Method to prepare bis(haloimides)

A method for preparing a bis(chlorophthalimide);

• said method comprising:
• (A) preparing a mixture comprising 3-chlorophthalic anhydride, 4-chlorophthalic anhydride and at least one solvent;
• (B) adding to the mixture formed in step (A) at least one aromatic diamine, to form a reaction mixture, said reaction mixture being characterized by an initial molar ratio of 3-chlorophthalic anhydride and 4-chlorophthalic anhydride to aromatic diamine;
• (C) heating the reaction mixture formed in step (B) optionally in the presence of an imidization catalyst, to a temperature of at least 100° C.;
• (D) analyzing the reaction mixture formed by the combination of steps (A)-(C) to determine the initial molar ratio of 3-chlorophthalic anhydride and 4-chlorophthalic anhydride to aromatic diamine;
• and
• (E) performing one step selected from the group consisting of:
• (i) adding a mixture of 3-chlorophthalic anhydride and 4-chlorophthalic anhydride, or aromatic diamine to the reaction mixture formed by the combination of steps (A)-(C) to achieve a corrected molar ratio of 3-chlorophthalic anhydride and 4-chlorophthalic anhydride to aromatic diamine, said corrected molar ratio being in a range between about 2.01 and about 2.3, and heating to a temperature of at least 100° C., optionally in the presence of an imidization catalyst, to obtain a bis(chlorophthalimide) product mixture that is substantially free of water;
• and
• (ii) heating to a temperature of at least 100° C., optionally in the presence of an imidization catalyst, the reaction mixture formed by the combination of steps (A)-(C) to obtain a bis(chlorophthalimide) product mixture that is substantially free of water.

A method for preparing a bis(4-chlorophthalimide);

• said method comprising:
• (A) preparing a mixture comprising 4-chlorophthalic anhydride and orthodichlorobenzene;
• (B) adding to the mixture formed in step (A) a mixture of meta-phenylene diamine and para-phenylene diamine[ ], to form a reaction mixture, said reaction mixture being characterized by an initial molar ratio of 4-chlorophthalic anhydride to meta-phenylene diamine and para-phenylene diamine;
• (C) heating the reaction mixture formed in step (B) in the presence of a catalyst, to a temperature of at least 100° C.;
• (D) analyzing the reaction mixture formed by the combination of steps (A)-(C) to determine the initial molar ratio of 4-chlorophthalic anhydride to meta-phenylene diamine and para-phenylene diamine;
• and
• (E) performing one step selected from the group consisting of:
• (i) adding 4-chlorophthalic anhydride, or a mixture of meta-phenylene diamine and para-phenylene diamine to the reaction mixture formed by the combination of steps (A)-(C) to achieve a corrected molar ratio of 4-chlorophthalic anhydride to meta-phenylene diamine and para-phenylene diamine, said corrected molar ratio being in a range between about 2.01 and about 2.3, and heating to a temperature of at least 100° C. to obtain a bis(4-chlorophthalimide) product mixture that is substantially free of water;
• and
• (ii) heating to a temperature of at least 100° C. the reaction mixture formed by the combination of steps (A)-(C) to obtain a bis(4-chlorophthalimide) product mixture that is substantially free of water.