WO2014153706A1 - Transparent composition comprising non polymeric organogelator - Google Patents

Transparent composition comprising non polymeric organogelator Download PDF

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Publication number
WO2014153706A1
WO2014153706A1 PCT/CN2013/073138 CN2013073138W WO2014153706A1 WO 2014153706 A1 WO2014153706 A1 WO 2014153706A1 CN 2013073138 W CN2013073138 W CN 2013073138W WO 2014153706 A1 WO2014153706 A1 WO 2014153706A1
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WO
WIPO (PCT)
Prior art keywords
composition
oil
ester
dextrin
fatty acid
Prior art date
Application number
PCT/CN2013/073138
Other languages
French (fr)
Inventor
Zhen Xu
Manlian HUANG
Original Assignee
L'oreal
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Filing date
Publication date
Application filed by L'oreal filed Critical L'oreal
Priority to PCT/CN2013/073138 priority Critical patent/WO2014153706A1/en
Priority to PCT/CN2014/073858 priority patent/WO2014154113A1/en
Priority to CN201480018449.9A priority patent/CN105050574B/en
Publication of WO2014153706A1 publication Critical patent/WO2014153706A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/001Preparations for care of the lips
    • 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
    • A61K8/04Dispersions; Emulsions
    • A61K8/042Gels
    • 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
    • A61K8/34Alcohols
    • A61K8/342Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • 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

Abstract

A transparent composition comprising: a) at least one non polymeric organogelator of N-acryl glutamic acid diamide having a straight or branched chain alkyl group; b) at least one ester of dextrin and a fatty acid, if needed; and c) at least one non-volatile oil phase, comprising at least one apolar oil, and at least one polar oil.

Description

TRANSPARENT COMPOSITION COMPRISING NON POLYMERIC
ORGANOGELATOR
The present invention relates, in general, to a transparent composition for application onto a targeted substrate. More particularly, the present invention relates to a transparent composition capable of forming a gel structure, and which has a good pay-off, good stability, and shiny effect, particularly with respect to variations in temperature, and does not require the use of amide or ester- terminated polyamide as a structuring agent.
BACKGROUND OF THE INVENTION
Conventional structured compositions typically employ various types of waxes as structuring agents in order to form user-friendly products having good pay-off (a term used to describe both the amount of product applied onto a target substrate, as well as, the way the product distributes onto the substrate), and stability properties, particularly with respect to temperature stability. The problem with wax-based stick compositions is that they possess an undesirable waxy feel and inherently reduce the shine of any shine-imparting ingredients present in the stick composition. And moreover, the products with wax is not transparent.
Attempts have been made to formulate structured gel compositions in the absence of wax. For example, various types of polyamides have been commercialized as gelators/structuring agents in order to form solid compositions. Similarly, various glutamides, as well as various types of polyurethanes have also been commercialized in order to form solid, preferably clear, compositions.
However, prior arts does not provide compositions that have a good balance between stability and usability properties such as pay-off and spreadability, while keeping a comfort feeling during application onto a target substrate.
It is therefore an object of the present invention to provide a transparent composition giving a good pay-off, a silky and comfortable feel, and moisturization effect and is capable of carrying various types of active ingredients and that does not suffer from the aforementioned technical problems.
DISCLOSURE OF INVENTION
The present invention relates to a transparent composition comprising: a) at least one non polymeric organogelator of N-acyl glutamic acid diamide having a straight or branched chain alkyl group; b) at least one ester of dextrin and a fatty acid, if needed; and c) at least one non-volatile oil phase, comprising at least one apolar oil, and at least one polar oil.
As additional advantages, the composition according to the present invention has the effect that it is stable under a wide range of temperatures. It has excellent pay-off effect and spreadability effect onto a target substrate during application.
The present invention also relates to a method of preparation of such a composition comprising the steps of: mixing the optional at least one ester of dextrin and a fatty acid in part of at least one oil phase comprising at least one apolar and at least one polar oil, heating the mixture to 50-125 °C under agitation, until the mixture is homogeneous; mixing at least one non polymeric organogelator of N-acyl glutamic acid diamide having a straight or branched chain alkyl group in part of at least one oil phase comprising at least one at least one polar oil under the temperature of less than 150 °C until the mixture is transparent and homogeneous; mixing the two mixtures until homogenization; adding to the mixture preferably frangrance. Another object of the invention is relating to a method for treating the keratin materials, preferably the skin and/or the lip, comprising the step of applying to the keratin material the composition previously defined.
