Composition containing 1,2-pentanediol

Abstract

To provide cosmetic and pharmaceutical compositions with improved olfactory performance and stability.SOLUTION: Provided is a cosmetic composition, a pharmaceutical composition and / or a detergent composition comprising 1,2 pentanediol, wherein the 1,2-pentanediol contains less than 10 ppm of butyric acid.SELECTED DRAWING: None

Description

Priority

[0001] This international application claims priority to U.S. provisional application US 62 / 733744, filed September 20, 2018. [Technical field]

[0002] The present invention refers to the field of cosmetic and pharmaceutical compositions with improved olfactory performance and stability, which contain a new quality of 1,2-pentanediol. [Background technology]

[0003] 1,2-alkanediols in general, and 1,2-pentanediol in particular, are well-known additives for cosmetic and pharmaceutical compositions, providing them with antimicrobial stability and improving the solubility of other ingredients within the formulation.

[0004] The qualities that can be found on the market are usually prepared from 1-pentene or 1,2-pentene oxide. However, the main drawback of these products is that they can have a slight odor that must be masked within the formulation. In fact, this odor becomes even stronger if the formulation is stored for a long period of time, especially at high temperatures.

[0005] There are alternative routes known to make 1,2-pentanediol available, such as for example hydrogenation of furfuryl alcohol in the presence of platinum dioxide. These products are more or less odorless and show better olfactory qualities when freshly prepared, but show the same tendency to generate the impression of a bad odor when incorporated into formulations and stored for long periods of time. Another drawback is that this manufacturing process is more expensive than the ring opening of epoxides. [Prior art documents] [Non-patent literature]

[0006] A suitable starting material for the production of 1,2-pentanediol is furfuryl alcohol, which is available in large quantities, for example from sugarcane bagasse. It is known from the literature that in the hydrogenation or hydrogenolysis of furfuryl alcohol, various compounds are formed.

[0007] For example, Adkins and Connor [Journal of American Chemical Society 53, 1091(1931)] reported that hydrogenation or hydrogenolysis of furfuryl alcohol at 175 °C in the liquid phase using copper chromite as a catalyst gives a mixture of 40% 1,2-pentanediol, 30% 1,5-pentanediol, 10% amyl alcohol, 20% tetrahydrofurfuryl alcohol and methyltetrahydrofuran. Kaufmann and Adams [Journal of American Chemical Society 45, 3029(1923)] reported that hydrogenolysis / hydrogenation of furfural in the presence of platinum black at room temperature gives a mixture of furfuryl alcohol, 1-pentanol, tetrahydrofurfuryl alcohol, 1,2-pentanediol and 1,5-pentanediol.

[0008] Furthermore, a study of the catalytic hydrogenation or hydrogenolysis of furan and furan derivatives in the liquid phase with platinum dioxide catalysts is found in the work of Smith and Fuzek [Journal of American Chemical Socience 71, 415 (1949)]. The reactions were carried out in acetic acid at hydrogen pressures of 20, 40, or 60 psi (60 psi corresponds to approximately 4 bar), and the catalysts mentioned were prepared by literature [Organic Synthesis 8, 92 (1928)]. In the hydrogenation or hydrogenolysis of furfuryl alcohol using platinum dioxide as a catalyst, 1,2-pentanediol is said to be formed in almost quantitative yield. 1,2-pentanediol was isolated from acetic acid in the form of diacetate.

[0009] US Patent 6,528,665 B1 proposes a process for preparing alkanediols that are as pure as possible. According to US Patent 6,528,665 B1, purification is carried out at the epoxyalkane stage before the epoxyalkane is hydrolyzed to the corresponding alkanediol.

[0010] EP 1876162 A1 describes the preparation of alkanediols from the corresponding olefins by epoxidation and subsequent hydrolysis. The crude products thus obtained were further purified therein by subsequent treatment to remove secondary products having an unpleasant odor.

[0011] The preparation of 1,2-pentanediol is today generally carried out from n-penten-1-ene available from petrochemical sources, which is reacted with the aid of peroxides (such as hydrogen peroxide) to give the corresponding epoxides, which are then converted to 1,2-pentanediol with organic acids such as formic acid or mineral acids.

[0012] This preparation method is described in EP 0257243 A1 or EP 0141775 A1 and has economic and ecological disadvantages. For example, the diester of 1,2-pentanediol formed as an intermediate in this process has to be saponified to obtain 1,2-pentanediol. If the epoxidation of n-penten-1-ene is carried out, for example, with hydrogen peroxide and formic acid, sodium formate is formed as a coupling product in the subsequent saponification of the diformate of 1,2-pentanediol with sodium hydroxide solution. It has to be disposed of, which leads to a high load of organics in the wastewater. In addition, the very low boiling point and high volatility of n-penten-1-ene require special and costly protective measures when handling and storing n-penten-1-ene. Furthermore, it would be desirable to find a simple synthesis route that is feasible on an industrial scale, preferably without the use of petrochemical feedstocks.

[0013] Finally, WO2012152849A1 (SYMRISE) discloses an alternative process for producing 1,2-pentanediol. This patent involves reacting a starting material containing one or both compounds selected from the group consisting of furfuryl alcohol and furfural with hydrogen in the presence of a heterogeneous catalyst to form a mixture. The mixture comprises 1,2-pentanediol and, optionally, one or more compounds selected from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural. Here, the heterogeneous catalyst comprises one or more metals selected from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium in metallic form, and / or one or more compounds of metals selected from the group consisting of platinum, rhodium, ruthenium, nickel, palladium, iridium, and one or more support materials selected from the group consisting of activated carbon, aluminum oxide, silicon dioxide, and silicon carbide. Objects of the invention

[0014] It is therefore an object of the present invention to provide cosmetic compositions incorporating 1,2-pentanediol and optionally further 1,2-alkanediols, with improved olfactory qualities and stability within the formulation. Summary of the Invention

[0015] A first object of the present invention refers to a cosmetic or pharmaceutical or cleansing composition comprising 1,2-pentanediol, wherein said 1,2-pentanediol is obtained from a process comprising the following steps: (a) providing at least one starting material selected from furfuryl alcohol and furfural; (b) reacting at least one of said starting materials with hydrogen in the presence of a heterogeneous catalyst to form 1,2-pentanediol, wherein said heterogeneous catalyst comprises: one or more metals selected from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium in metallic form, and / or one or more compounds of a metal selected from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium, and - one or more support materials selected from the group consisting of activated carbon, aluminum oxide, silicon dioxide, and silicon carbide. (c) The 1,2-pentanediol thus obtained is removed from the reaction mixture.

[0016] Surprisingly, it is observed that the 1,2-pentanediol obtained according to the process of International Publication WO2012 152849A1 is not only odorless when freshly prepared, but also maintains its excellent odor qualities even under harsh storage conditions and when incorporated into various cosmetic or pharmaceutical compositions. The applicant has discovered that these excellent properties are most likely related to the absence of traces of various by-products that are unstable when introduced into complex formulations and undergo chemical degradation with the generation of malodours.

[0017] Surprisingly, it has been observed that the 1,2-pentanediol obtained according to the process as described above is not only free or at least essentially free of malodorous compounds, but also from compounds that do not themselves provide malodor, but which, when incorporated into consumer product formulations, give off malodor, especially when such formulations exhibit alkaline pH values. Essentially free in the context of this specification means that the amount of malodorous compounds or compounds that cause malodor is less than 10 ppm, preferably less than 1 ppm, preferably ranging from 100 to 1.000 ppb. Typical examples of this type of impurity include butyric acid and butyric acid esters, the latter formed from traces of butyric acid when incorporated into alkaline consumer product formulations.

[0018] Preferred such compositions contain the 1,2-pentanediol in an amount from about 0.1 to about 10 weight percent, preferably from about 0.5 to about 5 weight percent, and more preferably from about 1 to about 2 weight percent.

[0019] Preferably, the composition contains from 16 to 12 carbon atoms in the 1,2-alkanediol, such as 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2-dodecanediol, 1,2-tetradecanediol, and mixtures thereof, more preferably from about 0.1 to about 5 weight percent, and most preferably from about 0.5 to about 2 weight percent. The presence of the additional 1,2-alkanediol synergistically improves the solubility of the oil component.

[0020] Preferably, the composition includes 4-hydroxyacetophenone, typically in an amount of from about 0.01 to about 2 weight percent, more preferably from about 0.1 to about 1 weight percent. The presence of 4-hydroxyacetophenone also synergistically improves the solubility of the oil component. Production of 1,2-pentanediol

[0021] As already explained above, the 1,2-pentanediol quality used according to the present invention is prepared according to the teachings of International Publication WO2012152849A1, which is therefore incorporated by reference.

[0022] Thus, the present invention provides a method for the preparation of 1,2-pentanediol, comprising stepwise reacting a starting material comprising one or both of the compounds from the group consisting of furfuryl alcohol and furfural with hydrogen in the presence of a heterogeneous catalyst to form a mixture comprising 1,2-pentanediol and, optionally, one or more compounds from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural, wherein the heterogeneous catalyst (i) comprises one or more metals from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium in metallic form and / or one or more compounds of metals from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium, and (ii) one or more support materials. Homogeneous Catalysts

[0023] Preferably, the heterogeneous catalyst comprises (i) platinum in metallic form and / or one or more platinum(IV) compounds. Particularly preferably, the heterogeneous catalyst is (i) platinum in metallic form and (ii) a catalyst comprising activated carbon, in particular platinum on activated carbon; Catalysts comprising (i) platinum in metallic form and (ii) aluminium oxide, in particular platinum on aluminium oxide; Catalysts comprising (i) platinum in metallic form and (ii) silicon dioxide, in particular platinum on silicon dioxide; Catalysts comprising (i) platinum in metallic form and (ii) silicon carbide, in particular platinum on silicon carbide; A catalyst comprising (i) platinum(IV) oxide and (ii) aluminium oxide, in particular platinum dioxide on aluminium oxide; is selected from the group consisting of:

[0024] Preferably, the heterogeneous catalyst used according to the invention is not a catalyst selected from the following list, which comprises a support material and two components: Activated carbon / Pt / ReO2, MgO / Pd / MnO2, Al2O3 / Rh / MoO3, CaO / Ru / Co3O4, Amorphous aluminosilicate / Co / TiO2, SiO2 / Ni / WO3, CeO / PtRh / Cr2O3, CaO / NiPd / Fe3O4, MgO--Al2O3 / RuFe / 2V'O5, MgO / Pt / ReO2, Al2O3 / Pd / MnO2, BaO / Rh / MoO3, Amorphous aluminosilicate / Ru / Co3O4, SiO2 / Co / TiO2, CeO / Ni / WO3, CoO / Pd / Cr2O3, Fe2O3 / Rh / Fe3O4, MnO2 / Ru / V2O5, and mixtures thereof.

[0025] Preferably, the heterogeneous catalyst used according to the invention is not a catalyst in which the following pairs of components are present: Pt / ReO2, Pd / MnO2, Rh / MoO3, Ru / Co3O4, Co / TiO2, Ni / WO3, PtRh / CrO3, NiPd / Fe3O4, RuFe / V2O5, Pd / Cr2O3, Rh / Fe3O4, Ru / V2O5, and mixtures thereof.

[0026] When component (i) of the heterogeneous catalyst consists only of platinum, the heterogeneous catalyst preferably does not contain ReO2 and Cr2O3, and preferably does not contain rhenium and chromium. This also preferably applies to heterogeneous catalysts whose component (i) contains platinum.

[0027] When component (i) of the heterogeneous catalyst consists only of palladium, the heterogeneous catalyst preferably does not contain Fe3O4 and MnO2 and Cr2O3, preferably does not contain iron and manganese and chromium. This also preferably applies to heterogeneous catalysts whose component (i) comprises palladium.

[0028] When component (i) of the heterogeneous catalyst consists only of rhodium, the heterogeneous catalyst preferably does not contain MoO3 and Fe2O3, does not contain Fe3O4, does not contain Cr2O3, and preferably does not contain molybdenum and iron and does not contain chromium. This also preferably applies to heterogeneous catalysts whose component (i) comprises palladium.

[0029] When component (i) of the heterogeneous catalyst consists only of ruthenium, the heterogeneous catalyst preferably does not comprise Co3O4 and V2O5, and preferably does not comprise cobalt and vanadium. This also preferably applies to heterogeneous catalysts whose component (i) comprises ruthenium.

[0030] When component (i) of the heterogeneous catalyst consists only of nickel, the heterogeneous catalyst preferably does not contain WO3 and Fe3O4, and preferably does not contain tungsten and iron. This also preferably applies to heterogeneous catalysts whose component (i) contains nickel.

[0031] Preferably, the heterogeneous catalyst used according to the invention does not contain oxides of the elements Re, Mo, Mn, Co, Ti, W, Cl, Fe, V and Ta.

[0032] In the heterogeneous catalyst, (i) the total concentration of platinum, rhodium, ruthenium, nickel, palladium and iridium in metallic form and in the form of platinum, rhodium, ruthenium, nickel, palladium and iridium in compounds of these metals is preferably from 0.1% to 50% by weight, preferably from 0.5% to 20% by weight, more preferably from 1 to 10% by weight and particularly preferably from 1% to 5% by weight, based on the total weight of all components of the heterogeneous catalyst.

[0033] The total concentration of (i) the metal forms of platinum, rhodium, ruthenium, nickel, palladium and iridium and the forms of platinum, rhodium, ruthenium, nickel, palladium and iridium contained in the compounds in the heterogeneous catalyst is preferably in the range of 0.01 to 10 mol %, preferably in the range of 0.05 to 5 mol %, more preferably in the range of 0.1 to 2 mol %, based on the total amount of furfuryl alcohol and furfural, and furfural is used.

[0034] Preferably, the total concentration of the metallic forms of platinum, rhodium, ruthenium, nickel, palladium and iridium and the forms of platinum, rhodium, ruthenium, nickel, palladium and iridium contained in the compounds of the metals (i) based on the total weight of all components of the heterogeneous catalyst, and the total concentration of the metallic forms of platinum, rhodium, ruthenium, nickel and the forms of platinum, rhodium, ruthenium, nickel, palladium and iridium contained in the compounds of the metals (i) of the heterogeneous catalyst based on the total amount of furfuryl alcohol and furfural used, are both in the above preferred ranges. Reaction conditions

[0035] In the case of the reaction according to the invention in the presence of a heterogeneous catalyst, molecular hydrogen should be metered in at least an equimolar amount. However, it has been found to be more advantageous to meter in excess hydrogen. Thus, in the reaction in the presence of a heterogeneous catalyst, the molar ratio of hydrogen to the total amount of furfuryl alcohol and / or furfural is greater than or equal to 1:1, preferably in the range of 4:1 to 100:1, particularly preferably in the range of 5:1 to 20:1.

[0036] In the reaction in the presence of a heterogeneous catalyst, the hydrogen partial pressure is preferably in the range from 1 bar to 20 bar, preferably in the range from 1 bar to 8 bar, more preferably in the range from 1 bar to 4 bar.

[0037] Reactions in the presence of heterogeneous catalysts take place in the liquid or gas phase.

[0038] If the reaction in the presence of a heterogeneous catalyst is carried out in the gas phase, it is preferably carried out at a temperature in the range of from 100° C. to 250° C., more preferably in the range of from 150° C. to 240° C., particularly preferably in the range of from 170° C. to 230° C. The temperature and hydrogen partial pressure are preferably within the preferred ranges given above.

[0039] The reaction in the presence of heterogeneous catalyst is preferably carried out in a reactor through which gas flow flows continuously.When entering the reactor, the gas flow comprises starting material (as described above), as well as hydrogen and optionally inert gas, and the flow rate of said gas flow is 500h-1 to 5000h-1, preferably 900h-1 to 3600h-1, based on the volume of heterogeneous catalyst (gas hourly space velocity GHSV), and / or the total concentration of furfuryl alcohol and furfural in the gas flow entering the reactor is 1mol% to 15mol%, preferably 3mol% to 10mol%.

[0040] Preferably, both the conditions regarding the flow rate and the total concentration of furfuryl alcohol and furfural in the gas stream entering the reactor are met.

[0041] The apparatus used for the reaction in the presence of a heterogeneous catalyst in the gas phase is preferably a tubular reactor filled with a heterogeneous catalyst as defined above. The feed stream fed to the tubular reactor via a suitable metering device consists of starting materials comprising one or both compounds from the group consisting of furfuryl alcohol and furfural, the required amount of hydrogen and optionally an inert gas. The furfuryl alcohol and furfural and the required amount of hydrogen are preferably in the above-mentioned molar ratio of hydrogen to the total amount of furfuryl alcohol and furfural. The furfuryl alcohol and / or furfural are converted to the gas phase by a saturator, which heats the liquid furfuryl alcohol and / or furfural to a temperature in the range of 80 to 120° C., particularly preferably 90 to 110° C., and flows with hydrogen or with hydrogen and an inert gas. Alternatively, the liquid starting materials are fed via a metering pump or similar device and an evaporator.

[0042] If the reaction in the presence of a heterogeneous catalyst is carried out in the liquid phase, it is preferably in the range of −20° C. to +100° C., preferably in the range of −20° C. to +50° C., more preferably in the range of −5° C. to +50° C., even more preferably in the range of −5° C. to +30° C., particularly preferably in the range of 0° C. to +30° C., most preferably in the range of 0° C. to +10° C. Preferably, the temperature and the hydrogen partial pressure are within the above preferred ranges.

[0043] The reaction time for the reaction in the presence of a heterogeneous catalyst as defined above is preferably in the range of from 1 hour to 20 hours, preferably in the range of from 2 hours to 12 hours, more preferably in the range of from 3 hours to 8 hours. Organic Diluents

[0044] According to the invention, the reaction of furfuryl alcohol with hydrogen is preferably carried out in an organic diluent having a pKs value at 25° C. of greater than or equal to 6, preferably greater than or equal to 8 at 25° C., more preferably greater than or equal to 10 at 25° C., and especially greater than or equal to 12 at 25° C.

[0045] Furthermore, organic diluents having a pKs value at 25° C. in the range of 12 to 25, particularly preferably in the range of 13 to 20, most preferably in the range of 14 to 18 are preferred.

[0046] The pKs value (also pKa value) corresponds to the negative common logarithm of the acid constant, Ks. Acetic acid has a pKs value of 4.75.

[0047] The diluents used according to the invention are preferably inert under the reaction conditions, ie under typical hydrogenation or hydrogenolysis conditions, the diluent itself preferably does not react, in particular is not itself reduced.

[0048] Preferably the diluent used is or comprises one or more alcohols having 1 to 4 carbon atoms, preferably selected from the group consisting of methanol, ethanol, n-propanol, isopropanol and mixtures thereof.

[0049] It is also possible to use non-polar and / or aprotic inert solvents such as dibutyl ether, methyl tert-butyl ether (MTBE), cyclohexane, n-octane, isooctane or decalin, optionally in combination with one or more of the above-mentioned alcohols having 1 to 4 carbon atoms.

[0050] In a preferred embodiment, an inorganic acid, preferably having a pKs value at 25° C. of less than 3, preferably having a pKs value at 25° C. of less than 0, can preferably be used, together with one of the diluents characterized as preferred above. A preferred inorganic acid is sulfuric acid, since it has been found to be particularly advantageous for the hydrogenolysis step in the process according to the invention.

[0051] In a particularly preferred embodiment, the reaction of furfuryl alcohol occurs in a diluent that comprises or consists of one or more alcohols selected from the group consisting of methanol, ethanol, n-propanol, isopropanol and mixtures thereof, and sulfuric acid. The combination of ethanol and sulfuric acid is particularly preferred.

[0052] When an inorganic acid, preferably sulfuric acid, is used, the total amount is preferably in the range of 0.0001 to 1% by weight, preferably in the range of 0.001 to 0.5% by weight, particularly preferably in the range of 0.01 to 0.1% by weight, based on the total mass of the diluent(s), the diluent(s) being preferably selected from the group consisting of methanol, ethanol, n-propanol, isopropanol and mixtures thereof.

[0053] The total amount of one or more diluents having a pKs value at 25° C. as characterized above and selected from the group of diluents as characterized above, is preferably in the range of 25 to 1000% by weight, preferably in the range of 50 to 500% by weight, more preferably in the range of 100 to 300% by weight, based on the total amount of furfuryl alcohol used. Preferred Embodiments

[0054] Heterogeneous catalysts preferably used according to the invention are heterogeneous catalysts comprising (i) platinum and / or one or more platinum compounds (especially platinum(IV) compounds) and (ii) one or more support materials. Heterogeneous platinum catalysts particularly preferred for use according to the invention comprise (i) platinum and / or one or more platinum(IV) compounds and (ii) one or more support materials.

[0055] Preferred platinum(IV) compounds are H2PtCl6 and its salts, preferably (NH4)2PtCl6, and platinum dioxide (of which PtO2 and PtO2 hydrate are preferred). A particularly preferred platinum(IV) compound is platinum dioxide PtO2.

[0056] Preference is given to elements, ie metals, platinum, which can be doped with iron, vanadium and / or ruthenium.

[0057] The support material is preferably solid at 25° C. and 1013 mbar and is preferably solid under hydrogenation conditions. The support material is preferably selected from the group consisting of activated carbon, silica, silicon dioxide, and / or aluminum oxide.

[0058] The platinum catalysts used according to the invention containing aluminum oxide and / or activated carbon provide the best yields and best selectivities to 1,2-pentanediol, with aluminum oxide and activated carbon being particularly preferred support materials.

[0059] Thus, preferably, the support material comprises activated carbon and / or aluminium oxide, consists exclusively of aluminium oxide or consists exclusively of activated carbon.

[0060] Gamma aluminum oxide has been found to be a particularly good support material.

[0061] Particularly good results in the process according to the invention have been achieved with platinum dioxide on aluminum oxide or platinum on activated carbon or aluminum oxide. The best results have been achieved with platinum dioxide on aluminum oxide, in particular platinum dioxide on gamma aluminum oxide.

[0062] The heterogeneous platinum catalysts used according to the invention are known per se and are available, for example, in Anal.Chem. 1956, 28(3)362-365 or Thermochimica Acta 1977, 20(3)297-308 or Proceedings of the 13th International Conference on X-ray Absorption Fine Structure (XAFS13), Stanford, Calif., 2006, editors B. Hedman and P. Pianetta, eConf C060709 (2006) (full text available at http: / / www.slaCstanford.edu / econf / C060709 / papers / 207_WEPO17.PDF) or similar thereto.

[0063] The amount of heterogeneous platinum catalyst is preferably in the range of 0.1 to 20% by weight, preferably in the range of 0.25 to 15% by weight, more preferably in the range of 0.5 to 12% by weight, based on the amount of furfuryl alcohol used.

[0064] The amount of component (i) of the heterogeneous platinum catalyst, i.e. the total content of platinum and / or platinum compounds, is preferably in the range of 0.5 to 50% by weight, preferably in the range of 0.5 to 20% by weight, more preferably in the range of 0.5 to 10% by weight, based on the total amount of the heterogeneous platinum catalyst.

[0065] Particularly preferred platinum catalysts in the process according to the invention are platinum dioxide on aluminum oxide, preferably platinum dioxide on gamma aluminum oxide, and / or platinum on activated carbon, the total platinum dioxide and / or platinum content being in the range of 0.5 to 10% by weight, based on the total amount of heterogeneous platinum catalyst used.

[0066] Preferably, the platinum catalyst (as defined above) used according to the present invention as a heterogeneous catalyst does not contain ReO2 and Cr2O3, preferably does not contain rhenium and chromium. Preferably, the platinum catalyst (as defined above) used according to the present invention as a heterogeneous catalyst does not contain CeO2, preferably does not contain cerium oxide, more preferably does not contain cerium, rhenium and chromium. Preferably, the platinum catalyst (as defined above) used according to the present invention as a heterogeneous catalyst does not contain the oxides of the elements Re, Mo, Mn, Co, Ti, W, Cl, Fe, V and Ta.

