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organic and aqueous phases. Furthermore, high-molecular-weight polymer is formed at the interface regardless of the overall percent conversion based on the bulk amounts of the two reactants. The overall percent conversion can be increased by employing a stirred system as a means of increasing the total area of reacting interface. Several reaction parameters must be controlled in order for interfacial polymerization to proceed successfully. An inorganic base must be present in the aqueous phase to neutralize the by-product hydrogen chloride. If it were not neutralized the hydrogen chloride would tie up the diamine as its unreactive amine hydrochloride salt leading to greatly lowered reaction rates. The acid chloride may undergo hydrolysis to the unreactive acid at high concentrations of the inorganic base or at low polymerization rates. Hydrolysis not only decreases the polymerization rate but also greatly limits the polymer molecular weight, since it converts the diacid chloride into the diacid, which is unreactive at the temperatures employed in interfacial polymerization. The slower the polymerization rate, the greater the problem of hydrolysis as the acid chloride will have more time to diffuse through the interface and into the water layer. Thus acid hydrolysis prevents the use of the interfacial technique for the synthesis of polyesters from diols, since the reaction is relatively slow (k $ 10 3 L mol 1 s 1). The reaction of diacid chlorides and diamines is so fast (k $ 104 105 L mol 1 s 1) that hydrolysis is usually completely absent. The choice of the organic solvent is very important in controlling the polymer molecular weight, since it appears that the polymerization actually occurs on the organic solvent side of the interface in most systems. The reason for this is the greater tendency of the diamine to

THE UNITED STATES IN THE TWENTIETH CENTURY: 1946 1990

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diffuse into the organic solvent compared to the diffusion of diacid chloride into the aqueous side of the interface (For some systems, eg, the reaction of the disodium salt of a dihydric phenol with a diacid chloride, the exact opposite is the case and polymerization occurs on the aqueous side of the interface) An organic solvent that precipitates the high-molecular-weight polymer but not the low-molecular-weight fractions is desirable Premature precipitation of the polymer will prevent the production of the desired high-molecular-weight product Thus, for example, xylene and carbon tetrachloride are precipitants for all molecular weights of poly (hexamethylene sebacate), while chloroform is a precipitant only for the high-molecularweight polymer Interfacial polymerization with the former organic solvents would yield only low-molecular-weight polymer The molecular weight distributions observed in interfacial polymerizations are usually quite different from the most probable distribution [Arai et al, 1985; Korshak, 1966; Morgan, 1965].

Most interfacial polymerizations yield distributions broader than the most probable distribution, but narrower distributions have also been observed The differences are probably due to fractionation when the polymer undergoes precipitation The effect is dependent on the organic solvent used and the solubility characteristics of the polymer The organic solvent can also affect the polymerization by affecting the diffusion characteristics of the reaction system A solvent that swells the precipitated polymer is desirable to maximize the diffusion of reactants through it to the reaction site However, the swelling should not decrease the mechanical strength of the polymer below the level that allows it to be continuously removed from the interface It has been found that the optimum molar ratio of the two reactants in terms of producing the highest yield and/or highest molecular weight is not always 1 : 1 and often varies with the organic solvent.

Neon lights are fun to experiment with and are used in electronic projects for indicator lights as well as in some equipment as frequency strobes (like in older pitch tuners Strobo-Tuners and as strobe lamps to help tune the speed of spinning record platters). The phosphor coating

Table 55 Examples of Terms, Yields, and Yield Spreads of New Issues of High-Grade Corporate Bonds: 1900 1989

The lower the tendency of the water-soluble reactant to diffuse into the organic phase, the greater must be its concentration relative to the other reactant s concentration The optimum ratio of concentrations of the two reactants is that which results in approximately equalizing the rates of diffusion of the two reactants to the interface 2-8c-2 Utility.

The interfacial technique has several advantages. Bulk stoichiometry is not needed to produce high-molecular-weight polymers and fast reactions are used. The low temperatures allow the synthesis of polymers that may be unstable at the high temperatures required in the typical step polymerization. The interfacial technique has been extended to many different polymerizations, including the formation of polyamides, polyesters, polyurethanes, polysulfonamides, polycarbonates, and polyureas. However, there are disadvantages to the process, which have limited its commercial utility. These include the high cost of acid chloride reactants and the large amounts of solvents that must be used and recovered. Commercial utilization has been limited to some polycarbonates, aliphatic polysul des, and aromatic polyamides. 2-8d Polyesters

Various combinations of reactant(s) and process conditions are potentially available to synthesize polyesters [Fakirov, 2002; Goodman, 1988]. Polyesters can be produced by direct esteri cation of a diacid with a diol (Eq. 2-120) or self-condensation of a hydroxy carboxylic acid (Eq. 2-119). Since polyesteri cation, like many step polymerizations, is an equilibrium reaction, water must be continuously removed to achieve high conversions and high molecular weights. Control of the reaction temperature is important to minimize side reactions such as dehydration of the diol to form diethylene glycol

THE UNITED STATES IN THE TWENTIETH CENTURY: 1946 1990

2-123

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