DETAILED DESCRIPTION OF THE INVENTION
Usually, the transparent compositions, when they are placed 0.01 m in front of a black line 2 mm thick in diameter drawn on a sheet of white paper, allow this line to be seen; in contrast, an opaque composition, i.e. a non-transparent composition, does not allow the line to be seen.
For the purposes of the invention, the term "transparent composition" can be understood as a composition which transmits at least 40% of light at a wavelength of 750 nm without scattering it, i.e. a composition in which the scattering angle of the light is less than 5° and is better still about 0°.
The transparent composition may transmit at least 50%, especially at least 60% and especially at least 70% of light at a wavelength of 750 nm.
The transmission measurement is made with a Cary 300 Scan UV-visible spectrophotometer from the company Varian, according to the following protocol:
- the composition is poured into a square-sided spectrophotometer cuvette with a side length of 10 mm;
- the sample of the composition is then maintained in a thermostatically-regulated chamber at 20°C for 24 hours;
- the light transmitted through the sample of the composition is then measured on the spectrophotometer by scanning wavelengths ranging from 700 nm to 800 nm, the measurement being made in transmission mode;
- the percentage of light transmitted through the sample of the composition at a wavelength of 750 nm is then determined.
Preferably, the "keratin material" according to the present invention is the skin. By "skin", we intend all the body skin, including the scalp. Still preferably, the keratin material is the lip.
The term "solid" composition means the form of the composition at 20°C, and in particular the term "solid" means a composition whose hardness at 20°C and at atmospheric pressure (760 mmHg) is greater than or equal to 30 Nm"1 when it is measured according to the protocol described below.
The hardness of a solid composition is measured according to the following protocol.
The composition whose hardness is to be determined is stored at 20°C for 24 hours before measuring the hardness.
The hardness may be measured at 20°C via the "cheese wire" method, which consists in transversely cutting a wand of product, which is preferably a circular cylinder, by means of a rigid tungsten wire 250 μηη in diameter, by moving the wire relative to the stick at a speed of 100 mm/minute.
The hardness of the samples of compositions of the invention, expressed in Nm"1 , is measured using a DFGS2 tensile testing machine from the company Indelco-Chatillon.
The measurement is repeated three times and then averaged.
The average of the three values read using the tensile testing machine mentioned above, noted Y, is given in grams. This average is converted into newtons and then divided by L which represents the longest distance through which the wire passes. In the case of a cylindrical wand,
L is equal to the diameter (in metres).
The hardness is converted into Nm1 by the equation below:
(Y x 10"3 9.8)/L
For a measurement at a different temperature, the stick is stored for 24 hours at this new temperature before the measurement.
For the purposes of the invention, the term "anhydrous composition" means a composition containing less than 2% and preferably less than 0.5% by weight of water relative to the total weight of the composition.
Where appropriate, such small amounts of water may be provided by ingredients of the composition that contain it in residual amount, but are not deliberately provided.
As indicated above, the transparent composition according to the invention comprises a) at least one non polymeric organogelator of N-acyl glutamic acid diamide having a straight or branched chain alkyl group; b) at least one ester of dextrin and a fatty acid, if needed; c) at least one non- volatile oil phase, comprising at least one apolar oil and at least one polar oil. Preferably, the composition is free of amide or ester-terminated polyamide of formula (I)
X(COR2CNOHR3NH)COR2COX (I) wherein X represents -N(R1)2 group or -ORi group, wherein represents C8-2o linear chain or branched chain alkyl group which may be same or different from each other, R2 represents a dimer acid residue, R3 represents an ethylenediamine residue, n represents an interger from 2 to 4.
According to a particular embodiment, the composition according to the invention is solid.
Preferably,_the composition according to the invention preferably has hardness at 20°C and at atmospheric pressure of greater than or equal to 40 Nm"1 and preferably greater than 50 Nm"1 (measured by the protocol described before).
