Title of Invention

"AQUEOUS DISPERSION FOR PROTECTING HUMAN SKIN FROM BROWNING AND AGING, COMPRISING BENZOPHENONE COMPOUND"

Abstract Disclosed is the use of an aqueous dispersion comprising (a) a micronized sparingly soluble organic compound which has a UV-Vims spectrum with a maximum from 380 to 420 nm and (b) an anionic dispersing agent for protecting the human in from browning and skin aging.
Full Text Use of transmission dyes for protecting Inhuman skin from browning and ageing

Tile present invention relates to tile use of specific transmisson dyes for protecting human
tear and skin against UV radiation and skin aging and preventing tanning and cosmetic or
dermatological compositions comprising these dyes.
It is known that certain photostable organic UV filters, for example bis- exhibit pronounced UV filtering properties in the UV-A range up to 380nm. In the range from 380nm to 420nm no satisfactory UV protection can be achieved.
However, it is known that in the region > 380nm the sun light significantly contributes to skin aging and enhanced skin cancer risk.
Surprisingly it was found that specific UV absorbers which have absorption maxima above Son show no significant color when applied to the skin.
Therefore the present invention relates to the use of an aqueous dispersion comprising
(a) a micronized sparingly soluble organic compound which has a UV-Vis spectrum with a maximum from 380 to 420 nm; and
(b) an anionic dispersing agent
for protecting the human skin from browning and skin aging.
Preferably the organic micronized UV absorbers are selected from benzophenone derivatives.



02 is a number from 1 to 3;
when Di is 3,
C2-C2oalkenyl is for example allyl, lethally, isopropenyl, 2-butenyl, 3-butenyl, isobutene, n-penta-2,4-dieny!, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, iso-dodecenyl, n-dodec-2-enyI or n-octadec-4-enyi.

substituted with one or more radicals they are preferably substituted with one, two, three or four, preferably with one or two equal or different radicals.
If Ri and R2 are heterocyclic radicals, these comprise one, two, three or four equal or different ring hetero atoms. Special preference is given to heterocycles which contain one, two or three, especially one or two, identical or different hetero atoms. The heterocycles may be mono- or poly-cyclic, for example mono-, bi- or tri-cyclic. They are preferably mono- or bi-cyclic, especially monocyclic. The rings preferably contain 5, 6 or 7 ring members. Examples of monocyclic and bicyclic heterocyclic systems from which radicals occurring in the compounds of formula (1) or (2) may be derived are, for example.
Most preferably the benzophenone derivative used for the present invention corresponds to formula




The compounds of formula (1) may be prepared according to known methods as described for example in EP-1,046,391 or WO 04/052837.
Sparingly soluble organic compounds which are used in the present invention are present in the micronized state. They may be prepared by any known process suitable for the preparation of microparticles, for example: wet-milling, wet-kneading, spray-drying from a suitable solvent, by expansion according to the RESS process (Rapid Expansion of Supercritical Solutions) of supercritical fluids (e.g. CO2, by reprecipitation from suitable solvents, including supercritical fluids (GASR process = Gas Anti-Solvent Recrystallisation / PGA process = Precipitation with Compressed Anti-solvents).
As milling apparatus for the preparation of the sparingly soluble micronised organic compounds there may be used, for example, a jet mill, ball mill, vibratory mill or hammer mill, preferably a high-speed mixing mill. Even more preferable mills are modern ball mills; manufacturers of these types of mill are, for example, Netzsch (LMZ mill), Drais (DCP-Viscoflow or Cosmo), Buhler AG (centrifugal mills) or Bachhofer.
Examples of kneading apparatus for the preparation of the micronised organic UV absorbers are typical sigma-blade batch kneaders but also serial batch kneaders (IKA-Werke) or continuous kneaders (Continua from Werner und Pfleiderer).

The grinding of the sparingly soluble organic compounds used in the present inventions preferably carried out with a grinding aid.
The dispersing agent (b) is used as a low molecular weight grinding aid for all the above micronisation processes.
Useful anionic, non-ionic or amphitricha surfactants are disclosed below in the sections entitled "specific dispersing agents".
Preferred useful grinding aids for an aqueous dispersion are anionic surfactants with a HLB (Hydrophile-Lipophile Balance) value higher than 8, more preferably higher than 10.
Any conventionally usable anionic, non-ionic or amphoteric surfactants can be used as dispersing agents (component (b)). Such surfactant systems may comprise for example: carboxylic acids and their salts: alkaline soap of sodium, potassium and ammonium, metallic soap of calcium or magnesium, organic basis soap such as Laurie, myristic, palmitic, sorbitan mono- and di-esters of saturated and unsaturated fatty acids having from 6 to 22 carbon atoms and ethylene oxide addition products. Po!ysorbate-n series, sorbitan esters such, sorbitan, PEG-(6}-isostearate sorbitan, PEG-(10)-sorbitan laurate, PEG-17- dioleate sorbitan. Glucose derivatives, C8-C22 alkyl-mono and oligo-glycosides and ethoxyiated analogues with

