US 12,258,306 B2
Diamine, polymer and film produced using the same
Hyun Kyu Cho, Daejeon (KR); Jin Hyung Park, Daejeon (KR); Hyo Shin Kwak, Daejeon (KR); Seung Min Jeon, Daejeon (KR); Jong Chan Kim, Daejeon (KR); and Joo Hyun Lee, Daejeon (KR)
Assigned to SK Innovation Co., Ltd., Seoul (KR); and SK ie technology Co., Ltd., Seoul (KR)
Filed by SK Innovation Co., Ltd., Seoul (KR); and SK ie technology Co., Ltd., Seoul (KR)
Filed on Sep. 30, 2022, as Appl. No. 17/957,519.
Claims priority of application No. 10-2021-0130533 (KR), filed on Oct. 1, 2021; and application No. 10-2021-0138409 (KR), filed on Oct. 18, 2021.
Prior Publication US 2023/0123199 A1, Apr. 20, 2023
Int. Cl. C07C 237/40 (2006.01); C08G 69/32 (2006.01); C08G 73/10 (2006.01); C08G 73/14 (2006.01); C08J 5/18 (2006.01)
CPC C07C 237/40 (2013.01) [C08G 69/32 (2013.01); C08G 73/1039 (2013.01); C08G 73/1042 (2013.01); C08G 73/1067 (2013.01); C08G 73/1078 (2013.01); C08G 73/14 (2013.01); C08J 5/18 (2013.01); C08J 2377/10 (2013.01); C08J 2379/08 (2013.01)] 21 Claims
 
1. A diamine represented by the following Chemical Formula 1:

OG Complex Work Unit Chemistry
where in Chemical Formula 1,
R1 and R2 are each independently (C2-C20) alkyl, (C1-C20) alkoxy, halo (C1-C20) alkyl, (C1-C20) alkylcarbonyl, (C1-C20) alkoxycarbonyl, (C6-C20) arylcarbonyl, tri(C1-C20) alkylsilyl, carboxyl, hydroxy, amino, nitro, cyano, or halogen;
R3 is (C1-C20) alkyl, (C1-C20) alkoxy, halo (C1-C20) alkyl, (C1-C20) alkylcarbonyl, (C1-C20) alkoxycarbonyl, (C6-C20) arylcarbonyl, tri(C1-C20) alkylsilyl, carboxyl, hydroxy, amino, nitro, cyano, or halogen;
Ra is hydrogen, (C1-C20) alkyl, or (C6-C20) aryl;
a and b are each independently an integer of 1 to 4;
c is an integer of 0 to 4;
when a, b, and c are integers of 2 or more, R1, R2, and R3 may be the same as or different from each other; and
p is an integer of 1 to 3.
 
6. A method of preparing a diamine, the method comprising preparing a diamine represented by the following Chemical Formula 1 by reducing a compound represented by the following Chemical Formula A under a reduction catalyst:

OG Complex Work Unit Chemistry
where in Chemical Formulas 1 and A,
Y1 is nitro or amino; and
the definitions of R1 to R3, Ra, a, b, c, and p are the same as those in Chemical Formula 1 of claim 1.