# US 10,863,739 B2 · Stable emulsion formulations of encapsulated volatile compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,863,739 B2 - Document ID: US10863739B2 - Status: Granted - Kind: B2 - Application number: 15/146,395 - Filed: 2016-05-04 - Published: 2016-11-10 - Granted: 2020-12-15 - Earliest claimed: 2015-05-06 - Assignees: Agrofresh Inc. - Applicants: AgroFresh Inc. - Inventors: Tirthankar Ghosh - Web page: https://patentgrep.com/patent/US10863739B2 ## CPC - A01N 25/04: Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16) - A01N 27/00: Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons - 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 ## Abstract The present invention is based on the discovery of a stable water-in-oil-in-water double emulsion. The double emulsion composition disclosed may contain molecular complex of volatile compounds for example 1-methylcyclopropene (1-MCP). In addition, the double emulsion composition disclosed can provide prolong or controlled release of the volatile compounds. ## Claims ### Claim 1 An aqueous-in-oil-in-aqueous double emulsion composition comprising: (a) an aqueous-in-oil emulsion composition comprising an aqueous phase and an oil phase; (b) a hydrophilic emulsifier, wherein the hydrophilic emulsifier is hydroxyethyl cellulose; (c) a surfactant, wherein the surfactant is an aqueous salt solution of a styrene-maleic anhydride copolymer and wherein the surfactant has a hydrophilic/lipophilic balance (HLB) of between 10-15; and (d) a second aqueous phase, wherein the aqueous-in-oil emulsion composition comprises i) a molecular complex of an encapsulated volatile compound, ii) a salt, and iii) water, wherein the molecular complex of the encapsulated volatile compound comprises a cyclopropene molecular encapsulating agent complex, and wherein the cyclopropene is 1-methylcyclopropene (1-MCP). ### Claim 2 (depends on 1) The aqueous-in-oil-in-aqueous double emulsion composition of claim 1, wherein the aqueous phase comprises an aqueous phase containing salt (APCS). ### Claim 3 (depends on 2) The aqueous-in-oil-in-aqueous double emulsion composition of claim 2, wherein the salt comprises magnesium sulfate or ammonium sulfate. ### Claim 4 (depends on 2) The aqueous-in-oil-in-aqueous double emulsion composition of claim 2, wherein the APCS comprises the molecular complex of the encapsulated volatile compound. ### Claim 5 (depends on 2) The aqueous-in-oil-in-aqueous double emulsion composition of claim 2, wherein the aqueous-in-oil emulsion composition comprises a lipophilic emulsifier. ### Claim 6 (depends on 5) The aqueous-in-oil-in-aqueous double emulsion composition of claim 5, wherein the lipophilic emulsifier is polyglycerol polyricinoleate (PGPR). ### Claim 7 (depends on 2) The aqueous-in-oil-in-aqueous double emulsion composition of claim 2, wherein the aqueous-in-oil emulsion composition comprises an oil soluble thickener. ### Claim 8 (depends on 1) The aqueous-in-oil-in-aqueous double emulsion composition of claim 1, wherein the hydroxyethyl cellulose is present at a concentration of 0.3% by weight of the second aqueous phase. ### Claim 9 (depends on 1) The aqueous-in-oil-in-aqueous double emulsion composition of claim 1, wherein the styrene-maleic anhydride copolymer is a partial ester of the styrene-maleic anhydride copolymer. ### Claim 10 (depends on 1) The aqueous-in-oil-in-aqueous double emulsion composition of claim 1, wherein the surfactant has a hydrophilic/lipophilic balance (HLB) between 11-15. ### Claim 11 (depends on 1) The aqueous-in-oil-in-aqueous double emulsion composition of claim 1, wherein the surfactant has a hydrophilic/lipophilic balance (HLB) selected from the group consisting of 12, 12.3, 13, 13.8, 14, 14.4, and 15. ### Claim 12 (depends on 1) The aqueous-in-oil-in-aqueous double emulsion composition of claim 1, wherein the surfactant has a hydrophilic/lipophilic balance (HLB) selected from the group consisting of 12.3, 13.8, and 14.4. ### Claim 13 A method for preparing an aqueous-in-oil-in-aqueous double emulsion composition, comprising: (a) preparing an aqueous-in-oil emulsion composition using an aqueous phase, an oil phase, a lipophilic emulsifier, and an oil soluble thickener; (b) combining an active ingredient into the aqueous-in-oil emulsion composition; and (c) dispersing the aqueous-in-oil emulsion composition into a second aqueous phase, (d) adding a hydrophilic emulsifier to the second aqueous phase, wherein the hydrophilic emulsifier is hydroxyethyl cellulose; (e) adding a surfactant to the second aqueous phase, wherein the surfactant is an aqueous salt solution of a styrene-maleic anhydride copolymer and wherein the surfactant has a hydrophilic/lipophilic balance (HLB) of between 10-15; wherein the aqueous-in-oil emulsion composition comprises i) a molecular complex of an encapsulated volatile compound, ii) a salt, and iii) water, wherein the molecular complex of the encapsulated volatile compound comprises a cyclopropene molecular encapsulating agent complex, and wherein the cyclopropene is 1-methylcyclopropene (1-MCP); and wherein the aqueous phase of the aqueous-in-oil composition is in direct contact with the oil phase of the aqueous-in-oil emulsion. ### Claim 14 (depends on 13) The method for preparing an aqueous-in-oil-in-aqueous double emulsion composition of claim 13, wherein the aqueous phase comprises an aqueous phase containing salt (APCS). ### Claim 15 (depends on 13) The method for preparing an aqueous-in-oil-in-aqueous double emulsion composition of claim 13, wherein the lipophilic emulsifier is polyglycerol polyricinoleate (PGPR). ### Claim 16 (depends on 13) The method for preparing an aqueous-in-oil-in-aqueous double emulsion composition of claim 13, wherein the hydroxyethyl cellulose is present at a concentration of 0.3% by weight of the second aqueous phase. ### Claim 17 (depends on 13) The method for preparing an aqueous-in-oil-in-aqueous double emulsion composition of claim 13, wherein the styrene-maleic anhydride copolymer is a partial ester of the styrene-maleic anhydride copolymer. ### Claim 18 (depends on 13) The method for preparing an aqueous-in-oil-in-aqueous double emulsion composition of claim 13, wherein the surfactant has a hydrophilic/lipophilic balance (HLB) of between 11-15. ### Claim 19 (depends on 13) The method for preparing an aqueous-in-oil-in-aqueous double emulsion composition of claim 13, wherein the surfactant has a hydrophilic/lipophilic balance (HLB) selected from the group consisting of 12, 12.3, 13, 13.8, 14, 14.4, and 15. ### Claim 20 (depends on 13) The method for preparing an aqueous-in-oil-in-aqueous double emulsion composition of claim 13, wherein the surfactant has a hydrophilic/lipophilic balance (HLB) selected from the group consisting of 12.3, 13.8, and 14.4.