# US 2025/0144589 A1 · Method for Producing Microcapsules > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2025/0144589 A1 - Document ID: US20250144589A1 - Status: Published application - Kind: A1 - Application number: 18/835,342 - Filed: 2023-02-02 - Published: 2025-05-08 - Earliest claimed: 2022-02-02 - Assignees: Symrise AG - Applicants: Symrise AG - Inventors: Ralf BERTRAM; Benjamin ROST; Andreas VOGEL; Britta BLANCHFIELD; Christina KOEPKE; Lisette HOFFARTH; Daniela GREGOR - Web page: https://patentgrep.com/patent/US20250144589A1 ## CPC - B01J 13/14: Polymerisation; cross-linking - A23P 10/30: Encapsulation of particles, e.g. foodstuff additives - A23P 10/35: with oils, lipids, monoglycerides or diglycerides - A61K 8/11: Encapsulated compositions - A61K 8/645: {Proteins of vegetable origin; Derivatives or degradation products thereof} - A61Q 13/00: Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) - A61Q 19/00: Preparations for care of the skin - B01J 13/206: {Hardening; drying} - C11D 3/382: Vegetable products, e.g. soya meal, wood flour, sawdust - C11D 17/0039: {Coated compositions or coated components in the compositions, (micro)capsules} - A61K 9/5052: {Proteins, e.g. albumin} - A61K 9/5089: {Processes} - A61K 2800/10: General cosmetic use - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - A23P: SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS - C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL ## Abstract The present invention relates to a process for the preparation of microcapsules, in particular plant protein-based microcapsules and dispersions of such microcapsules (microcapsule slurry), which include at least one hydrophobic active ingredient, preferably perfume- or aroma-containing plant protein-based microcapsules, which have a balance of stability and performance compared to microcapsules of the prior art. Furthermore, the present invention relates to plant protein-based microcapsules obtainable by the method according to the invention. In a further aspect, the present invention relates to the use of the plant protein-based microcapsules and dispersions according to the invention as a component of household products, textile care products, detergents, fabric softeners, cleaning agents, scent boosters or fragrance enhancers in liquid or solid form, cosmetics, personal care products, perfume compositions, agricultural products, pharmaceutical products or print coating for paper. Ultimately, the present invention relates to consumer products comprising such microcapsules or microcapsule dispersions according to the invention. ## Claims ### Claim 1 A process for preparing a plant protein-based microcapsule comprising the following steps in this order: (i) providing an internal non-aqueous phase comprising at least one aliphatic polyisocyanate as a crosslinking agent and at least one hydrophobic active ingredient and optionally at least one further crosslinking agent; (ii) providing an external aqueous phase comprising at least one plant protein and optionally at least one first polysaccharide and/or at least one further crosslinking agent and/or at least one polyhydroxyphenol and/or at least one protective colloid, and further optionally adjusting the pH of the aqueous phase to a pH below the isoelectric point of the plant protein; (iii) emulsifying or dispersing the internal non-aqueous phase in the external aqueous phase, optionally in the presence of at least one stabilizer and/or at least one emulsifier, to obtain an oil-in-water emulsion or dispersion; (iv) optionally adding at least one further polysaccharide and/or at least one further plant protein; (v) carrying out a first cross-linking to obtain a microcapsule slurry; (vi) curing the microcapsule slurry at a temperature of at least 60° C. and optionally adding a further polysaccharide and/or a further plant protein; (vii) cooling and optionally carrying out a further crosslinking by addition of at least one further crosslinking agent; and (viii) optionally, separating the microcapsules from the microcapsule slurry and, if necessary, drying the microcapsules or adjusting the viscosity of the microcapsule slurry by adding at least one thickening agent. ### Claim 2 (depends on 1) The process according to claim 1, wherein at least one of the aliphatic polyisocyanates or the one aliphatic polyisocyanate is a cycloaliphatic polyisocyanate having two or more isocyanate groups. ### Claim 3 (depends on 1) The process according to claim 1, wherein the total amount of polyisocyanate, based on the amount of wall former, is 10 to 70% by weight, or wherein the total amount of polyisocyanates used as crosslinking agents together is 0.5% to 4%, based on the total amount of hydrophobic active ingredient used. ### Claim 4 (depends on 1) The process according to claim 1, wherein the polysaccharide or the at least one further polysaccharide is hyaluronic acid or wherein the polyhydroxyphenol is a tannin. ### Claim 5 (depends on 4) The process according to claim 4, wherein the amount of hyaluronic acid relative to the amount of wall former is 1 to 15 percent by weight. ### Claim 6 (depends on 1) The process according to claim 1, wherein in step (i) an internal non-aqueous phase is provided comprising (a) an aliphatic polyisocyanate as a crosslinking agent and a cycloaliphatic polyisocyanate as crosslinking agent, or (b) two different aliphatic polyisocyanates as crosslinking agents wherein the aliphatic polyisocyanate and the cycloaliphatic polyisocyanate, or the two different aliphatic polyisocyanates, are used in a respective molar ratio of 85:15 to 15:85. ### Claim 7 (canceled) ### Claim 8 (depends on 