Note: Descriptions are shown in the official language in which they were submitted.
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Skin Care Compositions
Technical Field
The present invention relates to cosmetic compositions. In particular it relates to
cosmetic compositions in the form of emulsions which provide improved
moisturization, skin feel, skin care and appearamce benefits and reduced greasiness,
together with excellent rub-in and absorption characteristics. The compositions
also display excellent stability characteristics at normal and elevated temperatures.
Back~round of the Invention
Skin is made up of several layers of cells which coat and protect the keratin and
collagen fibrous proteins that form the skeleton of its structure. The outerrnost of
these layers, referred to as the ~ lulll corneum, is known to be composed of 25nm
protein bundles surrounded by 8nm thick layers. Anionic surfactants and organic
solvents typically penetrate the stratum corneunn membrane and, by delipidization
(i.e. removal of the lipids from the stratum corneum~, destroy its integrity. This
destruction of the skin surface topography leads to a rough feel and may eventually
permit the surfactant or solvent to interact with the keratin, creating irritation.
It is now recognised that m~int~inin~ the proper water gradient across the stratum
corneum is important to its functionality. Most of this water, which is sometimes
considered to be the ~Llalulll corneum's plasticizer, comes from inside the body. If
the humidity is too low, such as in a cold climate, insufficient water remains in the
outer layers of the stratum corneum to properly p}asticize the tissue, and the skin
begins to scale and becomes itchy. Skin permeability is also decreased somewhat
when there is inadequate water across the stratum corneum. On the other hand, too
much water on the outside of the skin causes the stratum comeum to llltim~tely
sorb three to five times its own weight of bound water. This swells and puckers
the skill and results in approximately a two to three fold increase in the
permeability of the skin to water and other polar molecules.
r
Thus, a need exists for compositions which will assist the sL~ corneum in
m~int~ining its barrier and water-retention functions at optimum performance in
spite of deleterious interactiolls which the skin ~nay encounter ul washing, work,
and recreation.
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Conventiollal co~smetic cream and lotion compositions as described, for example, in
Sagarin, Cosmetics Science and Technology, 2nd Edition, Vol.l, Wiley
Interscience (1972) and Encyclopaedia of Chemical Teclmology, Third Edition,
Volume 7 are known to provide varying degrees of emolliency, bamer and water-
retention (moisturizing) benefits. However, they can also suffer serious negatives
in terms of skin feel (i.e. they can often feel very greasy on the skin), have poor
rub-in and residue characteristics, and have slow absorption into tlle skin.
Thus, there remains a need for compositions which will assist the stratum corneu~n
in m~int~ining its water gradient, but which do so with improved skin feel, rub-in
and residue characteristics and absorption into the skin.
Compounds exhibiting liquid crystalline properties are known for use in skin care
compositions. Liquid crystals are a special phase of matter. The liquid crystal
phase exists between the boundaries of the solid phase and the isotropic liquid
phase (i.e. an intermediate between the three dimensionally ordered crystalline
state and the disordered dissolved state). In the liquid crystal state, some of the
molecular order characteristics of the solid phase are retained in the liquid state
because of molecular association structure and long range intermolecular order.
Tlle ability of some compounds to form a liquid crystalline mesophase had been
observed nearly a century ago. Since that time many compounds exhibiting liquid
crystalline properties have been synthesized and have been used to encapsulate and
act as a delivery vehicle for drugs, flavours, nutrients and other compounds and for
use in skin care compositions.
Parhculates such as silicon dioxide, titanium dioxide and zinc oxide are known for
use m cosmetics as pigments/colouring agents and also to provide benefits such as
UV absorption and oil absorption. There is still a need however for improvementsin skin feel, rate of absorption and reduced tackiness/greasiness of the skin.
It has now been surprisingly found that by incorporating a material capable of
forlning liquid clystals into a cosmetic emulsion composition together with a
particulate component having an average particle size of about 50 microns or less,
a composition is provided which enhances moisturisation and skin feel and which
in particular provides faster absorption and at the same time reduces stickiness and
greasy feel on the skin.
Sumrnary of the Invention
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According to one aspect of the present invention there is provided a skin care
composition in the form of an oil-in-water emulsion comprising:
(a) ~om about 0.1% to about 10% by weight of a particulate
component having an average particle size of about 50
microns or less;
(b) ~om about 0.1% to about 20% by weight of an organic
liquid crystal-forming amphiphilic surfactant;
(c) emulsified oil phase; and
(d) water.
According to a further aspect of the present invention there is provided a leave-on
moisturising emulsion comprising:
(a) ~om about 0.1% to about 10% by weight of a particulate
component having an average particle size of about 50 microns or
less;
(b) em~ ified oil phase; and
(c) water.
The compositions of the invention provide improved skin feel, reduced
greasiness/stickiness and faster absorption.
According to a further aspect of the present invention there is provided a
cosmetic method of treatment of the skin, wherein the method comprises
applying to the skin a skin care composition according to the present
invention.
Deta~led Description of the Invention
The compositions of the present invention take the form of an oil-in-water emulsion
cont~inin~ one or more distinct emulsified oil phases together with an essentialliquid crystal-forming emulsifier component as well as various optional ingredients
as indicated below. The compositions of the present invention essentially also
contain a particulate component having an average particle size of about 50
microns or less. All levels and ratios are by wei~ght of total composition, unless
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otherwise indicated. Chain length and degrees of ethoxylation are also specified on
a weight average basis.
The term "skin conditioning agent", as used herein means a material which
provides a "skin conditioning bene~t". As used herein, the term "skin
conditioning benefit" means any cosmetic conditioning benefit to the skin
including, but not limited to, moisturization, humectancy (i.e. the ability to
retain or hold water or moisture in the skin), emolliency, visual improvement
of the skin surface, soothing of the skin, softening of the skin, improvement
in skin feel, and the like.
The term "complete melting point", as used herein means a melting point as
measured by the well-known technique of Di~rential Sc~nnin~ Calorimetry
(DSC). The complete melting point is the temperalule at the intersection of
the baseline, i.e. the specific heat line, with the lil1e tangent to the trailing
edge of the endothermic peak. A sc~nning tempef~lule of 5~C/min~lte is
generally suitable in the present invention for measuring the complete
melting points. However, it should be recognised that more frequent
scanning rates may be deemed al~prol-liate by the analytical chemist skilled
in the art in specific circumstances. A DSC technique for measuring
complete melting points is also described in US Patent No. 5,306,514, to
Letton et al., issued, April 26, 1994, incorporated herein by reference.
The term "nonocclusive" as used herein, means that the component as so
described does not subst~nti~lly or block the passage of air and moisture
through the skin surface.
A first essential component of the compositions herein is a particulate component
having an average particle size of about 50 microns or less, preferably about 30microns or less, more preferably about 10 microns or less. In general the
particulate component preferably has an average particle size of at least about 0.5
microns, more preferably at least about 1 micron, most preferably from about 2 to
about 8 microns. In general, the particulates for use herein are preferably inert. As
used hereil1 the tenn "inert" means that they only have a limited ability to react
chemically. It has been found that the particulate component is especially valuable
for providing improvements in skin feel and application characteristics in a leave-
on moisturising emulsion. Therefore according to another aspect of the present
invention there is provided a leave-on moisturising emulsion comprising:
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~a) from about 0.1% to about 10% by weight of a particulate
component having an average particle size of about 50 microns or
less;
~ (b) emulsifiedoilphase; and
(c) water.
The particulate component is present in the compositions herein at a level of from
about 0.1% to about 10%, preferably from about 0.5% to about 5% by weight.
Suitable particulates for use herein include inorganic and organic particulates
suitable for use in skin care compositions. Such particulates include inorganic
metal oxides or nitrides, such as zinc oxide, titanium dioxide, iron oxides and
boron nitride, plastic-type particulates such as low density polyethylene, high
density polyethylene, polypropylene, nylon, Teflon, collagen treated nylon and
methacryla~e based balls, organic particulates such as starch, oat flour, siLk powder,
aluminium starch octenyl succinate, esters such as N-lauryl-l-lysine and siliconderived particulates such as mica, silicon dioxide, silica and magnesium
silicate/aluminium silicate.
P,erelled for use herein from the viewpoint of improving skin feel and application
characteristics are inorganic metal oxides and plastic-type particulates. In
preferred embodiments, the particulate component is selected from silicon dioxide,
polyethylene and mixtures thereof. In particulaLrly preferred embodiments, the
particulate material is a mixture of si~icon dioxide and polyethylene in a weight
ratio in the range offrom about 3:1 to about 1:3, ~refe-~bly from about 2:1 to about
1:2.
A preferred polyethylene for use herein is a low density polyethylene such as that
sold under the tradename Flo-Beads grade LE-1080, supplied by Sumitomo Seika
Chemicals Co. Ltd. This material has an average particle size of about 6 microns.
A preferred silicon dioxide particulate for use herein is silica bead SB-300,
m~nllf~ctured by Cosmo Trends Corporation.
