specified by reference to the amount contained in the polymerization system, for example, see Example 1 below. Based on the total weight of the polymerization system, the polymerization system may contain at least 0.1 wt%, preferably at least 0.5 wt%, more preferably at least 1 wt% of sugar or sugar alcohol. Based on the total weight of the polymerization system, the polymerization system may contain up to 5 wt%, preferably up to 4 wt%, more preferably up to 3 wt% of sugar or sugar alcohol.

[0069] Preferably, the optional other shell components comprise at least one polymer. Such polymers include, for example, polyamines and polyquaternium salts. In certain embodiments, the at least one polymer may be selected from amphoteric and cationic polymers having a weight average molecular weight ranging from 1,000 to 1,000,000 g / mol, preferably 10,000 to 500,000 g / mol.

[0070] Preferably, the polymer shell does not comprise polylysine.

[0071] Microcapsule core

[0072] The microcapsule core contains the active material. The core is generally hydrophobic. Preferably, the active material is hydrophobic.

[0073] Active materials can be volatile materials or non-volatile materials. The technical benefits provided by non-volatile active materials are different from the technical benefits from volatile active materials such as fragrances. Non-volatile active materials do not rely on the sense of smell, but provide other effects. In this specification, "non-volatile material" refers to an active material that does not volatilize too much. Flavors or fragrances are not non-volatile. When applied to a surface and left at 25°C, a non-volatile material will lose less than 50% of its mass over a period of 7 days. Non-volatile active materials generally have a boiling point greater than 250°C.

[0074] Preferably, the active material is selected from fragrances, fragrances, flavoring agents, UV absorbers, emollients, pesticides, phase change materials (PCMs), dyes, inks, conditioners (e.g., hair or skin conditioners), cleansers (e.g., hair or skin cleansers), cosmetic actives, personal care actives, home care actives, pharmaceutical actives, agrochemical actives, oxidants, bleaching agents, pharmaceuticals, fertilizers, nutrients, enzymes, liquid crystals, catalysts, and chemical reactants. The active material may not contain a pesticide.

[0075] More preferably, the active material is selected from fragrances, perfumes, flavorings, UV absorbers, emollients, pesticides, phase change materials (PCMs), dyes, inks, conditioners (e.g., hair or skin conditioners), cleansers (e.g., hair or skin cleansers), cosmetic actives, personal care actives, home care actives, pharmaceutical actives, and agrochemical actives. Preferably, the active material is selected from fragrances, perfumes, flavorings. Preferably, the active material comprises a fragrance.

[0076] Preferably, the active material is a volatile material. Preferably, the volatile material will lose more than 50% of its mass over a period of 7 days when applied to a surface and left at 25°C.

[0077] The core may comprise a mixture of active materials. Preferably, the active material is not a surfactant. The core may also comprise one or more oil-soluble diluents or solvents.

[0078] The core may comprise at least 40 wt %, preferably at least 60 %, in particular at least 70 %, ideally at least 80 % and especially at least 90 wt % of active material, based on the total weight of the core. The core may comprise 100 wt % of active material, based on the total weight of the core. The core may consist essentially of active material.

[0079] Preferably, the active material is a mixture of at least one flavor compound and at least one solvent. The properties and types of the flavor compounds present in the microcapsules are not guaranteed to be described in detail here, and they are in any case inexhaustible, and those skilled in the art can select them based on their common sense and according to the intended use or application and the desired sensory effect. Usually, the aromatic material is a mixture of flavor compounds. Flavor compounds can belong to different chemical categories, such as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen-containing or sulfur-containing heterocyclic compounds and essential oils, and the materials can be natural or synthetic sources. Many of these flavor compounds are listed in the references, such as S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA's book or its updated version, and its relevant parts are incorporated herein by reference.

[0080] Preferably the fragrance material comprises at least one fragrance compound selected from the group consisting of:

[0081] i) Hydrocarbons;

[0082] ii) aliphatic alcohols;

[0083] iii) aliphatic ketones and their oximes;

[0084] iv) aliphatic carboxylic acids and their esters;

[0085] v) acyclic terpene alcohols;

[0086] vi) acyclic terpene aldehydes and ketones;

[0087] vii) cyclic terpene alcohols;

[0088] viii) cyclic terpene aldehydes and ketones;

[0089] ix) cyclic alcohols;

[0090] x) alicyclic alcohols;

[0091] xi) cyclic and alicyclic ethers;

[0092] xii) (ethoxymethoxy)cyclododecane;

[0093] xiii) cyclic ketones;

[0094] xv) Esters of cyclic alcohols;

[0095] xvi) esters of cycloaliphatic carboxylic acids;

[0096] xvii) aromatic and aliphatic alcohols;

[0097] xviii) Esters of aliphatic alcohols and aliphatic carboxylic acids;

[0098] xix) aromatic and aliphatic aldehydes;

[0099] xx) aromatic and aliphatic ketones;

[0100] xxi) aromatic and aliphatic carboxylic acids and their esters;

[0101] xxii) nitrogen-containing aromatic compounds;

[0102] xxiii) phenols, phenyl ethers and phenyl esters;

[0103] xxiv) heterocyclic compounds;

[0104] xxv) lactones; and

[0105] xxvi) Essential oils.

