# US 11,077,417 B2 · Microcapsule comprising a polyester-urethane shell and a hydrophobic core material > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,077,417 B2 - Document ID: US11077417B2 - Status: Granted - Kind: B2 - Application number: 15/778,305 - Filed: 2016-11-08 - Published: 2018-12-06 - Granted: 2021-08-03 - Earliest claimed: 2015-11-23 - Assignees: BASF SE - Applicants: BASF SE - Inventors: Yannick Fuchs; Helmut Witteler; Matthias Bratz - Web page: https://patentgrep.com/patent/US11077417B2 ## CPC - B01J 13/16: Interfacial polymerisation - A01N 25/28: Microcapsules {or nanocapsules} - A61K 8/11: Encapsulated compositions - A61K 8/87: Polyurethanes - A61K 9/5031: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)} - A61K 9/5089: {Processes} - A61Q 19/00: Preparations for care of the skin - B01J 13/14: Polymerisation; cross-linking - A61K 2800/10: General cosmetic use - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - 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 ## Abstract Disclosed herein are microcapsules as core-shell-particles, including a polymeric shell, a method of making them, a dispersion of those microcapsules in a liquid medium and use thereof. The microcapsules include a core that contains a hydrophobic component. ## Claims ### Claim 1 A microcapsule comprising a capsule core and a polymeric shell, wherein the core comprises only hydrophobic components and the shell comprises in polymerized form: A) at least one poly(ester-urethane) comprising at least 2 isocyanate groups, obtainable by reacting at least one polyester-polyol comprising at least 2 OH groups with at least one polyisocyanate comprising at least 2 NCO groups, and; B1) at least one polymeric polyamine selected from the group consisting of polyaminosaccharides, polyamidoamines, polyesteramines, polyaminoacids and combinations thereof, having an average molecular weight of between about 375 g/mol and about 2500 g/mol, and comprising at least 3 amino groups reactive towards NCO groups. ### Claim 2 (depends on 1) The microcapsule according to claim 1, wherein the poly(ester-urethane) is a reaction product of the polyester-polyol with the polyisocyanate which is selected from the group consisting of hexamethylene diisocyanate, tetramethylene diisocyanate, dicyclohexylmethane-4,4′-diisocyanate, isophoronediisocyanate, 2,4- and 2,6-toluylene diisocyanate and isomer mixtures thereof, 2,4′- and 4,4′-diphenylmethane diisocyanate and isomer mixtures, biurets, allophanates and/or isocyanurates or mixtures thereof. ### Claim 3 (depends on 1) The microcapsule according to claim 1, wherein the polyester-polyol is a polylactonepolyol which comprises 2 or 3 OH groups. ### Claim 4 (depends on 1) The microcapsule according to claim 1, wherein the polyester-polyol is a compound of the formulae (2), (5), or mixtures thereof wherein Ra is selected from linear or branched C1-C10-alkylene group and C3-C20-cycloaliphatic radicals having 3 to 10 ring carbon atoms, Rb is a linear or branched C1-C10-alkantriyl group, l, m and n are independently an integer of 1 to 100, with the proviso that in the formula (2) n+m is an integer of 2 to 100, in the formula (5) n+m+1 is an integer of 2 to 100. ### Claim 5 (depends on 1) The microcapsule according to claim 1, wherein the polyester-polyol has a weight-average molecular weight of from 200 to 3000 g/mol. ### Claim 6 (depends on 1) The microcapsule according to claim 1, wherein the shell comprises in polymerized form a component B1) which comprises at least one polyamidoamine. ### Claim 7 (depends on 6) The microcapsule according to claim 6, wherein the at least one polyamidoamine is polylysine and wherein the polylysine has an average molecular weight of 375 to 2500 g/mol. ### Claim 8 (depends on 1) The microcapsule according to claim 1, wherein a core-shell ratio (w/w) of the microcapsule is 20:1 to 1:1. ### Claim 9 (depends on 1) The microcapsule according to claim 1, wherein a mean particle size of the microcapsule d(0.5) is in the range from 0.5 μm to 50 μm. ### Claim 10 (depends on 1) The microcapsule according to claim 1, wherein the hydrophobic components comprise a pesticide. ### Claim 11 (depends on 1) The microcapsule according to claim 1, wherein the hydrophobic components comprise a pesticide and an oil body selected from the group consisting of vegetable oils, modified vegetable oils, synthetic (tri)glycerides, fatty acid alkyl esters, fatty acid alkyl esters based on C6-C22 fatty acids, mineral oils, hydrocarbons, saturated or unsaturated C6-C30-fatty acids, aromatic compounds, esters of linear C6-C22-fatty acids and mixtures thereof. ### Claim 12 (depends on 1) A microcapsule dispersion comprising at least one microcapsule according to claim 1. ### Claim 13 (depends on 1) A process for the preparation of the microcapsule according to claim 1, wherein the capsule core is obtainable by a) providing a premix (Ib) comprising the hydrophobic component(s) to be encapsulated (Cb), and at least one component (A) as defined in claim 1, and b) mixing the premix (Ib) provided in step a) with a hydrophilic medium comprising at least one hydrophilic protective colloid, at least one component (B1) as defined in claim 1, and reacting a resulting mixture to form microcapsules dispersed in the hydrophilic medium. ### Claim 14 (depends on 1) A method of controlling phytopathogenic fungi and/or undesired plant growth and/or undesired insect or mite attack and/or for regulating the growth of plants, wherein the microcapsule according to claim 1, where the hydrophobic components comprise a pesticide, is allowed to act on the respective pests, their environment or the crop plants to be protected from the respective pest, on the soil and/or on undesired plants and/or on the crop plants and/or on their environment. ### Claim 15 (depends on 8) The microcapsule according to claim 8, wherein the core-shell ratio (w/w) of the microcapsule is 10:1 to 2:1. ### Claim 16 (depends on 15) The microcapsule according to claim 15, wherein the core-shell ratio (w/w) of the microcapsule is 6:1 to 3:1. ### Claim 17 (depends on 9) The microcapsule according to claim 9, wherein the mean particle size of the microcapsule d(0.5) is in the range from 0.7 μm to 30 μm. ### Claim 18 (depends on 10) The microcapsule according to claim 10, wherein the hydrophobic components further comprise an oil body. ### Claim 19 (depends on 13) The process according to claim 13, wherein said providing a premix comprises providing the premix further comprising a hydrophobic medium that is liquid at 20° C. and 1023 mbar different from the (Cb). ### Claim 20 (depends on 1) The microcapsule according to claim 1, wherein the microcapsule further comprises B2) at least one compound different from B1) which comprises at least 2 terminal groups which are reactive towards isocyanate-groups and which are selected from OH, NHR, or SH, wherein R is selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl.