U.S. patent application number 12/511762 was filed with the patent office on 2009-11-26 for use of alkylpolyglycosides as emulsifying agents for the preparation of oil-in-water emulsions comprising inorganic fillers or pigments, and oil-in-water emulsions comprising such alkylpolyglycosides.
This patent application is currently assigned to Societe D'Exploitation de Produits pour les Industries Chimiques (SEPPIC_. Invention is credited to Chantal Amalric, Jean-Pierre Boiteux, Nelly Michel, Alain Milius, Herve Rolland, Alicia Roso, Guy Tabacchi.
Application Number | 20090291052 12/511762 |
Document ID | / |
Family ID | 8868714 |
Filed Date | 2009-11-26 |
United States Patent
Application |
20090291052 |
Kind Code |
A1 |
Roso; Alicia ; et
al. |
November 26, 2009 |
USE OF ALKYLPOLYGLYCOSIDES AS EMULSIFYING AGENTS FOR THE
PREPARATION OF OIL-IN-WATER EMULSIONS COMPRISING INORGANIC FILLERS
OR PIGMENTS, AND OIL-IN-WATER EMULSIONS COMPRISING SUCH
ALKYLPOLYGLYCOSIDES
Abstract
A composition and process of preparation of emulsifier agents
based on an alkylpolyglycoside structure with a length of alkyl
chain having from 6 to 12 carbon atoms to be used. The resulting
emulsions exhibit an excellent dispersion of the fillers and/or
pigments without it being necessary to add coemulsifier or
dispersant. The emulsifier makes it possible, by itself alone, to
prevent the reagglomeration of the fillers and/or pigments.
Inventors: |
Roso; Alicia; (Saix, FR)
; Amalric; Chantal; (Blan, FR) ; Michel;
Nelly; (Maisons-Alfort, FR) ; Boiteux;
Jean-Pierre; (Saix, FR) ; Rolland; Herve;
(Castres, FR) ; Tabacchi; Guy; (Paris, FR)
; Milius; Alain; (Nice, FR) |
Correspondence
Address: |
YOUNG & THOMPSON
209 Madison Street, Suite 500
ALEXANDRIA
VA
22314
US
|
Assignee: |
Societe D'Exploitation de Produits
pour les Industries Chimiques (SEPPIC_
Paris
FR
|
Family ID: |
8868714 |
Appl. No.: |
12/511762 |
Filed: |
July 29, 2009 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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10493726 |
Apr 23, 2004 |
|
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|
PCT/FR2002/003609 |
Oct 22, 2002 |
|
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|
12511762 |
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Current U.S.
Class: |
424/59 ; 424/63;
536/4.1 |
Current CPC
Class: |
C07H 15/10 20130101;
A61Q 1/02 20130101; C07H 15/04 20130101; Y10S 514/844 20130101;
B01F 17/0092 20130101; A61K 8/062 20130101; Y10S 514/845 20130101;
A61K 8/604 20130101; A61K 8/06 20130101; B01F 17/0028 20130101;
A61Q 17/04 20130101; B01F 17/0021 20130101 |
Class at
Publication: |
424/59 ; 536/4.1;
424/63 |
International
Class: |
A61K 8/30 20060101
A61K008/30; C07H 15/00 20060101 C07H015/00; A61Q 17/04 20060101
A61Q017/04; A61Q 1/00 20060101 A61Q001/00 |
Foreign Application Data
Date |
Code |
Application Number |
Oct 25, 2001 |
FR |
FR 01/13808 |
Claims
1. An alkylpolyglycoside composition of formula (Ia) or (Ib)
HO--RO--X(.sub.r (Ia) (X).sub.aO--RO--(X).sub.t (Ib) wherein: a) X
represents the residue of a C.sub.5 or C.sub.6 sugar; b) R
represents an alkylene or alkylidene group having from 6 to 12
carbon atoms; and c) r, s, and t represent the mean degree of
polymerization of each sugar residue, and are greater than 1 and
less than or equal to 5.
2. The alkylpolyglycoside composition of claim 1, wherein X
represents the residue of glucose or xylose.
3. A method of preparing an oil-in-water emulsion, containing
inorganic fillers and/or pigments, comprising the step of adding an
emulsifying agent which comprises said at least one
alkylpolyglycoside of formula (Ia) or (Ib) of claim 1.
4. An oil-in-water emulsion comprising: inorganic pigments and/or
fillers; and at least one compound wherein the compound is of the
formula (Ia) or (Ib) of claim 1.
5. The emulsion of claim 4, which is an antisun or a makeup
emulsion.
Description
[0001] This application is a division of application Ser. No.:
10/493,726 filed on Apr. 23, 2004; which is the 35 U.S.C. 371
national stage of International application PCT/FR02/03609 filed on
Oct. 22, 2002; which claimed priority to French application FR
01/13808 filed Oct. 25, 2001. The entire contents of each of the
above-identified applications are hereby incorporated by
reference.