Amphiphilic Surfactant
A further essential component of the compositions herein is an organic
amphiphilic surfactant which is capable of forming smectic Iyotropic
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crystals in product or when the product is being applied to the skin at
ambient or elevated temperatures. Preferably the amphiphilic surfactant is
capable of forming liquid crystals at a temperature in the range from about
20~C to about 4û~C. Preferably the amphiphilic surfactant is capable of
forming smectic lyotropic liquid crystals. Once application of the product
to the skin has been completed, liquid crystals may not be identifiable on
the skin surface or stratum corneum. The amphiphilic surfactant is
present at a level of from about 0.1~ to about 20%, preferably from
about 0.1 % to about 10%, by weight.
The liquid-crystal forming amphiphilic surfactants suitable for use herein
contain both hydrophilic and lipophilic groupings and exhibit a marked
tendency to adsorb at a surface or interface, i.e. they are surface-active.
Amphiphilic surface-active materials for use herein include nonionic (no
charge), anionic (negative charge), cationic (positive charge) and
amphoteric (both charges) based on whether or not they ionize in aqueous
media.
In the literature, liquid crystals are also referred to as anisotropic fluids, afourth state of matter, surfactant association structure or mesophases.
Those terms are often used interchangeably. The term "lyotropic" means
a liquid crystalline system cont~inin~ a polar solvent, such as water. The
liquid crystals used herein are preferably lamellar, hexagonal, rod or
vesicle structures or mixtures thereof.
The liquid crystalline phase utilized in the compositions of the invention
can be identifled in various ways. A liquid crystal phase flows under
shear and is characterised by a viscosity that is signif1cantly different from
the viscosity of its isotropic solution phase. Rigid gels do not flow under
shear like liquid crystals. Also, when viewed with a polarized light
microscope, liquid crystals show identifiable birefringence, as, for
example, planar lamellar birefringence, whereas when isotropic solutions
and rigid gels are viewed under polarized light, both show dark fields.
Other suitable means for identi~ying liquid crystals include X-ray
diffraction, NMR spectroscopy and transmission electron microscopy.
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In the literature, liquid crystals are also referred to as anisotropic fluids, afourth state of matter, surfactant association structure or mesophases.
Those terms are often used interchangeably. The term "lyotropic" means a
liquid crystalline system cont~ining a polar solvent, such as water. The
liquid crystals used herein are preferably lamellar, hexagonal, rod or
vesicle structures or mixtures thereof.
The liquid crystalline phase utilized in the compositions of the invention
can be identified in various ways. A liquid crystal phase flows under shear
and is characterised by a viscosity that is significantly different from the
viscosity of its isotropic solution phase. lRigid gels do not flow under shear
like liquid crystals. Also, when viewed with a polarized light microscope,
liquid crystals show identifiable birefringence, as, for example, planar
lamellar birefringence, whereas when isotropic solutions and rigid gels are
viewed under polarized light, both show dark fields.
Other suitable means for identifying liquid crystals include X-ray
diffraction, NMR spectroscopy and transmission electron microscopy.
In general terms, the organic amphiphilic surfactant preferred for use
herein can be described as a liquid, semi-solid or waxy water-dispersible
material having the formula X-Y where ~ represents a hydrophilic,
especially nonionic moiety and Y represents a lipophilic moiety.
Organic amphiphilic surfactants suitable ~or use herein include those having
a weight average HLB (Hydrophilic Lipophilic Balance) in the range from
about 2 to about 12, preferably from about 4 to about 8.
Preferred organic amphiphilic surfactants employed herein have a long
~ saturated or lln~ lrated branched or linear lipophilic chain having from
about 12 to about 30 carbon atoms such as oleic, lanolic, tetradecylic,
~ hexadecylic, isostearylic, lauric, coconut, stearic or alkyl phenyl chains.
When the hydrophilic group of the amphiphilic material forming the liquid
crystal phase is a nonionic group, a polyoxyethylene, a polyglycerol, a
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polyol ester, oxyalkylated or not, and, for example, a polyoxyalkylated
sorbitol or sugar ester, can be employed. When the hydrophilic group of
the amphiphilic surfactant forming the liquid crystal phase is an ionic
group, advantageously there can be used, as the hydrophilic group, a
phosphatidylcholine residue as found in lecithin.
Hydrophilic moieties suitable for use herein are selected from:
(1) ethers of linear, or branched, polyglycerol having the following
formula:
R-(Gly)n-OH
wherein n is a whole nurnber between 1 and 6, R is selected from aliphatic,
linear or branched, saturated or lln~ rated chains of 12 to 30 carbon
atoms, the hydrocarbon radicals of lanolin alcohols and the 2-hydroxy alkyl
residue of long chain, alpha-diols, and Gly represents a glycerol residue;
(2) polyethoxylated fatty alcohols, for example those of the formula
R1 (C2 R40)X OH wherein Rl is C12-C30 linear or branched alkyl
or alkenyl and x averages from about 0 to about 20, preferably from
about 0.1 to about 6, more preferably from about 1 to about 4;
(3) polyol esters and polyalkoxylated polyol esters, and mixtures thereof,
the polyols preferably being selected from sugars, C2-C6 alkylene
glycols, glycerol, polyglycerols, sorbitol, sorbitan, polyethylene
glycols and polypropylene glycols and wherein the polyalkoxylated
polyol esters contain from about 2 to about 20 preferably from about
2 to about 4 moles of alkylene oxide (especially ethylene oxide) per
mole of polyol ester;
(4) natural and synthetic phosphoglycerides, glycolipids and
sphingolipids, for example cerebrosides, ceramides and lecithin.
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Examples of amphiphilic surfactants suitable for use herein include Cg-C30
alkyl and acyl-cont~inin~ amphoteric, anionic, cationic and nonionic
surfactants as set out below.
Amphoteric
N-alkyl amino acids (e.g., sodium N-alkylaminoacetate);
N-lauroylglutamic acid cholesterol ester (e.g., Eldew CL-301 Ajinomoto)
Anionic
Acylglllt~m~tes (e.g., disodium N-lauroylglut~m~te);
Sarcosinates (e.g., sodium lauryl sarcosinate. Grace, Seppic);
Taurates (e.g., sodium lauryl taurate. sodium methyl cocoyl taurate);
Carboxylic acids and salts (e.g., potassium oleate; potassium laurate;
potassium-10-un~l~cenoate; potassium 1 l-(p-styryl) - un~lec~noate);
Ethoxylated carboxylic salts (e.g., sodium carboxy methyl alkyl
ethoxylate);
Ether carboxylic acids;
Phosphoric acid esters and salts (e.g., lecithin; DEA-oleth-10 phosphate);
Acyl isethionates (e.g., sodium 2-lauroyloxyethane sulfonate);
Alkane sulfonates (e.g., branched sodium x-alkane sulfonate (x/l);
Sulfosuccinates e.g.,
Sodium dibutyl sulfosuccinate,
Sodium di-2-pentyl sulfosuccinate,
Sodium di-2-ethylbutyl sulfosuccinate,
Sodium di-hexyl-sulfosuccinate,
Sodium di-2 ethylhexyl sulfosuccinate (AOT),
Sodium di-2-ethyldodecyl sulfosuccinate,
Sodium di-2-ethyloctadecyl sulfosuccinate,
Dioctyl sodium sulfosuccinate,
~isodium laureth sulfosuccinate ~MacK~n~te El, McIntyre Group
Ltd.)
Sulfuric acid esters (e.g., sodium 2-ethylhept-6-enyl sulfate; sodium 11-
heneicosyl sulfate; sodium ~-heptadecyl sulfate).
