Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
COMPOSITIONS CONTAINING SELECT SOLID POLYOL FATTY ACID
POLYESTERS
TECHNICAL FIELD
The present invention relates to compositions suitable for topical application
to human hair or skin, which comprise a select combination of solid polyol
fatty acid
1o polyesters having a melting point of from about 30°C to about
80°C and liquid oils
having a melting point of less than about 30°C to about -30°C.
BACKGROUND OF THE INVENTION
Topical compositions containing emollients have been used for many years in
the treatment of human hair or skin. For example, occlusive hydrocarbons such
as
petrolatum have been used as topical emollients to provide a protective film
onto
human skin to prevent water loss to the environment. Petrolatum has also been
used
in hair care products such as conditioners and grooming aids.
However, the most effective and widely used compositions containing
occlusive emollients suffer from negative aesthetic qualities such as
greasiness and
2o stickiness. Moreover, some occlusive emollients that are used to provide a
protective film on the skin results in clogging the skin pores and preventing
the flow
of oxygen. This obstruction of the skin surface or blockage of the passage or
circulation of air and moisture limits the use of such heavy, occlusive
emollient
materials. Additionally, European Patent No. 458,600 B1, published March 2,
1994,
discloses occlusive skin care compositions containing a polyol fatty acid
polyester
having at least 4 free hydroxyl groups, at least 60% of which are esterified
with one
or more fatty acids having from 8 to 22 carbon atoms which can form an
occlusive
film on the skin following topical application thereon. U.S. Patent No.
5,160,738, to
Macaulay et al., issued November 3,1992, further discloses occlusive
compositions
3o containing a blend of two or more polyol fatty acid polyesters which has
the
appearance and physical properties of petrolatum. However, these compositions
also
have the disadvantage of being heavy and can clog the skin pores preventing
the
flow of oxygen.
It has now been found that compositions containing occlusive emollients can
be formulated without being heavy, sticky, or greasy. These compositions
contain a
select combination of solid polyol fatty acid polyesters having a melting
point of
from about 30°C to about 80°C, and liquid oils having a melting
point less than
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
2
about 30°C to about -30°C, and such compositions are applicable
in a variety of
products to provide both efficacy and aesthetic benefits.
It is therefore an object of the present invention to provide a composition
which has both effective emolliency and acceptable aesthetic qualities, and
which
contain an occlusive emollient used in combination with a liquid oil. It is a
further
object of the present invention to provide topical compositions containing
polyol
fatty acid polyesters which are not heavy, sticky, and greasy, and which are
effective
in the treatment of human hair or skin.
SUMMARY OF THE INVENTION
1o The present invention relates to a composition suitable for topical
application to
the human hair or skin, which comprises a combination of a solid polyol fatty
acid
polyester having a melting point of from about 30°C to about
80°C, and a liquid oil
other than a liquid polyol fatty acid polyester having a melting point of less
than
about 30°C to about -30°C, wherein said solid polyol fatty acid
polyester has a
polyol moiety and at least 1 fatty acid moiety, the polyol moiety having at
least 4
free hydroxyl groups wherein at least 60% of these free hydroxyl groups are
esterified with one or more fatty acid moieties having from about 8 to about
22
carbon atoms. The composition preferably further comprises a topical carrier
for the
solid polyol fatty acid polyester and liquid oil combination.
2o All percentages and ratios used herein are by weight and all measurements
made are at 25oC, unless otherwise designated. The invention hereof can
comprise,
consist of, or consist essentially of, the essential as well as optional
ingredients and
components described herein.
DETAILED DESCRIPTION OF THE INVENTION
The term "topical composition" as used herein means a composition suitable
for topical application to human hair or skin. The term is used to encompass a
wide
variety of personal care, beauty care, and cosmetic compositions. Nonlimiting
examples of topical compositions include lotions, creams, hand and body
lotions,
skin conditioning lotions and creams, skin protectant compositions, sunscreen
compositions, cold creams, anti-acne compositions, skin renewal products, non-
lathering cleansing lotions, moisturizers, facial moisturizers, make-ups,
foundations,
lipsticks, lip protectants, skin cleansers, hand, face, and body cleansers,
shower
products, shampoos, and the like.
The term "topical carrier", as used herein, is well-known to one of ordinary
skill in the art, and means one or more compatible solid or liquid filler
diluents or
vehicles which are suitable for administration to a human. The term
"compatible",
as used herein, means that the components of the topical carrier are capable
of being
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
3
comingled with the components of the present invention, and with each other,
in a
manner such that there is no interaction which would substantially reduce the
efficacy or aesthetics of the cosmetic composition under ordinary use
situations. The
topical carrier must be a pharmaceutically acceptable carrier. The term
"pharmaceutically-acceptable", as used herein, means that the topical carrier
must be
of sufficiently high purity and be suitable for use in contact with human hair
or skin
without undue toxicity, incompatibility, instability, allergic response, and
the like.
The melting point of the solid polyol fatty acid polyesters and liquid oils
can
be determined using conventional techniques. Such techniques are well defined
in
i o the art, and include thermometric as well as calorimetry methodology. A
particularly
preferred technique for determining the melting point is described in U.S.
Patent No.
5,306,514, to Letton et al., issued April 26, 1994, which is incorporated by
reference
herein in its entirety. This technique typically involves measuring melting
points
using Differential Scanning Calorimetry (DSC) whereby a scanning temperature
of 5
l5 °C/minute is used to measure the melting point. The melting point is
the
temperature at the intersection of the baseline, i.e. the specific heat line,
with the line
tangent to the trailing edge of the endothermic peak.