BACKGROUND OF THE INVENTION
[0002] 1. Field of the Invention
[0003] A subject-matter of the present invention is the use of
specific alkylpolyglycosides as emulsifying agents for the
preparation of oil-in-water emulsions comprising inorganic fillers
or pigments.
[0004] The invention finds application in particular in the
cosmetics and pharmaceutical field.
[0005] 2. Related Art
[0006] The formulation of fillers and pigments, in particular of
inorganic fillers and pigments, in an emulsion is complex. This is
because the presence of fillers or pigments introduces electrical
charges into the emulsion which disrupt this emulsion. The latter
is difficult to stabilize, often forcing the formulator to use a
complex emulsifying system, one or more stabilizers for the aqueous
phase, or a dispersing surfactant, to prevent reagglomeration of
the fillers over time.
[0007] In the case of antisun emulsions, this reagglomeration of
the fillers results in a low or unstable UV protection factor which
decreases over time. In the case of makeup emulsions,
reagglomeration of the fillers can also occur, resulting in poor
homogeneity of the color in the emulsion itself or when it is
applied to the skin. In both these cases, the reagglomeration of
the fillers, if it is significant, detrimentally affects the
texture of the emulsion, which, instead of appearing smooth and
glossy, becomes dull and granular.
[0008] To overcome these difficulties, recourse is often had:
[0009] either to complex emulsifying systems, which are generally
based on fatty chains with a length of 16 and 18 carbon atoms
(saturated, unsaturated or branched); [0010] or to complex
manufacturing processes; for example, inorganic filters with a
UV-inhibiting role are very often predispersed in the oil phase or
in the water phase.
[0011] The problem to be solved thus consists in having available
oil-in-water emulsions, comprising inorganic fillers or pigments,
which are easy to prepare and which are stable over time, that is
to say in which the pigments or fillers do not reagglomerate.
[0012] It has now been discovered unexpectedly, and this is the
basis of the invention, that an emulsifier based on an
alkylpolyglycoside structure with a length of alkyl chain having
from 6 to 12 carbon atoms makes it possible to readily formulate
oil-in-water (hereinafter "O/W") emulsions comprising inorganic
fillers and/or pigments. This result is all the more surprising
since short-chain surfactants are not supposed to exhibit good
emulsifying properties. These emulsions exhibit an excellent
dispersion of the fillers without it being necessary to add
coemulsifier or dispersant and without it being useful either to
apply specific manufacturing processes as described above. The
dispersion obtained with the emulsifier according to the invention
is furthermore stable over time, that is to say that, surprisingly,
the emulsifier makes it possible, by itself alone, to prevent the
reagglomeration of the fillers and/or pigments, including in fluid
emulsions such as milks.
SUMMARY OF THE INVENTION
[0013] Thus, according to a first aspect, a subject matter of the
invention is alkylpolyglycosides represented by the following
formulae (Ia) or (Ib):
HO--R--O(X).sub.r (Ia)
(X).sub.s--OR--O--(X).sub.t (Ib)
in which:
[0014] X represents the residue of a C.sub.5 or C.sub.6 sugar,
preferably the glucose or xylose residue;
[0015] R represents an alkylene or alkylidene group having from 6
to 12 carbon atoms;
[0016] r, s and t represent the mean degree of polymerization of
each sugar residue. They are greater than 1 and less than or equal
to 5, and more particularly less than or equal to 2.5.
DESCRIPTION OF PREFERRED EMBODIMENTS
[0017] One aspect of the invention is alkylpolyglycosides
represented by the following formulae (Ia) or (Ib):
HO--R--O(X).sub.r (Ia)
(X).sub.s--OR--O--(X).sub.t (Ib)
in which:
[0018] X represents the residue of C.sub.5 or C.sub.6 sugar,
preferably the glucose or xylose residue;
[0019] R represents an alkylene or alkylidene group having from 6
to 12 carbon atoms;
[0020] r, s and t represent the mean degree of polymerization of
each sugar residue. They are greater than 1 and less than or equal
to 5, and more particularly less than or equal to 2.5.
[0021] When X represents the xylose residue, r, s and t are more
particularly between 1.005 and 1.5.
[0022] When X represents the glucose residue, r, s and tare more
particularly between 1.05 and 2.
[0023] The compounds of formula (Ia) or (Tb) in accordance with the
present invention can be prepared by reaction of a reducing sugar
and of an alkanediol having from 6 to 12 carbon atoms, preferably
hexanediol, octanediol, decanediol or dodecanediol, in desired
predetermined proportions.
