Biodegradable microcapsules made from pectin enzymatically crosslinked by laccase

Abstract

This disclosure relates to a biodegradable core-shell microcapsule that includes (a) a microcapsule core comprising an active material; and (b) a microcapsule shell comprising a pectin crosslinked in the presence of a laccase. This disclosure also relates to a process for producing such biodegradable core-shell microcapsule. The process involves: (a) providing an aqueous phase comprising a pectin; (b) providing an oil phase comprising an active material; (c) emulsifying the oil phase with the aqueous phase to form an emulsion; and (d) mixing a laccase with the emulsion at a temperature of from about 20 °C to about 60 °C to form a microcapsule slurry comprising the biodegradable core-shell microcapsule.

Description

[0001] IFF10015-WO-PCT

[0002] TITLE

[0003] Biodegradable Microcapsules Made from Pectin Enzymatically Crosslinked by Laccase

[0004] BACKGROUND

[0005] Field of the Disclosure

[0006] The present disclosure relates to a biodegradable core-shell microcapsule. Particularly, the microcapsule shell comprises a pectin enzymatically crosslinked using a laccase. The present disclosure also relates to a process of producing such biodegradable core-shell microcapsule.

[0007] Description of Related Art

[0008] Microcapsules are useful in a variety of applications where there is a need to deliver, apply, or release a fragrance or other active material in a time-delayed and controlled manner.

[0009] Current commercial fragrance capsules including melamine-formaldehyde and polyurea are made from synthetic materials, which are not readily biodegradable. This is an issue for several reasons. Firstly, consumers are demanding more environmentally friendly products. Secondly, new regulation from the European Chemicals Agency (ECHA) has banned the use of microplastics in a variety of consumer goods products (e.g., cosmetics, detergents, etc.). As a result, there is an ever-increasing demand for fragrance delivery technologies where the capsule wall material is more biodegradable and / or sustainable, and will satisfy the requirements set out in any currently existing and newly proposed regulations banning the use of microplastics.

[0010] BRIEF SUMMARY OF THE DISCLOSURE

[0011] The present disclosure provides a biodegradable core-shell microcapsule comprising: (a) a microcapsule core comprising an active material; and (b) a microcapsule shell comprising a pectin crosslinked in the presence of a laccase. The present disclosure also provides a process for producing such biodegradable core-shell microcapsule. The process comprises: (a) providing an aqueous phase comprising a pectin; (b) providing an oil phase comprising an active material; (c) emulsifying the oil phase with the aqueous phase to form an emulsion; and (d) mixing a laccase with the emulsion at a temperature of from about 20 °C to about 60 °C to form a microcapsule slurry comprising the biodegradable core-shell microcapsule. IFF10015-WO-PCT

[0012] DETAILED DESCRIPTION

[0013] The foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention, as defined in the appended claims. Other features and benefits of any one or more of the embodiments will be apparent from the following detailed description, and from the claims.

[0014] As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing” or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Further, unless expressly stated to the contrary, “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

[0015] Also, use of “a” or “an” are employed to describe elements and components described herein. This is done merely for convenience and to give a general sense of the scope of the invention. This description should be read to include one or at least one and the singular also includes the plural unless it is obvious that it is meant otherwise.

[0016] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, the present specification, including definitions, will control. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0017] When an amount, concentration, or other value or parameter is given as either a range, preferred range or a list of upper preferable values and / or lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. Where a range of numerical values is recited herein, unless otherwise stated, the range is intended to include the endpoints thereof, and all integers and fractions within the range. For example, when a IFF10015-WO-PCT range of "1 to 10" is recited, the recited range should be construed as including ranges "1 to 8", “3 to 10”, "2 to 7", "1.5 to 6", “3.4 to 7.8”, "1 to 2 and 7-10", “2 to 4 and 6 to 9”, “1 to 3.6 and 7.2 to 8.9”, "1 -5 and 10", “2 and 8 to 10”, “1 .5-4 and 8”, and the like.

[0018] The present disclosure illustratively described herein suitably may be practiced in the absence of any element or elements, limitation or limitations that are not specifically disclosed herein. While compositions and methods are described herein in terms of “comprising” various components or steps, the compositions and methods also can “consist essentially of” or “consist of” the various components or steps, unless stated otherwise.

[0019] All parts, percentages and proportions referred to herein and in the claims are by weight unless otherwise indicated.

[0020] Before addressing details of embodiments described below, some terms are defined or clarified.

[0021] The term “elevated temperature”, as used herein, means a temperature higher than the room temperature (e.g., 22 °C).

[0022] The terms “obtainable” and “obtained” can be used interchangeably in this disclosure and do not mean to indicate that, e.g., a product must be obtained by, e.g., the sequence of steps following the term “obtained” though such a limited understanding is always included by the terms as a preferred aspect of the present disclosure.

[0023] The term “microcapsule slurry”, as used herein, means an aqueous suspension of the biodegradable core-shell microcapsule. In some embodiments, the biodegradable core-shell microcapsule product produced in accordance with the methods and examples described in the present disclosure is in the form of a microcapsule slurry. The microcapsule slurry may be used directly in a consumer product. The microcapsule slurry may also be washed, coated, dried (e.g., spray-dried) and / or combined with one or more other microcapsules, active materials, and / or carrier materials.

[0024] The term “self-condensed polyisocyanate”, as used herein, means the polyurea formed by the self-polymerization of polyisocyanate in the presence of water. A person skilled in the art appreciates that isocyanate can react with water to form amine which can further react with isocyanate to form urea linkage. Accordingly, polyisocyanate can selfpolymerize in the presence of water to form polyurea. The self-condensed polyisocyanate is non-biodegradable. IFF10015-WO-PCT

[0025] The term “polyisocyanate”, as used herein, means a chemical compound having two or more isocyanate (-NCO) functional groups. The term “polyaldehyde”, as used herein, means a chemical compound having two or more aldehyde (-CHO) functional groups.

[0026] As used herein, the term “w / w” means weight by weight, and the term “w / v” means weight per volume. As used herein, the term “wt%” means percentage by weight.

[0027] As used herein, the terms “kg”, “g”, “mg” and “pg” refer to “kilogram”, “gram”, “milligram” and “microgram” respectively. The terms “L”, “mL” and “pL” refer to “liter”, “milliliter” and “microliter” respectively. The terms “cm”, “mm”, “pm” and “nm” refer to “centimeter”, “millimeter”, “micrometer” and “nanometer” respectively. The terms “mM” and “M” refer to molar concentration units “millimolar” (mmol / L) and “molar” (mol / L) respectively. Pectin

[0028] Pectin is a heteropolysaccharide derived from plants. The principal chemical component of pectin is galacturonic acid. The pectin can be a hydrolyzed pectin or an unhydrolyzed pectin. In some embodiments, the pectin comprises or is a sugar beet pectin, that is, the pectin is extracted or derived from sugar beet. Laccase

[0029] Laccase (EC 1 .10.3.2) is a copper-containing enzyme found in plants, fungi, and bacteria. It is an oxidase which can catalyze oxidation of a wide range of organic and inorganic substances, including phenols, ketones, phosphates, ascorbate, amines, and lignin. In some embodiments, the laccase is derived from fungi such as Trametes Versicolor. In some embodiments, laccase used in this disclosure is a native enzyme. In some embodiments, laccase used in this disclosure is a mutant enzyme. Laccase used in this disclosure has enzyme activity. In some embodiments, laccase used in this disclosure is in its properly folded and / or assembled form, which is operative and functional in catalyzing a chemical reaction. In some embodiments, laccase used in this disclosure is not denatured or unfolded.

[0030] Phenol Compound

[0031] The phenol compound of this disclosure is a chemical compound having one or more hydroxyl groups (-OH) bonded directly to an aromatic hydrocarbon group. In some embodiments, the phenol compound is selected from the group of gallic acid, ferulic acid, IFF10015-WO-PCT hydroquinone, protocatechuic acid, tannic acid, and combinations thereof. In some embodiments, the phenol compound is selected from the group of gallic acid, ferulic acid, hydroquinone, and combinations thereof. In some embodiments, the phenol compound comprises or is gallic acid.

