Biodegradable microcapsules containing low log P perfume

Abstract

The present disclosure relates to a core-shell microcapsule slurry comprising (a) a core-shell microcapsule, the core of the microcapsule comprising an active material and the shell of the microcapsule comprising a self-condensing polyisocyanate; (b) a dispersant containing denatured pea protein; and (c) a hydrocolloid containing Arabic gum; wherein the active material comprises a low logP perfume having a logP value ranging from 0.5 to 2.2, the amount of the low logP perfume being from 3% to 18% by weight based on the weight of the active material, and the core-shell microcapsule slurry being white. The present disclosure also relates to a method of producing such a core-shell microcapsule slurry. The disclosure also relates to a consumer product containing such a core-shell microcapsule slurry.

Description

Technical Field

[0001] This disclosure relates to a biodegradable core-shell microcapsule slurry comprised of microcapsules. Specifically, the microcapsules have a wall formed by the self-polymerization of a polyisocyanate in the presence of denatured pea protein as a dispersant. The microcapsules also have a core containing a low-logP fragrance. Also disclosed are consumer products containing this core-shell microcapsule slurry and methods for producing this core-shell microcapsule slurry. Background Art

[0002] Microcapsules are useful in a variety of applications where it is desirable to deliver, administer, or release a fragrance or other active material in a delayed and controlled manner.

[0003] Conventional microcapsules each have a polymer shell that encapsulates the active material within the microcapsule core. The polymer shell is typically formed via interfacial polymerization (i.e., polymerization occurring at the interface between the aqueous and oil phases). These microcapsules have been developed to provide good performance in various consumer products, such as laundry detergents. See, for example, US 7,491,687, US 6,045,835, US 2014 / 0287008, and WO 2015 / 023961. Polyurea microcapsules have been developed for the delivery of fragrances. Their preparation involves a polymerization reaction between wall-forming materials (e.g., polyisocyanates and polyamines). During the polymerization reaction, polyisocyanates can react with many fragrance ingredients, such as primary alcohols found in fragrance accords. Polyamines, another wall-forming material, are also reactive with aldehyde fragrance ingredients. Primary alcohols and aldehydes are common ingredients in many fragrance accords. Such fragrances are not suitable for encapsulation using conventional microcapsules. Furthermore, fragrance ingredients with high water solubility are not suitable for conventional encapsulation because these ingredients tend to remain in the aqueous phase rather than being encapsulated in the microcapsule oil core. Encapsulating fragrances and other active materials without losing reactive or water-soluble ingredients remains a challenge.

[0004] Methods for incorporating biodegradable polymers into microcapsule compositions have been described. For example, US 10,034,819 B2 and US 2019 / 0240124 A1 teach microcapsules having an inner shell and an outer shell, wherein the outer shell is produced by complex coacervation of a first polyelectrolyte (such as gelatin) and a second polyelectrolyte (such as carboxymethylcellulose, sodium carboxymethyl guar, xanthan gum, and vegetable gum).

[0005] Similarly, EP 2588066 B1 describes coacervate capsules prepared with a coating consisting of a protein and optionally a non-protein polymer.

[0006] Furthermore, EP 2811846 B1 describes the use of protein aggregates as an interface layer around hydrophobic substances.

[0007] EP 1855544 B8 teaches the use of encapsulating active ingredients in a matrix consisting of 0.5-95 wt% of anionic polysaccharides and 0.5-95 wt% of peptides having a molecular mass in the range of 0.3-12 kDa.

[0008] EP 3746217 A1 and WO 2020 / 195132 A1 describe the preparation of core-shell microcapsules by crosslinking proteins into the microcapsule wall.

[0009] US 10,166,196 B2 discloses agglomerates of primary microcapsules composed of a primary shell and an outer shell, wherein the outer shell is a primary shell and the outer shell is a product of a complex coacervation reaction of a first protein (such as pea or soy protein) and a second polymer (such as agar, gellan gum, gum Arabic, casein, prolamin, pectin, alginate, carrageenan, xanthan gum, canola, dilutan gum, locust bean gum or welan gum).

[0010] Therefore, these existing solutions still have limitations and do not adequately teach how to overcome the above problems.Therefore, there is still a need to develop a microcapsule composition suitable for encapsulating active materials with sustainable and biodegradable ingredients. Summary of the Invention

[0011] The present disclosure provides a core-shell microcapsule slurry. The core-shell microcapsule slurry comprises: (a) core-shell microcapsules, wherein the core of the microcapsule comprises an active material and the shell of the microcapsule comprises a self-condensing polyisocyanate; (b) a dispersant comprising denatured pea protein; and (c) a hydrocolloid comprising gum arabic; wherein the active material comprises a low logP fragrance having a logP value ranging from 0.5 to 2.2, the amount of the low logP fragrance being 3% to 18% by weight based on the weight of the active material, and the core-shell microcapsule slurry is white. BRIEF DESCRIPTION OF THE DRAWINGS

[0012] Embodiments are illustrated in the accompanying drawings to improve understanding of the concepts as presented herein.

[0013] Figure 1Shown are force curves generated in capsule rupture experiments for capsules prepared with: whey protein according to Example 7 of WO 2020 / 131875 A2 (where citric acid was added prior to curing to achieve a curing pH of 5) (left, whey); pea protein according to Example 2 herein (center, pea); and pea protein with an optimized curing temperature and pH as described in Example 9 herein (right, temperature- and pH-optimized pea). This analysis demonstrates that capsule wall properties can be modified by protein selection and, more importantly, by optimizing the curing profile and pH of the capsule-forming reaction. DETAILED DESCRIPTION

[0014] The foregoing general description and the following detailed description are exemplary and explanatory only and do not limit the invention as defined in the appended claims. Other features and benefits of any one or more embodiments will be apparent from the following detailed description and from the claims.

[0015] As used herein, the terms “comprise,” “comprising,” “include,” “including,” “have,” “having,” “contain,” “containing,” or any other variations 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. Furthermore, unless expressly stated to the contrary, “or” refers to an inclusive or and not to an exclusive or. For example, condition A or B is satisfied by any of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exists).

[0016] Furthermore, "a" and "an" are used 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. The 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 intended otherwise.

[0017] 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 the invention pertains. In the event of a conflict, the present specification (including definitions) shall prevail. 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. Furthermore, the materials, methods, and examples are illustrative only and are not intended to be limiting.

[0018] When amount, concentration or other value or parameter are given with scope, preferred range or a series of upper preferred value and / or lower preferred value, this should be understood as particularly disclosing all scopes formed by any pairing of any range upper limit or preferred value and any range lower limit or preferred value, and no matter whether these scopes are disclosed separately.When numerical range is enumerated herein, unless otherwise stated, the scope is intended to include its endpoints, and all integers and fractions within the scope.For example, when enumerating the scope of "1 to 10", the scope enumerated should be interpreted as including scopes such as "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".

[0019] The present disclosure illustratively described herein suitably can be practiced in the absence of any element or elements, limitation or limitations not specifically disclosed herein. Although compositions and methods are described herein as "comprising" various components or steps, unless otherwise indicated, these compositions and methods can also "consist essentially of" or "consist of" the various components or steps.

[0020] Unless otherwise indicated, all parts, percentages and ratios referred to herein and in the claims are by weight.

[0021] Before presenting details of the following embodiments, some terms are defined or clarified.

[0022] As used herein, the term "elevated temperature" means a temperature above room temperature (22°C).

[0023] 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" contains the active material or material in microencapsulation. The terms "wall" and "shell" are used interchangeably to refer to a structure formed by a microencapsulating polymer surrounding a core of microencapsulated active material.

[0024] As used herein, the term "logP" refers to the octanol / water partition coefficient (P) of a fragrance ingredient, given as the base-10 logarithm of logP. The octanol / water partition coefficient of a fragrance ingredient is the ratio between its equilibrium concentration in octanol and in water. LogP values ​​for many fragrance ingredients have been reported, for example, in the Pomona92 database available from Daylight Chemical Information Systems, Inc. (Daylight CIS) in Irvine, California, USA.

[0025] As used herein, the term "self-condensing polyisocyanate" means a polyurea formed by the self-polymerization of a polyisocyanate in the presence of water. Those skilled in the art understand that an isocyanate can react with water to form an amine, which can further react with an isocyanate to form a urea linkage. Thus, a polyisocyanate can self-polymerize in the presence of water to form a polyurea.

[0026] As used herein, the terms "g," "mg," and "μg" refer to "gram," "milligram," and "microgram," respectively. The terms "L" and "mL" refer to "liter" and "milliliter," respectively.

[0027] polyisocyanates

[0028] As used herein, the terms "polyfunctional isocyanate" and "polyisocyanate" are used interchangeably and refer to compounds having two or more isocyanate (-NCO) groups. Polyisocyanates can be aromatic, aliphatic, linear, branched, or cyclic. In some embodiments, the polyisocyanate contains an average of 2 to 4 isocyanate groups. In some embodiments, the polyisocyanate contains at least three isocyanate functional groups. In some embodiments, the polyisocyanate is water-insoluble. In certain aspects, the polyisocyanate is an oligomeric polyisocyanate obtained from hexamethylene diisocyanate (HDI), which is a monomeric diisocyanate. In certain aspects, the polyisocyanate is an oligomeric polyisocyanate having a biuret, isocyanurate, allophanate, uretdione, and / or oligomeric HDI structure. Exemplary polyisocyanates are sold under the following trade names: TAKENATE ® (For example, TAKENATE ® D-110N; Mitsui Chemicals, DESMODUR ® (Covestro), BAYHYDUR ® (Covestro) and LUPRANATE ® (BASF).

[0029] In certain embodiments, the polyisocyanate is an aromatic polyisocyanate. Desirably, the aromatic polyisocyanate comprises a phenyl, tolyl, xylyl, naphthyl or diphenyl moiety as an aromatic component. In certain embodiments, the aromatic polyisocyanate is selected from the group consisting of: a polyisocyanurate of toluene diisocyanate, a trimethylolpropane adduct of toluene diisocyanate, a trimethylolpropane adduct of xylylene diisocyanate, and a mixture thereof.

[0030] In some embodiments, the aromatic polyisocyanate has the structural formula shown below, and includes structural isomers thereof.

[0031]

[0032] wherein n can vary from 0 to a desired number (e.g., 0-50, 0-20, 0-10, or 0-6). Preferably, the value of n is limited to less than 6. The polyisocyanate may also be a mixture of polyisocyanates, wherein the value of n can vary from 0 to 6. In the case where the polyisocyanate is a mixture of various polyisocyanates, the average value of n preferably falls between 0.5 and 1.5.

[0033] In some embodiments, the aromatic polyisocyanate has the structural formula shown below, and includes structural isomers thereof.

[0034]

[0035] Where R can be C1-C 10 Alkyl, C1-C 10 Representative polyisocyanates with this structure are sold under the trademarks TAKENATE® D-110N (Mitsui Industries, Ltd.), DESMODUR® L75 (Covestro), and DESMODUR® IL (Covestro).

[0036] The trimethylolpropane adduct of xylylene diisocyanate has the structural formula shown below:

[0037]

[0038] In some embodiments, the aromatic polyisocyanate is selected from the group consisting of 1,5-naphthalene diisocyanate, 4,4'-diphenylmethane diisocyanate (MDI), hydrogenated MDI (H12MDI), xylylene diisocyanate (XDI), tetramethylxylene diisocyanate (TMXDI), 4,4'-diphenyldimethylmethane diisocyanate, dialkyldiphenylmethane diisocyanates and tetraalkyldiphenylmethane diisocyanates, 4,4'-dibenzyl diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, isomers of tolylene diisocyanate (TDI), 4,4'-diisocyanatophenylperfluoroethane, diisocyanatoethyl phthalate, aromatic polyisocyanates having reactive halogen atoms, and mixtures thereof. In some embodiments, the aromatic polyisocyanate having a reactive halogen atom is selected from the group consisting of 1-chloromethylphenyl 2,4-diisocyanate, 1-bromomethyl-phenyl 2,6-diisocyanate, 3,3-bischloromethyl ether 4,4'-diphenyl diisocyanate, and mixtures thereof.

[0039] In some embodiments, the polyisocyanate is an aliphatic polyisocyanate.In some embodiments, the aliphatic polyisocyanate is selected from the group consisting of a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate, a biuret of hexamethylene diisocyanate, and mixtures thereof. In some embodiments, the aliphatic polyisocyanate is selected from the group consisting of 1-methyl-2,4-diisocyanatocyclohexane, 1,6-diisocyanato-2,2,4-trimethylhexane, 1,6-diisocyanato-2,4,4-trimethylhexane, 1-isocyanatomethyl-3-isocyanato-1,5,5-trimethylcyclohexane, chlorinated aliphatic diisocyanates, brominated aliphatic diisocyanates, phosphorus-containing aliphatic diisocyanates, tetramethoxybutane 1,4-diisocyanate, butane 1,4-diisocyanate, hexane 1,6-diisocyanate (HDI), dicyclohexylmethane diisocyanate, cyclohexane 1,4-diisocyanate, ethylene diisocyanate, and mixtures thereof. In some embodiments, the polyisocyanate comprises a sulfur-containing polyisocyanate, which can be obtained, for example, by reacting hexamethylene diisocyanate with thiodiglycol or dihydroxydihexyl sulfide. In some embodiments, the polyisocyanate is an aliphatic diisocyanate selected from the group consisting of trimethylhexamethylene diisocyanate, 1,4-diisocyanatobutane, 1,2-diisocyanatododecane, dimerized fatty acid diisocyanate, and mixtures thereof.