[0106] Preferably, the microcapsule core comprises at least one solvent. The solvent may assist in the encapsulation of the active material by helping to retain the active material in the core phase during polymerization of the shell. The solvent may comprise at least one ester, preferably an ester oil.

[0107] The solvent can be a hydrophobic material miscible with the fragrance compound. The solvent can provide at least one of the following benefits: i) increasing the compatibility of the compound in the active material, ii) increasing the overall hydrophobicity of the core, iii) affecting the vapor pressure of the core, and iv) providing a rheological structure for the core. Suitable solvents are those with reasonable affinity for the fragrance compound. The group contribution method of the predicted partition coefficient (which can be represented by the ClogP value) can be used to determine the affinity. Preferably, the ClogP of the solvent is greater than 2.5, preferably greater than 3.5, and more preferably greater than 5.5. It should be noted that selecting a solvent and total active material with high affinity to each other will lead to an improvement in the stability of the core.

[0108] Preferably, the compound in the active material has a ClogP of 0.5 to 15. Preferably, the active material has a weight average ClogP of at least 2. The use of perfume compounds to prepare perfume materials having a weight average ClogP of at least 2 may be suitable for encapsulation. The active compound is generally water-insoluble and can be delivered to consumer products at different stages, such as wet and dry fabrics, by the microcapsules of the present invention. In the absence of encapsulation, free perfume compounds may evaporate or dissolve in water during use (e.g., during a washing cycle). Higher ClogP perfume compounds are generally well delivered from conventional (non-encapsulated) perfumes in consumer products, but are also suitable for encapsulation for overall aromatic properties purposes, more durable perfume delivery, or to overcome incompatibility with consumer products. For example, active compounds can be encapsulated to overcome these shortcomings, and the active compounds would otherwise be unstable, resulting in product thickening or discoloration or otherwise adversely affecting the desired consumer product properties.

[0109] The amount of active material in the microcapsules can be specified by reference to the amount of active material contained in the polymerization system, for example see Example 1 below. The polymerization system may contain at least 10 wt%, preferably at least 15 wt%, more preferably at least 20 wt%, and in particular at least 25 wt% of active material, based on the total weight of the polymerization system. The polymerization system may contain up to 45 wt%, preferably up to 40 wt%, more preferably up to 35 wt%, and in particular up to 30 wt% of active material, based on the total weight of the polymerization system.

[0110] Deposition Additives

[0111] Preferably, the microcapsules further comprise a deposition additive on their surface. The deposition additive may be polymeric. Preferably, the deposition additive is cationic. Cationic deposition additives may assist in the deposition of the microcapsules on fiber surfaces such as textiles or hair. Preferably, the deposition additive comprises a quaternary nitrogen group. Preferably, the deposition additive is a polyquaternium salt, more preferably polyquaternium-11 (available from BASF as Luviquat PQ11). The deposition additive may be selected from Luviquat PQ11, Lupamin9030, Salcare SC60, SoftCAT SX 1300X, Jaguar C17, Merquat 550. The deposition additive may be added to the polymerization system during the preparation of the microcapsules, preferably after the microcapsules are formed. Preferably, the polymerization system is heated after the deposition additive is added to bind the deposition additive to the surface of the microcapsules. The deposition additive may comprise hydrolyzed protein.

[0112] The polymerization system may comprise at least 2 wt%, preferably at least 4 wt%, more preferably at least 6 wt%, and in particular at least 8 wt% of the deposition additive, based on the total weight of the polymerization system. The polymerization system may comprise up to 20 wt%, preferably up to 18 wt%, more preferably up to 16 wt%, and in particular up to 14 wt% of the deposition additive, based on the total weight of the polymerization system.

[0113] Polymerization system

[0114] Preferably, the microcapsules are produced in a polymerization system. The polymerization system may comprise an aqueous phase and an oil phase. The oil phase may be a dispersed and / or emulsified oil phase. The aqueous phase, oil phase, shell component and all other ingredients used in the method for forming microcapsules will be referred to herein as the "polymerization system".

[0115] One or more components of the microcapsule may be present in the oil phase. Preferably, the active material is present in the oil phase. Preferably, the polyisocyanate is present in the oil phase. Preferably, the polycaprolactone polyol is present in the oil phase. Preferably, the alkyl silicate (when included) is present in the oil phase.

[0116] During formation of the microcapsules, the shell components react to form a polymer shell surrounding the core. The shell components are reacted preferably to form a microcapsule having a core comprising an oil phase within the polymer shell. The core comprises a fragrance material.

[0117] The polymeric system may comprise a sugar or sugar alcohol (including but not limited to glucose and sorbitol), preferably a monosaccharide, more preferably glucose. Glucose monohydrate is particularly preferred. Preferably, the sugar or sugar alcohol is present in the aqueous phase. The sugar or sugar alcohol may react with a polyisocyanate to be incorporated into the polymer shell of the microcapsule as a shell component.

