US20180344599A1 - Use of 1,3 diglyceride in a topical composition for countering the weakening of the skin barrier - Google Patents

Use of 1,3 diglyceride in a topical composition for countering the weakening of the skin barrier Download PDF

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US20180344599A1
US20180344599A1 US15/778,343 US201615778343A US2018344599A1 US 20180344599 A1 US20180344599 A1 US 20180344599A1 US 201615778343 A US201615778343 A US 201615778343A US 2018344599 A1 US2018344599 A1 US 2018344599A1
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skin
diglyceride
weakening
skin barrier
represent
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Daniel Redoules
Gwendal JOSSE
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Pierre Fabre Dermo Cosmetique SA
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Pierre Fabre Dermo Cosmetique SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/005—Preparations for sensitive skin

Definitions

  • This invention relates to a cosmetic or dermatological composition, intended to be administered topically, comprising at least one 1,3 diglyceride defined hereinafter, as well as its use for improving the resistance of the stratum corneum, in particular to environmental factors such as the cold or heat, and as such preserve its properties as a skin barrier.
  • One of the main functions of the skin is to form a physical barrier that, in addition to its protective role with respect to the environment by preventing the penetration of aggressive microbial or chemical elements, must provide the maintaining of the physiological medium of the organism by limiting water loss, thanks to a relative hydrophobicity.
  • a relative hydrophobicity Although there is still controversy concerning the various paths of transcutaneous passage, it is admitted for the most part that the penetration via the intercorneocytory spaces also serves as an element for regulating the permeability of the skin [1].
  • the substantial number of adsorption-desorption sequences associated with the diffusion of molecules through lamellar layers of the corneum determines the effectiveness of the skin barrier.
  • the transepidermal flow of water (also called TransEpidermal Water Loss—TEWL) is about 5 mg/cm 2 [5] but it can reach higher values in case of external aggressions due to various environmental factors such as the cold or heat.
  • TEWL TransEpidermal Water Loss
  • Such an elevation in the skin temperature then causes a fluidification of the lipids of the intercorneocytory spaces, which change to a state of the liquid crystal type giving rise to a substantial increase in transepidermal water loss [4].
  • the altering/weakening of the skin barrier allows for an increased penetration of exogenous substances (polluting agents, irritant agents or allergenic substances (also called allergens)), preferably lipophilic exogenous substances, which can sometimes cause irritations or allergic reactions or oxidative stress.
  • exogenous substances polyluting agents, irritant agents or allergenic substances (also called allergens)
  • lipophilic exogenous substances preferably lipophilic exogenous substances
  • Diglycerides are known in literature and have biological, cosmetics and/or therapeutic activities. It is known in document KR 2013058299 the use of a composition comprising 1,3-diolein or 1,3-dilinoleoyl-rac-glycerol for preventing or treating hyperpigmentation. Likewise, preparations with a fatty acid derivative base among which diglycerides have been able to be claimed for countering the ageing of the skin (WO 03/014073 A1), as an emollient (JP02115117 A) or used in sticks for caring for lips (JP52061240A). Certain diglycerides are used at a low concentration ( ⁇ 1% by weight) as a texturising agent in cosmetic compositions. However, to date, no document describes or suggests that 1,3 diglycerides can have interesting properties in order to overcome the weakening in the skin barrier function, in particular under the effect of environmental factors (cold, heat).
  • This invention as such aims to overcome the disadvantages of prior art by proposing active stabilisers of the intercorneocytory spaces and their use in cosmetic or dermatological compositions so as to counter the weakening of the skin barrier, in particular under the effect of environmental factors.
  • active stabilisers of the intercorneocytory spaces and their use in cosmetic or dermatological compositions so as to counter the weakening of the skin barrier, in particular under the effect of environmental factors.
  • the obtaining of greater stability of the intercorneocytory spaces will as such make it possible to open new perspectives in the fields of cosmetics and dermatology for skincare and/or make-up products for the skin, including facial skin, body skin and scalp.