[0067] In a preferred variant of the process according to the invention using a heterogeneous platinum catalyst as defined above, the mass ratio of furfuryl alcohol to the total amount of component (i) of the heterogeneous platinum catalyst is preferably in the range of 2000:1 to 10:1, preferably in the range of 1000:1 to 25:1, more preferably in the range of 500:1 to 50:1, most preferably in the range of 300:1 to 100:1.

[0068] Preferably, the hydrogenolysis of furfuryl alcohol in the process according to the invention is carried out at a temperature in the range of -20°C to +50°C, preferably in the range of -5°C to +30°C, more preferably in the range of 0°C to +10°C.

[0069] The hydrogen pressure in the preferred variants of the process according to the invention using a heterogeneous platinum catalyst as defined above is preferably in the range from 1 to 20 bar, preferably in the range from 1 to 8 bar, preferably in the range from 1 to 8 bar. More preferably in the range from 1 to 4 bar.

[0070] The reaction time in the preferred variant of the process according to the invention with the heterogeneous platinum catalyst defined above is preferably in the range from 1 to 20 hours, preferably in the range from 2 to 12 hours, more preferably in the range from 3 to 8 hours.

[0071] The process according to the invention produces a product mixture in which 1,2-pentanediol is generally the predominant product.

[0072] The following reaction scheme shows the reaction of furfuryl alcohol in the process according to the invention, resulting in the desired main product 1,2-pentanediol and generally obtained secondary products. Moreover, the secondary products shown in the reaction scheme are formed only in small amounts due to the good yield and / or good selectivity of the process according to the invention. In particular, in addition to the target product 1,2-pentanediol, 1-hydroxy-2-pentanone is formed. In an advantageous further development of the process according to the invention (see below), 1-hydroxy-2-pentanone is also reacted in a further reaction step to form the target product 1,2-pentanediol.

[0073] Preferably, the reaction is carried out in such a way that at least 80% by weight, preferably at least 90% by weight, more preferably at least 95% by weight of the furfuryl alcohol used is reacted.

[0074] Preferably, the reaction is carried out in such a way that the reaction mixture present when the reaction is complete comprises at least 40% by weight, preferably at least 50% by weight, more preferably at least 60% by weight, particularly preferably at least 70% by weight, of 1,2-pentanediol, based on the total amount of product formed.

[0075] For clarity, the amount by weight of 1,2-pentanediol in the reaction mixture is based only on the total amount of product formed from furfuryl alcohol. Thus, the amount of unreacted furfuryl alcohol present in the reaction mixture when the reaction is complete, and the amount of platinum catalyst and diluent, should not be taken into account when determining the amount by weight of 1,2-pentanediol set forth above.

[0076] The weight of 1,2-pentanediol in the reaction mixture is based on the total amount of, specifically, 1-pentanol, 2-pentanol, tetrahydrofurfurol, 1,2-pentanediol and 1,5-pentanediol in the reaction mixture when the reaction of furfuryl alcohol is completed.

[0077] The process according to the invention can be carried out in the liquid or gas phase.

[0078] The reaction can be carried out continuously, semi-continuously, or batchwise.

[0079] The reaction is preferably carried out in a batch process, preferably in a reaction vessel, with furfuryl alcohol and optionally a diluent, preferably present in the liquid phase and mixed with the catalyst used according to the invention according to the following:

[0080] The reaction is preferably carried out in a reaction tube, the catalyst used according to the invention is in the form of a fixed bed and furfuryl alcohol, preferably the optionally used diluent is in liquid phase and in contact with the fixed catalyst bed.

[0081] The respective process for the preparation of 1,2-pentanediol by reaction of furfuryl alcohol in the presence of a heterogeneous platinum catalyst is preferably characterized by the following steps: (a) providing a starting material comprising one or both compounds from the group consisting of furfuryl alcohol and furfural; (b) providing a heterogeneous catalyst as defined above; (c) optionally providing one or more diluents; (d) preparing a mixture comprising the components provided in steps (a), (b) and optionally (c) and contacting the mixture with hydrogen; or (d') preparing a mixture comprising the starting material provided in step (a), hydrogen and optionally an inert gas, and contacting the mixture with the heterogeneous catalyst provided according to step (b); (e) reacting the mixture prepared in step (d) or (d') with hydrogen in the presence of a heterogeneous catalyst to form a mixture comprising 1,2-pentanediol and, optionally, one or more compounds from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol, and furfural; (f) Optional separation of 1,2-pentanediol by distillation.

[0082] The diluents indicated above are correspondingly preferred or particularly preferred.

[0083] The heterogeneous catalysts indicated above are thereby correspondingly preferred or particularly preferred.

[0084] Some or all of the above indicated reaction conditions are thereby preferably or particularly preferably established.

[0085] The order in which the ingredients provided in steps (a) through (c) are mixed together in step (d) is not important.

[0086] In a particularly preferred variant, the process according to the invention comprises the following steps: (a) Providing furfuryl alcohol. (b) providing at least a heterogeneous catalyst as defined above, preferably a heterogeneous platinum catalyst comprising (i) platinum and / or a platinum compound and (ii) one or more support materials. (c) optionally providing one or more diluents, preferably having a pKs value at 25° C. of 6 or greater. (d) preparing a mixture comprising the components provided in steps (a) and (b), and preferably (c). (e) contacting the mixture prepared in step (d) with hydrogen.

[0087] In an alternative preferred variant, the process according to the invention comprises the following steps: (a) providing a starting material comprising one or both compounds from the group consisting of furfuryl alcohol and furfural; (b) providing a heterogeneous catalyst as defined above; (c) preparing a mixture comprising the starting material provided in step (a), hydrogen and optionally an inert gas; and (d) in the mixture prepared in step (c), contacting the mixture with a heterogeneous catalyst provided according to step (b). (e) Reacting the starting material with hydrogen in the presence of a heterogeneous catalyst to form a mixture comprising 1,2-pentanediol and optionally one or more compounds from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural.

[0088] In the above-described process according to the invention, it is possible to achieve the following yields of 1,2-pentanediol by reaction of starting materials containing one or both compounds from the group consisting of furfuryl alcohol and furfural. This is superior to the known prior art. A further advantageous feature of the process according to the invention is the formation of the secondary product 1-hydroxy-2-pentanone with high yield and selectivity. In contrast, other secondary products typically formed in processes known from the prior art are formed only in small amounts in the process according to the invention. In particular, cyclic compounds can hardly be detected in the mixture obtained by the process according to the invention.

[0089] The sum of the selectivities of 1-hydroxy-2-pentanone and 1,2-pentanediol is generally greater than 80%, even in the case of almost complete conversion. In tests of processes known from the prior art for preparing 1,2-pentanediol, the compound 1-hydroxy-2-pentanone was not detected as a secondary product. The formation of 1-hydroxy-2-pentanone is advantageous compared to other secondary products, since 1-hydroxy-2-pentanone can be easily and very selectively hydrogenated to 1,2-pentanediol under suitable conditions in the presence of a second heterogeneous catalyst. This is the subject of an advantageous further development of the process according to the invention, which is described herein below. Thus, in an advantageous further development, the process according to the invention, in particular in the above-mentioned preferred variant, comprises a further step reaction of a compound from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural from the mixture. In the above-mentioned reaction in the presence of a heterogeneous catalyst, hydrogen is formed in the presence of a second heterogeneous catalyst to form 1,2-pentanediol. The second heterogeneous catalyst comprises (i') one or more metals from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium in metallic form and / or one or more compounds of metals from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium, and (ii') one or more support materials.

[0090] This advantageous further development of the process according to the invention makes it possible to increase the overall selectivity of 1,2-pentanediol to more than 80%. It is not necessary to separate the 1,2-pentanediol before reacting in the presence of the second heterogeneous catalyst. Cocatalyst

[0091] If a promoter is applied, the total concentration of platinum, rhodium, ruthenium, nickel, palladium and iridium in metallic form contained in the compound, and of the forms platinum, rhodium, ruthenium, nickel, palladium and iridium, is preferably in the range of 0.1% to 20% by weight, preferably 0.5% to 10% by weight, based on the total weight of all components of the second heterogeneous catalyst.

[0092] In a preferred variant of this advantageous further development of the process according to the invention, the heterogeneous cocatalysts have the same composition.

[0093] Preferably, the support material (ii) of the heterogeneous catalyst and / or the support material (ii') of the heterogeneous cocatalyst is a solid at 25° C. and 1013 mbar, preferably also at 230° C. and 1013 mbar. The support material (ii) and / or the support material (ii') is preferably selected from the group consisting of activated carbon, silica, silicon dioxide, silicon carbide, aluminum oxide, zirconium dioxide, titanium dioxide, niobium trioxide, silicon dioxide and mixtures thereof.

[0094] The reaction in the presence of the heterogeneous cocatalyst takes place in the liquid or gas phase. If the reaction in the presence of the second heterogeneous catalyst takes place in the gas phase, the temperature is preferably in the range of 25° C. to 240° C., particularly preferably in the range of 100° C. to 130° C., and / or the hydrogen partial pressure is in the range of 1 bar to 10 bar. Preferably, the temperature and the hydrogen partial pressure are in the preferred ranges described herein.

[0095] Preferably, the reaction in the presence of the second heterogeneous catalyst is carried out in a reactor through which a gas stream flows continuously. Upon entering the reactor, the gas stream contains the mixture formed in the reaction in the presence of the heterogeneous catalyst described above, as well as hydrogen and optionally an inert gas. The flow rate of the gas stream is 500h-1 to 5000h-1, preferably 900h-1 to 3600h-1, based on the volume of the second heterogeneous catalyst (gas hourly space velocity GHSV), and / or the total concentration of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural in the gas stream entering the reactor is 1 mol% to 15 mol%, preferably 3 mol% to 10 mol%.

[0096] Preferably, both the conditions regarding the flow rate and the total concentration of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural in the gas stream entering the reactor are met. Hydrogenation

[0097] In a preferred variant of the process according to the invention, both the reaction in the presence of the heterogeneous catalyst and the reaction in the presence of the second heterogeneous catalyst are carried out in the gas phase. This variant has the advantage that no diluent (solvent) is required. This represents a considerable economic and ecological advantage. In this variant of the process according to the invention, preferably an apparatus is used which comprises a reaction tube and a second reaction tube connected downstream of the reaction tube. The heterogeneous catalyst is arranged in the reaction tube and the second heterogeneous catalyst is arranged in the second reaction tube. This makes it possible to set a temperature of the reaction tube different from that of the second reaction tube.

[0098] If the reaction in the presence of the second heterogeneous catalyst is carried out in the liquid phase, the temperature is in the range of −20° C. to +150° C., preferably −20° C. to +50° C., more preferably −5 to +50° C., even more preferably −5 to +30° C., particularly preferably 0 to +30° C., most preferably -particularly preferably 0 to +10° C. and / or the hydrogen partial pressure is in the range of 1 bar to 100 bar, preferably 1 bar to 50 bar, more preferably 1 bar to 20 bar. Preferably, the temperature and hydrogen partial pressure are in the preferred ranges described herein.

[0099] Preferably, the liquid phase comprises one or more, preferably polar, diluents, the diluent or diluents being preferably selected from the group consisting of water, alcohols having 1 to 4 carbon atoms, terminally hydroxy-functionalized ethers of aliphatic ether oligomers and cyclic ethers, and mixtures thereof. The diluents used according to the invention are preferably inert under hydrogenation conditions, i.e., the diluents preferably do not react themselves, in particular are not reduced themselves, under typical hydrogenation conditions.

[0100] Alcohols having 1 to 4 carbon atoms preferably used as diluents are selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol. Preferred ethers used as diluents are selected from the group consisting of aliphatic ethers such as methyl tert-butyl ether, oligomeric terminal hydroxy-functionalized ethers such as diethylene glycol and triethylene glycol, cyclic ethers such as tetrahydrofuran and dioxane, or mixtures thereof.

[0101] The stirred vessel reactor is preferably used as the apparatus for the reaction in the presence of the second heterogeneous catalyst. The reaction time of the reaction in the presence of the second heterogeneous catalyst in the stirred vessel reactor is preferably in the range of 0.25 to 20 hours, preferably in the range of 2 to 12 hours, more preferably in the range of 3 to 8 hours.

[0102] In a particularly preferred variant of the process according to the invention, the reaction of the starting material, which comprises one or both compounds from the group consisting of furfuryl alcohol and furfural, in the presence of a heterogeneous catalyst, takes place in the gas phase. And the reaction of the compounds from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural from the mixture formed in the presence of the heterogeneous catalyst with hydrogen in the presence of a second heterogeneous catalyst takes place in the liquid phase. To that end, the organic components of the mixture formed in the presence of the heterogeneous catalyst are condensed (i.e. converted into the liquid phase) in a suitable device. The condensate obtained is then transferred to a reactor, preferably a stirred vessel reactor, to carry out the reaction in the presence of the second heterogeneous catalyst. Preferably, the reaction conditions established in this procedure for the reaction in the presence of a heterogeneous catalyst are such that an almost complete conversion of the starting compounds furfuryl alcohol or furfural is achieved.

[0103] One or more diluents are preferably added to the condensate that is formed, the total amount of diluent added to the condensate preferably ranging from 25 to 1000% by weight, preferably from 50 to 500% by weight, more preferably from 100 to 300% by weight, based on the mass of the condensate.

[0104] (i) The total concentration of platinum, rhodium, ruthenium, nickel, palladium and iridium in metallic form and of the forms platinum, rhodium, ruthenium, nickel, palladium and iridium contained in the compound of the metals of the second heterogeneous catalyst is preferably in the range of 0.01 to 10 mol %, based on the amount of 1-hydroxy-2-pentanone contained in the condensate.

[0105] The method according to the invention according to the above advantageous further development is preferably characterized by the following steps: (a) providing a starting material comprising one or both compounds from the group consisting of furfuryl alcohol and furfural; (b) providing a heterogeneous catalyst as defined above; (c) optionally providing one or more diluents; (d) preparing a mixture comprising the components provided in steps (a) and (b) and optionally (c) and contacting the mixture with hydrogen; or (d') preparing a mixture comprising the starting material provided in step (a) and hydrogen and optionally an inert gas and contacting the mixture with a heterogeneous catalyst provided according to step (b), (e) reacting the mixture prepared in step (d) or (d') with hydrogen in the presence of a heterogeneous catalyst to form a mixture comprising 1,2-pentanediol and one or more compounds from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol, and furfural; (f) providing a second heterogeneous catalyst as defined above; (g) optionally providing one or more dilutions; (h) optionally, condensing the organic components of the mixture formed in step (e), and preparing a mixture comprising the mixture formed in step (e) or the organic components condensed therefrom, and contacting the components and mixture provided in steps (f) and, optionally, (g) with hydrogen; or (h') contacting the mixture formed in step (e) with a second heterogeneous catalyst provided according to step (f) in the presence of hydrogen and optionally an inert gas; (i) reacting a compound from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural from the mixture formed in step (e) with hydrogen in the presence of a second heterogeneous catalyst to form 1,2-pentanediol; (j) Optional separation of 1,2-pentanediol by distillation.

[0106] The diluents indicated above as preferred or particularly preferred are accordingly preferred or particularly preferred.

[0107] Thereby, the heterogeneous catalysts indicated above are accordingly preferred or particularly preferred.

[0108] One, more or all of the reaction conditions set forth above are thereby established. The order in which the compounds provided in steps (a) through (c) are mixed together in step (d) is not important.

[0109] In all process variants according to the invention, the unreacted hydrogen can be very easily separated from the organic components of the reaction mixture, for example in a condenser, and fed to the reaction again in the presence of a heterogeneous catalyst.

[0110] In a preferred variant, the process according to the invention comprises the following steps: (a) providing a starting material comprising one or both compounds from the group consisting of furfuryl alcohol and furfural; (b) providing a heterogeneous catalyst as defined above; (d') preparing a mixture comprising the starting material provided in step (a) and hydrogen and optionally an inert gas, and contacting the mixture with the heterogeneous catalyst provided according to step (b); (e) reacting the mixture prepared in step (d') with hydrogen in the presence of a heterogeneous catalyst to form a mixture comprising 1,2-pentanediol and one or more compounds from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural; (f) providing a second heterogeneous catalyst as defined above; (h') contacting the mixture formed in step (e) with a second heterogeneous catalyst provided according to step (f) in the presence of hydrogen and optionally an inert gas; (i) reacting a compound from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural from the mixture formed in step (e) with hydrogen in the presence of a second heterogeneous catalyst to form 1,2-pentanediol; (j) optionally isolating 1,2-pentanediol by distillation.

[0111] In a second preferred variant, the process according to the invention comprises the following steps: (a) providing a starting material comprising one or both compounds from the group consisting of furfuryl alcohol and furfural; (b) providing a heterogeneous catalyst as defined above; (c) optionally providing one or more diluents; (d) preparing a mixture comprising the components provided in steps (a) and (b), and optionally (c), and contacting the mixture with hydrogen; (e) reacting the mixture prepared in step (d) with the starting materials and hydrogen in the presence of a heterogeneous catalyst to form a mixture comprising 1,2-pentanediol and one or more compounds from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol, and furfural; (f) providing a second heterogeneous catalyst as defined above; (g) optionally providing one or more diluents; (h) preparing a mixture comprising the mixture formed in step (e), the catalyst provided in step (f), and optionally a diluent provided in step (g), and contacting the mixture with hydrogen; (i) reacting a compound from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural from the mixture formed in step (e) with hydrogen in the presence of a second heterogeneous catalyst to form 1,2-pentanediol; (j) Optional separation of 1,2-pentanediol by distillation.

[0112] In a third preferred variant, the process according to the invention comprises the following steps: (a) providing a starting material comprising one or both compounds from the group consisting of furfuryl alcohol and furfural; (b) providing a heterogeneous catalyst as defined above; (d') preparing a mixture comprising the starting material provided in step (a) and hydrogen and optionally an inert gas, and contacting the mixture with the heterogeneous catalyst provided according to step (b); (e) reacting the mixture prepared in step (d') with hydrogen in the presence of a heterogeneous catalyst to form a mixture comprising 1,2-pentanediol and one or more compounds from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol, and furfural; (f) providing a second heterogeneous catalyst as defined above; (g) optionally providing one or more dilutions; (h) condensing the organic component of the mixture formed in step (e), preparing a mixture comprising the organic component condensed from the mixture formed in step (e) and the components provided in steps (f) and optionally (g), and contacting the mixture with hydrogen; (i) reacting a compound from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural from the mixture formed in step (e) with hydrogen in the presence of a second heterogeneous catalyst to form 1,2-pentanediol; (j) Optional separation of 1,2-pentanediol by distillation.

[0113] In a fourth preferred variant, the process according to the invention comprises the following steps: (a) providing a starting material comprising one or both compounds from the group consisting of furfuryl alcohol and furfural; (b) providing a heterogeneous catalyst as defined above; (c) the optional provision of one or more diluents; (d) preparing a mixture comprising the components provided in steps (a) and (b) and optionally (c) and contacting the mixture with hydrogen; (e) reacting the mixture prepared in step (d) with hydrogen in the presence of a heterogeneous catalyst to form a mixture comprising one or more compounds from the group consisting of 1,2-pentanediol and 1-hydroxy-2-pentanone, furfuryl alcohol and furfural; (f) providing a second heterogeneous catalyst as defined above; (h') contacting the mixture formed in step (e) with a second heterogeneous catalyst provided according to step (f) in the presence of hydrogen and optionally an inert gas; (i) reacting a compound from the group consisting of 1-hydroxy-2-pentanone, furfuryl alcohol and furfural from the mixture formed in step (e) with hydrogen in the presence of a second heterogeneous catalyst to form 1,2-pentanediol; (j) Optional separation of 1,2-pentanediol by distillation.

[0114] In the process according to the invention, in particular in the preferred variants and the abovementioned advantageous further developments, a product mixture is produced in which 1,2-pentanediol generally represents the main product.

[0115] The following reaction scheme shows the reaction of furfural or furfuryl alcohol in the process according to the invention with the intermediate 1-hydroxy-2-pentanone to give the desired main product 1,2-pentanediol and generally secondary products obtained thereby. When furfural is used as a starting material, it is first converted to furfuryl alcohol.

[0116] If the process according to the invention is carried out as a single-stage process (comprising a reaction step in the presence of a heterogeneous catalyst as described above, but without a further reaction step in the presence of a heterogeneous cocatalyst), then in addition to the target product 1,2-pentanediol, a secondary product is formed, as shown in brackets at the bottom of the scheme, as well as 1-hydroxy-2-pentanone. If the process according to the invention is carried out according to an advantageous manner, then in an advantageous further development as a two-stage process (comprising a reaction step in the presence of a heterogeneous catalyst as described above and a further reaction step in the presence of a second heterogeneous catalyst as described above), then in addition to the target product 1,2-pentanediol, a secondary product is formed, as shown in brackets at the bottom of the scheme, while the 1-hydroxy-2-pentanone formed in the reaction in the presence of a heterogeneous catalyst is mainly converted to 1,2-pentanediol in the reaction in the presence of the second heterogeneous catalyst. This variant is represented in the above scheme by a two-part arrow labeled "two-stage process".

[0117] Preferably, the reaction is carried out so that at least 80% by weight, preferably at least 90% by weight, more preferably at least 95% by weight, of the furfural and / or furfuryl alcohol used is reacted.

[0118] Preferably, the reaction is carried out so that the reaction mixture present after the one-stage or two-stage process contains at least 30% by weight 1,2-pentanediol, preferably at least 50% by weight, more preferably at least 70% by weight, particularly preferably at least 80% by weight, based on the total amount of products formed. The amount of 1,2-pentanediol or 1-hydroxy-2-pentanone in the reaction mixture is based on the total amount of products formed from furfuryl alcohol or furfural. Therefore, when determining the amount Y of 1,2-pentanediol, the amount of unreacted furfuryl alcohol or furfural still present in the reaction mixture when the reaction is completed, as well as the amount of catalyst and diluent, should not be taken into account. The amount Y of 1,2-pentanediol or 1-hydroxy-2-pentanone in the reaction mixture is based on the total amount of, inter alia, 1-pentanol, 2-pentanol, pentane, tetrahydrofurfuryl alcohol, 1-hydroxy-2-pentanone, methylfuran, methyltetrahydrofuran, 1,2-pentanediol and 1,5-pentanediol in the reaction mixture when the reaction is complete. Cosmetic and / or pharmaceutical compositions

[0119] The cosmetic or pharmaceutical compositions according to the present invention are representative of skin care, hair care, personal care, sun care and / or oral care products, such as cosmetic creams, lotions, sprays, emulsions, ointments, gels or mousses.