[0118] The polymerization system may further comprise one or more emulsifiers and / or other surfactants. An emulsifier, which may have a high HLB (preferably an HLB of 10 to 20, more preferably 15 to 20), may be present in the water phase to aid in the emulsification of the oil phase.

[0119] The polymerization system may also include at least one additive to assist in the production of the microcapsules. The additive may include a hydrophilic polymer, such as a polymer containing pendant hydroxyl groups, such as polyvinyl alcohol. The polyvinyl alcohol may be present in the aqueous phase. The polyvinyl alcohol may be used in aqueous solution. The polyvinyl alcohol may be derived from polyvinyl acetate, and preferably 75 to 99% of the vinyl acetate groups are hydrolyzed to vinyl alcohol units.

[0120] The polymeric system may comprise a carboxyalkyl cellulose, preferably carboxymethyl cellulose, especially sodium carboxymethyl cellulose.

[0121] Based on the total weight of the polymerization system, the polymerization system may contain at least 0.1 wt%, preferably at least 0.5 wt%, more preferably at least 1 wt% of sugar or sugar alcohol.Based on the total weight of the polymerization system, the polymerization system may contain up to 8 wt%, preferably up to 6 wt%, more preferably up to 4 wt% of sugar or sugar alcohol.

[0122] The polymerization system may comprise at least 0.05 wt%, preferably at least 0.1 wt% carboxymethyl cellulose, based on the total weight of the polymerization system. The polymerization system may comprise up to 2 wt%, preferably up to 1.5 wt%, more preferably up to 1 wt% carboxymethyl cellulose, based on the total weight of the polymerization system.

[0123] The polymerization system may comprise at least 1 wt%, preferably at least 2 wt% urea based on the total weight of the polymerization system. The polymerization system may comprise up to 8 wt%, preferably up to 6 wt%, more preferably up to 4 wt% urea based on the total weight of the polymerization system.

[0124] Based on the total weight of the polymerization system, the polymerization system may contain at least 0.1 wt%, preferably at least 0.15 wt% xanthan gum.Based on the total weight of the polymerization system, the polymerization system may contain up to 2 wt%, preferably up to 1.5 wt%, more preferably up to 1 wt% xanthan gum.

[0125] Preferably, the microcapsules of the present invention are produced in the form of a slurry. The slurry may comprise microcapsules, water and at least one surfactant.

[0126] An advantage of the microcapsules of the present invention is that they are biodegradable, preferably readily biodegradable. The biodegradability of the microcapsules, preferably the biodegradability of the polymer shell, can be measured by the standard manometric respirometry method described in OECD 301F. When testing biodegradability using the method described in OECD 301F, the polymer shell preferably has an average degradation value of at least 60%, preferably at least 70%, more preferably at least 80%, and even more preferably at least 90% after 28 days. The polymer shell may have an average degradation value of at most 100%, preferably at most 99% after 28 days.

[0127] Preferably, the microcapsules do not contain waxes having a melting point above 40°C.

[0128] Preferably, the microcapsules do not contain aminoplast resins.

[0129] Method for forming microcapsules

[0130] The method for forming microcapsules according to the present invention comprises the following steps:

[0131] a) forming a polymerization system comprising an aqueous phase and a dispersed oil phase, wherein the oil phase comprises the active material, the polyisocyanate shell component and the polycaprolactone polyol shell component;

[0132] b) reacting the polyethyleneimine shell component by adding it to the aqueous phase to form microcapsules comprising a core of the oil phase within the polymer shell;

[0133] c) optionally, adding a deposition additive to the surface of the microcapsules; and

[0134] d) Optionally, adjusting the pH of the microcapsules using a metal hydroxide or an inorganic acid.

[0135] The polymerization system may comprise polyvinyl alcohol. Preferably, the polymerization system does not comprise polyvinyl alcohol. The polymerization system may comprise a sugar or sugar alcohol (including but not limited to glucose and sorbitol), preferably a monosaccharide, more preferably glucose, and particularly preferably glucose monohydrate. The polymerization system may comprise carboxymethyl cellulose, preferably sodium carboxymethyl cellulose. The polymerization system may comprise any of the features of the polymerization system described herein. Once the microcapsules are formed by polymerization, one or more optional post-polymerization steps may be taken.

[0136] Preferably, the method comprises the step c) adding a deposition additive to the surface of the microcapsules. Preferably, the deposition additive is a cationic polymer. Preferably, the deposition additive comprises a hydrolyzed protein. The deposition additive may comprise any of the features of the deposition additives described herein.

[0137] If an acidic shell monomer is used, the resulting microcapsules or microcapsule slurry may be acidic. Such microcapsules may be neutralized using a hydroxide, preferably a metal hydroxide, more preferably an alkali metal hydroxide, in particular sodium hydroxide. Examples of suitable alkali metal hydroxides are NaOH and KOH. The microcapsules may also be neutralized using an amine, such as ammonia, monoethanolamine, diethanolamine or triethanolamine, preferably ammonia. Alternatively, if the pH is too high, a mineral acid, preferably hydrochloric acid, may be used to neutralize the microcapsules.

