WO2022087666A1 - Compositions de rétinol, leurs procédés de préparation et d'utilisation - Google Patents

Compositions de rétinol, leurs procédés de préparation et d'utilisation Download PDF

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Publication number
WO2022087666A1
WO2022087666A1 PCT/AU2021/051249 AU2021051249W WO2022087666A1 WO 2022087666 A1 WO2022087666 A1 WO 2022087666A1 AU 2021051249 W AU2021051249 W AU 2021051249W WO 2022087666 A1 WO2022087666 A1 WO 2022087666A1
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Prior art keywords
composition
skin
retinol
optionally
ingredient
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PCT/AU2021/051249
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English (en)
Inventor
Toni OVENELL
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International Waters Pty Ltd T/A Alpha-H
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Priority claimed from AU2020903892A external-priority patent/AU2020903892A0/en
Application filed by International Waters Pty Ltd T/A Alpha-H filed Critical International Waters Pty Ltd T/A Alpha-H
Priority to AU2021369845A priority Critical patent/AU2021369845A1/en
Priority to GB2307416.4A priority patent/GB2618220A/en
Publication of WO2022087666A1 publication Critical patent/WO2022087666A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P3/06—Antihyperlipidemics
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    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/07—Retinol compounds, e.g. vitamin A
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    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
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    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
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    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
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    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
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    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
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    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
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    • 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
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    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
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    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
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    • A61K2800/88—Two- or multipart kits
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Definitions

  • the present invention relates to retinol, retinoid and retinyl ester compositions suitable for application to the skin, uses thereof and methods of their preparation.
  • the majority of the dermis of the skin is collagen.
  • the collagen both supports the skin structure and retains moisture.
  • Collagen fibres in the skin are reduced by exposure to ultraviolet radiation, a dry environment, and oxidation.
  • the amount of collagen in the skin also reduces with age. Reduction of collagen is associated with reduced resilience and elasticity in the skin.
  • Retinol also known as vitamin A
  • Retinol is one of the most effective ingredients for softening the appearance of wrinkles, refining skin texture, and improving uneven skin tone. This is achieved by increasing collagen production and promoting skin turnover.
  • Retinol, retinoids (derivatives of retinol), and retinyl esters are common ingredients used in cosmetic and dermatological products. Retinols have high photoreactivity and require protection from light (UV) and air (oxygen) for stable storage. They are also sensitive to heat, acid and alkaline conditions.
  • Alpha-hydroxy acids are class of chemical exfoliants commonly used in skin care products.
  • the common AHAs are glycolic acid, lactic acid, and citric acid.
  • AHA-containing products cause exfoliation, or shedding of the surface skin.
  • the extent of exfoliation depends on the type and concentration of the AHA, its pH, and other ingredients in the product. The exfoliation occurs chemically by the dissolution of bonds between skin cells as opposed to manually by scrubbing the skin.
  • AHAs such as glycolic acid and lactic acid are thermally stable, although may be subject to polymerisation at high temperatures (above 50°C).
  • the present invention includes a composition which is surprisingly able to combine a retinol and an alpha hydroxy acid in a stable formulation.
  • the present invention provides, a composition including 0.01-0.2% w/w one or more retinol, 5-20% w/w one or more alpha hydroxy acid, at least one emollient, at least one aqueous solvent, at least one emulsifying agent, at least one antioxidant, optionally at least one emulsion stabiliser, and optionally at least one skin conditioning agent, wherein the composition has a pH of 3.5 to 4.5.
  • the pH is 3.7 to 4.3. More preferably, the PH is 3.8 to 4.2. Even more preferably, the pH is 3.9 to 4.1. Most preferably, the pH is about 4.
  • the one or more retinol ingredient is optionally hydroxypinacolone retinoate, retinol, retinyl acetate, retinyl linoleate, retinyl palmitate, retinyl proprionate, or combinations thereof.
  • the one or more retinol ingredient is optionally hydroxypinacolone retinoate, retinol, or combinations thereof.
  • the one or more retinol ingredient is hydroxypinacolone retinoate.
  • the one or more retinol ingredient is retinol.
  • the alpha hydroxy acid is optionally glycolic acid, lactic acid, citric acid, hydroxycaproic acid, hydroxycaprylic acid, malic acid, tartaric acid or combinations thereof.
  • the alpha hydroxy acid is glycolic acid, lactic acid or combinations thereof.
  • the alpha hydroxy acid is glycolic acid.
  • the alpha hydroxy acid is lactic acid.
  • the one or more retinol ingredient is alternatively 0.05-0.2% w/w of the composition. In some embodiments, the one or more retinol ingredient is 0.07-0.15% w/w of the composition. Preferably, the one or more retinol ingredient is about 0.1% w/w of the composition.
  • the one or more retinol ingredient is included as a 1 :9 w/w ratio of one or more retinol ingredient and the solvent dimethyl isosorbide.
  • These compositions are 0.1-2.0% w/w of the one or more retinol ingredient and dimethyl isosorbide.
  • the composition is 0.5-2.0% w/w a 1 :9 w/w ratio of one or more retinol ingredient and the solvent dimethyl isosorbide. In some embodiments, the composition is 0.7-1 .5% w/w a 1 :9 w/w ratio of one or more retinol ingredient and the solvent dimethyl isosorbide. Preferably, the 1 :9 w/w one or more retinol ingredient and the solvent dimethyl isosorbide is 1% w/w of the composition.
  • the composition is 10-20% w/w one or more alpha hydroxy acid.
  • the composition is 12-16% w/w one or more alpha hydroxy acid.
  • the composition is 14% w/w one or more alpha hydroxy acid.
  • the at least one emollient is optionally 5-20% w/w of the formulation.
  • the one or more retinol ingredient is oil soluble and will be solubilised within the oil phase formed by the oil phase formed by the at least one emollient.
  • the at least one emollient is 8-15% w/w of the composition.
  • the composition is about 10-11 % w/w emollient.
  • the at least one emollient is selected from the group consisting of glycerin, dimethocone, dicaprylyl carbonate, helianthus annuus seed oil, hippophae rhamnoides fruit extract and combinations thereof.
  • at least one emollient comprises all of the group consisting of glycerin, dimethocone, dicaprylyl carbonate, helianthus annuus seed oil, and hippophae rhamnoides fruit extract.
  • the aqueous solvent is preferably water.
  • the water and the one or more alpha hydroxy acid comprise the water phase of the composition.
  • the water is 40- 90% w/w of the composition.
  • the water is 40-70% w/w or 50-60% w/w of the composition.
  • the composition is about 55% w/w water.
  • the at least one emulsifying agent is optionally 1 .0-2.5% w/w of the composition. Preferably, the at least one emulsifying agent is about 2% w/w of the composition.
  • the at least one emulsifying agent will emulsify the emollient oil phase and the water/one or more alpha hydroxy acid aqueous phase of the emulsion.
  • the at least one emulsifying agent is selected from the group consisting of cetyl alcohol, glyceryl stearate, PEG-100 stearate, and combinations thereof.
  • at least one emulsifying agent comprises all of the group consisting of cetyl alcohol, glyceryl stearate, and PEG-100 stearate.
  • the at least one antioxidant is optionally 0.5-2.0% w/w of the composition.
  • the at least one antioxidant is about 0.6% w/w of the composition (excluding the water and glycerin) or about 1 .6% w/w including the water and/or glycerin included with the antioxidants.
  • the at least one antioxidant is selected from the group consisting of ubiquinone (coenzyme Q10), ferulic acid, Tasmannia lanceolata fruit/leaf extract, and combinations thereof.
  • at least one emulsifying agent comprises all of the group consisting of ubiquinone (coenzyme Q10), ferulic acid, and Tasmannia lanceolata fruit/leaf extract.
  • the Tasmannia lanceolata fruit/leaf extract is present in a composition further including glycerin and water, for example, 70% water, 28% glycerin, and 2% Tasmannia lanceolata fruit/leaf extract (ie Tazman Pepper).
  • the at least one emulsion stabiliser is optionally 0.5-1 .5% w/w of the composition.
  • the at least one emulsion stabiliser is about 1 % w/w of the composition.
  • the at least one emulsion stabiliser is sodium polyacryloyldimethyl taurate.
  • the at least one skin conditioning agent is optionally 5-20% w/w of the composition. Alternatively, the at least one skin conditioning agent is about 12-17% w/w of the composition. Preferably, the at least one skin conditioning agent is about 12-13% or 15-17% w/w of the composition. [0027] Optionally, the at least one skin conditioning agent is selected from the group consisting of palmitoyl tripepetide-5, hydrolysed jojoba esters, tocopherol, hibiscus sabdariffa flower extract, ammonium glycyrrhizate, sodium hyaluronate, butylene glycol, propanediol and combinations thereof.
  • formulations include palmitoyl tripepetide-5 and/or hibiscus sabdariffa flower extract.
  • at least one skinconditioning agent comprises all of the group consisting of palmitoyl tripepetide-5, hydrolysed jojoba esters, tocopherol, hibiscus sabdariffa flower extract, ammonium glycyrrhizate, butylene glycol, propanediol and sodium hyaluronate.
  • composition optionally further comprises one or more preservatives.
  • Suitable preservatives include phenoxyethanol and/or caprylyl glycol.
  • composition optionally further comprises one or more further solvents.
  • suitable solvents include dimethyl isosorbide.
  • the skin conditioners propandiol and butylene glycol can also function as solvents.
  • composition optionally further comprises one or more humectants.
  • Suitable humectants include methyl gluceth-20 and/or glycerin.
  • composition of the invention includes:
  • a retinol composition comprising 10% one or more retinol ingredient in 90% dimethyl isosorbide
  • the Tasmannia lanceolata fruit/leaf extract is in the form of Tazman Pepper (70% water, 28% glycerin and 2% Tasmannia lanceolata fruit/leaf extract).
  • composition has a pH of 3.9 to 4.1 (preferably, the pH is about 4).
  • composition of the invention includes:
  • a retinol composition comprising 10% one or more retinol ingredient in 90% dimethyl isosorbide
  • Tazman Pepper (70% water, 28% glycerin and 2% Tasmannia lanceolata fruit/leaf extract),
  • composition has a pH of 3.9 to 4.1 (preferably, the pH is about 4).
  • composition of the invention includes:
  • a retinol composition comprising 10% one or more retinol ingredient in 90% dimethyl isosorbide
  • emollient selected from glycerin, dimethocone, dicaprylyl carbonate, helianthus annuus seed oil, hippophae rhamnoides fruit extract, and combinations thereof,
  • emulsifying agent selected from cetyl alcohol, glyceryl stearate, PEG-100 stearate, and combinations thereof,
  • At least one antioxidant selected from ubiquinone (coenzyme Q10), ferulic acid, Tasmannia lanceolata fruit/leaf extract, and combinations thereof,
  • composition has a pH of 3.9 to 4.1 (preferably, the pH is about 4).
  • composition of the invention includes:
  • a retinol composition comprising 10% one or more retinol ingredient in 90% dimethyl isosorbide
  • emollient selected from glycerin, dimethocone, dicaprylyl carbonate, helianthus annuus seed oil, hippophae rhamnoides fruit extract, and combinations thereof,
  • emulsifying agent selected from cetyl alcohol, glyceryl stearate, PEG-100 stearate, and combinations thereof,
  • w/w preferably 0.5-2.0% w/w (preferably 0.6%) of at least one antioxidant selected from ubiquinone (coenzyme Q10), ferulic acid, Tasmannia lanceolata fruit/leaf extract, and combinations thereof, - 0.5-1.5% w/w (preferably 1 % w/w) of at least one emulsion stabiliser selected from sodium polyacryloyldimethyl taurate; and
  • composition has a pH of 3.9 to 4.1 (preferably, the pH is about 4).
  • composition of the invention includes:
  • a retinol composition comprising 10% of hydroxypinacolone retinoate in 90% dimethyl isosorbide
  • composition has a pH of 3.9 to 4.1 (preferably, the pH is about 4).
  • 90, 95, 98, 99 or 99.5% w/w one or more retinol ingredient added to the composition remains retinol ingredient following preparation of the composition.
  • 70, 80, 85 or 90% w/w of the one or more alpha hydroxy acid added to the composition remains alpha hydroxy acid following preparation of the composition.
  • the composition is stored in an opaque inert packaging, for example, a high density polyethylene bottle or jar.
  • the opaque packaging will protect the composition from light.
  • 70, 80, 85, 90, 95, or 98% w/w of the one or more retinol ingredient added to the composition remains retinol ingredient following storage of the composition in its packaging at room temperature and standard relative humidity for 90 days.
  • 70, 80, 85 or 90% w/w of the one or more alpha hydroxy acid added to the composition remains alpha hydroxy acid following storage of the composition in its packaging at 40 +/- 2 °C at 75% relative humidity for 90 days.
  • the composition is stored in opaque inert packaging, for example, a high-density polyethylene bottle or jar.
  • the amount of retinol ingredient remaining in the composition following storage of the composition in opaque inert packaging at 40 +/- 2 °C at standard relative humidity for 14 days is at least 90% or at least 93% or at least 95% of the original amount.
  • the amount of retinol ingredient remaining in the composition following storage of the composition in opaque inert packaging at 40 +/- 2 °C at standard relative humidity for 10 weeks is at least 75% or at least 78% or at least 80% or at least 85%, or at least 90% or at least 93%.
  • the amount of retinol ingredient remaining in the composition following storage of the composition in opaque inert packaging at 40 +/- 2 °C at standard relative humidity for 12 weeks is at least 60%, at least 70%, at least 80%, at least 85%, at least 87% or at least 90%.
  • the retinol ingredient is hydroxypinacolone retinoate and the amount of retinol ingredient remaining in the composition following storage of the composition in opaque inert packaging at 40 +/- 2 °C at standard relative humidity for 12 weeks is at least 80% (optionally at least 90%).
  • the amount of retinol ingredient remaining in the composition following storage of the composition in its packaging at 40 +/- 2 °C at standard relative humidity for 12 weeks is at least 60% (optionally at least 75 % or 78%).
  • the composition is stored in an opaque inert packaging, for example, a high-density polyethylene bottle or jar.
  • an opaque inert packaging for example, a high-density polyethylene bottle or jar.
  • at least 70% or at least 73% or at least 75% or at least 80% w/w w/w of the one or more retinol ingredient added to the composition remains retinol ingredient following storage of the composition in opaque inert packaging at room temperature and standard relative humidity for 12 months.
  • At least 70% or at least 73% or at least 75% or at least 80% w/w of the one or more alpha hydroxy acid added to the composition remains alpha hydroxy acid following storage of the composition in opaque inert packaging at room temperature and standard relative humidity for 12 months.
  • the alpha hydroxy acid is glycolic acid
  • at least 80% of the alpha hydroxyl acid remains alpha hydroxy acid following storage of the composition in opaque inert packaging at room temperature and standard relative humidity for 12 months.
  • the present invention provides a method of exfoliating the skin comprising application of a composition of the invention to the skin.
  • the skin is the face, neck, decolletage and/or scalp.
  • 0.3 ml of the composition is applied to the face, neck, decolletage and/or scalp.
  • the composition is applied once per day.
  • the composition has similar irritation levels to the use of the same composition containing no retinol or retinol ingredient.
  • the method results in exfoliation of the skin that is 30%, 40% or 50% faster than natural exfoliation of the skin.
  • the present invention provides the use of one or more retinol ingredient in the preparation of a composition of the invention for exfoliating skin.
  • the skin is the face, neck, decolletage and/or scalp.
  • 0.3 ml of the composition is applied to the face, neck, decolletage and/or scalp.
  • the composition is applied once per day.
  • the composition has similar irritation levels to the use of the same composition containing no retinol or retinol ingredient.
  • the method results in exfoliation of the skin that is 30%, 40% or 50% faster than natural exfoliation of the skin.
  • the present invention provides the composition of the invention for exfoliating skin.
  • the skin is the face, neck, decolletage and/or scalp.
  • 0.3 ml of the composition is applied to the face, neck, decolletage and/or scalp.
  • the composition is applied once per day.
  • the composition has similar irritation levels to the use of the same composition containing no retinol or retinol ingredient.
  • the method results in exfoliation of the skin that is 30%, 40% or 50% faster than natural exfoliation of the skin.
  • the present invention provides a method of exfoliating the skin and one or more of (i) skin lightening by breaking down of hyperpigmentation, (ii) reducing of pore numbers and/or pore size, (iii) improving the skin's texture, (iv) increasing collagen and/or elastin production in the skin, (v) reducing fine lines and/or wrinkles, (vi) reducing sebum production, (vii) improving acne breakouts and blemishes, (viii) increasing hydration and/or a plumping the skin comprising application of a composition of the invention to the skin.
  • the skin is the face, neck, decolletage and/or scalp.
  • 0.3 ml of the composition is applied to the face, neck, decolletage and/or scalp.
