WO2024099690A1 - A personal care composition - Google Patents
A personal care composition Download PDFInfo
- Publication number
- WO2024099690A1 WO2024099690A1 PCT/EP2023/078588 EP2023078588W WO2024099690A1 WO 2024099690 A1 WO2024099690 A1 WO 2024099690A1 EP 2023078588 W EP2023078588 W EP 2023078588W WO 2024099690 A1 WO2024099690 A1 WO 2024099690A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- carboxymethyl
- retinyl
- carboxymethyl cysteine
- retinoid
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 104
- -1 carboxymethyl cysteine compound Chemical class 0.000 claims abstract description 43
- 150000004492 retinoid derivatives Chemical class 0.000 claims abstract description 28
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- CBKLICUQYUTWQL-XWGBWKJCSA-N methyl (3s,4r)-3-methyl-1-(2-phenylethyl)-4-(n-propanoylanilino)piperidine-4-carboxylate;oxalic acid Chemical compound OC(=O)C(O)=O.CCC(=O)N([C@]1([C@H](CN(CCC=2C=CC=CC=2)CC1)C)C(=O)OC)C1=CC=CC=C1 CBKLICUQYUTWQL-XWGBWKJCSA-N 0.000 claims description 18
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- SAGXGPWVLUSDSQ-RVZXSAGBSA-N (2r)-2-amino-3-(carboxymethylsulfanyl)propanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CSCC(O)=O SAGXGPWVLUSDSQ-RVZXSAGBSA-N 0.000 claims description 15
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- 150000002314 glycerols Chemical class 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
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- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940031575 hydroxyethyl urea Drugs 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
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- 229920001206 natural gum Polymers 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- BWOROQSFKKODDR-UHFFFAOYSA-N oxobismuth;hydrochloride Chemical compound Cl.[Bi]=O BWOROQSFKKODDR-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
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- 229920000058 polyacrylate Polymers 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- NCYCYZXNIZJOKI-OVSJKPMPSA-N retinal group Chemical group C\C(=C/C=O)\C=C\C=C(\C=C\C1=C(CCCC1(C)C)C)/C NCYCYZXNIZJOKI-OVSJKPMPSA-N 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229940057910 shea butter Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 239000003549 soybean oil Substances 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
Definitions
- the present invention relates to a personal care composition
- a personal care composition comprising carboxymethyl cysteine compound and retinoid, wherein the weight ratio of carboxymethyl cysteine compound to retinoid is 1:1.6 to 25:1. It was unexpectedly found that the expression of collagen type I alpha I chain was significantly enhanced by such composition.
- the skin is a primary barrier of the human body. It protects the organs in the body from external stimulations. It is subject to intrinsic aging and extrinsic aging. Skin aging is a complex process, and alterations in human skin due to aging have distinct characteristics as compared to other organs. Characteristics of intrinsic or chronological skin aging include dryness, visible free lines and wrinkles, uneven skin pigmentation, loss of elasticity and skin sagging. Extrinsic factors including exposure to sunlight, pollutants and cigarette smoke can accelerate the skin aging process, especially on the face.
- Collagen the predominant matrix of the skin protein, is known to impart tensile strength to skin. It has been shown that collagen is significantly reduced with age and UV exposure. The degradation or destruction of the architecture of collagen decreases the tensile strength of the skin and therefore causing wrinkles and laxity. Collagen destruction is thought to underlie the characteristic alterations in the appearance of aged skin.
- One of the most efficient ways for providing the effect of anti-aging is to promote the production of collagen. Upregulating the expression of collagen synthesizing genes typically leads to an increase in collagen production.
- the present inventors have recognized that there is a need to develop solution to enhance the expression of collagen synthesizing genes, for example collagen type I alpha I chain (COL1A 1). It was surprisingly found that by combining carboxymethyl cysteine and retinoid in a specific weight ratio, the expression of COL1A1 was significantly upregulated.
- the present invention is directed to a personal care composition
- a personal care composition comprising carboxymethyl cysteine compound and retinoid, wherein the weight ratio of carboxymethyl cysteine compound to retinoid is 1 :1.6 to 25:1.
- the present invention is directed to a method of providing the skin benefits selected from the group consisting of enhancing collagen production in the skin, improving skin elasticity, reducing the appearance of wrinkles, reducing sagging, anti-aging and upregulating the expression of collagen synthesizing gene comprising a step of topically applying to the skin the composition of the composition of the present invention.
- the present invention is directed to use of the composition of the present invention for providing the skin benefits selected from the group consisting of enhancing collagen production in the skin, improving skin elasticity, reducing the appearance of wrinkles, reducing sagging, anti-aging and upregulating the expression of collagen synthesizing gene.
- the carboxymethyl cysteine compound refers to compound selected from carboxymethyl cysteine, salt of carboxymethyl cysteine, ester of carboxymethyl cysteine, amide of carboxymethyl cysteine or a mixture thereof.
- the carboxymethyl cysteine compound comprises carboxymethyl cysteine, ester of carboxymethyl cysteine, and/or salt of carboxymethyl cysteine.
- the carboxymethyl cysteine compound comprises carboxymethyl cysteine, and/or salt of carboxymethyl cysteine.
- carboxymethyl cysteine compound comprises salt of carboxymethyl cysteine.
- the carboxymethyl cysteine compound comprises lysine carboxymethyl cysteinate and most preferably, the carboxymethyl cysteine compound is lysine carboxymethyl cysteinate.
- the carboxymethyl cysteine compound is present in amount of at least 0.00001%, more preferably at least 0.0001 %, even more preferably at least 0.001 %, still even more preferably at least 0.01%, and most preferably at least 0.1 % by weight of the composition.
- the carboxymethyl cysteine compound is present in amount of no greater than 10%, more preferably no greater than 5%, even more preferably no greater than 3%, still even more preferably no greater than 1 %, and most preferably no greater than 0.5% by weight of the composition.
