EP4580614A1 - Composition for caring for keratin materials and mask containing the same - Google Patents

Composition for caring for keratin materials and mask containing the same

Info

Publication number
EP4580614A1
EP4580614A1 EP22956878.7A EP22956878A EP4580614A1 EP 4580614 A1 EP4580614 A1 EP 4580614A1 EP 22956878 A EP22956878 A EP 22956878A EP 4580614 A1 EP4580614 A1 EP 4580614A1
Authority
EP
European Patent Office
Prior art keywords
composition
ascorbyl
mask
hydroxyhydrocinnamate
alginate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP22956878.7A
Other languages
German (de)
French (fr)
Inventor
Libing CAI
Liang Zhang
Zhenxi LEE
Bingxiang LIU
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP4580614A1 publication Critical patent/EP4580614A1/en
Pending legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0212Face masks
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67Vitamins
    • A61K8/671Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67Vitamins
    • A61K8/676Ascorbic acid, i.e. vitamin C
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67Vitamins
    • A61K8/678Tocopherol, i.e. vitamin E
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/733Alginic acid; Salts thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52Stabilizers
    • A61K2800/522Antioxidants; Radical scavengers

Definitions

  • Skin aging is part of the aging process of human body, which not only relates to the age itself, but also closely relates to external factors, such as sunlight exposure.
  • the light induced skin aging ( “light-aging” ) is mainly caused by sunlight irradiation, and as depletion of the ozone layer is aggravating, the light-aging of the skin becomes more and more serious, which affects the appearance of the skin.
  • lipophilic active ingredient such as retinoids cannot be delivered into the skin effectively.
  • the present invention provides a composition for caring for keratin materials, comprising:
  • the present invention provides a mask for caring for keratin materials, comprising:
  • the present invention also provides a non-therapeutic process for caring for keratin materials, in particular the skin, comprising the step of applying the composition or the mask according to the present invention on the keratin materials.
  • retinoids are stable for a relatively long term and can be delivered into the skin effectively.
  • keratin material is intended to cover the skin. Facial skin and eye skin are most particularly considered according to the present invention.
  • stable means that retinol or its derivatives contained in the mask will not decompose substantially for at least 2 months.
  • composition for caring for keratin materials comprises:
  • the composition according to the present invention comprises at least one retinoid.
  • the retinoids according to the present invention include retinol (vitamin A) , retinal (vitamin A aldehyde) , retinoic acid (vitamin A acid) , or an ester of retinol and of a C 2 -C 20 acid, such as the propionate, the acetate, the linoleate or the palmitate of retinol (retinyl palmitate) , among others.
  • the retinoid is selected from retinol, retinal, retinoic acid, esters of retinol and of a C 2 -C 20 acid, and a combination thereof.
  • retinoids mention may more particularly be made of retinol, retinal, retinoic acid, in particular all-trans retinoic acid and 13-cis retinoic acid, retinol derivatives, such as retinyl acetate, propionate or palmitate, and the retinoids described in the following patent applications: FR 2 370 377, EP 0 199 636, EP 0 325 540 and EP 0 402 072.
  • the retinoid is retinol or a pro-retinol.
  • retinol is intended to mean all the isomers of retinol, i.e. all-trans retinol, 13-cis retinol, 11-cis retinol, 9-cis retinol and 3, 4-didehydro retinol.
  • retinyl palmitate the palmitate of retinol
  • the retinoid is selected from retinol, retinyl palmitate, and a combination thereof.
  • the composition according to the present invention comprises retinol and/or retinyl palmitate.
  • the retinoid is present in an amount ranging from 0.1 wt.%to 5 wt. %, preferably from 0.1 wt. %to 2 wt. %, more preferably from 0.15 wt. %to 1 wt. %, relative to the total weight of the composition.
  • composition according to the present invention an antioxidant combination of i) ascorbic acid or its derivative, ii) tocopherol or its derivative, and iii) at least one hydroxyhydrocinnamate antioxidant.
  • derivatives of ascorbic acid include aminopropyl ascorbyl phosphate, ascorbic acid polypeptide, ascorbyl dipalmitate, ascorbyl glucoside, ascorbyl linoleate, ascorbyl methylsilanol pectinate, ascorbyl palmitate, ascorbyl tetraisopalmitate, trisodium ascorbyl palmitate phosphate, disodium ascorbyl sulfate, calcium ascorbate, methylsilanol ascorbate, sodium ascorbate, sodium ascorbyl phosphate, sodium ascorbyl/cholesteryl phosphate, tetrahexyldecyl ascorbate, magnesium ascorbyl phosphate, among others.
  • the composition according to the present invention comprises one or more of ascorbic acid, aminopropyl ascorbyl phosphate, ascorbic acid polypeptide, ascorbyl dipalmitate, ascorbyl glucoside, ascorbyl linoleate, ascorbyl methylsilanol pectinate, ascorbyl palmitate, ascorbyl tetraisopalmitate, trisodium ascorbyl palmitate phosphate, disodium ascorbyl sulfate, calcium ascorbate, methylsilanol ascorbate, sodium ascorbate, sodium ascorbyl phosphate, sodium ascorbyl/cholesteryl phosphate, tetrahexyldecyl ascorbate, magnesium ascorbyl phosphate.
  • the composition according to the present invention comprises ascorbic acid and/or ascorbyl glucoside.
  • ascorbic acid or its derivative is present in an amount ranging from 0.05 wt. %to 3 wt. %, preferably from 0.1 wt. %to 2 wt. %, more preferably from 0.15 wt. %to 1 wt. %, relative to the total weight of the composition.
  • derivatives of tocopherol include tocopheryl acetate, tocopheryl linoleate, tocopheryl linoleate/oleate, tocopheryl nicotinate, tocopheryl retinoate, sodium tocopheryl phosphate, dioleyl tocopheryl methylsilanol, among others.
  • the composition according to the present invention comprises one or more of tocopherol, tocopheryl acetate, tocopheryl linoleate, tocopheryl linoleate/oleate, tocopheryl nicotinate, tocopheryl retinoate, sodium tocopheryl phosphate, and dioleyl tocopheryl methylsilanol.
  • composition according to the present invention comprises tocopherol.
  • tocopherol or its derivative is present in an amount ranging from 0.05 wt. %to 3 wt. %, preferably from 0.1 wt. %to 2 wt. %, more preferably from 0.15 wt. %to 1 wt. %, relative to the total weight of the composition.
  • the hydroxyhydrocinnamate antioxidant is selected from pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate, octadecyl di-t-butyl-4-hydroxyhydrocinnamate, tetradibutyl pentaerithrityl hydroxylhydrocinnamate, and a combination thereof.
  • the hydroxyhydrocinnamate antioxidant is present in an amount ranging from 0.05 wt. %to 3 wt. %, preferably from 0.1 wt. %to 2 wt.%, more preferably from 0.15 wt. %to 1 wt. %, relative to the total weight of the composition.
  • composition of the present invention may comprise an aqueous phase.
  • Said aqueous phase comprises water.
  • the aqueous phase comprises an organic solvent miscible with water (at room temperature 25°C) selected from glycols and polyols having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferentially having from 2 to 6 carbon atoms, such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; and combinations thereof, so as to provide a hydration effect.
  • an organic solvent miscible with water selected from glycols and polyols having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferentially having from 2 to 6 carbon atoms, such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; and combinations thereof, so as to provide