Alkyl sulfates (e.g., MEA alkyl sulfate such as MEA-lauryl sulfate)
Catio~ic
Alkyl Imidazolines (e.g., alkyl hydroxyethyl imidazoline, stearyl
hydroxyethyl imidazoline (supplier Akzo, Finetex and Hoechst));
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Ethoxylated Amines (e.g., PEG-n alkylamine, PEG-n alkylamino
propyl~mine, Poloxamine, PEG-cocopolyamine, PEG-15 tallow amine);
Alkylamines (e.g., dimethyl alkylamine; dihydroxyethyl alkylamine
dioleate)
Quaternaries:
Alkylbenzyl dimethylammonium salts (e.g., stearalkonium chloride);
Alkyl betaines (e.g., dodecyl dimethyl ammonio acetate, oleyl betaine);
Heterocylic ammonium salts (e.g., alkylethyl morpholinium ethosulfate);
Tetraalkylammonium salts (e.g., dimethyl distearyl quaternary ammonium
chloride (Witco));
Bis-isostearamidopropyl hydroxypropyl diammonium chloride (Schercoquat
21AP from Scher Chemicals);
1.8-Bis (decyldimethylammonio)-3, 6 dioxaoctane ditosylate
Nonionic Surfactants
Ethoxylated glycerides;
Monoglycerides (e.g., monoolein; monolinolein; monolaurin; 1-
dodecanoyl-glycerol monolaurin; 1, 13-docosenoyl-glycerol monoerucin
diglyceride fatty acid (e.g., diglycerol monoisostearate Cosmol 41,
fractionated. Nisshin Oil Mills Ltd.);
Polyglyceryl esters (e.g., triglycerol monooleate (Grindsted TS-T122),
diglycerol monooleate (Grindsted TST-T101);
Polyhydric alcohol esters and ethers (e.g., sucrose cocoate, cetostearyl
glucoside (Montanol, Seppic), B octyl glucofuranoside esters, all~yl
glucoside such Clo-C16 (Henkel));
Diesters of phosphoric acid (e.g., sodium dioleyl phosphate);
Alkylamido propyl betaine (e.g., cocoamido propyl betaine);
Amide: (e.g., N-(dodecanoylaminoethyl)-2-pyrrolidone);
Amide oxide: e.g., 1, 1 Dihydroperfluorooctyldimethylamine oxide,
Dodecyldimethyl~mine oxide,
2-Hydroxydodecyldimethylamine oxide,
2-Hydroxydodecyl-bis (2-hydroxyethyl) amine oxide,
2-Hydroxy-4-oxahexadecyldimethyl~mine oxide,
Ethoxylated amides (e.g., PEG-n acylamide);
Ammonio phosphates (e.g., didecanoyl lecithin);
Amine (e.g., octylamine);
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Il
Ammonio amides e.g.,-
N-trimethylammoniodec~n~midate,
N-trimethylammoniodol1ec~n~midate,
Ammonio carboxylates e.g.,
dodecyldimethylammonioacetate,
6-didodecylmethylammoniohexanoate,
Phosphonic and phosphoric esters and amides e.g.,
methyl-N-me~yl-dodecylphosphonamidate,
dimethyl dodecylphosphonate,
dodecyl methyl methylphosphonate,
N,N-dimethyl dodecylphosphonic dLiamide
Ethoxylated alcohols
Polyoxyethylene (Cg) e.g.,
pentaoxyethylene glycol p-n-octylphenyl ether
hexaoxye~ylene glycol p-n-octylphenyl ether
nonaoxyethylene glycol p-n-octylphenyl ether
Polyoxyethylene (Clo) e.g.,
pentaoxyethylene glycol p-n-decylphenyl ether,
decyl glyceryl ether, 4-oxatetr~lec~n-l~ 2-diol,
nonaoxyethylene glycol p-n-decylphenyl ether
Polyoxyethylene ( Cll) e.g.,
Tetraoxyethylene glycol undecyl ether
Polyoxyethylene (C12) e.g.,
3, 6, 9, 13-tetraoxapentacosan 1, ll-diol,
3, 6, 10-trioradocosan-1, 8-diol,
3, 6, 9, 12, 16-pentaoxaoctacosan 1, 14-diol,
3 , 6 , 9 ,1 2 ,1 5 -pentaoxanonacosan- 1, 1 7-diol ,
3, 7-dioxanon~tlec~n-1, 5-diol,
3, 6, 12, 15, l9-hexaoxahentriacontan-1, 16-diol,
pentaoxyethylene glycol dodecyl ether,
monaoxyethylene glycol p-n-dodecylphenyl ether,
Polyoxyethylene(C14~ e.g.,
3, 6, 9, 12, 16-pentaoxaoctacosan-1, 14-diol,
3, 6, 9, 12,15, l9-heraoxatriacontan-1, 17-diol,
Sulfone ~iiimines e.g.,
decyl methyl sulfone diimine
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12
Sulfoxides e.g.,
3-decyloxy-2-hydro~ypropyl methyl sulfoxide
4-decyloxy-3-hydroxybutyl methyl sulfoxide
Sulfoximines e.g.,
N-methyl dodecyl methyl sulfoximine
Preferred organic amphiphilic surfactants for use herein are nonionic
amphiphilic surfactants having a hydrophilic moiety selected from polyol
esters and polyalkoxylated polyol esters, and mixtures thereof, the polyols
preferably being selected from sugars, C2-C6 alkylene glycols, glycerol,
polyglycerols, sorbitol, sorbitan, polyethylene glycols and polypropylene
glycols and wherein the polyalkoxylated polyol esters contain from about 2
to about 20 preferably from about 2 to about 4 moles of aL~ylene oxide
(especially ethylene oxide) per mole of polyol ester, and a lipophilic moiety
selected from long saturated or lln~hlrated branched chain or linear
lipophilic chains having from about 12 to about 30 carbon atoms such as
oleic, lanolic, tetradecylic, hexadecylic, isostearylic, lauric, coconut,
stearic or alkyl phenyl chains.
Highly preferred organic amphiphilic surfactants for use herein are selected
from polyhydric alcohol esters and ethers. Especially preferred
amphiphilic surf~çt~nt~ for use herein are sugar esters and polyalkoxylated
sugar esters.
The sugar esters for use in this invention can be classified as hydrocarbyl
and alkyl polyoxyalkylene esters of cyclic polyhydroxy saccharides wherein
one or more of the hydroxyl groups on the saccharide moiety is substituted
with an acyl or polyoxyalkylene group. Hydrocarbyl sugar esters can be
prepared in well-known fashion by heating an acid or acid halide with
sugar, i.e., by a simple esteri~lcation reaction.
The sugars employed in the preparation of the sugar esters include
monosaccharides, di-saccharides and oligo-saccharides well known in the
art, for example, the dextrorotatory and levorotatory forms of glucose,
fructose, mannose, galactose, arabinose and xylose. Typical di-saccharides
include maltose, cellibiose, lactose, and trehalose. Typical tri-saccharides
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include raffinose and gentianose. The di-saccharides are preferred for use
herein, especially sucrose.
Sucrose can be esterified at one or more of its eight hydroxyl groups to
provide the sucrose esters useful herein. When sucrose is combined with
an esterification agent in a 1:1 mole ratio, sucrose monoesters are forrned;
when the ratio of esterification agent to sucrose is 2:1, or greater, the di-,
tri-, etc., esters are formed, up to a maximum of the octa-ester.
Preferred sugar esters herein are those prepared by the esterification of
sugars at a mole ratio of esterification agent:sugar of 1:1 and 3:1 i.e., the
mono-acyl and di- or higher acyl sugar esters. Especially preferred are the
mono-, di- and tri-acyl sugar esters and mixtures thereof wherein the acyl
substituents contain from about 8 to about 24, preferably from about 8 to
about 20 carbon atoms and 0,1 or 2 nn~hlrated moieties. Of the mono-
acyl and di-acyl sugar esters, the respective esters of di-saccharide sugars,
especially sucrose, wherein the acyl groups contain from about 8 to about
20 carbon atoms are especially preferred. Preferred sugar esters herein are
sucrose cocoate, sucrose monooctanoate, sucrose monodecanoate, sucrose
monolaurate, sucrose monomyristate, sucrose monop~lmit~te, sucrose
monostearate, sucrose monooleate, sucrose monolinoleate, sucrose
dioleate, sucrose dip~lmit~te, sucrose distearate, sucrose dilaurate and
sucrose dilinoleate, and mixtures thereof. Sucrose cocoate has been found
to be particularly efficacious in the compositions herein. In mixtures of
mono-acyl with di-, tri- and higher acyl sugar esters, the mono- and di-
acyl esters preferably comprise at least about 40%, more preferably from
about 50 5~ to about 95 ~ by weight of the total sugar ester mixture.
Other sugar esters suitable for use in the compositions of this invention are
the alkyl polyoxyalkylene sugar esters wherein one hydroxyl group is
substituted with a Cg-C1g alkyl group and wherein one or more of the
hydroxyl groups on the sugar molecule are replaced by an ester or ether
substituent cont~inin~; the moiety [(CH2)~-O]y wherein x is an integer from
2 to about 4, preferably 2, and wherein y is an integer from about 1 to
about 50, preferably 8 to 30 polyoxyalkylene substituents. Especially
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14
preferred herein are sugar esters wherein the polyoxyalkylene substituent is
a polyoxyethylene substituent cont~ining from about 8 to about 30
polyoxyethylene groups. Such materials wherein sorbitan is the sugar
moiety are commercially available under the tradename "Tweens". Such
mixed esters can be prepared by ~lrst acylating a sugar at a 1: ~ mole ratio
with a hydrocarbyl acid halide followed by reaction with the corresponding
polyoxyalkylene acid halide or alkylene oxide to provide the desired
material. The simple polyoxyalkylene ester of di-saccharides, especially
sucrose, wherein the polyoxyalkylene groups contain up to about 20
alkylene oxide moieties are another useful class of sugar esters herein.
preferred sugar ester of this class is sorbitol trioleate ethoxylated with 20
moles of ethylene oxide. Mixtures of sugar esters with other polyol esters,
eg. glycerol esters, are also suitable for use herein, for example, Palm Oil
Sucroglyceride (Rhone-Poulenc).
As used herein, the term "lecithin" refers to a material which is a
phosphatide. Naturally occurring or synthetic phosphatides can be used.
Phosphatidylcholine or lecithin is a glycerine esteri~led with a choline ester
of phosphoric acid and two fatty acids, usually a long chain saturated or
un~ rated fatty acid having 16-20 carbons and up to 4 double bonds.
Other phosphatides capable of forming lamellar or hexagonal liquid crystals
can be used in place of the lecithin or in combination with it. These
phosphatides are glycerol esters with two fatty acids as in the lecithin, but
the choline is replaced by ethanolamine (a cephalin), or serine ( -
aminopropanoic acid; phosphatidyl serine) or an inositol (phosphatidyl
inositol). While the invention herein is exemplified with lecithin, it is
understood that these other phosphatides can be used herein.
