WO2023060376A1 - Petrolatum substitute and cosmetic composition comprsing the same - Google Patents

Petrolatum substitute and cosmetic composition comprsing the same Download PDF

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Publication number
WO2023060376A1
WO2023060376A1 PCT/CN2021/123008 CN2021123008W WO2023060376A1 WO 2023060376 A1 WO2023060376 A1 WO 2023060376A1 CN 2021123008 W CN2021123008 W CN 2021123008W WO 2023060376 A1 WO2023060376 A1 WO 2023060376A1
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WO
WIPO (PCT)
Prior art keywords
oil
butter
petrolatum
dimer
ester
Prior art date
Application number
PCT/CN2021/123008
Other languages
French (fr)
Inventor
Fan Wang
Yirui ZHU
Original Assignee
L'oreal
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 L'oreal filed Critical L'oreal
Priority to PCT/CN2021/123008 priority Critical patent/WO2023060376A1/en
Priority to FR2111812A priority patent/FR3127882A1/en
Publication of WO2023060376A1 publication Critical patent/WO2023060376A1/en

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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
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/98Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
    • A61K8/981Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin of mammals or bird
    • A61K8/986Milk; Derivatives thereof, e.g. butter
    • 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
    • A61K8/31Hydrocarbons
    • 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
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8111Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; Compositions of derivatives of such polymers
    • 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
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin

Definitions

  • the present invention relates to a petrolatum substitute and a composition comprising the same, in particular, a cosmetic composition comprising the same.
  • the present invention also relates to a cosmetic process for caring for and/or making up keratin materials.
  • Petrolatum is an oily component and it has superior barrier function, a highly thixotropic viscosity profile, and unique desirable sensory properties including non-sticky and easy-spreading with film residual.
  • petrolatum is commonly used as a raw material in cosmetics to achieve good barrier function and unique sensory profiles.
  • petrolatum is a by-product from the petroleum industry, therefore it is made from non-renewable source.
  • An object of the present invention is thus to develop a petrolatum substitute derived from renewable sources.
  • the present invention provides a petrolatum substitute, comprising:
  • the petrolatum substitute according to the present invention has petrolatum-like behavior.
  • petrolatum-like behavior means the petrolatum substitute has barrier function, thixotropic behaviour, and sensory profile especially the spreading behaviour, greasy texture, and greasy film comparable to that of petrolatum.
  • the petrolatum substitute according to the present invention is made from renewable ingredients and can be used in many applications, for example, it can be used in cosmetic compositions.
  • the present invention provides a cosmetic composition comprising:
  • the total amount of the solid fatty substance: the pasty compound: the oil is 0.1 wt. %-50 wt. %, relative to the total weight of the composition.
  • the present invention provides a cosmetic process for caring for and/or making up keratin materials comprising applying the cosmetic composition as described above to the keratin materials.
  • keratin materials is intended to cover human skin, mucous membranes such as the lips. Facial skin and lips are most particularly considered according to the present invention.
  • the petrolatum substitute according to the present invention comprises at least one solid fatty substance.
  • the cosmetic composition according to the present invention comprises at least one solid fatty substance.
  • fatty substance means an organic compound that is insoluble in water at room temperature (25°C) and at atmospheric pressure (1.013x10 5 Pa) (solubility of less than 5%by weight, preferably less than 1%by weight and even more preferentially less than 0.1%by weight) . They have in their structure at least one hydrocarbon-based chain including at least 6 carbon atoms.
  • the fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF) , liquid petroleum jelly or decamethylcyclopentasiloxane.
  • solid fatty substance means a fatty substance which is solid at room temperature (25°C) and at atmospheric pressure (760 mmHg) .
  • the solid fatty substance is derived from plant origin or other renewable origins.
  • the solid fatty substance has a melting point of no less than 30°C.
  • the melting point of a solid fatty substance can be measured using a differential scanning calorimeter (DSC) , for example the calorimeter sold under the name “DSC Q100” by the company TA Instruments with the software "TA Universal Analysis” .
  • DSC differential scanning calorimeter
  • the measurement protocol is as follows:
  • a solid fatty substance sample of 5 mg placed in a crucible is subjected to a first temperature rise ranging from -20°C. to 100°C at a heating rate of 10°C. /minute, then is cooled from 100°C. to -20°C at a cooling rate of 10°C. /minute and is finally subjected to a second temperature rise ranging from -20°C to 100°C at a heating rate of 5°C/minute.
  • the variation in the difference in power absorbed by the empty crucible and by the crucible containing the sample is measured as a function of the temperature.
  • the melting point of the sample is the temperature value corresponding to the top of the peak of the curve representing the variation in the difference in power absorbed as a function of the temperature.
  • the solid fatty substance is a plant butter.
  • plant butter means a butter from plant origin.
  • the solid fatty substance is selected from butyrospermum parkii (shea) butter, Theobroma Grandiflorum Seed Butter, almond butter, aloe butter, apricot kernel butter, avocado butter, coconut cream butter, cupuacu butter, dhupu butter, hemp butter, Simmondsia Chinensis (Jojoba) Butter, kokum butter, macadamia nut butter, Mangifera Indica (Mango) Seed Butter and combinations thereof.
  • the solid fatty substance used is selected from butyrospermum parkii (shea) butter, Theobroma Grandiflorum Seed Butter, and combinations thereof.
  • the solid fatty substance is present in the petrolatum substitute according to the present invention in an amount ranging from 5 wt. %to 80 wt. %, preferably from 10 wt. %to 50 wt. %, more preferably from 25 wt. %to 35 wt. %, relative to the total weight of the petrolatum substitute.
  • the solid fatty substance is present in the cosmetic composition according to the present invention in an amount ranging from 0.1 wt. %to 50 wt. %, preferably from 0.1 wt. %to 20 wt. %, relative to the total weight of the composition.
  • the petrolatum substitute comprises at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof.
  • the cosmetic composition comprises at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof.
  • an ester of dimer dilinoleic acid and polyol (s) or an ester thereof is intended to denote one of the derivatives of these dimer dilinoleic acid esters of polyol (s) obtained either by reaction of alcohol function (s) of the polyol, which are not employed in bonds of ester type with acid functions of the dilinoleic acid, with one or more carboxylic functions of acid molecules other than dilinoleic acid or alternatively by reaction of acid functions of the dilinoleic dimer, which are not employed in bonds of ester type with alcohol functions of the polyol, with alcohol functions of alcohol molecules other than the polyol.
  • the dimer dilinoleic acid that is suitable for use in the present invention may be obtained by polymerization reaction, especially by intermolecular dimerization of at least one linoleic acid.
  • the oxidation stability of the compound may be improved by hydrogenating the double bonds remaining after the dimerization reaction.
  • the linoleic acid dimer may also be obtained by dimerization of the hydrogenated form of linoleic acid.
  • the hydrogenated form of the acid or of the diacid may be partial or total, and may correspond, for example, to the saturated form, which is more oxidation stable.
  • the carboxylic functions of the dimer dilinoleic acid residue not engaged in the ester bond with the polyol residue (s) may be engaged in other ester bonds with other alcohol functions of alcohol molecules other than the polyol (s) .
  • These alcohol molecules or residues may be monoalcohols or polyols.
  • hydrocarbon-based compounds comprising a hydroxyl function and containing from 4 to 40 carbon atoms, in particular from 6 to 36 carbon atoms, in particular from 8 to 32 carbon atoms, in particular from 16 to 28 carbon atoms and more particularly from 18 to 24 carbon atoms.
  • monoalcohols that are suitable for the present invention, mention may be made, in a non-limiting manner, of butanol, pentanol, propanol, hexanol, heptanol, octanol, decanol, dodecanol, hexadecanol, octadecanol, eicosadecanol, phytosterol, isostearol, stearol, cetol, behenol, etc.