  • the aqueous phase is present in the composition of the present invention in an amount ranging from 50%to 95%by weight, preferably from 60%to 85%by weight, relative to the total weight of the composition.
  • composition of the present invention may comprise an oily phase.
  • Said oily phase comprise at least one oil.
  • the oil can be volatile or non-volatile.
  • oil means a water-immiscible non-aqueous compound that is liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg) .
  • non-volatile oil means an oil that may remain on keratin materials at room temperature and atmospheric pressure for at least several hours and that especially has a vapour pressure of less than 10 -3 mmHg (0.13 Pa) .
  • a non-volatile oil may also be defined as having an evaporation rate such that, under the conditions defined previously, the amount evaporated after 30 minutes is less than 0.07 mg/cm 2 .
  • oils may be of plant, mineral or synthetic origin.
  • Said oil can be selected from hydrocarbon-based, silicone or fluorinated oils.
  • hydrocarbon-based oil means an oil formed essentially from, or even constituted by, carbon and hydrogen atoms, and optionally O and N atoms, and free of Si and F heteroatoms. Such oil can contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • silicon oil means an oil containing at least one silicon atom, especially containing Si-O groups.
  • fluorinated oil means an oil containing at least one fluorine atom.
  • the oil is selected from hydrocarbon-based oils.
  • the oily phase is present in the composition of the present invention in an amount ranging from 1 wt. %to 20 wt. %, preferably from 2 wt. %to 10 wt. %, relative to the total weight of the composition of the present invention.
  • composition according to the present invention can comprises one or more additional cosmetic active ingredients.
  • enzymes for example, enzymes; flavonoids; humetants (for example, biosaccharide gum-1, mannose, sodium hyaluronate) ; tensioning agents; soothing agents; among others.
  • composition of the present invention may comprise conventional cosmetic adjuvants or additives, for instance, fragrances, surfactants (for example, non-ionic surfactants) , chelating agents (for example, trisodium ethylenediamine disuccinate) , preserving agents (for example, chlorphenesin and phenoxyethanol) and bactericides (for example, hydroxyacetophenone) , thickeners (for example, xanthan gum, ammonium polyacryloyldimethyl taurate) , pH adjusting agents (for example, sodium citrate) , and combinations thereof.
  • fragrances for instance, fragrances, surfactants (for example, non-ionic surfactants) , chelating agents (for example, trisodium ethylenediamine disuccinate) , preserving agents (for example, chlorphenesin and phenoxyethanol) and bactericides (for example, hydroxyacetophenone) , thickeners (for example, xanthan gum, ammonium polyacryloyld
  • the present invention provides a composition for caring for keratin materials comprising, relative to the total weight of the composition:
  • hydroxyhydrocinnamate antioxidant selected from pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate, octadecyl di-t-butyl-4-hydroxyhydrocinnamate, tetradibutyl pentaerithrityl hydroxylhydrocinnamate, and a combination thereof.
  • composition of the present invention may be in the form of gel, lotion, or emulsion.
  • composition according to the present invention can be impregnated into a mask tissue to form a mask.
  • the present invention relates to a mask for caring for keratin materials, comprising:
  • the mask according to the present invention comprises a hydrophilic mask tissue.
  • the mask tissue is water-insoluble.
  • water-insoluble means that the mask tissue is not dissolvable in water and it doesn’ t break apart upon immersion in water.
  • the skilled in the art can choose a suitable mask tissue and the weight ratio of the mask tissue used and the composition according to the present invention based on the nature of the composition.
  • Alginate tissues are known in the art and are described in WO2020001069A1.
  • an alginate tissue may comprise a water-insoluble alginate chosen from calcium alginate, strontium alginate, zinc alginate, copper alginate, manganese alginate, or a combination thereof, preferably calcium alginate, preferably in an amount ranging from 20 wt. %to 100 wt. %, relative to the total weight of the tissue.
  • the composition according to the present invention comprises a pH adjusting agent selected from sodium acetate, sodium citrate, sodium tartrate, and a combination thereof in an amount ranging from 0.01 wt. %to 1.0 wt. %, preferably from 0.05 wt. %to 0.45 wt. %, more preferably from 0.15 wt. %to 0.3 wt. %, relative to the total weight of the composition according to the present invention.
  • a pH adjusting agent selected from sodium acetate, sodium citrate, sodium tartrate, and a combination thereof in an amount ranging from 0.01 wt. %to 1.0 wt. %, preferably from 0.05 wt. %to 0.45 wt. %, more preferably from 0.15 wt. %to 0.3 wt. %, relative to the total weight of the composition according to the present invention.
  • the mask tissue can have a wide variety of shapes, depending on the desired use and characteristic of the mask.
  • the mask tissue is typically designed to fit the area of the skin to which topical application is desired.
  • the mask tissue is designed to correspond to the shape of the face avoiding the eye, nostril, and mouth areas, as necessary.
  • the weight ratio of the water insoluble substrate and the composition ranges from 1: 3 to 1: 20. More preferably, the weight ratio of the water insoluble substrate and the composition ranges from 1: 10 to 1: 18.
  • composition or mask according to the present invention is intended for topical application and can especially be used for caring for keratin materials, and especially the skin.
  • composition according to the present invention can be used for anti-wrinkling.
  • the present invention provides a non-therapeutic process for caring for keratin materials, in particular the skin, comprising the step of applying the composition or the mask as defined above on the keratin materials.
  • the keratin materials are facial skin and/or eye skin.
  • the present invention provides a non-therapeutic process for caring for keratin materials, in particular skin, comprising:
  • compositions according to invention example (IE. ) 1 and comparative examples (CE. ) 1-4 were prepared with the ingredients listed in Table 2 (the contents are expressed as weight percentages of active material with regard to the total weight of each composition, unless otherwise indicated) :
  • Composition of invention example 1 represents composition according to the present invention.
  • Composition of comparative example 1 does not comprise an antioxidant.
  • Composition of comparative example 2 does not comprise ascorbic acid or its derivative.
  • Composition of comparative example 3 does not comprise ascorbic acid or its derivative, and hydroxyhydrocinnamate antioxidant.
  • invention example (IE. ) 4 20 g of the composition in Table 4 was impregnated into a tissue comprising 100 wt. %of alginate fiber derived from seaweed relative to the total weight of the tissue for 12 hours, wherein the weight ratio of the tissue and the composition is 1: 13.5. Then the procedure of invention example 2 was followed to determine the content of retinyl palmitate in the composition squeezed out.
  • comparative example (CE. ) 5 20 g of the composition in Table 4 was impregnated into a tissue made of viscose fiber, wherein the weight ratio of the water insoluble substrate and the composition is 1: 13.5. Then the procedure of invention example 2 was followed to determine the content of retinyl palmitate in the composition squeezed out.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)