[0040] In some embodiments, the weight average molecular weight of the polyisocyanate ranges from 250 Da to 1000 Da, or from 275 Da to 500 Da. In some embodiments, the polyisocyanate used to prepare the shell of the microcapsule is a single polyisocyanate. In other embodiments, the polyisocyanate is a mixture of polyisocyanates. In some embodiments, the mixture of polyisocyanates comprises an aliphatic polyisocyanate and an aromatic polyisocyanate. In some embodiments, the polyisocyanate is a mixture of a biuret of hexamethylene diisocyanate and a trimethylolpropane adduct of xylylene diisocyanate. In some embodiments, the polyisocyanate is an aliphatic polyisocyanate or a combination of aliphatic polyisocyanates, without any aromatic polyisocyanate. In some embodiments, the polyisocyanate is a trimethylolpropane adduct of xylylene diisocyanate, and the shell of the microcapsule comprises a self-condensed trimethylolpropane adduct of xylylene diisocyanate.

[0041] Active Materials

[0042] The core of the microcapsule comprises an active material encapsulated therein. Non-limiting examples include those described in WO 2016 / 049456. These active materials include fragrances, fragrance precursors, flavorings, malodor counteractive agents, vitamins or derivatives thereof, anti-inflammatory agents, anesthetics, analgesics, antimicrobial actives, antivirals, anti-infectives, anti-acne agents, skin lighteners, insect repellents, veterinary repellents, parasite repellents, emollients, skin moisturizers, wrinkle control agents, UV protectants, fabric softener actives, hard surface cleaning actives, skin or hair conditioners, flame retardants, antistatic agents, flavor modifiers, cells, probiotics, antioxidants, self-tanning agents, dihydroxyacetone, cooling agents, sensates, malodor-reactive materials, cosmetic actives, agricultural actives, pesticides, insecticides, herbicides, fungicides, or combinations thereof. Cosmetic actives include vitamins, sun filters and sunscreens, anti-aging agents, anti-wrinkle agents, antioxidants, lifting agents, firming agents, anti-spot agents, anti-redness agents, thinning agents, draining agents, moisturizers, soothing agents, scrubbing agents or exfoliants, matting agents, sebum regulators, skin lightening actives, tanning actives, tanning accelerators, or combinations thereof. In some embodiments, the active material comprises natural extracts and / or essential oils.

[0043] In certain embodiments, the active material is selected from the group consisting of: spices, pro-fragrances, malodor counteractants, and combinations thereof. In certain embodiments, the active material comprises spices. In certain embodiments, the active material comprises low logP spices with a logP value in the range of 0.5 to 2.2, and the amount of low logP spices is 3% to 18% by weight based on the weight of the active material. In certain embodiments, the amount of low logP spices is at least 1.5%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, or 10% by weight based on the weight of the active material. In certain embodiments, the amount of low logP spices is no more than 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, or 7% by weight based on the weight of the active material. In certain embodiments, the amount of low logP spices ranges from 3% to 15%, 4% to 12%, or 5% to 10% by weight based on the weight of the active material.

[0044] In some embodiments, the low logP fragrance has an aqueous solubility of at least 1 g / L, 1.5 g / L, 2 g / L, 2.5 g / L, 3 g / L, or 3.5 g / L measured at 22.5° C. In some embodiments, the low logP fragrance is selected from the group consisting of ethyl vanillin, coumarin, 4-(4-hydroxyphenyl)butan-2-one (oxyphenylon, CAS No. 5471-51-2), p-anisaldehyde, 2-ethyl-3-hydroxy-4H-pyran-4-one (veltol or ethyl maltol, CAS No. 4940-11-8), benzaldehyde, cinnamaldehyde, and combinations thereof. In some embodiments, the low logP fragrance is selected from the group consisting of coumarin, 4-(4-hydroxyphenyl)butan-2-one (hydroxybenzone, CAS No. 5471-51-2), p-anisaldehyde, 2-ethyl-3-hydroxy-4H-pyran-4-one (veltol or ethyl maltol, CAS No. 4940-11-8), benzaldehyde, cinnamaldehyde, and combinations thereof. In some embodiments, the low logP fragrance is selected from the group consisting of coumarin, p-anisaldehyde, benzaldehyde, cinnamaldehyde, and combinations thereof. In some embodiments, the low logP fragrance comprises ethyl vanillin.

[0045] Low-logP fragrances are difficult to encapsulate due to their high water solubility. They also tend to leak out of the microcapsules, resulting in poor capsule stability and performance during the drying phase of laundry. Furthermore, ethyl vanillin can cause discoloration of the slurry and, consequently, of the commercial products to which it is added. It has now been discovered that the core-shell microcapsules of the present disclosure are capable of encapsulating active materials (e.g., fragrances) containing high levels of low-logP fragrance ingredients. Accordingly, the present disclosure provides a core-shell microcapsule slurry comprising: (a) core-shell microcapsules; (b) a dispersant comprising denatured pea protein; and (c) a hydrocolloid comprising gum arabic. In some embodiments, the hydrocolloid comprises gum arabic added to the aqueous phase during slurry formation prior to the emulsification step. In some embodiments, the microcapsule slurry is an aqueous suspension of microcapsules. In some embodiments, the microcapsule slurry is white. The microcapsule slurry can be used directly in consumer products. The microcapsule slurry can also be washed, coated, dried (e.g., spray-dried), and / or combined with one or more other microcapsules, active materials, and / or carrier materials. Core-shell microcapsules comprise a microcapsule core (i.e., core or microcapsule core) and a microcapsule shell (i.e., shell or microcapsule shell). The microcapsule core comprises the active material, and the microcapsule shell comprises a self-condensing polyisocyanate. The microcapsules of the present disclosure need not be perfectly spherical. In some embodiments, the core-shell microcapsules have a diameter of 1 to 100 microns. As used herein, the term "diameter" with respect to a microcapsule refers to the diameter of a sphere having the same volume as the microcapsule.

[0046] The core of the microcapsule contains an active material. The active material includes a low-logP fragrance having a logP value ranging from 0.5 to 2.2, and the amount of the low-logP fragrance is 3% to 18% by weight based on the weight of the active material. In some embodiments, the core of the microcapsule further includes an auxiliary core material, such as a solvent, an emollient, and / or a core modifier material. Examples of auxiliary core materials include nanoscale solid particulate materials, polymer core modifiers, solubility modifiers, density modifiers, stabilizers, humectants, viscosity modifiers, pH modifiers, or combinations thereof. Examples of suitable auxiliary core materials also include those described in WO 2016 / 049456 and US 2016 / 0158121. In some embodiments, the solvent includes caprylic / capric triglyceride. In some embodiments, the solvent includes benzyl benzoate. In some embodiments, the auxiliary core material may also be present in the capsule wall or outside the capsule in the slurry. In some embodiments, the auxiliary core material may be present in the core in an amount of 0.01% to 25% (e.g., 0.5% to 10%) by weight of the capsule.

[0047] The microcapsule shell is formed by the self-polymerization of a polyisocyanate in the presence of water, denatured pea protein, and gum arabic. In some embodiments, the polyisocyanate includes or is a trimethylolpropane adduct of xylylenediisocyanate. It has been discovered that, upon reaction with water to form amine groups, polyisocyanates (such as trimethylolpropane adduct of xylylenediisocyanate) can self-polymerize in the presence of denatured pea protein (as a dispersant) to form a wall material suitable for encapsulating active materials. In some embodiments, the polyisocyanate does not cross-link with the denatured pea protein. In some embodiments, no more than 10%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.2%, or 0.1% of the polyisocyanate is cross-linked with the denatured pea protein. Instead, the denatured pea protein appears to act as a scaffold, promoting the self-polymerization of the polyisocyanate to form the wall polymer that encapsulates the active material. Furthermore, the addition of gum arabic prior to emulsification facilitates the solubility of the denatured pea protein in the aqueous phase, thereby preventing aggregation. In some embodiments, the shell of the microcapsule comprises a single type of polymer (i.e., a self-condensing polyisocyanate). In this regard, the shell of the microcapsule is formed by self-polymerization of one or more polyisocyanates. In some embodiments, the self-condensing polyisocyanate is formed in the absence of an exogenous (i.e., added) cross-linking agent (such as a polyamine and a polyol). In some embodiments, the shell of the microcapsule is substantially free of or free of biopolymers (e.g., pea protein and gum arabic) and / or polyelectrolytes. In some embodiments, the microcapsule shell comprises no more than 15%, 10%, 5%, 3%, 1%, 0.5%, 0.2%, or 0.1% of a biopolymer relative to the total weight of the microcapsule shell. In some embodiments, the microcapsule shell comprises no more than 15%, 10%, 5%, 3%, 1%, 0.5%, 0.2%, or 0.1% of a polyelectrolyte relative to the total weight of the microcapsule shell.

[0048] In some embodiments, the microcapsule shell is biodegradable. As used herein, the term "biodegradable" with respect to a material (e.g., a microcapsule shell as a whole or a polymer of a microcapsule shell) means that the material has no real or perceived health and / or environmental issues and is capable of and / or does undergo physical, chemical, thermal, microbiological, biological, and / or UV or light degradation. Ideally, the microcapsule shell and / or polymer is considered "biodegradable" when it passes one or more of the following tests, including respirometry biodegradation in aquatic media, available from the Organization for Economic Co-operation and Development (OECD), the International Organization for Standardization (ISO), and the American Society for Testing and Materials (ASTM), including, but not limited to, OECD 301F or 310 (ready biodegradation), OECD 302 (intrinsic biodegradation), ISO 17556 (solid irritation study), ISO 14851 (freshwater irritation study), ISO 18830 (marine sediment irritation study), OECD 307 (soil irritation study), OECD 308 (sediment irritation study), and OECD 309 (water irritation study). Preferably, the microcapsules are readily biodegradable as determined using respirometry biodegradation, OECD 301F, or OECD 310 tests in aquatic media. More preferably, the microcapsule shell and / or polymer is biodegradable if it has a biodegradation rate of at least 20%, 30%, 40%, 50% or 60% based on the weight of the shell and / or polymer within 60 days as tested according to OECD 301F or OECD 310, or most preferably at least 20% within 60 days as tested according to OECD 301F.

[0049] In some embodiments, the shell of the microcapsule has a biodegradation rate of at least 20%, 30%, 40%, 50%, or 60% based on the weight of the shell within 60 days according to OECD 301F or OECD 310. In some embodiments, the shell of the microcapsule has a biodegradation rate of at least 20% based on the weight of the shell within 60 days according to OECD 301F or OECD 310.

[0050] The shell of the microcapsule comprises a self-condensing polyisocyanate. In some embodiments, the amount of the self-condensing polyisocyanate ranges from 0.1% to 10%, preferably from 0.1% to 8%, more preferably from 0.2% to 5%, and even more preferably from 1.5% to 3.5% or from 0.1% to 5%, all by weight based on the weight of the core-shell microcapsule slurry. In some embodiments, the amount of the self-condensing polyisocyanate does not exceed 1%, 0.9%, 0.8%, 0.7%, 0.6%, 0.5%, 0.4%, 0.3%, or 0.2% by weight based on the weight of the core-shell microcapsule slurry.

[0051] In some embodiments, the core-shell microcapsules have a diameter ranging from 0.1 micron to 1000 microns (e.g., 0.5 micron to 500 microns, 1 micron to 200 microns, 1 micron to 100 microns, or 1 micron to 50 microns). In some embodiments, the core-shell microcapsules have a diameter of at least 0.1 micron, 0.5 micron, 1 micron, 2 microns, 5 microns, or 20 microns. In some embodiments, the core-shell microcapsules have a diameter of no more than 1000 microns, 500 microns, 200 microns, 100 microns, 75 microns, 50 microns, 30 microns, 20 microns, 10 microns, or 5 microns.

[0052] In some embodiments, the core-shell microcapsule slurry includes a microcapsule forming aid. In some embodiments, the microcapsule forming aid is a dispersant that promotes the formation of a stable emulsion containing nano- or micron-sized oil droplets to be encapsulated. The microcapsule forming aid can also improve the performance of the microcapsules by stabilizing the capsules and / or depositing them to the target area or releasing them into the environment. Performance is measured by the intensity of the fragrance released during each contact point of the user experience (such as the pre- and post-friction stages in the laundry experience). The pre-friction stage is the stage when the microcapsules are deposited on the cloth, for example, after using a fabric softener containing microcapsules during the wash cycle. The post-friction stage is after the microcapsules are deposited on the cloth and the microcapsules are broken by friction or other similar mechanisms. The amount of the microcapsule forming aid can be 0.1% to 40%, 0.1% to 10%, or 0.1% to 5% by weight based on the weight of the microcapsules.

[0053] Examples of microcapsule-forming aids include polyvinyl pyrrolidone, polyvinyl alcohol, poly(styrene sulfonate), carboxymethyl cellulose, sodium salt of naphthalene sulfonate condensate, copolymers of ethylene and maleic anhydride, alginate, hyaluronic acid, poly(acrylic acid), carboxymethyl cellulose, copolymers of acrylic acid and acrylamide, copolymers of acrylamide and acrylamidopropyltrimethylammonium chloride, terpolymers of (acrylic acid, acrylamide, and acrylamidopropyltrimethylammonium chloride), partially or fully hydrolyzed polyvinyl acetate polymers (i.e., polyvinyl alcohol), or combinations thereof.