  • the composition is applied once per day.
  • the method results in exfoliation of the skin that is 30%, 40% or 50% faster than natural exfoliation of the skin.
  • the present invention provides the use of one or more retinol ingredient in the preparation of a composition of the invention for exfoliating the skin and one or more of (i) skin lightening by breaking down of hyperpigmentation, (ii) reducing of pore numbers and/or pore size, (iii) improving the skin's texture, (iv) increasing collagen and/or elastin production in the skin, (v) reducing fine lines and/or wrinkles, (vi) reducing sebum production, (vii) improving acne breakouts and blemishes, (viii) increasing hydration and/or a plumping the skin.
  • the skin is the face, neck, decolletage and/or scalp.
  • 0.3 ml of the composition is applied to the face, neck, decolletage and/or scalp.
  • the composition is applied once per day.
  • the composition has similar irritation levels to the use of the same composition containing no retinol or retinol ingredient.
  • the method results in exfoliation of the skin that is 30%, 40% or 50% faster than natural exfoliation of the skin.
  • the present invention provides the composition of the invention for exfoliating the skin and one or more of (i) skin lightening by breaking down of hyperpigmentation, (ii) reducing of pore numbers and/or pore size, (iii) improving the skin's texture, (iv) increasing collagen and/or elastin production in the skin, (v) reducing fine lines and/or wrinkles, (vi) reducing sebum production, (vii) improving acne breakouts and blemishes, (viii) increasing hydration and/or a plumping the skin.
  • the skin is the face, neck, decolletage and/or scalp.
  • 0.3 ml of the composition is applied to the face, neck, decolletage and/or scalp.
  • the composition is applied once per day.
  • the composition has similar irritation levels to the use of the same composition containing no retinol or retinol ingredient.
  • the method results in exfoliation of the skin that is 30%, 40% or 50% faster than natural exfoliation of the skin.
  • composition of the invention comprising:
  • step (i) combining the one or more alpha hydroxy acid and at least one aqueous solvent and, if needed, adjusting the pH to 3.8-4.2 using a pH adjuster; (ii) optionally combining the mixture prepared in step (i) with one or more water soluble emollients, one or more skin conditioning agents, one or more humectants, or combinations thereof;
  • step (iii) combining the at least one emulsifying agent, at least one oil phase emollient, and optionally at least one emulsion stabiliser with the mixture prepared in step (ii) and homogenising;
  • step (iv) combining the one or more antioxidants, one or more retinol ingredient, and optionally one or more heat or shear sensitive ingredients such as skin conditioning agents into the mixture prepared in step (iii);
  • the mixture is heated to 60-80 °C (preferably about 70 °C) after step (i) and then cooled after step (iii) 45 °C or less (preferably about 40 °C).
  • the one or more antioxidants include one or more of ubiquinone (coenzyme Q10), ferulic acid, and Tasmannia lanceolata fruit/leaf extract.
  • the heat or sheer sensitive skin conditioning agents added in step (iv) are one or more of tocopherol, hibiscus sabdariffa flower extract, and palmitoyl tripepetide-5.
  • one or more of glycerin, butylene glycol, propanediol and sodium hyalonurate are combined with mixture (i) in step (ii).
  • one or more humectant is added to the mixture.
  • the humectant is methyl gluceth-20.
  • the humectant is optionally added with one or more skin conditioner, preferably, ammonium glycyrrhizate.
  • At least one emulsifying agent and at least one oil phase emollient are combined before mixing with the mixture of step (ii).
  • the at least one emulsifying agent and at least one oil phase emollient are heated to 60-80 °C (preferably about 70 °C) before combining with the mixture of step (ii).
  • the at least one emulsifying agent is one or more of cetyl alcohol, glyceryl stearate, and PEG- 100 stearate.
  • the at least one oil phase emollient is dimethicone and/or dicaprylyl carbonate.
  • the at least one emulsifying agent and at least one oil phase emollient are added to the mixture of step (ii) and homogenised, then the at least one emulsion stabiliser is added to the mixture and the mixture homogenised again.
  • one or more of emulsion stabiliser is added to the mixture following the addition of the at least one emulsifying agent and at least one oil phase emollient, and homogenisation, at least one emulsion stabiliser is combined with the mixture.
  • the at least one emulsion stabiliser is sodium polyacryloyldimethyl taurate.
