NONANIC ACID ESTERS

Abstract

n-Nonanoic esters of xylitol, sorbitol or erythritol are made, especially for cosmetic or household care compositions, and a process for their preparation is developed.

Claims

1. A mixture of n-nonanoic esters of xylitol, sorbitol or erythritol, comprising: at least two of the esters which differ with regard to at least one esterification position of at least one nonanoyl radical in the xylitol, sorbitol or erythritol, with the proviso that n-nonanoic esters of erythritol with an average level of esterification of greater than 3.2 are excluded.

2. The mixture of n-nonanoic esters according to claim 1, wherein it comprises at least two regioisomers of the mono-n-nonanoic ester.

3. The mixture of n-nonanoic esters according to claim 1, wherein it comprises mono-n-nonanoic ester and di-n-nonanoic ester.

4. The mixture of n-nonanoic esters according to claim 1, wherein it has an average level of esterification of 1.0 to 4.0.

5. A mixed composition comprising the mixture of n-nonanoic esters according to claim 1, wherein said composition comprises less than 25% by weight of free n-nonanoic acid, where the percentages by weight are based on the sum total of all n-nonanoic esters of xylitol, sorbitol and erythritol and n-nonanoic acid.

6. The mixed composition according to claim 5, wherein said composition comprises 0.05% by weight to 40% by weight of free xylitol, sorbitol and/or erythritol, where the percentages by weight are based on the sum total of all n-nonanoic esters of xylitol, sorbitol and erythritol and all xylitol, sorbitol and erythritol.

7. The mixed composition according to claim 5, wherein said composition comprises 0.1% by weight to 60% by weight of at least one solvent.

8. A process for enzymatic preparation of a mixture of n-nonanoic esters of xylitol, sorbitol or erythritol according to claim 1, comprising: A) providing xylitol, sorbitol or erythritol and at least one n-nonanoyl group donor, B) reacting xylitol, sorbitol or erythritol with the at least one n-nonanoyl group donor in the presence of a lipase at a temperature of 75? C. to 110? C. to give an n-nonanoic ester of xylitol, sorbitol or erythritol, and optionally C) purifying the n-nonanoic ester of xylitol, sorbitol or erythritol.

9. The process according to claim 8, wherein A) comprises blending the xylitol, sorbitol or erythritol with the at least one n-nonanoyl group donor for at least ten minutes.

10. The process according to claim 8, wherein the xylitol, sorbitol or erythritol with the at least one n-nonanoyl group donor accounts for at least 80% by weight based on the overall reaction mixture at the start of B).

11. The process according to claim 8, wherein the lipase is at least one selected from the group comprising the lipase from Thermomyces lanuginosus (accession number 059952), lipases A and B (accession number P41365) from Candida antarctica, and the lipase from Mucor miehei (accession number P19515), the lipase from Humicola sp. (accession number OS9952), the lipase from Rhizomucor javanicus (accession number S32492), the lipase from Rhizopus oryzae (accession number P61872), the lipases from Candida rugosa (accession number P20261, P32946, P32947, P3294 and P32949), the lipase from Rhizopus niveus (accession number P61871), the lipase from Penicillium camemberti (accession number P25234), the lipases from Aspergillus niger (ABG73613, ABG73614 and ABG37906), the lipase from Penicillium cyclopium (accession number P61869), and their respective at least 60% homologues at the amino acid level.

12. The process according to claim 8, wherein B) is conducted at a pressure of less than 1 bar.

13. The process according to claim 8, wherein, in A), as well as the xylitol, sorbitol or erythritol, at least one other sugar or sugar alcohol is provided, selected from the group consisting of agarose, allitol, allulose, altritol, amylopectin, amylose, arabinitol, arabinose, cellobiose, cellulose, chitin, cyclodextrins, deoxyribose, dextrans, erythritol, fructans, fructose, fucose, galactitol, galactose, glucitol, glucose, glycogen, hyaluronic acid, iditol, inulin, isomalt, isomaltulose, isomelizitose, lactitol, lactose, lactulose, maltitol, maltohexose, maltopentose, maltose, maltotetrose, maltotriose, maltulose, mannitol, mannose, melizitose, pectins, raffinose, rhamnose, ribitol, ribose, sucrose, sorbitol, sorbose, stachyose, starch, starch hydrolysate, threitol, trehalulose, umbelliferose, xylitol and xylose, and this also passes through the further process steps.

14. The n-nonanoic ester of xylitol, sorbitol or erythritol, obtainable by a process according to claim 8.

15. A method of making a product, comprising: producing at least one selected from the group consisting of a viscosity regulator, active care ingredient, foam booster or solubilizer, antimicrobial, antistat, binder, corrosion inhibitor, dispersant, emulsifier, film former, humectant, opacifier, oral care agent, preservative, skincare agent, hydrophilic emollient, foam stabilizer and/or nonionic surfactant with at least one of the mixture of n-nonanoic esters of xylitol, sorbitol, or erythritol according to claim 1.

16. The mixture of n-nonanoic esters according to claim 1, wherein it comprises mono-n-nonanoic ester, di-n-nonanoic ester, and tri-n-nonanoic ester.

17. The mixture of n-nonanoic esters according to claim 1, wherein it has an average level of esterification of 1.0 to 3.0.

18. The mixture of n-nonanoic esters according to claim 1, wherein it has an average level of esterification of 1.1 to 2.7.

19. The mixture of n-nonanoic esters according to claim 1, wherein it has an average level of esterification of 1.3 to 2.6.

Description

[0172] The following figures are an integral part of the examples:

[0173] FIG. 1: Gas chromatography of Example 1

[0174] FIG. 2: Gas chromatography of Example 4

[0175] FIG. 3: Gas chromatography of Example 6

EXAMPLES

Example 1: Enzymatic Esterification of Xylitol with 1.50 Equiv. of n-Nonanoic Acid (Inventive)

[0176] A mixture of xylitol (176.3 g, 1.16 mol, 1.00 equiv.) and n-nonanoic acid (acid number=355 mg KOH/g, 99%, 275.0 g, 1.74 mol, 1.50 equiv.) was heated to 90? C. with stirring and while passing N.sub.2 through, and after 1 h immobilized Candida antarctica lipase B enzyme (13.5 g; Purolite D5619, corresponding to 117234 PLU) was added. The mixture was stirred at 85? C. and 50 mbar for 24 h, during which the water formed was distilled off continuously. Subsequently, the mixture was filtered at 80? C. through a Buchner funnel with black band filter to remove the enzyme. The product obtained was homogeneous in the melt and pale yellowish, and had an acid number of 1.5 mg KOH/g. Analysis by GC-FID showed a mixture of mono-, di- and triesters that each consisted of more than one regioisomer.

[0177] This is apparent in FIG. 1: For instance, the signals at 11.55 min and 11.93 min correspond to the regioisomers of the monoester, and the signals at 15.51 min, 15.57 min and 16.06 min to the regioisomers of the diester.

Example 2: Enzymatic Esterification of a Mixture of 0.90 Equiv. of Xylitol and 0.10 Equiv. of Xylose with 1.50 Eq of n-Nonanoic Acid (Inventive)

[0178] A mixture of xylitol (77.0 g, 0.506 mol, 0.90 equiv.), xylose (8.56 g, 0.057 mol, 0.10 equiv.) and n-nonanoic acid (acid number=355 mg KOH/g, 99%, 129.1 g, 0.816 mol, 1.45 equiv.) was heated to 90? C. with stirring and while passing N.sub.2 through, and after 1 h immobilized Candida antarctica lipase B enzyme (6.44 g; Purolite D5619, corresponding to 55925 PLU) was added. The mixture was stirred at 85? C. and 50 mbar for 24 h, during which the water formed was distilled off continuously. Subsequently, the mixture was filtered at 80? C. through a B?chner funnel with black band filter to remove the enzyme. The product obtained was slightly cloudy in the melt and pale yellowish, and had an acid number of 5.6 mg KOH/g. Analysis by GC-FID showed a mixture of mono-, di- and triesters that each consisted of more than one regioisomer.

