IP Library Granted Patent US 10,863,739
Granted Patent B2
US 10,863,739 · App. 15/146,395 · Granted Dec 15, 2020

Stable emulsion formulations of encapsulated volatile compounds

Inventor: Tirthankar Ghosh (Oreland, PA)
Assignee: AGROFRESH INC.
A01N25/04A01N27/00
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Quick Facts
Patent No.
US 10,863,739
App. No.
15/146,395
Granted
Dec 15, 2020
Kind
B2
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 (34)

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).

2. The aqueous-in-oil-in-aqueous double emulsion composition of claim 1 , wherein the aqueous phase comprises an aqueous phase containing salt (APCS).

3. The aqueous-in-oil-in-aqueous double emulsion composition of claim 2 , wherein the salt comprises magnesium sulfate or ammonium sulfate.

4. The aqueous-in-oil-in-aqueous double emulsion composition of claim 2 , wherein the APCS comprises the molecular complex of the encapsulated volatile compound.

5. The aqueous-in-oil-in-aqueous double emulsion composition of claim 2 , wherein the aqueous-in-oil emulsion composition comprises a lipophilic emulsifier.

6. The aqueous-in-oil-in-aqueous double emulsion composition of claim 5 , wherein the lipophilic emulsifier is polyglycerol polyricinoleate (PGPR).

7. The aqueous-in-oil-in-aqueous double emulsion composition of claim 2 , wherein the aqueous-in-oil emulsion composition comprises an oil soluble thickener.

8. 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.

9. 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.

10. The aqueous-in-oil-in-aqueous double emulsion composition of claim 1 , wherein the surfactant has a hydrophilic/lipophilic balance (HLB) between 11-15.

11. 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.

12. 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.

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.

14. 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).

15. The method for preparing an aqueous-in-oil-in-aqueous double emulsion composition of claim 13 , wherein the lipophilic emulsifier is polyglycerol polyricinoleate (PGPR).

16. 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.

17. 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.

18. 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.

19. 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.

20. 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.

Assignments (4)
AGREEMENT OF AGENT RESIGNATION, APPOINTMENT AND ACCEPTANCE & MASTER ASSIGNMENT OF SECURITY DOCUMENTS Recorded Jun 24, 2024
From: JPMORGAN CHASE BANK, N.A.
To: ALTER DOMUS US LLC
Reel/Frame 067914/0941 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT REEL 053316, FRAME 0561 Recorded Apr 3, 2023
From: BANK OF MONTREAL
To: AGROFRESH, INC.
Reel/Frame 063238/0901 →
SECURITY INTEREST Recorded Mar 31, 2023
From: AGROFRESH INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063214/0683 →
PATENT SECURITY AGREEMENT Recorded Jul 27, 2020
From: AGROFRESH, INC.
To: BANK OF MONTREAL, AS COLLATERAL AGENT
Reel/Frame 053316/0561 →
Continuity (2)
Provisional Application 62157588 · May 6, 2015
Related Publication 20160324147A1 · Nov 10, 2016