In this paper, the use of surfactants for solubilization of hydrophobic organic dyes (mainly solvent and disperse dyes) has been reviewed. The effect of parameters such as the chemical structures of the surfactant and the dye, addition of salt and of polyelectrolytes, pH, and temperature on dye solubilization has been discussed. Surfactant self-assemble into micelles in aqueous solution and below the concentration where this occurs—the critical micelle concentration (CMC)—there is no solubilization. Above the CMC, the amount of solubilized dye increases linearly with the increase in surfactant concentration. It is demonstrated that different surfactants work best for different dyes. In general, nonionic surfactants have higher solubilization power than anionic and cationic surfactants. It is likely that the reason for the good performance of nonionic surfactants is that they allow dyes to be accommodated not only in the inner, hydrocarbon part of the micelle but also in the headgroup shell. It is demonstrated that the location of a dye in a surfactant micelle can be assessed from the absorption spectrum of the dye-containing micellar solution.
Three ester-containing cationic gemini surfactants, two with decanoyl chains and either a three-carbon or a six-carbon spacer unit and one with dodecanoyl chains and a three-carbon spacer, were synthesized and evaluated. A corresponding monomeric cationic ester surfactant was used for comparison. This type of amphiphile, a so-called esterquat, is known to undergo rapid hydrolysis above the critical micelle concentration because of micellar catalysis. The esterquat geminis of this work were found to be much more susceptible to hydrolysis than the esterquat monomer. This difference is believed to be caused by anchimeric assistance by the second cationic headgroup in the gemini amphiphiles. However, there is no correlation between the rate of chemical hydrolysis and the rate of biodegradation. The monomeric esterquat, which is the most stable in the chemical hydrolysis experiments, was the only surfactant that passed the test for "readily biodegradable". We also observed a considerable difference in the hydrolysis rate within the small series of gemini surfactants. The amphiphile with two decanoyl chains and a three-carbon spacer, N,N'-bis(2-(decanoyloxy)ethyl)-N,N,N',N'-tetramethyl-1,3-propanediammonium dibromide, had the fastest rate of hydrolysis. This surfactant also exhibited a considerably lower degree of micelle ionization than the other surfactants, which is believed to be due to the closer proximity of the charged groups on the micelle surface. A small distance between headgroups will give more pronounced neighboring group participation, accounting for the increased rate of hydrolysis. An interesting property of the surfactant that is the most susceptible to hydrolysis is that it gives rise to an extremly stable foam. We propose that the foam stability is a result of the partial hydrolysis of the surfactant generating sodium decanoate, an anionic surfactant, that forms a mixed film with the starting cationic gemini surfactant. It is known that mixed monolayers in which there is a strong attractive interaction between surfactant headgroups can lead to stable foams.
A sustainable approach that highly mimics bone-material deposition is reported to produce mechanically stable, degradable composites with nanostructures resembling that of natural bone. Molecular self-assembly combining intermolecular crosslinking leads to resilient matrices possessing long-range ordered aqueous domains, inside which moderately aligned poorly crystalline apatite is converted from the transient amorphous calcium phosphate phase.
Epoxy resin monomers, including diglycidyl ethers of bisphenol A and F (DGEBA and DGEBF), are extensively used as building blocks for thermosetting polymers. However, they are known to cause widespread contact allergy. This research describes a number of alternative epoxy resin monomers, designed with the aim of reducing the skin sensitizing potency whilst maintaining the ability to form thermosetting polymers. The compounds were designed, synthesized, assessed for skin sensitizing potency using the in vivo murine local lymph node assay, and tested for technical applicability using thermogravimetric analysis and differential scanning calorimetry. All the novel epoxy resin monomers had decreased skin sensitization potencies compared to DGEBA and DGEBF. With respect to EC3 values, which is the estimated concentration of a substance required to induce a 3-fold increase in sensitization compared to a control, the best of the new monomers had a value approximately 2.5 times higher than those of DGEBA and DGEBF. The diepoxides were reacted with triethylenetetramine and four out of the six novel monomers gave polymers with a thermal stability comparable to that obtained with DGEBA and DGEBF. The new epoxy resin monomers have the potential to replace DGEBA and DGEBF, leading to a decreased incidence of contact allergy due to epoxy resins, decreased healthcare costs, and an increased quality of life for those handling thermosetting materials.
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