FR3113244A1 - Capsules containing ceramide, ceramide compositions, and related cosmetic compositions - Google Patents

Abstract

Capsules containing ceramide, compositions of ceramide, and related cosmetic compositions The ceramide composition includes capsules dispersed in the ceramide composition, the capsules comprising a shell and a core. The shell includes a polycaprolactone, a block copolymer, and a surfactant. The core includes ceramide NP, hydroxypalmitoyl sphinganine, 2-oleamido-1,3-octadecanediol, and a hydrophobic solvent. The core has a weight ratio of ceramide NP of (i) and hydroxypalmitoyl sphinganine of (ii) to 2-oleamido-1,3-octadecanediol of (iii) is 1:2.5 to 1:5 . Additionally, the ceramide composition includes hydroxyacetophenone and a hydrophilic solvent. Figure: none

Description

Capsules containing ceramide, ceramide compositions, and related cosmetic compositions

Domain of disclosure

The present disclosure relates to ceramide-containing capsules, ceramide compositions including such ceramide-containing capsules, and cosmetic compositions produced therefrom. In addition, the present disclosure relates to methods of producing the ceramide compositions and capsules containing ceramide.

Context of the disclosure

The skin acts as a natural barrier between indoor and outdoor environments and therefore plays an important role in vital biological functions such as protection against mechanical and chemical injury, microorganisms, and ultraviolet damage. Human skin is mainly made up of two main layers, the dermis and the epidermis, which superficially covers the dermis. The dermis provides the epidermis with a solid support. The dermis is composed primarily of fibroblasts and an extracellular matrix of collagen, elastin, and a substance known as ground substance. These components are synthesized by fibroblasts.

The epidermis, which covers the dermis and is in direct contact with the external environment, has the main role of protecting the body against dehydration and external attacks. The natural human epidermis is mainly composed of three types of cells, namely keratinocytes, which constitute the vast majority, melanocytes and Langerhans cells. Each of these cell types contributes to protecting the body against external attacking factors (weather, ultraviolet rays, tobacco, etc.). The epidermis is a stratified and keratinized pavement of epithelium which is approximately 90% keratinocytes. The gradual differentiation of cells from the basal membrane, which separates the dermis from the epidermis, towards the surface of the epidermis includes the differentiation of keratinocytes, which migrate towards the surface of the skin, where they desquamate.

The aging of the epidermis leads to a reduction in thickness. Atrophy of the epidermis is the consequence of the slowing down of keratinocyte proliferation and the accumulation of senescent keratinocytes. The outer layer becomes dull. The cells that make up the epidermis are delimited by a lipid domain. During differentiation, phospholipids, whose role is to produce the fluid structure of the cell membranes of the living layers of the epidermis, are gradually replaced by a mixture mainly composed of fatty acids, cholesterol and ceramides (sphingolipids) .

These lipids are organized into specific lamellar structures, the integrity of which depends on the quality of the fractions present, but also on their respective proportions. This lamellar structure of lipids in the lipid domain of the epidermis is responsible for the fluidity and therefore the suppleness of the skin. Lipids are also responsible for the "barrier" properties of the epidermis, in particular the stratum corneum.

Epidermal lipids are mainly synthesized in the living epidermis. They consist mainly of phospholipids, sphingolipids, cholesterol, free fatty acids, triglycerides, cholesterol esters and alkanes. Phospholipids are essential for the constitution of cell membranes. They play an important role in mediating extracellular signals and forming free aliphatic chains used for energy production. They constitute a reservoir of free fatty acids necessary for the constitution of sphingolipids. Cholesterol plays a fundamental role in skin hydration and in the "barrier" function of the epidermis. Free fatty acids play a major role in maintaining the lamellar structure of lipids in the stratum corneum, and also in the constitution of cell membranes, where they are responsible for the fluidity of the membrane, but also for physiological processes such as functioning of receptors or enzymatic activity.

Ceramides are lipids that play an essential role in the metabolism of the epidermis, and are necessary to preserve the multi-lamellar structure of intercorneocyte lipids. They are also essential to the "barrier" function of the epidermis and to water exchange, in particular to overcome age-related hydration problems.

Accordingly, there is a need for improved compositions and products which deliver ceramides to the skin.

Disclosure Summary

The present disclosure relates to ceramide-containing capsules, ceramide compositions including such ceramide-containing capsules, and cosmetic compositions produced from any of the foregoing. It is well recognized that it is difficult to incorporate ceramides into cosmetic compositions, and in particular cosmetic compositions having large amounts of water. The ceramide-containing capsules and ceramide compositions disclosed herein advantageously allow ceramides to be easily incorporated into various types of cosmetic compositions, including water-based cosmetic compositions via the addition of the ceramide compositions and/or capsules containing ceramide.

The ceramide compositions preferably improve the appearance and/or functionality of the skin. For example, cosmetic compositions comprising the ceramide compositions can impart improved skin barrier functionality to a user's skin. In some cases, the ceramide compositions promote regeneration, renewal, repair and/or improved moisture retention of compromised skin, for example, when the ceramide compositions are incorporated into a cosmetic composition and applied to the compromised skin. In additional instances, ceramide compositions and cosmetic compositions produced therefrom provide improved skin appearance, such as anti-inflammation, improved skin pigmentation, and the like.

The inventors have discovered a unique blend of ceramides in specific weight ratios that provide enhanced stability, and can surprisingly be used with hydroxyacetophenone as a preservative instead of, for example, phenoxyethanol and/or phenylethyl alcohol. For example, ceramide compositions and/or cosmetic compositions can be free or substantially free of phenoxyethanol. In some cases, the ceramide and/or cosmetic composition includes 3 wt% or less, 2 wt% or less, or 1 wt% or less of phenoxyethanol, based on the total weight of the respective composition. In another instance, the ceramide and/or cosmetic compositions include about 0% by weight phenoxyethanol, based on the respective weight of the composition. The ceramide and/or cosmetic composition may also be free or substantially free of phenylethyl alcohol. The ceramide and/or cosmetic compositions may include 3% by weight or less, 2% by weight or less, or 1% by weight or less of phenylethyl alcohol, based on the respective weight of the composition. In at least one instance, the ceramide and/or cosmetic compositions include about 0% by weight of phenylethyl alcohol, based on the respective weight of the composition. Additionally or alternatively, the ceramide and/or cosmetic compositions may be free or substantially free of all preservatives other than hydroxyacetophenone. In some cases, the ceramide and/or cosmetic composition includes 3% by weight or less, 2% by weight or less, 1% by weight or less, or about 0% by weight of preservatives other than hydroxyacetophenone, based on respective weight of the composition.

In accordance with one aspect of the disclosure, there is provided a ceramide composition comprising capsules containing ceramide. The ceramide composition of the present disclosure typically includes:

(I) capsules dispersed in the ceramide composition, the capsules comprising:

(a) a shell comprising:

(i) a polycaprolactone,

(ii) a block copolymer, and

(iii) a surfactant, and

(b) a core comprising:

(i) ceramide NP,

(ii) hydroxypalmitoyl sphinganine,

(iii) 2-oleamido-1,3-octadecanediol,

wherein a weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is from 1:2.5 to 1:5, And

(iv) a hydrophobic solvent;

(II) hydroxyacetophenone; And

(III) a hydrophilic solvent.

Ceramide composition capsules can have an average diameter of about 200 to about 400 nm. The capsules can include a shell comprising a surfactant that includes a phospholipid group.

The capsule core typically includes ceramide NP, hydroxypalmitoyl sphinganine, 2-oleamido-1,3-octadecanediol, and a hydrophobic solvent. In some instances, the capsule core comprises (i) about 2 to about 8% by weight ceramide NP, (ii) about 2 to about 8% by weight hydroxypalmitoyl sphinganine, (iii) about 10 to about 40% by weight of 2-oleamido-1,3-octadecanediol, and (iv) about 44 to about 86% by weight of a hydrophobic solvent, wherein the above weight percentages of (i) to (iv) are based on the total weight of the kernel of (b). Additionally or alternatively, the weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) can vary from 1:2.5 to 1:4, 1:2.6 to 1:4, 1:2.7 to 1:4, or 1:2.8 to 1:4. The core of the capsules may also comprise a ceramide or a derivative thereof chosen from at least one ceramide and/or a derivative thereof chosen from ceramide-EOS, ceramide-NS, ceramide-EOH, ceramide-AS, ceramide-NH, ceramide-AP, ceramide-AH, ceramide-OS, ceramide-OH, and a mixture thereof.

The hydrophobic solvent preferably comprises a fatty alcohol. For example, the fatty alcohol can be chosen from cetearyl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, arachidyl alcohol, eicosyl alcohol, myristyl alcohol, 2-dodecylhexadecanol , 2-tetradecyl-1-octadecanol, 2-tetradecyl-1-eicosanol, 2-hexadecyl-1-octadecanol, 2-hexadecyl-1-eicosanol, octyldodecanol, 2-octyl-1-dodecanol, and one of their mixtures. In some cases, the fatty alcohol is 2-octyl-1-dodecanol.

The ceramide composition can comprise a hydrophilic solvent comprising water. In some instances, the ceramide composition may be phenoxyethanol free. The ceramide composition may additionally or alternatively be free of phenylethyl alcohol. In some instances, the ceramide composition may further comprise at least one of (IV) an emulsifier; (V) a polyol; (VI) a fatty compound; and (VII) a monoalcohol.

In accordance with another aspect of the disclosure, there is provided a cosmetic composition containing the ceramide composition. The cosmetic composition typically includes:

(A) about 1% to about 20% by weight of a ceramide composition, the ceramide composition comprising:

(I) capsules dispersed in the ceramide composition, the capsules comprising:

(a) a shell comprising:

(i) a polycaprolactone,

(ii) a block copolymer, and

(iii) a surfactant, and

(b) a core comprising:

(i) ceramide NP,

(ii) hydroxypalmitoyl sphinganine,

(iii) 2-oleamido-1,3-octadecanediol,

wherein a weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is from 1:2.5 to 1:5, And

(iv) a hydrophobic solvent;

(II) hydroxyacetophenone; And

(III) a hydrophilic solvent.

(B) optionally, an emulsifier;

(C) optionally, a polyol;

(D) optionally, a fatty compound; And

(E) optionally, a monoalcohol.

The cosmetic compositions preferably improve the barrier function of the skin.

In accordance with a further aspect of the disclosure, there is provided a process for producing the ceramide composition. Typically, processes for producing ceramide compositions include:

(I) the provision of a mixture at room temperature comprising:

(a) an oily phase comprising:

(i) ceramide NP,

(ii) hydroxypalmitoyl sphinganine,

(iii) 2-oleamido-1,3-octadecanediol, and

wherein a weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is from 1:2.5 to 1:5, And

(iv) a hydrophobic solvent,

(b) a liposome precursor which is immiscible with water and with the oil phase, wherein the liposome precursor comprises:

(i) a polycaprolactone, and

(ii) a surfactant,

(c) acetone, wherein a weight ratio of the oil phase of (a) and the liposome precursor of (b) to the acetone of (c) is from 1:20 to about 1:40,

(II) homogenization of the oily phase and the liposome precursor at a temperature of 30°C or more;

(III) the dispersion of the homogeneous mixture of (II) in a preheated aqueous phase, in order to obtain an emulsion, the preheated aqueous phase comprising a block copolymer;

(IV) distilling the solvent of (III) to remove the acetone and the concentrate resulting from the mixture for the coacervation of the liposome precursor and for the coating of drops of said oily phase with the coacervates to obtain a suspension;

(V) cooling the suspension of step (IV) to a temperature for the formation of capsules by precipitation and/or crystallization of the coacervates; And

(VI) addition of hydroxyacetophenone.

In some cases, polycaprolactone has a weight average molecular weight of about 400 to about 10,000. Polycaprolactone can include up to 100 monomer units. Additionally or alternatively, the weight ratio of ceramide NP of (i) and hydroxypalmitoyl sphinganine of (ii) to 2-oleamido-1,3-octadecanediol of (iii) is 1:2.5 to 1:4.

Detailed description of the disclosure

The present disclosure relates to ceramide-containing capsules, ceramide compositions including such ceramide-containing capsules, and cosmetic compositions produced therefrom. Additionally, the present disclosure relates to methods of producing the ceramide compositions and capsules containing ceramide.

Ceramide compositions

Ceramide-containing capsules and ceramide compositions advantageously make it possible to easily incorporate ceramides into various types of cosmetic compositions, including aqueous-based cosmetic compositions.

Ceramide compositions typically include:

(I) capsules dispersed in the ceramide composition, the capsules comprising:

(a) a shell comprising:

(i) a polycaprolactone,

(ii) a block copolymer, and

(iii) a surfactant, and

(b) a core comprising:

(i) ceramide NP,

(ii) hydroxypalmitoyl sphinganine,

(iii) 2-oleamido-1,3-octadecanediol,

wherein a weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is from 1:2.5 to 1:5 ( [(i)+(ii)] :(iii)), and

(iv) a hydrophobic solvent;

(II) hydroxyacetophenone; And

(III) a hydrophilic solvent.

(I) Caps

The ceramide compositions include ceramide-containing capsules dispersed in the ceramide composition. Although ceramide compositions can be prepared to have capsules of various sizes, capsules typically have an average diameter of about 100 µm or less. For example, the capsules can have an average diameter of about 90 µm or less, about 80 µm or less, about 70 µm or less, about 60 µm or less, about 50 µm or less, about 40 µm or less, about 30 µm or less, about 20 µm or less, about 10 µm or less, or about 1 µm or less. The capsules can be prepared to have an average diameter of less than 1 µm or less, for example, to reduce the tactile sensation of the individual capsules for a user. In some instances, the capsules may have an average diameter of about 50 nm to about 900 nm, about 50 nm to about 800 nm, about 50 nm to about 700 nm, about 50 nm to about 600 nm, about 50 nm to about 500 nm, about 50 nm to about 400 nm, about 50 nm to about 300 nm, about 50 nm to about 200 nm; about 100 nm to about 900 nm, about 100 nm to about 800 nm, about 100 nm to about 700 nm, about 100 nm to about 600 nm, about 100 nm to about 500 nm, about 100 nm to about 400 nm, about 100 nm to about 300 nm, about 100 nm to about 200 nm; about 200 nm to about 900 nm, about 200 nm to about 800 nm, about 200 nm to about 700 nm, about 200 nm to about 600 nm, about 200 nm to about 500 nm, about 200 nm to about 400 nm, or about 200 nm to approximately 300 nm, including ranges and subranges. Capsules can be prepared to have sizes that fall within ranges derived from any of the limits described herein.

Further disclosure relating to ceramide-containing capsules, ceramide compositions and methods of producing capsules can be found in US Patent Publication No. 20030084914; U.S. Patent Publication No. 20070065379; U.S. Patent No. 3,691,090; U.S. Patent No. 4,460,563; U.S. Patent No. 4,752,496; U.S. Patent No. 5,051,304; Japanese Patent Publication No. 5285210; Japanese Patent Publication No. 8325117; and French Patent Publication No. 2795928, which are incorporated herein in their entirety for all intents and purposes.

(a) Carapace

The capsules consist of a shell and a core. The capsule shell typically encapsulates the core, for example, so that the core is contained within the shell. In some cases, the shell of the capsules completely encapsulates the liquid core at its periphery. The shell generally comprises a polycaprolactone, a block copolymer, and a surfactant.

(i) polycaprolactone

The capsule shell includes a polycaprolactone. The amount of polycaprolactone in the shell can vary, but is typically present in an amount of from about 1 to about 70% by weight based on the total weight of the shell. For example, the amount of polycaprolactone in the shell can be about 10 to about 70% by weight, about 20 to about 70% by weight, about 30 to about 70% by weight, about 40 to about 70% by weight, about 50 to about 70% by weight; about 10 to about 60 wt%, about 20 to about 60 wt%, about 30 to about 60 wt%, about 40 to about 60 wt%; about 10 to about 50 wt%, about 20 to about 50 wt%, about 30 to about 50 wt%, about 40 to about 50 wt%; about 10 to about 40 wt%, about 20 to about 40 wt%, about 30 to about 40 wt%, including all ranges and subranges, based on the total weight of shell components.

