Compositions containing n-nonanoic acid esters of xylitol and / or sorbitan

Abstract

The present invention relates to compositions comprising n-nonanoic acid esters of xylitan and / or sorbitan, methods for making said compositions, formulations containing said compositions and uses of said compositions.

Description

[Technical field]

[0001] The present invention relates to compositions comprising n-nonanoic acid esters of xylitan and / or sorbitan, methods for making said compositions, formulations containing said compositions and uses of said compositions.

[0002] prior art EP 2 410 979 discloses a formulation for cleaning and caring for human or animal body parts comprising a sorbitan carboxylic acid ester, the carboxylic acid moiety of which is derived from a carboxylic acid containing 6 to 10 carbon atoms and which has a hydroxyl number (OH number) of more than 350.

[0003] European Patent No. 3744310 states: A) at least one sorbitan carboxylate of at least one carboxylic acid selected from carboxylic acids having 6 to 12 carbon atoms, all of the sorbitan carboxylates present in component A together having an average degree of esterification of 0.7 to 2.1 carboxylic acid groups per sorbitan carboxylate; B) at least one glycerol carboxylic acid ester of at least one carboxylic acid selected from carboxylic acids having 6 to 22 carbon atoms, all glycerol carboxylic acid esters present in component B together having an average degree of esterification of 0.7 to 1.5 carboxylic acid groups per glycerol carboxylic acid ester; C) Water and Including, A composition is disclosed, characterized in that the sum of components A) and B) is present in the range of at least 50% by weight of the total composition.

[0004] Korean Patent Publication No. 10-1939851 describes esters of anhydrous xylitol and the use of said carboxylic acid esters of anhydrous xylitol as rheological additives / viscosity modifiers in emulsions.

[0005] Dishes and cutlery that are washed repeatedly in a dishwasher often pick up traces of the rinse aid and / or detergent used, which often results in foods tasting bitter when consumed from such dishes and cutlery, as well as glasses and beverages.

[0006] An object of the present invention is to reduce deposits caused by dishwashing.

[0007] Detailed Description of the Invention Surprisingly, it has been found that n-nonanoic acid esters of xylitan and / or sorbitan solve this problem.

[0008] Accordingly, the present invention provides an anhydrosugar alcohol n-nonanoic acid ester composition comprising an anhydrosugar alcohol and a different anhydrosugar alcohol mono n-nonanoic acid ester, wherein the anhydrosugar alcohol is selected from sorbitan and xylitan, preferably sorbitan.

[0009] The present invention further provides a method for producing the anhydrosugar alcohol n-nonanoic acid ester compositions according to the present invention, formulations comprising said compositions, and uses of the anhydrosugar alcohol n-nonanoic acid ester compositions according to the present invention to prevent and / or reduce build-up on dishes, glasses and cutlery from the dishwashing process.

[0010] One advantage of the compositions of the present invention is their improved odor profile.

[0011] Another advantage of the present invention is that although sorbitan esters are known suds boosters, the compositions of the present invention do not induce high suds in automatic dishwashing processes.

[0012] A further advantage is that the compositions of the present invention are cleaning boosters for the cleaning industry with excellent good wetting properties.

[0013] Another advantage of the present invention is that the compositions of the present invention have fast soil penetration.

[0014] A further advantage is that the compositions of the present invention have excellent cleaning power, especially for removing stains, even if the stains are very difficult or messy to remove.

[0015] Another advantage of the present invention is that the compositions of the present invention have high dispersibility and emulsification properties.

[0016] A further advantage is that the compositions of the present invention effectively prevent soil redeposition.

[0017] Another advantage of the present invention is that the compositions of the present invention support a sheeting effect during the rinsing step, resulting in a fast, residue-free dry surface.

[0018] Another advantage is that the compositions of the present invention exhibit superior properties in terms of taste as well as undesirable residue of fragrance and / or odor on rinsed dishes.

[0019] Another advantage of the present invention is that the compositions of the present invention are readily biodegradable.

[0020] Another advantage of the present invention is that the compositions of the present invention exhibit effective makeup removal properties.

[0021] Another advantage of the present invention is that the compositions of the present invention provide effective solubilizing properties for emollients and fragrances.

[0022] Another advantage of the present invention is that the compositions of the present invention provide effective thickening properties in water-based cosmetic cleansing formulations.

[0023] Another advantage of the present invention is that the compositions of the present invention exhibit effective co-emulsifying properties in cosmetic creams and lotions.

[0024] Another advantage of the present invention is that the compositions of the present invention provide effective moisturizing properties in cosmetic formulations.

[0025] Another advantage of the present invention is that the compositions of the present invention do not require preservation because they contain no water or have low water content.

[0026] Another advantage of the present invention is that the compositions of the present invention have a long shelf life of more than 12 months due to being water-free or having low water content, thereby avoiding hydrolysis.

[0027] Another advantage of the present invention is that the compositions of the present invention are free of petrochemical-based polyethylene glycols.

[0028] Another advantage of the present invention is that the compositions of the present invention are low temperature processable, resulting in low energy consumption during processing.

[0029] Another advantage of the present invention is that the compositions of the present invention are derived from palm-free sources, which helps in mitigating climate change by reducing deforestation of tropical rainforests.

[0030] Thus, what is claimed in accordance with the present invention is: A) an anhydrous sugar alcohol; B) anhydrosugar alcohol mono-n-nonanoic acid ester; C) Anhydrosugar alcohol di-n-nonanoic acid ester wherein the anhydrosugar alcohol is selected from sorbitan and xylitan, preferably sorbitan.

[0031] Nonanoic Acid / Pelargonic Acid n-Nonanoic acid (pelargonic acid, CAS 112-05-0) can be obtained by oxidation of n-nonanal of petrochemical origin (“Carboxylic Acids, Aliphatic,”: Ullmann's Encyclopedia of Industrial Chemistry 2014). n-Nonanoic acid can also be obtained by ozonolysis of ω-9-fatty acids, such as oleic acid and erucic acid or their esters. However, ozonolysis is a process with high energy demands and specific process requirements, such as the use of ozone generators. Moreover, the ω-9-fatty acids used are often obtained from tropical vegetable oils, such as palm oil, palm kernel oil and coconut oil. Even more sustainable methods for producing n-nonanoic acid are based on hydrogen peroxide (Soutelo-Maria et al. in Catalysts 2018, 8, 464), especially when such processes, such as those described in US9272975, US8846962, US8222438, WO2007039481 and WO2011080296, proceed also from omega-9-fatty acids or their esters not obtained from tropical vegetable oils.

[0032] Sorbitan Sorbitan is generally understood to mean the product mixture of the self-condensation products of sorbitol, mainly 1,4-anhydrosorbitol, 2,5-anhydrosorbitol, 1,5-anhydrosorbitol (Advances in Carbohydrate Chemistry and Biochemistry, 1983, 41, 27-66) and isosorbide (1,4:3,6-dianhydrosorbitol; ChemSusChem. 5 (1): 167-176), which are essentially five- and six-membered, mono- and bicyclic, hydroxyl-functional ethers of polyol nature, as illustratively shown in the following formula: [ka]

[0033] Such mixtures also generally contain minor amounts of further condensation products and sorbitol.

[0034] Sorbitan esters are esters of sorbitan and thus are the esterification products of the polyol mixtures described above with organic acids.

[0035] A review of sorbitan esters is provided, for example, in Treon, Soap Perfumery Cosmetics, January 1965, p. 47.

[0036] Xylitan Xylitane is generally understood to mean the product mixture of the self-condensation products of xylitol.

[0037] The three main condensation products of xylitol contained in xylitan are the anhydropentitols 1,4-anhydroxylitol, 1,4-anhydroarabinitol and 1,4-anhydroribitol (J. Carbohydr. Chem. 2004, 23, 4, 169-177 and Adv. Carbohydr. Chem. Biochem., 1983, 41, 27-66). As discussed above for sorbitan, those skilled in the art will appreciate that xylitan may also contain small amounts of uncondensed xylitol.

[0038] Xylitane esters are esters of xylitane and thus are the esterification products of the above-mentioned polyol mixtures with organic acids.

[0039] Unless otherwise stated, all percentages (%) listed are by weight.