[0120] The compositions according to the invention may be used in the form of abrasives, anti-acne agents, agents against skin aging, anti-cell inflammation agents, anti-dandruff agents, anti-inflammatory agents, irritation prevention agents, irritation suppressing agents, antioxidants, astringents, antiperspirants, disinfectants, antistatic agents, binders, buffers, carrier materials, chelating agents, cell stimulants, cleaning agents, care agents, depilatories, surface active substances, deodorants, antiperspirants, softeners, emulsifiers, enzymes, essential oils, fibres, film formers, fixatives, foam formers, foam stabilizers, foam prevention substances, foam boosters, gelling agents, gel formers, hair care agents, hair setting agents, hair straightening agents, moisturising agents, moisturising agents, bleaching agents, strengthening agents, stain removers, optical brighteners, impr rash agents, antifouling agents, friction reducing agents, lubricants, moisturising creams, ointments, opacifiers, plasticisers, coating agents, abrasives, polishing agents, polymers, powders, proteins, re-oiling agents, polishing agents, silicones, skin soothing agents, skin cleansing agents, skin care agents, skin healing agents, skin whitening agents, skin protection agents, skin softeners, hair growth agents, cooling agents, skin cooling agents, warming agents, skin warming agents, stabilizers, UV absorbers, UV filters, detergents, fabric conditioning agents, suspending agents, skin tanning agents, thickeners, vitamins, oils, waxes, fats, phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, alpha-hydroxy acids, polyhydroxy fatty acids, liquefying agents, dyes, colour protection agents, pigments, corrosion inhibitors, fragrances, flavours, aromatic substances, polyols, surfactants, electrolytes, organic solvents or silicone derivatives as additional auxiliaries and additives. Surfactants

[0121] Preferred auxiliaries and additives are anionic and / or amphoteric or zwitterionic surfactants.Typical examples of anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, alkyl ethersulfonates, glycerol ethersulfonates, methyl estersulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, isethionate fatty acids, sarcosinate fatty acids, tauride fatty acids, N-acyl amino acids such as acyl lactate, acyl tartrate, acyl glutamate and acyl aspartate, alkyl oligoglucoside sulfates, protein fatty acid condensates (especially wheat-based vegetable products) and alkyl (ether) phosphates. If the anionic surfactants contain polyglycol ether chains, they preferably have a narrow range homologue distribution, but may have a conventional homologue distribution. Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolium betaines and sulfobetaines. All the mentioned surfactants are known compounds. Information on their structure and production can be found in the relevant synoptic works. For example, J. Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp. 54-124, or J. Falbe (ed.), "Katalysatoren, Tenside und Mineraloladditive (Cat-alysts, Surfactants and Mineral Oil Additives)", Thieme Verlag, Stuttgart, 1978, pp. 123-217. The percentage content of surfactants in the preparation may be from 0.1 to 10% by weight, preferably from 0.5 to 5% by weight, based on the preparation. oil body

[0122] Suitable oil bodies which form a constituent of the O / W emulsions are, for example, gelbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C6-C22-fatty acids with linear or branched C6-C22-fatty alcohols or esters of branched C6-C13-carboxylic acids with linear or branched C6-C22-fatty alcohols, such as, for example, myristate myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, Myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl behenate, oleate isostearyl oleate, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl erucate, erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenate and erucyl erucate.Furthermore, esters of linear C6-C22-fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of C18-C38-alkylhydroxycarboxylic acids with linear or branched C6-C22-fatty alcohols, in particular dioctyl malate, Esters of linear and / or branched fatty acids with polyhydric alcohols (such as, for example, propylene glycol, dimerdiol or trimertriol) and / or Guerbet alcohols, triglycerides based on C6-C10 fatty acids, liquid mono- / di- / triglyceride mixtures based on C6-C18 fatty acids, esters of C6-C22-fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C2-C12-dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon atoms or polyols having 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C22-fatty alcohol carbonates, Also suitable are, for example, dicaprylyl carbonate (Cetiol® CC), Guerbet carbonates based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of benzoic acid with linear and / or branched C6-C22 alcohols (e.g. Fin-solv® TN), linear or branched, symmetrical or asymmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, such as, for example, dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicone, silicone methicone grades, etc.) and / or aliphatic or naphthenic hydrocarbons, such as, for example, squalene, squalene or dialkylcyclohexanes. emulsifier

[0123] Other surfactants may also be added to the formulation as emulsifiers including, for example: · Products of addition of 2-30 mol of ethylene oxide and / or 0-5 mol of propylene oxide to linear C8-22 fatty alcohols, C12-22 fatty acids, and alkylphenols containing 8-15 carbon atoms in the alkyl group. ·C12 / 18 fatty acid mono- and diesters of addition products of 1-30 moles of ethylene oxide to glycerol. Glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated fatty acids containing 6 to 22 carbon atoms and their ethylene oxide addition products. · Addition products of 15-60 mol of ethylene oxide onto castor oil and / or hydrogenated castor oil. Polyol esters, in particular polyglycerol esters such as polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimerate isostearate. Mixtures of several compounds from these classes are also suitable. Addition products of 2-15 mol of ethylene oxide to castor oil and / or hydrogenated castor oil. · Partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, -dipentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (e.g. cellulose). Mono-, di- and trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates and their salts. · Wool wax alcohol. ·Polysiloxane / polyalkylpolyether copolymers and corresponding derivatives. Mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohols, and / or mixed esters of C6-22 fatty acids, methyl glucose and a polyol, preferably glycerol or polyglycerol. Polyalkylene glycols. Glycerol carbonate.

[0124] The addition products of ethylene oxide and / or propylene oxide to fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters and sorbitan mono- and diesters of fatty acids or to castor oil are known commercial products. They are homolog mixtures, the average degree of alkoxylation of which corresponds to the ratio between the amount of ethylene oxide and / or propylene oxide and the substrate with which the addition reaction is carried out. C12 / 18 fatty acid monoesters and diesters of the addition products of ethylene oxide to glycerol are known as lipid layer enhancers in cosmetic formulations. Preferred emulsifiers are described in more detail below.

[0125] Partial glycerides. Typical examples of suitable partial glycerides are hydroxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid monoglyceride, isostearic acid diglyceride, oleic acid monoglyceride, oleic acid diglyceride, ricinoleic acid monoglyceride, ricinoleic acid diglyceride, linoleic acid monoglyceride, linoleic acid diglyceride, linolenic acid monoglyceride, linolenic acid diglyceride, erucic acid monoglyceride, erucic acid diglyceride, tartaric acid monoglyceride, tartaric acid diglyceride, citric acid monoglyceride, malic acid monoglyceride, malic acid diglyceride and technical mixtures thereof. They may still contain small amounts of triglycerides from the manufacturing process. Also suitable are the addition products of 1 to 30, preferably 5 to 10 mol of ethylene oxide to the above partial glycerides.

[0126] Sorbitan esters. Suitable sorbitan esters include sorbitan monoisostearate, sorbitan sesquiisostearate, sorbitan diisostearate, sorbitan triisostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, sorbitan monoerucate, sorbitan sesquierucate, sorbitan diricinoleate, sorbitan trierucate, sorbitan monoricinoleate, sorbitan sesquierucate, sorbitan diricinoleate, sorbitan triricinole ... triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan triricinoleate, sorbitan hydroxystearate, sorbitan sesquihydroxystearate, sorbitan dihydroxystearate, sorbitan trihydroxystearate, sorbitan monotartrate, sorbitan sesquitartrate, sorbitan ditartrate, sorbitan tritartrate, sorbitan monocitrate, sorbitan sesquicitrate, sorbitan dicitrate, sorbitan tricitrate, sorbitan monomaleate, sorbitan sesquimaleate, sorbitan dimaleate, sorbitan trimaleate and technical mixtures thereof. Also suitable are addition products of 1 to 30, preferably 5 to 10 mol of ethylene oxide onto the abovementioned sorbitan esters.

[0127] Polyglycerol ester. Typical examples of suitable polyglycerol esters are Polyglyceryl-2 Dipolyhydroxystearate (Dehymuls® PGPH), Polyglycerin-3-Diisostearate (Lameform® TGI), Polyglyceryl-4 Isostearate (Isolan® GI 34), Polyglyceryl-3 Oleate, Diisostearoyl Polyglyceryl-3, Diisostearic Acid (Isolan® PDI), Polyglyceryl-3 Methylglucose Distearate (TegoCare® 450), Polyglyceryl-3 Beeswax (CeraBellina®), Polyglyceryl-4 Caprate (Polyglycerin Caprate T2010 / 90), Polyglyceryl-3 Cetyl Ether. (Chimexane® NL), polyglyceryl-3 distearate (Cremophor® GS32) and polyglyceryl polyricinoleate (Admul® WOL1403), polyglyceryl dimerate isostearate and mixtures thereof. Examples of other suitable polyol esters are mono-, di-, triesters of trimethylolpropane or of pentaerythritol, lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid, and the like, optionally reacted with 1 to 30 moles of ethylene oxide.

[0128] Anionic emulsifier. Typical anionic emulsifiers are aliphatic C12-22 fatty acids, such as palmitic acid, stearic acid or behenic acid, and C12-22 dicarboxylic acids, such as azelaic acid or sebacic acid.

[0129] Amphoteric emulsifier. Other suitable emulsifiers are amphoteric or zwitterionic surfactants. Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylic acid group and one sulfonic acid group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines, which are N-alkyl-N,N-dimethylammonium glycinates, such as cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinates, such as cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinates, which contain 8 to 18 carbon atoms in the alkyl or acyl group. Particularly preferred are fatty acid amide derivatives known under the CTFA name of cocamidopropyl betaine. Ampholytic surfactants are also suitable emulsifiers. Amphoteric surfactants are surface-active compounds that contain at least one free amino group and at least one -COOH- or -SO3H- group in the molecule in addition to a C8 / 18 alkyl or acyl group and can form salts internally. Examples of suitable amphoteric surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkyl amino butyric acids, N-alkyl imino dipropionic acids, N-hydroxyethyl-N-alkyl-amidopropyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkyl amino propionic acids, and alkyl amino acetic acids containing about 8 to 18 carbon atoms in the alkyl group. Particularly preferred amphoteric surfactants are N-coco alkyl amino propionates, coco acylmino ethyl amino propionates, and C12 / 18 acylsarcosines. Superfatting and consistency factors

[0130] Superfatting agents may be selected from materials such as lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the fatty acid alkanolamides also functioning as foam stabilizers.

[0131] The consistency factors mainly used are fatty alcohols or hydroxyfatty alcohols containing from 12 to 22, preferably from 16 to 18, carbon atoms, as well as partial glycerides, fatty acids or hydroxyfatty acids. Combinations of these substances with alkyl oligoglucosides of the same chain length and / or fatty acid N-methylglucamides and / or polyglycerol poly-12-hydroxystearates are preferably used. Thickeners and Rheology Additives

[0132] Suitable thickeners are polymeric thickeners such as Aerosil® types (hydrophilic silicas), polysaccharides, more particularly xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethylcellulose and hydroxyethylcellulose, relatively high molecular weight polyethylene glycol monoesters and diesters of fatty acids, polyacrylates (for example Carbopols® [Goodrich] or Synthalens® [Sigma]), polyacrylamides, polyvinyl alcohols and polyvinylpyrrolidones, surfactant acids, for example ethoxylated fatty glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylolpropane, narrow range fatty alcohol ethoxylates and electrolytes, such as sodium chloride or ammonium chloride. polymer

[0133] Suitable cationic polymers are, for example, quaternized hydroxyethylcellulose available from Amerchol under the name Polymer JR400®, cationic starch, cationic cellulose derivatives, such as copolymers of diallyl ammonium salt and acrylamide, vinylpyrrolidone / vinylimidazole polymers, such as, for example, Luviquat® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides, such as, for example, lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat® L, Grunau), quaternized wheat polypeptides, polyethyleneimines, cationic silicone polymers, such as, for example, amodimethicone, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine®, Sandoz), copolymers of acrylic acid and dimethyldiallylammonium chloride. These include copolymers with chitinamides (Merquat® 550, Chemviron), polyaminopolyamides and their crosslinked water-soluble polymers, such as cationic chitin derivatives, such as chitosan, optionally quaternized in microcrystalline distribution, condensation products of dihaloalkyls, such as dibromobutane, with bis-dialkylamines, such as bis-dimethylamino-1,3-propane, valuable guar gums, such as Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers, such as Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol, and the various polyquaternium types (6, 7, 32, 37, etc.) marketed under the trade names Rheocare® CC or Ultragel® 300.

[0134] Suitable anionic, zwitterionic, amphoteric and nonionic polymers are, for example, vinyl acetate / crotonic acid copolymers, pyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and their esters, non-crosslinked and polyol-crosslinked polyacrylic acids, acrylamidopropyltrimethylammonium chloride / acrylate copolymers, octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, vinylpyrrolidone / dimethylaminoethyl methacrylate / vinyl caprolactam terpolymers and optionally derivatized cellulose ethers and silicones. Pearl Wax

[0135] Suitable pearlescent waxes are, for example, alkylene glycol esters, in particular ethylene glycol distearate; fatty acid alkanolamides, in particular coco fatty acid diethanolamide; partial glycerides, in particular stearic acid monoglyceride; esters of polybasic, optionally hydroxy-substituted carboxylic acids with fatty alcohols containing 6 to 22 carbon atoms, in particular long-chain esters of tartaric acid; fatty compounds such as, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates containing at least 24 carbon atoms in total, in particular laurone and distearyl ether; fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring-opening products of olefin epoxides containing 12 to 22 carbon atoms with fatty alcohols containing 12 to 22 carbon atoms and / or polyols containing 2 to 15 carbon atoms and 2 to 10 hydroxyl groups and mixtures thereof. silicone

[0136] Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones, and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glycoside-, and / or alkyl-modified silicone compounds, which can exist both as liquids and resins at room temperature. Another suitable silicone compound is simethicone, which is a mixture of dimethicone and hydrogenated silicate with an average chain length of 200 to 300 dimethylsiloxane units. A detailed overview of suitable volatile silicones is disclosed in Todd et al. Cosm. Toil. 91, 27 (1976). Waxes and stabilizers

[0137] In addition to the natural oils used, waxes may also be present in the preparation, such as candelilla wax, carnauba wax, Japan wax, esparto grass wax, cork wax, guaruma wax, rice oil wax, sugarcane wax, olicury wax, montan wax, beeswax, shellac wax, spermaceti, lanolin (wool wax), uropygial fat, ceresin, ozocerite (earth wax), petrolatum, paraffin wax and microwaxes, chemically modified waxes (hard waxes), such as montan ester wax, sasol wax, hydrogenated jojoba wax, synthetic waxes such as polyalkylene waxes and polyethylene glycol waxes.

[0138] For example, magnesium, aluminum and / or zinc stearate or metal salts of fatty acids such as ricinoleic acid can be used as stabilizers. Main sun protection factors

[0139] Primary sun protection agents in the context of the invention are, for example, organic substances (light filters) that are liquid or crystalline at room temperature and are capable of absorbing ultraviolet radiation and releasing the absorbed energy in the form of long-wave radiation, such as heat.

[0140] The formulations according to the invention advantageously comprise at least one UV-A filter and / or at least one UV-B filter and / or a broadband filter and / or at least one inorganic pigment. The formulations according to the invention preferably comprise at least one UV-B filter or a broadband filter, more particularly at least one UV-A filter and at least one UV-B filter.

[0141] Preferred cosmetic compositions, preferably topical formulations according to the invention, comprise one, two, three or more sun protection factors selected from the group consisting of 4-aminobenzoic acid and derivatives, salicylic acid derivatives, benzophenone derivatives, dibenzoylmethane derivatives, diphenylacrylates, 3-imidazol-4-ylacrylic acid and its esters, benzofuran derivatives, benzylidene malonate derivatives, polymeric UV absorbers comprising one or more organosilicone radicals, cinnamic acid derivatives, camphor derivatives, trianilino-s-triazine derivatives, 2-hydroxyphenylbenzotriazole derivatives, phenylbenzimidazole sulfonic acid derivatives and their salts, anthranilic acid menthyl esters, benzotriazole derivatives and indole derivatives.

[0142] In addition, it is advantageous to combine the compound of formula (I) with an active ingredient that penetrates into the skin, protects skin cells from the inside against damage caused by sunlight, and reduces the level of skin matrix metalloproteases.Preferred components, so-called aryl hydrocarbon receptor antagonists, are described in WO2007 / 128723, which is incorporated herein by reference.Preferred is 2-benzylidene-5,6-dimethoxy-3,3-dimethylindan-1-one.

[0143] The UV filters cited below which can be used within the context of the present invention are preferred, but are not limiting.

[0144] The UV filters preferably used are selected from the group consisting of: p-Aminobenzoic acid p-Aminobenzoic acid ethyl ester (25 mol) ethoxylated (INCI name: PEG-25 PABA) p-Dimethylaminobenzoic acid-2-ethylhexyl ester p-Aminobenzoic acid ethyl ester (2 mol) N-propoxylated p-Aminobenzoic acid glycerol ester Salicylic acid homomenthyl ester (homosalate) (NeoHeliopan® HMS) Salicylic acid-2-ethylhexyl ester (NeoHeliopan® OS) Triethanolamine salicylate 4-Isopropylbenzyl Salicylate Anthranilic acid menthyl ester (NeoHeliopan® MA) Diisopropyl cinnamate ethyl ester p-Methoxycinnamic acid-2-ethylhexyl ester (NeoHeliopan® AV) Diisopropyl cinnamate methyl ester p-Methoxycinnamic acid isoamyl ester (NeoHeliopan® E1000) p-Methoxycinnamic acid diethanolamine salt p-Methoxycinnamic acid isopropyl ester 2-Phenylbenzimidazole sulfonic acid and salts (NeoHeliopan® Hydro) 3-(4'-trimethylammonium)benzylidenebornan-2-one methyl sulfate Beta-imidazole-4(5)-acrylic acid (urocanic acid) 3-(4'-sulfo)benzylidenebornan-2-one and salts 3-(4'-Methylbenzylidene)-D,L-Camphor (NeoHeliopan® MBC) 3-Benzylidene-D,L-camphor N-[(2 and 4)-[2-(oxoborn-3-ylidene)methyl]benzyl]acrylamide polymer 4,4'-[(6-[4-(1,1-dimethyl)aminocarbonyl)phenylamino]-1,3,5-triazine-2,4-diyl)diimino]-bis-(benzoic acid-2-ethylhexyl ester) (Uvasorb® HEB) Benzylidenemalonic acid polysiloxane (Parsol® SLX) Glyceryl ethylhexanoate dimethoxycinnamate Dipropylene glycol salicylate Tris(2-ethylhexyl)-4,4',4''-(1,3,5-triazine-2,4,6-triyltriimino)tribenzoate (=2,4,6-trianilino-(p-carbo-2'-ethylhexyl-1'-oxy)-1,3,5-triazine) (Uvinul® T150).

[0145] Broadband filters which are preferably combined with one or more compounds of formula (I) in the preparation according to the invention are selected from the group consisting of: 2-Ethylhexyl-2-cyano-3,3-diphenylacrylate (NeoHeliopan® 303) Ethyl 2-cyano-3,3'-diphenylacrylate 2-Hydroxy-4-methoxybenzophenone (NeoHeliopan® BB) 2-Hydroxy-4-methoxybenzophenone-5-sulfonic acid Dihydroxy-4-methoxybenzophenone 2,4-Dihydroxybenzophenone Tetrahydroxybenzophenone 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone 2-Hydroxy-4-n-octoxybenzophenone 2-Hydroxy-4-methoxy-4'-methylbenzophenone Sodium hydroxymethoxybenzophenone sulfonate 2,2'-Dihydroxy-4,4'-dimethoxy-5,5'-disulfobenzophenone disodium Phenol, 2-(2H-benzotriazol-2-yl)-4-methyl-6-(2-methyl-3(1,3,3,3-tetramethyl-1-(trimethylsilyl)oxy)disiloxyanyl)propyl) (Mexoryl® XL) 2,2'-Methylenebis-(6-(2H-benzotriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)phenol) (Tinosorb® M) 2,4-Bis-[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-1,3,5-triazine 2,4-Bis-[{4-(2-ethylhexyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine (Tinosorb® S) 2,4-Bis-[{(4-(3-sulfonato)-2-hydroxypropyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine sodium salt 2,4-Bis-[{(3-(2-propyloxy)-2-hydroxypropyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine 2,4-Bis-[{(4-(2-ethylhexyloxy)-2-hydroxy}phenyl]-6-(4-(2-methoxyethylcarbonyl)phenylamino)-1,3,5-triazine 2,4-Bis-[{(4-(3-(2-propyloxy)-2-hydroxypropyloxy)-2-hydroxy}phenyl]-6-(4-(2-ethylcarboxyl)phenylamino)-1,3,5)-triazine 2,4-Bis-[{(4-(2-ethylhexyloxy)-2-hydroxy}phenyl]-6-(1-methylpyrrol-2-yl)-1,3,5-triazine 2,4-Bis-[{(4-tris-(trimethylsiloxysilylpropyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine 2,4-Bis-[{(4-(2''-methylpropenyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine 2,4-Bis-[{(4-(1',1',1',3',5',5',5'-heptamethylsiloxy-2''-methylpropyloxy)-2-hydroxy}phenyl]-6(-4-methoxyphenyl)-1,3,5-triazine.

[0146] The composition may contain further cleansing composition ingredients, such as typical detergents and UV-A filters, which are preferably combined with one or more compounds of formula (I) in the preparations according to the invention and are selected from the group consisting of: 4-Isopropyldibenzoylmethane Terephthalylidene dibornane sulfonic acid and salts (Mexoryl® SX) 4-t-Butyl-4'-methoxydibenzoylmethane (Avobenzone) / (NeoHeliopan® 357) Phenylenebis-benzimidazyltetrasulfonic acid disodium salt (NeoHeliopan® AP) 2,2'-(1,4-phenylene)-bis-(1H-benzimidazole-4,6-disulfonic acid), monosodium salt 2-(4-Diethylamino-2-hydroxybenzoyl)benzoic acid hexyl ester (Uvinul® APlus) Indanylidene compounds according to DE 100 55 940 A1 (= WO 2002 038537A1)

[0147] The compositions may contain further typical detergent and cleansing composition ingredients, such as UV filters, which are more preferably combined with one or more compounds of formula (I) in preparations according to the invention, selected from the group consisting of: p-Aminobenzoic acid 3-(4'-trimethylammonium)benzylidenebornan-2-one methyl sulfate Salicylic acid homomenthyl ester (NeoHeliopan® HMS) 2-Hydroxy-4-methoxybenzophenone (NeoHeliopan® BB) 2-Phenylbenzimidazole Sulfonic Acid (NeoHeliopan® Hydro) Terephthalylidene dibornane sulfonic acid and salts (Mexoryl® SX) 4-tert-Butyl-4'-methoxydibenzoylmethane (NeoHeliopan® 357) 3-(4'-sulfo)benzylidenebornan-2-one and salts 2-Ethylhexyl-2-cyano-3,3-diphenylacrylate (NeoHeliopan® 303) N-[(2 and 4)-[2-(oxoborn-3-ylidene)methyl]benzyl]acrylamide polymer p-Methoxycinnamic acid-2-ethylhexyl ester (NeoHeliopan® AV) p-Aminobenzoic acid ethyl ester (25 mol) ethoxylated (INCI name: PEG-25 PABA) p-Methoxycinnamic acid isoamyl ester (NeoHeliopan® E1000) 2,4,6-Trianilino-(p-carbo-2'-ethylhexyl-1'-oxy)-1,3,5-triazine (Uvinul® T150) Phenol, 2-(2H-benzotriazol-2-yl)-4-methyl-6-(2-methyl-3(1,3,3,3-tetramethyl-1-(trimethylsilyl)oxy)-disiloxyanyl)propyl) (Mexoryl® XL) 4,4'-[(6-(4-(1,1-dimethyl)aminocarbonyl)phenylamino]-1,3,5-triazine-2,4-diyl)diimino]-bis-(benzoic acid-2-ethylhexyl ester) (Uvasorb HEB) 3-(4'-Methylbenzylidene)-D,L-Camphor (NeoHeliopan® MBC) 3-Benzylidene camphor Salicylic acid-2-ethylhexyl ester (NeoHeliopan® OS) 4-Dimethylaminobenzoic acid-2-ethylhexyl ester (Padimate O) Hydroxy-4-methoxybenzophenone-5-sulfonic acid and sodium salt 2,2'-Methylenebis-(6-(2H-benzotriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)phenol) (Tinosorb® M) Phenylenebis-benzimidazyltetrasulfonic acid disodium salt (NeoHeliopan® AP) 2,4-Bis-[{(4-(2-ethylhexyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine (Tinosorb® S) Benzylidenemalonic acid polysiloxane (Parsol® SLX) Menthyl anthranilate (NeoHeliopan® MA) 2-(4-Diethylamino-2-hydroxybenzoyl)benzoic acid hexyl ester (Uvinul® APlus) Indanylidene compounds according to DE 100 55 940 (= WO 02 / 38537).

