COSMETIC AND/OR DERMATOLOGICAL COMPOSITION CONTAINING A

MEROCYANINE DERIVATIVE COMPRISING SPECIFIC POLAR GROUPS

CONSISTING OF HYDROXYL- AND ETHER-FUNCTIONALITIES.

The present invention relates to new cosmetic and/or dermatological compositions for a topical use, in particular intended for controlling the darkening of the skin and/or preventing the photo-aging of keratinic materials in particular the skin under exposure of UV radiatons comprising in a physiologically acceptable medium at least one merocyanine derivative comprising specific polar groups consisting of hydroxyl- and ether-functionalities of formula (1) or (2) which will be detailed below.

It relates also to cosmetic and/or dermatological compositions comprising in a physiologically acceptable medium at least one merocyanine of formula (1) or (2) and further a system for screening out both UVA radiation and UVB radiation

It is known that light radiation with wavelengths between 280 nm and 400 nm permits tanning of the human epidermis and that rays with wavelengths between 280 and 320 nm, which are known as UV-B rays, harm the development of a natural tan. This exposure is also susceptible to also induce an alteration of the biomechanical properties of epidermis which is expressed by the appearance of wrinkles leading to a premature ageing of the skin.

It is also known that UV-A rays, with wavelengths between 320 and 400 nm, penetrate more deeply into the skin than the UV-B rays. UV-A rays promote an immediate and persistent darkening of the skin. A daily exposure to the UVA radiation, even in a short time, in normal conditions, can generate a degradation of the collagen fibers and elastin which is expressed by a modification of the skin micro-relief, the appearance of wrinkles and an irregular pigmentation (ie brown spots, unhomogeneity of the complexion...) .

A protection against UVA and UVB radiations is therefore necessary. An efficient photoprotective product must protect both UVA and UVB radiations.

Many photoprotective cosmetic compositions for the skin have been proposed to date. They contain generally organic UV filters and inorganic UV filters which work according to their own chemical nature and according to their own physical properties by absorption, reflexion or diffusion of the UV radiations. They generally contain combinations of organic oil-soluble UV filters and/or organic water-soluble UV filters associated to metal oxide pigments as titanium dioxide (Ti02) ·

Many cosmetic compositions intended for limiting the darkening of the skin, improving the colour and the homogeneity of the complexion have been proposed to date. In order to obtain such compositions, it is well-known for a skilled man in the field of suncare products to use UV filters in particular UVB filters. Certain compositions may further contain UVA filters. This filtering system has to cover the UVB protection in order to limit and control the neo-synthesis of melanin promoting the global pigmentation but also has to cover the UVA protection in order to limit and control the oxidation of already present melanins leading to a darkening of the skin color.

But no composition contains a particular combination of UV filters which is specifically adapted to the photoprotection of the skin and particularly to an improvement of the quality of the skin both at the level of the colour and of its elasticity mechanical properties .

In an advantageous way, this improvement is particularly visible on already pigmented skins in order not to increase the pigmentary load in melanin neither the structure of the melanin which is already present into the skin.

In fact, most of the organic UV screening agents are aromatic compounds absorbing in the zone between 280 nm and 370 nm. Besides their filtering power of the solar radiation, the desired photoprotecting compounds must also present good cosmetic properties, a good solubility in usual solvents and in particular in fatty substances as oils, greases and also a good photostability alone and in association with other UV filters. They must be also colorless or at least present a cosmetically acceptable colour for the consumer .

One of the major drawbacks of those compositions known until this day is that those filtering systems are insufficiently photoprotective against UV radiations and particularly against long UVA radiations with wavelengths beyond 370nm in order to control the photo-induced pigmentation and its evolution by an appropriate UV filtering system covering the whole UV spectrum.

Amongst all the compounds which were recommended for this effect, we can mention the particularly interesting UV filters family which consists in carbonated merocyanine derivatives which is disclosed in the patent US4195999 or the application WO2004/006878. Those compounds present very good filtering properties in the long UVA rays but have a little satisfactory solubility in usual solvents and in particular in fatty substances as the oils and a not satisfactory photostability for certain families of merocyanines

Therefore, there is still a need for finding new merocyanine compounds active in the long UVA which present good cosmetic properties, a good solubility in cosmetic oily or aqueous solvents, a good compatibility with other complementary UVA filters as the dibenzoylmethane derivatives, specifically regarding photostability and also a cosmetically acceptable colour for the consumer.

