Boosting SPF with Copolymers and Other Topics: Literature Findings

This month’s survey of recent patent and research literature describes moneymaking ideas for personal care development, including an anti-inflammatory to soothe the skin post raw material irritation, lactulose for hair styling, reducing the damage caused by perms, boosting SPF with copolymers and the treatment of skin with heated lotion, among others.

Skin and Skin Care
Light activation of cytochrome C oxidase: L’Oréal has disclosed the activation of a cytochrome C oxidase substrate with light radiation to improve the appearance of skin and/or hair.1 The invention comprises the simultaneous and/or sequential administration of: at least one cytochrome C oxidase substrate, at least one agent to increase the expression of said substrate, and at least one light radiation source with a predominant wavelength ranging 550–1,000 nm, preferably 640–680 nm, to activate the cytochrome C oxidase. A radiation dose ranging 0.01– 200 J/cm2, specifically 5–30 J/cm2, was applied in the described method. The invention also relates to a kit including all three components. An example of a skin improvement cream is shown in Formula 1.

Refreshing DHA self-tanner: Coty Prestige Lancaster Group GmbH has patented a self tanner comprised of 1.0–3.0% w/w dihydroxyacetone (DHA), 8.0–35 % w/w water, 5.0–30 % w/w wax and 3.0–35% w/w oil, 1.0–7.0% w/w pigments and additional cosmetic agents and excipients.2 The compositions are free from emulsifiers, and the ratio of water to oil is 0.8–1:1.5–3. This storage-stable composition is said to produce instantaneous, even and continuous tanning with a feeling of freshness. An example is shown in Formula 2.

Anti-inflammatory to soothe irritation: Symrise GmbH and Co. has disclosed the use of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone in cosmetic and pharmaceutical preparations as an anti-inflammatory agent to soothe the irritation caused by other cosmetic ingredients.3 The described compositions contain additional anti-inflammatory agents and sunscreens with SPF > 2. P-hydroxyacetophenone was reacted with vanillin to prepare 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propene-1-one, followed by the catalytic hydrogenation of the product to obtain the title compound. An example of a skin lightening cream with the anti-inflammatory agent is shown in Formula 3.

Hair and Hair Care
Cationic surfactant hair conditioners: L’Oréal has patented the use of two separate cationic surfactants as conditioners in hair care compositions, as well as a process for treating hair with the compounds.4 The first composition utilizes cationic quaternary ammonium esters derived from 2-[2-(diethylamino)ethoxy] ethanol as the conditioning agent. 2-[2-(Diethylamino)ethoxy]ethyl decanoate was reacted with diethylsulfate to obtain 2-[2-(decanoyoxy)ethoxy]-N,N,N-triethylethanaminium chloride. A hair preparation composed of 15% inulin, 2% pectin, 1% 2-[2-(decanoyoxy)ethoxy]-N,N,N-triethylethanaminium chloride and balance of water is provided.

The cationic surfactant N,N,N-trimethyl-3-{8-(2-octylcyclopropyl)octa-noyloxy}propan- 1-aminium methyl sulfate also was used as a conditioner for hair care.5 The surfactant was prepared by the reaction of 3-(dimethylamino)propyl-8-(2-octylcyclopropyl)octanoate with dimethylsulfate. In addition to its use in hair care, N,N,N-trimethyl-3-{8-(2-octylcyclopropyl)octa-noyloxy}propan-1-aminium methyl sulfate can be formulated into pharmaceutical compositions. A hair conditioner containing 3.00% w/w N,N,N-trimethyl-3-{8-(2-octylcyclopropyl)octa-noyloxy}propan-1-aminium methyl sulfate with and a balance of water was provided.

Cationic polymers for hair dye: Another patent issued to L’Oréal covers the use of cationic or amphoteric polymers in a hair dye composition, along with an oxidative dye and a chelating agent.6 The ingredient combination prevents the degradation of hair color by acting as an antioxidant or free radical scavenger. An example is shown in Formula 4.

Lactulose for hair styling: Unilever disclosed a hair styling composition containing anhydrous lactulose and at least one suitable carrier, styling polymer or surfactant.7 Lactulose showed substantial styling and anti-humidity benefits when tested on hair swatches.

Stable, smooth hair products: Shiseido Co., Ltd. discloses oily products such as conditioners, hair oils or foams that exhibit stable gelation properties, excellent applicability, nonstickiness and smoothness.8 The hair products described had continuous oil phases and contained 0.1–60% w/w block alkylene oxide derivatives, 0.1–99% w/w volatile hydrocarbon and/or silicone oils, 0.1–99% silicones and 0.1–10% w/w water. The alkylene oxide derivative used has the following formula:


where AO = C3-4 oxyalkylene; EO = oxyethylene; m = 1-70; l + n = 1-70; R1, R2 = C1-4 hydrocarbyl, H; and the ratio of EO to all oxyalkylene units is 20–80% w/w. An example, shown in Formula 5, exhibited low irritation to the skin, good spreadability and hair damage-repairing properties.

