Water-soluble UV Filters and Other Topics

Feb 1, 2009 | Contact Author | By: Charles Fox, Independent Consultant
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Title: Water-soluble UV Filters and Other Topics
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Skin and Skin Care
Skin smoothing: Beiersdorf AG discloses a method for reducing the signs of skin aging, particularly for mitigating and preventing wrinkles and expression lines, by using a rotating or oscillating brush for the application of skin-smoothing active ingredients.1 It also relates to methods for smoothing the skin and improving surface structure. Accordingly, a cosmetic preparation is applied either to the skin requiring treatment or to a brush and subsequently worked into the skin by means of rotating or oscillating the brush. The cosmetic preparation in both approaches comprises at least one skin-smoothing active ingredient, such as coenzyme Q10. A skin-smoothing composition is shown in Formula 1.

Skin cleansing: Amorepacific Corp. discloses skin-cleansing compositions containing microcapsules including stabilized enzymes.2 These microcapsules have a central core composed of white sugar or microcrystalline cellulose. Surrounding the core is a layer of stabilized enzymes, and surrounding this layer are seven coating layers composed successively of shellac, polymer, wax, cationic surfactant, polymer, anionic surfactant and polymer, from innermost to outermost layer. The microcapsules with stabilized enzymes in the enzyme layer have a triple-layer structure: an enzyme core is surrounded by a coating layer of hydrophobic macromolecular (> 1000 g/mol) polyol, and an outer layer of macromolecular wall material. The enzymes are selected from more than one of: hydrolase of lipase, amylase, pepsin, trypsin, urease, asparaginase and papain. The macromolecular polyol is selected from more than one of: polyethylene glycol, polypropylene glycol, and their copolymers. The macromolecular wall material is selected from more than one of numerous polymers made from various acids, esters, styrene, methacrylates and other monomers cited in the patent.

Even in a skin-cleansing composition having a high concentration (> 15%) surfactant system, the enzymes contained in these microcapsules are not degraded and maintain the enzyme activity enabling excellent skin cleansing.

Preservability: Kuraray Co., Ltd., and Pola Chemical Industries Inc. disclose skin preparations containing phospholipids and 4-alkylresorcinols with good transdermal absorption and storage stability.3 The 4-alkylresorcinols and/or their salts inhibit a decrease in preservability due to the phospholipids. The preparations may also contain antimicrobial polyols, N-acyl amino acids and/or phenoxyethanol as optional ingredients. Thus, hydrogenated soya lecithin liposomes were mixed with water, ultrasonicated, mixed with 1,3-butanediol, and 4-butylresorcinol, and emulsified upon gradual addition to a mixture of glyceryl triisooctanoate, sorbitan sesquistearate, and polyoxy ethylene sorbitan monostearate to give an emulsion containing liposomes dispersed in the inner aqueous phase. The emulsion showed good antifungal activity against Aspergillus niger.

Free radical scavenger: Faming Zhuanli Shenqing Gongkai Shuomingshu discloses a free radical scavenger used in cosmetics for resisting aging, preventing sunburn and repairing skin after sunburn.4 The free radical scavenger is prepared from Sophora japonica flower bud, Canarium album fruit and Chaenomeles speciosa fruit at 5.6–51.2, 2.9–38.3 and 10.7–43.1 parts by weight, respectively. Optional ingredients include Eugenia caryophyllata, Scutellaria baicalensis and Sophora japonica flower at 0.9–33.3, 1.9–17.5 and 3.2–41.4 parts by weight, respectively. These botanicals are extracted with a solvent such as methanol, 70% ethanol or absolute ethanol. The mixture is effective against such free radicals as 1-diphenyl-2-picrylhydrazyl (DPPH) free radicals, superoxide anion radicals, hydroxyl radicals, or mixtures thereof.

