Aqueous personal care rinse-off composition

By using the alcohol ethoxysulfate surfactant of formula I in the personal care rinse composition, the problem of the generation of 1,4-dioxane during the preparation and use of the existing AES surfactant is solved, and the effect of low content and high thermal stability is achieved.

CN119894494APending Publication Date: 2025-04-25DOW GLOBAL TECHNOLOGIES LLC +1
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Patent Information

Application Number
CN202380065215.9
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Priority Date
2022-09-20
Filing Date
2023-09-13
Publication Date
2025-04-25

AI Technical Summary

Technical Problem

The existing AES surfactants are prone to produce 1,4-dioxane during preparation and use, resulting in the 1,4-dioxane content in the product exceeding the standard and making it difficult to meet the increasingly stringent regulatory requirements.

Method used

An aqueous personal care wash-off composition comprising an alcohol ethoxy sulfate surfactant of formula I was developed which is able to resist the formation of 1,4-dioxane under sulfation process and under high temperature conditions.

Benefits of technology

It has achieved a significant reduction in the formation of 1,4-dioxane under sulfation process and high temperature conditions, ensuring that the 1,4-dioxane content in the product is less than 9ppm, meeting strict regulatory requirements, and improving the thermal stability of the product.

✦ Generated by Eureka AI based on patent content.

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Abstract

There is provided an aqueous personal care rinse-off composition, the aqueous personal care rinse-off composition comprising: a dermatologically acceptable aqueous vehicle; and a dermatologically acceptable cleansing surfactant wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula (I) wherein R1 and R2 are each independently a C1-16 alkyl group; wherein the sum of carbon atoms in R1 and R2 is from 7 to 17; wherein M + is a negatively charged cation that neutralizes the-SO3-anion of formula (I); and wherein n is 1 in 95 mol% to 100 mol% of the alcohol ethoxysulfate surfactant of formula (I).
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Description

[0001] The present invention relates to a personal care rinse-off composition. Specifically, the present invention relates to a personal care rinse-off composition, the personal care rinse-off composition comprising: a dermatologically acceptable aqueous carrier; and a dermatologically acceptable cleansing surfactant, wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula I

[0002]

[0003] Where R 1 and R 2 Each independently is C 1-16 Alkyl group; wherein R 1 and R 2 The total number of carbon atoms in the + It is -SO in the neutralization formula I 3 - anionic negatively charged cation; and wherein n is 1 in 95 mol % to 100 mol % of the alcohol ethoxysulfate surfactant of formula I.

[0004] Alkyl ethoxy sulfate anionic surfactants (e.g., alcohol ethoxy sulfate surfactants) have been widely used in a variety of personal care cleaning formulations, such as shampoo and body wash formulations. However, conventional AES anionic surfactants are associated with undesirable 1,4-dioxane content. Regulatory agencies have been tightening restrictions on the amount of 1,4-dioxane that may be present in consumer products. For example, New York State has allowed only trace amounts of 1,4-dioxane in cosmetics, personal care products, and cleaning products. Typically, the content of 1,4-dioxane in consumer products must be less than 10 parts per million (ppm) by weight to comply with regulations. One reason for the unexpected incorporation of 1,4-dioxane in consumer products may be the introduction of alkyl ethoxy sulfate anionic surfactants.

[0005] Conventional AES surfactants are believed to introduce 1,4-dioxane at multiple points in time. It is believed that the first point in time for the formation of 1,4-dioxane in conventional AES surfactants occurs during the sulfation process of alcohol ethoxylates, which is used to make alcohol ethoxysulfates. The alcohol ethoxylate intermediates used to produce conventional alcohol ethoxysulfate surfactants are prepared by an ethoxylation reaction (i.e., the reaction of an alcohol with ethylene oxide), which typically results in an alcohol ethoxylate oligomeric distribution. It is believed that 1,4-dioxane can be formed under the sulfation process conditions during the preparation of conventional AES surfactants. It is believed that the second point in time for the formation of 1,4-dioxane associated with conventional AES surfactants occurs during the handling and processing of conventional AES surfactants. The handling and processing of conventional AES surfactants typically involves acidic conditions at ambient or elevated temperatures. Prolonged exposure of conventional AES surfactants and their alcohol ethoxylate precursors to acidic environments can lead to the formation of 1,4-dioxane. Furthermore, exposure to high temperatures (eg, up to 280° C.) during processing, storage, and / or handling can cause conventional AES surfactants to decompose, resulting in the formation of dioxanes.