- the lysine carboxymethyl cysteinate is present in amount of no greater than 10%, more preferably no greater than 5%, even more preferably no greater than 3%, still even more preferably no greater than 1 %, and most preferably no greater than 0.5% by weight of the composition.
- the lysine carboxymethyl cysteinate is present in amount of at least 0.00001%, more preferably at least 0.0001 %, even more preferably at least 0.001%, still even more preferably at least 0.01 %, and most preferably at least 0.1% by weight of the composition.
- the composition of the present invention comprises a retinoid.
- the retinoid is selected from retinyl ester, retinol, retinal, retinoic acid or a mixture thereof. More preferably the retinoid comprises retinol, retinyl ester, or a mixture thereof and even more preferably the retinoid is selected from retinol, retinyl ester, or a mixture thereof.
- retinol includes the following isomers of retinol: all-trans-retinol, 13-cis-retinol, 11 -cis- retinol, 9-cis-retinol, 3,4-didehydro-retinol, 3, 4-didehydro-13-cis-retinol; 3, 4-didehydro- 11 -cis- retinol; 3,4-didehydro-9-cis-retinol.
- Preferred isomers are all-trans-retinol, 13-cis-retinol, 3,4- didehydro-retinol, 9-cis-retinol.
- Most preferred retinol is all-trans-retinol, due to its wide commercial availability.
- Retinyl ester is an ester of retinol.
- the term “retinol” has been defined above.
- Retinyl esters suitable for use in the present invention are preferably C1-C30 esters of retinol, more preferably C2-C20 esters of retinol, and most preferably C2, C3, and C esters of retinol.
- retinyl esters include but are not limited to: retinyl palmitate, retinyl formate, retinyl acetate, retinyl propionate, retinyl butyrate, retinyl valerate, retinyl isovalerate, retinyl hexanoate, retinyl heptanoate, retinyl octanoate, retinyl nonanoate, retinyl decanoate, retinyl undecanoate, retinyl laurate, retinyl tridecanoate, retinyl myristate, retinyl pentadecanoate, retinyl heptadecanoate, retinyl stearate, retinyl isostearate, retinyl nonadecanoate, retinyl arachidonate, retinyl behenate, retin
- the retinyl ester for use in the present invention is preferably selected from retinyl palmitate, retinyl acetate, retinyl linoleate, retinyl oleate, retinyl propionate or a mixture thereof. More preferably the retinyl ester is selected from retinyl palmitate, retinyl acetate, retinyl propionate, or a mixture thereof. Even more preferably the retinyl ester is selected from retinyl palmitate, retinyl propionate, or a mixture thereof.
- Particularly preferred retinoid is selected from all-trans-retinol, retinyl palmitate, retinyl acetate, retinyl propionate, or a mixture thereof. More preferably the retinoid is selected from retinyl palmitate, retinyl propionate, or a mixture thereof. Even more preferably the retinoid is retinyl propionate.
- the amount of the retinoid is preferably in the range of 0.00001 to 10%, more preferably from 0.0001 to 8%, even more preferably from 0.001 to 5%, still even more preferably from 0.02 to 2%, most preferably from 0.1 to 0.6% by weight of the total amount of the composition.
- the total amount retinol and retinyl ester in the composition is preferably in the range of 0.00001 to 10%, more preferably from 0.0001 to 8%, even more preferably from 0.001 to 5%, still even more preferably from 0.02 to 2%, most preferably from 0.1 to 0.6% by weight of the total amount of the composition.
- the total amount of retinyl palmitate and retinyl propionate in the composition is preferably in the range of 0.00001 to 10%, more preferably from 0.0001 to 8%, even more preferably from 0.001 to 5%, still even more preferably from 0.02 to 2%, most preferably from 0.1 to 0.6% by weight of the total amount of the composition.
- the amount of retinyl propionate in the composition is preferably in the range of 0.00001 to 10%, more preferably from 0.0001 to 8%, even more preferably from 0.001 to 5%, still even more preferably from 0.02 to 2%, most preferably from 0.1 to 0.6% by weight of the total amount of the composition.
- the weight ratio of the carboxymethyl cysteine compound to the retinoid is 1 :1.6 to 20: 1 , more preferably 1 : 1.6 to 10: 1 , even more preferably, still even more preferably 1 : 1.5 to 3: 1 and most preferably 1 :1.3 to 2:1.
- the weight ratio of the lysine carboxymethyl cysteinate to the retinoid is 1 :1.6 to 20:1 , more preferably 1:1.6 to 10:1 , even more preferably, still even more preferably 1 :1.5 to 3:1 and most preferably 1 :1.3 to 2:1.
- the weight ratio of the carboxymethyl cysteine compound to the total amount of retinol and retinyl ester in the composition is 1 : 1.6 to 20: 1 , more preferably 1 : 1.6 to 10: 1 , even more preferably, still even more preferably 1 :1.5 to 3:1 and most preferably 1 :1.3 to 2:1.
- the weight ratio of lysine carboxymethyl cysteinate to total amount of retinyl propionate and retinyl palmitate in the composition is 1 :1.6 to 20: 1 , more preferably 1 : 1.6 to 10: 1 , even more preferably, still even more preferably 1 : 1.5 to 3: 1 and most preferably 1 :1.3 to 2:1.
- the weight ratio of lysine carboxymethyl cysteinate to retinyl propionate in the composition is 1 :1.6 to 20:1, more preferably 1 :1.6 to 10:1 , even more preferably, still even more preferably 1 :1.5 to 3:1 and most preferably 1 :1.3 to 2:1.
- the present invention also provides a personal care composition comprising carboxymethyl cysteine compound and retinoid, wherein the molar ratio of carboxymethyl cysteine compound to retinoid is 1 :1.6 to 25:1.