  • polyol is intended to denote any hydrocarbon-based compound comprising at least two hydroxyl functions and containing from 4 to 40 carbon atoms, in particular from 6 to 36 carbon atoms, in particular from 8 to 32 carbon atoms, in particular from 16 to 28 carbon atoms and more particularly from 18 to 24 carbon atoms.
  • the hydrocarbon-based chains may be interrupted, where appropriate, by the presence of at least one hetero atom, and especially an oxygen atom.
  • a polyol or a polyol ester that is suitable for use in the present invention may comprise, for example, from 2 to 12 hydroxyl functions, in particular from 2 to 8 hydroxyl functions, and more particularly from 4 to 6 hydroxyl functions.
  • the hydroxyl functions other than those already employed in an ester bond with the dimer dilinoleic acid, may also be employed, wholly or partly with other ester bonds via reactivity with acid molecules other than the dimer dilinoleic acid.
  • the polyol or an ester thereof that is suitable for use in the present invention may be selected especially from linear, branched, cyclic or polycyclic, saturated or unsaturated alcohols.
  • the polyol may be selected, for example, from a diol, a triol, a tetraol, or a pentaol, or an ester thereof.
  • the polyol may be a diol, or an ester thereof, selected especially from a fatty alcohol dimer, a monoglycerol or polyglycerol, a C 2-4 monoalkylene or polyalkylene glycol, 1, 4-butanediol and pentaerythritol.
  • diols that are also suitable for use in the present invention, mention may be made, in a non-exhaustive manner, of butanediol, pentanediol, propanediol, hexanediol, hexylene glycol, heptanediol, octanediol, nonanediol, decanediol, 1-decanediol, dodecanediol, tridecanediol, tetradecanediol, pentadecanediol, hexadecanediol, nonadecanediol, octadecanediol, cyclohexanediol, diglycerol, erythritol, pentaerythritol, xylitol, sorbitol, ethylene glycol and xylene glycol
  • a fatty alcohol dimer may also be the product of hydrogenation, for example catalytic hydrogenation, of a fatty acid dimer, which is itself obtained by dimerization of at least one unsaturated fatty acid, especially of C 8 to C 34 , especially of C 12 to C 22 , in particular of C 16 to C 20 and more particularly of C 18 .
  • a fatty alcohol dimer may be a diol dimer that can be the product of hydrogenation of dilinoleic diacid. It may be in a saturated form.
  • a fatty alcohol dimer may be, for example, a dilinoleol dimer.
  • This compound is a glycerol dimer resulting from the condensation of two molecules of glycerol, with the loss of a water molecule.
  • diglycerol denotes any isomer combination that can result from such a condensation, for instance linear isomers, branched isomers and, where appropriate, cyclic isomers resulting from an intramolecular dehydration of a diglycerol molecule.
  • the diglycerol may be obtained via any process known to those skilled in the art and especially those described in patent EP 0 750 848.
  • acid molecules that can interact with one or more hydroxyl functions of the polyol, not employed in the ester bond with the dimer dilinoleic acid, mention may be made, in a non-limiting manner, of molecules derived from isostearic acid, behenic acid, phytosteric acid, stearic acid or cetylic acid.
  • An ester of dimer dilinoleic acid and polyol (s) that is suitable for use in the present invention may be obtained by reacting a polyol or an ester thereof with a dimer dilinoleic acid, in a molar ratio of about 1.0: 0.2-1.0.
  • An ester that may be suitable for use in the present invention may especially be obtained by reacting a dimer dilinoleic acid with a dilinoleol and, where appropriate, at least one additional monoalcohol selected especially from behenol, isostearol, phytosterol, stearol and cetol, and mixtures thereof.
  • an ester used in the context of the present invention may be used in the form of a mixture of various esters, for example.
  • An ester of dimer dilinoleic acid and polyol (s) or an ester thereof that is suitable for the present invention may be obtained, for example, by reacting a glycerol, an isostearic acid and a dimer dilinoleic acid, especially, in a molar ratio of 1.0: 0.2-1.0: 0.5-0.9.
  • esters of dimer dilinoleic acid and polyol (s) or an ester thereof suitable for the present invention mention may be made of the esters described in patent applications JP 2004-256515 and JP 2005-179377.
  • An ester of dimer dilinoleic acid and polyol (s) or an ester thereof suitable for use in the present invention may have a molecular weight ranging from about 2000 to about 25 000 g/mol, in particular from about 4000 to about 20 000 g/mol, in particular from about 7000 to about 15 000 g/mol and more particularly from about 8000 to about 10 000 g/mol.
  • an ester in accordance with the present invention may comprise an alternating sequence of dimer dilinoleate residue (s) and of residue (s) related to said polyol (s) , and especially to the said diol (s) , said polyols or diols being, for example, as defined above.
  • each of the two ends of the said sequence may bear, respectively, a unit OR' and OR" with R' and R" representing, independently of each other, a hydrogen atom or OR' and OR" representing, independently of each other, a C 2 to C 36 , especially C 8 to C 24 , in particular C 12 to C 20 and more particularly C 16 to C 18 hydrocarbon-based monoalcohol residue.
  • R' and R" may both represent a hydrogen atom.
  • OR' and OR" may both represent an identical or different hydrocarbon-based monoalcohol residue.
  • hydrocarbon-based monoalcohol residues OR' and OR" that may be suitable for the present invention, mention may be made of fatty alcohol residues.
  • an ester of dimer dilinoleic acid and polyol (s) or an ester thereof that may be suitable for use in the present invention may have the general formula (I) below:
  • OR 2 O represents a fatty alcohol dimer residue having from 16 to 68, from 24 to 44, in particular from 32 to 40, and more particularly 36 carbon atoms.
  • OR 3 represents a monoalcohol residue having from 4 to 40, in particular from 6 to 36, in particular from 8 to 32, in particular from 16 to 28, and more particularly from 18 to 24 carbon atoms, and
  • - n is an integer ranging from 1 to 15, in particular from 2 to 10 and more particularly from 5 to 7.
  • OR 2 O may represent a dimer dilinoleyl residue.
  • OR 3 may represent a hydrocarbon-based monoalcohol residue selected, for example, from behenyl, isostearyl and phytosteryl residues, and mixtures thereof.
  • ester of dimer dilinoleic acid and polyol (s) or an ester thereof that may be suitable for use in the present invention may, especially, have the general formula (II) below:
  • - n is an integer ranging from 1 to 15, especially from 2 to 10 and in particular from 5 to 7;
  • R' 3 represents H or OR' 3 represents a fatty acid residue having from 8 to 34, especially from 12 to 22, in particular of 16 to 20 and more particularly 18 carbon atoms.
  • the fatty acid residue represented by OR' 3 may be an isostearyl residue.
  • the viscosity of an ester of dimer dilinoleic acid and polyol (s) or an ester thereof may be measured according to any process known to those skilled in the art, and especially according to the conventional process described hereinbelow.
  • the viscosity of an ester of dimer dilinoleic acid and polyol (s) or an ester thereof suitable for use in the present invention may range from about 20 000 mPa. s to about 5 000 000 mPa. s, especially from about 40 000 mPa. s to about 4 500 000 mPa. s and in particular from about 50 000 mPa. s to about 4 500 000 mPa. s.
  • the viscosity can be measured with an Anton Paar MCR 301 rheometer equipped with a CP-25 plate and cone geometry at 25°C under a steady state flowtest with the shear rate ramping from 1.0-1000 s- 1 . The viscosity was then determined using the viscosity at the shear rate of 0.1/s.
  • An ester of dimer dilinoleic acid and polyol (s) or an ester thereof that is suitable for the present invention may be selected especially from the esters having the following INCI nomenclature: polyglyceryl-2 isostearate dimer dilinoleate copolymer, bis-behenyl/isostearyl/phytosteryl dimer dilinoleyl dimer dilinoleate, and mixtures thereof.
  • Such compounds may be obtained, for example, under the reference Hailucent ISDA (Kokyu Alcohol) and Plandool-G (Nippon Fine Chemical Company Ltd) .