The polycaprolactone can be selected from polycaprolactone having a weight average molecular weight of 100 to 900,000. In some cases, the polycaprolactone has a weight average molecular weight of 100 to 900,000; 200 to 900,000; 400 to 900,000; 700 to 900,000; 1,000 to 900,000; 10,000 to 900,000; 50,000 to 900,000; 75,000 to 900,000; 100,000 to 900,000; 200,000 to 900,000; 400,000 to 900,000; 600,000 to 900,000; 700,000 to 900,000; from 100 to 800,000; 200 to 800,000; 400 to 800,000; 700 to 800,000; 1,000 to 800,000; 10,000 to 800,000; 50,000 to 800,000; 75,000 to 800,000; 100,000 to 800,000; 200,000 to 800,000; 400,000 to 800,000; 600,000 to 800,000; from 100 to 700,000; 200 to 700,000; 400 to 700,000; 700 to 700,000; 1,000 to 700,000; 10,000 to 700,000; 50,000 to 700,000; 75,000 to 700,000; 100,000 to 700,000; 200,000 to 700,000; 400,000 to 700,000; from 100 to 600,000; 200 to 600,000; 400 to 600,000; 700 to 600,000; 1,000 to 600,000; 10,000 to 600,000; 50,000 to 600,000; 75,000 to 600,000; 100,000 to 600,000; 200,000 to 600,000; 400,000 to 600,000; from 100 to 500,000; 200 to 500,000; 400 to 500,000; 700 to 500,000; 1,000 to 500,000; 10,000 to 500,000; 50,000 to 500,000; 75,000 to 500,000; 100,000 to 500,000; or 200,000 to 500,000 including all ranges and subranges. In other cases, polycaprolactone has a weight average molecular weight of 100 to 20,000; 200 to 20,000; 400 to 20,000; 700 to 20,000; 1,000 to 20,000; from 100 to 15,000; 200 to 15,000; 400 to 15,000; 700 to 15,000; 1,000 to 15,000; from 100 to 10,000; 200 to 10,000; 400 to 10,000; 700 to 10,000; 1,000 to 10,000; from 100 to 5,000; 200 to 5,000; 400 to 5,000; 700 to 5,000; 1000 to 5000, including all ranges and subranges included. Additionally and/or alternatively, the polycaprolactone comprises up to 100 monomer units. For example, the polycaprolactone can comprise up to 80 monomer units, up to 70 monomer units, up to 60 monomer units, up to 50 monomer units, or up to 40 monomer units.

The capsule shell can include a polycaprolactone that is substituted or unsubstituted. In some cases, the polycaprolactone is chosen from polycaprolactone diols. For example, polycaprolactone may be commercially available under the trade name, CAPA ^™ , which is manufactured by Perstorp.

( ii) a block copolymer

The amount of block copolymer in the shell can vary, but is typically about 1 to about 70% by weight based on the total weight of the shell. For example, the amount of the block copolymer in the shell can be about 10 to about 70% by weight, about 20 to about 70% by weight, about 30 to about 70% by weight, about 40 to about 70% by weight , about 50 to about 70% by weight; about 10 to about 60 wt%, about 20 to about 60 wt%, about 30 to about 60 wt%, about 40 to about 60 wt%; about 10 to about 50 wt%, about 20 to about 50 wt%, about 30 to about 50 wt%, about 40 to about 50 wt%; about 10 to about 40 wt%, about 20 to about 40 wt%, about 30 to about 40 wt%, including all ranges and subranges, based on total shell weight.

The block copolymer can be selected from a block copolymer having a weight average molecular weight of 1,000 to 900,000. In some cases, the block copolymer has a weight average molecular weight of 1,000 to 900,000; 10,000 to 900,000; 50,000 to 900,000; 75,000 to 900,000; 100,000 to 900,000; 200,000 to 900,000; 400,000 to 900,000; 600,000 to 900,000; 700,000 to 900,000; from 1,000 to 800,000; 10,000 to 800,000; 50,000 to 800,000; 75,000 to 800,000; 100,000 to 800,000; 200,000 to 800,000; 400,000 to 800,000; 600,000 to 800,000; from 1,000 to 700,000; 10,000 to 700,000; 50,000 to 700,000; 75,000 to 700,000; 100,000 to 700,000; 200,000 to 700,000; 400,000 to 700,000; from 1,000 to 600,000; 10,000 to 600,000; 50,000 to 600,000; 75,000 to 600,000; 100,000 to 600,000; 200,000 to 600,000; 400,000 to 600,000; from 1,000 to 500,000; 10,000 to 500,000; 50,000 to 500,000; 75,000 to 500,000; 100,000 to 500,000; or 200,000 to 500,000 including all ranges and subranges.

Preferably, the block copolymer is a poloxamer. In some cases, poloxamer has a structure in accordance with the following formula:

where a is an integer from 10 to 110 and b is an integer from 20 to 60. In some cases, a may be 12 and/or b may be 20. When a is 12 and b is 20, this is known as poloxamer 124. In other cases, a may be 80 and/or b may be 27. When a is 80 and b is 27, it is known as poloxamer 188. Additional poloxamers which may be useful include, for example, poloxamer 108, poloxamer 182, poloxamer 183, poloxamer 212, poloxamer 217, poloxamer 238, poloxamer 288, poloxamer 331, poloxamer 338, poloxamer 335, and poloxamer 407.

( iii ) a surfactant

The shell includes surfactant in an amount which may vary, but is typically present in an amount of from about 10 to about 70% by weight, based on the total weight of the shell. For example, the amount of surfactant in the shell can be about 10 to about 70% by weight, about 20 to about 70% by weight, about 30 to about 70% by weight, about 40 to about 70% by weight, about 50 to about 70% by weight; about 10 to about 60 wt%, about 20 to about 60 wt%, about 30 to about 60 wt%, about 40 to about 60 wt%; about 10 to about 50 wt%, about 20 to about 50 wt%, about 30 to about 50 wt%, about 40 to about 50 wt%; about 10 to about 40 wt%, about 20 to about 40 wt%, about 30 to about 40 wt%, including all ranges and subranges included, based on the total weight of the shell components.

The surfactant is preferably chosen from phospholipid surfactants. For example, the surfactant can comprise or be chosen from lecithin. In some cases, the surfactant may include a proportion of lecithin or fractions of lecithin, lysolecithin (such as hydrolyzed lecithin, enzymatically treated lecithin). Lecithin can be obtained from natural sources of any vegetable or animal source, such as, for example, eggs, soya, sunflowers, rapeseed, etc. Non-limiting examples of commercial lecithin products include, for example, soy lecithins, such as Lecico F 600, Lecico F 580, Lecico F300, Lecico F 200, Lecico F 100, Lecico P900, Lecico P 700, Lecico P 300 ; sunflower lecithins, such as Lecico SUN 400, Lecico SUN FM 580; rapeseed lecithin, such as Lecico RAP 200. Further disclosure relating to lecithin, surfactants, and capsules can be found in U.S. Patent Publication No. 20180110254, which is incorporated herein by reference in its entirety for all purposes. useful. Additionally or alternatively, the surfactant may be selected from coating surfactants, such as those taught by U.S. Patent Publication No. 2015/0313809, which is incorporated herein, in its entirety, for all intents and purposes.

( iv) water soluble polymers

The shell can optionally include a water-soluble polymer. The water-soluble polymer can be chosen from poly(vinyl alcohol), polyvinyl-pyrrolidone, carboxymethylcellulose, poly(carboxylic acids) and their crosslinked derivatives. Additionally or alternatively, the water-soluble polymer can be chosen from natural gums, such as xanthans, starch, sodium alginate, pectins, chitosan, guar, carob, carrageenan or hyaluronic acid.

The water-soluble polymer may be included in the shell, if desired, in an amount ranging from 0.001 to 10% by weight, based on the total weight of the components comprising the shell. For example, the water-soluble polymer can be in an amount ranging from 0.001 to 10 wt%, 0.01 to 10 wt%, 0.1 to 10 wt%, 1 to 10 wt%, 2 10 wt%, 3 to 10 wt%, 4 to 10 wt%, 5 to 10 wt%; 0.01 to 8% by weight, 0.01 to 8% by weight, 0.1 to 8% by weight, 1 to 8% by weight, 2 to 8% by weight, 3 to 8% by weight, 4 to 8% by weight, 5 to 8% by weight; 0.001 to 6 wt%, 0.01 to 6 wt%, 0.1 to 6 wt%, 1 to 6 wt%, 2 to 6 wt%, 3 to 6 wt%; 0.001-4% by weight, 0.01-4% by weight, 0.1-4% by weight, 1-4% by weight, 2-4% by weight, including all ranges and sub-ranges included, relative to the total weight of the shell components.

(a ) Core

The capsule core includes a mixture of ceramides, typically including (i) ceramide NP, (ii) hydroxypalmitoyl sphinganine, (iii) 2-oleamido-1,3-octadecanediol, and (iv) a hydrophobic solvent ( octyldodecanol). A further description of the mixture of ceramides and hydrophobic solvent is provided below.

(i) to (iii) Blend of ceramides

The capsule core includes ceramide NP, hydroxypalmitoyl sphinganine, and 2-oleamido-1,3-octadecanediol, in a weight ratio of ceramide NP of (i) and hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) from 1:2.5 to 1:5. Preferably, the weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is from 1:2.5 to 1:4 , 1:2.6 to 1:4, 1:2.7 to 1:4, 1:2.8 to 1:4, 1:2.9 to 1:4, 1:3 to 1:4, 1 :3.1 to 1:4, 1:3.2 to 1:4, 1:3.3 to 1:4, 1:3.4 to 1:4. In some cases, the weight ratio of ceramide NP from (i) and hydroxypalmitoyl sphinganine from (ii) to 2-oleamido-1,3-octadecanediol from (iii) is 1:2.5 to 1: 4, 1:2.5 to 1:3.9, 1:2.5 to 1:3.8, 1:2.5 to 1:3.7, 1:2.5 to 1:3.6, 1:2.5 to 1:3.5, 1:2.5 to 1:3.4, 1:2.5 to 1:3.3, or 1:2.5 to 1:3.2.

The amount of ceramide NP in the core can vary, but is typically present in an amount of about 1 to about 15 wt%, about 2 to about 15 wt%, about 3 to about 15 wt%, about 4 to about 15 wt%, about 5 to about 15 wt%, about 6 to about 15 wt%, about 7 to about 15 wt%; about 1 to about 13 wt%, about 2 to about 13 wt%, about 3 to about 13 wt%, about 4 to about 13 wt%, about 5 to about 13 wt%, about 6 to about 13 wt%, about 7 to about 13 wt%; about 1 to about 11% by weight, about 2 to about 11% by weight, about 3 to about 11% by weight, about 4 to about 11% by weight, about 5 to about 11% by weight, about 6 to about 11 wt%, about 7 to about 11 wt%; about 1 to about 9 wt%, about 2 to about 9 wt%, about 3 to about 9 wt%, about 4 to about 9 wt%, about 5 to about 9 wt%, about 6 to about 9 wt%, about 7 to about 9 wt%; about 1 to about 8 wt%, about 2 to about 8 wt%, about 3 to about 8 wt%, about 4 to about 8 wt%, about 5 to about 8 wt%, about 6 to about 8 % in weight ; about 1 to about 6 wt%, about 2 to about 6 wt%, about 3 to about 6 wt%, about 4 to about 6 wt%, inclusive of all ranges and subranges included, based on weight total kernel components.

The amount of hydroxypalmitoyl sphinganine in the core can vary, but is typically present in an amount of about 1 to about 15 wt%, about 2 to about 15 wt%, about 3 to about 15 wt%, about 4 about 15 wt%, about 5 to about 15 wt%, about 6 to about 15 wt%, about 7 to about 15 wt%; about 1 to about 13 wt%, about 2 to about 13 wt%, about 3 to about 13 wt%, about 4 to about 13 wt%, about 5 to about 13 wt%, about 6 to about 13 wt%, about 7 to about 13 wt%; about 1 to about 11% by weight, about 2 to about 11% by weight, about 3 to about 11% by weight, about 4 to about 11% by weight, about 5 to about 11% by weight, about 6 to about 11 wt%, about 7 to about 11 wt%; about 1 to about 9 wt%, about 2 to about 9 wt%, about 3 to about 9 wt%, about 4 to about 9 wt%, about 5 to about 9 wt%, about 6 to about 9 wt%, about 7 to about 9 wt%; about 1 to about 8 wt%, about 2 to about 8 wt%, about 3 to about 8 wt%, about 4 to about 8 wt%, about 5 to about 8 wt%, about 6 to about 8 % in weight ; about 1 to about 6 wt%, about 2 to about 6 wt%, about 3 to about 6 wt%, about 4 to about 6 wt%, inclusive of all ranges and subranges included, based on weight total kernel components.

The amount of 2-oleamido-1,3-octadecanediol in the core can vary, but is typically present in an amount of about 1 to about 60 wt%, about 5 to about 60 wt%, about 10 to about 60 wt%, about 15 to about 60 wt%, about 20 to about 60 wt%, about 25 to about 60 wt%, about 30 to about 60 wt%; about 1 to about 50% by weight, about 5 to about 50% by weight, about 10 to about 50% by weight, about 15 to about 50% by weight, about 20 to about 50% by weight, about 25 to about 50 wt%, about 30 to about 50 wt%; about 1 to about 40% by weight, about 5 to about 40% by weight, about 10 to about 40% by weight, about 15 to about 40% by weight, about 20 to about 40% by weight, about 25 to about 40 wt%, about 30 to about 40 wt%; about 1 to about 35 wt%, about 5 to about 35 wt%, about 10 to about 35 wt%, about 15 to about 35 wt%, about 20 to about 35 wt%, about 25 to about 35 % in weight ; about 1 to about 30% by weight, about 5 to about 30% by weight, about 10 to about 30% by weight, about 15 to about 30% by weight, about 20 to about 30% by weight, including all ranges and subranges included, relative to the total weight of the core components.

In some instances, the mixture of ceramides in the core comprises: (i) about 2 to about 8% by weight ceramide NP, (ii) about 2 to about 8% by weight hydroxypalmitoyl sphinganine, and (iii) about 10 to about 40% by weight of 2-oleamido-1,3-octadecanediol.

In addition to the ceramides mentioned above, the capsule core can be chosen from or comprises one or more of ceramide 1, ceramide 2, ceramide 3, ceramide 4, ceramide 5, ceramide 1A, ceramide 6 II, ceramide AP, ceramide AH , ceramide EOP, ceramide EOS, ceramide NP, ceramide NH, ceramide NG, ceramide NS, ceramide OH, ceramide OS, ceramide AS, and/or ceramide NS dilaurate.

(iv) Hydrophobic solvent

The capsule core includes a hydrophobic solvent. The amount of hydrophobic solvent in the core can vary, but is typically present in an amount of about 35 to about 90% by weight, based on the total weight of the core components. For example, the amount of hydrophobic solvent present in the core can range from about 35 to about 90% by weight, about 40 to about 90% by weight, about 44 to about 90% by weight, about 50 to about 90% by weight, about 55 to about 90% by weight, about 60 to about 90% by weight, about 65 to about 90% by weight, about 70 to about 90% by weight, about 75 to about 90% by weight; about 35 to about 86% by weight, about 40 to about 86% by weight, about 44 to about 86% by weight, about 50 to about 86% by weight, about 55 to about 86% by weight, about 60 to about 86 wt%, about 65 to about 86 wt%, about 70 to about 86 wt%, about 75 to about 86 wt%; about 35 to about 80% by weight, about 40 to about 80% by weight, about 44 to about 80% by weight, about 50 to about 80% by weight, about 55 to about 80% by weight, about 60 to about 80 wt%, about 65 to about 80 wt%, about 70 to about 80 wt%; about 35 to about 75% by weight, about 40 to about 75% by weight, about 44 to about 75% by weight, about 50 to about 75% by weight, about 55 to about 75% by weight, about 60 to about 75 wt%, about 65 to about 75 wt%; about 35 to about 70 wt%, about 40 to about 70 wt%, about 44 to about 70 wt%, about 50 to about 70 wt%, about 55 to about 70 wt%, about 60 to about 70 % by weight, including all inclusive ranges and sub-ranges, based on the total weight of core components.

The hydrophobic solvent can be a fatty compound, such as oils, mineral oil, fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, fatty esters, fatty ethers, waxes, etc. Preferably, the hydrophobic solvent is chosen from or comprises a fatty alcohol. For example, the fatty alcohol can be chosen from cetearyl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, arachidyl alcohol, eicosyl alcohol, myristyl alcohol, 2-dodecylhexadecanol , 2-tetradecyl-1-octadecanol, 2-tetradecyl-1-eicosanol, 2-hexadecyl-1-octadecanol, 2-hexadecyl-1-eicosanol, octyldodecanol, 2-octyl-1-dodecanol, and one of their mixtures. In some cases, the fatty alcohol is 2-octyl-1-dodecanol.

Non-limiting examples of fatty compounds are provided below:

fatty alcohols

The one or more fatty compounds can be glycerolated and/or oxyalkylenated, include from 8 to 30 carbon atoms, and/or be saturated or unsaturated. Fatty alcohols useful herein include those having about 8 to about 30 carbon atoms, about 12 to about 22 carbon atoms, and about 14 to about 22 carbon atoms. These fatty alcohols can be straight or branched chain alcohols and can be saturated or unsaturated. Non-limiting examples of fatty alcohols include decyl alcohol, undecyl alcohol, dodecyl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, isocetyl alcohol, behenyl alcohol, linalool, oleyl alcohol, cis4-t-butylcyclohexanol, myricyl alcohol and one of their mixtures. In some instances, the fatty alcohols include at least one or may be selected from myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, isotridecyl alcohol, and one of their mixtures.

Saturated liquid fatty alcohols can be branched and optionally contain in their structure at least one aromatic or non-aromatic ring. In some cases, however, fatty alcohols are acyclic. Non-limiting examples of liquid saturated fatty alcohols include octyldodecanol, isostearyl alcohol, and 2-hexyldecanol.

Unsaturated liquid fatty alcohols can include in their structure at least one double or triple bond. For example, fatty alcohols can include multiple double bonds (such as 2 or 3 double bonds), which can be conjugated or unconjugated. Unsaturated fatty alcohols can be linear or branched and can be acyclic or include in their structure at least one aromatic or non-aromatic ring. The liquid unsaturated fatty alcohols can include or be selected from oleyl alcohol, linoleyl alcohol, linolenyl alcohol and undecylene alcohol.

Non-limiting examples of solid fatty alcohols include saturated or unsaturated, linear or branched alcohols containing from 8 to 30 carbon atoms, for example, myristyl alcohol, cetyl alcohol, stearyl alcohol and mixtures thereof, cetylstearyl alcohol.

Fatty esters

The fatty compounds of the ceramide composition can be liquid or solid fatty esters at 25°C, 1 atm. The fatty esters can include esters of a C ₆ to C ₃₂ fatty acid and/or of a C ₆ to C ₃₂ fatty alcohol. For example, the fatty compounds can include or be selected from fatty acid monoesters and diesters, polyol esters, polyglycerol esters, polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate, isostearate dimerate polyglycerol, ethyl hexanoate, polyglycerol esters, and one of their mixtures. These esters may be linear or branched, saturated or unsaturated C ₁ to C ₂₆ aliphatic mono or polyacid esters, and linear or branched, saturated or unsaturated C ₁ to C ₂₅ aliphatic mono or polyalcohols, the total number of carbon atoms in the esters being greater than or equal to 10. In one case, the fatty compounds comprise one or more fatty acid monoesters. For monoalcohol esters, at least one of the alcohol or acid from which the esters result is branched. Among the monoesters of monoacids and monoalcohols, mention may be made of ethyl palmitate, isopropyl palmitate, alkyl myristates such as isopropyl myristate or ethyl myristate, isocetyl stearate, 2-ethylhexyl isononanoate , isononyl isononanoate, isodecyl neopentanoate and isostearyl neopentanoate.

In some cases, the fatty esters are cetyl esters, such as esters of saturated fatty acids and fatty alcohols. For example, the fatty esters can include or be selected from cetyl palmitate, cetyl stearate, myristyl myristate, myristyl stearate, cetyl myristate, stearyl stearate, cetearyl ethylhexanoate, and their mixtures. In one case, the fatty esters can be one or more or be chosen from isopropyl isostearate, n-propyl myristate, isopropyl myristate, hexyl laurate, hexadecyl isostearate, hexyldecyl laurate, hexyldecyl octanoate, n-propyl palmitate, isopropyl palmitate, and mixtures thereof. In another instance, the fatty esters include or may be selected from diisobutyl adipate, 2-hexyldecyl adipate, di-2-heptylundecyl adipate, monoisostearic acid N-alkyl glycol, isocetyl isostearate, trimethylolpropane triisostearate, ethylene glycol di-2-ethylhexanoate, cetyl 2-ethylhexanoate, trimethylolpropane tri-2-ethylhexanoate, pentaerythritol tetra-2-ethylhexanoate, cetyl, octyldodecyl ester gum, oleyl oleate, octyldodecyl oleate, decyl oleate, neopentyl glycol dicaprate, triethyl citrate, 2-ethylhexyl succinate, stearate d isocetyl, butyl stearate, diisopropyl sebacate, di-2-ethylhexyl sebacate, cetyl lactate, myristyl lactate, isopropyl palmitate, 2-ethylhexyl palmitate, 2- hexyldecyl, 2-heptylundecyl palmitate, cholesteryl 12-hydroxystearate, dipenta fatty acid ester erythritol, isopropyl myristate, octyldodecyl myristate, 2-hexyldecyl myristate, myristyl myristate, hexyldecyl dimethyl octanoate, ethyl laurate, hexyl laurate, diisostearyl malate, dicaprylyl carbonate, cetearyl ethylhexanoate, and mixtures thereof. In yet another instance, the ceramide composition includes one or more or may include fatty compounds selected from cetearyl alcohol, cetearyl ethylhexanoate, isopropyl myristate, and mixtures thereof.

Non-limiting examples of solid fatty acid esters and/or fatty acid esters which may be mentioned include solid esters obtained from C ₉ to C ₂₆ fatty acids and from fatty alcohols in C ₉ to C ₂₅ . Among these esters, mention may be made of octyldodecyl behenate, isocetyl behenate, cetyl lactate, stearyl octanoate, octyl octanoate, cetyl octanoate, decyl oleate, myristyl stearate, octyl palmitate, peargonate octyl, octyl stearate, alkyl myristates such as cetyl myristate, myristyl myristate or stearyl myristate, and hexyl stearate.

Non-limiting examples of liquid fatty acid include triglyceride oils of vegetable or synthetic origin, such as liquid fatty acid triglycerides containing 6 to 30 carbon atoms, for example triglycerides of heptanoic or octanoic acid, or alternatively, for example, sunflower oil, corn oil, soybean oil, pumpkin seed oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, olive oil, rapeseed oil, coconut oil, wheat germ oil, sweet almond oil, apricot oil, safflower oil, bancoul oil, coconut oil , camelina oil, tamanu oil, babassu oil and pracaxi oil, jojoba oil, shea butter oil, and mixtures thereof.

In one case, the one or more fatty compounds include at least one of or are selected from fatty acid triglycerides, oils, mineral oil, alkanes, fatty alcohols, fatty acids, derivatives of fatty alcohol, alkoxylated fatty acids, polyethylene glycol esters of fatty acids, propylene glycol esters of fatty acids, butylene glycol esters of fatty acids, neopentyl glycol esters of fatty acids, polyglycerol/glycerol esters of fatty acids, glycol diesters, ethylene glycol fatty acid diesters, fatty acid fatty alcohol esters, short chain alcohol esters and fatty acids, fatty alcohol esters, hydroxy-substituted fatty acids, waxes, and one of their mixtures. In another instance, the one or more fatty compounds include one or more fatty acid triglycerides, such as caprylic/capric triglyceride.

Fatty alcohol derivatives

Ceramide compositions may, in some cases, include fatty alcohol derivatives such as fatty alcohol alkyl ethers, fatty alcohol alkoxylates, fatty alcohol alkoxylate alkyl ethers, fatty alcohol esters and one of their mixtures. Non-limiting examples of fatty alcohol derivatives include materials such as methyl stearyl ether; 2-ethylhexyl dodecyl ether; stearyl acetate; cetyl propionate; the ceteth range of compounds such as ceteth-1 through ceteth-45, which are ethylene glycol ethers of cetyl alcohol, wherein the numerical designation indicates the number of ethylene glycol moieties present; the steareth range of compounds such as steareth-1 through 10, which are ethylene glycol ethers of alcohol steareth, in which the numerical designation indicates the number of ethylene glycol moieties present; ceteareth 1 to ceteareth-10, which are the ethylene glycol ethers of ceteareth alcohol, i.e. a mixture of fatty alcohols containing mainly cetearyl and stearyl alcohol, in which the numerical designation indicates the number of fractions ethylene glycol present; the C ₁ to C ₃₀ alkyl ethers of the ceteth, steareth and ceteareth compounds which have just been described; polyoxyethylenated ethers of branched alcohols such as octyldodecyl alcohol, dodecylpentadecylic alcohol, hexyldecyl alcohol, and isostearyl alcohol; polyoxyethylene ethers of behenyl alcohol; PPG ethers such as PPG-9 steareth-3, PPG-11 stearyl ether, PPG8 ceteth-1, and PPG-10 cetyl ether; and one of their mixtures. The liquid fatty ethers can be chosen from liquid dialkyl ethers such as dicaprylyl ether. The non-liquid fatty ethers can also be chosen from dialkyl ethers and in particular dicetyl ether and distearyl ether, alone or as a mixture.

Esters of C ₄ to C ₂₂ dicarboxylic or tricarboxylic acids and of C ₁ to C ₂₂ alcohols and esters of monocarboxylic, dicarboxylic or tricarboxylic acids of non-sugar dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy C ₄ to C ₂₆ can also be used. Mention may be made in particular of diethyl sebacate; diisopropyl sebacate; diisopropyl adipate; di-n-propyl adipate; triisopropyl citrate; glyceryl trilactate; glyceryl trioctanoate; neopentyl glycol diheptanoate; and diethylene glycol diisononanoate.

Fatty acid derivatives

Ceramide compositions may, in some cases, include fatty acid derivatives. Fatty acid derivatives are defined here as including fatty acid esters of fatty alcohols as defined above, fatty acid esters of fatty alcohol derivatives as mentioned above when such derivatives fatty alcohol compounds include an esterifiable hydroxyl group, fatty acid esters of alcohols other than the fatty alcohols and fatty alcohol derivatives described above, hydroxy-substituted fatty acids, and a mixture thereof . In some cases, the fatty acid derivative may comprise or be selected from alkoxylated fatty acids or polyethylene glycol esters of fatty acids or propylene glycol esters of fatty acids or butylene glycol esters of fatty acids or neopentyl glycol esters of fatty acids or polyglycerol/glycerol esters of fatty acids or glycol diesters or ethylene glycol diesters of fatty acids or esters of fatty acids and fatty alcohols, esters of short chain alcohols and fatty acids), glyceryl esters (glycerol esters), fatty alcohol alkyl ethers, fatty acid esters of fatty alcohol alkyl ethers, esters of fatty acid of alkoxylated fatty alcohols, fatty acid esters of alkyl ethers of alkoxylated fatty alcohols, fatty alcohol esters, hydroxy-substituted fatty acids, waxes, triglyceride compounds, lanolin, and one of their blends.

Non-limiting examples of fatty acid derivatives include ricinoleic acid, glycerol monostearate, 12-hydroxy stearic acid, ethyl stearate, cetyl stearate, cetyl palmitate, cetyl ether polyoxyethylene stearate , polyoxyethylene stearyl ether stearate, polyoxyethylene lauryl ether stearate, ethylene glycol monostearate, polyoxyethylene monostearate, polyoxyethylene distearate, propylene glycol monostearate, propylene glycol distearate, trimethylolpropane distearate, sorbitan stearate, polyglyceryl, dimethyl sebacate, PEG-15 cocoate, PPG-15 stearate, glyceryl monostearate, glyceryl distearate, glyceryl tristearate, PEG-8 laurate, PPG-2 isostearate , PPG-9 laurate, and a mixture thereof.

(II) Hydrophilic Solvent

The ceramide composition typically includes a hydrophilic solvent. The hydrophilic solvent is preferably chosen such that the capsules can stably reside in the hydrophilic solvent. The hydrophilic solvent may include or be selected from water, polyols, glycols, and/or any other suitable hydrophilic solvent disclosed herein. The hydrophilic solvent can be chosen according to the desired cosmetic composition or the product to be produced using the ceramide composition.

Non-limiting examples of polyols include those selected from polyols having 2 to 15 carbon atoms and at least two hydroxyl groups. Examples of polyols that can be used in the ceramide composition include and/or can be selected from alkanediols such as glycerine, 1,2,6-hexanetriol, trimethylolpropane, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, dipropylene glycol, 2-butene-1,4-diol, 2-ethyl-1,3-hexanediol, 2-methyl-2,4- pentanediol, caprylyl glycol, 1,2-hexanediol, 1,2-pentanediol, and 4-methyl-1,2-pentanediol; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono -n-propyl ether, ethylene glycol mono-iso-propyl ether, diethylene glycol mono-iso-propyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-t-butyl ether, diethylene glycol mono-t-butyl ether, 1-methyl-1-methoxybutanol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-t-butyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-iso-propyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, and dipropylene glycol mono-iso-propyl ether; sorbitol; sorbitan; triacetin; and one of their mixtures.

The one or more polyols can be glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol or ethers thereof such as, for example, monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol as well as alkyl ethers of diethylene glycol, for example, monoethyl ether or monobutyl ether of diethylene glycol. In one instance, the one or more polyols include or are selected from ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, pentylene glycol, 1,3-propanediol, diethylene glycol, dipropylene glycol , caprylyl glycol, glycerin, and a mixture thereof. In another case, the cosmetic composition includes or is chosen from caprylyl glycol, glycerin, and one of their mixtures.

The total amount of polyols in the ceramide composition can vary, for example, from about 0.1 to about 99% by weight, based on the total weight of the ceramide composition. For example, the total amount of polyols can be about 0.1 to about 25 wt%, about 0.1 to about 20 wt%, about 0.1 to about 15 wt%, about 0, 1 to about 10% by weight, about 0.1 to about 8% by weight, about 0.1 to about 6% by weight, about 2 to about 99% by weight about 2 to about 25% by weight, about 2 to about 20% by weight, about 2 to about 15% by weight, about 2 to about 10% by weight, about 2 to about 8% by weight, or about 2 to about 6% by weight, from about 3 to about 99% by weight about 3 to about 25% by weight, about 3 to about 20% by weight, about 3 to about 15% by weight, about 3 to about 10% by weight, about 3 to about 8% by weight, or about 3 to about 6% by weight, inclusive of ranges and subranges, based on the total weight of the ceramide composition.

(III) Hydroxyacetophenone

The ceramide composition typically includes hydroxyacetophenone. The amount of hydroxyacetophenone in the ceramide composition can vary, but is typically about 0.01 to about 10% by weight based on the total weight of the ceramide composition. For example, the amount of hydroxyacetophenone present in the ceramide composition can range from about 0.01 to about 10% by weight, about 0.01 to about 8% by weight, about 0.01 to about 6% by weight , about 0.01 to about 5 wt%, about 0.01 to about 4 wt%, about 0.01 to about 3 wt%, about 0.01 to about 2 wt%; 0.1 to about 10% by weight, about 0.1 to about 8% by weight, about 0.1 to about 6% by weight, about 0.1 to about 5% by weight, about 0.1 to about 4 wt%, about 0.1 to about 3 wt%, about 0.1 to about 2 wt%; 1 to about 10% by weight, about 1 to about 8% by weight, about 1 to about 6% by weight, about 1 to about 5% by weight, about 1 to about 4% by weight, about 1 to about 3% by weight, about 1 to about 2% by weight, inclusive of all ranges and subranges included, based on the total weight of the ceramide composition. The ceramide composition may include one or more preservatives in addition to hydroxyacetophenone.

Cosmetic composition

The present disclosure also relates to cosmetic compositions which include the ceramide composition and/or ceramide-containing capsules disclosed herein. The cosmetic composition can be in the form of an oil-in-water emulsion, a water-in-oil emulsion, a suspension, a solution, or the like.

Cosmetic compositions typically include:

(A) about 1% to about 20% by weight of a ceramide composition, the ceramide composition comprising:

(I) capsules dispersed in the ceramide composition, the capsules comprising:

(a) a shell comprising:

(i) a polycaprolactone,

(ii) a block copolymer, and

(iii) a surfactant, and

(b) a core comprising:

(i) ceramide NP,

(ii) hydroxypalmitoyl sphinganine,

(iii) 2-oleamido-1,3-octadecanediol,

wherein a weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is from 1:2.5 to 1:5, And

(iv) a hydrophobic solvent,

(II) a hydrophilic solvent, and

(III) hydroxyacetophenone;

(B) optionally, an emulsifier;

(C) optionally, a polyol;

(D) optionally, a fatty compound; And

(E) optionally, a monoalcohol.

The cosmetic compositions preferably include an amount of the ceramide composition to improve the appearance and/or functionality of the skin. In some cases, the cosmetic compositions provide improved skin barrier functionality to a user's skin. For example, the cosmetic composition can promote regeneration, renewal, and/or repair of compromised skin. Additionally or alternatively, the cosmetic compositions can impart an improved appearance of the skin, such as anti-inflammation, improved skin pigmentation, etc.

Suitable components, such as those listed below, may be included or excluded from formulations for cosmetic compositions depending on the specific combination of other components, the form of the cosmetic compositions, and/or the use of the formulation (e.g. , lotion, serum, gel, cream, etc.).

(A) Ceramide Composition

The amount of the ceramide composition in the cosmetic composition can vary, but is typically present in an amount ranging from about 1% to about 20% by weight, based on the total weight of the cosmetic composition. For example, the amount of ceramide composition in the cosmetic composition can range from about 1 to about 25% by weight, about 1 to about 20% by weight, about 1 to about 18% by weight, about 1 to about 16% by weight, about 1 to about 14% by weight, about 1 to about 12% by weight, about 1 to about 10% by weight, about 1 to about 9% by weight, about 1 to about 8% by weight, about 1 about 7% by weight, about 1 to about 6% by weight, about 1 to about 5% by weight, about 1 to about 4% by weight; about 3 to about 25 wt%, about 3 to about 20 wt%, about 3 to about 18 wt%, about 3 to about 16 wt%, about 3 to about 14 wt%, about 3 to about 12 wt%, about 3 to about 10 wt%, about 3 to about 9 wt%, about 3 to about 8 wt%, about 3 to about 7 wt%; about 5 to about 25 wt%, about 5 to about 20 wt%, about 5 to about 18 wt%, about 5 to about 16 wt%, about 5 to about 14 wt%, about 5 to about 12 wt%, about 5 to about 10 wt%, about 5 to about 9 wt%, about 5 to about 8 wt%; about 8 to about 25 wt%, about 8 to about 20 wt%, about 8 to about 18 wt%, about 8 to about 16 wt%, about 8 to about 14 wt%, about 8 to about 12 % in weight ; about 10 to about 25 wt%, about 10 to about 20 wt%, about 10 to about 18 wt%, about 10 to about 16 wt%, about 10 to about 14 wt%; about 13 to about 25 wt%, about 13 to about 20 wt%, about 13 to about 18 wt%; about 15 to about 25 wt%, about 15 to about 20 wt%, about 15 to about 18 wt%; about 18 to about 25% by weight; about 20 to about 25% by weight, based on the total weight of the cosmetic composition.

(B) Emulsifiers

The cosmetic compositions described herein include one or more emulsifiers. For example, the emulsifier can be an amphoteric, anionic, cationic or non-ionic emulsifier, used alone or in admixture, and optionally with a co-emulsifier. The emulsifiers are chosen appropriately according to the emulsion to be obtained.

For W/O emulsions, examples of emulsifiers which may be mentioned include dimethicone copolyols, such as the mixture of cyclomethicone and dimethicone copolyol sold under the trade name DC 5225 C by the company Dow Corning, and alkyl dimethicone copolyols such as the lauryl dimethicone copolyol sold under the trade name Dow Corning 5200 Formulation Aid by the company Dow Corning, and the cetyl dimethicone copolyol sold under the name Abil EM 90TM by the company Goldschmidt.

For O/W emulsions, examples of emulsifiers which may be mentioned include nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylene) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylene) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylene) fatty alcohol ethers; sugar esters such as sucrose stearate; and their mixtures.

The one or more emulsifiers can be oxyalkylenated organosiloxane emulsifiers. The oxyalkylenated organosiloxane emulsifiers can be totally or partially crosslinked and/or be elastomeric or non-elastomeric. They are sometimes referred to as "emulsifying elastomers" because they have both elastomeric and emulsifying properties. In some instances, the one or more emulsifiers include an organosiloxane emulsifier, including cross-linked organosiloxane emulsifiers. For example, the cosmetic compositions may comprise one or more cross-linked oganosiloxane emulsifiers including or selected from a cross-linked polymer of PEG/PPG 15 of dimethicone/dimethicone, a cross-linked polymer of PEG-10 of dimethicone, a cross-linked polymer of PEG-10/15 dimethicone, cross-linked polymer of dimethicone PEG-15, cross-linked polymer of dimethicone polyglycerin-3, cross-linked polymer of dimethicone PPG-20, cross-linked polymer of dimethiconol/methylsilanol/silicate; cross-linked polymer of dimethiconol/silicate, cross-linked polymer of PEG-15 of lauryl dimethicone, cross-linked polymer of polyglycerin-3 of lauryl dimethicone, cross-linked polymer of PEG-8 dimethicone polysorbate-20, cross-linked polymer of PEG-10 dimethicone/vinyl dimethicone, cross-linked polymer of PEG-10 lauryl dimethicone, cross-linked polymer of PEG-15/lauryl dimethicone, cross-linked polymer of PEG-15 laurylpolydimethylsiloxyethyl, and mixtures thereof.

In another case, the cosmetic compositions include one or more linear organosiloxane emulsifiers selected from cyclotetrasiloxane (and) cyclopentasiloxane (and) PEG/PPG-18 dimethicone, cyclopentasiloxane (and) PEG/PPG-18/18 dimethicone; PEG/PPG-18/18 dimethicone; lauryl PEG/PPG-18/18 methicone; cetyl PEG/PPG-14/14 dimethicone; bis-cetyl PEG/PPG-14/14 dimethicone; cetyl PEG/PPG-10/1 dimethicone; PEG-11 methyl ether dimethicone; PEG/PPG-20/22 butyl ether dimethicone; PEG-9 dimethicone; PEG-3 dimethicone; PEG-9 methyl ether dimethicone; PEG-10 dimethicone; lauryl PEG-9 polydimethylsiloxyethyl dimethicone; and their mixtures.

The cosmetic composition may, in certain cases, include an oxyalkylenated organosiloxane emulsifier. The oxyalkylenated organosiloxane emulsifier may have a structure in accordance with the following general formula:

where p is 0 to 40 (the range including all numbers between and subranges such as 2, 3, 4, 13, 14, 15, 16, 17, 18, etc.), and PE is (-C2H4O )a-(-C3H6O)b-H wherein a is 0 to 25, b is 0 to 25 provided that both a and b are not 0 simultaneously, x, y, and z are each independently between 0 and 1 million provided that x and y are not 0 simultaneously. In some cases, x, y, z, a, and b are such that the molecular weight of the polymer is about 5,000 to about 500,000, about 10,000 to 100,000, or about 50,000, and the polymer is generically referred to as dimethicone copolyol. In additional cases, p is such that the long alkyl chain is cetyl or lauryl, and the compound is referred to, generically, as cetyl dimethicone copolyol or lauryl dimethicone copolyol respectively. In some cases, the number of ethylene oxide or propylene oxide repeating units in the polymer is also specified, such as dimethicone copolyol which is also referred to as PEG-15/PPG-10 dimethicone, which refers to dimethicone having substituents containing 15 ethylene glycol units and 10 propylene glycol units in the siloxane backbone. It is also possible for one or more of the methyl groups in the general structure above to be substituted with a longer chain alkyl (e.g. ethyl, propyl, butyl, etc.) or ether, such as methyl ether, ethyl ether, propyl ether, butyl ether, and the like.

The oxyalkylenated organosiloxane emulsifier may alternatively have a structure in accordance with the following general formula:

where each n is independently 0 to 100 provided there can be at least one PE radical. In some cases, where each n is independently about 2 to 30, and PE(-C2H4O)a-(-C3H6O)b-H where a is 0 to 25, b is 0 to 25 provided that both a and b cannot simultaneously equal 0; and wherein w, x, y, and z are each independently 0 to 1,000,000 provided there is at least one PE. In some embodiments, the organosiloxane emulsifier is lauryl PEG-9 polydimethylsiloxyethyl dimethicone. The oxyalkylenated organosiloxane emulsifiers disclosed in US 9,095,543 may be useful in cosmetic compositions. U.S. Patent No. 9,095,543 is incorporated herein by reference in its entirety for all purposes.

Additional examples of organosiloxane emulsifiers include those having the names C.T.F.A. Bis-Butyldimethicone Polyglyceryl-3; Bis-PEG/PPG-14/14 Dimethicone; Bis-butyldimethicone Polyglyceryl-3; Bis-isobutyl PEG/PPG-10/7 Dimethicone copolymer; Bis-PEG/PPG-18/6 Dimethicone; Bis-PEG/PPG-20/20 Dimethicone; Bis-PEG/PPG-16/16 PEG/PPG-16/16 Dimethicone; Bis(PPG-7 Undeceneth-21-Dimethicone; Cetyl Dimethicone PEG-7 Acetate; Cetyl PEG-8 Dimethicone; Cetyl PEG/PPG-15/16 Butyl Ether Dimethicone; Cetyl PEG/PPG-15/15 Butyl Ether Dimethicone; Cetyl PEG /PPG-7/3 Dimethicone;Cetyl PEG/PPG-10/1 Dimethicone;Dimethicone PEG-15 Acetate;Dimethicone PEG-7 Cocoate;Dimethicone PEG-7 Phosphate;Dimethicone PEG-10 Phosphate;Dimethicone PEG/PPG-7/4 Phosphate; Dimethicone PEG/PPG-12/4 Phosphate; Dimethicone PEG-7 Undecylenate; Lauryl Dimethicone PEG-10 Phosphate; Isopolyglyceryl-3 Dimethicone; Isopolyglyceryl-3 Dimethiconol; Isostearyl Carboxyldecyl PEG-8 Dimethicone; Lauryl Methicone PEG-10 Phosphate; Lauryl PEG-8 Dimethicone; Lauryl PEG-10 Methyl Ether Dimethicone; Lauryl PEG/PPG-18/18 Methicone; PEG-6 Methyl Ether Dimethicone; PEG-7 Methyl Ether Dimethicone; PEG-9 Methyl Ether Dimethicone; PEG-10 Methyl Ether Dimethicone PEG-11 Methyl Ether Dimethicone PEG-11 Methyl Ether Dimethicone PEG-32 Methyl Ether Dimethicone PEG-PEG/PPG-28/21 Acetate Dime thicone; PEG/PPG-22/22 Butyl Ether Dimethicone; PEG/PPG-23/23 Butyl Ether Dimethicone; PEG/PPG-24/18 Butyl Ether Dimethicone; PEG/PPG-3/10 Dimethicone; PEG/PPG-4/12 Dimethicone; PEG/PPG-6/11 Dimethicone; PEG/PPG-8/14 Dimethicone; PEG/PPG-12/16 Dimethicone; PEG/PPG-12/18 Dimethicone; PEG/PPG-14/4 Dimethicone; PEG/PPG-15/5 Dimethicone; PEG/PPG-15/15 Dimethicone; PEG/PPG-16/2 Dimethicone; PEG/PPG-16/8 Dimethicone; PEG/PPG-17/18 Dimethicone; PEG/PPG-18/12 Dimethicone; PEG/PPG-19/19 Dimethicone; PEG/PPG-20/6 Dimethicone; PEG/PPG-20/15 Dimethicone; PEG/PPG-20/20 Dimethicone; PEG/PPG-20/29 Dimethicone; PEG/PPG-22/23 Dimethicone; PEG/PPG-22/24 Dimethicone; PEG/PPG-25/25 Dimethicone; PEG/PPG-27/27 Dimethicone; PEG/PPG-30/10 Dimethicone; PEG/PPG-10/3 Oleyl Ether Dimethicone; PEG-8 trisiloxane; Polyglyceryl-3 Polydimethylsiloxyethyl Dimethicone; PPG-12 Butyl Ether Dimethicone; Quaternium-17 silicone; TEA-Dimethicone PEG-7 Phosphate; and their mixtures.

Additional examples of commercial linear organosiloxane emulsifiers are those sold by Dow Corning under the trade name Dow Corning 3225C Formulation Aid having the CTFA name cyclotetrasiloxane (and) cyclopentasiloxane (and) PEG/PPG-18 dimethicone; or 5225C Formulation Aid, designated as CTFA cyclopentasiloxane (and) PEG/PPG-18 dimethicone; or 5225C Formulation Aid, having the CTFA name cyclopentasiloxane (and) PEG/PPG-18/18 dimethicone; or Dow Corning 190 Surfactant having the CTFA name PEG/PPG-18/18 dimethicone; or Dow Corning 193 Fluid, Dow Corning 5200 having the CTFA name lauryl PEG/PPG-18/18 methicone; or Abil EM 90 having the CTFA name cetyl PEG/PPG-14/14 dimethicone sold by Goldschmidt; or Abil EM 97 having the CTFA name bis-cetyl PEG/PPG-14/14 dimethicone sold by Goldschmidt; or Abil WE 09 having the CTFA name cetyl PEG/PPG-10/1 dimethicone in a mixture also containing polyglyceryl-4 isostearate and hexyl laurate; or KF-6011 sold by Shin-Etsu Silicones having the CTFA name PEG-11 methyl ether dimethicone; KF-6012 sold by Shin-Etsu Silicones having the CTFA name PEG/PPG-20/22 butyl ether dimethicone; or KF-6013 sold by Shin-Etsu Silicones having the CTFA name PEG-9 dimethicone; or KF-6015 sold by Shin-Etsu Silicones having the CTFA name PEG-3 dimethicone; or KF-6016 sold by Shin-Etsu Silicones having the CTFA name PEG-9 methyl ether dimethicone; or KF-6017 sold by Shin-Etsu Silicones having the CTFA name PEG-10 dimethicone; or KF-6038 sold by Shin-Etsu Silicones having the CTFA name lauryl PEG-9 polydimethylsiloxyethyl dimethicone.

Additional examples of cross-linked organosiloxane emulsifiers include, but are not limited to, dimethicone/dimethicone PEG/PPG 15 cross-linked polymer; the cross-linked polymer dimethicone PEG-10; the cross-linked polymer dimethicone PEG-10/15; the cross-linked polymer dimethicone PEG-15; the cross-linked polymer dimethicone polyglycerin-3; the cross-linked polymer dimethicone PPG-20; the dimethiconol/methylsilanol/silicate cross-linked polymer; dimethiconol/silicate cross-linked polymer; the cross-linked polymer lauryl dimethicone PEG-15; the cross-linked polymer lauryl dimethicone polyglycerin-3; the cross-linked polymer PEG-8 dimethicone polysorbate-20; the cross-linked polymer PEG-10 dimethicone/vinyl dimethicone; the cross-linked polymer PEG-10 lauryl dimethicone; the cross-linked polymer PEG-15/lauryl dimethicone; and the cross-linked polymer PEG-15 laurylpolydimethylsiloxyethyl.

The one or more emulsifiers may, in certain cases, be polyoxyalkylenated silicone elastomers, such as, for example, those sold by Shin-Etsu Silicones under the names KSG-21, KSG-20, KSG-30, KSG-31, KSG-32, KSG-33; KSG-210 which is a dimethicone/PEG-10/15 cross-linked polymer dispersed in dimethicone; KSG-310 which is a cross-linked polymer of PEG-15 lauryl dimethicone; KSG-320 which is a cross-linked polymer of PEG-15 lauryl dimethicone dispersed in isododecane; KSG-330 (this one dispersed in triethylhexanoin), KSG-340 which is a mixture of cross-linked polymer of PEG-10 lauryl dimethicone and cross-linked polymer of PEG-15 lauryl dimethicone. The polyglycerolated silicone elastomers can include or be selected from dimethicone/polyglycerin-3 cross-linked polymer dispersed in dimethicone; or a lauryl dimethicone/polyglycerin-3 cross-linked polymer dispersed in a variety of solvents such as isododecane, dimethicone, triethylhexanoin, sold under the trade names of Shin-Etsu KSG-810, KSG-820, KSG-830, or KSG-840. Silicones sold by Dow Corning under the brand names 9010 and DC9011 are also suitable.

