Polyimides and processes of making and using same

A process of making a diamine monomer, said process comprising:

• a.) combining, under an inert atmosphere, a polar aprotic solvent and a first molecule having structure of Formula 1 and a second molecule having structure of Formula 2 or Formula 3 below to form the first mixture, said first molecule and said second molecule being combined in a molar ratio from about 1:0.5 to about 1:2;
• wherein for Formula 1, R1, and R2 are each independently H, CH3, CF3, F, Cl or Br;
• preferably for Formula 1 R1, and R2, are each independently CF3 or F;
• and the second molecule having structure of Formula 2 or Formula 3 below:
• wherein for Formula 2, R3 and R4, are each independently H, CH3, CF3, F, Cl or Br;
• Z1 is H, NO2 or F;
• and X is an amino, nitro or acetamido group;
• wherein Formula 3, R3, R4, X1, X2, X3 and X4, are each independently H, CH3, CF3, F, Cl or Br;
• Z1 is H, NO2, F;
• X is an amino, nitro or acetamido group;
• to form a first mixture;
• b.) adding a base to said first mixture to form a second mixture, said base being added to said first mixture in a molar ratio of base to the said first molecule in said first mixture of from about 1:1 to about 5:1;
• c.) stirring said second mixture for about 1 hour to about 24 hours under an inert atmosphere;
• d.) adding an acid to said second mixture to yield a third molecule having Formula 4 or Formula 5 below
• wherein Formula 4, R3 and R4 are each independently H, CH3, CF3, F, Cl or Br;
• X is an amino, nitro or acetamido group;
• wherein for Formula 5, R3, R4, X1, X2, X3, and X4 are each independently H, CH3, CF3, F, Cl or Br;
• X is an amino, nitro or acetamido group;
• e) oxidizing said third molecule to yield a fourth molecule, said fourth molecule having Formula 6 or Formula 7 below:
• wherein Formula 6, R3 and R4 are each independently H, CH3, CF3, F, Cl or Br;
• X is an amino, nitro or acetamido group. preferably R3 and R4 are each independently is H, CF3 or F;
• wherein for Formula 7, R3, R4, X1, X2, X3 and X4 are each independently H, CH3, CF3, F, Cl or Br;
• X is an amino, nitro or acetamido group, preferably R3, R4, X1, X2, X3 and X4 are each independently is H, CF3 or F;
• f) combing said second molecule, an acid, said fourth molecule and a solvent, to form a fourth mixture, heating said fourth mixture to a temperature of about 40° C. to about 150° C. and holding said fourth mixture at said temperature for 1 to 48 hours to yield a fifth molecule, said fifth molecule having Formula 8, 9 or 10 below:
• wherein for Formula 11, R1, R2, R3, R4, R5 and R6 are each independently H, CH3, CF3, F, Cl or Br;
• X and X′ are each independently an amino, nitro or acetamido group;
• wherein for Formula 12:
• R1, R2, R3, R4, R5, R6, X1, X2, X3 and X4 are each independently H, CH3, CF3, F, Cl or Br, X and X′ are each independently an amino, nitro or acetamido group;
• wherein for Formula 13:
• R1, R2, R3, R4, R5, R6, X1, X2, X3, X4, X5, X6, X7, and X8 are each independently H, CH3, CF3, F, Cl or Br, and X and X′ are each independently an amino, nitro or acetamido group;
• and
• g) when for said fifth molecule, X and/or X′ are not amino groups, said X and/or X′ are converted into amino groups by reducing any of X and X′ that is a nitro group and by hydrolyzing any X or X′ that is an acetamido groups.