Skin brightener: Shuomingshu also discloses the use of N-acetyl-D-glucosamine as a skin brightener in cosmetics.5 N-acetyl-D-glucosamine inhibits tyrosinase activity, melanocyte proliferation, melanin formation, and tyrosinase protein and gene expression to brighten the skin. Cosmetics containing N-acetyl-D-glucosamine have good brightening effect, low cost and irritation, and are said to avoid occurrence of contact dermatitis, exogenous ochronosis or skin allergy.

Shower oil: Beiersdorf AG discloses a new shower oil containing turbidity preventing agents.6 These shower oils are liquid at room temperature. They contain oil at 30–90% by weight, water at 0–1%, turbidity inhibitors at 3–10%, and foam-forming, oil-soluble surfactants at 3–50%. The shower oil can be packaged in a self-dissolving bag prepared from polyvinyl alcohol foil. An example of a shower oil is shown in Formula 2.

Protection for fragile lips: L’Oréal discloses the use of active agents to increase the ceramide content of the lips for protective benefits.7 Active agents include ceramide precursors such as 6-hydroxy-4-sphingenine. Additional active agents are ascorbic acid and its analogs. The composition of a lipstick for fragile lips is shown in Formula 3.

Hair and Hair Care
Hair growth promotion: Hwang et al. have published on in vivo hair growth promotion effects of cosmetic preparations containing hinokitiol-loaded poly(epsilon-caprolactone) nanocapsules.8 Nanocapsules containing hinokitiol (HKL) were prepared by an emulsion-diffusion method. In an emulsification step to prepare the nanocapsules, cetyltri- methylammonium chloride (CTAC) was employed as a cationic emulsifier, poly(epsilon-caprolactone) (PCL) was used as a wall material, and HKL dissolved in octyl salicylate (OS) was used as a core material.

The submicron-sized nanoparticle was observed on a transmission electron microscope. The size ranged 55–234 nm and the mean diameters were 223 nm, which were determined by a dynamic light scattering method. According to the results of pH-dependent microelectrophoresis, the absolute value of the surface potential of the nanocapsules was greater than 20 mV.

The nanocapsules were colloidally stable over a pH range of 3–11. The nanocapsules were included in two kinds of preparations, namely shampoo and hair tonic, and the preparations were applied every day for three weeks on the clipped backs of six-week-old mice (C57BL/6) to investigate the hair growth-promoting effect. The degree of hair growth was evaluated by image-analyzing the photographs of the backs and, in parallel, by the histological observation of the formation and the growth of hair or hair bulbs. The results were compared with those of commercially available minoxidil solution (3%). Phosphate buffered saline was used as a control. The in vivo hair growth-promoting effects of the two preparations were comparable to those of minoxidil solution. These results are in a good agreement with the histological and structural changes of follicles of the model animals, whose skins were treated with either the testing samples or the control in the same way the in vivo hair growth-promotion experiments were performed.

Simultaneous hair dyeing and waving: Ceres Cosmetic Co., Ltd., discloses a method for manufacturing a hair dye capable of forming a permanent wave.9 The method calls for the following steps:
• Add a dye, an antioxidant, an emulsifier and purified water to a pressurizing tank, slowly stirring and heating to 85°C to completely dissolve the ingredients, and then cooling the mixture to 35°C.
• Add a permanent wave-forming agent, and stir to dissolve.
• Add a stabilizer with stirring.
• Add a pH adjusting agent to obtain a first solution.
• Dissolve a reducing agent and additives to purified water to obtain a second solution.

The first solution comprises dyes, thioglycolic acid (antioxidant), polyoxyethylene nonyl phenyl ether (emulsifier), a permanent wave-forming agent, a polyquaternium-10 (stabilizer) and pH adjusting agent at 0.1–13.0, 0.05–0.5, 0.1–3.0, 1.1–12.0, 0.1–1.0 and 0.1–7.0% by weight, respectively, with purified water as balance. The second solution is composed of hydrogen peroxide, sodium lauryl sulfate solution, glycerin and EDTA at 1.0–20.0, 0.5–5.0, 0.5–5.0 and 0.5–1.0%, respectively, with purified water as balance. The hair dye can be used for dyeing hair and simultaneously forming a permanent wave, and has the advantages of lasting and good dyeing effect, high reliability without deterioration, and no damage to hair.

