# US 2017/0281986 A1 · Controlled release microcapsules > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2017/0281986 A1 - Document ID: US20170281986A1 - Status: Published application - Kind: A1 - Application number: 15/629,286 - Filed: 2017-06-21 - Published: 2017-10-05 - Earliest claimed: 2014-10-16 - Assignees: Encapsys, LLC - Applicants: Encapsys, LLC - Inventors: Linsheng Feng; Todd Arlin Schwantes; Robert Stanley Bobnock; Nianxi Yan - Web page: https://patentgrep.com/patent/US20170281986A1 ## CPC - C11B 9/00: Essential oils; Perfumes - A61K 8/11: Encapsulated compositions - A61K 8/8152: {Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers} - A61Q 5/02: Preparations for cleaning the hair - A61Q 15/00: Anti-perspirants or body deodorants (deodorisation of air A61L9/00) - A61Q 19/10: Washing or bathing preparations - B01F 23/00: Mixing according to the phases to be mixed, e.g. dispersing or emulsifying - B01J 13/16: Interfacial polymerisation - C11D 3/505: {encapsulated or adsorbed on a carrier, e.g. zeolite or clay} - A61K 2800/412: Microsized, i.e. having sizes between 0.1 and 100 microns - A61K 2800/594: Mixtures of polymers - A61K 2800/63: More than one coating - A61Q 13/00: Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) - C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F) - 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 - B01F: MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING (mixing paints B44D3/06) - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL ## Abstract A method of forming microcapsules having improved physical properties and release control as well as the microcapsules formed by the process wherein the capsule wall is formed by the concurrent polymerization of monomers, oligomer and/or prepolymers on the inside of the capsule wall and different monomers, oligomers and/or prepolymers on the exterior of the capsule wall as it forms. ## Claims ### Claim 1 A method of making microcapsules whose shell wall comprises on one surface a first (meth)acrylate polymer and on its other surface a second (meth)acrylate polymer, said first (meth)acrylate polymer derived from an aqueous phase (meth)acrylate polymer wall forming composition and said second (meth)acrylic polymer derived from an oil phase first (meth)acrylate polymer wall forming composition, and an intermediate region comprising an interpenetrating network and/or copolymer of the two wall forming compositions, said method comprising: (i) forming an oil-in-water or a water-in-oil emulsion of the two (meth)acrylate polymer wall forming compositions, (ii) subjecting the emulsion to conditions for concurrently, at last in part, polymerizing the wall forming materials of each of the oil phase and water phase, and (iii) allowing the reaction to continue until the microcapsules of desired wall thickness are attained wherein said first (meth)acrylate polymer is derived from one or more polyethylene glycol di(meth)acrylates, ethoxylated mono- or multi-functional (meth)acrylates, and/or (meth)acrylate monomers and/or oligomers. ### Claim 2 (depends on 1) The method of claim 1 wherein oil phase (meth)acrylate polymer wall forming composition comprises either (A) a combination of (a) at least one oil soluble or dispersible amine (meth)acrylate, (b) at least one oil soluble or dispersible acidic (meth)acrylate or at least one oil soluble or dispersible simple acid or both, and (c) at least one oil soluble or dispersible multifunctional (meth)acrylate monomer or oligomer, (B) a combination of (a) at least one oil soluble or dispersible acidic (meth)acrylate, (b) at least one oil soluble or dispersible simple base, and (c) at least one oil soluble or dispersible multifunctional (meth)acrylate monomer or oligomer, or (C) one or more oil soluble or dispersible mono-, di- or multi-functional (meth)acrylate monomers or oligomers. ### Claim 3 (depends on 2) The method of claim 2 wherein the method further comprises the step of oligomerizing and/or prepolymerizing some or all of the (meth)acrylate polymer wall forming components of the oil phase composition, the aqueous phase composition or both prior to forming the emulsion. ### Claim 4 (depends on 2) The method of claim 2 wherein the method further comprises the step of oligomerizing and/or prepolymerizing some or all of the (meth)acrylate polymer wall forming components of the oil phase composition, the aqueous phase composition or both subsequent to forming the emulsion but prior to initiating wall formation. ### Claim 5 (depends on 2) The method of claim 2 wherein the process uses oligomers and/or prepolymers of the oil phase composition, the aqueous phase composition or both. ### Claim 6 (depends on 2) The method of claim 2 wherein the oil phase wall forming composition comprises (A) (a) at least one oil soluble or dispersible amine (meth)acrylate, (b) at least one oil soluble or dispersible acidic (meth)acrylate, and (c) at least one oil soluble or dispersible multifunctional (meth)acrylate monomer or oligomer. ### Claim 7 (depends on 2) The method of claim 2 wherein the oil phase wall forming composition comprises (A) (a) at least one oil soluble or dispersible amine (meth)acrylate, (b) at least one oil soluble or dispersible simple acid, and (c) at least one oil soluble or dispersible multifunctional (meth)acrylate monomer or oligomer. ### Claim 8 (depends on 2) The method of claim 2 wherein the oil phase wall forming composition comprises (A) (a) at least one oil soluble or dispersible amine (meth)acrylate, (b) the combination of at least one oil soluble or dispersible acidic (meth)acrylate and at least one oil soluble or dispersible simple acid, and (c) at least one oil soluble or dispersible multifunctional (meth)acrylate monomer or oligomer. ### Claim 9 (depends on 2) The method of claim 2 wherein the oil phase wall forming composition comprises (B) (a) at least one oil soluble or dispersible acidic (meth)acrylate, (b) at least one oil soluble or dispersible simple base, and (c) at least one oil soluble or dispersible multifunctional (meth)acrylate monomer or oligomer. ### Claim 10 (depends on 2) The method of claim 2 wherein the oil phase wall forming composition comprises (C) one or more oil soluble or dispersible mono-, di- or multi-functional (meth)acrylate monomers or oligomers. ### Claim 11 (depends on 1) The method of claim 1 wherein the water phase further comprises a polymeric emulsifier. ### Claim 12 (depends on 1) The method of claim 1 wherein the wall formation is a two-step reaction process where the first reaction step comprises subjecting the emulsion to such conditions as will form oligomers and/or prepolymers of the wall forming materials and the second reaction step comprises subjecting the emulsion to a second set of conditions which effectuates the formation of the shell wall. ### Claim 13 (depends on 1) The method of claim 1 wherein the wall formation is a three-step reaction process where the first step comprising subjecting the emulsion to such conditions as will form oligomers and/or prepolymers of the wall forming materials, the second step comprises subjecting the emulsion to a second set of conditions which effectuates building of the shell wall and the third step comprises subjecting the emulsion to a third set of conditions, which may be merely an extension or continuation of the second set of conditions, to cross-link the polymer(s) of the shell wall. ### Claim 14 (depends on 13) The method of claim 13 wherein the third step effects the cross-linking of the oil phase derived (meth)acrylate polymer. ### Claim 15 (depends on 1) The method of claim 1 wherein initiation of wall formation from the oil phase and the aqueous phase is concurrent. ### Claim 16 (depends on 1) The method of claim 1 wherein initiation of the wall formation from one of the oil phase and the aqueous phase is staggered relative to the other. ### Claim 17 (depends on 16) The method of claim 16 wherein wall formation of the second wall forming composition is initiated after the shell wall is partially formed from the first wall forming material but before the shell wall is impermeable to the wall forming material of the second wall forming composition. ### Claim 18 (depends on 16) The method of claim 16 wherein wall formation of the second wall forming composition is initiated after a seed capsule is formed of the first wall forming material. ### Claim 19 A method of making microcapsules whose shell wall comprises on one surface a first (meth)acrylate polymer and on its other surface a second (meth)acrylate polymer, said first (meth)acrylate polymer derived from an aqueous phase (meth)acrylate polymer wall forming composition and said second (meth)acrylic polymer derived from an oil phase first (meth)acrylate polymer wall forming composition, and an intermediate region comprising an interpenetrating network and/or copolymer of the two wall forming compositions, said method comprising: (i) forming a first oil phase composition comprising the wall forming monomers, oligomers and/or prepolymers, (ii) forming a second oil phase composition comprising either (a) a first initiator for effecting oligomerization and/or polymerization of the (meth)acrylate monomers/oligomers of the first oil phase composition, (b) the ingredient(s) to be encapsulated or (c) both (a) and (b), provided that at least one of the first oil phase composition and the second oil phase composition includes the first initiator for effecting oligomerization and/or polymerization of the (meth)acrylate monomers/oligomers of the first oil phase composition and at least one of the first oil phase composition and the second oil phase composition includes at least