[0006] Traditionally, the 1,4-dioxane content of conventional AES surfactants and products incorporating such surfactants has been controlled by using stripping techniques. For example, when the 1,4-dioxane concentration is above a target threshold, a stripping process is used to remove excess 1,4-dioxane from the conventional AES surfactant or the product incorporating such surfactant. This stripping process is not only expensive and time-consuming, but also does not guarantee compliance with increasingly stringent regulatory requirements. In addition, since 1,4-dioxane may be formed over time during the handling and further processing of conventional AES surfactants or related products, any stripping technology previously employed may be ineffective due to the generation of new 1,4-dioxane. Therefore, it is a daunting challenge to ensure that products containing AES surfactants comply with relevant regulations when sold to end consumers.

[0007] Therefore, there is still a need to develop a personal care cleansing formulation containing an alcohol ethoxysulfate surfactant that can resist the formation of 1,4-dioxane during the sulfation process to form the surfactant and when the alcohol ethoxysulfate surfactant is subsequently exposed to high temperatures up to 280°C.

[0008] The present invention provides an aqueous personal care rinse-off composition, the aqueous personal care rinse-off composition comprising: a dermatologically acceptable aqueous carrier; and a dermatologically acceptable cleansing surfactant, wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula I

[0009]

[0010] Where R 1 and R 2 Each independently is C 1-16 Alkyl group; wherein R 1 and R 2 The total number of carbon atoms in the + It is -SO in the neutralization formula I 3 - anionic negatively charged cation; and wherein n is 1 in 95 mol % to 100 mol % of the alcohol ethoxy sulfate surfactant of formula I.

[0011] The present invention provides an aqueous personal care rinse-off composition, the aqueous personal care rinse-off composition comprising: a dermatologically acceptable aqueous carrier; and a dermatologically acceptable cleansing surfactant, wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula I; wherein R 1 and R 2 Each independently is C 1-16 Alkyl group; wherein R 1 and R 2 The total number of carbon atoms in the + It is -SO in the neutralization formula I 3 - anionic negatively charged cation; wherein n is 1 in 95 mol % to 100 mol % of the alcohol ethoxy sulfate surfactant of formula I; and wherein the alcohol ethoxy sulfate surfactant of formula I contains <9 ppm of 1,4-dioxane.

[0012] The present invention provides an aqueous personal care rinse-off composition, the aqueous personal care rinse-off composition comprising: a dermatologically acceptable aqueous carrier; and a dermatologically acceptable cleansing surfactant, wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula I; wherein R 1 and R 2 Each independently is C 1-16 Alkyl group; wherein R 1 and R 2 The total number of carbon atoms in the + It is -SO in the neutralization formula I 3 -anionic negatively charged cation; wherein n is 1 in 95 mol % to 100 mol % of the alcohol ethoxy sulfate surfactant of formula I; wherein the alcohol ethoxy sulfate surfactant of formula I contains <9 ppm of 1,4-dioxane; and wherein the alcohol ethoxy sulfate surfactant of formula I is capable of resisting the formation of 1,4-dioxane when exposed to temperatures up to 280°C.

[0013] The present invention provides an aqueous personal care rinse-off composition, the aqueous personal care rinse-off composition comprising: a dermatologically acceptable aqueous carrier; and a dermatologically acceptable cleansing surfactant, wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula I; wherein R 1 and R 2 Each is independently C 1-16 Alkyl group; wherein R 1 and R 2 The total number of carbon atoms in the + It is -SO in the neutralization formula I 3 - anionic negatively charged cation; wherein n is 1 in 95 mol % to 100 mol % of the alcohol ethoxy sulfate surfactant of formula I; and wherein the aqueous personal care rinse-off composition contains <2 wt % of the alcohol sulfate surfactant of formula II based on the solid weight of the aqueous personal care rinse-off composition

[0014]

[0015] Where R 3 and R 4 Each is independently C 1-16 Alkyl group; wherein R 3 and R 4 The total number of carbon atoms in the + It is -SO in the neutralization formula II 3 - Anions are negatively charged cations.