Preventing alopecia: Uniherb Skincare Co., Ltd., discloses a shampoo composition containing a medicinal herbal extract for preventing alopecia.10 The herbs included Angelica dahurica, Zanthoxylum pericarpium, Ocimum sanctum, Chrysanthemum indicum, Cnidium officinale, Eclipta prostrata, Morus alba, Sophora flavescens and Cynanchum wilfordii at 8–20%, 10–25%, 5–20%, 5–25%, 10–17%, 5–15%, 7–15%, 9–12% and 9–15% by weight, respectively. The extract is prepared by crushing the herbs to 70–95 mesh, extracting with 2 L of distilled water at 90°C for 6–10 hr, centrifuging at 700–900 rpm for 30–50 min to obtain supernatant fluid, and freezing for preservation. The shampoo composition described in the patent is prepared by adding the medicinal herbal extract according to the designated ratio. The shampoo composition can be used to treat dandruff, prevent alopecia and promote hair growth.

Black hair dye: Shuomingshu also discloses a two-component, nonoxidative permanent black hair dye composition containing Chinese medicinal materials as coloring agent and Eugenia caryophyllata as penetrant, and its preparation method.11 The Chinese medicinal materials are Galla chinensis, Terminalia chebula (Fructus chebulae) and Cynips gallae-tinctoriae, which are present in the composition at 3–10%, 2–6% and 1–4% by weight, respectively.

Component A contains the Chinese medicinal materials as well as Eugenia caryophyllata (penetrant), cysteine (reducing agent), Angelica sinensis (a nutritional ingredient), a preservativea, and sodium sulfite (antioxidant) at 2–6%, 3–7.5%, 0.5–2%, 0.0015% and 0.5% by weight, respectively, with deionized water as balance. Component B contains ferrous sulfate (color developing agent) and a preservativea at 0.3–1% and 0.0015% by weight, respectively, with deionized water as balance.

The preparation method for component A requires mixing the Chinese medicinal materials, adding deionized water, heating to 45–60°C, maintaining the temperature for 24 hr, filtering, adding reducing agent, antiseptic and antioxidant to the filtrate, adding deionized water under stirring, cooling, and packaging. Component B is prepared by mixing ferrous sulfate and preservative, adding deionized water, heating to 40°C under stirring, maintaining the temperature for 20–30 min, cooling, and packaging.

The penetrant (Eugenia caryophyllata) and reducing agent (cysteine) can break the disulfide bond of hair keratin, allowing the internal area to expand so the Chinese medicinal coloring agent can penetrate more deeply. This black hair dye composition provides good dyeing fastness and convenient application.

Preventing hair dryness: Arimino Co., Ltd., discloses an emulsion composition that prevents dry hair.12 The composition is in a form that is easy to apply and consists of an oil component, a surfactant and water. It also contains 0.5–15% by weight of at least one polyhydric alcohol selected from the group consisting of glycerin, diglycerin and dipropylene glycol. The composition also contains 0.005–1% of a highly polymerized polyethylene glycol and 0.05–10% of lanolin and/or a lanolin derivative.

Permanent waving: L’Oréal discloses a method for permanent waving of hair or other keratinous fibers including a step of applying an oxidizing composition containing a cationic polymer thickener.13

The first step is applying a reducing composition on the keratinous fibers to reduce the keratin disulfide bonds. Waving of the keratinous fibers can occur before, during or after this application.