[0032] Chitosan

[0033] Chitosan is a linear polysaccharide composed of randomly distributed |3-(1 -4)-linked D-glucosamine (deacetylated unit) and / V-acetyl-D-glucosamine (acetylated unit). Important characteristics in determining the functionality of chitosan are the degree of deacetylation (DDA) and weight average molecular weight (Mw). Chitosan with higher percentage DDA possesses more positively charged amine groups when dissolved in solution. In some embodiments, the chitosan has a degree of deacetylation (DDA) of from 50% to 95%, or from 65% to 90%. In some embodiments, the chitosan has a DDA of at least 80%. In some embodiments, the chitosan has weight average molecular weight of from 500 Da (daltons) to 1 ,000,000 Da, or from 2,000 Da to 500,000 Da, or from 10,000 Da to 400,000 Da, or from 50,000 Da to 250,000 Da.

[0034] Chitosan is derived from shellfish or fungi. In some embodiments, the chitosan comprises or is a fungal chitosan. Fungal production of chitosan allows for very high percentage DDA values due to the nature of the fermentation, with the ability to routinely produce a fungal chitosan with DDA as high as 99%. In some embodiments, chitosan is obtained from a fungal source or derived from fungal chitin by chemical deacetylation. Exemplary fungal sources that may be used in the preparation of fungal chitosan include, but are not limited to, Pleurotus ostreatus and Aspergillus niger. Active Material

[0035] The core of the biodegradable core-shell microcapsule comprises an active material. In some embodiments, the active material is hydrophobic. In some embodiments, the active material has a logP value (partition coefficient) of less than 2. In some embodiments, the active material comprises fragrance, flavor, agricultural active, pesticide, insecticide, herbicide, fungicide, pharmaceutical active, nutraceutical active, animal nutrition active, food active, microbio active, malodor counteractant, and / or cosmetic active. In some embodiments, the active material is selected from the group of fragrance, pro-fragrance, malodor counteractive agent, and combinations thereof. In some embodiments, the active material comprises or is a fragrance. IFF10015-WO-PCT

[0036] In some embodiments, the active material comprises agricultural active, pesticide, insecticide, herbicide, and / or fungicide. Encapsulation of agricultural actives, pesticides, insecticides, herbicides, and / or fungicides can increase their efficacy, extend their effective period and protect the environment. In some embodiments, the insecticide is an organophosphate insecticide. In some embodiments, the insecticide can be an organophosphate insecticide selected from the group of acephate, azinphos-mehyl, chlorfenvinphos, chlorethoxyfos, chlorpyriphos-methyl, diazinon, dimethoate, disulfoton, ethoprophos, fenitrothion, fenthiom, fenamiphos, fosthiazate, malathion, methamidophos, methidathion, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phorate, phosmet, profenofos, trichlorfon, and mixtures thereof. In some embodiments, the insecticide is selected from the group of cypermethrin, bifenthrin, A-cyhalothrin, and mixtures thereof. In some embodiments, the herbicide is selected from the group of clomazone, acetochlor, pendimethalin, and mixtures thereof. In some embodiments, the fungicide is tebuconazole.

[0037] It has been surprisingly discovered that laccase, as an enzyme, can catalyze the crosslinking of pectin, that is, pectin can be enzymatically crosslinked by laccase to form microcapsule shell. It has also been surprisingly discovered that a phenol compound can significantly improve the microcapsule shell made from pectin. It has also been surprisingly discovered that chitosan can further improve the microcapsule shell. Accordingly, the present disclosure provides a biodegradable core-shell microcapsule which comprises: (a) a microcapsule core comprising an active material; and (b) a microcapsule shell comprising a pectin crosslinked in the presence of a laccase. In some embodiments, the microcapsule shell further comprises a phenol compound crosslinked in the presence of a laccase. In some embodiments, the microcapsule shell further comprises a chitosan crosslinked with the pectin and / or the phenol compound in the presence of a laccase.

[0038] As used herein, the terms “capsule”, “microcapsule” and “core-shell microcapsule” are used interchangeably and refer to a substantially spherical structure having a well- defined core and a well-defined envelope or wall or shell. The “core” comprises an active material or material submitted to encapsulation. The terms “wall” and “shell” are used interchangeably to denote the structure formed by the encapsulating polymer surrounding the core being encapsulated. In general, the wall of the microcapsule is made of a continuous, polymeric phase with an inner surface and outer surface. The inner surface is IFF10015-WO-PCT in contact with the microcapsule core. The outer surface is in contact with the environment in which the microcapsule resides, e.g., an aqueous phase, skin, or hair. Ideally, the wall protects the core against deterioration by oxygen, moisture, light, and effect of other compounds or other factors; limits the losses of volatile core materials; and releases the core material under desired conditions. In this respect, the core-shell microcapsule of the present disclosure provides controlled release and / or diffusional release of the active material. As used herein, “controlled release” refers to retention of the active material in the core until a specified triggering condition occurs. Such triggers include, e.g., friction, swelling, a pH change, an enzyme, a change in temperature, a change in ionic strength, or a combination thereof.

[0039] The microcapsule core comprises an active material. In some embodiments, the microcapsule core further comprises an adjunct core material such as a solvent, an emollient, and / or a core modifier material. Examples of adjunct core materials include nanoscale solid particulate materials, polymeric core modifiers, solubility modifiers, density modifiers, stabilizers, humectants, viscosity modifiers, pH modifiers, or a combination thereof. In some embodiments, the solvent is selected from the group of caprylic / capric triglyceride, benzyl benzoate, ethyl acetate, 3-methoxybutyl acetate, phenyl ethyl benzoate, and combinations thereof. In some embodiments, the adjunct core material can be present in the core in an amount of from 0.01 % to 25% (e.g., from 0.5% to 10%) by weight of the capsule.

[0040] In some embodiments, the amount of the active material (e.g., fragrance) present in the microcapsule core is in a range of from about 50 wt% to about 90 wt%, or from about 50 wt% to about 85 wt%, or from about 55 wt% to about 80 wt%, or from about 60 wt% to about 80 wt%, or from about 65 wt% to about 75 wt%, based on the weight of the microcapsule. In some embodiments, the amount of the active material (e.g., fragrance) present in the microcapsule core is at least 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, or 75 wt%, based on the weight of the microcapsule. In some embodiments, the amount of the active material (e.g., fragrance) present in the microcapsule core is no more than 95 wt%, 92 wt%, 90 wt%, 85 wt%, 80 wt%, 75 wt%, or 70 wt%, based on the weight of the microcapsule. In some embodiments, the microcapsule core comprises an active material (e.g., fragrance) and a solvent. In some IFF10015-WO-PCT embodiments, the weight ratio of the active material to the solvent is from about 90:10 to about 60:40, or from about 85:15 to about 60:40, or from about 80:20 to about 65:35.

[0041] The microcapsule shell comprises a pectin crosslinked in the presence of a laccase. In some embodiments, the pectin comprises or is a sugar beet pectin. In some embodiments, the microcapsule shell comprises a polymeric network comprising a crosslinked pectin. In some embodiments, the microcapsule shell further comprises a phenol compound crosslinked in the presence of a laccase. In the present disclosure, the crosslinking is performed enzymatically using laccase as the crosslinking agent, that is, laccase, as an enzyme, can catalyze the crosslinking of pectin, phenol compound, and / or chitosan. In some embodiments, the pectin and the phenol compound are covalently bonded or crosslinked to form a polymeric network, that is, in the microcapsule shell, the pectin moiety and the phenol compound moiety are connected or crosslinked together via covalent bonds. In some embodiments, the microcapsule shell comprises a polymeric network comprising a pectin covalently bonded or crosslinked with a phenol compound. In some embodiments, the pectin, the phenol compound and the chitosan are covalently bonded or crosslinked to form a polymeric network, that is, in the microcapsule shell, the pectin moiety, the phenol compound moiety and the chitosan moiety are connected or crosslinked together via covalent bonds. In some embodiments, the microcapsule shell comprises a polymeric network comprising a pectin covalently bonded or crosslinked with a phenol compound and a chitosan. In some embodiments, the phenol compound and the chitosan are also covalently bonded or crosslinked with each other in the polymeric network.

