Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations
Reexamination Certificate
2001-12-14
2004-06-08
Dodson, Shelley A. (Department: 1616)
Drug, bio-affecting and body treating compositions
Topical sun or radiation screening, or tanning preparations
C424S060000, C424S400000, C424S401000, C514S241000
Reexamination Certificate
active
06746666
ABSTRACT:
The present invention relates to the use of mixtures of micronised organic UV filters in protecting human and animal skin and hair against the damaging effect of UV radiation and to their use in cosmetic and pharmaceutical formulations.
It is known that certain organic UV filters, for example sparingly soluble benzotriazole or triazine compounds, exhibit pronounced UV filtering properties when they are in the form of single compounds in micronised form. By virtue of their specific, substance-typical properties, however, they only ever absorb, reflect or scatter a certain portion of the damaging UV range.
There is strong interest in light-protective filters that cover a broad UV spectrum and thus offer better UV protection.
The aim of the present invention is therefore to find micronised organic UV filters that cover a broader portion of the UV range, with which it is thus possible to achieve better UV protection.
It has now been found, surprisingly, that mixtures of at least two micronised UV filters are able to achieve that aim.
The present invention therefore relates to the use of mixtures of micronised organic UV filters in protecting human and animal skin and hair against the damaging effect of UV radiation.
UV filters suitable for use according to the invention are organic, in some cases sparingly soluble, compounds, for example triazine derivatives, especially hydroxyphenyltriazine compounds or benzotriazole derivatives, amides containing a vinyl group, cinnamic acid derivatives, sulfonated benzimidazoles, Fischer base derivatives, diphenylmalonic acid dinitriles, oxalyl amides, camphor derivatives, diphenyl acrylates, para-aminobenzoic acid (PABA) and derivatives thereof, salicylates, benzophenones and further classes of substances known as UV filters.
Preferred triazine derivatives suitable for use according to the invention correspond to formula
wherein
R
1
, R
2
and R
3
are each independently of the others hydrogen; OH; C
1
-C
18
alkoxy; —NH
2
; —NH—R
4
; —N(R
4
)
2
; —OR
4
,
R
4
is C
1
-C
5
alkyl; phenyl; phenoxy; anilino; pyrrolo, wherein phenyl, phenoxy, anilino and pyrrolo are unsubstituted or may be substituted by one, two or three OH groups, carboxy, —CO—NH
2
, C
1
-C
5
alkyl or C
1
-C
5
alkoxy; a methylidene-camphor group; a group of formula —(CH═CH)
m
C(═O)—OR
4
; a group of formula
or a corresponding alkali metal, ammonium, mono-, di- or tri-C
1
-C
4
alkylammonium, mono-, di- or tri-C
2
-C
4
alkanolammonium salt, or a C
1
-C
3
alkyl ester thereof; or a radical of formula
R
5
is hydrogen; C
1
-C
5
alkyl unsubstituted or substituted by one or more OH groups; C
1
-C
5
alkoxy; amino; mono- or di-C
1
-C
5
alkylamino; M; a radical of formula
wherein
R′, R″ and R′″ are each independently of the others C
1
-C
14
alkyl unsubstituted or substituted by one or more OH groups;
R
6
is hydrogen; M; C
1
-C
5
alkyl; or a radical of formula —(CH
2
)
m
2
—O—T
1
;
M is a metal cation;
T
1
is hydrogen; or C
1
-C
8
alkyl;
m is 0 or 1;
m
2
is from 1 to 4; and
m
3
is from 2 to 14.
Further preferred triazine derivatives suitable for use according to the invention correspond to formula
wherein
R
7
and R
8
are each independently of the other C
1
-C
18
alkyl; C
2
-C
18
alkenyl; a radical of formula —CH
2
—CH(—OH)—CH
2
—O—T
1
; or
R
7
and R
8
are a radical of formula
R
9
is a direct bond; a straight-chain or branched C
1
-C
4
alkylene radical or a radical of formula —C
m
1
H
2m
1
—O—;
R
10
, R
11
and R
12
are each independently of the others C
1
-C
18
alkyl; C
1
-C
18
alkoxy or a radical of formula
R
13
is C
1
-C
5
alkyl;
m
1
is from 1 to 4;
p
1
is from 0 to 5;
A
1
is a radical of formula
or of formula
R
14
is hydrogen; C
1
-C
10
alkyl, —(CH
2
CHR
16
—O)
n
1
—R
15
; or a radical of formula —CH
2
—CH(—OH)—CH
2
—O—T
1
;
R
15
is hydrogen; M; C
1
-C
5
alkyl; or a radical of formula —(CH
2
)
m
2
—O—(CH
2
)
m
3
—T
1
;
R
16
is hydrogen; or methyl;
T
1
is hydrogen; or C
1
-C
8
alkyl;
Q
1
is C
1
-C
18
alkyl;
M is a metal cation;
m
2
and m
3
are each independently of the other from 1 to 4; and
n
1
is from 1 to 16.