Solid Polyol Fatty Acid Polyester
The composition of the present invention comprises a solid polyol fatty acid
2o polyester at concentrations ranging from about 0.1 % to about 99.9%,
preferably from
about 0.5% to about 75%, more preferably from about 1 % to about 50%, even
more
preferably from about 2% to about 25%, by weight of the composition. These
solid
polyol fatty acid polyesters have melting points of from about 30°C to
about 80°C,
and are derived from any aliphatic or aromatic polyol which has at least 4
free
25 hydroxyl groups, of which at least 60% of these free hydroxyl groups are
then
esterified with one or more fatty acids having from about 8 to about 22 carbon
atoms. The fatty acids can also be described as carboxylic acids, because the
terms
fatty acid and carboxylic acid are often used interchangeably by those skilled
in the
art.
3o The solid polyol polyesters employed in this invention are polyol esters or
polyesters wherein the fatty acid ester groups of the polyester comprise a
combination of: (a) long chain unsaturated fatty acid moieties or a mixture of
long
' chain unsaturated fatty acid moieties and short chain saturated fatty acid
moieties,
and (b) long chain saturated fatty acid moieties, the ratio of (a) to (b)
being from
' 35 about 1 to 15 to about 2 to 1. At least about 15%, preferably at least
about 30%,
more preferably at least about 50%, and most preferably at least about 60% by
weight of the total fatty acid moieties of the polyesters are C20 or higher
saturated
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
4
fatty acid moieties. The long chain unsaturated fatty acid moieties are
typically
straight chain and contain at least about 12, preferably about 12 to about 22,
more
preferably about 18 to about 22 carbon atoms. The most preferred unsaturated
fatty
acids are the C 18 mono and/or di unsaturated fatty acids. The short chain
saturated
fatty acids are typically unbranched and contain about 2 to about 12,
preferably
about 6 to about 12, and most preferably about 8 to about 12 carbon atoms. The
long chain saturated fatty acids are typically straight chain and contain at
least about
20, preferably about 20 to about 22, and most preferably about 22 carbon
atoms.
The molar ratio of Group (a) fatty acid moieties to Group (b) fatty acid
moieties in
to the polyester molecule is from about 1:15 to about 2:1, preferably about I
:7 to about
5:3, and more preferably about 1:7 to about 3:~. The average degree of
esterification of these fatty acid esters is such that at least about 60% of
the
hydroxyl groups of the polyol are esterified. In the case of sucrose
polyesters from
about 7 to about 8 of the hydroxyl groups of the polyol are preferably
esterified.
is Typically, substantially all, e.g., at least about 85%, preferably at least
about 95%,
of the hydroxyl groups of the polyol are esterified.
Preferred polyols of the solid polyol fatty acid esters are sugars, including
monosaccharides and disaccharides and trisaccharides, containing from about 4
to
about 11 hydroxyl groups. Most preferred sugars are those which contain about
4 to
2o about 8, more preferably about 6 to about 8 hydroxyl groups. Examples of
those
containing four hydroxyl groups are the monosaccharides xylose, arabinose, and
combinations thereof. Suitable five hydroxyl group-containing polyols are the
monosaccharides galactose, fructose, mannose, glucose, and combinations
thereof.
Examples of disaccharide polyols which can be used include maltose, lactose,
25 sucrose, and combinations thereof, all of which contain eight hydroxyl
groups. The
preferred polyol is sucrose.
Examples of long chain unsaturated fatty acid moieties include, but are not
limited to, lauroleate, myristoleate, palmitoleate, oleate, elaidate, erucate,
linoleate,
linolenate, arachidonate, eicosapentaentoate, and docosahexaenoate. For
oxidative
3o stability, the mono- and diunsaturated fatty acid moieties are preferred.
Examples of suitable short chain saturated fatty acid moieties include, but
are not limited to, acetate, caproate, caprylate, caprate, and laurate.
Examples of suitable long chain saturated fatty acid moieties include, but are
not limited to, arachidate, behenate, lignocerate, and cerotate.
35 Of course, the long chain unsaturated fatty acid moieties can be used
singly
or in mixtures with each other or in mixtures with the short chain saturated
fatty
acid moieties, in all proportions. Likewise, the long chain saturated fatty
acid
CA 02289696 1999-11-15
WO 98/52531 PCTlIB98/00787
- _
moieties can be used in combination with each other in all proportions. Mixed
fatty
acid moieties from source oils which contain substantial amounts of the
desired
unsaturated or saturated acids can be used as the acid moieties to prepare
compounds for use herein. The mixed fatty acids from the oils should contain
at
5 least about 30%, preferably at least about 50%, and most preferably at least
about
. 80% of the desired unsaturated or saturated acids. For example, rapeseed oil
fatty
acids or soybean oil fatty acids can be used instead of pure C 12-C 16
unsaturated
fatty acids. Hardened, i.e. hydrogenated, high erucic rapeseed oil fatty acids
can be
used instead of pure C20-C22 saturated acids. Preferably the C20 and higher
acids,
or their derivatives, e.g. methyl or other low alkyl esters, are concentrated
for
example by distillation. The fatty acids from palm kernal oil or coconut oiI
can be
used as a source of C8 to C12 acids, An example of the use of source oils to
make
solid polyol polyesters for use in the compositions herein is the preparation
of solid
sucrose polyester, employing the fatty acids of high oleic sunflower oil and
1 s substantially completely hydrogenated high erucic rapeseed oil. When
sucrose is
substantially completely esterified with a 1:3 by weight blend of the methyl
esters of
the fatty acids of these two oils, the resulting sucrose polyester will have a
molar
ratio of unsaturated C 18 acid radicals to C20 and higher saturated acid
radicals of
about 1:1 and about 28.6 weight percent of the total fatty acids in the
polyester will
2o be C22 fatty acids.
The higher the proportions of the desired unsaturated and saturated acids in
the fatty acid stocks used in making the solid polyol polyester, the more
efficient the
ester will be in its ability to bind with the liquid oils described
hereinbelow.