However, after considerable research conducted in the field of photoprotection mentioned above, the Applicant has now discovered, surprisingly, that this objective could be reached with a new family of merocyanine derivatives comprising specific polar groups consisting of hydroxyl- and ether-functionalities and corresponding to the formula (1) or (2) which will be detailed below.

This discovery forms the basis of the present invention.

A first object of the present invention relates to a cosmetic and/or dermatological composition comprising in a physiologically acceptable medium at least one merocyanine derivative of formula (1) or (2) which will be detailed below.

Another object of the present invention related to a cosmetic and/or dermatological composition comprising in a physiologically acceptable medium at least one merocyanine of formula (1) or (2) and further a system for screening out both UVA radiation and UVB radiation

Another object of the present invention related to a cosmetic and/or dermatological composition comprising in a physiologically acceptable medium at least one merocyanine derivative of formula (1) or (2) and at least one dibenzoylmethane derivative.

A third object of the present invention relates to a cosmetic process for controlling and/or improving the darkening of the skin under exposure to UV radiation and the homogeneity of the colour of the complexion which comprises the application onto the skin of a cosmetic composition as above defined.

Another object of the present invention relates to a cosmetic process for protecting the keratinic materials and particularly the skin against photo-ageing which comprises the application onto the keratinic material of a cosmetic composition as above defined.

Other characteristics, aspects and advantages of the present invention will emerge on reading the detailed description that follows.

The term "physiologically acceptable" means compatible with the skin and/or its integuments, which has a pleasant colour, odour and feel and which does not cause any unacceptable discomfort (stinging, tautness or redness) liable to put the consumer off using this composition .

The term "keratinic materials" includes the skin, the scalp, the hair, eyelashes, eyebrows and nails.

In the rest of the present description, the expression "system for screening out both UVA radiation and UVB radiation" is intended to mean an agent for screening out UVA radiation with wavelengths between 320 and 400 nm and UVB radiation with wavelengths between 280 and 320 nm, constituted of either a mixture of several organic compounds and/or inorganic compounds for screening out said UV radiation, for example a mixture comprising a UVA screening agent and a UVB screening agent, or else an organic compound for screening out both UVA radiation and UVB radiation.

According to the present invention the merocyanine derivatives correspond to the following formula (1) or (2)

Ri and R2 independently of each other are hydrogen; Ci -C22alkyl, C2-C22alkenyl , C2-C22alkinyl , which are optionally substituted by at least one hydroxy; or RI and R2 together with the nitrogen atom linking them form a -(CH2) n~ ring which is optionally interrupted by -0- or by -NH- ;

R3 is a - ( C=0) OR6group; or a - ( CO ) HR6group;

Re is Ci-C22alkyl, C2 - C22alkenyl , C2 - C22alkinyl , C3- C22cycloalkyl or C3-C22cycloalkenyl , which is optionally substituted by one or more than one OH ;

R4 and R5 are hydrogen; or R4 and R5 form a -(CH2)n~ ring which is optionally substituted by Ci-C4alkyl and/or interrupted by one or more than one -0- or by -NH- ;

n is a number from 2 to 7;

R7 and Rs independently of each other are hydrogen; Ci -C22alkyl, C2-C22alkenyl , C2-C22alkinyl , which is optionally interrupted by one or more than one 0 and/or substituted by one or more than one OH , C3-C22cycloalkyl or C3-C22cycloalkenyl , wherein said C3-C22cycloalkyl or C3-C22cycloalkenyl is optionally interrupted by one or more than one -0-;

or R7 and Rs together with the nitrogen atom linking them form a -(CH2)n~ ring which is optionally interrupted by one or more than one -0- ;

R9 and Ri o are hydrogen; or R9 and RI O form a -(CH2) n~ ring which is optionally substituted by Cl-C4alkyl and/or interrupted by - O- or by -NH- ;

