Heated Sunless Tanning for Rapid Color and Other Topics: Literature Findings

This month’s survey of recent patent and research literature describes money-making ideas for personal care product development, including whitening and skin wrinkle-fighting women’s underwear, heated sunless tanners for rapid color development and collagen stimulation via beta-thujaplicin, among others.

Skin and Skin Care
Skin lightening preparation:
Beiersdorf AG used 3-(4-hydroxy-3- methoxyphenyl)-1-(4-hydroxyphenyl)-propane-1-one to address hyper- pigmentation in cosmetic and dermatological preparations.1 An example of a skin lightening cream is shown in Formula 1.

Heated sunless tanner for rapid color: Unilever PLC disclosed a sunless tanning product that imparts faster color to skin when dispensed through a heating device.2 At RT, a body lotion containing 1.50% dihydroxyacetone as the tanning agent was prepared and applied to a panelist. The preheated sample delivered a bronze glow within five minutes while an identical, non-heated sample required more than double the time to achieve similar coloration.

Improved moisturization with heated niacinamide: Unilever PLC has also found that heated niacinamide improves skin moisturization.3 A body lotion containing 1.50% niacinamide together with glycerin, stearic acid, magnesium aluminum silicate, silicone, glyceryl monostearate/stearamide AMP, isopropyl myristate, petrolatum, triethanolamine, glycerol monostearate, cetyl alcohol, fragrance, DMDM hydantoina, titanium dioxide, disodium EDTA and water was prepared and applied to a panelist. The preheated composition imparted more rapid moisturization than expected when compared with the non-heated sample at RT, which resulted in drier, less moisturized skin.

Protecting skin from osmotic shock: Sederma published a patent on homarine and erythritol in a moisturizing cosmetic or dermopharmaceutic composition.4 The company also disclosed a method to non-therapeutically treat the skin to improve cutaneous hydration, prevent and/or treat cutaneous dryness signs, restore and/or protect the cutaneous barrier function and protect cells of the skin and/or the scalp from osmotic shock such as that which is UV-induced. After inducing hyperosmotic shock in cultured human keratinocytes, researchers showed the combination of homarine and erythritol to produce osmo-protective effects. Various products containing this combination were provided.

Self-emulsifying bath compositions: Kao Corp. disclosed a self-emulsifying bath composition that forms a uniform milky emulsion when combined with water.5 The composition includes a liquid hydrocarbon oil, glycerin, at least two different nonionic surfactants with a hydrophilic-lipophilic balance range of 8.5–16 HLB, and water. The composition was found to have good storage stability; an example is shown in Formula 2.

Tyrosinase inhibitors: Eastman Chemical Co. has incorporated 5-hydroxy-2-methyl-4H-pyran-4-one esters as novel tyrosinase inhibitors in skin-brightening cosmetic compositions.6 The company also has disclosed how to make and use the compositions.

Kojic acid (50.0 g; 352 mmol), a tyrosinase inhibitor with an EC50 of 17.0 muM, was carefully added in portions over a period of 30 min to a stirring solution of 150 mL thionyl chloride containing 100 mL hexane. After an additional 3.5 hr of stirring, chlorokojic acid (50.9 g; 90% yield) was produced from the mixture and this acid was found to be a more potent inhibitor of tyrosinase than kojic acid, with an EC50 of 6.8 muM.

Chlorokojic acid (20.0 g; 125 mmol) was then added in portions to water (60 mL) and heated to approximately 50°C. To the water and chlorokojic acid mixture, zinc dust (16.2 g) was carefully added in portions, and concentrated hydrochloric acid (37 mL) was added dropwise over 60 min. The reaction was vigorously stirred for an additional 3 hr and excess zinc was removed. The resulting allomaltol was found to be a more potent inhibitor of tyrosinase than kojic acid, with an EC50 of 3.4 muM.

Finally, allomaltol (600 mg; 4.76 mmol) was diluted with approximately 20 mL of anhydrous tetrahydrofuran (THF) and stirred to afford a solution. Trimethylamine (833 mul; 6.33 mmol) was added dropwise to the allomaltol and THF, and the contents were stirred for approximately 5 min. Acetic anhydride (641 mul; 5.00 mmol) was then added dropwise, capped and stirred at RT. Once complete, the reaction mixture was concentrated under reduced pressure, and the contents were purified by silica gel chromatography to afford 650 mg of 6-methyl-4-oxo-4H-pyran-3-yl acetate (3.87 mmol; 81% yield), which exhibited an EC50 of 106 muM.

Stimulating collagen with beta-thujaplicin: Hinoki Shinyaku KK sourced beta-thujaplicin to stimulate collagen production in skin care applications.7 At 0.00001–2.0% w/w, beta-thujaplicin was found to produce collagen in topical drug and skin care applications to prevent wrinkles or promote wound repair.