[0138] Preferably, the method comprises step d) neutralizing the microcapsules using a metal hydroxide or an inorganic acid. Preferably, the pH of the microcapsules is adjusted to 7 to 8. Preferably, the metal hydroxide is NaOH and / or the inorganic acid is hydrochloric acid.

[0139] The method may optionally include a step of adding urea after the microcapsules are formed. Urea may improve the curing efficiency and / or the physicochemical and barrier properties of the microcapsules.

[0140] The method may optionally include a step of adding xanthan gum after the microcapsules are formed. Xanthan gum can increase the viscosity of the slurry and improve the stability of the microcapsules, for example, by preventing separation of the slurry.

[0141] Preparations containing microcapsules

[0142] The microcapsules of the present invention can be included in formulations having many different applications, such as crop care formulations, health care formulations, pharmaceutical formulations, personal care formulations, and home care formulations.

[0143] According to one aspect, the present invention provides a personal care formulation comprising the microcapsules or slurry according to the present invention. Preferably, the personal care formulation is for topical application to the skin or hair.

[0144] The personal care formulation may be selected from hand soaps; bar soaps; liquid soaps; face and body washes; personal care cleansers; shampoos; conditioners; toothpastes; shaving creams or gels; foot care products, moisturizers, sunscreens, after-sun products, body butters, gel creams, high fragrance content products, fragrance creams, baby care products, hair treatments, hair colorants, skin toning and skin lightening products, anhydrous products, antiperspirant and deodorant products, tanning products, 2-in-1 foaming emulsions, multiple emulsions, preservative-free products, mild formulations, scrubbing formulations (e.g. containing solid beads), silicone-in-water formulations, pigmented products, sprayable emulsions, cosmetics, color cosmetics, conditioners, shower products, foaming emulsions, make-up removers, eye make-up removers and wipes. Preferably, the personal care formulation is selected from hair care products, skin care products, cosmetics, personal care cleansers, deodorants and antiperspirants.

[0145] Personal care formulations preferably comprise the microcapsules or slurries according to the invention and at least one additional personal care ingredient. The personal care ingredients may be selected from cleansers, hair conditioners, hair fixatives, anti-dandruff agents, hair growth promoters, fragrances, sunscreens, sunscreens, pigments, humectants, film formers, hair dyes, make-up agents, thickeners, emulsifiers, moisturizers, emollients, preservatives, deodorant actives, dermatologically acceptable carriers, surfactants, abrasives, absorbents, fragrances, colorants, essential oils, astringents, anti-acne agents, anti-caking agents, defoamers, antioxidants, binders, enzymes, enzyme inhibitors, enzyme activators, coenzymes, plant extracts, ceramides, buffers, fillers, chelating agents, cosmetic biocides, topical analgesics, substantivity increasing agents, sunscreens, pH adjusters, reducing agents, sequestrants, skin bleaching and / or lightening agents, skin conditioning agents, skin soothing and / or healing agents, skin treatment agents, vitamins or preservatives. Preferably, the personal care ingredients are selected from cleansers, hair conditioners, skin conditioners, hair fixatives, anti-dandruff agents, hair growth promoters, fragrances, sunscreen compounds, pigments, humectants, film formers, moisturizers, alpha-hydroxy acids, hair colorants, make-up agents, thickeners, preservatives, deodorants, surfactants. The personal care formulation may comprise the microcapsules according to the present invention and at least one surfactant. The at least one surfactant may be selected from anionic, cationic, nonionic and zwitterionic surfactants, preferably anionic and cationic surfactants.

[0146] According to one aspect, the present invention provides a home care formulation comprising the microcapsules or slurry according to the present invention. Preferably, the home care formulation is for application to fabrics or textiles.

[0147] The home care formulation may be selected from fabric detergents (liquid, powder, concentrate, unit dose or tablet form), fabric softeners (liquid, powder, concentrate, unit dose or tablet form), fabric wash additives, fabric fragrance enhancers (liquid, gel, tablet, powder or granular form), freshening sprays, air care products, cleaning products, fabric cleaners, fabric conditioners, stain removers, hard surface cleaners, hand dishwashing detergents, machine dishwashing detergents, polishes and floor finishes. Preferably, the home care formulation is selected from fabric conditioners, fabric detergents, fabric softeners, fabric wash additives, fabric fragrance enhancers, freshening sprays, air care products and cleaning products. Preferably, the home care formulation is a fabric detergent or a fabric softener.