A is -0-; or -NH ;

Rn is Ci - C22alkyl, C2 - C22alkenyl , C2 - C22alkinyl , C3- C22cycloalkyl or C3-C22cycloalkenyl , which is optionally interrupted by one or more than one 0; or Ci-C22alkyl or C2-C22alkenyl which is substituted by C3-C22cycloalkyl or C3-C22cycloalkenyl , wherein said C3-C22cycloalkyl or C3-C22cycloalkenyl is optionally interrupted by one or more than one -0-;

with the proviso that

(I) at least one of Ri, R2 and R6 is substituted by hydroxy;

(II) if one of Ri is hydroxyethyl , R2 is not hydrogen, methyl or ethyl or hydroxyethyl; and if Ri is hydrogen, R2 is not l-hydroxy-3-methyl-but-2-yl ;

(III) if R6 is substituted by one or more than one OH; one of Ri and R2 is C4-C22alkyl; or Ri and R2 together with the linking nitrogen form a piperidyl or morpholinyl radical;

(IV) at least one of R7 and Rs, or Rn is interrupted by one or more than one -0- .

Preferred are compounds of formula (1) or (2), wherein

Ri and R2 independently of each other are hydrogen; Ci-C22alkyl, C2-C22alkenyl , C2-C22alkinyl , which are optionally substituted by at least one hydroxy; or Ri and R2 together with the nitrogen atom linking them form a -(CH2)n~ ring which is optionally interrupted by -0- or by -NH-;

R3 is a - (C=0) OR6group; or a - (CO) NHR6group;

R6 is Ci-C22alkyl, C2-C22alkenyl , C2-C22alkinyl , C3-C22cycloalkyl or C3-C22cycloalkenyl , which is optionally substituted by one or more than one OH;

R4 and R5 are hydrogen; or R4 and R5 form a -(CH2)n~ ring which is optionally substituted by Ci-C4alkyl and/or interrupted by -0- or by -NH-;

n is a number from 2 to 7 ;

R7 and Rs independently of each other are hydrogen; Ci-C22alkyl, C2-C22alkenyl , C2-C22alkinyl , which is optionally interrupted by one or more than one 0 and/or substituted by one or more than one OH; or R7 and R8 together with the nitrogen atom linking them form a -(CH2)n- ring which is optionally interrupted by one or more than one -0- ;

Rg and Rio are hydrogen; or Rg and Rio form a -(CH2)n~ ring which is optionally substituted by Ci-C4alkyl and/or interrupted by -O- or by -NH-;

A is -0-; or -NH;

Rii is Ci-C22alkyl, C2-C22alkenyl , C2-C22alkinyl , C3-C22cycloalkyl or C3-C22cycloalkenyl , which is optionally interrupted by one or more than one O;

with the proviso that

(I) at least one of Ri, R2 and R6 is substituted by hydroxy;

(II) if one of Ri is hydroxyethyl , R2 is not hydrogen, methyl or ethyl or hydroxyethyl; and if Ri is hydrogen,

R2 is not l-hydroxy-3-methyl-but-2-yl ;

(III) if R6 is substituted by one or more than one OH; one of Ri and R2 is C4-C22alkyl; or Ri and R2 together with the linking nitrogen form a piperidyl or morpholinyl radical;

(IV) at least one of R7 and Rs, or Rn is interrupted by one or more than one -O- .

Preferred are compounds of formula (1) or (2), wherein Ri and R2 independently of each other are hydrogen; C4-Ci2alkyl; or hydroxy-C3-Ci2alkyl ;

wherein at least one of Ri and R2 is hydroxy-C3-Ci2alkyl ; and

R3, R4 and R5 are defined as in claim 1.

Preferred are also compounds of formula (1), wherein

R6 is Ci-Ci2alkyl, which is optionally substituted by one or more than one hydroxy.

More preferred are also compounds of formula (1), wherein

R6 is Ci-Ci2alkyl which is substituted by one or more than one hydroxy;

one of Ri and R2 is C4-C22 lkyl; or Ri and R2 together with the nitrogen atom linking them form a -(C¾)n-ring which is optionally interrupted by -0- and/or -NH-; and R4 and R5 and n are defined as in claim 1.

