Complexes of 1-methylcyclopropene with metal coordination polymer networks

Patent metadata

Field	Value
Publication number	US-9908827-B2
Application number	US-201615206707-A
Country	US
Kind code	B2
Filing date	Jul 11, 2016
Priority date	Nov 10, 2014
Publication date	Mar 6, 2018
Grant date	Mar 6, 2018

Abstract

Disclosed are adsorption complexes that include 1-methylcyclopropene (1-MCP) and a metal coordination polymer network (MCPN), wherein the MCPN is a porous material, and the 1-MCP is adsorbed into the MCPN. Also disclosed are kits for containing 1-MCP that include the adsorption complex in a 1-MCP-impermeable package. Also disclosed are methods of releasing 1-methylcyclopropene (1-MCP) from the kit that include the application of aqueous fluids, heat, and/or pressure.

First claim

What is claimed is:

1. An adsorption complex, comprising:
1-methyl cyclopropene (1-MCP); and
a metal coordination polymer network (MCPN), comprising a metal node selected from Mg, Mn, Ca, Cu, Al, Zn, Fe, Co, or a combination thereof, and one or more ligands coupled to the metal node; wherein the 1-MCP is adsorbed on the MCPN.

2. The adsorption complex of claim 1 , wherein the one or more ligands comprise one or more carboxylate groups.

3. The adsorption complex of claim 1 , wherein the one or more ligands are selected from an amino acid or citric acid.

4. The adsorption complex of claim 1 , wherein the one or more ligands are selected from 2,4,6-tris(3,5-dicarboxylphenylamino)-1,3,5-triazine, biphenyldicarboxylate, 4,4′-bipyridine, 1,2-bipyridylethene, − O(O)C—C 10 —H 6 —C(O)O − , formate, terephthalate, benzene-1,3,5-tricarboxylate, 2-methylimidazole, fumarate, —OH, a reaction product of tetra-(4-bromo-phenyl)ethylene and 4-(methoxycarbonyl) phenylboronic acid, 4,4′-sulfonyldibenzoate, or a combination thereof.

5. The adsorption complex of claim 1 , wherein the MCPN has a mean pore diameter of 1 to 50 Å.

6. The adsorption complex of claim 1 , wherein the MCPN is a magnesium coordination polymer network or a calcium coordination polymer network.

7. The adsorption complex of claim 1 , wherein the MCPN is Co 3 (biphenyldicarboxylate) 3 4,4′bipyridine].4DMF.H 2 O or [Co(biphenyldicarboxylate)(4,4′bipyridine)].0.5DMF.

8. The adsorption complex of claim 1 , wherein the MCPN is thermally stable at a temperature of 100° C. to 575° C.

9. The adsorption complex of claim 1 , wherein the MCPN has an accessible pore volume of 1% to 50%.

10. The adsorption complex of claim 1 , wherein a particle size of the MCPN is 0.05 mm to 3 mm.

11. A kit, comprising:
the adsorption complex of claim 1 ; and
a 1-MCP-MCPN complex container that contains the adsorption complex.

12. The kit of claim 11 , wherein the adsorption complex comprises 0.001 weight percent to 25 weight percent 1-MCP adsorbed on the MCPN.

13. The kit of claim 11 , wherein the 1-MCP-MCPN complex container is a capsule, a sachet, or a rigid container.

14. The kit of claim 11 , wherein the 1-MCP-MCPN complex container is at least partially water-soluble.

15. The kit of claim 11 , wherein the MCPN is [Co 3 (biphenyldicarboxylate) 3 4,4′bipyridine].4DMF.H 2 O or [Co(biphenyldicarboxylate)(4,4′bipyridine)].0.5DMF.

16. The kit of claim 11 , wherein the MCPN is configured to release 1-MCP from the adsorption complex when the MCPN is exposed to heat or positive or negative pressure, or when the MCPN is contacted with an aqueous fluid.

17. The kit of claim 11 , wherein the 1-MCP-MCPN complex container further contains a filler selected from a non-aqueous material or a non-aqueous material comprising less than 2% of an aqueous material.

18. A method, comprising:
contacting the adsorption complex of claim 1 with an aqueous fluid, wherein the adsorption complex comprises 0.001 weight percent to 25 weight percent 1-MCP adsorbed into the MCPN.

19. The method of claim 18 , wherein contacting comprises contacting the adsorption complex with an aqueous fluid produced via transpirational moisture evolution from packaged plants or plant parts.

20. The method of claim 18 , wherein the adsorption complex is contained within a 1-MCP-MCPN complex container.

21. The method of claim 20 , wherein contacting comprises contacting the 1-MCP-MCPN complex container with an aqueous fluid produced via transpirational moisture evolution from packaged plants or plant parts.

22. A method, comprising:
contacting an adsorption complex comprising 1-methyl cyclopropene (1-MCP) and a magnesium formate-containing coordination polymer network (MCPN) with an aqueous fluid.

Assignees

• Agrofresh Inc

Inventors

• Mir Nazir

Classifications

• C07C317/44

  having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton · CPC title

• C07F3/06

  Zinc compounds · CPC title

• C07F3/02

  Magnesium compounds · CPC title

• A01N27/00

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

• C07C7/10

  by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids · CPC title