[0148] Advantageous primary and secondary sun protection factors are described in International Publication WO2005123101A1. Advantageously, these preparations contain at least one UVA filter and / or at least one UVB filter and / or at least one inorganic pigment. The preparations may be present here in various forms as are conventionally used for sunscreen preparations. They may thus be in the form of solutions, water-in-oil (W / O) or oil-in-water (O / W) emulsions, or multiple emulsions, such as, for example, water, oil-in-water (W / O / W), gels, aqueous dispersions, solid sticks, or aerosols.

[0149] In a further preferred embodiment, the formulation according to the invention comprises a total amount of sunscreens, i.e. in particular UV filters and / or inorganic pigments (UV filtering pigments), so that the formulation according to the invention has a photoprotection factor equal to or greater than 2, preferably greater than or equal to 5. Such preparations according to the invention are particularly suitable for protecting the skin and hair. Secondary Sun Protection Factors

[0150] In addition to the group of primary sunscreen factors mentioned above, secondary sunscreen factors of the antioxidant type can also be used. Secondary sunscreen factors of the antioxidant type interrupt the photochemical reaction chain that is initiated when ultraviolet radiation penetrates the skin. Typical examples are amino acids (e.g., glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g., urocanic acid) and their derivatives, peptides, e.g., D,L-carnosine, D-carnosine, L-carnosine, and their derivatives (e.g., anserine), carotenoids, carotenes (e.g., alpha-carotene, beta-carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, liponic acid and its derivatives (e.g., dihydroliponic acid), Aurothioglucose, propylthiouracil and other thiols (e.g., thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, α-linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and very small compatible doses of sulfoximine compounds (e.g. buthionine sulfoximine, homocysteine ​​sulfoximine, buthionine sulfone, penta-, hexa- and hepta-thionine sulfoximine), as well as (metal) chelating agents (e.g. α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid, bile acids, bile extracts, bilirubin, bilirubin, Liverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g., linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and its derivatives (e.g., ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate), tocopherol and derivatives (e.g., vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl benzoate of benzoin resin,Rutinic acid and its derivatives, glycosyl rutin, ferulic acid, furfurylidene glucitol, carnosine, butylated hydroxytoluene, butylated hydroxyanisole, nordihydroguaiac resin acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, superoxide dismutase, titanium dioxide (for example, dispersion in ethanol), zinc and its derivatives (for example, ZnO, ZnSO4), selenium and its derivatives (for example, selenium methionine), stilbene and its derivatives (for example, stilbene oxide, trans-stilbene oxide), and derivatives of these active substances suitable for the purposes of the present invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids).

[0151] Advantageous inorganic secondary shading pigments are finely dispersed metal oxides and metal salts, which are also described in WO2005123101A1. The total amount of inorganic pigments, in particular hydrophobic inorganic micropigments, in the finished cosmetic preparation according to the invention is advantageously from 0.1 to 30% by weight, preferably from 0.5 to 10.0% by weight, each based on the total weight.

[0152] Also preferred are particulate UV filters or inorganic pigments, which can optionally be hydrophobized, such as oxides of titanium (TiO2), zinc (ZnO), iron (Fe2O3), zirconium (ZrO2), silicon (SiO2), manganese (such as MnO), aluminum (Al2O3), cerium (such as Ce2O3) and / or mixtures thereof. Active substances that correct skin and / or hair pigmentation

[0153] Preferred active ingredients for skin and / or hair lightening are selected from the group consisting of: Kojic acid (5-hydroxy-2-hydroxymethyl-4-pyranone), kojic acid derivatives, preferably kojic acid dipalmitate, arbutin, ascorbic acid, ascorbic acid derivatives, preferably magnesium ascorbyl phosphate, hydroquinone, hydroquinone derivatives, resorcinol, resorcinol derivatives, preferably 4-alkylresorcinols and 4-(1-phenylethyl)1,3-dihydroxybenzene (phenylethylresorcinol), cyclohexyl carbamates (preferably one or more of the cyclohexyl carbamates disclosed in WO2010 / 122178 and WO2010 / 097480), sulfur-containing molecules, preferably glutathione or cysteine, α-hydroxy acids (preferably or citric acid, lactic acid, malic acid), their salts and esters, N-acetyl tyrosine and derivatives, undecenoyl phenylalanine, gluconic acid, chromone derivatives, preferably aloesin, flavonoids, 1-aminoethylphosphinic acid, thiourea derivatives, ellagic acid, nicotinamide (nicasinamide), zinc salts, preferably zinc chloride or zinc gluconate, thujaplicin and derivatives, triterpenes, preferably maslinic acid, sterols, preferably ergosterol, benzofuranones, preferably senkyunolide, vinyl guacol, ethyl guacol, dionic acids, preferably octodecenedioic acid and / or azelanic acid, inhibitors of nitric oxide synthesis, preferably L-nitroarginine and derivatives thereof, 2,7-dinitroindazole or thiocitrulline, metal chelators (preferably α-hydroxy fatty acids, phytic acid, humic acid, bile acids, bile extracts, EDTA, EGTA and their derivatives), retinoids, soy milk and extracts, serine protease inhibitors or lipoic acid or other synthetic or natural active ingredients for skin and hair lightening, the latter preferably used in the form of extracts from plants, preferably bearberry extract, rice extract, papaya extract, turmeric extract, mulberry extract, bengkoan extract, nutgrass extract, liquorice root extract or components concentrated or isolated therefrom, preferably selected from the group consisting of glabridin or licochalcone A, Artocarpus extract, extracts of Rumex and Ramulus species, extracts of Pinus species (Pinus), extracts of Vitis species or stilbene derivatives isolated or concentrated therefrom, saxifrage extract, scutellaria extract, grape extract and / or microalgae extract, in particular Tetraselmis suecica extract,

[0154] Preferred skin whitening agents as component (b) are kojic acid and phenylethylresorcinol as tyrosinase inhibitors, beta-arbutin and alpha-arbutin, hydroquinone, nicotinamide, diacids, Mg ascorbyl phosphate and vitamin C and its derivatives, mulberry extract, benkoan extract, papaya extract, turmeric extract, nut grass extract, licorice extract (including glycyrrhizin), alpha-hydroxy acids, 4-alkylresorcinols, 4-hydroxyanisole. These skin whitening agents are preferred due to their very good activity, especially in combination with sclareolide according to the present invention. Moreover, said preferred skin whitening agents are readily available.

[0155] Advantageous skin and hair tanning active ingredients in this respect are substrates or substrate analogues of tyrosinase, such as L-tyrosine, N-acetyltyrosine, L-DOPA or L-dihydroxyphenylalanine, xanthine alkaloids and their derivatives, such as caffeine, theobromine and theophylline, proopiomelanocortin peptides, such as ACTH, α-MSH, and their peptide analogues, and other substances that bind to the melanocortin receptor, peptides, such as Val-Gly-Val-Ala-Pro-Gly, Lys-lle-Gly-Arg-Lys or Leu-lle-Gly-Lys, purines, pyrimidines, folic acid, copper salts, such as copper gluconate, chloride or pyrrolidonic acid, 1,3,4-oxadiazole-2-thiols, such as 5-pyrazin-2-yl-1,3,4-oxadiazole-2-thiol, curcumin, zinc diglycinate (Zn(GIy) 2) manganese(II) bicarbonate complexes ("pseudo cat-alase"), as described, for example, in EP 0584178, tetrasubstituted cyclohexene derivatives, as described, for example, in WO 2005 / 032501, isoprenoids, as described, for example, in WO 2005 / 102252 and WO 2006 / 010661, melanin derivatives, such as Melasyn-100 and MelanZe, diacylglycerols, aliphatic or cyclic diols, psoralens, prostaglandins and their analogues, activators of adenylate cyclase and of compounds which activate the transfer of melanosomes into keratinocytes, such as agonists of serine proteases and PAR-2 ​​receptors, extracts of plants and plant parts of the Chrysanthemum and Sanguinea species, walnut extracts, urcuma extracts, rhubarb extracts, microalgae extracts, in particular Isochrysis galbana, trehalose, erythrulose and dihydroxyacetone. Flavonoids that cause skin and hair tinting or browning (e.g., quercetin, rhamnetin, kaempferol, fisetin, genistein, daidzein, chrysin, apigenin, epicatechin, diosmin, diosmetin, morin, quercitrin, naringenin, hesperidin, phloridzin, and phloretin) may also be used.

[0156] The amounts of the aforementioned examples of additional active ingredients for regulating skin and hair pigmentation (one or more compounds) in the products according to the invention preferably range from 0.00001 to 30% by weight, preferably from 0.0001 to 20% by weight, particularly preferably from 0.001 to 5% by weight, based on the total weight of the preparation. Anti-Aging Active

[0157] In the context of the present invention, anti-aging or biogenic agents are, for example, antioxidants, matrix metalloproteinase inhibitors (MMPIs), skin moisturizers, glycosaminoglycan stimulators, anti-inflammatory agents, TRPV1 antagonists and plant extracts.

[0158] Antioxidant. Suitable antioxidants are amino acids (preferably glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (preferably urocanic acid) and derivatives thereof, peptides, preferably D,L-carnosine, D-carnosine, L-carnosine and derivatives thereof (preferably anserine), carnitine, creatine, matrikin peptides (preferably lysyl-threonyl-threonyl-lysyl-serine) and palmitoylated pentapeptides, carotenoids, carotenes (preferably alpha-carotene, β-carotene, lycopene) and their derivatives, lipoic acid and its derivatives (preferably dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (preferably thioredoxin, glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl, lauryl, palmitoyl, oleyl, gamma-linoleyl, cholesteryl, glyceryl and oligoglyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and preferably very small tolerated doses (pmol to μmol / kg) of sulfoximine compounds (preferably buthionine sulfoximine, homocysteine ​​sulfoximine, buthionine sulfone, penta-, hexa-, or heptathionine sulfoximine), as well as (metal) chelating agents (preferably α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin, α-hydroxy acids (preferably citric acid, lactic acid, malic acid), humic acid, bile acids, bile extracts, tannins, bilirubin, biliverbin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives, (preferably gamma-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and its derivatives, ubiquinol and its derivatives, vitamin C and derivatives (preferably ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate, ascorbyl glucoside), tocopherol and derivatives (preferably vitamin E acetate),Vitamin A and derivatives (vitamin A palmitate) and coniferyl benzoate of benzoic acid resin, rutinic acid and its derivatives, flavonoids and their glycosylated precursors, in particular quercetin and its derivatives, preferably α-glucosylrutin, rosmarinic acid, carnosol, carnosolic acid, resveratrol, caffeic acid and its derivatives, sinapic acid and its derivatives, ferulic acid and its derivatives, curcuminoids, chlorogenic acid and its derivatives, retinoids, preferably retinyl palmitate, retinol or tretinoin, ursolic acid, levulinic acid, butylated hydroxytoluene, butylated hydroxyanisole, nordihydroguaiacic acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (preferably ZnO, Zn SO4), selenium and its derivatives (preferably selenomethionine), superoxide dismutase, stilbene and its derivatives (preferably stilbene oxide, trans-stilbene oxide) and derivatives (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these cited active ingredients suitable according to the invention or extracts or fractions of plants having antioxidant effect, preferably green tea, rooibos, honeybush, grape, rosemary, sage, melissa, thyme, lavender, olive, oats, cocoa, ginkgo, ginseng, licorice, honeysuckle, sophora, pueraria, pinus, citrus, phyllanthus emblica or St. John's wort, grape seed, wheat germ, phyllanthus emblica, preferably coenzyme Q10, plastoquinone, menaquinone. Preferred antioxidants are selected from the group consisting of vitamin A and derivatives, vitamin C and derivatives, tocopherol and derivatives, preferably tocopheryl acetate, and ubiquinone.

[0159] When vitamin E and / or its derivatives are used as antioxidants, it is advantageous to select their concentration from the range of about 0.001 to about 10% by weight, based on the total weight of the formulation.When vitamin A or vitamin A derivatives or carotene or their derivatives are used as antioxidants, it is advantageous to select their concentration from the range of about 0.001 to about 10% by weight, based on the total weight of the formulation.

[0160] Matrix metalloproteinase inhibitors (MMPIs). Preferred compositions include matrix metalloproteinase inhibitors, particularly those that inhibit matrix metalloproteinases that enzymatically cleave collagen, such as ursolic acid, retinyl palmitate, propyl gallate, precocenes, 6-hydroxy-7-methoxy-2,2-dimethyl-1(2H)-benzopyran, 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1(2H)-benzopyran, benzamidine hydrochloride, the cysteine ​​proteinase inhibitor N-ethylmalemide and the serine protease inhibitors epsilon-amino-n-caproic acid:phenylmethylsulfonyl fluoride, Colibin (Pentapharm, INCI: Hydrolyzed Rice Protein), Oenoterol (Soliance, INCI: Propylene Glycol, Aqua, Oenothera biennis root extract, ellagic acid, ellagitannins, e.g. from pomegranate), phosphoramido hinokitiol, EDTA, galardin, EquiStat (Collaborative; apple fruit extract, soybean seed extract, ursolic acid, soybean isoflavones and soybean proteins), sage extract, MDI (Atrium; INCI: glycosaminoglycans), Fermiskin (Silab / Mawi; INCI: water and Lentinus edodes extract), actimp 1.9.3 (Expan-science / Rahn; INCI: hydrolyzed lupin proteins), lip obersoya glycone (Mibelle; INCI: alcohol, polysorbate 80, lecithin and soybean isoflavones), extracts from green and black tea, and WO02 / 069992 A1 (see Tables 1-12, incorporated herein), hydrolyzed proteins from soybean, rice, pea or lupin, plant extracts which inhibit MMPs, preferably extracts from Shitake mushroom, extracts from leaves of the Rosaceae family, in particular extracts of blackberry leaves (preferably as described in WO2005123101A1, incorporated herein by reference) e.g. SymMatrix (Symrise, INCI: Maltodextrin, Rubus Fruticosus (Blackberry) leaf extract).Preferred active substances are selected from the group consisting of retinyl palmitate, ursolic acid, extracts from the leaves of the Rosaceae family, subfamily Rosaceae, genistein and daidzein.

[0161] Skin moisturizer. Preferred skin moisturizers are selected from the group consisting of alkanediols or alkanetriols containing 3 to 12 carbon atoms, preferably C3-C10-alkanediols and C3-C10-alkanetriols.More preferably, the skin moisturizer is selected from the group consisting of glycerol, 1,2-propylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,2-pentanediol, 1,2-hexanediol, 12-octanediol and 1,2-decanediol.

[0162] Glycosaminoglycan stimulator. Preferred compositions include hyaluronic acid and derivatives or salts, Subliskin (Sederma, INCI: Sinorhizobium meliloti ferment filtrate, cetyl hydroxyethylcellulose, lecithin), Hyalufix (BASF, INCI: Water, Butylene Glycol, Alpinia galanga leaf extract, Xanthan gum, Caprylic / capric triglyceride), Stimulhyal (Soliance, INCI: Calcium ketogluconate), Syn-Glycan (DSM, INCI: Tetradecylaminobutyroylvalylaminobutyric acid urea trifluoroacetate, glycerin, magnesium chloride) Kalpariane (Biotech Marine), DC Upregulex (Characteristic cosmetic ingredient, INCI: Water, Butylene Glycol, Phospholipids, Hydrolyzed sericin), Glucosamine, N-acetylglucosamine, Retinoids, preferably Retinol and Vitamin A, Arctium lappa fruit extract, Eriobotrya The preferred active substances are selected from the group consisting of hyaluronic acid and derivatives or salts, retinol and derivatives, (-)-α-bisabolol or synthetic alpha-bisabolol, such as Dragosantol and Dragosantol 100 from Symrise, oat glucan, Echinacea purpurea extract, Sinorhizobium meliloti fermentation filtrate, calcium ketogluconate, Alpinia galanga leaf extract and tetradecylaminobutyroylvalylaminobutyric acid urea trifluoroacetate.

[0163] TRPV1 antagonist. Suitable compounds which reduce the hypersensitivity of skin nerves based on their action as TRPV1 antagonists are, for example, trans-4-tert-butylcyclohexanol, as described in WO2009087242A1, or indirect modulators of TRPV1 by activating the μ receptor, such as acetyl tetrapeptide-15, which are preferred.

[0164] Stripping agent. The composition may also contain a stripping agent (component b5) in an amount of about 0.1 to about 30% by weight, preferably about 0.5 to about 15% by weight, particularly preferably about 1 to about 10% by weight, based on the total weight of the formulation. The expression "stripping agent" is understood to mean a compound capable of carrying out any of the following: For direct exfoliation by promoting exfoliation. β-hydroxy acids, especially salicylic acid and its derivatives (including 5-n-octanoylsalicylic acid); α-hydroxy acids such as glycolic acid, citric acid, lactic acid, tartaric acid, malic acid, mandelic acid; urea; gentisic acid; oligofucosyl; cinnamic acid; extract of Sophora japonica; some derivatives of resveratrol and jasmonic acid; ·For enzymes involved in the delamination or decomposition of corneodesmosomes, glycosidases, stratum corneum chymotryptic enzymes (SCCE) or other proteases (trypsin, chymotrypsin-like).For enzymes involved in the delamination or decomposition of corneodesmosomes, glycosidases, stratum corneum chymotryptic enzymes (SCCE) or other proteases (trypsin, chymotrypsin-like).Agents that chelate inorganic salts may be mentioned. EDTA; N-acyl-N,N',N'-ethylenediaminetriacetic acid; aminosulfone compounds, in particular (N-2-hydroxyethylpiperazine-N-2-ethane)sulfonic acid (HEPES); derivatives of 2-oxothiazolidine-4-carboxylic acid (procysteine); derivatives of α-amino acids of the glycine type (sodium methylglycine diacetate, as described in EP 0 852 949 and sold under the name TRILONM by BASF); honey; sugar derivatives such as O-octanoyl-6-D-maltose or N-acetylglucosamine; chestnut extracts, such as those sold under the name Recoverine® by the company SI-LAB, prickly pear extracts marketed under the name Exfolactive® by the company SILAB, or phytosphingosine SLC® (phytosphingosine grafted with salicylic acid) marketed by the company Degussa.

[0165] Exfoliants suitable for the present invention can be selected from the group comprising: sulfonic acids, calcium chelating agents, alpha-hydroxy acids such as glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid, ascorbic acid and its derivatives, for example ascorbyl glucoside and magnesium ascorbyl phosphate, nicotinamide, urea, beta-hydroxy acids such as (N-2-hydroxyethylpiperazine-N-2-ethane)sulfonic acid (HEPES), salicylic acid and its derivatives, retinoids such as retinol and its esters, retinal, retinoic acid and its derivatives, in particular chestnut or prickly pear extracts marketed by SILAB, reducing compounds such as cysteine ​​and cysteine ​​precursors.

[0166] Exfoliants which can be used are also nicotinic acid and its esters and nicotinamide (also called vitamin B3 or vitamin PP), and ascorbic acid and its precursors, as described in particular in application EP 1 529 522 A1.

[0167] Anti-cellulite agent. The anti-cellulite and lipolytic agents are preferably selected from the group consisting of those described in WO2007 / 077541, beta-adrenergic receptor agonists such as synephrine and its derivatives, and cyclohexyl carbamates described in WO2010 / 097479. Agents that enhance or potentiate the activity of the anti-cellulite agents, in particular agents that stimulate and / or depolarize C-nerve fibers, are preferably selected from the group consisting of capsaicin and its derivatives, vanillylnonylamide and its derivatives, L-carnitine, coenzyme A, isoflavonoids, soybean extract, ananas extract and conjugated linoleic acid.

[0168] Fat enhancer. Formulations and products according to the invention may also include one or more fat enhancing and / or adipogenic agents, as well as agents that enhance or potentiate the activity of the fat enhancing agents, such as hydroxymethoxyphenylpropylmethylmethoxybenzofuran (trade name: Sym3D®). Hair growth activators or inhibitors

[0169] Formulations and products according to the invention may also contain one or more hair growth activators, ie agents that stimulate hair growth.Hair growth activators are preferably selected from the group consisting of pyrimidine derivatives such as 2,4-diaminopyrimidine-3-oxide (aminexyl), 2,4-diamino-6-piperidinopyrimidine-3-oxide (minoxidil) and derivatives, 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine and its derivatives, xanthine alkaloids and their derivatives such as caffeine, theobromine and theophylline, quercetin and derivatives, dihydroquercetin (taxifolin) and derivatives, potassium channel openers, antiandrogens, synthetic or natural 5-reductase inhibitors, nicotinic acid esters such as tocopheryl nicotinate, benzyl nicotinate and C1-C6 alkyl nicotinates, proteins such as the tripeptide Lys-Pro-Val, diphencyprene, hormones, finasteride, phenanthrene ... Sterides, dutasteride, flutamide, bicalutamide, pregnane derivatives, progesterone and its derivatives, cyproterone acetate, spironolactone and other diuretics, calcineurin inhibitors such as FK506 (tacrolimus, fujimycin) and its derivatives, cyclosporin A and its derivatives, zinc and zinc salts, polyphenols, procyanidins, proanthocyanidins, plant sterols such as beta-sitosterol, biotin, eugenol, (±)-beta-citronellol, panthenol, glycogen from e.g. mussels, plants and plant parts of e.g. the dandelion genus (Leontodon or Taraxacum), Orthosiphon, Vitex, Coffea, Guarana, Theobroma, Asiasarum, Cucurbita or Styphnolobium, Serenoa repens (saw palmetto), Sophora flavescens, African prune, millet, Cimicifuga racemosa, Glycine max, Eugenia caryophyllata, Cotinus cog-gygria, Hibiscus rosa-sinensis, Camellia sinensis, Ilex paraguariensis, Isochrysis galbana, licorice, grapes, apples, barley or hops from rice or wheat.

