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Scheme 3. Baeyer Villiger oxidation of ethylene-vinyl alcohol copolymer.

Polycarboxylates Carboxylate derivatives of poly(vinyl alcohol) are biodegradable and functional in detergents as co-builders, although too costly to be practical replacements for polyacrylic acid at this time. Matsumura et al. polymerized vinyloxyacetic acid [69, 70] and Lever has patented polymers based on vinyl carbamates obtained from the reaction of vinyl chloroformates and amino acids such as aspartic and glutamic acids [71]. Both hydrolyze (Scheme 4), to polyvinyl alcohol, which is biodegradable.

Copolymers of vinyl alcohol with acrylic and/or maleic acid have been evaluated in detergents as potentially biodegradable co-builders in a number of laboratories [72-74], but the results were not encouraging for balancing biodegradation and performance. Higher than 80 mol % of vinyl alcohol is required for biodegradation, and less than 20 mol % for acceptable performance.

The use of polycarboxylic acids in detergents, particularly poly(acrylic acids), and the search for biodegradable alternatives is well established and has been well reviewed in many articles mentioned earlier [12, 18-21] and by Hunter

CH2CO2H CH2CO2H Polyvinyloxyacetic acid


chco2h Chco2h Ch2co2h C

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