[0054] Other microcapsule-forming aids include water-soluble salts of alkyl sulfates, alkyl ether sulfates, alkyl isothionates, alkyl carboxylates, alkyl sulfosuccinates, alkyl succinamates, alkyl sulfates such as sodium lauryl sulfate, alkyl sarcosinates, alkyl derivatives of protein hydrolysates, acyl aspartates, alkyl or alkyl ether or alkyl aryl ether phosphates, sodium lauryl sulfate, phospholipids or lecithin, or soaps, sodium stearate, potassium stearate or ammonium stearate, oleates or palmitates, alkylaryl sulfonates such as sodium dodecylbenzenesulfonate, sodium dialkylsulfosuccinate, dioctylsulfosuccinate, sodium dilaurylsulfosuccinate, poly(styrenesulfonic acid) sodium salt, isobutylene-maleic anhydride copolymer, sodium alginate, cellulose sulfate and pectin, isobutylene-maleic anhydride copolymer, gum arabic, carrageenan, pectic acid, tragacanth gum, almond gum, semi-synthetic polymers such as sulfated cellulose, sulfated methyl cellulose, carboxymethyl starch, phosphorylated starch, lignin sulfonic acid; synthetic polymers such as maleic anhydride copolymers (including their hydrolysates), polyacrylic acid, polymethacrylic acid, acrylic acid-butyl acrylate copolymers or crotonic acid homopolymers and copolymers, vinylbenzenesulfonic acid or 2-acrylamido-2-methylpropanesulfonic acid homopolymers and copolymers, and partial amides or partial esters of such polymers and copolymers, carboxyl-modified polyvinyl alcohol, sulfonic acid-modified polyvinyl alcohol and phosphoric acid-modified polyvinyl alcohol, phosphated or sulfated tristyrylphenol ethoxylates.

[0055] In some embodiments, the microcapsule forming aid is a surfactant. Examples of surfactants include, but are not limited to, those sold under the trade name MORWET ® Sulfonated naphthalene formaldehyde condensate sold under the trade name MOWIOL ® Partially hydrolyzed polyvinyl alcohols are sold as, for example, MOWIOL ® 3-83 (Air Products), or SELVOL ® 203 (Sekisui), or polyvinyl alcohol such as Ultalux FP, Ultalux FA, Ultalux AD, OKS-8089 (Sourus); also known as PLURONIC ® SYNPERONIC ® or PLURACARE ® Materials (BASF Corporation) sells ethylene oxide-propylene oxide block copolymers or poloxamers; sold under the trade name FLEXAN ®Sulfonated polystyrene sold by II (Akzo Nobel); sold under the trade name ZEMAC ® Ethylene-maleic anhydride polymers sold by Vertellus Specialties Inc. under the trade name SALCARE ® SC 60 (BASF), a copolymer of acrylamide and acrylamidopropyltrimethylammonium chloride; and the polyquaternium series, such as Polyquaternium 11 ("PQ11"; a copolymer of vinylpyrrolidone and quaternized dimethylaminoethyl methacrylate; sold by BASF as Luviquat PQ11 AT 1). Surfactants MOWIOL ® 3-83 has a viscosity of 2-4 mPa·S (e.g., 3 mPa·S), a degree of hydrolysis of 80%-85% (e.g., 83%), an ester value of 170-210 mg KOH / g (e.g., 190 mg KOH / g), and a residual unhydrolyzed acetyl content of 13%-18% (e.g., 15%). In certain aspects, the surfactant is a sulfonated polystyrene, such as that sold under the trade name FLEXAN ® II is sold as high molecular weight polystyrene sulfonate sodium salt.

[0056] In some embodiments, the microcapsule formation aid is a processing aid, such as a hydrocolloid, which can improve the colloidal stability of the slurry and prevent coagulation, sedimentation, and creaming. In some embodiments, the hydrocolloid is added to the aqueous phase during slurry formation prior to the emulsification step. The term "hydrocolloid" refers to a broad class of water-soluble or water-dispersible polymers having anionic, cationic, zwitterionic, or nonionic characteristics. Suitable hydrocolloids include, but are not limited to, polysaccharides such as starch, modified starch, dextrin, maltodextrin and cellulose derivatives, and quaternized forms thereof; natural gums such as alginates, carrageenan, xanthan gum, agar, pectin, pectic acid, gum arabic, tragacanth and gum karaya, guar gum and quaternized guar gum; gelatin, protein hydrolysates and quaternized forms thereof; synthetic polymers and copolymers such as poly(vinylpyrrolidone-co-vinyl acetate), poly(vinyl alcohol-co-vinyl acetate), poly((meth)acrylic acid), poly(maleic acid), poly(alkyl(meth)acrylate-co-(meth)acrylic acid), poly(acrylic acid-co-maleic acid) copolymers, polyalkylene oxides, poly(vinyl methyl ether), poly(vinyl ether-co-maleic anhydride), and the like, as well as poly(ethylene imine), poly((meth)acrylamide), poly(alkylene oxide-co-dimethylsiloxane), poly(aminodimethylsiloxane), Ultrez 20 (Acrylates / C10-30 Alkyl Acrylate Crosspolymer), sold under the trade name CARBOPOL ®Ultrez 30 is a crosslinked homopolymer of acrylic acid polymerized in a cosolvent system of cyclohexane and ethyl acetate, sold under the trade name ACULYN ® Excel (acrylate copolymers) sells acrylate copolymers under the trade name CARBOPOL ® In some aspects, the core-shell microcapsule slurry is prepared in the presence of gum arabic as a hydrocolloid. In some aspects, the core-shell microcapsule slurry comprises a hydrocolloid containing gum arabic.

[0057] In some embodiments, a microcapsule forming aid may be used in combination with carboxymethyl cellulose ("CMC"), polyvinyl pyrrolidone, polyvinyl alcohol, alkyl naphthalene sulfonate formaldehyde condensate, and / or a surfactant to facilitate capsule formation during processing. Examples of surfactants that may be used in combination with the microcapsule forming aid include, but are not limited to, cetyltrimethylammonium chloride (CTAC), available under the trade name PLURONIC ® (e.g. PLURONIC ® F127), PLURAFAC ® (e.g. PLURAFAC ® F127), or poloxamers sold by Miranet-N, under the trade name Q-NATURALE ® Saponins, such as those sold by National Starch Food Innovation; or gum arabic, such as Seyal or Senegal.

[0058] In some aspects, the CMC polymer has a molecular weight ranging from about 90,000 daltons to 1,500,000 daltons, preferably from about 250,000 daltons to 750,000 daltons, and more preferably from 400,000 daltons to 750,000 daltons. The CMC polymer has a degree of substitution from about 0.1 to about 3, preferably from about 0.65 to about 1.4, and more preferably from about 0.8 to about 1.0. The CMC polymer can be present in the microcapsule slurry in an amount of about 0.1% to about 2% and preferably from about 0.3% to about 0.7% based on the weight of the microcapsule slurry. In other aspects, the polyvinyl pyrrolidone used in this disclosure is a water-soluble polymer and has a molecular weight from 1,000 to 10,000,000 daltons. Suitable polyvinyl pyrrolidones include polyvinyl pyrrolidone K12, K15, K17, K25, K30, K60, K90, or a combination thereof. The amount of polyvinyl pyrrolidone can be 2%-50%, 5%-30%, or 10%-25% by weight of the microcapsule slurry. Commercially available alkyl naphthalene sulfonate formaldehyde condensates include MORWET ® D-425, a sodium salt of a naphthalenesulfonate condensate, is available from Akzo Nobel, Fort Worth, Texas.

[0059] In some embodiments, the microcapsule-forming aid is a food-grade dispersant. The term "food-grade dispersant" refers to a dispersant of food quality suitable for human consumption. They can be natural or non-natural dispersants. Natural dispersants are dispersants that occur naturally and are derived from natural sources. Natural dispersants, including their derivatives, can be salted, desalted, deoiled, fractionated, or modified using natural enzymes or microorganisms. Non-natural dispersants are dispersants that are chemically synthesized by chemical methods that do not involve enzyme modification.

[0060] Natural dispersants include quillaja saponins, lecithin, gum arabic, pectin, carrageenan, chitosan, chondroitin sulfate, modified cellulose, cellulose gum, modified starch, whey protein, pea protein, egg white protein, silk protein, fish gelatin, porcine or bovine protein, ester gum, fatty acid, or a combination thereof. In some aspects, the microcapsule slurry is prepared in the presence of a denatured protein (e.g., denatured pea protein) as a dispersant. In some aspects, the core-shell microcapsule slurry comprises a dispersant comprising a denatured protein, such as denatured pea protein, particularly a denatured pea protein isolate.

[0061] In certain embodiments, the natural dispersant is a plant storage protein. Plant storage proteins are proteins that accumulate in various plant tissues and serve as biological reserves for metal ions and amino acids. Plant storage proteins can be divided into two categories: seed or grain storage proteins and vegetative storage proteins. Seed / grain storage proteins are a group of proteins that accumulate to high levels in seeds / grains during the late stages of seed / grain development, while vegetative storage proteins are proteins that accumulate in vegetative tissues such as leaves, stems, and tubers (depending on the plant species). During germination, seed / grain storage proteins degrade, and the amino acids produced are used as a nutrient source by the developing seedlings. In some aspects, the dispersant for preparing microcapsules is a leguminous storage protein, particularly a protein extracted from soybean, lupin, pea, chickpea, alfalfa, broad bean, lentil, kidney bean, or a combination thereof. In certain embodiments, the plant storage protein is pea protein.

[0062] Pea protein includes pea protein isolate, pea protein concentrate, or a combination thereof. Pea protein isolates and concentrates are generally understood to be composed of several proteins. For example, pea protein isolates and concentrates can include legumin, vicilin, and convicilin protein. The term "pea protein" is also intended to include partially or completely modified or denatured pea proteins. Individual plant storage proteins (e.g., legumin, vicilin, or convicilin) ​​can also be used to prepare the microcapsules of the present disclosure.

[0063] Ideally, the pea protein disclosed herein is denatured, preferably without causing gelation of the pea protein. Exemplary conditions for denaturing proteins (e.g., pea protein) include, but are not limited to, exposure to heat or cold, changes in pH, exposure to denaturants (such as detergents, urea, or other chaotropic agents), or mechanical stress (including shear forces). In some aspects, the pea protein is partially denatured, e.g., 50%, 60%, 70%, 80%, or 85% denatured based on the total weight of the pea protein. In other aspects, the pea protein is substantially or completely denatured, e.g., at least 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, or 100% denatured based on the total weight of the pea protein. For example, when using an 8% pea protein solution (w / v), the solution can be treated at a temperature of 80°C to 90°C for 20 to 30 minutes (or preferably at 85°C for 25 minutes) to produce substantially denatured pea protein. Therefore, depending on the degree of denaturation desired, it will be understood that higher temperatures and shorter times may also be employed.

[0064] In particular, it has been found that chaotropic agents are particularly useful in providing denatured proteins (e.g., denatured pea protein) for use in preparing the microcapsules of the present disclosure. As is conventional in the art, chaotropic agents are compounds that disrupt hydrogen bonds in aqueous solutions, thereby increasing entropy. Typically, this reduces the hydrophobic effect necessary for the three-dimensional structure of proteins. Chaotropic agents can be used to provide ... by having a positive chaotropic value (i.e., kJ kg on the Hallsworth scale). -1 An example of a value for the chaotropic property is, for example, CaCl2 + 92.2 kJ kg -1 、MgCl2 kJ kg -1 + 54.0, butanol + 37.4 kJ kg -1 , Guanidine hydrochloride + 31.9 kJkg -1 and urea + 16.6 kJ kg -1 In certain aspects, the chaotropic agent is a guanidine salt, such as guanidine sulfate, guanidine carbonate, guanidine nitrate, or guanidine chloride. In specific aspects, the pea protein is partially or completely denatured with guanidine carbonate.

[0065] In addition to natural dispersants, non-natural dispersants are also used to prepare the microcapsules of the present disclosure. Non-natural dispersants include N-lauroyl-L-arginine ethyl ester, sorbitan esters, polyethoxylated sorbitan esters, polyglycerol esters, fatty acid esters, or combinations thereof.

[0066] Other food-safe dispersants can also be used in the microcapsule slurry of the present disclosure. Examples include ammonium phosphate, acetic acid esters of mono- and diglycerides (Acetem), lactic acid esters of mono- and diglycerides (Lactem), citrate esters of mono- and diglycerides (Citrem), mono- and diacetyltartaric acid esters of mono- and diglycerides (Datem), succinate esters of monoglycerides (SMG), ethoxylated monoglycerides, sucrose esters of fatty acids, sucrose glycerides, polyglycerol polyricinoleate, propane-1,2-diol esters of fatty acids, thermally oxidized soybean oil interacting with mono- or diglycerides of fatty acids, sodium stearoyl lactylate (SSL), calcium stearoyl lactylate (CSL), stearyl tartarate, polyglycerol esters of transesterified ricinoleic acid (E476), sodium stearyl lactylate, sodium lauryl sulfate, polyoxyethylated hydrogenated castor oil (e.g., sold under the trade name CREMO-PHOR ® Sold under the trade name PLURONIC ® sold), polyoxyethylene fatty alcohol ether, and polyoxyethylene stearate.