Preferred are compounds of formula (2), wherein

R11 is a radical of — (CH2)— O— R12 , wherein

R12 is Ci-Ci2alkyl ; or Ci-C6alkoxy-Ci-C6alkyl ;

m is a number from 1 to 5; and

R7, R8, Rg, Rio and A are defined as in claim 1.

Even more preferred are compounds of formula (1) or (2) wherein

Ri and R2 and R7 and Rs respectively together with the linking nitrogen atom form a piperidyl radical or a morpholinyl radical.

Preferred are also compounds of formulas (1) and (2), wherein R4 and R5 and R9 and Rio respectively form a carbocyclic ring which contains 6 carbon atoms.

Most preferred are compounds of formula (1), wherein

Ri and R2 independently of each other are hydrogen; or Ci-C22 lkyl ; or hydroxy-Ci-C22alkyl ; or Ri and R2 together with the nitrogen atom are linked together to form a piperidyl or morpholinyl radical;

R3 is a - (C=0) ORegroup; or a - (CO) NHR6group;

R6 is Ci-C22alkyl, which may be substituted by one or more than one -OH;

R4 and R5 are hydrogen; or R4 and R5 are linked together to form a carbocyclic ring which contains 6 carbon atoms .

Most preferred are compounds of formula (1), wherein Ri and R2 independently of each other are hydrogen; or hydroxy-Ci-C22alkl ; wherein at least one of Ri and R2 is hydroxy-Ci-C22alkyl ;

R3 is a -(C=0)OR6 group; or a -(C=0)NHR6 group;

R6 is Ci-C22alkyl; and

R4 and R5 are hydrogen; or R4 and R5 are linked together to form a carbocyclic ring which contains 6 carbon atoms .

Most preferred are compounds of formula (2), wherein R7 and Rs independently of each other are hydrogen or

Ci-Csalkyl, which is optionally interrupted by one or more than one -0-;

A is -0-; or -NH;

R11 is Ci-C22alkyl; and

R9 and Rio are hydrogen; or Rg and Rio are linked together to form a carbocyclic ring which contains 6 carbon atoms .

Most preferred are compounds of formula (2), wherein R7 and Rs together with the nitrogen atom form a morpholinyl or piperidyl radical;

A is -0-; or -NH;

R11 is Ci-C22alkyl; which is interrupted by one or more than one -0-; and

Rg and Ri o are hydrogen; or Rg and Ri o are linked together to form a carbocyclic ring which contains 6 carbon atoms .

Even more preferred are compounds of formula (2), wherein

Ri i is a radical of — (CH2)— O— R12 , wherein

Ri2 is Ci-C4alkyl; or Ci-C4alkoxy-Cl-C4alkyl ;

m is a number from 1 to 3;

R7 and Rs , independently of each other are hydrogen; Ci-Ci2alkyl, which is optionally interrupted by one or more than one 0; or R7 and Rs together with the nitrogen atom form a morpholinyl or piperidyl radical;

Rg and Ri o are hydrogen; or form a carbocyclic ring which contains 6 carbon atoms; and

A is -0-; or -NH.

The merocyanine compounds of the invention may be in the E/E-, E/Z- or Z/Z geometrical isomer forms.

Alkyl, cycloalkyl, alkenyl, alkylidene or cycloalkenyl may be straight chained or branched, monocyclic or polycyclic .

Ci-C22alkyl is for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tert. -butyl, n-pentyl, 2-pentyl, 3-pentyl, 2, 2-dimethylpropyl, n-hexyl, n-octyl, 1 , 1 , 3 , 3-tetramethylbutyl , 2-ethylhexyl, nonyl, decyl, n-octadecyl, eicosyl or dodecyl .

Substituted alkyl is for example methoxyethyl , ethoxypropyl , 2-ethylhexyl, hydroxyethyl , chloropropyl , N, -diethylaminopropyl , cyanoethyl, phenethyl, benzyl, p-tert-butylphenethyl , p-tert-octylphenoxyethyl, 3-

(2, 4-di-tert-amylphenoxy) -propyl, ethoxycarbonylmethyl-2- (2-hydroxyethoxy) ethyl or 2-furylethyl .

