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STEP POLYMERIZATION
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N N H LIIIa
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N N H
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2-216
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Marvel, 1975; Ueda et al., 1985]. The reaction probably proceeds by a sequence of two nucleophilic reactions: a nucleophilic substitution to form an amine amide (Eq. 2-217) followed by cyclization via nucleophilic addition (Eq. 2-218).
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2-217
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H N N H OH
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2-218
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Polymerization is often carried out as a two-stage melt polymerization. Oxygen is removed from the reaction system by vacuum and the system purged with nitrogen to avoid loss of stoichiometry by oxidation of the tetramine reactant. The reaction mixture is heated to about 290 C in the rst stage with the reaction starting soon after the reactants form a melt (150 C). The high-volume foam produced in this stage is removed, cooled, and crushed to a ne powder. The second-stage reaction involves heating of the powder at 370 390 C under nitrogen.
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HIGH-PERFORMANCE POLYMERS
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Considerable efforts have centered on carrying out the synthesis of polybenzimidazoles at more moderate temperatures. Polymerization of the isophthalic acid or its diphenyl ester have been successfully carried out in polyphosphoric acid or methanesulfonic acid phosphorous pentoxide at 140 180 C, but the reaction is limited by the very low solubilities (<5%) of the reactants in that solvent. The lower reaction temperature is a consequence of activation of the carboxyl reactant via phosphorylation. Lower reaction temperatures are also achieved in hot molten nonsolvents such as sulfolane and diphenyl sulfone, but the need to remove such solvents by a ltration or solvent extraction is a disadvantage. The PBI in Eq. 2-216 is commercially available in the form of ber, composite resin, and formed objects (trade name: Celazole). It has good stability and mechanical behavior up to 300 C and higher (about 25 C higher than the most stable polyimides), does not burn and is self-extinguishing. PBI has better hydrolytic stability than aromatic polyamides and polyimides. It has been used to make ight suits for Apollo, Skylab, MIR, and ISS astronauts and cosmonauts, and escape suits for Space Shuttle astronauts. Fiber is spun from PBI using lyotropic solutions of the polymer in solvents such as N; N-dimethylacetamide, in which it is reasonably soluble at the processing temperature of 250 C. Sulfonated PBI has potential for clothes for re ghters. PBI itself is not approriate for such use since it undergoes extensive shrinkage when exposed to ames. Sulfonation of PBI (on the aromatic rings) greatly reduces this shrinkage problem. Other applications include bushings in injection-molding equipment, electrical connectors in aircraft engines, and ball valve seats in hot- uid-handling piping. It should be noted that structure LIIIa is an oversimpli cation for the polymer formed from 3,3-diaminobenzidene and diphenyl isophthalate. Dehydration after ring closure can occur toward either of the two nitrogens, and one would expect more or less random placements of the carbon nitrogen double bonds. Thus, the PBI structure is a random copolymer of repeating units LIIIa, LIIIb, and LIIIc.
H N N
H N N
LIIIb H N N N N H LIIIc
Polybenzoxazoles (PBO) and polybenzthiazoles (PBT) are related to and synthesized in a manner similar to polybenzimidazoles [Chow et al., 1989; Evers et al., 1981; Hergenrother, 1987; Krause et al., 1988; Maier, 2001; Maruyama et al., 1988; So et al., 1998; Wolfe, 1988]. Synthesis of PBO (LIV) and PBT (LV) is accomplished by the reactions of a dicarboxyl reactant with a bis-o-aminophenol X O and bis-o-aminothiophenol X S , respectively (Eqs. 2-219 and 2-220).
STEP POLYMERIZATION
H2N HOOC COOH + HX N X
NH2 XH N X
2-219
LIV H2N HOOC COOH + HX N X NH2 X
2-220
A wide range of polymers based on other heterocyclic 5-membered rings have been investigated, including oxadiazole, pyrazole, triazole, tetrazole, and thiophene [Bass et al., 1987; Briffaud et al., 2001; Cassidy, 1980; Critchley et al., 1983; Gebben et al., 1988; Ueda and Sugita, 1988].
R N N N Pyrazole N N Triazole
O N N Oxadiazole
N NR N N Tetrazole
Thiophene
2-14i 6-Membered Ring Heterocyclic Polymers Polyquinolines (PQ) are obtained by the Friedlander reaction of a bis-o-aminoaromatic aldehyde (or ketone) with an aromatic bisketomethylene reactant [Concilio et al., 2001; Stille, 1981]. The quinoline ring is formed by a combination of an aldol condensation and imine formation (Eq. 2-221). Polymerization is carried out at 135 C in m-cresol with poly (phosphoric acid) as the catalyst. The reaction also proceeds under base catalysis, but there