Natural Hair Dyes, Self-tanning Solutions and Other Topics: Literature Findings

Nov 1, 2009 | Contact Author | By: Charles Fox, Independent Consultant
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Title: Natural Hair Dyes, Self-tanning Solutions and Other Topics: Literature Findings
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Keywords: patent

Abstract: This month’s survey of recent patent and research literature describes moneymaking ideas for personal care product development, including fatty acid combinations for in-shower moisturization, stabilizing UV absorbers, travoprost to prevent hair loss and glycyrrhizine in self-tanners, among others.

Skin and Skin Care
Pyrus pyrifolia wrinkle reduction: Ansung Machum Association introduced an antiwrinkle and antiaging cosmetic composition containing 0.05–5.0% w/w Pyrus pyrifolia extract.1 The composition is said to exhibit: an antioxidant effect due to DPPH-eliminating activity; hydroxyl-eliminating, superoxide anion-eliminating and singlet-oxygen-eliminating activity; and a skin-lightening effect due to tyrosinase and melanin synthesis inhibition. In addition, the composition imparts an antiwrinkle effect due to elastase and collagenase inhibition, and an anti-inflammation effect due to lipoxygenase inhibition. The composition is said to inhibit skin aging and reduce the appearance of wrinkles. Also, it has low toxicity.

Urokinase inhibitors for barrier repair: Pentapharm AG published research on 4-amidinobenzylamine urokinase inhibitors for barrier repair in cosmetic and/or dermatological applications.2 In addition, compositions and non-therapeutic methods for the cosmetic treatment of skin and the scalp are disclosed. Urokinase inhibitors can be used to prevent damage to and restore the epidermal barrier. Barrier abnormalities and disruptions are often the starting point of a dry skin state and include itching, dandruff and the perception of sensitive skin. The described 4-amidinobenzylamine derivatives can be used in topical skin and scalp care creams, lotions, gels and shampoos to protect against these conditions.

An emulsion was prepared from four phases, the last of which contained benzylsulfonyl-D-der-gly-(4-aminobenzylamide). The correlation of transepithelial water loss and plasmin to urokinase activity in the stratum corneum (SC) was tested, showing that urokinase and plasmin are inhibited by the amidinobenzylamines on the top layers of the SC.

Carboxylic acids to clean aged skin: Henkel AG & Co. disclose hair and skin cleansers with low pH-containing hydroxycarboxylic acids and ketocarboxylic acids for application to aging skin.3 The cleansers contain water; a mild surfactant system with a maximum of 0.5–20% w/w surfactant; and at least 2% w/w alpha-hydroxycarboxylic acid, beta-hydroxycarboxylic acid and/or ketocarboxylic acid. The pH of the composition is 3.5–4.5. An example of an antiwrinkle cleansing gel is shown in Formula 1.

Fatty acid combos for shower moisturization: Unilever PLC discloses in-shower lotion compositions comprised of up to 10% w/w free fatty acids with the ratio of unsaturated to saturated fatty acids of at least 1:1.4 These rinse-off, skin-conditioning compositions comprise relatively low amounts of oil/emollient and aqueous phase stabilizer/structurant. Unexpectedly high hydration was found with the incorporation of an unsaturated fatty acid, such as oleic acid, as a percentage of the total fatty acid. In a second embodiment, superior hydration resulted from the use of a branched fatty acid, such as isostearic acid, with a minimum amount branched as a percentage of the total fatty acid. Mixtures of unsaturated and branched fatty acids also can be used.

Iridescent, continuous-phase soap bars: Unilever PLC, Unilever N.V. and Hindustan Unilever Ltd. have developed iridescent, continuous-phase soap bars with an ordered, layered microstructure comprising soap, water and ethoxylated alcohols.5 The phenomena of continuous-phase iridescence in a soap bar is characterized by a blue hue where the intensity depends upon the viewing angle and the background color used by the viewer for its observation. In a preferred embodiment, the iridescent soap bar is prepared with equipment capable of intensive mass shearing and generating high compression and extensional forces on the processed soap mass.

Moisturizing with cross-linked polyglutamate: Toyobo Co., Ltd. has researched skin moisturizing cosmetics containing water, alcohol and cross-linked poly-gamma-L-glutamic acid as a skin moisturizer. The cross-linked poly-gamma-L-glutamic acid had a gelation degree of 50–100% at 0.001– 5% w/w as a skin moisturizer.6 For example, sodium polyglutamate was obtained from a culture medium of Natrialba aegyptiaca and cross-linked using gamma-ray irradiation. The obtained cross-linked polyglutamate was mixed at 0.01% w/w with 10% w/w ethanol, 0.5% w/w fragrance and water to 100% w/w.