[0148] The home care formulation preferably comprises microcapsules or slurries according to the present invention and at least one other home care ingredient. The home care ingredient may be selected from surfactants, builders, chelants, dye transfer inhibitors, dispersants, enzymes, enzyme stabilizers, catalytic materials, bleach activators, hydrogen peroxide, hydrogen peroxide sources, preformed peracids, polymeric dispersants, soil removal / anti-redeposition agents, brighteners, foam suppressors, dyes, fabric softeners, carriers, structurants, hydrotropes, processing aids, solvents and / or pigments and mixtures thereof, preferably, the home care ingredient is selected from surfactants, builders, chelants, fabric softeners. The home care formulation may comprise microcapsules according to the present invention and at least one surfactant. The at least one surfactant may be selected from anionic, cationic, nonionic and zwitterionic surfactants, preferably anionic and cationic surfactants.

[0149] Any or all features described herein and / or any or all steps of any method or process described herein may be used in any combination in any aspect of the invention. Example

[0150] The present invention is illustrated by the following non-limiting examples. It should be understood that, unless otherwise stated herein, or unless otherwise stated in the referenced test methods and procedures, all test procedures and physical parameters described herein are measured at atmospheric pressure and room temperature (i.e., about 25° C.). Unless otherwise stated, all parts and percentages are by weight.

[0151] Test Method

[0152] In this specification, the following test methods are used:

[0153] (i) Particle size analysis of the microcapsules (including measurement of D10, D50, D90 volume mean diameters) was performed using a Malvern Mastersizer 3000E with the provided software and measurement unit Hydro EV. This is a laser diffraction particle size analysis device that uses Mie theory and the refractive index of the sample to determine the particle size distribution. The microcapsule sample was mixed thoroughly and then diluted into water for particle size measurement. Various particle size parameters and distributions were measured automatically.

[0154] (ii) The performance of the fragrance release of microcapsules in fabric softeners and liquid laundry detergents was evaluated using a towel washing regimen and scored by panelists. Fabric softeners and liquid detergents were prepared according to a standard formulation to which a controlled amount of microcapsules was added. One towel per sample was hand washed (at 40°C) in a formulation containing microcapsules. All towels were evaluated after drying for 24 hours. The purpose of these evaluations was to determine the effectiveness of fragrance release by the microcapsules after rubbing the dry towels. Panelists recorded their fragrance performance scores before and after rubbing. The scoring system was 1 to 10, with higher scores indicating higher fragrance intensity and better performance. The detailed procedures for evaluating fabric softeners and liquid detergents are as follows:

[0155] Fabric Softener:

[0156] 1) According to the number of panelists, 10 g of the sample is prepared and used for each towel.

[0157] 2) Dilute 10 grams of fabric softener into 1 liter at 40°C.

[0158] 3) Stir with a spatula to dissolve the product evenly in water.

[0159] 4) Put the towels in and rub the towels against each other about 5 times (the washer should wear disposable gloves) and let them soak for 25 minutes.

[0160] 5) Once the time was complete, the towels were wrung out and left to dry for 24 hours before evaluation (the towels were air dried in an unperfumed atmosphere).

[0161] Liquid laundry detergent:

[0162] The method is similar to the softener method, except that after step 4, and at the end of 25 minutes, the towels are rinsed with 1 liter of 40°C water for each towel used (5 times).

[0163] (iii) Biodegradability / Biodegradability is determined by method OECD 301F as described in the document "OECD Guidelines for the Testing of Chemicals: Ready Biodegradability" (adopted by the OECD Committee on July 17, 1992). Method OECD 301F is a standard manometric respirometry test. According to OECD 301F, a test material is considered to be readily biodegradable if more than 60% of the test material is degraded after 28 days.

[0164] Comparative Example A

[0165] Using the materials listed in Table 1, comparative microcapsules not according to the present invention (Comparative Microcapsules A) were synthesized.

[0166] Table 1: Polymerization system used for comparative microcapsules A

[0167]

[0168] Comparative microcapsules A were formed as follows using the materials of Table 1. Premix I was prepared by 4.42 g Poval 18-88, 600.60 g water and 1.95 g Finnfix 5, and heated until completely dissolved if necessary. Premix II was prepared by dropwise addition of 386.10 g fragrance 1 (containing standard fragrance compounds and solvents available from Iberchem), 27.95 g Takenate D131 N (from Mitsui Chemicals) and 13.00 g Wacker TES40 (from Wacker). The two premixes I and II were combined and emulsified at a speed of 9000 rpm at room temperature with the help of Ultraturrax T25. The pH of the emulsion was then adjusted to 2.5 using aqueous hydrochloric acid solution (10 wt %). Then, a solution of 2.60 g of Lupasol PR8515 (polyethyleneimine, from BASF) in 7% aqueous sodium bicarbonate solution was added to the emulsion over 2 hours at 35° C. and under stirring at 150 l / min. The reaction mixture was then subjected to the following temperature program: heating to 55° C. after those 2 hours, keeping this temperature for 2 hours, and then at 80° C. for 3 hours. Thereafter, 130.0 g of Luviquat PQ11 (from BASF) were added and mixed for 15 minutes at 8000 rpm using an Ultraturrax T25. A premix of urea and water (35.75 g each) was then prepared under heating at 60° C., added to the mixture, and when it dissolved, 2.6 g of Keltrol RD was added to the mixture under stirring, and the heating plate was turned off. The mixture was then cooled to room temperature. Finally, the pH of the resulting microcapsule slurry was adjusted to 7.5 using an aqueous sodium hydroxide solution or a formic acid solution.