  • Such active agents can be used in topical cosmetic or dermatological compositions for protecting the skin, including facial skin, body skin and scalp, in particular against some deleterious effects (such as allergy, irritation, etc.) due to the penetration into the skin of exogenous substances, such a cutaneous penetration being increased under the effect of environmental factors, such as heat.
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical
  • a cosmetic or dermatological composition made it possible, after being applied topically, to limit the weakening of the skin barrier that can be due to environmental factors.
  • the inventors have in particular revealed that these 1,3 diglycerides, when they are applied on the skin, stabilise the change in state of the lipids present in the intercorneocytory spaces; this change in state is observed in particular under the effect of the temperature.
  • infrared spectroscopy ATR-FTIR: Attenuated total reflectance-Fourier transform infrared Spectroscopy
  • ATR-FTIR Attenuated total reflectance-Fourier transform infrared Spectroscopy
  • the position of the absorption band, corresponding to the stretching of the CH 2 is located around wave number 2848 cm ⁇ 1 .
  • an increase in the temperature of the surface of the skin causes a displacement of this bands to the higher wave numbers.
  • the stabilising power of the 1,3 diglycerides, on the heated lipid phase increases with the length of the esterified chains (see example 2) and on the other hand, that the 1,3 diglycerides have a stabilising effect of the heated lipid phase that is much greater than that observed with diglycerides 1,2 (see example 3). It is however not excluded in the framework of this invention to use a 1,3 diglyceride that would be in a mixture with small quantities of 1,2 diglycerides often present due to industrial production conditions.
  • An object of this invention thus relates to a topical cosmetic or dermatological composition
  • a topical cosmetic or dermatological composition comprising at least one 1,3 diglyceride having the general formula (I),
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical; and further comprising at least one cosmetic or dermatological excipient for a topical application on the skin.
  • 1,3 diglycerides having the general formula (I) hereinabove can be prepared in particular as described in the article of Liu et al. [9]. They are used in the compositions according to the invention, as an active principle, and more particularly as a stabilising agent of the intercorneocytory spaces.
  • intercorneocytory spaces means the spaces containing a lipid phase which are located between the corneocytes of the cornea layer (also called stratum corneum—SC in abstract) which forms the skin barrier.
  • stabilising agent of the intercorneocytory spaces will be used more particularly to designate an agent that limits the destabilisation of the intercorneocytory spaces, in particular under the action of environmental factors, and which therefore has a barrier effect by opposing the penetration of exogenous substances, such as chemical or microbial agents that can be irritating and/or allergenic; or polluting agents that can generate an oxidative stress, in a skin in particular exposed to environmental factors.
  • exogenous substances such as chemical or microbial agents that can be irritating and/or allergenic; or polluting agents that can generate an oxidative stress, in a skin in particular exposed to environmental factors.
  • an ex vivo assay allows evidencing the fact that the bioavailability of benzo[a]pyrene is highly influenced by the skin temperature: it doubles when the skin temperature passes from 32° C. to 42° C. (increasing from 2.95 to 6.95% of the dose applied to the skin).
  • the term “environmental factors” means, in the terms of this invention, the external conditions such as heat or cold, preferably heat, that induce a variation in the skin temperature that can destabilise the intercorneocytory spaces.
  • heat such as that of a summer period or due to an exposure to the sun, can induce an elevation in the skin temperature, notably above about 35° C., in particular above about 40° C., and cause a fluidification of the lipids of the intercorneocytory spaces in terms of this invention.
  • the impact of the external temperature on the organisation of the intercorneocytory spaces of the stratum corneum can among others be evaluated according to the model of example 1 (analysis via infrared spectroscopy of the variation in the wave number of the ⁇ CH 2 vibration).
  • radicals R 1 and R 2 are identical and represent a C13 to C40 saturated and linear alkyl radical.
  • the radicals R 1 and R 2 represent, independently of one another, a C15 to C23, in particular a C15 to C19, saturated and linear alkyl radical.
  • the radicals R 1 and R 2 can also be identical and represent a C15 to C23, in particular a C15 to C19, saturated and linear alkyl radical.