Example 3: Enzymatic Esterification of a Mixture of 0.90 Equiv. of Xylitol and 0.10 Equiv. of Xylose with 1.27 Equiv. of n-Nonanoic Acid (Inventive)

[0179] A mixture of xylitol (82.9 g, 0.545 mol, 0.90 equiv.), xylose (9.21 g, 0.061 mol, 0.10 equiv.) and n-nonanoic acid (acid number=355 mg KOH/g, 99%, 121.75 g, 0.769 mol, 1.27 equiv.) was heated to 90? C. with stirring and while passing N.sub.2 through, and after 1 h immobilized Candida antarctica lipase B enzyme (6.42 g; Purolite D5619, corresponding to 55751 PLU) was added. The mixture was stirred at 85? C. and 50 mbar for 24 h, during which the water formed was distilled off continuously. Subsequently, the mixture was filtered at 80? C. through a B?chner funnel with black band filter to remove the enzyme. The product obtained was homogeneous in the melt and pale yellowish, and had an acid number of 5.0 mg KOH/g. Analysis by GC-FID showed a mixture of mono-, di- and triesters that each consisted of more than one regioisomer.

Example 4: Enzymatic Esterification of Erythritol with 1.5 Equiv. of n-Nonanoic Acid (Inventive)

[0180] A mixture of erythritol (125.0 g, 1.02 mol, 1.00 equiv.) and n-nonanoic acid (acid number=355 mg KOH/g, 99%, 226.31 g, 1.54 mol, 1.50 equiv.) was heated to 85? C. while stirring and passing N.sub.2 through. After 1 h, immobilized Candida antarctica lipase B enzyme (10.5 g; Purolite D5619, corresponding to 91258 PLU) was added and stirring of the mixture was continued at 85? C. and 15 mbar for 24 h, during which the water formed was distilled off continuously. Subsequently, the mixture was filtered at 80? C. through a Buchner funnel with black band filter to remove the enzyme. The product obtained had an acid number of 5.6 mg KOH/g.

[0181] Analysis by GC-FID showed a mixture of mono-, di-, tri- and tetraesters, where the mono-, di- and triesters each consisted of more than one regioisomer.

[0182] This is apparent in FIG. 2: The signals at 11.09 min and 11.34 min correspond to the regioisomers of the monoester; the signals at 15.56 min and 15.89 min to the regioisomers of the diester.

Example 5: Enzymatic Esterification of Sorbitol with 1.55 Equiv. of n-Nonanoic Acid (Inventive)

[0183] A mixture of sorbitol (96.5 g, 0.530 mol, 1.00 equiv.) and n-nonanoic acid (acid number=355 mg KOH/g, 99%, 129.9 g, 0.821 mol, 1.55 equiv.) was heated to 100? C. while stirring and passing N.sub.2 through. After 1 h, the mixture was cooled down to 85? C., immobilized Candida antarctica lipase B enzyme (6.79 g; Purolite D5619, corresponding to 58807 PLU) was added and the mixture was stirred further at 85? C. and 15 mbar for 24 h, during which the water formed was continuously distilled off. Subsequently, the mixture was filtered at 80? C. through a Buchner funnel with black band filter to remove the enzyme. The product obtained had an acid number of 3.2 mg KOH/g. Analysis by GC-FID showed a mixture of mono-, di-, tri- and tetraesters that each consisted of more than one regioisomer.

Example 5a: Enzymatic Esterification of Sorbitol with 2.90 Equiv. of n-Nonanoic Acid (Inventive)

[0184] A mixture of sorbitol (96.5 g, 0.530 mol, 1.00 equiv.) and n-nonanoic acid (acid number=355 mg KOH/g, 99%, 243.2 g, 1.54 mol, 2.90 equiv.) was heated to 100? C. while stirring and passing N.sub.2 through. After 1 h, the mixture was cooled down to 85? C., immobilized Candida antarctica lipase B enzyme (10.2 g; Purolite D5619, corresponding to 88236 PLU) was added and the mixture was stirred further at 85? C. and 15 mbar for 24 h, during which the water formed was continuously distilled off. Subsequently, the mixture was filtered at 80? C. through a B?chner funnel with black band filter to remove the enzyme. The product obtained had an acid number of 3.9 mg KOH/g. Analysis by GC-FID showed a mixture of mono-, di-, tri- and tetraesters that each consisted of more than one regioisomer.

Example 6: Enzymatic Esterification of a Mixture of 0.74 Equiv. of Xylitol and 0.26 Equiv. of Sorbitol with 1.30 Eq of n-Nonanoic Acid (Inventive)

[0185] A mixture of xylitol (65.5 g, 0.430 mol, 0.74 equiv.), sorbitol (28.1 g, 0.154 mol, 0.26 equiv.) and n-nonanoic acid (acid number=355 mg KOH/g, 99%, 120.2 g, 0.759 mol, 1.30 equiv.) was heated to 90? C. with stirring and while passing N.sub.2 through, and after 1 h immobilized Candida antarctica lipase B enzyme (6.41 g; Purolite D5619, corresponding to 55500 PLU) was added. The mixture was stirred at 85? C. and 50 mbar for 24 h, during which the water formed was distilled off continuously. Subsequently, the mixture was filtered at 80? C. through a B?chner funnel with black band filter to remove the enzyme. The product obtained had an acid number of 1.5 mg KOH/g. Analysis by GC-FID showed a mixture of mono-, di-, tri- and tetraesters that each consisted of more than one regioisomer.

[0186] This is apparent in FIG. 3: The signals at 12.32 min and 12.73 min correspond to the regioisomers of the xylityl monoester; the signals at 13.85 min and 14.52 min correspond to the regioisomers of the sorbityl monoester; the signals at 16.08 min, 16.45 min and 16.97 min correspond to the regioisomers of the xylityl diesters; the signals at 17.63 min and 18.41 min correspond to the regioisomers of the sorbityl diester.

Example 7: Enzymatic Esterification of Xylitol with 1.50 Equiv. of Caprylic/Capric Acid (Non-Inventive)

[0187] A mixture of xylitol (75.7 g, 0.497 mol, 1.00 equiv.) and a mixture of caprylic acid and capric acid (acid number=362 mg KOH/g, mixing ratio of caprylic acid to capric acid 60:40, 115.7 g, 0.746 mol, 1.50 equiv.) was heated to 90? C. with stirring and while passing N.sub.2 through for 1 h and, after cooling to 85? C., immobilized Candida antarctica lipase B enzyme (5.74 g; Purolite D5619, corresponding to 49710 PLU) was added. The mixture was stirred at 85? C. and 50 mbar for 24 h, during which the water formed was distilled off continuously. Subsequently, the mixture was filtered at 80? C. through a B?chner funnel with black band filter to remove the enzyme. The product obtained had an acid number of 1.5 mg KOH/g.

Example 8: Enzymatic Esterification of a Mixture of 0.74 Equiv. of Xylitol and 0.26 Equiv. of Sorbitol with 1.30 Eq of Caprylic/Capric Acid (Noninventive)

[0188] A mixture of xylitol (131.5 g, 0.864 mol, 0.74 equiv.), sorbitol (56.4 g, 0.309 mol, 0.26 equiv.) and a mixture of caprylic acid and capric acid (acid number=362 mg KOH/g, mixing ratio of caprylic acid to capric acid 60:40, 239.6 g, 1.53 mol, 1.30 equiv.) was heated to 90? C. with stirring and while passing N.sub.2 through, and after 30 min immobilized Candida antarctica lipase B enzyme (12.8 g; Purolite D5619, corresponding to 110827 PLU) was added. The mixture was subsequently stirred at 80? C. and 20 mbar for 24 h, during which the water formed was continuously distilled off. Subsequently, the mixture was filtered at 80? C. through a B?chner funnel with black band filter to remove the enzyme. The product obtained had an acid number of 3.0 mg KOH/g.

Examples 9a to 9f: Chemical Esterification of Xylitol and Sorbitol (Inventive)

[0189] Xylitol or sorbitol (or aqueous solutions thereof) were initially charged together with n-nonanoic acid and, after the catalyst had been added, the reaction mixture was heated to reaction temperature while stirring at the pressure specified within 1 h, and the water formed was removed continuously until the acid number specified had been attained. Finally, the mixture was filtered through a filter press.