Hair and Hair Care
Natural hair dyes: Henkel AG & Co. KGaA discloses hair dyes containing natural dyes and 1,3-dihydroxyacetone.7 The natural dyes incorporated into this composition include derivatives of: diarylmethane, naphthoquinone, anthraquinone, flavonoids, betalain, gallotannin and indigoids. The dyes are intense and resilient. An example is shown in Formula 2.

Travoprost for hair loss: Galderma Research & Development utilizes travoprost to treat hair loss.8 The invention described indicates the topical application of a travoprost composition to stimulate or induce the growth and/or reduce the loss and/or increase the diameter and/or reduce the heterogeneousness of the diameter of the human hair stem with at least 24 hr between applications. The efficacy of a daily topical application of 0.01% w/w travoprost was shown to stimulate hair growth in guinea pigs.

Hair relaxer kit: Nippon Fine Chemical Co. discloses a relaxer kit and method for processing smoother hair.9 The kit was shown to improve hair smoothness and elasticity in a shorter time. The first of the two products in the kit contained a trialkoxyalkylsilane, an inorganic acid, an organic acid, a lower alcohol and polyoxyalkylene-modified silicone. The trialkoxyalkylsilane is represented by a general formula R1Si(OR2)3, where R1 and R2 = C1-4 alkyl. The second product in the kit contained a basic substance and a lower alcohol. The method for producing smoother hair included mixing the first and second products and applying them to the hair with heat to form a coated membrane on the hair. An example is shown in Formula 3.

Preventing damage in permanents: Nakano Co., Ltd. discloses an alkoxysilane hydrolyzate (Si oligomer) setting intermediate agent as part of a permanent wave-setting method that prevents hair damage.10 The method begins with the application of a reducing agent followed by treatment with an intermediate agent containing a keratin hydrolyzate with an average molecular weight of 25,000–35,000, and wool- or human hair-derived proteins with a molecular weight of 800–1,200, which include proteins having an average molecular weight (measured by gel-filtration column chromatogram) of 11,000 and 9,700. After the intermediate agent is applied, hair is treated with an acid-containing rinsing agent and finally, an oxidizing agent. The intermediate processing agent may contain Porphyra yezoensis hydrolyzate.

Color Cosmetics
Wax, paste to enhance eyelashes: L’Oréal has disclosed a color cosmetic composition for eyelashes consisting of a 10% w/w hard wax and paste compound.11 The composition can be used to enhance eyelashes. An example of a mascara is shown in Formula 4.

Lip gloss: Coty S.A.S. introduced a lip gloss comprising stearoyl inulin, fatty acid derivatives, hydrogenated polyisobutene and fumed silica di-Me silicate gels in a sugar matrix.12 The sugar gel matrix is made up of stearoyl inulin and an ester or ether with the formula R1COOR2, in which R1 is a residue of a fatty acid with 6–29 carbon atoms and R2 is a hydrocarbon-comprising chain with 3–30 carbon atoms. Also part of the sugar gel matrix is a hydrogenated polyisobutene gel and a fumed silica di-Me silicate gel in C15-19 hydrocarbon. An example of a lip gloss is shown in Formula 5.

Sun Care Stabilizing UV absorbers: Ciba Holding Inc. has addressed the stabilization of UV absorbers in cosmetic compositions.13 Such absorbers, including diphenylacrylates, triazines, benzotriazole derivatives, cinnamic acid derivatives and dibenzoylmethane derivatives, can be stabilized with octocrylene and/or a trisbiphenyltriazine. In a photodegradation study, the addition of octocrylene to a combination of ethylhexyl methoxycinnamate and 2,4,6-tribiphenylyl-1,3,5-triazine stabilized the ethylhexyl methoxycinnamate.

Glycyrrhizine in self-tanning: Beiersdorf AG introduced the use of glycyrrhetic acid and/or glycyrrhizine for self-tanning preparations.14 The compositions also can contain sunscreens. The composition of such a self-tanning product is shown in Formula 6. Beiersdorf AG also published a patent on the combination of erythrulose and glycyrrhetic acid and/or glycyrrhizine in cosmetic preparations for self-tanning.15

Biofunctional DHA derivatives for self-tanning: Merck Patent GmbH created biofunctional dihydroxyacetone derivatives for self-tanning preparations.16 The formulations may further contain sunscreens, vitamins, insect repellents, preservatives, etc. Dihydroxyacetone-o-ethyl acetate was synthesized from dihydroxyacetone and triethylorthoacetate in dioxane using (+/-)-camphor-10-sulfonic acid catalyst. An example of an o/w self-tanning cream is shown in Formula 7.