[0016] The present invention provides an aqueous personal care rinse-off composition, the aqueous personal care rinse-off composition comprising: a dermatologically acceptable aqueous carrier; a thickening salt and a dermatologically acceptable cleansing surfactant, wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula I; wherein R 1 and R 2 Each is independently C 1-16 Alkyl group; wherein R 1 and R 2 The total number of carbon atoms in the +It is -SO in the neutralization formula I 3 - anionic negatively charged cation; wherein n is 1 in 95 mol % to 100 mol % of the alcohol ethoxy sulfate surfactant of formula I; wherein the aqueous personal care rinse-off composition contains <2 wt % of the alcohol sulfate surfactant of formula II based on the solid weight of the aqueous personal care rinse-off composition; wherein R 3 and R 4 Each is independently C 1-16 Alkyl group; wherein R 3 and R 4 The total number of carbon atoms in the + It is -SO in the neutralization formula II 3 - Anions are negatively charged cations.

[0017] The present invention provides a method for cleansing at least one of mammalian skin and hair, the method comprising: (a) applying an aqueous personal care rinse-off composition according to the present invention to the mammalian skin or hair; and (b) rinsing the aqueous personal care rinse-off composition from the skin or hair with rinse water. DETAILED DESCRIPTION

[0018] We have unexpectedly discovered that the alcohol ethoxysulfate surfactant of formula I

[0019]

[0020] Where R 1 and R 2 Each is independently C 1-16 Alkyl group; wherein R 1 and R 2 The total number of carbon atoms in the + It is -SO in the neutralization formula I 3 - anionic negatively charged cation; and wherein n is 1 in 95 mol % to 100 mol % of the alcohol ethoxy sulfate surfactant of formula I, the alcohol ethoxy sulfate surfactant of formula I during the sulfation process to form the alcohol ethoxy sulfate surfactant of formula I, and when the alcohol ethoxy sulfate surfactant is subsequently exposed to high temperatures up to 280° C. during processing, storage and / or handling., can resist the formation of 1,4-dioxane.

[0021] We have also surprisingly found that the alcohol ethoxysulfate surfactant of formula I

[0022]

[0023] Where R1 and R 2 Each is independently C 1-16 Alkyl group; wherein R 1 and R 2 The total number of carbon atoms in the + It is -SO in the neutralization formula I 3 - anionic negatively charged cation; and wherein n is 1 in 95 mol % to 100 mol % of the alcohol ethoxy sulfate surfactant of formula I, compared with conventional sodium lauryl polyoxyethylene ether sulfate surfactant, the alcohol ethoxy sulfate surfactant of formula I can reduce the salt content required for aqueous personal care rinse-off compositions containing the alcohol ethoxy sulfate surfactant of formula I when diluted and thickened.

[0024] Unless otherwise indicated, ratios, percentages, parts, etc., are by weight (eg, "ppm" means parts per million by weight).

[0025] The term "cosmetically acceptable" as used herein and in the appended claims refers to ingredients typically used in personal care compositions, and is intended to emphasize that materials that are toxic when present in amounts typically found in personal care compositions are not contemplated as part of the present invention.

[0026] As used herein and in the appended claims, when referring to aqueous personal care rinse-off compositions and the alcohol ethoxysulfate surfactant of Formula I, the term "solids weight" refers to dry weight, ie, excluding any water that may be present.

[0027] Preferably, the aqueous personal care rinse-off composition of the present invention is selected from the group consisting of shampoo, conditioning shampoo, body wash formulation, exfoliating body wash formulation, facial cleanser formulation, exfoliating facial cleanser formulation, liquid hand soap formulation and mild cleaning formulation, etc. More preferably, the aqueous personal care rinse-off composition of the present invention is selected from the group consisting of shampoo, conditioning shampoo, body wash formulation, exfoliating body wash formulation, facial cleanser formulation, exfoliating facial cleanser formulation, liquid hand soap formulation and mild cleaning formulation. Still more preferably, the aqueous personal care rinse-off composition of the present invention is selected from the group consisting of shampoo, conditioning shampoo, body wash formulation, facial cleanser formulation and liquid hand soap formulation. Most preferably, the aqueous personal care rinse-off composition of the present invention is a shampoo or body wash formulation.

