Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations
Reexamination Certificate
2002-06-25
2003-01-21
Dodson, Shelley A. (Department: 1616)
Drug, bio-affecting and body treating compositions
Topical sun or radiation screening, or tanning preparations
C424S060000, C424S400000, C424S401000, C514S241000
Reexamination Certificate
active
06509008
ABSTRACT:
The present invention relates to a composition comprising at least one 1,3,5-triazine derivative and also to its use in or for the manufacture of cosmetic or dermatological compositions for protecting the skin and/or the lips and/or integuments against ultraviolet radiation, in particular solar radiation.
It is known that light radiation with wavelengths of between 280 nm and 400 nm permits tanning of the human epidermis, and that light rays with wavelengths of between 280 nm and 320 nm, known as UV-B rays, cause skin burns and erythema which may be harmful to the development of a natural tan; this UV-B radiation should thus be screened out.
It is also known that UV-A rays, with wavelengths of between 320 nm and 400 nm, which cause tanning of the skin, are liable to induce an adverse change in the latter, especially in the case of sensitive skin or of skin which is continually exposed to solar radiation. UV-A rays cause in particular a loss of elasticity of the skin and the appearance of wrinkles, leading to premature skin aging. They promote triggering of the erythemal reaction or amplify this reaction in certain individuals and may even be the cause of phototoxic or photoallergic reactions. It is thus desirable also to screen out UV-A radiation.
Many cosmetic compositions intended for the photoprotection (UV-A and/or UV-B) of the skin have been proposed to date.
These anti-sun compositions are quite often in the form of an emulsion of oil-in-water type (that is to say a cosmetically acceptable vehicle consisting of a continuous aqueous dispersing phase and a discontinuous. 1,3,5-Triazine derivatives are particularly desired in anti-sun cosmetics due to the fact that they are highly active in the UV-B range, and even in the UV-A range for some of these compounds, depending on the nature of the substituents involved. Furthermore, they are photostable, i.e., they show little or no chemical degradation under the action of UV radiation. They are especially described in U.S. Pat. No. 4,617,390, EP 863 145, EP 517 104, EP 570 838, EP 796 851, EP 775 698, EP 878 469 and EP 933 376, and the following are known in particular:
2,4,6-tris[p-(2′-ethylhexyl-1′-oxycarbonyl) anilino]-1,3,5-triazine or “Ethylhexyl Triazone” (INCI name), sold under the trade name “Uvinul T 150” by BASF,
2-[(p-(tert-butylamido)anilino]-4,6-bis-[(p-(2′ethylhexyl-1′-oxycarbonyl)anilino]-1,3,5-triazine or “Diethylhexyl Butamido Triazone” (INCI name), sold under the trade name “Uvasorb HEB” by Sigma 3V, and
2,4-bis{[4-2-ethylhexyloxy)]-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine or “Anisotriazine” (INCI name), sold under the trade name “Tinosorb S” by Ciba Specialty Chemicals.
It has been proposed in the prior art to use 1,3,5-triazine derivatives in oils such as esters and more particularly C
12
-C
15
alkyl benzoates (“Finsolv TN” from Finetex), or triglycerides and especially C
8
-C
12
fatty acid triglycerides (“Miglyol 812” from Hüls), or alternatively oxyethylenated or oxypropylenated fatty monoalcohols or polyols (“Cetiol HE” from Henkel or “Witconol AM” from Witco).
However, it has been observed that the photoprotective power of these triazine derivatives in the absence of other sunscreens is very limited and that their cosmetic properties are generally considered to be insufficient.
The problem posed underlying the present invention was that of improving the photoprotective efficacy of compositions containing such 1,3,5-triazine derivatives.
