DDS Liposomes for Cosmetic Delivery and Other Recent Literature Findings

Jul 1, 2009 | Contact Author | By: Charles Fox, Independent Consultant
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Title: DDS Liposomes for Cosmetic Delivery and Other Recent Literature Findings
patentsx DDS liposomesx
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Keywords: patents | DDS liposomes

Abstract: In this month’s survey of recent patent and literature research, the author describes money-making ideas in the personal care industry, ranging from regulating sebum with spheroids to transparent film UV protection, copolymer water repellents and an aqueous amino acid preservative.

In this month’s survey of recent patent and literature research, the author describes money-making ideas in the personal care industry, ranging from regulating sebum with spheroids to transparent film UV protection, copolymer water repellents and an aqueous amino acid preservative.

Skin and Skin Care
Peptides for antiaging: The Research Foundation of the State University of New York disclosed peptides of fibronectin and vitronectin and variants thereof that have certain cosmetic activities, including growth factor-binding.1 Also described are fragments of growth factors that bind to fibronectin and inhibit binding of full-length growth factors to the same. Compositions containing such fragments are useful in wound care, cancer treatment and cosmetic treatments for wrinkles or UV photodamage of skin. These fragments allow the growth factor to retain biological activity and can be used to complement the loss of fibronectin or vitronectin from cells. The identification of minimal domains of fibronectins to promote the survival of fibronectin-null cells is demonstrated.

Regulating sebum with spheroids: Unilever PLC introduced a skin care composition comprising spheroids and optional thickening agents, and a method for regulating sebum flow from sebocytes.2 A spheroid and sebum mixture is created upon application and the resulting mixture leaves a pleasant, silky and powdery sensation. Thus, a skin care composition was prepared as shown in Fomula 1.

Hair and Hair Care
 Microemulsion shampoo formulation: Cognis IP Management GmbH launched a microemulsion-containing shampoo composition with improved hair care properties.3 This cosmetic preparation contains at least one surfactant selected from anionic, zwitterionic or amphoteric surfactants; a microemulsion; and at least one cationic polymer. An example is shown in Formula 2.

Frizz reduction with conditioning copolymers: Lion Corp. disclosed hair conditioners containing copolymers with methacrylic acid, dialkyldiallylammonium salt units and fatty acid polyglycerin esters.4 The disclosed hair rinses, hair treatments and hair conditioners also contain optional alditols and cationic surfactants, and suppress increased hair volume in high-moisture environments. A rinse-off hair conditioner containing a copolymer of acrylic acid-dimethyldiallylammonium chloride and acrylamidea, diglyceryl diisostearate, sorbitol, behenyltrimethylammonium chloride and additives was applied to a bleached and shampooed hair bundle. This composition was found to suppress an increase in maximum diameter of the hair bundle after 24 hr storage at 25°C with a relative humidity of 90%.

Copolymer for permanent hair waving: Kao Professional Salon Services GmbH has created a composition for the permanent shaping of waving of human hair through a copolymer of vinylpyrrolidone and quaternized vinylimidazole at a concentration in the range of 0.1–2.5% w/w.5 The composition of a permanent wave composition for normal hair is shown in Formula 3.

Transparent film UV protection:
Kosei Co., Ltd. discloses sunscreen cosmetics containing metal oxide particles and polysiloxanes.6 Disclosed are w/o sunscreens that provide a transparent film with UV blocking effects. The sunscreen is comprised of volatile organopolysiloxanes; fine particles of metal oxides; polysiloxanes having hydrophilic groups; oil-soluble, organic, UV ray absorbents; and organopolysiloxanes. An example is shown in Formula 4.

Copolymer water repellants in sunscreens: Beiersdorf AG has disclosed copolymers in cosmetic sun protection agents for use as water repellents.7 The invention relates to a cosmetic preparation containing styrene/acrylate copolymers and one or more UV light filters, as shown in Formula 5.

Color Cosmetics
Three-step process for nail color: L’Oréal discloses a three-step color application process for nails comprising color precursor, color activator and color deactivator compositions.8 The first step of this process involves applying a composition containing at least: one color precursor, one film former, one volatile solvent and one optional buffer or colorant. The second step is to apply a second composition comprised of a color activator on top of at least a portion of the first composition. The final step is to apply an optional third composition comprised of at least one color deactivator on top of at least a portion of the second composition. An example is shown in Formula 6.