  • radicals R 1 and R 2 identical or different, preferably identical, represent in particular the hydrocarbon chain of palmitic, stearic or arachidic acid, namely a pentadecyle, heptadecyle or nonadecyle radical.
  • the diglyceride 1,3 according to the invention will be more particularly glyceryl 1,3 dipalmitate, glyceryl 1,3 distearate or a mixture thereof.
  • the 1,3 diglycerides having the formula (I) according to the invention represent preferably from 0.5 to 10%, more particularly from 1 to 5%, and even more particularly from 3 to 5% by weight of the total weight of the composition.
  • the 1,3 diglycerides having the formula (I) according to the invention represent from 5 to 10% by weight of the total weight of the composition.
  • compositions according to this invention can also contain a 1,2 diglyceride.
  • the 1,3 diglycerides used generally contain small residual quantities of 1,2 diglyceride.
  • the quantity of 1,2 diglyceride in the compositions according to the invention will not exceed advantageously 10% by weight, in particular 5% by weight, of the total weight of the 1,3 and 1,2 diglycerides.
  • compositions according to the invention are intended to be applied on the skin.
  • These compositions can be more or less fluid and have the aspect of a cream, a lotion, a milk, a serum, an ointment, a gel or a foam. They can also have the form of a solid, such as a stick or be applied on the skin in the form of an aerosol.
  • These compositions can in particular have the form of an oily solution; of an oil-in-water, water-in-oil emulsion, or multiple emulsions.
  • the 1,3 diglycerides having the formula (I) according to the invention will preferably be introduced into the compositions in dispersed form.
  • the 1,3 diglyceride having the formula (I) according to the invention is in the form of solid particles which are dispersed in a dispersing phase.
  • compositions according to the invention will comprise advantageously at least one 1,3 diglyceride having the formula (I) according to the invention in a dispersed form, i.e. present in the composition in the form of dispersed solid particles.
  • the average diameter of the solid particles of 1,3-diglyceride of formula (I) according to the invention is greater than 100 nm and less than 50 ⁇ m. A measure of the particle size distribution by laser diffraction allows obtaining such a value.
  • the 1,3-diglycerides of formula (I) according to the invention will be dispersed in a fatty phase, for example a silicone and preferably a non-volatile silicone, an ester, a mineral oil or a vegetable oil, or a mixture thereof.
  • a fatty phase for example a silicone and preferably a non-volatile silicone, an ester, a mineral oil or a vegetable oil, or a mixture thereof.
  • the silicones dimethicone (non-volatile) can be mentioned.
  • composition according to the invention provides a protection of the skin barrier, that remains comfortable all throughout the day. It can in particular be applied to sensitive, fragile and/or reactive skin, and in particular to the skin of a baby.
  • This invention also has for object a composition according to the invention described hereinabove for use in the protection of the skin, including facial skin, body skin and scalp.
  • This invention also relates to the use of a composition described hereinabove in order to protect the skin, including facial skin, body skin and scalp.
  • This invention also relates to a method for protecting the skin, including facial skin, body skin and scalp, comprising the administration to a person in need thereof of an effective quantity of a composition described hereinabove.
  • This invention also has for object a composition according to the invention described hereinabove for use in countering the weakening of the skin barrier.
  • This invention also relates to the use of a composition described hereinabove in order to counter the weakening of the skin barrier.
  • This invention also relates to a method for countering the weakening of the skin barrier comprising the administration to a person in need thereof of an effective quantity of a composition described hereinabove.
  • This invention also has for object the compositions described hereinabove for use for preventing or reducing the penetration of exogenous molecules into the skin following a weakening of the skin barrier.
  • This invention also relates to the use of a composition described hereinabove for preventing or reducing the penetration of exogenous molecules into the skin following a weakening of the skin barrier.
  • This invention also relates to a method for preventing or for reducing the penetration of exogenous molecules following a weakening of the skin barrier comprising the administration to a person in need thereof of an effective quantity of a composition described hereinabove.