Hydroxysubstituted alkyl is for example hydroxymehtyl , hydroxyethyl , hydroxypropyl , hydroxybutyl , hydroxypentyl , hydroxyhexyl , hydroxyheptyl , hydroxyoctyl , hydroxynonyl or hydroxydecyl .

C2-C22alkenyl is for example straight-chain C2-Ci2alkenyl or preferably branched C3-Ci2alkenyl . Ci-Ci2alkyl, like vinyl, allyl, 2-propen-2-yl, 2-buten-l-yl, 3-buten-l-yl, 1, 3-butadien-2-yl, 2-cyclobuten-l-yl, 2-penten-l-yl, 3-penten-2-yl, 2-methyl-l-buten-3-yl, 2-methyl-3-buten-2-yl, 3-methyl-2-buten-l-yl, 1, 4-pentadien-3-yl, 2-cyclopenten-l-yl, 2-cyclohexen-l-yl, 3-cyclohexen-l-yl, 2, 4-cyclohexadien-l-yl, l-p-menthen-8-yl, 4(10)-thujen-10-yl, 2-norbornen-l-yl, 2, 5-norbornadien-l-yl, 7 , 7-dimethyl-2 , 4-norcaradien-3-yl or the different isomers of hexenyl, octenyl, nonenyl, decenyl or dodecenyl .

C3-Ci2cycloalkyl is for example cyclopropyl, cyclobutyl, cyclopentyl, trimethylcyclohexyl or preferably cyclohexyl .

