Synthesis and characterization of the solution properties of novel amine functional surfactants

Critical micelle concentration (cmc) values have been determined for the mixed zwitterionic/cationic gemini systems of N-dodecyl- N,N-dimethyl-3-ammonio-1-propanesulfonate (ZW3-12)/N,N 'bis(dimethyldodecyl)-1,4-butanediammonium dibromide (12-4-12) and ZW3-12/N,N'bis(dimethyldodecyl)-1,5-pentanediammonium dibromide (12-5-12). The cmc's for the mixed systems were determined through conductivity measurements. The degree of nonideality of the interaction in the mixed micelle (betam), for each system, was determined according to Rubingh's nonideal solution theory. The systems mixed in near ideal fashion with greater negative deviations displayed at high mole fractions of zwittergent. The ZW3-12/12-4-12 system displayed -betam values at alphaZW3-12 ≥ 0.5, while the ZW3-12/12-5-12 system displayed -betam values over the entire mole fraction range. The slightly favourable interactions can be attributed to increased hydrophobic interactions and decreased repulsions between the ammonium functional groups of the gemini surfactant upon intercalation of zwitterionic head groups. The systems demonstrated almost identical behaviour to the DTAB/12-2-12 system studied by Bakshi et al.74 providing further evidence that ZW3-12 tends to behave as a cationic surfactant in mixed surfactant systems. The 2-D NOESY spectra indicated strong interaction between the head group regions of the gemini and zwitterionic surfactants. These interactions appeared to be stronger in the ZW3-12/12-5-12 system.; Surface tension data were collected for Surfynol CT-121 and blends of Agri-SC with EnviroGem AD-01, Surfynol 104 PG-50, and Surfynol CT-211. The Surfynol and EnviroGem surfactants are produced by Air Products. The surfactant blends as well as Surfynol CT-121 displayed low C20 values and very low surface tension plateaus (in the range of 26-30 mN/m) and are therefore excellent candidates for further trials in the development of solids-washing and bioremediation processes.; Several direct alkylation and reductive amination methods were employed in the attempted N-alkylation of glucosamine. The intention was to synthesize a novel amine surfactant for use in reversible, invert emulsion drilling fluids. Direct alkylation with alkyl halide as well as reductive amination via reduction with metallic magnesium, and potassium formate/catalytic palladium acetate failed largely due to solubility problems and tendency for glucosamine to degrade when heated. Reduction with sodium dithionite resulted in products consisting mainly of sodium sulfate and long chain aldehyde. Reductive amination via reduction with sodium borohydride (NaBH4) produced the most desirable results. The products produced persistent foams and displayed excellent surface tension lowering abilities. The mass spectra of the products indicated the presence of two alkylation products, one being the desired N-alkyl glucosamine product and the other an unknown product with head group corresponding to mass of 327 g/mol. Mass spectra, 1H nmr spectra and elemental results indicated that a number of other undesirable products were also present including borates, un-reacted glucosamine and possible pyrazine-based structures. The future development of better separation techniques may result in the extraction of the pure N-alkylation product.