Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-05-18
2001-03-13
Jarvis, William R. A. (Department: 1614)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
Reexamination Certificate
active
06201000
ABSTRACT:
The present invention relates to the use of selected benzotriazole derivatives for protecting human and animal hair and skin from the harmful effects of UV radiation.
It is known that UV radiation having a wavelength of 285 to 400 nm causes or accelerates a very wide range of skin damages in humans, for example erythemas, accelerated skin ageing, phototoxic and photoallergic reactions and the like. If human hair is exposed to sunlight over a prolonged period of time it may be damaged in different ways. Under the influence of sunlight, dyed hair can change its colour and shade. Blond hair turns yellowish. The hair surface becomes rougher and at the same time drier. Furthermore, the hair gradually loses its sheen.
Chemical compounds in the form of cosmetic formulations recommending themselves for the topical protection of human skin and of the hair surface are therefore those which are able to reduce or prevent the mentioned harmful effects of UV radiation.
Surprisingly, it has now been found that specific benzotriazole derivatives have excellent substantivity for human hair while at the same time providing effective UV protection for hair and human skin.
Accordingly, this invention relates to the use of selected benzotriazole derivatives for protecting human and animal hair and skin from the harmful effects of UV radiation.
The selected benzotriazole compounds are compounds of formula
wherein
R
1
, R
2
and R
3
are each independently of one another hydrogen; straight-chain or branched C
1
-C
22
alkyl; hydroxy; carboxy; carbo-C
1
-C
22
alkoxy; nitro; C
2
-C
22
alkylcarbonylamino; C
5
-C
8
-Cacycloalkyl; carbamoyl; sulfonyl; sulfamoyl; sulfonamido; C
2
-C
22
alkylcarbonyloxy; cyano; halogen; C
6
-C
12
aryl or C
4
-C
12
heteroaryl which is unsubstituted or substituted by one or several C
1
-C
4
alkyl; C
7
-C
10
aralkyl which is unsubstituted or substituted by one or several C
1
-C
4
alkyl; C
8
-C
12
aryloxy; or a radical of formula
&Parenopenst;alkylene-Q&Parenclosest;
m
1
A
1
, (1a)
wherein
A
1
is straight-chain or branched C
1
-C
8
alkyl; C
5
-C
8
cycloalkyl; C
5
-C
12
aryl which is unsubstituted or substituted by one or several C
1
-C
4
alkyl; or C
7
-C
10
aralkyl which is unsubstituted or substituted by one or several C
1
-C
4
alkyl;
m
1
is 1to 10;
Q is —O—; —S—; or —NH—; or
R
1
and R
2
, together with the benzene ring of the benzotriazole, are a C
5
-C
18
aryl ring or a C
4
-C
16
heteroaryl ring, which rings are unsubstituted or substituted by C
1
-C
22
alkyl or C
1
-C
22
alkoxy;
R
4
is hydrogen; C
1
-C
22
alkyl which is unsubstituted or substituted by 1 to 5 halogen atoms and/or which is interrupted by a —C(O)—O— or —SO
2
—O— group;
R
5
, R
6
, R
7
are each independently of one another hydrogen; halogen; cyano; straight-chain or branched C
1
-C
22
alkyl; straight-chain or branched C
1
-C
22
alkoxy; C
5
-C
12
aryl; straight-chain or branched C
1
-C
22
thioalkyl; mono- or di-C
1
-C
22
alkylamino; mono- or di-C
6
-C
12
-arylamino; R
5
≠R
6
≠R
7
;
X is
the carbonyl carbon atom being bound to the nitrogen atom of the
moiety; or —SO
2
—;
L is a divalent radical consisting of 1 to 20 atoms; and
p is 0 or 1.
Straight-chain and branched C
1
-C
22
alkyl is typically methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl. isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, heptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or eicosyl.
C
5
-C
8
Cycloalkyl is typically cyclopentyl, cycloheptyl, cyclooctyl and, in particular, cyclohexyl.
Examples of C
6
-C
12
aryl to be mentioned are, in particular, phenyl, naphthyl and biphenyl.
Typical examples of C
7
-C
10
aralkyl are benzyl, phenethyl, &agr;-methylphenethyl or &agr;,&agr;-dimethylbenzyl.
“Alkylene” in formula (1a) is a divalent alkylene group containing 2 to 5, preferably 2 to 4 carbon atoms. It is preferably the —CH
2
—CH
2
—; —CH
2
CH
2
CH
2
—;
group. Of these alkylene groups, the —CH
2
—CH
2
— and the
group are very particularly preferred.
Halogen is fluoro, bromo or, preferably, chloro.
The compound of formula (1) is preferably a 60:40 to 40:60 mixture of two enantiomers relative to the asymmetrical C* atom.