[0042] In some embodiments, the amount of the pectin moiety present in the microcapsule shell is in a range of from about 60 wt% to 100 wt%, or from about 70 wt% to about 98 wt%, or from about 80 wt% to about 95 wt%, or from about 85 wt% to about 92 wt%, based on the total weight of the microcapsule shell. In some embodiments, the amount of the pectin moiety present in the microcapsule shell is at least 50 wt%, 60 wt%, 70 wt%, 75 wt%, 80 wt%, or 85 wt%, based on the total weight of the microcapsule shell. In some embodiments, the amount of the pectin moiety present in the microcapsule shell is no more than 100 wt%, 99 wt%, 98 wt%, 97 wt%, 96 wt%, 95 wt%, 92 wt%, 90 wt%, 85 wt%, or 80 wt%, based on the total weight of the microcapsule shell. IFF10015-WO-PCT

[0043] In some embodiments, the amount of the phenol compound moiety present in the microcapsule shell is in a range of from about 1 wt% to about 50 wt%, or from about 2 wt% to about 40 wt%, or from about 3 wt% to about 25 wt%, or from about 5 wt% to about 15 wt%, based on the total weight of the microcapsule shell. In some embodiments, the amount of the phenol compound moiety present in the microcapsule shell is at least 1 wt%, 2 wt%, 3 wt%, 5 wt%, 8 wt%, 10 wt%, 12 wt%, or 15 wt%, based on the total weight of the microcapsule shell. In some embodiments, the amount of the phenol compound moiety present in the microcapsule shell is no more than 50 wt%, 40 wt%, 30 wt%, 25 wt%, 20 wt%, 15 wt%, or 10 wt%, based on the total weight of the microcapsule shell.

[0044] In some embodiments, the amount of the chitosan moiety present in the microcapsule shell is in a range of from about 0.5 wt% to about 15 wt%, or from about 1 wt% to about 10 wt%, or from about 2 wt% to about 5 wt%, based on the total weight of the microcapsule shell. In some embodiments, the amount of the chitosan moiety present in the microcapsule shell is at least 0.5 wt%, 1 wt%, 1 .5 wt%, 2 wt%, 3 wt%, or 4 wt%, based on the total weight of the microcapsule shell. In some embodiments, the amount of the chitosan moiety present in the microcapsule shell is no more than 15 wt%, 10 wt%, 8 wt%, 7 wt%, 6 wt%, or 5 wt%, based on the total weight of the microcapsule shell.

[0045] In some embodiments, the microcapsule shell is substantially free of or free of a polyisocyanate moiety. In some embodiments, the amount of the polyisocyanate moiety present in the microcapsule shell is no more than 5 wt%, 2 wt%, 1 wt%, 0.5 wt%, 0.2 wt%, 0.1 wt%, 0.05 wt%, 0.02 wt%, or 0.01 wt%, based on the total weight of the microcapsule shell. In some embodiments, the microcapsule shell is substantially free of or free of a selfcondensed polyisocyanate. In some embodiments, the amount of the self-condensed polyisocyanate present in the microcapsule shell is no more than 5 wt%, 2 wt%, 1 wt%, 0.5 wt%, 0.2 wt%, 0.1 wt%, 0.05 wt%, 0.02 wt%, or 0.01 wt%, based on the total weight of the microcapsule shell. In some embodiments, the microcapsule shell is substantially free of or free of a polyaldehyde moiety. In some embodiments, the amount of the polyaldehyde moiety present in the microcapsule shell is no more than 5 wt%, 2 wt%, 1 wt%, 0.5 wt%, 0.2 wt%, 0.1 wt%, 0.05 wt%, 0.02 wt%, or 0.01 wt%, based on the total weight of the microcapsule shell. In some embodiments, the microcapsule shell is substantially free of or free of a siloxane group (Si-O-Si). In some embodiments, the amount of the siloxane group present in the microcapsule shell is no more than 5 wt%, 2 wt%, 1 wt%, 0.5 wt%, 0.2 wt%, IFF10015-WO-PCT

[0046] 0.1 wt%, 0.05 wt%, 0.02 wt%, or 0.01 wt%, based on the total weight of the microcapsule shell.

[0047] The term “biodegradable” as used herein with respect to a material, such as a microcapsule shell as a whole or a polymer (e.g., biodegradable polymer) of the microcapsule shell, means that the material has no real or perceived health and / or environmental issues, and is capable of undergoing and / or does undergo physical, chemical, thermal, microbial, biological and / or UV or photo-degradation. Ideally, a microcapsule shell and / or polymer is deemed “biodegradable” when the microcapsule shell and / or polymer passes one or more of the following tests including: a respirometry biodegradation method in aquatic media, available from Organization for Economic Cooperation and Development (OECD), International Organization for Standardization (ISO) and the American Society for Testing and Material (ASTM) tests including, but not limited to OECD 301 F or 310 (Ready biodegradation), OECD 302 (inherent biodegradation), ISO 17556 (solid stimulation studies), ISO 14851 (fresh water stimulation studies), ISO 18830 (marine sediment stimulation studies), OECD 307 (soil stimulation studies), OECD 308 (sediment stimulation studies), and OECD 309 (water stimulation studies). In some embodiments, the microcapsule shell has a biodegradation rate of at least 30%, 40%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, or 98%, based on the weight of the microcapsule shell, within 60 days according to the OECD301 F test. In some embodiments, the microcapsule shell has a biodegradation rate of at least 60%, based on the weight of the microcapsule shell, within 60 days according to the OECD301 F test.

[0048] The microcapsules in the present disclosure do not have to be perfectly spherical. The term “diameter”, as used herein with respect to a microcapsule, means the diameter of a sphere having the same volume as the microcapsule. In some embodiments, at least 80% (by volume) of the microcapsules have diameter ranging from 1 pm to 200 pm, or from 2 pm to 150 pm, or from 3 pm to 100 pm, or from 4 pm to 80 pm, or from 5 pm to 75 pm, or from 6 pm to 75 pm, or from 7 pm to 75 pm, or from 8 pm to 75 pm. In some embodiments, at least 80% (by volume) of the microcapsules have diameter of at least 0.5 pm, 1 pm, 2 pm, 3 pm, 4 pm, 5 pm, 6 pm, 7 pm, 8 pm, 10 pm, 12 pm, 15 pm, 18 pm, or 20 pm. In some embodiments, at least 80% (by volume) of the microcapsules have diameter of no more than 400 pm, 300 pm, 200 pm, 150 pm, 120 pm, 1 10 pm, 100 pm, 90 pm, 85 pm, 80 pm, 75 pm, 70 pm, 65 pm, 60 pm, 55 pm, or 50 pm. IFF10015-WO-PCT

[0049] The present disclosure also provides a process for producing the biodegradable core-shell microcapsules described in this disclosure or a microcapsule slurry comprising such microcapsule. The process comprises: (a) providing an aqueous phase comprising a pectin; (b) providing an oil phase comprising an active material; (c) emulsifying the oil phase with the aqueous phase to form an emulsion; and (d) mixing a laccase with the emulsion at a temperature of from about 20 °C to about 60 °C to form a microcapsule slurry comprising the biodegradable core-shell microcapsule. In some embodiments, the pectin comprises or is a sugar beet pectin.

[0050] In step (a), an aqueous phase is prepared and provided. In some embodiments, the aqueous phase is homogenous. In step (a), pectin is dissolved in an aqueous solution at an elevated temperature. In some embodiments, pectin is dissolved in an aqueous solution at a temperature of from about 25 °C to about 60 °C, or from about 30 °C to about 50 °C. In some embodiments, pectin is dissolved in water. In some embodiments, the aqueous phase further comprises a phenol compound. In some embodiments, the aqueous phase further comprises a chitosan. In some embodiments, the aqueous phase consists essentially of or consists of pectin, water, optionally phenol compound, and optionally chitosan. In some embodiments, the total amount of pectin, water, phenol compound (if present) and chitosan (if present) present in the aqueous phase is at least 90 wt%, 92 wt%, 95 wt%, 96 wt%, 97 wt%, 98 wt%, 99 wt%, 99.2 wt%, 99.5 wt%, 99.8 wt%, 99.9 wt%, 99.92 wt%, or 99.95 wt%, based on the total weight of the aqueous phase.