  • the weakening of the skin barrier can be induced in particular under the effect of environmental factors such as the cold or heat, and more particularly heat, in particular in case of exposure to the sun.
  • the exogenous molecules can be in particular irritant substances (hygiene products, solvents, etc.) or allergenic substances (perfumes, house dust, microbial agents, etc.).
  • the exogenous molecules are lipophilic.
  • This invention also has for object a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical, for use in the protection of the skin, including facial skin, body skin and scalp.
  • This invention also relates to the use of a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical, for the manufacture of a topical cosmetic or dermatological composition intended to protect the skin, including facial skin, body skin and scalp.
  • This invention also relates to the use of a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical, in order to protect the skin, including facial skin, body skin and scalp.
  • This invention also relates to a method for protecting the skin, including facial skin, body skin and scalp, comprising the administration to a person in need thereof of an effective quantity of a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical.
  • This invention also has for object a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical, for use to counter the weakening of the skin barrier.
  • This invention also relates to the use of a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical, for the manufacture of a topical cosmetic or dermatological composition intended to counter the weakening of the skin barrier.
  • This invention also relates to the use of a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical, in order to counter the weakening of the skin barrier.
  • This invention also relates to a method for countering the weakening of the skin barrier comprising the administration to a person in need thereof of an effective quantity of a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical.
  • This invention also has for object a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical, for its topical use in preventing or reducing the penetration of exogenous molecules following a weakening of the skin barrier.
  • This invention also relates to the use of a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical, for the manufacture of a topical cosmetic or dermatological composition intended to prevent or reduce the penetration of exogenous molecules following a weakening of the skin barrier.
  • This invention also relates to the use of a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical, for preventing or reducing the penetration of exogenous molecules following a weakening of the skin barrier.
  • the exogenous molecules are lipophilic.
  • This invention also relates to a method for preventing or for reducing the penetration of exogenous molecules following a weakening of the skin barrier comprising the administration to a person in need thereof of an effective quantity of a 1,3 diglyceride having the general formula (I) hereinbelow:
  • radicals R 1 and R 2 represent, independently of one another, a C13 to C40 saturated and linear alkyl radical.
  • the weakening of the skin barrier can be induced in particular under the effect of environmental factors such as the cold or heat, and more particularly heat, in particular in case of exposure to the sun.
  • the exogenous molecules can be in particular irritant substances (hygiene products, solvents, etc.) or allergenic substances (perfumes, house dust, microbial agents, etc.).
  • radicals R 1 and R 2 are identical and represent a C13 to C40 saturated and linear alkyl radical.
  • the radicals R 1 and R 2 represent, independently of one another, a C15 to C23, in particular a C15 to C19, saturated and linear alkyl radical.
  • the radicals R 1 and R 2 can also be identical and represent a C15 to C23, in particular a C15 to C19, saturated and linear alkyl radical.
  • radicals R 1 and R 2 identical or different, more preferably identical, represent in particular the hydrocarbon chain of palmitic, stearic or arachidic acid, namely a pentadecyle, heptadecyle or nonadecyle radical.
  • the 1,3 diglyceride according to the invention shall be more particularly glyceryl 1,3 dipalmitate, glyceryl 1,3 distearate or a mixture thereof.
  • FIG. 1 shows the wave number of the ⁇ CH 2 vibration of the aliphatic chains of the intercorneocytory lipids in function of temperature.
  • FIG. 2 shows the variation in the wave number of the ⁇ CH 2 vibration of the aliphatic chains of the intercorneocytory lipids, between the situations with or without 1,3 diglyceride, according to the length of the chain of the 1,3 diglyceride.
  • FIGS. 3 and 4 represent the CH 2 symmetric stretching band shift at 28° C. and 43° C. with or without pre-treatment of the skin.
