Synthesis and characterization of TRITON™ X-based surfactants with carboxylic or amino groups in the oxyethylene chain end

This paper describes the synthesis and characterization of a series of TRITON (TM) X-based surfactants with a predominantly alkyl phenol ethoxylate (APE) backbone and carboxylic or amino chain ends. Three carboxylic acid-containing TRITON X (or APE)-derivatives, [OPE2-COOH], [OPE5-COOH], and [OPE10-COOH], were prepared from commercially available octyl phenol ethoxylate (OPE) of different oxyethylene units (i.e., n = 2, 5, and 10) and ethyl bromoacetate via a simple etherification reaction followed by saponification. Two amine-containing TRITON X-derivatives, [NPE10-NH2] and [NPE10-imidazole], were prepared based on modifications of mesylate of nonyl phenol ethoxylate (NPE) of 10 oxyethylene units reacted with ammonia and imidazole, respectively. Depending on their composition and chain length of oxyethylene units used in the reaction, the surfactants show different thermal degradation behaviors. The carboxylic acid-containing surfactants give no char at high temperatures under air condition. (c) 2007 Wiley Periodicals, Inc.