Black Truffle, Nanocrystals and Flexible Films: Recent Literature Findings

In this monthly survey of recent patent and literature research, the author describes money-making ideas in the personal care industry, ranging from a water-soluble scrubbing agent and black truffle for cell proliferation, to ascorbyl palmitate nanocrystals and an o/w emulsion for eyelash-volumizing and lengthening, among others.

Skin and Skin Care

Water-soluble scrubbing agent for oily cleansers: Kosei Co., Ltd., discloses a water-soluble scrubbing agent with an average particle diameter of 200 μm that is suitable for use in an oily skin cleanser.¹ The scrubbing agent contains a solid polyethylene glycol as a paste or solid and a water-soluble silicone-based surfactant with a HLB value > 7. An example of an oily skin cleanser incorporating the scrubbing agent also is disclosed (see Formula 1).

The formula is prepared by incorporating 50 parts polyethylene glycol with a molecular weight of 20,000 and 50 parts polyoxyethylene methylpolysiloxane copolymer with an HLB of 9. This skin cleanser was reported to exhibit an excellent cleansing effect for removal of lipstick from the skin without leaving a sticky after feel.

Emulsion bathing preparations: Kao Corp. discloses emulsion-type liquid bathing preparations containing hydrocarbon oils and polyoxyethylene alkyl phosphate esters.² These bath preparations have a median emulsion particle diameter of 0.1–0.4 μm and contain 10–45% w/w oily ingredients, containing 10–40% w/w hydrocarbon oils containing petrolatum; and 0.1–5.0% w/w polyoxyethylene C10-14-alkyl phosphate esters or their salts. The final preparation exhibited a whey-like, transparent appearance when added to bath water and produced a moisturizing effect. An example is shown in Formula 2.

Leucine, isoleucine in skin whitening: S.S. Pharmaceutical Co., Ltd., discloses skin-whitening compositions containing leucine and/or isoleucine as active components.³ The compositions may further contain alanine and/or glycine. An example of a skin-whitening lotion is shown in Formula 3.

Alkyleneoxide derivatives for anti-acne: Shiseido Co., Ltd., discloses skin compositions containing alkyleneoxide derivatives that are reported to have excellent acne prevention effects.⁴ The disclosed compositions are characterized by containing: a) an alkyleneoxide derivative represented by the formula: 

R₁O[(AO)_m(EO)_n]R₂

where AO = C3-4 oxyalkylene; EO = oxyethylene; m and n = 1–70; the ratio of (EO)_n to (AO)_m(EO)_n = 20–80%; AO and EO may form block or randomly adduct; and R₁, R₂ = C1-4 alkyl; b) an anti-inflammatory agent; and c) a keratin-softening/peeling agent, antibacterial/antiseptic agent, and/or a sebum-preventing/absorbing agent. An example of an anti-acne composition is shown in Formula 4.

Skin-freshening, softening o/w emulsion: Shiseido Co., Ltd., also discloses o/w cosmetic emulsions containing polyoxyethylene sorbitan fatty derivatives, surfactants and higher alcohols.⁵ This oil-in-water composition demonstrates skin-freshening and softening effects and has good skin permeability and storage stability. The disclosed composition is characterized by containing: a) a C14-18 linear saturated fatty acid-derived polyoxyethylene sorbitan fatty acid ester; b) an anionic or nonionic surfactant; c) a C14-22 unbranched higher alcohol, and d) glycerin monoalkyl ester, glycerin monoalkyl ether, sorbitan monoalkyl ester, sorbitan monoalkyl ether, sterol and/or a branched higher alcohol.

The composition shows molar ratios of (1):(2) = 1:0.05–1:1.5; and [(1) + (2)] : [(3) + (4)] = 1:3–1:6; but (3)/[(3) + (4)] = > 0.3. The composition may further contain an organic acid or its salt. The composition also specifically contains a minimized amount of a water-soluble thickener (< 0.1%). An example is shown in Formula 5.

Tuber enzymic hydrolyzates for cell proliferation: Kao Corp. discloses epidermal cell proliferation stimulators containing tuber enzymic hydrolyzates from Tuber mycelium; e.g., Tuber magnatum and/or Tuber melanosporum mycelium.⁶ The epidermal cell proliferation stimulator is suitable for use in antiaging, skin-lightening or wound-healing applications. For example, freeze-dried and crushed Tuber melanosporum (black truffle) mycelium was treated with Actinase E and Tunicase FN to obtain an enzymic hydrolyzate for studying its effect on epidermal cell proliferation in vitro.