  • FIG. 2 shows the effect of the chain length of the 1,3 diglyceride on the ⁇ CH 2 parameter, with the measurements taken at 40° C.
  • a treated zone (with application in vivo of glyceryl 1,3 distearate) and a control zone (without application of glyceryl 1,3 distearate) were determined.
  • the skin is first heated to between 30 and 45° C.
  • the data obtained is gathered together in tables 2 and 3 and allows several observations to be made.
  • Tables 2 and 3 express the variation of the wave number associated with the ⁇ CH 2 vibration of the aliphatic chains of the intercorneocytory lipids at 40° C. in the presence of glyceryl 1,3-distearate comparatively to the reference measurement without glyceryl 1,3-distearate.
  • Example 5 Examples of Compositions According to the Invention
  • Composition 1 O/W Formula
  • Composition 2 W/O Formula
  • Composition 3 Creamy Gel
  • composition 4 Cream
  • B(a)P The solubility of B(a)P is well documented in the literature. Due to its physicochemical properties, B(a)P has a very poor solubility in water. The software Episuite predict a solubility of 13.3 ⁇ g/L and experimental data confirmed this result at 25° C. [11]. In the present study, the percentage of B(a)P found in the receptor fluid reach 0.13% of the applied dose in the worst case, corresponding to 12.51 ⁇ g/L. Based on these data, we have added 4% of bovine serum albumin (BSA) to increase the solubility of B(a)P and avoid to damage the skin. Surfactants and ethanol were prohibited in order to avoid modification of skin barrier function.
  • BSA bovine serum albumin
  • the skin samples were heated at the rate of 1° C./min, and spectra were collected between 28° C. and 43° C.
  • the classical temperature at the surface of the skin for skin delivery studies is 32° C. This temperature corresponds to the temperature at the surface of the skin in vivo.
  • FTIR measurements were performed to evaluate the molecular organization of the lipid matrix in the stratum corneum.
  • the procedure is based on the study of the position of the CH 2 symmetric stretching band, around 2850 cm ⁇ 1 , depending on the temperature: the skin samples were heated at the rate of 1° C./min and spectra were collected between 28° C. and 43° C. with and without pre-treatment.
  • the position of the CH 2 symmetric stretching band is characteristic of the lipid organization and can be related to the barrier function.
  • B(a)P recovery should be comprised between 85% and 115% of the applied dose, in accordance with OECD 428 and SCCS guidelines.
  • the inter-group comparison was performed by a paired Student's t-test with Graph Pad Prism software. The statistical analysis can be interpreted if n>5.
  • FTIR measurements were performed on human skin explants (8 donors) with or without pre-treatment.
  • the skin samples were heated at the rate of 1° C./min, and spectra were collected between 28° C. and 43° C.
  • FIGS. 3 and 4 show the impact of the temperature on the CH 2 symmetric stretching band. Without pre-treatment, a significant difference on lipid organization can be seen when the skin is heated, with a shift of the CH 2 symmetric stretching band from 2851.2 cm ⁇ 1 at 28° C. to 2852.12 cm ⁇ 1 at 43° C. (T test, p value ⁇ 0.05).
  • T test p value ⁇ 0.05
  • the pre-treatment with 3% or 15% of glyceryl 1,3 distearate permits to decrease significantly (T tests, p value ⁇ 0.05) the impact of the heating on the lipid organization.
  • a shift of the CH 2 symmetric stretching band from 2852.12 cm ⁇ 1 (43° C.
  • the total recovery for all the diffusion cells was in the acceptance criteria, ranging between 94.9% and 97.6% of the applied dose, and permits to validate the study.
  • B(a)P bioavailability skin+receptor fluid
  • B(a)P bioavailability skin+receptor fluid
  • B(a)P bioavailability increases significantly and reaches 6.95% of the applied dose when the skin is heated at 42° C. (T test, p value ⁇ 0.05).
  • the pre-treatment with the vehicle alone does not modify significantly the bioavailability of B(a)P whatever the temperature of the skin (T test, p value ⁇ 0.05).
  • T test p value ⁇ 0.05
  • glyceride 1,3 distearate as diglyceride at 3% or 15%
  • a significant decrease of the bioavailability of B(a)P is observed at 43° C. Indeed, 7.57% of the applied dose is bioavailable with the vehicule (dimethicone) and decreases to 5.35% and 4.35% of the applied dose after pre-treatment with 3% and 15% of glyceride 1,3 distearate, respectively.
  • the percentage of B(a)P found in the stratum corneum decreases after application of glyceride 1,3 distearate.
  • stratum corneum which is a lipophilic compartment, acts as a reservoir. Decreasing the percentage of B(a)P recovered in the stratum corneum thus prevents the diffusion of this compound in the deeper layers of the skin even if the skin is not heated.