Reducing perm damage: Mandom Corp. has patented permanent wave-setting kits that suppress damage and condition hair.9 The first agent applied from the kit contains a reductant. The second agent applied contains an oxidant, monoalkyl quaternary ammonium-type cationic surfactants, amino-modified silicones, lanolin fatty acid aminopropylethyldimethylammonium ethyl sulfate and polyether-modified silicone surfactants. A permanent wave solution for bleached hair, shown in Formula 6, resulted in good gloss, smooth feel and excellent combing properties.

Swelling effect for lip care: Coty Deutschland GmbH has disclosed two-part lip compositions that are combined and applied to the lips for a swelling effect.10 The first composition comprises: a siloxane polymer with at least two hydroxy-functionalized terminal groups or hydroxy-functionalized side chains, and/or a polyol with at least two hydroxyl groups; and either a catalyst or a hydrosiloxane with at least two Si-H units; the second composition contains either the catalyst or hydrosiloxane—whichever is not present in the first composition.

When the two parts of the composition are combined, the catalyst catalyzes in situ cross-linking of the siloxane polymer or polyol and the hydrosiloxane with dehydrogenative coupling to form a foamed elastomeric transfer-resistant film. The formula for a two-part lipstick composition is shown in Formula 7.

Spray congealing for avobenzone: Albertini et al. have evaluated spray congealing as a technique for the preparation of highly loaded, solid lipid microparticles (SLMs) containing the sunscreen agent butyl methoxydibenzoylmethane (avobenzone) to potentially reduce its photoinstability.11 The microparticles were produced using the lipidic material carnauba wax and the surfactant phosphatidylcholine via either the classical melt dispersion method or spray congealing through a pneumatic atomizer.

Avobenzone was included at 40.1–48.5% w/w. Release studies indicated that spray congealing enabled a more efficient modulation of avobenzone release from the SLMs—spray congealing released 26% of encapsulated avobenzone after 2 hr, compared with 60% released for the melt dispersion.

The photoprotective efficacy of the SLMs was evaluated after their introduction into a model cream. A statistically significant decrease in the light-induced degradation of avobenzone was obtained by the SLMs prepared via the melt dispersion procedure—the extent of degradation was 38.6 ± 3.6% for nonencapsulated avobenzone and 32.1 ± 4.3% for the microparticle-entrapped sunscreen. In the case of SLMs produced by spray congealing, a more marked reduction in avobenzone photodecomposition was noted, up to 15.4 ± 4.1%. Therefore, the spray congealing technique was found to be superior to the classical melt dispersion method for rapid and solvent free production of SLMs with a high avobenzone loading capacity.

High SPF for allergic skin: Stada Arzneimittel AG has patented a sunscreen hydrodispersion for allergic skin with ≥ SPF 50.12 The described composition is free from emulsifiers, fats, preservatives and perfume oils. An example is shown in Formula 8.

O/W sunscreens with ≥ SPF 50: Stada Arzneimittel also patented o/w sunscreen emulsions with ≥ SPF 50 that contain titanium dioxide, zinc oxide, methylene bis-benzotriazolyl tetramethylbutylphenola and other sunscreens.13 An example is shown in Formula 9.

Boosting SPF with copolymers: Playtex Products Inc. has patented photoprotective compositions with glycol and styrene-acrylate copolymer spheres.14 The compositions described include: one or more photoactive agents such as a UV filter; one or more optimizing agents such as caprylyl glycol; and a styrene-acrylate copolymer such as an SPF booster. Such a composition was reported to provide an unexpected synergistic combination of the optimizing agents and copolymer booster to possibly increase SPF, the UVA/UVB ratio, critical wavelength, the photostability of the UVA absorber and UVA protection factor.

Interesting Compositions, Ingredients
Solid, powder cosmetics: Kao Corp. has disclosed solid powdered cosmetics containing oils and polyols, as well as the manufacture of such compositions.15 Specifically, the compositions contain: powders with an average particle size of 0.1–200 mum; 15–30% w/w oils that are liquid at 25°C; and 15–30% w/w polyols that are liquid at 25°C. To manufacture the powder, vibration is applied at a frequency of 10–40 kHz and an amplitude of 10–100 mum during pressure forming. An example is shown in Formula 10. The composition described was formed under a pressure of 4.2 kg/cm2 and a vibration of 20 kHz and 20 mum to give a solid, powdered cosmetic with good impact resistance and surface appearance, a moist feeling and long-lasting effects.

Heated lotion for skin care: Unilever PLC has patented a heated, flowable lotion and a method for treating skin with it.16 The invention involves dispensing the lotion from a heating device and includes instructions for application to the skin. The formula includes an inorganic structurant material such as a clay, which functions to retain viscosity over a wide temperature range. Even under shear, the clay reportedly allows for a clean cut-off at the nozzle of the heating device.

