Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations – Aromatic acid or derivative containing
Reexamination Certificate
2002-04-10
2004-03-02
Seaman, D. Margaret (Department: 1621)
Drug, bio-affecting and body treating compositions
Topical sun or radiation screening, or tanning preparations
Aromatic acid or derivative containing
C424S070100, C424S070900, C514S531000, C514S532000, C514S538000, C560S008000, C560S019000, C560S020000, C560S021000, C560S022000, C560S037000, C560S038000, C560S039000, C560S041000, C564S161000, C564S163000, C564S164000, C564S166000, C564S169000, C564S182000, C558S020000, C558S027000, C558S028000
Reexamination Certificate
active
06699463
ABSTRACT:
BACKGROUND OF THE INVENTION
Photofilters and UV-absorbers have been employed for a number of years to protect coloring dyes from fading from exposure to light. UV-sunscreens have also been employed to protect skin from damage from exposure to sunlight. Representative references related to UV-sunscreens are:
U.S. Pat. No. 5,922,310 (Chaudhuri et al.) discloses a composition which includes a cationic antioxidant phenol in an amount of about 0.01-1% wt/wt.
U.S. Pat. No. 5,427,773 (Chaudhuri et al.); U.S. Pat. No. 5,427,774 (Chaudhuri et al.); and U.S. Pat. No. 5,451,394 (Chaudhuri et al.) discloses non-hydrolysable, non irritating, hair, skin and textile substantive quaternary salts of p-dialkylaminobenzamides.
U.S. Pat. No. 5,633,403 (Gallagher et al.) discloses substantive UV-absorbing cinnamido amine cationic quaternary salts.
U.S. Pat. No. 5,830,441 (Wang et al.) discloses a photostable UV absorbent with maximum absorption above 340 nm.
Hair is largely comprised of polypeptide chains that are held together by disulfide bonds which link adjacent polypeptide chains. The disulfide bonds are largely responsible for the mechanical strength and extensibility of hair. Exposure to sun tends to cause these disulfide bonds to break making the hair stiff and brittle in dry weather and frizzy in humid weather. Additionally, the hair also loses its color and luster in such conditions.
The essential first event in hair photo damage, as in all processes, is light absorption by the fiber. Only wavelengths above 290 nm will be consequential in natural photo damage since shorter wavelength UV light the stratosphere will effectively filter out. The most significant chromophores in proteins that absorb in the UV-B region are the amino acids, tyrosine (&lgr;max 275 nm), tryptophan (&lgr;max 280 nm), and the disulfide bonds (weak absorption at 290 nm). The longer wavelength UV-A and the visible light are not likely to cause damage directly since proteins do not absorb them. However, UV-A light is well known for generating free radicals; consequently damage to cholesterol and fatty acids occur.
The photodegradation of hair results in a variety of physical and chemical changes. Among the physical changes are elimination of cuticle cells, roughening of the hair surface, loss of mechanical and elastic strength, and increased porosity. Chemically, we find photooxidation of cysteine, cholesterol, and fatty acids; the decomposition of tryptophan; breakage of disulfide bonds; and bleaching of melanin and artificial hair colors can occur.
Human hair damage caused by sunlight in the UV spectrum is more severe than that resulting from all other factors such as weather, wind, atmospheric pollution, salt water, chlorinated water, perming, coloring, bleaching and improperly applied or repetitive treatments. Sunscreens used for skin are not suitable for hair because they are either not substantive or leave the hair dull and tacky. For hair protection, several approaches have been described, such as the deposition of photofilters on the hair surface, and the use of antioxidants or free radical scavengers.
Recently, sunscreens also have been added to hair care products to guard against the deleterious effects of solar irradiation on the hair. Two sunscreens have been developed especially for hair, Escalol® HP 610 (U.S. Pat. No. 5,451,394) and Incroquat® UV-283 (U.S. Pat. No. 5,633,403). Unfortunately, they both suffer from inadequate photostability, meaning that they degrade in the presence of light, and they lack desired hair substantivity, meaning that they can not be effectively applied and retained on hair.