The second step is fixing by oxidation and reshaping those bonds by applying an oxidizing composition containing at least an oxidizing agent and at least a cationic polymer thickener. The thickener is the product of the polymerization of a mixture of monomers. The monomer mixture includes at least one of each of the following: a nonionic hydrophobic vinyl monomer, a surfactant vinyl semi-hydrophobic monomer, and a vinyl monomer substituted by at least an amine group.

In one example from the patent, a reducing composition was applied on the hair in an iron curler for 15 min. Then the hair was washed and the oxidant composition shown in Formula 4 was applied to obtain a permanent hair wave.

Hair removal: Reckitt Benckiser (UK) Ltd. discloses epilatory compositions comprised of a rosin-based or sugar-based material and, mixed with the matrix material, particulate silica, and a polymer or copolymer.14 Preferably the silica is fumed and colloidal; and the polymer is polyethylene or block copolymers of hydrocarbon-polyether-polyamide or polyether-hydrocarbon types. The particles reduce the tendency of the epilatory composition to flow, under warm ambient conditions. Also disclosed is an epilatory product and a method of epilation.

An example is shown in Formula 5. Hair removal percentage for the composition was at least 10% higher than with no polymer/copolymer.

Makeup
Water resistance:
Coty B.V. discloses water-resistant and abrasion-resistant eye and lip cosmetics containing film-forming acrylate copolymers.15 These decorative lipsticks and cosmetics for eyebrows and eyelashes have a gel structure comprised of water, a nonionic emulsifier, 1–30% by weight of a film-forming agent, and 0.01–35% by weight of an aliphatic hydrocarbon solvent or a volatile silicone derivative that cannot be mixed with water, but can be emulsified with water-based ingredients and solvents in the presence of an emulsifier. The water-emulsifiable, film-forming agent is based on an ethylacrylate-methylmethacrylate copolymer or acrylic acid or methacrylic acid or an ester thereof. One to 45% by weight of the cosmetic composition is a solid phase. An example is shown in Formula 6.

Powders: Shiseido Co., Ltd., discloses cosmetic compositions containing powders treated with perfluorooctyltriethoxysilane (POS) and powders containing hydroxyapatite (HA).16 The compositions contain 5–50% by weight of POS-treated powders or powders treated with POS and acrylic silicone copolymer. The compositions also contain 1–30% by weight of HA powder or HA-containing composite powder. The compositions may also contain zinc oxide, synthetic mica and/or spherical powders.

A solid powder cosmetic foundation containing 5% POS-treated powders (sericite, talc, mica) and 10% HA-coated mica also contained synthetic fluorophlogopite, zinc oxide and silicone-treated powders. This foundation showed a smooth feel, uniform finish and long-lasting makeup effect.

Sunscreens
Vinylpyrrolidone/acrylic acid copolymer: Beiersdorf AG discloses a cosmetic preparation with vinylpyrrolidone/acrylic acid copolymer.17 In addition to the copolymer, the cosmetic preparations of this invention contain one or more water-soluble UV photoprotective filters selected from the following group: 2-phenylbenzimidazole-5-sulfonic acid; phenylene-1,4-bis-(2-benzimidazyl)-3,3’,5,5’-tetrasulfonic acid; and the sodium, potassium and triethanolammonium salts of those two compounds. An example is shown in Formula 7.

Interesting Vehicles
Fragrance retention:
Kao Corp. discloses isotropic one-phase liquid cosmetic compositions with excellent transparency, detergency, processability, and fragrance retention.18 The compositions contain nonionic surfactants with HLB > 9, nonionic surfactants with HLB 3–9, liquid oils, polyhydric alcohols, water and compositions of one or more perfumes selected from limonene, α-pinene, β-pinene, linalyl acetate, etc. Thus, a cleansing emulsion containing 11% polyoxyethylene octyl dodecyl ether (PODE, HLB = 13), 0.9% diglyceryl stearate, 1% PODE (HLB = 7), 2% ethoxylated hydrogenated castor oil (EHCO, 10 EO), 2% polyoxyethylene glyceryl ether triisostearate, 3% EHCO (20 EO), 20% 2-ethylhexanoic acid triglyceride, 10% sorbitol, 10% glycerin, 10% 1,3-butylene glycol, 30% water and 0.1% perfume showed good spreadability on the skin and fragrance retention until washed out.