one of the ingredients to be encapsulated, (iii) combining and mixing the two oil phase compositions, (iv) subjecting the combined oil phase composition to such conditions and for such period of time as is effective for causing the oligomerization/prepolymerization of the (meth)acrylate monomers/oligomers; (v) combining the product of step (iii) with an excess of a first aqueous composition comprising an emulsifier suitable for emulsifying the oil phase composition in water, water, and, optionally, either (a) a second initiator, (b) an alkali or alkali salt, or (c) both, and intimately mixing/milling the same to form droplets of the combined oil phase composition dispersed in the first aqueous composition; (vi) applying or subjecting the so formed dispersion to heat or such other conditions as will effect polymerization of the oligomer/prepolymer product of step (iii) at the interface of the oil phase and water phase materials, with or without applying or inducing conditions to cause the reaction product of step (iii) to migrate to said interface, to initiate capsule wall formation at the interface; (vii) adding to and mixing with said reaction mix a second aqueous composition comprising water soluble or dispersible (meth)acrylate monomers and/or oligomers, water and, optionally, (a) an emulsifier, (b) a chain transfer agent, (c) a third initiator or (d) a combination of (a) and (b), (a) and (c), (b) and (c) or (a), (b) and (c); (viii) subjecting the so formed reaction mix to conditions sufficient to effect deposition and polymerization of the water soluble or dispersible (meth)acrylate at the interface of the droplet and the aqueous continuous phase concurrent with the continued building of the capsule wall through the polymerization of the oligomer/prepolymer of step (iii), and (ix) continuing said polymerization process for a sufficient period of time and under such conditions as are necessary to attain the desired microcapsule size and/or capsule wall thickness; wherein said first (meth)acrylate polymer is derived from one or more polyethylene glycol di(meth)acrylates, ethoxylated mono- or multi-functional (meth)acrylates, and/or (meth)acrylate monomers and/or oligomers and wherein said first initiator comprises at least one oil soluble or dispersible initiator capable of effecting oligomerization/prepolymerization of the (meth)acrylate monomers/oligomers of the first oil phase composition, said second initiator comprises at least one water soluble or dispersible initiator, which may be the same as or include, in whole or in part, the first initiator, alone or together with another initiator capable of effecting oligomerization or polymerization of the aqueous phase wall forming materials, and said third initiator comprises at least one water soluble or dispersible initiator capable of effecting polymerization of the water soluble or water dispersible acrylate monomers and/or oligomers of the aqueous phase. ### Claim 20 (depends on 19) The method of claim 19 wherein steps (iv) and (v) are reversed such that the oligomerization/prepolymerization of the oil phase materials occurs following the combining of the oil phase composition and the first water phase composition. ### Claim 21 (depends on 19) The method of claim 19 wherein steps (vi) and (vii) are reversed whereby the second water phase composition is added before conditions are imposed for formation of the shell wall. ### Claim 22 (depends on 19) The method of claim 19 wherein shell wall formation is initiated concurrently, or nearly so, from the oil phase and the aqueous phase. ### Claim 23 (depends on 19) The method of claim 19 wherein step (vii) is effected once at least a partial seed capsule is formed from the oil phase wall forming materials but prior to the seed capsule attaining a state where the oil phase and the aqueous phase are completely isolated from one another. ### Claim 24 (depends on 19) The method of claim 19 wherein step (vii) is effected once the capsule wall formed from the oil phase has attained a state where the oil phase and the aqueous phase are completely isolated from one another by the capsule wall material. ### Claim 25 (depends on 19) The method of claim 19 wherein the oil phase (meth)acrylate polymer wall forming composition comprises either (A) a combination of (a) at least one oil soluble or dispersible amine (meth)acrylate, (b) at least one oil soluble or dispersible acidic (meth)acrylate or at least one oil soluble or dispersible simple acid or both, and (c) at least one oil soluble or dispersible multifunctional (meth)acrylate monomer or oligomer, or (B) a combination of (a) at least one oil soluble or dispersible acidic (meth)acrylate, (b) at least one oil soluble or dispersible simple base, and (c) at least one oil soluble or dispersible multifunctional (meth)acrylate monomer or oligomer.