FTIR Spectroscopy Study of the Formation of Cyclic Anhydride Intermediates of Polycarboxylic Acids Catalyzed by Sodium Hypophosphite

Abstract

In recent years, extensive efforts have been made to find formaldehyde-free durable press finishes to replace the traditional formaldehyde-based N-methylol compounds. 1,2,3,4-Butane-tetracarboxylic acid (BTCA) has been the most efficient nonformaldehyde crosslinking agent for cotton, with sodium hypophosphite (NaH2PO2) being the most effective catalyst. In our previous research, we found that a polycarboxylic acid esterifies cellulose through the formation of a five-membered cyclic anhydride intermediate by the dehydration of two adjacent carboxyl groups. In this research, we use Fourier transform infrared spectroscopy (FTIR) to study the formation of cyclic anhydride intermediates by BTCA and poly(maleic acid) (PMA) with and without the presence of NaH2PO2. In the absence of NaH2PO2, BTCA forms the cyclic anhydride only when the temperature reaches the vicinity of its melting point. In the presence of NaH2PO2, however, the anhydride forms at much lower temperatures. We have found that NaH2PO2 weakens the hydrogen bonding between the carboxylic acid groups of BTCA, contributing to accelerated anhy dride formation at lower temperatures. Sodium hypophosphite also accelerates the for mation of the anhydride intermediates by polycarboxylic acids in an amorphous state. The FTIR spectroscopy data show that there is a chemical reaction between the anhydride intermediate and NaH2PO2 when the temperature climbs above 200°C.