[0067] In some embodiments, the core-shell microcapsule slurry further comprises a rheology modifier (e.g., xanthan gum), a preservative, an emulsifier, or a combination thereof. In some embodiments, the core-shell microcapsule slurry further comprises a rheology modifier. One or more rheology modifiers or viscosity control agents can be added to the microcapsule slurry to achieve the desired viscosity of the slurry so that the microcapsules are dispersed in the slurry for an extended period of time. During capsule preparation, the rheology modifier is preferably added before emulsification of the aqueous and oil phases and is typically uniformly dispersed in the microcapsule slurry and on the outside of the microcapsule walls of the microcapsules. Suitable rheology modifiers include acrylate copolymers, cationic acrylamide copolymers, polysaccharides, or a combination thereof. Preferably, the addition of a rheology modifier to the slurry provides a viscosity modifier having a viscosity of at least 21 s. -1 A slurry having a viscosity of less than 600 cps (centipoise) or less than 580 cps at 22°C as measured at a shear rate of 1000 rpm.

[0068] Commercially available acrylate copolymers include those sold under the trade name ACULYN ® Those from Dow Chemical Company, such as ACULYN ® 22 (Copolymer of Acrylates and Steareth-20 Methacrylate), ACULYN ® 28 (Copolymer of Acrylates and Beheneth-25 Methacrylate), ACULYN ® 33 (copolymer of acrylic acid and acrylates), ACULYN ® 38 (crosspolymer of acrylates and vinyl neodecanoate), and ACULYN ® 88 (crosspolymer of acrylates and steareth-20 methacrylate). Particularly useful acrylate copolymers are anionic acrylate copolymers such as ACULYN ® 33. An alkali-soluble anionic acrylic polymer emulsion (ASE) synthesized from acrylic acid and acrylate comonomers by emulsion polymerization. It is marketed under the trade name CARBOPOL ® Commercially available acrylate copolymers are also suitable for use in the present invention. An example is CARBOPOL ® ETD 2020 Polymers (Acrylates and Acrylic C 10 -C 30 cross-linked polymers of alkyl esters), CARBOPOL ® ETD 2691 and CARBOPOL ® ETD 2623 (cross-linked acrylate copolymer).

[0069] Polysaccharides Another class of agents suitable as rheology modifiers. In certain aspects, polysaccharides useful as rheology modifiers include starch, pectin, and plant gums such as algin, guar gum, locust bean gum, and xanthan gum, such as those sold under the trade name KELTROL ® Xanthan gum sold as T (80 mesh food grade) is commercially available from CP Kelco, Atlanta, GA. Preferably, the rheology modifier comprises or is xanthan gum.

[0070] In some embodiments, the active material is a fragrance and the microcapsule slurry has: (a) less than 0.3% or less than 0.25% non-encapsulated fragrance based on the total weight of the fragrance in the slurry, (b) -1 A viscosity of less than 600 cps or less than 580 cps at 22°C measured at a shear rate of 100 Å / min, or (c) a combination of (a) and (b).

[0071] In some embodiments, the core-shell microcapsule slurry further comprises a capsule deposition aid. The amount of the capsule deposition aid in the slurry can range from 0.01% to 25% by weight, more preferably from 5% to 20% by weight, based on the weight of the microcapsules. The capsule deposition aid can be added during capsule preparation or after the capsules are prepared.

[0072] Deposition aids are used to help the capsules deposit onto surfaces such as fabrics, hair or skin. Examples of capsule deposition aids include anionic, cationic, nonionic or amphoteric water-soluble polymers. Suitable capsule deposition aids include polyquaternium-4, polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-16, polyquaternium-22, polyquaternium-24, polyquaternium-28, polyquaternium-39, polyquaternium-44, polyquaternium-46, polyquaternium-47, polyquaternium-53, polyquaternium-55, polyquaternium-67, polyquaternium-68, polyquaternium-69, polyquaternium-73, polyquaternium-74, polyquaternium-77, polyquaternium- -78, polyquaternium-79, polyquaternium-80, polyquaternium-81, polyquaternium-82, polyquaternium-86, polyquaternium-88, polyquaternium-101, polyethyleneamine, polyethyleneimine, polyethyleneamine and vinylformamide copolymer, acrylamidopropyltrimethylammonium chloride / acrylamide copolymer, methacrylamidopropyltrimethylammonium chloride / acrylamide copolymer, a polymer comprising units derived from polyethylene glycol and terephthalate, a polyester, a polymer derived from a dicarboxylic acid and a polyol, or a combination thereof. Other suitable capsule deposition aids include those described in WO 2016 / 049456, pages 13-27. Additional capsule deposition aids are described in US 2013 / 0330292, US 2013 / 0337023, and US 2014 / 0017278.

[0073] In certain embodiments, the core-shell microcapsule slurry also includes a preservative. One or more preservatives can be added to the microcapsule slurry to prevent microorganisms from damaging or unintentionally growing within a specific period of time, thereby extending the shelf life. The preservative can be any organic preservative that does not damage the microcapsule slurry. Suitable water-soluble preservatives include organosulfur compounds, halogenated compounds, cyclic organic nitrogen compounds, low molecular weight aldehydes, parahydroxybenzoates, propylene glycol materials, isothiazolinones, quaternary compounds, and benzoates. Examples of preservatives include low molecular weight alcohols, dehydroacetic acid, phenyl and phenoxy compounds, or combinations thereof.

[0074] A non-limiting example of a commercially available water-soluble preservative is a mixture of about 77% 5-chloro-2-methyl-4-isothiazolin-3-one and 23% 2-methyl-4-isothiazolin-3-one. Additional antimicrobial preservatives include those available from Rohm & Haas under the trade name KATHON ® 1.5% aqueous solution of CG; 5-bromo, sold under the trade name BRONIDOXL by Henkel ® Available: 2-bromo-2-nitro-1,3-propanediol, sold under the trade name BRONOPOL from Inorex ®Available; 1,1'-hexamethylenebis(5-(p-chlorophenyl)biguanide) and its salts, such as acetate and digluconate; 1,3-bis(hydroxy)-1,3-diol, from Ronza under the trade name GLYDANT PLUS ® Available: glutaraldehyde; ICI polyaminopropyl biguanide; dehydroacetic acid; and 1,2-benzisothiazolin-3-one, as PROXEL ® Sold under the GXL brand name.

[0075] The microcapsule slurry of the present disclosure is shown to be an effective delivery system that can deliver fragrances in consumer products such as fabric conditioners. In addition, the microcapsule slurry can also be used in a wide range of consumer applications, such as personal care products, including shampoos, hair conditioners, conditioners, hair fresheners; personal washing products, such as bar soaps, body washes, personal cleansers and disinfectants; fabric care products, such as fabric refreshers, softeners and dryer sheets, ironing water, industrial cleaners, liquid and powder detergents (including unit dose capsules), rinse conditioners, and scent enhancement products; fine fragrances, such as body sprays and eau de toilette products; deodorants; roll-on products, and aerosol products.

[0076] The present disclosure also provides a method for producing a core-shell microcapsule slurry as described herein. The method comprises: (a) preparing an aqueous phase by: (i) denaturing pea protein, (ii) adjusting the pH of the aqueous phase to below 6, and (iii) adding gum arabic as a hydrocolloid to the aqueous phase; (b) preparing an oil phase comprising an active material and a polyisocyanate; (c) emulsifying the oil phase with the aqueous phase to form a slurry comprising core-shell microcapsules; and (d) curing the shells of the microcapsules at a temperature below 80°C. The produced core-shell microcapsule slurry comprises: (a) core-shell microcapsules, the core of the microcapsule comprising an active material and the shell of the microcapsule comprising a self-condensing polyisocyanate; (b) a dispersant comprising denatured pea protein; and (c) a hydrocolloid comprising gum arabic; wherein the active material comprises a low logP fragrance having a logP value ranging from 0.5 to 2.2, the amount of the low logP fragrance is 3% to 18% by weight based on the weight of the active material, and the core-shell microcapsule slurry is white.

[0077] As described herein, upon reaction with water to form an amine, the polyisocyanate, in the presence of denatured pea protein as a dispersant, will self-polymerize and form a wall material suitable for encapsulating active materials in core-shell microcapsules. Without wishing to be bound by theory, it is hypothesized that the denatured pea protein provides a scaffold that promotes the self-polymerization of the polyisocyanate. Advantageously, the inclusion of denatured pea protein allows for the use of reduced levels of polyisocyanate and improves the sustainability and biodegradability of the resulting core-shell microcapsules. Furthermore, by adjusting the pH of the emulsion or slurry to below 6 and / or curing the microcapsule shell at a temperature below 80°C, desired microcapsule properties, such as good drying properties, low discoloration, and / or reduced aggregation or agglomeration, can be achieved.

[0078] Pea protein can be denatured in an aqueous phase by exposure to heat or cold, pH changes, denaturants (such as detergents, urea or other chaotropic agents), or mechanical stress (including shear forces). In some embodiments, the pea protein is denatured by heating the aqueous pea protein solution to a temperature of 80°C to 170°C, or 80°C to 140°C, or 80°C to 120°C, or 80°C to 105°C, or 80°C to 90°C. In some embodiments, the pea protein is denatured by a denaturant. In some embodiments, the pea protein is denatured by a chaotropic agent. In some embodiments, the chaotropic agent comprises or is a guanidine salt. In some embodiments, the guanidine salt is selected from the group consisting of guanidine sulfate, guanidine carbonate, guanidine nitrate, guanidine chloride, and mixtures thereof. In some embodiments, the chaotropic agent comprises guanidine carbonate. In some embodiments, the denaturing step (a)(i) comprises mixing the pea protein and guanidine carbonate in an aqueous solution (e.g., an aqueous phase).

[0079] The pH of the aqueous phase (e.g., an aqueous solution containing a mixture of pea protein and guanidine carbonate) is adjusted to less than 6 or no more than 6. In some embodiments, the pH of the aqueous phase is adjusted to less than 5.5 or no more than 5.5. In some embodiments, the pH of the aqueous phase is adjusted to at least 2, 3, 3.5, 4, or 4.5. In some embodiments, the pH of the aqueous phase is adjusted to a range of 2 to 6, or 3 to 5.5, or 3.5 to 4.5, or 3.8 to 4.2. Gum arabic is added to the aqueous phase as a hydrocolloid.

[0080] The oil phase can be prepared by mixing the active material and the polyisocyanate. In some embodiments, an auxiliary core material (e.g., a solvent) is also mixed with the active material and the polyisocyanate. In some embodiments, the polyisocyanate is dissolved in a solution comprising a solvent (e.g., caprylic / capric triglyceride) and the active material. In some embodiments, the active material is selected from the group consisting of: fragrances, fragrance precursors, malodor counteractants, and combinations thereof. The active material comprises a low logP fragrance having a logP value in the range of 0.5 to 2.2, and the amount of the low logP fragrance is 3% to 18% by weight based on the weight of the active material. In some embodiments, the active material is a fragrance and the slurry has: (a) less than 0.3% or less than 0.25% of non-encapsulated fragrance based on the total weight of the fragrance, (b) as in 21 s -1 The viscosity of the microcapsules and microcapsule slurry is less than 600 cps or less than 580 cps at 22 ° C, measured at a shear rate of 100 ℃ or less, or (c) a combination of (a) and (b). In some embodiments, the amount of polyisocyanate used to prepare the microcapsules and microcapsule slurry is 0.1% to 8% based on the weight of the core-shell microcapsule slurry. In some embodiments, the amount of polyisocyanate used to prepare the microcapsules and microcapsule slurry ranges from 0.1% to 10%, or 0.1% to 8%, or 0.2% to 5%, or 1.5% to 3.5%, or 0.1% to 5% by weight based on the weight of the core-shell microcapsule slurry. In some embodiments, the amount of polyisocyanate used to prepare the microcapsules and microcapsule slurry is no more than 1%, 0.9%, 0.8%, 0.7%, 0.6%, 0.5%, 0.4%, 0.3%, or 0.2% by weight based on the weight of the core-shell microcapsule slurry. In some embodiments, the polyisocyanate includes or is a trimethylolpropane adduct of xylylene diisocyanate.

[0081] In step (c), the oil phase is emulsified with an aqueous phase to form a slurry comprising core-shell microcapsules. In some embodiments, the slurry is an emulsion. In step (d), the shell of the microcapsule is cured at a temperature lower than 80°C (e.g., in the range of 63°C to 67°C). As used herein, the term "curing" means a process in which a polymer is toughened or hardened by heat, chemical additives, and / or light radiation. In some embodiments, the microcapsule shell is cured at high temperatures. In some embodiments, the microcapsule shell is cured at a temperature lower than 80°C or lower than 70°C. In some embodiments, the microcapsule shell is cured at a temperature in the range of 15°C to 80°C, or 55°C to 65°C, or 55°C to 70°C, or 55°C to 80°C, or 63°C to 67°C. In some embodiments, the microcapsule shell can be cured for 1 minute to 10 hours, or 0.1 hour to 5 hours, or 0.2 hour to 4 hours, or 0.5 hour to 3 hours. In some embodiments, the microcapsule slurry can be heated to the desired curing temperature at a linear rate of 0.5 to 20°C / minute (eg, 1 to 5°C / minute, 2 to 8°C / minute, or 2 to 10°C / minute).

[0082] In some embodiments, the method for producing a microcapsule slurry further comprises adding a rheology modifier, a preservative, an emulsifier, or a combination thereof to the microcapsule slurry. In some embodiments, a rheology modifier (e.g., xanthan gum) is added to the aqueous phase prior to step (c).

[0083] In some embodiments, no catalyst, such as 1,4-diazabicyclo[2,2,2]octane (DABCO), N-methylimidazole, diaminobicyclooctane, 2,2'-dimorpholinodiethyl ether, is used to form the shell of the microcapsules. In some embodiments, the amount of catalyst used for shell formation is no more than 50 wppm (parts per million by weight), 20 wppm, 10 wppm, 5 wppm, 2 wppm, 1 wppm, 0.5 wppm, or 0.2 wppm based on the weight of the microcapsule slurry.