- the molar ratio of the carboxymethyl cysteine compound to the retinoid is 1 :1.6 to 20:1 , more preferably 1:1.6 to 10:1 , even more preferably, still even more preferably 1 :1.5 to 3:1 and most preferably 1 :1.3 to 2:1.
- the molar ratio of the lysine carboxymethyl cysteinate to the retinoid is 1 :1.6 to 20:1, more preferably 1 :1.6 to 10:1, even more preferably, still even more preferably 1 :1.5 to 3:1 and most preferably 1 :1.3 to 2:1.
- the molar ratio of the carboxymethyl cysteine compound to the total amount of retinol and retinyl ester in the composition is 1 :1.6 to 20:1 , more preferably 1 :1.6 to 10:1 , even more preferably, still even more preferably 1:1.5 to 3:1 and most preferably 1 :1.3 to 2:1.
- the molar ratio of lysine carboxymethyl cysteinate to total amount of retinyl propionate and retinyl palmitate in the composition is 1 :1.6 to 20:1 , more preferably 1:1.6 to 10:1 , even more preferably, still even more preferably 1:1.5 to 3:1 and most preferably 1 :1.3 to 2:1.
- the molar ratio of lysine carboxymethyl cysteinate to retinyl propionate in the composition is 1 :1.6 to 20:1, more preferably 1:1.6 to 10:1 , even more preferably, still even more preferably 1:1.5 to 3:1 and most preferably 1 :1.3 to 2:1.
- the composition may optionally comprise whitening pigment.
- Whitening pigments are typically particles of high refractive index materials.
- the whitening pigment may have a refractive index of greater than 1.3, more preferably greater than 1.8 and most preferably from 2.0 to 2.7.
- Examples of such whitening pigment are those comprising bismuth oxy-chloride, boron nitride, barium sulfate, mica, silica, titanium dioxide, zirconium oxide, aluminium oxide, zinc oxide or combinations thereof.
- More preferred whitening pigment are particles comprising titanium dioxide, zinc oxide, zirconium oxide, mica, iron oxide or a combination thereof.
- Even more preferred whitening pigment are particles comprising zinc oxide, zirconium oxide, titanium dioxide or a combination thereof as these materials have especially high refractive index.
- the whitening pigment is selected from titanium dioxide, zinc oxide or a mixture thereof and most preferred whitening pigment is titanium dioxide.
- the average diameter of whitening pigment is typical from 15 nm to 1 micron, more preferably from 35 nm to 800 nm, even more preferably from 50 nm to 500 nm and still even more preferably from 100 to 300 nm.
- Amount of whitening pigment may be 0.1 to 15%, preferably 0.5 to 5% by weight of the composition.
- the composition comprises a glutamate source selected from the group consisting of glutamine, glutamine ester, glutamic acid, pyroglutamic acid, salts, and mixtures thereof. More preferably, the composition comprises pyroglutamic acid and/or salt of pyroglutamic acid. Even more preferably, the composition comprises sodium salt of pyroglutamic acid.
- the glutamate source is present in amount of 0.0001 to 10% by weight of the composition, more preferably 0.001 to 6%, even more preferably 0.01 to 3% by weight of the composition.
- the composition comprises polyhydric alcohol.
- Polyhydric alcohols may be selected from group of glycerin, propylyene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1 ,3-butylene glycol, isoprene glycol, ethoxylated glycerol, propoxylated glycerol or a mixture thereof.
- Most preferred polyhydric alcohol is glycerol known also as glycerin.
- the amount of polyhydric alcohol may range anywhere from 0.1 to 20%, preferably 0.5 to 15% and more preferably 2 and 10% by weight of the composition.
- the composition comprises emollient materials.
- Suitable emollient materials include silicones, hydrocarbons, triglycerides or a mixture thereof. These silicones may be organic, silicone-containing or fluorine-containing, volatile or non-volatile, polar or non-polar. Hydrocarbons may include mineral oil, petrolatum and polyalpha-olefins. Examples of preferred volatile hydrocarbons include polydecanes such as isododecane and isodecane (e.g. Permethyl- 99A which is available from Presperse Inc.) and the C7-C8 through C12-C15 isoparaffins (such as the Isopar Series available from Exxon Chemicals).
- Illustrative triglycerides but not limiting are sunflower seed oil, cotton oil, canola oil, soybean oil, castor oil, borage oil, olive oil, shea butter, jojoba oil and mixtures thereof. Mono- and di- glycerides may also be useful. Particularly preferable are glyceryl monostearate and glyceryl distearate.
- the composition comprises moisturizing agents.
- moisturizing agents includes, petrolatum, aquaporin manipulating actives, oat kernel flour, substituted urea like hydroxyethyl urea, hyaluronic acid and/or its precursor N-acetyl glucosamine, hyaluronic acid and/or its precursor N-acetyl glucosamine, or a mixture thereof.
- compositions may include thickeners. These may be selected from cellulosics, natural gums and acrylic polymers but not limited by this thickening agent types.
- cellulosics sodium carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl methylcellulose and combinations thereof.
- Suitable gums include xanthan, pectin, karaya, agar, alginate gums and combinations thereof.
- acrylic thickeners are homopolymers and copolymers of acrylic and methacrylic acids including carbomers such as Carbopol 1382, Carbopol 982, llltrez, Aqua SF-1 and Aqua SF-2 available from the Lubrizol Corporation.
- Amounts of thickener may range from 0.01 to 3% by weight of the active polymer (outside of solvent or water) in the compositions.
- compositions of the invention may further include 0.5 to 10% by weight of sequestering agents, such as tetra sodium ethylenediaminetetraacetate (EDTA), EHDP or mixtures; opacifiers and pearlizers such as ethylene glycol distearate, titanium dioxide or Lytron 621 (Styrene/Acrylate copolymer); all of which are useful in enhancing the appearance or properties of the product.
