IP Library Granted Patent US 10,207,968
Granted Patent B2
US 10,207,968 · App. 15/986,387 · Granted Feb 19, 2019

Complexes of 1-methylcyclopropene with metal coordination polymer networks

Inventor: Nazir Mir (Somerset, NJ)
Assignee: AGROFRESH INC.
C07C7/12A01N3/00A01N25/10A01N27/00B01J20/226C07C7/10C07C53/06C07C55/02C07C317/14C07C317/44C07D251/12C07F1/08C07F3/02C07F3/06C07F15/02C07F15/06
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Quick Facts
Patent No.
US 10,207,968
App. No.
15/986,387
Granted
Feb 19, 2019
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 (34)

1. A composition comprising:

i. 1-methylcyclopropene (1-MCP) and

ii. a metal coordination polymer network (MCPN), wherein the MCPN is a porous material selected from the group consisting of magnesium formate; [Ca(4,4′-sulfonyldibenzoate).H 2 O]; Cu-2,4,6-tris(3,5-dicarboxylphenylamino)-1,3,5-triazine); Zn 2 (tcbpe) (wherein tcbpe is a reaction product of tetra-(4-bromo-phenyl)ethylene (tpe-Br) and 4-(methoxycarbonyl) phenylboronic acid); [Zn 2 (biphenyldicarboxylate) 2 (1,2-bipyridylethene)].2DMF, Mg 3 (O 2 C—C 10 —H 6 —CO 2 ) 3 ; aluminum terephthalate; Cu 3 (benzene-1,3,5-tricarboxylate) 2 ; Fe(1,3,5-benzenetricarboxylate); 2-methylimidazole zinc salt; Co(2-methylimidazole) 2 ; and Al(OH)fumarate,

wherein the 1-MCP is adsorbed to a surface of the MCPN.

2. The composition of claim 1 , wherein the surface of the MCPN is a surface defining a pore in the MCPN.

3. The composition of claim 1 , wherein the surface of the MCPN is a surface outside of a pore in the MCPN.

4. The composition of claim 1 , wherein the MCPN is [Ca(4,4′-sulfonyldibenzoate).H 2 O].

5. The composition of claim 1 , wherein the MCPN is Cu-2,4,6-tris(3,5-dicarboxylphenylamino)-1,3,5-triazine).

6. The composition of claim 1 , wherein the MCPN is Zn 2( tcbpe) (wherein tcbpe is a reaction product of tetra-(4-bromo-phenyl)ethylene (tpe-Br) and 4-(methoxycarbonyl) phenylboronic acid).

7. The composition of claim 1 , wherein the MCPN is [Zn 2 (biphenyldicarboxylate) 2 (1,2-bipyridylethene)].2DMF.

8. The composition of claim 1 , wherein the MCPN is Mg 3 (O 2 C—C 10 —H 6 —CO 2 ) 3 .

9. The composition of claim 1 , wherein the MCPN is aluminum terephthalate.

10. The composition of claim 1 , wherein the MCPN is Cu 3 (benzene-1,3,5-tricarboxylate) 2 .

11. The composition of claim 1 , wherein the MCPN is Fe(1,3,5-benzenetricarboxylate).

12. The composition of claim 1 , wherein the MCPN is 2-methylimidazole zinc salt.

13. The composition of claim 1 , wherein the MCPN is Co(2-methylimidazole) 2 .

14. The composition of claim 1 , wherein the MCPN is Al(OH)fumarate.

15. The composition of claim 1 , wherein the MCPN is magnesium formate.

16. The composition of claim 15 , wherein the surface of the MCPN is a surface defining a pore in the MCPN.

17. The composition of claim 15 , wherein the surface of the MCPN is a surface outside of a pore in the MCPN.

18. A kit for containing 1-MCP, the kit comprising the composition of claim 1 and a 1-MCP-impermeable package,

wherein the 1-MCP-impermeable package contains the composition, and

wherein the 1-MCP-impermeable package is a barrier through which 1-MCP cannot pass.

19. The kit of claim 18 , wherein the surface of the MCPN is a surface defining a pore in the MCPN.

20. The kit of claim 18 , wherein the surface of the MCPN is a surface outside of a pore in the MCPN.

21. The kit of claim 18 , wherein the MCPN is magnesium formate.

22. A kit for containing 1-MCP, the kit comprising the composition of claim 1 and a unit formulation containing the composition, wherein the unit formulation is selected from the group consisting of a tablet, a capsule, and a sachet.

23. The kit of claim 22 , wherein the surface of the MCPN is a surface defining a pore in the MCPN.

24. The kit of claim 22 , wherein the surface of the MCPN is a surface outside of a pore in the MCPN.

25. The kit of claim 22 , wherein the MCPN is magnesium formate.

26. A method comprising the step of contacting the composition of claim 1 with an aqueous fluid.

27. The method of claim 26 , wherein the surface of the MCPN is a surface defining a pore in the MCPN.

28. The method of claim 26 , wherein in the surface of the MCPN is a surface outside of a pore in the MCPN.

29. The method of claim 26 , wherein the MCPN is magnesium formate.

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 (5)
Continuation 15673054 · Aug 9, 2017
Continuation 15206707 · Jul 11, 2016
Continuation 14726004 · May 29, 2015
Provisional Application 62077867 · Nov 10, 2014
Related Publication 20180265431A1 · Sep 20, 2018