  • the emulsion stabiliser is combined with the emollients helianthus annuus seed oil, and/or hippophae rhamnoides fruit extract, and/or the skin conditioner hydrolysed jojoba esters before addition to the mixture.
  • a preservative is combined with the emulsion stabiliser.
  • the mixture is homogenised again.
  • homogenisation is for 5 minutes.
  • the one or more retinol ingredient is added to a cooled mixture after any homogenisation step(s).
  • the one or more retinol ingredient is the final ingredient added to the composition before the final pH adjustment.
  • room temperature refers to about 20 °C.
  • standard humidity refers to 30 to 50% relative humidity. Optionally, 40% relative humidity.
  • Vitamin A is the first vitamin approved by the Food and Drug Administration as an anti-wrinkle agent that changes appearance of the skin surface and has anti-aging effects.
  • Vitamin A is in a group of fat-soluble substances and belongs to the category of retinoids.
  • Retinoic acid is the only registered therapeutic agent.
  • the other retinoids are used in cosmetic applications. Apart from retinol, that group includes structurally related substances with the biological properties of retinol.
  • Vitamin A and its derivatives are among the most effective substances slowing the appearance of the aging process.
  • Retinoids regulate the cell apoptosis, differentiation and proliferation.
  • Anti-wrinkle properties of retinoids promote keratinocytes proliferation, strengthen the protective function of the epidermis, restrain transepidermal water loss, protect collagen against degradation and inhibit metalloproteinases activity.
  • HPR Hydroxypinacolone Retinoate
  • HPR is a retinoic acid ester. HPR binds directly to retinoid receptors like retinoic acid. This makes its use more straight forward that the use of retinol and retinyl palmitate, which have to convert to retinoic acid in the skin to be effective.
  • HPR is the preferred retinoid of this invention. It has the following chemical structure:
  • retinols or derivatives thereof include retinol (1), retinyl acetate (12), retinyl proprionate (3), retinyl linoleate (4) and retinyl palmitate (5).
  • retinol (1) retinol (1), retinyl acetate (12), retinyl proprionate (3), retinyl linoleate (4) and retinyl palmitate (5).
  • the structures are shown below.
  • the benefits of retinoids include (1) skin lightening by breaking down of hyperpigmentation, (2) Reduction of pore numbers and pore size, (3) Improving the skin's texture, (4) Providing a youthful glow, (5) Increased collagen and elastin production, (6) A reduction of fine lines and wrinkles, (7) Acting as an antioxidant, (8) Reducing sebum production, (9) Improving acne breakouts and blemishes, (10) Increasing hydration and a plumping effect of the skin.
  • Granactive Retinoid is supplied by Grant Industries.
  • the INCI (International Nomenclature Cosmetic Ingredient) name for the product is dimethyl isosorbide (and) hydroxypinacolone retinoate.
  • the product is an anhydrous matrix containing 10% pinacolyl ester of all-trans retinoic acid in the solvent dimethyl isosorbide.
  • Dimethyl isosorbide is a solvent that assists with delivery of the retinoid into the skin.
  • the product is for decreasing the effects of UV induced skin damage and assisting clearing of acne related symptoms.
  • the ingredient is for addition to the oil phase of emulsions. It is recommended to formulate without infusing air/oxygen into the product.
  • the product has a specific gravity of 1.1-1.2 at 25 °C and a refractive index of 1.45-1.52 at 25 °C.
  • Alpha-hydroxy acids are class of chemical exfoliants commonly used in skin care products.
  • the common AHAs are glycolic acid and lactic acid.
  • AHA-containing products cause exfoliation, or shedding of the surface skin.
  • Exfoliation refers to a process where the skin cells on the surface shed off. This helps remove dead skin cells but also makes way for new skin cell generation. As you age, your natural skin cell cycle slows down, which can make dead skin cells build up. When you have too many dead skin cells, they can accumulate and make your complexion look dull. The extent of exfoliation depends on the type and concentration of the AHA, its pH, and other ingredients in the product. The exfoliation occurs chemically by the dissolution of bonds between skin cells as opposed to manually by scrubbing the skin.
  • AHA products are usually between 10 and 15% w/w AHA. AHA products are usually applied every few days, then alternate days and then everyday as the skin builds tolerance. Some AHA products are designed for once a week use.