[0051] In step (b), an oil phase is prepared and provided. The oil phase comprises an active material (e.g., fragrance). In some embodiments, the oil phase further comprises an adjunct core material such as a solvent, an emollient, and / or a core modifier material. In some embodiments, the solvent is selected from the group of caprylic / capric triglyceride, benzyl benzoate, ethyl acetate, 3-methoxybutyl acetate, phenyl ethyl benzoate, and mixtures thereof. In some embodiments, the oil phase further comprises a phenol compound. In some embodiments, the oil phase further comprises a chitosan. In some embodiments, the oil phase consists essentially of or consists of an active material (e.g., fragrance), an adjunct core material (e.g., solvent), optionally phenol compound, and optionally chitosan. In some embodiments, the total amount of active material (e.g., fragrance), adjunct core material (e.g., solvent), phenol compound (if present) and chitosan (if present) present in the oil phase is at least 90 wt%, 92 wt%, 95 wt%, 96 wt%, IFF10015-WO-PCT

[0052] 97 wt%, 98 wt%, 99 wt%, 99.2 wt%, 99.5 wt%, 99.8 wt%, 99.9 wt%, 99.92 wt%, or 99.95 wt%, based on the total weight of the oil phase. In some embodiments, the oil phase is at room temperature. In some embodiments, the temperature of the oil phase is in a range of from 10 °C to 60 °C, or from 15 °C to 55 °C, or from 20 °C to 40 °C, or from 20 °C to 30 °C.

[0053] In step (c), the oil phase is emulsified with the aqueous phase to form an emulsion. In some embodiments, an emulsifier is used in step (c), that is, the emulsion formed in step (c) comprises an emulsifier. In some embodiments, pectin or chitosan can function as an emulsifier, and the emulsion formed in step (c) is substantially free of or free of an emulsifier. The term “emulsifier”, as used herein, means an emulsifier other than pectin and chitosan used in the present disclosure. In some embodiments, the emulsifier comprises or is an amphiphilic compound selected from the group of partially neutralized acid esters, polyvinyl alcohol and modified polyvinyl alcohol, polystyrene sulfonates (e.g., Flexan® II), sodium salt of alkylnaphthalene sulfonate condensate (Morwet® D-425), poloxamers, polysorbates, copolymer of vinyl pyrrolidone and quaternized dimethylaminoethyl methacrylate (Polyquaternium 11 ), tristyrylphenol ethoxylates, phosphated or sulfated tristyrylphenol ethoxylates, polyvinyl pyrrolidone, carboxymethyl cellulose (CMC), polyacrylic acid, polymethacrylic acid, copolymers of acrylic acid and acrylamide, copolymer of acrylamide and acrylamidopropyltrimonium chloride, terpolymers of (acrylic acid, acrylamide, and acrylamidopropyltrimonium chloride), co-polymers of ethylene and maleic anhydride (ZeMac), maleic anhydride copolymers and their hydrolysates, acrylic acid butyl acrylate copolymer, cratonic acid homopolymers and copolymers, vinyl benzenesulfonate homopolymers and copolymers, 2-acrylamido-2- methylpropanesulfonate homopolymers and copolymers, phospholipids, glycolipids, fatty acids, saponins, quillaia extract, surfactant salts with carboxylate, sulfate, sulfonate, phosphate, betaine, and / or linear alcohol groups, and mixtures thereof. In some embodiments, the amount of the emulsifier present in the emulsion formed in step (c) is no more than 1 wt%, 0.5 wt%, 0.2 wt%, 0.1 wt%, 0.05 wt%, 0.02 wt%, 0.01 wt%, 0.005 wt%, or 0.002 wt%, based on the total weight of the emulsion formed in step (c).

[0054] The emulsifying process can be carried out using technologies known in the art. For example, a stirrer, an agitator or a homogenizer (e.g., high shear homogenizer) can be used for emulsification. In some embodiments, the emulsifying process is carried out at IFF10015-WO-PCT room temperature. In some embodiments, the emulsifying process is carried out at a temperature of from 10 °C to 60 °C, or from 15 °C to 55 °C, or from 20 °C to 40 °C, or from 20 °C to 30 °C.

[0055] In some embodiments, the process of this disclosure further comprises adjusting the pH of the emulsion formed in step (c) to within a range of from about 3 to about 8, or from about 3 to about 7, or from about 3 to about 5, or from about 4.5 to about 6, or from about 4.5 to about 5.5, or from about 5 to about 7. In some embodiments, the emulsion formed in step (c) has pH of at least 2, 2.5, 3, 3.5, 4, 4.5, or 5. In some embodiments, the emulsion formed in step (c) has pH of no more than 8, 7.5, 7, 6.5, 6, 5.5, or 5. In some embodiments, the pH value of the emulsion can be adjusted by adding an acid (e.g., hydrochloric acid) or a base (e.g., sodium hydroxide) into the emulsion.

[0056] In some embodiments, the amount of the pectin provided or used in the process for producing the biodegradable core-shell microcapsule is in a range of from about 0.2 wt% to about 10 wt%, or from about 0.5 wt% to about 5 wt%, or from about 1 wt% to about 3 wt%, based on the total weight of the microcapsule slurry formed in step (d). In some embodiments, the amount of the pectin provided or used in the process for producing the microcapsule is at least 0.1 wt%, 0.2 wt%, 0.5 wt%, 0.6 wt%, 0.7 wt%, 0.8 wt%, 0.9 wt%, or 1 wt%, based on the total weight of the microcapsule slurry formed in step (d). In some embodiments, the amount of the pectin provided or used in the process for producing the microcapsule is no more than 15 wt%, 10 wt%, 8 wt%, 6 wt%, 5 wt%, 4 wt%, 3 wt%, or 2 wt%, based on the total weight of the microcapsule slurry formed in step (d).

[0057] In some embodiments, the amount of the phenol compound provided or used in the process for producing the biodegradable core-shell microcapsule is in a range of from about 0.01 wt% to about 3 wt%, or from about 0.02 wt% to about 2 wt%, or from about 0.05 wt% to about 1 .5 wt%, or from about 0.1 wt% to about 1 wt%, based on the total weight of the microcapsule slurry formed in step (d). In some embodiments, the amount of the phenol compound provided or used in the process for producing the microcapsule is at least 0.01 wt%, 0.02 wt%, 0.03 wt%, 0.04 wt%, 0.05 wt%, 0.06 wt%, 0.08 wt%, or 0.1 wt%, based on the total weight of the microcapsule slurry formed in step (d). In some embodiments, the amount of the phenol compound provided or used in the process for producing the microcapsule is no more than 5 wt%, 4 wt%, 3 wt%, 2 wt%, 1 .5 wt%, 1 wt%, IFF10015-WO-PCT

[0058] 0.8 wt%, or 0.5 wt%, based on the total weight of the microcapsule slurry formed in step (d).

[0059] In some embodiments, the amount of the chitosan provided or used in the process for producing the biodegradable core-shell microcapsule is in a range of from about 0.01 wt% to about 0.5 wt%, or from about 0.02 wt% to about 0.2 wt%, or from about 0.04 wt% to about 0.15 wt%, based on the total weight of the microcapsule slurry formed in step (d). In some embodiments, the amount of the chitosan provided or used in the process for producing the microcapsule is at least 0.005 wt%, 0.01 wt%, 0.02 wt%, 0.03 wt%, 0.04 wt%, or 0.05 wt%, based on the total weight of the microcapsule slurry formed in step (d). In some embodiments, the amount of the chitosan provided or used in the process for producing the microcapsule is no more than 1 wt%, 0.5 wt%, 0.4 wt%, 0.3 wt%, 0.2 wt%, 0.15 wt%, or 0.1 wt%, based on the total weight of the microcapsule slurry formed in step (d).