Lip and skin color with polyester: L’Oréal also has disclosed skin and lip cosmetics containing a certain polyester and a branched hydrocarbon, along with a treatment method for employing the composition and use of the composition for treating or coloring the skin or lips.9 Pentaerythrityl benzoate/isophthalate/isostearate is prepared from pentaerythritol, and the corresponding acids and this ester are applied in a lipstick formulation.

Polyester and gelling agent lipstick: L’Oréal has patented a transparent cosmetic composition formulated with a polyester and a gelling agent.10 This composition is comprised of 0.1–70% polyester, 1–90% w/w oil and 0.01–50% w/w gelling agent. The polyester is obtained by the reaction of: at least one polyol comprising 3–6 hydroxyl groups; at least one non-aromatic monocarboxylic acid; at least one aromatic monocarboxylic acid and polycarboxylic acid comprising at least two carboxylic groups and/or a cyclic anhydride of such a polycarboxylic acid. Benzoic acid, isostearic acid, isophthalic acid and pentaerythritol were reacted to obtain pentaerythrityl/benzoate/isostearate/isophthalate polycondensate as a thick oil. A formulation of a lipstick containing the above polycondensate is also disclosed.

Hydroxyl compound makeup: L’Oréal again discloses a makeup composition comprising a hydroxyl compound.11 This w/o emulsion comprises 10–60% water; a hydrocarbon surfactant; excipients; and a hydroxyl compound selected from propylene glycol, a mixture of mono- and/or di-glycerides of caprylic and capric acid, and their mixture. An example of a cosmetic foundation is shown in Formula 7.

Interesting Compositions and Raw Materials
Congealed o/w dispersion/emulsion: Henkel AG and Co., KGaA has created an antiperspirant stick based on a congealed o/w dispersion/emulsion.12 An example is shown in Formula 8.

Aqueous amino acid preservative: Ajinomoto Co., Inc. discloses an aqueous preservative solution with a high amino acid content and compositions formulated with this solution.13 The preservative solution is made up of pyrrolidone carboxylic acid and/or its salts, a basic amino acid and/or its salts, an acid amino acid and/or its salts, a neutral amino acid and/or its salts, lactic acid and/or its salts, and water, wherein the pH of the solution is 3.5–6.0. This preservative solution comprises: 15% sodium L-pyrrolidone carboxylate, 4.00% DL-pyrrolidone carboxylate, 8.00% L-arginine, 0.15% L-histidine, 5.20% L-aspartic acid, 1.30% glycine, 1.20% L-alanine, 0.40% L-proline, 0.80% L-serine, 0.40% L-threonine, 0.65% L-valine, 0.40% L-isoleucine, 0.15% L-phenylalanine and 12.00% sodium DL-lactate at pH 5. Formulation of a shampoo containing 5% of the above solution is disclosed. Low pH and viscosity emulsion: Kosei Co., Ltd. has patented a cosmetic emulsion containing polyoxyethylene sorbitan monostearate and higher alcohols.14 The stable o/w emulsified cosmetic described has both a low pH and low viscosity. The cosmetic compositions comprise twenty moieties of polyoxyethylene sorbitan monostearate (INCI: Polysorbate 60), C16-22 higher alcohols, water, polysaccharide-type, water-soluble polymers and acidic substances, wherein the weight ratio of polyoxyethylene sorbitan monostearate to C16-22 higher alcohols is 0.05–10. The emulsion has a pH 3–4.5 and viscosity of 1,000–7,500 m•Pas at 25°C. An example is shown in Formula 9.

2-propyl heptyl octanoate emulsion: Beiersdorf AG has created a stabile cosmetic o/w emulsion containing 2-propyl heptyl octanoate, cetearyl alcohol, sodium cetearyl sulfate and glyceryl stearate.15 An example of a sunscreen is shown in Formula 10.

