Alicyclic nylons

The fiftieth anniversary of the announcement of nylon as the first synthetic organic textile fiber by the Du Pont Co. on October 27,1938 was celebrated as a significant event by the textile industry in 1988 (1,2). The announcement was the culmination of the fundamental research efforts of W. H. Carothers and his team at Du Pont (3). Carothers synthesized diamines from C2 to C18 in order for them to react with a variety of aliphatic dicarboxylic acids to make polyamides for evaluation as fibers (4—10). Alicyclic and aromatic diamines and dicarboxylic acids were also included. Nylon-6,6 was ultimately selected for scale-up and development because of its favorable melting point ( 260° C), best balance of properties, and lower manufacturing cost. The pilot plant for nylon-6,6 was completed in Wilmington, Delaware, in July, 1938, and a product was introduced on the market as Exton brisdes for Dr. West s toothbrushes (2). The first nylon filament plant was built in 1939 at Seaford, Delaware, and nylon stockings went on sale on October 24,1939 only to residents of Wilmington, and then nationally, on May 15, 1940 (2). 

Uses The alicyclic hydrocarbons have numerous industrial applications. Cyclopropane (C3H6) is used as an anesthetic. Cyclohexane (CgH ) is used as a chemical intermediate as an organic solvent for oils, fats, waxes, and resins and for the extraction of essential oils in perfume manufacturing industries. Cyclohexene (C6H10) is used in the manufacture of maleic acid, cyclohexane carboxylic acid, and adipic acid. Methyl cyclohexane (C7H14) is used for the production of organic synthetics such as cellulose ethers. These compounds are used in different industries such as adipic acid makers, benzene makers, fat processors, fungicide makers, lacquerers, nylon makers, oil processors, paint removers, plastic molders, resin makers, rubber makers, varnish removers, and wax makers. 

Aliphatic and alicyclic molecules such as cyclohexane undergo photosubstitution with nitrosyl chloride (Pape, l%7). The reaction is of considerable industrial importance in the synthesis of 6-caprolactam, an intermediate in the manufacture of polyamides (nylon 6). (Cf. Fischer, 1978.) At long wavelengths a cage four-center transition state between alkane and an excited nitrosyl chloride molecule is involved, as indicated in Scheme 63. In contrast to light-induced halogenation, photonitrosation has a quantum yield smaller than unity, and is not a chain reaction. 

Ferroelectridty has been observed in nylon-7, nylon-11, nylon-75, nylon-77, fluor-inated nykm-3S, nylon-SS, nyloo-75 and nylon-95, as well as several alicyclic and aromatic nylons. Ferroelectridty has been observed in nylons prepared from m-xylylenedi-amine and aliphatic dicaiboxylic adds, referred as nylon-hOCDs. Alicyclic and aromatic nylons picpaied from 13-bis(aminamethyl)cyclobexane (BAC) and aliphatic dicarboxylk adds were also found to be ferroelectric. The newly developed fluoro-nylons having odd... 

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