Use of fluorescent whitening agents

Details Use of fluorescent whitening agents Use of fluorescent whitening agents

2002-06-11

2004-11-16

Dodson, Shelley A. (Department: 1616)

Drug, bio-affecting and body treating compositions

Topical sun or radiation screening, or tanning preparations

C424S060000, C424S400000, C424S401000

Reexamination Certificate

active

06818205

ABSTRACT:

The present invention relates to the use of a polymeric carrier material treated with a fluorescent whitening agent, for lightening human skin and for protecting human skin against UV radiation.
Melanin is a dark pigment that is found in the hair, the eyes and, especially, the skin, and that is formed in the so-called melanocytes by the conversion of the amino acid tyrosine in the presence of the enzyme tyrosinase. The number of melanocytes varies widely according to individual skin type.
Frequently, local areas of skin are to be found that have an increased melanin density. In such areas the number of melanocytes is significantly elevated, resulting in a skin colour that is far darker than the colour of the rest of the skin. Such local, hyperpigmented areas are known as brown spots, age spots or liver spots.
Women who have borne children and/or have taken the contraceptive pill for a prolonged period are frequently more especially subject to such spot formation. This undesired colour change is considered in particular by many women to be a disfigurement, and frequently leads to serious emotional disorders. Also, in many cultures in which parts of the population are coloured, especially in the Asiatic region, a naturally dark skin type that has elevated melanin concentration is undesirable. In regions such as those, depigmentation compositions are preferably used to lighten the skin.
In the past a number of topical preparations have been proposed for the prevention of hyperpigmentation that comprise one or more components, so-called depigmentation agents or bleaching agents, e.g. hydroquinone, hydroquinone derivatives, hydrocortisone and retinic acid, benzyloxyphenol (U.S. Pat. No. 3,060,097) or methoxyphenol. Such components bring about depigmentation by the oxidation or reduction of melanin, but a disadvantage of those active ingredients is that they may cause undesired skin reactions, or satisfactory formulation thereof into cosmetic preparations is not possible.
The problem of the present invention is to make available skin-lightening compositions that on the one hand have the effect of lightening the skin and that on the other hand are well tolerated by the skin and can be formulated cosmetically.
Surprisingly, it has now been found that a polymeric carrier material treated with a fluorescent whitening agent meets those requirements. In addition, such a material protects the human skin from the damaging effect of UV rays.
The present invention accordingly relates to the use of a polymeric carrier material treated with a fluorescent whitening agent for lightening human skin and for protecting human skin against UV radiation.
Preferred fluorescent whitening agents that can be used in accordance with the invention correspond to the formula
wherein
R
1
is a radical of formula
R
3
is M; unsubstituted or substituted alkyl or unsubstituted or substituted aryl;
R
4
is hydrogen; unsubstituted or substituted alkyl or unsubstituted or substituted aryl; or —NR
6
R
7
, wherein R
6
and R
7
are each independently of the other hydrogen; unsubstituted or substituted alkyl or unsubstituted or substituted aryl; or R
6
and R
7
together with the nitrogen atom binding them form a heterocyclic radical, especially a morpholino or piperidino radical,
R
5
is hydrogen, unsubstituted or substituted alkyl or unsubstituted or substituted aryl, or a radical of formula (1a) —(CH
2
)
x
2
—O—SO
3
—M;
R
2
is hydrogen, unsubstituted or substituted alkyl or unsubstituted or substituted aryl; or a radical of formula
 —OH, —NH
2
, —N(OH
2
OH
2
OH)
2
; —N[CH
2
CH(OH)CH
3
]
2
; —NH—R
3
; —N(R
3
)
2
or —OR
3
; or
R
1
and R
2
are each independently of the other —OH, —Cl; —NH
2
, —O—C
1
-C
4
alkyl, —O—aryl, —NH—C
1
-C
4
alkyl, —N(C
1
-C
4
alkyl)
2
, —N(C
1
-C
4
alkyl), —N(hydroxy-C
1
-C
4