Surfactant-coated, methacrylic polymer: Kao Corp. disclosed surfactant-coated, crosslinked, methacrylic polymer particles for cosmetics, and the production of these polymer particles.16 These particles impart smoothness and good dispersibility in a hydrophobic medium. In this medium a crosslinked, methacrylic acid ester-based polymer particle is prepared from a methacrylate ester and a carboxyl group-containing compound. In addition, the polymer particle is coated with a surfactant represented by a general formula:


in which R1 is C7-22 monovalent hydrocarbon, and R2, R3 is either a hydrogen atom or any hydroxylalkyl group containing two or three carbon atoms. The polymer particle may be further coated with a sulfonate group-containing surfactant. A method for production of the polymer particle is also disclosed. For example, a polymer particle dispersion was prepared from lauryl methacrylate, ethylene glycol dimethacrylate, methacrylic acid, lauroyl peroxide, and N-stearoyl-N-methyl taurine sodium salt; and treated with palm kernel oil fatty acid diethanolamide to result in the present invention.

DDS liposomes for cosmetics: Miyajima et al. have published research on the application of drug delivery systems technology in liposomes for cosmetic materials.17 The cosmetic effect of acetyl hydroxyproline (AHYP) internally enveloped in liposomes was examined with the aim of enhancing the quality of cosmetic products. Also examined was the method for analyzing the enveloped AHYP in order to give credibility to cosmetic products.

The preparation of the liposomes AHYP, hydrogenated lecithin and cholesterol, and/or other cosmetic additives was dissolved by heating the preparation in dipropylene glycol. The solution was dispersed in a buffer solution, was particle-sized through an extruder, and was used as a cosmetic preparation. AHYP and cholesterol were quantified by using a high-performance liquid chromatography (HPLC) method; and the method for extracting AHYP from the liposomes also was examined to establish the method. After non-enveloped AHYP had been removed by using a dialysis tube, the enveloped AHYP was determined. The forearm flexor surface parts of monitors were washed and, after drying, the cosmetic preparation was painted on the parts. The moisturizing effect of the cosmic preparations was periodically measured on the keratinous water content at the painted partsb and on the evaporation of moisturec.

The moisturizing effect of AHYP, dependent to the amounts of dipropylene glycol (1–8%), was confirmed and silicone oil acted negatively on the positive effect of AHYP. The cosmetic liposomes are capable of being formulated as a lotion containing 50% liposome. Reproduction of all or part of this article is strictly prohibited


1. WO 2008 157,483, Growth factor-binding peptides of fibronectin and vitronectin for cosmetic use, The Research Foundation of State University of New York, USA (Dec 24, 2008)
2. US 2008 254,074, Composition comprising spheroids and method for regulating sebum flow, Unilever PLC, USA (Oct 16, 2008) 3. WO 2008 155,073, Microemulsion-containing shampoo composition having improved care properties, Cognis IP Management GmbH, Germany (Dec 24, 2008)
4. JP 2008 308,415, Hair conditioners containing copolymers having (meth)acrylic acid unit and dialkyldiallylammonium salts unit and fatty acid polyglycerin esters, Lion Corp, Japan (Dec 25, 2008)
5. US 2009 4,129, Composition for the permanent shaping of human hair containing a copolymer of vinylpyrrolidone and quaternized vinylimidazole, KAO Professional Salon Services GmbH, Germany (Jan 1, 2009)
6. JP 2008 247,816, Sunscreen cosmetics containing metal oxide particles and polysiloxanes, Kosei Co, Ltd, Japan (Oct 16, 2008) 7. DE 102,007,028,497, Styrene/acrylate copolymers in cosmetic sun protection agents for use as water repellents, Beiersdorf AG, Germany (Dec 24, 2008)
8. US 2008 253,980, Method for making up nails comprising compositions containing a color precursor, a color activator and a color deactivator, L’Oréal, France (Oct 16, 2008)
9. US 2008 317,693, Skin and lip cosmetics containing a polyester and a branched hydrocarbon, L’Oréal, France (Dec 25, 2008)
10. FR 2,917,617, Transparent cosmetic composition including a polyester and a gelling agent, L’Oréal, France (Dec 26, 2008)
11. FR 2,917,609, Make-up composition comprising a hydroxyl compound, L’Oréal, France (Dec 26, 2008)
12. WO 2008 155,391, Cosmetic stick based on a congealed oil-in-water dispersion/emulsion, Henkel AG and Co KGaA, Germany (Dec 24, 2008)
13. FR 2,914,854, Aqueous preservative solution with a high amino acid content and cosmetics containing it, Ajinomoto Co, Inc, Japan (Oct 17, 2008)
14. JP 2008 247,866, Cosmetic emulsions containing polyoxyethylene sorbitan monostearate and higher alcohols, Kosei Co, Ltd, Japan (Oct 16, 2008)
15. DE 102,007,017,434, Stabile cosmetic O/W emulsions containing octanoate, glyceryl stearate, cetearyl alcohol and sodium cetearyl sulfate, Beiersdorf AG, Germany (Oct 16, 2008)
16. JP 2008 255,072, Surfactant-coated crosslinked (meth)acrylic polymer particles for cosmetics, and production thereof, Kao Corp, Japan, (Oct 23, 2008)
17. Y Miyajima et al., Application of DDS technology-liposomes for cosmetic materials, Frag J 36(11) 69–71 (2008) (in Japanese)