- sequestering agents such as tetra sodium ethylenediaminetetraacetate (EDTA), EHDP or mixtures
- opacifiers and pearlizers such as ethylene glycol distearate, titanium dioxide or Lytron 621 (Styrene/Acrylate copolymer); all of which are useful in enhancing the appearance or properties of the product.
- the composition may comprise water in amount of 10 to 96% by weight of the composition, more preferably from 25 to 92%, even more preferably from 42 to 88%, most preferably from 55 to 82% by weight of the composition.
- the composition has a viscosity of at least 10 mPa s, more preferably in the range 30 to 10000 mPa s, even more preferably 50 to 5000 mPa s, and most preferably 100 to 2000 mPa s, when measured at 20 degrees C at a relatively high shear rate of about 20 s’ 1 .
- the composition is an emulsion, more preferably an oil-in-water emulsion.
- the composition is a fluid liquid at 25 °C and atmospheric pressure.
- the personal care composition is a skin care composition.
- Skin care composition refers to a composition suitable for topical application to human skin, including leave-on and wash-off products but preferably leave-on compositions.
- leave-on as used with reference to compositions herein means a composition that is applied to or rubbed on the skin, and left thereon.
- wash-off as used with reference to compositions herein means a skin cleanser that is applied to or rubbed on the skin and rinsed off substantially immediately subsequent to application.
- skin as used herein includes the skin on the face, neck, chest, abdomen, back, arms, under arms, hands, and legs.
- skin means includes the skin on the face and under arms, more preferably skin means skin on the face other than lips and eyelids.
- the composition is particularly preferably a moisturizer rather than a make-up product.
- the composition is a topical composition.
- the composition may be in the form of cream, lotion, ointment, solution, suspension, emulsion, paste, gel, powder, powder foundation, emulsion foundation, wax foundation, or spray. More preferably, the composition may be formulated in the form of cream, lotion, ointment, emulsion, gel, or a spray.
- the use is non-therapeutic.
- the method is non-therapeutic.
- non-therapeutic typically means for cosmetic purposes and not curative or therapeutic purposes.
- the composition is capable of upregulating the expression of collagen type I alpha I chain (COL1A1) gene by at least 1.45 fold change, more preferably 1.55 to 5 and most preferably 1.75 to 3.5 and most preferably 1.75 to 2.5 fold change, typically in comparison to personal care composition comprising neither carboxymethyl cysteine compound nor retinoid.
- This Example demonstrates the synergistic anti-aging effect by combining lysine carboxymethyl cysteinate and retinyl propionate within a specific ratio.
- NHDF normal human dermal fibroblasts
- Biocell, Xi’an, China, Lot: Fb20081902 The normal human dermal fibroblasts (NHDF) (Biocell, Xi’an, China, Lot: Fb20081902) were incubated in medium together with or without actives for 48 hours. After incubation, the total RNA for each NHDF was extracted using RNAex Pro reagent (Accurate Biotechnology, Cat: AG21102) according to manufacturer’s protocol.
- the leve of actives is weight percentage based on the amount of medium a: not significantly better (p ⁇ 0.05) than either of single active with at same level, b: significantly better (p ⁇ 0.05) than either of single active at same level. It was evident from Table 1 that only when combining the lysine carboxymethyl cysteinate and retinyl propionate in a specific weight ratio of the present invention, the expression of COL1A 1 was significantly upregulated (1 vs. G and E). In contrast, when combining retinyl propionate with lysine carboxymethyl cysteinate in a weight ratio not within the range of the present invention, the expression of COL 1A 1 was not significantly upregulated (C vs. A and B; F vs. D and E).
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Abstract
Disclosed is a personal care composition comprising carboxymethyl cysteine compound and retinoid, wherein the weight ratio of carboxymethyl cysteine compound to retinoid is 1:1.6 to 25:1.
Description
A PERSONAL CARE COMPOSITION
Field of the Invention
The present invention relates to a personal care composition comprising carboxymethyl cysteine compound and retinoid, wherein the weight ratio of carboxymethyl cysteine compound to retinoid is 1:1.6 to 25:1. It was unexpectedly found that the expression of collagen type I alpha I chain was significantly enhanced by such composition.
Background of the Invention
The skin is a primary barrier of the human body. It protects the organs in the body from external stimulations. It is subject to intrinsic aging and extrinsic aging. Skin aging is a complex process, and alterations in human skin due to aging have distinct characteristics as compared to other organs. Characteristics of intrinsic or chronological skin aging include dryness, visible free lines and wrinkles, uneven skin pigmentation, loss of elasticity and skin sagging. Extrinsic factors including exposure to sunlight, pollutants and cigarette smoke can accelerate the skin aging process, especially on the face.
Collagen, the predominant matrix of the skin protein, is known to impart tensile strength to skin. It has been shown that collagen is significantly reduced with age and UV exposure. The degradation or destruction of the architecture of collagen decreases the tensile strength of the skin and therefore causing wrinkles and laxity. Collagen destruction is thought to underlie the characteristic alterations in the appearance of aged skin.
One of the most efficient ways for providing the effect of anti-aging is to promote the production of collagen. Upregulating the expression of collagen synthesizing genes typically leads to an increase in collagen production.
Therefore, the present inventors have recognized that there is a need to develop solution to enhance the expression of collagen synthesizing genes, for example collagen type I alpha I chain (COL1A 1). It was surprisingly found that by combining carboxymethyl cysteine and retinoid in a specific weight ratio, the expression of COL1A1 was significantly upregulated.
Summary of the Invention
In a first aspect, the present invention is directed to a personal care composition comprising carboxymethyl cysteine compound and retinoid, wherein the weight ratio of carboxymethyl cysteine compound to retinoid is 1 :1.6 to 25:1.