1) The process according to claim 1, wherein in step (i) an internal non-aqueous phase is provided comprising three crosslinking agents, wherein the three crosslinking agents are aliphatic or cycloaliphatic polyisocyanates different from each other, wherein at least one cycloaliphatic polyisocyanate and at least one aliphatic polyisocyanate are present, and wherein the three polyisocyanates each are used in amounts of 20% to 60% based on the total weight of the three polyisocyanates. ### Claim 9 (depends on 1) The process according to claim 1, wherein in step (i) at least one further crosslinking agent and/or in step (ii) and/or in step (vii) a further crosslinking agent is added, wherein the at least one further crosslinking agent and/or the further crosslinking agent is selected from the group consisting of transglutaminase, peroxidase, secondary plant substances selected from the group consisting of polyphenols and polyhydroxyphenols, and mixtures of two or more of the aforementioned crosslinking agents. ### Claim 10 (depends on 1) The process according to claim 1, wherein the at least one hydrophobic active ingredient is selected from the group consisting of fragrances or odorants, flavorings, cooling agents, TRPV1 and TRPV3 modulators, substances that produce a sharp taste or a warmth or heat sensation on the skin or mucous membranes or a fizzing or tingling sensation in the mouth or throat or active ingredients with pungent or acrid or astringent effects, pesticides, biocides, insecticides, a substance from the group of repellents, food additives, cosmetic active substances, pharmaceutical active substances, agrochemicals, dyes, colorants, dye precursors; luminous paint, optical brighteners, solvents, waxes, silicone oils, lubricants, printing coatings for paper and mixtures of two or more of the aforementioned active ingredients. ### Claim 11 (depends on 1) The process according to claim 1, wherein the at least one first polysaccharide and/or the at least one further polysaccharide is selected from the group consisting of indigestible fibers and dietary fibers; starches and starch derivatives sugar alcohols; gellan; glucose, glycosaminoglycans; and mixtures of the aforementioned polysaccharides. ### Claim 12 (depends on 1) The process according to claim 1, wherein the at least one plant protein or the at least one further plant protein is selected from the group consisting of protein isolates, plant proteins in the form of fractions, and partial or complete hydrolysates or intermediates produced by physico-chemical processes or fermentative or enzymatic treatment of the proteins. ### Claim 13 (depends on 1) The process according to claim 1, wherein the at least one protective colloid is selected from the group consisting of diols polyols, polyvinylpyrrolidone, maleic acid vinyl copolymers, sodium lignosulfonates, maleic acid anhydride/styrene copolymers, ethylene/maleic acid anhydride copolymers, copolymers of ethylene oxide, propylene oxide and acid esters of polyethoxylated sorbitol, sodium dodecyl sulfate, vegetable polymers, and mixtures of the aforementioned compounds; and/or wherein the protective colloid is used in combination with starch. ### Claim 14 (depends on 1) The process according to claim 1, wherein in step (v) the first crosslinking is carried out to obtain a microcapsule slurry by adding at least one catalyst; wherein the at least one catalyst is selected from the group consisting of diazobicyclo[2.2.2]octane (DABCO), bismuth catalyst, tin catalyst, and mixtures of two or more of the aforementioned catalysts. ### Claim 15 (depends on 1) The process according to claim 1, wherein the total amount of crosslinking agent added as polyisocyanates in step (i) is 0.5% to 4% based on the total amount of hydrophobic active ingredient used in step (i). ### Claim 16 (canceled) ### Claim 17 A plant protein-based microcapsule comprising (a) a core comprising at least one hydrophobic active ingredient; (b) a capsule shell comprising a crosslinking matrix or crosslinking units of at least one plant protein and at least one aliphatic polyisocyanate as a crosslinking agent and optionally at least one polysaccharide, and optionally at least one protective colloid, and/or optionally at least one further crosslinking agent. ### Claim 18 (depends on 17) The microcapsule according to claim 17, wherein the capsule shell comprises: a crosslinking matrix or crosslinking units of a polymerization and/or crosslinking of at least one plant protein with a mixture of at least two different crosslinking agents, and a crosslinking matrix or crosslinking units of a polymerization and/or crosslinking of at least one polysaccharide, with a mixture of the at least two different crosslinking agents. ### Claim 19 (depends on 17) The microcapsule according to claim 17, wherein the at least two crosslinking agents are each different aliphatic or cycloaliphatic polyisocyanates having two or more isocyanate groups. ### Claim 20 (depends on 17) The microcapsule according to claim 17, wherein the total amount of the polyisocyanates used as crosslinking agents together is 0.5% to 4% based on the total amount of hydrophobic active ingredient used. ### Claim 21 (depends on 17) The microcapsule according to claim 17, wherein the microcapsule comprises hyaluronic acid. ### Claim 22 (canceled) ### Claim 23 (depends on 17) Household products, fabric care products, laundry detergents, fabric softeners, cleaning agents, scent boosters and fragrance enhancers, cosmetics, personal care products, perfume compositions, agricultural products or pharmaceutical products, comprising a microcapsule according to claim 17.