aMerquat Plus 3330 (INCI: Polyquaternium-39) is a product of Nalco.

bSKICON-200 is a device manufactured by I.B.S. Co., Ltd.

cVAPO-SCAN is a device manufactured by Asahi Biomed.

Formula 1. Sebum flow regulator2

Lauric acid  11.50%w/w
Oleic acid 11.50
Isostearic acid 5.75
Tricaprin 11.50
Triolein 11.50
Glyceryl isostearates 5.75
Oleyl oleate 10.40
Myristyl myristate 10.40
Isostearyl isostearate 5.20
Squalene 12.00
Cholesterol oleate 3.00
Cholesterol 1.50
Artificial sebum mixture in A 40.00
Polyethylene (CL-2080, Kobo Products) 60.00

Formula 2. Microemulsion shampoo3

Microemulsion Composition
Decyl glucoside (Plantacare 2000 UP, Cognis) 17.50%w/w
Glyceryl oleate (Monomuls 90-O 18, Cognis) 8.00
Dicaprylyl ether (Cetiol OE, Cognis) 20.00
Water (aqua) qs to 100.00
Shampoo Composition
Sodium laureth sulfate (Texapon N 70, Cognis) 9.00
Cocamidopropyl betaine (Dehyton PK 45, Cognis) 3.00
Microemulsion (above) 1.78
Polyquaternium-10 (Dekaquat 400 KC, Dekker) 0.20
PEG/PPG-120/10 trimethylolpropane trioleate (Arlypon TT, Cognis) 0.65
Methyldibromo glutaronitile (and) phenoxyethanol (Euxyl K 400, schülke inc.) 0.10
Water (aqua) qs to 100.00

Formula 3. Permanant wave composition5

Ammonium thioglycolate 21.30%w/w
Ammonium bicarbonate 5.00
Butylene glycol 3.00
Polyquaternium-16 0.50
PEG-40 hydrogenated castor oil 0.70
Fragrance (parfum) 0.40
Ammonia, 25% qs to pH 8.3
Water (aqua) qs to 100.00


Formula 4. Sunscreen with zinc oxide6

Zinc oxide microparticles 20.00%w/w
Lauryl PEG-9 polydimethylsiloxyethyldimethicone (KF 6038, Shin-Etsu) 5.00
Decamethylcyclopentasiloxane 25.00
Dimethylpolysiloxane 5.00
2-Ethylhexyl-p-methoxycinnamate 10.00
Dimethylsilanediol-hexylmethylsilanediol copolymer 5.00
PEG-9 dimethicone 1.00
Butylene glycol 5.00
Ethanol 3.00
Sodium chloride 0.50
Preservative qs
Water (aqua) qs to 100.00