[0024] This reaction results either in the products resulting from
the acetalization of one of the two hydroxyl groups of the diol
(compounds (Ia)), on in the products resulting from the
acetalization of both hydroxyl groups of the diol (compounds (Ib)),
or in the mixture of the compounds (Ia) and (Ib).
[0025] On an industrial scale, these compounds will preferably be
prepared according to one of the two routes conventionally used for
the synthesis of alkylpolyglycosides, for example by reaction, in
an acidic medium, between the alkanediol having from 6 to 12 carbon
atoms and a reducing sugar, such as glucose or xylose.
[0026] Such synthetic routes are well known to a person skilled in
the art.
[0027] If appropriate, this synthesis can be supplemented by
neutralization, filtration or decoloration operations or operations
for the partial distillation or extraction of the excess diol.
[0028] According to a second aspect of the present invention, a
subject matter of the latter is a concentrate (C), characterized in
that it consists essentially of: [0029] from 30% to 100% by weight
of a mixture (M) of at least one compound of formula (IIIa)
[0029] R.sub.1--O(X.sub.1).sub.p1 (IIIa)
in which
[0030] R.sub.1 represents a linear or branched alkyl radical
comprising from 6 to 12 carbon atoms,
[0031] X.sub.1 represents the xylose residue,
[0032] p.sub.1, which represents the mean degree of polymerization
of the xylose residue, is a decimal number of greater than 1 and
less than or equal to 2.5,
and of at least one compound of formula (IIIb)
R.sub.2--O(G).sub.n (IIIb)
in which
[0033] R.sub.2 represents a linear or branched alkyl radical
comprising from 6 to 12 carbon atoms,
[0034] G represents the glucose residue,
[0035] n, which represents the mean degree of polymerization of the
xylose residue, is a decimal number of greater than 1 and less than
or equal to 2.5, and [0036] from 0% to 70% by weight of a topically
acceptable solvent.
[0037] In the concentrate (C) as defined above, the mixture (M) of
compounds of formula (IIIa) and of formula (IIIb) is composed
essentially: [0038] of 20% to 99% by weight of at least one
compound of formula (IIIa), and [0039] of 1% to 80% by weight of at
least one compound of formula. (IIIb).
[0040] Examples of topically acceptable solvents are water,
alcohols, such as ethanol, propanol or isopropanol, glycols, such
as propylene glycol, butylene glycol or hexylene glycol, or
water/alcohol or water/glycol mixtures.
[0041] According to preferred aspects of the present invention, the
concentrate (C) as defined above exhibits one or another or some
following specific characteristics: [0042] the concentrate (C) does
not comprise solvent; [0043] the concentrate (C) is an aqueous
solution of the mixture (M); [0044] the mixture (M) consists
essentially of: from 20% to 30% by weight of at least one compound
of the formula (IIIa) and from 70% to 80% by weight of at least one
compound of formula (IIIb); [0045] in the formula (IIIa), p is
.gtoreq.1.005 and >1.5; [0046] in the formula (IIIb), n is
.gtoreq.1.05 and >2.
[0047] According to a third aspect, a subject matter of the
invention is the use of at least one alkylpolyglycoside of formula
(Ia) or (Ib) as emulsifying agent for the preparation of
oil-in-water emulsions comprising inorganic fillers and/or
pigments.
[0048] According to a fourth aspect, a subject matter of the
invention is the use of at least one alkylpolyglycoside of general
formula (II):
R--O(X).sub.p (II)
in which: [0049] R represents a linear or branched alkyl radical
having from 6 to 11 carbon atoms; [0050] X represents the residue
of a C.sub.5 or C.sub.6 sugar, preferably the glucose or xylose
residue; and [0051] p, which represents the mean degree of
polymerization of the sugar residue, is a decimal number of greater
than 1 and less than or equal to 5, and more particularly of less
than or equal to 2.5, as emulsifying agent for the preparation of
oil-in-water emulsions comprising inorganic fillers and/or
pigments.
[0052] In the formula R--O--(X).sub.p, the R--O-- group is bonded
to X via the anomeric carbon of the sugar residue, so as to form an
acetal functional group.
[0053] When X represents the xylose residue, p is more particularly
between 1.005 and 1.5.
[0054] When X represents the glucose residue, p is more
particularly between 1.05 and 2.
[0055] The compound of formula R--O--(X).sub.p can be prepared
according to methods well known to a person skilled in the art.
[0056] The alkylpolyglycosides in the concentrate (C) in accordance
with the invention make it possible to prepare oil-in-water (O/W)
emulsions comprising inorganic fillers and/or pigments.
[0057] They advantageously represent from 0.2 to 10% by weight,
preferably from 0.5 to 5% by weight, of the O/W emulsion.