[0170] Alternatively, the formulations and products according to the invention may comprise one or more hair growth inhibitors (as described above), i.e. agents for reducing or preventing hair growth. The hair growth inhibitors are preferably selected from the group consisting of: Activins, activin derivatives or activin agonists, ornithine decarboxylase inhibitors such as α-difluoromethylornithine or pentacyclic triterpenes such as, for example, ursolic acid, betulin, betulinic acid, oleanolic acid and its derivatives, 5α-reductase inhibitors, androgen receptor antagonists, S-adenosylmethionine decarboxylase inhibitors, γ-glutamyltranspeptidase inhibitors, transglutaminase inhibitors, serine protease inhibitors from soybean, extracts from microorganisms, algae, different microalgae or plants and plant parts of, for example, the families Fabaceae, Solanaceae, Poaceae, Asclepiadaceae or Cucurbitaceae, Chondrus spp., Gloiopeltis spp., Ceramium spp., Durvillea spp., Glycine max spp., Sanguisorba officinalis spp., Calendula officinalis spp., Hamamelis virginiana spp., Arnica montana spp., Salix alba spp., Hypericum spp. perforatum, and Gymnemasylvestre. Physiological Coolants

[0171] The composition may also contain one or more substances having a physiological cooling effect (cooling agents), which are preferably selected here from the following list: Menthol and menthol derivatives (e.g., L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol, neomenthol), menthyl ethers (e.g., (I-menthoxy)-1,2-propanediol, (1-menthoxy)-2-methyl-1,2-propanediol, 1-menthyl-methyl ether), mentholglyceryl acetal or menthol glyceryl ketal or a mixture of both, menthyl esters (e.g., menthyl formiate, menthyl acetate, menthyl isobutyrate, menthyl hydroxyisobutyrate, menthyl lactate, L-menthyl-L-lactate, L-menthyl-D-lactate, menthyl-(2-methoxy)acetate, menthyl-(2-methoxyethoxy)acetate, menthyl pyroglucose, Menthyl carbonates (e.g., menthyl propylene glycol carbonate, menthyl ethylene glycol carbonate, menthyl glycerol carbonate or mixtures thereof), semiesters of menthol with dicarboxylic acids or derivatives thereof (e.g., monomenthyl succinate, monomenthyl glutarate, monomenthyl malonate, O-menthyl succinate-N,N-(dimethyl)amide, O-menthyl succinate-amide), menthane carboxylic acid amides (in this case preferably menthane carboxylic acid-N-ethylamide [WS3] or Nα-(menthanecarbonyl)glycine ethyl ester [WS5], as described in U.S. Pat. No. 4,150,052, menthane carboxylic acid-N-(4-cyanophenyl)amide or menthane- Carboxylic acid-N-(alkoxyalkyl)amides described in WO2005 / 049553A1, menthone and menthone derivatives (e.g. for L-menthone glycerol ketal), 2,3-dimethyl-2-(2-propyl)-butyric acid derivatives (e.g. 2,3-dimethyl-2-(2-propyl)-butyric acid-N-methylamide [WS23]), isopulegol or its esters (I-(-)-isopulegol, I-(-)-isopulegol acetate), menthane derivatives (e.g. p-menthane-3,8-diols), cubols, or pyrrolidone derivatives of cycloalkyldione derivatives (e.g. 3-methyl-2(1-pyrrolidinyl)-2-cyclopenten-1-one) or tetrahydropyrimidin-2-ones (e.g. icilin or related compounds described in WO2004 / 026840), further carboxamides (e.g. N-(2-(pyridin-2-yl)ethyl)-3-p-menthane carboxamide or related compounds), (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-isopropyl)cyclohexane-carboxamide [WS12], oxamates (preferably those described in EP 2033688 A2) and [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] 2-(ethylamino)-2-oxo-acetate (Xcool). Anti-inflammatory agents

[0172] The composition may also contain anti-inflammatory and / or reddening and / or itching-relieving evaluated components, in particular steroid substances of the corticosteroid type selected from the group consisting of hydrocortisone, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone. These are advantageously used as anti-inflammatory active ingredients or active ingredients for relieving redness and itching, the list of which can be expanded by the addition of other steroidal anti-inflammatory agents. Non-steroidal anti-inflammatory agents can also be used. More particularly, (i) steroidal anti-inflammatory substances of the corticosteroid type, in particular hydrocortisone derivatives such as hydrocortisone, hydrocortisone 17-butyrate, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone; (ii) non-steroidal anti-inflammatory substances, in particular oxicams such as piroxicam or tenoxicam, salicylates such as aspirin, disalcid, solprin or fendosal, acetate derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin or clindanac, mefenamics such as fenamates, meclofenamic, flufenamic or niflumic, propionate derivatives such as ibuprofen, naproxen or benoxaprofen, pyrazoles such as phenylbutazone, oxyphenylbutazone, febrazone or azapropazone, (iii) natural or naturally occurring anti-inflammatory substances or substances which reduce redness and / or itching, in particular extracts or fractions from chamomile, Aloe vera, Commiphora spp., Rubia spp., willow, willow, oats, calendula, arnica, St. John's wort, honeysuckle, rosemary, Passiflora incarnata, witch hazel, ginger, echinacea, or single active compounds thereof; (iv) Histamine receptor antagonists, serine protease inhibitors (e.g., soybean extract), TRPV1 antagonists (e.g., 4-t-butylcyclohexanol), NK1 antagonists (e.g., aprepitant, hydroxyphenylpropamidobenzoic acid), cannabinoid receptor agonists (e.g., palmitoylethanolamine), and TRPV3 antagonists.

[0173] Examples which may be cited here are oxicams such as piroxicam or tenoxicam, salicylates such as aspirin, disalcid, solprin or fendosal, acetic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin or clindanac, fenamates such as mefenamic acid, meclofenamic acid, flufenamic acid or niflumic acid, propionic acid derivatives such as ibuprofen, naproxen, benoxaprofen or pyrazoles such as phenylbutazone, oxyphenylbutazone, febrazone or azapropazone. Anthranilic acid derivatives, in particular the avenanthramides described in WO2004 047833 A1, are preferred antipruritic ingredients in the compositions according to the invention.

[0174] Natural or naturally occurring anti-inflammatory mixtures of substances, or mixtures of substances that reduce redness and / or itching, particularly extracts or fractions from chamomile, aloe vera, Commiphora species, Rubia species, willow, willow herb, oats, calendula, arnica, St. John's wort, honeysuckle, rosemary, Passiflora incarnata, witch hazel, ginger, or echinacea, are also useful. Preferably, the active ingredient is selected from the group consisting of chamomile, aloe vera, oats, calendula, arnica, honeysuckle, rosemary, witch hazel, ginger or echinacea, and / or pure substances, preferably alpha-bisabolol, apigenin, apigenin-7-glucoside, gingerol, shogaol, gingerdiol, dehydrogingerdione, paradol, natural or naturally occurring avenanthramides, preferably tranilast, avenanthramide A, avenanthramide B, avenanthramide C, non-natural or non-naturally occurring avenanthramides, preferably dihydroavenanthramide D, dihydroavenanthramide E, avenanthramide D, avenanthramide E, avenanthramide F, boswellic acid, phytosterols, glycyrrhizin, glabridin and licochalcone A; Also preferably selected from the group consisting of alpha-bisabolol, natural avenanthramides, non-natural avenanthramides, preferably dihydroavenanthramide D (described in WO 2004 / 047833 A1), boswellic acid, phytosterols, glycyrrhizin and licochalcone A, and / or allantoin, panthenol, lanolin, (pseudo)ceramides (preferably ceramide 2, hydroxypropyl bispalmitamide MEA, cetyloxypropyl glyceryl methoxy-propyl myristamide, N-(1-hexadecanoyl)-4-hydroxy-L-proline (1-hexadecyl) ester, hydroxyethyl palmityloxyhydroxypropyl palmitamide), glycosphingolipids, phytosterols, chitosan, mannose, lactose and alpha-glucans, in particular 1,3-1,4-alpha-glucan from oats.

[0175] When bisabolol is used in the context of the present invention, it can be of natural or synthetic origin, preferably "alpha-bisabolol".Preferably, the bisabolol used is synthetically prepared or natural (-)-alpha-bisabolol and / or synthetic mixed isomer alpha-bisabolol.When natural (-)-alpha-bisabolol is used, it can also be used as a component of essential oils or plant extracts or fractions thereof, for example as a component of oils (fractions) or extracts of chamomile or vanillosmopsis (especially vanillosmopsis erythropappa or vanillosmopsis arborea).Synthetic alpha-bisabolol is available, for example, under the name "Dragosantol" from Symrise.

[0176] When using ginger extract in the context of the present invention, the preferred solvents are methanol, ethanol, isopropanol, acetone, ethyl acetate, carbon dioxide (CO2), hexane, methylene chloride, chloroform or other solvents or mixtures of solvents of comparable polarity. The extract is characterized by the presence of active skin irritation reducing amounts of components such as gingerols, shogaols, gingerdiols, dehydrogingerdione and / or paradols. Antibacterial agents

[0177] Suitable antibacterial agents are in principle, for example, 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)urea, 2,4,4'-trichloro-2'-hydroxy-diphenyl ether (triclosan), 4-chloro-3,5-dimethyl-phenol, 2,2'-methylenebis(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)phenol, 2-benzyl-4-chloro-phenol, 3-(4-chlorophenoxy)-1,2-propanediol, 3-iodo-2-propynyl Butyl carbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), antibacterial fragrances, thymol, thyme oil, eugenol, clove oil, menthol, mint oil, farnesol, phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid N-alkylamides, e.g., n-octyl salicylamide or n-decyl salicylamide, are all substances that are effective against gram-positive bacteria. Enzyme inhibitors

[0178] Suitable enzyme inhibitors are, for example, esterase inhibitors. These are preferably trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, and especially triethyl citrate (HydagenCAT). These substances inhibit enzyme activity, thereby reducing the formation of odor. Other substances that are suitable ester enzyme inhibitors are, for example, sterol sulfates or phosphates, such as lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and their esters, such as tartaric acid, monoethyl glutaric acid, diethyl glutaric acid, adipic acid, monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and their esters, such as citric acid, malic acid, tartaric acid or diethyl tartrate, and zinc glycinate. Odor absorbents and antiperspirant actives

[0179] Suitable odor absorbers are substances that are able to absorb odor-forming compounds and retain a large part of them. They reduce the partial pressure of the individual components and therefore also their diffusion rate. In this process, it is important that the perfume is not spoiled. Odor absorbers are ineffective against bacteria. They contain, for example, as the main ingredient, complex zinc salts of ricinoleic acid, or certain, mainly odor-neutral fragrances known to the skilled artisan as "fixatives", such as extracts of labdanum or storax or certain abietic acid derivatives. Odor masking agents are fragrances and perfume oils which, in addition to their function as odor masking agents, give the deodorant its respective fragrance scent. Perfume oils that may be mentioned are, for example, mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flowers, stems and leaves, fruits, fruit peels, roots, woods, herbs and grasses, needles and branches, resins and balsams. Also suitable are animal products, such as, for example, civet or beaver incense. Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol, and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, p-tert-butylcyclohexyl acetate, linalyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, allylcyclohexyl propionate, styrallyl propionate, and benzyl salicylate. The ethers include, for example, benzyl ethyl ether, and the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial, and brujonal. The ketones include, for example, the ionones and methyl cedryl ketone, the alcohols include anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, and the hydrocarbons include mainly the terpenes and balsams. However, preference is given to using mixtures of different fragrances which together produce a pleasant fragrance note.Essential oils of relatively low volatility which are primarily used as aroma ingredients are also suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, linden flower oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, labdanum oil, and lavandin oil. Preference is given to the use of bergamot oil, dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, α-hexylcinnamaldehyde, geraniol, benzyl acetone, cyclamen aldehyde, linalool, boisambrene forte, ambroxan, indole, hedione, sandelice, lemon oil, mandarin oil, orange oil, allyl amyl glycolate, cyclovertal, lavandin oil, clary sage oil, β-damascene, geranium oil bourbon, cyclohexyl salicylate, Vertofix coeur, iso-E-super, Fixolide NP, evernyl, evernyl, iraldine gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romirat, irotyl and floramat alone or in mixtures.

[0180] Suitable astringent antiperspirant active ingredients are primarily salts of aluminum, zirconium, or zinc C. Such suitable antiperspirant active ingredients include, for example, aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, and complex compounds thereof, such as 1,2-propylene glycol, aluminum hydroxyalanthoate, aluminum tartrate chloride, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate, and complex compounds thereof, and amino acids, such as glycine. Film-forming and anti-dandruff agents

[0181] Standard film-forming agents are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid and their salts and similar compounds.

[0182] Suitable antidandruff agents include Piroctone Olamine (1-hydroxy-4-methyl-6-(2,4,4-trimethyl-pentyl)-2-(1H)-pyridinone monoethanolamine salt), Baypival® (Climbazol), Ketoconazole® (4-acetyl-1-({4-[2-(2,4-dichlorophenyl)r-2-(1H-imidazol-1-ylmethyl)-1,3-dioxiran-c-4-ylmethoxyphenyl}-piperazine, ketoconazole, elbiphenyl, ol, selenium disulfide, colloidal sulfur, sulfur polyethylene glycol sorbitan monooleate, sulfur ricinol polyethoxylate, sulfur tar distillate, salicylic acid (or in combination with hexachlorophene), undecylenic acid, monoethanolamide sulfosuccinic acid Na salt, Lamepon® UD (protein / undecylenic acid condensate), zinc pyrithione, aluminum pyrithione and magnesium pyrithione / dipyrithione magnesium sulfate. Carriers and hydrotropes

[0183] Preferred cosmetic carrier materials are solid or liquid at 25°C and 1013 mbar (including high viscosity substances), such as, for example, glycerol, 1,2-propylene glycol, 1,2-butylene glycol, 1,3-propylene glycol, 1,3-butylene glycol, ethanol, water, and mixtures of two or more of the above liquid carrier materials with water. Optionally, these preparations according to the invention can be produced using preservatives or solubilizers. Other preferred liquid carrier materials that may be components of the preparations according to the invention are selected from the group consisting of oils, such as vegetable oils, neutral oils and mineral oils.

[0184] Preferred solid carrier materials which may be components of the preparation according to the invention are hydrocolloids, such as starch, degraded starch, chemically or physically modified starch, dextrin, (powdered) maltodextrin (preferably with a dextrose equivalent of 5 to 25, preferably 10 to 20), lactose, silicon dioxide, glucose, modified cellulose, gum arabic, ghatti gum, tragacanth, karaya, carrageenan, pullulan, curdlan, xanthan gum, gellan gum, guar wheat, carob flour, alginates, agar, pectin, inulin and mixtures of two or more of these solids, in particular maltodextrin (preferably with a dextrose equivalent of 15 to 20), lactose, silicon dioxide and / or glucose.

[0185] In addition, hydrotropes, such as ethanol, isopropyl alcohol or polyols, can be used to improve the flow behavior. Suitable polyols preferably contain 2 to 15 carbon atoms and at least two hydroxyl groups. The polyols may contain other functional groups, more particularly amino groups, or may be modified with nitrogen. Typical examples are: Glycerol. Alkylene glycols, such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol, and polyethylene glycols having an average molecular weight of 100 to 1000 daltons. Technical oligoglycerol mixtures having a degree of self-condensation of 1.5 to 10, such as, for example, technical diglycerol mixtures having a diglycerol content of 40 to 50% by weight. Particularly methylol compounds such as trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol. ·Lower alkyl glucosides, especially those containing 1 to 8 carbon atoms in the alkyl group, such as methyl and butyl glucoside. · Sugar alcohols containing 5 to 12 carbon atoms (such as sorbitol and mannitol). ·Sugars containing 5 to 12 carbon atoms, e.g. glucose and sucrose. Amino sugars, e.g. glucamine. · Dialcoholamines such as diethanolamine and 2-aminopropane-1,3-diol. Preservatives

[0186] Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid, as well as other classes of compounds listed in Annex 6, parts A and B of the Kosmetikverordnung ("Cosmetics Directive"). Fragrance oils and fragrances

[0187] Suitable perfume oils are mixtures of natural and synthetic fragrances. Natural fragrances include extracts of flowers (lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peels (bergamot, lemon, orange), roots (nutmeg, angelica, celery, cardamom, costus, iris, calamus), woods (pinewood, sandalwood, guaiacwood, cedarwood, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animal sources such as civet and beaver can also be used. Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol, and hydrocarbon type. Examples of fragrance compounds of the ester type are benzyl acetate, phenoxyethyl isobutyrate, linalyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethylmethylphenylglycinate, ethylmethylphenyl propionate, styraryl propionate, and benzyl salicylate. Ethers include, for example, benzyl ethyl ether, while aldehydes include, for example, linear alkanals containing 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial, and bourgeonal. Examples of suitable ketones are ionone, -isomethylionone, and methyl cedryl ketone. Suitable alcohols are anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol. Hydrocarbons include mainly terpenes and balsams. However, it is preferred to use mixtures of different fragrance compounds which together produce a pleasant fragrance. Other suitable perfume oils are relatively low volatility essential oils which are mainly used as fragrance ingredients.Examples are sage oil, chamomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, lime blossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, ladanum oil, lavendin oil. The following are preferably used individually or in the form of a mixture: Bergamot Oil, Dihydromyrcenol, Lilial, Lyral, Citronellol, Phenylethyl Alcohol, Hexylcinnamaldehyde, Geraniol, Benzyl Acetone, Cyclamen Aldehyde, Linalool, Boisambrene Forte, Ambroxan, Indole, Hedione, Sandelice, Citrus Oil, Mandarin Oil, Orange Oil, Allyl Glycolate, Cyclobaltal, Lavendin Oil, Clary Oil, Damascus Cone, Geranium Oil Bourbon, Cyclohexyl Salicylate, Vertofix Coeur, Iso-E-Super, Fixolide NP, Evernyl, Iraldein Gamma, Phenylacetic Acid, Geranyl Acetate, Benzyl Acetate, Rose Oxide, Romilat, Irotyl, Floramat. dye

[0188] Suitable dyes are any of the substances suitable and approved for cosmetic purposes, as described, for example, in the publication of the Farbstoff-kommission der Deutschen Forschungsgemeinschaft, Verlag Chemie, Weinheim, Kosmetische Farbemittel, 1984. Examples include cochineal red A (CI.16255), patent blue V (CI.42051), indigotine (CI.73015), chlorophyllin (CI.75810), quinoline yellow (CI.47005), titanium dioxide (CI.77891), indanthrene blue RS (CI.69800) and madder lake (CI.58000). Luminol may also be present as a luminescent pigment. Advantageous color pigments are, for example, titanium dioxide, mica, iron oxides (e.g. Fe2O3 Fe3O4, FeO(OH)) and / or tin oxide. Advantageous dyes are, for example, carmine, Berlin blue, chromium oxide green, ultramarine blue and / or manganese violet. preparation

[0189] Preferred compositions according to the invention are preferably selected from the group of leave-on products for the treatment, protection, care and cleansing of the skin and / or hair or as make-up products, in which the compound or compounds of formula (I) remain on the skin and / or hair for a longer period of time compared to rinse-off products, so that their moisturizing action in moisturizing and / or anti-aging and / or in promoting wound healing is more pronounced.

[0190] The formulations according to the invention are preferably in the form of emulsions, e.g. W / O (water in oil), O / W (oil in water), W / O / W (water in oil in water), O / W / O (oil in water in oil) emulsions, PIT emulsions, Pickering emulsions, low oil emulsions, micro- or nanoemulsions, solutions, e.g. in oil (fatty acids or fatty acid esters, in particular C6-C32 fatty acid C2-C30 esters) or silicone oils, dispersions, suspensions, creams, lotions or milk, depending on the production method and ingredients. gels (including hydrogels, water-dispersed gels, oleogels), sprays (e.g. pump sprays or sprays with propellants) or foams or impregnating solutions for cosmetic wipes, detergents, e.g. soaps, detergents, liquid washes, shower and bath preparations, bath products (capsules, oils, tablets, salts, bath salts, soaps, etc.), boiling agents, skin care products, e.g. emulsions (as above), ointments, pastes, gels (as above), oils, balsams, serums, powders (e.g. face powders, body powders), masks, pencils, sticks, roll-ons, pumps, aerosols (foaming, non-foaming or post-foaming), deodorants and / or antiperspirants, mouthwashes and mouth rinses, foot care products (including keratolytics, deodorants), insect repellents, sunscreens, after-sun preparations, shaving products, after-shave balms, pre-shave and after-shave lotions, deodorants, such as shampoos (including 2-in-1 shampoos, anti-dandruff shampoos, baby shampoos, shampoos for dry scalp, concentrated shampoos), conditioners, hair tonics, hair waters, hair rinses, styling creams, pomades, perms, setting lotions, hairsprays, styling aids (e.g. gels or waxes), hair smoothing agents (detanglers, relaxers), e.g. temporary direct hair dyes, semi-permanent hair dyes, permanent hair dyes, hair conditioners, hair mousses, eye care products, make-up, make-up removers or baby products.

[0191] The formulations according to the invention are particularly preferably in the form of an emulsion, in particular a W / O, O / W, W / O / W, O / W / O emulsion, a PIT emulsion, a Pickering emulsion, an emulsion with a low oil content, a micro- or nanoemulsion, a gel (including hydrogels, water-dispersed gels, oleogels), a solution, i.e. in oil (fatty acids or fatty acid esters, in particular C6-C32 fatty acid C2-C30 esters) or silicone oil, or a spray (e.g. pump spray or spray with propellant).

[0192] The auxiliary substances and additives may be included in an amount of 5 to 99% by weight, preferably 10 to 80% by weight, based on the total weight of the formulation. The amount of cosmetic or dermatological auxiliary and additives and fragrances to be used in each case can be easily determined by the skilled artisan by simple trial and error, depending on the nature of the particular product.

[0193] The preparation may also contain water in an amount of 5 to 99% by weight, preferably 10 to 80% by weight, based on the total weight of the preparation. Detergent Composition

[0194] Another object of the present invention relates to a detergent composition comprising said 1,2-pentanediol of improved quality. Suitable examples of detergents are heavy duty powder detergents, heavy duty liquid detergents, light duty powder detergents, light duty liquid detergents, fabric softeners, manual dishwashing agents, all-purpose detergents, etc.

[0195] The detergent compositions according to the invention may comprise any of the ingredients normally found in such compositions, such as, for example, anionic, nonionic, cationic, amphoteric or zwitterionic (co)surfactants, organic solvents, builders, enzymes, additional adjuvants such as soil release agents, thickeners, colourants, fragrances etc. Anionic Co-Surfactants

[0196] Preferably, surfactants of the sulfonate type, alkyl(alkenyl)sulfonates, alkoxylated alkyl(alkenyl)sulfates, ester sulfonates and / or soaps are used as anionic surfactants. Suitable surfactants of the sulfonate type are advantageously C9-13 alkylbenzenesulfonates, olefinsulfonates, i.e. mixtures of alkenes and hydroxyalkanesulfonates, and disulfonates, for example obtained by sulfonation of C12-18 monoolefins with gaseous sulfur trioxide, followed by alkaline or acidic hydrolysis of the terminal or internal double bonds of the sulfonation products.

[0197] Alkyl(en)yl sulfates. Preferred alkyl(en)yl sulfates are the sodium salts of the alkali, especially sulfuric acid half esters of C12-C18 fatty alcohols, such as coconut butter alcohol, tallow alcohol, lauryl, myristyl, cetyl or stearyl alcohol or C8-C20 oxoalcohols and the half esters of secondary alcohols of these chain lengths. Alkyl sulfates of the cited chain lengths, including synthetic linear alkyl groups produced petrochemically, are also preferred. C12-C16 alkyl sulfates and C12-C15 alkyl sulfates, as well as C14-C15 alkyl sulphates and C14-C16 alkyl sulfates, are particularly preferred for reasons of laundry performance. 2,3-alkyl sulfates available under the trade name DANTM from Shell Oil Company are also suitable anionic surfactants.

[0198] Alkyl(en)yl ether sulfates. Also suitable are sulfuric acid monoesters derived from linear or branched C7-C21 alcohols ethoxylated with 1 to 6 moles of ethylene oxide, such as 2-methyl-branched C9-C11 alcohols containing an average of 3.5 moles of ethylene oxide (EO) or C12-C18 fatty alcohols with 1 to 4 EO.

[0199] Ester sulfonates. Likewise suitable are the esters of alpha sulfo fatty acids (ester sulfonates), for example the alpha sulfonated methyl esters of hydrogenated coconut acid, palm nut acid, or tallow acid.

[0200] soap. Soaps in particular can be considered as further anionic surfactants. Saturated fatty acid soaps such as the salts of lauric acid, myristic acid, palmitic acid, stearic acid, hydrogenated erucic acid and behenic acid are particularly suitable, in particular soap mixtures derived from natural fatty acids such as coconut oil fatty acids, palm kernel fatty acids, oily fatty acids or tallow fatty acids. Particularly preferred are these soap mixtures composed of 50 to 100% by weight of saturated C12-C24 fatty acid soaps and 0 to 50% by weight of oleic acid soaps.