Preferably, the composition according to the invention especially has a hardness at 20°C of less than 500 Nm"1, especially less than 400 Nm"1 and preferably less than 300 Nm"1 (measured by the protocol described before).
More preferably, the composition according to the invention especially has hardness at 20°C of from 40 Nm"1 to 200 Nm"1.
According to another embodiment, the composition according to the invention is anhydrous. Organogelator
As previously mentioned, the composition according to the invention comprises at least one non polymeric organogelator, being selected from N-acyl glutamic acid diamide (or dialkyl N- acylglutamide) having a straight or branched chain alkyl group. An "organogelator" is defined herein to include a non-polymeric organic compound whose molecules may be capable of establishing, between themselves, at least one physical interaction leading to self-aggregation of the molecules with formation of a three-dimensional macromolecular network that may be responsible for the gelation of the liquid fatty phase.
The term "gelation" means structuring or, more generally, thickening of the medium, which may lead according to the invention to a fluid to pasty or even solid consistency.
.More particularly the non polymeric organogelators used in the composition according to the invention are selected from (C2-C6) dialkyl N-acylglutamides in which the acyl group comprises a linear C8 to C22 alkyl chain, ,, from (C2-C6) dialkyl N-acylglutamides in which the acyl group comprises a branched C8 to C22 alkyl chain, or a micture thereof. Advantageously, the non polymeric organogelator is selcted from lauroylglutamic acid dibutylamide (or dibutyl lauroyl glutamide), N-2-ethylhexanoyl glutamic acid dibutylamide (or dibutyl ethylhexanoyi glutamide) or a mixture thereof.
Lauroylglutamic acid dibutylamide is for instance sold by the company Ajinomoto under the name GP-1 , of INCI name: Dibutyl Lauroyl Glutamide, and N-2-ethylhexanoylglutamic acid dibutylamide is for instance sold by the company Ajinomoto under the name EB-21 , of INCI name: Dibutyl Ethylhexanoyi Glutamide. Moreover, such a type of compounds is described in patent application JP2005-298635.
In one embodiment, the N-acyl glutamic acid diamide with a linear alkyl chain is used in a content ranging from 0.1 % to 10%, preferably 0.5% to 5% and more preferably 1.0% to 3.0% by weight relative to the total weight of the composition.
In another embodiment, N-acyl glutamic acid diamide with a branched alkyl chain is used in an amount ranging from 0.1 % to 10%, preferably 0.5% to 7% and more preferably 1.0% to 3.0% by weight relative to the total weight of the composition.
Dextrin ester According to the invention, the composition further comprises at least one ester of dextrin if needed, preferably an ester of dextrin and a fatty acid, saturated or unsaturated, linear or branched, preferably a C12 to C24 fatty acid.
Preferably, the dextrin ester is an ester of dextrine and a Ci4-Ci8 fatty acid. More preferably, the dextrin ester is Dextrin Myristate, for example such as those
commercialized under the references Rheopearl MKL2® by the company CHIBA FLOUR.
Preferably a composition according to the invention may comprise a content of dextrin ester ranging from 0.1 % to 15% by weight and preferably from 1 % to 5% by weight, if needed, relative to the total weight of the composition. Non-volatile oil phase
The composition according to the invention comprises at least one non-volatile oil phase.
The term "oil" means any fatty substance that is in liquid form at room temperature (20-25°C) and at atmospheric pressure.
The term "non-volatile oil" means oil that remains on the skin or the keratin fibre at room temperature and atmospheric pressure. More specifically, a non-volatile oil has an evaporation rate strictly less than 0.01 mg/cm2/min.
To measure this evaporation rate, 15 g of oil or of oil mixture to be tested are placed in a crystallizing dish 7 cm in diameter, which is placed on a balance in a large chamber of about 0.3 m3 that is temperature-regulated, at a temperature of 25°C, and hygrometry-regulated, at a relative humidity of 50%. The liquid is allowed to evaporate freely, without stirring it, while providing ventilation by means of a fan (Papst-Motoren, reference 8550 N, rotating at 2700 rpm) placed in a vertical position above the crystallizing dish containing said oil or said mixture, the blades being directed towards the crystallizing dish, 20 cm away from the bottom of the crystallizing dish. The mass of oil remaining in the crystallizing dish is measured at regular intervals. The evaporation rates are expressed in mg of oil evaporated per unit of area (cm2) and per unit of time (minutes).