[0058] The inorganic fillers and/or pigments can be lamellar or
spherical and without specific limitation with respect to the
particle size. Mention may in particular be made, as examples of
inorganic fillers and pigments, of titanium dioxide; zinc oxide;
iron oxide (black, red or yellow); iron titanate; carbon black;
chromium oxide; chromium hydroxide; zirconium oxide; cerium oxide;
cobalt titanate; ultramarine; Prussian blue; titanium oxide-coated
mica; bismuth oxychloride; pearl essence; talc; aluminum powder;
copper powder; gold powder; mica; sericite; boron nitride;
photochromic pigments; or interferential pigments. These fillers
may have been subjected to a surface treatment or may be
encapsulated, such as, for example, in nylon matrices or
polymers.
[0059] These fillers and pigments generally represent from 0.5 to
40% by weight, preferably from 2 to 25% by weight, of the O/W
emulsion.
[0060] The O/W emulsion also comprises from 1 to 50% by weight,
preferably from 5 to 35% by weight and more preferably from 5 to
25% by weight of a fatty phase composed of one or more oils and/or
of one or more waxes.
[0061] The oil is advantageously chosen from the following oils:
[0062] oils of vegetable origin, such as sweet almond oil, coconut
oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil,
sunflower oil, wheat germ oil, corn germ oil, soybean oil,
cottonseed oil, alfalfa oil, poppy oil, pumpkinseed oil, evening
primrose oil, millet oil, barley oil, rye oil, safflower oil,
candlenut oil, passionflower oil, hazelnut oil, palm oil, karite
butter, apricot kernel oil, calophyllum oil, sisymbrium oil,
avocado oil or calendula oil; [0063] vegetable oils and their
methyl esters which are ethoxylated; [0064] oils of animal origin,
such as squalene or squalane; [0065] mineral oils, such as liquid
paraffin, liquid petrolatum and isoparaffins; [0066] synthetic
oils, in particular fatty acid esters, such as butyl myristate,
propyl myristate, cetyl myristate, isopropyl palmitate, butyl
stearate, hexadecyl stearate, isopropyl stearate, octyl stearate,
isocetyl stearate, dodecyl oleate, hexyl laurate, propylene glycol
dicaprylate, esters derived from lanolic acid, such as isopropyl
lanolate or isocetyl lanolate, or fatty acid monoglycerides,
diglycerides and triglycerides, such as glyceryl triheptanoate,
alkyl benzoates, poly-.alpha.-olefins, polyolefins, such as
polyisobutene, synthetic isoalkanes, such as isohexadecane or
isododecane, perfluorinated oils and silicone oils.
[0067] This oil can also be chosen from fatty acids, fatty
alcohols, waxes of natural or synthetic origin and more generally
still any fatty substance of vegetable, animal or synthetic
origin.
[0068] The wax is advantageously chosen from fatty substances which
are solid at ambient temperature, such as, for example, beeswax;
carnauba wax, candelilla wax; ouricury wax; Japan wax; cork fiber
or sugarcane wax; paraffin waxes; lignite waxes; microcrystalline
waxes; lanolin wax; ozokerite; polyethylene wax, hydrogenated oils;
silicone waxes; vegetable waxes; fatty alcohols and fatty acids
which are solid at ambient temperature; or glycerides which are
solid at ambient temperature.
[0069] The O/W emulsion in accordance with the invention can also
comprise up to 10% by weight, for example from 0.1 to 10% by
weight, of a stabilizing system.
[0070] The stabilizing system can be composed of one or more
compounds chosen from magnesium silicate; aluminum silicate; sodium
silicate; xanthan gum; acacia gum; locust bean gum; scleroglucan
gum; gellan gum; alginates; cellulose and cellulose derivatives;
clays; starches and starch derivatives; carbomer; acrylic acid
polymers and copolymers; acryloyldimethyl taurate polymers and
copolymers; polyvinylpyrrolidone; acrylamide polymers and
copolymers; or polyurethanes.
[0071] The O/W emulsion can also comprise up to 30% by weight of
one or more additives generally used in cosmetics and chosen from:
[0072] coemulsifiers, such as, for example, fatty acids and fatty
acid soaps; ethoxylated fatty acids; fatty acid esters; ethoxylated
fatty acid esters, including polysorbates; polyglycerol esters;
sucrose esters; alkylpolyglycosides with a chain length of greater
than 12 carbon atoms; ethoxylated fatty alcohols; sulfated fatty
alcohols; or phosphated fatty alcohols; [0073] preservatives
generally used in cosmetics; [0074] fragrances or other additives
with a scenting function (such as, in particular, essential oils
and essential waxes); [0075] cosmetic active principles; [0076]
cosolvents, such as, for example, glycerol; sorbitol; PEG;
monopropylene glycol; butylene glycol; isoprene glycol; 2-methyl-,
3-propanediol; ethanol; or hexylene glycol; [0077] inorganic or
organic bases, such as, for example, sodium hydroxide; potassium
hydroxide; ammonia; triethanolamine;
tetrahydroxypropylethylenediamine; trishydroxyaminomethane; or
aminomethylpropanol; [0078] acids, in particular lactic acid,
citric acid, acetic acid or tartaric acid.