  • the pasty compound is present in the petrolatum substitute according to the present invention in an amount ranging from 5 wt. %to 80 wt. %, preferably from 10 wt. %to 50 wt. %, more preferably from 25 wt. %to 35 wt. %, relative to the total weight of the petrolatum substitute.
  • the pasty compound is present in the cosmetic composition according to the present invention in an amount ranging from 0.1 wt. %to 20 wt. %, preferably from 0.5 wt. %to 15 wt. %, more preferably from 0.5 wt. %to 10 wt. %, relative to the total weight of the composition.
  • the petrolatum substitute according to the present invention comprises at least one oil.
  • the cosmetic composition according to the present invention comprises at least one oil.
  • oil means any fatty substance that is in liquid form at room temperature (25°C) and at atmospheric pressure (1.013x10 5 Pa) .
  • the oil is derived from plant origin or other renewable origins.
  • plant oil means an oil extracted from a plant or an oil synthsized from an ingredient from a plant.
  • the plant oil (s) are selected from oils of plant origin such as phytostearyl esters, such as phytostearyl oleate, phytostearyl isostearate and lauroyl/octyldodecyl/phytostearyl glutamate, for example sold under the name Eldew PS203 by Ajinomoto, triglycerides constituted of fatty acid esters of glycerol, the fatty acids of which may have chain lengths ranging from C4 to C24, these chains possibly being linear or branched, and saturated or unsaturated; these oils are notably heptanoic or octanoic triglycerides, sweet almond oil, argan oil, avocado oil, groundnut oil, camellia oil, safflower oil, beauty-leaf oil, rapeseed oil, coconut oil (or coconut kernel oil) , coriander oil, marrow oil, wheatgerm oil, jojoba oil, linseed oil, maca
  • the plant oil is selected from sweet almond oil, argan oil, avocado oil, groundnut oil, camellina oil, safflower oil, beauty-leaf oil, rapeseed oil, coconut oil (or coconut kernel oil) , coriander oil, marrow oil, wheat germ oil, jojoba oil, linseed oil, macadamia oil, corn germ oil, hazelnut oil, walnut oil, vernonia oil, apricot kernel oil, olive oil, evening-primrose oil, palm oil, passion flower oil, grapeseed oil, rose oil, castor oil, rye oil, sesame oil, rice bran oil, camelina oil, soybean oil, sunflower oil, pracaxi oil, babassu oil, mongongo oil, marula oil, arara oil, shea butter oil, Brazil nut oil, caprylic/capric acid triglycerides, and mixtures thereof; more preferentially from soybean oil, jojoba oil, castor oil and coconut oil (or coconut kernel oil) ,
  • the plant oil used is caprylic/capric acid triglycerides.
  • oils from other renewable origins mention can be made of oils from microbiologic origins such as algae oils, and oils from mineral origins such as silicone oils.
  • the oil is present in the petrolatum substitute according to the present invention in an amount ranging from 5 wt. %to 80 wt. %, preferably from 10 wt. %to 50 wt. %, more preferably from 25 wt. %to 35 wt. %, relative to the total weight of the petrolatum substitute.
  • the oil is present in the cosmetic composition according to the present invention in an amount ranging from 0.1 wt. %to 50 wt. %, preferably from 0.1 wt. %to 20 wt. %, relative to the total weight of the composition.
  • the petrolatum substitute consists of at least one solid fatty substance, at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof, and at least one oil, wherein the weight ratio of the solid fatty substance: the pasty compound: the oil is 0.06-16: 1: 0.06-16.
  • the petrolatum substitute comprises at least one solid fatty substance, at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof; at least one oil, and an optional component such as a colorant, an antioxidant, etc., provided that the optional component does not negatively affect the petrolatum-like behavior, wherein the weight ratio of the plant butter: the pasty compound: the plant oil is 0.06-16: 1: 0.06-16.
  • the weight ratio of the solid fatty substance: the pasty compound: the oil is 1-2: 1: 1-2; more preferably, 1-2: 1: 1-1.5.
  • the cosmetic composition according to the present invention may comprise other components usually used in the field under consideration.
  • the cosmetic composition may further comprise an additional component selected from cosmetic active ingredients, thickeners, surfactants, antioxidants, preserving agents, fragrances, neutralizers, antiseptics, pigments and dyes, and mixtures thereof.
  • an additional component selected from cosmetic active ingredients, thickeners, surfactants, antioxidants, preserving agents, fragrances, neutralizers, antiseptics, pigments and dyes, and mixtures thereof.
  • the cosmetic composition of the present invention is suitable to be used as a skincare product, a makeup product.
  • the petrolatum substitute and the cosmetic composition according to the present invention may be prepared in a conventional manner.
  • the present invention provides a cosmetic process for caring for/making up keratin materials comprising applying the cosmetic composition as described above to the keratin materials.
  • Petrolatum substitutes of invention examples (IE. ) 1-3 and comparative examples (CE. ) 1-3 were prepared according to the amounts of components given in Table 2. The amount of each component is given in%by weight of the active material relative to the total weight of the petrolatum substitute containing it.
  • Petrolatum substitutes of invention examples 1-3 are petrolatum substitutes according to the present invention.
  • Petrolatum substitute of comparative example 1 is a petrolatum substitute comprising Polyamide-8, instead of at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof.
  • Petrolatum substitute of comparative example 2 is a petrolatum substitute comprising Poly (C10-30 Alkyl Acrylate) , instead of at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof.
  • Petrolatum substitutes of comparative example 1-2 are petrolatum substitute, wherein the weight ratio of the plant butter: the pasty compound: the plant oil is 4/1/20, out of 0.06-16: 1: 0.06-16.
  • TEWL Transepidermal water loss
  • the recovery of consistence index can be used to characterize the thixotropic property of a material. Higher%recovery indicates stronger thixotropic behavior where a material can recovery to its original viscosity after shear.
  • the sensory profiles of the petrolatum substitute have been evaluated by either trained sensory panellists or volunteers to compare the spreading, greasy texture, and greasy film.
  • the sensory profile of petrolatum substitutes and petrolatum has been compared by 7 trained panellists with 14 duplicates on a 15-point hedonic scale.
  • Panellists have been trained with standard anchor sets with different sensory scores throughout the 15-point scale, and samples for sensory evaluation were then scored based on their training using anchors as the reference. For example, if a panel were trained with anchors scored at 1, 5, 10, 15, then a sample feels between 10 and 15 but closerto 10 then maybe it is 12. The average score from 7 panels could be 12.4.
  • 0.5 mL of sample was used for evaluation.
  • Spreading was defined as the size of surface area of the sample being spread during the 10 th motion on hand.
  • Greasy texture was defined as the sensation of fat content on spreading duringthe 10 th motion on arm.
  • Greasy film was defined as the quantity of greasy film remaining on the skin during the 20 th motion waited for two minutes.
  • the sensory profiles of the petrolatum substitutes were also compared to petrolatum by 5 volunteers. If at least 4 out of 5 volunteers feel these sensory profiles are similar to petrolatum, then they are considered to be similar.
  • the petrolatum substitute of IE. 1 and petrolatum have no significant difference on TEWL. Meanwhile, the petrolatum substitute of IE. 1 shows significantly better recovery of consistence index, easier spreading and less greasiness, and slightly higher greasy film than petrolatum.
  • the petrolatum substitute according to the present invention can be used as a petrolatum substitute.
  • Cosmetic compositions of invention example (IE. ) 4 and comparative examples (CE. ) 4-5 were prepared according to the amounts of components given in Table 4. The amount of each component is given in%by weight of the active material relative to the total weight of the composition containing it.
  • Cosmetic composition of invention example 4 is a cosmetic composition according to the present invention.
  • Cosmetic composition of comparative example 4 is a cosmetic composition contains no pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof.
  • Cosmetic composition of comparative example 5 is a cosmetic composition comprising petrolatum.