In a second aspect, the present invention is directed to a method of providing the skin benefits selected from the group consisting of enhancing collagen production in the skin, improving skin elasticity, reducing the appearance of wrinkles, reducing sagging, anti-aging and upregulating the expression of collagen synthesizing gene comprising a step of topically applying to the skin the composition of the composition of the present invention.
In a third aspect, the present invention is directed to use of the composition of the present invention for providing the skin benefits selected from the group consisting of enhancing collagen production in the skin, improving skin elasticity, reducing the appearance of wrinkles, reducing sagging, anti-aging and upregulating the expression of collagen synthesizing gene.
All other aspects of the present invention will more readily become apparent upon considering the detailed description and examples which follow.
Detailed Description of the Invention
Except in the examples, or where otherwise explicitly indicated, all numbers in this description indicating amounts of material or conditions of reaction, physical properties of materials and/or use may optionally be understood as modified by the word “about”.
All amounts are by weight of the composition, unless otherwise specified.
It should be noted that in specifying any range of values, any particular upper value can be associated with any particular lower value.
For the avoidance of doubt, the word “comprising” is intended to mean “including” but not necessarily “consisting of’ or “composed of’. In other words, the listed steps or options need not be exhaustive.
The disclosure of the invention as found herein is to be considered to cover all embodiments as found in the claims as being multiply dependent upon each other irrespective of the fact that claims may be found without multiple dependency or redundancy.
Where a feature is disclosed with respect to a particular aspect of the invention (for example a composition of the invention), such disclosure is also to be considered to apply to any other aspect of the invention (for example a method of the invention) mutatis mutandis.
The carboxymethyl cysteine compound refers to compound selected from carboxymethyl cysteine, salt of carboxymethyl cysteine, ester of carboxymethyl cysteine, amide of carboxymethyl cysteine or a mixture thereof. Preferably, the carboxymethyl cysteine compound comprises carboxymethyl cysteine, ester of carboxymethyl cysteine, and/or salt of carboxymethyl cysteine. More preferably, the carboxymethyl cysteine compound comprises carboxymethyl cysteine, and/or salt of carboxymethyl cysteine. Even more preferably, carboxymethyl cysteine compound comprises salt of carboxymethyl cysteine. Still even more preferably the carboxymethyl cysteine compound comprises lysine carboxymethyl cysteinate and most preferably, the carboxymethyl cysteine compound is lysine carboxymethyl cysteinate.
Preferably, the carboxymethyl cysteine compound is present in amount of at least 0.00001%, more preferably at least 0.0001 %, even more preferably at least 0.001 %, still even more preferably at least 0.01%, and most preferably at least 0.1 % by weight of the composition. Preferably, the carboxymethyl cysteine compound is present in amount of no greater than 10%, more preferably no greater than 5%, even more preferably no greater than 3%, still even more preferably no greater than 1 %, and most preferably no greater than 0.5% by weight of the composition.
Preferably, the lysine carboxymethyl cysteinate is present in amount of no greater than 10%, more preferably no greater than 5%, even more preferably no greater than 3%, still even more preferably no greater than 1 %, and most preferably no greater than 0.5% by weight of the composition. Preferably, the lysine carboxymethyl cysteinate is present in amount of at least 0.00001%, more preferably at least 0.0001 %, even more preferably at least 0.001%, still even more preferably at least 0.01 %, and most preferably at least 0.1% by weight of the composition.
The composition of the present invention comprises a retinoid. Typically, the retinoid is selected from retinyl ester, retinol, retinal, retinoic acid or a mixture thereof. More preferably the retinoid comprises retinol, retinyl ester, or a mixture thereof and even more preferably the retinoid is selected from retinol, retinyl ester, or a mixture thereof.
The term “retinol” includes the following isomers of retinol: all-trans-retinol, 13-cis-retinol, 11 -cis- retinol, 9-cis-retinol, 3,4-didehydro-retinol, 3, 4-didehydro-13-cis-retinol; 3, 4-didehydro- 11 -cis- retinol; 3,4-didehydro-9-cis-retinol. Preferred isomers are all-trans-retinol, 13-cis-retinol, 3,4- didehydro-retinol, 9-cis-retinol. Most preferred retinol is all-trans-retinol, due to its wide commercial availability.
Retinyl ester is an ester of retinol. The term “retinol” has been defined above. Retinyl esters suitable for use in the present invention are preferably C1-C30 esters of retinol, more preferably C2-C20 esters of retinol, and most preferably C2, C3, and C esters of retinol. Examples of retinyl esters include but are not limited to: retinyl palmitate, retinyl formate, retinyl acetate, retinyl propionate, retinyl butyrate, retinyl valerate, retinyl isovalerate, retinyl hexanoate, retinyl heptanoate, retinyl octanoate, retinyl nonanoate, retinyl decanoate, retinyl undecanoate, retinyl laurate, retinyl tridecanoate, retinyl myristate, retinyl pentadecanoate, retinyl heptadecanoate, retinyl stearate, retinyl isostearate, retinyl nonadecanoate, retinyl arachidonate, retinyl behenate, retinyl linoleate, retinyl oleate. The retinyl ester for use in the present invention is preferably selected from retinyl palmitate, retinyl acetate, retinyl linoleate, retinyl oleate, retinyl propionate or a mixture thereof. More preferably the retinyl ester is selected from retinyl palmitate, retinyl acetate, retinyl propionate, or a mixture thereof. Even more preferably the retinyl ester is selected from retinyl palmitate, retinyl propionate, or a mixture thereof.
Particularly preferred retinoid is selected from all-trans-retinol, retinyl palmitate, retinyl acetate, retinyl propionate, or a mixture thereof. More preferably the retinoid is selected from retinyl palmitate, retinyl propionate, or a mixture thereof. Even more preferably the retinoid is retinyl propionate.