A variety of lecithins can be used. American Lecithin Company supplies a
Nattermann Phospholipid, Phospholipan 80 and Phosal 75. Other lecithins
which can be used alone or in combination with these are: Actifla Series,
Centrocap series, Central Ca, Centrol series, Centrolene, Centrolex,
Centromix, Centrophase and Centrolphil Series from Central Soya; Alcolec
and Alcolec 439-C from American Lecithin; Canaspersa from Canada
Packers, Lexin K and Natipide from American Lecithin; and L-Clearate,
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Clearate LV and Clearate WD from the W.A. Cleary Co. Lecithins are
supplied dissolved in ethanol, fatty acids, triglycerides and other solvents.
They are usually mixtures of lecithins and range from 15 % to 50~ o~ the
solution as supplied.
Both natural and synthetic lecithins can be used. Natural lecithins arederived from oilseeds such as sunflower seeds, soybeans, safflower seeds
and cottonseed. The lecithins are separated from the oil during the refining
process.
The organic amphiphilic surfactant has been found to be especially valuable
herein for improving the stability and skin feel of the compositions of the
invention.
The amphiphilic surfactant is preferably incorporated into the composition in anamount of from about 0.1 % to about 20%, preferably from about 0.1% to about
10%, and more preferably from about 0.1% to about 8% by weight of
composition.
Highly preferred herein is a fatty acid ester blend based on a mixture of sorbitan or
sorbitol fatty acid ester and sucrose fatty acid ester, the fatty acid in each instance
being preferably ~g-C24, more preferably C1o-C20. The preferred fatty acid esteremulsifier ~rom the viewpoint of moisturisation is a blend of sorbitan or sorbitol
C16-C20 fatty acid ester with sucrose Clo-C16 fatty acid ester, especially sorb;tan
stearate and sucrose cocoate. This is commercially available from ICI under the
trade name Arlatone 2121.
The compositions herein comprise an oil or mixture of oils. In physical terms, the
compositions generally take the form of an emulsion of one or more oil phases inan aqueous continuous phase, each oil phase comprising a single oily component
or a mixture of oily components in miscible or homogeneous form but said
dirrelent oil phases cont~inin~ different materials or combinations of materialsfrom each other. The overall level of oil phase components in the compositions of
the invention is preferably from about 0.1% to about 60%, preferably from about
1% to about 30% and more preferably from about 1% to about 10% by weight.
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16
The present compositions preferably comprise, as either all or a portion of the oil
phase or oil phases referred to above a first silicone-cont~inin~; phase comprising a
crosslinked polyorganosiloxane polymer and a silicone oil, wherein the
composition comprises 0.1% to about 20%, preferably from about 0.5% to about
10%, more preferably from about 0.5% to about 5%, by weight of composition, of
the combination of crosslinked silicone and si}icone oil.
The first silicone-cont~ining phase comprises from about 10% to about 40%, more
preferably from about 20% to about 30%, by weight of the first silicone-
cont~inin~; phase, of the crosslinked polyorganosiloxane polymer and from about
60% to about 90%, preferably from about 70% to about 80%, by weight of the
first silicone-cont~ininp; phase, of the silicone oil.
The crosslinked polyorganosiloxane polymer comprises polyorganosiloxanepolymer crosslinked by a crosslinking agent. Crosslinkin~ agents for use herein
include any crosslinkin~; agents useful for the preparation of crosslinked silicones.
Suitable cros~linking agents herein include those represented by the following
general formula:
(R)3Si--O--Si--O ---Si(R)3
R2
_ Z
wherein R1 is methyl, ethyl, propyl or phenyl, R2 is H or
-(CH2~nCH=CH2, where n is in the range of from about 1 to about 50, z is
in the range of from about 1 to about 1000, preferably from about 1 to about
100 and R is an alkyl group having from 1 to 50 carbon atoms.
Preferably the crosslinking agent has the general formula
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17
~CH3)3Si--O ----Si--- O -- Si(CH3)3
R2
where R1, R2 and z are as defined above.
In espec;ally preferred embodiments, the crosslink;ng agent has the following
general formula:
R1
(CH3)3Si--O ---Si--O--Si(CH3)3
R2
wherein z is in the range of from about 1 to about 1000, preferably from
about 1 to about 100.
The crosslinked polysiloxane polymer preferably comprises from about 10%
to about 50%, more preferably from about 20% to about 30%, by weight the
crosslinked polysiloxane polymer, of crosslinking agent.
Any polyorganosiloxane polymers suitable for use in skin care compositions
can be used herein. Su;table polyorganosiloxane polymers for use herein
include those represented by the following general formula:
R3 R1
(R)3Si--O -- Si--O - Si---- O ---Si(R)3
R4 R2
_ p
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18
wherein Rl is methy}, ethyl, propyl or phenyl, R2 is H or
-(CH2)nCH=CH2, where n is in the range of from about 1 to about 50, R3
and R4 are independently selected from methyl, ethyl, propyl and phenyl, R
is an end-gap, such as an optionally hydroxy-substituted alkyl group having
from 1 to 50 carbon atoms, preferably an alkyl group having from 1 to 5
carbon atoms, more preferably an alkyl group having 1 or 2 carbon atoms, p
is an integer in the range of from about 1 to about 2000, preferably from
about 1 to about 500, q is an integer in the range of from about 1 to about
1000, preferably from about 1 to about 500.
In preferred embodiments the polyorganosiloxane is selected from polymers
having the following general structure:
R3 R~
~CH3)3Si--O--Si--O ---Si--O--Si(CH3)3
R4 R2
_ q
wherein Rl, R2, R3, R4, p and q are as defined above.
As defined herein, p and ~ reflect the number of Si-O linkages in the
polymer chain and Rl and R2 and R3 and R4 may vary going from one
monomer unit to the next. For example, suitable polyorganosiloxane
polymers for use herein include methyl vinyl dimethicone, methyl vinyl
diphenyl dimethicone and methyl vinyl phenyl methyl diphenyl
dimethicone.
In order to achieve crosslinking between the polyorganosiloxane polymerand the crosslinking agent, an (-Si-H) group must crosslink with a
-Si-(CH2)nCH=CH2 group, so that for any specific crosslink, the group R2
must be different in the polyorganosiloxane polymer and the crosslinkin~
agent. For example, for any specific crosslink, when R2 is
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-(CH2)nCH=CH2 in the polyorganosiloxane polymer, R2 must be H in the
crosslinkin~ agent, and vice versa. However, there can be mixtures o~R2
for each of the polyorganosiloxane polymer and crosslinkin~ agent.
In preferred embodiments, the polyorganosiloxane polymer is selected from
an alkylarylpolysiloxane polymer having the general formula:
CH3 C6H5 CH3
(CH3)3Si--O-- Si--O--Si ---O--Si--O--Si(CH3)3
CH3 C6H5 R2
- I - -m_ _ n
wherein R2 is selected from -(~H=CH2 or H, preferably -CH=CH2, and
wherein 1 is an integer in the range of from about 1 to about 1000, preferably
from about 1 to about 500, m is an integer in the range from 0 to about
1000, preferably from about 0 to about 500, and n is an integer in the range
of from about 1 to about 1000, preferably from about 1 to about 100.
In particularly preferred embodiments the polyorganosiloxane polymer isselected from an alkylarylpolysiloxane polymer having the general formula:
CH3 C6H5 CH3
(CH3)3Si--O Si--O--Si--O--Si--O--- Si(CH3)3
3 _ I _ 6 5 ~m 2
wherein 1, m and n are as defined above. In preferred embodiments m is in
the range of from about 1 to about 1000, preferably from about 200 to about
800.
The first silicone-cont~inin~; phase also comprises a silicone oil. Anystraight chain, branched and cyclic silicones suitable for use in skin care
compositions can be used herein. The silicone oils can be volatile or non-
volatile. Suitable silicone oils for use herein include silicone oils having a
weight average molecular weight of about 100,000 or less, preferably about
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50,000 or less. Preferably the silicone oil is selected from silicone oils
having a weight average molecular weight in the range from about 100 to
about 50,000, and preferably from about 200 to about 40,000. In preferred
embodiments, the silicone oil is selected from dimethicone,
decamethylcyclopentasiloxane, octamethylcyclotetrasiloxane and phenyl
methicone, and mixtures thereof, most preferably phenyl methicone.
Suitable materials for use in the first silicone-cont~inin~ phase are available
under the tradename KSG supplied by Shinetsu Chemical Co., Ltd, for
example KSG-15, KSG-16, KSG-17, KSG-18. These materials contain a
combination of crosslinked polyoragnosiloxane polymer and silicone oil.
Particularly preferred for use herein especially in combination with the
organic amphiphilic emulsifier material is KSG- 18. The assigned INCI
names for KSG-15, KSG-16, KSG-17 and KSG-18 are Cyclomethicone
Dimethicone/Vinyl Dimethicone Crosspolymer, Dimethicone
Dimethicone/Vinyl Dimethicone ~rosspolymer, Cyclomethicone
Dimethicone/Vinyl Dimethicone Crosspolymer and Phenyl Trimethicone
Dimethicone/Phenyl Vinyl Dimethicone Crosspolymer, respectively.
Compositions herein preferably also comprise a second non-crosslinked silicone-
containing phase. In preferred embodiments the second silicone-containing phase
is present in a level of from about 0.1% to about 20%, especially from about 0.1%
to about 10% by weight of composition.
