Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations
Reexamination Certificate
2002-06-19
2004-06-15
Dodson, Shelley A. (Department: 1616)
Drug, bio-affecting and body treating compositions
Topical sun or radiation screening, or tanning preparations
C424S060000, C424S400000, C424S401000
Reexamination Certificate
active
06749839
ABSTRACT:
The present invention relates to cosmetic compositions for topical use, in particular intended for photo-protecting the skin and/or the hair, comprising an effective amount of at least one aromatic amide, sulphonamide or carbamate derivative of acrylonitrile, to novel aromatic amide, sulphonamide or carbamate derivatives of acrylonitrile and to a non-therapeutic process for treating the skin using these compositions.
It is known that radiation with wavelengths of between 280 nm and 400 nm permit tanning of the human epidermis and that radiation with wavelengths of between 280 and 320 nm, known as UV-B radiation, cause skin burns and erythema that may be harmful to the development of a natural tan. For these reasons, and also for aesthetic reasons, there is increasing demand for means for controlling this natural tanning. This UV-B radiation should thus be screened out.
It is also known that UV-A rays, with wavelengths of between 320 and 400 nm, which cause tanning of the skin, are liable to induce adverse changes therein, especially in the case of sensitive skin and/or skin that is continually exposed to solar radiation. In particular, UV-A rays bring about a loss of elasticity of the skin and the appearance of wrinkles, leading to premature ageing of the skin. They promote the onset of the erythemal reaction or amplify this reaction in certain individuals and may even be the cause of phototoxic or photoallergic reactions. Thus, for aesthetic and cosmetic reasons such as maintenance of the natural elasticity of the skin, an increasingly large number of people wish to control the effect of UV-A rays on their skin. It is thus desirable also to screen out UV-A radiation.
UV-A rays are divided into UV-A-1 rays known as “long WV-A” with wavelengths of between 340 and 400 nm, and UV-A-2 rays known as “short UV-A” with wavelengths of between 320 and 340 nm. A good UV-A screening agent should cover these two ranges of wavelengths as much as possible, i.e. it should be a broad UV-A screening agent, without, however, having an intrinsic coloration due to the absorption of light at wavelengths in the visible range. Specifically, an important problem associated with the cosmetic use of coloured screening agents is the staining of fabrics liable to come into contact with these screening agents, such as towels and clothing.
Many compounds intended for protecting the skin against UV-A and/or UV-B radiation have been proposed to date.
Most of these are aromatic compounds that absorb UV radiation in the region between 280 nm and 315 nm, or in the region between 315 nm and 400 nm and above, or alternatively in both these regions. They are usually formulated in antisun compositions that are in the form of oil-in-water emulsions, the lipophilic or hydrophilic organic screening agents being present in dissolved form, in one or other of these phases, in amounts that are suitable to obtain the desired sun protection factor (SPF).
The expression “sun protection factor” means the ratio of the irradiation time required to reach the erythema-forming threshold in the presence of the test screening agent to the irradiation time required to reach this same threshold in the absence of screening agent.
Besides their screening power on solar radiation, photoprotective compounds must also have good cosmetic properties, good resistance to water and perspiration (remanence) and also satisfactory photostability.
Among all the aromatic compounds derived from 2-cyano-acrylic acid that have been proposed for this purpose, mention may be made of the compounds described in patent FR 1 368 808, international patent applications WO 99/36049 and WO 97/15279, and those described in European patent applications EP-A-0 911 020, EP-A-0 716 089 and EP-A-0 005 182. However, none of these screening agents simultaneously satisfies the three conditions of being a broad UV screening agent, that is to say of screening out both long UV-A and short UV-A, and of being uncoloured and photostable.
Mention may also be made of 4-(tert-butyl)-4′-methoxy-dibenzoylmethane, sold under the trade name Parsol® 1789 by the company Hoffman Laroche, which is an uncoloured long UV-A screening agent with a broad spectrum of absorption in the UV-A range, but which has the major drawback of degrading under the effect of solar radiation, that is to say of not being photostable.
The Applicant has discovered, surprisingly, that a particular family of aromatic amide, sulphonamide or carbamate derivatives of acrylonitrile have, simultaneously:
a broad spectrum of UV-A absorption, while at the same time being long UV-A screening agents,
an absence of coloration,
satisfactory photostability, and
good cosmetic properties,
and thus constitute excellent sunscreens that may be used, in replacement for Parsol® 1789, in cosmetic compositions, in particular to protect the skin and the hair against the harmful effects of sunlight.
One subject of the present invention is, consequently, a cosmetic composition for topical use, in particular intended for photoprotecting the skin and/or the hair, containing, in a cosmetically acceptable support, at least one compound chosen from the aromatic amide, sulphonamide or carbamate derivatives of acrylonitrile of formula (1) below or the corresponding dimers of formula (2) below.
A subject of the present invention is also the novel compounds of formula (2) below.
Finally, a subject of the present invention is a non-therapeutic process for protecting the skin and/or the hair against solar radiation, which consists in applying to the skin and/or the hair an effective amount of the cosmetic composition defined above.
The aromatic amide, sulphonamide or carbamate derivatives of acrylonitrile used as broad-spectrum UV-A screening agents in the cosmetic compositions of the present invention are compounds corresponding to the general formula (1)
or dimers of such compounds, corresponding to formula (2):
in which
X
1
represents a radical R
3
—(C═O)—, R
3
—SO
2
— or R
3
—O—(C═O)—,
X
2
represents a divalent radical of formula —(C═O)—R′
3
—(C═O)—, —SO
2
—R′
3
—SO
2
— or —(C═O)—O—R′
3
—O—(C═O)—,
Y represents a radical —(C═O)—R
4
or —SO
2
R
5
,
R
2
represents a linear or branched C
1-8
alkyl group,
n is 0, 1 or 2,
R
3
represents a linear or branched C
1-30
alkyl or C
3-30
alkenyl radical, possibly bearing one or more hydroxyl substituents and possibly containing, in the carbon chain, one or more hetero atoms chosen from oxygen, nitrogen and silicon atoms,
R′
3
represents a single bond or a linear or branched divalent C
1-30
alkylene or C
3-30
alkenylene radical, possibly bearing one or more hydroxyl substituents and possibly containing, in the carbon chain, one or more hetero atoms chosen from oxygen, nitrogen and silicon atoms,
R
4
represents a radical —OR
6
or —NHR
6
,
R
5
represents a linear or branched C
1-30
alkyl radical or a phenyl nucleus that is unsubstituted or substituted with C
1-4
alkyl or alkoxy radicals,
R
6
represents a linear or branched C
1-30
alkyl or C
3-30
alkenyl radical, possibly bearing one or more hydroxyl substituents and possibly containing, in the carbon chain, one or more hetero atoms chosen from oxygen, nitrogen and silicon atoms.
Although, in formula (1) above, only the isomers in which the cyano substituent is in the cis position relative to the para-aminophenyl substituent have been represented, this formula should be understood as also encompassing the corresponding trans isomer. This is likewise the case for formula (2) in which, for each of the two double bonds, and independently, the cyano and para-aminophenyl substituents may be in a cis or trans configuration relative to each other.
The compounds of formula (2) above are novel compounds.
As mentioned above, the compounds of formulae (1) and (2) have excellent screening power in the broad UV-A range, i.e. in the wavelength range from 320 nm to 400 nm, show satisfactory photostability and are substantially colourless.
Among the compounds of formulae (1) and (2) that are
Luppi Bernadette
Richard Herve
Dodson Shelley A.
L'Oreal
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