Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2001-10-31
2003-02-04
Kumar, Shailendra (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C252S391000, C424S059000, C514S629000, C554S035000
Reexamination Certificate
active
06515178
ABSTRACT:
The present invention relates to a novel composition, in particular a cosmetic composition, comprising specific amides and pulverulent materials. The invention also relates to the use of certain amides as dispersants for pulverulent materials, as well as to a process for dispersing pulverulent materials.
It is known practice to use pulverulent materials such as pigments or fillers in cosmetic compositions for the purpose in particular of giving these compositions a desired colour. Certain metal oxide pigments, such as titanium dioxide, are also used for their known appreciable anti-UV properties. However, the incorporation of these pulverulent materials into cosmetic compositions is not always easy to carry out. The reason for this is that the appearance of aggregates is frequently observed and the pigments often tend to sediment out over time; the dispersion of the pigments in the composition is then no longer homogeneous. The sedimentation of the pigments no longer makes it possible to conserve the uniformity of the colour of the composition, in particular when it is applied to the skin. This sedimentation can also give rise to a substantial reduction in the efficacy of the antisun protection imparted by pigments with anti-UV properties.
To prevent the aggregation and/or sedimentation of pigments, it has been proposed to use dispersing agents, and in particular branched alkyl esters. For example, patents U.S. Pat. Nos. 5,476,637 and 5,516,506 describe the use of neopentyl glycol esters to help disperse pigments. According to patent application WO 94/18940, it is also known practice to improve the dispersion of titanium oxide pigments by using branched organic compounds such as esters, ethers, hydrocarbons or silicones, and in particular octyldodecyl neopentanoate.
Although these dispersants described in the prior art make it possible to disperse the pigments commonly used in cosmetics, the stability over time of these dispersions is, however, unsatisfactory. The reason for this is that, after storage for several hours, or even several days, it is found that the pigment dispersion does not retain its homogeneity since the pigments sediment out over time.
Moreover, it is known practice from patent U.S. Pat. No. 5,162,315 and patent application JP-A-62-215,537, to use amides comprising at least two alkyl chains to improve the penetration of pharmaceutical active agents into the skin. In patent application WO 88/04167, amides comprising two alkyl chains are used in an antisun or moisturizing composition, in the form of an emulsion, to impart moisture resistance to the composition.
An object of the present invention is to allow the preparation and production of a composition which comprises homogeneously dispersed pulverulent materials and which is stable over time.
The Applicant has discovered, surprisingly and unexpectedly, that by using certain branched amides, an entirely stable dispersion of pulverulent materials can be obtained. Furthermore, the stability of the dispersion thus obtained can be preserved for more than one week, or even more than one month.
Thus, the invention relates to a composition comprising at least one pulverulent material and at least one amide of formula (I) below:
R
1
—CO—NH—R
2
(I)
in which R
1
and R
2
, independently of each other, denote a saturated or unsaturated, branched alkyl radical comprising from 3 to 30 carbon atoms. Preferably, R
1
and R
2
, independently of each other, denote a saturated branched alkyl radical containing from 3 to 20 carbon atoms. More preferably, R
1
comprises from 3 to 10 carbon atoms and R
2
comprises from 10 to 20 carbon atoms.
Advantageously, R
2
denotes a branched radical of formula (II):
in which R
3
and R
4
, independently of each other, denote a linear alkyl radical containing from 1 to 27 carbon atoms, with the proviso that the total number of carbon atoms in the radical of formula (II) is less than or equal to 30. Preferably, R
3
and R
4
, independently of each other, contain from 2 to 12 carbon atoms, and more preferably from 2 to 10 carbon atoms.
Groups R
1
which may be mentioned, for example, are tert-butyl and 2,4,4-trimethylpentyl groups.
Groups R
2
which may be mentioned are, in particular, 2-octyldodecyl and 2-butyloctyl groups.
Among the preferred compounds corresponding to the general formula (I), mention may be made in particular of:
N-neopentanoyl-2-octyldodecylamine,
N-neopentanoyl-2-butyloctylamine,
N-(3,5,5-trimethylhexanoyl)-2-octyldodecylamine,
N-(3,5,5-trimethylhexanoyl)-2-butyloctylamine.
The compounds of formula (I) are preferably present in a content ranging from 0.1% to 50% by weight relative to the total weight of the composition, and better still from 2 to 20%.
The pulverulent materials present in the composition can be chosen from pigments, nacres and/or fillers. They are preferably present in a proportion of from 0.1 to 80% by weight relative to the total weight of the composition.
Among the pigments which may be mentioned are inorganic pigments such as titanium oxide, zinc oxide, iron oxide, zirconium oxide and cerium oxide, or mixtures thereof. Nanopigments of these metal oxides which are known for their anti-VU properties can also be used. These nanopigments are used in a known manner in antisun compositions. The term “nanopigments” means pigments whose average primary particle size does not exceed 100 nm, this size preferably being between 5 nm and 100 nm and even more preferably between 10 and 50 nm. Such coated or uncoated metal oxide nanopigments are products known to those skilled in the art and are described in particular in patent application EP-A-0,518,773, the teaching of which is, in this respect, included in the present description by way of reference.
Inorganic Pigments which may also be mentioned are chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue. The organic pigments can be chosen from carbon black, pigments of D & C type, and lakes based on cochineal carmine.
The nacres can be chosen from white nacreous pigments such as mica coated with titanium oxide or with bismuth oxychloride, coloured nacreous pigments such as titanium mica coated with iron oxides, titanium mica with, in particular, ferric blue or chromium oxide, titanium mica with an organic pigment of the abovementioned type, as well as nacreous pigments based on bismuth oxychloride.
The fillers can be inorganic or organic, and lamellar or spherical. Mention may be made of talc, mica, silica, kaolin, Nylon powder, poly-&bgr;-alanine powder and polyethylene powder, Teflon, lauroyllysine, starch, titanium mica, natural mother-of-pearl, boron nitride, tetrafluoroethylene polymer powders, hollow microspheres such as Expancel (Nobel Industrie), Polytrap (Dow Corning) and silicone resin microbeads (Tospearls from Toshiba, for example), zinc oxide, titanium oxide, precipitated calcium carbonate, magnesium carbonate and hydrocarbonate, hydroxyapatite, hollow silica microspheres (Silica Beads from Maprecos), glass or ceramic microcapsules; metal soaps derived from organic carboxylic acids containing from 8 to 22 carbon atoms, preferably from 12 to 18 carbon atoms, for example zinc, magnesium or lithium stearate, zinc laurate or magnesium myristate.
A subject of the invention is also the amides of formula (I′) below:
in which
R
1
denotes a saturated or unsaturated, branched alkyl radical containing from 3 to 30 carbon atoms,
R
3
and R
4
, independently of each other, denote a linear alkyl radical containing from 1 to 27 carbon atoms, with the proviso that the total number of carbon atoms in the radical —CH
2
—CH(R
3
) (R
4
) of formula (I′) is less than or equal to 30.
Preferably, R
1
, R
3
and R
4
have the preferred meanings mentioned above for the compounds of formula (I).
These compounds are generally in the form of an oily liquid. It has thus been observed that the dispersion of pulverulent materials in the amides according to the invention is better, more homogeneous and more stable over time than the dispersion of these same pulverulent ma
Philippe Michel
Semeria Didier
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
Kumar Shailendra
L'Oreal
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