U.S. patent application number 09/380651 was filed with the patent office on 2002-03-14 for combination of erythrulose and a reducing sugar with self-tanning properties.
Invention is credited to JERMANN, ROLAND, SCHREIER, THOMAS.
Application Number | 20020031482 09/380651 |
Document ID | / |
Family ID | 4188843 |
Filed Date | 2002-03-14 |
United States Patent
Application |
20020031482 |
Kind Code |
A1 |
SCHREIER, THOMAS ; et
al. |
March 14, 2002 |
COMBINATION OF ERYTHRULOSE AND A REDUCING SUGAR WITH SELF-TANNING
PROPERTIES
Abstract
The invention relates to an active ingredient combination
containing erythrulose and a further reducing sugar with
self-browning properties, for example dihydroxyacetone, which
combination is used for artificially tanning the skin. Compared
with compounds containing, for example, only dihydroxyacetone, said
active ingredient combination and cosmetic compounds based thereon
result in an even and longer-lasting colouring of the skin and
prevent skin dehydration and uneven flaking.
Inventors: |
SCHREIER, THOMAS;
(BUBENDORF, CH) ; JERMANN, ROLAND; (LAUFEN,
CH) |
Correspondence
Address: |
PENNIE & EDMONDS
1155 AVENUE OF THE AMERICAS
NEW YORK
NY
100362711
|
Family ID: |
4188843 |
Appl. No.: |
09/380651 |
Filed: |
January 5, 2000 |
PCT Filed: |
February 27, 1998 |
PCT NO: |
PCT/CH98/00083 |
Current U.S.
Class: |
424/59 ; 424/401;
424/60; 514/23; 514/937; 514/938 |
Current CPC
Class: |
Y10S 514/937 20130101;
A61K 2800/592 20130101; A61Q 19/04 20130101; A61K 8/60 20130101;
A61K 8/35 20130101; Y10S 514/938 20130101 |
Class at
Publication: |
424/59 ; 424/401;
424/60; 514/23; 514/937; 514/938 |
International
Class: |
A61K 031/70; A61K
007/42; A61K 007/44; A61K 006/00; A61K 007/00 |
Foreign Application Data
Date |
Code |
Application Number |
Mar 5, 1997 |
CH |
518/97 |
Claims
1. An active substance combination for the artificial tanning of
the skin containing a combination of erythrulose in D- or L-form or
also as the racemate with an additional reducing sugar having
self-tanning properties.
2. An active substance combination according to claim 1
characterised in that the ratio between erythrulose and the
additional reducing sugar having self-tanning properties lies
between 10:1 to 1:10, advantageously at about 1:1 to 1:3, ca. 1:2
being particularly preferred.
3. An active substance combination according to claim 1 or claim 2
characterised in that DHA is used as additional reducing sugar
having self-tanning properties.
4. A cosmetic formulation containing an active substance
combination according to one of claims 1 or 2 characterised in that
1-5% erythrulose and 1-15% of an additional reducing sugar having
self-tanning properties, advantageously about 1.5% erythrulose and
3.5% of an additional reducing sugar having self-tanning properties
are used.
5. A cosmetic formulation containing an active substance
combination according to one of claims 1 or 2 characterised in that
DHA is used as additional reducing sugar having self-tanning
properties.
6. A cosmetic formulation according to one of claims 4 or 5 in the
form of an O/W emulsion.
7. A cosmetic formulation according to claim 6 characterised in
that the oily phase amounts to 5-45% by weight, in particular about
10-30% by weight of the total formulation.
8. A cosmetic formulation according to one of claims 4-7
characterised in that it contains at least one penetration
enhancer.
9. A cosmetic formulation according to one of claims 4-8
characterised in that it contains at least one compound acting as
sunscreen, advantageously octyl methoxycinnamate and/or butyl
methoxydibenzoylmethane.
10. A process for the topical use of an active substance
combination according to one of claims 1-3 or of a cosmetic
formulation according to one of claims 4-9, by topically applying
to the skin an effective amount of an active substance combination
or of a cosmetic formulation.