  • the cosmetic composition of invention example 4 has similar spreadability, greasy film, and greasy texture during and after application, as compared with the cosmetic composition containing the same weight of petrolatum.

Abstract

It relates to a petrolatum substitute, comprising: a) at least one solid fatty substance; b) at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof; and c) at least one oil, wherein the weight ratio of the solid fatty substance: the pasty compound: the oil is 0.06-16: 1: 0.06-16. It also relates to a cosmetic composition comprising the petrolatum substitute. It also relates to a cosmetic process for caring for and/or making up keratin materials comprising applying the cosmetic composition as described above to the keratin materials.

Description

PETROLATUM SUBSTITUTE AND COSMETIC COMPOSITION COMPRSING THE SAME TECHNICAL FIELD
The present invention relates to a petrolatum substitute and a composition comprising the same, in particular, a cosmetic composition comprising the same. The present invention also relates to a cosmetic process for caring for and/or making up keratin materials.
BACKGROUND ART
Petrolatum is an oily component and it has superior barrier function, a highly thixotropic viscosity profile, and unique desirable sensory properties including non-sticky and easy-spreading with film residual. Thus, petrolatum is commonly used as a raw material in cosmetics to achieve good barrier function and unique sensory profiles.
However, petrolatum is a by-product from the petroleum industry, therefore it is made from non-renewable source.
Efforts have been made to develop petrolatum replacements derived from renewable sources.
There are some literatures related to sustainable petrolatum replacements. For example, Engineering phytosterol-based oleogels is studied in Chen et al., Engineering phytosterol-based oleogels for potential application as sustainable petrolatum replacement, The Royal Society of Chemistry, 2020, 10, 244-252. Some petrolatum replacements still contain ingredients from non-renewable source.
Thus, there is still a need to develop petrolatum substitutes, for which majority materials are from renewable sources.
SUMMARY OF THE INVENTION
An object of the present invention is thus to develop a petrolatum substitute derived from renewable sources.
Thus, according to a first aspect, the present invention provides a petrolatum substitute, comprising:
a)at least one solid fatty substance;
b)at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof; and
c)at least one oil;
wherein the weight ratio of the solid fatty substance: the pasty compound: the oil is 0.06-16: 1: 0.06-16.
It has been found that with the combination of a) at least one solid fatty substance, b) at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof, and c) at least one oil at a specific weight ratio, a petrolatum substitute can be obtained.
The petrolatum substitute according to the present invention has petrolatum-like behavior.
As used herein, “petrolatum-like behavior” means the petrolatum substitute has barrier function, thixotropic behaviour, and sensory profile especially the spreading behaviour, greasy texture, and greasy film comparable to that of petrolatum.
The petrolatum substitute according to the present invention is made from renewable ingredients and can be used in many applications, for example, it can be used in cosmetic compositions.
According to a second aspect, the present invention provides a cosmetic composition comprising:
a) at least one solid fatty substance;
b) at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof; and
c) at least one oil,
wherein the weight ratio of the solid fatty substance: the pasty compound: the oil is 0.06-16: 1: 0.06-16;
wherein the total amount of the solid fatty substance: the pasty compound: the oil is 0.1 wt. %-50 wt. %, relative to the total weight of the composition.
According to a third aspect, the present invention provides a cosmetic process for caring for and/or making up keratin materials comprising applying the cosmetic composition as described above to the keratin materials.
Other advantages and aspects of the present invention will emerge more clearly on reading the description and the examples that follow.
DETAILD DESCRIPTION OF THE INVENTION
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art 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 art the present invention belongs to, the definition described herein shall apply.
In that which follows and 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... " .
Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" .
Throughout the instant application, the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well 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 specified, all numerical values expressing amount of ingredients and the like which are 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 accordingto the desired purpose as required.
For the purposes of the present invention, the term “keratin materials” is intended to cover human skin, mucous membranes such as the lips. Facial skin and lips are most particularly considered according to the present invention.
All percentages in the present invention refer to weight percentage, unless otherwise specified.
Solid fatty substance
According to the first aspect, the petrolatum substitute according to the present invention comprises at least one solid fatty substance.
According to the second aspect, the cosmetic composition according to the present invention comprises at least one solid fatty substance.
The term “fatty substance” means an organic compound that is insoluble in water at room temperature (25℃) and at atmospheric pressure (1.013x10 5Pa) (solubility of less than 5%by weight, preferably less than 1%by weight and even more preferentially less than 0.1%by weight) . They have in their structure at least one hydrocarbon-based chain including at least 6 carbon atoms. In addition, the fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance  chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF) , liquid petroleum jelly or decamethylcyclopentasiloxane.
The term “solid fatty substance” means a fatty substance which is solid at room temperature (25℃) and at atmospheric pressure (760 mmHg) .
Preferably, the solid fatty substance is derived from plant origin or other renewable origins.
Preferably, the solid fatty substance has a melting point of no less than 30℃.
The melting point of a solid fatty substance can be measured using a differential scanning calorimeter (DSC) , for example the calorimeter sold under the name "DSC Q100" by the company TA Instruments with the software "TA Universal Analysis" .
The measurement protocol is as follows:
A solid fatty substance sample of 5 mg placed in a crucible is subjected to a first temperature rise ranging from -20℃. to 100℃ at a heating rate of 10℃. /minute, then is cooled from 100℃. to -20℃ at a cooling rate of 10℃. /minute and is finally subjected to a second temperature rise ranging from -20℃ to 100℃ at a heating rate of 5℃/minute. During the second temperature rise, the variation in the difference in power absorbed by the empty crucible and by the crucible containing the sample is measured as a function of the temperature. The melting point of the sample is the temperature value corresponding to the top of the peak of the curve representing the variation in the difference in power absorbed as a function of the temperature.
Preferably, the solid fatty substance is a plant butter.
As used herein, “plant butter” means a butter from plant origin.
Preferably, the solid fatty substance is selected from butyrospermum parkii (shea) butter, Theobroma Grandiflorum Seed Butter, almond butter, aloe butter, apricot kernel butter, avocado butter, coconut cream butter, cupuacu butter, dhupu butter, hemp butter, Simmondsia Chinensis (Jojoba) Butter, kokum butter, macadamia nut butter, Mangifera Indica (Mango) Seed Butter and combinations thereof.
In some embodiments, the solid fatty substance used is selected from butyrospermum parkii (shea) butter, Theobroma Grandiflorum Seed Butter, and combinations thereof.
Advantageously, the solid fatty substance is present in the petrolatum substitute according to the present invention in an amount ranging from 5 wt. %to 80 wt. %, preferably from 10 wt. %to 50 wt. %, more preferably from 25 wt. %to 35 wt. %, relative to the total weight of the petrolatum substitute.
Advantageously, the solid fatty substance is present in the cosmetic composition according to the present invention in an amount ranging from 0.1 wt. %to 50 wt. %, preferably from 0.1 wt. %to 20 wt. %, relative to the total weight of the composition.
Pasty compound (s)
According to the first aspect of the present invention, the petrolatum substitute comprises at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof.
According to the first aspect of the present invention, the cosmetic composition comprises at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof.
In the expression "an ester of dimer dilinoleic acid and polyol (s) or an ester thereof” , the term "an ester thereof” is intended to denote one of the derivatives of these dimer dilinoleic acid esters of polyol (s) obtained either by reaction of alcohol function (s) of the polyol, which are not employed in bonds of ester type with acid functions of the dilinoleic acid, with one or more carboxylic functions of acid molecules other than dilinoleic acid or alternatively by reaction of acid functions of the dilinoleic dimer, which are not employed in bonds of ester type with alcohol functions of the polyol, with alcohol functions of alcohol molecules other than the polyol.
Dimer dilinoleic acid
The dimer dilinoleic acid that is suitable for use in the present invention may be obtained by polymerization reaction, especially by intermolecular dimerization of at least one linoleic acid.