L can consist, in particular, of 1 to 20 atoms and can be a straight-chain or branched alkylene group which may be interrupted by 1 to 5 oxygen, sulfur or nitrogen atoms or by a —C(O)—O— group which is unsubstituted or substituted by C
1
-C
10
alkoxy, C
1
-C
10
alkylcarbonyloxy, C
1
-C
10
alkyl sulfide, amino, mono-C
1
-C
10
alkylamino, di-C
1
-C
10
alkylmino or halogen; or the divalent radical of a 4- to 6-membered alicyclic ring or of a heterocyclic ring containing 1 to 3 hetero atoms.
Illustrative examples of alicyclic and heterocyclic radicals are heterocyclic radicals containing cyclohexylene, pyrrolidinylene, tetrahydofuranylene, tetrahydrothienylene, piperidinylene, pyrrolylene, furylene, thienylene, pyrridylene or Spiro ethers, for example
In particular, L may also be a methine group which is unsubstituted or substituted by C
1
-C
12
-alkyl or C
1
-C
12
alkoxy, amino, mono- or di-C
1
-C
6
alkylamino or halogen, wherein C
1
-C
12
alkyl or C
1
-C
12
alkoxy may be interrupted by 1 or 2 oxygen atoms.
Typical examples of L defined as divalent radicals are:
alkylene groups, such as —CH
2
—; CH
2
—CH
2
—; —CH
2
CH
2
CH
2
—;
group. Of these alkylene groups, the —CH
2
— and the —CH
2
—CH
2
— group are very particularly preferred.
Radicals containing oxygen atoms or —C(O)—O— groups, such as —CH
2
—O—CH
2
—CH
2
—O—; —(CH
2
—O—CH
2
—CH
2
—O)
2
—; —CH
2
—C(O)OCH
2
—; —CH
2
C(O)OCH
2
CH(OCOCH
3
)CH
2
O—;
heterocyclic radicals, such as
R
5
, R
6
, R
7
in formula (1) are preferably each hydrogen; or, independently of one another, straight-chain or branched C
1
-C
22
alkyl.
According to this invention, it is very particularly preferred to use benzotriazole derivatives of formula
wherein
R
1
and R
2
are each independently of one another hydrogen; halogen; C
1
-C
5
alkyl; C
1
-C
5
-alkoxy; mono- or di-C
1
-C
5
alkylamino; or C
1
-C
5
alkyl sulfide;
R
3
is hydrogen; hydroxy; or halogen;
R
4
is hydrogen; C
1
-C
5
alkyl which is unsubstituted or substituted by 1 to 5 halogen atoms and/or which may be interrupted by a —C(O)—O— or —SO
2
—O— group;
L is a straight-chain or branched alkylene group which may be interrupted by 1 to 5 oxygen atoms or by a —C(O)—O— group which may be substituted by C
1
-C
10
alkoxy or C
1
-C
10
-alkylcarbonyloxy; and
R
5
, R
6
, R
7
are each independently of one another hydrogen or C
1
-C
10
alkyl; R
5
≠R
6
≠R
7
; and
X is
the carbonyl carbon atom being bound to the nitrogen atom of the
moiety; or —SO
2
—.
Very particularly preferred benzotriazole derivatives are those of formula
wherein
R
3
is hydrogen; halogen or hydroxy;
R
4
is hydrogen; C
1
-C
5
alkyl which is unsubstituted or substituted by 1 to 5 halogen atoms and/or which may be interrupted by a —C(O)—O— or —SO
2
—O— group;
R
5
, R
6
, R
7
are each independently of one another hydrogen or C
1
-C
10
alkyl; R
5
≠R
6
≠R
7
;
L is a straight-chain or branched alkylene group which may be interrupted by 1 to 5 oxygen atoms or by a —C(O)—O— group which may be substituted by C
1
-C
10
alkoxy or C
1
-C
10
-alkylcarbonyloxy; and
X is
the carbonyl carbon atom being bound to the nitrogen atom of the
moiety; or —SO
2
—.
Some of the benzotriazole derivatives of formula (1) are known compounds. Some of them are, however, novel compounds. These novel compounds correspond to formula
or to formula
The benzotriazole derivatives of formula (1) can be prepared by reacting the chromophore of formula
with the compound of formula
with the compound of formula
R
1
, R
2
, R
Luther Helmut
Reinehr Dieter
Zink Rudolf
Ciba Specialty Chemicals Corporation
Jarvis William R. A.
Kim Vickie
Mansfield Kevin T.
LandOfFree
Use of selected benzotriazole derivatives for protecting... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Use of selected benzotriazole derivatives for protecting..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Use of selected benzotriazole derivatives for protecting... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2472921