[0040] A preferred anhydrosugar alcohol n-nonanoic acid ester composition according to the present invention comprises: D) anhydrosugar alcohol tri-n-nonanoic acid esters and / or, preferably, E) Anhydrosugar alcohol tetra-n-nonanoic acid ester The present invention is characterized by further comprising:

[0041] As mentioned above, sorbitan and xylitan may contain some sorbitol or xylitol, respectively, so the sugar alcohol n-nonanoate ester composition of the present invention will of course preferably contain some sorbitol n-nonanoate and / or xylitol n-nonanoate, respectively.

[0042] When sorbitol n-nonanoate and / or xylitol n-nonanoate are included in the sugar alcohol n-nonanoate composition of the present invention, all parameters described below relate to their contents.

[0043] The anhydrosugar alcohol n-nonanoic acid ester composition according to the present invention comprises: F) Free n-nonanoic acid It is preferred if the

[0044] The free n-nonanoic acid may be in the protonated or neutralized form.

[0045] The content of free n-nonanoic acid in the anhydrosugar alcohol n-nonanoic acid ester composition according to the present invention is determined by first determining the acid number, which can be used to determine the weight percentage of n-nonanoic acid by its molar mass.

[0046] Suitable methods for determining the acid number are, in particular, those according to DGF CV 2, DIN EN ISO 2114, Ph.Eur. 2.5.1, ISO 3682 and ASTM D 974.

[0047] The saponification number is determined by a person skilled in the art in accordance with DGF CV 3 or DIN EN ISO 3681.

[0048] Suitable methods for determining the hydroxyl number are, in particular, those according to DGF CV 17 a (53), Ph.Eur. 2.5.3 Method A and DIN 53240.

[0049] A preferred anhydrosugar alcohol n-nonanoic acid ester composition of the present invention is characterized in that the anhydrosugar alcohol n-nonanoic acid ester has an average degree of esterification of 0.7 to 4.0, preferably 0.8 to 2.5, and particularly preferably 1.0 to 2.0.

[0050] A preferred anhydrosugar alcohol n-nonanoic acid ester composition of the present invention is characterized in that the anhydrosugar alcohol n-nonanoic acid ester has a saponification value of 100 to 350, preferably 125 to 300, and particularly preferably 150 to 275 mg KOH / g.

[0051] A preferred anhydrosugar alcohol n-nonanoic acid ester composition of the present invention is characterized in that the anhydrosugar alcohol n-nonanoic acid ester has an acid value of 0.1 to 40, preferably 0.5 to 30, and particularly preferably 1 to 20 mg KOH / g.

[0052] A preferred anhydrosugar alcohol n-nonanoic acid ester composition of the present invention is characterized in that the anhydrosugar alcohol n-nonanoic acid ester has a hydroxyl value (OH value) of 50 to 600, preferably 100 to 550, and particularly preferably 150 to 500 mg KOH / g.

[0053] A preferred anhydrosugar alcohol n-nonanoic acid ester composition of the present invention is characterized in that the weight ratio of the anhydrosugar alcohol to its corresponding sugar alcohol (sorbitol / xylitol) in the anhydrosugar alcohol n-nonanoic acid ester composition of the present invention is preferably greater than 60:40 (60 / 40), preferably greater than 70:30 (70 / 30), more preferably greater than 80:20 (80 / 20), and particularly preferably greater than 85:15 (85 / 15), as determined by HPLC analysis. A detailed description of suitable analytical methods is given in WO2021122972 for xylitol esters, including xylitol esters, and in WO2021122973 for sorbitol esters, including sorbitan esters.

[0054] A further subject of the present invention is a method for producing an anhydrosugar alcohol n-nonanoic acid ester composition, preferably an anhydrosugar alcohol n-nonanoic acid ester composition according to the invention, wherein the anhydrosugar alcohol is selected from sorbitan and xylitan, the method comprising the steps of: I) providing sorbitol and / or xylitol, preferably sorbitol; II) dehydrating at least a portion of the sorbitol and / or xylitol to obtain sorbitan and / or xylitan, preferably sorbitan; III) esterifying sorbitan and / or xylitol, preferably sorbitan, with n-nonanoic acid, and optionally IV) isolating the anhydrosugar alcohol n-nonanoic acid ester composition formed in process step III); The method includes:

[0055] In process step II) of the method according to the invention, the dehydration of sorbitol and / or xylitol gives a mixture of various isomers, such as a mixture of 1,4-anhydrosorbitol, 2,5-anhydrosorbitol, 1,5-anhydrosorbitol, isosorbide and, if any, residual sorbitol.

