Preparation, Characterization and Evaluation of Organogel-Based Lipstick Formulations: Application in Cosmetics

1,3:2,4-Dibenzylidene-D-sorbitol (DBS) and 12-hydroxystearic acid (12-HSA) are well-known as low-molecular-weight organogelators (LMOGs) capable of gelling an organic liquid phase. Considering their unique chemical and physical properties, we assessed their potential effects in new lipstick formulations by discrimination testing; in vitro measurements of the sun protection factor (SPF); and thermal, mechanical and texture analyzes. DBS and 12-HSA were used to formulate four types of lipsticks: L1 (1% DBS), L2 (10% 12-HSA), L3 (1.5% DBS) and L4 (control, no LMOGs). The lipsticks were tested for sensory perception with an untrained panel of 16 consumers. LMOG formulations exhibited higher UVA protection factor (UVA-PF) and in vitro SPF, particularly in the 12-HSA-based lipstick. Regarding thermal properties, the 12-HSA-based lipstick and those without LMOGs were more heat-amenable compared to thermoresistant DBS-based lipsticks. The results also showed the viscoelastic and thermally reversible properties of LMOGs and their effect of increasing pay-off values. In general, the texture analysis indicated that 12-HSA-based lipstick was significantly harder to bend compared to control, while the other formulations became softer and easier to bend throughout the stability study. This work suggests the potential use of LMOGs as a structuring agent for lipsticks, paving the way towards more photoprotective and sustainable alternatives.

Preliminary Study of the Potential Photoprotective Effect of Organogel-Based Lipstick Formulations: Texture Analysis, Rheological, Thermal and Sensory Properties

With the increase in occupation-specific risks of lip cancer associated with solar radiation, there is a need for developing photoprotective lipsticks to protect skin against harmful effects of UV radiation. Considering the unique chemical and physical properties of low-molecular-weight organogelators (LMOGs), the present study intended to assess the UV protective properties of LMOGs-based lipstick formulations. In this study, dibenzylidene-D-sorbitol (DBS) and 12-hydroxystearic acid (12-HSA) were used to formulate lipsticks : L1 (1% DBS), L2 (10% 12-HSA), L3 (1.5% DBS) and L4 (control, no LMOGs). The lipstick formulations were tested for in vitro sun protection factors (SPF), UVA protection factor (UVA-PF), thermal, mechanical and texture analyses. Lipsticks with LMOGs exhibited higher UVA-PF and SPF, and more particularly 12-HSA-based lipstick. Results showed also the viscoelastic and heat-resistant properties of LMOGs and their effect of increasing pay-off values. In general, texture analysis indicating that 12-HSA-based lipstick was significantly harder to bend compared to control, while other formulations became softer and easier to bend throughout the stability study. Finally, sensorial and instrumental analyses permitted to classify lipsticks into two groups. This work suggests the potential use of LMOGs as a structuring agent for lipsticks paving the way towards more photoprotective and sustainable-derived alternatives.

(R)-10-Hydroxystearic Acid: Crystals vs. Organogel

The chiral (R)-10-hydroxystearic acid ((R)-10-HSA) is a positional homologue of both (R)-12-HSA and (R)-9-HSA with the OH group in an intermediate position. While (R)-12-HSA is one of the best-known low-molecular-weight organogelators, (R)-9-HSA is not, but it forms crystals in several solvents. With the aim to gain information on the structural role of hydrogen-bonding interactions of the carbinol OH groups, we investigated the behavior of (R)-10-HSA in various solvents. This isomer displays an intermediate behavior between (R)-9 and (R)-12-HSA, producing a stable gel exclusively in paraffin oil, while it crystallizes in other organic solvents. Here, we report the X-ray structure of a single crystal of (R)-10-HSA as well as some structural information on its polymorphism, obtained through X-ray Powder Diffraction (XRPD) and Infrared Spectroscopy (IR). This case study provides new elements to elucidate the structural determinants of the microscopic architectures that lead to the formation of organogels of stearic acid derivatives.

Pteridine derivatives: novel low-molecular-weight organogelators and their piezofluorochromism

Here, π-conjugated compounds based on pteridine derivatives were synthesized and their self-assembling behaviors in a variety of organic solvents and piezofluorochromism were studied.

In situ formation of low molecular weight organogelators for slick solidification

Instantaneous gelation: a reactive precursors approach for the near-instant gelation of oil-on-water slicks down to −5 °C.

Gelating Abilities of Two-Component System of Catecholic Derivatives and a Boronic Acid

In the last two decades, various kinds of the low-molecular-weight organogelators (LMOGs) have been investigated in terms of technological applications in various fields as well as their fundamental scientific properties. The process of gelation is generally considered to arise from immobilization of the solvents in the three-dimensional networks formed by the assembly of gelator molecules through weak intermolecular noncovalent interactions. From these points of view a huge number of organogelators have been developed so far. In the course of our research on LMOGs we have noticed a mixture of two gelators could show a different trend in gelation compared to the single gelator. It is well known that the catecholic moiety easily forms cyclic boronate esters with the boronic acid. Thus, we have investigated the two-component system based on cyclic boronate esters formed by the catechols and a boronic acid in terms of the control of gelation capability. Basic gelation properties of the constituent catecholic gelators have also been clarified. The catecholic gelators with the amide unit form no gel by addition of the boronic acid. In contrast, the catecholic gelators with the glutamic acid moiety improve their gelation abilities by mixing with the boronic acid. Furthermore, the gelation ability of the catecholic gelators having the urea unit is maintained after addition of the boronic acid. It has been found that gelation abilities of the catecholic gelators are highly affected by addition of the boronic acid. In terms of practical applications some gels can be obtained by on-site mixture of two kinds of solutions.