[0060] In step (d), a laccase is added into the emulsion to enzymatically crosslink pectin, phenol compound and / or chitosan to form a microcapsule shell encapsulating the active material, thereby forming a microcapsule slurry comprising a biodegradable core-shell microcapsule wherein the microcapsule core comprises the active material. In some embodiments, the laccase is added as an aqueous solution into the emulsion. In some embodiments, the laccase can be mixed with the emulsion using technologies known in the art such as a stirrer. In some embodiments, the amount of the laccase provided or added in the emulsion is in a range of from about 0.01 mg / mL to about 4 mg / mL, or from about 0.02 mg / mL to about 2 mg / mL, or from about 0.05 mg / mL to about 1 mg / mL, or from about 0.1 mg / mL to about 0.5 mg / mL, based on the total volume of the microcapsule slurry formed in step (d). In some embodiments, the amount of the laccase provided or added in the emulsion is at least 0.005 mg / mL, 0.01 mg / mL, 0.02 mg / mL, 0.05 mg / mL, 0.1 mg / mL, or 0.2 mg / mL, based on the total volume of the microcapsule slurry formed in step (d). In some embodiments, the amount of the laccase provided or added in the emulsion is no more than 10 mg / mL, 5 mg / mL, 4 mg / mL, 3 mg / mL, 2 mg / mL, 1 mg / mL, or 0.5 mg / mL, based on the total volume of the microcapsule slurry formed in step (d). As used herein, the term “mg / mL” means weight (in mg) per volume (in mL).

[0061] In some embodiments, the temperature of the emulsion or the microcapsule slurry in step (d) is in a range of from about 20 °C to about 60 °C, or from about 25 °C to about IFF10015-WO-PCT

[0062] 55 °C, or from about 30 °C to about 50 °C. In some embodiments, the temperature of the emulsion or the microcapsule slurry in step (d) is at least 15 °C, 20 °C, 22 °C, 25 °C, 27 °C, 30 °C, 32 °C, or 35 °C. In some embodiments, the temperature of the emulsion or the microcapsule slurry in step (d) is no more than 60 °C, 55 °C, 50 °C, 45 °C, 42 °C, 40 °C, 38 °C, 35 °C, 32 °C, or 30 °C.

[0063] Using the process of the present disclosure, a relatively high encapsulation efficiency (EE) can be achieved. The term “encapsulation efficiency”, as used herein with respect to the preparation or production of microcapsule, means the amount (in weight) of the active material being encapsulated relative to the total amount (in weight) of the active material used in the preparation or production of the microcapsule. In some embodiments, the encapsulation efficiency of the microcapsule produced in the process is at least 30%, 40%, 50%, 55%, 60%, 65%, or 70%.

[0064] The present disclosure also provides a biodegradable core-shell microcapsule obtainable by the process of this disclosure. In some embodiments, the obtained or produced microcapsule has the composition and / or property of the biodegradable coreshell microcapsule described in this disclosure.

[0065] The biodegradable core-shell microcapsule of the present disclosure is well-suited for inclusion in consumer products where controlled release of active material (e.g., fragrances or flavors) is desired. The present disclosure also provides a consumer product comprising the biodegradable core-shell microcapsule of this disclosure. In some embodiments, the consumer product is selected from the group of fabric softener, fabric conditioner, detergent, scent booster, fabric refresher spray, body wash, body soap, shampoo, hair conditioner, body spray, hair refresher spray, hair dye, hair moisturizer, skin moisturizer, hair treatment, skin treatment, antiperspirant, deodorant, insect repellant, candle, surface cleaner, bathroom cleaner, bleach, cat litter, refresher spray, pesticide, insecticide, herbicide, fungicide, paint, and combinations thereof.

[0066] Many aspects and embodiments have been described above and are merely exemplary and not limiting. After reading this specification, skilled artisans appreciate that other aspects and embodiments are possible without departing from the scope of the invention.

[0067] EXAMPLES IFF10015-WO-PCT

[0068] The concepts described herein will be further described in the following examples, which do not limit the scope of the invention described in the claims.

[0069] General

[0070] Unless otherwise specified, Magnitude is a fragrance commercially available from International Flavors & Fragrances Inc., NY; pectin is GENU® Beta pectin from CP Kelco; laccase is Trametes Versicolor laccase from Sigma-Aldrich; chitosan is KiOsmetine® P chitosan from KitoZyme; NEOBEE® oil is caprylic / capric triglyceride used as a solvent for fragrance composition; homogenizer is a Silverson L5M-A homogenizer with 1 ” or 3 / 4” tubular mixer; and microscope is Olympus DP26 at 20X or 50X magnification.

[0071] Example 1 : Microcapsule Prepared with Pectin

[0072] In this example, we aimed to prepare microcapsules with pectin using laccase as the enzymatic crosslinking agent.

[0073] An aqueous phase was prepared by dissolving pectin in DI (deionized) water using a magnetic stirrer at 40 °C for one hour. Separately, an oil phase was prepared by mixing Magnitude fragrance with NEOBEE® oil. Subsequently, the oil phase was emulsified with the aqueous phase to form an oil-in-water emulsion. The emulsification was carried out by using the homogenizer at 9600 RPM (revolutions per minute) for 3 minutes. The pH of the emulsion was adjusted to 5.0-5.5 using either sodium hydroxide or hydrochloric acid solution. The resulting emulsion was homogenized at 9600 RPM for an additional minute. The emulsion contained 1 .5 wt% pectin, 30 wt% Magnitude fragrance and 7.5 wt% NEOBEE® oil, based on the weight of the emulsion.

[0074] Subsequently, to a glass reactor containing 115.2 mL of the emulsion prepared above was added 4.8 mL of an aqueous solution of laccase with concentration of 20 mg / mL. The reactor was sealed, and the enzymatic crosslinking reaction was carried out at 27 °C with an overhead mixing at 300 RPM for 94 hours. Microcapsule slurry samples were drawn by serological pipette at different time points for assessment of the reaction progress and microcapsule formation by the microscope. At the end of the reaction, microcapsule slurry samples were also analyzed for free oil content, and encapsulation efficiency was calculated to be 23.3%.

[0075] Example 2: Microcapsule Prepared with Pectin and Tannic Acid IFF10015-WO-PCT

[0076] In this example, we aimed to prepare microcapsules with pectin and tannic acid using laccase as the enzymatic crosslinking agent.

[0077] In this example, the microcapsule was prepared using the same process as described in Example 1 , except that an oil phase was prepared by mixing Magnitude fragrance, NEOBEE® oil and tannic acid together; the emulsion contained 1 .5 wt% pectin, 30 wt% Magnitude fragrance, 7.5 wt% NEOBEE® oil, and 1 wt% tannic acid, based on the weight of the emulsion; and the encapsulation efficiency was calculated to be 33.7%. Comparing with Example 1 , more capsule formation was observed in this example under microscope at the end of the reaction. Example 2 demonstrated that using a combination of pectin and tannic acid can improve the capsule formation.

[0078] Example 3: Microcapsule Prepared with Pectin and Hydroquinone

[0079] In this example, we aimed to prepare microcapsules with pectin and hydroquinone using laccase as the enzymatic crosslinking agent.

[0080] An aqueous phase was prepared by dissolving pectin in DI (deionized) water using a magnetic stirrer at 40 °C for one hour. Separately, four oil phases were prepared respectively by mixing Magnitude fragrance, NEOBEE® oil and a differing amount of hydroquinone together. Subsequently, each oil phase was emulsified with a portion of the aqueous phase to form an oil-in-water emulsion. Each emulsification was carried out by using the homogenizer at 1200 RPM for 3 minutes. The pH of each emulsion was adjusted to 5.0-5.5 using either sodium hydroxide or hydrochloric acid solution. Each resulting emulsion was homogenized at 1200 RPM for an additional minute. Four separate emulsions were generated. Each of them contained 1.8 wt% pectin, 30 wt% Magnitude fragrance and 7.5 wt% NEOBEE® oil, based on the weight of the emulsion. The first emulsion also contained 0.05 wt% hydroquinone, the second emulsion also contained 0.1 wt% hydroquinone, the third emulsion also contained 0.2 wt% hydroquinone, and the fourth emulsion also contained 0.4 wt% hydroquinone, all based on the weight of the respective emulsion.