The oxidation stability of the compound may be improved by hydrogenating the double bonds remaining after the dimerization reaction.
The linoleic acid dimer may also be obtained by dimerization of the hydrogenated form of linoleic acid.
The hydrogenated form of the acid or of the diacid may be partial or total, and may correspond, for example, to the saturated form, which is more oxidation stable.
As indicated previously, the carboxylic functions of the dimer dilinoleic acid residue not engaged in the ester bond with the polyol residue (s) may be engaged in other ester bonds with other alcohol functions of alcohol molecules other than the polyol (s) .
These alcohol molecules or residues may be monoalcohols or polyols.
As examples of alcohol residues that are suitable for use in the present invention, mention may be made of hydrocarbon-based compounds comprising a hydroxyl function  and containing from 4 to 40 carbon atoms, in particular from 6 to 36 carbon atoms, in particular from 8 to 32 carbon atoms, in particular from 16 to 28 carbon atoms and more particularly from 18 to 24 carbon atoms.
As examples of monoalcohols that are suitable for the present invention, mention may be made, in a non-limiting manner, of butanol, pentanol, propanol, hexanol, heptanol, octanol, decanol, dodecanol, hexadecanol, octadecanol, eicosadecanol, phytosterol, isostearol, stearol, cetol, behenol, etc.
Polyol (s)
The term "polyol" is intended to denote any hydrocarbon-based compound comprising at least two hydroxyl functions and containing from 4 to 40 carbon atoms, in particular from 6 to 36 carbon atoms, in particular from 8 to 32 carbon atoms, in particular from 16 to 28 carbon atoms and more particularly from 18 to 24 carbon atoms. The hydrocarbon-based chains may be interrupted, where appropriate, by the presence of at least one hetero atom, and especially an oxygen atom.
A polyol or a polyol ester that is suitable for use in the present invention may comprise, for example, from 2 to 12 hydroxyl functions, in particular from 2 to 8 hydroxyl functions, and more particularly from 4 to 6 hydroxyl functions.
Where appropriate, the hydroxyl functions, other than those already employed in an ester bond with the dimer dilinoleic acid, may also be employed, wholly or partly with other ester bonds via reactivity with acid molecules other than the dimer dilinoleic acid. The polyol or an ester thereof that is suitable for use in the present invention may be selected especially from linear, branched, cyclic or polycyclic, saturated or unsaturated alcohols.
Thus, the polyol may be selected, for example, from a diol, a triol, a tetraol, or a pentaol, or an ester thereof.
The polyol may be a diol, or an ester thereof, selected especially from a fatty alcohol dimer, a monoglycerol or polyglycerol, a C 2-4 monoalkylene or polyalkylene glycol, 1, 4-butanediol and pentaerythritol.
As examples of diols that are also suitable for use in the present invention, mention may be made, in a non-exhaustive manner, of butanediol, pentanediol, propanediol, hexanediol, hexylene glycol, heptanediol, octanediol, nonanediol, decanediol, 1-decanediol, dodecanediol, tridecanediol, tetradecanediol, pentadecanediol, hexadecanediol, nonadecanediol, octadecanediol, cyclohexanediol, diglycerol, erythritol, pentaerythritol, xylitol, sorbitol, ethylene glycol and xylene glycol, and isomers thereof.
A fatty alcohol dimer may also be the product of hydrogenation, for example catalytic hydrogenation, of a fatty acid dimer, which is itself obtained by dimerization of at least one unsaturated fatty acid, especially of C 8 to C 34, especially of C 12 to C 22, in particular of C 16 to C 20 and more particularly of C 18.
According to one particular embodiment, a fatty alcohol dimer may be a diol dimer that can be the product of hydrogenation of dilinoleic diacid. It may be in a saturated form.
A fatty alcohol dimer may be, for example, a dilinoleol dimer.
As an example of a diol that may be suitable for use in the present invention, mention may be made especially of diglycerol.
This compound is a glycerol dimer resulting from the condensation of two molecules of glycerol, with the loss of a water molecule.
The term "diglycerol" denotes any isomer combination that can result from such a condensation, for instance linear isomers, branched isomers and, where appropriate, cyclic isomers resulting from an intramolecular dehydration of a diglycerol molecule.
The diglycerol may be obtained via any process known to those skilled in the art and especially those described in patent EP 0 750 848.
As examples of acid molecules that can interact with one or more hydroxyl functions of the polyol, not employed in the ester bond with the dimer dilinoleic acid, mention may be made, in a non-limiting manner, of molecules derived from isostearic acid, behenic acid, phytosteric acid, stearic acid or cetylic acid.
An ester of dimer dilinoleic acid and polyol (s) that is suitable for use in the present invention may be obtained by reacting a polyol or an ester thereof with a dimer dilinoleic acid, in a molar ratio of about 1.0: 0.2-1.0.
An ester that may be suitable for use in the present invention may especially be obtained by reacting a dimer dilinoleic acid with a dilinoleol and, where appropriate, at least one additional monoalcohol selected especially from behenol, isostearol, phytosterol, stearol and cetol, and mixtures thereof.
Thus, an ester used in the context of the present invention may be used in the form of a mixture of various esters, for example.
An ester of dimer dilinoleic acid and polyol (s) or an ester thereof that is suitable for the present invention may be obtained, for example, by reacting a glycerol, an isostearic acid and a dimer dilinoleic acid, especially, in a molar ratio of 1.0: 0.2-1.0: 0.5-0.9.
As examples of an ester of dimer dilinoleic acid and polyol (s) or an ester thereof suitable for the present invention, mention may be made of the esters described in patent applications JP 2004-256515 and JP 2005-179377.
An ester of dimer dilinoleic acid and polyol (s) or an ester thereof suitable for use in the present invention may have a molecular weight ranging from about 2000 to about 25 000 g/mol, in particular from about 4000 to about 20 000 g/mol, in particular from about 7000 to about 15 000 g/mol and more particularly from about 8000 to about 10 000 g/mol.
According to one embodiment, an ester in accordance with the present invention may comprise an alternating sequence of dimer dilinoleate residue (s) and of residue (s) related to said polyol (s) , and especially to the said diol (s) , said polyols or diols being, for example, as defined above.
Thus, in such a configuration, each of the two ends of the said sequence may bear, respectively, a unit OR' and OR" with R' and R" representing, independently of each other, a hydrogen atom or OR' and OR" representing, independently of each other, a C 2to C 36, especially C 8 to C 24, in particular C 12 to C 20 and more particularly C 16 to C 18 hydrocarbon-based monoalcohol residue.
According to one embodiment, R' and R" may both represent a hydrogen atom.
According to one embodiment, OR' and OR" may both represent an identical or different hydrocarbon-based monoalcohol residue.
As examples of hydrocarbon-based monoalcohol residues OR' and OR" that may be suitable for the present invention, mention may be made of fatty alcohol residues.
According to one embodiment, an ester of dimer dilinoleic acid and polyol (s) or an ester thereof that may be suitable for use in the present invention may have the general formula (I) below:
R 3-OCO-R 1 (-COO-R 2-OCO-R 1n-COO-R 3 (I)
in which:
- COR 1CO represents a dimer dilinoleate residue,
- OR 2O represents a fatty alcohol dimer residue having from 16 to 68, from 24 to 44, in particular from 32 to 40, and more particularly 36 carbon atoms.
- OR 3 represents a monoalcohol residue having from 4 to 40, in particular from 6 to 36, in particular from 8 to 32, in particular from 16 to 28, and more particularly from 18 to 24 carbon atoms, and
- n is an integer ranging from 1 to 15, in particular from 2 to 10 and more particularly from 5 to 7.
According to one embodiment, OR 2O may represent a dimer dilinoleyl residue.
Moreover, OR 3 may represent a hydrocarbon-based monoalcohol residue selected, for example, from behenyl, isostearyl and phytosteryl residues, and mixtures thereof.
