Synthesis and Properties of Poly(Arylene Ether Pyrazole)S

Abstract

Poly(arylene ether pyrazole)s containing N–H and N-phenyl groups have been prepared by the aromatic nucleophilic displacement reaction of two new bisphenols containing a pyrazole ring with activated aromatic dihalides in N,N-dimethylacetamide at 155 °C in the presence of anhydrous potassium carbonate. The polymers exhibited glass transition temperatures (T_g ) ranging from 190–296 °C and inherent viscosities from 0.44–1.96 dl g⁻¹. Poly(arylene ether-pyrazole)s containing N–H groups exhibited higher T _g and mechanical properties than the corresponding N-phenyl-containing poly(arylene ether pyrazole)s. The chemistry, physical and mechanical properties of these polymers are discussed.

Get full access to this article

View all access options for this article.

References

[1] Korshak V V , Krongauz Y S and Berlin A M 1965 J. Polym. Sci. A 3 2425-2425

[2] Schaefer J P and Bertram J L 1965 Polym. Lett. 3 9-9

[3] Neuse E W 1968 Macromolecules 1 171-171

[4] Gilliams Y Smets G 1969 Makromol. Chem. 128 263-363

[5] Gilliams Y and Smets G 1968 Makromol. Chem. 1 1-1

[6] Ueda M , Funayama M , Kawaharasaki N and Imai Y 1981 Makromol. Chem. 182 837-837

[7] Moore J A and Mehta P C 1988 Macromolecules 21 2644-2644

[8] Connell J W , Bass R G , Sinsky M S and Waldbauer R O 1987 J. Polym. Sci. Polym. Chem. Ed. 25 2531-2531

[9] Johnson R N , Farnham A G , Clendenning F A , Hale W F and Merrian C N 1967 J. Polym. Sci. A (1) 5 2375-2375

10.

[10] Vogel H A 1970 J. Polym. Sci. A (1) 8 2035-2035

11.

[11] Ueda M and Sata M 1987 Macromolecules 20 2675-2675

12.

[12] Hay A S , Blanchard H S , Endres G F and Eustance J W 1959 J. Am. Chem. Soc. 81 6335-6355

13.

[13] Van Dort H M , HoefsCAM , Magre E P , Schoff A J and Ynetma K 1968 Eur. Polym. J. 4 275-275

14.

[14] Percec V and Nava H 1988 J. Polym. Sci., A., Polym. Chem. Ed. 26 783-783

15.

[15] Colon I and Kwiatkowski G T 1990 J. Polym. Sci., A, Polym. Chem. Ed. 28 367-367

16.

[16] Colquhoun H M , Dudman C C , Thomas M , O’Mahoney C A and Williams D J 1990 J. Chem. Soc. Chem. Commun. 336

17.

[17] White D M , Takekoshi T , William F J , Relles H M , Donahue P E , Klopfer H J , Loucks G R , Manello J S , Matthews T O and Schelluenz R W 1981 J. Polym. Sci., A, Polym. Chem. Ed. 19 1635-1635

18.

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

19.

[19] Connell J W and Hergenrother P M 1988 Polym. Prepr. Am. Chem. Soc. Div. 29 (1) 172-172; 1992 Polymer 33 3739-3739

20.

[20] Harris F W and Kosleski J E 1989 Polym. Mater. Sci. Eng. Proc. 61 870-870

21.

[21] Connell J W and Hergenrother P M 1989 Polym. Mater. Sci. Eng. Proc. 60 527-527; 1991 J. Polym. Sci., A, Polym. Chem. Ed. 29 1677-1677

22.

[22] Connell J W and Hergenrother P M 1990 Sci. Adv. Mater. Pro. Eng. Ser. 35 432-432; High Perform. Polym. 2 211-211

23.

[23] Connell J W and Croall C I 1991 Polym. Prepr. Am. Chem. Soc. Div. 32 (2) 162-162

24.

[24] Connell J W , Hergenrother P M and Wolf P W 1990 Polym. Mater. Sci. Eng. Proc. 63 366-366; 1992 Polymer 33 3507-3507

25.

[25] Carter K R , Jonsson H , Twig R , Miller R D and Hedrick J L 1992 Polym. Prepr. Am. Chem. Soc. Div. 33(1) 388-388

26.

[26] Hilborn J G , Labadie J W and Hedrick J L 1990 Macromolecules 23 2854-2854

27.

[27] Smith J G Jr , Connell J W and Hergenrother P M 1991 Polym. Prepr. Am. Chem. Soc. Div. 32 (1) 646-646; 1992 Polymer 33 1742-1742

28.

[28] Smith J G Jr , Connell J W and Hergenrother P M 1991 Polym. Prepr. Am. Chem. Soc. Div. 32 (3) 193-193

29.

[29] Smith J G Jr , Connell J W and Hergenrother P M 1992 Polym. Prepr. Am. Chem. Soc. Div. 33 (1) 411-411

30.

[30] Hergenrother P M , SmithJGJrand Connell J W 1993 Polym. Prepr. Am. Chem. Soc. Div. 34 (4) 856-856

31.

[31] Smith J G Jr , Connell J W and Hergenrother P M 1992 Polym. Prepr. Am. Chem. Soc. Div. 33 (1) 1098-1098; 1993 J. Polym. Sci., A, Polym. Chem. Ed. 31 3099-3099

32.

[32] Bass R G and Srinivasan K R 1991 Polym. Prepr. Am. Chem. Soc. Div. 32 (1) 619-619

33.

[33] Bass R G , Srinivasan K R and SmithJGJr 1991 Polym. Prepr. Am. Chem. Soc. Div. 32 (2) 160-160

34.

[34] Pfender R , Wolf J P , Kainmueller T , Kramer A , Hoffmann K and Stockinger F 1993 Ger. Offen. DE 4230 839 25 March; 1994 Chem. Abstr. 120 135439s-135439s

35.

[35] Hergenrother P M , Jensen B J and Havens S J 1988 Polymer 29 359-359

36.

[36] Ohta K , Muroki H , Hatada K , Takagi A , Ema H , Yamamoto I and Matsuzaki K 1986 Mol. Cryst. Liq. Cryst. 140 63-63

37.

[37] Anselme J P 1967 J. Org. Chem. 32 716-716

38.

[38] van Steenis J 1947 Rec. Trav. Chim. 66 29-29

39.

[39] Schoefield K , Grimmett M R and KeeneBRT 1976 The Azoles (London: Cambridge University Press) p 1-1

40.

[40] Percec V , Clough R S , Rinaldi P L and Litman V E 1991 Polym. Prepr. Am. Chem. Soc. Div. 32 (1) 353-353; 1991 Macromolecules 24 5889-5899