Examples of solid polyol fatty acid polyesters for use in the composition
25 herein include, but are not limited to, the octaester of raffinose in which
the
esterifying fatty acid moieties are linoleate and behenate in a 1:3 molar
ratio; the
heptaester of maltose wherein the esterifying fatty acid moieties are
sunflower seed
oil fatty acids and lignocerate in a 3:4 molar ratio; the octaester of sucrose
wherein
the esterifying fatty acid moieties are oleate and behenate in a 2:6 molar
ratio; and
3o the octaester of sucrose wherein the esterfying fatty acid moieties are
laurate,
linoleate and behenate in a 1:3:4 molar ratio. A preferred material is sucrose
polyester in which the degree of esterification is 7-8, and in which the fatty
acid
moieties are C 18 mono- and/or di-unsaturated and behenic, in a molar ratio of
unsaturates:behenic of 1:7 to 3:5. A particularly preferred polyol ester is
the
35 octaester of sucrose in which there are about 7 behenic fatty acid moieties
and about
1 oleic moiety in the molecule.
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
6
The solid fatty acid polyesters herein can be made according to prior art
known methods for preparing polyesters of poiyols. See, for example U.S.
Patent
No. 5,306,516, to Letton et al:, issued April 26, 1994; U.S. Patent No.
5,306.515, to
Letton et al., issued April 26, 1994; U.S. Patent No. 5,305,514, to Letton et
aL, '
issued April 26, 1994; U.S. Patent No. 4,797,300, to Jandacek et al., issued
January
10, 1989; U.S. Patent No. 3,963,699, to Rizzi et al., issued June 15, 1976;
U.S.
Patent No. 4,518,772, to Volpenhein, issued May 21, 1985; and U.S. Patent No.
4,517,360, to Volpenhein, issued May 21, 1985; all of which are incorporated
by
reference herein in their entirety.
to Liquid Oil
The composition of the present invention comprises a liquid oil used in
combination with the solid polyol fatty acid polyester described herein. The
liquid
oil can be used as an individual liquid oil or a combination of liquid oils,
and is
included at concentrations ranging from about 0.1 % to about 99.9%, preferably
from
about 0.5% to about 75%, more preferably from about 1% to about 50%, even more
preferably from about 2% to about 25%, by weight of the composition.
Liquid oils useful herein are those materials which have a melting point less
than about 30°C, preferably less than about 30°C to about -
30°C, more preferably
less than about 27.5oC to about -30oC, and even more preferably less than
about
25oC to about -30oC The liquids oils generally have a low solubility in water,
generally less than about 1% by weight at 25°C. Examples of suitable
liquid oils
include, but are not limited to, mineral oil, hydrocarbons having from about 5
to
about 16 carbon atoms, fatty alcohol esters having from about 3 to about 22
carbon
atoms, fatty acid esters having from about 3 to about 30 carbon atoms,
vegetable
oils, and mixtures thereof. Other liquid oils suitable for use herein are
described in
WO 95-00166, to Gordon et al., published January 5, 1995, which is
incorporated by
reference herein in its entirety.
Mineral oil, which is also known as petrolatum liquid, is suitable for use
herein. This compound is a mixture of liquid hydrocarbons obtained from
3o petroleum. See The Merck Index, Tenth Edition, Entry 7048, p. 1033 (1983)
and
International Cosmetic Ingredient Dictionary, Fifth Edition, vol. 1, p.415-417
(1993), which are incorporated by reference herein in their entirety.
Suitable hydrocarbons for use herein include straight and branched chain
hydrocarbons having from about S to about 16 carbon atoms. Nonlimiting
examples
of these hydrocarbon materials include dodecane, isododecane, hydrogenated
polyisobutylene, hexadecane, isohexadecane (a commercially available
hydrocarbon
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
7
sold as Permethyl~ 1 O1 A by Presperse, South Plainfield, NJ). Also useful are
the
CS-C 16 isoparaffins, which are CS-C 16 branched hydrocarbons.
Suitable fatty alcohol esters for use herein include esters and diesters of
fatty
alcohols which have from about 3 to about 22 carbon atoms. Also useful are
fatty
acid esters having from about 3 to about 30 carbon atoms. Nonlimiting examples
of
these ester materials include isopropyl myristate, isopropyl palmitate,
isopropyl
stearate, diisopropyl adipate, and dioctyl sebacate (dioctyl ester of
decanedioic acid).
Vegetable oils which are liquid at ambient temperatures of from about
20°C to
about 25°C are also useful herein. Examples of suitable vegetable oils
include cod
to liver oil, dolphin oil, lard oil, peat's-foot oil, porpoise oil, seal oil,
sperm oil, whale
oil, acorn oil, almond oil, beechnut oil, chaulmoogra oil, rapeseed, soybean
oil,
sunflower-seed oil, groundnut oil, cottonseed oil, corn oii, safflower oil,
olive oil,
menhaden oil, sesame seed, castor oil, hazelnut oil, hemp-seed oil, linseed
oil,
mustard (black) oil, neem oil, peanut oil, pistachio-nut oil, poppy-seed oil,
pumpkin
seed oil, Tung oil, white-mustard-seed oil, pine oil, wheat germ oil,
derivatives
thereof and mixtures thereof.
Topical Carrier
The composition of the present invention comprises from about 0.1 % to about
99.9%, preferably from about 50% to about 99%, and more preferably from about
2o 60% to about 95% by weight of a topical carrier for the solid polyol fatty
acid
polyester and liquid oil combination, and for any other optional components of
the
present invention.
The solid polyol fatty acid polyester and liquid oil combination of the
present
invention can be formulated into a wide variety of product types, including
creams,
lotions, milks, gels, hand and body lotions, cold creams, non-lathering
cleansing
lotions, facial moisturizers, sunscreens, anti-acne preparations, topical
analgesics,
mascaras, lipsticks, skin cleansers, hand, face, and body cleansers, shower
products,
shampoos, and the like. The carriers and any additional components required to
formulate such products vary with product type and can be routinely chosen by
one
3o skilled in the art.