Raw Materials
Organopolysiloxanes as emulsifiers or dispersing agents: Evonik Goldschmidt disclosed the use of ester-modified polyether-free organopolysiloxanes as emulsifiers or dispersing agents in w/o, o/w and w/s cosmetic, pharmaceutical or cleaning formulations.17 Coco fatty acid was enzymatically esterified with allyloxyethanol and the product was reacted with glycerinmonoallylether and a polymethylsiloxane in the presence of a Karstedt catalyst. The obtained glycerinmonoallylether-, and allyloxyethanol coco fatty acid ester-modified polymethylsiloxane was formulated at 2.0% w/w in a cosmetic w/o emulsion along with 0.1% w/w hydrogenated castor oil, 0.1% w/w microcrystalline wax, 11.8% w/w liquid paraffin, 6.0% w/w ethylhexyl palmitate, 0.8% w/w sodium chloride, 3.1% w/w glycerin, 76% w/w water and 0.10% w/w 2-bromo-2-nitropropane-1,3-diol. Lipase inhibitors: Asahi Kasei Chemicals Corp. discussed lipase inhibitors containing water-soluble, beta-linked oligosaccharides in addition to disclosing cosmetic, (quasi) drug, or hair preparations containing the lipase inhibitors.18

Lipase inhibitors are useful to prevent or treat acne or body odor. They contain water-soluble carbohydrates comprising ≥ 2 beta-linked monosaccharides. An aqueos cellulose dispersion, prepared by grinding HCl hydrolyzates of dissolving pulp, was incubated with Trichoderma reesei-derived crude cellulase preparation at 55°C for 4 hr to give a composition containing 1.5% cellobiose.

The composition was filtered with an ultrafiltration membrane, treated with cation ion exchange resin and anion ion exchange resin for deionization, and vacuum-distilled at 70°C. The concentrate was gradually cooled at 10°C/hr, from 70°C to 5°C, and precipitated with ethanol. The precipitate was further processed to produce cellooligosaccharide powder containing 96.4% cellobiose and 0.8% additional cellooligosaccharides. The cellobiose-rich fraction inhibited Propionibacterium acnes lipase in a dose-dependent manner. A hair lotion containing the fraction imparted a refreshing feeling and smoothness to hair.

Reproduction of this article without permission is strictly prohibited.

References
1. KR 2009 13,293, Antiwrinkle and antiaging cosmetic composition containing Pyrus pyrifolia extract, Ansung Machum Association (Feb 5, 2009)
2. WO 2009 26,949, 4-Amidinobenzylamine urokinase inhibitors for cosmetic and/or dermatological use, Pentapharm AG, Switzerland (March 5, 2009)
3. DE 102,007,041,494, Cosmetic cleaning agent with low pH containing hydroxycarboxylic acids and ketocarboxylic acids for use especially on aging skin, Henkel AG & Co., KgaA ( March 5, 2009)
4. US 2009 62,389, In-shower lotion compositions comprising up to 10% free fatty acids with the ratio of unsaturated to saturated fatty acids is at least 1:1, Unilever PLC (March 5, 2009)
5. WO 2009 30,573, Iridescent soap bars with ordered layered microstructure containing ethoxylated alcohols, Unilever PLC, Unilever N.V. and Hindustan Unilever Ltd., UK, (March 12, 2009)
6. JP 2009 57,349, Skin-moisturizing cosmetics containing cross-linked poly-gamma-L-glutamic acid, Toyobo Co., Ltd. (March 19, 2009)
7. DE 102,007,042,286, Hair dyes containing natural dyes and 1,3-dihydroxyacetone, Henkel AG & Co., KGaA (March 12, 2009)
8. WO 2009 30,862, Use of travoprost for treating hair loss, Galderma Research & Development, France (March 12, 2009)
9. JP 2009 57,339, Cosmetic kit and method for processing hair, Nippon Fine Chemical Co., Ltd., Japan (March 19, 2009)
10. JP 2009 57,334, Hair permanent wave-setting method and permanent wave-setting intermediate agent, Nakano Co., Ltd. (March 19, 2009)
11. EP 2,030,609, Care or make-up composition consisting of a hard wax and a paste compound, method of care or make-up for eyelashes, L’Oréal, France (March 4, 2009)
12. US 2009 60,857, Lip gloss comprising stearoyl inulin, fatty acid derivatives, hydrogenated polyisobutene and fumed silica di-Me silicate gels in sugar matrix, Coty S.A.S., France (March 5, 2009)
13. WO 2009 27,390, UV absorbers stabilization of cosmetic compositions, Ciba Holding Inc., Switzerland (March 5, 2009)
14. DE 102,007,041,473, Use of glycyrrhetic acid and/or glycyrrhizine for suntanning preparations, Beiersdorf AG (March 5, 2009)
15. DE 102,007,041,475, Use of a combination of erythrulose and glycyrrhetic acid and/or glycyrrhizine in cosmetic preparations for suntanning, Beiersdorf AG (March 5, 2009)
16. DE 102,007,041,854, Biofunctional dihydroxyacetone derivatives for suntanning preparations, Merck Patent GmbH (March 5, 2009)
17. EP 2,030,605, Use of ester-modified organopolysiloxanes as emulsifiers for producing cosmetic or pharmaceutical compositions, Evonik Goldschmidt GmbH (March 4, 2009)
18. JP 2009 46,434, Lipase inhibitors containing water-soluble beta-linked oligosaccharides, and cosmetics, (quasi) drugs, and hair preparations containing them, Asahi Kasei Chemicals Corp., (March 5, 2009)

