Soluble Polyimides Bearing Long-Chain Alkyl Groups on Their Side Chain via Polymer Reaction

Table 4

Solubility behavior and water contact angles of polyimides and copolyimides containing phenolic OH groups and these polyimides reacted with 12GA.

Solubility^c

Dianhydride^a; mol%

Diamine mol%

12GA^b; mol%

NMP

DMF

DMAc

DMSO

DMI

m-; Cresol

THF

CH2C12

Acetone

Hexane

CHCl3

Ethyl; acetate

Cyclohexene-; DA

HAB

DDE

20

80

0

S

S

S

S

S

S

I

PS

I

I

PS

I

77.0

50

50

0

S

S

S

S

S

S

I

PS

I

I

PS

I

71.4

100

0

0

S

S

S

S

S

S

I

I

I

I

I

I

87.6

20

80

40

S

S

S

S

S

S

I

S

I

I

PS

I

92.3

50

50

100

PS

S

S

S(h)

S

S

I

PS

I

I

PS

I

100.3

100

0

200

S(h)

S(h)

S(h)

S(h)

S(h)

S

I

PS

I

I

I

I

100.1

6FDA

HAB

DDE

20

80

0

S

S

S

S

S

S

S

S

I

I

S

I

86.4

50

50

0

S

S

S

S

S

S

S

S

PS

I

S

I

82.3

100

0

0

S

S

S

S

S

S

S

PS

S

I

PS

I

82.0

20

80

40

S

S

S

PS

S

S

S

S

I

I

S

I

87.5

50

50

100

S

S(h)

S

PS

S

S

S

S

PS

I

S

I

101.2

100

0

200

S

S(h)

S(h)

PS

S(h)

S

S

PS

S

I

PS

I

104.8

DSDA

HAB

DDE

20

80

0

PS

PS

PS

PS

PS

PS

I

I

I

I

I

I

77.0

50

50

0

PS

PS

PS

PS

PS

PS

I

I

I

I

I

I

76.2

100

0

0

S

S

S

S

S

S

I

I

I

I

I

I

75.5

20

80

40

S

PS

PS

S(h)

S

PS

I

I

I

I

I

I

95.9

50

50

100

S

PS

PS

S(h)

S

PS

I

I

I

I

I

I

94.5

100

0

200

S(h)

S(h)

S(h)

S(h)

S(h)

S(h)

I

I

I

I

I

I

101.3

^aEquimolar amount of tetracarboxylic dianhydride was used to the total amount of diamines. ^bEquimolar amount of 12GA was used to the total amount of phenolic OH groups, and the reaction was proceeded using a equimolar amount of DCC as a catalyst. ^cThe qualitative solubility was determined in the 3 mL of solvent at 5 wt% concentration. S: soluble after standing at room temperature for 12 h; S(h): soluble after heating at 70°C for 12 h; PS: partially soluble after standing at heating at 70°C for 12 h; I: insoluble even after heating at 70°C for 12 h. ^dWater contact angles (deg) using contact angle meter (CA-D, Kyowa Interface Science Co., Ltd., Japan).