[0056] Preferably, at least 60% by weight, more preferably at least 70% by weight, even more preferably at least 80% by weight, most preferably at least 85% by weight of the provided sorbitol and / or xylitol is dehydrated in process step II) of the method according to the invention.

[0057] The reaction conditions in process step II) influence the composition of the dehydrated product.

[0058] Process step II) of the method according to the invention is preferably carried out at temperatures between 100°C and 300°C, preferably between 120°C and 240°C, in particular between 130°C and 200°C.

[0059] Furthermore, process step II) of the method according to the invention is preferably carried out at a pressure between 0.001 bar and 1.5 bar, preferably between 0.5 bar and 1.25 bar, in particular between 0.8 bar and 1.2 bar.

[0060] In a preferred alternative embodiment, the production process step II) of the method according to the invention is carried out at a pressure of 0.001 bar to 0.9 bar, preferably 0.005 bar to 0.5 bar, in particular 0.006 bar to 0.01 bar, and at a temperature of 80°C to 140°C, preferably 90°C to 130°C, in particular 95°C to 120°C.

[0061] The use of acid catalysts, as described for example in EP 0 280 780 A, may affect the dehydration product. Process step II) of the method according to the invention is preferably carried out with an acid catalyst, preferably phosphoric acid.

[0062] Process step III) of the method according to the invention can be carried out by classical chemical or enzymatic routes.

[0063] The rapid and possibly quantitative reaction in process step III) of the method according to the invention by the classical chemical route depends on various parameters such as pressure, temperature and the qualitative ratio of the reaction partners, which also influence the anhydrosugar alcohol n-nonanoic acid ester composition, for example in terms of the statistical distribution of the various isomers, which may result in various mixtures of mono-, di- and tri-esters, for example, generated by the different choices of esterification positions in the molecule.

[0064] A preferred process according to the invention is characterized in that process step III) of the process according to the invention is carried out at a temperature between 140° C. and 300° C., preferably between 160° C. and 250° C., in particular between 200° C. and 230° C. Likewise, it is preferred that process step III) is carried out at a pressure between 0.001 bar and 1.5 bar, preferably between 0.5 bar and 1.25 bar, in particular between 0.8 bar and 1.2 bar.

[0065] In a preferred alternative embodiment of the method according to the invention, process step III) is carried out at a pressure of 0.001 bar to 0.9 bar, preferably 0.05 bar to 0.5 bar, in particular 0.006 bar to 0.01 bar, and at a temperature of 80°C to 250°C, preferably 120°C to 220°C, in particular 150°C to 200°C.

[0066] Just like in process step II) of the method according to the invention, the use of a catalyst, such as an alkali metal hydroxide, an alkali metal carbonate or an alkali metal salt of phosphoric acid, phosphorous acid or hypophosphorous acid, in process step III) of the method according to the invention can affect the anhydrosugar alcohol n-nonanoic acid ester composition.

[0067] Preferably, in process step III) of the method according to the invention, at least one catalyst selected from the group consisting of alkali metal salts and alkaline earth metal salts, preferably sodium hydroxide, is employed.

[0068] To carry out process step III) of the method according to the invention by an enzymatic route, the method of EP-A-3839052 can be applied.

[0069] It is evident that the sorbitol and / or xylitol present in process step III) of the method according to the invention is also esterified with n-nonanoic acid.

[0070] Preferably, process step II) and process step III) are carried out in a one-pot process, which means that at least a part of the catalyst used for the esterification is already present during the dehydration.

[0071] Thus, sorbitol and / or xylitol, preferably sorbitol, n-nonanoic acid and a catalyst are provided and the mixture is heated to a temperature of 100° C. to 300° C., preferably 120° C. to 275° C., more preferably 140° C. to 250° C., even more preferably 180° C. to 240° C., in particular 200° C. to 230° C., while applying a pressure of 0.01 bar to 1.5 bar, preferably 0.1 bar to 1.25 bar, in particular 0.8 bar to 1.2 bar.