[0079] Thus, according to a fifth aspect, a subject matter of the
present invention is an oil-in-water emulsion comprising at least
one alkylpolyglycoside corresponding in particular to the formula
(Ia), (Ib) or (II), and pigments and/or fillers.
[0080] According to a sixth aspect of the present invention, a
subject matter of the latter is an oil-in-water emulsion comprising
from 0.5% to 10% by weight and more particularly from 1% to 5% by
weight of the concentrate (C) as defined above, and inorganic
pigments and/or fillers.
[0081] The O/W emulsion in accordance with the invention can be
prepared by processes known to a person skilled in the art, such
as, for example, a process which comprises the following stages:
[0082] a.sub.1) The aqueous phase comprising the fillers is milled
using, for example, a bead mill or a device with a rotor-stator
turbine mixer of Silverson type. This aqueous phase is subsequently
heated to a temperature of 70 to 85.degree. C. [0083] b.sub.1) At
the same time, the fatty phase, comprising the emulsifier and the
oils, is heated to an identical temperature of 70 to 85.degree. C.
[0084] c.sub.1) The compositions according to the invention are
introduced without distinction into the fatty phase or the aqueous
phase. [0085] d.sub.1) The two phases are subsequently mixed and
emulsified using, for example, a rotor-stator emulsifying device
(for example, a laboratory mixer of Silverson type). After
emulsifying for a few minutes, the emulsion is cooled with moderate
stirring.
[0086] Another example of the process for the preparation of the
O/W emulsion comprises the following stages: [0087] a.sub.2) The
aqueous phase is heated to 70-85.degree. C. [0088] b.sub.2) The
fatty phase, comprising the fillers, emulsifier and the oils, is
heated to an identical temperature of 70 to 85.degree. C. [0089]
c.sub.2) The compositions according to the invention are introduced
without distinction into the fatty phase or the aqueous phase.
[0090] d.sub.2) The two phases are subsequently mixed and
emulsified using, for example, a rotor-stator emulsifying device
(Silverson laboratory mixer). After emulsifying for a few minutes,
the emulsion is cooled with moderate stirring.
[0091] It is also possible, provided all the constituents of the
emulsion are liquid at ambient temperature, to prepare said
emulsion by a process devoid of heating.
[0092] According to a final aspect of the present invention, a
subject matter of the latter is a process for the preparation of a
cosmetic or pharmaceutical oil-in-water emulsion for topical use,
characterized in that between 0.2% and 10% by weight and more
particularly between 0.5% and 5% by weight of a concentrate (C) as
defined above is mixed with the other constituents of said
composition.
EXAMPLES
[0093] The invention is illustrated by the nonlimiting examples
below. In these examples, the emulsions prepared are monitored:
[0094] by monitoring using a microscope with a magnification of 40.
[0095] by visual (macroscopic) monitoring of the stability of the
emulsions with checking after 3 months of the appearance of the
emulsions in the flask; smooth or granular appearance, glossy or
matt appearance, monitoring of phenomena of phase separation, of
release of pigments at the surface of the emulsion or of
stratification of the pigments with a nonuniform visual effect. The
optimum criteria are a glossy, perfectly smooth and homogeneous
emulsion without phase separation or release or stratification of
the pigments and fillers. The grading is as follows: + if all the
criteria are satisfactory, +/- if at least one of the criteria is
unsatisfactory, 0 if none of the criteria is satisfactory. [0096]
by monitoring of the texture with the preparation, on a
Plexiglas.RTM. sheet, of films calibrated to 120 .mu.m and checking
for the absence of agglomerates of fillers and pigments. The
grading is as follows: + in the absence of specks 3 months after
the manufacture of the emulsion, +/- in the presence of a few
specks, 0 in the presence of numerous specks.
[0097] In the case of the emulsions comprising fillers with the
role of protecting from UV radiation, the protection factor is
evaluated according to the method described below:
[0098] The protection factor is evaluated in vitro by measuring the
absorbing power with respect to UV-B and UV-A radiation after
spreading a film of emulsion over a support which models the skin
surface.
[0099] The emulsion is spread in a calibrated way (2 mg/cm.sup.2)
over a prehydrated collagen matrix sold under the name
Vitroskin.RTM. by IMS. After drying the film for a period of 15
minutes, the coated support is subjected to exposure to UV
radiation using a Labsphere.RTM. spectro-photometer. The sun
protection coefficient is calculated by the software of the device
according to the Diffey formula from the transmission of the UV
radiation over the whole spectrum between 280 and 400 nm.
