A new diamine, 1,1-bis[4-(4-aminophenoxy)phenyl]-1-(4-hydroxyphenyl)ethane, was synthesized in three steps starting from 1,1,1-tris(4-hydroxyphenyl)ethane. New aromatic polyimides having hydroxy side groups were prepared from this diamine and various tetracarboxylic dianhydrides by the conventional two-step procedure that included ring-opening polymerization in N-methyl-2-pyrrolidone (NMP) and subsequent thermal cyclic dehydration. The polyimides were characterized by X-ray diffraction, differential scanning calorimetry (DSC), thermogravimetry (TG), and dynamic mechanical analysis (DMA). All the polyimides were amorphous, and had glass transition temperature (Tg) in the range of 232—304 °C. The properties of polyimides were compared with those of polyimides prepared from 1,1-bis[4-(4-aminophenoxy)phenyl]-1-phenylethane, which had no hydroxy side groups. The effects of the hydroxy side groups were observed in the thermal properties, thermal mechanical properties and solubility of polyimides.
Imai, Y. ( 1995). Synthesis of Novel Organic Soluble High-Temperature Aromatic Polyimides, High. Perform. Polym., 7: 337-347.
2.
Jeong, H.-J. , Ohishi, Y., Kakimoto, M. and Imai Y. (1994). Synthesis and Characterization of Novel Aromatic Polyimides from 3,4-Bis(4-aminophenyl)-2,5-diphenylthiophene and Aromatic Tetracarboxylic Dianhydrides, Polym. J., 26: 373-377.
3.
Jeong, H.-J. , Ohishi, Y., Kakimoto, M. and Imai, Y. (1991). Synthesis and Characterization of New Soluble Aromatic Polyimides from 3,4-bis(4-aminophenyl)-2,5-diphenylfuran and Aromatic Tetracarboxylic Dianhydrides, J. Polym. Sci., Polymer. Chem; Ed., 29: 39-43.
4.
Jeong, H.-J. , Kakimoto, M. and Imai, Y. (1991). Synthesis and Characterization of New Soluble Aromatic Polyimides from 3,4-bis(4-aminophenyl)-2,5-diphenylpyrrole and Aromatic Tetracarboxylic Dianhydrides, J. Polym. Sci., Polymer. Chem. Ed., 29: 1691-1695.
5.
Ohishi, Y. , Ishida, M., Kakimoto, M., Imai, Y. and Kurosaki, T. (1991). Preparation of Properties of Novel Soluble Aromatic Polyimides from 4,4¢-diaminotriphenylamine and Aromatic Tetracarboxylic Dianhydrides, J. Polym. Sci., Polymer. Chem. Ed., 30: 1027-1035.
6.
Morikawa, A. and Hatakeyama, T. (1999). Synthesis and Characterization of New Soluble Aromatic Polyimides from 1,4-Bis(4-aminophenyl)-2,3-diphenynaphtharene and Aromatic Tetracarboxylic Dianhydrides, Polym. J., 31: 76-78.
7.
Morikawa, A., Furukawa, T. and Moriyama, Y. (2005). Synthesis and Characterization of Novel Aromatic Polyimides from Bis(4-amino-2-biphenyl)ether and Aromatic Tetracarboxylic Dianhydrides, Polym. J., 37: 759-766.
8.
Morikawa, A., Furukawa, T. and Moriyama, Y. (2006). Synthesis and Characterization of Novel Aromatic Polyimides from Bis(4-amino-2-biphenyl)ether and Aromatic Tetracarboxylic Dianhydrides, High. Perform. Polym., 18: 593-602.
9.
Yang, C.-P. , Chen, R.-S. and Chiang, H.-C. (2003). Organosoluble and Light-Colored Fluorinated Polyimides Based on 1,2-Bis(4-amino-2-trifluoromethylphenoxy)benzene and Aromatic Dianhydrides, Polym. J., 35: 662-670.
10.
Yang, C.-P. , Chiang, H.-C. and Su, Y.-Y. (2004). Fluorinated Polyimides Based on 3,3-Bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]phtalide. Polym. J., 36: 979-991.
11.
Yang, C.-P. , Su, Y.-Y. and Hsu, M.-Y. (2006). Organo-soluble and Lighty-colored Fluorinated Polyimides Based on 2,2-Bis[4-(3,4-dicarboxyphenoxy)phenyl. Hexafluoropropane Dianhydride and Aromatic Bis(ether-amine)s Bearing Pendant Trifluoromethyl GroupsPolym. J., 38: 132-144.
12.
Ueda, M. and Nakayama, T. ( 1996). A New Negative-Type Photosensitive Polyimide Based on Poly(hydroxyimide), a Cross-Linker, and a Photoacid Generator, Macromolecules, 29: 6427-6431.
13.
Schab-Balcerzack, E. and Sek, D. (2001). New Soluble Polyimides Containing Hydroxy Groups; I. Synthesis and Characterization. High. Perform. Polym., 13: 45-53.
14.
Akimoto, S., Jikei, M. and Kakimoto, M. (2001). Preparetion and Properties of Novel Aromatic Polyimides from 4,4′-diamino-4′′-hydroxytriphenylamine and Aromatic Dianhydrides. High. Perform. Polym., 12: 197-203.
15.
Okabe, T. and Morikawa, A. ( 2008). Synthesis of Polyimides from 3,3′-dihydroxybenzidine and Conversion to Polybenzoxazoles. High. Perform. Polym. , 20: 53-66.
16.
Morikawa, A. ( 2000). Synthesis and Characterization of Novel Aromatic Polyimides from Aromatic Diamine and 3,3′′′, 4,4′′′-p-Quaterphenyltetracarboxylic Dianhydride, Polym. J., 32: 275-279.
17.
Morikawa, A. and Hosoya, Y. ( 2002). Synthesis and Characterization of Novel Aromatic Polyimides from Aromatic Diamine and 3,3′′′′, 4,4′′′′-p-Quinquephenyltetracarboxylic Dianhydride, Polym. J., 34: 544-549.
18.
Morikawa, A. and Ono, K. ( 2000). Synthesis and Characterization of Novel Aromatic Polyimides from Aromatic Diamine and 3,3′′′′′, 4,4′′′′′-p-Sexiphenyltetracarboxylic Dianhydride, Polym. J., 32: 948-953.
19.
Morikawa, A. and Ono, K. ( 2001). Aromatic Polyimides Containing p-quaterphenyl and p-sexiphenyl Units, High. Perform. Polym., 13: S73-S83.
20.
Akimoto, S., Jikei, M. and Kakimoto, M. ( 2000). A Novel Photosensitive Polyimide: a Polyimide Containing the Hydroxytriphenylamine Structure with Diazonaphtoquinone. High. Perform. Polym., 12: 177-184.
21.
Bes, L., Rousseau, A., Bouteviv, B., Mercier, R., Silion, B. and Toussaere, E.M. (2000). Synthesis and Characterization of Aromatic Polyimides Bearing Nonlinear Optical Chromophores, High. Perform. Polym., 12: 169-176.
22.
Walsh, C.J. and Mandal, B.K. (2001). A New Class of Aromatic Dianhydrides for Thermostable Polyimides, Macromolecules, 13: 2472-2475.
23.
Hasegawa, M. and Koseki, K. (2006). Poly(ester imide)s Possessing Low Coefficient of Thermal Expansion and Low Water Absorption. High Perform. Polym., 18: 697-717.