Abstract

It relates to a composition for caring for keratin materials and a mask containing the same. It also relates to a non-therapeutic process for caring for keratin materials with said composition or mask.

Description

    COMPOSITION FOR CARING FOR KERATIN MATERIALS AND MASK CONTAINING THE SAME TECHNICAL FIELD
  • The present invention relates to a cosmetic composition and mask containing the same. In particular, the present invention relates to a composition for caring for keratin materials and a mask containing the same, as well as a non-therapeutic process for caring for keratin materials with said composition or mask.
  • BACKGROUND ART
  • Skin is the protective barrier for the human body. It protects the interior of the body form physical injury (such as trauma) and biological injury (such as bacterial, viruses or fungi) .
  • Skin aging is part of the aging process of human body, which not only relates to the age itself, but also closely relates to external factors, such as sunlight exposure. The light induced skin aging ( “light-aging” ) is mainly caused by sunlight irradiation, and as depletion of the ozone layer is aggravating, the light-aging of the skin becomes more and more serious, which affects the appearance of the skin.
  • The development of formulations dedicated to caring for the skin is permanent.
  • There are many challenges in formulating cosmetic compositions. Some active ingredients such as retinoids are not stable. In order to be commercially acceptable, the active ingredient contained in the cosmetic products must be stable for a certain period of time. No matter how efficacious a product is, the product will not be commercially acceptable if it deteriorates under storage conditions prior to sale.
  • Also, some lipophilic active ingredient such as retinoids cannot be delivered into the skin effectively.
  • Thus, it is still a goal to develop cosmetic products which can deliver retinoids into the skin effectively and retinoids contained therein are stable for a relatively long term.
  • SUMMARY OF THE INVENTION
  • It is an object of the present invention to develop cosmetic products, retinoids contained therein are stable for a relatively long term, for example, at least two months.
  • It is another object of the present invention to develop cosmetic products which can deliver retinoids into the skin effectively.
  • Thus, according to a first aspect, the present invention provides a composition for caring for keratin materials, comprising:
  • a) at least one retinoid; and
  • b) an antioxidant combination of
  • i) ascorbic acid or its derivative,
  • ii) tocopherol or its derivative, and
  • iii) at least one hydroxyhydrocinnamate antioxidant.
  • According to a second aspect, the present invention provides a mask for caring for keratin materials, comprising:
  • A) a hydrophilic mask tissue, and
  • B) a composition according to the present invention impregnated into the mask tissue.
  • According to a third aspect, the present invention also provides a non-therapeutic process for caring for keratin materials, in particular the skin, comprising the step of applying the composition or the mask according to the present invention on the keratin materials.
  • The inventors found that retinoids are stable for a relatively long term and can be delivered into the skin effectively.
  • Other subjects and characteristics, aspects and advantages of the present invention will emerge even more clearly on reading the detailed description and the examples that follow.
  • DETAILED DESCRIPTION OF THE INVENTION
  • As used herein, unless otherwise indicated, the limits of a range of values are included within this range, in particular in the expressions "between…and…" and "from…to …” .
  • As used herein, the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well as optional, additional, unspecified ones.
  • As used herein, the use of the term “comprising” also discloses the embodiment wherein no features other than the specifically mentioned features are present (i.e. “consisting of” ) .
  • Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the field the present invention belongs to. When the definition of a term in the present description conflicts with the meaning as commonly understood by those skilled in the field the present invention belongs to, the definition described herein shall apply.
  • Unless otherwise specified, all numerical values expressing amount of ingredients and the like used in the description and claims are to be understood as being modified by the term “about” . Accordingly, unless indicated to the contrary, the numerical values and parameters described herein are approximate values which are capable of being changed according to the desired performance obtained as required.
  • As used herein, the expression "at least one" used in the present description is equivalent to the expression "one or more" .
  • For the purposes of the present invention, the term “keratin material” is intended to cover the skin. Facial skin and eye skin are most particularly considered according to the present invention.
  • As used herein, “stable” means that retinol or its derivatives contained in the mask will not decompose substantially for at least 2 months.
  • The composition for caring for keratin materials according to the present invention comprises:
  • a) at least one retinoid; and
  • b) an antioxidant combination of
  • i) ascorbic acid or its derivative,
  • ii) tocopherol or its derivative, and
  • iii) at least one hydroxyhydrocinnamate antioxidant.
  • Retinoids
  • According to the first aspect, the composition according to the present invention comprises at least one retinoid.
  • The retinoids according to the present invention include retinol (vitamin A) , retinal (vitamin A aldehyde) , retinoic acid (vitamin A acid) , or  an ester of retinol and of a C 2-C 20 acid, such as the propionate, the acetate, the linoleate or the palmitate of retinol (retinyl palmitate) , among others.