Description
[0001] The present invention relates to a combination of
erythrulose in D- or L-form or as the racemate and at least one
additional reducing sugar having self-tanning properties and
cosmetic compositions containing these for the artificial tanning
of the skin. The cosmetic compositions bring about a more even and
longer-lasting coloration of the skin and prevent the drying out
and uneven peeling thereof compared to known compositions that, for
example, contain dihydroxyacetone alone.
[0002] Hydroxyketones and hydroxyaldehydes are known active
substances for self-tanning agents. The active substances generally
processed into creams react with free amino groups of the Stratum
corneum and result in brownish-coloured pigments that are bound to
proteins of the Stratum corneum. This conversion of reducing sugars
with amino acids, peptides or proteins, known as the Maillard
reaction, leads to compounds having a carbonyl function that
polymerise to brown melanoids.
[0003] The hitherto most frequently used active substance is
dihydroxyacetone (hereinafter referred to as "DHA"). The fast
tanning active substance (4-7 hours) does, however, have some
disadvantages. The skin colour achieved is yellowish-brown, which
produces an unnatural colour, particularly in pale skin. In
addition, the tan is irregular and soon pales again because the
top-most layers of the epidermis are quickly shed.
[0004] It has now been found that a combination of DHA--or another
reducing sugar having similar properties--with erythrulose does not
display the above disadvantages. This may be attributed to the fact
that erythrulose dyes the skin more slowly (the colour takes about
20-24 hours to develop) and less intensively, but instead also
penetrates lower layers of the Stratum corneum where it is also
able to react with the free amino groups. This not only results in
more even tanning, but also in a retarded effect, with the result
that the tan lasts longer. Moreover the skin becomes less dried out
than, for example, with DHA alone. The synergistic effect, that
will subsequently also be shown with reference to examples, of the
active substance combination erythrulose/other reducing sugars,
such as for example DHA, was not predictable.
[0005] Erythrulose alone can also be used as sole active substance
for slightly tanning day creams. The advantage of erythrulose
compared to other reducing sugars having a self-tanning effect, in
particular DHA, lies in the fact that the skin is tanned more
evenly and without forming undesirable streaks.
[0006] Erythrulose is a C4-ketosugar of the general structural
formula 1,3,4-trihydroxy-butan-2-one that occurs naturally or that
can be prepared chemically or biotechnologically in a manner known
per se. Erythrulose can be used in D- or L-form or also as the
racemate. DHA is a C3-ketosugar having the general structural
formula 1,3-dihydroxy-propan-2-one that can be prepared in a manner
known per se.
[0007] Other reducing sugars having self-tanning properties that
can be used in combination with erythrulose are, for example,
glucose, xylose, fructose, reose, ribose, arabinose, allose,
tallose, altrose, mannose, galactose, lactose, sucrose, erythrose
and glyceraldehyde.
[0008] The active substance combination contains a ratio of
erythrulose to reducing sugar of about 10:1 to 1:10, advantageously
about ca. 1:1 to 1:3; 1:2 being particularly preferred.
[0009] A cosmetic formulation uses about 1-5% erythrulose and about
1-15% reducing sugar, advantageously about 1.5% erythrulose and
3.5% reducing sugar.
[0010] The stability of erythrulose with a reducing sugar in a
cosmetic formulation depends on many factors. The active substance
combination can be used in O/W (e.g. cream or lotion) and also W/O
emulsions and other types of cosmetic formulations (e.g. multiple
emulsions such as O/W/O or W/O/W emulsions, gels, ointments,
aerosols). The stability of the active substances can be
quantitatively determined using chromatography. To do this, the
emulsion is diluted, membrane filtered and analysed using HPLC.
[0011] The oily phase in emulsions can, for example, contain
hydrocarbon oils such as paraffin oil or mineral oils, waxes such
as beeswax or paraffin wax, silicon oils such as cyclomethicone or
dimethicone, fatty alcohols such as stearyl alcohol or cetyl
alcohol, natural oils such as jojoba oil, sesame oil or sunflower
oil, fatty acid esters such as isopropyl myristate or glyceryl
stearate or mono-, di- or triglycerides such as for example
caprylic / capric acid triglyceride.
[0012] In the case of oil-in-water emulsions, the oil phase
advantageously comprises 5-45% by weight, in particular about
10-30% by weight of the total formulation.