The topical carrier can be in a wide variety of forms. For example, emulsion
carriers, including, but not limited to, oil-in-water, water-in-oil, water-in-
oil-in-
water, and oil-in-water-in-silicone emulsions, are useful herein. These
emulsions
can cover a broad range of viscosities, e.g., from about 100 cps to about
200,000 cps.
Other suitable topical carriers include anhydrous liquid solvents such as
alcohols,
and silicones (e.g., ethanol, isopropanol, dimethicone, cyclomethicone, and
the like);
aqueous-based single phase liquid solvents (e.g., hydro-alcoholic solvent
systems);
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
8 _
and thickened versions of these anhydrous and aqueous-based single phase
solvents
(e.g., where the viscosity of the solvent has been increased to form a solid
or semi-
solid by the addition of appropriate gums, resins, waxes, polymers, salts, and
the
like). Examples of topical carrier systems useful in the present invention are
described in the following references all of which are incorporated herein by
reference in their entirety: "Sun Products Formulary" Cosmetics & Toiletries,
vol.
105, pp. 122-139 (December 1990); "Sun Products Formulary", Cosmetics &
Toiletries, vol. 102, pp. 117-136 (March 1987); U.S. Patent No. 4,960,764 to
Figueroa et al., issued October 2, 1990; U.S. Patent No. 4,254,105 to Fukuda
et al.,
l o issued March 3, 1981; U. S. Patent No. 4,976,953, to On et al., issued
December I 1,
1990; U.S. Patent No. 5,073,372, to Turner et al., issued December 17, 1991;
U.S.
Patent No. 5,585,104, to Ha et al., issued December 17, 1996; U.S. Patent No.
5,607,678, to Moore et al., issued March 4, 1997; U.S. Patent No. 5,607,980,
to
McAtee et al., issued March 4, 1997; and U.S. Patent No. 5,618,522, to Kaleta
et al.,
~ 5 issued April 8, I 997.
The topical carrier can also comprise an oil-in-water emulsion system having
complex structures such as liquid crystals and crystalline gel networks. The
nature
of liquid crystals, the formation of liquid crystals, the properties and
advantages of
liquid crystals are described further in G. Dahms, Properties of O/W Emulsions
With
2o Anisotropic Lameliar Phases, 101 Cosmetics & Toiletries, 113-I15 (1986); P.
Loll,
Liquid Crystals in Cosmetic Emulsions, ICI Surfactants' Publication RP9-I-93E;
and
G. M. Eccleston, Multiple-Phase Oil-In-Water Emulsions, 41, J. Soc. Cosmet.
Chem., I-22, (January/February 1990); ail of which are incorporated herein by
reference in their entirety.
25 Additional Components
A wide variety of additional components can be employed in the compositions
herein. Non-limiting examples include the following:
Pharmaceutical Actives
The compositions of the present invention can comprise a safe and effective
3o amount of a pharmaceutical active. The phrase "safe and effective amount",
as used
herein, means an amount of an active high enough to significantly or
positively
modify the condition to be treated, but low enough to avoid serious side
effects (at a
reasonable benefitlrisk ratio), within the scope of sound medical judgment. A
safe
and effective amount of the pharmaceutical active will vary with the specific
active,
35 the ability of the composition to penetrate the active through the skin,
the amount of
composition to be applied, the particular condition being treated, the age and
CA 02289696 1999-11-15
WO 98!52531 PCT/IB98/00787
9
physical condition of the patient being treated, the severity of the
condition, the
duration of the treatment, the nature of concurrent therapy, and like factors.
The pharmaceutical actives which can be used in the compositions of the
present invention preferably comprise from about 0.1 % to about 20% by weight
of
the compositions, more preferably from about 0.1% to about 10%, and most
preferably from about 0.1 % to about 5%. Mixtures of pharmaceutical actives
may
also be used.
Nonlimiting examples of pharmaceutical actives can include the following:
Useful pharmaceutical actives in the compositions of the present invention
1 o include anti-acne drugs. Anti-acne drugs for use herein include the
keratolytics such
as salicylic acid, sulfur, lactic acid, glycolic, pyruvic acid, resorcinol,
and N-
acetylcysteine; retinoids such as retinoic acid and its derivatives (e.g., cis
and trans);
antibiotics and antimicrobials such as benzoyl peroxide, octopirox,
erythromycin,
zinc, tetracyclin, triclosan, azeIaic acid and its derivatives, phenoxy
ethanol and
phenoxy propanol, ethylacetate, clindamycin and meclocycline; sebostats such
as
flavinoids; alpha and beta hydroxy acids; and bile salts such as scymnol
sulfate and
its derivatives, deoxycholate, and cholate. Preferred anti-acne actives are
those
selected from the group consisting of salicylic acid, sulfur, resorcinol,
lactic acid,
zinc, erythromycin, benzoyl peroxide, and mixtures thereof. More preferred is
2o salicylic acid.
Useful pharmaceutical actives in the compositions of the present invention
include non-steroidal anti-inflammatory drugs (NSAIDS). The NSAIDS can be
selected from the following categories: propionic acid derivatives; acetic
acid
derivatives; fenamic acid derivatives; biphenylcarboxylic acid derivatives;
and
oxicams. All of these NSAIDS are fully described in the U.S. Patent 4,985,459
to
Sunshine et al., issued January 15, 1991, incorporated by reference herein.
Most
preferred are the propionic NSAIDS including but not limited to aspirin,
acetaminophen, ibuprofen, naproxen, benoxaprofen, flurbiprofen, fenoprofen,
fenbufen, ketoprofen, indoprofen, pirprofen, carprofen, oxaprozin,
pranoprofen,
3o miroprofen, tioxaprofen, suprofen, alminoprofen, tiaprofenic acid,
fluprofen and
bucloxic acid. Also useful are the steroidal anti-inflammatory drugs including
hydrocortisone and the like.