  • Thus, in some embodiments, the retinoid is selected from retinol, retinal, retinoic acid, esters of retinol and of a C 2-C 20 acid, and a combination thereof.
  • Among the retinoids, mention may more particularly be made of retinol, retinal, retinoic acid, in particular all-trans retinoic acid and 13-cis retinoic acid, retinol derivatives, such as retinyl acetate, propionate or palmitate, and the retinoids described in the following patent applications: FR 2 370 377, EP 0 199 636, EP 0 325 540 and EP 0 402 072.
  • Preferably, the retinoid is retinol or a pro-retinol.
  • The term “retinol” is intended to mean all the isomers of retinol, i.e. all-trans retinol, 13-cis retinol, 11-cis retinol, 9-cis retinol and 3, 4-didehydro retinol.
  • As a representative of pro-retinol, mention may in particular be made of retinyl palmitate (the palmitate of retinol) .
  • Preferably, the retinoid is selected from retinol, retinyl palmitate, and a combination thereof.
  • Thus, in some preferred embodiments, the composition according to the present invention comprises retinol and/or retinyl palmitate.
  • Advantageously, the retinoid is present in an amount ranging from 0.1 wt.%to 5 wt. %, preferably from 0.1 wt. %to 2 wt. %, more preferably from 0.15 wt. %to 1 wt. %, relative to the total weight of the composition.
  • Antioxidants
  • According to the first aspect, the composition according to the present invention an antioxidant combination of i) ascorbic acid or its derivative, ii) tocopherol or its derivative, and iii) at least one hydroxyhydrocinnamate antioxidant.
  • Ascorbic acid and its derivatives
  • As used herein, derivatives of ascorbic acid include aminopropyl ascorbyl phosphate, ascorbic acid polypeptide, ascorbyl dipalmitate, ascorbyl glucoside, ascorbyl linoleate, ascorbyl methylsilanol  pectinate, ascorbyl palmitate, ascorbyl tetraisopalmitate, trisodium ascorbyl palmitate phosphate, disodium ascorbyl sulfate, calcium ascorbate, methylsilanol ascorbate, sodium ascorbate, sodium ascorbyl phosphate, sodium ascorbyl/cholesteryl phosphate, tetrahexyldecyl ascorbate, magnesium ascorbyl phosphate, among others.
  • Thus, in some embodiments, the composition according to the present invention comprises one or more of ascorbic acid, aminopropyl ascorbyl phosphate, ascorbic acid polypeptide, ascorbyl dipalmitate, ascorbyl glucoside, ascorbyl linoleate, ascorbyl methylsilanol pectinate, ascorbyl palmitate, ascorbyl tetraisopalmitate, trisodium ascorbyl palmitate phosphate, disodium ascorbyl sulfate, calcium ascorbate, methylsilanol ascorbate, sodium ascorbate, sodium ascorbyl phosphate, sodium ascorbyl/cholesteryl phosphate, tetrahexyldecyl ascorbate, magnesium ascorbyl phosphate.
  • Preferably, the composition according to the present invention comprises ascorbic acid and/or ascorbyl glucoside.
  • Advantageously, ascorbic acid or its derivative is present in an amount ranging from 0.05 wt. %to 3 wt. %, preferably from 0.1 wt. %to 2 wt. %, more preferably from 0.15 wt. %to 1 wt. %, relative to the total weight of the composition.
  • Tocopherol and its derivatives
  • As used herein, derivatives of tocopherol include tocopheryl acetate, tocopheryl linoleate, tocopheryl linoleate/oleate, tocopheryl nicotinate, tocopheryl retinoate, sodium tocopheryl phosphate, dioleyl tocopheryl methylsilanol, among others.
  • Thus, in some embodiments, the composition according to the present invention comprises one or more of tocopherol, tocopheryl acetate, tocopheryl linoleate, tocopheryl linoleate/oleate, tocopheryl nicotinate, tocopheryl retinoate, sodium tocopheryl phosphate, and dioleyl tocopheryl methylsilanol.
  • Preferably, the composition according to the present invention comprises tocopherol.
  • Advantageously, tocopherol or its derivative is present in an amount ranging from 0.05 wt. %to 3 wt. %, preferably from 0.1 wt. %to 2 wt. %, more  preferably from 0.15 wt. %to 1 wt. %, relative to the total weight of the composition.
  • Hydroxyhydrocinnamate antioxidants
  • Preferably, the hydroxyhydrocinnamate antioxidant is selected from pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate, octadecyl di-t-butyl-4-hydroxyhydrocinnamate, tetradibutyl pentaerithrityl hydroxylhydrocinnamate, and a combination thereof.
  • Advantageously, the hydroxyhydrocinnamate antioxidant is present in an amount ranging from 0.05 wt. %to 3 wt. %, preferably from 0.1 wt. %to 2 wt.%, more preferably from 0.15 wt. %to 1 wt. %, relative to the total weight of the composition.
  • Aqueous phase
  • The composition of the present invention may comprise an aqueous phase.
  • Said aqueous phase comprises water.
  • Optionally, the aqueous phase comprises an organic solvent miscible with water (at room temperature 25℃) selected from glycols and polyols having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferentially having from 2 to 6 carbon atoms, such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; and combinations thereof, so as to provide a hydration effect.
  • Advantageously, the aqueous phase is present in the composition of the present invention in an amount ranging from 50%to 95%by weight, preferably from 60%to 85%by weight, relative to the total weight of the composition.
  • Oily phase
  • The composition of the present invention may comprise an oily phase.
  • Said oily phase comprise at least one oil.
  • The oil can be volatile or non-volatile.
  • The term “oil” means a water-immiscible non-aqueous compound that is liquid at room temperature (25℃) and at atmospheric pressure (760  mmHg) . The term “non-volatile oil” means an oil that may remain on keratin materials at room temperature and atmospheric pressure for at least several hours and that especially has a vapour pressure of less than 10 -3 mmHg (0.13 Pa) . A non-volatile oil may also be defined as having an evaporation rate such that, under the conditions defined previously, the amount evaporated after 30 minutes is less than 0.07 mg/cm 2.
  • These oils may be of plant, mineral or synthetic origin.
  • Said oil can be selected from hydrocarbon-based, silicone or fluorinated oils.