alkyl), —N(hydroxy-C
1
-C
4
alkyl)
2
; —NH-aryl, morpholino; or S—C
1
-C
4
alkyl(aryl);
R
8
and R
9
are each independently of the other hydrogen, C
1
-C
4
alkyl, phenyl or a radical of formula
R
10
is hydrogen, Cl or SO
3
M;
R
11
is —CN, —SO
3
M, —S(C
1
-C
4
alkyl)
2
or S(aryl)
2
;
R
12
is hydrogen, —SO
3
M, —O—C
1
-C
4
alkyl, —CN, —Cl, —COO—C
1
-C
4
alkyl or CON(C
1
-C
4
alkyl)
2
;
R
13
is hydrogen; —C
1
-C
4
alkyl, —Cl or —SO
3
M;
R
14
and R
15
are each independently of the other hydrogen, C
1
-C
4
alkyl, —SO
3
M, —Cl or —O—C
1
-C
4
alkyl;
R
16
is hydrogen or C
1
-C
4
alkyl;
R
17
is hydrogen, C
1
-C
4
alkyl, —CN, —Cl, —COO—C
1
-C
4
alkyl, —CON (C
1
-C
4
alkyl)
2
, aryl or —O-aryl;
M is hydrogen, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-C
1
-C
4
alkylammonium, mono-, di- or tri-C
1
-C
4
hydroxyalkylammonium, or ammonium di- or tri-substituted by a mixture of C
1
-C
4
alkyl and C
1
-C
4
hydroxyalkyl groups;
n
1
, n
2
and n
3
are each independently of the others 0 or 1;
x
1
is 1 or 2; and
x
2
is from 1 to 3.
R
2
, R
3
, R
4
, R
5
, R
6
and R
7
in the meaning of (unsubstituted or) substituted alkyl is C
1
-C
12
alkyl, preferably C
1
-C
4
alkyl. The alkyl groups may be branched or unbranched and may be unsubstituted or substituted by halogen, e.g. fluorine, chlorine or bromine, by C
1
-C
4
alkoxy, e.g. methoxy or ethoxy, by phenyl or carboxyl, by C
1
-C
4
alkoxycarbonyl, e.g. acetyl, by mono- or di-C
1
-C
4
alkylamino or by —SO
3
M.
R
2
, R
3
, R
4
, R
5
, R
6
and R
7
in the meaning of (unsubstituted or) substituted aryl is preferably a phenyl or naphthyl group that may be unsubstituted or substituted by C
1
-C
4
alkyl, e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, by C
1
-C
4
alkoxy, e.g. methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy or tert-butoxy, by halogen, e.g. fluorine, chlorine or bromine, by C
2
-C
5
alkanoylamino, e.g. acetylamino, propionylamino or butyrylamino, by nitro, by sulfo or by di-C
1
-C
4
alkylated amino.
The compounds of formula (1) are preferably used in neutral form, that is to say M is preferably a cation of an alkali metal, especially sodium, or an amine.
In the compounds of formula (1), R
1
is preferably a radical of formula
wherein R
3
has the meanings given above and is preferably C
1
-C
4
alkyl, especially methyl or ethyl; or a radical of formula
wherein R
4
has the meanings given above and is preferably C
1
-C
4
alkyl, especially methyl or ethyl, or —NR
6
R
7
, wherein R
6
and R
7
have the meanings given above and are preferably hydrogen, C
1
-C
4
alkyl, especially methyl or ethyl, a morpholino or piperidino radical, more especially hydrogen, or a radical of formula
wherein R
5
has the meanings given above and is preferably C
1
-C
4
alkyl substituted by —SO
3
M, especially methyl or ethyl substituted by —SO
3
M, wherein M has the meanings given above and Is preferably sodium; and R
2
is preferably
—NH
2
, —N(CH
2
CH
2
OH)
2
of —N[CH
2
CH(OH)CH
3
]
2
.
The compounds of formula (1) can be prepared under known reaction conditions by the reaction of cyanuric chloride with the corresponding aminostilbenesulfonic acids and with an amino compound that is capable of introducing a group R
1
and with a compound that is capable of introducing a group R
2
, R
1
and R
2
having the meanings given above.
The fluorescent whitening agents that can be used with advantage in the present invention are listed by way of example in the following Table 1:
TABLE 1
Compound
of formula
 (9)

(10)

(11)

(12)

(13)

(14)

(15)

(16)

(17)

(18)

(19)

(20)

(21)

(22)

(23)

(24)

(25)

(26)

(27)

(28)

(29)

(30)
In principle, as polymeric carriers for use in accordance with the invention there come into consideration materials that are suitable for cosmetic or pharmaceutical preparations. The polymeric materials may be of natural origin or are obtainable synthetically, e.g. starch, starch derivatives, e.g. hydroxypropyl-distarch phosphate, polyvinylpyrrolidones, polyvinyl-polypyrrolidones, polyacrylates, acrylates/steareth-20, methacrylate copolymers, acrylate copolymers, acrylate-octylpropenamide copolymer (Dermacryl 79), acrylate/vinyl isodecanoate cross polym

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