 

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Formula 1. Antiwrinkle cleansing gel3

1,6-Hexanediol 6.00% w/w
Glycolic acid 3.80
Decyl glucoside 3.00
Sodium hydroxide 1.05
Dehydroxanthan gum 1.03
L-arginine 0.40
PEG-7 glyceryl cocoate 0.40
Fragrance (parfum) 0.10
Olea europea (olive) leaf extract 0.20
 Water (aqua) qs to 100.00

Formula 2. Hair dye with natural dyes7

Xanthan gum (Keltrol CG, CP Kelco) 0.50% w/w
Algin (Texamid 558, Cognis) 0.50
Glycerin 10.00
Ethanol 12.00
Coco-glucoside (Plantacare 818, Cognis) 0.40
Dipropylene glycol (and) Lawsonia inermis (henna) leaf extract (Henna Concentrate Red Coloring HS 2686 G, Grau) 0.40
Dipropylene glycol (and) Lawsonia inermis (henna) leaf extract (and) Indigofera tinctoria extract (Henna Concentrate Black Coloring HS 2687 G, Grau) 2.00
1,3-Dihydroxyacetone 2.00
Erythrulose  3.00
Orange oil 0.10
Water (aqua) qs to 100.00

Formula 3. Hair relaxer9

First Agent  
Isopropanol 0.260%w/w
Hydrochloric acid, 1M 0.700
Methyltriethoxysilane 1.000
Tetraethoxysilane 0.110
Acetic acid 0.100
Polyoxyethylene-modified dimethicone 0.001
Polyacetal resin 0.170
Triethanolamine 0.001
Ethanol qs to 100.000
Second Agent  
Tetrahydroxypropylethylenediamine 0.300
Ethanol qs to 100.000

Formula 4. Mascara11

Candelilla wax 16.00% w/w
Carnauba wax 4.00
Jojoba oil 5.00
Black iron oxide 7.00
Gum arabic 3.40
Hydroxyethyl cellulose 0.90
Potassium cetyl phosphate 2.50
Steareth-20 5.00
Steareth-2 2.00
Cetyl alcohol 2.30
Preservatives  qs
Water (aqua) qs to 100.00

Formula 5. Lip gloss12

Diisostearyl malate 9.35% w/w
Stearoyl inulin 1.15
C15-19 alkane 9.24
Silica di-Me silicate 1.26
Hydrogenated polyisobutene gel 27.00
Polybutene 32.00
Polyethylene  1.00
Vinylpyrrolidone/hexadecene copolymer   4.00
Diisopropyl dimer dilinoleate 4.80
Preservatives 0.10
Pigments 0.10
Mica 10.00
  100.00

Formula 6. Self-tanning lotion14

Stearic acid 2.00% w/w
Dicaprylyl ester 3.00
Octyldodecanol 2.00
C12-15 alkyl benzoate 4.00
Cetyl alcohol 2.00
Cetearyl ethylhexanoate (and) isopropylmyristate 2.00
Glycerin 6.00
Ethylhexyl methoxycinnamate 2.00
Titanium dioxide 1.00
Cetyl palmitate 1.00
Glyceryl stearate 1.00
Phenoxyethanol 0.40
Butyl-methyoxydibenzoyl methane 2.00
Fragrance (parfum) qs
EDTA 0.20
Carbomer 0.20
Magnesium aluminum silicate 0.20
Methylparaben  0.10
Vitamin A acetate 0.10
Glycyrrhetic acid 0.10
Propylparaben 0.05
BHT 0.05
Dihydroxyacetone 1.00
Water (aqua) qs to 100.00

Formula 7. O/W self-tanning cream16

Ceteareth-11 (Marlipal 1618/11, Sasol Gmbh-Marl) 3.00% w/w
Cetearyl alcohol (Lanette O, Cognis) 7.00
Cetearyl ethylhexanoate (Luvitol EHO, BASF ) 5.00
C12-15 alkyl benzoate (Tegosoft TN, Degussa) 2.50
Caprylic/capric triglyceride (Miglyol 812N, Sasol ) 2.50
Propylparaben 0.05
Dihydroxyacetone-ortho-ethyl acetate 5.00
Propylene glycol 4.00
Methylparaben 0.15
Water (aqua) qs to 100.00

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