Tomato antioxidants for skin: Cefali et al. report the use of tomato as a topical antioxidant.8 Tomatoes are the principal source of lycopene, a carotenoid with high antioxidant activity that can be used topically as a phytocosmetic to combat skin aging. The aim of this study was to develop a lycopene-rich extract from tomato pulp. The extract was analyzed using UV/vis spectroscopy, thin layer chromatography and high performance liquid chromatography. Oxidant activity was analyzed using the free radical DPPH method.

In the apolar tomato fraction rich in carotenoids, the presence of 96.70% lycopene was confirmed, and evaluation of the antioxidant capacity revealed activity (IC50 = 0.311 mg/mL). The authors concluded that tomato could be used as a source of antioxidants for topical use.

Hair and Hair Care
Foaming, cleansing shampoos: Kracie Home Products Ltd. disclosed shampoos containing surfactants and polyhydric alcohols.9 The shampoos provided excellent foam and cleansing and conditioning effects, and were stable at low temperatures. The compositions consisted of fatty acid soaps containing lauric, myristic, palmitic and/or stearic acids; amphoteric and/or semipolar surfactants; polyhydric alcohols; and water-soluble polymers. An example is shown in Formula 3.

Softness via amino-modified silicones: Milbon Co., Ltd. has developed hair compositions containing amino-modified silicones to provide softness to damaged hair; these compositions displayed good storage stability and did not yellow.10 The described compositions are suitable for hair conditioning and as a pre- or post-treatment agents for permanent hair wave-setting. They contain C12-22 alcohol, a cationic surfactant, a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene alkyl ether and an amino-modified silicone. The amino-modified silicone has an amino content of 0.5–3.0%. The amount of cationic surfactant formulated in the composition was less than the sum of the polyoxyethylene alkyl ether and the amino-modified silicone. The composition could further contain a glycerin fatty acid ester. An example of such an emulsified hair cosmetic composition at pH 4 is shown in Formula 4.

Sun Care
Stable, long-lasting sunscreen: Kosei Co., Ltd. disclosed a w/o sunscreen composition that is stable and long-lasting, provides a good afterfeel to the skin, and blocks UV radiation.11 The composition is comprised of: a partially cross-linked polyether-modified organopolysiloxane; organotitanate-treated zinc oxide fine particles and/or organotitanate-treated titanium oxide particles; a silicone oil; glyceryl trioctanoate, glyceryl tri(caprate/caprylate) and/or neopentyl glycol dioctanoate; and inulin fatty acid ester and/or inulin hydrolyzate fatty acid ester. An example is shown in Formula 5.

Color Cosmetics
Cationic copolymer for added radiance: Unilever PLC formulated a composition containing a cationic copolymer with a monomer unit of acryloylethyl tri(C1-C3 alkyl)ammonium salt in a cosmetically acceptable carrier with a starch to impart radiance with soft focus effects on the skin.12 Acrylamide/acryloylethyltrimethylammonium chloride/tris(hydroxymethyl)acrylamidomethane copolymer was the preferred cationic copolymer. In addition, a cross-linked cationic copolymer was used to significantly enhance the tanning effect, and no streaking was observed.

Pentaerythritol ester for gloss: Shiseido Co., Ltd. disclosed cosmetic compositions containing pentaerythritol mono(2-ethylhexanoate) tribenzoate and a carrier.13 The compositions apply smoothly and provide a glossy look. An example of a lipstick is shown in Formula 6.

Quick-drying nail polish: Mandom Corp. has utilized styrene copolymers, fatty acid esters, alkanediols and lower alcohols to create a nail polish that dries quickly and forms a long-lasting glossy film on the nails with good pigment dispersibility.14 The composition contains a styrene copolymer, a fatty acid ester nonionic surfactant, a C5-10 1,2-alkanediol, a lower alcohol and water. The composition may further contain a viscous mineral oil and/or a water-soluble polysaccharide. An example of a nail polish composition is shown in Formula 7.

Antibacterial peptides: Spiderbiotech S.r.l published a patent on monomeric and multimeric peptidic compounds that have antimicrobial activity, particularly against Gram positive and Gram negative bacteria.15 The compositions can be used for medical purposes, as disinfectants, in detergents or as preservatives. Methylbutyrate (1.9%), prenyl acetate (1.4%), 2-methylbutyl 2-methylbutyrate (1.2%) and 2-methylbutyl acetate (1.2%), were studied for their antimicrobial effects. Specifically, a Roman chamomile sample showed high antimicrobial activity against all strains of tested microbes.