[0084] The microcapsule slurry of the present disclosure can be formulated into a microcapsule delivery system for consumer products. The microcapsule delivery system can be a microcapsule slurry suspended in an external solvent (e.g., water, ethanol, or a combination thereof), wherein the microcapsules are present at a level of 0.1% to 80% (e.g., 70%-75%, 40%-55%, 50%-90%, 1% to 65%, or 5% to 45%) by weight of the microcapsule delivery system.

[0085] Alternatively or additionally, the microcapsules and slurries thereof prepared according to the present disclosure may be subsequently purified. See US 2014 / 0017287. Purification may be achieved by washing the microcapsule slurry with water until a neutral pH is obtained.

[0086] The microcapsule delivery system may optionally contain one or more other delivery systems, such as polymer-assisted delivery compositions (see US 8,187,580), fiber-assisted delivery compositions (US 2010 / 0305021), cyclodextrin host-guest complexes (US 6,287,603 and US 2002 / 0019369), fragrance precursors (WO 2000 / 072816 and EP 0922084), or combinations thereof. The microcapsule delivery system may also contain one or more (e.g., two, three, four, five, or six or more) different microcapsules, including those disclosed herein and other microcapsules, such as aminoplasts, hydrogels, sol-gels, polyurea / polyurethane microcapsules, and melamine formaldehyde microcapsules. Further exemplary delivery systems that may be incorporated are coacervate microcapsules (see WO 2004 / 022221) and cyclodextrin delivery systems (see WO 2013 / 109798 and US 2011 / 03085560).

[0087] The microcapsule slurry of the present disclosure is very suitable for inclusion in any of the various consumer products that require controlled release of active materials (e.g., spices or flavors). The present disclosure also provides consumer products comprising the core-shell microcapsule slurry of the present disclosure. In some embodiments, the consumer product is selected from the group consisting of: fabric conditioners, fabric softeners, fabric refreshers, liquid laundry detergents, powder detergents, scent enhancers, shower gels, bath soaps, shampoos, hair conditioners, body sprays, hair freshening sprays, hair dyes, hair moisturizers, skin moisturizers, hair conditioners, antiperspirants, deodorants, skin conditioners, insect repellents, candles, surface cleaners, bathroom cleaners, bleach, cat litter, freshening sprays, pesticides, insecticides, herbicides, fungicides, paints, and combinations thereof.

[0088] application

[0089] The microcapsule slurries and delivery systems of the present disclosure are well suited for, but not limited to, use in, laundry detergents, liquid laundry detergents, powdered laundry detergents, tablet laundry detergents, laundry detergent bars, laundry detergent creams, hand laundry detergents, fabric conditioners or softeners, fabric refreshers, fragrance enhancers, shampoos, hair conditioners, bar soaps, shower gels, body washes, antiperspirants, body sprays, body sprays, body lotions, candles, or textiles.

[0090] More specifically, the microcapsules of the present disclosure can be used in the following products:

[0091] A) Fabric care products such as rinse conditioners (containing from 1 to 30 wt. % fabric conditioning actives), fabric liquid conditioners (containing from 1 to 30 wt. % fabric conditioning actives), tumble dryer softener sheets, fabric refreshers, fabric refresher sprays, ironing liquids, and fabric softener systems such as those described in US 6,335,315, US 5,674,832, US 5,759,990, US 5,877,145, US 5,574,179, US 5,562,849, US 5,545,350, US 5,545,340, US 5,411,671, US 5,403,499, US 5,288,417, US 4,767,547 and US 4,424,134.

[0092] Liquid fabric softener / freshener contains at least one fabric softener, which is preferably present in a concentration of 1% to 30% (e.g., 4% to 20%, 4% to 10%, and 8% to 15%) by weight of the liquid fabric softener / freshener. The ratio between the active material and the fabric softener can be 1:500 to 1:2 (e.g., 1:250 to 1:4 and 1:100 to 1:8). As an illustration, when the fabric softener is 5% by weight of the fabric softener, the active material is 0.01% to 2.5%, preferably 0.02% to 1.25%, and more preferably 0.1% to 0.63%. As another example, when the fabric softener is 20% by weight of the fabric softener, the active material is 0.04% to 10%, preferably 0.08% to 5%, and more preferably 0.4% to 2.5%. The active material is a fragrance, a malodor counteractant, or a combination thereof. Liquid fabric softeners can have 0.15% to 15% capsules (e.g., 0.5% to 10%, 0.7% to 5%, and 1% to 3%). When capsules are included at these levels, the pure oil equivalent (NOE) in the softener is 0.05% to 5% (e.g., 0.15% to 3.2%, 0.25% to 2%, and 0.3% to 1%).

[0093] Suitable fabric softeners include cationic surfactants. Non-limiting examples are quaternary ammonium compounds (QACs), such as alkylated quaternary ammonium compounds, cyclic or cyclic quaternary ammonium compounds, aromatic quaternary ammonium compounds, diquaternary ammonium compounds, alkoxylated quaternary ammonium compounds, amidoamine quaternary ammonium compounds, ester quaternary ammonium compounds, or combinations thereof.

[0094] The fabric softening product comprises an aqueous solution of QAC characterized by:

[0095] a) the viscosity of the final product ranges from 5 cps to 300 cps at 106 s-1, preferably from 20 cps to 150 cps;

[0096] b) QAC levels range from 0.5 wt% to 20 wt%, preferably 1 wt% to 16 wt%, more preferably 6 wt% to 12 wt% softening active. Preferred, typical cationic fabric softening components include water-insoluble quaternary ammonium fabric softeners, most commonly di-long alkyl chain ammonium chloride or methyl sulfate. Preferred cationic softeners include, but are not limited to, the following:

[0097] a. Rapidly biodegradable quaternary ammonium compounds containing one or more ester linkages between the quaternary ammonium group and a long alkyl chain (e.g., TEA esterquats, DEEDMAC, and HEQ);

[0098] b. Non-ester quaternary ammonium compounds (e.g., ditallow dimethyl ammonium chloride (DTDMAC); dihydrogenated tallow dimethyl ammonium chloride; dihydrogenated tallow dimethyl ammonium methylsulfate; distearyl dimethyl ammonium chloride; dioleyl dimethyl ammonium chloride; dipalmityl hydroxyethyl methyl ammonium chloride; stearyl benzyl dimethyl ammonium chloride; tallow trimethyl ammonium chloride; hydrogenated tallow trimethyl ammonium chloride; C12-14 alkyl hydroxyethyl dimethyl ammonium chloride; C12-18 alkyl dihydroxyethyl methyl ammonium chloride; di(stearoyloxyethyl)dimethyl ammonium chloride (DSOEDMAC); di(tallowyloxyethyl)dimethyl ammonium chloride; ditallow imidazolinium methylsulfate; 1-(2-tallowamidoethyl)-2-tallow imidazolinium methylsulfate).

[0099] A first group of quaternary ammonium compounds (QACs) suitable for use in accordance with the present disclosure is represented by formula (I):

[0100] (I)

[0101] wherein each R is independently selected from C1-C 35 Alkyl or alkenyl; R 1 represents a C1-C4 alkyl, C2-C4 alkenyl, or C1-C4 hydroxyalkyl group; T is typically O-CO (i.e., an ester group bonded to R via its carbon atom), but may alternatively be CO-O (i.e., an ester group bonded to R via its oxygen atom); n is a number selected from 1 to 4; m is a number selected from 1, 2, or 3; and X is an anionic counterion, such as a halide or alkyl sulfate, for example, chloride or methyl sulfate. Di-ester variants (i.e., m = 2) of formula (I) are preferred and typically have mono- and tri-ester analogs associated therewith.

[0102] Particularly preferred agents are formulations rich in the diester of triethanolammonium methylsulfate (also known as "TEA esterquats"). Commercial examples include STEPANTEX® UL85 (from Stepan), Prapagen™ TQL (from Clariant), and Tetranyl™ AHT-1 (from Kao) (all di-[hardened tallow ester] of triethanolammonium methylsulfate), AT-1 (di-[tallow ester] of triethanolammonium methylsulfate), and L5 / 90 (di-[palmityl ester] of triethanolammonium methylsulfate) (all from Kao), as well as REWOQUAT® WE15 (with a C10-C15 derivative). 20 and C 16 -C 18 Di-ester of fatty acyl residues of unsaturated fatty acids with triethanolammonium methylsulfate) (from Evonik).

[0103] Also suitable are soft quaternary ammonium active substances such as STEPANTEX® VK90, STEPANTEX® VT90, SP88 (from Stepan), Prapagen™ TQ (from Clariant), DEHYQUART® AU-57 (from Cognis), REWOQUAT® WE18 (from Degussa), and Tetranyl™ L190 P, Tetranyl™ L190 SP and Tetranyl™ L190 S (all from Kao Corporation).

[0104] A second group of QACs suitable for use in accordance with the present disclosure is represented by formula (II):

[0105] (R 1 )2-N + -[(CH2) n -TR 2 ]2X - (II)

[0106] Each R 1 Groups are independently selected from C l -C4 alkyl, or C2-C4 alkenyl; and wherein each R 2 Groups are independently selected from C8-C 28 and n, T and X- are as defined above. Preferred materials of this second group include bis(2 tallow acyloxyethyl)dimethylammonium chloride and hardened forms thereof.

[0107] A third group of QACs suitable for use in accordance with the present disclosure is represented by formula (III):

[0108]

[0109] Each R 1 Groups are independently selected from C1-C4 alkyl, hydroxyalkyl or C2-C4 alkenyl; and wherein each R 2 Groups are independently selected from C8-C 28 alkyl or alkenyl; and wherein n, T, and X are as defined above. Preferred materials of this second group include 1,2-bis[tallowoyloxy]-3-trimethylammoniumpropane chloride, 1,2-bis[hardened tallowoyloxy]-3-trimethylammoniumpropane chloride, 1,2-bis[oleoyloxy]-3-trimethylammoniumpropane chloride, and 1,2-bis[stearoyloxy]-3-trimethylammoniumpropane chloride. Such materials are described in US Pat. No. 4,137,180 (Lever Brothers). Preferably, these materials also contain an amount of the corresponding mono-ester.

[0110] Co-softeners. Co-softeners (also known as co-softeners) and fatty complexing agents can be used in the fabric conditioner compositions of the present disclosure. When used, they are typically present in an amount of 0.1% to 20%, and particularly 0.1% to 5%, based on the total weight of the composition. Preferred co-softeners include fatty alcohols, fatty esters, and fatty N-oxides. Fatty esters that can be used include fatty monoesters such as glyceryl monostearate, and fatty sugar esters such as those disclosed in WO 01 / 46361 (Unilever).

[0111] In some embodiments, the compositions of the present disclosure may include a co-active substance. Particularly suitable fatty complexing agents include fatty alcohols and fatty acids. Of these, fatty alcohols are most preferred. Without being bound by theory, it is believed that the fatty complexing material improves the viscosity characteristics of the composition by complexing with the mono-ester component of the fabric conditioner material, thereby providing a composition with relatively high levels of di- and tri-ester-linked components. Di- and tri-ester-linked components are more stable and do not adversely affect the initial viscosity as much as mono-ester components. It is also believed that the high levels of mono-ester-linked components present in compositions containing TEA-based quaternary ammonium materials may destabilize the composition through depletion flocculation. By using a co-active material to complex with the mono-ester-linked components, depletion flocculation is significantly reduced. In other words, as required by the present disclosure in some embodiments, the increased levels of the co-active substance "neutralize" the mono-ester-linked components of the quaternary ammonium material. This di-ester generated in situ from the mono-ester and fatty alcohol also improves the softening of the composition.

[0112] Silicones. In some embodiments, the compositions of the present disclosure may further contain a silicone-based fabric softener. Preferably, the fabric softening silicone is polydimethylsiloxane. Fabric softening silicones include, but are not limited to, 1) non-functionalized silicones, such as polydimethylsiloxane (PDMS) or alkyl (or alkoxy)-functionalized silicones; and 2) functionalized silicones or copolymers having one or more different types of functional groups, such as amino, phenyl, polyether, acrylate, silicon hydride, carboxylic acid, quaternized nitrogen, and the like. Suitable silicones can be selected from polydialkylsiloxanes, preferably polydimethylsiloxane, more preferably amino-functionalized silicones; anionic silicones, and carboxyl-functionalized silicones. Aminosilicones, such as Arristan 64 from CHT or Wacker CT45E from Wacker, may also be used.

[0113] For silicone emulsions, particle size can range from about 1 nm to 100 microns and preferably from about 10 nm to about 10 microns, including microemulsions (< 150 nm), standard emulsions (about 200 nm to about 500 nm), and macroemulsions (about 1 micron to about 20 microns).

[0114] Nonionic surfactant. In some embodiments, the composition may further comprise a nonionic surfactant. Typically, these nonionic surfactants may be included for the purpose of stabilizing the composition. Suitable nonionic surfactants include addition products of ethylene oxide with fatty alcohols, fatty acids, and fatty amines. Any of the specific types of alkoxylated materials described below can be used as nonionic surfactants. Suitable surfactants are substantially water-soluble surfactants having the general formula (V): R-(C2H4O)z-CH2-CH2-OH (V), wherein R is selected from the group consisting of: primary, secondary, and branched alkyl and / or acyl hydrocarbon groups; primary, secondary, and branched alkenyl hydrocarbon groups; and primary, secondary, and branched alkenyl-substituted phenolic hydrocarbon groups; hydrocarbon groups having a chain length of 8 to about 25, preferably 10 to 20 (e.g., 14 to 18) carbon atoms. In the general formula of the ethoxylated nonionic surfactant, Y is typically: -O-, -C(O)O-, -C(O)N(R)- or -C(O)N(R)R, wherein R has the meaning given above for formula (V), or can be hydrogen; and Z is at least about 8, preferably at least about 10 or 11.