According to a particular embodiment, the non-volatile oil phase comprises oils with high refractive index Cf about 1.48, preferably about 1.48+/-0.01. It has to be noted that the refractive index mentioned above is a final refractive index of the oil phase. There is no limitation on the refractive index of each oil in the oil phase. The oils chosen to be present in the oil phase of the current invention shall reach the condition that the refractive index of the oil phase is about 1.48, preferably about 1.48+/-0.01. Non-volatile Apolar oils
According to the invention, the non-volatile oil phase comprises at least one apolar oil, preferably being a hydrocarbon-based apolar oil.
For the purposes of the present invention, the term "apolar oil" means an oil whose solubility parameter at 25°C, 5a, is equal to 0 (J/cm3)1/2. The definition and calculation of the solubility parameters in the Hansen three-dimensional solubility space are described in the article by CM. Hansen: "The three dimensional solubility parameters", J. Paint Technol. 39, 105 (1967).
According to this Hansen space:
- 5D characterizes the London dispersion forces derived from the formation of dipoles induced during molecular impacts;
- δρ characterizes the Debye interaction forces between permanent dipoles and also the Keesom interaction forces between induced dipoles and permanent dipoles;
- 5h characterizes the specific interaction forces (such as hydrogen bonding, acid/base, donor/acceptor, etc.); and - 5a is determined by the equation: 5a = (δρ2 + 5h2)½.
The parameters δρ, 5h, 5D and 5a are expressed in (J/cm3)½.
The term "hydrocarbon-based oil" means an oil formed essentially from, or even constituted by, carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms, and not containing any silicon or fluorine atoms. Preferably, the non volatile apolar oils are chosen from non volatile apolar hydrocarbon-based oils free of oxygen, nitrogen atoms. In some embodiment, the viscosity of at least one apolar oil is preferably at least 200 cSt under 100°C. More preferably, the viscosity of at least one apolar of the present invention is at least 2000 cSt under 100°C, more preferably at least 5000 cSt under 100°C.
Preferably, the nonvolatile apolar hydrocarbon-based oil may be chosen from linear or branched hydrocarbons of mineral or synthetic origin, such as:
- liquid paraffin or derivatives thereof,
- squalane,
- isoeicosane,
- liquid petroleum jelly,
- naphthalene oil,
- polybutylenes, such as Indopol H-100 (molar mass or MW = 965 g/mol), Indopol H-300 (MW = 1340 g/mol) and Indopol H-1500 (MW = 2160g/mol) sold or manufactured by the company Amoco,
- hydrogenated polyisobutylenes, such as Parleam® sold by the company Nippon Oil Fats, Panalane H-300 E sold or manufactured by the company Amoco (MW = 1340 g/mol), Viseal 20000 sold or manufactured by the company Synteal (MW = 6000 g/mol) and Rewopal PIB 1000 sold or manufactured by the company Witco (MW = 1000 g/mol),
- decene/butene copolymers, polybutene/polyisobutene copolymers, especially Indopol L-
14,
- polydecenes and hydrogenated polydecenes, such as: Puresyn 10 (MW = 723 g/mol) and Puresyn 150 (MW = 9200 g/mol) sold or manufactured by the company Mobil Chemicals,
- and mixtures thereof.
Preferably, the nonvolatile apolar hydrocarbon-based oil is polybutene.
The composition according to the invention comprises from 5% to 80%, preferably from 7% to 50% and more preferably from 10% to 30% by weight of apolar oil relative to the total weight of the composition.
Non volatile polar oils The non-volatile oil phase of the composition according to the invention may also comprise at least one non volatile polar oil.
According to one preferred mode, the composition does not comprise any nonvolatile silicone oil(s). The term "silicone oil" means oil containing at least one silicon atom, and especially containing Si-0 groups.
The term "fluoro oil" means oil containing at least one fluorine atom.