[0169] The resulting microcapsule slurry will be referred to as Comparative Microcapsule A.

[0170] Example 1

[0171] The materials listed in Table 2 were used to synthesize microcapsules according to the present invention (microcapsule 1).

[0172] Table 2: Polymerization system used for microcapsule 1

[0173]

[0174]

[0175] The materials of Table 2 were used to form microcapsules 1 according to the invention as follows. Premix I was prepared from 5.20 g Poval 18-88, 567.58 g water and 1.95 g Finnfix 5, heated if necessary until completely dissolved. Premix II was prepared from 386.10 g fragrance 1 (containing standard fragrance compounds and solvents, purchased from Iberchem), 27.95 g Takenate D131N (from Mitsui Chemicals), 13.00 g Wacker TES40 (from Wacker), added dropwise and 4.94 g CAPA 2043 (from Perstorp). The two premixes I and II were combined and emulsified at room temperature at a speed of 9000 rpm with the help of an Ultraturrax T25. The pH of the emulsion was then adjusted to 2.5 using aqueous hydrochloric acid solution (concentration of 10 wt%). Then, a solution of 2.60 g of Lupasol PR8515 (polyethyleneimine, from BASF) in 7% aqueous sodium bicarbonate solution was added to the emulsion over 2 hours at 35° C. and under stirring at 150 l / min. The reaction mixture was then subjected to the following temperature program: heating to 55° C. after those 2 hours, keeping this temperature for 2 hours, and then at 80° C. for 3 hours. Thereafter, 130.0 g of Luviquat PQ11 (from BASF) were added and mixed for 15 minutes at 8000 rpm with an Ultraturrax T25. Then, under heating at 60° C., a premix of urea and water (35.75 g each) was prepared, added to the mixture, and when it dissolved, 2.6 g of Keltrol RD was added to the mixture under stirring, and the heating plate was turned off. The mixture was then cooled to room temperature. Finally, the pH of the resulting microcapsule slurry was adjusted to 7.5 using aqueous sodium hydroxide solution or hydrochloric acid solution.

[0176] The microcapsule slurry prepared according to the present invention will be referred to as Microcapsule 1.

[0177] Using the materials listed in Table 2, microcapsules 2 and 3 according to the present invention were synthesized using the method described in this example, wherein the materials were changed as follows:

[0178] a) Microcapsules 2 were prepared by replacing CAPA 2043 with the same weight of CAPA 2101 (1000 Mw linear polycaprolactone diol);

[0179] b) Microcapsules 3 were prepared by replacing CAPA 2043 with the same weight of CAPA 3050 (500 Mw polycaprolactone triol).

[0180] Using the materials listed in Table 3, microcapsules 4 according to the present invention were synthesized using the method described in this example, wherein the polyvinyl alcohol (Poval 18-88) of microcapsules 1 was replaced by glucose monohydrate.

[0181] Table 3: Polymerization system used for microcapsule 4

[0182] Ingredient name Dosage (wt% of the entire polymerization system) Fragrance 1 29.70 Takenate D131N 1.79 Wacker TES40 1.00 Polycaprolactone diol (PCLD) CAPA 2043 0.38 Glucose monohydrate CAS 5996-10-1 1.92 Finnfix 5(CMC) 0.15 Lupasol PR 8515 0.20 <![CDATA[NaHCO 3 Solution 7%]]> 4.66 Luviquat PQ 11 10.00 water Up to 100.00 Keltrol RD 0.30 total 100.00

[0183] Using the materials listed in Table 4, microcapsules 5 according to the invention were synthesized using the method described in this example, wherein CAPA 2043 of microcapsules 1 was replaced by CAPA 3050, and Takenate D131N polyisocyanate was replaced by Takenate D110N.

[0184] Table 4: Polymerization system for microcapsule 5

[0185]

[0186]

[0187] Microcapsules 6 according to the invention were synthesized using the materials listed in Table 5 using the method described in this example, wherein Keltrol RD was replaced by Polyquaternium 10 and the polyvinyl alcohol (Poval 18-88) of microcapsules 1 was replaced by glucose monohydrate.

[0188] Table 5: Polymerization system for microcapsules 6

[0189]

[0190]

[0191] Example 2

[0192] Comparative Microcapsules A from Example A and Microcapsules 1 from Example 1 were compared as follows. Particle size analysis was performed as described in the Test Methods herein to obtain the D10, D50 and D90 volume average diameters of the microcapsules. The results are given in Table 5.

[0193] Table 5: Particle size analysis

[0194] sample D10(μm) D50(μm) D90(μm) Comparison microcapsule A 3.20 9.77 18.4 Microcapsule 1 2.16 6.44 12.7

[0195] As can be seen from Table 5, the microcapsule 1 of the present invention has smaller volume average diameters D10, D50 and D90 than the comparative microcapsule A.