[0081] Subsequently, to four separate glass reactors respectively containing 1 17 mL of each of the four emulsions prepared above was respectively added 3 mL of an aqueous solution of laccase with concentration of 2 mg / mL. The reactors were respectively sealed, and all four enzymatic crosslinking reactions were respectively carried out at 40 °C with an IFF10015-WO-PCT overhead mixing at 300 RPM for 49 hours. Microcapsule slurry samples were respectively drawn by serological pipette at different time points for assessment of the reaction progress and microcapsule formation by the microscope. At the end of each reaction, microcapsule slurry samples were also respectively analyzed for free oil content, and encapsulation efficiency was respectively calculated. The first microcapsule preparation (with 0.05 wt% hydroquinone in the emulsion) had an encapsulation efficiency of 70.65%, the second microcapsule preparation (with 0.1 wt% hydroquinone in the emulsion) had an encapsulation efficiency of 59%, the third microcapsule preparation (with 0.2 wt% hydroquinone in the emulsion) had an encapsulation efficiency of 55.3%, and the fourth microcapsule preparation (with 0.4 wt% hydroquinone in the emulsion) had an encapsulation efficiency of 59%. Example 3 demonstrated that using hydroquinone in addition to pectin in the enzymatic crosslinking reaction can improve the capsule formation.

[0082] Example 4: Microcapsule Prepared with Pectin and Protocatechuic Acid

[0083] In this example, we aimed to prepare microcapsules with pectin and protocatechuic acid using laccase as the enzymatic crosslinking agent.

[0084] An aqueous phase was prepared by dissolving pectin in DI (deionized) water using a magnetic stirrer at 40 °C for one hour. Separately, an oil phase was prepared by mixing Magnitude fragrance, NEOBEE® oil and protocatechuic acid together. Subsequently, the oil phase was emulsified with the aqueous phase to form an oil-in-water emulsion. The emulsification was carried out by using the homogenizer at 1200 RPM for 3 minutes. The pH of the emulsion was adjusted to 5.0-5.5 using either sodium hydroxide or hydrochloric acid solution. The emulsion contained 1 .8 wt% pectin, 30 wt% Magnitude fragrance, 7.5 wt% NEOBEE® oil and 0.2 wt% protocatechuic acid, based on the weight of the emulsion.

[0085] Subsequently, to a glass reactor containing 117 ml_ of the emulsion prepared above was added 3 mL of an aqueous solution of laccase with concentration of 2 mg / mL. The reactor was sealed, and the enzymatic crosslinking reaction was carried out at 40 °C with an overhead mixing at 300 RPM for 48 hours. Microcapsule slurry samples were drawn by serological pipette at different time points for assessment of the reaction progress and microcapsule formation by the microscope. At the end of the reaction, microcapsule slurry samples were also analyzed for free oil content, and encapsulation efficiency was IFF10015-WO-PCT calculated to be 50.9%. Example 4 demonstrated that using protocatechuic acid in addition to pectin in the enzymatic crosslinking reaction can improve the capsule formation.

[0086] Example 5: Microcapsule Prepared with Pectin and Gallic Acid

[0087] In this example, we aimed to prepare microcapsules with pectin and gallic acid using laccase as the enzymatic crosslinking agent.

[0088] An aqueous phase was prepared by dissolving pectin in DI (deionized) water using a magnetic stirrer at 40 °C for one hour. Gallic acid was then added to the pectin solution and mixed to dissolve. Separately, two oil phases were prepared respectively by mixing Magnitude fragrance with NEOBEE® oil. Subsequently, the two oil phases were emulsified with a portion of the aqueous phase respectively to form two oil-in-water emulsions. The first emulsion was generated by using the homogenizer at 3000-3500 RPM for 4 minutes, and the second emulsion was generated by using the homogenizer at 5000-6000 RPM for 4 minutes. The pH of each emulsion was adjusted to 5.0-5.5 using either sodium hydroxide or hydrochloric acid solution. Subsequently, the first emulsion was homogenized at 3000- 3500 RPM for an additional minute, and the second emulsion was homogenized at 5000- 6000 RPM for an additional minute. Both emulsions respectively contained 1 .5 wt% pectin, 30 wt% Magnitude fragrance, 7.5 wt% NEOBEE® oil and 0.1 wt% gallic acid, based on the weight of the respective emulsion.

[0089] Subsequently, to two separate glass reactors respectively containing 115.2 mL of each of the two emulsions prepared above was respectively added 4.8 mL of an aqueous solution of laccase with concentration of 20 mg / mL. The two reactors were respectively sealed, and the two enzymatic crosslinking reactions were respectively carried out at 27 °C with an overhead mixing at 300 RPM for 74 hours. Microcapsule slurry samples were respectively drawn by serological pipette at different time points for assessment of the reaction progress and microcapsule formation by the microscope. At the end of each reaction, microcapsule slurry samples were also respectively analyzed for free oil content, and encapsulation efficiency was respectively calculated. The first microcapsule preparation (with 3000-3500 RPM homogenization) had an encapsulation efficiency of 51 %, and the second microcapsule preparation (with 5000-6000 RPM homogenization) had an encapsulation efficiency of 48%. Example 5 demonstrated that using gallic acid in IFF10015-WO-PCT addition to pectin in the enzymatic crosslinking reaction can improve the capsule formation.

[0090] Example 6: Microcapsule Prepared with Pectin and Gallic Acid

[0091] In this example, we aimed to prepare microcapsules with pectin and gallic acid using laccase as the enzymatic crosslinking agent.

[0092] An aqueous phase was prepared by dissolving pectin in DI (deionized) water using a magnetic stirrer at 40 °C for one hour. Separately, an oil phase was prepared by mixing Magnitude fragrance with NEOBEE® oil. Gallic acid was then added to the oil phase and mixed to dissolve. Subsequently, the oil phase was emulsified with the aqueous phase to form an oil-in-water emulsion. The emulsification was carried out by using the homogenizer at 3000-3500 RPM for 4 minutes. The pH of the emulsion was adjusted to 5.0-5.5 using either sodium hydroxide or hydrochloric acid solution. The resulting emulsion was homogenized at 3000 RPM for an additional minute. The emulsion contained 1 .5 wt% pectin, 30 wt% Magnitude fragrance, 7.5 wt% NEOBEE® oil and 0.05 wt% gallic acid, based on the weight of the emulsion.

[0093] Subsequently, to a glass reactor containing 115.2 mL of the emulsion prepared above was added 4.8 mL of an aqueous solution of laccase with concentration of 20 mg / mL. The reactor was sealed, and the enzymatic crosslinking reaction was carried out at 27 °C with an overhead mixing at 300 RPM for 48 hours. Microcapsule slurry samples were drawn by serological pipette at different time points for assessment of the reaction progress and microcapsule formation by the microscope. At the end of the reaction, microcapsule slurry samples were also analyzed for free oil content, and encapsulation efficiency was calculated to be 48.3%. Example 6 demonstrated that using gallic acid in addition to pectin in the enzymatic crosslinking reaction can improve the capsule formation.

[0094] Example 7: Microcapsule Prepared with Pectin and Gallic Acid

[0095] In this example, we aimed to prepare microcapsules with pectin and gallic acid using laccase as the enzymatic crosslinking agent.

[0096] In this example, the microcapsule was prepared using the same process as described in Example 6, except that a different amount of gallic acid was used; the emulsion contained 1 .5 wt% pectin, 30 wt% Magnitude fragrance, 7.5 wt% NEOBEE® oil IFF10015-WO-PCT and 0.2 wt% gallic acid, based on the weight of the emulsion; and the encapsulation efficiency was calculated to be 46.9%. Example 7 demonstrated that using gallic acid in addition to pectin in the enzymatic crosslinking reaction can improve the capsule formation.

[0097] Example 8: Microcapsule Prepared with Pectin and Gallic Acid

[0098] In this example, we aimed to prepare microcapsules with pectin and gallic acid using laccase as the enzymatic crosslinking agent.

[0099] In this example, the microcapsule was prepared using the same process as described in Example 7, except that a different amount of pectin was used; the emulsion contained 1 .0 wt% pectin, 30 wt% Magnitude fragrance, 7.5 wt% NEOBEE® oil and 0.2 wt% gallic acid, based on the weight of the emulsion; the enzymatic crosslinking reaction was carried out at 27 °C with an overhead mixing at 300 RPM for 72 hours; and the encapsulation efficiency was calculated to be 47.2%. Example 8 demonstrated that using gallic acid in addition to pectin in the enzymatic crosslinking reaction can improve the capsule formation.