[0013] As emulsifiers for oil-in-water and water-in-oil emulsions
it is possible to use emulsifiers known per se, such as silicons,
sesquioleates, sorbitan esters, alkoxylated sorbitan and fatty acid
esters, alkoxylated mono-, di- and triglycerides, optionally
alkoxylated polymers such as cross-polymers of ethylene oxide and
propylene oxide, optionally alkoxylated fatty alcohols, fatty
acids, esters of natural oil derivatives, ethers such as
polyethylene glycol(n)stearyl ether and polyethylene
cetyl(n)stearyl ether.
[0014] The emulsifiers are advantageously used in amounts of 0.115%
by weight related to the total formulation.
[0015] The formulations of the invention may also contain
additional auxiliary substances such as for example stabilisers
such as mannitol or cyclodextrin, moisturizers such as glycerol and
propylene glycol, thickening agents such as acrylic acid polymers
or cellulose derivatives, antioxidants such as tocopheryl acetate,
pH-correcting agents such as sodium phosphate, film-forming agents
such as PVP, preservatives such as phenoxyethanol and paraben,
colorants, fragrances, softeners, antiseptics, bactericides,
vitamins, pigments,-propellants as well as other compounds that are
cosmetically or medicinally desirable. Examples of other compounds
of this nature are set out in the CTFA International Cosmetic
Ingredient Dictionary, 6.sup.th edition, The Cosmetic, Toiletry and
Fragrance Association, Inc., Washington D.C., 1995.
[0016] Lipophilic systems are quite generally more suitable for
cosmetic formulations of self-tanning agents. Tanning can be
accelerated and the colour intensity significantly increased by
adding penetration enhancers. The following have proved to be
particularly suitable as penetration enhancers: dimethicone,
cyclomethicone, propylene glycol dipelargonate, propylene glycol or
ethoxy diglycol. The colour intensity measured was up to 55% higher
with formulations containing penetration enhancers as compared to
the basic formulation without penetration enhancers.
[0017] Synthetic oils such as Miglyol 812, isopropyl palmitate and
silicon oils and natural lipids such as jojoba oil and sesame oil
are particularly compatible with the active substance combination
and are therefore particularly preferred.
[0018] Gels can also be used as formulation base for the
compositions of the invention. Carbomers, cellulose derivatives and
other gellants can be contained as gel-forming substances.
[0019] Insofar as the cosmetic formulation is intended to provide
both a self-tanning effect and also protection against solar
radiation, it-is also possible to add to the formulation one or
several sunscreens, such as for example octyl methoxycinnamate
and/or butyl methoxydibenzoylmethane.
[0020] When processing the active substances into cosmetic
formulations, care must be taken to ensure that the active
substances are only added at lower temperatures of about
<40.degree. C. and that the pH value 5 is not exceeded in the
cosmetic formulations, this being easily achieved through
buffering.
[0021] The active substance combination of the invention, or the
cosmetic formulations based thereon, can be applied to the human
skin in conventional manner.
[0022] The invention will now be explained in greater detail with
reference to examples, the percentages in each case constituting %
by weight.
EXAMPLE 1
[0023] A self-tanning body lotion is prepared by mixing together an
oily phase composed of 12.00% Cutina GMS (glyceryl stearate), 1.50%
Eumulgin B1 (Ceteareth-12), 1.50% Eumulgin B2 (Ceteareth-20), 4.00%
isopropyl myristate, 7.00% paraffin oil and 4.00% Miglyol 812
(caprylic / capric acid triglyceride) and heating to 70.degree. C.
and mixing together an aqueous phase composed of 51.20%
demineralised water, 0.50% Phenonip and 3.00% glycerol and heating
to 75.degree. C. The aqueous phase is then added to the oily phase
with stirring and cooled to 50.degree. C., homogenised and cooling
continued to 30.degree. C. and an additional aqueous phase composed
of 10.00% demineralised water, 1.50% erythrulose and 3.50%
dihydroxyacetone is then added to the mixture and stirred until
cold. This produces a body lotion that is agreeable to use.