' Useful pharmaceutical actives in the compositions of the present invention
include antipruritic drugs. Antipruritic drugs preferred for inclusion herein
include
pharmaceutically-acceptable salts of methdilizine and trimeprazine.
Useful pharmaceutical actives in the compositions of the present invention
include anesthetic drugs. Anesthetic drugs preferred for inclusion herein
include
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
'
pharmaceutically-acceptable salts of lidocaine, bupivacaine, chlorprocaine,
dibucaine, etidocaine, mepivacaine, tetracaine, dyclonine, hexylcaine,
procaine,
cocaine, ketamine, pramoxine and phenol.
Useful pharmaceutical actives in the compositions of the present invention -
5 include antimicrobial drugs (antibacterial, antifungal, antiprotozoal and
antiviral
drugs). Antimicrobial drugs preferred for inclusion herein include
pharmaceutically-
acceptable salts of b-lactam drugs, quinolone drugs, ciprofloxacin,
norfloxacin,
tetracycline, erythromycin, amikacin, triclosan, doxycycline, capreomycin,
chlorhexidine, chlortetracycline, oxytetracycline, clindamycin, ethambutoi,
to metronidazole, pentamidine, gentamicin, kanamycin, lineomycin,
methacycline,
methenamine, minocycline, neomycin, netilmicin, paromomycin, streptomycin,
tobramycin, miconazole and amanfadine. Antimicrobial drugs preferred for
inclusion herein include tetracycline hydrochloride, erythromycin estolate,
erythromycin stearate (salt), amikacin sulfate, doxycycline hydrochloride.
capreomycin sulfate, chlorhexidine gluconate, chlorhexidine hydrochloride,
chlortetracycline hydrochloride, oxytetracycline hydrochloride, clindamycin
hydrochloride, ethambutol hydrochloride, metronidazole hydrochloride,
pentamidine
hydrochloride, gentamicin sulfate, kanamycin sulfate, lineomycin
hydrochloride,
methacycline hydrochloride, methenamine hippurate, methenamine mandelate,
minocycline hydrochloride, neomycin sulfate, netilmicin sulfate, paromomycin
sulfate, streptomycin sulfate, tobramycin sulfate, miconazole hydrochloride,
amanfadine hydrochloride, amanfadine sulfate, triclosan, octopirox,
parachlorometa
xylenol, nystatin, tolnaftate and clotrimazole.
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
Technolosv, all
of which are incorporated herein by reference in their entirety. Preferred
among
3o those sunscreens which are useful in the compositions of the instant
invention are
those selected from the group consisting of 2-ethylhexyl p-methoxycinnamate, 2-
ethylhexyl N,N-dimethyl-p-aminobenzoate, p-aminobenzoic acid, 2-
phenylbenzimidazole-5-sulfonic acid, octocrylene, oxybenzone, homomenthyl
salicylate, octyl salicylate, 4,4'-methoxy-t-butyldibenzoylmethane, 4-
isopropyl
dibenzoylmethane, 3-benzylidene camphor, 3-(4-methylbenzylidene) camphor,
titanium dioxide, zinc oxide, silica, iron oxide, and mixtures thereof.
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
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; these two references are incorporated by reference
herein in
their entirety. 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 predominantly in
the
UVB radiation range and the other absorbs strongly in the UVA radiation range.
These sunscreening agents provide higher efficacy, broader LTV absorption.
lower
skin penetration and longer lasting efficacy relative to conventional
sunscreens.
to Especially preferred examples of these sunscreens include those selected
from the
group consisting of 4-N,N-(2-ethyihexyl)methylaminobenzoic 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-hydroxyethoxy)dibenzoylmethane, and
mixtures thereof.
Generally, the compositions can comprise from about 0.5% to about 20% of
the sunscreens useful herein. Exact amounts will vary depending upon the
sunscreen
chosen and the desired Sun Protection Factor (SPF). SPF is a commonly used
2o measure of photoprotection of a sunscreen against erythema. See Federal Re
ig ster,
Vol. 43, No. 166, pp. 38206-38269, August 25, 1978, which is incorporated
herein
by reference in its entirety.
Also useful in the compositions of the present invention are sunless tanning
agents including dihydroxyacetone, glyceraldehyde, indoles and their
derivatives,
and the like. These sunless tanning agents can also be used in combination
with the
sunscreen agents.
Other useful actives include skin bleaching (or lightening) agents including
but not limited to hydroquinone, ascorbic acid, kojic acid and sodium
metabisulfite.
Humectants and Moisturizers
3o The compositions of the present invention can also contain one or more
additional humectant or moisturizing materials other than those described
herein. A
variety of these materials can be employed and each can be present at a level
of from
about 0.1 % to about 20%, more preferably from about 1 % to about 10% and most
preferably from about 2% to about 5%, by weight of the composition. These
materials include guanidine; glycolic acid and glycolate salts (e.g. ammonium
and
quaternary alkyl ammonium); lactic acid and lactate salts (e.g. ammonium and
quaternary alkyl ammonium); aloe vera in any of its variety of forms (e.g.,
aloe vera
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
12 -
gel); poiyhydroxy alcohols such as sorbitol, glycerol, hexanetriol, propylene
glycol,
butylene glycol, hexylene glycol and the like; polyethylene glycols; sugars
and
starches; sugar and starch derivatives (e.g., aIkoxylated glucose); hyaiuronic
acid;
Iactamide monoethanolamine; acetamide monoethanolamine; and mixtures thereof.
Emulsifiers
The compositions herein can contain various emulsifiers. These emulsifiers
are useful for emulsifying the various carrier components of the compositions
herein.