[0201] Ether carboxylic acids. A further class of anionic surfactants are those of the ether carboxylic acids obtained by treating fatty alcohol ethoxylates with sodium chloroacetate in the presence of a basic catalyst. Their general formula is: RO(CH2CH2O)pCH2COOH, R=C1-C18 and p=0.1-20 Ether carboxylic acids are not affected by water hardness and have excellent surfactant properties. Nonionic (CO-) Surfactants

[0202] Alcohol alkoxylates. The nonionic surfactants added are preferably alkoxylated and / or propoxylated, particularly preferably primary alcohols having 8 to 18 carbon atoms and an average of 1 to 12 moles of ethylene oxide (EO) and / or 1 to 10 moles of propylene oxide (PO) per mole of alcohol. C8-C16-alcohol alkoxylates, advantageously ethoxylated and / or propoxylated C10-C15-alcohol alkoxylates, in particular C12-C14 alcohol alkoxylates, with a degree of ethoxylation between 2 and 10, preferably 3 to 8, and / or a degree of propoxylation between 1 to 6, preferably 1.5 to 5, are particularly preferred. The quoted degrees of ethoxylation and propoxylation constitute statistical average values ​​which may be integers or fractions for a particular product. Preferred alcohol ethoxylates and propoxylates are those with a narrow homolog distribution (narrow range ethoxylates / propoxylates, NRE / NRP). In addition to these nonionic surfactants, fatty alcohols with more than 12 EO can also be used, examples of which are 14 EO, 16 EO, 20 EO, 25 EO, 30 EO or 40 EO (tallow) fatty alcohols.

[0203] Alkyl glycosides (APG®). Furthermore, as additional nonionic surfactants, alkyl glycosides satisfying the general formula RO(G)x can be added, for example, as compounds, especially together with anionic surfactants. R denotes a branched aliphatic group, primary linear or methyl-branched, especially 2-methyl-branched, containing 8 to 22, preferably 12 to 18 carbon atoms. And G denotes a glycose unit of 5 or 6 carbon atoms, preferably glucose. The degree of oligomerization x, which defines the distribution of monoglycosides and oligoglycosides, is any number between 1 and 10, preferably between 1.1 and 1.4.

[0204] Fatty acid ester alkoxylates. Another class of preferred nonionic surfactants, used as the sole nonionic surfactant or in combination with other nonionic surfactants, in particular in combination with alkoxylated fatty alcohols and / or alkyl glycosides, are alkoxylated, preferably ethoxylated or ethoxylated and propoxylated fatty acid alkyl esters, preferably containing 1 to 4 carbon atoms in the alkyl chain, more particularly fatty acid methyl esters, for example as described in JP 58 / 217598A or preferably as described in International Patent Application WO90 / 13533A. Particularly preferred are C12-C18 methyl esters with fatty acids containing an average of 3 to 15 EO, in particular an average of 5 to 12 EO.

[0205] Amine oxide. Nonionic surfactants of the amine oxide type, such as N-cocoalkyl-N,N-dimethylamine oxide and N-tallowalkyl-N,N-dihydroxyethylamine oxide, and fatty acid alkanolamides, may also be suitable. The amount of these nonionic surfactants used is preferably equal to or less than the amount of the ethoxylated fatty alcohols used, in particular equal to or less than half that amount.

[0206] Gemini surfactants. The so-called gemini surfactants can be considered as further surfactants. Generally speaking, such compounds are understood to mean compounds with two hydrophilic and two hydrophobic groups per molecule. As a rule, these groups are separated from each other by a "spacer". The spacer is usually a hydrocarbon chain intended to be long enough so that the hydrophilic groups are separated by a sufficient distance so that they can act independently of each other. These types of surfactants are generally characterized by an unusually low critical micelle concentration and the ability to significantly reduce the surface tension of water. However, in exceptional cases, not only dimeric but also trimeric surfactants are meant by the term gemini surfactants. Suitable gemini surfactants are, for example, sulfated hydroxy mixed ethers according to German patent application DE 4321022 A1, or dimeric alcohol bis- and trimeric alcohol tris sulfates and ether sulfates according to international patent application WO 96 / 23768 A1. The dimeric and trimeric mixed ethers with blocked end groups according to German Patent Publication DE 19513391 A1 are particularly characterized by their bifunctionality and multifunctionality. Gemini polyhydroxy fatty acid amides or polyhydroxy fatty acid amides, as described in International Patent Applications WO 95 / 19953 A1, WO 95 / 19954 A1 and WO 95 / 19955 A1, etc., can also be used. Cationic Co-Surfactant

[0207] Tetraalkylammonium salts. Cationic active surfactants contain a hydrophobic polymeric group necessary for the surface activity of the cation by dissociation in aqueous solution. An important representative group of cationic surfactants are the tetraalkylammonium salts of the general formula (R1R2R3R4N+)X-, where R1 represents C1-C8 alkyl(alkenyl) and R2, R3 and R4, independently of each other, represent alkyl(alkenyl) radicals having 1 to 22 carbon atoms. X is a counterion, preferably selected from the group of halides, alkyl sulfates and alkyl carbonates. Particularly preferred are cationic surfactants in which the nitrogen group is substituted with two long acyl groups and two short alkyl(alkenyl) groups.

[0208] Esterquat. A further class of cationic surfactants that is particularly useful as co-surfactant of the present invention is represented by so-called esterquats. Ester compounds are generally understood to be quaternized fatty acid triethanolamine ester salts. These are known compounds that can be obtained by the relevant methods of preparative organic chemistry. In this context, reference is made to International Patent Application WO91 / 01295A1, in which triethanolamine is partially esterified with fatty acid in the presence of hypophosphorous acid, air is passed through the reaction mixture, and then the whole is quaternized with dimethyl sulfate or ethylene oxide. Furthermore, German Patent DE4308794C1 describes a method for preparing solid esterquats, in which the quaternization of triethanolamine esters is carried out in the presence of a suitable dispersant, preferably a fatty alcohol.

[0209] Typical examples of esterquats suitable for use according to the invention are products whose acyl component is derived from a monocarboxylic acid corresponding to the formula RCOOH, where RCO is an acyl group containing from 6 to 10 carbon atoms, and whose amine component is triethanolamine (TEA). Examples of such monocarboxylic acids are caproic acid, caprylic acid, capric acid and technical mixtures thereof, such as the so-called head fraction fatty acids. Esterquats whose acyl component is derived from a monocarboxylic acid containing from 8 to 10 carbon atoms are preferably used. Other esterquats are those whose acyl component is derived from a dicarboxylic acid, such as malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, sorbic acid, pimelic acid, azelaic acid, sebacic acid and / or dodecanedioic acid, but preferably adipic acid. Overall, esterquats whose acyl component is derived from a mixture of a monocarboxylic acid containing from 6 to 22 carbon atoms and adipic acid are preferably used. The molar ratio of mono- and dicarboxylic acids in the final esterquat can be in the range of 1:99 to 99:1, preferably in the range of 50:50 to 90:10, more specifically in the range of 70:30 to 80:20. In addition to the quaternized fatty acid triethanolamine ester salts, other suitable esterquats are quaternized ester salts of mono- / dicarboxylic acids with diethanolalkylamines or 1,2-dihydroxypropyldialkylamines. Esterquats can be obtained both from fatty acids and the corresponding triglycerides mixed with the corresponding dicarboxylic acids. One such process, which is intended to be representative of the relevant prior art, is proposed in European patent EP0750606B1. To produce the quaternized esters, a mixture of mono- and dicarboxylic acids with triethanolamine (based on the available carboxyl functional groups) can be used in a molar ratio of 1.1:1 to 3:1. Bearing in mind the performance properties of the esterquats, ratios of 1.2:1 to 2.2:1, preferably 1.5:1 to 1.9:1, have proven particularly advantageous. Preferred ester compounds are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9. Amphoteric or zwitterionic co-surfactants

[0210] Betaine. Amphoteric or amphoteric surfactants have multiple functional groups that can be ionized in aqueous solution, thereby giving the compound anionic or cationic properties, depending on the conditions of the medium (see DIN 53900, July 1972). Near the isoelectric point (around pH 4), amphoteric surfactants form internal salts and therefore become poorly soluble or insoluble in water. Amphoteric surfactants are subdivided into ampholytes and betaines, the latter being present as zwitterions in solution. Ampholytes are ampholytes; that is, compounds that have both acidic and basic hydrophilic groups and act as acids or bases depending on the conditions. Betaines in particular are known surfactants that are mainly produced by carboxyalkylation, preferably carboxymethylation, of amine compounds. The starting material is preferably condensed with a halocarboxylic acid or its salt, more specifically sodium chloroacetate, so that one mole of salt is formed per mole of betaine. The addition of unsaturated carboxylic acids, such as, for example, acrylic acid, is also possible. Examples of suitable betaines are the carboxyalkylation products of secondary, especially tertiary amines corresponding to the formula R1R2R3N-(CH2)qCOOX, where R1 is an alkyl radical having 6 to 22 carbon atoms and R2 is hydrogen or an alkyl group containing 1 to 4 carbon atoms. R3 is an alkyl group containing 1 to 4 carbon atoms, q is a number from 1 to 6 and X is an alkali and / or alkaline earth metal or ammonium. Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, decyldimethylamine, C12 / 14-cocoalkyldimethylamine, myristyldimethylamine, cetyldimethylamine, stearyldimethylamine, stearylethylmethylamine, oleyldimethylamine, C16 / 18-tallowalkyldimethylamine, especially dodecylmethylamine, dodecyldimethylamine, dodecylethylmethylamine and technical mixtures thereof.

[0211] Alkylamidobetaine. Other suitable betaines are the carboxyalkylation products of amidoamines corresponding to the formula R1CO(R3)(R4)-NH-(CH2)pN-(CH2)qCOOX, where R1CO is an aliphatic acyl radical having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds, R2 is hydrogen or an alkyl radical having 1 to 4 carbon atoms, R3 is an alkyl radical having 1 to 4 carbon atoms, p is a number from 1 to 6, q is a number from 1 to 3, and X is an alkali and / or alkaline earth metal or ammonium. Typical examples are reaction products of fatty acids having 6 to 22 carbon atoms, such as caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, eleostearic acid, arachidonic acid, gadoleic acid, behenic acid, erucic acid. and N,N-dimethylaminoethylamine, N,N-dimethylaminopropylamine, N,N-diethylaminoethylamine and N,N-diethylaminopropylamine condensed with sodium chloroacetate and technical mixtures thereof. Commercially available products include Dehyton® K and Dehyton® PK (Cognis Deutschland GmbH & Co., KG), and Tego® Betaine (Goldschmidt).

[0212] Imidazolines. Other suitable starting materials for the betaines used for the purposes of the present invention are imidazolines. These materials are also known and can be obtained, for example, by cyclizing the condensation of one or two moles of C6-C22 fatty acids with polyfunctional amines, such as, for example, aminoethylethanolamine (AEEA) or diethylenetriamine. The corresponding carboxyalkylation products are mixtures of different open-chain betaines. Typical examples are the condensation products of the above fatty acids with AEEA, preferably imidazolines based on lauric acid, which are then dyed with sodium chloroacetate. Commercially available products include Dehyton® G (Cognis Deutschland GmbH&Co.,KG).

[0213] The amount of (co)surfactant contained in the composition according to the invention is advantageously between 0.1 and 90% by weight, in particular between 10 and 80% by weight and particularly preferably between 20 and 70% by weight. Organic Solvents

[0214] Liquid light or heavy duty detergents may contain organic solvents, preferably those miscible with water. Polydiols, ethers, alcohols, ketones, amides and / or esters are preferably used as organic solvents for this in amounts of 0 to 90% by weight, preferably 0.1 to 70% by weight, in particular 0.1 to 60% by weight. Low molecular weight polar substances, such as methanol, ethanol, propylene carbonate, acetone, acetonylacetone, diacetone alcohol, ethyl acetate, 2-propanol, ethylene glycol, propylene glycol, glycerin, diethylene glycol, dipropylene glycol monomethyl ether and dimethylformamide or mixtures thereof, are preferred. enzyme

[0215] Cellulase enzyme. The cellulase enzymes optionally used in the instant detergent compositions, if present, are preferably incorporated at a level sufficient to provide up to about 5 mg, more preferably from about 0.01 mg to about 3 mg, of active enzyme per gram of composition. Unless otherwise specified, the compositions herein preferably contain from about 0.001% to about 5%, preferably 0.01% to 1%, by weight of a commercially available enzyme preparation.

[0216] Suitable cellulases for the present invention include either bacterial or fungal cellulases. Preferably, they will have an optimum pH between 5 and 9.5. Suitable cellulases are fungal cellulases produced by Humicolainsolens and Humicola strain DSM1800 or cellulase 212 producing fungi belonging to the genus Aeromonas, and cellulases extracted from the hepatopancreas of marine mollusc Dolabella Auricula Solander, suitable cellulases are also disclosed in GB 2,075,028A. Furthermore, cellulases particularly suitable for use herein are disclosed in WO1992 013057A1. Most preferably, the cellulases used in the instant detergent composition are commercially available from NOVO Industries A / S under the product names CAREZYMEO and CELLUZYMEO.

[0217] Other enzymes. The additional enzymes are intended for a wide variety of fabric washing, including, for example, the removal of protein-based, carbohydrate-based, or triglyceride-based stains, and for preventing refugee dye transfer and fabric repair. Additional enzymes that are incorporated include proteases, amylases, lipases, and peroxidases, as well as mixtures thereof. Other types of enzymes can also be included. They can be of any suitable origin, such as vegetable, animal, bacterial, fungal, and yeast origin. However, their selection depends on several factors, such as pH activity and / or stability optimum, thermal stability, stability against active detergents, builders, and the potential to cause malodour during use. In this respect, bacterial or fungal enzymes, such as bacterial amylases and proteases, are preferred.

[0218] Enzymes are typically incorporated at levels sufficient to provide up to about 5 mg, more typically about 0.01 mg to about 3 mg of active enzyme per gram of composition. In other words, the compositions herein typically contain about 0.001% to about 5% by weight, preferably 0.01% to 1% by weight, of a commercial enzyme preparation. Protease enzymes are typically present in such commercial preparations at levels sufficient to provide 0.005 to 0.1 Anson Units (AU) of activity per gram of composition.

[0219] Suitable examples of proteases are Bacillus subtilis and subtilisin obtained from certain strains of Bacillus subtilis. Another suitable protease is developed and sold by Novo Industries A / S under the registered trade name ESPERASE® and is obtained from a Bacillus strain with maximum activity throughout the pH range of 8 to 12. The preparation of this enzyme and similar enzymes is described in GB 1,243,784 by Novo. Commercially available proteolytic enzymes suitable for removing protein-based soils include those sold under the trade names ALCALASE® and SAVINASE® by Novo Industries A / S and MAXATASE® by International Bio-Synthetics, Inc. Other proteases include Protease A and Protease B manufactured by Genencor International Inc. according to U.S. Patent No. 5,204,015 and U.S. Patent No. 5,244,791.

[0220] Amylases include alpha-amylases such as, for example, RAPIDASE® from International Bio-Synthetics, Inc. and TERMAMYL® from Novo Industries.

[0221] Lipase enzymes suitable for detergent use include those produced by microorganisms of the Pseudomonas group, such as Pseudomonas stutzeri ATCC 19154. This lipase is available under the trade name Lipase P "Amano" from Amano Pharmaceuticals. Other commercially available lipases include Amano-CES, Chromobacterium viscosum, such as lipase ex Chromobacter viscosum var. lipolyticum NRRLB 3673 available from Toyo Jozo Co., Ltd., as well as Chromobacter viscosum lipases from US Biochemical and Disoynth, and lipases from Pseudomonas gladioli. The LIPOLASE® enzyme from Humicola lanuginosa (available from Novo Industries A / S) is a preferred lipase for use herein.

[0222] Peroxidase enzymes are used in combination with oxygen sources such as percarbonates, perborates, persulfates, hydrogen peroxide, etc. They are used for "solution bleaching", i.e., to prevent the transfer of dyes or pigments removed from a substrate to other substrates in the wash liquor during the washing operation. Peroxidase enzymes are known in the art and include, for example, horseradish peroxidase, ligninase, and haloperoxidases such as chloroperoxidase and bromoperoxidase. Peroxidase-containing surfactant compositions are disclosed, for example, in WO1989099813A1.

[0223] Enzyme stabilizer. The enzymes used herein are stabilized by the presence of a water-soluble source of calcium and / or magnesium ions in the finished detergent composition that provides such ions to the enzyme. (Calcium ions are generally somewhat more effective than magnesium ions and are preferred herein when only one type of cation is used.) Additional stability can be provided by the presence of various other art-disclosed stabilizers, particularly borate species. See U.S. Pat. No. 4,537,706, which is incorporated herein in its entirety. A typical detergent, especially a liquid, contains about 1 to about 30, preferably about 2 to about 20, more preferably about 5 to about 15, and most preferably about 8 to about 12, millimoles of calcium ions per liter of finished product. In solid detergent compositions, the formulation can contain a water-soluble calcium ion source in an amount sufficient to provide such an amount in the wash liquor. Alternatively, natural water hardness may be sufficient.

[0224] It should be understood that the aforementioned levels of calcium and / or magnesium ions are sufficient to provide enzyme stability. More calcium and / or magnesium ions can be added to the composition to provide an additional measure of grease removal performance. Thus, as a general proposition, the compositions herein will typically contain about 0.05% to about 2% by weight of a water-soluble source of calcium or magnesium ions, or both. Naturally, the amount may vary depending on the amount and type of enzyme used in the composition.

[0225] The compositions of the present specification may also optionally, but preferably, contain various additional stabilizers, particularly borate-type stabilizers. Typically, such stabilizers are compounds that can form boric acid in the composition (calculated based on boric acid), used at a level of about 0.25% to about 10% by weight, preferably about 0.5% to about 5% by weight, more preferably about 0.75% to about 3% by weight of boric acid or other borate salts. Boric acid is preferred, but other compounds such as boron oxide, borax and other alkali metal borates (e.g., sodium orthoborate, sodium metaborate, sodium pyroborate, and sodium pentaborate) are suitable. Substituted boric acids (e.g., phenylboronic acid, butaneboronic acid, and p-bromophenylboronic acid) can also be used instead of boric acid. builder

[0226] Zeolite. Microcrystalline synthetic zeolites containing bound water can be used as builders, for example zeolite A and / or P. Zeolite MAP.RTM. (commercial product of the company Crosfield) is particularly preferred as zeolite P. However, zeolites X and mixtures of A, X, Y and / or P are also suitable. Also of particular interest is the co-crystallized sodium / potassium aluminum silicate from zeolite A and zeolite X, available as the commercial product Vegobond® RX from Condea Augusta SpA. Preferably, the zeolite can be used as a spray-dried powder. If the zeolite is added as a suspension, it may contain small amounts of nonionic surfactants as stabilizers, for example 1 to 3% by weight, based on the zeolite, of ethoxylated C12-C18 fatty alcohols with 2 to 5 ethylene oxide groups, of C12-C14 fatty alcohols with 4 to 5 ethylene oxide groups, or of ethoxylated isotridecanol. Suitable zeolites have an average particle size of less than 10 μm (test method: volume distribution Coulter Counter) and preferably contain 18 to 22% by weight, especially 20 to 22% by weight, of bound water. Apart from this, phosphates can also be used as builders.

[0227] Layered silicate. A suitable substitute or partial substitute for phosphate and zeolite is crystalline layered sodium silicate.These types of crystalline layered silicates are described, for example, in European Patent Publication EP0164514A1.Preferred crystalline layered silicates are obtained, for example, from the process described in International Patent Application WO91 / 08171 A1.

[0228] Amorphous silicates. Preferred builders also include amorphous sodium silicates with a modulus (Na2O:SiO2 ratio) of 1:2 to 1:3.3, preferably 1:2 to 1:2.8, more preferably 1:2 to 1:2.6, which dissolve with delay and show multiple wash cycle properties. The delay in dissolution compared to conventional amorphous sodium silicates can be obtained in various ways, for example by surface treatment, compounding, compaction / compression or overdrying. In the context of the present invention, the term "amorphous" also means "X-ray amorphous". In other words, silicates do not produce sharp X-ray reflections typical of crystalline substances in X-ray diffraction experiments, but one or more scattered X-ray maxima with a width of several degrees of the diffraction angle. However, particularly good builder properties may be achieved even if the silicate particles produce unclear or sharp diffraction maxima in electron diffraction experiments. This should be interpreted as meaning that the product has microcrystalline regions with a size of 10 to several hundreds of nm, with values ​​of up to 50 nm at most, and in particular up to 20 nm at most, being preferred. X-ray amorphous silicates of this type also have a delayed dissolution compared to normal water glass, but are described, for example, in DE 4400024 A1. Compacted / densified amorphous silicates, compounded amorphous silicates and overdried X-ray amorphous silicates are particularly preferred.

[0229] Phosphates. Commonly known phosphates can also be added as builders, insofar as their use must not be avoided for ecological reasons. Orthophosphates, pyrophosphates and especially the sodium salts of tripolyphosphate are particularly suitable. Their content is generally not more than 25% by weight, preferably not more than 20% by weight, each based on the finished composition. In some cases, especially tripolyphosphates, already in small amounts up to 10% by weight, based on the finished composition, in combination with other builders, leads to a synergistic improvement of the secondary detergency. The preferred amount of phosphates is less than 10% by weight, in particular 0% by weight. Cobuilder

[0230] Polycarboxylic acids. Useful organic cobuilders are, for example, polycarboxylic acids, which can be used in the form of sodium salts of polycarboxylic acids, and polycarboxylic acids are understood to be carboxylic acids with multiple acid functions.These include, for example, citric acid, adipic acid, succinic acid, glutaric acid, malic acid, tartaric acid, maleic acid, fumaric acid, sugar acid, aminocarboxylic acid, nitrilotriacetic acid (NTA) and their derivatives and their mixtures.Preferred salts are the salts of polycarboxylic acids such as citric acid, adipic acid, succinic acid, glutaric acid, tartaric acid, sugar acid and their mixtures.

[0231] organic acid. Acid itself can also be used.In addition to their construction effect, acid also typically has the property of acidifying component, and therefore also helps to establish a relatively low and moderate pH in detergent or cleansing composition.In this regard, citric acid, succinic acid, glutaric acid, adipic acid, gluconic acid, and any mixture thereof are particularly mentioned.Furthermore suitable acidifying agents are known pH adjusters such as sodium hydrogen carbonate and sodium hydrogen sulfate.

[0232] polymer. Particularly suitable polymeric cobuilders are polyacrylates, which preferably have a molecular weight of 2,000 to 20,000 g / mol. Thanks to their excellent solubility, preferred representatives of this group are also short-chain polyacrylates, which have a molecular weight of 2,000 to 10,000 g / mol, more particularly 3,000 to 5,000 g / mol. Suitable polymers can also include substances that consist partially or entirely of vinyl alcohol units or their derivatives.

[0233] Further suitable copolymeric polycarboxylates are in particular copolymers of acrylic acid and methacrylic acid and of acrylic acid or methacrylic acid and maleic acid. Copolymers of acrylic acid and maleic acid, having 50-90% by weight of acrylic acid and 50-10% by weight of maleic acid, have proven to be particularly suitable. Their relative molecular weight based on the free acid is generally in the range of 2,000-70,000 g / mol, preferably 20,000-50,000 g / mol, in particular 30,000-40,000 g / mol. The (co)polymeric polycarboxylates can be added as aqueous solutions or preferably as powders. To improve water solubility, the polymers can also contain allylsulfonic acid as monomer, such as, for example, allyloxybenzenesulfonic acid and methallylsulfonic acid, as in EP 0727448 B1.

[0234] Particularly preferred are biodegradable polymers which contain two or more different monomer units, for example those which contain as monomers salts of acrylic acid and maleic acid and vinyl alcohol or vinyl alcohol derivatives, such as in DE 4300772 A1, or those which contain as monomers salts of acrylic acid and 2-alkylarylsulfonic acid and sugar derivatives.Further preferred copolymers are those described in German published patent applications DE 4303320 A1 and DE 4417734 A1, preferably those which contain as monomers acrolein and acrylic acid / acrylates or acrolein and vinyl acetate.