TABLE-US-00001 TABLE 1 Acid Sugar Sugar Pelargonic Pelargonic Pelargonic number of Sugar alcohol alcohol acid acid acid Reaction the product alcohol m [g] n [mol] m/g n [mol] Equiv. Catalyst conditions [mg KOH/g] 9a Xylitol 290.1 1.91 467.6 2.96 1.55 3.7 g H.sub.3PO.sub.4 230? C., 7.9 and 6.6 g 1 atm NaOH 9b Xylitol 290.0 1.91 392.1 2.48 1.30 0.8 g para- 160? C., 5.7 toluenesulfonic 1 atm acid 9c Xylitol 275.0 1.81 486.2 3.07 1.70 19.4 g K.sub.2CO.sub.3 180? C., 7.1 50 mbar 9d Sorbitol 390.5 1.50 368.0 2.33 1.55 2.9 g H.sub.3PO.sub.4 230? C., 8.6 (70% aqueous and 5.0 g 1 atm solution) NaOH 9e Sorbitol 389.7 1.50 308.0 1.95 1.30 0.6 g para- 160? C., 5.6 (70% aqueous toluenesulfonic 1 atm solution) acid 9f Sorbitol 370.2 1.42 382.6 2.42 1.70 15.3 g K.sub.2CO.sub.3 180? C., 6.9 (70% aqueous 50 mbar solution)

Example 9g: Preparation of Xylitol Caprylate (=Xylitol Octanoate) in Analogy to Example 3 from WO94/12651A1 (Non-Inventive)

[0190] A mixture of xylitol (0.5 g, 3.3 mmol) and octanoic acid (99%, 3.35 g, 23.2 mmol) was heated to 50? C. under mechanical stirring. Then, sodium octanoate (0.85 g, 5.1 mmol) was added as well as Candida antarctica lipase B enzyme (0.5 mL of an aqueous solution containing 5000 PLU/mL) and the mixture was subsequently stirred at 50? C. for 20 h, Subsequently, the mixture was filtered at 50? C. through a Buchner funnel with black band filter.

Example 10: Thickening Performance in a Cosmetic Formulation at Relatively Low Concentration

[0191] The thickening effect of inventive examples 1 and 4 was evaluated in comparison with non-inventive thickeners. For this purpose, a cosmetic formulation consisting of 4.8% Cocoamphoacetate, 4.8% Cocamidopropyl Betaine, 3.6% Sodium Lauroyl Sarcosinate in water was produced. The pH of this formulation was adjusted to 5.2 with citric acid. 0.6% of the abovementioned example substances was incorporated into each of these formulations at 60? C. by stirring for 30 min, and the viscosities were measured with the aid of a Brookfield viscometer (spindle 62, 30 rpm) at 22? C. The results of the viscosity measurements are shown in Table 2.

TABLE-US-00002 TABLE 2 Reference Composition Viscosity Inventive Example 1 Xylityl nonanoate 5269 mPa .Math. s Inventive Example 4 Erythrityl nonanoate 4289 mPa .Math. s Inventive Example 5 Sorbityl nonanoate 4401 mPa .Math. s Non- Example 7 Xylityl caprylate caprate 5216 inventive mPa .Math. s Non- as per Sorbitan sesquicaprylate 4245 inventive DE102009001748A mPa .Math. s Non- as per EP879872 Sorbityl hexanonanoate 150 inventive mPa .Math. s Non- as per Goodby et 1-O-Nonanoyl-D,L-xylitol 3951 inventive al. in Liquid mPa .Math. s Crystals 1997, 22, 367-378 Non- as per example 3 Xylitol Caprate (=Xylitol 1589 inventive of WO94/12651A1 decanoate) mPa .Math. s Non- Example 9g Xylitol Caprylate (=Xylitol 874 inventive octanoate) mPa .Math. s

Example 11: Thickening Performance in a Cosmetic Formulation at Relatively High Concentration

[0192] The thickening effect of inventive examples 3, 4, 5 and 6 was evaluated in comparison with non-inventive thickeners. For this purpose, a cosmetic formulation consisting of 4.8% Cocoamphoacetate, 4.8% Cocamidopropyl Betaine, 3.6% Sodium Lauroyl Sarcosinate in water was produced. The pH of this formulation was adjusted to 5.2 with citric acid. 0.8% of the abovementioned example substances was incorporated into each of these formulations at 60? C. by stirring for 30 min, and the viscosities were measured with the aid of a Brookfield viscometer (spindle 62, 30 rpm) at 22? C. The results of the viscosity measurements are shown in Table 3.

TABLE-US-00003 TABLE 3 Reference Composition Viscosity Inventive Example 3 Xylityl xylose nonanoate 2902 mPa .Math. s Inventive Example 4 Erythrityl nonanoate 2853 mPas Inventive Example 5 Sorbityl nonanoate 3010 mPas Inventive Example 6 Xylityl sorbityl 3392 nonanoate mPas Non- Example 8 Xylityl sorbityl caprylate/ 2709 inventive caprate mPas Non- as per Sorbitan sesquicaprylate 2763 inventive DE102009001748A mPas Non- as per EP879872 Sorbityl hexanonanoate 705 inventive mPas Non- as per Goodby et 1-O-Nonanoyl-D,L-xylitol 2703 inventive al. in Liquid mPas Crystals 1997, 22, 367-378 Non- as per example 3 Xylitol Caprate (=Xylitol 800 inventive of WO94/12651A1 decanoate) mPas Non- Example 9g Xylitol Caprylate 1141 inventive (=Xylitol octanoate) mPas

Example 12: Thickening Performance in a Cosmetic Formulation

[0193] The thickening effect of inventive examples 1, 4, 5 and 6 was evaluated in comparison with non-inventive thickeners. For this purpose, a cosmetic formulation consisting of 9% SLES, 3% Cocamidopropyl Betaine and 0.7% NaCl in water was produced. The pH of this formulation was adjusted to 5.2 with citric acid. 1.1% of the abovementioned example substances was incorporated into each of these formulations at 60? C. by stirring for 30 min, and the viscosities were measured with the aid of a Brookfield viscometer (spindle 62, 30 rpm) at 22? C. The results of the viscosity measurements are shown in Table 4.

TABLE-US-00004 TABLE 4 Reference Composition Viscosity Inventive Example 1 Xylityl 3157 nonanoate mPas Inventive Example 4 Erythrityl 3100 nonanoate mPas Inventive Example 5 Sorbityl 3213 nonanoate mPas Inventive Example 6 Xylityl sorbityl 4843 nonanoate mPas Non-inventive as per Xylitan 3061 KR101939851B1 Sesquicaprylate mPas Non-inventive as per Sorbityl 50 EP879872 hexanonanoate mPas Non-inventive as per Goodby 1-O-Nonanoyl- 2974 et al. in Liquid D,L-xylitol mPas Crystals 1997, 22, 367-378

Example 13: Hand Wash Test

[0194] To evaluate the skin feel during the washing a test was performed with a trained sensory panel. The formulations from Example 10 were used in sensory hand wash test. For this purpose, the group of at least 10 trained test persons washed their hands according to a well-defined procedure. Before application the hands have to be cleaned before the test in a standardized way with 2 g of a standard surfactant solution for 10 seconds and the formulation is rinsed off for 10 seconds. After this pre-washing step 2 g of the formulation containing the given composition were applied on the wet palm of a hand. Foam is generated between both hands and the skin feel during washing is judged on a grading scale from 1 (very bad) to 5 (very good). The formulation is rinsed off for 15 seconds. Afterwards two separate judgements for the skin smoothness and the skin softness are given on a grading scale from 1 (very bad) to 5 (very good). This is performed directly after drying and after 3 minutes.

TABLE-US-00005 TABLE 5 skin skin skin skin skin softness smoothness feel softness smoothness after after during after after 3 3 Total Reference Composition washing washing washing min min Score Inventive Example 1 Xylityl nonanoate 3.0 3.2 3.0 3.2 3.2 3.1 Inventive Example 4 Erythrityl nonanoate 3.2 3.5 3.4 3.6 3.6 3.43 Inventive Example 5 Sorbityl nonanoate 2.9 3.1 3.3 3.4 3.5 3.2 Inventive Example 5a Sorbityl nonanoate 2.7 2.8 2.5 2.3 2.5 2.56 Non- Example 7 Xylityl caprylate caprate 2.0 2.1 2.1 2.2 2.4 2.12 inventive Non- as per Sorbitan sesquicaprylate 1.8 1.8 2.0 2.0 1.8 1.86 inventive DE102009001748A Non- as per EP879872 Sorbityl hexanonanoate 2.0 1.9 2.2 1.8 2.2 1.99 inventive Non- as per Goodby et al. in 1-O-Nonanoyl-d.I-xylitol 1.4 1.6 1.7 1.5 1.5 1.51 inventive Liquid Crystals 1997. 22. 367-378 Non- as per WO94/12651A1 Xylitol Caprate (=Xylitol 1.8 2.1 2.2 2.0 2.0 1.99 inventive decanoate) Non- Example 9g Xylitol Caprylate 2.0 1.7 1.7 2.0 2.0 1.84 inventive (=Xylitol octanoate) Non- As per example 17 of Erythrityl nonanoate 2.0 1.8 1.8 2.0 2.0 1.92 inventive WO2020116411A1 (Hydroxyl value: 40 mg KOH/g)

[0195] It can be seen from the measurement results in table 5 that washing hands with the formulations according to the invention using the compositions according to the invention causes the highest score for skin feel after application.