  • AHAs are primarily used to exfoliate. They can also help promote collagen and blood flow, correct discoloration from scars and age spots, improve appearance of surface lines and wrinkles, prevent acne breakouts, brighten your complexion, and increase product absorption.
  • Example 1 Composition 1
  • Table 1 below shows the formulation of composition 1.
  • composition with the above formulation has a pH of 3.8-4.2.
  • the formulation can be alternatively described in table 2 below.
  • Step 1 The Part A ingredients were added and the pH of the solution adjusted to 3.8- 4.2
  • Step 2 The solution was heated to 70°C
  • Step 3 The Part B ingredients were combined, and then added to Part A while stirring.
  • Step 4 The Part C ingredients were added with stirring.
  • Step 5 The Part D ingredients were combined in a separate vessel and heated to 70°C
  • Step 6 The Part D mixture was added to the vessel containing the combined part A B and C ingredients while stirring.
  • Step 7 The mixture was homogenised for 5 minutes.
  • Step 8 The Part E ingredients were added, and homogenised for 5 minutes.
  • Step 9 The mixture is cooled to 40°C while stirring.
  • Step 10 The Part F ingredients were added while stirring, and the mixture cooled until the desired consistency is reached.
  • Step 11 The part G ingredients were added
  • composition 1 was stored in final packaging (50mL in an opaque high density polyethylene bottle with a polypropylene cap) at 40 +/- 2°C, at 75% relative humidity for 90 days.
  • composition was tested to evaluate stability by an independent third-party laboratory BioTest. There was no change in appearance, pH or specific gravity measured after 90 days shelf life test.
  • LGMRS did not change in appearance over 12 month’s storage at room temperature. There was no separation or colour change.
  • the concentration of glycolic acid was measured as glycolate ions in two different samples of Composition 1 using ion chromatography (IC) analysis by third-party lab. Each batch was sealed in opaque high density polyethylene following manufacture and stored until testing on 15 October 2020.
  • IC ion chromatography
  • the samples were diluted by a ratio of approximately 1 :1000 with ultra-pure deionized water and shaken on an orbital platform shaker for 10 minutes at 350 RPM.
  • the sample solutions were prepared once and analyzed in duplicate injections using suppressed conductivity detection on a Metrohm ion chromatography system. Peak identification was based on the retention time of the glycolate in the standards.
  • a seven point linear calibration curve ranging from 0.05 to 50 ppm glycolate was used for quantitation.
  • the samples needed to be run with an inline dilution factor of 5 in order to bring the measurements within this range.
  • the total dilution factor of 5000 was applied to the concentration measured in the sample solutions.
  • glycolic acid concentration in a further sample of Composition 1 was tested 2 months and about 12 months post manufacture as shown in the Table 6 below. Each batch was sealed in opaque amber high density polyethylene bottles at manufacture and stored at room temperature and standard humidity until testing.
  • the formulation did not change in appearance over the 12 months. There was no change in colour or separation of the emulsion.
  • HPR Hydroxypinacolone Retinoate
  • HPR concentration in a further sample of Composition 1 was tested 2 months and 12 months post manufacture as shown in the Table 8 below. Each batch was sealed in opaque amber high density polyethylene bottles at room temperature following manufacture and stored until testing.
  • the assay results show a slight decrease in HPR over the time (0.095% to 0.073% - approximately 80% of original amount (ie 77% or at least 75%).
  • the reduction in HPR is acceptable due to the nature of this raw material and the pH of the final product.
  • the stability of HPR claimed by Grant Industries, based on accelerated stability studies, is approximately 80% in the absence of glycolic acid.
  • Composition 1 is intended for application of 3-6 drops (approximately 0.3 ml) per application to the face, neck, and decolletage by gently spreading across the surface with fingers. It may also be applied to hair.
  • the product is a leave-on product. It is intended to be used once per day.
  • composition 1 is not more irritating that the use of glycolic acid alone.
  • N 10 female Caucasian subjects with even toned skin of the upper arms
  • composition 1 was applied on the treated site and rubbed in.
  • the untreated site was wiped without product. 6. After 48 and 72 hours color was measured again followed by treatment with the product
  • composition with the above formulation has a pH of 4.0.
  • the formulation can be alternatively described in Table 10 below.