The emulsifiers can, in certain cases, be a nonionic surfactant, such as chosen from: alkanolamides; alkyl polyglucosides; polyoxyalkylenated nonionic surfactants; polyglycerolated nonionic surfactants; ethoxylated fatty esters; alcohols, alpha-diols, alkylphenols and fatty acid esters, which are ethoxylated, propoxylated or glycerolated; ethylene oxide and/or propylene oxide copolymers; condensates of ethylene oxide and/or propylene oxide with fatty alcohols; polyethoxylated fatty amides; sorbitan ethoxylated fatty acid esters comprising from 2 to 30 moles of ethylene oxide; ethoxylated oils of vegetable origin; sucrose fatty acid esters; polyethylene glycol fatty acid esters; mono or diesters of polyethoxylated fatty acids of glycerol alkyl (C ₆ to C ₂₄ ) polyglycosides; N-alkyl (C ₆ to C ₂₄ ) glucamine derivatives, amine oxides such as alkyl (C ₁₀ to C ₁₄ ) amine oxides or N-acyl (C ₁₀ to C ₁₄ ) aminopropylmorpholine oxides ; and their mixtures.

Additional nonionic surfactants which may in some cases be suitable include, for example, alcohols, alpha-diols, alkylphenols and fatty acid esters, which are ethoxylated, propoxylated or glycerolated and having at least one fatty chain. comprising, for example, from 8 to 18 carbon atoms, knowing that the number of ethylene oxide or propylene oxide groups can range from 2 to 50, and that the number of glycerol groups can range from 1 to 30. also make non-limiting mention of copolymers of ethylene oxide and/or propylene oxide; condensates of ethylene oxide and/or propylene oxide with fatty alcohols; polyethoxylated fatty amides comprising, for example, from 2 to 30 moles of ethylene oxide; polyglycerolated fatty amides comprising, for example, from 1.5 to 5 glycerol groups, such as 1.5 to 4; sorbitan ethoxylated fatty acid esters comprising 2 to 30 moles of ethylene oxide; ethoxylated oils of plant origin; sucrose fatty acid esters; polyethylene glycol fatty acid esters; mono or diesters of polyethoxylated fatty acids of glycerol alkyl (C ₆ to C ₂₄ ) polyglycosides; derivatives of N-alkyl (C ₆ to C ₂₄ ) glucamine, amine oxides such as alkyl (C ₁₀ to C ₁₄ ) amine oxides or N-acyl oxides (C ₁₀ to C ₁₄ ) aminopropylmorpholine; and their mixtures.

In certain cases, the nonionic surfactant can be chosen from polyol esters with saturated or unsaturated chain fatty acids containing for example from 8 to 24 carbon atoms, and their alkoxylated derivatives; C ₈ to C ₂₄ polyethylene glycol esters; C ₈ to C ₂₄ sorbitol esters; C ₈ to C ₂₄ sugar esters (sucrose, glucose, alkylglycose), preferably one or more C ₁₂ to C ₂₂ fatty acids, and their alkoxylated derivatives; sugar ethers and a C ₈ to C ₂₄ , preferably C ₁₂ to C ₂₂ , fatty alcohol or alcohols; and their mixtures. In one case, the nonionic surfactant is an ethoxylated fatty ester chosen from adducts of ethylene oxide with esters of lauric acid, palmitic acid, stearic acid or behenic acid, and mixtures thereof. Examples of ethoxylated fatty esters which may be suitable include those containing from 9 to 100 oxyethylene groups, such as PEG-9 to PEG-50 laurate (under the CTFA names: PEG-9 laurate to PEG-50 laurate); PEG-9 to PEG-50 palmitate (under the CTFA names: PEG-9 palmitate to PEG-50 palmitate); PEG-9 to PEG-50 stearate (under the CTFA names: PEG-9 stearate to PEG-50 stearate); palmitostearate from PEG-9 to PEG-50; PEG-9 to PEG-50 behenate (under the CTFA names: PEG-9 behenate to PEG-50 behenate); polyethylene glycol monostearate 100 EO (CTFA name: PEG-100 stearate); and their mixtures.

The nonionic surfactant can be chosen from glyceryl esters of fatty acids, glyceryl stearate (mono-, di- and/or glyceryl tristearate) (CTFA name: glyceryl stearate); glyceryl ricinoleate); glyceryl esters of C ₈ to C ₂₄ alkoxylated fatty acids, such as polyethoxylated glyceryl stearate (mono-, di- and/or glyceryl tristearate), and PEG-20 glyceryl stearate; and their mixtures.

In some cases, the cosmetic composition may include an emulsifier such as dimeric surfactants called "gemini surfactants", which comprise at least two identical or different surfactant fractions, and consisting of a hydrophilic head group and a lipophilic group linked to one the other through the head groups, thanks to a spacer. For example, the one or more emulsifiers can include or be chosen from those sold by the company Sasol under the name CERALUTIOM, for example, Ceralution H: behenyl alcohol, glyceryl stearate, glyceryl citrate stearate and dicocoyl ethylenediamine PEG-15 sulphate of sodium, Ceralution F: sodium lauroyl lactylate and sodium dicocoyl ethylenediamine PEG-15 sulfate, Ceralution C: water, capric/caprylic triglyceride, ceteareth-25, sodium dicocoyl ethylenediamine PEG-15 sulfate, sodium lauroyl lactylate, behenyl alcohol, glyceryl stearate, glyceryl citrate stearate, gum arabic, xanthan gum, phenoxyethanol, methylparaben, ethylparaben, butylparaben, isobutylparaben. In at least one embodiment, the emulsifier of the cosmetic composition consists of sodium lauroyl lactylate or consists essentially of sodium lauroyl lactylate. In additional embodiments, the emulsifier(s) of the cosmetic composition include (include) sodium lauroyl lactylate with one or more additional emulsifiers, such as a nonionic emulsifier or an anionic emulsifier.

The total amount of emulsifiers in the cosmetic compositions can vary, for example, from about 0.001 to about 25% by weight, based on the total weight of the composition. For example, the total amount of emulsifiers can be about 0.001 to about 25% by weight, about 0.001 to about 20% by weight, about 0.001 to about 15% by weight, about 0.001 to about 10% by weight , about 0.001 to about 8% by weight, about 0.001 to about 6% by weight, about 0.5 to about 25% by weight about 0.5 to about 20% by weight, about 0.5 to about 15% by weight, about 0.5 to about 10% by weight, about 0.5 to about 8% by weight, about 0.5 to 6% by weight, about 1 to about 25% by weight, about 1 to about 20% by weight, about 1 to about 15% by weight, about 1 to about 10% by weight, about 1 to about 8% by weight, or about 1 to about 6% by weight, from about 2 to about 25% by weight, about 2 to about 20% by weight, about 2 to about 15% by weight, about 2 to about 10% by weight, about 2 to about 8% by weight, or about 2 to about 6% by weight, d about 3 to about 25% by weight, about 3 to about 20% by weight ds, about 3 to about 15% by weight, about 3 to about 10% by weight, about 3 to about 8% by weight, or about 3 to about 6% by weight, about 4 to about 25% by weight, about 4 to about 20 wt%, about 4 to about 15 wt%, about 4 to about 10 wt%, about 4 to about 8 wt%, or about 4 to about 6 wt%, of about 5 about 25% by weight, about 0.05 to about 20% by weight, about 0.05 to about 15% by weight, about 0.05 to about 10% by weight, about 0.05 to about 8% by weight , or about 0.05 to about 6% by weight including ranges and subranges, based on the total weight of the cosmetic composition. In one instance, the total amount of emulsifiers in the cosmetic composition is typically in an amount of 0.5, 0.6, 0.7, 0.8, 0.9 or 1.0% by weight to 5.6 , 7, 8, 9, or 10% by weight, based on the total weight of the cosmetic composition.

(C) Polyols

The polyols of the cosmetic composition can comprise or be chosen from polyols comprising from 2 to 15 carbon atoms and at least two hydroxyl groups. Examples of polyols which can be used in the cosmetic composition include and/or can be chosen from alkanediols such as glycerine, 1,2,6-hexanetriol, trimethylolpropane, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, dipropylene glycol, 2-butene-1,4-diol, 2-ethyl-1,3-hexanediol, 2-methyl-2,4-pentanediol , caprylyl glycol, 1,2-hexanediol, 1,2-pentanediol, and 4-methyl-1,2-pentanediol; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, ethylene glycol mono-iso-propyl ether, diethylene glycol mono-iso-propyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-t-butyl ether , diethylene glycol mono-t-butyl ether, 1-methyl-1-methoxybutanol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-t-butyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-iso-propyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, and dipropylene glycol mono-iso-propyl ether; sorbitol; sorbitan; triacetin; and one of their mixtures.

The polyol(s) can (can) be glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol or their ethers such as, for example, monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol as well as alkyl ethers of diethylene glycol, for example, monoethyl ether or monobutyl ether of diethylene glycol. In one instance, the one or more polyols include or are selected from ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, pentylene glycol, 1,3-propanediol, diethylene glycol, dipropylene glycol , caprylyl glycol, glycerin, and a mixture thereof. In another case, the cosmetic composition includes or is chosen from caprylyl glycol, glycerin, and one of their mixtures.

The total amount of polyols in the ceramide composition can vary, for example, from about 0.1 to about 99% by weight, based on the total weight of the cosmetic composition. For example, the total amount of polyols can be about 0.1 to about 25 wt%, about 0.1 to about 20 wt%, about 0.1 to about 15 wt%, about 0, 1 to about 10% by weight, about 0.1 to about 8% by weight, about 0.1 to about 6% by weight, about 2 to about 99% by weight about 2 to about 25% by weight, about 2 to about 20% by weight, about 2 to about 15% by weight, about 2 to about 10% by weight, about 2 to about 8% by weight, or about 2 to about 6% by weight, from about 3 to about 99% by weight about 3 to about 25% by weight, about 3 to about 20% by weight, about 3 to about 15% by weight, about 3 to about 10% by weight, about 3 to about 8% by weight, or about 3 to about 6% by weight, inclusive of ranges and subranges, based on the total weight of the cosmetic composition.

(D) Fatty compound(s)

The cosmetic composition can include one or more fatty compounds, which can be liquid or solid at ambient temperature and at atmospheric pressure (25° C., 1 atm). Fatty compounds are typically organic compounds that are not soluble in water at normal temperature (25°C) and atmospheric pressure (750 mmHg) (solubility below 10%). In some cases, the water solubility may be below 5%, below 1%, or below 0.1%.

The total quantity of fatty compounds in the cosmetic composition can vary, for example, from about 0.1 to about 25% by weight, based on the total weight of the cosmetic composition. For example, the total amount of fatty compounds can be about 0.1 to about 25 wt%, about 0.1 to about 20 wt%, about 0.1 to about 15 wt%, about 0 1 to about 10 wt%, about 0.1 to about 8 wt%, about 0.1 to about 6 wt%, about 0.5 to about 25 wt% about 0.5 to about 20 % by weight, about 0.5 to about 15% by weight, about 0.5 to about 10% by weight, about 0.5 to about 8% by weight, about 0.5 to 6% by weight, about 1 to about 25% by weight, about 1 to about 20% by weight, about 1 to about 15% by weight, about 1 to about 10% by weight, about 1 to about 8% by weight, or about 1 to about 6 % by weight, from about 1.5 to about 25% by weight, about 1.5 to about 20% by weight, about 1.5 to about 15% by weight, about 1.5 to about 10% by weight, about 1.5 to about 8 wt%, or about 1.5 to about 6 wt%, about 2 to about 25 wt%, about 2 to about 20 wt% oids, about 2 to about 15% by weight, about 2 to about 10% by weight, about 2 to about 8% by weight, or about 2 to about 6% by weight, about 2.5 to about 25% by weight, about 2.5 to about 20% by weight, about 2.5 to about 15% by weight, about 2.5 to about 10% by weight, about 2.5 to about 8% by weight, or about 2, 5 to about 6 wt%, about 3 to about 25 wt%, about 3 to about 20 wt%, about 3 to about 15 wt%, about 3 to about 10 wt%, about 3 to about 8% by weight, or about 3 to about 6% by weight, about 3.5 to about 25% by weight, about 3.5 to about 20% by weight, about 3.5 to about 15% by weight, about 3.5 to about 10% by weight, about 3.5 to about 8% by weight, or about 3.5 to about 6% by weight, inclusive ranges and subranges, based on the total weight of the cosmetic composition.

Non-limiting examples of fatty compounds of the cosmetic composition include or may be chosen from oils, mineral oil, fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives (for example, alkoxylated fatty acids or polyethylene glycol esters of fatty acids or propylene glycol esters of fatty acids or butylene glycol esters of fatty acids or neopentyl glycol esters and fatty acids or polyglycerol/glycerol esters of fatty acids or glycol diesters or ethylene glycol diesters and fatty acids or esters of fatty acids and fatty alcohols, esters of short-chain alcohols and fatty acids), glyceryl esters (glycerol esters), fatty alcohol alkyl ethers, fatty acid esters of fatty alcohol alkyl ethers, fatty acid esters of alkoxylated fatty alcohols, fatty acid esters of alkoxylated fatty alcohol alkyl ethers , fatty alcohol esters, hydroxy-substituted fatty acids, waxes, c triglyceride compounds, lanolin, and a mixture thereof. In some instances, the one or more fatty compounds may include or be selected from fatty alcohols, fatty acids, fatty acid esters, and/or fatty alcohol esters (e.g., cetyl palmitate, cetyl stearate , myristyl myristate, myristyl stearate, cetyl myristate, and stearyl stearate (a mixture which is referred to as "cetyl esters"). Additionally or alternatively, the one or more fatty compounds may include or be selected from hydrocarbons, fatty alcohols, fatty alcohol derivatives, fatty acids, fatty acid derivatives, fatty esters, fatty ethers , oils, waxes, etc. In one instance, the one or more fatty compounds is a hydrocarbon that is linear, branched, and/or cyclic, such as C ₆ -C ₁₆ cyclic alkanes, hexane, undecane, dodecane, tridecane, and isoparaffins, for example isohexadecane, isododecane and isodecane. In addition, linear or branched hydrocarbons can be composed only of carbon and hydrogen atoms of mineral, vegetable, animal or synthetic origin with more than 16 carbon atoms, such as volatile or non-volatile liquid paraffins, petroleum jelly, liquid petroleum jelly, polydecenes, hydrogenated polyisobutene, and squalane.

fatty alcohols

The one or more fatty compounds can be glycerolated and/or oxyalkylenated, can include from 8 to 30 carbon atoms, and can be saturated or unsaturated. Fatty alcohols useful herein include those having from about 8 to about 30 carbon atoms, from about 12 to about 22 carbon atoms, and from about 14 to about 22 carbon atoms. These fatty alcohols can be straight or branched chain alcohols and can be saturated or unsaturated. Non-limiting examples of fatty alcohols include decyl alcohol, undecyl alcohol, dodecyl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, isocetyl alcohol, behenyl alcohol, linalool, oleyl alcohol, cis4-t-butylcyclohexanol, myricyl alcohol and one of their mixtures. In some instances, the fatty alcohols include at least one or may be selected from myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, isotridecyl alcohol, and one of their blends.

Saturated liquid fatty alcohols can be branched and optionally contain in their structure at least one aromatic or non-aromatic ring. In some cases, however, fatty alcohols are acyclic. Non-limiting examples of liquid saturated fatty alcohols include octyldodecanol, isostearyl alcohol, and 2-hexyldecanol.

Liquid unsaturated fatty alcohol can include in its structure at least one double or triple bond. For example, fatty alcohols can include multiple double bonds (such as 2 or 3 double bonds), which can be conjugated or unconjugated. Unsaturated fatty alcohols can be linear or branched and can be acyclic or include in their structure at least one aromatic or non-aromatic ring. The liquid unsaturated fatty alcohols can include or be selected from oleyl alcohol, linoleyl alcohol, linolenyl alcohol and undecylene alcohol.

Non-limiting examples of solid fatty alcohols include linear or branched, saturated or unsaturated alcohols containing from 8 to 30 carbon atoms, for example, myristyl alcohol, cetyl alcohol, stearyl alcohol and mixtures thereof, cetylstearyl alcohol.