Formulation Examples

Recipes 1a, 1b, 1c and 1d: Shower Cream

[0196]

TABLE-US-00006 1a 1b 1c 1d Water to 100.0% to 100.0% to 100.0% to 100.0% Composition from Example 1 1.5% Composition from Example 3 1.5% Composition from Example 4 1.5% Composition from Example 5 1.5% Sodium Laureth Sulfate (Texapon NSO, BASF, 28%) 25.0% 25.0% 25.0% 25.0% Coco-Glucoside (Plantacare 818 UP, BASF, 51%) 8.0% 8.0% 8.0% 8.0% Cocamidopropyl Betaine (TEGO? Betain F 50, Evonik, 8.0% 8.0% 8.0% 8.0% 38%) PEG-18 Glyceryl Oleate/Cocoate (ANTIL? 171, Evonik) 1.5% 1.5% 1.5% 1.5% Sorbitan Sesquicaprylate (ANTIL? Soft SC, Evonik) 0.8% 0.8% 0.8% 0.8% Glyceryl Oleate (TEGIN? O V, Evonik) 0.8% 0.8% 0.8% 0.8% Perfume Spicy Herbs (IFF) 0.2% 0.2% 0.2% 0.2% Polyglyceryl-4 Caprate (TEGOSOFT? PC 41, Evonik) 0.6% 0.6% 0.6% 0.6% Helianthus Annuus Seed Oil (AEC Sunflower Oil, A & E 0.2% 0.2% 0.2% 0.2% Connock, Perfumery & Cosmetics Ltd.) Linalool (Lipofresh, Lipo Chemicals, Inc,) 0.1% 0.1% 0.1% 0.1% Coumarin (Rhodiascent extra pure, Solvay Rhodia) 0.1% 0.1% 0.1% 0.1% Glycerol (Glycerol EP, vegetable, Spiga Nord) 0.4% 0.4% 0.4% 0.4% Hydroxypropyl Methylcellulose (TEGOCEL? HPM 50, 0.2% 0.2% 0.2% 0.2% Evonik) Glycol Distearate (TEGIN? G 1100 Pellets, Evonik) 0.4% 0.4% 0.4% 0.4% Sodium Chloride 0.5% 0.5% 0.5% 0.5% Hydroxypropyl Guar Hydroxypropyltrimonium Chloride 0.2% 0.2% 0.2% 0.2% (Jaguar C-162, Solvay Rhodia) dermofeel TOCO 70 non GMO 0.1% 0.1% 0.1% 0.1% Disodium EDTA (Dissolvine NA-2-P, AkzoNobel) 0.1% 0.1% 0.1% 0.1% Preservative q.s. q.s. q.s. q.s. Citric Acid to pH 5.2 to pH 5.2 to pH 5.2 to pH 5.2

Recipes 2a, 2b, 2c and 2d: Body Shampoo

[0197]

TABLE-US-00007 2a 2b 2c 2d Phase Composition from Example 1 0.5% A Composition from Example 3 0.5% Composition from Example 4 0.5% Composition from Example 5 0.5% Lavandula Angustifolia (Lavender) Oil (AEC 0.2% 0.2% 0.2% 0.2% Lavender Oil, A&E Connock Ltd.) Perfume 0.1% 0.1% 0.1% 0.1% Phase Sodium Cocoamphoacetate (REWOTERIC? AM 10.0% 10.0% 10.0% 10.0% B C, Evonik, 32%) Phase Water to 100.0% to 100.0% to 100.0% to 100.0% C Xanthan Gum (Keltrol CG-SFT, CP Kelco) 1.2% 1.2% 1.2% 1.2% Phase Sodium Lauroyl Methyl Isethionate (Iselux, 4.5% 4.5% 4.5% 4.5% D Innospec Active Chemicals) Capryl/Capramidopropyl Betaine (TEGO? 4.5% 4.5% 4.5% 4.5% Betaine 810, Evonik, 38%) Citric Acid 1.2% 1.2% 1.2% 1.2% Phase Water 10.0% 10.0% 10.0% 10.0% E Polyquaternium-7 (Merquat 550, Nalco) 0.4% 0.4% 0.4% 0.4% Preservative q.s. q.s. q.s. Body cream

Recipes 3a, 3b, 3c and 3d: Shampoo

[0198]

TABLE-US-00008 3a 3b 3c 3d Phase Composition from Example 1 3.5% A Composition from Example 3 3.5% Composition from Example 4 3.5% Composition from Example 5 3.5% Isopropyl Myristate (TEGOSOFT? M, 0.2% 0.2% 0.2% 0.2% Evonik) Perfume 0.1% 0.1% 0.1% 0.1% Phase Water to 100.0% to 100.0% to 100.0% to 100.0% B Phase Sodium Lauryl Sulfate (Texapon LS 35, 28.0% 28.0% 28.0% 28.0% C BASF, 30%) Phase Cocamidopropyl Betaine (TEGO? 9.0% 9.0% 9.0% 9.0% D Betain F 50, Evonik, 38%) Phase Cocamide MEA (REWOMID? C 212, 2.0% 2.0% 2.0% 2.0% E Evonik) Xanthan Gum (Keltrol CG-SFT, CP 0.3% 0.3% 0.3% 0.3% Kelco) Water 10.0% 10.0% 10.0% 10.0% Phase Water 10.0% 10.0% 10.0% 10.0% F Polyquaternium-10 (Polymer JR 400, 0.2% 0.2% 0.2% 0.2% Amerchol) Phase Citric Acid to pH 5.0 to pH 5.0 to pH 5.0 to pH 5.0 G Phase Preservative q.s. q.s. q.s. Body H cream

Recipes 4a, 4b, 4c and 4d: Shampoo

[0199]

TABLE-US-00009 Recipes 4a 4b 4c 4d Water to 100.0% to 100.0% to 100.0% to 100.0% Composition from Example 1 2.5% 2.5% Composition from Example 3 1.5% 1.5% Composition from Example 4 2.5% 2.5% Composition from Example 5 1.5% 1.5% Cocamidopropyl Betaine (TEGO? Betain F 50, 22.0% 22.0% 22.0% 22.0% Evonik, 38%) Lauryl Glucoside (Plantacare 1200 UP, BASF, 50%) 6.0% 6.0% 6.0% 6.0% Sodium Cocoyl Glutamate (Plantapon ACG HC, 1.5% 1.5% 1.5% 1.5% BASF) Sodium Cocoyl Glycinate (Hostapon SG, Clariant) 0.8% 0.8% 0.8% 0.8% Zinc Pyrithione (Microcare ZP, Thor) 0.1% 0.1% 0.1% 0.1% PEG-120 Methyl Glucose Dioleate (ANTIL? 120 0.4% 0.4% 0.4% 0.4% Plus, Evonik) Sodium Chloride 0.5% 0.5% 0.5% 0.5% Isostearamide MIPA; Glyceryl Laurate (ANTIL? SPA 0.5% 0.5% 0.5% 0.5% 80, Evonik) Xanthan Gum (Keltrol CG-SFT, CP Kelco) 0.3% 0.3% 0.3% 0.3% Hydroxypropyl Guar Hydroxypropyltrimonium 0.3% 0.3% 0.3% 0.3% Chloride (Jaguar C-162, Solvay Rhodia) Quaternium-80 (ABIL? Quat 3272, Evonik) 0.4% 0.4% 0.4% 0.4% Palmitamidopropyltrimonium Chloride (VARISOFT? 0.4% 0.4% 0.4% 0.4% PATC, Evonik) Argania Spinosa Oil (Argan Oil, DSM Nutritional 0.1% 0.1% 0.1% 0.1% Products Ltd.) Glycerol (Glycerol EP, vegetable, Spiga Nord) 0.6% 0.6% 0.6% 0.6% Tetrasodium EDTA (Versene 100, The Dow 0.1% 0.1% 0.1% 0.1% Chemical Company) Caffeine (Merck KGaA/EMD Chemicals, Inc.) 0.1% 0.1% 0.1% 0.1% Hydrolyzed Wheat Protein (Gluadin WLM, BASF) 0.1% 0.1% 0.1% 0.1% Limonene (Dipentene No, 122, Hercules Inc.) 0.1% 0.1% 0.1% 0.1% Citric Acid to pH 5.5 to pH 5.5 to pH 5.5 to pH 5.5 Sodium Phytate; Aqua; Alcohol (dermofeel? PA-3; 0.1% 0.1% 0.1% Evonik Dr, Straetmans GmbH (PA-3) Perfume 0.2% Preservative q.s. Aqua; Sodium Levulinate; Sodium Benzoate 1.2% 1.2% 1.2% (Verstatil? BL non GMO; Evonik Dr. Straetmans GmbH)