  • The term “hydrocarbon-based oil” means an oil formed essentially from, or even constituted by, carbon and hydrogen atoms, and optionally O and N atoms, and free of Si and F heteroatoms. Such oil can contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • The term “silicone oil” means an oil containing at least one silicon atom, especially containing Si-O groups.
  • The term “fluorinated oil” means an oil containing at least one fluorine atom.
  • Preferably, the oil is selected from hydrocarbon-based oils.
  • Advantageously, the oily phase is present in the composition of the present invention in an amount ranging from 1 wt. %to 20 wt. %, preferably from 2 wt. %to 10 wt. %, relative to the total weight of the composition of the present invention.
  • Additional cosmetic active ingredients
  • Depend on the final purpose, the composition according to the present invention can comprises one or more additional cosmetic active ingredients.
  • As cosmetic active ingredients that may be used in the composition of the present invention, examples that may be mentioned include enzymes; flavonoids; humetants (for example, biosaccharide gum-1, mannose, sodium hyaluronate) ; tensioning agents; soothing agents; among others.
  • It is easy for the skilled in the art to adjust the amount of the additional cosmetic active ingredient based on the final use of the composition according to the present invention.
  • Additional adjuvants or additives
  • The composition of the present invention may comprise conventional cosmetic adjuvants or additives, for instance, fragrances, surfactants (for example, non-ionic surfactants) , chelating agents (for example, trisodium ethylenediamine disuccinate) , preserving agents (for example, chlorphenesin and phenoxyethanol) and bactericides (for example, hydroxyacetophenone) , thickeners (for example, xanthan gum, ammonium polyacryloyldimethyl taurate) , pH adjusting agents (for example, sodium citrate) , and combinations thereof.
  • The skilled in the art can select the amount of the additional adjuvants or additive so as not to adversely impact the final use of the composition according to the present invention.
  • According to a preferred embodiment, the present invention provides a composition for caring for keratin materials comprising, relative to the total weight of the composition:
  • a) from 0.15 wt. %to 1 wt. %of retinol and/or retinyl palmitate; and
  • b) an antioxidant combination of
  • i) from 0.15 wt. %to 1 wt. %of ascorbic acid or ascorbyl glucoside,
  • ii) from 0.15 wt. %to 1 wt. %of tocopherol, and
  • iii) from 0.15 wt. %to 1 wt. %of at least one hydroxyhydrocinnamate antioxidant selected from pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate, octadecyl di-t-butyl-4-hydroxyhydrocinnamate, tetradibutyl pentaerithrityl hydroxylhydrocinnamate, and a combination thereof.
  • Galenic form
  • The composition of the present invention may be in the form of gel, lotion, or emulsion.
  • Masks
  • The composition according to the present invention can be impregnated into a mask tissue to form a mask.
  • According to the second aspect, the present invention relates to a mask for caring for keratin materials, comprising:
  • A) a hydrophilic mask tissue, and
  • B) a composition according to the present invention impregnated into the mask tissue.
  • Hydrophilic mask tissues
  • According to the first aspect, the mask according to the present invention comprises a hydrophilic mask tissue.
  • Preferably, the mask tissue is water-insoluble.
  • For the purpose of the invention, the term “water-insoluble” means that the mask tissue is not dissolvable in water and it doesn’ t break apart upon immersion in water.
  • The skilled in the art can choose a suitable mask tissue and the weight ratio of the mask tissue used and the composition according to the present invention based on the nature of the composition.
  • The mask tissue can be a woven or non-woven fabric.
  • Preferably, the mask tissue is an alginate tissue.
  • Alginate tissues are known in the art and are described in WO2020001069A1.
  • For example, an alginate tissue may comprise a water-insoluble alginate chosen from calcium alginate, strontium alginate, zinc alginate, copper alginate, manganese alginate, or a combination thereof, preferably calcium alginate, preferably in an amount ranging from 20 wt. %to 100 wt. %, relative to the total weight of the tissue.
  • Preferably, when the mask tissue is an alginate tissue, the composition according to the present invention comprises a pH adjusting agent selected from sodium acetate, sodium citrate, sodium tartrate, and a combination thereof in an amount ranging from 0.01 wt. %to 1.0 wt. %, preferably from 0.05 wt. %to 0.45 wt. %, more preferably from 0.15 wt. %to 0.3 wt. %, relative to the total weight of the composition according to the present invention.
  • The mask tissue may be consisted of one or more layers. If a multilayer tissue is used, the material of each layer may be the same or different from each other. The multilayer tissue can be prepared by laminating multiple layers made from the materials mentioned above.
  • The mask tissue can have a wide variety of shapes, depending on the desired use and characteristic of the mask.
  • The mask tissue is typically designed to fit the area of the skin to which topical application is desired. For example, when the mask is applied to the face, the mask tissue is designed to correspond to the shape of the face avoiding the eye, nostril, and mouth areas, as necessary.
  • Preferably, the weight ratio of the water insoluble substrate and the composition ranges from 1: 3 to 1: 20. More preferably, the weight ratio of the water insoluble substrate and the composition ranges from 1: 10 to 1: 18.
  • Use
  • The composition or mask according to the present invention is intended for topical application and can especially be used for caring for keratin materials, and especially the skin.
  • In particular, the composition according to the present invention can be used for anti-wrinkling.