Fatty esters

The fatty compounds of the cosmetic composition can be liquid or solid fatty esters at 25° C., 1 atm. The fatty esters can include the esters of a C ₆ to C ₃₂ fatty acid and/or of a C ₆ to C ₃₂ fatty alcohol. For example, the fatty compounds can include or be selected from fatty acid monoesters and diesters, polyol esters, polyglycerol esters, polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate, polyglycerol isostearate dimerate , ethyl hexanoate, polyglycerol esters, and one of their mixtures. These esters may be esters of saturated or unsaturated, linear or branched C ₁ to C ₂₆ aliphatic mono or polyacids and of saturated or unsaturated, linear or branched C ₁ to C ₂₅ aliphatic mono or polyalcohols, the total number of atoms of carbon in the esters being greater than or equal to 10. In one case, the fatty compounds comprise one or more fatty acid monoesters. For monoalcohol esters, at least one of the alcohol or acid from which the esters result is branched. Among the monoesters of monoacids and monoalcohols, mention may be made of ethyl palmitate, isopropyl palmitate, alkyl myristates such as isopropyl myristate or ethyl myristate, isocetyl stearate, 2-ethylhexyl isononanoate , isononyl isononanoate, isodecyl neopentanoate and isostearyl neopentanoate.

In some cases, the fatty esters are cetyl esters, such as esters of saturated fatty acids and fatty alcohols. For example, the fatty esters can include or be selected from cetyl palmitate, cetyl stearate, myristyl myristate, myristyl stearate, cetyl myristate, stearyl stearate, cetearyl ethylhexanoate, and their mixtures. In one case, the fatty esters can be one or more of or be chosen from isopropyl isostearate, n-propyl myristate, isopropyl myristate, hexyl laurate, hexadecyl isostearate, hexyldecyl laurate, hexyldecyl octanoate, n-propyl palmitate, isopropyl palmitate, and mixtures thereof. In another instance, the fatty esters include or may be selected from diisobutyl adipate, 2-hexyldecyl adipate, di-2-heptylundecyl adipate, monoisostearic acid N-alkyl glycol, isocetyl isostearate, trimethylolpropane triisostearate, ethylene glycol di-2-ethylhexanoate, cetyl 2-ethylhexanoate, trimethylolpropane tri-2-ethylhexanoate, pentaerythritol tetra-2-ethylhexanoate, cetyl, octyldodecyl ester gum, oleyl oleate, octyldodecyl oleate, decyl oleate, neopentyl glycol dicaprate, triethyl citrate, 2-ethylhexyl succinate, stearate d isocetyl, butyl stearate, diisopropyl sebacate, di-2-ethylhexyl sebacate, cetyl lactate, myristyl lactate, isopropyl palmitate, 2-ethylhexyl palmitate, 2- hexyldecyl, 2-heptylundecyl palmitate, cholesteryl 12-hydroxystearate, dipenta fatty acid ester erythritol, isopropyl myristate, octyldodecyl myristate, 2-hexyldecyl myristate, myristyl myristate, hexyldecyl dimethyl octanoate, ethyl laurate, hexyl laurate, diisostearyl malate, dicaprylyl carbonate, cetearyl ethylhexanoate, and mixtures thereof. In yet another case, the cosmetic composition includes one or more or may comprise fatty compounds selected from cetearyl alcohol, cetearyl ethylhexanoate, isopropyl myristate, and mixtures thereof.

Non-limiting examples of liquid fatty acid include triglyceride oils of vegetable or synthetic origin, such as liquid fatty acid triglycerides containing 6 to 30 carbon atoms, for example triglycerides of heptanoic or octanoic acid, or alternatively, for example, sunflower oil, corn oil, soybean oil, pumpkin seed oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, olive oil, rapeseed oil, coconut oil, wheat germ oil, sweet almond oil, apricot oil, safflower oil, bancoul oil, coconut oil , camelina oil, tamanu oil, babassu oil and pracaxi oil, jojoba oil, shea butter oil, and mixtures thereof.

Non-limiting examples of solid fatty acid esters and/or fatty acid esters which may be mentioned include solid esters obtained from C ₉ to C ₂₆ fatty acids and from fatty alcohols in C ₉ to C ₂₅ . Among these esters, mention may be made of octyldodecyl behenate, isocetyl behenate, cetyl lactate, stearyl octanoate, octyl octanoate, cetyl octanoate, decyl oleate, myristyl stearate, octyl palmitate, pelargonate octyl, octyl stearate, alkyl myristates such as cetyl myristate, myristyl myristate or stearyl myristate, and hexyl stearate.

Fatty alcohol derivatives

The cosmetic compositions may, in some cases, include fatty alcohol derivatives such as fatty alcohol alkyl ethers, alkoxylated fatty alcohols, alkoxylated fatty alcohol alkyl ethers, fatty alcohol esters and one of their mixtures. Non-limiting examples of fatty alcohol derivatives include materials such as methyl stearyl ether; 2-ethylhexyl dodecyl ether; stearyl acetate; cetyl propionate; the ceteth range of compounds such as ceteth-1 through ceteth-45, which are ethylene glycol ethers of cetyl alcohol, wherein the numerical designation indicates the number of ethylene glycol moieties present; the steareth range of compounds such as steareth-1 through 10, which are ethylene glycol ethers of alcohol steareth, in which the numerical designation indicates the number of ethylene glycol moieties present; ceteareth 1 to ceteareth-10, which are the ethylene glycol ethers of ceteareth alcohol, i.e. a mixture of fatty alcohols containing mainly cetearyl and stearyl alcohol, in which the numerical designation indicates the number of fractions ethylene glycol present; the C ₁ to C ₃₀ alkyl ethers of the ceteth, steareth and ceteareth compounds which have just been described; polyoxyethylenated ethers of branched alcohols such as octyldodecyl alcohol, dodecylpentadecylic alcohol, hexyldecyl alcohol, and isostearyl alcohol; polyoxyethylene ethers of behenyl alcohol; PPG ethers such as PPG-9 steareth-3, PPG-11 stearyl ether, PPG8 ceteth-1, and PPG-10 cetyl ether; and one of their mixtures. The liquid fatty ethers can be chosen from liquid dialkyl ethers such as dicaprylyl ether. The non-liquid fatty ethers can also be chosen from dialkyl ethers and in particular dicetyl ether and distearyl ether, alone or as a mixture.

Esters of C ₄ to C ₂₂ dicarboxylic or tricarboxylic acids and C ₁ to C ₂₂ alcohols and esters of monocarboxylic, dicarboxylic or tricarboxylic acids of C ₄ dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy non-sugar alcohols at C ₂₆ can also be used. Mention may be made in particular of diethyl sebacate; diisopropyl sebacate; diisopropyl adipate; di-n-propyl adipate; triisopropyl citrate; glyceryl trilactate; glyceryl trioctanoate; neopentyl glycol diheptanoate; and diethylene glycol diisononanoate.

Fatty acid derivatives

Cosmetic compositions may, in some cases, include fatty acid derivatives. Fatty acid derivatives are defined herein to include fatty acid esters of fatty alcohols as defined above, fatty acid esters of fatty alcohol derivatives as discussed above when such derivatives fatty alcohol compounds include an esterifiable hydroxyl group, fatty acid esters of alcohols other than the fatty alcohols and fatty alcohol derivatives described above, hydroxy-substituted fatty acids, and a mixture thereof . Non-limiting examples of fatty acid derivatives include ricinoleic acid, glycerol monostearate, 12-hydroxy stearic acid, ethyl stearate, cetyl stearate, cetyl palmitate, cetyl ether polyoxyethylene stearate , polyoxyethylene stearyl ether stearate, polyoxyethylene lauryl ether stearate, ethylene glycol monostearate, polyoxyethylene monostearate, polyoxyethylene distearate, propylene glycol monostearate, propylene glycol distearate, trimethylolpropane distearate, sorbitan stearate, polyglyceryl, dimethyl sebacate, PEG-15 cocoate, PPG-15 stearate, glyceryl monostearate, glyceryl distearate, glyceryl tristearate, PEG-8 laurate, PPG-2 isostearate , PPG-9 laurate, and a mixture thereof.

(E) Monoalcohol(s)

The cosmetic compositions include one or more monoalcohols comprising from 2 to 6 carbon atoms. For example, the one or more monoalcohols can include or be selected from ethanol, propanol, butanol, pentanol, hexanol, isopropyl alcohol, cycohexanol, isobutyl alcohol, 2-methyl-2-butanol (2-methylbutan-2-ol), and one of their blends. In one instance, the one or more monoalcohols include ethanol and optionally one or more additional monoalcohols having 2 to 6 carbon atoms. In another case, the one or more monoalcohols include only ethanol or essentially only ethanol.

The total amount of monoalcohols can vary but is typically about 0.05 to about 70% by weight, based on the total weight of the composition. For example, the total amount of monoalcohols is about 0.05 to about 30% by weight, about 0.5 to about 25% by weight, about 1 to about 20% by weight, about 1.5 to about 15% by weight, about 2 to about 10% by weight, about 2.5 to about 5% by weight, including ranges and subranges included, based on the total weight of the cosmetic composition. Additionally or alternatively, the cosmetic compositions can include an amount of ethanol ranging from about 0.05 to about 30% by weight, about 0.5 to about 25% by weight, about 1 to about 20% by weight, about 1.5 to 15 wt%, about 2 to 10 wt%, about 2.5 to about 5 wt%, inclusive ranges and subranges, based on the total weight of the composition. The amount of ethanol in the cosmetic composition can be about 0.05 to about 30% by weight, about 0.5 to about 25% by weight, about 1 to about 20% by weight, about 1.5 to about 15% by weight, about 2 to about 10% by weight, about 2.5 to about 5% by weight, including ranges and subranges included, based on the total weight of the cosmetic composition.

Thickener(s)

The cosmetic compositions described herein can optionally include a thickener. The thickener can be in an amount of about 0.1 wt% to about 20 wt%, about 0.1 to about 10 wt%, about 0.1 wt% to about 9 wt%, about 0.2 wt% to about 9 wt%, about 0.3 wt% to about 9 wt%, about 0.4 wt% to about 8 wt%, about 0.5 wt% to about 5 wt%, about 1 wt% to about 5 wt%, or about 2 wt% to about 4 wt%, inclusive ranges and subranges, based on the total weight of the cosmetic composition. Also, the amount of thickener can be 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0 , or 1.5% by weight at 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, or 20% by weight, including ranges and subranges thereof, based on the total weight of the cosmetic composition.

The thickener(s) may be chosen from xanthan gum, guar gum, a biosaccharide gum, cellulose, acacia gum from Senegal, sclerotium gum, agarose, pectin, gelan gum, hyaluronic acid. Additionally, the one or more thickeners may include polymeric thickeners selected from the group consisting of ammonium polyacryloyldimethyl taurate, ammonium acryloyldimethyltaurate/VP copolymer, poly(sodium acrylate), acrylate copolymers , polyacrylamide, a carbomer, and a crosslinked polymer of acrylates/C ₁₀ to C ₃₀ alkyl acrylate. In some cases, the composition includes ammonium polyacryloyldimethyl taurate and/or poly(sodium acrylate).

Many thickeners are soluble in water, and increase the viscosity of water or form an aqueous gel when the cosmetic composition of the invention is dispersed/dissolved in water. The aqueous solution can be heated and cooled, or neutralized, to form the gel, if necessary. The thickener can be dispersed/dissolved in an aqueous solvent which is soluble in water, for example, ethyl alcohol when dispersed/dissolved in water. Non-limiting examples of various types of thickeners include:

Polymers of carboxylic acids

These polymers are crosslinked compounds containing one or more monomers derived from acrylic acid, substituted acrylic acids, and salts and esters of these acrylic acids and substituted acrylic acids, wherein the crosslinking agent contains two or more carbon-carbon double bonds and is derived from a polyhydric alcohol.

Examples of commercially available carboxylic acid polymers useful herein include carbomers, which are homopolymers of acrylic acid crosslinked with allyl ethers of sucrose or pentaerytritol. Carbomers are available under the Carbopol.RTM range. 900 from BF Goodrich (for example, Carbopol® 954). Additionally, other suitable polymeric carboxylic acid agents include Ultrez® 10 (BF Goodrich) and copolymers of C ₁₀ -C ₃₀ alkyl acrylates with one or more acrylic acid monomers, methacrylic acid , or one of their short chain esters (i.e., C ₁ -C ₄ alcohol), in which the crosslinking agent is an allyl ether of sucrose or pentaerytritol. These copolymers are known as acrylate/C ₁₀ -C ₃₀ alkyl acrylate cross-linked polymers and are commercially available under the names Carbopol.RTM. 1342, Carbopol® 1382, Pemulen TR-1, and Pemulen TR-2, from BF Goodrich. In other words, examples of carboxylic acid polymer thickeners useful herein are those selected from carbomers, crosslinked C ₁₀ -C ₃₀ alkyl acrylate/acrylate polymers, and mixtures thereof.

Cross-linked polyacrylate polymers

The cosmetic compositions may optionally contain cross-linked polyacrylate polymers useful as thickeners or gelling agents including cationic and nonionic polymers. Examples of useful cross-linked nonionic polyacrylate polymers and cross-linked cationic polyacrylate polymers are those described in U.S. Patent No. 5,100,660, U.S. Patent No. 4,849,484, U.S. Patent No. 4,835,206, U.S. Patent No. 4,628,078, US Patent No. 4,599,379 and EP 228,868, all of which are incorporated herein by reference in their entirety for all purposes.

Polyacrylamide polymers

The cosmetic compositions may optionally contain polyacrylamide polymers, especially nonionic polyacrylamide polymers including branched or unbranched substituted polymers. Among these polyacrylamide polymers, there is the nonionic polymer of CTFA designation polyacrylamide and isoparaffin and laureth-7, available under the trade name Sepigel 305 from Seppic Corporation.

Other polyacrylamide polymers useful herein include multi-block copolymers of acrylamides and substituted acrylamides with acrylic acids and substituted acrylic acids. Commercially available examples of such multi-block copolymers include Hypan SR150H, SS500V, SS500W, SSSA100H, from Lipo Chemicals, Inc.

The cosmetic composition may also contain thickening and texturizing gels of the type exemplified by the product line called Lubrajel® from United Guardian. These gels have moisturizing, viscosifying and stabilizing properties.

Polysaccharides

A wide variety of polysaccharides can be useful here. "Polysaccharides" refers to gelling agents that contain a backbone of repeating sugar (ie, carbohydrate) units. Non-limiting examples of polysaccharide gelling agents include those selected from the group consisting of cellulose, carboxymethyl hydroxyethyl cellulose, cellulose acetate propionate carboxylate, hydroxyethyl cellulose, hydroxyethyl ethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose , methyl hydroxyethyl cellulose, microcrystalline cellulose, sodium sulfate cellulose, and mixtures thereof. Also useful herein are alkyl-substituted celluloses. Among the alkyl hydroxyalkyl cellulose ethers is the CTFA designation material cetyl hydroxyethyl cellulose, which is the ether of cetyl alcohol and hydroxyethyl cellulose. This material is sold under the tradename Natrosol® CS Plus from Aqualon Corporation.

Other useful polysaccharides include scleroglucans comprising a linear chain of glucose (1-3) units linked with one glucose (1-6) linked every three units, a commercially available example of which is Clearogel ^TM . CS11 at Michel Mercier Products Inc.

Erasers

Other thickening and gelling agents useful herein include materials which are primarily derived from natural sources. Non-limiting examples of such gelling agent gums include acacia, agar, algin, alginic acid, ammonium alginate, amylopectin, calcium alginate, calcium carrageenan , carnitine, carrageenan, dextrin, gelatin, gelan gum, guar gum, guar hydroxypropyltrimonium chloride, hectorite, hyaluronic acid, hydrated silica, hydroxypropyl chitosan, hydroxypropyl guar, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, sclerotium gum, sodium carboxymethyl dextran, sodium carrageenan, gum tragacanth, xanthan gum, and mixtures thereof.

