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CYCLIZATION
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9-7 CYCLIZATION Natural rubber and other 1,4-poly-1,3-dienes are cyclized by treatment with strong protonic acids or Lewis acids [Golub, 1969; Subramaniam, 1988]. The reaction involves protonation of the double bond (Eq. 9-40) followed by cyclization via attack of the carbocation on the double bond of an adjacent monomer unit (Eq. 9-41). Some bicyclic and polycyclic
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fused-ring structures are formed by propagation of the cyclization reaction through more than two successive monomer units. However, the average number of fused rings in a sequence is only 2 4 because of the steric restrictions involved in the polymer reaction as well as competing transfer reactions and the isolation of unreacted monomer units between pairs of cyclized units. Cyclized rubbers have been used for shoe soles and heels, adhesives, hard moldings, and coatings. Cyclization is a key reaction in the production of carbon bers from polyacrylonitrile (PAN) (acrylic ber; see Sec. 3-14d-2). The acrylic ber used for this purpose usually contains no more than 0.5 5% comonomer (usually methyl acrylate or methacrylate or methacrylic acid). Highly drawn (oriented) bers are subjected to successive thermal treatments initially 200 300 C in air followed by 1200 2000 C in nitrogen [Riggs, 1985]. PAN undergoes cyclization via polymerization through the nitrile groups to form a ladder structure (XXVII). Further reaction results in aromatization to the polyquinizarine structure (XXVIII)
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while some of the rings remain as hydrogenated polyquinizarine structures (XXIX). Further heating at temperatures above 2500 C in nitrogen or argon for brief periods eliminates all elements except carbon to yield carbon bers with graphitelike morphology. The carbon
XXVIII
XXIX
REACTIONS OF POLYMERS
bers are subjected to a nal oxidizing atmosphere such as a mixture of gaseous nitrogen and oxygen at 350 1100 C to oxidize the surface for purposes of imparting adhesive properties. The process for producing carbon bers is expensive because of the large energy expenditures required as well as the need to treat the volatile by-products (which include toxic HCN). Carbon bers combine ultrahigh strength and low density when used in composite formulations with epoxy and other resins. More than 50% of carbon ber use is in air and spacecraft applications where weight and fuel savings are achieved without sacri cing performance. A variety of components of air and spacecraft are fabricated from carbon ber epoxy composites. Carbon ber epoxy composites have been used to produce the entire aircraft structure of a business jet (Lear 2100) and the payload bay doors of a space shuttle. Carbon bers combined with higher-performance matrix materials such as polyimides or polybenzimidazole offer the potential for further improvements. Civilian applications include sporting goods golf-club shafts, tennis racquets, shing rods, and boat masts. The lighter weight of the carbon ber composite (compared to the metal component it replaces) allows a redesign of the item for improved performance. The lighter golf-club shaft allows a heavier head design. Other applications include high-quality loudspeakers and various medical applications, including arti cial limbs and surgical implants. Other polymers undergo cyclization, but there are no commercial applications. Poly (methacrylic acid) cyclizes by anhydride formation and poly(methyl vinyl ketone) by condensation (with dehydration) between methyl and carbonyl groups. 9-8 OTHER REACTIONS Hydrogenation of double bonds is practiced with some elastomers such as SBR and NBR to increase high temperature and oxidative resistance [Hsieh, 1998; Hsieh and Quirk, 1996, Wrana et al., 2001]. Only partial hydrogenation is performed since some double bonds are required to achieve the subsequent crosslinking required to achieve elastic behavior. Epoxidation of double bonds in poly(1,3-dienes) yield epoxy resins that are subsequently crosslinked (Sec. 2-12d). 9-9 GRAFT COPOLYMERS Graft and block copolymers contain long sequences of each of two different monomers in the copolymer chain. A block copolymer contains the sequences of the two monomers in a continuous arrangement along the copolymer chain while a graft copolymer contains a long sequence of one monomer (often referred to as the backbone polymer) with one or more branches (grafts) of long sequences of a second monomer (Secs. 2-13a, 6-1b). A variety of techniques for synthesizing such structures have been studied. Most methods of synthesizing graft copolymers involve radical polymerization, but ionic graft polymerizations are also possible [Battaerd and Tregear, 1967; Ceresa, 1973, 1976; Dreyfuss and Quirk, 1986; Gnanou, 1996; Gnanou and Taton, 2002; Rempp and Lutz, 1989]. Graft polymerizations are carried out in heterogeneous as well as homogeneous systems. Three methods exist for synthesizing graft copolymers. Grafting onto involves the reaction between functional groups on two different polymers: