Lyotropic Liquid Crystals for Damaged Hair and Other Topics: Literature Findings

Aug 1, 2009 | Contact Author | By: Charlie Fox, Independent Consultant
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Title: Lyotropic Liquid Crystals for Damaged Hair and Other Topics: Literature Findings
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This month’s survey of recent patent and research literature describes moneymaking ideas for personal care product development, including an integral collagen treatment, CoQ10 for UVB-induced wrinkles, fullerene in cosmetics, a melatonin hair treatment and biotin for hair growth, among others.

Skin and Skin Care
TiO2 nanoparticles on AD lesions: Yanagisawa et al. have found that titanium dioxide nanoparticles aggravate atopic dermatitis (AD)-like skin lesions in NC/Nga mice.1 Titanium dioxide (TiO2) nanoparticles are produced abundantly and used ubiquitously in various cosmetic products. However, the effects of transdermal exposure of AD skin to TiO2 nanoparticles had yet to be determined.

In the described work, the authors investigated the effects of differently sized TiO2 nanoparticles on AD-like skin lesions in NC/Nga mice assumed to show skin barrier dysfunction/defects. Male mice were injected intradermally with TiO2 nanoparticles of 15 nm, 50 nm or 100 nm and/or mite allergen into their right ears. The authors evaluated clinical scores, ear thickening, histological findings and the protein expression of T helper (Th) 1 and Th2 cytokines in the ear, and the levels of immunoglobulin (Ig) and histamine in serum. TiO2 nanoparticles aggravated AD-like skin lesions related to mite allergen in NC/Nga mice. The enhancing effects were paralleled by the overproduction of interleukin-4 (IL-4) in the skin and the overall levels of total immunoglobulin E (IgE) and histamine in serum. In contrast, TiO2 nanoparticles decreased the local expression of IFN-gamma in the presence of an allergen.

Additionally TiO2 nanoparticles alone significantly increased histamine levels in serum and IL-13 expression in the ear. However, different effects related to size variances of the TiO2 nanoparticles were not observed. Thus, researchers concluded that exposure to TiO2 nanoparticles under skin barrier dysfunction/defects could exacerbate AD symptoms. Furthermore, TiO2 nanoparticles could play a significant role in the initiation and/or progression of skin diseases following the barrier dysfunction/defect by histamine release even in the absence of an allergen.

CoQ10 on UVB-induced wrinkles: Inui et al. studied the mechanisms of inhibitory effects of coenzyme Q10 (CoQ10) on UVB-induced wrinkle formation in vitro and in vivo.2 Photo-damaged skin exhibits wrinkles, pigmented spots, dryness and tumors. Solar UV radiation induces cyclobutane pyrimidine dimers (CPD) and further produces base oxidation by reactive oxygen species (ROS). ROS are thought to be a major factor to initiate the up-regulation of matrix metalloproteinases (MMPs) in keratinocytes and fibroblasts via activation of receptor proteins on the cell membrane of keratinocytes and fibroblasts, and to degrade fiber components in the dermis, leading to wrinkle formation.

CoQ10 was reported to reduce ROS production and DNA damage triggered by UVA irradiation in human keratinocytes in vitro. Further, CoQ10 was shown to reduce UVA-induced MMPs in cultured human dermal fibroblasts. The authors thus speculated that UVB radiation-induced cytokine production in keratinocytes may be inhibited by CoQ10, resulting in the reduction of MMPs in fibroblasts leading to wrinkle reduction.

In vitro studies showed that UVB-induced IL-6 production of normal human keratinocytes (NHKC) decreased in the presence of CoQ10. Furthermore, MMP-1 production of fibroblasts cultured with the medium containing CoQ10 collected from UVB-irradiated NHKC significantly decreased during 24 h culture. In the clinical trial study, the researchers found that the use of 1% CoQ10 cream for five months reduced the wrinkle score grade, as observed by a dermatologist. The combined results indicate that CoQ10 may inhibit the production of IL-6, which stimulates fibroblasts in the dermis in a paracrine manner, thus up-regulating the production of MMPs and protecting the dermal fiber components from degradation, leading to rejuvenation of wrinkled skin.

Fullerene in cosmetics: Li et al. have published a study indicating that fullerene exhibits the ability to remove free radicals and inhibit the formation of melanin.3 Formulating chemists have developed various ways for fullerene to dissolve in water, which extends its application fields greatly. In this paper, the application of fullerene progresses in cosmetics are introduced in detail.

Flavanone for antiaging skin care: Bio Spectrum Inc. disclosed antiaging compositions containing flavanone compounds and their use for skin care products.4 The antiaging composition contains 7-hydroxyflavanone and 7-methoxyflavanone compounds, their derivatives or their mixture. These flavanone compounds stimulated collagen synthesis in fibroblasts and inhibited collagenase activity, thus eliminating wrinkles. The antiaging composition is recommended for products to reduce wrinkles.

Hair and Hair Care
 Lyotropic liquid crystals for damaged hair: The Procter & Gamble Company introduced a shampoo for treating damaged hair comprising an anionic surfactant and a cationic polymer, the combination of which forms lyotropic liquid crystals.5 Chemically treated and damaged hair was washed with the shampoo composition consisting of: 5–50% w/w anionic surfactant, water, and 0.025–5% w/w synthetic cationic polymer with a cationic charge of 2–7 meq/gm, wherein the synthetic cationic polymer forms lyotropic liquid crystals upon combination with the anionic surfactant and water. The composition was then rinsed from the hair and researchers found that, after the treatment, the surface energy of the hair was reduced, compared with its surface energy prior to the treatment. An example of the shampoo is shown in Formula 1.

Natural plant conditioning shampoos: Faming Zhuanli Shenqing Gongkai Shuomingshu has developed hair and scalp cleansing and conditioning shampoos using natural plants.6 An example is shown in Formula 2. To mix the shampoo, researchers heated palm oil, hempseed oil and Gleditsia sinensis powder to 80°C. Then, water was heated to 90°C, and the oil phase was added to the water phase while stirring at 600 rpm. An emulsifier was added to the batch and it was cooled to 40°C while Zanthoxylum bungeanum and Angelica dahurica were added. The batch was stirred for an additional 30 min.

Nonsticky, aqueous hair styler: Kao Corp. has developed nonsticky aqueous hair styling compositions.7 The compositions exhibit good spreadability and strong styling power while imparting a fluffy appearance to hair. They contain: 1–20% solid or pasty oily ingredients; 1–5% liquid oils selected from silicone oils, hydrocarbon oils and ester oils; 0.01–5% anionic surfactants except higher fatty acid salts; 3–10% higher molecular weight fatty alcohols; 0.01–0.5% high molecular-weight polyethylene glycol; and (optionally): 5–30% polyhydric alcohols; 1–10% higher fatty acids or their salts; and 3–10% nonionic surfactants. Thus, a hair styling wax was formulated containing microcrystalline waxa; petrolatum; dipentaerythritol esters of hydroxystearic acid, stearic acid and rosin acid; diisostearyl malate; methylpolysiloxane; octyldodecyl myristate; polyoxyethylene lauryl ether sodium phosphate; cetanol; polyethylene glycol (MW = 2,500,000); glycerin; sorbitol solution; stearic acid; polyoxyethylene sorbitan monostearate; glyceryl stearate; and isostearyl glyceryl ether.

Melatonin/agomelatine hair treatment: Henkel AG & Co. has disclosed a hair treatment agent with conditioner(s) and melatonin/agomelatine8 to protect hair against external aggressors. The treatment contains at least 0.1–10% of a cationic conditioner; 0.001–5% of one or more fatty components; 0.001–5% melatonin and/or a salt thereof and/or agomelatine and/or a salt thereof; and at least one conditioning enhancer from the group of: L-carnitine and/or a salt thereof; pantolactone, taurine and/or a salt thereof; vitamins, specifically niacinamide; biotin, pantothenic acid and tocopherol and/or derivatives thereof; ubiquinone; ectoin; allantoin; plant extracts such as echinacea or moringa; plants; xanthines such as caffeine; theophylline and theobromine; and flavonoids such as flavonols, bisabolol and creatine. An example of a hair conditioning cream is shown in Formula 3.

Chitosan for hair volume or hold: Henkel AG & Co. also disclosed cosmetic compositions with chitosan and silicone elastomers.9 The hair treatments comprise 0.05–5% w/w of at least one chitosan and/or chitosan derivative and 0.05–5% w/w of at least one elastomeric silane or siloxane with quaternary ammonium groups to improve fullness, volume and long-term hold in hair. An example is shown in Formula 4.

Sulfonic acid hair compositions: Kao Corp. introduced hair cosmetics containing sulfonic acids with excellent spreadability and a smooth and flexible finish.10 The rinses, treatments, conditioners, creams, gels and foams, contain C6-18 hydrocarbyl-containing sulfonic acids or their salts, quaternary ammonium salts, C8-30 alcohols and liquid crystal-forming agents. An example is shown in Formula 5. Rinsing the hair with this preparation resulted in good coatability and a smooth, soft and nonsticky finish.

Hair dye compositions: L’Oréal has created hair dye compositions comprising an aminopyrazolopyridine oxidation base, a coupler and a surfactant.11 These compositions contain C8-30 alkylether carboxylic acids and their salts or C12-30 alkyl polyglycosides as surfactants. The compositions are applied to hair in the presence of an oxidizing agent for a sufficient time to develop the desired color. The color obtained has a different tone and is resistant to adverse conditions. A hair dye composition contained 0.006 mol 2-[(3-aminopyrazolo-1,5-a]pyridin-2-yl)oxyethanol hydrochloride, 0.006 mol 1-methyl-2-hydroxy-4-aminobenzene, and excipients to 100 g. The composition gave a strong blue color to the hair.

Permanent deformation of keratin fibers: Henkel AG & Co. have published a hair styling method for the permanent deformation of keratin fibers but with the appearance of temporary hair styling, without the use of perm rods. The method incorporates a reducing substance followed by an oxidizing composition containing film-forming polymers.12 Hair fibers are treated with an aqueous preparation of a keratin-reducing substance, rinsed after an exposure time, fixed with an aqueous solution of an oxidizing agent, rinsed after a second exposure time, and optionally treated. Even when used at home, the method permits long-lasting hair styling that resists damage over time, endures unfavorable weather conditions and can be employed in daily hair care routines without appearing “severe” or “old-fashioned” like the classic permanent wave. No formulation example is presented.

Promoting hair growth with biotin and purine: Henkel AG & Co. also was issued a patent on hair growth-promoting preparations.13 The invention relates to hair treatment agents for activating hair growth that are contained in a cosmetic carrier. These agents include at least one biotin compound; at least one taurine compound; purine and/or at least one purine derivative; and at least one glycoprotein. The invention further relates to a method for activating hair growth, improving hair structure and reducing hair loss. An example is shown in Formula 6.

Raw Materials
Ceramides from wool for skin and hair: Ramirez et al. report on ceramides extracted from wool and a pilot plant solvent extraction method for obtaining those ceramides.14 Ceramides extracted from wool fibers have proven beneficial in pharmaceutical and cosmetic formulations for the treatment and care of skin and human hair. This work sought to obtain internal wool lipid extracts enriched in ceramides at a pilot plant level without causing significant damage to the wool fiber.

Two extraction methodologies were performed using two solvents—acetone and methanol. Analyses of wool extracts were performed with thin layer chromatography coupled to an automated ionization detector, and chemical and mechanical evaluations of extracted wool were conducted. Larger amounts of ceramides were obtained when wool fibers were extracted with methanol than with acetone, with only some modification of the fiber properties. This lipid extract could prove to be a highly valuable by-product for the wool industry.

Skin care fabric with cyclodextrin fixation: Yamamoto et al. have published on a complex fixation technology for the production of a functional skin care fabric.15 The practical application of the fixation technology was examined using cyclodextrin, which was stabilized and fixed on the surface of the synthetic fiber using a mixture of isocyanate and glyoxal cross-linking agents. During development, the process was put into practical use using a production machine. The woven fabric was fixed with vitamin E by means of the described technology, and the resulting fabric provided skin care benefits. Integral collagen treatment: Puig et al. describe a multifunctional ingredient for an integral collagen treatment.16 The ingredientb is comprised of active peptides and proteins that improve overall collagen quality via three primary mechanisms: decreased synthesis, altered fibril organization and increased destruction. By combining actives to tackle each problem independently, the researchers found it possible to create a trifunctional product that provided significant antiaging activity.

Dipolar ionic compounds: Evonik Goldschmidt GmbH disclosed dipolar ionic compounds, sample formulations, and use of the compounds in cosmetics.17 Formic acid and 3-dimethylaminopropylamine were reacted under a nitrogen atmosphere at 175°C for 4–5 hr and the obtained amide amine was reacted with sodium monochloroacetate. The result, in aqueous solution, was a product consisting of 38.5% component along with 11.5% sodium chloride and 50% water. A test formulation was created with 1.0% w/w of the above product solution, 3% polyglyceryl-3-methylglucose distearate, 2.0% glyceryl stearate, 1.0% stearyl alcohol, 5.0% cetearyl ethylhexanoate, 14.0% mineral oil, and water to 100%. Reproduction of all or part of this article is strictly prohibited.

References
1. R Yanagisawa et al, Titanium dioxide nanoparticles aggravate atopic dermatitis-like skin lesions in NC/Nga mice, Experimental Biology and Medicine 234(3) 314–322 (2009)
2. M Inui et al, Mechanisms of inhibitory effects of CoQ10 on UVB-induced wrinkle formation in vitro and in vivo, BioFactors 32(1–4) 237–243 (2008) (In English)
3. Q Li et al, Application of fullerene in cosmetics, Jingxi Yu Zhuanyong Huaxuepin 16(13) 18–20 (2008) (in Chinese)
4. KR 2009 10,283, Antiaging composition containing flavanone compounds and its use for skin care products, Bio Spectrum Inc., South Korea (Jan 30, 2009)
5. WO 2009 24,936, Method for treating damaged hair with shampoo comprising anionic surfactant and cationic polymer, the combination forming lyotropic liquid crystals, The Procter & Gamble Company, USA (Feb 26, 2009)
6. CN 101,357,110, Hair conditioning shampoos containing natural plants, Faming Zhuanli Shenqing Gongkai Shuomingshu, Taiwan (Feb 4, 2009)
7. JP 2009 40,740, Nonsticky aqueous hair styling compositions containing solid or pasty oily ingredients, liquid oils, anionic surfactants, higher alcohols and high molecular weight polyethylene glycol, Kao Corp., Japan (Feb 26, 2009)
8. DE 102,007,039,745, Hair treatment agent with conditioner(s) and melatonin/agomelatine, Henkel AG & Co., KGaA, Germany (Feb 26, 2009)
9. DE 102,007,039,519, Cosmetic compositions with chitosan and silicone elastomers, Henkel AG & Co., KGaA, Germany (Feb 26, 2009)
10. JP 2009 40,687, Hair cosmetics containing sulfonic acids with excellent spreadability and smooth and flexible finish, Kao Corp., Japan, (Feb 26, 2009)
11. FR 2,920,090, Hair dye composition comprising a aminopyrazolopyridine oxidation base, a coupler and a surfactant, L’Oréal, France (Feb 27, 2009)
12. WO 2009 27,238, Hair styling method using a reducing substance without perm rods followed by an oxidizing composition containing film-forming polymers, Henkel AG & Co. KGaA, Germany (Mar 5, 2009)
13. WO 2009 27,112, Hair growth promoting perparations containing biotin, taurine, purine or their derivatives and at least one glycoprotein, Henkel AG & Co., KGaA, Germany (Mar 2009)
14. R Ramirez et al, Ceramides extracted from wool: Pilot plant solvent extraction, Textile Research J 78(1) 73–80 (2008)
15. T Yamamoto et al, Development of inclusion complex fixation technology and its practical application. Development of skin-care fabric with cyclodextrin fixation technology, Ishikawa-ken Kogyo Shikenjo Kenkyu Hokoku 2007, 57, 29–34 (2008) (in Japanese)
16. A Puig et al, A trifunctional ingredient for an integral collagen treatment, Speciality Chemicals Magazine 27(10) 50–51 (2007)
17. DE 102,007,040,001, Novel dipolar ionic compounds comprising formulations and the use thereof in cosmetics, Evonik Goldschmidt GmbH, Germany (Feb 26, 2009)

 

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Footnotes

aMultiwax W 44 (INCI: Microcrystalline wax) is a product of Sonneborn.
bTrylagen (INCI: Water (aqua) (and) Pseudoalteromonas Ferment Extract (and) Hydrolyzed Wheat Protein (and) Hydrolyzed Soy Protein (and) Tripeptide-10 Citrulline (and) Tripeptide-1 (and) Lecithin (and) Xanthan Gum (and) Carbomer (and) Triethanolamine (and) Phenoxyethanol (and) Butylene Glycol (and) Caprylyl Glycol) is a product of Lipotec SA.