I/We Claims :
1. Cosmetic and/or dermatological composition
comprising in a physiologically acceptable medium at
least one merocyanine derivative of formula (1) or (2)
and/or its E/E-, E/Z- or Z/Z geometrical isomer forms:
z2&\ and
(1) R;
\N (2)
'3.3 '35
'39 R,,
wherein
R1 and R2 independently of each other are hydrogen; C1-
CZ2al kyl , C2-C22al kenyl, C2-C22al kinyl, which are
optionally substituted by at least one hydroxy; or R1
and R2 together with the nitrogen atom linking them form
a -(CH2),- ring which is optionally interrupted
by -0- or by -NH-;
R3 is a - (~=0)0~6group;o r a -(CO)NHRsgroup;
R6 is C1-C22alky1, C2-C22al kenyl, Cz-C22alkiny1, C3-
Cz2cycloalkyl or C3-C22cycloalkenyl, which is optionally
substituted by one or more than one OH;
R4 and R5 are hydrogen; or R4 and R5 form a -(CH2),- ring
which is optionally substituted by C1-C4alkyl and/or
interrupted by one or more than one -0- or by -NH-;
n is a number from 2 to 7;
R7 and Ra independently of each other are hydrogen; CIC22alkyl1
C2-C22alkeny1, C2-C22alkinyl, which is
optionally interrupted by one or more than one 0 and/or
substituted by one or more than one OH, C3-C22cycloalkyl
or C3-C22cycloalkeny1, wherein said C3-C22cycloalkyl or
C3-C22cycloalkenyl is optionally interrupted by one or
more than one -0-;
or R7 and Re together with the nitrogen atom linking
them form' a -(CH2),- ring which is optionally
interrupted by one or more than one -0- ;
Rg and Rlo are hydrogen; or R9 and R10 form
a -(CH2),- ring which is optionally substituted by C1-
C4alkyl and/or interrupted by -0- or by -NH-;
A is -0-; or -NH;
R11 is C1-C22al kyl, C2-C22al kenyl, C2-C22al kinyl, C3-
C2zcycloalkyl or C3-Ci2cycloalkenyl, which is optionally
interrupted by one or more than one 0; or C~-C~~alkoyrl
C2-C22alkenyl which is substituted by C3-C22cycloalkyl or
C3-C22~y~1~alkenywlhe,r ein said C3-C22cycloalk yl or C3-
C22cycloalkenyl is optionally interrupted by one or
more than one -0-;
with the proviso that
(I) at least one of R1, R2, R2 and R6 is substituted by
hydroxy ;
(11) if one of R1 is hydroxyethyl, R2 is not hydrogen,
methyl or ethyl or hydroxyethyl; and if R1 is hydrogen,
R2 is not 1-hydroxy-3-methyl-but-2-yl;
(111) if R6 is substituted by one or more than one OH;
one of R1 and R2 is Cs-Cz2alkyl; or R1 and R2 together
with the linking nitrogen form a piperidyl or
morpholinyl radical;
(IV) at least one of R7 and Re, or RI1 is interrupted by
one or more than one -0-.
2. Composition according to claim 1, wherein
R1 and Rp independently of each other are hydrogen; C1-
C22al kyl, C2-C22al kenyl, C2-C22al kinyl, which are
optionally substituted by at least one hydroxy; or R1
and RZ together with the nitrogen atom linking them form
a -(CH2).- ring which is optionally interrupted
by -0- or by -NH-;
Rg is Cl-C22al kyl , CZ-Czzal kenyl, C2-C22al kinyl, Cj-
C2zc ycloalkyl or C3-C22cycloalkeny1, which is optionally
substituted by one or more than one OH;
5 R4 and Rg are hydrogen; or R4 and Rs form a - (CH2),- ring
which is optionally substituted by C1-Cdalkyl and/or
interrupted by -0- or by -NH-;
n is a number from 2 to 7;
R7 and Rs independently of each other are hydrogen; C1-
10 C2zalky1, C2-C22al kenyl, C2-C22al kinyl, which is
optionally interrupted by one or more than one 0 and/or
substituted by one or more than one OH; or R7 and R8
together with the nitrogen atom linking them form
a - (CH2),- ring which is optionally interrupted by one
15 or more than one -0- ;
R9 and Rlo are hydrogen; or R9 and Rlo form
a -(CH2)n- ring which is optionally substituted by C1-
C4alkyl and/or interrupted by -0- or by -NH-;
A is -0-; or -NH;
20 R11 is C1-C2~alkyl, C2-C22alkenyl, C2-C22al kinyl, Cg-
Cz2cycloalkyl or C3-C22cycloalkeny1, which is optionally
interrupted by one or more than one 0;
with the proviso that
(I) at least one of R1, R2 and R6 is substituted by
25 hydroxy;
(11) if one of R1 is hydroxyethyl, R2 is not hydrogen,
methyl or ethyl or hydroxyethyl; and if R1 is hydrogen,
Rz is not 1-hydroxy-3-methyl-but-2-yl;
(111) if R6 is substituted by one or more than one OH;
30 one of R1 and R2 is C4-C22alkyl; or R1 and R2 together
with the linking nitrogen form a piperidyl or
morpholinyl radical;
(IV) at least one of R7 and RE, or R11 is interrupted by
