Synthesis of fluorinated N‐alkyl substituted polyamides

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Abstract
Methods of synthesizing linear, N‐alkyl substituted, fluorine‐containing polyamides of two types were investigated. Type I is represented by the general formula magnified image and Type II by the formula magnified image The method most suitable for Type I polymers consisted in reacting N,N′‐dialkyl substituted diamines with dimethyl perfluoroglutarate, while the technique most suitable for Type II polymers was reaction of N,N′‐dialkyl substituted 2,2,3,3,4,4‐hexafluoropentanediamines with adipyl chloride. Type I polyamides formed more readily and were of higher molecular weights than Type II polyamides. The difficulty in the formation of high molecular weight Type II polyamides is due to the weakly basic properties of the fluorinated diamines. All the higher molecular weight polymers were dark brown rubberlike gums. In general, solubility of the polymers in organic solvents increased as the size of the N‐substituent progressed, from methyl to n‐butyl. Type I polyamides readily hydrolyzed whereas Type II did not. A minimum in the approximate brittle temperatures was noted when R = ethyl for Type I polyamides, and when R = n‐butyl for Type II polyamides.

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