  • Step 1 The Part A ingredients were added and the pH of the solution adjusted to 3.8- 4.2
  • Step 2 The solution was heated to 70°C
  • Step 3 The Part B ingredients were combined in a separate vessel and heated to 70°C
  • Step 4 The Part B mixture was added to the vessel containing the combined part A ingredients while stirring.
  • Step 5 The mixture was homogenised for 5 minutes.
  • Step 6 The Part C ingredients were added, and homogenised for 5 minutes.
  • Step 7 The mixture is cooled to 40°C while stirring.
  • Step 8 The Part D ingredients were added while stirring, and the mixture cooled until the desired consistency is reached.
  • composition 2 The Hydroxypinacolone Retinoate (HPR) concentration in composition 2 was tested using HPLC.
  • the manufactured batch (LGMS (BARE)) of composition 2 was sealed in opaque high density polyethylene following manufacture and one sample was tested after 13 days storage and a second sample was tested after stored at 40°C and at standard relative humidity for 1 month. The sample was 1 month old at the time of testing.
  • the concentration of glycolic acid was measured by measuring the concentration of glycolate ions using the assay procedure as described in example 3.
  • Composition 2 was tested after 13 days storage at room temperature and standard relative humidity and a second sample of Composition 2 was tested after being stored at room temperature and standard humidity for approximately 1 month and then stored at 40°C and standard relative humidity for 1 month. Composition 2 did not change in appearance over the 1 month when stored. There was no separation or colour change. The assay results show a slight decrease in HPR over the time (0.086% to 0.083% - approximately 97% of original amount). Glycolic acid assays have shown that the amount of glycolate (as glycolic acid) reduces very slightly over time (97% of original after 1 month at 40°C. and standard relative humidity)
  • Example 8 Composition 2
  • Test formula 1 HPR/retinyl palmitate
  • test formula 2 HPR/retinyl palmitate
  • Test formula 1 is the same as Composition 1 optionally with the HPR substituted for retinyl palmitate
  • Test formula 2 is the same as Composition 2, optionally with the HPR substituted for retinyl palmitate. Both were prepared in accordance with the method of Example 1.
  • the samples were aged using accelerated aging (storage at 40°C, standard relative humidity) for 12 weeks.
  • the amount of retinol ingredient remaining in the composition was measured using HPLC after 2, 4, 10 and 12 weeks. The results are shown in figures 4 and 5.
  • Test formulas made with HPR but without glycolic acid also showed a stability after 12 weeks accelerated aging of around 80%.

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Abstract

L'invention concerne une composition comprenant 0,01 à 0,2 % en poids de rétinol, 5 à 20 % p/p d'acide hydroxy alpha, au moins un émollient, au moins un solvant aqueux, au moins un agent émulsifiant, au moins un antioxydant, éventuellement au moins un stabilisateur d'émulsion, et éventuellement au moins un agent de conditionnement de la peau, la composition ayant un pH de 3,5 à 4,5.
PCT/AU2021/051249 2020-10-27 2021-10-27 Compositions de rétinol, leurs procédés de préparation et d'utilisation WO2022087666A1 (fr)

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CN115154373A (zh) * 2022-08-05 2022-10-11 广州夕木生物科技有限公司 一种抗衰组合物及其制备方法
CN117582383A (zh) * 2023-11-30 2024-02-23 梅晔生物医药股份有限公司 一种改善皮肤衰老组合物及其应用、日化品

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WO1998014167A1 (fr) * 1996-10-03 1998-04-09 Johnson & Johnson Consumer Companies, Inc. Compositions cosmetiques
EP1449514A1 (fr) * 2003-02-13 2004-08-25 Beiersdorf AG Préparations pour le soin de la peau contenant des rétinoides, des ubiquinones, et de la biotine ou de la carnitine
WO2006048671A1 (fr) * 2004-11-05 2006-05-11 Bioforskning As Formules de polyamine
WO2007104981A1 (fr) * 2006-03-14 2007-09-20 Bioforskning Pharma As Utilisation de polyamines dans le traitement du psoriasis
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Publication number Priority date Publication date Assignee Title
CN115154373A (zh) * 2022-08-05 2022-10-11 广州夕木生物科技有限公司 一种抗衰组合物及其制备方法
CN117582383A (zh) * 2023-11-30 2024-02-23 梅晔生物医药股份有限公司 一种改善皮肤衰老组合物及其应用、日化品

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