[0072] Optionally, process step II) and / or process step III) or the one-pot process described above can be carried out in the presence of activated carbon.

[0073] This has the effect that the anhydrosugar alcohol n-nonanoic acid ester compositions produced by the methods of the present invention have an improved color profile.

[0074] Optionally, the obtained xylitol and / or sorbitan n-nonanoate esters can be treated with an aqueous solution of hydrogen peroxide, preferably by applying 0.01-1.0%, preferably 0.05-0.5% net / active amount of hydrogen peroxide at 60-140° C. for 5-500 minutes.

[0075] A further subject of the present invention is a formulation comprising an anhydrosugar alcohol n-nonanoic acid ester composition according to the invention or obtainable by the process of the invention, characterized in that the formulation comprises from 0.01% to 10% by weight of the anhydrosugar alcohol n-nonanoic acid ester composition relative to the total formulation.

[0076] The formulations according to the invention are preferably cosmetic or household care formulations, preferably cleaning formulations. Preferred formulations are dishwashing formulations and laundry detergents.

[0077] Thus, preferably, the formulation according to the invention preferably comprises at least one surfactant.

[0078] Although the anhydrosugar alcohol n-nonanoic acid ester compositions according to the present invention may have surface activity, in the context of the present invention, these anhydrosugar alcohol n-nonanoic acid ester compositions are not counted as surfactants.

[0079] The surfactants contained in the formulations according to the invention may be, for example, anionic, nonionic or amphoteric surfactants.

[0080] Representative examples of anionic surfactants are fatty alcohol sulfates, fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurates, fatty acid glutamates, fatty acid glycinates, alkyl ether carboxylates.

[0081] Non-ionic surfactants are, for example, alkyl oligoglucosides, fatty acid glucamides, rhamnolipids, sophorolipids and / or protein fatty acid condensates, the latter being, for example, based on wheat proteins.

[0082] Amphoteric surfactants are, for example, alkylamidoalkylhydroxysultaines, alkylamidoalkylbetaines, alkylbetaines, amphoacetates and amphopropionates, the terminal acyl or alkyl group of which typically contains from 8 to 18 carbon atoms.

[0083] Surfactants especially included according to the invention are fatty alcohol sulfates, fatty alcohol polyglycol ether sulfates, mono- and / or dialkyl sulfosuccinates, amphoacetates, amphopropionates, alkyl betaines, cocamidopropyl betaine, alkyl oligoglucosides and fatty acid glutamates.

[0084] Surfactants which are particularly preferably included according to the invention are the polyether-free surfactants mono- and / or dialkyl sulfosuccinates, amphoacetates, amphopropionates, betaines, in particular cocamidopropyl betaine, alkyl oligoglucosides and fatty acid glutamates.

[0085] According to the invention, the preferred amount of surfactant included is used such that the resulting formulation contains at least 2% by weight, preferably at least 4% by weight, particularly preferably at least 6% by weight of total surfactant based on the total formulation.

[0086] Preferred formulations according to the invention are characterized in that they have a pH between 2 and 13, preferably between 4 and 12.

[0087] "pH" in the context of the present invention is defined as the value measured on the composition at 25°C after stirring for 5 minutes using a pH electrode calibrated according to ISO 4319 (1977).

[0088] If the formulation is used as a rinse aid and / or bathroom cleaner, it is preferred that the formulation according to the invention is characterized in that it has a pH of 2.5 to 6.5, preferably 3.0 to 5.4.

[0089] When the formulation is used as a hand dishwashing detergent, it is preferred that the formulation according to the invention is characterized by having a pH of between 4.0 and 7.0, preferably between 5.0 and 6.0.

[0090] If the formulation is used as a dishwasher detergent, general purpose cleaner, hard surface cleaner, floor cleaner, metal cleaner, car shampoo, kitchen cleaner, laundry detergent, glass cleaner, food and beverage cleaner, it is preferred that the formulation according to the invention is characterized by having a pH of 7.0 to 14.0, preferably 7.5 to 12.5.