[0196] Example 3

[0197] The fragrance release performance of Microcapsules 1 from Example 1 and Comparative Microcapsules A from Example A in liquid laundry detergent was compared as described in the Test Methods herein. The results are given in Table 6.

[0198] Table 6: Fragrance release performance in liquid laundry detergents

[0199] Laundry detergent Before friction After friction Microcapsule 1 2 8 Comparison microcapsule A 2 6

[0200] Surprisingly, as can be seen in Table 6, in liquid laundry detergent, microcapsules 1 according to the invention have better fragrance release properties after rubbing than comparative microcapsules A. Without being bound by theory, this advantage can be attributed to the presence of polycaprolactone polyol in the shell component of microcapsules 1.

[0201] Example 4

[0202] Microcapsules 1 and 3 from Example 1 were compared for fragrance release performance in liquid laundry detergent and fabric softener as described in the Test Methods herein. The results are given in Tables 7 and 8.

[0203] Table 7: Fragrance release performance in liquid laundry detergents

[0204] Laundry detergent Before friction After friction Microcapsule 1 1 8 Microcapsule 3 1 9

[0205] Table 8: Fragrance release performance in fabric softeners

[0206] Laundry detergent Before friction After friction Microcapsule 1 3 9 Microcapsule 3 3 10

[0207] Surprisingly, as can be seen in Tables 7 and 8, microcapsule 3 performs better than microcapsule 1. Without being bound by theory, this advantage may be attributed to the presence of polycaprolactone triol in the shell component of microcapsule 3.

[0208] Example 5

[0209] Comparative Microcapsules A from Example A and Microcapsules 1 and 4 from Example 1 were compared for fragrance release performance in liquid laundry detergents and fabric softeners as described in the Test Methods herein. The results are given in Tables 9 and 10.

[0210] Table 9: Fragrance release performance in liquid laundry detergents

[0211] Laundry detergent Before friction After friction Microcapsule 1 2 7 Microcapsules 4 2 9 Comparison microcapsule A 2 5

[0212] Table 10: Fragrance release performance in fabric softeners

[0213] Laundry detergent Before friction After friction Microcapsule 1 2 8 Microcapsule 4 2 10 Comparison microcapsule A 2 7

[0214] Surprisingly, as can be seen in Tables 9 and 10, microcapsules 1 and 4 outperformed comparative microcapsule A. Without being bound by theory, this advantage can be attributed to the presence of polycaprolactone polyol in the shell component of microcapsules 1 and 4 and the presence of glucose monohydrate in the shell component of microcapsule 4.

[0215] Example 6

[0216] Microcapsules 1 and 5 from Example 1 were compared for fragrance release performance in liquid laundry detergent and fabric softener as described in the Test Methods herein. The results are given in Tables 11 and 12.

[0217] Table 11: Fragrance Release Performance in Liquid Laundry Detergents

[0218] Laundry detergent Before friction After friction Microcapsule 1 2 7 Microcapsules 5 3 9

[0219] Table 12: Fragrance release performance in fabric softeners

[0220] Laundry detergent Before friction After friction Microcapsule 1 2 8 Microcapsules 5 2 9

[0221] Surprisingly, as can be seen in Tables 11 and 12, microcapsule 5 performs better than microcapsule 1. Without being bound by theory, this advantage may be attributed to the presence of polycaprolactone triol in the shell component of microcapsule 5.

[0222] Example 7

[0223] As described in the test methods herein, the biodegradability of the capsule shells of Comparative Microcapsules A from Example A and Microcapsules 1 from Example 1 were compared according to OECD 301 F. The shells of the capsules were isolated and prepared for OECD 301 F testing using the following procedure:

[0224] 1) Filtration to remove water- and water-soluble components

[0225] 2) Wash the filtrate several times

[0226] 3) Dry the filtrate using an infrared dryer

[0227] 4) Grind the obtained solid material to break the capsule

[0228] 5) Wash with solvent to remove fragrance

[0229] 6) Repeat steps 3 to 5 several times until all the fragrance is removed.

[0230] 7) Finally, the solid wall material was reconstituted at 5% in sterile water for biodegradability testing.

[0231] Under the OECD 301F test, at 28 days, the average degradation of the comparative microcapsule A was 89%, and the average degradation of microcapsule 1 was 95%. This indicates that microcapsule 1 is more biodegradable than comparative microcapsule A.

[0232] It will be appreciated that the invention is not restricted to the details of the above embodiments which have been described merely by way of example. Many variations are possible.

Claims

1. Microcapsules comprising a hydrophobic core within a polymer shell, in: a) the polymer shell is formed from a shell component, the shell component comprising: i) a polyisocyanate, wherein the polyisocyanate is selected from xylylene diisocyanate (XDI) and its oligomers, adducts and derivatives; ii) polycaprolactone polyols containing 2 to 4 free hydroxyl groups; iii) polyethyleneimine; iv) optionally, other shell components; and b) The hydrophobic core comprises an active material.

2. The microcapsule according to claim 1, wherein the polymer shell further comprises an alkyl silicate, preferably an ethyl silicate polymer.