Refreshing, milky skin preparation: Shiseido Company Ltd. has patented an emulsified, o/w, milky skin cosmetic preparation incorporating 2-acrylamide 2-methylpropanesulfonate copolymer to impart a refreshing feeling, astringent and moisturizing effects, and softening benefits to skin.17 The preparation is excellent in terms of emulsion stability despite its high water content and low viscosity, appearing a milk-white color. The preparation has a viscosity at 25°C of 10,000 mPa·s and is preferably formulated with: 0.005–2.0% w/w copolymer of 2-acrylamide 2-methylpropanesulfonic acid or a salt thereof/polyoxyethylene alkyl ether methacrylate; 0.005–1.5% w/w alkyl modified carboxyvinyl polymer; and 0.005–15.0% w/w alkylene oxide derivative. The skin cosmetic preparation may further contain an oil with a viscosity at 25°C of 100 mPa·s or less that is a liquid at an ordinary temperature. Furthermore, the preparation preferably comprises 55–80% w/w water.

O/W emulsion: Beiersdorf AG has disclosed cosmetic or dermatological preparations containing 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxphenyl)-propane-1-one and one or more anionic, nonionic or polymeric emulsifiers.18 P-hydroxyacetophenone was reacted with vanillin to prepare 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propene-1-one, followed by the catalytic hydrogenation of the product to obtain the title compound. An o/w emulsion containing the material is shown in Formula 11. Reproduction of the article without expressed consent is strictly prohibited.

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1. WO 2009 101,344, Combination of a light ray with a cytochrome c oxidase substrate particularly for improving the appearance of the skin and/or hair, L’Oréal, France (Aug 20, 2009)
2. EP 2,087,879, Skin tanning agent with dihydroxyacetone on a water-wax-oil basis, Coty Prestige Lancaster Group GmbH, Germany (Aug 12, 2009)
3. EP 2,090,301, 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone and its use in cosmetic and pharmaceutical preparations as anti-inflammatory agent, Symrise GmbH & Co KG, Germany (Aug 19, 2009)
4. WO 2009 101,322, Cosmetic composition comprising a cationic surfactant compound, novel compounds, use as conditioner and cosmetic treatment method, L’Oréal, France (Aug 20, 2009)
5. WO 2009 101,321, Cationic surfactant compounds, use thereof as conditioner, cosmetic treatment method, and cosmetic or pharmaceutical compositions comprising same, L’Oréal, France (Aug 20, 2009)
6. EP 2,092,933, Use of particular cationic polymers in a hair dye composition associated with a chelating agent as antioxidants or free-radical scavengers, L’Oreal, France (Aug 26, 2009)
7. WO 2009 97,885, Hair styling composition containing anhydrous lactulose, Unilever PLC and NV, and Hindustan Unilever Ltd, UK (Aug 13, 2009)
8. JP 2009 184,949, Oily hair cosmetics with stable gelation properties and excellent applicability, nonstickiness, and smoothness, Shiseido Co, Ltd, Japan (Aug 20, 2009)
9. JP 2009 191,062, Kits of permanent wave-setting preparations with suppressed damages to hair and excellent hair-conditioning properties, Mandom Corp, Japan (Aug 27, 2009)
10. EP 2,090,294, Two-part cosmetic product with swelling effect to biological surfaces comprising a siloxane polymer, polyol and hydrosiloxane, Coty Deutschland GmbH, Germany (Aug 19, 2009)
11. B Albertini et al, Evaluation of spray congealing as technique for the preparation of highly loaded solid lipid microparticles containing the sunscreen agent, avobenzone, J Pharm Sci 98(8) 2759–2769 (2009) (in English)
12. EP 2,092,928, Sunscreen hydrodispersion with SPF equal or greater than 50 for application to allergic skin, Stada Arzneimittel AG, Germany (Aug 26, 2009)
13. EP 2,092,930, O/W sunscreen emulsions with SPF equal or greater than 50 and containing titania, zinc oxide and methylene bis-benzotriazolyl tetramethylbutylphenol (Tinosorb M), Stada Arzneimittel AG, Germany (Aug 26, 2009)
14. US 2009 202,459, Photoprotective compositions with glycol and styrene-acrylate copolymer spheres, Playtex Products, Inc, USA (Aug 13, 2009)
15. JP 2009 184,944, Solid powdered cosmetics containing oils and polyols, and their manufacture, Kao Corp, Japan (Aug 20, 2009)
16. US 2009 208,592, Thickened product and method for transferring heated flowable cosmetic onto skin, Unilever PLC, USA (Aug 20, 2009)
17. US 2009 202,600, Oil-in-water emulsified milky skin cosmetic preparation comprising a 2-acrylamide 2-methylpropanesulfonate copolymer, Shiseido Company Ltd, Japan (Aug 13, 2009)
18. EP 2,090,286, Cosmetic or dermatological preparations containing 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxphenyl)-propane-1-one and one or more emulsifier, Beiersdorf AG, Germany (Aug 19, 2009)

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