Polyetherimides, methods of manufacture, and articles formed therefrom

A polymer composition comprising a polyetherimide of the formula

• wherein
• n is greater than 1,
• each R is the same or different, and is wherein R is selected from an aromatic hydrocarbon group having 6 to 30 carbon atoms, a halogenated derivative thereof, a straight or branched chain alkylene group having 2 to 10 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, or a divalent group of the formula
• wherein Q1 is selected from —O—, —S—, —C(O)—, —SO2—, —SO—, —CyH2y— wherein y is 1 to 5, and a halogenated derivative thereof,
• each Z is the same or different and is an aromatic C6-24 monocyclic or polycyclic moiety optionally substituted with 1 to 6 C1-8 alkyl groups, 1 to 8 halogen atoms, or a combination thereof, and
• the divalent bonds between the —O—Z—O— group and the phenyl substituents are in the 3,3′, 3,4′, 4,3′, and 4,4′ positions;
• the divalent bonds of the —O—Z—O— group being made from a bis(halophthalimide) composition comprising, based on the weight of the bis(halophthalimide) composition,
• from more than 45 to less than 75 weight percent of a 3,3′-bis(halophthalimide) of the formula
• less than 10 weight percent of a 3,4′-bis(halophthalimide) of the formula
• and
• from more than 45 to less than 75 weight percent of a (4,4′-bis(halophthalimide) of the formula
• wherein R is as defined above.

A method for the manufacture of a polyetherimide composition, the method comprising reacting, in the presence of a catalytically active amount of a phase transfer catalyst, an alkali metal salt of a dihydroxy aromatic compound of the formula

• MO—Z—OM
• wherein M is an alkali metal salt and Z is an aromatic C6-24 monocyclic or polycyclic moiety optionally substituted with 1 to 6 C1-8 alkyl groups, 1 to 8 halogen atoms, or a combination thereof, with
• a bis(chlorophthalimide) composition comprising, based on the weight of the bis(chlorophthalimide) composition,
• from more than 45 to less than 75 weight percent of a 3,3′-bis(chlorophthalimide) of the formula
• less than 10 weight percent of a 3,4′-bis(chlorophthalimide) of the formula
• and
• from more than 45 to less than 75 weight percent of a (4,4′-bis(chlorophthalimide) of the formula
• wherein each R is selected from an aromatic hydrocarbon group having 6 to 30 carbon atoms, a halogenated derivative thereof, a straight or branched chain alkylene group having 2 to 10 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, or a divalent group of the formula
• wherein Q1 is selected from —O—, —S—, —C(O)—, —SO2—, —SO—, and —CyH2y— wherein y is 1 to 5 and a halogenated derivative thereof, to form a polyetherimide of the formula
• wherein n is greater than 1, each R is the same or different, each Z is the same or different, and are as defined above, and the divalent bonds between the —O—Z—O— group and the phenyl substituents are in the 3,3′, 3,4′, 4,3′, and 4,4′ positions.

A method for the manufacture of a bis(halophthalimide) composition from a combination of a 4-halophthalic anhydride isomer of the formula

• and a 3-halophthalic anhydride isomer of the formula
• wherein X is a halogen, in a ratio of the 4-halophthalic anhydride to 3-halophthalic anhydride of 90:10 to 10:90, the method comprising
• reacting at least 80 mole percent of the total amount of one isomer with a diamine of the formula
• H2N—R—NH2
• wherein R is selected from an aromatic hydrocarbon group having 6 to 30 carbon atoms, a halogenated derivative thereof, a straight or branched chain alkylene group having 2 to 10 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, or a divalent group of the formula
• wherein Q1 is selected from —O—, —S—, —C(O)—, —SO2—, —SO—, —CyH2y— wherein y is 1 to 5, and a halogenated derivative thereof, to form a bis(halophthalimide) to form a reaction mixture comprising a bis(halophthalimide);
• and
• adding at least 80 mole percent of the total amount of the other isomer and another portion of the diamine to the reaction mixture, to form a bis(halophthalimide) composition comprising, based on the total weight of the composition,
• from more than 45 to less than 75 weight percent of a 3,3′-bis(halophthalimide) of the formula
• less than 10 weight percent of a 4,3′-bis(halophthalimide) of the formula
• and
• from more than 45 to less than 75 weight percent of a (4,4′-bis(halophthalimide) of the formula
• wherein X and R are as defined above.

A polyetherimide of the formula

• wherein,
• based on the total mole percent of the —O—Z—O— groups in the polyetherimide,
• more than 45 to less than 75 mole percent the divalent bonds of the —O—Z—O-groups are in the 3,3′ position,
• more than 0 to less than 10 mole percent of the —O—Z—O— groups are in the 3,4′, and 4′,3 positions, and
• more than 45 to less than 75 mole percent of the —O—Z—O— groups are 4,4′ position;
• n is greater than 1;
• each R is independently an aromatic hydrocarbon group having 6 to 30 carbon atoms, a halogenated derivative thereof, a straight or branched chain alkylene group having 2 to 10 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, or a divalent group of the formula
• wherein Q1 is selected from —O—, —S—, —C(O)—, —SO2—, —SO—, and —CyH2y— wherein y is 1 to 5 and a halogenated derivative thereof;
• and
• each Z is independently an aromatic C6-24 monocyclic or polycyclic moiety optionally substituted with 1 to 6 C1-8 alkyl groups, 1 to 8 halogen atoms, or a combination thereof.