[0100] In view of the role of UV-A radiation in the onset of skin
cancers, the relative importance of the protection with respect to
UV-A radiation is calculated by producing the ratio of the area
under the absorbance curve in the UV-A spectrum to the area under
the absorbance curve in the UV-B spectrum. A UV-A/UV-B ratio of
>0.6 is recommended for effective protection with respect to
UV-A radiation.
Example 1
Preparation of an alkylpolyxyloside of Formula (I)
[0101] 908.4 g of 1,10-decanediol, sold by Cognis under the name
Speziol.RTM. C10/2, are gradually introduced into a two liter glass
reactor. The reactor is brought to a temperature of 90.degree. C.,
so as to effectively melt the 1,10-decanediol, stirring is started
and 390.0 g of xylose are dispersed in the presence of a catalytic
amount of sulfuric acid. After two hours at 80.degree.
C./85.degree. C. under vacuum and neutralization with sodium
hydroxide, the product exhibits the following analytical
characteristics: [0102] Appearance (visual): off-white solid [0103]
Color of a molten product (NFT 20 030): 1 vcs [0104] pH of a 5%
dispersion (NFT 73 206): 7.8 [0105] Water content: 0.47% [0106]
Acid number (NFT 60 204): 0.25 [0107] Hydroxyl number: 689 [0108]
Residual 1,10-decanediol: 37.3%
Example 2
Preparation of an alkylpolyxyloside of Formula (I)
[0108] [0109] The procedure of example 1 is repeated but 500.6 g of
1,10-decanediol being reacted with 430 g of xylose to result in a
product exhibiting the following analytical characteristics: [0110]
Appearance (visual): black solid [0111] pH of a 5% dispersion (NFT
73 206): 7.8 [0112] Water content: 2.0% [0113] Acid number (NFT 60
204): 4.9 [0114] Hydroxyl number: 726 [0115] Residual
110-decanediol: 9.0%
Example 3
Preparation of O/W Emulsions Intended for UV Protection
[0116] O/W emulsions are prepared which comprise the following
ingredients:
TABLE-US-00001 A Emulsifier 02.50% C.sub.12-C.sub.15 Alkyl benzoate
20.00% Titanium oxide (20 nm/dimethicone coating) 10.00% B
Cyclomethicone 05.00% Glycerol 07.00% C Tetrasodium EDTA 00.20%
Water q.s. for 100% Carbomer .RTM. 00.05% Tromethamine q.s. pH >
7 Magnesium silicate/Aluminum silicate 01.00% Xanthan gum 00.15% D
DL-.alpha.-Tocopherol 00.05% Preservatives q.s.
[0117] The Carbomer.RTM., the magnesium silicate/aluminum silicate
and the xanthan gum are dispersed in the aqueous phase. The aqueous
phase is heated to 70-85.degree. C. and then the EDTA and the
tromethamine are added.
[0118] The fatty phase, comprising the titanium oxide, the
emulsifier and the C.sub.12-C.sub.15 alkyl benzoate, is heated to
an identical temperature of 70 to 85.degree. C. The cyclo-methicone
and the glycerol are added to this hot fatty phase.
[0119] The two phases are subsequently mixed and emulsified using a
rotor-stator emulsifying device (Silverson laboratory mixer). After
emulsifying for a few minutes, the emulsion is cooled with moderate
stirring.
[0120] The tocopherol and the preservatives are added at the end of
cooling with moderate stirring.
[0121] The results are presented in table 1.
TABLE-US-00002 TABLE 1 Microscopic Texture Brookfield appearance of
the viscosity Stability of the Emulsifier emulsion (mPa s) at AT
emulsion Decylglucoside Smooth 9500 >3 months Fine and (p =
1.45) milk homogeneous Decylglucoside Smooth 7000 >3 months Fine
and (p = 1.9) milk homogeneous Example 1 Smooth 9000 >3 months
Fine and milk homogeneous Ethylhexyl- Smooth 10 500 >3 months
Fine end glucoside milk homogeneous (p = 1.45)
Comparative Example 1
[0122] The procedure of example 3 is repeated by using
alkylpolyglucoside-based emulsifiers having a chain with 4 and 12
carbon atoms and ethoxylated emulsifiers. The results are presented
in table 2.