Suitable emulsifiers can include any of a wide variety of nonionic, cationic,
anionic,
and zwitterionic emulsifiers disclosed in the prior patents and other
references. _See
to McCutcheon's, Detergents and Emulsifiers, North American Edition (1986),
published by Allured Publishing Corporation; U.S. Patent No. S,OI 1,681 to
Ciotti et
al., issued April 30, 1991; U.S. Patent No. 4,421,769 to Dixon et al., issued
December 20, 1983; and U.S. Patent No. 3,755,560 to Dickert et al., issued
August
28, 1973; these four references are incorporated herein by reference in their
entirety.
Suitable emulsifier types include esters of glycerin, esters of propylene
glycol,
fatty acid esters of polyethylene glycol, fatty acid esters of polypropylene
glycol,
esters of sorbitol, esters of sorbitan anhydrides, carboxylic acid copolymers,
esters
and ethers of glucose, ethoxylated ethers, ethoxylated alcohols, alkyl
phosphates,
polyoxyethylene fatty ether phosphates, fatty acid amides, acyl lactylates,
soaps and
2o mixtures thereof.
Suitable emulsifiers can include, but are not limited to, polyethylene glycol
20
sorbitan monolaurate (Polysorbate 20), polyethylene glycol 5 soya sterol,
Steareth-
20, Ceteareth-20, PPG-2 methyl glucose ether distearate, Ceteth-10,
Polysorbate 80,
cetyl phosphate, potassium cetyl phosphate, diethanolamine cetyl phosphate,
Polysorbate 60, glyceryl stearate, PEG-100 stearate, and mixtures thereof.
The emulsifiers can be used individually or as a mixture of two or more and
can be included at concentrations ranging from about 0. I % to about 10%, more
preferably from about 1 % to about 7%, and most preferably from about I % to
about
S%, by weight of the composition.
3o Carboxylic Acid Copolymer Thickeners
Another component useful in the compositions herein is a carboxylic acid
copolymer thickener. These crosslinked polymers contain one or more monomers
derived from acrylic acid, substituted acrylic acids, and salts and esters of
these
acrylic acids and the substituted acrylic acids, wherein the crosslinking
agent
contains two or more carbon-carbon double bonds and is derived from a
polyhydric
alcohol. The preferred polymers for use herein are of two general types. The
first
type of polymer is a crosslinked homopolvmer of an acrylic acid monomer or
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
l3 - _
derivative thereof (e.g., wherein the acrylic acid has substituents on the two
and
three carbon positions independently selected from the group consisting of C 1
_4
alkyl, -CN, -COOH, and mixtures thereofj. The second type of polymer is a
crosslinked copolymer having a first monomer selected from the group
consisting of
an acrylic acid monomer or derivative thereof (as just described in the
previous
sentence), a short chain alcohol (i.e. a C1-4) acrylate ester monomer or
derivative
thereof (e.g., wherein the acrylic acid portion of the ester has substituents
on the two
and three carbon positions independently selected from the group consisting of
C 1 _4
alkyl, -CN, -COOH, and mixtures thereofj, and mixtures thereof; and a second
to monomer which is a long chain alcohol (i.e. C8-40) acrylate ester monomer
or
derivative thereof (e.g., wherein the acrylic acid portion of the ester has
substituents
on the two and three carbon positions independently selected from the group
consisting of C1-4 alkyl, -CN, -COOH, and mixtures thereof). Combinations of
these two types of polymers are also useful herein.
t5 In the first type of crosslinked homopolymers the monomers are preferably
selected from the group consisting of acrylic acid, methacrylic acid,
ethacrylic acid,
and mixtures thereof, with acrylic acid being most preferred. In the second
type of
crosslinked copolymers the acrylic acid monomer or derivative thereof is
preferably
selected from the group consisting of acrylic acid, methacrylic acid,
ethacrylic acid,
2o and mixtures thereof, with acrylic acid, methacrylic acid, and mixtures
thereof being
most preferred. The short chain alcohol acrylate ester monomer or derivati~ye
thereof
is preferably selected from the group consisting of C 1 _4 alcohol acrylate
esters, C 1 _4
alcohol methacrylate esters, C 1 _4 alcohol ethacrylate esters, and mixtures
thereof,
with the C 1 _4 alcohol acrylate esters, C 1 _4 alcohol methacrylate esters,
and mixtures
25 thereof, being most preferred. The long chain alcohol acrylate ester
monomer is
selected from Cg~O alkyl acrylate esters, with C 10-30 alkyl acrylate esters
being
preferred.
The crosslinking agent in both of these types of polymers is a polyalkenyl
polyether of a polyhydric alcohol containing more than one alkenyl ether group
per
3o molecule, wherein the parent polyhydric alcohol contains at least 3 carbon
atoms and
at least 3 hydroxyl groups. Preferred crosslinkers are those selected from the
group
consisting of allyl ethers of sucrose and allyl ethers of pentaerythritol, and
mixtures
thereof. These polymers useful in the present invention are more fully
described in
U.S. Patent No. 5,087,445, to Haffey et al., issued February 11, 1992; U.S.
Patent
35 No. 4,509,949, to Huang et al., issued April 5, 1985; U.S. Patent No.
2,798,03, to
Brown, issued July 2, 1957; which are incorporated by reference herein. See
also,
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
14
CTFA International Cosmetic Ingredient Dictionary, fourth edition, 1991, pp.
12 and
80; which is also incorporated herein by reference.
Examples of commercially available hompolymers of the first type useful
herein include the carbomers, which are homopolymers of acrylic acid
crosslinked
with allyl ethers of sucrose or pentaerytritol. The carbomers are available as
the
Carbopol~ 900 series from B.F. Goodrich. Examples of commercially available
copolymers of the second type useful herein include copolymers of C 10-30
alkyl
acrylates with one or more monomers of acrylic acid, methacrylic acid, or one
of
their short chain (i.e. C1-4 alcohol) esters, wherein the crosslinking agent
is an allyl
1 o ether of sucrose or pentaerytritol. These copolymers are known as
acrylates/C 10-30
alkyl acrylate crosspolymers and are commercially available as Carbopol~ 1342,
Pemulen TR-1, and Pemulen TR-2, from B.F. Goodrich. In other words, examples
of carboxylic acid polymer thickeners useful herein are those selected from
the group
consisting of carbomers, acrylates/C10-C30 alkyl acrylate crosspolymers, and
mixtures thereof.