According to another embodiment, the ester of dimer dilinoleic acid and polyol (s) or an ester thereof that may be suitable for use in the present invention may, especially, have the general formula (II) below:
Figure PCTCN2021123008-appb-000001
in which:
- n is an integer ranging from 1 to 15, especially from 2 to 10 and in particular from 5 to 7;
- OCR' 1CO represents a dimer dilinoleate residue,
- OR' 2O represents a diglyceryl residue of general formula (III) below:
Figure PCTCN2021123008-appb-000002
in which:
R' 3 represents H or OR' 3 represents a fatty acid residue having from 8 to 34, especially from 12 to 22, in particular of 16 to 20 and more particularly 18 carbon atoms.
Accordingto one embodiment, the fatty acid residue represented by OR' 3 may be an isostearyl residue.
The viscosity of an ester of dimer dilinoleic acid and polyol (s) or an ester thereof may be measured according to any process known to those skilled in the art, and especially according to the conventional process described hereinbelow.
The viscosity of an ester of dimer dilinoleic acid and polyol (s) or an ester thereof suitable for use in the present invention may range from about 20 000 mPa. s to about 5 000 000 mPa. s, especially from about 40 000 mPa. s to about 4 500 000 mPa. s and in particular from about 50 000 mPa. s to about 4 500 000 mPa. s.
The viscosity can be measured with an Anton Paar MCR 301 rheometer equipped with a CP-25 plate and cone geometry at 25℃ under a steady state flowtest with the shear rate ramping from 1.0-1000 s- 1. The viscosity was then determined using the viscosity at the shear rate of 0.1/s.
An ester of dimer dilinoleic acid and polyol (s) or an ester thereof that is suitable for the present invention may be selected especially from the esters having the following INCI nomenclature: polyglyceryl-2 isostearate dimer dilinoleate copolymer, bis-behenyl/isostearyl/phytosteryl dimer dilinoleyl dimer dilinoleate, and mixtures thereof.
Such compounds may be obtained, for example, under the reference Hailucent ISDA (Kokyu Alcohol) and Plandool-G (Nippon Fine Chemical Company Ltd) .
Advantageously, the pasty compound is present in the petrolatum substitute according to the present invention in an amount ranging from 5 wt. %to 80 wt. %, preferably from 10 wt. %to 50 wt. %, more preferably from 25 wt. %to 35 wt. %, relative to the total weight of the petrolatum substitute.
Advantageously, the pasty compound is present in the cosmetic composition according to the present invention in an amount ranging from 0.1 wt. %to 20 wt. %, preferably from 0.5 wt. %to 15 wt. %, more preferably from 0.5 wt. %to 10 wt. %, relative to the total weight of the composition.
Oils
According to the first aspect, the petrolatum substitute according to the present invention comprises at least one oil.
According to the second aspect, the cosmetic composition according to the present invention comprises at least one oil.
The term “oil” means any fatty substance that is in liquid form at room temperature (25℃) and at atmospheric pressure (1.013x10 5Pa) .
Preferably, the oil is derived from plant origin or other renewable origins.
As used herein, “plant oil” means an oil extracted from a plant or an oil synthsized from an ingredient from a plant.
Preferably, the plant oil (s) are selected from oils of plant origin such as phytostearyl esters, such as phytostearyl oleate, phytostearyl isostearate and lauroyl/octyldodecyl/phytostearyl glutamate, for example sold under the name Eldew PS203 by Ajinomoto, triglycerides constituted of fatty acid esters of glycerol, the fatty acids of which may have chain lengths ranging from C4 to C24, these chains possibly being linear or branched, and saturated or unsaturated; these oils are notably heptanoic or octanoic triglycerides, sweet almond oil, argan oil, avocado oil, groundnut oil, camellia oil, safflower oil, beauty-leaf oil, rapeseed oil, coconut oil (or coconut kernel oil) , coriander oil, marrow oil, wheatgerm oil, jojoba oil, linseed oil, macadamia oil, corn germ oil, hazelnut oil, walnut oil, vernonia oil, apricot kernel oil, olive oil, evening primrose oil, palm oil,  passion flower oil, grapeseed oil, rose oil, castor oil, rye oil, sesame oil, rice bran oil, camelina oil, soybean oil, sunflower oil, pracaxi oil, babassu oil, mongongo oil, marula oil, arara oil, shea butter oil, Brazil nut oil; or alternatively caprylic/capric acid triglycerides, for instance those sold by the company Stearinerie Dubois, those sold under the name 
Figure PCTCN2021123008-appb-000003
E7000 LR01-1/MB by the company PT MUSIM MAS, or those sold under the names Miglyol
Figure PCTCN2021123008-appb-000004
and
Figure PCTCN2021123008-appb-000005
by the company Dynamit Nobel, and the refined plant-based perhydrosqualene sold under the name Fitoderm by the company Cognis; the plant-based squalene sold, for example, under the name Squalive by the company Biosynthis.
More preferably, the plant oil is selected from sweet almond oil, argan oil, avocado oil, groundnut oil, camellina oil, safflower oil, beauty-leaf oil, rapeseed oil, coconut oil (or coconut kernel oil) , coriander oil, marrow oil, wheat germ oil, jojoba oil, linseed oil, macadamia oil, corn germ oil, hazelnut oil, walnut oil, vernonia oil, apricot kernel oil, olive oil, evening-primrose oil, palm oil, passion flower oil, grapeseed oil, rose oil, castor oil, rye oil, sesame oil, rice bran oil, camelina oil, soybean oil, sunflower oil, pracaxi oil, babassu oil, mongongo oil, marula oil, arara oil, shea butter oil, Brazil nut oil, caprylic/capric acid triglycerides, and mixtures thereof; more preferentially from soybean oil, jojoba oil, castor oil and coconut oil (or coconut kernel oil) , caprylic/capric acid triglycerides, and mixtures thereof.
In some embodiments, the plant oil used is caprylic/capric acid triglycerides.
As oils from other renewable origins, mention can be made of oils from microbiologic origins such as algae oils, and oils from mineral origins such as silicone oils.
Advantageously, the oil is present in the petrolatum substitute according to the present invention in an amount ranging from 5 wt. %to 80 wt. %, preferably from 10 wt. %to 50 wt. %, more preferably from 25 wt. %to 35 wt. %, relative to the total weight of the petrolatum substitute.
Advantageously, the oil is present in the cosmetic composition according to the present invention in an amount ranging from 0.1 wt. %to 50 wt. %, preferably from 0.1 wt. %to 20 wt. %, relative to the total weight of the composition.
In some embodiments, the petrolatum substitute consists of at least one solid fatty substance, at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof, and at least one oil, wherein the weight ratio of the solid fatty substance: the pasty compound: the oil is 0.06-16: 1: 0.06-16.
In some embodiments, the petrolatum substitute comprises at least one solid fatty substance, at least one pasty compound selected from an ester of dimer dilinoleic acid  and polyol (s) or an ester thereof; at least one oil, and an optional component such as a colorant, an antioxidant, etc., provided that the optional component does not negatively affect the petrolatum-like behavior, wherein the weight ratio of the plant butter: the pasty compound: the plant oil is 0.06-16: 1: 0.06-16. Preferably, the weight ratio of the solid fatty substance: the pasty compound: the oil is 1-2: 1: 1-2; more preferably, 1-2: 1: 1-1.5.
Other components
In addition to at least one solid fatty substance, at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof and at least one oil, the cosmetic composition according to the present invention may comprise other components usually used in the field under consideration.
For example, the cosmetic composition may further comprise an additional component selected from cosmetic active ingredients, thickeners, surfactants, antioxidants, preserving agents, fragrances, neutralizers, antiseptics, pigments and dyes, and mixtures thereof.
It is a matter of routine operations for a person skilled in the art to adjust the nature and amount of the other ingredients present in the cosmetic compositions in accordance with the present invention such that the advantageous properties of the composition used according to the present invention are not, or are not substantially, adversely affected by the envisaged addition.