Suitable silicone fluids for use in the second silicone-containing phase herein
include water-insoluble silicones inclusive of non-volatile polyalkyl and polyaryl
siloxane gums and fluids, volatile cyclic and linear polyalkylsiloxanes,
polyalkoxylated silicones, amino and quaternary ammonium modif1ed silicones,
and mixtures thereof.
In preferred embodiments the second silicone-cont~inin~ phase comprises a
silicone gum or a mixture of silicones including the silicone gum. As used herein,
the term "silicone gum" means high molecular weight silicone-based fluids havinga mass-average molecular weight in excess of about 200,000 and preferably from
about 200,000 to about 400,000. Silicone oils generally have a molecular weight
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21
of less than about 200,000. Typically, silicone gums have a viscosity at 25~C inexcess of about 1,000,000 mm2.s~1. The silicone gums include dimethicones as
described by Petrarch and others including US-A-4,152,416, May 1, 1979 to
Spitzer, et al, and Noll, Walter, Chemistry and Technology of Silicones~ New
York: Academic Press 196g. Also describing silicone gums are General Electric
Silicone Rubber Product Data Sheets SE 30, SE 33, SE 54 and SE 76.
Silicone gums for use herein include any silicone gum suitable for use in a skincare composition. Suitable silicone gums for use herein are silicone gums havinga molecular weight of from about 200,000 to about 4,000,000 selected from
dimethiconol, fluorosilicone and dimethicone and mixtures thereof.
Dimethiconol-based silicones su;table for use herein can have the chemical
structure (II):
Ho(cH3)2sio[(cH3)2sio]n(cH3)2sioH
where n is from about 2000 to about 40,000, preferably from about 3000 to about
30,000.
Exemplary fluorosilicones useful herein can have a molecular weight of from
about 200,000 to about 300,000, preferably from about 240,000 to about 260,000
and most preferably about 250,000.
Specific examples of silicone gums include polydimethylsiloxane,
(polydimethylsiloxane)(methylvinylsiloxane) copolymer,
poly(dimethylsiloxane)(diphenyl)(methy~vinylsiloxane) copolymer and mixtures
thereof.
The silicone gum used herein can be incorporated into the composition as part of a
mixture of silicones. When the silicone gum is incorporated as part of a mixtureof silicones, the silicone gum preferably constitutes from about 5% to about 40%,
especially from about 10% to 20% by weight of the silicone mixture. The siliconeor silicone mixture preferably constitutes from about 0.1% to about 20%, more
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22
preferably from about 0.1% to about 15%, and especially from about 0.1% to
about 10% by weight of composition.
Suitable silicone gum-based silicone mixtures for use in the second silicone-
containing phase of the compositions herein include mixtures consisting
essentially of:
(i~ a silicone having a molecular weight of from about 200,000 to about 4,000,000 selected from dimethiconol, fluorosilicone and
dimethicone and mixtures thereof; and
(ii) a silicone-based carrier having a viscosity from about 0.65 mm2.s~ 1 to
about 100 mm2.S-l,
wherein the ratio of i) to ii) is from about 10:90 to about 20:80 and wherein
said silicone gum-based component has a final viscosity of from about 500
mm2.S-1 to about 10,000 mm2.s~l.
of about 1,000,000 mm2.s~l .
The silicone-based carriers suitable for use herein include certain silicone fluids.
The silicone fluid can be either a polyalkyl siloxane, a polyaryl siloxane, a
polyalkylaryl siloxane or a polyether siloxane copolymer. Mixtures of these fluids
can also be used and are preferred in certain executions.
The polyalkyl siloxane fluids that can be used include, for example,
polydimethylsiloxanes with viscosities r~np;inp from about 0.65 to
600,000 mm2.S~1, preferably from about 0.65 to about 10,000 mm2.s-1 at 25~C.
These siloxanes are available, for example, from the General Electric Company asthe Viscasil (RTM) series and from Dow Corning as the Dow Corning 200 series.
The essentially non-volatile polyalkyl~rylsiloxane fluids that can be used include,
for example, polymethylphenylsiloxanes, having viscosities of about 0.65 to
30,000 mm2.s~1 at 25~C. These siloxanes are available, for example, from the
General Electric Company as SF 1075 methyl phenyl fluid or from Dow Corning
as 556 Cosmetic Grade Fluid. Also suitable for use herein are certain volatile
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23
cyclic polydimethylsiloxanes having a ring structure incorporating from about 3 to
about 7 (CH3)2SiO moiet;es.
The viscosity can be measured by means of a glass capillary viscometer as set
forth in Dow Corning Corporate Test Method CTM0004, July 29, 1970.
Preferably the viscosity of the silicone blend constituting the second fluid phase
ranges from about 500 mm2.s~l to about 100,000 mm2.s~1,.preferably from about
1000 mm2.s~1 to about 10,000 mm2.s~1.
An especially preferred silicone-gum based component for use in the compositionsherein is a dimethiconol gum having a molecular weight of from about 200,000 to
about 4,000,000 along with a silicone carrier with a viscosity of about 0.65 to 100
mm2.s~1. An example ofthis silicone component is Dow Corning Q2-1403 (g5%
S mm2.s~l Dimethicone Fluid/15% Dimethiconol) and Dow Corning Q2-1401
available from Dow ~orning.
Another class of silicone suitable for use in the second silicone-cont~inin~; phase
herein include polydiorganosiloxane-polyoxyalkylene copolymers cont~inin~ at
least one polydiorganosiloxane segment and at least one polyoxyalkylene
segment, said polydiorganosiloxane segment consisting essentially of
RbSiO(4-b)/2
siloxane units wherein b has a value of from about 0 to about 3, inclusive,
there being an average value of approximately 2 R radicals per silicon for all
siloxane units in the copolymer, and R denotes a radical selected from
methyl, ethyl, vinyl, phenyl and a divalent radical bonding said
polyoxyalkylene segment to the polydiorganosiloxane segment, at least
about 95% of all R radicals being methyl; and said polyoxyalkylene
segment having an average molecular weight of at least about 1000 and
consisting of from about 0 to about 50 mol percent polyoxypropylene units
and from about 50 to about 100 mol percent polyoxyethylene units, at least
one terminal portion of said polyoxyalkylene segment being bonded to said
polydiorganosiloxane segment, any terminal portion of said
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24
polyoxyalkylene segment not bonded to said polydiorganosiloxane segment
being satisf1ed by a terminating radical; the weight ratio of
polydiorganosiloxane segments to polyoxyalkylene segments in said
copolymer having a value of from about 2 to about 8. Such polymers are
described in US-A-4,268,499.
Preferred for use herein are polydiorganosiloxane-polyo~yalkylene
copolymers having the general formula:
IH3 IH3 IH3 IH3
H3C- Si - O - (si o)~ i o) - si CH3
CH3 3 i3H6 CH3
o- -- (C2H4O)a(c3H6O)bR
wherein x and y are selected such that the weight ratio of polydiorgano-
siloxane segments to polyo~lk~lkylene segments is from about 2 to about
8, the mol ratio of a:(a+b) is from about 0.5 to about 1, and R is a chain
termin~tin~ group, especially selected from hydrogen; hydroxyl; alkyl, such
as methyl, ethyl, propyl, butyl, benzyl; aryl, such as phenyl; alkoxy such as
methoxy, ethoxy, propoxy, butoxy; benzyloxy; aryloxy, such as phenoxy;
alkenyloxy, such as vinyloxy and allyloxy; acyloxy, such as acetoxy,
acryloxy and propionoxy and amino, such as dimethylamino.
The number of and average molecular weights of the segments in the
copolymer are such that the weight ratio of polydiorganosiloxane segments
to polyoxyalkylene segments in the copolymer is preferably from about 2.5
to about 4Ø
Suitable copolymers are available commercially under the kadenames Belsil
(RTM) from Wacker-Chemie Gmb~I, Geschaftsbereich S, Postfach D-8000
Munich 22 and Abil (RTM) from Th. Goldschmidt Ltd., Tego House, Victoria
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Road, Ruislip, Middlesex, HA4 0YL, for example Belsil (RTM) 6031 and Abil
(RTM) B88 183 . A particularly preferred copolymer for use herein includes Dow
Corning DC3225C which has the CTFA designation Dimethicone/Dimethicone
copolyol.
Optional In~redients
In preferred embodiments, a third oil phase is present in an amount of from about
0.1% to about 15%, more preferably from about 1% to about 10% by weight of
composition. The third oil phase can be either a separate phase or can form one
phase together with either or both of the first and second silicon phases.
Preferably, the third oil phase is a separate phase.
The third oil phase preferably comprises a non-silicone organic oil, such as a
natural or synthetic oil selected from mineral, vegetable, and ~nim~l oils, fats and
waxes, fatty acid esters, fatty alcohols, fatty acids and mixtures thereof, which
ingredients are useful for achieving emollient cosmetic properties. The first oil
phase component is preferably essentially silicone-free, i.e., it contains no more
than about 10%, preferably no more than about 5% by weight of silicone-based
materials. It will be understood that the oil phase may contain, for example, up to
about 25%, preferably up to only about 10% of oil phase soluble emulsifier
ingredients. Such ingredients are not to be considered as oil phase components
from the viewpoint of determinin~; the oil phase level and required HLB. In
preferred embodiments, the overall required HLB of the oil phase is from about 8to about 12, especially from about 9 to about 1 1, required HLB being determinedby sllmmin~; the individual required HLB values for each component of the oil
phase multiplied by its W/W percentage in the oil phase (see ICI Literature on
HLB system; ICI reference paper ref 51/0010/303/lSm., first printed in 1976,
revised in 1984 and May 1992).
