IP Library › Granted Patent US 10,364,210
Granted Patent B2
US 10,364,210 · App. 15/507,009 · Granted Jul 30, 2019

Diamine compounds, dinitro compounds and other compounds, and methods of producing thereof and uses related thereof

Inventors: Alex B. Wood (Sacramento, CA); Makoto Nathanael Masuno (Elk Grove, CA); Ryan L. Smith (Sacramento, CA); John Albert Bissell, II (Sacramento, CA); Robert Joseph Araiza (Sacramento, CA); Dimitri A. Hirsch-Weil (Sacramento, CA)
Assignee: MICROMIDAS, INC.
C07C211/51C07C205/04C07C209/32C07C211/09C07C211/27C07C255/35C07D307/14C07D307/38C07D307/42C07D307/52C07D307/54C08F210/02C08G69/04C08G69/08C08G69/26C08G69/28C08G73/02C07C2601/16
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Quick Facts
Patent No.
US 10,364,210
App. No.
15/507,009
Granted
Jul 30, 2019
Kind
B2
Abstract

Provided herein are (phenylene)dialkanamines, and methods of producing such (phenylene)dialkanamines from various furanyl and benzyl compounds. Such furanyl compounds may include, for example, bis(nitroalkyl)furans, bis(aminoalkyl)furans, and nitroalkyl(furan)acetonitriles. Such compounds may include, for example, bis(nitroalkyl)benzenes. Provided herein are also alkyldiamines, and methods for producing such alkyldiamines from furanyl compounds.

Claims (17)

1. A composition, comprising:

a compound of formula (Q):

wherein Y is halo.

2. The composition of claim 1 , wherein Y is chloro or bromo.

3. The composition of claim 1 , wherein the composition further comprises a compound of formula (R):

or any isomers thereof, wherein Y is halo.

4. The composition of claim 3 , wherein the composition comprises the (Z) isomer of the compound of formula (R).

5. The composition of claim 3 , wherein the composition comprises 2-(chloromethyl)-5-[(Z)-2-nitroethenyl]furan.

6. The composition of claim 3 , wherein the composition comprises the (E) isomer of the compound of formula (R).

7. The composition of claim 3 , wherein the composition comprises 2-(chloromethyl)-5-[(E)-2-nitroethenyl]furan.

8. The composition of claim 7 , wherein the composition comprises a crystalline form of 2-(chloromethyl)-5-[(E)-2-nitroethenyl]furan.

9. The composition of claim 7 , wherein the composition comprises 2-(chloromethyl)-5-[(E)-2-nitroethenyl]furan having an X-ray powder diffraction pattern substantially as shown in FIG. 5 .

10. The composition of claim 7 , wherein the composition comprises 2-(chloromethyl)-5-[(E)-2-nitroethenyl]furan having an X-ray powder diffraction pattern that comprises at least one peak at about 39.8 degrees 2θ.

11. The composition of claim 10 , wherein the 2-(chloromethyl)-5-[(E)-2-nitroethenyl]furan has an X-ray powder diffraction pattern that further comprises at least one additional peak at about 13.0 degrees 2θ, about 26.2 degrees 2θ, about 53.9 degrees 2θ, or about 69.0 degrees 2θ.

12. The composition of claim 1 , further comprising a polymerization catalyst.

13. The composition of claim 3 , wherein Y is chloro or bromo.

14. The composition of claim 3 , further comprising a polymerization catalyst.

Assignments (3)
CHANGE OF NAME Recorded Feb 14, 2022
From: MICROMIDAS, INC.
To: ORIGIN MATERIALS OPERATING, INC.
Reel/Frame 059109/0403 →
SECURITY INTEREST Recorded Nov 12, 2019
From: MICROMIDAS, INC,
To: PM OPERATING, LTD.
Reel/Frame 050980/0661 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 11, 2017
From: WOOD, ALEX B.; MASUNO, MAKOTO NATHANAEL; SMITH, RYAN L.; BISSELL, JOHN ALBERT, II; ARAIZA, ROBERT JOSEPH; HIRSCH-WEIL, DIMITRI A.
To: MICROMIDAS, INC.
Reel/Frame 042976/0657 →
Continuity (2)
Provisional Application 62043284 · Aug 28, 2014
Related Publication 20170275236A1 · Sep 28, 2017