Galenic form
The cosmetic composition of the present invention is suitable to be used as a skincare product, a makeup product.
The petrolatum substitute and the cosmetic composition according to the present invention may be prepared in a conventional manner.
According to the third aspect, the present invention provides a cosmetic process for caring for/making up keratin materials comprising applying the cosmetic composition as described above to the keratin materials.
The examples that follow are given as non-limiting illustrations of the present invention.
Examples
Main raw materials used, trade names and supplier thereof are listed in Table 1.
Figure PCTCN2021123008-appb-000006
Invention examples 1-3 and comparative examples 1-3
Petrolatum substitutes of invention examples (IE. ) 1-3 and comparative examples (CE. ) 1-3 were prepared according to the amounts of components given in Table 2. The amount of each component is given in%by weight of the active material relative to the total weight of the petrolatum substitute containing it.
Table 2
Figure PCTCN2021123008-appb-000007
Petrolatum substitutes of invention examples 1-3 are petrolatum substitutes according to the present invention.
Petrolatum substitute of comparative example 1 is a petrolatum substitute comprising Polyamide-8, instead of at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof.
Petrolatum substitute of comparative example 2 is a petrolatum substitute comprising Poly (C10-30 Alkyl Acrylate) , instead of at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof.
Petrolatum substitutes of comparative example 1-2 are petrolatum substitute, wherein the weight ratio of the plant butter: the pasty compound: the plant oil is 4/1/20, out of 0.06-16: 1: 0.06-16.
Preparation process:
The detailed procedure of preparing above examples is as below:
1) . weighing all ingredients in the same vessel;
2) . heating gently until the ingredients fully melt, mixing them until a homogeneous mixture is obtained; and
3) . coolingthe mixture with gentle scrapping.
Evaluation
Evaluation on transepidermal water loss (TEWL) , recovery of consistence index, spreading, greasy texture, and greasy film of the petrolatum substitutes obtained above as well as petrolatum was performed.
Transepidermal water loss (TEWL)
In order to compare the barrier function between the petrolatum substitute with petrolatum through clinical studies on 24 female volunteers aged between 31 and 61 with dry skin, each sample was applied on the forearms of the volunteers at 2mg/cm 2and remained at 21℃ 45±5%RH for one hour. Lower TEWL indicates better barrier function.
Recovery of consistence index
The recovery of consistence index can be used to characterize the thixotropic property of a material. Higher%recovery indicates stronger thixotropic behavior where a material can recovery to its original viscosity after shear.
The viscosity of a sample was measured with an Anton Paar MCR 301 rheometer equipped with a CP-25 plate and cone geometry at 25℃ under a steady state flow test with the shear rate ramping from 20-200 s- 1 to get the initial viscosity. It was followed immediately by a ramp of 200-20 s- 1 to obtain its immediate viscosity recovery. After the initial measurement, samples were collected and measured again under the same experimental conditions after 24 hours to collect 24-hour recovery. Three replicates were measured for each sample. A power law mode σ=k×γ h was fitted to each viscosity versus shear rate flow curve. The value of the consistency coefficient k (Pa·s) in the power law model is an indicator of viscosity. The%recovery of k immediately and after 24 hours was calculated.
Sensory
The sensory profiles of the petrolatum substitute have been evaluated by either trained sensory panellists or volunteers to compare the spreading, greasy texture, and greasy film.
The sensory profile of petrolatum substitutes and petrolatum has been compared by 7 trained panellists with 14 duplicates on a 15-point hedonic scale. Panellists have been trained with standard anchor sets with different sensory scores throughout the 15-point scale, and samples for sensory evaluation were then scored based on their training using anchors as the reference. For example, if a panel were trained with anchors scored  at 1, 5, 10, 15, then a sample feels between 10 and 15 but closerto 10 then maybe it is 12. The average score from 7 panels could be 12.4.
0.5 mL of sample was used for evaluation. Spreading was defined as the size of surface area of the sample being spread during the 10 th motion on hand. Greasy texture was defined as the sensation of fat content on spreading duringthe 10 th motion on arm. Greasy film was defined as the quantity of greasy film remaining on the skin during the 20 th motion waited for two minutes.
The sensory profiles of the petrolatum substitutes, focusing on the spreading, greasy texture, and greasy film, were also compared to petrolatum by 5 volunteers. If at least 4 out of 5 volunteers feel these sensory profiles are similar to petrolatum, then they are considered to be similar.
The evaluation results were summarized in Table 3.
Table 3
Figure PCTCN2021123008-appb-000008
N/A: not measured
It was found that the petrolatum substitute of IE. 1 and petrolatum have no significant difference on TEWL. Meanwhile, the petrolatum substitute of IE. 1 shows significantly better recovery of consistence index, easier spreading and less greasiness, and slightly higher greasy film than petrolatum.
It can be concluded that the petrolatum substitute according to the present invention can be used as a petrolatum substitute.
Invention example 4 and comparative examples 4-5
Cosmetic compositions of invention example (IE. ) 4 and comparative examples (CE. ) 4-5 were prepared according to the amounts of components given in Table 4. The amount of each component is given in%by weight of the active material relative to the total weight of the composition containing it.
Table 4
Figure PCTCN2021123008-appb-000009
Cosmetic composition of invention example 4 is a cosmetic composition according to the present invention.
Cosmetic composition of comparative example 4 is a cosmetic composition contains no pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof.
Cosmetic composition of comparative example 5 is a cosmetic composition comprising petrolatum.
Preparation process:
The detailed procedure of preparing above cosmetic compositions is as below:
1. heating Phase A and Phase B in separate vessels until all materials were fully dissolved;
2. adding Phase A to Phase B upon homogenization, mixing evenly then cooling to room temperature;
3. adjusting the pH with Phase C;
4. adding Phase D and mixing until the system was homogenized;
5. adding Phase E and mixing until the system was homogenized; and
6. adding Phase F and mixing until the system was homogenized.
Evaluation
The sensory profiles of the cosmetic compositions of invention example 4 and comparative example were compared with the cosmetic composition that contains the same weight of petrolatum (CE. 5) . Specific focuses were given to the spreading, greasiness, and greasy film during and after application of the cosmetic compositions.
Samples were evaluated by 5 volunteers and If at least 4 out of 5 volunteers feel these sensory profiles are similar to petrolatum then they are considered to be similar.
The evaluation results were summarized in Table 5.
Table 5
Figure PCTCN2021123008-appb-000010
It was found that the cosmetic composition of invention example 4 has similar spreadability, greasy film, and greasy texture during and after application, as compared with the cosmetic composition containing the same weight of petrolatum.

Claims (15)

  1. A petrolatum substitute, comprising:
    a) at least one solid fatty substance;
    b) at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof; and
    c) at least one oil,
    wherein the weight ratio of the solid fatty substance: the pasty compound: the oil is 0.06-16: 1: 0.06-16.
  2. The petrolatum substitute according to claim 1, wherein the solid fatty substance is selected from butyrospermum parkii (shea) butter, Theobroma Grandiflorum Seed Butter, almond butter, aloe butter, apricot kernel butter, avocado butter, coconut cream butter, cupuacu butter, dhupu butter, hemp butter, Simmondsia Chinensis (Jojoba) Butter, kokum butter, macadamia nut butter, Mangifera Indica (Mango) Seed Butter and combinations thereof.
  3. The petrolatum substitute according to claim 1 or 2, wherein the solid fatty substance is present in an amount ranging from 5 wt. %to 80 wt. %, preferably from 10 wt. %to 50 wt. %, more preferably from 25 wt. %to 35 wt. %, relative to the total weight of the petrolatum substitute.