[0115] Preferably, the nonionic surfactant has an HLB of about 7 to about 20, more preferably 10 to 18 (e.g., 12 to 16). GENAPOL® C200 (Clariant), which is based on a coconut oil chain and has 20 EO groups, is an example of a suitable nonionic surfactant. If present, the nonionic surfactant is present in an amount of 0.01% to 10%, more preferably 0.1% to 5%, by weight, based on the total weight of the composition. LUTENSOL® AT25 (BASF), which is based on a coconut oil chain and has 25 EO groups, is an example of a suitable nonionic surfactant. Other suitable surfactants include RENEX® 36 (Trideceth-6) (from Croda); TERGITOL® 15-S3 (from Dow Chemical Co.); Dihydrol LT7 (from Thai Ethoxylate Ltd.); CREMOPHOR® CO40 (from BASF) and NEODOL® 91-8 (from Shell).

[0116] Cationic polysaccharides. In some embodiments, the composition may further comprise at least one cationic polysaccharide. Cationic polysaccharides can be obtained by chemically modifying polysaccharides, typically natural polysaccharides. Through such modification, cationic side groups can be introduced into the polysaccharide backbone. Cationic polysaccharides are not limited to: cationic cellulose and its derivatives, cationic starch and its derivatives, cationic guaiac and its derivatives, cationic xylan and its derivatives, cationic mannan and its derivatives, cationic galactomannans and its derivatives, such as cationic guar gum and its derivatives. Suitable cationic celluloses include cellulose ethers containing quaternary ammonium groups, cationic cellulose copolymers, or cellulose grafted with water-soluble quaternary ammonium monomers.

[0117] Cellulose ethers containing quaternary ammonium groups are described in French Patent No. 1,492,597 and include, in particular, polymers sold by Dow under the names "JR" (JR 400, JR 125, JR 30M) or "LR" (LR 400, LR 30M). These polymers are also defined in the CTFA dictionary as quaternary hydroxyethylcelluloses that have been reacted with an epoxide substituted with trimethylammonium groups. Suitable cationic celluloses also include LR3000 KC from Solvay. Cationic cellulose copolymers or cellulose grafted with water-soluble quaternary ammonium monomers are described, inter alia, in US Pat. No. 4,131,576, such as hydroxyalkylcelluloses, for example, hydroxymethyl-, hydroxyethyl-, or hydroxypropylcellulose grafted with methacryloyl-ethyltrimethylammonium, methacrylamidopropyltrimethylammonium, or dimethyl-diallylammonium salts.

[0118] Commercial products corresponding to this definition are more particularly the products sold under the names CELQUAT® L 200 and CELQUAT® H 100 by Akzo Nobel. Cationic starches suitable for the present disclosure include the products sold under the names POLYGELO® (cationic starches from Sigma), SOFTGEL®, AMYLOFAX® and SOLVITOSE® (cationic starches from Avebe), CATO from National Starch. Suitable cationic galactomannans may be those derived from fenugreek gum, konjac gum, tara gum, cassia gum or guar gum.

[0119] In some embodiments, the cationic polysaccharides of the present disclosure may have an average molecular weight (Mw) between 100,000 Daltons and 3,500,000 Daltons, preferably between 100,000 Daltons and 1,500,000 Daltons, more preferably between 100,000 Daltons and 1,000,000 Daltons.

[0120] In some embodiments, the fabric conditioner compositions of the present disclosure preferably comprise 0.01 to 2 wt% of a cationic polysaccharide, based on the total weight of the composition. More preferably, the cationic polysaccharide comprises 0.025 to 1 wt% based on the total weight of the composition. Most preferably, the cationic polysaccharide comprises 0.04 to 0.8 wt% based on the total weight of the composition. In the context of this application, the term "degree of substitution (DS)" of a cationic polysaccharide (such as cationic guar gum) refers to the average number of substituted hydroxyl groups per sugar unit. DS can particularly refer to the number of carboxymethyl groups per sugar unit. DS can be determined by titration.

[0121] The DS of the cationic polysaccharide is preferably in the range of 0.01 to 1, more preferably 0.05 to 1, and most preferably 0.05 to 0.2. In the context of the present application, the "charge density (CD)" of a cationic polysaccharide (such as cationic guar gum) refers to the ratio of the number of positive charges on the monomer units contained in the polymer to the molecular weight of the monomer units. The CD of a cationic polysaccharide (such as cationic guar gum) is preferably in the range of 0.1 to 3 (meq / gm), more preferably 0.1 to 2 (meq / gm), and most preferably 0.1 to 1 (meq / gm).

[0122] Nonionic polysaccharides. In some embodiments, the fabric conditioner composition may further comprise at least one nonionic polysaccharide. The nonionic polysaccharide may be a modified nonionic polysaccharide or an unmodified nonionic polysaccharide. The modified nonionic polysaccharide may include hydroxyalkylation and / or esterification. In the context of the present disclosure, the level of modification of the nonionic polysaccharide may be characterized by molar substitution (MS), which refers to the average number of moles of substituents (e.g., hydroxypropyl) per mole of monosaccharide units. MS may be determined by the Zeisel-GC method, particularly based on the following literature reference: Hodges et al. (1979) Anal. Chem. [Analytical Chemistry] 51(13). Preferably, the modified nonionic polysaccharide has an MS in the range of 0 to 3, more preferably 0.1 to 3, and most preferably 0.1 to 2.

[0123] In some embodiments, the nonionic polysaccharides of the present disclosure may be selected from, inter alia, glucans, modified or non-modified starches such as those derived from, for example, cereals (e.g., wheat, corn, or rice), vegetables (e.g., yellow peas), and tubers (e.g., potato or cassava), amylose, amylopectin, glycogen, dextran, cellulose and its derivatives (methylcellulose, hydroxyalkylcellulose, ethylhydroxyethylcellulose), mannans, xylans, lignin, arabinans, galactans, galacturonans, chitin, chitosan, glucuronoxylans, arabinoxylans, xyloglucans, glucomannans, pectic acid and pectin, arabinogalactans, carrageenans, agar, gum arabic, tragacanth, gum ghatti, gum karaya, carob gum, galactomannans such as guar gum and its nonionic derivatives (hydroxypropyl guar), and mixtures thereof.

[0124] Among these celluloses, hydroxyethyl cellulose and hydroxypropyl cellulose are particularly useful. Suitable non-limiting examples include the products sold by Aqualon under the trade names KLUCEL® EF, KLUCEL® H, KLUCEL® LHF, KLUCEL® MF, and KLUCEL® G, and the products sold by Amerchol under the trade name CELLOSIZE® Polymer PCG-10, and the products sold by Ashland under the trade names HEC, HPMC K200, and HPMC K35M.

[0125] In certain embodiments, the fabric conditioner composition of the present disclosure preferably comprises 0.01 wt% to 2 wt% of the nonionic polysaccharide based on the total weight of the composition. More preferably, 0.025 wt% to 1 wt% of the nonionic polysaccharide based on the total weight of the composition. Most preferably, 0.04 wt% to 0.8 wt% of the nonionic polysaccharide based on the total weight of the composition. Preferably, the fabric conditioning composition comprises 0.02 wt% to 4 wt%, more preferably 0.05 wt% to 2 wt% and most preferably 0.08 wt% to 1.6 wt% of the combined weight of the cationic polysaccharide and the nonionic polysaccharide. Preferably, the ratio of the weight of the cationic polysaccharide in the composition to the weight of the nonionic polysaccharide in the composition is between 1: 10 and 10: 1, more preferably between 1: 3 and 3: 1.

[0126] In a preferred embodiment, the cationic polysaccharide and the nonionic polysaccharide are mixed before being added to the fabric conditioner composition. Preferably, the mixture is prepared as a suspension in water. Preferably, the ratio of the weight of the quaternary ammonium compound in the composition to the total weight of the cationic polysaccharide and the nonionic polysaccharide in the composition is between 100:1 and 2:1, more preferably between 30:1 and 5:1.

[0127] Water. In some embodiments, the fabric conditioner compositions of the present disclosure include water. These compositions are softening compositions suitable for rinse addition in laundry processes. These compositions are pourable liquids. These liquid compositions have a pH ranging from about 2.0 to about 7, preferably from about 2 to about 4, more preferably from about 2.5 to about 3.5. These compositions may also contain a pH regulator, preferably hydrochloric acid, lactic acid or sodium hydroxide. The composition is preferably a ready-to-use liquid comprising an aqueous phase. The aqueous phase may include water-soluble substances such as mineral salts or short-chain (C1-C4) alcohols. The composition is preferably used in the rinse cycle of household textile washing operations, wherein it can be added directly to the washing machine in an undiluted state, for example, through a dispenser drawer, or for top-loading washing machines, directly to a tub. These compositions may also be used for household handwashing laundry operations.

[0128] Fabric conditioner compositions can typically be prepared by combining a melt containing the fabric softener with an aqueous phase. The polymer can be combined with the aqueous phase, or it can be post-dosed into the composition after the melt and aqueous phase have been combined. A preferred preparation method is as follows:

[0129] 1. Heat water to about 40°C to 50°C, preferably above 45°C.

[0130] 2. Slowly add the rheology modifier to the water, preferably over about 1 minute with stirring.

[0131] 3. Mix thoroughly, preferably for 1 to 10 minutes.

[0132] 4. Add any minor ingredients such as defoamers, chelating agents and preservatives.

[0133] 5. Melt the softening active and optional fatty alcohol together to form a eutectic.

[0134] 6. Add the eutectic to the heated water.

[0135] 7. If necessary, add acid to the preferred pH.

[0136] 8. Add dyes and fragrances.

[0137] 9. Cool down.

[0138] B) Liquid dishwashing detergents, such as those described in US 6,069,122 and US 5,990,065.

[0139] C) Automatic dishwashing detergents, such as those described in US 6,020,294, US 6,017,871, US 5,968,881, US 5,962,386, US 5,939,373, US 5,914,307, US 5,902,781, US 5,705,464, US 5,703,034, US 5,703,030, US 5,679,630, US 5,597,936, US 5,581,005, US 5,559,261, US 4,515,705, US 5,169,552 and US 4,714,562.

[0140] D) All-purpose cleaners, including bucket-dilutable and toilet cleaners, bathroom cleaners, bath towels, carpet deodorizers, candles (e.g., scented candles), room deodorizers, floor cleaners, disinfectants, window cleaners, garbage bags / trash can liners, air fresheners (e.g., room deodorizers, car deodorizers, sprays, essential oil air fresheners, automatic spray air fresheners, and neutralizing gel beads), moisture absorbers, household devices (e.g., paper towels and disposable wipes), and moth balls / traps / cakes.

[0141] E) Personal care products: cosmetic or pharmaceutical preparations. More specifically, personal cleansers (e.g., bar soaps, shower gels, and shower gels), in-shower conditioners, sunscreens (e.g., sprays, lotions, and sticks), insect repellents, hand sanitizers, anti-inflammatory agents (e.g., creams, ointments, and sprays), antibacterial agents (e.g., ointments and creams), sensates, deodorants and antiperspirants (including aerosols, pump sprays, and wax-based), lotions, body and foot powders, body sprays or mists, shaving creams and men's grooming products, bath products, and exfoliating scrubs.

[0142] F) Hair care products. More specifically, shampoos (liquid and dry powder), hair conditioners (e.g., rinse-off conditioners, leave-in conditioners, and cleansing conditioners), conditioners, hair refreshers, hair fragrances, hair straightening products, hair styling products, hair fixatives and styling aids, combing creams, waxes, hair foams, hair sprays, non-aerosol pump sprays, hair bleaches, dyes and colorants, perms, and hair wipes.

[0143] In particular aspects, the core-shell microcapsule slurry of the present disclosure is used to improve the freshness of fabrics.Thus, in certain aspects, the microcapsules of the present disclosure are contained in a fabric conditioner or softener having a pH of 2 to 4, preferably a pH of 2.5 to 3.5.

[0144] Many aspects and embodiments have been described above and are intended to be exemplary rather than restrictive. After reading this specification, skilled artisans will appreciate that other aspects and embodiments are possible without departing from the scope of the invention.

[0145] Examples

[0146] The following non-limiting examples are provided to further illustrate the present invention and should not be construed as limitations of the invention as many variations thereof are possible without departing from the spirit or scope of the invention.

[0147] Overview

[0148] The caprylic / capric triglyceride used in the examples is sold under the trade name NEOBEE ® M-5 is a commercial product from Stepan Corporation of Chicago, IL. The polyisocyanate used in the examples is a commercial product of Mitsue Chemicals Inc., Japan, under the trade name TAKENATE ®D110N is a commercially available trimethylolpropane adduct of xylylene diisocyanate. One of ordinary skill in the art will appreciate that some commercial polyisocyanate products are solutions of polyisocyanates in solvents. The polyisocyanates indicated in this disclosure (e.g., TAKENATE ® The amount D110N) refers to the amount of polyisocyanate itself, ie excluding the amount of solvent.

