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 (Tg) 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 Tg 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.
[1] Korshak V V, Krongauz Y S and Berlin A M1965J. Polym. Sci. A32425-2425
2.
[2] Schaefer J P and Bertram J L1965Polym. Lett.39-9
[6] Ueda M, Funayama M, Kawaharasaki N and Imai Y1981Makromol. Chem.182837-837
7.
[7] Moore J A and Mehta P C1988Macromolecules212644-2644
8.
[8] Connell J W, Bass R G, Sinsky M S and Waldbauer R O1987J. Polym. Sci. Polym. Chem. Ed.252531-2531
9.
[9] Johnson R N, Farnham A G, Clendenning F A, Hale W F and Merrian C N1967J. Polym. Sci. A (1) 52375-2375
10.
[10] Vogel H A1970J. Polym. Sci. A (1) 82035-2035
11.
[11] Ueda M and Sata M1987Macromolecules202675-2675
12.
[12] Hay A S, Blanchard H S, Endres G F and Eustance J W1959J. Am. Chem. Soc.816335-6355
13.
[13] Van Dort H M, HoefsCAM, Magre E P, Schoff A J and Ynetma K1968Eur. Polym. J.4275-275
14.
[14] Percec V and Nava H1988J. Polym. Sci., A., Polym. Chem. Ed.26783-783
15.
[15] Colon I and Kwiatkowski G T1990J. Polym. Sci., A, Polym. Chem. Ed.28367-367
16.
[16] Colquhoun H M, Dudman C C, Thomas M, O’Mahoney C A and Williams D J1990J. 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 W1981J. Polym. Sci., A, Polym. Chem. Ed.191635-1635
18.
[18] Hedrick J L and Labadie J W1988Macromolecules211883-1883
19.
[19] Connell J W and Hergenrother P M1988Polym. Prepr. Am. Chem. Soc. Div.29 (1) 172-172; 1992Polymer333739-3739
20.
[20] Harris F W and Kosleski J E1989Polym. Mater. Sci. Eng. Proc.61870-870
21.
[21] Connell J W and Hergenrother P M1989Polym. Mater. Sci. Eng. Proc.60527-527; 1991J. Polym. Sci., A, Polym. Chem. Ed.291677-1677
22.
[22] Connell J W and Hergenrother P M1990Sci. Adv. Mater. Pro. Eng. Ser.35432-432; High Perform. Polym. 2 211-211
23.
[23] Connell J W and Croall C I1991Polym. Prepr. Am. Chem. Soc. Div.32 (2) 162-162
24.
[24] Connell J W, Hergenrother P M and Wolf P W1990Polym. Mater. Sci. Eng. Proc.63366-366; 1992Polymer333507-3507
25.
[25] Carter K R, Jonsson H, Twig R, Miller R D and Hedrick J L1992Polym. Prepr. Am. Chem. Soc. Div.33(1) 388-388
26.
[26] Hilborn J G, Labadie J W and Hedrick J L1990Macromolecules232854-2854
27.
[27] Smith J G Jr, Connell J W and Hergenrother P M1991Polym. Prepr. Am. Chem. Soc. Div.32 (1) 646-646; 1992Polymer331742-1742
28.
[28] Smith J G Jr, Connell J W and Hergenrother P M1991Polym. Prepr. Am. Chem. Soc. Div.32 (3) 193-193
29.
[29] Smith J G Jr, Connell J W and Hergenrother P M1992Polym. Prepr. Am. Chem. Soc. Div.33 (1) 411-411
30.
[30] Hergenrother P M, SmithJGJrand Connell J W1993Polym. Prepr. Am. Chem. Soc. Div.34 (4) 856-856
31.
[31] Smith J G Jr, Connell J W and Hergenrother P M1992Polym. Prepr. Am. Chem. Soc. Div.33 (1) 1098-1098; 1993J. Polym. Sci., A, Polym. Chem. Ed.313099-3099
32.
[32] Bass R G and Srinivasan K R1991Polym. Prepr. Am. Chem. Soc. Div.32 (1) 619-619
33.
[33] Bass R G, Srinivasan K R and SmithJGJr1991Polym. Prepr. Am. Chem. Soc. Div.32 (2) 160-160
34.
[34] Pfender R, Wolf J P, Kainmueller T, Kramer A, Hoffmann K and Stockinger F1993Ger. Offen. DE 4230 839 25 March; 1994Chem. Abstr.120135439s-135439s
35.
[35] Hergenrother P M, Jensen B J and Havens S J1988Polymer29359-359
36.
[36] Ohta K, Muroki H, Hatada K, Takagi A, Ema H, Yamamoto I and Matsuzaki K1986Mol. Cryst. Liq. Cryst.14063-63
37.
[37] Anselme J P1967J. Org. Chem.32716-716
38.
[38] van Steenis J1947Rec. Trav. Chim.6629-29
39.
[39] Schoefield K, Grimmett M R and KeeneBRT1976The Azoles (London: Cambridge University Press) p 1-1
40.
[40] Percec V, Clough R S, Rinaldi P L and Litman V E1991Polym. Prepr. Am. Chem. Soc. Div.32 (1) 353-353; 1991Macromolecules245889-5899