Additional examples of water-soluble thickeners include natural water-soluble polymers, synthetic water-soluble polymers, clay minerals and silicic anhydride. Non-limiting examples of water-soluble natural polymers include gum arabic, gum tragacanth, karaya gum, guar gum, gelan gum, tara gum, locust bean gum, tamarind gum , sodium alginate, propylene glycol ester of alginic acid, carrageenan, farcelluran, agar-agar, high-methoxylated pectin, low-methoxylated pectin, xanthine, chitosan, starch (for starch derived from corn, potato, wheat, rice, sweet potato and tapioca, α-starch, soluble starch), a fermentation polysaccharide (e.g. xanthan gum, pullulan, carcirane, dextran), an acid hetero-polysaccharide derived from the callus of plants belonging to Polyantes sp. (eg, a tuberous polysaccharide), proteins (eg, sodium casein, gelatin, albumin), chondroitin sulfate, and hyaluronic acid.

Non-limiting examples of water-soluble synthetic polymers include poly(vinyl alcohol), poly(sodium acrylate), poly(sodium methacrylate), poly(acrylic acid) glycerin ester, carboxyvinyl polymer, polyacrylamide, polyvinyl pyrrolidone, polyvinyl methyl ether, polyvinyl sulfone, maleic acid copolymer, poly(ethylene oxide), polydiallyl amine, polyethylene imine, water-soluble cellulose derivatives water (eg, carboxymethyl cellulose, methyl cellulose, methylhydroxypropyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, cellulose sulfate sodium salt), and starch derivatives (eg, oxide of starch, dialdehyde starch, dextrin, achroodextrin, acetyl starch, starch phosphate, carboxymethyl starch, hydroxyethyl starch, hydroxypropyl starch).

Active ingredients

The cosmetic composition and/or ceramide compositions can include one or more active ingredients. The cosmetic and/or ceramide composition may include 10 ppm to 10 wt% (100,000 ppm), 10 ppm to 5 wt% 50,000 ppm), 10 ppm to 2.5 wt% (25,000 ppm), 10 ppm at 1 wt% (10,000 ppm), 10 ppm at 0.5 wt% (5,000 ppm), 10 ppm at 0.1 wt% (1,000 ppm), or 10 ppm at 500 ppm one or more active ingredients. In some cases, the one or more active ingredients is (are) present in an amount of 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 150, or 200 ppm at 500, 600, 700, 800, 900, 0.1 wt% (1,000 ppm), 0.5 wt% (5,000 ppm), 1 wt% (10,000 ppm), 5 wt% (50,000 ppm ), or 10% by weight (100,000 ppm), based on the total weight of the ceramide or cosmetic composition.

Non-limiting examples of the one or more active agents include adenosine, 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid (HEPES), hyaluronic acid, lanolin, citric acid, malic acid, lactic acid, tartaric acid, salicylic acid, vitamin C, vitamin, retinoid, retinal, retinoic acid, carotenoid, amino acid, protein, an enzyme, and a coenzyme. In some cases, the active ingredient is adenosine.

In one embodiment, the formulation includes an active ingredient such as a humectant and moisturizing ingredients, an anti-aging agent, a depigmenting agent, an anti-wrinkle agent, or an agent that treats oily skin.

Humectants and moisturizing ingredients can be included in the cosmetic composition and/or the ceramide compositions. For example, the active ingredient can include or be chosen from glycerol and its derivatives, urea and its derivatives, in particular Hydrovance marketed by National Starch, lactic acid, hyaluronic acid, AHA, BHA, pidolate of sodium, xylitol, serine, sodium lactate, ectoin and its derivatives, chitosan and its derivatives, collagen, plankton, an extract of Imperata cylindra sold under the name Moist 24 by Sederma, homopolymers of acrylic acid under the name Lipidure-HM from NOF Corporation, beta-glucan and in particular sodium carboxymethyl beta-glucan Mibelle-AG-Biochemistry, a mixture of oils of passion flower, apricot, corn , and rice bran sold by Nestle under the name NutraLipids, a C-glycoside derivative, in particular C-13-D-xylopyranoside-2-hydroxypropane in the form of a solution with 30% by weight of active ingredient in a water/propylene glycol mixture (60/40% by weight) such as the product produced by the company Chimex under the trade name co mmercial "Mexoryl SBB", a rosehip oil marketed by Nestle, a zinc-enriched Prophyridium cruentum micro-algae extract, marketed as Vincience Algualane Zinc spheres of collagen and marine-derived chondroitin sulfate (Atelocollagen) sold by the company Engelhard Lyon under the name Marine Filling Spheres, spheres of hyaluronic acid such as those marketed by Engelhard Lyon, and arginine.

Depigmentation agents include vitamin C and its derivatives and in particular vitamin CG, CP and 3-O ethyl vitamin C, alpha and beta arbutin, ferulic acid, lucinol and its derivatives, kojic acid , resorcinol and its derivatives, tranexamic acid and its derivatives, gentisic acid, homogentisic acid, methyl gentisate or homogentisate, dioic acid, D pantheteine calcium sulfonate, lipoic acid, ellagic acid, vitamin B3, linoleic acid and its derivatives, ceramides and their counterparts, derived from plants such as chamomile, bearberry, aloe family (vera, ferox, bardensis), blackberry, skullcap , a water kiwi (Actinidia chinensis) marketed by Gattefosse, a root extract of Paeonia suffruticosa, such as that sold by Ichimaru Pharcos under the name Liquid Botanpi Be and an extract of brown sugar (Saccharum officinarum) such as the extract of molasses marketed by Taiyo Kagaku under the name Liquid Mol asses, without this list being exhaustive. Particular depigmentation agents include vitamin C and its derivatives and in particular vitamin CG, CP and 3-O ethyl vitamin C, alpha and beta arbutin, ferulic acid, kojic acid, resorcinol and derivatives, D panthetein calcium sulfonate, lipoic acid, ellagic acid, vitamin B3, a water kiwi (Actinidia chinensis) marketed by Gattefosse, an extract of Paeonia suffruticosa root, such as that sold by the company Ichimaru Pharcos under the name Botanpi Liquid B.

The expression "anti-wrinkle active" refers to a natural or synthetic compound producing a biological effect, such as the synthesis and/or the increased activity of certain enzymes, when it is brought into contact with an area of wrinkled skin, this having the effect of reducing the appearance of wrinkles and/or fine lines. By way of example, anti-wrinkle active agents can be chosen from: desquamation agents, anti-glycation agents, NO-synthase inhibitors, agents stimulating the synthesis of dermal or epidermal macromolecules and/or preventing their degradation, agents for stimulating the proliferation of fibroblasts and/or keratinocytes, or for stimulating agents for reducing the differentiation of keratinocytes; muscle relaxants and/or dermo-decontracting agents, anti-free radical agents, and mixtures thereof.

Examples of such compounds are: adenosine and its derivatives and retinol and its derivatives such as retinol palmitate, ascorbic acid and its derivatives such as magnesium ascorbyl phosphate and ascorbyl glucoside; tocopherol and its derivatives such as tocopheryl acetate, nicotinic acid and its precursors such as nicotinamide; ubiquinone; glutathione and its precursors such as L-2-oxothiazolidine-4-carboxylic acid, C-glycoside compounds and their derivatives as described in particular in document EP-1345919, in particular C-beta-D-xylopyranoside- 2-hydroxy-propane as described in particular in document EP-1345919, plant extracts including sea fennel and olive leaf extracts, as well as plants and their hydrolysates such as rice protein hydrolysates or soy protein; seaweed extracts and in particular bacterial extracts of laminaria, sapogenins such as diosgenin and extracts of dioscorean plants, in particular hairy yam, comprising: α-hydroxy acids, β-hydroxy acids, such as salicylic acid and n-octanoyl-5-salicylic oligopeptides and pseudodipeptides and their acyl derivatives, in particular {2-[acetyl-(3-trifluoromethyl-phenyl)-amino]-3-methyl-}acetic acid and lipopeptides marketed by the company under the trade names SEDERMA Matrixyl 500 and Matrixyl 3000; lycopene, manganese salts and magnesium salts, in particular gluconates, and mixtures thereof.

Adenosine derivatives include in particular non-adenosine phosphate derivatives, such as in particular 2′-deoxyadenosine, 2′,3′-adenosine isopropoylidene; toyocamycin, 1-methyladenosine, N-6-methyladenosine; adenosine N-oxide, 6-methylmercaptopurine riboside, and 6-chloropurine riboside.

Other derivatives include adenosine receptor agonists such as phenylisopropyl adenosine ("PIA") adenosine, 1-methylisoguanosine, N6-cyclohexyladenosine (CHA), N6-cyclopentyladenosine (CPA), 2-chloro -N6-cyclopentyladenosine, 2-chloroadenosine, N6-phenyladenosine, 2-phenylaminoadenosine, MECA, N6-phenethyladenosine, 2-p-(2-carboxy-ethyl) phenethyl-amino-5'--N- ethylcarboxamido adenosine (CGS-21680), N-ethylcarboxamido-adenosine (NECA), 5'(N-cyclopropyl)-carboxamidoadenosine, DPMA (PD 129.944) and metrifudile.

In some cases, the cosmetic and/or ceramide composition includes an active ingredient that addresses the issue of oily skin. These active agents can be sebum-regulating or anti-seborrheic agents capable of regulating the activity of the sebaceous glands. These include: retinoic acid, benzoyl peroxide, sulfur, (pyridoxine or) vitamin B6 chloride, selenium, glasswort-cinnamon extract blends, tea, and octanoylglycine such as - 15 Sepicontrol A5 TEA from Seppic - the mixture of cinnamon, sarcosine and octanoylglycine marketed in particular by Seppic under the trade name Sepicontrol A5 - zinc salts such as zinc gluconate, zinc pyrrolidonecarboxylate (or zinc), zinc lactate, zinc aspartate, zinc carboxylate, zinc salicylate, zinc cysteate; - derivatives in particular copper and copper pidolate such as extracts of Cuivridone Solabia - of plants of Arnica montana, Cinchona succirubra, Eugenia caryophyllata, Humulus lupulus, Hypericum perforatum, Mentha pipenta 25 Rosmarinus officinalis, Salvia officinalis and Thymus vulgaris , all marketed for example by Maruzen - extracts of meadowsweet (Spiraea ulmaria), such as that sold under the name Sebonormine by Silab - extracts of the seaweed Laminaria saccharina, such as that sold under the name Phlorogine by Biotechmarine - extracts of burnet mix root (Sanguisorba officinalis/Poterium officinale), ginger rhizomes (Zingiber officinalis) and cinnamon bark (Cinnamomum cassia), such as that sold under the name Sebustop by Solabia - extracts of flax seeds such as that sold under the name Linumine by Lucas Meyer - Phellodendron extracts such as those sold under the name Phellodendron extract BG by M aruzen or Oubaku Liquid B by Ichimaru Pharcos - mixtures of argan oil extracted from Serenoa serrulata (sweet palm) and sesame seeds such as that sold under the name Regu SEB by Pentapharm - mixtures of willowherb extracts , Terminalia chebula, nasturtium and bioavailable zinc (microalga), such as that sold under the name Seborilys Green Tech; - extracts of Pygeum afrianum such as that sold under the name sterolic lipid extract of Pygeum afrianum by Euromed - extracts of Serenoa serrulata such as that sold under the name Viapure Sabal by Actives International, and that sold by the company Euromed - extracts of mixtures of plantain, Berberis aquifolium and sodium salicylate 20 such as that sold as Seboclear Rahn - clove extract such as that sold as Clove extract powder by Maruzen - argan oil such as that sold under the name Lipofructyl Laboratories Serobiologiques; lactic protein filtrates, such as that sold under the name Normaseb by Sederma - seaweed laminaria extracts, such as that sold under the name Laminarghane by Biotechmarine - seaweed oligosaccharides Laminaria digitata, such as that sold under the name Phycosaccharide 30 AC by the company Codif - sugar cane extracts such as that sold under the name Policosanol by the company Sabinsa, sulphonated shale oil, such as that sold under the name Ichthyol Pale by Ichthyol - extracts of meadowsweet (Spiraea ulmaria) such as that sold under the name Cytobiol Ulmaire by the company Libiol - sebacic acid, in particular sold in the form of sodium polyacrylate gel under the name Sebosoft by Sederma - glucomannans extracts of konjac tuber and modified with alkylsulfonate chains such as that sold under the name Biopol Beta by Arch Chemical - extracts of Sophora angustifolia, such as that sold under the no m Sophora powder or extract of Sophora by Bioland - extracts of cinchona succirubra bark such as that sold under the name Red Bark HS by Alban Muller - extracts of Quillaja saponaria such as that sold under the name 15 Panama wood HS by Alban Muller - glycine grafted on an undecylenic chain, such as that sold under the name Lipacide UG OR by SEPPIC - the mixture of oleanolic acid and nordihydroguaiaretic acid, such as that sold in the form of a gel under the name AC.Net by Sederma; tri(C ₁₂ -C ₁₃ ) citrate of 20-phthalimidoperoxyhexanoic acid sold under the name COSMACOL.RTM. ECI by Sasol; a trialkyl (C14-C15) citrate sold under the name COSMACOL.RTM. ECL by Sasol - 10-Hydroxydecanoic acid, including mixtures of 25 October hydroxydecanoic acid, sebacic acid and 1,10-decandiol such as that sold as Acnacidol BG by Vincience and mixtures thereof.

Methods for producing capsule containing ceramide

The present disclosure also relates to methods of preparing the ceramide-containing capsules and/or ceramide compositions disclosed herein. A non-limiting example of a method of preparing a ceramide composition typically includes:

(I) the provision of a mixture at room temperature comprising:

(a) an oily phase comprising:

(i) ceramide NP,

(ii) hydroxypalmitoyl sphinganine,

(iii) 2-oleamido-1,3-octadecanediol, and

wherein a weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is from 1:2.5 to 1:5, And

(iv) a hydrophobic solvent,

(b) a liposome precursor which is immiscible with water and with the oil phase, wherein the liposome precursor comprises:

(i) a polycaprolactone,

(ii) a block copolymer, and

(ii) a surfactant,

(c) acetone, wherein a weight ratio of the oil phase of (a) and the liposome precursor of (b) to the acetone of (c) is from 1:20 to about 1:40,

(II) homogenization of the oily phase and the liposome precursor at a temperature of 30°C or more;

(III) the dispersion of the homogeneous mixture of (II) in a preheated aqueous phase, in order to obtain an emulsion, the preheated aqueous phase comprising a block copolymer;

(IV) distilling the solvent of (III) to remove the acetone and the concentrate resulting from the mixture for the coacervation of the liposome precursor and for the coating of drops of said oily phase with the coacervates to obtain a suspension;

(V) cooling the suspension of step (IV) to a temperature for the formation of capsules by precipitation and/or crystallization of the coacervates; And

(VI) addition of hydroxyacetophenone.

The mixture typically includes a weight ratio of the oil phase combination of (a) and the liposome precursor of (b) to the acetone of (c) of from 1:20 to about 1:40. In some cases, however, the weight ratio of oil phase from (a) and liposome precursor from (b) to acetone from (c) is 1:20 to 1:40, 1:25 to 1 :40, 1:27 to 1:40, 1:20 to 1:35, 1:25 to 1:33, or 1:27 to 1:33, including included ranges and sub-ranges. In yet a further embodiment, the weight ratio of the oily phase of (a) and liposome precursor of (b) to the acetone of (c) may be about 1:30.

The homogenization of the oily phase and the liposome precursor occurs at a temperature greater than room temperature. For example, the homogenization of step (II) typically occurs at a temperature of 30°C or higher, preferably about 40°C or higher, about 45°C or higher, or about 50°C or higher. Additionally, it may be desirable to homogenize the oil phase and the liposome precursor at a temperature that does not exceed 100°C, for example, does not exceed 80°C and/or 60°C. In at least one case, the homogenization of step (II) occurs at a temperature of about 50°C.

Additional subject matter relating to steps (I) through (VI) or methods of producing capsules can be found in US Patent Publication No. 2009/0047341, which is incorporated herein in its entirety for convenience. One of ordinary skill in the art would understand how to perform the methods of producing ceramide-containing capsules and/or ceramide compositions from the incorporated references and this disclosure.

Methods of use

In accordance with one aspect of the disclosure, methods are provided for preparing cosmetic compositions from the ceramide compositions and/or the ceramide-containing capsule. Advantageously, cosmetic compositions comprising capsules containing ceramide can be prepared by adding the ceramide compositions during or after the procedures for preparing the cosmetic compositions.