[0091] A further subject of the present invention is the use of an anhydrosugar alcohol n-nonanoic acid ester composition according to the present invention or obtainable by the process according to the present invention, or of a formulation according to the present invention, for preventing and / or reducing fouling on dishes, glasses and cutlery from the dishwashing process.

[0092] The examples presented below are provided by way of illustration of the present invention, and are not intended to limit the present invention, the scope of which is clear from the entire specification and claims, to the embodiments specified in the examples. [Brief description of the drawings]

[0093] [Figure 1] FIG. 13 shows cleaning performance results.

[0094] Working Example: Examples 1a to 1f: Synthesis of n-nonanoic acid esters of xylitol or sorbitan (according to the invention) Xylitol or sorbitol (or an aqueous solution thereof) was initially charged together with n-nonanoic acid, and after adding the catalyst, the reaction mixture was heated to the reaction temperature under stirring at a given pressure within 1 hour, and the water formed was continuously removed until the given acid value was reached. Finally, the mixture was filtered through a filter press.

[0095] [Table 1]

[0096] Example 1g: Synthesis of n-octanoic / n-decanoic esters of sorbitan (not according to the invention) This product was synthesized as an analog of Example 1d, only by replacing pelargonic acid with a 75:25 (w / w) mixture of caprylic and capric acids, and the acid value of this product was analyzed to be 13.4 mg KOH / g.

[0097] Example 2: Scent panel The products of Example 1d and Example 1g were compared in an odor panel test according to the state of the art. A group of seven experienced judges, previously qualified in the triangle test procedure, smelled 30ml of the two products, which had been previously stored in sealed 100ml amber wide-mouth glass bottles for 12 hours. The seven judges rated the odor based on a rating scale of 1 (good), 2 (acceptable), and 3 (poor).

[0098] As a result of this testing, the product of Example 1d received an average panel rating of 1.43, and the product of Example 1g received an average panel rating of 2.14.

[0099] Example 3: This example demonstrates the cleaning enhancing benefits of the composition of Example 1f compared to the composition described in Example 1g when used in a household cleaning formulation.

[0100] The exemplary formulations listed in Table 1 were prepared according to the following protocol: First, a measured amount of water was introduced into an appropriately sized glass beaker. Then, the additional ingredients were added with vigorous stirring at room temperature. The order of addition to the solution is not important, so the ingredients were not added in any particular or uniform order. Finally, the remaining amount of water was added to ensure the desired concentration of each ingredient. All ingredients were mixed on a magnetic stirrer, and the pH of the solution was adjusted to 8.0 by adding citric acid. The mixture was then stirred for 5 minutes to ensure a homogenous solution. The exemplary compositions were easily pourable and stable at room temperature for extended periods of time.

[0101] Following the method described above, three formulations were prepared (Table 1): Reference Formulation 1 was then used as a control formulation to evaluate the effectiveness of the tested cleaning booster additives. Reference Formulation 2, comprising the components of Reference Formulation 1 and a benchmark cleaning booster, the composition of which is described in Example 1g. - Test Formulation 1 comprising the components of Reference Formulation 1 and the composition of Example 1f which is the subject of the present invention.

[0102] [Table 2]

[0103] The cleaning performance of Test Formulation 1 was then evaluated against two reference formulations shown in Table 1. The procedure used to evaluate the cleaning performance is described in the test protocol below.

[0104] The cleaning performance tests were carried out according to an internal test method based on the recommendation of the German Cosmetics, Toiletries, Perfumes and Detergents Association (IKW) “IKW Recommendation for the Quality Assessment of the Product Performance of All-Purpose Cleaners 2014” (IKW test protocol). The basic principle of the test was to evaluate the cleaning power of the test formulations by evaluating their effectiveness in removing stubborn dirt from melamine tiles. White melamine tiles (herein referred to as test monitors) covered with black stubborn dirt consisting of a mixture of grease and carbon black were purchased from the Center for Testmaterials BV (available under the name DM-40 Tile). To ensure high reproducibility of the results, all test monitors belonged to the same production batch and were conditioned for 24 h in a climatic chamber at 20 °C before use.

