Hexafluoroisopropanol group-containing diamine, polyimide and polyamide using same, cyclized product thereof, and method for producing same

A method for producing a diamine represented by the general formula (1),

• the method comprising reacting a diamine represented by the general formula (5),
• with hexafluoroacetone or its hydrate;
• wherein A represents a single bond,
• each R1 independently represents a C1-4 alkyl group or a halogen group, and
• each of “a” and “b” independently represents an integer of 0-2, and 1≦a+b≦4.

A polyamic acid comprising a repeating unit represented by the general formula (6),

• wherein A represents a single bond or CH2,
• each R1 independently represents a C1-4 alkyl group or a halogen group,
• R2 represents a tetravalent organic group containing at least one group selected from the group consisting of an aliphatic ring, a heterocyclic ring, an aromatic ring, or a straight-chain or branched-chain aliphatic hydrocarbon group,
• hydrogen atoms in the tetravalent organic group of R2 may partially be replaced with alkyl group, fluoroalkyl group, carboxyl group, hydroxy group, cyano group or halogen group, and
• each of “a” and “b” independently represents an integer of 0-2, and 1≦a+b≦4.

A polyimide comprising a repeating unit represented by the general formula (9),

• wherein A represents a single bond or CH2,
• each R1 independently represents a C1-4 alkyl group or a halogen group,
• R2 represents a tetravalent organic group containing at least one selected from the group consisting of an aliphatic ring, a heterocyclic ring, an aromatic ring, or a straight-chain or branched-chain aliphatic hydrocarbon group,
• hydrogen atoms in the tetravalent organic group of R2 may partially be replaced with alkyl group, fluoroalkyl group, carboxyl group, hydroxy group, cyano group or halogen group, and
• each of “a” and “b” independently represents an integer of 0-2, and 1≦a+b≦4.

A method for producing a polyimide, comprising:

• polymerizing a diamine represented by the general formula (1),
• with a tetracarboxylic dianhydride represented by the general formula (11),
• to produce a polyamic acid containing a repeating unit represented by the general formula (6),
• and
• dehydrating the polyamic acid to obtain a polyimide containing a repeating unit represented by the general formula (9),
• wherein each A independently represents a single bond or CH2,
• each R1 independently represents a C1-4 alkyl group or a halogen group,
• R2 represents a tetravalent organic group containing at least one selected from the group consisting of an aliphatic ring, a heterocyclic ring, an aromatic ring, or a straight-chain or branched-chain aliphatic hydrocarbon group,
• hydrogen atoms in the tetravalent organic group of R2 may partially be replaced with alkyl group, fluoroalkyl group, carboxyl group, hydroxy group, cyano group or halogen group, and
• each of “a” and “b” independently represents an integer of 0-2, and 1≦a+b≦4.

A polyamide comprising a repeating unit represented by the general formula (12),

• wherein A represents a single bond or CH2,
• each R1 independently represents a C1-4 alkyl group or a halogen group,
• R5 represents a bivalent organic group containing at least one selected from the group consisting of an aliphatic ring, a heterocyclic ring, an aromatic ring, or a straight-chain or branched-chain aliphatic hydrocarbon group,
• hydrogen atoms in the bivalent organic group of R5 may partially be replaced with alkyl group, fluoroalkyl group, carboxyl group, hydroxy group, cyano group or halogen group, and
• each of “a” and “b” independently represents an integer of 0-2, and 1≦a+b≦4.

A method for producing a polyamide containing a repeating unit represented by the general formula (12),

• by polycondensing a diamine represented by the general formula (1),
• with a dicarboxylic acid or a derivative thereof, represented by the general formula (13),
• or a dicarboxylic acid derivative represented by the general formula (14),
• wherein A represents a single bond or CH2,
• each R1 independently represents a C1-4 alkyl group or a halogen group,
• each of “a” and “b” independently represents an integer of 0-2, and 1≦a+b≦4,
• R5 represents a bivalent organic group containing at least one selected from the group consisting of an aliphatic ring, a heterocyclic ring, an aromatic ring, or a straight-chain or branched-chain aliphatic hydrocarbon group,
• hydrogen atoms in the bivalent organic group of R5 may partially be replaced with alkyl group, fluoroalkyl group, carboxyl group, hydroxy group, cyano group or halogen group,
• each R6 independently represents at least one group selected from a hydrogen atom, a C1-10 alkyl group or a benzyl group, and
• X represents a halogen group.

A polymer comprising a repeating unit represented by the general formula (15),

• wherein A represents a single bond or CH2,
• each R1 independently represents a C1-4 alkyl group or a halogen group,
• R5 represents a bivalent organic group containing at least one selected from the group consisting of an aliphatic ring, a heterocyclic ring, an aromatic ring, or a straight-chain or branched-chain aliphatic hydrocarbon group, and
• hydrogen atoms in the bivalent organic group of R5 may partially be replaced with alkyl group, fluoroalkyl group, carboxyl group, hydroxy group, cyano group or halogen group.

A method for producing a polymer represented by the general formula (15),

• the method comprising conducting a cyclocondensation of a polyamide containing a repeating unit represented by the general formula (12),
• wherein A represents a single bond or CH2,
• each R1 independently represents a C1-4 alkyl group or a halogen group,
• R5 represents a bivalent organic group containing at least one selected from the group consisting of an aliphatic ring, a heterocyclic ring, an aromatic ring, or a straight-chain or branched-chain aliphatic hydrocarbon group,
• hydrogen atoms in the bivalent organic group of R5 may partially be replaced with alkyl group, fluoroalkyl group, carboxyl group, hydroxy group, cyano group or halogen group, and
• each of “a” and “b” independently represents an integer of 0-2, and 1≦a+b≦4.