According to a first preferred embodiment, said nonvolatile polar oil is hydrocarbon-based oil.
For the purposes of the present invention, the term "polar oil" means an oil whose solubility parameter at 25°C, 5a, is other than 0 (J/cm3)1/2.
These oils may be of vegetable, mineral or synthetic origin.
The term "hydrocarbon-based oil" means oil formed essentially from, or even constituted by, carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms, and not containing any silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
Nonvolatile hydrocarbon-based oil
In particular, the nonvolatile polar hydrocarbon oil may be chosen from the list of oils below, and mixtures thereof:
- hydrocarbon-based plant oils such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, for instance heptanoic or octanoic acid triglycerides, jojoba oil, sesame oil (820.6 g/mol);
- hydrocarbon-based mono- or di- esters the carboxylic acid residue contains from 2 to 30 carbon atoms, and the alcohol residue represents a hydrocarbon-based chain containing from 1 to 30 carbon atoms, such as isononyl isononanoate, isotridecyl isononanoate, diisostearyl malate, oleyl erucate or 2-octyldodecyl neopentanoate; isopropyl myristate;
- polyesters obtained by condensation of an unsaturated fatty acid dimer and/or trimer and of diol, such as those described in patent application FR 0 853 634, in particular such as dilinoleic acid and 1 ,4-butanediol. Mention may especially be made in this respect of the polymer sold by Biosynthis under the name Viscoplast 14436H (INCI name: Dilinoleic
Acid/Butanediol Copolymer), or copolymers of polyols and of diacid dimers, and esters thereof, such as Hailuscent ISDA,
- fatty alcohols containing from 12 to 26 carbon atoms, saturated or unsaturated, which are branched or linear, for instance octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2- undecylpentadecanol, oleyl alcohol or isostearyl alcohol; Preferably, the said alcohols are branched; mentions maybe made of octyldodecanol such as the product with the trade name Eutanol G® sold by the company BASF;
- saturated or unsaturated C12-C22 fatty acids, such as oleic acid, linoleic acid and linolenic acid, and mixtures thereof;
- dialkyl carbonates, the two alkyl chains possibly being identical or different, such as dicaprylyl carbonate sold under the name Cetiol CC® by Cognis; and
- nonvolatile oils of high molecular mass, for example between 650 and 10 000 g/mol, for instance: i) vinylpyrrolidone copolymers such as the vinylpyrrolidone/1-hexadecene copolymer, Antaron V-216 sold or manufactured by the company ISP (MW = 7300 g/mol), ii) ester oils such as: a) linear fatty acid esters with a total carbon number ranging from 35 to 70, for instance pentaerythrityl tetrapelargonate (MW = 697.05 g/mol), b) hydroxylated esters such as polyglycerol-2 triisostearate
(MW = 965.58 g/mol); c) aromatic esters such as tridecyl trimellitate (MW = 757.19 g/mol), d) esters of C24-C28 branched fatty acids or fatty alcohols such as those described in patent application EP-A-0 955 039, and especially triisoarachidyl citrate
(MW = 1033.76 g/mol), pentaerythrityl tetraisononanoate (MW = 697.05 g/mol), glyceryl triisostearate (MW = 891.51 g/mol), glyceryl tris(2-decyl)tetradecanoate (MW = 1 143.98 g/mol), pentaerythrityl tetraisostearate (MW = 1202.02 g/mol), polyglyceryl-2 tetraisostearate
(MW = 1232.04 g/mol) or else pentaerythrityl tetrakis(2-decyl)tetradecanoate
(MW = 1538.66 g/mol), e) esters and polyesters of a diol dimer and of a monocarboxylic or dicarboxylic acid, such as esters of a diol dimer and of a fatty acid and esters of a diol dimer and of a dicarboxylic acid dimer; mention may be made especially of the esters of dilinoleic diacids and of dilinoleyl diol dimers sold by the company Nippon Fine Chemical under the trade names Lusplan DD-DA5® and DD-DA7®, and diisostearyl malate sold by the company Lubrizol under the trade name Schercemol™ Dism Ester;
- and mixtures thereof.
