IP Library Granted Patent US 9,908,827
Granted Patent B2
US 9,908,827 · App. 15/206,707 · Granted Mar 6, 2018

Complexes of 1-methylcyclopropene with metal coordination polymer networks

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Quick Facts
Patent No.
US 9,908,827
App. No.
15/206,707
Granted
Mar 6, 2018
Kind
B2
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.

Claims (28)

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.

Assignments (7)
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 →
COURT ORDER Recorded Sep 19, 2017
From: MIR, NAZIR; MIRTECH, INC.
To: AGROFRESH INC.
Reel/Frame 043629/0173 →
COURT OPINION Recorded Aug 9, 2017
From: MIR, NAZIR
To: AGROFRESH INC.
Reel/Frame 043506/0183 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 11, 2016
From: MIR, NAZIR
To: MIRTECH, INC.
Reel/Frame 039126/0325 →