  4. The petrolatum substitute according to any of claims 1-3, wherein the at least one pasty compound is selected from the compound of formula (I) :
    R 3-OCO-R 1 (-COO-R 2-OCO-R 1n-COO-R 3 (I)
    in which:
    - COR 1CO represents a dimer dilinoleate residue,
    - OR 2O represents a fatty alcohol dimer residue having from 16 to 68, from 24 to 44, in particular from 32 to 40, and more particularly 36 carbon atoms,
    - OR 3 represents a monoalcohol residue having from 4 to 40, in particular from 6 to 36, in particular from 8 to 32, in particular from 16 to 28, and more particularly from 18 to 24 carbon atoms, and
    - n is an integer ranging from 1 to 15, in particular from 2 to 10 and more particularly from 5 to 7.
  5. The petrolatum substitute according to any of claims 1-4, wherein the at least one pasty compound is selected from the group consisting of esters having the following INCI nomenclature: polyglyceryl-2 isostearate dimer dilinoleate copolymer, bis-behenyl/isostearyl/phytosteryl dimer dilinoleyl dimer dilinoleate, and mixtures thereof.
  6. The petrolatum substitute according to any of claims 1-5, wherein the pasty compound is present in an amount ranging from 5 wt. %to 80 wt. %, preferably from 10 wt. %to 50 wt. %, more preferably from 25 wt. %to 35 wt. %, relative to the total weight of the petrolatum substitute.
  7. The petrolatum substitute according to any of claims 1-6, wherein the oil is selected from sweet almond oil, argan oil, avocado oil, groundnut oil, camellina oil, safflower oil, beauty-leaf oil, rapeseed oil, coconut oil (or coconut kernel oil) , coriander oil, marrow oil, wheat germ oil, jojoba oil, linseed oil, macadamia oil, corn germ oil, hazelnut oil, walnut oil, vernonia oil, apricot kernel oil, olive oil, evening-primrose oil, palm oil, passion flower oil, grapeseed oil, rose oil, castor oil, rye oil, sesame oil, rice bran oil, camelina oil, soybean oil, sunflower oil, pracaxi oil, babassu oil, mongongo oil, marula oil, arara oil, shea butter oil, Brazil nut oil, caprylic/capric acid triglycerides, and mixtures thereof; more preferentially from soybean oil, jojoba oil, castor oil and coconut oil (or coconut kernel oil) , caprylic/capric acid triglycerides, and mixtures thereof.
  8. The petrolatum substitute according to any of claims 1-7, wherein the oil is present in an amount 5 wt. %to 80 wt. %, preferably from 10 wt. %to 50 wt. %, more preferably from 25 wt. %to 35 wt. %, relative to the total weight of the petrolatum substitute.
  9. A cosmetic composition comprising:
    a) at least one solid fatty substance;
    b) at least one pasty compound selected from an ester of dimer dilinoleic acid and polyol (s) or an ester thereof; and
    c) at least one oil,
    wherein the weight ratio of the solid fatty substance: the pasty compound: the oil is 0.06-16: 1: 0.06-16;
    wherein the total amount of the solid fatty substance: the pasty compound: the oil is 0.1 wt. %-50 wt. %relative to the total weight of the composition.
  10. The cosmetic composition according to claim 9, wherein the solid fatty substance is selected from butyrospermum parkii (shea) butter, Theobroma Cacao (Cocoa) Seed Butter, almond butter, aloe butter, apricot kernel butter, avocado butter, coconut cream butter, cupuacu butter, dhupu butter, hemp butter, Simmondsia Chinensis (Jojoba) Butter, kokum butter, macadamia nut butter, Mangifera Indica (Mango) Seed Butter and combinations thereof.
  11. The cosmetic composition according to claim 9 or 10, wherein the at least one pasty compound is selected from the compound of formula (I) :
    R 3-OCO-R 1 (-COO-R 2-OCO-R 1n-COO-R 3 (I)
    in which:
    - COR 1CO represents a dimer dilinoleate residue,
    - OR 2O represents a fatty alcohol dimer residue having from 16 to 68, from 24 to 44, in particular from 32 to 40, and more particularly 36 carbon atoms,
    - OR 3 represents a monoalcohol residue having from 4 to 40, in particular from 6 to 36, in particular from 8 to 32, in particular from 16 to 28, and more particularly from 18 to 24 carbon atoms, and
    - n is an integer ranging from 1 to 15, in particular from 2 to 10 and more particularly from 5 to 7.
  12. The cosmetic composition according to any of claims 9-11, wherein the at least one pasty compound is selected from the group consisting of esters having the following INCI nomenclature: polyglyceryl-2 isostearate dimer dilinoleate copolymer, bis-behenyl/isostearyl/phytosteryl dimer dilinoleyl dimer dilinoleate, and mixtures thereof.
  13. The cosmetic composition according to any of claims 9-12, wherein the oil is selected from sweet almond oil, argan oil, avocado oil, groundnut oil, camellina oil, safflower oil, beauty-leaf oil, rapeseed oil, coconut oil (or coconut kernel oil) , coriander oil, marrow oil, wheat germ oil, jojoba oil, linseed oil, macadamia oil, corn germ oil, hazelnut oil, walnut oil, vernonia oil, apricot kernel oil, olive oil, evening-primrose oil, palm oil, passion flower oil, grapeseed oil, rose oil, castor oil, rye oil, sesame oil, rice bran oil, camelina oil, soybean oil, sunflower oil, pracaxi oil, babassu oil, mongongo oil, marula oil, arara oil, shea butter oil, Brazil nut oil, caprylic/capric acid triglycerides, and mixtures thereof; more preferentially from soybean oil, jojoba oil, castor oil and coconut oil (or coconut kernel oil) , caprylic/capric acid triglycerides, and mixtures thereof.
  14. The cosmetic composition according to any of claims 9-13, wherein the weight ratio of the solid fatty substance: the pasty compound: the oil is 1-2: 1: 1-2; more preferably, 1-2: 1: 1-1.5.
  15. A cosmetic process for caring for and/or making up keratin materials comprising applying the cosmetic composition as defined in any of claims 9-14 to the keratin materials.
PCT/CN2021/123008 2021-10-11 2021-10-11 Petrolatum substitute and cosmetic composition comprsing the same WO2023060376A1 (en)

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WO2007066309A2 (en) * 2005-12-08 2007-06-14 L'oreal Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a semi-crystalline polymer
WO2011118497A1 (en) * 2010-03-25 2011-09-29 日清オイリオグループ株式会社 Vaseline-like composition, and cosmetic preparation
WO2013072243A2 (en) * 2011-11-14 2013-05-23 Beiersdorf Ag Vaseline substitute
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WO2018119762A1 (en) * 2016-12-28 2018-07-05 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials
WO2019127211A1 (en) * 2017-12-28 2019-07-04 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials
WO2021081859A1 (en) * 2019-10-31 2021-05-06 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials
WO2021081876A1 (en) * 2019-10-31 2021-05-06 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials

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JP4331584B2 (en) 2003-02-04 2009-09-16 日本精化株式会社 Oily base and cosmetics and skin external preparations containing the same
JP2005179377A (en) 2005-03-10 2005-07-07 Kokyu Alcohol Kogyo Co Ltd Cosmetic
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WO2007066309A2 (en) * 2005-12-08 2007-06-14 L'oreal Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a semi-crystalline polymer
WO2011118497A1 (en) * 2010-03-25 2011-09-29 日清オイリオグループ株式会社 Vaseline-like composition, and cosmetic preparation
WO2013072243A2 (en) * 2011-11-14 2013-05-23 Beiersdorf Ag Vaseline substitute
WO2013120758A1 (en) * 2012-02-17 2013-08-22 Basf Se Mixed esters as vaseline substitute
WO2018119762A1 (en) * 2016-12-28 2018-07-05 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials
WO2019127211A1 (en) * 2017-12-28 2019-07-04 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials
US20200268627A1 (en) * 2017-12-28 2020-08-27 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials
WO2021081859A1 (en) * 2019-10-31 2021-05-06 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials
WO2021081876A1 (en) * 2019-10-31 2021-05-06 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials

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