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Suncare formulations containing monomeric benzylidene malonate UV absorbers

IP.com Disclosure Number: IPCOM000202153D
Publication Date: 2010-Dec-06
Document File: 191 page(s) / 1M

Publishing Venue

The IP.com Prior Art Database

Abstract

It has been found that specific benzylidene malonates (MBM) have very good properties as UV absorbers. The use of specific benzylidene malonates for cosmetic preparations and other applications is described.

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Page 01 of 191

Suncare formulations containing monomeric benzylidene malonate UV absorbers 1/191

The present invention relates to the use of specific UV filter combinations comprising benzylidene

malonates (MBM) for cosmetic preparations.

It is well known that ultraviolet radiation (light) is harmful to human skin. Depending on the wavelength UV radiation causes different types of skin damage. UV-B radiation (about 290 to about 320 nm) is responsible for sunburn and can cause skin cancer. UV-A radiation (about 320 to about 400 nm) while producing tanning of the skin, contributes also to sunburn and the induction of skin cancers. Moreover, the harmful effects of the UV-B radiation may be aggravated by UV-A radiation.

Therefore, an effective sunscreen formulation preferably comprises both at least one UV-A and UV-B filter and a broad band UV filter covering the full range from about 290nm to about 420 nm to prevent the human skin from the damage of sunlight.

Besides their screening power on solar radiation UV filters must also have good resistance to water and perspiration and also satisfactory photostability.

The present invention relates to the use of specific monomeric benzylidene malonates for cosmetic

preparations and new monomeric benzylidene malonates.

Specific monomeric benzylidene malonates have very good properties as cosmetic UV absorbers.

Therefore, the present invention relates to the use of benzylidene malonates of formula

(1)

O OR

O

, wherein

R1 is methyl; ethyl; propyl; or n-butyl; if R1 is methyl, then

R is tert. butyl; * ; * ; * ; a radical of formula

R4

H

OR

R1

O

(1a)

  R2 *

R3

H ; or a radical of forumula (1b) *

R5

; wherein

R2 and R3, independently from each other are hydrogen; or methyl;

R4 is methyl; ethyl; or n-propyl;

R5 and R6 independently from each other are hydrogen; or C1-C3alkyl;
if R1 is ethyl; propyl; or n-butyl, then
R is isopropyl;
for the protection of human and animal hair and skin against UV radiation.

Preferably compounds of formula (1) are used, wherein

R1 is methyl; ethyl; propyl; or n-butyl;
if R1 is methyl, then

R6


Page 02 of 191

Suncare formulations containing monomeric benzylidene malonate UV absorbers 2/191

R is tert. butyl; * ; * ; a radical of formula (1a)

  R2 *

R3

R4

H

H ; or a radical of

; wherein

R2 and R3, independently from each other are hydrogen; or methyl; R4 is methyl; ethyl; or n-propyl;

R5 and R6 independently from each other are hydrogen; or C1-C3alkyl; if R1 is ethyl; propyl; or n-butyl, then
R is isopropyl.

Prefereably, in formula (1)

R is a radical of formula

*

; * ; * ; * ; * ;

* ; * ; * ;

* ; * ; or * ; and

forumula (1b) *

R5

R6

R1 is methyl.

Most preferred are compounds of formula (1), wherein in formula (1a) at least one of R2 or R3 is methyl.

Most preferred are also compounds of formula (1), wherein in formula (1a) R2 and R3 are methyl.

Preferred are also compounds, wherein R1 is ethyl; propyl; or n-butyl; and
R is isopropyl.


Page 03 of 191

Suncare formulations containing monomeric benz...