  • According to the third aspect, the present invention provides a non-therapeutic process for caring for keratin materials, in particular the skin, comprising the step of applying the composition or the mask as defined above on the keratin materials.
  • In particular, the keratin materials are facial skin and/or eye skin.
  • In some embodiments, the present invention provides a non-therapeutic process for caring for keratin materials, in particular skin, comprising:
  • applying the mask according to the present invention on the keratin materials;
  • allowing the mask to remain on the keratin materials for a period of time; and
  • removing the mask from the keratin materials.
  • The present invention is illustrated in greater detail by the examples described below, which are given as non-limiting illustrations.
  • Examples
  • Main raw materials used, trade names and supplier thereof are listed in Table 1.
  • Table 1
  • Invention Example 1 and Comparative Examples 1-4
  • Compositions according to invention example (IE. ) 1 and comparative examples (CE. ) 1-4 were prepared with the ingredients listed in Table 2 (the contents are expressed as weight percentages of active material with regard to the total weight of each composition, unless otherwise indicated) :
  • Table 2
  • Composition of invention example 1 represents composition according to the present invention.
  • Composition of comparative example 1 does not comprise an antioxidant.
  • Composition of comparative example 2 does not comprise ascorbic acid or its derivative.
  • Composition of comparative example 3 does not comprise ascorbic acid or its derivative, and hydroxyhydrocinnamate antioxidant.
  • Composition of comparative example 4 does not comprise ascorbic acid or its derivative, and tocopherol or its derivative.
  • Preparation procedure:
  • Each composition was prepared as follows, taking composition of invention example 1 for illustration:
  • 1) . adding water (40 wt. %of the total amount of water) , xanthan Gum, citric acid, and sodium citrate into a blender, heating to 75 ℃ with stirring;
  • 2) . adding dicaprylyl ether, PEG-6 caprylic/capric glycerides, pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate, dicaprylyl carbonate, PPG-6-decyltetradeceth-30, octyldodecanol, and glyceryl isostearate into the blender, heating to Mixing and heating to 75 ℃ with stirring;
  • 3) . adding tocopherol into the blender to obtain an emulsion;
  • 4) . adding water (39.5 wt. %of the total amount of water) into the blender to dilute the emulsion;
  • 5) . adding ammonium polyacryloyldimethyl taurate into the blender to jellify the emulsion;
  • 6) cooling the obtained system to 30℃;
  • 7) adding ascorbyl glucoside into the blender with stirring;
  • 8) cooling the obtained system to 30℃; and
  • 9) adding retinyl palmitate with stirring to obtain an uniform composition, then discharging it via a 80 mesh filter.
  • Evaluation:
  • The contents of retinyl palmitate of the compositions of invention example 1 and comparative examples 1-4 were tested upon preparation (T0) and after being remained at 55 ℃ for one week (T1W) . The results are summarized in Table 3.
  • Table 3
  • It can be seen from Table 3 that retinyl palmitate is more stable in the composition of invention example 1, as compared with compositions of comparative examples 1-4.
  • Invention Examples 2-4 and Comparative Example 5
  • Invention examples 2-4 and comparative example 5 were carried out to study the delivery capacity for retinyl palmitate with different mask tissues. The composition listed in Table 4 was used in each of invention examples 2-4 and comparative example 5.
  • Table 4
  • *:The indicated amount is based on the total amount of the composition.
  • In invention example (IE. ) 2, 20 g of the composition in Table 4 was impregnated into a tissue comprising 20 wt. %of alginate fiber derived from seaweed and 80 wt. %of Tencel fiber relative to the total weight of the tissue for 12 hours, wherein the weight ratio of the issue and the composition is 1: 13.5. Then the tissue was squeezed and the composition squeezed out from the tissue was dissolved in isopropanol. The solution obtained was stirred for 0.5 hours and filtrated for a Ultra-high Performance Liquid Chromatography (UPLC) analysis and the retinyl palmitate was quantified by a standard method to determine the content of retinyl palmitate in the composition squeezed out.
  • In invention example (IE. ) 3, 20 g of the composition in Table 4 was impregnated into a tissue comprising 50 wt. %of alginate fiber derived from seaweed and 50 wt. %of Tencel fiber relative to the total weight of the tissue for 12 hours, wherein the weight ratio of the tissue and the composition is1: 13.5. Then the procedure of invention example 2 was followed to determine the content of retinyl palmitate in the composition squeezed out.
  • In invention example (IE. ) 4, 20 g of the composition in Table 4 was impregnated into a tissue comprising 100 wt. %of alginate fiber derived from seaweed relative to the total weight of the tissue for 12 hours, wherein the weight ratio of the tissue and the composition is 1: 13.5. Then the procedure of invention example 2 was followed to determine the content of retinyl palmitate in the composition squeezed out.
  • In comparative example (CE. ) 5, 20 g of the composition in Table 4 was impregnated into a tissue made of viscose fiber, wherein the weight ratio of the water insoluble substrate and the composition is 1: 13.5. Then the procedure of invention example 2 was followed to determine the content of retinyl palmitate in the composition squeezed out.
  • The content of retinyl palmitate in each composition squeezed out in invention examples 2-4 and comparative example 5 are summarized in Table 5.
  • Table 5
  •   RETINYL PALMITATE (%)
    IE. 2 0.19
    IE. 3 0.2
    IE. 4 0.2
    CE. 5 0.18
  • It can be seen from Table 5 that the content of Retinyl Palmitate is higher when impregnated into alginate tissues as compared with tissue made of viscose fiber. And the dosage will get higher as the composition of alginate fiber increased in the tissue.