The amount of the retinoid is preferably in the range of 0.00001 to 10%, more preferably from 0.0001 to 8%, even more preferably from 0.001 to 5%, still even more preferably from 0.02 to 2%, most preferably from 0.1 to 0.6% by weight of the total amount of the composition. The total amount retinol and retinyl ester in the composition is preferably in the range of 0.00001 to 10%, more preferably from 0.0001 to 8%, even more preferably from 0.001 to 5%, still even more preferably from 0.02 to 2%, most preferably from 0.1 to 0.6% by weight of the total amount of the composition. The total amount of retinyl palmitate and retinyl propionate in the composition is preferably in the range of 0.00001 to 10%, more preferably from 0.0001 to 8%, even more preferably from 0.001 to 5%, still even more preferably from 0.02 to 2%, most preferably from 0.1 to 0.6% by weight of the total amount of the composition. The amount of retinyl propionate in the composition is preferably in the range of
0.00001 to 10%, more preferably from 0.0001 to 8%, even more preferably from 0.001 to 5%, still even more preferably from 0.02 to 2%, most preferably from 0.1 to 0.6% by weight of the total amount of the composition.
Preferably, the weight ratio of the carboxymethyl cysteine compound to the retinoid is 1 :1.6 to 20: 1 , more preferably 1 : 1.6 to 10: 1 , even more preferably, still even more preferably 1 : 1.5 to 3: 1 and most preferably 1 :1.3 to 2:1. Preferably, the weight ratio of the lysine carboxymethyl cysteinate to the retinoid is 1 :1.6 to 20:1 , more preferably 1:1.6 to 10:1 , even more preferably, still even more preferably 1 :1.5 to 3:1 and most preferably 1 :1.3 to 2:1. Preferably, the weight ratio of the carboxymethyl cysteine compound to the total amount of retinol and retinyl ester in the composition is 1 : 1.6 to 20: 1 , more preferably 1 : 1.6 to 10: 1 , even more preferably, still even more preferably 1 :1.5 to 3:1 and most preferably 1 :1.3 to 2:1. Preferably, the weight ratio of lysine carboxymethyl cysteinate to total amount of retinyl propionate and retinyl palmitate in the composition is 1 :1.6 to 20: 1 , more preferably 1 : 1.6 to 10: 1 , even more preferably, still even more preferably 1 : 1.5 to 3: 1 and most preferably 1 :1.3 to 2:1. Preferably, the weight ratio of lysine carboxymethyl cysteinate to retinyl propionate in the composition is 1 :1.6 to 20:1, more preferably 1 :1.6 to 10:1 , even more preferably, still even more preferably 1 :1.5 to 3:1 and most preferably 1 :1.3 to 2:1.
The present invention also provides a personal care composition comprising carboxymethyl cysteine compound and retinoid, wherein the molar ratio of carboxymethyl cysteine compound to retinoid is 1 :1.6 to 25:1. -Preferably, the molar ratio of the carboxymethyl cysteine compound to the retinoid is 1 :1.6 to 20:1 , more preferably 1:1.6 to 10:1 , even more preferably, still even more preferably 1 :1.5 to 3:1 and most preferably 1 :1.3 to 2:1. Preferably, the molar ratio of the lysine carboxymethyl cysteinate to the retinoid is 1 :1.6 to 20:1, more preferably 1 :1.6 to 10:1, even more preferably, still even more preferably 1 :1.5 to 3:1 and most preferably 1 :1.3 to 2:1. Preferably, the molar ratio of the carboxymethyl cysteine compound to the total amount of retinol and retinyl ester in the composition is 1 :1.6 to 20:1 , more preferably 1 :1.6 to 10:1 , even more preferably, still even more preferably 1:1.5 to 3:1 and most preferably 1 :1.3 to 2:1. Preferably, the molar ratio of lysine carboxymethyl cysteinate to total amount of retinyl propionate and retinyl palmitate in the composition is 1 :1.6 to 20:1 , more preferably 1:1.6 to 10:1 , even more preferably, still even more preferably 1:1.5 to 3:1 and most preferably 1 :1.3 to 2:1. Preferably, the molar ratio of lysine carboxymethyl cysteinate to retinyl propionate in the composition is 1 :1.6 to 20:1, more preferably 1:1.6 to 10:1 , even more preferably, still even more preferably 1:1.5 to 3:1 and most preferably 1 :1.3 to 2:1.
The composition may optionally comprise whitening pigment. Whitening pigments are typically particles of high refractive index materials. For example, the whitening pigment may have a refractive index of greater than 1.3, more preferably greater than 1.8 and most preferably from 2.0 to 2.7. Examples of such whitening pigment are those comprising bismuth oxy-chloride, boron nitride, barium sulfate, mica, silica, titanium dioxide, zirconium oxide, aluminium oxide, zinc oxide or combinations thereof. More preferred whitening pigment are particles comprising titanium dioxide, zinc oxide, zirconium oxide, mica, iron oxide or a combination thereof. Even more preferred whitening pigment are particles comprising zinc oxide, zirconium oxide, titanium dioxide or a combination thereof as these materials have especially high refractive index. Still even more preferably the whitening pigment is selected from titanium dioxide, zinc oxide or a mixture thereof and most preferred whitening pigment is titanium dioxide. The average diameter of whitening pigment is typical from 15 nm to 1 micron, more preferably from 35 nm to 800 nm, even more preferably from 50 nm to 500 nm and still even more preferably from 100 to 300 nm. Amount of whitening pigment may be 0.1 to 15%, preferably 0.5 to 5% by weight of the composition.
Preferably, the composition comprises a glutamate source selected from the group consisting of glutamine, glutamine ester, glutamic acid, pyroglutamic acid, salts, and mixtures thereof. More preferably, the composition comprises pyroglutamic acid and/or salt of pyroglutamic acid. Even more preferably, the composition comprises sodium salt of pyroglutamic acid. Preferably, the glutamate source is present in amount of 0.0001 to 10% by weight of the composition, more preferably 0.001 to 6%, even more preferably 0.01 to 3% by weight of the composition.
