Benzimidazole diamine-based polyetherimide compositions and methods for making them

A polyetherimide composition comprising structural units of the formula:

• derived from at least one benzimidazole diamine, wherein R1 and R2 are independently selected from hydrogen and C1–C6 alkyl groups;
• “A” comprises structural units of the formulae:
• or mixtures of the foregoing structural units;
• wherein and “k” and “l” are integers independently having a value of greater than 1;
• “B” comprises substituted and unsubstituted arylene groups having from about 6 to about 25 carbon atoms.

A polyetherimide composition comprising structural units of the formula:

• derived from 2-(4-aminophenyl)-5(6)-aminobenzimidazole;
• wherein “A” comprises structural units of the formulae:
• or mixtures of the foregoing structural units;
• wherein “k” and “l” are integers independently having a value of greater than 1;
• “B” is an arylene group derived from at least one second diamine selected from the group consisting of 1,3-phenylene diamine, 1,4-phenylene diamine, 2,6-diethyl-4-methyl-1,3-phenylene diamine, 4,6-diethyl-2-methyl-1,3-phenylene diamine, 4-methyl-1,3-phenylene diamine, methylene bis(2-chloro-3,5-diethyl-4-phenylene) diamine, 2-methyl-1,3-phenylene diamine, 4,4′-oxydianiline, 3,4′-oxydianiline, 3,3′-oxydianiline, 4,4′-diaminodiphenylsulfone, 3,3′-diaminodiphenylsulfone, and mixtures of the foregoing diamines.

A polyetherimide composition consisting essentially of structural units of the formula:

• derived from 2-(4-aminophenyl)-5(6)-aminobenzimidazole;
• wherein “A” consists essentially of structural units of the formulae:
• or mixtures of the foregoing structural units;
• wherein “k” and “l” are integers independently having a value of greater than 1;
• and
• “B” is an arylene group derived from at least one second diamine selected from the group consisting of 1,3-phenylene diamine, 1,4-phenylene diamine, 2,6-diethyl-4-methyl-1,3-phenylene diamine, 4,6-diethyl-2-methyl-1,3-phenylene diamine, 4-methyl-1,3-phenylene diamine, methylene bis(2-chloro-3,5-diethyl-4-phenylene) diamine, 2-methyl-1,3-phenylene diamine, 4,4′-oxydianiline, 3,4′-oxydianiline, 3,3′-oxydianiline, 4,4′-diaminodiphenylsulfone, 3,3′-diaminodiphenylsulfone, and mixtures of the foregoing diamines.

A method of producing a polyetherimide composition, said method comprising:

• reacting a dianhydride composition with a first diamine composition comprising a benzimidazole diamine and a second diamine in a solvent to form a poly(amic acid), and
• imidizing said poly(amic acid) to form said polyetherimide composition,
• wherein said polyetherimide composition comprises structural units of the formula:
• wherein R1 and R2 are independently selected from hydrogen, and C1–C6 alkyl groups;
• “A” comprises structural units of the formulae:
• wherein “D” is a divalent aromatic group, R3 is selected from hydrogen, halogen, and C1–C6 alkyl groups;
• “q” is an integer having a value of 1 up to the number of positions available on the aromatic ring for substitution;
• k” and “l” are integers independently having a value greater than 1;
• “B” comprises substituted and unsubstituted arylene groups having from about 6 to about 25 carbon atoms.

A method of producing a polyetherimide composition, said method comprising:

• reacting a dianhydride composition comprising 2,2′-isopropylidene-bis-(4-phenyleneoxy-4-phthalic acid)dianhydride with a diamine composition comprising 2-(4-aminophenyl)-5(6)-aminobenzimidazole and meta-phenylenediamine in a solvent to form a poly(amic acid),
• adding a chain-stopper comprising aliphatic mono-anhydrides, aromatic mono-anhydrides, phthalic anhydride, substituted phthalic anhydrides, aliphatic mono-amines, aromatic mono-amines, aniline, alkylated anilines or t-butyl aniline;
• and
• imidizing said poly(amic acid) to form said polyetherimide composition.