Makeup

Oligomers, powders for eyelashes and brows: Kosei Co., Ltd., discloses makeup for eyelashes and eyebrows comprising olefin oligomers and surface-treated powders.⁷ The disclosed makeup contains alpha-olefin oligomers, powders that are surface-treated with siloxy group-containing methacrylate copolymers, volatile solvents and, optionally, solid oils. An example of a mascara gel is shown in Formula 6.

Colored fibers, treated powders for eyelashes, brows: Kosei Co., Ltd., has diclosed cosmetics for eyelashes and eyebrows comprising colored fibers and surface-treated powders.⁸ The described cosmetics include colored fibers and powders that are surface-treated with siloxy group-containing methacrylate copolymers, in addition to membrane-forming ingredients and, optionally, solid oils. An example of a mascara cream is shown in Formula 7.

O/W emulsions for eyelashes: Kosei Co., Ltd., also discloses o/w emulsions for eyelashes containing water-soluble polymers and modified organopolysiloxane.⁹ This cosmetic composition provides a volumizing and lengthening effect and contains a stringing, water-soluble polymer and a solid or paste, long-chain alkyl-modified organopolysiloxane or long-chain alkoxy-modified organopolysiloxane having a melting point < 60°C. The composition may further contain a film-forming polymer emulsion and/or a wax. An example of a cream-type mascara composition is shown in Formula 8.

Monodisperse particles for keratin surfaces: L’Oréal discloses a cosmetic composition for keratinous surfaces comprising monodisperse particles in a liquid medium.¹⁰ The invention is designed for, but not limited to, application to keratinous materials, in particular the skin, lips, nails or eyelashes. The composition comprises: a physiologically acceptable liquid medium that is anhydrous and non-pulverulent, including an oily phase such as a polysiloxane; and monodisperse particles suitable for forming an ordered lattice of monodisperse particles on a substrate, onto which the composition is applied.

A kit is described comprising a first composition for application onto keratinous materials, and a second composition for application onto the first composition. The second composition comprises a physiologically acceptable medium and monodisperse particles. Thus, an eyeshadow composition contained 30% polystyrene particles, 67.5% pentaerythrityl tetraisostearate and 2.5% PEG dimethicone. A blue-green color is obtained after the composition has been applied. A base coat containing 80% acrylates/ammonium methacrylate copolymer^a, 10% black colorant^b and 10% water may be applied to the eyelids prior to application of the above composition. ^a Ultrasol 2075 (INCI: Acrylates/ammonium methacrylate copolymer) is a product of Presperse.
^b Cab-O-Jet 200 is a black colorant from Cabot that is used for inks.

Interesting Raw Materials

Water-, oil-repellent cosmetics: Kao Corp. discloses water- and oil-repellent cosmetics containing fluorine-modified silicones and perfluoroalkyl-containing liquid oils.¹¹ The described compositions contain, a):

R₆SiR₇R₈O­[SiR₁[(CH₂)_mO(CH₂)_nR_f]O]_p (SiR₂R₃O)_q­(SiR₄R₅O)_r­SiR₆R₇R₈

where R_f = C1-20 perfluoroalkyl; R₁, R₂, R₄, R₅, R₆ and R₇ = C1-4 linear or branched hydrocarbyl phenyl; R₃ = a linear or branched hydrocarbyl having an average carbon number above 20 and less than or equal to 50; R₈ = C1-4 linear or branched hydrocarbyl, linear or branched hydrocarbyl having an average carbon number above 20 and less than or equal to 50; m = 2-3; n = 1-6; p = 1-50; q and r = 0-50; and when R₈ = C1-4 linear or branched hydrocarbyl, then q = 1-50; b) liquid oils having perfluoroalkyl groups; and, optionally, c) powders treated with fluoride-containing compounds.

Thus, the reaction of Me₃SiO(SiMeHO)₃₂SiMe₃ with C₁₀F₂₁(CH₂)₂­OCH₂CH:CH₂ and alpha-olefin with an average carbon number of 24 yielded Me₃SiO[SiMe­[(CH₂)₃O(CH₂)₂C₁₀F₂₁]O]₁₇­[SiMe(CaH₂a+1)O]₁₅SiMe₃ or I. A cosmetic foundation containing 20% w/w octamethylcyclotetrasiloxane, 3% w/w I, 6% w/w fluoroalkoxyalkyl-modified silicone oil and fluoro compound-treated pigment powders, etc., showed good water and oil repellency, a good skin feel and low color migration to clothing.