[0149] Example 1: Synthesis of reference microcapsules

[0150] Melamine formaldehyde capsules were prepared as described in Example 1 of US 2012 / 0093899. Briefly, 80 parts by weight of Helion flavor (International Flavors & Fragrance Inc., Union Beach, NJ) were mixed with 20 parts by weight of caprylic / capric triglyceride solvent to form a flavor / solvent composition. Uncoated capsules were prepared by creating a polymer wall to encapsulate droplets of the flavor / solvent composition. First, a copolymer of acrylamide and acrylic acid (available under the trade name ALCAPSOL ® 200) and methylated melamine formaldehyde resin (sold under the trade name CYMEL ® The two components were allowed to react under acidic conditions for at least one hour.

[0151] The fragrance / solvent composition was then added to the wall polymer solution and droplets of the desired size were obtained by high shear homogenization. For the microcapsule slurry, the polymer layer surrounding the fragrance / solvent composition droplets was cured at 125°C. After cooling to room temperature, ethylene urea was added to the microcapsule slurry. Additionally, a rheology modifier and preservative were added. The pH was adjusted using NaOH. The slurry components are listed in Table 1. The slurry contained a total fragrance loading of 28.0%.

[0152] Table 1 - Slurry composition

[0153]

[0154] 1 AS ACULYN ® 33A available.

[0155] 2 As PROXEL ® GXL available.

[0156] Example 2: Preparation of polyisocyanate microcapsules in the presence of denatured pea protein, modified starch / polystyrene sulfonate sodium salt

[0157] The oil phase was prepared by mixing 80 parts by weight of Helion fragrance with 20 parts by weight of caprylic / capric triglyceride solvent to form a fragrance / solvent composition. The aqueous phase was prepared by dispersing pea protein powder (15.4% by weight) in water. Guanidine carbonate was added as a denaturant, and the pH was adjusted to 5 using citric acid. These components were allowed to react for 15 minutes.

[0158] Then it will be sold under the trade name PURITY GUM ® Modified starches sold by Ingredion, Inc. (Ingredion, Westchester, IL) and those sold under the trade name FLEXAN ® High molecular weight polystyrene sulfonate sodium salt sold by TANOPHOSPHATE II was added to the aqueous phase as an emulsifier, and the mixture was mixed for 15 minutes. Tanal-02 (high molecular weight general purpose hydrolyzable tannin; Ajinomoto Natural Specialties, Tokyo, Japan) was then added to the aqueous phase.

[0159] A polyisocyanate was added to the oil phase at 5% by weight. The oil phase was then emulsified into the aqueous phase at a shear rate of 7400 revolutions per minute (RPM) for 3 minutes to form an oil-in-water emulsion (i.e., microcapsule slurry). For the microcapsule slurry, the polymer layer (i.e., shell) surrounding the fragrance / solvent composition droplets was cured at 55°C for 3.5 hours and 80°C for 30 minutes. Subsequently, a rheology modifier and preservative (1,2-benzisothiazolin-3-one) were added. The slurry components are listed in Table 2. The slurry contained a total fragrance loading of 31.2%.

[0160] Table 2 - Slurry composition

[0161]

[0162] 1 As FLEXAN ® II available.

[0163] 2 As PURITY GUM ® Ultra available.

[0164] 3 As TAKENATE ® D110N is available.

[0165] 4 As PROXEL ® GXL available.

[0166] Example 3: Preparation of polyisocyanate microcapsules in the presence of denatured pea protein, modified starch / polystyrene sulfonate sodium salt at pH 4 and a curing temperature of 65°C

[0167] The general procedure of Example 2 was followed with the following changes: the pH of the aqueous phase was adjusted to 4 instead of 5, and curing was carried out at 65° C. for 4 hours. The components of the slurry are listed in Table 3. The slurry contained a total fragrance load of 31.2%.

[0168] Table 3 - Slurry composition

[0169]

[0170] 1 As FLEXAN ® II available.

[0171] 2 As PURITY GUM ® Ultra available.

[0172] 3 As TAKENATE ® D110N is available.

[0173] 4 As PROXEL ® GXL available.

[0174] Example 4: Preparation of microcapsules with reduced levels of denatured pea protein

[0175] The general procedure of Example 3 was followed with reduced concentrations of pea protein. The components of the slurry are listed in Table 4. The slurry contained a total flavor load of 31.2%.

[0176] Table 4 - Slurry composition

[0177]

[0178] 1 As FLEXAN ® II available.

[0179] 2 As PURITY GUM ® Ultra available.

[0180] 3 As TAKENATE ® D110N is available.

[0181] 4 As PROXEL ®GXL available.

[0182] Example 5: Preparation of microcapsules at lower pH

[0183] The general procedure of Example 3 was followed except that the pH of the aqueous phase was adjusted to 3 instead of 4. The components of the slurry are listed in Table 5. The slurry contained 30.3% total fragrance loading.

[0184] Table 5 - Slurry composition

[0185]

[0186] 1 As FLEXAN ® II available.

[0187] 2 As PURITY GUM ® Ultra available.

[0188] 3 As TAKENATE ® D110N is available.

[0189] 4 As PROXEL ® GXL available.

[0190] Example 6: Preparation of microcapsules by adjusting pH using phosphoric acid

[0191] The general procedure of Example 3 was followed except that the pH of the aqueous phase was adjusted by using phosphoric acid instead of citric acid. The components of the slurry are listed in Table 6. The slurry contained a total fragrance load of 32.2%.

[0192] Table 6 - Slurry composition

[0193]

[0194] 1 As FLEXAN ® II available.

[0195] 2 As PURITY GUM ® Ultra available.

[0196] 3 As TAKENATE ® D110N is available.

[0197] 4 As PROXEL ® GXL available.

[0198] Example 7: Preparation of microcapsules with increased fragrance loading

[0199] The general procedure of Example 3 was followed, but with a reduced amount of water. The components of the slurry are listed in Table 7. The slurry contained a total fragrance load of 34.6%.

[0200] Table 7 - Slurry composition

[0201]

[0202] 1 As FLEXAN ® II available.

[0203] 2 As PURITY GUM ® Ultra available.

[0204] 3 As TAKENATE ® D110N is available.

[0205] 4 As PROXEL ® GXL available.

[0206] Example 8: Preparation of microcapsules using higher concentrations of surfactant

[0207] The general procedure of Example 3 was followed, using a higher amount of surfactant. The composition of the slurry is listed in Table 8. The slurry contained a total perfume load of 28.6%.

[0208] Table 8 - Slurry composition

[0209]

[0210] 1 As FLEXAN ® II available.

[0211] 2 As PURITY GUM ® Ultra available.

[0212] 3 As TAKENATE ® D110N is available.

[0213] 4 As PROXEL ® GXL available.

[0214] Example 9: Microcapsules prepared with denatured pea protein and gum arabic

[0215] The oil phase was prepared by mixing 80 parts by weight of Helion fragrance with 20 parts by weight of caprylic / capric triglyceride solvent to form a fragrance / solvent composition. Polyisocyanate was added to the oil phase at 5% by weight.

[0216] The aqueous phase was prepared by dispersing 12.43 grams of pea protein powder in 124 grams of water and adjusting the pH to 9-9.5 using 0.3 grams of 25% sodium hydroxide solution. To promote the dissolution of pea protein isolate and inhibit its aggregation (Liu et al. (2010) Food Res. International. [Food Research International] 43:489-495), 85 grams of instant gum arabic AA (Nexira, Somerville, NJ; 10% solution) was included as a hydrocolloid. The aqueous mixture was high sheared at 7400 rpm for 20 seconds. A 10% slurry of ... ® II (15 grams of a 10% solution) was added to the aqueous phase, and the resulting aqueous mixture was high sheared at 7400 rpm for 20 seconds. In a separate beaker, 38 grams of a 20% guanidine carbonate solution was adjusted to a pH of 4 using 31 grams of a 50% citric acid solution, and the resulting solution was foamed. The resulting guanidine citrate solution was added to the pea protein / gum arabic aqueous mixture and allowed to react at room temperature for 15 minutes. 48 grams of a 1% xanthan gum solution was then added to the aqueous phase, followed by 10 grams of a 30% Tanal-02 solution.

[0217] The oil phase was then emulsified into the water phase at a shear rate of 7400 rpm for 3 minutes to form an oil-in-water emulsion (i.e., microcapsule slurry). For the microcapsule slurry, the polymer layer (i.e., shell) surrounding the fragrance / solvent composition droplets was cured at 65°C for 4 hours. Additionally, a preservative was added to the slurry. The components of the slurry are listed in Table 9. The slurry contained a total fragrance load of 31.2%.

[0218] Table 9 - Slurry composition

[0219]

[0220] 1 As FLEXAN ® II available.

[0221] 2 As TAKENATE ® D110N is available.

[0222] 4 As PROXEL ®GXL available.

[0223] The same microcapsule slurry was prepared without gum arabic. However, without gum arabic, the emulsion completely failed and no microcapsules formed. This indicates that polyisocyanate / pea protein microcapsules cannot form in the absence of gum arabic.

[0224] Example 10: Fabric Conditioner Sample Containing Microcapsules

[0225] An unperfumed model fabric conditioner with 10% holes in the formulation was used to allow for the addition of water and microcapsules. The microcapsules described in Examples 1-3 were premixed with water and then added to the model fabric conditioner. The resulting samples were homogenized using an overhead stirrer at 300 rpm. The finished fabric conditioner samples contained 0.2% pure oil equivalent, resulting in the microcapsules in Examples 2 and 3 having 0.65% by weight of encapsulated fragrance, and the reference microcapsules in Example 1 having 0.72% by weight of encapsulated fragrance.

[0226] 35 grams of the finished fabric conditioner, containing the microcapsule dosage cited above, was added to a front-loading Miele Professional PW 6065 Vario washing machine. The wash load contained 2.2 kg of laundry, including eight large towels, two T-shirts, two pillowcases, two dish towels, and two small hand towels for evaluation. The wash temperature was set to 40°C, with 15.5 L of water used for the main wash and 34 L for both rinses. The total wash cycle was 60 minutes. Some towels were reserved for wet evaluation, and the remainder were air-dried at room temperature for dry evaluation.

[0227] Randomly selected damp samples were evaluated by several panelists using a 0-5 intensity scale, where 0 indicates "no performance" and 5 indicates "strong performance." The evaluations were conducted blindly, with each sample receiving a randomly assigned number. Dry evaluations were conducted the day after the dampness and by the same panelists using the same 0-5 intensity scale. Sensory scores were recorded before and after each randomly selected piece of cloth (contained in an individual polyethylene bag) was gently handled. The results of these analyses are presented in Table 10.

[0228] Compared to both the melamine formaldehyde microcapsules (Example 1) and the pea protein / isocyanate microcapsules with high pH and high curing temperature (Example 2), Example 3 (pea protein / isocyanate microcapsules with low pH and low curing temperature) performed better by providing a strong aroma burst during the drying evaluation (post-treatment). Furthermore, the microcapsules of Example 3 demonstrated their ability to survive the wet stage on cloth, despite being relatively weak compared to the microcapsules of Example 2. Furthermore, when compared to the microcapsules of Examples 1 and 2, the microcapsules of Example 3 demonstrated improved processability, lack of aggregate formation, and improved slurry color.

[0229] Table 10 – Sensory evaluation results

[0230]

[0231] Example 11: Analytical evaluation of different microcapsules

[0232] Characteristics of the microcapsules produced in Examples 1, 3, 4, 5, 6, and 9, including fragrance loading, encapsulation efficiency, free oil, viscosity, and size, were determined. The results of these analyses are presented in Table 11.

[0233] Table 11 – Analysis and evaluation results

[0234]

[0235] 1 Fr. Load = Fragrance Load.

[0236] 2 EE = encapsulation efficiency.

[0237] 3 Viscosity was measured on a Hake plate rheometer using shear rates of 5, 21, and 64 seconds.

[0238] 4 PSD = particle size distribution. Tbm, to be measured.

[0239] Furthermore, the wall strength of the microcapsules prepared in Example 9 was determined in comparison with whey microcapsules prepared according to Example 7 of WO 2020 / 131875 A2 and microcapsules prepared according to Example 2. The wall strength was measured by contacting and gradually compressing a single microcapsule with a probe tip. Figure 1The analysis presented in shows that the choice of protein has less influence on the wall strength and flexibility of the microcapsules. The pH and the curing profile have a stronger influence on the wall strength while maintaining the flexibility (deformation) of the wall. This combination allows for minimal wet performance but a very strong burst with minimal friction in the drying phase. The wall strength is so weak that minimal energy breaks the wall but the flexibility is sufficient to withstand the wash cycle of an EU washing machine and the wet phase on a cloth. Although relatively weak compared to whey microcapsules or melamine formaldehyde microcapsules, the polyisocyanate / pea protein based microcapsules have good stability in the product and maintain the processability of the slurry. In Figure 1 , the X (horizontal) axis is the position or displacement of the probe tip, and the Y (vertical) axis is the force exerted by the probe tip on the microcapsule surface.

[0240] Example 12: Malodor Absorption Capacity

[0241] To test the malodor absorption capacity of the microcapsules disclosed herein, diethyl phthalate and caprylic / capric triglyceride solvents were encapsulated according to the methods presented in Example 1 (melamine formaldehyde) and Example 9 (polyisocyanate microcapsules prepared with pea protein and gum arabic), respectively, to produce odorless microcapsules.

[0242] The microcapsules were exposed to the malodor and the reduction in malodor concentration was measured by headspace analysis. More specifically, 100 grams of a 1.5% malodor solution was placed in a wide-mouth bottle and allowed to equilibrate for 30 minutes. The towel was "activated" by rubbing the towel five times with a tongue depressor on the side marked with an "X". The "activated" towel was placed with the "X" side facing up in a second wide-mouth bottle (16 oz) equipped with a septum injection cap. 100 mL of the malodor vapor was transferred to the second wide-mouth bottle containing the towel sample using a 100 mL airtight syringe. The towel sample was stored for 1.5 hours and then the headspace was analyzed using an SKC pump with a flow rate of 150 ml / min, sampling for 10 minutes onto a tenax tube.