Claims (13)

  1. A composition for caring for keratin materials, comprising:
    a) at least one retinoid; and
    b) an antioxidant combination of
    i) ascorbic acid or its derivative,
    ii) tocopherol or its derivative, and
    iii) at least one hydroxyhydrocinnamate antioxidant.
  2. Composition of claim 1, wherein the retinoid is selected from retinol, retinal, retinoic acid, esters of retinol and of a C 2-C 20 acid, and a combination thereof, preferably, the retinoid is selected from retinol, retinyl palmitate, and a combination thereof.
  3. The composition according to Claim 1 or 2, wherein the retinoid is present in an amount ranging from 0.1 wt. %to 5 wt. %, preferably from 0.1 wt. %to 2 wt. %, more preferably from 0.15 wt. %to 1 wt. %, relative to the total weight of the composition.
  4. Composition of any of claims 1 to 3, comprising one or more of ascorbic acid, aminopropyl ascorbyl phosphate, ascorbic acid polypeptide, ascorbyl dipalmitate, ascorbyl glucoside, ascorbyl linoleate, ascorbyl methylsilanol pectinate, ascorbyl palmitate, ascorbyl tetraisopalmitate, trisodium ascorbyl palmitate phosphate, disodium ascorbyl sulfate, calcium ascorbate, methylsilanol ascorbate, sodium ascorbate, sodium ascorbyl phosphate, sodium ascorbyl/cholesteryl phosphate, tetrahexyldecyl ascorbate, and magnesium ascorbyl phosphate, preferably the composition comprises ascorbic acid and/or ascorbyl glucoside.
  5. Composition of any of claims 1 to 4, wherein ascorbic acid or its derivative is present in an amount ranging from 0.05 wt. %to 3 wt. %, preferably from 0.1 wt. %to 2 wt. %, more preferably from 0.15 wt. %to 1 wt.%, relative to the total weight of the composition.
  6. Composition of any of claims 1 to 5, comprising one or more of tocopherol, tocopheryl acetate, tocopheryl linoleate, tocopheryl linoleate/oleate, tocopheryl nicotinate, tocopheryl retinoate, sodium tocopheryl phosphate, and dioleyl tocopheryl methylsilanol, preferably, the composition comprises tocopherol.
  7. Composition of any of claims 1 to 6, wherein tocopherol or its derivative is present in an amount ranging from 0.05 wt. %to 3 wt. %, preferably from 0.1 wt. %to 2 wt. %, more preferably from 0.15 wt. %to 1 wt.%, relative to the total weight of the composition.
  8. Composition according to any of claims 1 to 7, wherein the hydroxyhydrocinnamate antioxidant is selected from pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate, octadecyl di-t-butyl-4-hydroxyhydrocinnamate, tetradibutyl pentaerithrityl hydroxylhydrocinnamate, and a combination thereof.
  9. Composition according to any of claims 1 to 8, wherein the hydroxyhydrocinnamate antioxidant is present in an amount ranging from 0.05 wt. %to 3 wt. %, preferably from 0.1 wt. %to 2 wt. %, more preferably from 0.15 wt. %to 1 wt. %, relative to the total weight of the composition.
  10. Composition according to claim 1 comprising, relative to the total weight of the composition:
    a) from 0.15 wt. %to 1 wt. %of retinol and/or retinyl palmitate; and
    b) an antioxidant combination of
    i) from 0.15 wt. %to 1 wt. %of ascorbic acid or ascorbyl glucoside,
    ii) from 0.15 wt. %to 1 wt. %of tocopherol, and
    iii) from 0.15 wt. %to 1 wt. %of at least one
    hydroxyhydrocinnamate antioxidant selected from pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate, octadecyl di-t-butyl-4-hydroxyhydrocinnamate, tetradibutyl pentaerithrityl hydroxylhydrocinnamate, and a combination thereof.
  11. A mask for caring for keratin materials, comprising:
    A) a hydrophilic mask tissue, and
    B) a composition according to any of claims 1-10 impregnated into the mask tissue.
  12. Mask according to claim 11, wherein the water insoluble mask tissue is an alginate tissue comprising a water insoluble alginate chosen from calcium alginate, strontium alginate, zinc alginate, copper alginate, manganese alginate, or a combination thereof, preferably calcium alginate, preferably in an amount ranging from 20 wt. %to 100 wt.%, preferably from 20 wt. %to 50 wt. %, relative to the total weight of the tissue.
  13. A non-therapeutic process for caring for keratin materials, comprising the step of applying the composition of any of claims 1 to 10 or the mask of claim 11 or 12 on the keratin materials.
EP22956878.7A 2022-08-31 2022-08-31 Composition for caring for keratin materials and mask containing the same Pending EP4580614A1 (en)