Surprisingly and unexpectedly, the inventors of the present patent application have shown that the use of at least one ester chosen from N-acyl amino acid esters of formula:
R′
1
(CO)N(R′
2
)CH(R′
3
)(CH
2
)
n
(CO)OR′
4
in which:
n is an integer equal to 0, 1 or 2,
R′
1
represents a linear or branched C
5
to C
21
alkyl or alkenyl radical,
R′
2
represents a hydrogen atom or a C
1
to C
3
alkyl group,
R′
3
represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group and a linear or branched C
3
or C
4
alkyl chain, and
radical or a sterol residue, makes it possible to obtain a composition containing 1,3,5-triazine derivatives that have improved cosmetic and photoprotective properties. These N-acyl amino acid esters, and also the process for preparing them, are described in EP 1 044 676 and EP 0 928 608 to Ajinomoto Co.
The main advantage of these N-acyl amino acid esters is that they allow the production of anti-sun compositions containing 1,3,5-triazine derivatives and have a sun protection factor that is greater than that of the compositions of the prior art containing 1,3,5-triazine derivatives.
These compositions also have improved cosmetic qualities. They allow good moisturization of the skin, i.e., no drying of the skin is observed, nor, on the contrary, any excessively greasy feel.
One subject of the present invention is thus a composition containing at least one 1,3,5-triazine derivative and at least one ester chosen from N-acyl amino acid esters.
Another subject of the invention consists in using such a composition to manufacture cosmetic or dermatological compositions.
A subject of the invention is also a cosmetic treatment process comprising the application of a composition according to the present invention, and also the use of at least one N-acyl amino acid ester of formula:
R′
1
(CO)N(R′
2
)CH(R′
3
)(CH
2
)
n
(CO)OR′
4
in which:
n is an integer equal to 0, 1 or 2,
R′
1
represents a linear or branched C
5
to C
21
alkyl or alkenyl radical,
R′
2
represents a hydrogen atom or a C
1
to C
3
alkyl group,
R′
3
represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group and a linear or branched C
3
or C
4
alkyl chain, and
R′
4
represents a linear or branched C
1
to C
10
alkyl radical or a linear or branched C
2
to C
10
alkenyl radical or a sterol residue, in anti-sun compositions containing a 1,3,5-triazine derivative, in order to improve the sun protection factor of this composition.
Other subjects of the invention will become apparent on reading the description and the examples that follow.
The composition that is the subject of the invention preferably comprises, in a physiologically acceptable medium:
(i) at least one 1,3,5-triazine derivative, and
(ii) at least one ester chosen from N-acyl amino acid esters of formula:
R′
1
(CO)N(R′
2
)CH(R′
3
)(CH
2
)
n
(CO)OR′
4
in which:
n is an integer equal to 0, 1 or 2,
R′
1
represents a linear or branched C
5
to C
21
alkyl or alkenyl radical,
R′
2
represents a hydrogen atom or a C
1
to C
3
alkyl group,
R′
3
represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group and a linear or branched C
3
or C
4
alkyl chain, and
R′
4
represents a linear or branched C
1
to C
10
alkyl radical or a linear or branched C
2
to C
10
alkyl radical or a sterol residue.
In the formula for the amino acid esters presented above, the group R′
1
(CO)— is an acyl group of an acid preferably chosen from the group formed by capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, linoleic acid, linolenic acid, oleic acid, isostearic acid, 2-ethylhexanoic acid, coconut oil fatty acids and palm kernel oil fatty acids. These fatty acids may also contain a hydroxyl group. Even more preferably, the fatty acid is lauric acid.
The portion —N(R′
2
)CH(R′
3
)(CH
2
)
n
(CO)— of the amino acid ester is preferably chosen from the following amino acids: glycine, alanine, valine, leucine, isoleucine, serine, threonine, proline, hydroxyproline, &bgr;-alanine, aminobutyric acid, aminocaproic acid, sarcosine and N-methyl-&bgr;-alanine.
Even more preferably, the amino acid is sarcosine.
The portion of the amino acid esters corresponding to the group OR′
4
may be obtained from alcohols chosen from the group formed by methanol, ethano
Dodson Shelley A.
L'Oreal
Price D. Douglas
Steptoe & Johnson LLP
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