Recipes 5a, 5b, 5c and 5d: Liquid Soap

[0200]

TABLE-US-00010 5a 5b 5c 5d Water to 100% to 100.0% to 100.0% to 100.0% Glycerol (Glycerol EP, vegetable, Spiga Nord) 4.0% 4.0% 4.0% 4.0% Alcohol 4.0% 4.0% 4.0% 4.0% Sodium Coco-Sulfate (Texapon HC G, BASF) 3.0% 3.0% 3.0% 3.0% Lauryl Glucoside (Plantacare 1200 UP, BASF, 50%) 6.0% 6.0% 6.0% 6.0% Composition from Example 1 0.1% Composition from Example 3 0.1% Composition from Example 4 0.1% Composition from Example 5 0.1% Xanthan Gum (Keltrol CG-SFT, CP Kelco) 1.5% 1.5% 1.5% 1.5% Mangifera Indica (Mango) Fruit Extract (Mango 0.5% 0.5% 0.5% 0.5% Extract, Draco Natural Products) Limonene (Dipentene No, 122, Hercules Inc.) 0.1% 0.1% 0.1% 0.1% Linalool (Lipofresh, Lipo Chemicals, Inc.) 0.1% 0.1% 0.1% 0.1% Citric Acid to pH 4.9 to pH 4.9 to pH 4.9 to pH 4.9 Preservative q.s. q.s. q.s. q.s. Dyes Body q.s. q.s. q.s. cream

Recipes 6a, 6b, 6c and 6d: Cream Soap

[0201]

TABLE-US-00011 6a 6b 6c 6d Water to 100% to 100% to 100% to 100% Propylene Glycol (Euxyl K 320, Schulke & Mayr 2.0% 2.0% 2.0% 2.0% GmbH) Coco-Glucoside (Plantacare 818 UP, BASF, 51%) 10.0% 10.0% 10.0% 10.0% Glycerol (Glycerol EP, vegetable, Spiga Nord) 5.0% 5.0% 5.0% 5.0% Composition from Example 1 2.5% Composition from Example 3 2.5% Composition from Example 4 2.5% Composition from Example 5 2.5% Disodium Cocoyl Glutamate (Planatpon ACG LC, 2.5% 2.5% 2.5% 2.5% BASF) Xanthan Gum (Keltrol CG-SFT, CP Kelco) 1.2% 1.2% 1.2% 1.2% Stearic Acid (Pristerene 4922, Croda Europe, Ltd.) 1.2% 1.2% 1.2% 1.2% Citric Acid to pH 5.5 to pH 5.5 to pH 5.5 to pH 5.5 Olea Europaea Fruit Oil (Cropure Olive, Croda 0.2% 0.2% 0.2% 0.2% Europe, Ltd.) Glyceryl Oleate (TEGIN? O V, Evonik) 1.0% 1.0% 1.0% 1.0% Sodium Cocoyl Glutamate (Plantapon ACG HC, 0.8% 0.8% 0.8% 0.8% BASF) Tetrasodium EDTA (Versene 100, The Dow 0.2% 0.2% 0.2% 0.2% Chemical Company) Perfume 0.1% 0.1% 0.1% 0.1% Preservative q.s. q.s. q.s. q.s. Dyes q.s. q.s. q.s. Body cream

Recipes 7a, 7b, 7c and 7d: Oil Bath

[0202]

TABLE-US-00012 7a 7b 7c 7d Water to 100.0% to 100.0% to 100.0% to 100.0% Glycine Soja Oil (Cropure Soybean, Croda Europe, 20.0% 20.0% 20.0% 20.0% Ltd.) Composition from Example 1 12.0% Composition from Example 3 12.0% Composition from Example 4 12.0% Composition from Example 5 12.0% Polyglyceryl-3 Palmitate (Dermofeel? PP, Evonik 4.5% 4.5% 4.5% 4.5% Dr. Straetmans) Glyceryl Caprylate (Dermosoft? GMCY, Evonik Dr. 3.0% 3.0% 3.0% 3.0% Straetmans) Simmondsia Chinensis Seed Oil (AEC Jojoba Oil 1.2% 1.2% 1.2% 1.2% Refined, A & E Connock, Perfumery & Cosmetics Ltd.) Prunus Amygdalus Dulcis (Sweet Almond) Oil 1.0% 1.0% 1.0% 1.0% (Cropure Almond, Croda Europe, Ltd.) Triticum Vulgare Germ Oil (Cropure Wheatgerm, 0.5% 0.5% 0.5% 0.5% Croda Europe, Ltd.) Tocopherol (Euxyl K 700, Sch?lke & Mayr GmbH) 0.2% 0.2% 0.2% 0.2% Limonene (Dipentene No, 122, Hercules Inc.) 0.1% 0.1% 0.1% 0.1% Citral 0.1% 0.1% 0.1% 0.1% Preservative q.s. q.s. q.s. q.s. Dyes q.s. q.s. q.s. q.s.

Recipes 8a, 8b, 8c and 8d: Micellar Water for Make-Up Removal

[0203]

TABLE-US-00013 8a 8b 8c 8d Water to 100.0% to 100.0% to 100.0% to 100.0% Perfume 0.1% 0.1% 0.1% 0.1% Composition from Example 1 2.0% Composition from Example 3 2.0% Composition from Example 4 2.0% Composition from Example 5 2.0% Capryl/Capramidopropyl Betaine (TEGO? Betain 1.3% 1.3% 1.3% 1.3% 810, Evonik, 38%) Polyglyceryl-6 Caprylate; Polyglyceryl-3 Cocoate; 1.0% 1.0% 1.0% 1.0% Polyglyceryl-4 Caprate; Polyglyceryl-6 Ricinoleate (TEGO? Solve 61, Evonik) Betaine (TEGO? Natural Betaine, Evonik) 2.0% 2.0% 2.0% 2.0% Glycerol (Glycerol EP, vegetable, Spiga Nord) 1.0% 1.0% 1.0% 1.0% Preservative q.s. q.s. q.s. q.s.

Recipes 9a, 9b, 9c and 9d: Solution for Wet Wipes

[0204]

TABLE-US-00014 Recipe 9a 9b 9c 9d Composition from Example 1 3.5% Composition from Example 3 3.5% Composition from Example 4 3.5% Composition from Example 5 3.5% Aloe Barbadensis Leaf Extract (Aloe-Con UP 40, 0.2% 0.2% 0.2% 0.2% Florida Food Products Inc.) Isopropyl Myristate (TEGOSOFT? M, Evonik) 0.2% 0.2% 0.2% 0.2% Disodium Cocoamphodiacetate (REWOTERIC? 1.5% 1.5% 1.5% 1.5% AM 2 C NM, Evonik, 39%) Perfume 0.2% 0.2% 0.2% 0.2% Propylene Glycol (Euxyl K 320, Sch?lke & Mayr 2.5% 2.5% 2.5% 2.5% GmbH) Hydrolyzed Silk (Crosilk 10000, Croda Inc.) 0.2% 0.2% 0.2% 0.2% Caprylyl/Capryl Glucoside (Plantacare 810 UP, 1.0% 1.0% 1.0% 1.0% BASF) Water to 100.0% to 100.0% to 100.0% to 100.0% Citric Acid to pH 5.0 to pH 5.0 to pH 5.0 to pH 5.0 Phenoxyethanol (S&M Phenoxyethanol, Sch?lke & 0.5% 0.5% 0.5% 0.5% Mayr GmbH) Dehydroacetic Acid (Unisept DHA (Universal 0.1% 0.1% 0.1% 0.1% Preserv-A-Chem, Inc.) Sodium Benzoate (Euxyl K 712, Sch?lke & Mayr 0.4% 0.4% 0.4% 0.4% GmbH) Salicylic Acid (Salicylic acid nat,; Evonik Dr. 0.5% 0.5% 0.5% 0.5% Straetmans GmbH)

