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Merocyanine derivatives for cosmetic use

IP.com Disclosure Number: IPCOM000022279D
Publication Date: 2004-Mar-04
Document File: 194 page(s) / 1M

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The IP.com Prior Art Database

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IPCOM000126303D: IP.COM

Abstract

Cosmetic or pharmaceutical compositions comprise a merocyanine derivative as sunscreen to protect human and animal hair and skin from UV radiation. For example, delta- aminopentadienoate derivatives or [3-Amino-cyclohex-2-enylidene]- acetic acid ester compounds are used in skin-care formulations together with other UV absorbers, lecithins, griglyceride waxes, emulsifiers, associative polymers, fatty alcohols, esters of fatty acids, other adjuvants and additives, pearlescent waxes, hydrocarbon oils, silicones and/or siloxanes, fluorinated and/or perfluorinated oils, superfatting agents, surfactants, consistency regulators/thickeners and/or rheology modifiers, biogenic active ingredients, deodorising active ingredients, anti-dandruff agents, film formers, antioxidants, hydrotropic agents, preservatives and/or bacteria-inhibiting agents, perfume oils, colorants, polymeric beads and/or hollow spheres.

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Page 1 of 194

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Merocyanine derivatives for cosmetic use

The present invention relates to the use of merocyanine derivatives in protecting human and animal hair and skin from UV radiation and to cosmetic compositions comprising such com- pounds.

The compounds for use in accordance with the invention correspond to formula

=No(1) k `e

oO

Z1

=

å

oP

oQ

oP

oQ

`e `e

, (2) k `

oN

`e `e

or

å

Z2

oO

oP

oQ

(3) k ` oN

`e `

Z2

n

wherein
R1 and R2 are each independently of the other hydrogen; C1-C22alkyl; cyclo-C3-C8alkyl; or un- substituted or C1-C6alkyl- or C1-C6alkoxy-substituted C6-C20aryl; or R1 and R2 together with the nitrogen atom linking them form a -(CH2)m- ring which is uninterrupted or inter- rupted by -O- or by -NH-;

R3 is a cyano group; -COOR5; -CONHR5; -COR5; or -SO2R5; -CONR1R5; R4 is a cyano group; -COOR6; -CONHR6; -COR6; or -SO2R6; -CONR2R6; R5 and R6 are each independently of the other C1-C22alkyl; cyclo-C3-C8alkyl; or unsubstituted or C1-C6alkyl-substituted C6-C20aryl;
or R3 and R4 together or R5 and R6 together form a 5- to 7-membered, monocyclic, carbo- cyclic or heterocyclic ring;

Z1 and Z2 are each independently of the other a -(CH2)l- group which is uninterrupted or inter- rupted by -O-, -S-, or by -NR7-, and/or is unsubstituted or substituted by C1-C6alkyl;

R7 is C1-C5alkyl; l is from 1 to 4; m is from 1 to 7; n is from 1 to 4; when n = 2, R1, R5 or R6 is a bivalent alkyl group; or R1 and R2 together with the 2 nitrogen atoms linking them form a -(CH2)m- ring;
when n = 3, R1, R5 or R6 is a trivalent alkyl group;

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Page 2 of 194

- 2 -

when n = 4, R1, R5 or R6 is a tetravalent alkyl group; and R1 and R2 in formula (1) are not simultaneously hydrogen.

Preference is given to the use of compounds of formula

(1) or (2a) k `

oN

w

=

å

oP

oQ

wherein

R1 and R2 are each independently of the other hydrogen; C1-C22alkyl; or unsubstituted or C1-C5alkyl- or C1-C5alkoxy-substituted C6-C20aryl; or R1 and R2 together with the nitrogen atom linking them form a -(CH2)m- ring which is uninterrupted or interrupted by -O- or by - NH-;

R3 is a cyano group; -COOR5; -CONHR5; -COR5; or -SO2R5; R4 is a cyano group; -COOR6; -CONHR6; -COR6; or -SO2R6; R5 and R6 are each independently of the other C1-C22alkyl; or unsubstituted or C1-C5alkyl- substituted C6-C20aryl; or R5 and R6 together form a 5- to 7-membered, monocyclic, carbo- cyclic or heterocyclic ring;

Z is a -(CH2)l- group which is uninterrupted or interrupted by -O-, -S-, or by -NR7-, and/or is unsubstituted or substituted by C1-C6alkyl;

R7 is C1-C6alkyl; l is from 1 to 4; m is from 1 to 7; n is from 1 to 4; when n = 2, R1, R5 or R6 is a bivalent alkyl group; or R1 and R2 together with the 2 nitrogen atoms linking them form a -(CH2)m- ring;
when n = 3, R1, R5 or R6 is a trivalent alkyl group;
when n = 4, R1, R5 or R6 is a tetravalent alkyl group; and
R1 and R2 in formula (1) are not simultaneously hydrogen.

The compounds of formula (1) may be p...