[0235] Likewise, other preferred builders are polymeric aminodicarboxylic acids, salts or precursors thereof. Particular preference is given to those polyaspartic acids or their salts and derivatives which are disclosed in DE 19540086 A1 as having bleach stabilizing action in addition to cobuilder properties.

[0236] Further suitable builders are the polyacetals which can be obtained by treating dialdehydes with polyol carboxylic acids having 5 to 7 carbon atoms and at least 3 hydroxyl groups, as described in EP 0 280 223 A1. Preferred polyacetals are obtained from dialdehydes such as glyoxal, glutaraldehyde, terephthalaldehyde, and mixtures thereof, and polycarboxylic acids such as gluconic acid and / or glucoheptonic acid.

[0237] carbohydrates. Further suitable organic cobuilders are dextrins, oligomers or polymers of carbohydrates obtainable by partial hydrolysis of starch. Hydrolysis can be carried out using typical processes, for example acid or enzyme catalyzed processes. The hydrolysis products preferably have an average molecular weight in the range of 400 to 500,000 g / mol. Polysaccharides with a dextrose equivalent (DE) of 0.5 to 40, more particularly 2 to 30, are preferred, DE being a recognised measure of the reducing effect of polysaccharides compared to dextrose, which has a DE of 100. Maltodextrins with a DE of 3 to 20 and dried glucose syrups with a DE of 20 to 37 can be used, as well as so-called yellow dextrins and white dextrins of relatively high molecular weight of 2,000 to 30,000 g / mol. Preferred dextrins are described in British Patent Application No. 9419091.

[0238] The oxidized derivatives of such dextrins relate to their reaction products with oxidizing compositions capable of oxidizing at least one alcohol function of the sugar ring to a carboxylic acid function. Such oxidized dextrins and methods for their preparation are known, for example, from EP 0 232 202 A1. Products oxidized at C6 of the sugar ring may be particularly advantageous.

[0239] Other derivatives of oxydisuccinate and disuccinate, preferably ethylenediamine disuccinate, are also suitable costructuring agents. Here, ethylenediamine-N,N'-disuccinate (EDDS), the synthesis of which is described, for example, in US Pat. No. 3,158,615, is preferably used in the form of its sodium or magnesium salt. In this context, glycerol disuccinate and glycerol trisuccinate are also particularly preferred, as those described in US Pat. No. 4,524,009. The suitable loading amount in zeolite-containing and / or silicate-containing formulations is in the range of 3 to 15% by weight.

[0240] Lactone. Other useful organic cobuilders are, for example, acetylated hydroxycarboxylic acids and their salts, which may also be present in lactone form and contain at least 4 carbon atoms, at least one hydroxyl group and at most two. Such cobuilders are, for example, described in International Patent Publication WO 1995 / 020029 A1. Bleaching agents, bleaching agents and bleach activators

[0241] The detergent compositions herein may optionally include a bleaching agent or a bleaching composition comprising a bleaching agent and one or more bleach activators. When present, the bleaching agent will typically be at a level of about 1% to about 30%, more typically about 5% to about 20% of the detergent composition, especially for fabric washing. When present, the amount of bleach activator is typically about 0.1% to about 60%, more typically about 0.5% to about 40% of the bleaching composition comprising the bleaching agent plus bleach activator.

[0242] The bleaching agent used herein can be any bleaching agent useful in detergent compositions for fabric cleaning, hard surface cleaning, or other cleaning purposes that are currently known or will become known. These include oxygen bleaching agents and other bleaching agents. Perborate bleaching agents, such as sodium perborate (e.g., monohydrate or tetrahydrate), can be used herein.

[0243] Another category of bleaching agents that can be used without limitation includes percarboxylic acid bleaching agents and their salts. Suitable examples of this class of agents include magnesium monoperoxyphthalate hexahydrate, the magnesium salt of metachloroperbenzoic acid, 4-nonylamino-4-oxoperoxybutyric acid, and diperoxydodecanedioic acid.

[0244] Peroxygen bleaches can also be used. Suitable peroxygen bleaching compounds include sodium carbonate peroxyhydrate and equivalent "percarbonate" bleaches, sodium pyrophosphate peroxyhydrate, urea peroxyhydrate, and sodium peroxide. Persulfate bleaches (e.g., OXONEO®, commercially manufactured by DuPont) can also be used.

[0245] A preferred percarbonate bleaching agent comprises dry particles having an average particle size ranging from about 500 micrometers to about 1,000 micrometers, with about 10% or less by weight of the particles being smaller than about 200 micrometers, about 10% or less by weight being larger than about 1,250 micrometers. If desired, the percarbonate can be coated with a silicate, borate, or water-soluble surfactant. Percarbonate is available from a variety of commercial sources.

[0246] Mixtures of bleaching agents may also be used.

[0247] Peroxygen bleaches, perborates, percarbonates, etc. are preferably combined with bleach activators to result in the in situ generation in aqueous solution (i.e., during the cleaning process) of the peroxyacid corresponding to the bleach activator. Nonanoyloxybenzenesulfonate (NOBS) and tetraacetylethylenediamine (TAED) activators are typical, and mixtures thereof may also be used.

[0248] Preferred amide derived bleach activators include (6-octanamido-caproyl)oxybenzenesulfonate, (6-nonanamido-caproyl)oxybenzenesulfonate, (6-decanamido-caproyl)-oxybenzenesulfonate, and mixtures thereof.

[0249] Another class of bleach activators includes the benzoxazine type activators disclosed in US Pat. No. 4,966,723, incorporated herein by reference.

[0250] Highly preferred lactam activators include benzoylcaprolactam, octanoylcaprolactam, 3,5,5-trimethylhexanoylcaprolactam, nonanoylcaprolactam, decanoylcaprolactam, undecenoylcaprolactam, benzoylvalerolactam, octanoylvalerolactam, decanoylvalerolactam, undecenoylvalerolactam, nonanoylvalerolactam, 3,5,5-trimethylhexanoylvalerolactam and mixtures thereof, optionally adsorbed on a solid support, such as an acylcaprolactam, preferably benzoylcaprolactam, and adsorbed on sodium perborate.

[0251] Bleaching agents other than oxygen bleaches are also known in the art and can be utilized herein.One type of non-oxygen bleaching agent of particular interest includes photoactivated bleaches such as sulfonated zinc and / or aluminum phthalocyanines.When used, the detergent composition will typically contain about 0.025% to about 1.25% by weight of such bleaching agents, particularly sulfonated zinc phthalocyanines.

[0252] Optionally, the bleaching compound can be catalyzed by a manganese compound. Such manganese-based catalysts are well known in the art and include MnIV2(uO)3(1,4,7-trimethyl-1,4,7-triazacyclononane)2(PF6)2, MnIII2(uO)1(u-OAc)2(1,4,7-trimethyl-1,4,7-triazacyclononane)2(ClO4)2, MnIV4(uO)6(1,4,7-triazacyclononane)4(ClO4)4, MnIIIMnIV4(uO)1(u-OAc)2(1,4,7-trimethyl-1,4,7-triazacyclononane)2(ClO4)3, MnIV(1,4,7-trimethyl-1,4,7-triazacyclononane)-(OCH3)3(PF6), and mixtures thereof.

[0253] As a practical matter and not a limitation, the compositions and processes herein can be tailored to provide on the order of parts per million of active bleach catalyst species in the aqueous wash liquor, preferably providing from about 0.1 ppm to about 700 ppm, more preferably from about 1 ppm to about 500 ppm of catalyst species in the wash liquor. Polymer Soil Release Agent

[0254] Any polymeric soil release agent known to those skilled in the art can be optionally used in the detergent composition and process of the present invention. The polymeric soil release agent is characterized by having both a hydrophilic segment that hydrophilizes the surface of hydrophobic fibers such as polyester and nylon, and a hydrophobic segment that deposits on the hydrophobic fibers and remains attached until the completion of the washing and rinsing cycle. It acts as an anchor for the hydrophilic segment. This allows the soil that occurs after treatment with the soil release agent to be more easily cleaned in the subsequent washing procedure.

[0255] Polymeric soil release agents useful herein include, inter alia: (a) essentially comprising (i) a polyoxyethylene segment having a degree of polymerization of at least 2, or (ii) an oxypropylene or polyoxypropylene segment having a degree of polymerization of 2 to 10, said hydrophilic segment not including any oxypropylene units unless it is joined at each end to an adjacent moiety by an ether bond, or (iii) a mixture of oxyethylene and oxyalkylene units containing from 1 to about 30 oxypropylene units, said mixture containing a sufficient amount of oxyethylene units such that the hydrophilic component has a hydrophilicity great enough to enhance the hydrophilicity of a conventional polyester synthetic fiber surface when a soil release agent is deposited on such surface, said hydrophilic segment preferably containing at least about 25% oxyethylene units, and more preferably containing at least about 50% oxyethylene units, particularly for such components having from about 20 to 30 oxypropylene units; or (b) the one or more hydrophobic components are (i) a C3 oxyalkylene terephthalate segment, where if said hydrophobic component also comprises oxyethylene terephthalate, the ratio of oxyethylene terephthalate:C3 oxyalkylene terephthalate units is about 2:1 or less, (ii) a C4-C6 alkylene or oxyC4-C6 alkylene segment, or a mixture therein, (iii) a poly(vinyl ester) segment having a degree of polymerization of at least 2, preferably polyvinyl acetate, or (iv) a C1-C4 alkyl ether or C4 hydroxyalkyl ether substituent, or a mixture therein, where said substituent is present in the form of a C1-C4 alkyl ether or C4 hydroxyalkyl ether cellulose derivative, or a mixture therein. wherein said substituents are present in the form of C1-C4 alkyl ether or C4 hydroxyalkyl ether cellulose derivatives, or mixtures thereof, and such cellulose derivatives are amphiphilic such that they have a sufficient level of C1-C4 alkyl ether and / or C4 hydroxyalkyl ether units to deposit on conventional polyester synthetic fiber surfaces and retain a sufficient level of hydroxyl upon attachment to such conventional synthetic fiber surfaces to enhance the hydrophilicity of the fiber surface. Or a combination of (a) and (b).

[0256] Typically, the polyoxyethylene segment of (a)(i) has a degree of polymerization of about 200, although higher levels can be used, preferably from 3 to about 150, more preferably from 6 to about 100. Suitable oxy C4-C6 alkylene hydrophobic segments include, but are not limited to, the end caps of the polymeric soil release agents.

[0257] Polymeric soil release agents useful in the present invention also include cellulose derivatives such as hydroxyether cellulose polymers, copolymer blocks of ethylene terephthalate or propylene terephthalate and polyethylene oxide or polypropylene oxide terephthalate. Such agents are commercially available and include hydroxyethers of cellulose such as METHOCEL® (Dow). Cellulosic soil release agents for use herein also include those selected from the group consisting of C1-C4 alkyl and C4 hydroxyalkyl celluloses.

[0258] Soil release agents featuring poly(vinyl ester) hydrophobic segments include poly(vinyl ester), e.g., graft copolymers of C1-C6 vinyl esters, preferably poly(vinyl acetate) grafted to a polyalkylene oxide backbone, such as a polyethylene oxide backbone. See EP 0219048, incorporated herein in its entirety. Commercially available soil release agents of this type include SOKALAN® type materials available from BASF, e.g., SOKALAN® HP-22.

[0259] One type of preferred soil release agent is a copolymer having random blocks of ethylene terephthalate and polyethylene oxide (PEO) terephthalate. The molecular weight of this polymeric soil release agent preferably ranges from about 25,000 to about 55,000.

[0260] Another preferred polymeric soil release agent is a polyester having repeat units of ethylene terephthalate units, containing 10-15% by weight ethylene terephthalate units with 90-80% by weight polyoxyethylene terephthalate units derived from polyoxyethylene glycol having an average molecular weight of 300-5,000. Examples of this polymer include the commercially available materials ZELCON® 5126 (manufactured by DuPont) and MILEASE® T (manufactured by ICI).

[0261] Another preferred polymeric soil release agent is the sulfonated product of a substantially linear ester oligomer consisting of an oligomeric ester backbone of terephthaloyl and oxyalkyleneoxy repeating units and terminal moieties covalently bonded to the backbone. These soil release agents are fully described in U.S. Pat. No. 4,968,451. Other suitable polymeric soil release agents include the terephthalate polyesters of U.S. Pat. No. 4,711,730, the anionic end-capped oligomeric esters of U.S. Pat. No. 4,721,580, the block polyester oligomeric compounds of U.S. Pat. No. 4,702,857, and the anionic, particularly sulfoaroyl, end-capped terephthalate esters of U.S. Pat. No. 4,877,896, all of which are fully incorporated herein by reference.

[0262] Yet another preferred soil release agent is an oligomer having repeat units of terephthaloyl, sulfoisoterephthaloyl, oxyethyleneoxy and oxy-1,2-propylene units. The repeat units form the backbone of the oligomer and are preferably terminated with modified isethionate end caps. A particularly preferred soil release agent of this type contains about one sulfoisophthaloyl unit, five terephthaloyl units, a ratio of about 1.7 to about 1.8 oxyethyleneoxy and oxy-1,2-propyleneoxy units, and two end cap units of sodium 2-(2-hydroxyethoxy)-ethanesulfonate. The soil release agent also contains about 0.5% to about 20% by weight of the oligomer of a crystalline reduction stabilizer, preferably selected from the group consisting of xylene sulfonate, cumene sulfonate, toluene sulfonate, and mixtures thereof.

[0263] If utilized, soil release agents generally comprise from about 0.01% to about 10.0%, typically from about 0.1% to about 5%, and preferably from about 0.2% to about 3.0%, by weight of the detergent compositions herein. Polymer Dispersants

[0264] Polymeric dispersants can be advantageously utilized in the detergent compositions herein at levels of about 0.1% to about 7% by weight, especially in the presence of zeolite and / or layered silicate builders.Suitable polymeric dispersants include polymeric polycarboxylates and polyethylene glycols, although others known in the art can also be used.Without intending to be limited by theory, it is believed that polymeric dispersants improve overall detergent builder performance when used in combination with other builders (including low molecular weight polycarboxylates) by inhibiting crystal growth, deflocculating particulate soil release, and preventing redeposition.

[0265] Polymeric polycarboxylate materials can be prepared by polymerizing or copolymerizing suitable unsaturated monomers, preferably in their acid form. Unsaturated monomeric acids that can be polymerized to form suitable polymeric polycarboxylates include acrylic acid, maleic acid (or maleic anhydride), fumaric acid, itaconic acid, aconitic acid, mesaconic acid, citraconic acid, and methylenemalonic acid. The presence in the polymeric polycarboxylates herein or monomer segments that do not contain carboxylate radicals, such as vinyl methyl ether, styrene, ethylene, and the like, are suitable, provided that such segments do not constitute more than about 40% by weight.

[0266] Particularly suitable polymeric polycarboxylates can be derived from acrylic acid. Such acrylic acid-based polymers useful herein are water-soluble salts of polymerized acrylic acid. The average molecular weight of such polymers in acid form is preferably in the range of about 2,000 to 10,000, more preferably in the range of about 4,000 to 7,000, and most preferably in the range of about 4,000 to 5,000. Water-soluble salts of such acrylic acid polymers can include, for example, alkali metal, ammonium and substituted ammonium salts. Soluble polymers of this type are known materials. The use of this type of polyacrylate in detergent compositions is disclosed, for example, in U.S. Pat. No. 3,308,067.

[0267] Acrylic / maleic acid based copolymers can also be used as preferred components of the dispersant / anti-redeposition agent. Such materials include water-soluble salts of acrylic acid and maleic acid copolymers. The average molecular weight of such copolymers in the acid form preferably ranges from about 2,000 to 100,000, more preferably from about 5,000 to 75,000, and most preferably from about 7,000 to 65,000. The ratio of acrylate to maleate segments in such copolymers generally ranges from about 30:1 to about 1:1, more preferably from about 10:1 to 2:1. Water-soluble salts of such acrylic acid / maleic acid copolymers can include, for example, alkali metal, ammonium and substituted ammonium salts. Soluble acrylate / maleate copolymers of this type are known materials, described in EP 0 193 360 A1, which also describes such polymers containing hydroxypropyl acrylate. Still other useful dispersants include maleic / acrylic / vinyl alcohol terpolymers, such as a 45 / 45 / 10 terpolymer of acrylic / maleic / vinyl alcohol.

[0268] Another polymeric material that can be included is polyethylene glycol (PEG). PEG not only performs dispersant functions, but also acts as a clayey soil removal-antiredeposition agent. Typical molecular weight ranges for these purposes are from about 500 to about 100,000, preferably from about 1,000 to about 50,000, more preferably from about 1,500 to about 10,000.

[0269] Polyaspartic and polyglutamic acid dispersants may also be used, particularly in combination with zeolite builders. Dispersants such as polyaspartic acid preferably have a molecular weight (average) of about 10,000. Foam suppressors / SUD suppressors

[0270] It may be advantageous to add conventional foam inhibitors to the composition, especially when used in automatic cleaning processes. Suitable foam inhibitors include, for example, soaps of natural or synthetic origin with a high content of C18-C24 fatty acids. Suitable non-surface-active type foam inhibitors are, for example, organopolysiloxanes and their very fine mixtures, optionally silanized silica, and paraffins, waxes, microcrystalline waxes and their mixtures with silanized silica or bisstearylethylenediamide. Mixtures of various foam inhibitors, for example mixtures of silicones, paraffins or waxes, are also advantageously used. Preferably, the foam inhibitors, in particular silicone-containing and / or paraffin-containing foam inhibitors, are loaded into a granular water-soluble or dispersible carrier material. In particular in this case, mixtures of paraffins and bisstearylethylenediamide are preferred.

[0271] Compounds for reducing or inhibiting suds formation can be incorporated into the detergent compositions of the present invention. Suds inhibition can be particularly important in the so-called "high concentration wash process" and in front-loading European washing machines.

[0272] A wide variety of materials can be used as suds suppressors, and suds suppressors are well known to those skilled in the art. For example, see Kirk Othmer Encyclopedia of Chemical Technology, Third Edition, Volume 7, pages 430-447 (John Wiley & Sons, Inc., 1979). One category of suds suppressors of particular interest includes monocarboxylic acid fatty acids and soluble salts therein. The monocarboxylic acids and their salts used as suds suppressors typically have hydrocarbyl chains of 10 to about 24 carbon atoms, preferably 12 to 18 carbon atoms. Suitable salts include alkali metal salts such as sodium, potassium, and lithium salts, as well as ammonium salts and alkanola ammonium salts.

[0273] The detergent compositions herein may also include non-surfactant suds suppressors. These include, for example, high molecular weight hydrocarbons such as paraffins, fatty acid esters (e.g., fatty acid triglycerides), fatty acid esters of monohydric alcohols, and aliphatic C18-C40 ketones (e.g., stearone). Other suds suppressors include tri- to hexaalkylmelamine or di- to tetraalkyldiamine chlorotriazines formed as products of cyanuric chloride with 2-3 moles of primary or secondary amines containing 1-24 carbon atoms, N-alkylated aminotriazines such as monostearyl phosphates such as propylene oxide and monostearyl alcohol phosphate esters and monostearyl dialkali metal (e.g., K, Na, and Li) phosphates and phosphate esters. Hydrocarbons such as paraffins and haloparaffins are available in liquid form. Liquid hydrocarbons are liquid at room temperature and atmospheric pressure, with a pour point in the range of about -40°C to about 50°C, and a minimum boiling point of about 110°C (atmospheric pressure) or higher. It is also known to utilize waxy hydrocarbons, preferably having a melting point below about 100° C. Hydrocarbon suds suppressors are known in the art and include aliphatic, alicyclic, aromatic, and heterocyclic saturated or unsaturated hydrocarbons having from about 12 to about 70 carbon atoms. The term "paraffin" as used in this discussion of suds suppressors is intended to include mixtures of true paraffins and cyclic hydrocarbons.

[0274] Another preferred category of non-surfactant suds suppressors includes silicone suds suppressors. This category includes the use of polyorganosiloxane oils, such as polydimethylsiloxane, dispersions or emulsions of polyorganosiloxane oils or resins, and combinations of polyorganosiloxanes with silica particles, where the polyorganosiloxane is chemisorbed or fused onto the silica. Silicone suds suppressors are well known in the art.

[0275] Other silicone suds suppressors are disclosed in U.S. Pat. No. 3,455,839, which is incorporated in its entirety, and which relates to a composition and process for defoaming aqueous solutions by incorporating small amounts of polydimethylsiloxane fluids therein.

[0276] Mixtures of silicones and silanated silicas are described, for example, in DE-OS 2124526, which is incorporated herein in its entirety. Silicone antifoam and foam control agents in granular detergent compositions are disclosed in U.S. Patent No. 4,652,392, which is incorporated herein in its entirety.

[0277] In the preferred silicone suds suppressors used herein, the solvent for the continuous phase is comprised of certain polyethylene glycols or polyethylene-polypropylene glycol copolymers or mixtures thereof (preferred), or polypropylene glycol. The primary silicone suds suppressors are branched / crosslinked and preferably not linear.

[0278] The silicone suds suppressors herein preferably include polyethylene glycol and polyethylene glycol / polypropylene glycol copolymers, all of which have an average molecular weight of less than about 1,000, preferably from about 100 to 800. The polyethylene glycol and polyethylene glycol / polypropylene copolymers herein have a solubility in water at room temperature of greater than about 2% by weight, preferably greater than about 5% by weight.

[0279] Preferred solvents herein are polyethylene glycols having an average molecular weight of less than about 1,000, more preferably between about 100 and 800, and most preferably between 200 and 400, and polyethylene glycol / polypropylene glycol copolymers, preferably PPG 200 / PEG 300. Preferred are polyethylene glycols and polyethylene-polypropylene glycol copolymers in a weight ratio of between about 1:1 and 1:10, and most preferably between 1:3 and 1:6.

[0280] Preferred silicone suds suppressors for use herein are specifically free of polypropylene glycols having a molecular weight of 4000. They also preferably are free of block copolymers of ethylene oxide and propylene oxide such as PLURONIC® L101.

[0281] Other suds suppressors useful herein include secondary alcohols (e.g., 2-alkyl alkanols) and mixtures of such alcohols with silicone oils. Secondary alcohols include C6-C16 alkyl alcohols having C1-C16 chains. A preferred alcohol is 2-butyl octanol available from Condea under the trademark ISOFOL® 12. A mixture of secondary alcohols is available from Enichem under the trademark ISALCHEM® 123. Mixed suds suppressors typically include a mixture of alcohol+silicone in a weight ratio of 1:5 to 5:1.

[0282] The compositions herein generally comprise 0% to about 5% of suds suppressor. When utilized as suds suppressors, monocarboxylic fatty acids, and salts therein, will typically be present in amounts up to about 5% by weight of the detergent composition. Preferably, about 0.5% to about 3% of fatty monocarboxylic suds suppressors are utilized. Silicone suds suppressors are typically utilized in amounts up to about 2.0% by weight of the detergent composition, although larger amounts can be used. This upper limit is practical in nature, primarily due to concerns regarding minimizing costs and the effectiveness of small amounts to effectively control suds. Preferably, about 0.01% to about 1% of silicone suds suppressors are utilized, more preferably about 0.25% to about 0.5%. As used herein, these weight percentage values ​​include any silica that may be utilized in combination with the polyorganosiloxane, as well as any auxiliary materials that may be utilized. Monostearyl phosphate suds suppressors are generally utilized in amounts ranging from about 0.1% to about 2% by weight of the composition. Hydrocarbon suds suppressors are typically utilized in amounts ranging from about 0.01% to about 5.0%, although higher levels can be used. Alcohol suds suppressors are typically used at 0.2% to 3% by weight of the finished composition. Sequence Tranz and Chelating Agents

[0283] The salts of polyphosphonic acids can be considered as sequestering agents or stabilizers, especially for peroxy compounds and enzymes sensitive to heavy metal ions, where, for example, the sodium salts of 1-hydroxyethane-1,1-diphosphonate, diethylenetriaminepentamethylenephosphonate or ethylenediaminetetramethylenephosphonate are used in amounts of 0.1 to 5% by weight.