[0028] Preferably, the aqueous personal care rinse-off composition of the present invention comprises a dermatologically acceptable aqueous carrier (preferably, 25 wt. % to 99 wt. % (more preferably, 30 wt. % to 95 wt. %; still more preferably, 40 wt. % to 92 wt. %; most preferably, 70 wt. % to 90 wt. %) of a dermatologically acceptable aqueous carrier, based on the weight of the aqueous personal care rinse-off composition); and a dermatologically acceptable cleansing surfactant (preferably, 0.5 wt. % to 60 wt. % (more preferably, 1 wt. % to 50 wt. %; still more preferably, 5 wt. % to 30 wt. %; most preferably, 7 wt. % to 20 wt. %) of a dermatologically acceptable aqueous carrier, based on the weight of the aqueous personal care rinse-off composition), wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula I

[0029]

[0030] Where R 1 and R 2 Each is independently C 1-16 Alkyl groups (preferably C 1-15 More preferably, C 1-14 Alkyl groups; most preferably, straight chain C 1-13 );where R 1 and R 2 The sum of carbon atoms in the alkylene oxide is 7 to 17 (preferably, 10 to 16; more preferably, 11 to 15; most preferably, 12 to 14) (preferably, wherein R 1 and R 2 is a straight chain alkyl group); wherein M + It is -SO in the neutralization formula I 3 - Anion negatively charged cation; (preferably, wherein M + is a cation selected from the group consisting of nitrogen-containing cations (e.g., ammonium cations), metal cations (e.g., alkali metal cations, alkaline earth metal cations), boron-containing cations, and phosphorus-containing cations; more preferably, ammonium cations, alkali metal cations, and alkaline earth metal cations; still more preferably, ammonium cations, sodium cations, and calcium cations; most preferably, sodium cations); and wherein n is 1 (preferably, as used in 95 mol % to 100 mol % (preferably, 96 mol % to 100 mol %; more preferably, 97 mol % to 100 mol %; most preferably, 97.5 mol % to 100 mol %) of the alcohol ethoxysulfate surfactant of formula I 13 C NMR characterization).

[0031] Preferably, the personal care rinse-off composition of the present invention comprises 25 wt % to 99 wt % (preferably, 30 wt % to 95 wt %; more preferably, 10 wt % to 92 wt %; most preferably, 70 wt % to 90 wt %) of a dermatologically acceptable carrier, based on the weight of the personal care composition. More preferably, the personal care rinse-off composition of the present invention comprises 25 wt % to 99 wt % (preferably, 30 wt % to 95 wt %; more preferably, 10 wt % to 92 wt %; most preferably, 70 wt % to 90 wt %) of a dermatologically acceptable carrier, based on the weight of the personal care composition; wherein the dermatologically acceptable aqueous carrier is selected from the group consisting of water and water and C 1-4 Still more preferably, the personal care rinse-off composition of the present invention comprises from 25 wt % to 99 wt % (preferably, from 30 wt % to 95 wt %; more preferably, from 10 wt % to 92 wt %; most preferably, from 70 wt % to 90 wt %) of a dermatologically acceptable carrier, based on the weight of the personal care composition; wherein the dermatologically acceptable carrier comprises water. Most preferably, the personal care rinse-off composition of the present invention comprises from 25 wt % to 99 wt % (preferably, from 30 wt % to 95 wt %; more preferably, from 10 wt % to 92 wt %; most preferably, from 70 wt % to 90 wt %) of a dermatologically acceptable carrier, based on the weight of the personal care composition; wherein the dermatologically acceptable carrier is water.

[0032] Preferably, the aqueous personal care rinse-off composition of the present invention comprises from 0.5 wt % to 60 wt % (preferably, from 1 wt % to 50 wt %; more preferably, from 5 wt % to 30 wt %; most preferably, from 7 wt % to 20 wt %) of a dermatologically acceptable cleansing surfactant, based on the weight of the aqueous personal care rinse-off composition, wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of Formula I

[0033]

[0034] Where R 1 and R 2 Each independently is C 1-16 Alkyl groups (preferably C 1-15 More preferably, C 1-14 Alkyl groups; most preferably, straight chain C 1-13 );where R 1 and R 2 The sum of carbon atoms in the alkylene oxide is 7 to 17 (preferably, 10 to 16; more preferably, 11 to 15; most preferably, 12 to 14) (preferably, wherein R 1 and R 2is a straight chain alkyl group); wherein M + It is -SO in the neutralization formula I 3 - Anion negatively charged cation; (preferably, wherein M + is a cation selected from the group consisting of nitrogen-containing cations (e.g., ammonium cations), metal cations (e.g., alkali metal cations, alkaline earth metal cations), boron-containing cations, and phosphorus-containing cations; more preferably, ammonium cations, alkali metal cations, and alkaline earth metal cations; still more preferably, ammonium cations, sodium cations, and calcium cations; most preferably, sodium cations); and wherein n is 1 (preferably, as used in 95 mol % to 100 mol % (preferably, 96 mol % to 100 mol %; more preferably, 97 mol % to 100 mol %; most preferably, 97.5 mol % to 100 mol %) of the alcohol ethoxysulfate surfactant of formula I 13 C NMR characterization).