[0243] The results of this analysis (Table 12) indicate that the polyisocyanate microcapsules prepared with pea protein and gum arabic have comparable malodor absorption capacity to that of melamine formaldehyde microcapsules.

[0244] Table 12 – Odor Absorption Evaluation Results

[0245]

[0246] Example 13: Microcapsules prepared with oils containing high concentrations of natural components

[0247] The performance of microcapsules encapsulating natural flavors (i.e., plant extracts or distilled products) or naturally derived flavors (i.e., chemically modified natural flavors) was also evaluated (Table 13). These microcapsules were prepared according to the method described in Example 9.

[0248] Table 13 – Evaluation Results

[0249]

[0250] "++" indicates excellent performance in terms of breakout and pleasant feel during dry down.

[0251] "+" indicates good performance in terms of breakout and pleasant sensation in the drydown.

[0252] “-” indicates poor performance in terms of dryness and pleasantness.

[0253] n / a, not available.

[0254] Perfume leakage from microcapsules prepared according to the method described in Example 9 was evaluated after storage at 37°C in a fabric conditioner. The results of this analysis (Table 14) show stable encapsulation of oils containing a large number of natural extracts and essential oils.

[0255] The performance of polyisocyanate microcapsules prepared according to the method described in Example 9 was compared with that of melamine formaldehyde microcapsules (Example 1) in the wet, pre-drying, gentle handling (GHD) and post-drying stages. "Pre-drying" refers to the stage after drying but before folding the cloth. "GHD" refers to the stage in which the cloth was folded twice and then evaluated by the panelists. "Post-drying" refers to the stage in which the cloth was rubbed at least once with both hands, applying mechanical force to rupture the test microcapsules, and then evaluated for signs of fragrance release. Fragrance intensity was determined on a scale of 0-5, with 0 indicating no effect and 5 indicating maximum effect. Perfumers and fragrance design managers evaluated intensity and pleasantness.

[0256] Table 14 – Evaluation Results

[0257]

[0258] *, failed due to high viscosity of the process.

[0259] ++, stable performance and pleasant feeling.

[0260] +, stable performance, but poor features.

[0261] + / -, poor performance and features.

[0262] ^, Release profile is different, but acceptable.

[0263] Expert evaluation by the fragrance design manager and perfumer indicated that the pleasantness of the microcapsules produced by the method described in Example 9 was stable for oils containing high levels of natural substances (Table 14). In contrast, the melamine formaldehyde microcapsules did not demonstrate good encapsulation or stable performance over time in the product.

[0264] Example 14: Microcapsules containing low logP fragrance

[0265] The stability and performance of microcapsules encapsulating low-logP fragrances were also evaluated (Tables 16 and 17). These test microcapsules were prepared according to the methods described in Example 1 (melamine formaldehyde capsules) and Example 9 (polyisocyanate capsules), respectively, except that the fragrance compositions to be encapsulated in these examples were mixtures of the fragrance bases indicated in Tables 16 and 17 and one or more low-logP fragrances. Ethyl vanillin had a logP value of 1.55, benzaldehyde had a logP value of 1.70, cinnamaldehyde had a logP value of 1.82, oxybenzone had a logP value of 1.48, veltol had a logP value of 0.50, coumarin had a logP value of 1.51, and aubepine had a logP value of 2.20. The fragrance bases had the composition shown in Table 15 below. The ingredients of the fragrance bases had logP values ​​ranging from 2.26 to 7.17.

[0266] Table 15 - Fragrance Base Composition

[0267]

[0268] Fabric softener samples containing test microcapsules were prepared by diluting a microcapsule slurry prepared according to the methods described in Example 1 or Example 9 (except that the fragrance composition was different) in water and adding it to an unperfumed fabric softener base. The resulting mixture was homogenized using an overhead stirrer at 300 rpm for 15 minutes. The finished fabric softener samples contained 0.1% pure oil equivalent. Samples were prepared one day prior to the wash experiment.

[0269] Stability Testing: Finished fabric softener samples were placed at 37°C for a period of up to 8 weeks. Test samples were removed at 4 and 8 weeks for sensory evaluation and fragrance leakage measurement. "Fresh" (Performance) in Table 17 means when the finished fabric softener samples were fresh and evaluated before being placed at 37°C for an extended period of time.

[0270] Sensory Performance Evaluation: The fragrance intensity of the fragrance composition encapsulated by the test microcapsules was evaluated using a European washing machine (Miele) using a recognized test protocol with samples of finished fabric softener. Terry towels were used for the wash test and washed with samples of finished fabric softener containing the test microcapsules. The washed terry towel samples were removed from the washing machine and line-dried overnight. Randomly selected damp terry towel samples were evaluated by several panelists using an intensity scale of 0-5, where 0 means "no performance" and 5 means "strong performance." The evaluations were conducted blindly, with each sample receiving a randomly assigned number. Dry evaluations were conducted the day after the dampness test and were performed by the same panelists using the same 0-5 intensity scale.

[0271] Table 16 – Evaluation Results

[0272]

[0273] Notes: (1) FB means fragrance base. (2) The amount of low logP fragrance ingredient in a fragrance composition (in percent) is based on the total weight of the fragrance composition. (3) FO means free oil. The amount of free oil in the slurry (in percent) is measured based on the total weight of the fragrance composition before the slurry is mixed with the fabric softener. (4) "Leakage at 4 weeks at 37°C" means the amount of fragrance leakage from the microcapsules measured after a sample of the finished fabric softener is placed at 37°C for a period of 4 weeks, based on the total weight of the fragrance composition. (5) "Leakage at 8 weeks at 37°C" means the amount of fragrance leakage from the microcapsules measured after a sample of the finished fabric softener is placed at 37°C for a period of 8 weeks, based on the total weight of the fragrance composition. (6) "Slurry color" means the color of the microcapsule slurry before the slurry is mixed with the fabric softener. (7) "Fabric softener color" is the color of a sample of the finished fabric softener containing 0.3% pure oil equivalent.

[0274] Table 17 – Sensory Properties

[0275]

[0276] Notes: (1) FB means fragrance base. (2) The amount (in percent) of the low logP fragrance ingredient in a fragrance composition is based on the total weight of the fragrance composition. (3) "Fresh Performance," "Fresh Performance Strength," "Performance at 8 Weeks at 37°C," and "Strength at 8 Weeks at 37°C" are evaluations of laundered terry towel samples after drying and gentle handling. (4) "8 Weeks at 37°C" means that the finished fabric softener samples were exposed to 37°C for a period of 8 weeks.

[0277] This example demonstrates that the core-shell microcapsules of the present disclosure can successfully encapsulate fragrance ingredients with low logP values ​​(0.5 to 2.2). Polyisocyanate microcapsules prepared according to the method described in Example 9 successfully encapsulated fragrance ingredients containing 15% ethyl vanillin, 15% oxybenzone, or 15% coumarin. These microcapsules exhibited high encapsulation efficiency (low free oil) for low-logP fragrance ingredients, good dry sensory properties, and stability. In contrast, melamine formaldehyde microcapsules prepared according to the method described in Example 1 exhibited low encapsulation efficiency (high free oil), high leakage, and poor dry sensory properties for low-logP fragrance ingredients. High leakage of ethyl vanillin caused the slurry to turn brown, which also discolored commercial products to which it was added. Therefore, the core-shell microcapsules of the present disclosure provide a superior delivery system for low-logP fragrances, bringing caring, creamy, sweet, oriental, sensory, and luxurious benefits to consumer products.

[0278] It should be noted that not all of the activities described above in the general description or examples are required, that a portion of a specific activity may not be required, and that one or more additional activities may be performed in addition to those described. Furthermore, the order in which the activities are listed is not necessarily the order in which they are performed.

[0279] In the foregoing description, the concepts have been described with reference to specific embodiments. However, it will be understood by those skilled in the art that various modifications and changes may be made without departing from the scope of the invention as set forth in the following claims. Therefore, this description is to be regarded as illustrative rather than restrictive, and all such modifications are intended to be included within the scope of the invention.

[0280] The benefits, other advantages, and solutions to problems have been described above in conjunction with specific embodiments. However, any benefit, advantage, solution to a problem, and any one or more features that may cause or make apparent any benefit, advantage, or solution should not be construed as a key, required, or essential feature of any or all claims.

[0281] It should be understood that certain features described herein for clarity in the context of separate embodiments may also be provided in combination in a single embodiment. Conversely, various features described for brevity in the context of a single embodiment may also be provided individually or in any subcombination.

[0282] Each document cited herein, including any cross-referenced or related patents or applications and any patent applications or patents to which this application claims priority or the benefit of, is hereby incorporated by reference in its entirety unless expressly excluded or otherwise limited. The citation of any document is not an admission that it is prior art with respect to any invention disclosed or claimed herein, nor is it an admission that it alone or in any combination with any other reference(s) teaches, suggests, or discloses any such invention. Furthermore, to the extent that any meaning or definition of a term in this document conflicts with any meaning or definition of the same term in a document incorporated by reference, the meaning or definition assigned to that term in this document shall govern.

Claims

1. A core-shell microcapsule slurry comprising: (a) core-shell microcapsules, the core of the microcapsule comprising an active material and the shell of the microcapsule comprising a self-condensing polyisocyanate; (b) a dispersant comprising denatured pea protein; and (c) hydrocolloids containing gum arabic; in, The active material comprises a low logP fragrance having a logP value ranging from 0.5 to 2.2, the amount of the low logP fragrance is 3 to 18% by weight based on the weight of the active material, and the core-shell microcapsule slurry is white.

2. The core-shell microcapsule slurry according to claim 1, wherein The low logP fragrance is selected from the group consisting of ethyl vanillin, coumarin, 4-(4-hydroxyphenyl)butan-2-one, p-anisaldehyde, 2-ethyl-3-hydroxy-4H-pyran-4-one, benzaldehyde, cinnamaldehyde, and combinations thereof.

3. The core-shell microcapsule slurry according to claim 1 or 2, wherein The low logP fragrance is selected from the group consisting of coumarin, p-anisaldehyde, benzaldehyde, cinnamaldehyde, and combinations thereof.

4. The core-shell microcapsule slurry according to any one of the preceding claims, wherein The polyisocyanate is a trimethylolpropane adduct of xylylene diisocyanate.

5. The core-shell microcapsule slurry of any one of the preceding claims, further comprising a rheology modifier, a preservative, an emulsifier, or a combination thereof.

6. The core-shell microcapsule slurry according to claim 5, wherein The rheology modifier includes xanthan gum.

7. The core-shell microcapsule slurry according to any one of the preceding claims, wherein The self-condensing polyisocyanate is present in an amount of 0.1% to 8% by weight of the core-shell microcapsule slurry.

8. The core-shell microcapsule slurry according to any one of the preceding claims, wherein The active material is a fragrance, a pro-fragrance, a malodor counteractant, or a combination thereof.

9. The core-shell microcapsule slurry according to claim 8, wherein The active material is a fragrance and the slurry has: (a) less than 0.3% or less than 0.25% non-encapsulated fragrance based on the total weight of the fragrance in the slurry, (b) as in 21 s -1 A viscosity of less than 600 cps or less than 580 cps at 22°C measured at a shear rate of 100 Å / min, or (c) a combination of (a) and (b).

10. A consumer product comprising the core-shell microcapsule slurry according to any one of claims 1 to 9, preferably the consumer product is a fabric conditioner, a fabric softener, a fabric refresher, a liquid laundry detergent, or a powder detergent.

11. A method for producing the core-shell microcapsule slurry according to claim 1, comprising: (a) Prepare the aqueous phase by (i) denaturing pea protein, (ii) adjusting the pH of the aqueous phase to below 6, and (iii) adding gum arabic as a hydrocolloid to the aqueous phase; (b) preparing an oil phase comprising an active material and a polyisocyanate; (c) emulsifying the oil phase with the aqueous phase to form a slurry containing core-shell microcapsules; and (d) curing the shell of the microcapsule at a temperature below 80°C.

12. The method of claim 11, wherein the polyisocyanate is a trimethylolpropane adduct of xylylene diisocyanate.

13. The method according to claim 11 or 12, wherein: The pH in (a)(ii) is adjusted to between 4.5 and 3.

5.

14. The method according to any one of claims 11 to 13, wherein The shells of the microcapsules in (d) are cured at a temperature of 63°C to 67°C.

15. The method according to any one of claims 11 to 14, wherein The active material is a fragrance, a pro-fragrance, a malodor counteractant, or a combination thereof.

16. The method of claim 15, wherein: The active material is a fragrance and the slurry has: (a) less than 0.3% or less than 0.25% non-encapsulated fragrance based on the total weight of the fragrance, (b) as in 21 s -1 A viscosity of less than 600 cps or less than 580 cps at 22°C measured at a shear rate of 100 Å / min, or (c) a combination of (a) and (b).

17. The method of any one of claims 11 to 16, further comprising adding a rheology modifier, a preservative, an emulsifier, or a combination thereof.

18. The method of claim 17, wherein: The rheology modifier is added prior to step (c), preferably the rheology modifier is xanthan gum.

19. The method according to any one of claims 11 to 18, wherein The amount of the polyisocyanate is 0.1% to 8% by weight of the core-shell microcapsule slurry.

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