Synthesis and Properties of Aromatic Poly(Ether Ketone Pyridazine)s

Abstract

A general method for the preparation of pyridazine-containing aromatic poly(ether ketone)s has been developed. Polymerization is based on a ketone-activated nucleophilic halo displacement in pyridazine containing bis(4-fluorobenzoyl) moieties by phenoxides. 3,6-Bis(4-fluorobenzoyl-4'-phenoxy-4"-phenoxy)pyridazine was prepared by reaction of 4-fluorobenzoyl chloride with 3,6-bis(4-phenoxyphenoxy)pyrfdazine in dichloromethane in the presence of aluminum chloride. Reaction 3,6-bis(4-fluorobenzoyl-(4-phenoxy-4phenoxy)pyridazine with diphenols in an aprotic solvent in the presence of potassium carbonate gave a series of aromatic poly(ether ketone pyridazine)s. Films of the aromatic poly(ether ketone pyrdazine)s displayed good thermal stability, flexibility, and T. values ranging from 159 to 198 'C. The dielectric constants of the films were characterized as a function of relative humidity (RH).

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References

[1] Denton D D , Day D R . Priore D F , Senturia S D , Anolick E S and Scheider D 1985 J. Elec. Mater, 14 119-136

[2] Larsen R A 1980 IBM J. Res. Dev. 24 268-268

[3] Mittal K (ed) 1984 Polyitmides: Synthesis, Characterization, and Applications vols 1, 2 (New York: Plenum)

[4] Frazer A H 1968 Polymer Reviews (New York: Wiley) pp 159-175

[5] Attwood T E . Davidson P C , Freeman J C , Hoy J C , Rose J B and Staniland P A 1981 Polymer 22 1096-1096

[6] Rose J B 1974 Polymer 15 456-456

[7] Hilbom J G , Labadie J W and Hedrick J L 1990 Macromolecules 23 2845-2845

[8] Smith J W Jr , Connell J W and Hergenrother P M 1992 Polymer 33 1743-1743

[9] Connell J W and Hergearother P M 1991 J. Polym. Sci, Potym. Chem. Edn. 29 1667-1667

10.

[10] Connell J W and Hergenrother P M 1992 Polymer 33 3739-3739

11.

[11] Hedrick J L and Labadie J W 1988 Macromolecules 21 1883-1883

12.

[12] Connell J W , Hergenrother P M and Wolf P W 1992 Polymer 33 3507-3507

13.

[13] Mercer F W 1992 Polym. Mater. Sci. Eng. Proc. 66 268-268

14.

[14] Johnson R N , Farnham A G , Clendinning R A , Hale W F and Merrian C N 1967 J. Polym. Sci. A-15 2375-2375

15.

[15] Mercer F W and McKenzie M T 1993 High Perform. Polym. 5 97-97

16.

[16] Mercer F W 1993 High Perform. Polym. 5 69-69

17.

[17] Mercer F W High Perform. Polym. 5 187-187

18.

[18] Mercer F W and Goodman T D 1991 High Perform. Polym. 3 297-297

19.

[19] Homrner P J, Jansons V and Gors J C 1986 Eur. Patent 0 178 184

20.

[20] Horner P J and Whiteley R H 1991 J. Mater. Chem. 1 271-271

21.

[21] Economy J 1984 Contemporary Topics in Polymer Science vol 5, ed E J Vandennerg (New York: Plenum Press)

22.

[22] Mercer F W and Goodman T D 1991 Polym. Preprints 32 189-189

23.

[23] Hougham G , Tesoro F and Shaw J 1989 Polym. Mater. Sci. Eng. 61 369-369

24.

[24] Hougham G , Tesoro G , Viehbeck A and Chapple-Sokol J 1993 Polym. Preprints 34 375-375

25.

[25] Mercer F Wand Goodman T D 1990 Int. Electron. Packaging Soc. Conf. Proc. (1990) (Wheaton, IL: International Electronics Packaging Soceity) pp 1042-1062

26.

[26] Sacher E and Susko J R 1979 J. Appl. Polym. Sci. 23 2355-2355

27.

[27] Moylan C R , Best M E and Ree M 1991 J. Polym. Sci. B 29 87-87

28.

[28] Ewing D F 1979 Org. Magn. Reson. 12 499-499