one or more than one -0-.
3. Composition of formula (1) according to claim 1 or
2, wherein 08 JAN 20\4
R1 and Rp independently of each other are hydrogen; Cq-
5 C12al kyl ; or hydroxy-C3-C12al kyl;
wherein at least one of R1 and R2 is hydroxy-C3-C12alkyl;
and
R3, Rs and Rs are defined as in claim 1.
10 4. Composition of formula (1) according to any of
claims 1 to 3, wherein
R6 is C1-C12alkyl, which is optionally substituted by
one or more than one hydroxy.
15 5. Composition of formula (1) according to claim 1 or
2, wherein
R6 is C1-C12alkyl which is substituted by one or more
than one hydroxy;
one of R1 and R2 is C4-C22alkyl; or R1 and R2 together
20 with the nitrogen atom linking them form a -(CH2)n-ring
which is optionally interrupted by -0- and/or -NH-; and
R4 and R5 and n are defined as in claim 1.
6. Composition of formula (2) according to claim 1 or
25 2, wherein
RI1 is a radical of
-(CH,);O-R,, , wherein
formula (la)
R12 is C1-Clsalkyl; or C1-Csalkoxy-C1-C6alkyl;
m is a number from 1 to 5; and
R7, RE, R9, Rlo and A are defined as in claim 1.
30 7. Composition according to any of claims 1 to 6,
wherein in formulas (1) and (2)
R1 and R2 and R7 and RE respectively together with the
linking nitrogen atom form a piperidyl radical or a
morpholinyl radical.
8. Composition according to any of claims 1 to 6,
wherein in formulas (1) and (2) :
Rq and R5 and R9 and Rlo respectively form a carbocyclic
ring which contains 6 carbon atoms.
9. Composition according to any of claims 1 to 5 and 7
to 8, in which the compounds of formula (1) are
selected from those wherein
R1 and R2 independently form each other are hydrogen; or
C1-Cz2alkyl; or hydro~y-C~-C~~alkoyrl ;R 1 and R2 together
with the nitrogen atom are linked together to form a
piperidyl or morpholinyl radical;
R3 is a - (C=O) OR6 group; or a - (CO) NHR~jgroup;
R6 is C1-Cz2alkyl, which may be substituted by one or
more than . one -OH;
R4 and R5 are hydrogen; or R4 and R5 are linked together
to form a carbocyclic ring which contains 6 carbon
atoms.
10. Composition according to any of claims 1 to 9, in
which the compounds of formula (1) are selected from
those wherein
R1 and Rz independently of each other are hydrogen; or
hydr~xy-C~-C~~alwkhle;r ein at least one of R1 and R2 is
hydroxy-C1-C22alk yl ;
R3 is a - (C=O) OR6group; or a - (C=O)NHRsgroup;
R6 is C1-Czzalkyl; and
R4 and R5 are hydrogen; or R4 and R5 are linked together
to form a carbocyclic ring which contains 6 carbon
atoms.
11. Composition according to claim 1, in which the
compounds of formula (2) are selected from those
wherein
R7 and R8 independently of each other are hydrogen or
5 C1-C~alkyl, which is optionally interrupted by one or
more than one -0-;
A is -0-; or -NH;
Rll is CI-Cz2alkyl; and
Rg and Rlo are hydrogen; or Rg and Rlo are linked
10 together to form a carbocyclic ring which contains 6
carbon atoms.
12. Composition according to claim 1, in which the
compounds of formula (2) are selected from those
15 wherein
R7 and RE together with the nitrogen atom form a
morpholinyl or piperidyl radical;
A is -0-; or -NH;
Rll is C1-C22alkyl; which is interrupted by one or more
20 than one -0-; and
Rg and Rlo are hydrogen; or Rg and Rlo are linked
together to form a carbocyclic ring which contains 6
carbon atoms.
25 13. Composition according to claim 12, in which the
compounds of formula (2) are selected from those,
wherein
Rll is a radical of -(CH2);O-R,, , wherein
R12 is C1-Cdal kyl; or C1-C4alkoxy-C1-C4alkyl;
m is a number from 1 to 3;
30 R7 and RE, independently of each other are hydrogen;
C1-Clzalkyl, which is optionally interrupted by one or
more than one 0; or R7 and R8 together with the nitrogen
atom form a morpholinyl or piperidyl radical;
Rg and Rlo are hydrogen; or form a carbocyclic ring
which contains 6 carbon atoms; and
A is -0-; or -NH.
08 JAM
5 14. Composition according to any of the claims 1 to
13, in which the merocyanine derivative is selected in
the group of the following compounds and their E/E, E,Z
or Z/Z geometrical isomer forms:
4
14
15
N
2-ethoxyethyl (2E, 4E) -2-
cyano-5-(piperidin-1-
y1)penta-2,4-dienoate
ethyl (2Z) -cyano{ 3- [ (3-
methoxypropyl)amino]cyclo
hex-2-en-lylidenelethanoate
I H
C . - o g ; , - O -
(2Z) -2-cyano-N- (3-
methoxypropyl) -2-{3- [ (3-