[0105] To evaluate the cleaning performance of the prepared formulations, the test monitors were placed in a TQC Sheen Cleanability Tester (Model AB5000) and secured in place. The test monitors were placed in the Cleanability Tester one at a time, ensuring that each cleaning formulation was tested at least once on each of the four tracks of the Cleanability Tester. A dry 9 cm x 4.5 cm sponge was then first moistened with tap water and excess water was squeezed from the sponge. 10 g of the test liquid was then placed on the sponge and the sponge was attached to the cleaning arm of the Cleanability Tester. The Cleanability Tester was then run and controlled to perform 10 cleaning cycles (i.e., 20 linear strokes) on the test monitor. The stroke speed was 20 cycles per minute and the test was performed at room temperature. After the 10 cleaning cycles were completed, the test monitor was removed from the Sheen Tester, rinsed with tap water and dried. The test was repeated several times to provide five replicates for each test composition.

[0106] The treated test monitors were visually evaluated by five panelists who were asked to evaluate the cleaning effect achieved by each composition. The panelists ranked the cleaning effect on a scale from 0 to 10, where 0 represented no cleaning observed and 10 represented complete removal of the stain. For comparison, each panelist was provided with a new soiled test monitor, representing no cleaning, and a completely cleaned test monitor, representing a score of 10. In addition, to allow for a more accurate cleanliness evaluation, the panelists were provided with an evaluation template according to the IKW test protocol. The scores were summed and averaged for each test composition, and the results are reported in Table 2.

[0107] [Table 3]

[0108] As is readily apparent from the results reported in Table 2, compositions incorporating the subject matter of the present invention provide superior cleaning performance results against both benchmarks. Test Formula 1 far exceeds the cleaning results achieved by Reference Formula 1, which does not contain a Cleaning Booster, and also provides significantly better cleaning than Reference Formula 2, a composition that includes the benchmark Cleaning Booster.

[0109] Figure 1 clearly shows the visible results.

[0110] Example 4: This example demonstrates the superior performance of the composition of Example 1f in terms of fragrance retained on rinsed dishes when compared to a benchmark surfactant such as a fatty alcohol ethoxylate.

[0111] The panel test was performed according to the following protocol: First, two test solutions were prepared. The benchmark solution contained 0.5 wt.% of the exemplary fatty alcohol ethoxylate in tap water. The test solution contained 0.5 wt.% of the composition of Example 1f in tap water. Then, two sets of clean ceramic dishes were used for the test. One set of dishes was immersed in the benchmark solution and the second set of dishes in the test solution. The dishes were then drained and subjected to blind test evaluation by a team of five panelists. Each panelist received two dishes, one of which had been pre-soaked in the benchmark solution and the other in the test solution. The panelists were asked to evaluate the odor of the two dishes and rate them according to the following method: - Rate the smell of the dish on a scale from -1 to +1, where -1 means unpleasant, 0 means neutral, and +1 means pleasant. - Panelists were also allowed to share additional comments about the odors they perceived.

[0112] As a result, four out of five panelists rated the odor of the dishes immersed in the benchmark solution as unpleasant, and one panelist rated it as neutral. Furthermore, three panelists rated the odor of the dishes immersed in the test solution as pleasant, and two panelists rated it as neutral. Furthermore, three panelists rated the odor of the dishes previously immersed in the composition of the solution of Example 1f as "reminiscent of a coconut odor," and four panelists rated the odor of the dishes immersed in the benchmark solution as "artificial" or "chemical." Such odors are believed to be a common characteristic of fatty alcohol ethoxylate surfactants.

[0113] [Table 4]

[0114] The same test was then repeated, this time using stainless steel spoons. Two sets of clean spoons were then tested. One set of spoons was dipped into the benchmark solution and the second set of spoons was dipped into the composition of solution of Example 1f. The spoons were then drained and subjected to a blind test evaluation by a team of five panelists. Each panelist received two spoons, one of which had been pre-soaked in the benchmark solution and the other in the composition of solution of Example 1f. The panelists were asked to evaluate the taste of the two spoons and rate them according to the following method: - Rate the taste of the spoon on a scale from -1 to +1, where -1 means unpleasant, 0 means neutral, and +1 means pleasant.