Formula 5. Water repellant sunscreen7

Glyceryl stearate citrate 0.50%w/w
Cetearyl alcohol 2.00
Styrene/acrylate copolymer 5.00
Vinylpyrrolidone/acrylic acid copolymer 0.50
Butylene glycol dicaprylate/dicaprate 10.00
Octyldodecanol 3.00
Myristyl myristate 1.00
Glycerin 2.00
Butylmethoxydibenzoyl methane 2.50
Octyl salicylate 4.00
Phenylbenzimidazole sulfonic acid 3.00
Sodium starch octenyl succinate 3.00
Alcohol 0.50
Taurine 0.10
Folic acid 0.01
Vitamin E acetate 0.20
Disodium EDTA 0.10
Fragrance (parfum) qs
Preservative qs
Dyes qs
Sodium hydroxide qs
Water (aqua) qs to 100.00

Formula 6. Three-step nail color8

Color precursor
Film formers 14.00%w/w
Plasticizers 5.00
Volatile solvent 79.00
3,3-bis(2-Methyl-1-octyl-1H-indol-3-yl)phthalide (color precursor) 0.50
Aminomethylpropanol 0.40
Pigments/fillers 1.00
Gelling agent 0.10
Color activator
Isopropyl alcohol 96.00
Citric acid 4.00
Color deactivator
Isopropyl alcohol 95.00
Aminomethyl propanol 5.00

Formula 7. Foundation lotion11

PEG-30 dipolyhydroxystearate (Arlacel P135, Croda) 5.00% w/w
C12-13 dimalate 8.00
Capric (and) caprylic acid glycerides 1.00
Modified hectorite 0.80
Propylene carbonate 0.50
Pigments coated with amino acids 10.00
Isododecane 15.00
Polymethylmethacrylate 5.00
Sodium chloride 0.70
Glycerol 2.50
Butylene glycol 3.50
Ethyl alcohol 10.00
Propylene glycol 1.00
Glycerol 2-ethylhexylether 1.00
Octane-1,2-diol 1.00
Water (aqua) qs to 100.00


Formula 9. Stable, low pH, low viscosity o/w emulsion14

Polysorbate 60 0.80% w/w
Lactic acid 0.10
Sodium lactate  0.10
Butylene glycol 12.00
Methylparaben 0.15
Dimethylpolysiloxane 0.40
Glyceryl stearate 0.40
Cetostearyl alcohol 0.35
Behenyl alcohol 0.35
Squalane 9.00
Hydrogenated phospholipids 0.20
Xanthan gum 0.10
Ethanol 5.00
Water (aqua) qs to 100.00

Formula 8. Antiperspirant stick12

Glycol distearate (Cutina AGS, Cognis) 2.40% w/w
Palmitic acid (and) stearic acid (Cutina FS45, Cognis) 2.75
Ceteareth-20 (Eumulgin B2, Cognis) 0.75
Ceteareth-30 (Eumulgin B3, Cognis) 0.75
Diisopropyl adipate (Ceraphyl 230, ISP) 6.00
Cocoglycerides (Novata AB, Cognis) 4.00
Cetyl palmitate (Cutina CP, Cognis) 5.00
Hydrogenated castor oil (Cutina HR, Cognis) 3.50
Cetearyl Behenate (Kesterwax K62, Koster Keunen) 4.50
Aluminum hydroxychloride, 50% in water 40.00
Talc 10.00
Tris (tetramethylhydroxypiperidenol) citrate (Tinogard Q, Ciba) 0.05
Propylene glycol 10.00
Water (aqua) qs to 100.00

Formula 10. Stable o/w sunscreen emulsion15

Cetearyl alcohol 1.00%w/w
Sodium cetearyl sulfate 0.20
Glyceryl stearate SE 0.20
Stearyl alcohol 1.00
Xanthan gum 0.10
Butylene glycol dicaprylate/dicaprate 5.00
C12-15 alkyl benzoate 5.00
Cyclomethicone 2.00
Glycerin 2.00
C12-38 acid triglyceride 1.00
2-propyl heptyl octanoate 3.00
Butyl methoxydibenzoylmethane 4.00
Phenylbenzimidazole sulfonic acid 2.00
Bis-ethylhexyloxyphenol methoxyphenyl triazine 2.00
Titanium dioxide 2.00
PVP-hexadecene copolymer 0.50
Starch 1.00
Vitamin E acetate 0.10
Disodium EDTA 0.10
Fragrance (parfum) 0.20
Preservative 0.30
Sodium hydroxide qs
Water (aqua) qs to 100.00

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