methoxypropyl)amino]cyclo
hex-2-en-lylidenelethanamide
methoxypropyl)amino]cyclo
hex-2-en-lylidenelethanoate
15. Composition according to claim 14, wherein the
merocyanine derivative is the compound 2-ethoxyethyl
5 (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-lylidenelethanoate
(25) in its E/Z geometrical isomer
form of formula :
and/or its E/E geometrical isomer form of formula :
16. Composition according to any of the claims 1 to 15,
further containing a system for screening out both UVA
radiation and UVB radiation.
17. Composition according to any of the .claims 1 to
16, further containing one or more complementary
hydrophilic, lipophilic or insoluble organic screening
agents and/or one or more inorganic screening agents
which are active in UVA and/or UVB.
18. Composition according to any of the claims 1 to
17, further containing at least one dibenzoylmethane
derivative and particularly Butyl Met hoxy
Dibenzoylmethane.
19. Composition according to any of the claims 1 to 18,
containing at least one dibenzoylmethane derivative and
particularly Butyl Methoxy Dibenzoylmethane and the
merocyanine compound the compound 2-ethoxyethyl (22)-
cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-
ylidenelethanoate (25) in its E/Z geometrical isomer
form of formula :
and/or its E/E geometrical isomer form of formula :
5 20. Composition according to any of the preceding
claims, containing at least one fatty substance
selected from oils and waxes.
21. Composition according to any of the the preceding
10 claims, containing at least one hydrophilic or
lipophilic thickener.
22. Composition according to any of the preceding
claims, containing at least one emulsifier of the type
15 hydrophobically modified inuline as Inuline Lauryl
Carbamate.
23. Composition according to any of the preceding
claims, containing at least one depigmenting agent, and
20 preferably at least one hydroxylated diphenylmethane
derivative, and particularly the compound of structure:
25 24. Cosmetic process for controlling and/or improving
the darkening of the skin under exposure to UV
.
k ,:-& 5 &+b ,, >
r * "
radiation and the homogeneity of the colour of the
complexion which comprises the application onto the
skin of a cosmetic composition as defined in any of the
preceding claims.
25. Cosmetic process for protecting the keratinic
materials and particularly the skin against photoageing
which comprises the application onto the
keratinic material of a cosmetic composition as defined
in any of the preceding claims.
26. Use of the merocyanines of formula
7'2 'J:",, ,+ and ( 2 , ) .. (1') R',
R', R',
*', \N
'3'9 R'l0
Rtl and Rtz independently of each other are hydrogen;
C1-C22alkyl, C2-CZ2alk enyl, C2-C22alkinyl, which are
optionally substituted by at least one hydroxy; or R1l
and Rf2 together with the nitrogen atom linking them
form a -(CH2)n- ring which is optionally interrupted
by -0- or by -NH-;
R t 3 is a - (C=O) ORsgroup; or a - (CO) NHRr6group;
R' 6 is C1-C22alk yl , C2-C22al kenyl , C2-C~2akli nyl, C3-
Cz2cycloalkyl or C3-C22cycloalkenyl, which is optionally
substituted by one or more than one OH;
Rrq and Rt5 are hydrogen; or Rr4 and Rr5 form
a -(CH2),- ring which is optionally substituted by C1-
C4alkyl and/or interrupted by -0- or by -NH-;
n is a number from 2 to 7;
R17 and R18 independently of each other are hydrogen;
C1-CZ2alk yl, C2-C22alkenyl, C2-CZ2alk inyl, which is
optionally interrupted by one or more than one 0 and/or
substituted by one or more than one OH; or Rt7 and R'e
f)~TlWL~%L 9 4
together with the nitrogen atom li
a -(CH2),- ring which is optionally interrupted by -0- ;
R'9 and Rflo are hydrogen; or R'9 and Rtlo form
a -(CH2)"- ring which is optionally substituted by C1-
5 Cdalkyl and/or optionally interrupted by -0- or by -NH-;
A is -0-; or -NH;
R' 11 is C1-Cz~alk yl, C2-Cz2alk enyl, C~-C2~kailn yl, C3-
Cz2cycloal kyl or C3-Cz2cycloal kenyl, which is opt ionally
interrupted by one or more than one 0;
10 for protecting body care products from photolytic and
oxidative degradation.
D a t e d this 0 8 d~ay ~of January 2 0 1 4
4 s
MALATHI LAKSHMIKUMARAN
IN/PA-1433
AGENT FOR THE APPLICANT
To
The C o n t r o l l e r of P a t e n t s
The P a t e n t s O f f i c e at New D e l h i