Suitable first oil phase components for use herein include, for example, optionally
hydroxy-substituted Cg-Cso unsaturated fatty acids and esters thereof, C1-C24
esters of Cg-C30 saturated fatty acids such as isopropyl myristate, isopropyl
palmitate, cetyl palmitate and octyldodecylmyristate (Wickenol 142), beeswax,
saturated and lln~tllrated fatty alcohols such as behenyl alcohol and cetyl alcohol,
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26
hydrocarbons such as mineral oils, petrolatum and squalane, fatty sorbitan esters
(see US-A-3988255, Seiden, issued October 26 1976), lanolin and lanolin
derivatives, ~nim~l and vegetable triglycerides such as almond oil, peanut oil,
wheat germ oil, linseed oil, jojoba oil, oil of apricot pits, walnuts, palm nuts,
pistachio nuts, sesame seeds, rapeseed, cade oil, corn oil, peach pit oil, poppyseed
oil, pine oil, castor oil, soybean oil, avocado oil, safflower oil, coconut oil,hazelnut oil, olive oil, grapeseed oil, shea butter, shorea butter, and sunflower seed
oil and Cl C24 esters of dimer and trimer acids such as diisopropyl dimerate,
diisosteary1m~1~te, diisostearyldimerate and triisostearyltrimerate. Of the above,
highly preferred are the mineral oils, petrolatums, 1m~t11rated fatty acids and
esters thereof and mixtures thereof.
Preferred embodiments herein comprise from about 0.1% to about l 0% by weight
of an 11n.c~t11rated fatty acid or ester. Preferred 11n.c~t11rated fatty acids and esters
for use herein are optionally hydroxy substituted Cg-Cso un~h1rated fatty acids
and esters, especially esters of ricinoleic acid. The 11n~turated fatty acid or ester
component is valuable herein in combination with the liquid crystal-forming
emulsifier for improving the skin feel and rub-in characteristics of the compositon.
Highly preferred in this respect is cetyl ricinoleate.
A preferred component of the compositions herein, in addition to the
organic amphiphilic surfactant is a polyol ester skin conditioning agent.
The compositions of the present invention preferably comprise from about
0.01% to about 20%, more preferably from about 0. l % to about 15%, and
especially from about 1% to about l 0% by weight of the polyol ester. The
level of polyol ester by weight of the oil in the composition is preferably
from about 1% to about 30%, more preferably from about 5% to about 20%.
The polyol ester preferred for use herein is a nonocclusive liquid or
liquifiable polyol carboxylic acid ester. These polyol esters are derived
from a polyol radical or moiety and one or more carboxylic acid radicals or
moieties. In other words, these esters contain a moiety derived from a
polyol and one or more moieties derived from a carboxylic acid. These
carboxylic acid esters can also be derived from a carboxylic acid. These
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27
carboxylic acid esters can also be described as liquid polyol fatty acid esters,because the terms carboxylic acid and fatty acid are often used
interchangeably by those skilled in the art.
The preferred liquid polyol polyesters employed in this invention comprise
certain polyols, especially sugars or sugar alcohols, esterified with at least
four fatty acid groups. Accordingly, the polyol starting material must have
at least four esterifiable hydroxyl groups. Examples of preferred polyols are
sugars, including monosaccharaides and disaccharides, and sugar alcohols.
Examples of monosaccharides cont~inin~ four hydroxyl groups are xylose
and arabinose and the sugar alcohol derived from xylose, which has five
hydroxyl groups, i.e., xylitol. The monosaccharide, erythrose, is not
suitable in the practice of this invention since it only contains three hydroxylgroups, but the sugar alcohol derived from erythrose, i.e., erythritol,
contains four hydroxyl groups and accordingly can be used. Suitable f1ve
hydroxyl group-cont~inin,~ monosaccharides are galactose, fructose, and
sorbose. Sugar alcohols cont~inin~ six -OH groups derived from the
hydrolysis products of sucrose, as well as glucose and sorbose, e.g., sorbitol,
are also suitable. Examples of disaccharide polyols which can be used
include maltose, lactose, and sucrose, all of which contain eight hydroxyl
groups.
Preferred polyols for preparing the polyesters for use in the present
invention are selected from the group consisting of erythritol, xylitol,
sorbitol, glucose, and sucrose. Sucrose is especially preferred.
The polyol starting material having at least four hydroxyl groups is
esterified on at least four of the -OH groups with a fatty acid cont~inin~;
from about 8 to about 22 carbon atoms. Examples of such fatty acids
include caprylic, capric, lauric, myristic, myristoleic, palmitic, palmitoleic,
stearic, oleic, ricinoleic, linoleic, linolenic, eleostearic, arachidic,
arachidonic, behenic, and erucic acid. The fiatty acids can be derived from
~ naturally occurring or synthetic fatty acids; they can be saturated or
n~tllrated, including positional and geometrical isomers. However, in
order to provide liquid polyesters preferred for use herein, at least about
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50% by weight of the fatty acid incorporated into the polyester molecule
should be l~n.~tllrated. Oleic and linoleic acids, and mixtures thereof, are
especially preferred.
The polyol fatty acid polyesters useful in this invention should contain at
least four fatty acid ester groups. It is not necessary that all of the hydroxylgroups of the polyol be esterified with fatty acid, but it is preferable that the
polyester contain no more than two unesterif1ed hydroxyl groups. Most
preferably, substantially all of the hydroxyl groups of the polyol are
esteri~1ed with fatty acid, i.e., the polyol moiety is substantially completely
esterified. The fatty acids esterified to the polyol molecule can be the same
or mixed, but as noted above, a substantial amount of the lln~turated acid
ester groups must be present to provide liquidity.
To illustrate the above points, a sucrose fatty triester would not be suitable
for use herein because it does not contain the required four fatty acid ester
groups. A sucrose teka-fatty acid ester would be suitable, but is not
preferred because it has more than two unesteri~led hydroxyl groups. A
sucrose hexa-fatty acid ester would be preferred because it has no more than
two unesterified hydroxyl groups. Highly preferred compounds in which all
the hydroxyl groups are esterified with fatty acids include the liquid sucrose
octa-substituted fatty acid esters.
The following are non-limiting examples of specific polyol fatty acid
polyesters containing at least four fatty acid ester groups suitable for use in
the present invention: glucose tetraoleate, the glucose tetraesters of soybean
oil fatty acids (unsaturated), the mannose tetraesters of mixed soybean oil
fatty acids, the galactose tetraesters of oleic acid, the arabinose tetraesters of
linoleic acid, xylose tetralinoleate, galactose pentaoleate, sorbitol
tetraoleate, the sorbitol hexaesters of Im~turated soybean oil fatty acids,
xylitol pentaoleate, sucrose tetraoleate, sucrose pentaoletate, sucrose
hexaoleate, sucrose hepatoleate, sucrose octaoleate, and mixtures thereof.
~s noted above, highly preferred polyol fatty acid esters are those wherein
the fatty acids contain from about 14 to about 18 carbon atoms.
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29
The preferred liquid polyol polyesters preferred for use herein have
complete melting points below about 30~C, preferably below about 27.5~C,
more preferably below about 25~C. Complete melting points reported
herein are measured by Differential Sc~nning Calorimetry (DSC).
The polyol fatty acid polyesters suitable for use herein can be prepared by a
variety of methods well known to those skilled in the art. These methods
include: transesterification of the polyol with methyl, ethyl or glycerol fatty
acid esters using a variety of catalysts; acylation of the polyol with a fatty
acid chloride; acylation of the polyol with a ~atty acid anhydride; and
acylation of the polyol with a fatty acid, per se. See U.S. Patent No.
2,831,854; U.S. PatentNo. 4,005,196, to Jandacek, issued January 25, 1977;
U.S. PatentNo. 4,005,196, to Jandacek, issued January 25, 1977.
A highly preferred ingredient of the compositions herein is urea which is
preferably present in a level of from about ~).1% to about 20%, more preferably
from about 0.5% to about 10% and especially from about 1% to about 5% by
weight of composition.
In preferred embodiments, the oil phase and organic amphiphilic surfactant
are premixed in water at a temperature above the Kraft Point of the organic
amphiphilic surfactant (but preferably below about 60~C) to form a liquid
crystal/oil in water dispersion prior to addition of the urea. The urea is
found to be especially effective herein in combination with the amphiphilic
emulsifier surfactant and the polyol fatty acid polyester for providing
outstanding skin moisturisation and softening in the context of an oil-in-
water skin care emulsion composition. Moreover, it is surprisingly found
that the urea is rendered more stable to hydrolytic degradation, thereby
allowing an increase in compositional pH.
A wide variety of optional ingredients such as non-occlusive moisturizers,
humectants, gelling agents, neutr~liYin~; agents, perfumes, colouring agents andsurfactants, can be added to the skin compositions herein.