[0115] Three out of five panelists rated the taste of the spoon dipped in the benchmark solution as neutral, two others as unpleasant, and three panelists rated the taste of the spoon dipped in the test solution as neutral, two others as pleasant.

[0116] [Table 5]

[0117] As is evident from the examples presented, the subject matter of the present invention allows the formulation of products intended to clean or rinse dishes without the risk of leaving the dishes with an unpleasant odor. Instead, the dishes can have a slight coconut odor, which is evaluated as pleasant by most panelists.

[0118] Exemplary Formulations [Table 6-1] [Table 6-2] [Table 6-3]

Table 6-4

Table 6-5

Table 6-6

Table 6-7

Table 6-8

Table 6-9

Table 6-10

Table 6-11

Table 6-12

Table 6-13

Table 6-14

Table 6-15

Table 6-16

Table 6-17

Table 6-18

Table 6-19

Table 6-20

Table 6-21

Table 6-22

Table 6-23

Table 6-24

Claims

1. below: A) an anhydrous sugar alcohol; B) anhydrosugar alcohol mono-n-nonanoic acid ester; C) anhydrosugar alcohol di-n-nonanoic acid ester and wherein the anhydrosugar alcohol is selected from sorbitan and xylitan.

2. below: D) anhydrosugar alcohol tri-n-nonanoic acid ester and / or E) Anhydrosugar alcohol tetra-n-nonanoic acid ester The anhydrosugar alcohol n-nonanoic acid ester composition of claim 1, further comprising:

3. below: F) Free n-nonanoic acid The anhydrosugar alcohol n-nonanoic acid ester composition according to claim 1 or 2, comprising:

4. 3. The anhydrosugar alcohol n-nonanoic acid ester composition according to claim 1, wherein the anhydrosugar alcohol n-nonanoic acid ester has an average degree of esterification of 0.7 to 4.

0.

5. 3. The anhydrosugar alcohol n-nonanoic acid ester composition according to claim 1, wherein the anhydrosugar alcohol n-nonanoic acid ester has a hydroxyl value of 50 to 600 mg KOH / g.

6. 3. The anhydrosugar alcohol n-nonanoic acid ester composition according to claim 1, wherein the anhydrosugar alcohol n-nonanoic acid ester has an acid value of 0.1 to 40 mg KOH / g.

7. 3. The anhydrosugar alcohol n-nonanoic acid ester composition according to claim 1, wherein the anhydrosugar alcohol n-nonanoic acid ester has a saponification value of 100 to 350 mg KOH / g.

8. 3. The anhydrosugar alcohol n-nonanoic acid ester composition according to claim 1 or 2, characterized in that the anhydrosugar alcohol n-nonanoic acid ester composition comprises sorbitol n-nonanoic acid ester and / or xylitol n-nonanoic acid ester, and the weight ratio of the anhydrosugar alcohol to its corresponding sugar alcohol in the anhydrosugar alcohol n-nonanoic acid ester composition is greater than 60:

40.

9. 1. A method for producing an anhydrosugar alcohol n-nonanoic acid ester composition, the anhydrosugar alcohol being selected from sorbitan and xylitan, the method comprising: I) providing sorbitol and / or xylitol; II) dehydrating the sorbitol and / or xylitol to obtain sorbitan and / or xylitan; III) esterifying said sorbitan and / or xylitan with n-nonanoic acid; and optionally IV) isolating the anhydrosugar alcohol n-nonanoic acid ester composition formed in process step III); A method comprising:

10. A formulation comprising the anhydrosugar alcohol n-nonanoic acid ester composition according to claim 1 or the anhydrosugar alcohol n-nonanoic acid ester composition obtainable by the process according to claim 9, The formulation comprises 0.01% to 10% by weight of the anhydrosugar alcohol n-nonanoic acid ester composition based on the total weight of the formulation.

11. The formulation of claim 10 further comprising a surfactant.

12. 10. Use of the anhydrosugar alcohol n-nonanoic acid ester composition according to claim 1 or obtainable by the process according to claim 9 for preventing and / or reducing deposits on dishes, glasses and cutlery from dishwashing processes.

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