The esters of a diol dimer and of a monocarboxylic acid may be obtained from a monocarboxylic acid containing from 4 to 34 carbon atoms and especially from 10 to 32 carbon atoms, which acids are linear or branched, and saturated or unsaturated.
As illustrative examples of monocarboxylic acids that are suitable for use in the invention, mention may be made especially of fatty acids.
The esters of diol dimer and of dicarboxylic acid may be obtained from a dicarboxylic acid dimer derived in particular from the dimerization of an unsaturated fatty acid especially of C8 to C34, especially C12 to C22, in particular C16 to C20 and more particularly C18.
According to one particular variant, it is more particularly the dicarboxylic acid dimer from which the diol dimer to be esterified is also derived.
The esters of a diol dimer and of a carboxylic acid may be obtained from a diol dimer produced by catalytic hydrogenation of a dicarboxylic acid dimer as described previously, for example hydrogenated dilinoleic diacid.
Preferably, the composition according to the invention comprises at least one polar nonvolatile oil chosen from hydrocarbon-based polar oils, preferably chosen from ester oils and alcohol oils, and mixtures thereof.
Preferably, the polar nonvolatile oil is octyldodecanol. Preferably, the hydrocarbon-based nonvolatile polar oil is present in a total content of between 1 % and 80%, preferably between 5% and 50%, more preferably between 10% and 30% relative to the total weight of the composition.
The nonvolatile oil may also be a fluoro oil. The term "fluoro oil" means an oil comprising at least one fluorine atom.
The fluoro oils that may be used according to the invention may be chosen from fluorosilicone oils, fluoro polyethers and fluorosilicones as described in document EP-A-847 752, and perfluoro compounds. According to the invention, the term "perfluoro compounds" means compounds in which all the hydrogen atoms have been replaced with fluorine atoms.
According to one particularly preferred embodiment, the fluoro oil according to the invention is chosen from perfluoro oils.
As examples of perfluoro oils that may be used in the invention, mention may be made of perfluorodecalins and perfluoroperhydrophenanthrenes.
According to one particularly preferred embodiment, the fluoro oil is chosen from
perfluoroperhydrophenanthrenes, and especially the Fiflow® products sold by the company Creations Couleurs. In particular, use may be made of the fluoro oil for which the INCI name is Perfluoroperhydrophenanthrene, sold under the reference Fiflow 220 by the company F2 Chemicals.
According to a particular embodiment of the invention, the above composition is anhydrous.
According to another embodiment, the composition of the above invention is solid.
The composition according to the present invention may be manufactured by the known processes that are generally used in cosmetics or dermatology. It may be manufactured by the process which comprises the steps of: mixing the optional at least one ester of dextrin and a fatty acid in part of at least one oil phase comprising at least one apolar and at least one polar oil, heating the mixture to 50-125 °C under agitation, until the mixture is homogeneous; mixing at least one non polymeric organogelator of N-acyl glutamic acid diamide having a straight or branched chain alkyl group in part of at least one oil phase comprising at least one at least one polar oil under the temperature of less than 150 °C until the mixture is transparent and homogeneous; mixing the two mixtures until homogenization; adding to the mixture preferably frangrance.
Another object of the invention is relating to a method for treating the keratin materials, preferably the skin and/or the lip, comprising the step of applying to the keratin material the composition previously defined. Galenic form
The composition of the present invention is suitable to be used as a skin care, make up or cosmetic treatment product. More particularly, the composition of the present invention is in the form of make up product such as lip balm, lip stick, lip gloss, and so on.
Additives In a particular embodiment, a cosmetic composition according to the invention further comprises at least one compound chosen from, hydrophilic solvents, lipophilic solvents, oils, and mixtures thereof.
A cosmetic composition according to the invention may also comprise any additive usually used in the field under consideration, chosen, for example, from gums, anionic, cationic, amphoteric or nonionic surfactants, silicone surfactants, resins, thickening agents, structuring agents such as waxes, dispersants, antioxidants, essential oils, preserving agents, fragrances, neutralizers, antiseptics, UV-screening agents, cosmetic active agents, such as vitamins, moisturizers, emollients or collagen-protecting agents, colorants, 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 additives present in the compositions in accordance with the invention such that the desired cosmetic properties and stability properties thereof are not thereby affected.