A similar result was found for 2-methylbutyl 2-methylbutyrate, 2-methylbutyl acetate and prenyl acetate. Surprisingly, no antimicrobial effects were observed with methyl, 2-methylbutyrate against Escherichia coli; with 2-methylbutyl angelate and methyl 2-methylbutyrate against Klebsiella pneumonia; or with isobutyl isobutyrate against Staphylococcus aureus. The researchers hypothesized that the high antimicrobial activity of Roman chamomile oil could result from the effects found in the main and minor constituents of the oil.

Interesting Compositions
Film-forming shaving compositions: The Procter & Gamble Company formulated cationic and lubricant polymers in a film-forming shaving composition.16 The composition comprised: a base composition consisting of a film-forming system containing one or more film-forming polymeric materials, i.e., a cationic polymer; one or more water-soluble or water-dispersible surface active agents; and an optional lathering agent disposed within the base composition. A shaving preparation containing hydroxyethyl cellulose, cationic polyquaternium-10b, PVP and copolymer of vinylidene chloride, acrylonitrile and methyl methacrylate was exemplified.

Fresh feel transparent gel: Kao Corp. published a patent on transparent cosmetic gel compositions containing urea, a urea stabilizer containing a hydroxyl acid or its salt, and 0.65–2.0% carboxyvinyl polymer.17 The composition had good storage stability and provided a fresh feeling on the skin with smooth stretchability. The composition could further contain a surfactant and/or a polyhydric alcohol. An example of a transparent gel lotion is shown in Formula 8.

Whitening and wrinkle-fighting women’s panties: Skin-whitening women’s panties containing one or more gel blocks of arbutin, kojic acid, L-ascorbic acid, collagen, ubiquinol and hydroquinone were recently patented in Taiwan.18 Each of these ingredients were covered by a release film attached to the panties that pressed close to the groin, waist and borders between hips and legs of the user. After the release film is torn and the panties are worn by the user, skin whitening, skin color lightening and wrinkle-softening agents contained in the gel blocks perform their functions to the skin covered by the panties while not disturbing the user’s daily life.

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1. DE 102,008,009,799, Use of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-propane-1-one against hyperpigmentation in cosmetic and dermatological preparations, Beiersdorf AG, Germany (August 20, 2009)
2. US 2009 208,429, Glow and sunless tanning via a heated flowable cosmetic transferred onto skin, Unilever PLC, USA (Aug 20, 2009)
3. US 2009 209,600, Moisturization improvement via a heated niacinamide containing flowable cosmetic transferred onto skin, Unilever PLC, USA (Aug 20, 2009)
4. WO 2009 104,118, Moisturizing cosmetic composition comprising a combination of homarine and erythritol, Sederma, France (Aug 27, 2009)
5. JP 2009 191,037, Self-emulsifying bath compositions, Kao Corp, Japan (Aug 27, 2009)
6. US 2009 215,887, 5-Hydroxy-2-methyl-4H-pyran-4-one esters as novel tyrosinase inhibitors for skin-brightening cosmetic compositions, Eastman Chemical Co, USA (Aug 27, 2009)
7. JP 2009 298,724, beta-Thujaplicin as collagen production stimulator for skin applications, Hinoki Shinyaku K K, Japan (Dec 24, 2009)
8. LC Cefali et al, Tomato salad: An alternative as antioxidant source for topic use, Latin American J Pharm 28(4) 589-593, 2009 (in Portuguese)
9. JP 2009 292,752, Shampoos containing surfactants and polyhydric alcohols, Kracie Home Products Ltd, Japan (Dec 17, 2009) 10. JP 2009 292,733, Emulsified hair cosmetic compositions containing amino-modified silicones, Milbon Co, Ltd, Japan (Dec 17, 2009)
11. JP 2009 191,033, Water-in-oil sunscreen compositions, Kosei Co, Ltd, Japan (Aug 27, 2009)
12. US 2009 208,443, Cationic copolymer and starches formulated cosmetic compositions exhibiting radiance with soft focus, Unilever PLC, USA (Aug 20, 2009)
13. JP 4,320,243, Cosmetic compositions containing pentaerythritol ester, Shiseido Co, Ltd, Japan (Aug 26, 2009)
14. JP 2009 190,995, Nail polish compositions containing styrene copolymers, fatty acid esters, alkanediols and lower alcohols, Mandom Corp, Japan (Aug 27, 2009)
15. WO 2009 146,886, Novel antibacterial peptides, Spiderbiotech Srl, Italy (Dec 10, 2009)
16. WO 2009 101,583, Film forming personal care compositions comprising cationic and lubricant polymers, The Procter & Gamble Company, USA (Aug 20, 2009)
17. JP 2009 191, 021 Transparent cosmetic gel compositions containing urea, urea stabilizer and carboxyvinyl polymer, Kao Corp, Japan (Aug 27, 2009)
18. US 7,581,262, Panties with skin-whitening effect, Chiu, Chien-Jung, Taiwan (Sept 1, 2009)

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