Preferably, the composition comprises polyhydric alcohol. Polyhydric alcohols may be selected from group of glycerin, propylyene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1 ,3-butylene glycol, isoprene glycol, ethoxylated glycerol, propoxylated glycerol or a mixture thereof. Most preferred polyhydric alcohol is glycerol known also as glycerin. The amount of polyhydric alcohol may range anywhere from 0.1 to 20%, preferably 0.5 to 15% and more preferably 2 and 10% by weight of the composition.
Preferably, the composition comprises emollient materials. Suitable emollient materials include silicones, hydrocarbons, triglycerides or a mixture thereof. These silicones may be organic, silicone-containing or fluorine-containing, volatile or non-volatile, polar or non-polar. Hydrocarbons may include mineral oil, petrolatum and polyalpha-olefins. Examples of preferred volatile hydrocarbons include polydecanes such as isododecane and isodecane (e.g. Permethyl- 99A which is available from Presperse Inc.) and the C7-C8 through C12-C15 isoparaffins (such
as the Isopar Series available from Exxon Chemicals). Illustrative triglycerides but not limiting are sunflower seed oil, cotton oil, canola oil, soybean oil, castor oil, borage oil, olive oil, shea butter, jojoba oil and mixtures thereof. Mono- and di- glycerides may also be useful. Particularly preferable are glyceryl monostearate and glyceryl distearate.
Preferably, the composition comprises moisturizing agents. Particularly preferred moisturizing agents includes, petrolatum, aquaporin manipulating actives, oat kernel flour, substituted urea like hydroxyethyl urea, hyaluronic acid and/or its precursor N-acetyl glucosamine, hyaluronic acid and/or its precursor N-acetyl glucosamine, or a mixture thereof.
Some compositions may include thickeners. These may be selected from cellulosics, natural gums and acrylic polymers but not limited by this thickening agent types. Among the cellulosics are sodium carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl methylcellulose and combinations thereof. Suitable gums include xanthan, pectin, karaya, agar, alginate gums and combinations thereof. Among the acrylic thickeners are homopolymers and copolymers of acrylic and methacrylic acids including carbomers such as Carbopol 1382, Carbopol 982, llltrez, Aqua SF-1 and Aqua SF-2 available from the Lubrizol Corporation. Amounts of thickener may range from 0.01 to 3% by weight of the active polymer (outside of solvent or water) in the compositions.
In addition, the compositions of the invention may further include 0.5 to 10% by weight of sequestering agents, such as tetra sodium ethylenediaminetetraacetate (EDTA), EHDP or mixtures; opacifiers and pearlizers such as ethylene glycol distearate, titanium dioxide or Lytron 621 (Styrene/Acrylate copolymer); all of which are useful in enhancing the appearance or properties of the product.
The composition may comprise water in amount of 10 to 96% by weight of the composition, more preferably from 25 to 92%, even more preferably from 42 to 88%, most preferably from 55 to 82% by weight of the composition.
Preferably, the composition has a viscosity of at least 10 mPa s, more preferably in the range 30 to 10000 mPa s, even more preferably 50 to 5000 mPa s, and most preferably 100 to 2000 mPa s, when measured at 20 degrees C at a relatively high shear rate of about 20 s’1.
Preferably, the composition is an emulsion, more preferably an oil-in-water emulsion. Preferably the composition is a fluid liquid at 25 °C and atmospheric pressure.
Preferably, the personal care composition is a skin care composition. Skin care composition refers to a composition suitable for topical application to human skin, including leave-on and wash-off products but preferably leave-on compositions. The term “leave-on” as used with reference to compositions herein means a composition that is applied to or rubbed on the skin, and left thereon. The term “wash-off” as used with reference to compositions herein means a skin cleanser that is applied to or rubbed on the skin and rinsed off substantially immediately subsequent to application. The term "skin" as used herein includes the skin on the face, neck, chest, abdomen, back, arms, under arms, hands, and legs. Preferably “skin” means includes the skin on the face and under arms, more preferably skin means skin on the face other than lips and eyelids. The composition is particularly preferably a moisturizer rather than a make-up product.
Preferably, the composition is a topical composition. Preferably, the composition may be in the form of cream, lotion, ointment, solution, suspension, emulsion, paste, gel, powder, powder foundation, emulsion foundation, wax foundation, or spray. More preferably, the composition may be formulated in the form of cream, lotion, ointment, emulsion, gel, or a spray.
Preferably the use is non-therapeutic. Preferably the method is non-therapeutic. The term non- therapeutic typically means for cosmetic purposes and not curative or therapeutic purposes.
Preferably, the composition is capable of upregulating the expression of collagen type I alpha I chain (COL1A1) gene by at least 1.45 fold change, more preferably 1.55 to 5 and most preferably 1.75 to 3.5 and most preferably 1.75 to 2.5 fold change, typically in comparison to personal care composition comprising neither carboxymethyl cysteine compound nor retinoid.
The following examples are provided to facilitate an understanding of the invention. The examples are not intended to limit the scope of the claims.
Examples
This Example demonstrates the synergistic anti-aging effect by combining lysine carboxymethyl cysteinate and retinyl propionate within a specific ratio.
The normal human dermal fibroblasts (NHDF) (Biocell, Xi’an, China, Lot: Fb20081902) were incubated in medium together with or without actives for 48 hours. After incubation, the total RNA for each NHDF was extracted using RNAex Pro reagent (Accurate Biotechnology, Cat: AG21102) according to manufacturer’s protocol.