EXAMPLE 2
[0024] A self-tanning white lotion is prepared by mixing together
an oily phase composed of 1.50% Arlatone 983 S (PEG-5 glyceryl
stearate), 2.20% Arlatone 985 (PEG-5 glyceryl stearate), 1.50% Brij
76 (Steareth-10), 5.00% Miglyol 812 (caprylic / capric acid
triglyceride), 4.00% paraffin oil and 1.00% silicon oil AK 500
(dimethicone) and heating to 70.degree. C. and mixing together an
aqueous phase composed of 59.30% demineralised water, 0.50%
Phenonip and 10.00% propylene glycol and heating to 75.degree. C.
The aqueous phase is then added to the oily phase with stirring and
cooled to 50.degree. C., homogenised and cooling continued to
30.degree. C. and an additional aqueous phase composed of 10.00%
demineralised water, 1.50% erythrulose and 3.50% dihydroxyacetone
is then added to the mixture and stirred until cold. This produces
a lotion that is agreeable to use.
EXAMPLE 3
[0025] A self
[0026] -tanning white lotion is prepared by analogy with Example 2,
except that 3.00% erythrulose and 2.00% DHA are used. As in Example
2, this produces a lotion that is agreeable to use.
EXAMPLE 4
[0027] A self-tanning cream is prepared by mixing together an oily
phase composed of 1.00% Cremophor A6 (Ceteareth 6 and stearyl
alcohol), 1.00% Cremophor A25 (Ceteareth 25), 3.00% Cutina GMS
(glyceryl stearate), 10.00% paraffin oil, 5.00% jojoba oil and
1.00% cetyl alcohol and heating to 70.degree. C. and mixing
together an aqueous phase composed of 48.50% demineralised water,
0.50% Phenonip and 5.00% propylene glycol and heating to 75.degree.
C. The aqueous phase is then added to the oily phase with stirring
and cooled to 50.degree. C., homogenised and cooling continued to
30.degree. C. and an additional aqueous phase composed of 15.00%
demineralised water, 5.00% cyclodextrin, 1.50% erythrulose and
3.50% dihydroxyacetone is then added to the mixture and stirred
until cold. This produces a cream that is agreeable to use.
EXAMPLE 5
[0028] A self-tanning O/W cream with sunscreen is prepared by
mixing together an oily phase composed of 5.00% of a mixture of
glyceryl stearate and PEG-100-stearate, 1.00% cetyl alcohol, 2.00%
stearic acid, 4.00% dimethicone, 2.00% cyclomethicone, 3.00%
caprylic / capric acid triglyceride, 1.00% jojoba oil, 4.00%
isopropyl palmitate, 2.00% octyl methoxycinnamate and 1.00% butyl
methoxydibenzoylmethane, heating to 75.degree. C. and adding an
aqueous phase heated to 80.degree. C. composed of 51.20%
demineralised water, 0.50% Phenonip, 6.00% propylene glycol and
2.00% glycerol and stirring thoroughly. The emulsion obtained is
cooled to 50.degree. C. and homogenised. At 30.degree. C. an
additional aqueous phase composed of 10.00% demineralised water,
1.50% erythrulose and 3.50% dihydroxyacetone is then added and
stirred thoroughly.
EXAMPLE 6
[0029] A self-tanning W/O/W cream is prepared by preparing an
aqueous solution of 2.00% Poloxamer, 0.10% Phenonip, 16.02%
demineralised water, 0.38% magnesium sulfate heptahydrate, 1.40%
xanthan gum, 0.10% Phenonip, and 20.00% demineralised water and
adding 60.00% of a previously prepared W/O emulsion consisting of
an oily phase containing 3.30% of a mixture of sorbitan ester and
polyglycerol ester, 3.00% polyglycerol ester, 15.00% isohexadecan,
14.00% caprylic / capric acid triglyceride and an aqueous phase
with 55.50% demineralised water, 0.20% Phenonip, 0.70% magnesium
sulfate heptahydrate, 2.50% erythrulose and 5.80% DHA and
homogenising.
EXAMPLE 7
[0030] A self-tanning gel is prepared by mixing together 1.00% PVM
(copolymer composed of vinyl chloride and vinylmethyl ether) /
MA-decadien crosspolymer, 0.50% Phenonip and 83.50% demineralised
water, adjusting the pH to 3.7 with sodium hydroxide solution and
adding 15% of a mixture of 66.70% demineralised water, 10.00%
erythrulose and 23.30% DHA.