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The compositions herein can comprise a humectant. Suitable humectants for use
herein include sorbitol, propylene glycol, butylene glycol, hexylene glycol,
ethoxylated glucose derivatives, hexanetriol, glycerine, glycine, hyaluronic acid,
arginine, Ajidew (NaPCA), water-soluble polyglycerylmethacrylate lubricants and
panthenols. A preferred humectant herein is glycerine (sometimes known as
glycerol or glycerin). Chemically, glycerine is 1,2,3-propanetriol and is a product
of commerce. One large source of the material is in the manufacture of soap.
Glycerine is especially preferred in the compositions of the invention from the
viewpoint of boosting moisturisation. Also preferred for use herein is butylene
glycol. Particularly preferred from the viewpoint of boosting moisturisation is a
combination of glycerine and urea.
In the present compositions, the humectant is preferably present at a level of from
about 0.1% to about 20%, more preferably from about 1% to about 15%, and
especially from about 5% to about 15% by weight of composition.
Suitable polyglycerylmethacrylate lubricants for use in the compositions of thisinvention are available under the trademark Lubrajel (RTM) from Guardian
Chemical Corporation, 230 Marcus Blvd., Hauppage, N.Y. 11787. In general,
Lubrajels can be described as hydrates or clathrates which are formed by the
reaction of sodium glycerate with a methacrylic acid polymer. Thereafter, the
hydrate or clathrate is stabilized with a small amount of propylene glycol,
followed by conkolled hydration of the resulting product. Lubrajels are marketedin a number of grades of varying glycerate: polymer ratio and viscosity. Suitable
Lubrajels include Lubrajel TW, Lubrajel CG and Lubrajel MS, I,ubrajel WA,
Lubrajel DV and so-called Lubrajel Oil.
At least part (up to about 5% by weight of composition) of the humectant
can be incorporated in the form of an admixture with a particulate lipophilic
or hydrophobic carrier material. The carrier material and humectant can be
added either to the aqueous or disperse phase.
This copolymer is particularly valuable for reducing shine and controlling
oil while helping to provide effective moisturization benefits. The cross-
linked hydrophobic polymer is preferably in the form of a copolymer lattice
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31
with at least one active ingredient dispersed uniformly throughout and
entl ~ed within the copolymer lattice. Alternatively, the hydrophobic
polymer can take the form of a porous particle having a surface area
(N2,BET) in the range from about 50 to 500, preferably 100 to 300m2.g-
and having the active ingredient absorbed therein.
The cross-linked hydrophobic polymer is preferably present in an amount of
from about 0.1% to about 10% by weight and is preferably incorporated in
the external aqueous phase. The active ingredient can be one or more or a
mixture of skin compatible oils, skin compatible humectants, emollients,
moisturizing agents and sunscreens. ~n one embodiment, the polymer
material is in the form of a powder, the powder being a combined system of
particles. The system of powder particles forms a lattice which includes unit
particles of less than about one micron in average diameter, agglomerates of
fused unit particles of sized in the range of about 20 to 100 microns in
average diameter and aggregates of clusters of fused agglomerates of sizes
in the range of about 200 to 1,200 microns in average diameter.
The powder material of this embodiment can be broadly described as a
cross-linked "post absorbed" hydrophobic polymer lattice. The powder
preferably has enkapped and dispersed therein, an active which may be in
the form of a solid, liquid or gas. The lattice is in particulate form and
constitutes free flowing discrete solid particles when loaded with the active
material. The lattice may contain a predetermined quantity of the active
material. A suitable polymer has the structural formula:
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32
CH3 CH3
-- ''CH2'-- C C CH2
C=O C=O
O O
R' - R" - Y
o
C-O
CH2 C-
- CH3 - X
where the ratio of x to y is 80:20, R' is -CH2CH2- and R" is -(CH2)1 1 CH3.
The hydrophobic polymer is a highly crosslinked polymer, more particularly
a highly cross-linked polymethacrylate copolymer. The material is
manufactured by the Dow Corning Corporation, Midland. Michigan, USA,
and sold under the trademark PO~YTRAP (RTM). It is an ultralight free-
flowing white powder and the particles are capable of absorbing high levels
of lipophilic liquids and some hydrophilic liquids while at the same time
maint~inin~ a f~ee-flowing powder character. The powder structure consists
of a lattice of unit particles less than one micron that are fused into
agglomerates of 20 to 100 microns and the agglomerates are loosely
clustered into macro-particles or aggregates of about 200 to about 1200
micron size. The polymer powder is capable of cont~ining as much as four
times its weight o~ fluids, emulsions, dispersion or melted solids.
Adsorption of actives onto the polymer powder can be accomplished using a
stainless steel mixing bowl and a spoon, wherein the active is added to the
powder and the spoon is used to gently fold the active into the polymer
powder. Low viscosity fluids may be adsorbed by addition of the fluids to a
sealable vessel containing the polymer and then tumbling the materials until
a consistency is achieved. More elaborate blending equipment such as
ribbon or twin cone blenders can also be employed. The preferred active
CA 0224782F7 1998-08-31
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33
ingredient for use herein is glycerine. Preferably, the weight ratio of
humectant: carrier is from about 1 :4 to about 3 :1.
Also suitable as a highly cross-linked polymethacrylate copolymer is
Microsponges 5647. This takes the form of generally spherical partic}es of cross-
linked hydrophobic polymer having a pore size of from about 0.01 to about
O.O5~m and a surface area of 200-300m2/g. Again, it is preferably loaded with
humectant in the levels described above.
The compositions of the invention can also contain a hydrophilic gelling agent at a
level preferably from about 0.01% to about 10%, more preferably from about
0.02% to about 2%, and especially from about 0.02% to about 0.5%. The gelling
agent preferably has a viscosity ( 1% aqueous solution, 20~C, Brookfield RVT) ofat least about 4000 mPa.s, more preferably at least about 10,000 mPa.s and
especially at least 50,000 mPa.s.
Suitable hydrophilic gelling agents can generally be described as water-soluble or
colloidally water-soluble polymers, and include cellulose ethers (e.g. hydroxyethyl
cellulose, methyl cellulose, hydroxypropylmethyl cellulose),
polyvinylpyrrolidone, polyvinylalcohol, guar gum, hydroxypropyl guar gum and
x~nt~n gum.
Preferred hydrophilic gelling agents herein, however, are acrylic acid/ethyl
acrylate copolymers and the carboxyvinyl polymers sold by the B.F. Goodrich
Company under the trade mark of Carbopol resins. These resins consist essentially
of a colloidally water-soluble polyalkenyl polyether crosslinked polymer of
acrylic acid crosslinked with from 0.75% to 2.00% of a crosslinking agent such as
for example polyallyl sucrose or polyallyl pentaerythritol. Examples include
Carbopol 934, Carbopol 940, Carbopol 950, Carbopol 954, Carbopol 980,
Carbopol 951 and Carbopol 981. Carbopol 934 is a water-soluble polymer of
acrylic acid crosslinked with about 1% of a polyallyl ether of sucrose having anaverage of about 5.8 allyl groups for each sucrose molecule. A most preferred
polymer is Carbopol 954. Also suitable for use herein are hydrophobically-
modified cross-linked polymers of acrylic acid having amphipathic properties
available under the Trade Name Carbopol 1382, Carbopol 1342 and Pemulen TR-
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1 (CTFA Designation: AcrylatestlO-30 Alkyl Acrylate Crosspolymer). A
combination of the polyalkenyl polyether cross-linked acrylic acid polymer and
the hydrophobically modified cross-linked acrylic acid polymer is also suitable
and is preferred for use herein. The gelling agents herein are particularly valuable
for providing excellent stability characteristics over both normal and elevated
temperatures.
Neutralizing agents suitable for use in neutr~li7in~ acidic group cont~ining
hydrophilic gelling agents herein include sodium hydroxide, potassium hydroxide,ammonium hydroxide, monoethanolamine, diethanolamine and triethanolamine.
The compositions of the invention are in emulsion forrn and are preferably
formulated so as to have a product viscosity of at least about 4,000 mPa.s and
preferably in the range from about 4,000 to about 300,000 mPa.s, more preferablyfrom about 8,000 to about 200,000 mPa.s and especially from about 10,000 to
about 100,000 mPa.s and even more especially from about 10,000 to about 50,000
mPa.s (2S~C, neat, Brookfield RVT ~pindle No. 5).
The compositions ofthe invention can also contain from about 0.1% to about
10%, preferably from about 1% to about 5% of a panthenol moisturizer. The
panthenol moisturizer can be selected from D-panthenol ([~]-2,4-dihydroxy-N-[3-
hydroxypropyl)]-~,3-dimethylbutamide), DL-panthenol, calcium pantothenate,
royal jelly, panthetine, pantotheine, panthenyl ethyl ether, p~n~;~mic acid,
pyridoxin, pantoyl lactose and Vitamin B complex. Highly preferred from the
viewpoint of skin care and tack reduction is D-panthenol.
The compositions of the present invention can additionally comprise from about
0.00~% to about 0.5%, preferably from about 0.002% to about 0.05%, more
preferably from about 0.005% to about 0.02% by weight of carboxymethylchitin.
Chitin is a polysaccharide which is present in the integument of lobsters and crabs
and is a mucopolysaccharide having beta (1-4) linkages of N-acetyl-D-
glucosamine. Carboxymethylchitin is prepared by keating the purified chitin
material with alkali followed by monochloracetic acid. It is sold commercially in
the form of a dilute (approximately 0.1% to 0.5% by weight) aqueous solution
.