The extracted RNA was quantified using Nanodrop spectrometer (Thermo Fisher Scientific, Waltham, MA, US) and reverse transcribed to generate the template cDNA using the Evo M-MLV RT Premix for qPCR (Accurate Biotechnology, Cat: AG11706) according to manufacturer’s protocol. Gene expression of COL1A 1 gene was analyzed by polymerase chain reaction (PCR) using SYBR® Green Premix Pro Taq HS qPCR Kit (Accurate Biotechnology, AG11701). The actin beta (ACTS) gene was selected as the housekeeping gene and all data on relative expression of the target genes was normalized to ACTB gene. The fold changes in expression were calculated relative to the blank control (medium having no active). All tests were conducted at least three times and Table 1 shows the fold changes in gene expression of COL1A 1.
* The leve of actives is weight percentage based on the amount of medium a: not significantly better (p<0.05) than either of single active with at same level, b: significantly better (p<0.05) than either of single active at same level.
It was evident from Table 1 that only when combining the lysine carboxymethyl cysteinate and retinyl propionate in a specific weight ratio of the present invention, the expression of COL1A 1 was significantly upregulated (1 vs. G and E). In contrast, when combining retinyl propionate with lysine carboxymethyl cysteinate in a weight ratio not within the range of the present invention, the expression of COL 1A 1 was not significantly upregulated (C vs. A and B; F vs. D and E).
Claims
1. A personal care composition comprising carboxymethyl cysteine compound and retinoid, wherein the weight ratio of carboxymethyl cysteine compound to retinoid is 1 :1.6 to 25:1.
2. The composition according to claim 1 wherein the carboxymethyl cysteine compound comprises carboxymethyl cysteine, ester of carboxymethyl cysteine, and/or salt of carboxymethyl cysteine.
3. The composition according to claim 2 wherein the carboxymethyl cysteine compound comprises salt of carboxymethyl cysteine and preferably the carboxymethyl cysteine compound comprises lysine carboxymethyl cysteinate.
4. The composition according to any one of the preceding claims wherein the carboxymethyl cysteine compound is present in amount of at least 0.00001% and no greater than 10% by weight of the composition, preferably carboxymethyl cysteine compound is present in amount of at least 0.01% and no greater than 3% by weight of the composition.
5. The composition according to any one of the preceding claims wherein the retinoid is selected from retinol, retinyl ester, or a mixture thereof, preferably the retinoid is retinyl propionate.
6. The composition according to any one of the preceding claims wherein the amount of the retinoid is in the range of 0.00001 to 10%, preferably from 0.02 to 2% by weight of the total amount of the composition.
7. The composition according to any one of the preceding claims wherein the weight ratio of the carboxymethyl cysteine compound to the retinoid is 1 :1.6 to 20:1 , preferably 1 :1.5 to 3:1.
8. The composition according to any one of the preceding claims wherein the weight ratio of lysine carboxymethyl cysteinate to retinyl propionate in the composition is 1 :1.6 to 20:1 , preferably 1 :1.5 to 3:1.
9. The composition according to any one of the preceding claims wherein the composition is an emulsion, preferably an oil-in-water emulsion.
The composition according to any one of the preceding claims wherein the composition is a fluid liquid at 25 °C and atmospheric pressure. The composition according to any one of the preceding claims wherein the composition comprises water in amount of 10 to 96% by weight of the composition, preferably from 42 to 88% by weight of the composition. A method of providing the skin benefits selected from the group consisting of enhancing collagen production in the skin, improving skin elasticity, reducing the appearance of wrinkles, reducing sagging, anti-aging and upregulating the expression of collagen synthesizing gene comprising a step of topically applying to the skin the composition of any one of the preceding claims. Use of the composition of any one of the preceding claims 1 to 11 for providing the skin benefits selected from the group consisting of enhancing collagen production in the skin, improving skin elasticity, reducing the appearance of wrinkles, reducing sagging, anti-aging and upregulating the expression of collagen synthesizing gene.
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Application Number | Priority Date | Filing Date | Title |
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CN2022131264 | 2022-11-11 | ||
CNPCT/CN2022/131264 | 2022-11-11 | ||
EP22212384.6 | 2022-12-09 | ||
EP22212384 | 2022-12-09 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3111M (en) * | 1963-12-02 | 1965-02-08 | Rech S Pharma Et Scient | Medicinal product based on a cysteine derivative. |
WO2000053176A1 (en) * | 1999-03-05 | 2000-09-14 | Uni-Ci S.R.L. | Pharmaceutic, dietetic and cosmetic compositions based on thioctic acid and cysteine |
US6153649A (en) * | 1995-10-30 | 2000-11-28 | L'oreal | Use of carboxylic acids having a sulphur function for promoting skin exfoliation or stimulating epidermal regeneration |
US20020041890A1 (en) * | 2000-06-30 | 2002-04-11 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Skin care cosmetic compositions containing phosphates and/or sulfates of branched alcohols and/or ethoxylates thereof |
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2023
- 2023-10-16 WO PCT/EP2023/078588 patent/WO2024099690A1/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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FR3111M (en) * | 1963-12-02 | 1965-02-08 | Rech S Pharma Et Scient | Medicinal product based on a cysteine derivative. |
US6153649A (en) * | 1995-10-30 | 2000-11-28 | L'oreal | Use of carboxylic acids having a sulphur function for promoting skin exfoliation or stimulating epidermal regeneration |
WO2000053176A1 (en) * | 1999-03-05 | 2000-09-14 | Uni-Ci S.R.L. | Pharmaceutic, dietetic and cosmetic compositions based on thioctic acid and cysteine |
US20020041890A1 (en) * | 2000-06-30 | 2002-04-11 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Skin care cosmetic compositions containing phosphates and/or sulfates of branched alcohols and/or ethoxylates thereof |
Non-Patent Citations (1)
Title |
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DATABASE GNPD [online] MINTEL; 2 June 2010 (2010-06-02), ANONYMOUS: "Balance Control Mask", XP093048871, retrieved from https://www.gnpd.com/sinatra/recordpage/1324988/ Database accession no. 1324988 * |
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