Ascorbyl palmitate nanocrystals for nanosuspension: Teeranachaideekul et al. have published on the development of ascorbyl palmitate nanocrystals for nanosuspension.¹² Ascorbyl palmitate (AP) is an antioxidant used in both the cosmetics and foods industries. Owing to its poor solubility and instability caused by oxidation, the aim of this study was to investigate the feasibility of applying the nanosuspension technology by high-pressure homogenization (HPH) to enhance the chemical stability of AP, followed by lyophilization.

Sodium dodecyl sulfate (SDS) and polysorbate 80 were chosen as emulsifying agents to stabilize the AP nanosuspensions. After three months of storage at 4°C, 25°C and 40°C, the photon correlation spectroscopy (PCS) analysis of AP nanosuspensions revealed that the mean particle size of those formulations stabilized with SDS significantly increased, as compared with those formulas stabilized with polysorbate 80. The results from both atomic force microscopy and SEM revealed AP nanocrystals with a cubic-like shape. The percentage of AP remaining in nanosuspensions stabilized with polysorbate 80 was higher than 90% after the three months of storage at 4°C, 25°C and 40°C.

To increase the chemical stability of AP nanosuspensions, a drug powder was prepared by lyophilization. The effect of the cryoprotectant trehalose on the physical stability was evaluated at different concentrations. After redispersing the lyophilized product, the mean size of AP nanosuspensions without trehalose was found to be significantly higher than those including trehalose. After three months of storage at 25°C, the mean size of lyophilized AP nanosuspensions remained constant. X-ray diffraction revealed the crystal character of AP nanocrystals after HPH and lyophilization.

Interesting New Vehicles/Formulations

Phospholipid, sphingosine derivatives in vesicle compositions: Kosei Co., Ltd., discloses vesicle compositions containing phospholipid and sphingosine derivatives, and skin compositions containing the same.¹³ The vesicle composition reportedly excels in skin permeability and storage stability without causing discoloration or odor. It has been shown to be suitable in a skin composition wherein the vesicle composition contains: at least one phospholipid derivative containing an unsaturated fatty acid residue in the second acyl group, and at least one sphingosine derivative. The vesicle composition may further contain cholesterol and/or phytosterol.

In a disclosed formula containing the vesicle composition (see Formula 9), hydrogenated soybean phosphatidylcholine was treated with phospholipase A2 to give 1-acyl-2-lysophosphatidylcholine, and further treated with oleic anhydride to obtain 1-acyl-2-oleoyl-3-phosphatidylcholine. The formula included 40 parts of the vesicle composition with other ingredients to create a cosmetic lotion.

Ascorbic acid glucoside, peptides in liquid cosmetics: Kosei Co., Ltd., also discloses liquid cosmetic compositions containing ascorbic acid glucoside and basic peptides.¹⁴ The liquid cosmetic composition disclosed is characterized by containing L-ascorbic acid glucoside and a basic peptide, e.g., N-beta-alanyl-L-histidine, wherein the use of the basic peptide improves storage stability of the ascorbyl glucoside without causing discoloration. An example is shown in Formula 10.

Cosmetic/therapeutic compositions, flexible solid films: Biofarmitalia S.p.A. discloses solid cosmetic and therapeutic compositions and flexible solid films comprising hyaluronic acid. These compositions are applicable to human skin and gel upon contact with water.¹⁵ The compositions prepared as flexible solid films can be used for cosmetic and/or therapeutic purposes. They may contain hyaluronic acid, a fine, inert powder, and water as essential components. Thus, a solid film with a hydrating and filling effect on cutaneous microprotuberances comprised: water as a solvent at 80.2 kg; hyaluronic acid as a filmogen at 9.8 kg; and lauroyl lysine, an inert powder, at 10 kg.

Silicone elastomers in cosmetics: L’Oréal discloses an anhydrous cosmetic composition comprising nonspherical silicone elastomers and a silicone elastomer encapsulated in silicone.¹⁶ The compounds can be used for makeup and hair compositions. An example is shown in Formula 11.