Formula 1. Shampo for damaged hair5

Ammonium laureth sulfate 6.50%w/w
Ammonium lauryl sulfate 8.10
Sodium lauryl sulfate 1.40
Cocamide MEA 1.00
Cetyl alcohol 0.35
Lauryl alcohol 0.20
Methyl (Bis-(hydrogenated tallow amidoethyl) 2 hydroxyethyl ammonium methyl sulfate (Evonik, Varisoft 110) 0.40
Trihydroxystearin 0.25
Fragrance (parfum) 0.55
Sodium chloride 0.30
Ammonium xylene sulfonate 0.20
Citric acid 0.04
Sodium citrate 0.40
Sodium benzoate 0.25
Diamine 0.10
Polydecene 0.40
Trimethylolpropane 0.10
Water (aqua) qs to 100.00

Formula 2. Hair conditioning shampoo6

Elaeis guineensis (palm) oil 15.00%w/w
Cannabis sativa (hempseed) seed oil 6.00
Gleditsia sinensis powder 8.00
Angelica dahurica 9.00
Zanthoxylum bungeanum 8.00
Emulsifier 2.00
Water (aqua) qs to 100.00

Formula 3. Hair conditioning cream8

Paraffinum liquidum (mineral) oil 1.00%w/w
Distearoylethyl hydroxyethylmonium methosulfate (and) cetearyl alcohol (Dehyquart F 75, Cognis) 2.00
Quaternium-87 (Varisoft W 575 PG, Evonik Degussa) 1.50
Cetearyl alcohol 3.50
Lecithin 0.40
Propylparaben 0.15
Glyceryl stearate 0.70
Stearamidopropyldimethylamine 1.00
Cetrimonium chloride (Dehyquart A CA, Cognis) 3.00
Citric acid 0.50
Methylparaben 0.15
Phenoxyethanol 0.40
D-panthenol, 75% 0.20
Hydrolyzed wheat protein (Gluadin W 20, Cognis) 1.00
Melatonin 0.10
Polyquaternium-37 (and) propylene glycol dicaprylate/dicaprate (and) PPG-1 trideceth-6 (Salcare SC96, Ciba) 1.00
Water (aqua) qs to 100.00

Formula 4. Hair treatment composition9

Benzophenone-4 0.05% w/w
Citric acid 0.01
Chitosan PCA (Kytamer PC, Amerchol) 1.00
Ethanol 15.00
Silicone quaternium-16/glycidoxyl dimethicone crosspolymer (and) trideceth-12) (DC 5-7070 emulsion, Dow Corning) 5.00
D-panthenol 0.25
PEG-40 hydrogenated castor oil 0.50
Fragrance (parfum) 0.10
Water (aqua) qs to 100.00

Formula 5. Hair rinse10

Sodium 2-naphthalenesulfonate 1.00% w/w
Cetyltrimethylammonium chloride 2.00
Cetyl alcohol 1.50
Stearyl alcohol 1.50
Isostearyl glyceryl pentaerythrityl ether 1.00
Water (aqua) qs to 100.00

Formula 6. Hair growth promoter10

Cetearyl alcohol (Hydrenol D, Cognis) 9.50%w/w
1-Dodecanol (and) 1- tetradecanol (and) lauryl myristyl alcohol (Lorol Spezial, Cognis) 2.40
Ceteareth-12 (Eumulgin B1, Cognis) 0.50
Ceteareth-20 (Eumulgin B2, Cognis) 0.50
Sodium laureth-6 carboxylate (Akypo Soft 45 NV, Kao) 10.00
Sodium myreth sulfate (Texapon K 14S 70C, Cognis) 2.80
Lauryl glucoside (Plantacare 1200 UP, Cognis) 2.00
Octyldodecanol (Eutanol G, Cognis) 1.00
L-arginine 0.50
Ascorbic acid 0.20
5,6-Dihydroxyindoline hydrobromide 1.30
Taurine 0.50
Caffeine 0.10
D-biotin 0.001
Phytodermine 0.10
Ammonia, 50% 1.20
Water (aqua) qs to 100.00

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