[0100] Example 9: Microcapsule Prepared with Pectin and Gallic Acid

[0101] In this example, we aimed to prepare microcapsules with pectin and gallic acid using laccase as the enzymatic crosslinking agent.

[0102] In this example, the microcapsule was prepared using the same process as described in Example 7, except that a different amount of pectin was used; the emulsion contained 1 .8 wt% pectin, 30 wt% Magnitude fragrance, 7.5 wt% NEOBEE® oil and 0.2 wt% gallic acid, based on the weight of the emulsion; and the encapsulation efficiency was calculated to be 58%. Example 8 demonstrated that using gallic acid in addition to pectin in the enzymatic crosslinking reaction can improve the capsule formation.

[0103] Example 10: Microcapsule Prepared with Pectin, Gallic Acid and Chitosan

[0104] In this example, we aimed to prepare microcapsules with pectin, gallic acid and chitosan using laccase as the enzymatic crosslinking agent.

[0105] An aqueous phase was prepared by dissolving pectin in DI (deionized) water using a magnetic stirrer at 40 °C for one hour. Separately, an oil phase was prepared by mixing Magnitude fragrance with NEOBEE® oil. Gallic acid and chitosan were then added to the oil phase and mixed to dissolve. Subsequently, the oil phase was emulsified with the IFF10015-WO-PCT aqueous phase to form an oil-in-water emulsion. The emulsification was carried out by using the homogenizer at 1200 RPM for 5 minutes. The pH of the emulsion was adjusted to about 5.0 using either sodium hydroxide or hydrochloric acid solution. The resulting emulsion was homogenized at 1200 RPM for an additional minute. The emulsion contained 1 .5 wt% pectin, 30 wt% Magnitude fragrance, 7.5 wt% NEOBEE® oil, 0.15 wt% gallic acid and 0.05 wt% chitosan, based on the weight of the emulsion.

[0106] Subsequently, to a glass reactor containing 117 mL of the emulsion prepared above was added 3 mL of an aqueous solution of laccase with concentration of 8 mg / mL. The reactor was sealed, and the enzymatic crosslinking reaction was carried out at 40 °C with an overhead mixing at 300 RPM for 45 hours. Microcapsule slurry samples were drawn by serological pipette at different time points for assessment of the reaction progress and microcapsule formation by the microscope. At the end of the reaction, microcapsule slurry samples were also analyzed for free oil content, and encapsulation efficiency was calculated to be 73.7%. Example 10 demonstrated that using chitosan in addition to pectin and gallic acid in the enzymatic crosslinking reaction can further improve the capsule formation.

[0107] Example 11 : Microcapsule Prepared with Pectin, Gallic Acid and Chitosan

[0108] In this example, we aimed to prepare microcapsules with pectin, gallic acid and chitosan using laccase as the enzymatic crosslinking agent.

[0109] In this example, the microcapsule was prepared using the same process as described in Example 10, except that different amounts of pectin, gallic acid and chitosan were used; the emulsion contained 1 .8 wt% pectin, 30 wt% Magnitude fragrance, 7.5 wt% NEOBEE® oil, 0.5 wt% gallic acid and 0.1 wt% chitosan, based on the weight of the emulsion; the enzymatic crosslinking reaction was carried out at 40 °C with an overhead mixing at 300 RPM for 70 hours; and the encapsulation efficiency was calculated to be 68.9%. Example 11 demonstrated that using chitosan in addition to pectin and gallic acid in the enzymatic crosslinking reaction can further improve the capsule formation.

[0110] Example 12: Microcapsule Prepared with Pectin, Gallic Acid and Chitosan

[0111] In this example, we aimed to prepare microcapsules with pectin, gallic acid and chitosan using laccase as the enzymatic crosslinking agent. IFF10015-WO-PCT

[0112] An aqueous phase was prepared by dissolving pectin in DI (deionized) water using a magnetic stirrer at 40 °C for one hour. Separately, an oil phase was prepared by mixing Magnitude fragrance with NEOBEE® oil. Gallic acid and chitosan were then added to the oil phase and mixed to dissolve. Subsequently, the oil phase was emulsified with the aqueous phase to form an oil-in-water emulsion. The emulsification was carried out by using the homogenizer at 1200 RPM for 5 minutes. The pH of the emulsion was adjusted to about 5.0 using either sodium hydroxide or hydrochloric acid solution. The resulting emulsion was homogenized at 1200 RPM for an additional minute. The emulsion contained 1 .5 wt% pectin, 24 wt% Magnitude fragrance, 6 wt% NEOBEE® oil, 0.15 wt% gallic acid and 0.05 wt% chitosan, based on the weight of the emulsion.

[0113] Subsequently, to a glass reactor containing 117 mL of the emulsion prepared above was added 3 mL of an aqueous solution of laccase with concentration of 8 mg / mL. The reactor was sealed, and the enzymatic crosslinking reaction was carried out at 40 °C with an overhead mixing at 300 RPM for 48 hours. Microcapsule slurry samples were drawn by serological pipette at different time points for assessment of the reaction progress and microcapsule formation by the microscope. At the end of the reaction, microcapsule slurry samples were also analyzed for free oil content, and encapsulation efficiency was calculated to be 72.3%. Example 12 demonstrated that using chitosan in addition to pectin and gallic acid in the enzymatic crosslinking reaction can further improve the capsule formation.

[0114] Note that not all of the activities described above in the general description or the examples are required, that a portion of a specific activity may not be required, and that one or more further activities may be performed in addition to those described. Still further, the order in which activities are listed are not necessarily the order in which they are performed.

[0115] In the foregoing specification, the concepts have been described with reference to specific embodiments. However, one of ordinary skill in the art appreciates that various modifications and changes can be made without departing from the scope of the invention as set forth in the claims below. Accordingly, the specification is to be regarded in an illustrative rather than a restrictive sense, and all such modifications are intended to be included within the scope of invention. IFF10015-WO-PCT

[0116] Benefits, other advantages, and solutions to problems have been described above with regard to specific embodiments. However, the benefits, advantages, solutions to problems, and any feature(s) that may cause any benefit, advantage, or solution to occur or become more pronounced are not to be construed as a critical, required, or essential feature of any or all the claims.

[0117] It is to be appreciated that certain features are, for clarity, described herein in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features that are, for brevity, described in the context of a single embodiment, may also be provided separately or in any subcombination.

[0118] EMBODIMENTS

[0119] For further illustration, additional non-limiting embodiments of the present disclosure are set forth below.

[0120] For example, embodiment 1 is a biodegradable core-shell microcapsule. The biodegradable core-shell microcapsule comprises: (a) a microcapsule core comprising an active material; and (b) a microcapsule shell comprising a pectin crosslinked in the presence of a laccase.

[0121] Embodiment 2 is a biodegradable core-shell microcapsule as set forth in embodiment 1 , wherein the microcapsule shell further comprises a phenol compound crosslinked in the presence of a laccase.

[0122] Embodiment 3 is a biodegradable core-shell microcapsule as set forth in embodiment 2, wherein the microcapsule shell further comprises a chitosan crosslinked with the pectin and / or the phenol compound in the presence of a laccase.

[0123] Embodiment 4 is a biodegradable core-shell microcapsule as set forth in embodiment 2 or 3, wherein the phenol compound is selected from the group of gallic acid, ferulic acid, hydroquinone, protocatechuic acid, tannic acid, and combinations thereof.

[0124] Embodiment 5 is a biodegradable core-shell microcapsule as set forth in embodiment 4, wherein the phenol compound is gallic acid.

[0125] Embodiment 6 is a biodegradable core-shell microcapsule as set forth in one of embodiments 3-5, wherein the amount of chitosan moiety present in the microcapsule shell is no more than 15 wt% based on the total weight of the microcapsule shell.

[0126] Embodiment 7 is a biodegradable core-shell microcapsule as set forth in one of embodiments 2-6, wherein the amount of the phenol compound moiety present in the IFF10015-WO-PCT microcapsule shell is in a range of from about 1 wt% to about 50 wt% based on the total weight of the microcapsule shell.