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US15/778,343 2015-12-08 2016-12-08 Use of 1,3 diglyceride in a topical composition for countering the weakening of the skin barrier Abandoned US20180344599A1 (en)

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FR1561994A FR3044556B1 (fr) 2015-12-08 2015-12-08 Utilisation de diglyceride 1,3 dans une composition topique pour lutter contre la fragilisation de la barriere cutanee
FR1561994 2015-12-08
PCT/EP2016/080295 WO2017097919A1 (en) 2015-12-08 2016-12-08 Use of 1,3 diglyceride in a topical composition for countering the weakening of the skin barrier

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4551332A (en) * 1981-08-05 1985-11-05 Theodore Stillman Vitamin E compositions and methods
US4957740A (en) * 1984-10-31 1990-09-18 Centerchem, Inc. Composition for preventing or alleviating skin irritation by formulations containing superoxide dismutase
WO2004084646A2 (en) * 2003-03-27 2004-10-07 Enzymotec Ltd. Cosmetic compositions comprising phytosterol esters

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5261240A (en) 1975-11-10 1977-05-20 Shiseido Co Ltd Lipstick composition
JPH0745394B2 (ja) * 1987-01-28 1995-05-17 花王株式会社 保湿用皮膚化粧料
JPH0825867B2 (ja) 1988-10-25 1996-03-13 花王株式会社 入浴剤
DE4430851C1 (de) * 1994-08-31 1995-09-07 Henkel Kgaa Dicarbonsäureesterderivate mit einem Diacyloxypropylrest
GB2318364B (en) * 1996-10-21 2000-09-13 Kao Corp Detergent composition
DE10063343A1 (de) * 2000-12-19 2002-06-20 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an unsymmetrisch substitutierten Triazinderivaten und oberflächenaktiven Zitronensäureestern
FR2828487B1 (fr) 2001-08-09 2005-05-27 Genfit S A Nouveaux composes derives d'acides gras, preparation et utilisations
RU2460511C1 (ru) * 2011-05-23 2012-09-10 Вагинак Львович Ханикян Композиция для получения косметических и лекарственных эмульсий и способ ее получения
KR101425966B1 (ko) 2013-05-23 2014-08-01 태림산업(주) 차량용 조향장치의 샤프트 가공장치 및 이를 이용한 가공방법

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4551332A (en) * 1981-08-05 1985-11-05 Theodore Stillman Vitamin E compositions and methods
US4957740A (en) * 1984-10-31 1990-09-18 Centerchem, Inc. Composition for preventing or alleviating skin irritation by formulations containing superoxide dismutase
WO2004084646A2 (en) * 2003-03-27 2004-10-07 Enzymotec Ltd. Cosmetic compositions comprising phytosterol esters

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
Mintel GNPD Hand Repair, 2015, pgs 1-2 (submitted by Applicant) (Year: 2015) *
MSDS "Glyceryl 1,3-distearate" (http://datasheets.scbt.com/sc-215081.pdf) 7 June 2011, pgs 1-7 (Year: 2011) *
MSDS http //datasheets.scbt.com/sc-215081.pdf *
Sigma (https://www.sigmaaldrich.com/catalog/substance/glyceryldistearate62502132383711?lang=en&region=US) accessed 8 October 2019, pg 1 (Year: 2019) *
Sigma https //www.sigmaaldrich.com/catalog/substance/glyceryldistearate62502132383711?lang=en&region=US *
Singer "High-throughput Screening Assays" (https://www.singerinstruments.com/resource/what-is-high-throughput-screening/) 24 March 2015, pgs 1-9 (Year: 2015) *

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BR112018010119A2 (pt) 2018-11-21
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US20200246236A1 (en) 2020-08-06
US11103432B2 (en) 2021-08-31
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CA3004979A1 (en) 2017-06-15
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WO2017097919A1 (en) 2017-06-15
AR107016A1 (es) 2018-03-14
JP2018536680A (ja) 2018-12-13
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CN108289815A (zh) 2018-07-17
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RU2757223C2 (ru) 2021-10-12
KR20180088461A (ko) 2018-08-03
EP3386471A1 (en) 2018-10-17
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FR3044556B1 (fr) 2019-10-18
FR3044556A1 (fr) 2017-06-09

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