Symmetrical Triazine derivatives
Publication Date: 2004-Sep-20
The IP.com Prior Art Database
Disclosed is the use organic UV filters selected from 1,3,5-triazines which are symmetrically by optionally substituted phenyl and aryl radicals, preferably by phenyl, bisphenyl and terphenyl for the protection of human and animal hair and skin against the damaging effect of UV radiation. Most preferably 2,4,6-tris[1,1'-biphenyl]-4-yl-1,3,5-triazine (registry number: 31274-51-8) is used as organic UV filter. The selected triazine derivatives are high effective UV absorbers for cosmetic formulations aund can – depending on their physical properties - be used in micronized or soluble form.
Symmetrical Triazine derivatives
The present invention relates to the use of specific symmetrical triazine derivatives for the protection of human and animal hair and skin against the damaging effect of UV radiation, cosmetic compositions comprising these triazine derivatives and process for preparation of these compounds.
Triazines which are symmetrically substituted by biphenyl or naphthyl are known, for example from US-A-6,225,467. They are used as for electroluminescent devices.
Surprisingly it has been found that these compounds can be used as highly effective UV absorbers for cosmetic applications.
Therefore, the present invention refers to the non-therapeutic use of the compounds of formula
(1) , wherein
A is a radical of formula (1a) ; or (1b) ;
R1 and R5 independently from each other are hydrogen; C1-C18alkyl; or C6-C12aryl;
R2, R3 and R4 independently from each other are hydrogen; or a radical of formula (1c) , wherein at least one of the radicals R2, R3 and R4 are a radical of formula (1c);
R6, R7, R8, R9 and R10 independently from each other are hydrogen; hydroxy; halogen; C1-C18alkyl; C1-C18alkoxy; C6-C12aryl; biphenylyl; C6-C12aryloxy; C1-C18alkylthio; carboxy; ‑COOM; C1-C18-alkylcarboxyl; aminocarbonyl; or mono- or di-C1-C18alkylamino; C1-C10acylamino; ‑COOH;
M is an alkali metal ion;
x is 1 or 2; and
y is a number from 2 to 10;
for the protection of human and animal hair and skin against the damaging effect of UV radiation.
C1-C18alkyl according to the definition for the radicals of the compound of formula (1) are straight-chain or branched alkyl radicals like methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.butyl, tert.butyl, amyl, isoamyl or tert.amyl, hexyl, 2-ethylhexyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl
C1-C18alkyl according to the definition for the radicals of the compound of formula (1) may be substituted by methoxyethyl, ethoxypropyl, 2-ethylhexyl, hydroxyethyl, chloropropyl, N,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.
C1-C18alkyl according to the definition for the radicals of the compound of formula (1) are for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec.butoxy, tert.butoxy, amyloxy, isoamyloxy or tert.amyloxy, hexyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy or octadecyloxy.
C6‑C10aryl according to the definition for the radicals of the compound of formula (1) is for example naphthyl und preferably phenyl.
Preferably compounds of formula
are used, wherein
R1, R5, R6, R7 und R8 are defined as in formula (1).
In formula (2) R1and R5 are preferably hydrogen.
Most preferably compounds of formula (1) or (2) are use...