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The table on page 419 reports market yields at the low prices of the 1930 s from seasoned standard and respectable domestic corporate bond issues that did not default The former illustrates a type of popular conventional risk, which usually invited disappointment, and the latter illustrates some unpopular unconventional opportunities, which involved little risk and brought large reward Not included in the table on page 419 are some examples from a long list of bonds that defaulted in the 1930 s Many of them sold at nominal prices Examples are Missouri Pacific Convertible Debenture 51 2s of 1949, low price 1 2; Missouri Pacific Refunding 5s of 1965, low price 121 2; Central of Georgia 51 2s of 1959, low price 3 4; Chicago, Rock Island & Pacific Refunding 4s of 1934 (Rocky Reefers), low price 4.

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Polymerization by the ester interchange route is carried out as a two-stage melt polymerization very similar to that described for poly(ethylene terephthalate) However, most industrial processes involve the phosgene reaction in a stirred interfacial polymerization Overall economics and easier control of polymer molecular weight favor the phosgene process over ester interchange Organic solvents such as chlorobenzene, 1,2-dichloroethane, tetrahydrofuran (THF), anisole, and dioxane are used The bisphenol A is usually dissolved in aqueous alkali to form the phenolate salt and then the organic solvent added followed by phosgene The organic solvent prevents the loss of phosgene by hydrolysis and precipitation of the polymer before it has reached the desired molecular weight Reaction temperatures in the range 0 50 C are used.

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Most issues of this type recovered handsomely in the 1940 s and reached values equal to many times these market lows Prime corporate bond issues, in contrast, were never seriously depressed in the 1930s The average yield of prime rails never exceeded 483% during that decade During speculative periods of the late 1960 s, those who sought high yields generally demanded equity kickers on their bond invest-.

Phase-transfer catalysts, such as quaternary ammonium and sulfonium salts and crown ethers, may be added to enhance the transfer of the phenolate salt across the interfacial boundary into the organic phase The polymerization is usually a two-stage reaction Oligomers are formed in the rst stage Tertiary amines are added in the second stage to catalyze the further reaction to high-molecular-weight polymer (An alternate route to polycarbonates, the ring-opening polymerization of cyclic polycarbonate oligomers, has some potential advantages over the step polymerization route; see Sec 7-5c) The IUPAC name of the polycarbonate based on bisphenol A is poly(oxycarbonyloxy-1,4phenylenedimethylmethylene-1,4-phenylene) (trade names: Lexan, Merlon, Calibre); it is usually referred to as polycarbonate or PC Although it can be crystallized Tm 270 C , most polycarbonates are amorphous Tg 150 C .

FIGURE C-13

Chain stiffening due to a combination of the benzene rings and bulky tetrasubstituted carbons in the polymer chain and the high Tg result in a good combination of mechanical properties over a considerable temperature range (15 130 C) PC has excellent resistance to acids and oxidants, better than PET, but is somewhat less resistant to bases compared to PET Polycarbonate is comparable to PET in resistance to organic solvents at ambient temperature At higher temperatures, PC is more resistant to aliphatic and aromatic solvents but less resistant to polar organic solvents Although its upper temperature limit (120 C for reinforced grades) and resistance to some solvents are low compared to other engineering plastics, polycarbonate nds many uses because of its exceptional transparency and impact resistance (toughness) as well as good dimensional and creep resistances.

Applications include compact disks, glazing (windows, doors, face shields, sunglasses, aircraft interiors), automotive (instrument panels and components, exterior panels, wheel covers), medical (components for dialysis, blood collection, and surgical devices), and other uses (power tool and appliance housings, refrigerator interiors, safety helmets, electrical connectors) The United States production of polycarbonates was more than 800 million pounds in 2001; the global production was about 3 billion pounds 2-8f Polyamides The synthesis of polyamides follows a different route from that of polyesters Although several different polymerization reactions are possible, polyamides are usually produced either by direct amidation of a diacid with a diamine or the self-amidation of an amino acid The polymerization of amino acids is not as useful because of a greater tendency toward cyclization (Sec 2-5b) Ring-opening polymerization of lactams is also employed to synthesize polyamides (Chap 7).

THE UNITED STATES IN THE TWENTIETH CENTURY: 1946 1990

Poly(hexamethylene adipamde) [IUPAC: poly(iminohexanedioyliminohexane-1,6-diyl) or poly(iminoadipoyliminohexane-1,6-diyl)], also referred to as nylon 6/6, is synthesized from hexamethylene diamine and adipic acid [Zimmerman, 1988; Zimmerman and Kohan, 2001] A stoichiometric balance of amine and carboxyl groups is readily obtained by the preliminary formation of a 1 : 1 ammonium salt (XIII) in aqueous solution at a concentration of 50% The salt is often referred to as a nylon salt Stoichiometric.

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