According to a preferred embodiment, the current invention comprises less than 1 %, preferably less than 0.1 % of pigments, relative to the total weight of the composition.
The invention is illustrated in greater detail in the examples which follow. The amounts are given as percentage by mass.
EXAMPLES
Formulation examples The following formulation examples are prepared (inv exp stands for invention example, compa exp stands for comparative example):
Figure imgf000015_0001
Octyldodecanol (Eutanol 30 30 30 30 30 30 30 G® from BASF)
Tridecyl trimellitate 20.8 20.8 32.3 20.8 10.8 50.8 40.8 (Liponate® TDTM from
Lipo Chemicals)
Bis-diglyceryl 10 10 10 10 10 10 10 polyacyladipate-2
(Softisan® 649 from
Cremer oleo)
Fragrance 0.2 0.2 0.2 0.2 0.2 0.2 0.2
Protocol of process
The formulation examples are prepared following the steps of: mixing dextrin myristate or dextrin palmitate respectively, at room temperature in part of tridecyl trimelitate and 10% of octyldocdecanol until homogenization under agitation; heating the mixture to 1 15°C under agitation until the mixture is transparent; mixing dibutyl lauroyl glutamide or dibutyl ethylhexanoyl glutamide respectively, in 20% of octyldocecanol at 150°C under the mixture is transparent; mixing the two mixtures together until homogenization; adding to the mixture the fragrance. Evaluation examples
Evaluation on the hardness, usability such as pay-off and spreadability, as well as the comfort feel, instant moisturization while applying the examples to a target substrate is taken place.
Hardness, transparency, spreadability, comfort of use and instant moisturization are evaluated by a group of 6 panelists. Invention examples 1 , 2 and 3, and comparative examples 1 and 2 are applied on the lips of the 6 panelists and scores of comfort are given to each of the examples. Transparency is evaluated by placing 0.01 m of the examples in front of a black line 2 mm thick in diameter drawn on a sheet of white paper, allow this line to be seen; in contrast, an opaque composition, i.e. a non-transparent composition, does not allow the line to be seen.
Pay-off properties are evaluated by 5 experts by the following steps: repeatly apply the product 3 times on the same area of the forearm using the same force; weigh the weight loss of the product; measure the size of the area on the forearm where the product is applied; calculate the weight loss per square centimeter.
Then shine is measured directly with the gloss meter Konica Minolta Multi Gloss 268 plus on the forearm using the setting "60 degree measuring angle".
The more the weight loss per square centimeter is, the better the pay-off of the example is. However, it has to be noted that if the example is too soft or liquid, it has negative impact on pay-off as it is very difficult to apply the example on the lip without too much residue outside of the targeted area. [Lenny: check if it is correct] Finally, comments or scores are given by the experts on the above mentioned properties.
5: very good;
4: basically good;
3: acceptable;
2: slightly poor and not acceptable; 1 : poor, not acceptable.
Figure imgf000017_0001
Transparency 5 5 5 4 2 4 4
Spreadability 5 4 5 4 1 5 5
Comfort of use 5 4 5 4 1 3 3
Instant 5 3 4 5 2 2 2 moisturization
Pay-off 2.23 1.90 2.04 1.76 0.45 1.01 0.96 mg/cm2
Shine 23.2 21.3 20.9 16.5 5.8 7.7 7.9
Based on the above listed evaluation results, the inventors discovered that the composition according to the present invention overcomes the technical issues existing in the prior art, and provides a stable, shiny, good pay-off, spreadability, instant moisturization, and comfort feel composition.

Claims

What is claimed is:
1. A transparent composition comprising:
a) at least one non polymeric organogelator selected from N-acyl glutamic acid diamide having a straight or branched chain alkyl group; and
c) at least one non-volatile oil phase, comprising at least one apolar oil, and at least one polar oil.
2. The composition of claim 1 is free of amide or ester-terminated polyamide of formula (I)
X(COR2CNOHR3NH)COR2COX (I) wherein X represents -N(R1)2 group or -ORi group, wherein
Figure imgf000019_0001
represents C8-2o linear chain or branched chain alkyl group which may be same or different from each other, R2 represents a dimer acid residue, R3 represents an ethylenediamine residue, n represents an interger from 2 to 4.