ceteareth-20 [Emulgade lOOONi, Cosmowax], cetearyl alcohol and PEG-40 castor oil [Emulgade F Special], cetearyl alcohol and PEG-40 castor oil and sodium cetearyl sulfate [Emulgade F], stearyl alcohol and steareth-7 and steareth-10 [Emulgator E 2155], cetearyl alcohol and szeareth-7 and steareth-10 [Emulsifying wax U.S.N.F], glyceryl stearate and PEG-75 stearate [Gelot 54], propylene glycol ceteth-3 acetate .[Hetester PCS], propylene glycol

isoceth-3 acetate [Hetester PHA], cetearyl alcohol and ceteth-12 and oleth-12 [Lanbritol Wax N 21], PEG -6 stearate and PEG-32 stearate [Tefose 1500], PEG-6 stearate and ceteth-20 and steareth-20 [Tefose 2000], PEG-6 stearate and ceteth-20 and glyceryl stearate and steareth-20 [Tefose 2561], glyceryl stearate and ceteareth-20 [Teginacid H, C, X].
Anionic emulsifiers such as PEG-2 stearate SE, glyceryl stearate SE [Monelgine, Cutina KD], propylene glycol stearate [Tegin P], cetearyl Alcohol and Sodium cetearyl sulfate [Lanette N, Cutina LE, Crodacol GP], cetearyl alcohol and sodium lauryl sulfate [Lanette W], trilaneth-4 phopshate and glycol stearate and PEG-2 stearate [Sedefos 75], glyceryl stearate and sodium lauryl Sulfate [Teginacid Special]. Cationic acid bases such as cetearyl alcohol and cetrimonium bromide.
Most prefen-ed dispersing agents (b) are sodium alkyl sulfates or sodium alkyl ether sulfates, such as sodium laureth sulfate [Texapon N70 from Cognis] or sodium myreth sulfate [Texapon K14 S from Cognis].
The specific dispersing agents may be used in an amount of, for example, from 1 to 30 % by weight, especially from 2 to 20 % by weight and preferably from 3 to 10 % by weight, based on the total weight of the composition.
Useful solvents are water, brine, (poly-)ethylene glycol, glycerol or cosmetically acceptable oils. Other useful solvents are disclosed below in the sections entitled "Esters of fatty acids", "Natural and synthetic triglycerides, including glyceryl esters and derivatives", "Pearlescent waxes", "Hydrocarbon oils" and "Silicones or siloxanes".
The micronised sparingly soluble organic compounds so obtained usually have an average particle size from 0.02 to 2 micrometres, preferably from 0.03 to 1.5 micrometres and more especially from 0.05 to 1.0 micrometres.
The aqueous dispersion used in the present invention generally comprises
30 - 60, preferably 35 to 55 parts of the sparingly soluble organic micronized substance;
2 - 20, preferably 2 to 20 parts of the dispersing agent;
0.1-1 part, preferably 0.1 to 0.5 parts of a thickening agent (for example xanthan gum); and
20 - 68 parts of water;









powders or ointments. In addition to the above mentioned UV filters, the cosmetic or pharma¬ceutical preparations may contain further adjuvants as described below.
As water- and oil-containing emulsions (e.g. W/0, 0/W, 0/W/O and W/OA/V emulsions or microemulsions) the preparations contain, for example, from 0.1 to 30 % by weight, pre¬ferably from 0.1 to 15 % by weight and especially from 0.5 to 10 % by weight, based on the total weight of the composition, of one or more UV absprbers, from 1 to 60 % by weight, especially from 5 to 50 % by weight and preferably from 10 to 35 % by weight, based on the total weight of the composition, of at least one oil component, from 0 to 30 % by weight, especially from 1 to 30 % by weight und preferably from 4 to 20 % by weight, based on the total weight of the composition, of at least one emulsifier, from 10 to 90 % by weight, es¬pecially from 30 to 90 % by weight, based on the total weight of the composition, of water, and from 0 to 88.9 % by weight, especially from 1 to 50 % by weight, of further cosmetically acceptable adjuvants.
The cosmetic or pharmaceutical compositions/preparations according to the invention may also contain one or one more additional compounds as like fatty alcohols, esters of fatty acids, natural or synthetic triglycerides including glyceryl esters and derivatives, pearlescent waxes, hydrocarbon oils, silicones or siloxanes (organosubstituted polysiloxanes), fluorinated or perfluohnated oils, emulsifiers, djuvants and additives, super-fatting agents, surfactants, consistency regulators/thickeners and rheology modifiers, polymers, biogenic active in¬gredients, deodorising active ingredients, anti-dandruff agents, antioxidants, hydrotropic agents, preservatives, bacteria-inhibiting agents, perfume oils, colourants, polymeric beads or hollow spheres as SPF enhancers.
Cosmetic or pharmaceutical preparations
Cosmetic or pharmaceutical formulations are contained in a wide variety of cosmetic prepa¬rations. There come into consideration, for example, especially the following preparations: skin-care preparations, bath preparations, cosmetic personal care preparations, foot-care preparations, light-protective preparations, skin-tanning preparations, depigmenting pre¬parations, insect-repellents, deodorants, antiperspirants, preparations for cleansing and caring for blemished skin, hair-removal preparations in chemical form (depilation), shaving preparations, fragrance preparations, cosmetic hair-treatment preparations,

Presentation forms
The final formulations listed may exist in a wide variety of presentation forms, for example:
in the form of liquid preparations as a W/0, OA/V, 0/\N/0, W/OA/V or PIT emulsion and all
kinds of microemulsions,
in the form of a gel.
In the form of an oil, a cream, milk or lotion,
in the form of a powder, a lacquer, a tablet or make-up,
in the form of a stick,
in the form of a spray (spray with propellent gas or pump-action spray) or an aerosol,
in the form of a foam, or
in the form of a paste.
Of special importance as cosmetic preparations for the skin are light-protective preparations, such as sun milks, lotions, creams, oils, sunblocks or tropicals, pretanning preparations or after-sun preparations, also skin-tanning preparations, for example self-tanning creams. Of particular interest are sun protection creams, sun protection lotions, sun protection milk and sun protection preparations in the form of a spray.
Of special importance as cosmetic preparations for the hair are the above-mentioned prepa¬rations for hair treatment, especially hair-washing preparations in the form of shampoos, hair conditioners, hair-care preparations, e.g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-straightening preparations, liquid hair-setting preparations, hair foams and hairsprays. Of special interest are hair-washing preparations in the form of shampoos.
Other typical ingredients in such formulations are preservatives, bactericides and bacterio¬static agents, perfumes, dyes, pigments, thickening agents, moisturizing agents, humectants, fats, oils, waxes or other typical ingredients of cosmetic and personal care formulations such as alcohols, poly-alcohols, polymers, electrolytes, organic solvents, silicon derivatives, emollients, emulsifiers or emulsifying surfactants, surfactants, dispersing agents, antioxidants, anti-irritants and anti-inflammatory agents etc.

The cosmetic preparation according to the invention is distinguished by excellent protection of human skin against the damaging effect of sunlight.


(prepared according to Example 1 of WO 204/052837) are dissolved in 250mt acetic acid
ethyl ester at room temperature.
8.6 g piperazine are added to this solution with stirnng whereas the temperature rises to
40°C.
The product precipitates during adding of the reaction mass.
Then the suspension is stirred for about 3h under refulux, filtered off and the residue is
recrystallized from 2-methoxy-ethanol.
After drying of the citric yellow crystals 67g of the end product are obtained.
Fp = 253-256°C.
The compound of formula (101) can be obtained in different forms. The single cristal forms are characterized


Claims
1. Use of an aqueous dispersion comprising
(a) a micron zed sparingly soluble organic compound which has a UV-Vis spectrum with a
maximum from 380 to 420 nm; and
(b) a dispersing agent selected from anionic, non-ionic and amphitricha surfactants;
for protecting the human skin from browning and aging.
2. Use according to claim 1, wherein the organic compound is selected from benzophenone derivatives.
3. Use according to claim 1 or 2, wherein the organic compound is selected from the compound of formula



Documents:

http://ipindiaonline.gov.in/patentsearch/GrantedSearch/viewdoc.aspx?id=axSk32bGU0jjvVEpM9Y8Yw==&loc=egcICQiyoj82NGgGrC5ChA==


Patent Number 272680
Indian Patent Application Number 3783/CHENP/2008
PG Journal Number 17/2016
Publication Date 22-Apr-2016
Grant Date 19-Apr-2016
Date of Filing 21-Jul-2008
Name of Patentee BASF SE
Applicant Address 67056, LUDWIGSHAFEN, GERMANY.
Inventors:
# Inventor's Name Inventor's Address
1 GIESINGER, JOCHEN BANDWEG 3, 79639 GRENZACH-WYHLEN
2 VOGT, MARTIN RITTERSTRASSE 20 A, 79639 GRENZACH-WYHLEN
3 MULLER, STEFAN DORFSTRASSE 46, 79576 WEIL AM RHEIN
4 HAASE, JURG HABERMARKWEG 45, CH-4126 BETTINGEN
5 EHLIS, THOMAS HARRIET-STRAUB-STRASSE 23, 79100 FREIBURG
6 KREYER, GILBERT RUE DES MARAICHERS 1, F-68300 SAINT-LOUIS
PCT International Classification Number A61Q17/04
PCT International Application Number PCT/EP06/69519
PCT International Filing date 2006-12-11
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 05112636.5 2005-12-21 EUROPEAN UNION
2 06114467.1 2006-05-24 EUROPEAN UNION