Preparation and surface-active properties of telomer-type anionic surfactants from maleic anhydride

Maleic acid alkyl ester and N-alkyl maleamic acid monomers (R_nMa and R_nMaAm; n is alkyl chain length; n=6, 8, 10, 12, 14) were synthesized by the reaction of maleic anhydride with alkyl alcohol or alkylamine. The telomerization of R_nMa or R_nMaAm in the presence of alkanethiol as a chain transfer agent gave telomer-type anionic surfactants (xR_nMa, xR_nMaAm; x is total average number of alkyl chains; x=2.8–3.3) having multialkyl chains and multicarboxylate groups. Their surface-active properties were investigated by several techniques such as surface tension, foaming property, and emulsification power measurements. Critical micelle concentrations (CMC) of xR_nMa were 1/110–1/14 of those of R_nMa with the same alkyl chain length. xR_nMa and xR_nMaAm gave higher efficiencies in lowering the surface tension than R_nMa and R_nMaAm in aqueous solutions. In particular, the surface tension of 3.2R₁₂MaAm was 24.4 mN m⁻¹ at the CMC. Foaming abilities and foam stabilities of xR_nMa and xR_nMaAm were higher than those of R_nMa and R_nMaAm. The addition of 300 ppm of Ca²⁺ to the aqueous solutions rendered the telomers less surface active. Shaking the aqueous solutions of telomers with toluene emulsified them. The highly stable oil-in-water type emulsion was formed by using 3.0R₁₀MaAm and 3.2R₁₂MaAm, and the degree of emulsification was kept at a level of about 80% after 60 min of standing. Thus, telomer-type surfactants showed excellent surface activities that were superior to the corresponding monomers as well as to conventional surfactants. The relationship between alkyl chain length of the telomers and the properties of surface tension, foaming, and emulsification was unclear.