EXAMPLE 8
[0031] A self-tanning day cream is prepared by mixing together
5.00% Arlacel 165 (glyceryl stearate, PEG-100-stearate), 1.00%
cetyl alcohol, 2.00% stearic acid, 4.00% Dow Corning 200 silicon
(dimethicone polymethylsiloxan), 2.00% Belsil CM 020
(cyclomethicone), 3.00% Miglyol 812 (caprylic / capric acid
triglyceride), 1.00% jojoba oil, 4.00% isopropyl palmitate, 2.00%
Parsol MCX (octyl methoxycinnamate) and 1.00% butyl
methoxydibenzoylmethane and heating this oily phase to 70.degree.
C. In parallel thereto, 57.20% deionised water, 0.50% Phenonip,
6.00% propylene glycol and 2.00% glycerol are mixed and this
aqueous phase is heated to 75.degree. C. The aqueous phase is then
added to the oily phase with stirring and the mixture cooled to
50.degree. C., homogenised and cooled further to 30.degree. C. A
mixture composed of 5.00% deionised water and-4.00% erythrulose is
then added and stirred until cold, whereupon the entire mixture is
then reacted with 0.30% Belamie 0/241710.
[0032] This produces a day cream that with daily application gives
the skin a slightly brownish coloration and healthy appearance. The
sunscreens also protect the skin from the effects of harmful UV
radiation.
EXAMPLE 9
[0033] To investigate the synergistic effect of erythrulose and DHA
on the tanning of the skin a tanning study was conducted to compare
an O/W lotion containing 1.5% erythrulose and 3.5% DHA according to
Example 1 with a lotion containing DHA.
[0034] Fields measuring 10.times.14 cm were marked on the back of 4
male and 4 female subjects. The subjects were neither allowed to
sunbathe nor to visit a solarium during the entire period of the
study.
[0035] Before the measurements, the subjects were acclimatised for
15 min in a skin laboratory at 26-28.degree. C. and 40-50% air
humidity. Immediately after measuring the initial value on day 0,
the marked test fields were treated with 0.3 ml of the appropriate
lotion with light rubbing in. This procedure was repeated on the
following 9 days. No more lotion was applied after the 10.sup.th
day.
[0036] From the first day to the 20.sup.th day the colour changes
as well as the skin moisture were in each case measured immediately
before the next application. The skin moisture was measured using
the CM 820 Corneometer (Courage and Khazaka). The skin colour was
measured using the Minolta CR 300 Chromameter.
[0037] The skin colour was quantified using the "CIE L*a*b* colour
system". This defines the colours in a three-dimensional colour
co-ordinate system. The a* value corresponds to the red-green axis,
the b* value to the yellow-blue axis and the L* value to the
pale-dark axis. The smaller the L* value, the darker the colour.
The difference between two measuring points in this
three-dimensional colour coordinate system can be calculated from
the absolute values using the following formula:
.DELTA.E(CIEL*a*b*)={square root}{square root over
((L.sub.1-*L.sub.2*)+(a-
.sub.1*-a.sub.2*).sup.2+(b.sub.1*-b.sub.2*).sup.2)}
[0038] The value calculated using this formula is a parameter for
the colour change of the skin.
[0039] FIG. 1 shows the different influence of the two formulations
tested on the colour intensity. The diagram shows the percentage
colour difference of the combination of erythrulose and DHA
compared to DHA. The use of DHA alone colours the skin faster
during the first few days. However, from the 10.sup.th day on, the
intensity of coloration of the combination erythrulose and DHA was
greater. After application was discontinued, the difference in the
intensity of coloration of the combination of erythrulose and DHA
compared to DHA alone was increasingly more marked because of the
delayed decrease in coloration. This shows that erythrulose
produces a visible retarded effect.
[0040] The skin coloration achieved with erythrulose and DHA does
not show any streak formation and the skin shows no peeling due to
greater drying out.
[0041] Measurements show that the use of erythrulose and DHA in an
O/W emulsion causes up to 30% less drying out of the skin (FIG. 2).
The skin feels less dry. When using the combination of erythrulose
and DHA in comparison to the DHA emulsion, the test subjects did
not feel any skin tightness.
* * * * *