[0035] Preferably, the alcohol ethoxy sulfate surfactant of formula I contains <9 ppm (preferably, <8 ppm; more preferably, <7 ppm; still more preferably, <6 ppm; still more preferably, <5 ppm; still yet more preferably, <4 ppm; still yet more preferably, <3 ppm; even still more preferably, <2 ppm; even yet more preferably, <1 ppm; even still yet more preferably, <0.25 ppm; most preferably, below the detection limit) of 1,4-dioxane based on the solid weight of the alcohol ethoxy sulfate surfactant of formula I (preferably, wherein the 1,4-dioxane content is measured by liquid injection cryogenic gas chromatography-mass spectrometry analysis for the organic layer and liquid chromatography-mass spectrometry analysis for the aqueous layer).

[0036] Preferably, the alcohol ethoxysulfate surfactant of formula I contains <2 wt% (preferably, <1.75 wt%; more preferably, <1.5 wt%; still more preferably, <1.25 wt%; still more preferably, <1.1 wt%; most preferably, ≤1 wt%) of the alcohol sulfate surfactant of formula II based on the solid weight of the alcohol ethoxysulfate surfactant of formula I.

[0037]

[0038] Where R 3 and R 4 Each is independently C 1-16 Alkyl groups (preferably C 1-15 More preferably, C 1-14 Alkyl groups; most preferably, straight chain C 1-13 );where R 1 and R2 The sum of carbon atoms in the alkylene oxide is 7 to 17 (preferably, 10 to 16; more preferably, 11 to 15; most preferably, 12 to 14) (preferably, wherein R 1 and R 2 is a straight chain alkyl group); and wherein A + It is -SO in the neutralization formula II 3 - Anion negatively charged cation; (preferably, wherein A + is a cation selected from the group consisting of a nitrogen-containing cation (e.g., an ammonium cation), a metal cation (e.g., an alkali metal cation, an alkaline earth metal cation), a boron-containing cation, and a phosphorus-containing cation; more preferably, an ammonium cation, an alkali metal cation, and an alkaline earth metal cation; still more preferably, an ammonium cation, a sodium cation, and a calcium cation; most preferably, a sodium cation).

[0039] Preferably, the personal care rinse-off composition of the present invention comprises an alcohol ethoxysulfate surfactant of formula I as described above, wherein the alcohol ethoxysulfate surfactant of formula I has improved thermal stability. More preferably, the personal care rinse-off composition of the present invention comprises an alcohol ethoxysulfate surfactant of formula I as described above, wherein the alcohol ethoxysulfate surfactant of formula I has enhanced thermal stability. As used herein and in the appended claims, the term "enhanced thermal stability" means that when heated to 110°C, the alcohol ethoxy sulfate surfactant of formula I contains <9 ppm (preferably, <8 ppm; more preferably, <7 ppm; still more preferably, <6 ppm; still more preferably, <5 ppm; still yet more preferably, <4 ppm; still yet more preferably, <3 ppm; even still more preferably, <2 ppm; even yet more preferably, <1 ppm; most preferably, <0.5 ppm) of 1,4-dioxane based on the solid weight of the alcohol ethoxy sulfate surfactant of formula I (preferably, wherein the 1,4-dioxane content is measured by liquid injection cryogenic gas chromatography-mass spectrometry analysis for the organic layer and liquid chromatography-mass spectrometry analysis for the aqueous layer). As used herein and in the appended claims, the term "enhanced thermal stability" means that when heated to 280°C, the alcohol ethoxy sulfate surfactant of Formula I contains <10 ppm of 1,4-dioxane based on the solid weight of the alcohol ethoxy sulfate surfactant of Formula I (preferably, wherein the 1,4-dioxane content is measured by liquid injection gas chromatography-mass spectrometry analysis for the organic layer and liquid chromatography-mass spectrometry analysis for the aqueous layer).