The compositions of the present invention can comprise from about 0.025% to
about 1%, more preferably from about 0.05% to about 0.75%, and most preferably
from about 0.10% to about 0.50%, by weight of the carboxylic acid polymer
thickeners.
2o Other Additional Components
The compositions of the present invention can comprise a wide range of other
additional components. The CTFA Cosmetic Ingredient Handbook, Second Edition,
1992, which is incorporated by reference herein in its entirety, describes a
wide
variety of nonlimiting cosmetic and pharmaceutical ingredients commonly used
in
hair and skin care industries, which are suitable for use in the compositions
of the
present invention. Nonlimiting examples of functional classes of ingredients
are
described at page 537 of this reference. Examples of these functional classes
include: absorbents, abrasives, anti-acne agents, anticaking agents,
antifoaming
agents, antimicrobial agents, antioxidants, binders, biological additives,
buffering
3o agents, bulking agents, chelating agents, chemical additives, colorants,
cosmetic
astringents, cosmetic biocides, denaturants, drug astringents, film formers,
fragrance
components, opacifying agents, pH adjusters, plasticizers, preservatives,
propellants,
reducing agents, additional skin-conditioning agents, suspending agents
(nonsurfactant), ultraviolet light absorbers, and viscosity increasing agents
(aqueous
and nonaqueous). Examples of other functional classes of materials useful
herein
that are well known to one of ordinary skill in the art include solubilizing
agents,
sequestrants, and the like.
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
Nonlimiting examples of these additional components cited in the CTFA
Cosmetic Ingredient Handbook, as well as other materials useful herein,
include the
following: vitamins and derivatives thereof [e.g., vitamin C, Vitamin A (i.e.
retinoic
acid), retinol, retinoids, and the like]; anti-oxidants; polyethyleneglycols
and
5 polypropyleneglycols; polymers for aiding the film-forming properties and
substantivity of the composition (such as a copolymer of eicosene and vinyl
pyrrolidone, an example of which is available from GAF Chemical Corporation as
Ganex~ V-220); preservatives for maintaining the antimicrobial integrity of
the
compositions; antioxidants; chelators and sequestrants; crosslinked and
to noncrosslinked nonionic and cationic polyacrylamides [e.g., Salcare SC92
which has
the CTFA designation polyquaternium 32 (and) mineral oil, and Salcare SC 95
which has the CTFA designation polyquaternium 37 (and) mineral oil (and) PPG-1
trideceth-6, and the nonionic Seppi-Gel polyacrylamides available from Seppic
Corp.]; and aesthetic components such as fragrances, pigments, colorings,
essential
1 s oils, skin senates, astringents, skin soothing agents, skin healing agents
and the like,
nonlimiting examples of these aesthetic components include clove oil, menthol,
camphor, eucalyptus oil, eugenol, menthyl lactate, witch hazel distillate,
bisabolol,
dipotassium glycyrrhizinate, and the like.
Method of Use
2o The compositions of the present invention are used in conventional ways to
provide cosmetic or pharmaceutical benefits appropriate to the product such as
sun
protection, anti-acne benefits, anti-wrinkle and anti-skin aging benefits,
artificial
tanning, analgesic benefits, skin conditioning benefits, facial
moisturization, lip
protection, skin cleansing benefits, grooming aids, and the like. Such methods
of
use depend upon the type of composition employed but generally involve topical
application of an effective amount of the product to the hair or skin. By
"effective
amount" is meant an amount sufficient to provide the benefit desired. Typical
amounts of the compositions of the present invention which are applied to the
hair or
skin will vary depending upon the type of composition and the benefit desired,
3o however, typical ranges are generally from about 1 gram to about 25 gram,
with
about 2 gram being typical.
Examples
The following examples further describe and demonstrate embodiments within
the scope of the present invention. The examples are given solely for the
purpose of
illustration and are not to be construed as limitations of the present
invention, as
many variations thereof are possible without departing from the spirit and
scope of
the invention.
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
16
Ingredients are identified by chemical or CTFA name.
Example 1
A topical composition in the form of an emollient cleanser is prepared by
combining the following ingredients using conventional mixing techniques. This
composition utilizes a mixture of a solid polyol fatty acid polyester ( solid
sucrose
polyester) and a liquid oil to provide emolliency and aesthetic benefits
without
leaving the skin feeling heavy, sticky or greasy.
In~ redients Weight Percent
Phase A
1 Disodium EDTA 0.100
s
Glycerin 4.000
Methylparaben 0.200
Acrylates/C10-30 alkyl acrylate 1 0.150
Crosspolymer
Carbomer 9542 0.250
20Water QS 100
Phase B
Stearic Acid 0.110
Stearyl Alcohol 0.875
Cetyl Alcohol 0.875
25Propylparaben 0.150
Steareth-2 0.250
Steareth-21 0.500
Solid Sucrose Polyester3 1.000
Phase C
30Sodium Hydroxide4 0.130
Phase D
Diisopropyl sebacate 1.500
Isohexadecane 5.000
Phase E
35Phenoxyethanol 0.500
Fragrance 0.150
Phase F
Glucose Amide 0.960 '
4o 1 Available as Pemulen~ TR-1 from B.F. Goodrich Corporation.
2 Available as Carbomer~ 954 from B.F. Goodrich Corporation.
3 Solid sucrose octaester esterified with 1 oleic and 7 behenic acid moieties.
4 50% aqueous solution.