[0127] Embodiment 8 is a biodegradable core-shell microcapsule as set forth in any of the preceding embodiments, wherein the amount of the pectin moiety present in the microcapsule shell is at least 50 wt% based on the total weight of the microcapsule shell.

[0128] Embodiment 9 is a biodegradable core-shell microcapsule as set forth in any of the preceding embodiments, wherein the pectin comprises a sugar beet pectin.

[0129] Embodiment 10 is a biodegradable core-shell microcapsule as set forth in any of the preceding embodiments, wherein the active material is selected from the group of fragrance, pro-fragrance, malodor counteractive agent, and combinations thereof.

[0130] Embodiment 11 is a biodegradable core-shell microcapsule as set forth in any of the preceding embodiments, wherein the microcapsule shell is substantially free of or free of a polyisocyanate moiety.

[0131] Embodiment 12 is a biodegradable core-shell microcapsule as set forth in any of the preceding embodiments, wherein the microcapsule shell is substantially free of or free of a self-condensed polyisocyanate.

[0132] Embodiment 13 is a biodegradable core-shell microcapsule as set forth in any of the preceding embodiments, wherein the microcapsule shell is substantially free of or free of a polyaldehyde moiety.

[0133] Embodiment 14 is a biodegradable core-shell microcapsule as set forth in any of the preceding embodiments, wherein the microcapsule shell is substantially free of or free of a siloxane group (Si-O-Si).

[0134] Embodiment 15 is a biodegradable core-shell microcapsule as set forth in any of the preceding embodiments, wherein the microcapsule shell has a biodegradation rate of at least 60%, based on the weight of the microcapsule shell, within 60 days according to the OECD301 F test.

[0135] Embodiment 16 is a biodegradable core-shell microcapsule as set forth in any of the preceding embodiments, wherein at least 80% (by volume) of the microcapsules have diameter ranging from 1 pm to 200 pm.

[0136] Embodiment 17 is a process for producing the biodegradable core-shell microcapsule as set forth in any of the preceding embodiments. The process comprises: (a) providing an aqueous phase comprising a pectin; (b) providing an oil phase comprising IFF10015-WO-PCT an active material; (c) emulsifying the oil phase with the aqueous phase to form an emulsion; and (d) mixing a laccase with the emulsion at a temperature of from about 20 °C to about 60 °C to form a microcapsule slurry comprising the biodegradable core-shell microcapsule.

[0137] Embodiment 18 is a process as set forth in embodiment 17, further comprising adjusting the pH of the emulsion to within a range of from about 3 to about 8.

[0138] Embodiment 19 is a process as set forth in embodiment 17 or 18, wherein the aqueous phase or the oil phase further comprises a phenol compound.

[0139] Embodiment 20 is a process as set forth in embodiment 19, wherein the aqueous phase or the oil phase further comprises a chitosan.

[0140] Embodiment 21 is a process as set forth in one of embodiments 17-20, wherein the pectin comprises a sugar beet pectin.

[0141] Embodiment 22 is a process as set forth in one of embodiments 19-21 , wherein the phenol compound is selected from the group of gallic acid, ferulic acid, hydroquinone, protocatechuic acid, tannic acid, and combinations thereof.

[0142] Embodiment 23 is a process as set forth in one of embodiments 17-22, wherein the amount of the pectin provided in the emulsion is in a range of from about 0.2 wt% to about 10 wt% based on the total amount of the microcapsule slurry formed in step (d).

[0143] Embodiment 24 is a process as set forth in one of embodiments 19-22, wherein the amount of the phenol compound provided in the emulsion is in a range of from about 0.01 wt% to about 3 wt% based on the total amount of the microcapsule slurry formed in step (d).

[0144] Embodiment 25 is a process as set forth in one of embodiments 20-22, wherein the amount of the chitosan provided in the emulsion is in a range of from about 0.01 wt% to about 0.5 wt% based on the total amount of the microcapsule slurry formed in step (d).

[0145] Embodiment 26 is a process as set forth in one of embodiments 17-25, wherein the amount of the laccase added in the emulsion is in a range of from about 0.01 mg / mL to about 4 mg / mL based on the total volume of the microcapsule slurry formed in step (d).

[0146] Embodiment 27 is a process as set forth in one of embodiments 17-26, wherein the aqueous phase is homogenous, and pectin is dissolved in an aqueous solution at an elevated temperature. IFF10015-WO-PCT

[0147] Embodiment 28 is a process as set forth in one of embodiments 17-27, wherein the emulsion formed in step (c) is substantially free of or free of an emulsifier.

[0148] Embodiment 29 is a process as set forth in one of embodiments 17-28, wherein the encapsulation efficiency of the microcapsule produced in the process is at least 30%, 40%, 50%, 55%, 60%, 65%, or 70%.

[0149] Embodiment 30 is a biodegradable core-shell microcapsule obtainable by the process as set forth in one of embodiments 17-29.

[0150] Embodiment 31 is a consumer product comprising the biodegradable core-shell microcapsule as set forth in one of embodiments 1 -16 and 30. Embodiment 32 is a consumer product as set forth in embodiment 31 , wherein the consumer product is selected from the group of fabric softener, fabric conditioner, detergent, scent booster, fabric refresher spray, body wash, body soap, shampoo, hair conditioner, body spray, hair refresher spray, hair dye, hair moisturizer, skin moisturizer, hair treatment, skin treatment, antiperspirant, deodorant, insect repellant, candle, surface cleaner, bathroom cleaner, bleach, cat litter, refresher spray, pesticide, insecticide, herbicide, fungicide, paint, and combinations thereof.

Claims

IFF10015-WO-PCTCLAIM(S)What is claimed is:1 . A biodegradable core-shell microcapsule comprising:(a) a microcapsule core comprising an active material; and(b) a microcapsule shell comprising a pectin crosslinked in the presence of a laccase.

2. The biodegradable core-shell microcapsule of claim 1 , wherein the microcapsule shell further comprises a phenol compound crosslinked in the presence of a laccase.

3. The biodegradable core-shell microcapsule of claim 2, wherein the microcapsule shell further comprises a chitosan crosslinked with the pectin and / or the phenol compound in the presence of a laccase.

4. The biodegradable core-shell microcapsule of claim 2 or 3, wherein the phenol compound is selected from the group of gallic acid, ferulic acid, hydroquinone, protocatechuic acid, tannic acid, and combinations thereof.

5. The biodegradable core-shell microcapsule of claim 4, wherein the phenol compound is gallic acid.

6. The biodegradable core-shell microcapsule of any one of claims 3-5, wherein the amount of chitosan moiety present in the microcapsule shell is no more than 15 wt% based on the total weight of the microcapsule shell.

7. The biodegradable core-shell microcapsule of any one of claims 2-6, wherein the amount of the phenol compound moiety present in the microcapsule shell is in a range of from about 1 wt% to about 50 wt% based on the total weight of the microcapsule shell.

8. The biodegradable core-shell microcapsule of any one of the preceding claims, wherein the amount of the pectin moiety present in the microcapsule shell is at least 50 wt% based on the total weight of the microcapsule shell.

9. The biodegradable core-shell microcapsule of any one of the preceding claims, wherein the pectin comprises a sugar beet pectin.IFF10015-WO-PCT10. The biodegradable core-shell microcapsule of any one of the preceding claims, wherein the active material is selected from the group of fragrance, pro-fragrance, malodor counteractive agent, and combinations thereof.1 1 . A process for producing the biodegradable core-shell microcapsule of any one of the preceding claims, comprising:(a) providing an aqueous phase comprising a pectin;(b) providing an oil phase comprising an active material;(c) emulsifying the oil phase with the aqueous phase to form an emulsion; and(d) mixing a laccase with the emulsion at a temperature of from about 20 °C to about 60 °C to form a microcapsule slurry comprising the biodegradable core-shell microcapsule.

12. The process of claim 11 , further comprising adjusting the pH of the emulsion to within a range of from about 3 to about 8.

13. The process of claim 11 or 12, wherein the aqueous phase or the oil phase further comprises a phenol compound.

14. The process of claim 13, wherein the aqueous phase or the oil phase further comprises a chitosan.

15. The process of any one of claims 1 1 -14, wherein the pectin comprises a sugar beet pectin.