The ideal sunscreen formulation for hair should be nontoxic and non-irritating to the skin tissue and be capable of convenient application in a uniform and continuous film. The product should be chemically and physically stable so as to provide an acceptable shelf life upon storage. It is particularly desirable that the preparation should retain its protective effect over a prolonged period after application. The product must be substantive to hair or skin so that it does not get washed-off quickly. Thus, the active agent when present on the hair or skin must be resistant to chemical and/or photodegradation and be substantive.
Techniques for stabilizing UV absorbent compositions are known. Representative disclosures in this area include U.S. Pat. Nos. 5,567,418, 5,538,716, 5,951,968 and 5,670,140.
Antioxidants are believed to function by providing protection from free-radical damage. To be an effective free radical quencher, it is believed the antioxidant must be present in an adequate concentration at the site of free radical generation. Since antioxidants are used in low concentrations and typically lack functionality to become substantive to hair or skin, they may not be available at the site of generation, thereby reducing the desired protection. Many existing antioxidants can also act as pro-oxidants instead of antioxidants in presence of iron and copper (see a review on Transition Metal-Induced Oxidation by Chaudhuri and Pucceti,
Cosm
&
Toil
, July issue, 2002). Based on these beliefs, it is desirable to provide the antioxidant (having no pro-oxidation activity induced my transition metals) and photostable sunscreen functionality in a single molecule, which is substantive to hair, skin or other substrates to enhance the effectiveness of the antioxidant properties.
SUMMARY OF THE INVENTION
There is provided by the present invention compounds with sunscreen activity, i.e. they are chromophoric within the ultra violet radiation range of from 290-400 nm and they also exhibit antioxidant properties. The sunscreen formulations of this invention preferably offer protection from UV radiation with wavelengths of about 290 nm to 400 nm and preferably from wavelengths in the range of about 290-370 nm.
The compounds of the invention herein are represented by the general Formula I
In Formula I, each R is independently linear or branched C, to C
8
alkyl, or linear or branched C
1
to C
8
alkoxy; or one R is H and the other R is linear or branched C
1
to C
8
alkyl, or linear or branched C
1
to C
8
alkoxy.
R
1
is selected from the group consisting of COCH
3
, CO
2
R
5
, CONH
2
, CONH(R
6
)
2
, CN, COX(CH
2
)n-N—(R
2
)(R
4
)(R
3
), and the quaternized salt form of the formula COX(CH
2
)n-N—(R
2
)(R
4
)(R
3
)
+
Y
−
;
X is O or NH;
n is an integer of 1 to 5;
Y is an anion;
R
2
, R
3
and R
4
are independently linear or branched C
1
to C
20
alkyl; and
R
5
and R
6
are independently hydrogen or linear or branched C
1
-C
20
alkyl.
Preferred compounds of Formula I for hair and other substrate protection are illustrated by Formula II
In Formula II, R
1
is as defined for Formula I but is preferably COCH
3
or CONH(CH
2
)
3
N
+
(CH
3
)
2
(CH
2
CH
3
) CH
3
CH
2
OSO
−
3
; and X is O or NH.
Concerning Formulae I and II, the integer n is preferably 2 to 3; and the anion Y is preferably Cl, Br, alkyl sulfate, alkyl sulfonate, or p-tolyl sulfonate. R
2
, R
3
and R
4
of formulae I and II are preferably independently linear or branched C
1
to C
8
. R
5
and R
6
are preferably C
1
to C
8
alkyl.
The invention is also directed to a hair care formulation containing the compound of the invention. The compound is typically used as a protective and conditioning ingredient in the hair care formulation against UV-A rays, UV-B rays, or both against UV-A and UV-B rays. The formulation can contain a single compound of formula I or a mixture of compounds of formula I.
Preferably, the hair care formulation contains a compound or a mixture of compounds of the invention which are substantive and capable of protecting hair, skin or fibers against illumination in the range of about 310 to 360 nm.
It is also preferable that the compound or a mixture of compounds of the invention be capable of stabilizing the hair care formulation against photodegradation, and be further capable of providing an antioxidant property to the formulation.
In another aspect, the invention is directed to a mixture containing at le
EM Industries
Millen White Zelano & Branigan P.C.
Seaman D. Margaret
LandOfFree
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