TABLE-US-00003 TABLE 2 Microscopic Texture of Brookfield appearance
the viscosity Stability of the Emulsifier emulsion (mPa s) at AT
emulsion Cetearyl- Granular 43 000 >3 months agglomerates
glucoside cream (p = 1.25) Dodecyl- Granular 7000 <7 days
agglomerates glucoside milk (p = 1.43) Butyl- Non- -- -- --
glucoside emulsifying (p = 1.45) Laureth-7 Granular 15 000 <3
months agglomerates Deceth-4 Granular 8000 <7 days agglomerates
milk Deceth-5 Granular 11 000 <7 days agglomerates cream
Deceth-3 Non- -- -- -- emulsifying
[0123] It is not possible with butylglucoside to obtain an emulsion
and dodecylglucoside results in emulsions which are less stable
than those obtained with the alkylglucosides according to the
invention. Cetearyl-glucoside and dodecylglucoside give
agglomerates. The ethoxylated nonionic surfactants are less
effective than the alkylpolyglycosides according to the
invention.
Example 4
Stability Over Time of the Dispersion of Pigments and of the
Protection Factor of O/W Emulsions
[0124] An emulsion is prepared which comprises the following
ingredients:
TABLE-US-00004 A Emulsifier 2.50% Diisopropyl adipate 25.00%
Titanium oxide (20 nm/dimethicone coating) 10.00% Zinc oxide (50
nm) 02.00% B Cyclomethicone 03.00% Glycerol 07.00% C Tetrasodium
EDTA 00.20% Water q.s. for 100% Carbomer .RTM. 00.05% Tromethamine
q.s. pH > 7 Magnesium silicate/Aluminum silicate 01.00% Xanthan
gum 00.15% D DL-.alpha.-Tocopherol 00.05% Preservatives q.s.
[0125] The Carbomer.RTM., the magnesium silicate/aluminum silicate
and the xanthan gum are dispersed in the aqueous phase. The aqueous
phase is heated to 70-85.degree. C. and then the EDTA and the
tromethamine are added.
[0126] The fatty phase, comprising the titanium oxide and the zinc
oxide, the emulsifier and the oil, is heated to an identical
temperature of 70 to 85.degree. C. The cyclomethicone and the
glycerol are added to this hot fatty phase.
[0127] The two phases are subsequently mixed and emulsified using a
rotor-stator emulsifying device (Silverson laboratory mixer). After
emulsifying for a few minutes, the emulsion is cooled wish moderate
stirring.
[0128] The tocopherol and the preservatives are added at the end of
cooling with moderate stirring.
[0129] The results are presented in table 3.
TABLE-US-00005 TABLE 3 (PEG 100 stearate + glycerol stearate) 1.7%
+ DEA cetyl Dodecyl- Decylglucoside phosphate 0.8% glucoside
Emulsifier (invention) (comparative) (comparative) Texture of the
Smooth milk Granular milk Granular milk emulsion >1 year at 1
month at 1 day Microscopic Fine and Onset of Onset of appearance
homogeneous agglomerates agglomerates dispersion beyond 15 days at
1 day >1 year Stability AT >1 year >1 year <1 month
40.degree. C. >6 months <3 months <1 month 50.degree. C.
>1 month <15 days <1 month Protection factor 7 days 14 15
8 1 month 16 8 -- 1 year 15 5 -- UV-A/UV-B Ratio 7 days 0.9 0.9
0.55 1 year 0.9 0.6 --
[0130] Decylglucoside, the emulsifier according to the invention,
makes it possible, in contrast to the comparative emulsifiers, to
retain a fine and homogeneous dispersion of the filters during the
storage with consequently a visual texture which remains perfectly
smooth over time and a stable protection factor, both in the UV-B
spectrum and in the UV-A spectrum, as is illustrated by the value
of the factor and that of the UV-A/UV-B ratio.
Example 5
Preparation of an O/W Emulsion Without Heating
[0131] An emulsion is prepared which comprises the following
ingredients:
TABLE-US-00006 A Emulsifier 03.00% Caprylic/capric triglycerides
20.00% Zinc oxide 05.00% Glycerol 05.00% C Tetrasodium EDTA 00.10%
Water q.s. for 100% Sepigel .RTM. 305 01.50% Tromethamine q.s. pH
> 7 Magnesium silicate/Aluminum silicate 01.00% Xanthan gum
00.15% D DL-.alpha.-Tocopherol 00.05% Preservatives q.s.
[0132] The Sepigel.RTM. 305 (polyacrylamide and C.sub.11-C.sub.13
isoparaffin and laureth-7; sold by Seppic), the magnesium
silicate/aluminum silicate and the xanthan gum are dispersed in the
aqueous phase. The EDTA and the tromethamine are added to the
aqueous phase.
[0133] The fatty phase is produced by simple mixing of the
constituents without heating.
[0134] The two phases are subsequently mixed and emulsified using a
rotor-stator emulsifying device (Silverson laboratory mixer). The
tocopherol and the preservatives are added with moderate
stirring.
[0135] The results are presented in table 4.