[0284] The detergent compositions herein may also optionally include one or more iron and / or manganese chelating agents. Such chelating agents may be selected from the group consisting of aminocarboxylates, aminophosphonates, polyfunctionally substituted aromatic chelating agents, and mixtures thereof, all of which are defined below. Without intending to be bound by theory, it is believed that the advantages of these materials are due in part to their extraordinary ability to remove iron and manganese ions from the wash solution by forming soluble chelates. It will be understood that some of the aforementioned detergent builders can function as chelating agents, and that when such detergent builders are present in sufficient amounts, they can provide both functions.

[0285] Aminocarboxylates useful as optional chelating agents include ethylenediaminetetraacetate, N-hydroxyethylethylenediaminetriacetate, nitrilotriacetate, ethylenediaminetetrapropionate, triethylenetetraaminehexaacetate, diethylenetriaminepentaacetate, and ethanoldiglycine, alkali metal, ammonium, and substituted ammonium salts therein.

[0286] Amino phosphonates are also suitable for use as chelating agents in the compositions of the present invention, where at least low levels of total phosphorus are acceptable in the detergent composition, and include ethylenediaminetetrakis(methylenephosphonate) as DEQEST.Preferably, these amino phosphonates do not contain alkyl or alkenyl groups having more than about 6 carbon atoms.

[0287] Polyfunctionally substituted aromatic chelating agents are also useful in the compositions herein. Preferred compounds of this type in the acid form are the dihydroxydisulfobenzenes, such as 1,2-dihydroxy-3,5-disulfobenzene.

[0288] A preferred biodegradable chelating agent for use herein is ethylenediaminedisuccinate ("EDDS"), particularly the [S,S] isomer.

[0289] When utilized, these chelating agents will generally comprise from about 0.1% to about 10% by weight of the detergent compositions herein. More preferably, when utilized, the chelating agents will comprise from about 0.1% to about 3.0% by weight of such compositions. Removes clay stains / prevents redeposition

[0290] The detergent compositions of the present invention can also optionally contain water-soluble ethoxylated amines with clay soil removal and anti-redeposition properties. Granular detergent compositions containing these compounds typically contain about 0.01% to about 10.0% by weight of water-soluble ethoxylate amines. Liquid detergent compositions usually contain about 0.01% to about 5%.

[0291] The most preferred clay soil removal and anti-redeposition agent is ethoxylated tetraethylenepentamine. Exemplary ethoxylated amines are further described in US Pat. No. 4,597,898. Other groups of preferred clay soil removal-anti-redeposition agents are cationic compounds as disclosed in EP 0111965 A1, ethoxylated amine polymers as disclosed in EP 0111984 A1, zwitterionic polymers as disclosed in EP 0112592 A1, and amine oxides as disclosed in US Pat. No. 4,548,744. Another type of preferred anti-redeposition agent includes carboxymethyl cellulose (CMC) materials. These materials are well known in the art. Grey Inhibitor

[0292] Graying inhibitors have the function of keeping the dirt removed from the fibers suspended in the wash liquor, thereby preventing the dirt from being redeposited. Mainly organic water-soluble colloids are suitable for this, for example water-soluble salts of (co)polymeric carboxylic acids, adhesives, gelatin, salts of ether carboxylic or ether sulfonic acids of starch or cellulose, or acid sulfates of cellulose or starch. Water-soluble acid group-containing polyamides are also suitable for this purpose. In addition, soluble starch preparations and others, for example degraded starch, aldehyde starch, etc., can be used as the abovementioned starch products. Polyvinylpyrrolidone can also be used. However, preference is given to the use of cellulose ethers such as carboxymethylcellulose (Na salt), methylcellulose, hydroxyalkylcellulose, and mixed ethers such as methylhydroxyethylcellulose, methylhydroxypropylcellulose, methylcarboxymethylcellulose and mixtures thereof, as well as polyvinylpyrrolidone, which can be added, for example, in amounts of 0.1% to 5% by weight based on the composition. Optical brighteners and UV absorbents

[0293] Any optical brightener or other brightening or whitening agent known in the art can be incorporated into the detergent compositions herein, typically at a level of about 0.05% to about 1.2% by weight. Commercially available optical brighteners that may be useful in the present invention can be divided into subgroups, including, but not necessarily limited to, derivatives of stilbenes, pyrazolines, coumarins, carboxylic acids, methine cyanines, dibenzothiophene-5,5-dioxides, azoles, 5- and 6-membered heterocycles, and other agents.

[0294] Preferred brighteners include the PHORWHITE® series of brighteners from Verona. Other brighteners disclosed in this reference include Tinopal® UNPA, Tinopal CBS, and Tinopal 5BM available from Ciba-Geigy; ArticWhite® CC and ArticWhite CWD available from Hilton-Davis; 2-(4-stryl-phenyl)-2H-naphthol[1,2-d]triazole, 4,4'-bis-(1,2,3-triazol-2-yl)-stilbene; 4,4'-bis(stryl)bisphenyl, and aminocoumarin. Specific examples of these brighteners include 4-methyl-7-diethyl-aminocoumarin; 1,2-bis(-benzimidazol-2-yl)ethylene; 1,3-diphenyl-furazoline; 2,5-bis(benzoxazol-2-yl)thiophene; 2-stryl-napth-[1,2-d]oxazole; and 2-(stilben-4-yl)-2H-naphth-[1,2-d]triazole. Anionic brighteners are preferred herein.

[0295] The composition may, for example, contain a derivative of diaminostilbene disulfonic acid or its alkali metal salt as an optical brightener. Suitable optical brighteners are, for example, salts of 4,4'-bis-(2-anilino-4-morpholino-1,3,5-triazinyl-6-amino)stilbene-2,2'-disulfonic acid or compounds of similar structure containing diethanolamino, methylamino, anilino or 2-methoxyethylamino groups instead of morpholino groups. Substituted diphenylstyryl type brighteners may also be present, for example, 4,4'-bis(2-sulfostyryl)diphenyl, 4,4'-bis(4-chloro-3-sulfostyryl)diphenyl or the alkali metal salt of 4, 4-(4-chlorostyryl)-4'-(2-sulfostyryl)diphenyl. Mixtures of the above-mentioned brighteners may also be used.

[0296] In addition, UV absorbers can be added. These are compounds with a clear absorption capacity for UV rays, which not only act as UV stabilizers, but also improve the photostability of colorants and pigments, both in the textile and in the skin of the wearer of the textile, by protecting them from UV rays penetrating the fabric. In general, efficient non-radiative inactivating compounds are derivatives of benzophenones, mainly substituted with hydroxyl and / or alkoxy groups in the 2- and / or 4-positions. Also preferred are substituted benzotriazoles, as well as acrylates (cinnamic acid derivatives) phenyl-substituted in the 3-position, salicylates, optionally with a cyano group in the 2-position, organic Ni complexes, and natural substances such as umbelliferone and endogenous urocanic acid. In a preferred embodiment, the UV absorber absorbs UV-A and UV-B radiation and possible UV-C radiation, and re-emits blue wavelength light so that they also have optical brightening effect.Preferred UV absorbers are triazine derivatives, such as hydroxyaryl-1,3,5-triazine, sulfonated 1,3,5-triazine, o-hydroxyphenyl-benzotriazole and 2-aryl-2H-benzotriazole, and bis(anilinotriazinyl-amino)stilbenedisulfonic acid and their derivatives.Ultraviolet absorbing pigments such as titanium dioxide can also be used as UV absorbers. Dye transfer inhibitors

[0297] The detergent composition of the present invention can also contain one or more materials that are effective in inhibiting the transfer of dye from one fabric to another during the washing process.Generally, such dye transfer inhibitors include polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, manganese phthalocyanine, peroxidase, and mixtures thereof.When used, these agents typically comprise about 0.01% to about 10% by weight of the composition, preferably about 0.01% to about 5% by weight, more preferably about 0.05% to about 2% by weight.

[0298] More specifically, preferred polyamine N-oxide polymers for use herein are described in US Pat. No. 6,491,728, which is incorporated herein by reference.

[0299] Any polymer backbone can be used so long as the amine oxide polymer formed is water soluble and has dye transfer inhibiting properties. Examples of suitable polymer backbones are polyvinyl, polyalkylene, polyester, polyether, polyamide, polyimide, polyacrylate, and mixtures thereof. These polymers include random or block copolymers in which one monomer type is an amine N-oxide and the other monomer type is an N-oxide. Amine N-oxide polymers typically have a ratio of amine to amine N-oxide of 10:1 to 1:1,000,000. However, the number of amine oxide groups present in a polyamine oxide polymer can be varied by appropriate copolymerization or by appropriate degrees of N-oxidation. Polyamine oxides can be obtained in almost any degree of polymerization. Typically, the average molecular weight is in the range of 500 to 1,000,000, with 1,000 to 500,000 being more preferred and 5,000 to 100,000 being most preferred. This preferred class of materials is sometimes referred to as "PVNO".

[0300] The most preferred polyamine N-oxide useful in the cleaning compositions herein is poly(4-vinylpyridine-N-oxide) having an average molecular weight of about 50,000 and an amine to amine N-oxide ratio of about 1:4.

[0301] Copolymers of N-vinylpyrrolidone and N-vinylimidazole polymers (referred to as a class as "PVPVI") are also preferred for use herein. Preferably, the PVPVI has an average molecular weight range of 5,000 to 1,000,000, more preferably 5000 to 200,000, and most preferably 10,000 to 20,000. PVPVI copolymers typically have a molar ratio of N-vinylimidazole to N-vinylpyrrolidone of 1:1 to 0.2:1, more preferably 0.8:1 to 0.3:1, and most preferably 0.6:1 to 0.4:1. These copolymers can be either linear or branched.

[0302] The compositions of the present invention may also use polyvinylpyrrolidone ("PVP") having an average molecular weight of about 5000 to about 400,000, preferably about 5000 to about 200,000, more preferably about 5000 to about 50,000. PVP is known to those skilled in the detergent art. Compositions containing PVP may also include polyethylene glycol ("PEG") having an average molecular weight of about 500 to about 100,000, preferably about 1,000 to about 10,000. Preferably, the ratio of PEG to PVP on a ppm basis delivered in the cleaning solution is about 2:1 to about 50:1, more preferably about 3:1 to about 10:1.

[0303] The detergent compositions herein can also optionally contain from about 0.005% to 5% by weight of certain types of hydrophilic optical brighteners that also provide dye transfer inhibition activity. If used, the compositions herein will preferably contain from about 0.01% to 1% by weight of such optical brighteners.

[0304] One preferred brightener is 4,4',-bis[(4-anilino-6-(N-2-bis-hydroxyethyl)-s-triazin-2-yl)amino]-2,2'-stilbenedisulfonic acid and disodium salt. This particular brightener species is commercially available from Ciba-Geigy Corporation under the trade name Tinopal-UNPA-GX®. Tinopal-UNPA-GX is a preferred hydrophilic optical brightener useful in the detergent compositions herein.

[0305] Another preferred brightener is 4,4'-bis[(4-anilino-6-(N-2-hydroxyethyl-N-methylamino)-s-triazin-2-yl)amino]2,2'-stilbenedisulfonic acid and disodium salt. This particular brightener species is commercially available from Ciba-Geigy Corporation under the trade name Tinopal 5BM-GX®.

[0306] Another preferred brightener is 4,4'-bis[(4-anilino-6-morpholino-s-triazin-2-yl)amino]2,2'-stilbenedisulfonic acid, sodium salt. This particular brightener species is commercially available from Ciba Geigy Corporation under the trade name Tinopal AMS-GX®.

[0307] The particular optical brightener species selected for use in the present invention, when used in combination with the aforementioned selected polymeric dye transfer inhibitors, provide the advantage of particularly effective dye transfer inhibition performance. The combination of such selected polymeric materials (e.g., PVNO and / or PVPVI) with such selected optical brighteners (e.g., Tinopal UNPA-GX, Tinopal 5BM-GX and / or Tinopal AMS-GX) provides significantly better dye transfer inhibition in aqueous wash solutions than either of these two detergent composition components when used alone. Without being bound by theory, it is believed that such brighteners function in this way because they have a high affinity for fabrics in the wash liquor and therefore deposit relatively quickly on these fabrics. The extent to which brighteners are attached to fabrics in the wash liquor can be defined by a parameter called the "exhaustion factor". The exhaustion factor is generally expressed as the ratio of a) the brightener material attached to the fabric and b) the initial brightener concentration in the wash liquor. Brighteners with a relatively high exhaustion factor are best suited to inhibit dye transfer in the context of the present invention.

[0308] Of course, it will be understood that other conventional optical brightener type compounds may optionally be used in the present compositions to provide a conventional fabric "brightness" benefit rather than a true dye transfer inhibition effect, and such use is conventional and well known in detergent formulations. Thickener

[0309] The composition may also include general thickening and anti-deposition compositions, as well as viscosity modifiers. Viscosity modifiers include, for example, polyacrylates, polycarboxylic acids, polysaccharides and their derivatives, polyurethanes, polyvinylpyrrolidones, castor oil derivatives, polyamine derivatives such as quaternized and / or ethoxylated hexamethylene diamines, and any mixtures thereof. Preferred compositions have a viscosity of less than 10,000 mPa*s, measured with a Brookfield viscometer at a temperature of 20°C and a shear rate of 50 min-1. Inorganic salts

[0310] Further suitable components of the composition are water-soluble inorganic salts such as bicarbonates, carbonates, amorphous silicates or mixtures thereof, alkali carbonates and amorphous silicates being particularly used, mainly sodium silicates with a molar ratio Na2O:SiO2 of 1:1 to 1:4.5, preferably 1:2 to 1:3.5. Preferred compositions contain alkali salts, builders and / or cobuilders, preferably sodium carbonate, zeolite, crystalline layered sodium silicate and / or trisodium citrate, in an amount of 0.5 to 70% by weight, preferably 0.5 to 50% by weight, in particular 0.5 to 30% by weight of anhydrous substances. Perfumes and colourants

[0311] The composition can include more typical detergent and cleansing composition ingredients such as fragrance and / or coloring agents, with coloring agents being preferred that leave no or negligible color on the washed fabric.The total preferred amount of coloring agents added is less than 1% by weight, preferably less than 0.1% by weight, based on the composition.The composition can also include a white pigment, such as TiO2. [Industrial Applicability]

[0312] Another object of the present invention is a method for providing a cosmetic and / or pharmaceutical composition with improved olfactory performance and stability, comprising or consisting of the following steps: (a) Providing a cosmetic and / or pharmaceutical composition. (b) adding an amount of 1,2-pentanediol, said 1,2-pentanediol being obtained by the following process: (i) providing at least one starting material selected from furfuryl alcohol and furfural; (ii) reacting at least one of said starting materials with hydrogen in the presence of a heterogeneous catalyst to form 1,2-pentanediol, wherein said heterogeneous catalyst comprises: one or more metals selected from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium in metallic form, and / or - one or more compounds of a metal selected from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium. - one or more support materials selected from the group consisting of activated carbon, aluminum oxide, silicon dioxide, and silicon carbide. (iii) The 1,2-pentanediol thus obtained is removed from the reaction mixture.

[0313] Finally, another object of the present invention is the use of 1,2-pentanediol as an additive for producing cosmetic and / or pharmaceutical compositions with improved olfactory performance and stability, said 1,2-pentanediol being obtained by the following process: (i) providing at least one starting material selected from furfuryl alcohol and furfural; (ii) reacting at least one of said starting materials with hydrogen in the presence of a heterogeneous catalyst to form 1,2-pentanediol, wherein said heterogeneous catalyst comprises: one or more metals selected from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium in metallic form, and / or - one or more compounds of metals selected from the group consisting of platinum, rhodium, ruthenium, nickel, palladium, and iridium. - one or more support materials selected from the group consisting of activated carbon, aluminum oxide, silicon dioxide, and silicon carbide. (iii) The 1,2-pentanediol thus obtained is removed from the reaction mixture. EXAMPLES

[0314] Example 1

[0315] Production of 1,2-pentanediol Preparation of 1,2-pentanediol according to the present invention 100 g (1.02 moles) of furfuryl alcohol were dissolved in 200 g of ethanol. 10 g of catalyst (5% by weight platinum dioxide on gamma aluminum oxide, corresponding to 0.5 g of platinum dioxide) were added and the hydrogenation was carried out at 0-5° C. and 1 bar of hydrogen pressure. After 5 hours, the absorption of hydrogen was complete. The catalyst was filtered off, the solvent ethanol and finally the product mixture were filtered off. 105 g of distillate was obtained with the following composition: 2% 2-pentanol 2% 1-pentaneol 15% tetrahydrofurfuryl alcohol 80% 1,2-pentanediol 1% 1,5-pentanediol.

[0316] Yield: 84 g (0.81 mol) of 1,2-pentanediol (corresponding to 80% of the theoretical yield)

[0317] The distillates from the six hydrogenation batches were combined (total 630 g) and subjected to fractional distillation in a 1 m packed column. 475 g of colorless 1,2-pentanediol with a purity of 99.9% was obtained as the main fraction.

[0318] The heterogeneous platinum catalyst used in Example 1 was prepared by dissolving 1.8 g of hexachloroplatinic acid in water and applying the solution to 10 g of the support material gamma aluminum oxide by the incipient wetness process. The solid thus obtained was introduced into a NaNO3 melt at a temperature in the range of 310-320°C, the temperature of the resulting mixture was gradually increased to 500°C, and then the mixture was maintained at 500°C for 1 hour. Comparative Example 1

[0319] Preparation of 1,2-Pentanediol by state-of-the-art technology According to the Journal of American Chemical Society 71, 415 (1949) or the cited literature references in Journal of American Chemical Society 67, 272 (1945), 100 g (1.02 mol) of furfuryl alcohol were dissolved in 200 g of acetic acid. 4 g of platinum dioxide (without carrier material; supplier: Acros) were added and hydrogenation was carried out at 0-5 ° C and 1 bar of hydrogen pressure. After 10 hours, the absorption of hydrogen was complete, the catalyst was filtered off and the solvent was distilled off. The distillation residue was then taken up in 500 g of methyl tert-butyl ether and stirred with 40 g (0.74 mol) of sodium methylate to deacetylate the diols present in the form of mono- or diacetates. After adding 50 g of water, the mixture was neutralized with semi-concentrated hydrochloric acid, the phases were separated and the solvent was removed. After distillation, 80 g of an oily liquid was obtained with the following composition: 26% 2-pentanol 10% 1-pentanol, 35% tetrahydrofurfuryl alcohol, 6% 1,2-pentanediol, 2% 1,5-pentanediol. Yield: 21 g (0.20 mol) of 1,2-pentanediol (corresponding to 20% of the theoretical yield). Olfactory evaluation Example 2

[0320] Comparative Example 2

[0321] Fragrance-free face cream formulations were prepared and 1,2-pentanediol was added in an amount of 2 weight percent according to Example 1 (invention) and 1 (comparison). The products were stored for one week at 20°C and 40°C, respectively, and their odor was evaluated by a panel of 10 experienced testers. The meaning of the scores is as follows: (0) = completely odorless; (1) = slightly malodorous; (2) severely malodorous; (3) dominate rancid. The average results are shown in Table 1.

[0322] [Table 1]

[0323] Both compositions immediately after preparation were completely odorless, whereas the comparative sample showed a bad odor already after one day and developed a strong bad odor when stored at high temperatures. In contrast, the sample according to the invention was almost stable over the entire period and even at higher temperatures. Example 3

[0324] Comparative Example 3

[0325] A fragrance-free sprayable wound cream formulation is prepared, Example 2 1,2-pentanediol according to the invention and according to 1 (for comparison) was added in an amount of 2% by weight. The products were stored for one week at 20°C and 40°C, respectively, and their odor was evaluated by a panel of 10 experienced testers. The meaning of the scores is as follows: (0) = completely odorless, (1) = slightly malodorous, (2) severely malodorous, (3) dominating rancidity. The average results are shown in Table 2. [Table 2]

[0326] Both compositions immediately after preparation were completely odorless, whereas the comparative sample showed a bad odor already after one day and developed a strong bad odor when stored at high temperatures. In contrast, the sample according to the invention was almost stable over the entire period and even at higher temperatures. Formulation example

[0327] The following examples show various cosmetic and pharmaceutical formulations containing 1,2-pentanediol in a quality according to the invention entitled "Hydrolite® 5 Green". All of these compositions are fragrance-free to show the advantages of using the new 1,2-pentanediol quality that does not require the presence of fragrance for masking purposes. Of course, it should be understood that all of these formulations may contain fragrances for other purposes. [Table F1] [Table F2]

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Claims

1. 1. A cosmetic, pharmaceutical and / or detergent composition comprising 1,2-pentanediol and 4-hydroxyacetophenone, wherein the 1,2-pentanediol contains less than 10 ppm of butyric acid.

2. 2. The cosmetic, pharmaceutical and / or detergent composition of claim 1, comprising said 1,2-pentanediol in an amount of from 0.1 to 10 weight percent, calculated on the basis of said composition.

3. 2. The cosmetic, pharmaceutical and / or detergent composition of claim 1, comprising said 4-hydroxyacetophenone in an amount of from 0.01 to 2 percent by weight, calculated on the composition.

4. 10. The cosmetic composition of claim 1, wherein the cosmetic composition represents a skin care, hair care, personal care, sun care or oral care composition.

5. 5. The cosmetic composition of claim 4 which is a cream, lotion, spray, emulsion, ointment, gel or mousse.

6. 10. The detergent composition of claim 1, wherein the detergent composition is a heavy duty powder detergent, a heavy duty liquid detergent, a light duty powder detergent, a light duty liquid detergent, a fabric softener, a manual dishwashing agent or an all-purpose cleaner.

7. 10. The cosmetic, pharmaceutical and / or detergent composition of claim 1, further comprising a 1,2-alkanediol having from 6 to 12 carbon atoms.

8. 8. The cosmetic, pharmaceutical and / or detergent composition of claim 7, wherein said 1,2-alkanediol is selected from the group consisting of 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2-dodecanediol, 1,2-tetradecanediol and mixtures thereof.

9. 8. The cosmetic, pharmaceutical and / or detergent composition of claim 7, comprising said 1,2-alkanediol in an amount of from 0.1 to 5 weight percent calculated on the composition.

10. 1. A method for providing an alkaline cosmetic and / or pharmaceutical and / or detergent composition with improved olfactory performance and stability, comprising: (a) providing a cosmetic composition and / or a pharmaceutical composition and / or a detergent composition; (b) adding 1,2-pentanediol containing less than 10 ppm butyric acid, and 4-hydroxyacetophenone.

11. 11. A method for providing a cosmetic, pharmaceutical and / or detergent composition according to claim 10, comprising said 1,2-pentanediol in an amount of from 0.1 to 10 weight percent, calculated on the basis of said composition.

12. 11. A method for providing a cosmetic, pharmaceutical and / or detergent composition according to claim 10, comprising said 4-hydroxyacetophenone in an amount of from 0.01 to 2 weight percent, calculated on the basis of said composition.

13. 1. Use of a mixture of 1,2-pentanediol and 4-hydroxyacetophenone as an additive for producing a cosmetic and / or pharmaceutical and / or detergent composition having improved olfactory performance and stability, comprising 1,2-pentanediol, wherein the 1,2-pentanediol contains less than 10 ppm of butyric acid.

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