Recipes 10a, 10b, 10c and 10d: Antiperspirant Deodorant

[0205]

TABLE-US-00015 10a 10b 10c 10d Phase Composition from Example 1 4.0% A Composition from Example 3 4.0% Composition from Example 4 4.0% Composition from Example 5 4.0% Dicaprylyl Ether (Cetiol OE, BASF) 0.3% 0.3% 0.3% 0.3% Geraniol (Nerol 800, International Flavors 0.1% 0.1% 0.1% 0.1% & Fragrances Inc.) Linalool (Lipofresh, Lipo Chemicals, Inc.) 0.1% 0.1% 0.1% 0.1% Perfume 0.1% 0.1% 0.1% 0.1% Phase Propylene Glycol (Euxyl K 320, Sch?lke & 1.0% 1.0% 1.0% 1.0% B Mayr GmbH) Butylene Glycol (Oxea Corparation) 0.2% 0.2% 0.2% 0.2% Water 5.0% 5.0% 5.0% 5.0% Palmitamidopropyltrimonium Chloride 1.0% 1.0% 1.0% 1.0% (VARISOFT? PATC, Evonik) Phase Water 50.0% 50.0% 50.0% 50.0% C Hydroxethyl Ethylcellulose (Structure Cel 0.8% 0.8% 0.8% 0.8% 4400 E, AkzoNobel) Sodium Hydroxide (10% in water) 0.3% 0.3% 0.3% 0.3% Phase Aluminium Chlorohydrate (Locron L, 15.0% 15.0% 15.0% 15.0% D Clariant) Phase Preservative q.s. q.s. q.s. q.s. E Water to 100.0% to 100.0% to 100.0% to 100.0%

Recipes 11a, 11b, 11c and 11d: Mouthwash

[0206]

TABLE-US-00016 11a 11b 11c 11d Composition from Example 1 0.4% Composition from Example 3 0.4% Composition from Example 4 0.4% Composition from Example 5 0.4% Glycolipids (Rheance One, Evonik) 0.2% 0.2% 0.2% 0.2% Flavor 0.2% 0.2% 0.2% 0.2% Water to 100.0% to 100.0% to 100.0% to 100.0% Sorbitol (Karion FP Liquid, Merck) 3.0% 3.0% 3.0% 3.0% Preservative q.s. q.s. q.s. q.s. Dyes q.s. q.s. q.s. q.s.

Recipes 12a, 12b, 12c and 12d: Toothpaste

[0207]

TABLE-US-00017 12a 12b 12c 12d A Sorbitol (Karion FP Liquid, Merck) 50.0% 50.0% 50.0% 50.0% Water to 100.0% to 100.0% to 100.0% to 100.0% Sodium Carboxymethylcellulose (Blanose 1.2% 1.2% 1.2% 1.2% 7MXF, Ashland) B Sodium Saccharine (Sigma Aldrich) 0.1% 0.1% 0.1% 0.1% Sodium Fluoride (Sigma Aldrich) 0.1% 0.1% 0.1% 0.1% C Titanium Dioxide (Caesar & Loretz) 0.4% 0.4% 0.4% 0.4% Hydrated Silica (Zeodent? 113, Evonik) 14.0% 14.0% 14.0% 14.0% Hydrated Silica (Zeodent? 165, Evonik) 8.0% 8.0% 8.0% 8.0% D Flavor oil 1.0% 1.0% 1.0% 1.0% E Glyceryl Caprylate (dermosoft? GMCY, 0.3% 0.3% 0.3% 0.3% Evonik) Composition from Example 1 3.5% Composition from Example 3 3.5% Composition from Example 4 3.5% Composition from Example 5 3.5%

Recipes 13a, 13b, 13c and 13d: Kitchen Cleaning Spray

[0208]

TABLE-US-00018 Ingredient 13a 13b 13c 13d REWOTERIC? AM V 0.5% 0.5% 0.5% 0.5% Composition from Example 1 1.0% Composition from Example 3 1.0% Composition from Example 4 1.0% Composition from Example 5 1.0% TOMAKLEEN? G-14 2.0% 2.0% 2.0% 2.0% Water (Dye, Perfume) 89.5% 89.5% 89.5% 89.5% Chelating Agent, GLDA 3.0% 3.0% 3.0% 3.0% Triethanolamine 4.0% 4.0% 4.0% 4.0%

Recipes 14a, 14b, 14c and 14d: Extra Mild Dish Wash Foam

[0209]

TABLE-US-00019 Ingredient 14a 14b 14c 14d C10-16 Alkylpolyglucoside, 50% 10.0% 10.0% 10.0% 10.0% Xanthan Gum 0.1% 0.1% 0.1% 0.1% Glycerin 2.0% 2.0% 2.0% 2.0% Water 76.9% 76.9% 76.9% 76.9% Composition from Example 1 1.0% Composition from Example 3 1.0% Composition from Example 4 1.0% Composition from Example 5 1.0% REWOFERM? SL ONE 2.0% 2.0% 2.0% 2.0% REWOPOL? SB CS 50 5.0% 5.0% 5.0% 5.0% TEGO? Betain C 60 3.0% 3.0% 3.0% 3.0% Preservative qs. qs. qs. qs.

Recipes 15a, 15b, 15c and 15d: Automatic Rinse Aid for Direct Use 1

[0210]

TABLE-US-00020 Ingredient 15a 15b 15c 15d TEGOTENS? EC 11 5.0% 5.0% 5.0% 5.0% Composition from Example 1 5.0% Composition from Example 3 5.0% Composition from Example 4 5.0% Composition from Example 5 5.0% Citric acid monohydrate 5.0% 5.0% 5.0% 5.0% Water (Dye, Perfume) 85.0% 85.0% 85.0% 85.0%

Recipes 16a, 16b, 16c and 16d: Automatic Rinse Aid for Direct Use 2

[0211]

TABLE-US-00021 Ingredient 16a 16b 16c 16d Citric acid monohydrate 5.0% 5.0% 5.0% 5.0% Sodium Cumene Sulfonate, 92% 1.5% 1.5% 1.5% 1.5% Water (Dye, Perfume) 83.5% 83.5% 83.5% 83.5% TEGOTENS? EC 11 6.0% 6.0% 6.0% 6.0% Composition from Example 1 4.0% Composition from Example 3 4.0% Composition from Example 4 4.0% Composition from Example 5 4.0%

Recipes 17a, 17b, 17c and 17d: Automatic Rinse Aid for Direct Use 3

[0212]

TABLE-US-00022 Ingredient 17a 17b 17c 17d Citric acid monohydrate 5.0% 5.0% 5.0% 5.0% Sodium Cumene Sulfonate, 92% 1.5% 1.5% 1.5% 1.5% Water (Dye, Perfume) 83.5% 83.5% 83.5% 83.5% TEGOTENS? EC 11 7.0% 7.0% 7.0% 7.0% Composition from Example 1 3.0% Composition from Example 3 3.0% Composition from Example 4 3.0% Composition from Example 5 3.0%
Recipes 18a, 18b, 18c and 18d: Glass Cleaner with Optimized Antifogging Efficiency

TABLE-US-00023 Ingredient 18a 18b 18c 18d REWOPOL? TS 35 1.0% 1.0% 1.0% 1.0% Composition from Example 1 0.2% Composition from Example 3 0.2% Composition from Example 4 0.2% Composition from Example 5 0.2% Isopropanol 15.0% 15.0% 15.0% 15.0% Chelating Agent MGDA 2.0% 2.0% 2.0% 2.0% Water (Dye, Perfume) 81.8% 81.8% 81.8% 81.8%

Recipes 19a, 19b, 19c and 19d: Oven Cleanser for Smoking Chamber

[0213]

