Systems and methods for solvent-free delivery of volatile compounds

Patent metadata

Field	Value
Publication number	US-9992995-B2
Application number	US-201414487569-A
Country	US
Kind code	B2
Filing date	Sep 16, 2014
Priority date	Sep 25, 2013
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

Provided are systems and methods for solvent-free delivery of volatile compounds, where an energy source is used to release the volatile compounds. The systems and methods provided herein have at least one advantage of (1) no solvent (for example water) is required; (2) immediate release of volatile compounds (for example 1-MCP can be released from HAIP within milliseconds or seconds instead of minutes or hours of the existing method using water); and/or (3) instantly starting and stopping the delivery of the volatile compound.

First claim

I claim:

1. A solvent-free system for delivery of a volatile compound, comprising
a molecular complex of the volatile compound and an inclusion complex;
a treatment compartment; and
a means of an energy source,
wherein the solvent-free system is configured to release the volatile compound from the molecular complex without water.

2. The system of claim 1 , further comprising an elastomer.

3. The system of claim 2 , wherein the elastomer comprises ethylene vinyl acetate.

4. The system of claim 1 , wherein the volatile compound comprises a cyclopropene.

5. The system of claim 4 , wherein the cyclopropene is of the formula:

wherein R is a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl, or naphthyl group; wherein the substituents are independently halogen, alkoxy, or substituted or unsubstituted phenoxy.

6. The system of claim 5 , wherein R is C 1 -C 8 alkyl.

7. The system of claim 5 , wherein R is methyl.

8. The system of claim 4 , wherein the cyclopropene is of the formula:

wherein R 1 is a substituted or unsubstituted C 1 -C 4 alkyl, C 1 -C 4 alkenyl, C 1 -C 4 alkynyl, C 1 -C 4 cycloalkyl, cycloalkylalkyl, phenyl, or naphthyl group; and R 2 , R 3 , and R 4 are hydrogen.

9. The system of claim 4 , wherein the cyclopropene is 1-methylcyclopropene (1-MCP).

10. The system of claim 1 , wherein the inclusion complex comprises an agent selected from the group consisting of substituted cyclodextrins, unsubstituted cyclodextrins, crown ethers, zeolites, and combinations thereof.

11. The system of claim 1 , wherein the inclusion complex comprises a cyclodextrin.

12. The system of claim 11 , wherein the cyclodextrin is selected from the group consisting of alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, and combinations thereof.

13. The system of claim 1 , wherein the treatment compartment is selected from the group consisting of a thermal desorption tube, a glass bottle, a Tedlar bag, an aluminum cup, and combinations thereof.

14. The system of claim 1 , wherein the energy source comprises at least one of electrical energy, magnetic energy, electromagnetic energy, ultrasonic energy, acoustic energy, and thermal energy.

15. The system of claim 1 , wherein the energy source comprises at least one energy characteristic of waveform, frequency, amplitude, or duration.

16. The system of claim 1 , wherein the means of the energy source comprises heating to a temperature between 100° C. and 300° C.

17. The system of claim 1 , wherein the means of the energy source comprises heating to a temperature between 150° C. and 250° C.

18. The system of claim 1 , wherein the means of the energy source is performed in an enclosed environment.

19. The system of claim 1 , wherein the means of the energy source is performed in an environment at a temperature between −30° C. and 10° C.

20. The system of claim 1 , wherein the means of the energy source is performed in a cold storage room or cold storage facility.

21. The system of claim 1 , wherein the inclusion complex comprises a molecular encapsulating agent and a cyclopropene.

22. The system of claim 10 , wherein the agent comprises a cavity.

23. The system of claim 22 , wherein the cavity comprises cyclopropene.

24. The system of claim 23 , wherein the cyclopropene is located within the cavity.

25. The system of claim 21 , wherein there are no covalent bonds between the cyclopropene and the molecular encapsulating agent.

26. The system of claim 21 , wherein there are no ionic bonds between the cyclopropene and the molecular encapsulating agent.

27. The system of claim 21 , wherein there is an electrostatic attraction between one or more polar moiety of the cyclopropene and one or more polar moiety of the molecular encapsulating agent.

28. The system of claim 21 , wherein there is no electrostatic attraction between one or more polar moiety of the cyclopropene and one or more polar moiety of the molecular encapsulating agent.

29. The system of claim 21 , wherein the interior of the cavity is substantially apolar, hydrophobic, or both.

30. The system of claim 21 , wherein the cyclopropene is substantially apolar, hydrophobic, or both.

31. The system of claim 30 , wherein the cyclopropene is apolar.

32. The system of claim 31 , wherein van der Waals forces, hydrophobic interactions, or both, keep the cyclopropene within the cavity.

33. The system of claim 21 , wherein the ratio of moles of molecular encapsulating agent to moles of cyclopropene is 0.1 or larger.

34. The system of claim 33 , wherein the ratio of moles of molecular encapsulating agent to moles of cyclopropene is 0.2 or larger.

35. The system of claim 34 , wherein the ratio of moles of molecular encapsulating agent to moles of cyclopropene is 0.5 or larger.

36. The system of claim 35 , wherein the ratio of moles of molecular encapsulating agent to moles of cyclopropene is 0.9 or larger.

37. The system of claim 21 , wherein the ratio of moles of molecular encapsulating agent to moles of cyclopropene is 2 or lower.

38. The system of claim 37 , wherein the ratio of moles of molecular encapsulating agent to moles of cyclopropene is 1.5 or lower.

39. The system of claim 1 , wherein the means of an energy source is selected from the group consisting of conduction, convection, and radiation.

40. The system of claim 39 , wherein the radiation energy source is selected from the group consisting of lasers, microwave, and infrared.

41. The system of claim 39 , wherein the convection energy source is provided by flowing heated gas or flowing heated liquid.

42. The system of claim 39 , wherein the means of an energy source is conduction.

Assignees

• Agrofresh Inc

Inventors

• Ghosh Tirthankar

Classifications

• A23B9/18

  in the form of gases, e.g. fumigation; Compositions or apparatus therefor · CPC title

• A01N27/00 Primary

  Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons · CPC title

• A23B7/144

  in the form of gases, e.g. fumigation; Compositions or apparatus therefor · CPC title

• A01N25/20 Primary

  Combustible or heat-generating compositions · CPC title

• A01N2300/00

  Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48 · CPC title