Cosmetic or dermatological light protection agent preparations

Details Cosmetic or dermatological light protection agent preparations Cosmetic or dermatological light protection agent preparations

2001-01-30

2002-07-09

Hartley, Michael G. (Department: 1617)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

C424S059000, C430S269000, C514S685000

Reexamination Certificate

active

06416773

ABSTRACT:

The invention relates to cosmetic or dermatological light protection agent preparations comprising a combination of one or more 3,3-diphenylacrylates and one or more dibenzoylmethane derivatives, and to the use thereof for the protection of human skin or human hair against UV rays.
The light protection agents used in cosmetic and dermatological preparations have the task of preventing or at least diminishing the extent of the harmful effects of sunlight on the human skin. In addition, these light protection agents, however, also serve to protect other ingredients from decomposition or degradation by UV radiation. In hair cosmetic formulations, the aim is to prevent damage to the keratin fiber by UV rays.
The sunlight which reaches the earth's surface contains UV-B radiation (280 to 320 nm) and UV-A radiation (>320 nm), which directly border the visible light region. The effect on human skin is evident, particularly in the case of UV-B radiation, from sunburn.
The erythema activity maximum of sunlight is given as the relatively narrow region around 308 nm.
Numerous compounds are known for protecting against UV-B radiation; these are, inter alia, derivatives of 3-benzylidenecamphor, of 4-aminobenzoic acid, of cinnamic acid, of salicylic acid, of benzophenone, and of 2-phenylbenzimidazole.
For the region between about 320 nm and about 400 nm, the UV-A region, it is also important to have available filter substances, since the rays of that region can also trigger reactions in cases of skin which is sensitive to light. It has been found that UV-A radiation leads to damage of the elastic and collagenic fibers of connective tissue, which leads to premature aging of the skin, and that it is to be regarded as a cause of numerous phototoxic and photoallergic reactions. The harmful effect of UV-B radiation can be intensified by UV-A radiation.
To protect against UV-A rays, derivatives of dibenzoylmethane are used, although their photostability is inadequate (Int. J. Cosm. Science 10, 53 (1988)).
French Patent Specification 2,440,933 describes 4-(1,1-dimethylethyl)-4′-methoxydibenzoylmethane as UV-A filter. It is proposed to combine this particular UV-A filter, which is sold by GIVAUDAN under the name “PARSOL 1789”, with different UV-B filters in order to absorb all the UV rays having a wavelength of from 280 to 380 nm.
However, this UV-A filter, when used alone or in combination with UV-B filters, is insufficiently photochemically stable to ensure lasting protection of the skin during a prolonged session of sunbathing, which requires repeated applications at regular and brief intervals if effective protection of the skin against all UV rays is desired.
For this reason, according to U.S. Pat. No. 5,587,150 and U.S. Pat. No. 5,576,354, the insufficiently photostable UV-A filters are stabilized by the addition of 2-cyano-3,3-diphenylacrylates, which themselves serve as filters in the UV-B region.
The combinations of dibenzoylmethane and 2-cyano-3,3-diphenylacrylate mentioned in U.S. Pat. No. 5,587,150 and U.S. Pat. No. 5,576,354 have the disadvantage that the preparations prepared therewith in many cases still have inadequate cosmetic properties, such as, for example, tackiness which is too high and, associated therewith, an unsatisfactory feel on the skin.
It is an object of the invention to provide novel stabilizers for UV-A filters from the class of dibenzoylmethanes which do not have the abovementioned disadvantages.