Hydrofluoro ethers, polyhydric alcohols and emulsifiers: Shiseido Co., Ltd., discloses cosmetic compositions containing hydrofluoro ethers, polyhydric alcohols and emulsifiers.¹⁷ The disclosed invention relates to a composition that provides a sensory cue of feeling cool then warm on the skin, without leaving a sticky residue. The described composition contains: a) a hydrofluoro ether having a viscosity at 25°C < 5 mPa•s; b) a polyhydric alcohol; and c) an emulsifier; and wherein the composition contains little or no water. An example is shown in Formula 12.

Kosei Co., Ltd., also discloses liquid o/w cosmetic emulsion compositions.¹⁸ These liquid o/w cosmetic emulsions contain higher amounts of oil with low viscosity, and having good storage stability. One example composition disclosed contained 0.5–2.0% isostearic acid; 1–3% basic amino acid; 7–20% of an oily component; 0.2–1.5% glyceryl stearate; and 0.2–1.5% of a higher alcohol. The composition reportedly showed a viscosity at 25°C of < 500 mPa•s. An example is shown in Formula 13.

Reproduction of all or part of this article is strictly prohibited.

References

1. JP 2008 88,093, Oily skin cleanser containing novel water-soluble scrubbing agent and the scrubbing agent, Kosei Co., Ltd., Japan (Apr 17, 2008)
2. JP 2008 81,426, Emulsion-type liquid bathing preparations containing hydrocarbon oils and polyoxyethylene alkyl phosphate esters, Kao Corp., Japan (Apr 10, 2008)
3. JP 2008 88,113, Skin-whitening compositions containing leucine and/or isoleucine, S.S. Pharmaceutical Co., Ltd., Japan (Apr 17, 2008)
4. JP 2008 88,127, Anti-acne skin compositions containing alkyleneoxide derivatives, Shiseido Co., Ltd., Japan (Apr 17, 2008)
5. JP 2008 88,129, Oil-in-water cosmetic emulsion compositions containing polyoxyethylene sorbitan fatty derivatives, surfactants and higher alcohols, Shiseido Co., Ltd., Japan (Apr 17, 2008)
6. JP 2008 88,121, Epidermal cell proliferation stimulators containing Tuber enzymic hydrolyzates, Kao Corp., Japan (Apr 17, 2008)
7. JP 2008 88,069, Makeup for eyelashes and eyebrows comprising olefin oligomer and surface-treated powders, Kosei Co., Ltd., Japan (Apr 17, 2008)
8. JP 2008 88,070, Cosmetics for eyelashes and eyebrows comprising colored fibers and surface-treated powders, Kosei Co., Ltd., Japan (Apr 17, 2008)
9. JP 2008 88,112, Oil-in-water cosmetics for eyelashes containing water-soluble polymers and modified organopolysiloxane, Kosei Co., Ltd., Japan (Apr 17, 2008)
10. US 2008 89,917, Cosmetic composition for keratinous surfaces comprising monodisperse particles in liquid medium, L’Oréal, France (Apr 17, 2008)
11. JP 2008 81,413, Water- and oil-repellent cosmetics containing fluorine-modified silicones and perfluoroalkyl-containing liquid oils, Kao Corp., Japan (Apr 10, 2008)
12. V Teeranachaideekul et al, Development of ascorbyl palmitate nanocrystals applying the nanosuspension technology, Intl Jrnl Pharma 354(1–2) 227–234 (2008) (in English)
13. JP 2008 88,133, Vesicle compositions containing phospholipid derivatives and sphingosine derivatives, and skin compositions containing the same, Kosei Co., Ltd., Japan (Apr 17, 2008)
14. JP 2008 88,088, Liquid cosmetic compositions containing ascorbic acid glucoside and basic peptides, Kosei Co., Ltd., Japan (Apr 17, 2008)
15. US 2008 85,291, Solid cosmetic and therapeutic compositions, flexible solid films, comprising hyaluronic acid, applicable to the human skin and gellable on contact with water, Biofarmitalia S.p.A., Italy (Apr 10, 2008)
16. EP 1,911,440, Cosmetic composition comprising silicone elastomers, L’Oréal, France (Apr 16, 2008)
17. JP 2008 88,081, Cosmetic compositions containing hydrofluoro ethers, polyhydric alcohols and emulsifiers, Shiseido Co., Ltd., Japan (Apr 17, 2008)
18. JP 2008 88,092, Liquid oil-in-water cosmetic emulsion compositions, Kosei Co., Ltd., Japan (Apr 17, 2008)