TABLE-US-00024 Ingredient 19a 19b 19c 19d Water 77.6% 77.6% 77.6% 77.6% Trilon A liquid 8.0% 8.0% 8.0% 8.0% Sodium carbonate 6.0% 6.0% 6.0% 6.0% REWOTERIC? AM KSF 40 5.0% 5.0% 5.0% 5.0% Laureth-6 1.2% 1.2% 1.2% 1.2% Composition from Example 1 1.2% Composition from Example 3 1.2% Composition from Example 4 1.2% Composition from Example 5 1.2% DOWANOL DPnB 1.0% 1.0% 1.0% 1.0%

Recipes 20a, 20b, 20c and 20d: All Purpose Cleanser (Microemulsion)

[0214]

TABLE-US-00025 Ingredient 20a 20b 20c 20d Water 73.0% 73.0% 73.0% 73.0% TEGOTENS? AM VSF 6.0% 6.0% 6.0% 6.0% Composition from Example 1 2.0% Composition from Example 3 2.0% Composition from Example 4 2.0% Composition from Example 5 2.0% REWOPOL? D 510 NC 5.0% 5.0% 5.0% 5.0% Undeceth-6 3.0% 3.0% 3.0% 3.0% Potassium hydroxide, 50% 5.0% 5.0% 5.0% 5.0% Chelating Agent MGDA 6.0% 6.0% 6.0% 6.0%

Recipes 21a, 21b, 21c and 21d: Low Foaming Hard Surface Degreaser

[0215]

TABLE-US-00026 Ingredient 21a 21b 21c 21d C9-11 FATTY ALCOHOL 2.0% 2.0% 2.0% 2.0% ETHOXYLATE - 8 MOLES OF EO Composition from Example 1 1.0% Composition from Example 3 1.0% Composition from Example 4 1.0% Composition from Example 5 1.0% TEGOTENS? G 826 C 4.0% 4.0% 4.0% 4.0% Chelating Agent MGDA 7.5% 7.5% 7.5% 7.5% Water (Dye, Perfume) 85.5% 85.5% 85.5% 85.5%

Recipes 22a, 22b, 22c and 22d: Low Foaming Hard Surface Degreaser (101630-23)

[0216]

TABLE-US-00027 Ingredient 22a 22b 22c 22d C9-11 FATTY ALCOHOL 2.0% 2.0% 2.0% 2.0% ETHOXYLATE - 8 MOLES OF EO Composition from Example 1 1.0% Composition from Example 3 1.0% Composition from Example 4 1.0% Composition from Example 5 1.0% TEGOTENS? G 826 C 4.0% 4.0% 4.0% 4.0% Chelating Agent MGDA 7.5% 7.5% 7.5% 7.5% Water (Dye, Perfume) 85.5% 85.5% 85.5% 85.5%

Recipes 23a, 23b, 23c and 23d: Foaming Hard Surface Degreaser 1

[0217]

TABLE-US-00028 Ingredient 23a 23b 23c 23d C9-11 FATTY ALCOHOL 2.0% 2.0% 2.0% 2.0% ETHOXYLATE - 8 MOLES OF EO TEGOTENS? AM VSF 6.0% 6.0% 6.0% 6.0% Composition from Example 1 1.0% Composition from Example 3 1.0% Composition from Example 4 1.0% Composition from Example 5 1.0% Chelating Agent MGDA 7.5% 7.5% 7.5% 7.5% Water (Dye, Perfume) 83.5% 83.5% 83.5% 83.5%

Recipes 24a, 24b, 24c, and 24d: Foaming Hard Surface Degreaser 2

[0218]

TABLE-US-00029 Ingredient 24a 24b 24c 24d C9-11 FATTY ALCOHOL 3.0% 3.0% 3.0% 3.0% ETHOXYLATE - 8 MOLES OF EO REWOTERIC? AM KSF 40 2.5% 2.5% 2.5% 2.5% Composition from Example 1 1.0% Composition from Example 3 1.0% Composition from Example 4 1.0% Composition from Example 5 1.0% Chelating Agent MGDA 10.0% 10.0% 10.0% 10.0% Water (Dye, Perfume) 83.5% 83.5% 83.5% 83.5%

Recipes 25a, 25b, 25c and 25d: Low Foaming Hard Surface Degreaser

[0219]

TABLE-US-00030 Ingredient 25a 25b 25c 25d Composition from Example 1 1.0% Composition from Example 3 1.0% Composition from Example 4 1.0% Composition from Example 5 1.0% C8-10 Alkylpolyglucosid 4.0% 4.0% 4.0% 4.0% Sodium C13-17 Alkane Sulfonate, 2.0% 2.0% 2.0% 2.0% 30% Chelating Agent MGDA 7.5% 7.5% 7.5% 7.5% Water (Dye, Perfume) 85.5% 85.5% 85.5% 85.5%
Recipes 26a, 26b, 26c and 26d: Hard Surface Degreaser from Renewable Surfactants

TABLE-US-00031 Ingredient 26a 26b 26c 26d Water 89.3% 89.3% 89.3% 89.3% Chelating Agent MGDA 4.0% 4.0% 4.0% 4.0% Sodium carbonate 3.0% 3.0% 3.0% 3.0% TEGOTENS? AM VSF 2.4% 2.4% 2.4% 2.4% Laureth-6 0.6% 0.6% 0.6% 0.6% Composition from Example 1 0.4% Composition from Example 3 0.4% Composition from Example 4 0.4% Composition from Example 5 0.4% TEGOR Polish Additiv Q 70 0.3% 0.3% 0.3% 0.3%

Recipes 27a, 27b, 27c and 27d: Highly Efficient Floor Cleanser

[0220]

TABLE-US-00032 Ingredient 27a 27b 27c 27d Water 89.3% 89.3% 89.3% 89.3% Chelating Agent MGDA 4.0% 4.0% 4.0% 4.0% Sodium carbonate 3.0% 3.0% 3.0% 3.0% TEGOTENS? AM VSF 2.4% 2.4% 2.4% 2.4% Laureth-6 0.6% 0.6% 0.6% 0.6% Composition from Example 1 0.4% Composition from Example 3 0.4% Composition from Example 4 0.4% Composition from Example 5 0.4% TEGOR Polish Additiv Q 70 0.3% 0.3% 0.3% 0.3%

Recipes 28a, 28b, 28c and 28d: Super Natural Wash Lotion for Textile Face Masks

[0221]

TABLE-US-00033 Ingredient 28a 28b 28c 28d Xanthan Gum 0.1% 0.1% 0.1% 0.1% Glycerin 2.0% 2.0% 2.0% 2.0% Water 76.9% 76.9% 76.9% 76.9% Composition from Example 1 1.0% Composition from Example 3 1.0% Composition from Example 4 1.0% Composition from Example 5 1.0% REWOFERM? SL ONE 2.0% 2.0% 2.0% 2.0% REWOPOL? SB CS 50 5.0% 5.0% 5.0% 5.0% C8-10 Alkylpolyglucosid 10.0% 10.0% 10.0% 10.0% TEGO? Betain C 60 3.0% 3.0% 3.0% 3.0% Preservative qs. qs. qs. qs.

Recipes 29a, 29b, 29c and 29d: Highly Effective Presoaker

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TABLE-US-00034 Ingredient 29a 29b 29c 29d Water 77.5% 77.5% 77.5% 77.5% Chelating Agent MGDA 8.0% 8.0% 8.0% 8.0% Sodium metasilicate 2.0% 2.0% 2.0% 2.0% Sodium gluconate 2.0% 2.0% 2.0% 2.0% Sodium carbonate 2.0% 2.0% 2.0% 2.0% TEGOTENS? AM VSF 6.5% 6.5% 6.5% 6.5% Undeceth-6 0.6% 0.6% 0.6% 0.6% Composition from Example 1 0.4% Composition from Example 3 0.4% Composition from Example 4 0.4% Composition from Example 5 0.4% DOWANOL DPnB 1.0% 1.0% 1.0% 1.0%

Recipes 30a, 30b, 30c and 30d: Presoaker (Basic Formula)