3. Composition of claim 1 or 2 is anhydrous.
4. Composition of any of the preceding claims 1 to 3 is solid.
5. Composition of any of the preceding claims 1 to 4 has hardness at 20°C and at
atmospheric pressure of greater than or equal to 40 Nm"1 and preferably greater than 50 Nm"1, more preferably from 60 Nm"1 to 150 Nm"1.
6. Composition of claim 1 , wherein the at least one non polymeric organogelator of N-acryl glutamic acid diamide is selected from (C2-C6) dialkyi N-acylglutamides in which the acyl group comprises a linear C8 to C22 alkyl chain, (C2-C6) dialkyi N-acylglutamides in which the acyl group comprises a branched C8 to C22 alkyl chain, or a mixture thereof, and preferably the at least one non polymeric organogelator of N-acryl glutamic acid diamide is selected from lauroylglutamic acid dibutylamide, N-2-ethylhexanoyl glutamic acid dibutylamide, or a mixture thereof.
7. Composition of claim 6, wherein the organogelator is dibutyl lauroyl glutamide.
8. Composition of any of the preceding claims 1 to 7, wherein the non polymeric
organogelator is present in the composition from 0.1 to 15%, preferably from 3 to 5% by weight relative to the total weight of the composition.
9. Composition of any of the preceding claims 1 to 8, wherein the composition further comprises: b) at least one ester of dextrin and a fatty acid.
10. Composition of claim 9, wherein the at least one ester of dextrin and a fatty acid is an ester of dextrin and a fatty acid, saturated or unsaturated, linear or branched, preferably a C12 to C24 fatty acid, more preferably C14-C18 fatty acid, more preferably myristic acid.
1 1. Composition of claim 10, wherein the ester of dextrin and a fatty acid is dextrin myristate.
12. Composition of any of the preceding claims 1 to 1 1 , wherein the ester of dextrin and a fatty acid is present in the composition from 0.1 to 15%, preferably 1 to 5% by weight relative to the total weight of the composition.
13. Composition of claim 1 or 9, wherein the at least one apolar oil is a hydrocarbon-based apolar oil.
14. Composition of claim 1 , 9 or 13, wherein the viscosity of the apolar oil is at least 200 cSt under 100°C , more preferably 2000cSt, even more preferably at least 5000 cSt under 100°C .
15. Composition of any of the preceding claims 1 to 14, wherein the apolar oil is chosen from liquid paraffin or derivatives thereof, squalane, isoeicosane, liquid petroleum jelly, naphthalene oil, polybutylene, hydrogenated polyisobutylene, decene / butene copolymers, polybutene / polyisobutene copolymers, polydecenes and hydrogenated polydecenes, and mixtures thereof, and preferably polybutene.
16. Composition according to anyone of the preceding claims 1 to 15, wherein the amount of apolar oil is from 5 to 80 %, preferably from 7% to 50%, more preferably from 10% to 30% by weight relative to the total weight of the composition.
17. Composition of claim 1 or 9, wherein the at least one polar oil is chosen from preferably fatty alcohols, polyols, and a mixture thereof, preferably the polar oil is chosen from Octyldodecanol, tridecyl trimellitate , bis-diglyceryl polyacyladipate-2, and a mixture thereof.
18. Composition according to anyone of the preceding claims 1 to 17, wherein the amount of the polar oil is from 1 % and 80%, preferably between 5% and 50%, more preferably between 10% and 30% by weight relative to the total weight of the composition.
19. Composition according to anyone of the preceding claims 1 to 18, wherein the at least one non volatile oil phase is present in the composition from 20 to 99.8%, preferably from 30 to 80%, more preferably from 40 to 65% by weight relative to the total weight of the composition.
PCT/CN2013/073138 2013-03-25 2013-03-25 Transparent composition comprising non polymeric organogelator WO2014153706A1 (en)

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CN201480018449.9A CN105050574B (en) 2013-03-25 2014-03-21 Transparent composition comprising non-polymeric organic gel agent

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