References

1. WO 2008 98,648, Method for reducing the signs of skin aging by using a rotating or oscillating brush for the application of skin-smoothing active ingredients, Beiersdorf AG, Germany (Aug 21, 2008)
2. KR 804,096, Skin-cleansing composition containing microcapsules including stabilized enzymes, Amorepacific Corp., South Korea (Aug 31, 2008)
3. JP 2008 184,431, Skin preparations containing phospholipids and 4-alkylresorcinols with good transdermal absorption and storage stability, Kuraray Co., Ltd.; Pola Chemical Industries Inc., Japan (Aug 14, 2008)
4. CN 101,229,114, A free radical scavenger used in cosmetics for resisting aging, preventing sunburn and repairing skin after sunburn, Faming Zhuanli Shenqing Gongkai Shuomingshu, China (Jul 30, 2008)
5. CN 101,229,104, Application of n-acetyl-d-glucosamine in brightening cosmetics, Faming Zhuanli Shenqing Gongkai Shuomingshu, China (Jul 30, 2008)
6. EP 1,955,690, New shower oil containing turbidity preventing agents, Beiersdorf AG, Germany (Aug 13, 2008)
7. EP 1,955,692, Use of active agents for increasing the ceramide content of the lips, as a protection agent for fragile lips, L’Oréal, France (Aug 13, 2008)
8. SL Hwang et al, In vivo hair growth promotion effects of cosmetic preparations containing hinokitiol-loaded poly(epsilon-caprolactone) nanocapsules, J Microencap 25(5) 351–356 (2008) (in English)
9. KR 806,078, Method for manufacturing hair dye capable of forming permanent wave, Ceres Cosmetic Co., Ltd., South Korea (Feb 21, 2008)
10. KR 805,692, Shampoo composition containing medicinal herb extract for preventing alopecia, Uniherb Skincare Co., Ltd., South Korea (Feb 21, 2008)
11. CN 101,229,110, Nonoxidative permanent black hair dye composition comprising Chinese medicinal materials as coloring agent and Eugenia caryophyllata as penetrant, and its preparation method, Faming Zhuanli Shenqing Gongkai Shuomingshu (Jul 30, 2008)
12. WO 2008 96,497, Emulsion composition for preparation for application to hair, Arimino Co., Ltd., Japan (Aug 14, 2008)
13. FR 2,912,309, Method for permanent waving of keratinous fibers including a step of application of an oxidizing composition containing cationic polymer thickener, L’Oréal, France (Aug 15, 2008)
14. GB 2,446,576, Epilatory compositions comprising a rosin- or sugar-based material, silica and polymer, Reckitt Benckiser (UK) Limited, UK (Aug 20, 2008)
15. DE 10,136,883, Water-resistant and abrasion-resistant eye and lip cosmetics containing film-forming acrylate copolymers, Coty BV, Netherlands (Aug 21, 2008) 16. JP 2008 184,399, Cosmetic powders containing perfluorooctyltriethoxysilane-treated powders and hydroxyapatite-containing powders, Shiseido Co., Ltd., Japan (Aug 14, 2008)
17. US 2008 193,395, Cosmetic preparation with vinylpyrrolidone/acrylic acid copolymer, Beiersdorf AG, Germany (Aug 14, 2008)
18. JP 2008 184,437, Isotropic one-phase liquid cosmetic compositions with excellent transparency, detergency, processability, and fragrance retention, Kao Corp., Japan (Aug 14, 2008)

 

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Footnote A

a Kathon CY-1 (Chemical name: 2-methyl-4-isothiazolin-3-one) is a product of Taicang City Yanlin Chemical Works, China.