TABLE-US-00007 TABLE 4 Emulsifier Decylglucoside Octylxyloside
Texture of the Smooth milk Smooth milk emulsion Microscopic Fine
and Fine and appearance homogeneous homogeneous dispersion
dispersion Stability AT >1 month >1 month 40.degree. C. >1
month >1 month 50.degree. C. >1 month >1 month Protection
factor 1 month 9 6 1 year 8.5 6
Example 6
Preparation of Emulsions Intended for Makeup
TABLE-US-00008 [0136] A Emulsifier 2.50% Isononyl isononanoate
08.00% Diisopropyl dimer dilinoleate 08.00% B Cyclomethicone 04.00%
Sepigel .RTM. 305 01.50% C Water q.s. for 100% Micropearl .RTM.
M305 02.00% (crosslinked methyl methacrylate polymer) Tetrasodium
EDTA 00.50% D Pigment paste Butylene glycol 04.00% Polyethylene
glycol 400 04.00% Titanium dioxide, E171 07.00% Talc, Luzenac 000C
02.00% Yellow iron oxide, 00.80% Sicovit yellow 10 E172 Red iron
oxide, Sicovit red 30 E172 00.30% Black iron oxide, Sicovit black
00.05% Water 20.00% NaOH q.s. for pH > 8 E Preservatives q.s.
Fragrance 00.20%
[0137] The pigment paste is milled beforehand on a bead mill.
[0138] The water is heated to 70-75.degree. C. and then the
Micropearl.RTM., the EDTA and the pigment paste are added to the
hot aqueous phase.
[0139] The fatty phase, comprising the emulsifier and the oils, is
heated to a temperature of 70 to 75.degree. C. The cyclomethicone
and the Sepigel.RTM. 305 are added to this hot fatty phase.
[0140] The two phases are subsequently mixed and emulsified using a
rotor-stator emulsifying device (Silverson laboratory mixer). After
emulsifying for a few minutes, the emulsion is cooled with moderate
stirring.
[0141] The preservatives and the fragrance are added at the end of
cooling with moderate stirring.
[0142] The results are presented in table 5.
TABLE-US-00009 TABLE 5 Sodium stearate 1.7% + Cetearyl- Steareth-10
Decylglucoside glucoside 0.8% Emulsifier (invention) (comparative)
(comparative) Visual + +/- +/- appearance after 3 months Texture
after + +/- 0 3 months Rendering of the color on application
(Minolta CR300 chromameter) after 3 months Parameter L 68.3
(.+-.0.7) 70.1 (.+-.0.4) 73.4 (.+-.0.6) Parameter a 2.3 (.+-.0.6)
18.2 (.+-.2.3) 16.5 (.+-.2.7) Parameter b 30 (.+-.0.9) 23.7
(.+-.1.5) 20.2 (.+-.2.8)
[0143] The fineness of the dispersion of the fillers is reflected
by an improvement in the spreading over the skin, by uniform color
and by a better rendering of the color on the skin: decrease in the
whiteness (parameter L) and an enhancement in the colored
parameters a (red hue) and b (blue hue). The non-uniformity in the
color with the comparative examples is clearly apparent with regard
to the standard deviation values for a and b, which are higher than
in the example according to the invention.
Example 7
Preparation of O/W Emulsions Intended for Makeup
TABLE-US-00010 [0144] A Isononyl isononanoate 08.00% Triisostearyl
citrate 08.00% Simulgel .RTM. NS 04.00% B Water q.s. for 100%
Tetrasodium EDTA 00.05% Emulsifier 0.8% C Pigment paste Butylene
glycol 04.00% Polyethylene glycol 400 04.00% Titanium dioxide, E171
05.00% Yellow iron oxide, 00.80% Sicovit yellow 10 E172 Red iron
oxide, Sicovit red 30 E172 00.30% Black iron oxide, Sicovit black
00.05% Water 20.00% NaOH q.s. for pH > 8 D Preservatives q.s.
Fragrance 00.20%
[0145] The pigment paste is milled beforehand on a bead mill.
[0146] The Simulgel.RTM. NS (sodium acryloyldimethyl
taurate/hydroxyethyl acrylate copolymer and squalane and
polysorbate 80; sold by Seppic) is mixed with the oils. The aqueous
phase B is added to phase A to form the cream gel. The pigment
paste (phase C) and subsequently phase D are then added directly to
the cream gel with moderate stirring.
[0147] The results are presented in table 6.
TABLE-US-00011 TABLE 6 Decylglucoside Laureth-7 Emulsifier
(invention) (comparative) Visual appearance + 0 After 3 months
Texture after + 0 3 months
[0148] It will be understood that many additional changes in the
details, materials, steps and arrangement of parts, which have been
herein described in order to explain nature of the invention, may
be made by those skilled in the art within the principle and scope
of the invention as expressed in the appended claims. Thus, the
present invention is not intended to be limited to the specific
embodiments in the examples given above.
* * * * *