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
17
In a suitable vessel, the Phase A ingredients are mixed at room temperature to
form a dispersion and heated with stirring to 70-80°C. In a separate
vessel, the
Phase B ingredients are heated with stirring to 70-80°C. Phase B is
then added to
Phase A with mixing to form the emulsion. Next, Phase C is added to neutralize
the
composition. The Phase D ingredients are added with mixing, followed by
cooling
to 45-50°C. The Phase E ingredients are then added with stirring,
followed by
cooling to 40°C. Phase F is heated with mixing to 40°C and added
to the emulsion,
which is cooled to room temperature.
to Example 2
A topical composition in the form of a shower product is prepared by
combining the following ingredients using conventional mixing techniques. This
composition utilizes a mixture of a solid polyol fatty acid polyester (solid
sucrose
polyester) and a liquid oil to provide emolliency and aesthetic benefits
without
leaving the skin feeling heavy, sticky or greasy.
Ingredients Weieht Percent
2o Sodium C 12/14 Alkyl Ether Glycerol12.0
Sulfonate
Ammonium Laureth-3 Sulfate 3.00
Myristic Acid 1.00
Myristic Alcohol 1.00
Cocamidopropyl Betaine 3.00
Trihydroxystearin 1.75
Solid Sucrose Polyesterl 1.20
Tetrasodium EDTA 0.13
Glycerin 6.24
Perfume 0.80
3o Polyquat-10 (JR-30M) 0.30
Glydant 0.20
Maleated Soybean Oil 1.00
Water QS 100
1 Solid sucrose octaester esterified with 1 oleic and 7 behenic acid moieties.
In a suitable vessel, the Polyquat-10 is added to distilled water and allowed
to
mix until fully hydrated. The surfactants, and water soluble ingredients, are
added
and the mixture is heated with stirring to 70-80°C. In a separate
vessel, the solid
sucrose polyester is combined with the liquid oils and trihydroxystearin,
heated with
mixing until uniform, and then added to the mixture heated at 70-80°C.
The mixture
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
18
is allowed to cool to 25-35°C while continuing to stir. The glydant and
perfume
ingredients are then added with stirring, and the mixture is cooled to room
temperature.
Example 3
A topical composition in the form of a shower product is prepared by
combining the following ingredients using conventional mixing techniques. This
composition utilizes a mixture of a solid polyol fatty acid polyester (solid
sucrose
polyester) and a liquid oil to provide emolliency and aesthetic benefits
without
leaving the skin feeling heavy, sticky or greasy.
In~~redients Weight Percent
Ammonium Lauryl Sulfate 3.15
Ammonium Laureth-3 Sulfate 9.45
Na Lauroamphoacetate 5.40
Polyquaternium-10 0.3
Trihydroxystearin 2.0
Solid Sucrose Polyesterl 1.20
Tetrasodium EDTA 0.13
Glycerin 3.0
2o Perfume 0.80
Citric Acid 0.76
Lauryl Alcohol 2.00
Mineral Oil 3.00
Water QS 100
1 Solid sucrose octaester esterified with 1 oleic and 7 behenic acid moieties.
In a suitable vessel, the Polyquaternium-10 is added to distilled water and
allowed to mix until fully hydrated. The surfactants, and water soluble
ingredients,
are added and the mixture is heated with stirring to 70-80°C. In a
separate vessel,
3o the solid sucrose polyester is combined with the liquid oils, iauryl
alcohol, and
trihydroxystearin, heated with mixing until uniform, and then added to the
mixture
heated at 70-80°C. The mixture is allowed to coot to 25-35°C
while continuing to
stir The glydant and perfume ingredients are then added with stirring, and the
mixture is cooled to room temperature.
Example 4
A topical composition in the form of a moisturizer is prepared by combining
the following ingredients using conventional mixing techniques. This
composition
utilizes a mixture of a solid polyol fatty acid polyester (solid sucrose
polyester) and a
CA 02289696 1999-11-15
WO 98/52531 PCT/IB98/00787
19
liquid oil to provide emolliency
and aesthetic benefits without
leaving the skin
feeling heavy, sticky or greasy.
Ingredients Wei;~ht Percent
Cetyl Alcohol 1.80
Stearic Acid 0.25
Stearyl Alcohol 1.20
Peg 100-stearate 0.25
Mineral Oil 2.00
Petrolatum 1.50
1o Isopropyl Palmitate 1.00
Cetyl Ricinoleate 1.00
Solid Sucrose Polyesterl 2.00
Dimethicone 3502 0.50
Propyl Paraben 0.10
Arlatone (RTM) 21213 1.00
Glycerin 9.00
Urea 2.00
Octyl Methoxycinnamate 2.00
Phenoxyethanol 0.25
2o Carbomer 13824 0.05
Carbomer 9545 0.35
Tetrasodium EDTA 0.10
Titanium Dioxide 0.15
Methyl Paraben 0.20
NaOH 0.22
Dimethicone Q-214036 1.00
Isohexadecane 1.00
Water qs 100
1 Solid sucrose octaester esterified with 1 oleic and 7 behenic acid moieties.
2 Dow Corning~ 200 Fluid (350 centistoke) from Dow Corning.
3 95% by weight sorbitan stearate and 5% by weight sucrose cocoate.
4 Carbopol~ 1382 from B.F. Goodrich.
5 Carbopol~ 954 from B.F. Goodrich.
6 Dow Corning~ Q-2 1403 from Dow Corning which is a mixture of 85% by
weight dimethicone and 15% by weight dimethiconal.
A first premix of the solid sucrose polyester, Arlatone 2121 and other water
soluble ingredients is prepared by admixing in water and heating. A second
premix
of oil phase ingredients other than the silicones is prepared by mixing and
heating
4o and is added to the aqueous premix. The resulting mixture is cooled. The
silicones
are then added to the resulting oil-in-water emulsion and the mixture is
cooled
before adding minor ingredients.