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TABLE-US-00035 Ingredient 30a 30b 30c 30d Water 82.6% 82.6% 82.6% 82.6% Trilon A 92 3.0% 3.0% 3.0% 3.0% Sodium metasilicate 2.0% 2.0% 2.0% 2.0% Sodium carbonate 2.0% 2.0% 2.0% 2.0% Bayhibit AM 1.0% 1.0% 1.0% 1.0% REWOTERIC? AM KSF 40 4.0% 4.0% 4.0% 4.0% C9-11 FATTY ALCOHOL 1.2% 1.2% 1.2% 1.2% ETHOXYLATE - 8 MOLES OF EO Composition from Example 1 1.2% Composition from Example 3 1.2% Composition from Example 4 1.2% Composition from Example 5 1.2% DOWANOL DPnB 3.0% 3.0% 3.0% 3.0%

Recipes 31a, 31b, 31c and 31d: Good Dispersing Presoaker

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TABLE-US-00036 Ingredient 31a 31b 31c 31d Water 80.0% 80.0% 80.0% 80.0% Trilon A 92 3.0% 3.0% 3.0% 3.0% Sodium metasilicate 2.0% 2.0% 2.0% 2.0% Sodium carbonate 2.0% 2.0% 2.0% 2.0% Sequion 10 Na 430 2.0% 2.0% 2.0% 2.0% TEGOTENS? 475 5.0% 5.0% 5.0% 5.0% C9-11 FATTY ALCOHOL 1.5% 1.5% 1.5% 1.5% ETHOXYLATE - 7 MOLES OF EO Composition from Example 1 1.5% Composition from Example 3 1.5% Composition from Example 4 1.5% Composition from Example 5 1.5% DOWANOL PnB 3.0% 3.0% 3.0% 3.0%

Recipes 32a, 32b, 32c and 32d: Cost Efficient Presoaker

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TABLE-US-00037 Ingredient 32a 32b 32c 32d Water 80.5% 80.5% 80.5% 80.5% Chelating Agent MDGA 8.0% 8.0% 8.0% 8.0% Sodium carbonate 6.0% 6.0% 6.0% 6.0% TEGOTENS? AM VSF 3.5% 3.5% 3.5% 3.5% Laureth-6 0.6% 0.6% 0.6% 0.6% Composition from Example 1 0.4% Composition from Example 3 0.4% Composition from Example 4 0.4% Composition from Example 5 0.4% DOWANOL DPnB 1.0% 1.0% 1.0% 1.0%

Recipes 33a, 33b, 33c and 33d: Rinse Aid to Minimize Remaining Water

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TABLE-US-00038 Ingredient 33a 33b 33c 33d REWOPAL? MPG 40 6.0% 6.0% 6.0% 6.0% Butyl Cellusolve (BG) 14.0% 14.0% 14.0% 14.0% Composition from Example 1 3.0% Composition from Example 3 3.0% Composition from Example 4 3.0% Composition from Example 5 3.0% REWOQUAT? CR 3099 10.0% 10.0% 10.0% 10.0% TEGOSOFT? OP 5.0% 5.0% 5.0% 5.0% Water 62.0% 62.0% 62.0% 62.0%
5 Recipes 34a, 34b, 34c and 34d: Rinse Aid with Optimal Oil Content

TABLE-US-00039 Ingredient 34a 34b 34c 34d DOWANOL DPnB 8.6% 8.6% 8.6% 8.6% REWOPAL? MPG 40 6.2% 6.2% 6.2% 6.2% REWOQUAT? CR 3099 10.0% 10.0% 10.0% 10.0% REWOCARE? DOC 4.0% 4.0% 4.0% 4.0% TEGOSOFT? OP 3.0% 3.0% 3.0% 3.0% Composition from Example 1 1.0% Composition from Example 3 1.0% Composition from Example 4 1.0% Composition from Example 5 1.0% Water 66.8% 66.8% 66.8% 66.8% TEGOPREN? 6923 0.4% 0.4% 0.4% 0.4%

Recipes 35a, 35b, 35c and 35d: Low Foaming all Purpose Cleaner

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TABLE-US-00040 Ingredient 35a 35b 35c 35d Water 82.0% 82.0% 82.0% 82.0% Trilon A 92 3.0% 3.0% 3.0% 3.0% Sodium metasilicate 2.0% 2.0% 2.0% 2.0% Sodium carbonate 2.0% 2.0% 2.0% 2.0% Sequion 10 Na 430 2.0% 2.0% 2.0% 2.0% TEGOTENS? 475 5.0% 5.0% 5.0% 5.0% C9-11 FATTY ALCOHOL 1.5% 1.5% 1.5% 1.5% ETHOXYLATE - 7 MOLES OF EO Composition from Example 1 1.5% Composition from Example 3 1.5% Composition from Example 4 1.5% Composition from Example 5 1.5% DOWANOL PnB 1.0% 1.0% 1.0% 1.0%

Recipes 36a, 36b, 36c and 36d: Low Foaming Alkaline Cleanser

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TABLE-US-00041 Ingredient 36a 36b 36c 36d Water 85.5% 85.5% 85.5% 85.5% Chelating Agent MDGA 4.0% 4.0% 4.0% 4.0% Sodium carbonate 6.0% 6.0% 6.0% 6.0% TEGOTENS? AM VSF 3.5% 3.5% 3.5% 3.5% Laureth-6 0.6% 0.6% 0.6% 0.6% Composition from Example 1 0.4% Composition from Example 3 0.4% Composition from Example 4 0.4% Composition from Example 5 0.4%

Recipes 37a, 37b, 37c and 37d: Low Foaming Alkaline Cleaner

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TABLE-US-00042 Ingredient 37a 37b 37c 37d Water 85.35% 85.35% 85.35% 85.35% TOMAKLEEN G-14 0.75% 0.75% 0.75% 0.75% TEGOTENS? AM VSF 3.5% 3.5% 3.5% 3.5% Composition from Example 1 0.4% Composition from Example 3 0.4% Composition from Example 4 0.4% Composition from Example 5 0.4% Sodium carbonate 6.0% 6.0% 6.0% 6.0% MGDA-Na3 (40%) 4.0% 4.0% 4.0% 4.0%

Recipes 38a, 38b, 38c and 38d: Alkaline Cleanser (Automatic Wash)

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TABLE-US-00043 Ingredient 38a 38b 38c 38d Water 59.0% 59.0% 59.0% 59.0% Tetra Potassium Pyrophosphate 15.0% 15.0% 15.0% 15.0% (TKPP) Trilon A liquid 5.0% 5.0% 5.0% 5.0% KOH, 45% 4.0% 4.0% 4.0% 4.0% Sequion 10 Na 430 10.0% 10.0% 10.0% 10.0% Sodium metasilicate 6.0% 6.0% 6.0% 6.0% Composition from Example 1 1.0% Composition from Example 3 1.0% Composition from Example 4 1.0% Composition from Example 5 1.0%

Recipes 39a, 39b, 39c and 39d: Metal Cleaner

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TABLE-US-00044 Ingredient 39a 39b 39c 39d Water 82.0% 82.0% 82.0% 82.0% TOMAKLEEN? G-14 12.0% 12.0% 12.0% 12.0% REWOTERIC? AM V 1.5% 1.5% 1.5% 1.5% Composition from Example 1 3.0% Composition from Example 3 3.0% Composition from Example 4 3.0% Composition from Example 5 3.0% Triethanolamine 1.5% 1.5% 1.5% 1.5%

Recipes 40a, 40b, 40c and 40d: Metal Cleanser

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TABLE-US-00045 Ingredient 40a 40b 40c 40d Water (Dye, Perfume) 82.0% 82.0% 82.0% 82.0% Triethanolamine 1.5% 1.5% 1.5% 1.5% DOWANOL PnP 6.0% 6.0% 6.0% 6.0% REWOTERIC? AM V 1.5% 1.5% 1.5% 1.5% Composition from Example 1 3.0% Composition from Example 3 3.0% Composition from Example 4 3.0% Composition from Example 5 3.0% C8-10 Fatty alcohol5 EO 6.0% 6.0% 6.0% 6.0%

Recipes 41a, 41b, 41c and 41d: Cost Efficient Facade Cleanser

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TABLE-US-00046 Ingredient 41a 41b 41c 41d Water 86.6% 86.6% 86.6% 86.6% Chelating Agent, MGDA 4.0% 4.0% 4.0% 4.0% Sodium carbonate 6.0% 6.0% 6.0% 6.0% TEGOTENS? AM VSF 2.4% 2.4% 2.4% 2.4% Laureth-6 0.6% 0.6% 0.6% 0.6% Composition from Example 1 0.4% Composition from Example 3 0.4% Composition from Example 4 0.4% Composition from Example 5 0.4%