Formula 1. Skin Smoothing Composition

Cetearyl glucoside 2.00% w/w
Myristyl myristate 1.00
Stearyl alcohol 4.00
C12-15 alkyl benzoate 2.00
Caprylic/capric triglyceride 3.00
Hydrogenated polydecene 1.00
Dicaprylyl carbonate 3.00
Polydecene 4.00
Ethylhexyl methoxycinnamate 5.00
Ethylhexyl cyanodiphenyl acrylate 3.00
Butylmethoxy dibenzoyl methane 2.00
Anise extract 0.50
Coenzyme Q10 0.05
Folic acid 0.03
Trisodium EDTA 0.10
Polyvinylpyrrolidone-hexadecene copolymer 0.40
Parabens  0.40
Ethylhexyl glycerol 0.40
Xanthan gum 0.10
Carrageenan 0.10
Aluminum starch octenyl succinate 1.00
Glycerin  6.00
Butylene glycol 2.00
Talc, BHT and coloring agents 1.00
Fragrance (parfum) qs
Water (aqua) qs to 100.00

Formula 2. Shower Oil

Castor oil 14.50% w/w
MIPA-laureth sulfate 20.50
Polyglyceryl-3 diisostearate 3.00
Laureth-4 12.50
Fragrance (parfum) 1.50
BHT 0.05
Benzophenone-3 0.50
Poloxamer 101 2.00
Water (aqua) 0.10
Soy oil qs to 100.00
    

Formula 3. Lipstick for Fragile Lips

Castor oil 20.00% w/w
Isopropyl lanolate 28.00
Microcrystalline wax 8.00
Carnauba wax 1.00
2-Oleoylamino-1, 3-octadecanediol 0.50
Jojoba oil qs to 100.00
     

Formula 4. Permanant waving oxidant composition

Hydrogen peroxide 4.800% w/w
Tetrasodium etidronate 0.200
Tetrasodium pyrophosphate 0.400
Sodium salicylate 0.035
Polyacrylate-1 crosspolymer 1.000
Phosphoric acid qs to pH 3
Water (aqua) qs to 100.000

Formula 5. Epilatory Composition

Triethylene glycol rosinate 64.877% w/w
Glyceryl rosinate 31.803
Silica 1.950
Polyethylene 1.050
Fragrance (parfum) 0.300
BHA 0.010
Preservative qs
Colors 0.010
  100.000
  

Formula 6. Water-resistant eyebrow liner

Gel Phase  
Ethyl acrylate/methyl methacrylate 24.50%w/w
Water (aqua) 25.20
Laureth-20 0.30
Isodecane 50.00
Makeup Phase  
Gel Phase (shown above) 16.00
Carnauba wax 4.90
Beeswax 3.30
Castor wax 1.40
Microcrystalline wax 5.00
PVP-eicosane copolymer 4.00
Pigments 6.00
Isododecane 38.50
Disteardimonium hectorite 4.00
Isododecane 13.00
Propylene carbonate 1.60
Trimethylsiloxy silicate (and) decamethylcyclopentasiloxane 2.00
Parabens 0.30
  100.00
                 

Formula 7. Sunscreen

Glyceryl stearate citrate 1.50% w/w
Cetearyl alcohol 2.00
Vinylpyrrolidone-acrylic acid copolymer 0.50
Butylene glycol 10.00
Octyldodecanol 3.00
Myristyl myristate 1.00
Glycerin 2.00
Butylmethoxydibenzoylmethane 2.50
Octyl salicylate 4.00
Phenylbenzimidazole 35.00
Sodium starch 3.00
Tapioca starch 0.50
Ethanol 0.10
Folic acid 0.01
Tocopherol acetate 0.20
Disodium EDTA 0.20
Fragrance (parfum), preservatives, color qs
Water (aqua)  qs to 100.00

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