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W O97/32560 PCTAUS97102554
under the name Chitin Liquid available from A & E Connock Ltd., Fordingbridge,
Hampshire, Fn,el~r~d.
Other optional materials include keratolytic agents such as salicylic acid; proteins
and polypeptides and derivatives thereof; water-soluble or solubilizable
preservatives such as Germall 115, methyl, ethyl, propyl and butyl esters of
hydroxybenzoic acid, benzyl alcohol, EDTA, Euxyl (RTM) K400, Bromopol (2-
bromo-2-nitropropane- 1,3-diol) and phenoxypropanol; anti-bacterials such as
Irgasan (RTM) and phenoxyethanol (preferably at levels of from 0.1% to about
5%); soluble or colloidally-soluble moisturising agents such as hylaronic acid and
starch-grafted sodium polyacrylates such as Sanwet (RTM) IM-1000, IM-1500
and IM-2500 available from Celanese Superabsorbent Materials, Portsmith, VA,
USA and described in USA-A-4,076,663; vitamins such as vitamin A, vitamin C,
vitamin E and vitamin K; alpha and beta hydroxyacids; aloe vera; sphingosines
and phytosphingosines, cholesterol; skin whitening agents; N-acetyl cysteine;
colouring agents; perfumes and perfume solubilizers and additional
surfactants/emulsifiers such as fatty alcohol ethoxylates, ethoxylated polyol fatty
acid esters, wherein the polyol can be selected ~om glycerine, propyleneglycol,
ethyleneglycol, sorbitol, sorbitan, polypropyleneglycol, glucose and sucrose.
Examples include glyceryl monohydroxy stearate and stearyl alcohol ethoxylated
with an average of from 10 to 200 moles of ethyleneoxide per mole of alcohol andPEG-6 caprylic/capric glycerides.
Also useful herein are sunscreening agents. A wide variety of sunscreening
agents are described in U.S. Patent No. 5,087,445, to Haffey et al., issued
February 11, 1992; U.S. Patent No. 5,073,372, to Turner et al., issued
December 17, 1991; U.S. Patent No. 5,073,371, to Turner et al. issued
December 17, 1991; and Segarin, et al., at Chapter VIII, pages 189 et seq.,
of Cosmetics Science and Technolo~y. Preferred among those sunscreens
which are useful in the compositions of the instant invention are those
selected from 2-ethylhexyl p-methoxycinn~m~te, 2-ethylhexyl N,N-
dimethyl-p-aminobenzoate, p-aminobenzoic acid, 2-phenylbenzimidazole-5-
sulfonic acid, octocrylene, oxybenzone, homomenthyl salicylate, octyl
salicylate, 4,4'-methoxy- -butyldibenzoylmethane, 4-;sopropyl
dibenzoylmethane, 3-benzylidene camphor, 3-(4-methylbenzylidene)
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36
camphor, titanium dioxide, zinc oxide, silica, iron oxide, Parsol MC~,
Eusolex 6300, Octocrylene, Parsol 1789, and mixtures thereof.
Still other useful sunscreens are those disclosed in U.S. Patent No.
4,937,370, to Sabatelli, issued June 26, 1990; and U.S. Patent No.
4,999,186, to Sabatelli et al., issued March 12, 1991. The sunscreening
agents disclosed therein have, in a single molecule, two distinct
chromophore moieties which exhibit different ultra-violet radiation
absorption spectra. One of the chromophore moieties absorbs pre-
dominantly in the UVB radiation range and the other absorbs strongly in the
WA radiation range. These sunscreening agents provide higher efficacy,
broader W absorption, lower skin penetration and longer lasting efficacy
relative to conventional sunscreens. Especially preferred examples of these
sunscreens include those selected from 4-N,N-(2-ethylhexyl)methyl-
aminobenzoic acid ester of 2,4-dihydroxybenzophenone, 4-N,N-(2-
ethylhexyl)methylaminobenzoic acid ester with 4-
hydroxydibenzoylmethane, 4-N,N- (2-ethylhexyl)methylaminobenzoic acid
ester of 2-hydroxy-4-(2-hydroxyethoxy)benzophenone, 4-N,N-(2-
ethylhexyl)-methylaminobenzoic acid ester of 4-(2-hydroxyeth-
oxy)dibenzoylmethane, and mixtures thereof.
Generally, the sunscreens can comprise from about 0.5% to about 20% of the
compositions useful herein. Exact amounts will vary depending upon the
sunscreen chosen and the desired Sun Protection Factor (SPF). SPF is a
commonly used measure of photoprotection of a sunscreen against erythema. See
Federal Re~;ister, Vol. 43, No. 166, pp. 38206-38269, August 25, 1978.
The compositions of the present invention can additionally comprise from about
0.1% to about 5% by weight of aluminium starch octenylsuccinate. Aluminium
starch octenylsuccinate is the aluminium salt of the reaction product of
octenylsuccinic anhydride with starch and is commercially available under the
trade name from Dry ~lo National Starch & Chemical Ltd. Dry Flo is useful
herein from the viewpoint of skin feel and application characteristics.
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37
Other optional materials herein include pigments which, where water-insoluble,
contribute to and are included in the total level of oil phase ingredients. Pigments
suitable for use in the compositions of the present invention can be organic and/or
t inorganic. Also included within the term pigment are materials having a low
colour or lustre such as matte fini~hin~; agents, and also light scattering agents.
Examples of suitable pigments are iron oxides, acyglllt~m~te iron oxides,
ultramarine blue, D&C dyes, carmine, and mixtures thereof. Depending upon the
type of composition, a mixture of pigments will normally be used. The preferred
pigments for use herein from the viewpoint of moisturisation, skin feel, skin
appearance and emulsion compatibility are treated pigments. The pigments can be
treated with compounds such as amino acids, silicones, lecithin and ester oils.
The pH of the compositions is preferably from about 4 to about 9, more
preferably from about 6 to about 8Ø
The balance of the composition is water or an aqueous carrier suitable for
topical application to the skin. The water content of the compositions herein
is generally from about 30% to about 98.89%, preferably from about 50% to
about 95% and especially from about 60% to about 90% by weight.
The compositions of the invention are preferably in the form of a
moisturising cream or lotion, which can be applied to the skin as a leave-on
product.
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38
The invention is illustrated by the following examples "
Examples I to V
I/% II/% III/% IV/% V/%
Cetyl Alcohol 0.72 0.5 0.8 0.65 0.75
Stearic Acid 0.11 0.2 0.1 0.2 0.1
Steareth 100 0.1 0.1 0.15 0.15 0.15
Propyl Paraben 0.17 0.08 0.07 0.15 0.07
Arlatone(RTM) 1.0 2.0 1.5 1.0 4.0
2121(1)
Glycerin 3 4 8 2.5 3.5
Carbopol (RTM) 0.1 0.075 0.08 0.075 0.075
1382
Carbopol (RTM)954 0.7 0.56 0.5 0.65 0.45
Na4 EDTA 0.1 0.2 0.1 0.1 0.1
Methyl Paraben 0.2 0.2 0.175 0.175 0.175
NaOH (40% solution) 1.0 0.8 0.8 0.8 0.8
Dimethicone Q21403 1.0 1.0 0.5 2.0 1.0
TiO2 0.15 0.15 0.15 0.15 0.15
Perfume 0.2 0.2 - 0.2
Urea 2.5 1.5 3 2 2.5
SEFA (2) 0.0 0.0 2.5 2.0 2.2
Octyldodecyl 0.0 0.0 0.0 1.0 1.0
benzoate
KSG-18(3) 3.0 0.0 2.0 0.0 0.0
SiliconDioxide(4~ 1.5 1.5 2.0 3.0 0.0
Polyethylene Beads 0.0 1.5 2.0 0.0 3.0
(5)
Colour 0.0004 0.0002 0.0003 0.0 0.0
Water to 100 to 100 to 100 to 100 to 100
1. Supplied by ICI
2. Liquid sucrose polyester which is a mixture of hexa-, hepta-, and
octa- sucrose esters esterified with mixed cottonseed oil fatty acids,
predomin~tely the octa-ester.
3. Supplied by Shinetsu Chemical Co. Ltd.
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4. Silica Bead SB-300 supplied by Miyoshi Kasei Inc.
5. Flo-Beads LE-1080 supplied by Sumitomo Seika Chemicals Co.
Ltd.
,,
The compositions are made as follows:
A first premix of thickening agents, silicon dioxide when present, methyl
paraben, glycerine/TiO2 premix, Arlatone 2121, and other water soluble
ingredients apart from urea, is prepared by admixing in water and heating to
about 80~C. A second premix of oil phase ingredients other than silicone
gum is prepared by mixing and heating and is added to the aqueous premix.
The resulting mixture is cooled to about 60~C. The NaOH solution, EDTA,
polyethylene when present, silicone gum, KSG- 18 when present and then
urea solution ( 1 g dissolved in 1 ml of water) are then added to the resulting
oil-in-water emulsion and the mixture is cooled before ~d-linp minor
ingredients. The composition is ready for pack~pin,e
The compositions display improved moisturisation, skin feel and skin care
characteristics together with reduced greasiness and excellent rub-in and fast
absorption characteristics.