Very especially preferred triazine derivatives of formula (2) correspond to formulae
wherein
R
17
and R
18
are each independently of the other C
3
-C
18
alkyl; or —CH
2
—CH(—OH)—CH
2
—O—T
1
;
R
19
is C
1
-C
10
alkyl or a radical of formula
R
20
is hydrogen; M; C
1
-C
5
alkyl; —NH—C
1
-C
5
alkyl; preferably —NH-tert-alkyl; or a radical of formula —(CH
2
)
m
—O—T
2
;
T
1
and T
2
are each independently of the other hydrogen; or C
1
-C
5
alkyl; and
m is from 1 to 4.
Of very special interest are compounds of formulae (2a) and (2b) wherein
R
17
and R
18
are each independently of the other C
1
-C
18
alkyl; or —CH
2
—CH(—OH)—CH
2
—O—T
1
;
R
19
is C
1
—C
10
alkyl;
and compounds of formulae (2c) and (2d) wherein
R
17
and R
18
are each independently of the other C
1
-C
18
alkyl or —CH
2
—CH(—OH)—CH
2
—O—T
1
; and
T
1
is hydrogen; or C
1
-C
5
alkyl.
Of very great interest are triazine compounds of formulae (2a)-(2d) wherein
R
17
and R
18
have the same meaning.
Further interesting triazine compounds suitable for use according to the invention correspond to formula
wherein
R
21
is C
1
-C
30
alkyl; C
2
-C
30
alkenyl; C
5
-C
12
cycloalkyl unsubstituted or mono or poly-substituted by C
1
-C
5
alkyl; C
1
-C
5
alkoxy-C
1
-C
12
alkyl; amino-C
1
-C
12
alkyl; C
1
-C
5
-monoalkylamino-C
1
-C
12
alkyl; C
1
-C
5
dialkylamino-C
1
-C
12
alkyl; a radical of formula
wherein
R
22
, R
23
and R
24
are each independently of the others hydrogen, —OH; C
1
-C
30
alkyl, C
2
-C
30
alkenyl,
R
25
is hydrogen; or C
1
-C
5
alkyl;
m
1
is 0 or 1; and
n
1
is from 1 to 5.
Preferred compounds correspond to formula
wherein
R
26
is
or
—O-2-ethylhexyl; —O—(CH
2
)
3
—N(C
2
H
5
)
2
;
and
r and s are each independently of the other from 0 to 20.
Examples of triazine derivatives suitable for use according to the invention correspond to the formulae
also 2,4,6-tris(diisobutyl-4′-aminobenzalmalonate)-s-triazine and 2,4-bis(diisobutyl-4-amino-benzalmalonate)-6-(4′-aminobenzylidenecamphor)-s-triazine.
Triazine compounds suitable for use according to the invention that are likewise preferred are described in EP-A-654 469, e.g. the compound of formula
Triazine compounds especially suitable for use according to the invention are described, for example, in EP-A-0 818 450, e.g. the compound of formula
Very especially preferred triazine derivatives suitable for use according to the invention correspond to formula
wherein
R
27
, R
28
and R
29
are each independently of the others a radical of formula
or
R
30
is hydrogen; an alkali metal; an ammonium group —N(R
33
)
4
,
R
33
is hydrogen, C
1
-C
5
alkyl; or a polyoxyethylene radical that has from 1 to 10 ethylene oxide units and the terminal OH group can be etherified with a C
1
-C
5
alcohol;
R
31
is hydrogen; —OH; or C
1
-C
6
alkoxy;
R
32
is hydrogen or —COOR
30
; and
n is 0 or 1.
When R
30
is an alkali metal, it is especially potassium or more especially sodium. (R
33
)
4
is especially a mono-, di- or tri-C
1
-C
4
alkylammonium salt, a mono-, di- or tri-C
2
-C
4
alkanol-ammonium salt or a C
1
-C
3
alkyl ester thereof.
When R
33
is a C
1
-C
3
alkyl group, it is especially a C
1
-C
2
alkyl group, more especially a methyl group, and when R
33
is a polyoxyethylene radical, that radical contains especially from 2 to 6 ethylene oxide units.
Preferred benzotriazole compounds suitable for use according to the invention correspond to formula
wherein
T
1
is C
1
-C
5
alkyl or preferably hydrogen; and
T
2
is C
1
-C
5
alkyl, preferably tert-butyl, or phenyl-substituted C
1
-C
4
alkyl, especially &agr;,&agr;-dimethylbenzyl.
A further preferred class of benzotriazole compounds suitable for use according to the invention corresponds to formula
wherein
T
2
is as defined for formula (26).
Further, especially preferred benzotriazole compounds suitable for use according to the invention correspond to formula
wherein
T
2
is as defined for formula (26) and is preferably methyl, tert-butyl or
Ciba Specialty Chemicals Corporation
Dodson Shelley A.
Mansfield Kevin T.
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