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PCT/CN2022/116226 WO2024045049A1 (en) 2022-08-31 2022-08-31 Composition for caring for keratin materials and mask containing the same

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DE2650851A1 (en) 1976-11-06 1978-05-11 Bosch Gmbh Robert POWER SUPPLY DEVICE FOR A DUAL-VOLTAGE SYSTEM IN A MOTOR VEHICLE
LU85849A1 (en) 1985-04-11 1986-11-05 Cird BENZONAPHTHALENIC DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION IN THE PHARMACEUTICAL AND COSMETIC FIELDS
LU87109A1 (en) 1988-01-20 1989-08-30 Cird AROMATIC ESTERS AND THIOESTERS, THEIR PREPARATION PROCESS AND THEIR USE IN HUMAN OR VETERINARY MEDICINE AND IN COSMETICS
JPH03119163A (en) 1989-06-05 1991-05-21 Sequa Chemicals Inc Binder for non-woven fiber
ES2975482T3 (en) * 2013-03-15 2024-07-08 Laboratory Skin Care Inc Compositions of fine dried particles of the retinoid active agent and topical formulations that include them
WO2017180440A1 (en) * 2016-04-11 2017-10-19 Amcol International Corporation Delivery system based on a natural microparticle for use in personal care and other topical applications
CN108456995B (en) * 2018-01-22 2021-03-19 潍坊广栗新材料科技有限公司 High-hydroscopicity non-woven fabric
WO2020001069A1 (en) * 2018-06-28 2020-01-02 L'oreal Kit for caring for the skin
WO2020093206A1 (en) * 2018-11-05 2020-05-14 L'oreal Kit for caring for the skin
CN113194921A (en) * 2018-12-29 2021-07-30 莱雅公司 Set for caring skin
FR3111074B1 (en) * 2020-06-08 2022-07-01 Oreal Composition based on retinol
FR3111075B1 (en) * 2020-06-08 2022-12-16 Oreal Composition based on retinol
EP4171476A1 (en) * 2020-06-30 2023-05-03 L'oreal Cosmetic compositions having stabilized retinol
WO2022205059A1 (en) * 2021-03-31 2022-10-06 L'oreal Compositions for caring for skin and a package for containing the same

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CN119654146A (en) 2025-03-18

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