It is furthermore an object of the present invention to propose light protection agents for cosmetic and dermatological purposes which absorb in the UV-A region with high absorbance, which are photostable, have low intrinsic color, i.e. a sharp band structure, and are readily processable in oil or water.
We have found that this object is achieved by cosmetic or dermatological preparations comprising
a) 0.1 to 10% by weight of one or more 3,3-diphenylacrylates of the formula I,
in which the substituents independently of one another have the following meanings:
R
1
and R
2
are hydrogen, C
1
-C
12
-alkyl, C
1
-C
12
-alkoxy;
R
3
is C
3
-C
10
-cycloalkyl, optionally substituted;
R
4
is hydrogen, CN and
b) 0.1 to 10% by weight of one or more dibenzoylmethane derivatives of the formula II,
 in which the substituents independently of one another have the following meanings:
R
5
to R
8
are hydrogen, C
1
-C
4
-alkyl;
R
9
and R
10
are hydrogen, C
1
-C
12
-alkyl, C
1
-C
12
-alkoxy.
Alkyl radicals for R
1
and R
2
and also R
9
and R
10
which may be mentioned are branched or unbranched C
1
-C
12
-alkyl chains, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, n-nonyl, n-decyl, n-undecyl, 1-methylundecyl, n-dodecyl.
Alkyl radicals for R
5
to R
8
which may be mentioned are branched or unbranched C
1
-C
4
-alkyl chains, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl.
Suitable alkoxy radicals for R
1
and R
2
and also R
9
and R
10
are straight-chain and branched radicals having 1 to 12 carbon atoms, preferably having 1 to 8 carbon atoms.
Examples which may be mentioned are:
methoxy ethoxy
isopropoxy n-propoxy
1-methylpropoxy n-butoxy
n-pentoxy 2-methylpropoxy
3-methylbutoxy 1,1-dimethylpropoxy
2,2-dimethylpropoxy hexoxy
1-methyl-1-ethylpropoxy heptoxy
octoxy 2-ethylhexoxy
Cycloalkyl radicals for R
3
which may be mentioned are C
3
-C
10
-cycloalkyl radicals, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl. Preference is given to C
5
-C
8
-cycloalkyl, such as cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, in particular cyclopentyl and cyclohexyl.
The cycloalkyl radicals can be optionally substituted by up to three radicals, including halogen, e.g. fluorine, chlorine or bromine, cyano, nitro, amino, C
1
-C
4
-alkylamino, C
1
-C
4
-dialkylamino, hydroxyl, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy, or contain 1 to 3 heteroatoms, such as sulfur, nitrogen whose free valencies may be saturated by hydrogen or C
1
-C
4
-alkyl, or oxygen.
The cycloalkyl radicals may also be present as bicyclic ring systems.
Preferred substituents on the cycloalkyl ring are C
1
-C
4
-alkyl groups, in particular methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl.
Particularly preferred substituents for R
3
are the cycloalkyl radicals listed below.
Preference is given to cosmetic or dermatological preparations comprising
a) 0.1 to 10% by weight of one or more 3,3-diphenylacrylates of the formula Ib,
 in which R
3
is C
5
-C
8
-cycloalkyl, optionally substituted and
b) 0.1 to 10% by weight of one or more dibenzoylmethane derivatives, chosen from the group consisting of
2-methyldibenzoylmethane, 4-methyldibenzoylmethane,
4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane,
2,4-dimethyldibenzoylmethane, 2,5-dimethyldibenzoylmethane,
4,4′-diisopropyldibenzoylmethane,
4-tert-butyl-4′-methoxydibenzoylmethane,
2-methyl-5-isopropyl-4′-methoxydibenzoylmethane,
2-methyl-5-tert-butyl-4′-methoxydibenzoylmethane,
2,4-dimethyl-4′-methoxydibenzoylmethane,
2,6-dimethyl-4-tert-butyl-4′-methoxydibenzoylmethane.
Particular preference is given to cosmetic or dermatological preparations comprising
a) 0.1 to 10% by weight of one or more 3,3-diphenylacrylates of the formula Ib,
 in which R
3
is C
5
-C
8
-cycloalkyl, optionally substituted and
b) 0.1 to 10% by weight of 4-tert-butyl-4′-methoxydibenzoylmethane.
The content of compone

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