3. The microcapsule according to claim 2, wherein the polymer shell comprises 7.5 to 25 weight percent of the alkyl silicate, based on the total weight of the shell components in the microcapsule.

4. The microcapsule according to any one of the preceding claims, wherein the polymer shell comprises 20 to 75% by weight of the polyisocyanate, based on the total weight of the shell components in the microcapsule.

5. Microcapsules according to any one of the preceding claims, wherein the polymer shell comprises only one polyisocyanate.

6. The microcapsule according to any one of the preceding claims, wherein the polymer shell comprises 2.5 to 30 wt% of the polycaprolactone polyol, based on the total weight of the shell components in the microcapsule.

7. The microcapsule according to any one of the preceding claims, wherein the polycaprolactone polyol is formed from a caprolactone monomer and a diol or triol initiator.

8. The microcapsule according to any one of the preceding claims, wherein the molecular weight of the polycaprolactone polyol is from 200 to 10,000 g / mol.

9. The microcapsule according to any one of the preceding claims, wherein the polymer shell comprises 1 to 10 wt% of the polyethyleneimine, based on the total weight of shell components in the microcapsule.

10. The microcapsule according to any one of the preceding claims, wherein the molecular weight of the polyethyleneimine is from 500 to 5,000 g / mol.

11. Microcapsules according to any one of the preceding claims, wherein the polyethyleneimine is cationic and has a branched structure.

12. Microcapsules according to any one of the preceding claims, wherein the polymer shell has an average degradation value of more than 60%, preferably more than 70%, more preferably more than 80%, even more preferably more than 90% after 28 days when tested for biodegradability using the method described in OECD 301F.

13. The microcapsule according to any one of the preceding claims, wherein the microcapsule does not contain wax having a melting point above 40°C.

14. The microcapsule according to any one of the preceding claims, wherein the active substance is selected from the group consisting of fragrances, perfumes, flavorings, UV absorbers, emollients, pesticides, phase change materials, dyes, inks, conditioners, cleaners, cosmetic actives, personal care actives, home care actives, pharmaceutical actives, agrochemical actives, oxidants, bleaches, pharmaceuticals, fertilizers, nutrients, enzymes, liquid crystals, catalysts and chemical reactants.

15. The microcapsule according to any one of the preceding claims, wherein the microcapsule does not contain an aminoplast resin.

16. Microcapsules according to any one of the preceding claims, further comprising deposited additives on the surface of the microcapsules, preferably comprising hydrolyzed proteins.

17. A slurry comprising the microcapsules according to any one of claims 1 to 16, water and at least one surfactant.

18. Home care formulation comprising the microcapsules according to any one of claims 1 to 16 or the slurry according to claim 17 and at least one further home care ingredient.

19. A home care formulation comprising the microcapsules according to any one of claims 1 to 16 or the slurry according to claim 17, wherein the home care formulation is selected from fabric conditioners, fabric detergents, fabric softeners, fabric wash additives, fabric fragrance enhancers, freshener sprays, air care products and cleaning products.

20. A personal care formulation comprising the microcapsules according to any one of claims 1 to 16 or the slurry according to claim 17 and at least one additional personal care ingredient.

21. A personal care formulation comprising the microcapsules according to any one of claims 1 to 16 or the slurry according to claim 17, wherein the personal care formulation is selected from the group consisting of hair care products, skin care products, cosmetics, personal care cleansers, deodorants and antiperspirants.

22. A method for producing microcapsules according to any one of claims 1 to 16, wherein the method The following steps are involved: a) forming a polymerization system comprising an aqueous phase and a dispersed oil phase, wherein the oil phase comprises the active material, the polyisocyanate shell component and the polycaprolactone polyol shell component; b) reacting the polyethyleneimine shell component by adding it to the aqueous phase to form microcapsules comprising a core of the oil phase within the polymer shell; c) optionally, adding a deposition additive to the surface of the microcapsules; and d) Optionally, neutralizing the microcapsules using a metal hydroxide or an inorganic acid.

23. The method of claim 22, wherein the polymeric system further comprises a sugar or a sugar alcohol.

24. The method of claim 22 or 23, wherein the polymerization system does not comprise polyvinyl alcohol.

25. The method of any one of claims 22 to 24, wherein the polymerization system further comprises carboxymethyl cellulose.

26. The method according to any one of claims 22 to 25, comprising the step c) adding a deposition additive to the surface of the microcapsules, wherein the deposition additive is a cationic polymer.

27. The method according to any one of claims 22 to 26, comprising a step d) of neutralizing the microcapsules, wherein the metal hydroxide is NaOH and / or the inorganic acid is hydrochloric acid.

28. The method according to any one of claims 22 to 27, comprising the step of adding urea to the polymerization system after forming the microcapsules.

29. The method according to any one of claims 22 to 28, comprising the step of adding xanthan gum to the polymerisation system after forming the microcapsules.

30. Microcapsules obtainable by the method according to any one of claims 22 to 29.

Images