According to another aspect of the present disclosure, methods of using the cosmetic compositions described herein are provided. For example, the cosmetic compositions can be used in a method for supporting the barrier function of the skin's natural lipids, wherein the method comprises applying the cosmetic composition to the skin or hair. The methods can also improve the skin barrier functionality of a user's skin. In some cases, the processes may promote regeneration, renewal, and/or repair of compromised skin. Additionally or alternatively, the methods may provide improved skin appearance, such as anti-inflammation, improved skin pigmentation, and the like.

Typically, the cosmetic compositions are applied to human skin or hair. In some cases, the composition is applied to the face. Additionally, the cosmetic composition can be used in methods of treating dry skin and/or hair, repairing damage to the skin and/or hair (e.g., damage associated with aging, exposure to UV, drought, etc.), and to diminish the appearance of wrinkles, blackheads, and uneven skin texture. These methods also involve applying the cosmetic compositions described herein to the skin and/or hair, and in some cases to the face. The aforementioned methods are typically non-therapeutic.

The cosmetic composition can be applied once a day, twice a day, or more than once or twice a day. In some cases, the cosmetic composition is applied in the evening before going to bed. In other cases, the cosmetic compositions are applied in the morning. In still other cases, the composition can be applied immediately after washing the skin and/or the hair. The compositions can be used once, or for a series of days, weeks, or months. For example, the compositions can be used daily for a period of 1, 2, 3, 4, 5, 6, 7, 8 or weeks or months, or longer.

Disclosure Embodiments

In certain embodiments, the ceramide compositions of the present disclosure include:

(I) capsules dispersed in the ceramide composition, the capsules comprising:

(a) a shell comprising:

(i) a polycaprolactone, such as about 10 to about 70% by weight, based on the total weight of the shell components, of a polycaprolactone selected from polycaprolactone diols having a weight average molecular weight of 100 to 20,000 and /or up to 100 monomer units,

(ii) a block copolymer of, for example, about 10 to about 70% by weight, based on the total weight of the shell components, of a poloxamer having a weight average molecular weight of 1,000 to 900,000, and

(iii) a surfactant, such as about 10 to about 70% by weight, based on the total weight of the shell components, of a surfactant selected from phospholipid surfactants, and

(b) a core comprising:

(i) ceramide NP, for example in an amount ranging from about 1 to about 15% by weight, based on the total weight of the core components,

(ii) hydroxypalmitoyl sphinganine, for example, in an amount ranging from about 1 to about 15% by weight, based on the total weight of the core components,

(iii) 2-oleamido-1,3-octadecanediol, for example, in an amount ranging from about 1 to about 60% by weight, based on the total weight of the core components,

wherein a weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is from 1:2.5 to 1:5 or from 1:2.5 to 1:4, and

(iv) a hydrophobic solvent, such as 2-octyl-1-dodecanol, for example, in an amount ranging from about 35 to about 90% by weight, based on the total weight of the core components;

(II) a hydrophilic solvent, such as water; And

(III) hydroxyacetophenone.

In additional embodiments, a method of preparing a ceramide composition includes:

(I) the provision of a mixture at room temperature comprising:

(a) an oily phase comprising:

(i) ceramide NP,

(ii) hydroxypalmitoyl sphinganine,

(iii) 2-oleamido-1,3-octadecanediol,

wherein a weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is from 1:2.5 to 1:5 or from 1:2.5 to 1:4, and

(iv) a hydrophobic solvent, such as 2-octyl-1-dodecanol;

(b) a liposome precursor which is immiscible with water and with the oil phase, wherein the liposome precursor comprises:

(i) a polycaprolactone, such as a polycaprolactone chosen from polycaprolactone diols having a weight-average molecular weight of 100 to 20,000 and/or up to 100 monomer units,

(ii) a block copolymer, such as a poloxamer having a weight average molecular weight of 1,000 to 900,000, and

(iii) a surfactant, such as those selected from phospholipid surfactants, and

(c) acetone, wherein a weight ratio of the oil phase of (a) and the liposome precursor of (b) to the acetone of (c) is from 1:20 to about 1:40,

(II) homogenization of the oily phase and the liposome precursor at a temperature of 30°C or more;

(III) the dispersion of the homogeneous mixture of (II) in a preheated aqueous phase, in order to obtain an emulsion, the preheated aqueous phase comprising a block copolymer;

(IV) distilling the solvent of (III) to remove the acetone and the concentrate resulting from the mixture for the coacervation of the liposome precursor and for the coating of drops of said oily phase with the coacervates to obtain a suspension;

(V) cooling the suspension of step (IV) to a temperature for the formation of capsules by precipitation and/or crystallization of the coacervates; And

(VI) addition of hydroxyacetophenone.

In a further embodiment, there is provided a cosmetic composition including:

(A) about 1% to about 20% by weight of a ceramide composition, the ceramide composition comprising:

(I) capsules dispersed in the ceramide composition, the capsules comprising:

(a) a shell comprising:

(i) a polycaprolactone, such as about 10 to about 70% by weight, based on the total weight of the shell components, of a polycaprolactone selected from polycaprolactone diols having a weight average molecular weight of 400 to 10,000 and /or up to 100 monomer units,

(ii) a poloxamer, for example, about 10 to about 70% by weight, based on the total weight of the shell components, of a poloxamer having a weight average molecular weight of 1,000 to 800,000, and

(iii) a surfactant comprising a phospholipid group, such as lecithin in an amount of from about 10 to about 70% by weight, based on the total weight of the shell components, and

(b) a core comprising:

(i) ceramide NP, for example, in an amount ranging from about 1 to about 15% by weight, based on the total weight of the core components,

(ii) hydroxypalmitoyl sphinganine, for example in an amount ranging from about 1 to about 15% by weight, based on the total weight of the core components,

(iii) 2-oleamido-1,3-octadecanediol, for example, in an amount ranging from about 1 to about 60% by weight, based on the total weight of the core components,

wherein a weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is from 1:2.5 to 1:5 or from 1:2.5 to 1:4, and

(iv) a hydrophobic solvent, such as 2-octyl-1-dodecanol, for example, in an amount ranging from about 35 to about 90% by weight, based on the total weight of the core components;

(II) a hydrophilic solvent, such as water; And

(III) hydroxyacetophenone;

(B) optionally, an emulsifier, such as those chosen from amphoteric, anionic, cationic or nonionic emulsifiers in an amount ranging from about 0.001 to about 25% by weight, based on the total weight of the cosmetic composition;

(C) optionally, a polyol, including polyols having 2 to 15 carbon atoms and at least two hydroxyl groups in an amount ranging from about 0.1 to about 25% by weight, based on the total weight of the cosmetic composition;

(D) optionally, a fatty compound, such as those selected from oils, mineral oil, fatty alcohols, fatty acids, fatty alcohol derivatives, and fatty acid derivatives in an amount ranging from about 0.1 to about 25% by weight, based on the total weight of the cosmetic composition; And

(E) optionally, a monoalcohol.

Examples

An implementation of this disclosure is provided using the following examples. The following examples serve to elucidate aspects of the technology without being limiting in nature.

Example 1

(Formulations)

An example of ceramide compositions was prepared (Example 1). Four comparative examples of ceramide compositions (Comparative Examples 1-4) were prepared in accordance with the method of preparation of Example 1. The formulations for Example 1 and Comparative Examples 1-4 are provided in Table 1. , below.

INCI Example 1 Comp. 1 Comp. 2 Comp. 3 Comp. 4 Shell Poloxamer POLOXAMER 188 0.5 0.5 0.5 0.5 0.5 Polycaprolactone POLYCAPROLACTONE DIOL 1 1 1 1 1 Liposome precursor LECITHIN 1 1 1 1 1 Core Ceramide (i) CERAMIDE III NP 0.2 0.25 0.25 0.25 0.2 (ii) CERAMIDE 5 – HYDROXYPALMITOYL SPHINGANINE 0.2 0.25 0.25 0.25 0.2 (iii) N-OLEYL DI-HYDROSPHINGOSINE TECHNICAL (2-OLEAMIDO-1,3-OCTADECANEDIOL) 1.1 1 1 1 1.1 weight ratio of (i) to (ii) to (iii) 1:1:5.5 1:1:4 1:1:4 1:1:4 1:1:5.5 fatty alcohol 2-OCTYL-1-DODECANOL 3.5 3.5 3.5 3.5 3.5 Conservatives PHENETHYL ALCOHOL 1 PHENOXYETHANOL 0.7 4'-HYDROXYACETOPHENONE 1 1 PENTANE-1,2-DIOL 10 10 Water WATER 91.5 90.8 91.5 82.5 82.5

Example 2

(Stability assessment)

Example 1 and Comparative Examples 1-4 were evaluated for temporal stability. Specifically, samples of Example 1 and Comparative Examples 1-4 were preserved in environmental chambers at temperatures of standard room temperature, 5 °C, and 45°C. The samples were then evaluated after one week.

Example 1 was determined to be stable and exhibit no coagulation/aggregation. Specifically, Example 1 was determined to show no coagulation because Example 1 had a uniform white to pinkish milky liquid appearance. Comparative Example 1 showed no coagulation. Comparative Example 2 showed slight coagulation. In particular, Comparative Example 2 exhibited slight coagulation forming lumps and having an uneven appearance. Comparative Example 3 showed coagulation. In particular, Comparative Example 3 was designated as exhibiting coagulation because Comparative Example 3 separated to form a significant amount of lumps and a liquid medium. Comparative Example 4 was determined to be unstable because Comparative Example 4 formed a thick paste.

Example 3

(Evaluation of ceramide weight ratios)

Three compositions (compositions A through C) containing different ratios of ceramides were prepared and evaluated. The formulation of the three compositions is provided in Table 2, below.

INCI Composition A Composition B Composition C (i) CERAMIDE III NP 0.25 0.2 0.15
(ii) CERAMIDE 5 – HYDROXYPALMITOYL SPHINGANINE 0.25 0.2 0.15 (iii) N-OLEYL DI-HYDROSPHINGOSINE TECHNICAL (2-OLEAMIDO-1,3-OCTADECANEDIOL) 1 1.1 1.2 weight ratio of (i) to (ii) to (iii) 1:1:4 1:1:5.5 1:1:8

Compositions A-C were prepared in a beaker by heating the three ceramides to 50°C in 2-octyl-1-dodecanol in the amounts and ratios provided in Table 2. Compositions A-C were visually clear and transparent at a temperature of 50°C. After compositions A through C were cooled to room temperature, composition A was visually determined to be slightly hazy, while compositions B and C were clear and transparent. The solubility of compositions B and C was better than the solubility of composition A.

The term "INCI" is an abbreviation of International Nomenclature of Cosmetic Ingredients, which is a naming system provided by the International Nomenclature Committee of the Personal Care Products Council for describing personal care ingredients.

As used herein, all ranges provided are intended to include each specific range within the given ranges, and a combination of the subranges therebetween. Thus, a range of 1 to 5, specifically includes 1, 2, 3, 4, and 5, as well as subranges such as 2 to 5, 3 to 5, 2 to 3, 2 to 4, 1 to 4, etc. .

All components and elements positively presented in the present disclosure can be negatively excluded from the claims. In other words, the hair cleansing compositions of this disclosure may be free or substantially free of all of the components and elements positively stated throughout this disclosure.

In some instances, the hair cleansing compositions of the present disclosure may be substantially free of significant amounts of the ingredient(s) or compound(s) described herein. A significant amount of an ingredient or compound is the amount of that ingredient or compound that is added to the hair cleansing composition itself. For example, a hair cleansing composition may be substantially free of a significant amount of an ingredient or compound, although such ingredient(s) or compound(s) may (may) be present as part of a starting material which is included as a mixture of two or more compounds.

Some of the various component categories identified may overlap. In such cases where an overlap may exist and the hair cleansing composition includes both components (or the composition includes more than two overlapping components), an overlapping compound does not represent more than one component. For example, some compounds can be characterized as both an emulsifier and a surfactant. If a particular hair composition includes both an emulsifier and a surfactant, compounds that can be characterized as both an emulsifier and a surfactant will only serve as either an emulsifier or a surfactant - not both.

All publications and patent applications cited in this specification are hereby incorporated by reference, and for all intents and purposes, as if each individual publication or patent application were specifically and individually indicated as being incorporated by reference. In the event of any inconsistency between this disclosure and any publication or patent application incorporated herein by reference, this disclosure prevails.

As used herein, the terms "comprising", "having", and "including" are used in their broad, non-limiting sense.

The terms "a", "an", "the" and "the" are understood to include the plural as well as the singular. Thus, the expression “one of their mixtures” also relates to “their mixtures”. Throughout the disclosure, the expression "one of their mixtures" is used, following a list of elements as shown in the following example where the letters A to F represent the elements: "a or more members selected from the group consisting of A, B, C, D, E, F, and a mixture thereof”. The term "any mixture thereof" does not require that the mixture include all of A, B, C, D, E, and F (although all of A, B, C, D, E, and F can be included). Rather, it indicates that a mixture of any two or more of A, B, C, D, E, and F may be included. In other words, it is equivalent to the expression "one or more elements selected from the group consisting of A, B, C, D, E, F, and a mixture of any two elements of A, B, C, D, E, and F or more.”

The term "one or more" means "at least one" and thus includes individual components as well as mixtures/combinations.

Other than in the working examples, or unless otherwise indicated, all numbers expressing quantities of ingredients and/or reaction conditions may in all cases be modified by the term "approximately", meaning to within +/- 5% the number indicated.

The term "treating" (and its grammatical variations) as used herein refers to the application of the compositions of the present disclosure to the surface of keratinous substrates such as hair or hair on the head and/or body of an user.

The term "substantially free" or "essentially free" as used herein means that there is less than about 2% by weight of a specific material added to a composition, based on the total weight of the compositions. However, the compositions may include less than about 1 wt%, less than about 0.5 wt%, less than about 0.1 wt%, or none of the specified material. All components shown herein may be optionally included or excluded from the compositions/methods/kits. When excluded, compositions/methods/kits may be free or substantially free of the component. For example, a particular composition may be free or substantially free of silicones.

Claims (10)

Ceramide composition comprising:
(I) capsules dispersed in the ceramide composition, the capsules comprising:
(a) a shell comprising:
(i) a polycaprolactone,
(ii) a block copolymer, and
(iii) a surfactant, and
(b) a core comprising:
(i) ceramide NP,
(ii) hydroxypalmitoyl sphinganine,
(iii) 2-oleamido-1,3-octadecanediol,
wherein a weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is from 1:2.5 to 1:5, And
(iv) a hydrophobic solvent;
(II) a hydrophilic solvent; And
(III) hydroxyacetophenone. Ceramide composition according to claim 1, wherein the weight ratio of the ceramide NP of (i) and the hydroxypalmitoyl sphinganine of (ii) to the 2-oleamido-1,3-octadecanediol of (iii) is 1: 2.5 to 1:4. A ceramide composition according to any preceding claim, wherein the capsules have an average diameter of about 200nm to about 400nm. A ceramide composition according to any preceding claim, wherein the surfactant comprises a phospholipid group. A ceramide composition according to any preceding claim, wherein the hydrophobic solvent comprises a fatty alcohol selected from cetearyl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, arachidyl alcohol, eicosyl alcohol, myristyl alcohol, 2-dodecylhexadecanol, 2-tetradecyl-1-octadecanol, 2-tetradecyl-1-eicosanol, 2-hexadecyl-1-octadecanol, 2-hexadecyl-1-eicosanol, l octyldodecanol, 2-octyl-1-dodecanol, and one of their mixtures. A ceramide composition according to any preceding claim, wherein the hydrophilic solvent comprises water. A ceramide composition according to any preceding claim, wherein the core comprises:
(i) about 2 to about 8% by weight of ceramide NP,
(ii) about 2 to about 8% by weight hydroxypalmitoyl sphinganine,
(iii) about 10 to about 40% by weight 2-oleamido-1,3-octadecanediol, and
(iv) about 44 to about 86% by weight hydrophobic solvent, wherein the foregoing weight percentages of (i) through (iv) are based on the total core weight of (b). A ceramide composition according to any preceding claim which is phenoxyethanol free. A ceramide composition according to any preceding claim, further comprising at least one of:
(IV) an emulsifier;
(V) a polyol;
(VI) a fatty compound; And
(VII) a monoalcohol. Cosmetic composition according to any one of the preceding claims, in which the cosmetic composition improves the barrier function of the skin.