[0040] Preferably, the aqueous personal care rinse-off composition of the present invention comprises 0.5 wt. % to 60 wt. % (preferably, 1 wt. % to 50 wt. %; more preferably, 5 wt. % to 30 wt. %; most preferably, 7 wt. % to 20 wt. %) of a dermatologically acceptable cleansing surfactant, based on the weight of the aqueous personal care rinse-off composition; wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula I and at least one additional surfactant; wherein the weight ratio of the alcohol ethoxysulfate surfactant of formula I to the at least one additional surfactant in the aqueous personal care rinse-off composition is from 10:1 to 1:10 (preferably, 7:1 to 1:7; more preferably, 5:1 to 1:1; most preferably, 3.5:1 to 1.75:1). More preferably, the aqueous personal care rinse-off composition of the present invention comprises from 0.5 wt. % to 60 wt. % (preferably, from 1 wt. % to 50 wt. %; more preferably, from 5 wt. % to 30 wt. %; most preferably, from 7 wt. % to 20 wt. %) of a dermatologically acceptable cleansing surfactant, based on the weight of the aqueous personal care rinse-off composition; wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of Formula I and at least one additional surfactant; wherein the at least one additional surfactant is selected from the group consisting of: alkyl polyglucosides (e.g., lauryl glucoside, cocoyl glucoside, decyl glucoside), alkyl polypentosides (e.g., C 5-18 alkyl glucosides), glycinates (e.g., sodium cocoyl glycinate), betaines (e.g., alkyl betaines (such as cetyl betaine) and amido betaines (such as cocamidopropyl betaine)), taurates (e.g., sodium methyl cocoyl taurate), glutamates (e.g., sodium cocoyl glutamate), sarcosinates (e.g., sodium lauroyl sarcosinate), isethionates (e.g., sodium cocoyl isethionate, sodium lauroyl methyl isethionate), sulfoacetates (e.g., sodium lauryl sulfoacetate), alaninates (e.g., sodium cocoyl alanine), amphoacetates (e.g., sodium cocoamphoacetate), sulfonates (e.g., C 14-16The invention relates to a composition comprising the following: a) a surfactant selected from the group consisting of sodium olefin sulfonate, sodium olefin sulfonate, sulfate (e.g., sodium lauryl sulfate), succinate (e.g., disodium lauryl sulfosuccinate), sophorolipids (e.g., lactone type, acid type), rhamnolipids and mixtures thereof; and wherein the weight ratio of the alcohol ethoxysulfate surfactant of formula I to the at least one additional surfactant in the aqueous personal care rinse-off composition is from 10:1 to 1:10 (preferably, from 7:1 to 1:7; more preferably, from 5:1 to 1:1; most preferably, from 3.5:1 to 1.75:1). More preferably, the aqueous personal care rinse-off composition of the present invention comprises 0.5 wt.% to 60 wt.% (preferably, 1 wt.% to 50 wt.%; more preferably, 5 wt.% to 30 wt.%; most preferably, 7 wt.% to 20 wt.%) of a dermatologically acceptable cleansing surfactant, based on the weight of the aqueous personal care rinse-off composition; wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula I and at least one additional surfactant; wherein the at least one additional surfactant is selected from the group consisting of sulfates, sophorolipids, rhamnolipids, betaines, glycinates, glucosides and succinates; and wherein the weight ratio of the alcohol ethoxysulfate surfactant of formula I to the at least one additional surfactant in the aqueous personal care rinse-off composition is from 10:1 to 1:10 (preferably, 7:1 to 1:7; more preferably, 5:1 to 1:1; most preferably, 3.5:1 to 1.75:1). Still more preferably, the aqueous personal care rinse-off composition of the present invention comprises 0.5 wt.% to 60 wt.% (preferably, 1 wt.% to 50 wt.%; more preferably, 5 wt.% to 30 wt.%; most preferably, 7 wt.% to 20 wt.%) of a dermatologically acceptable cleansing surfactant, based on the weight of the aqueous personal care rinse-off composition; wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula I and at least one additional surfactant; wherein the at least one additional surfactant is selected from the group consisting of: an alkyl polyglucoside (e.g., lauryl glucoside, cocoyl glucoside, decyl glucoside) and a betaine; and wherein the weight ratio of the alcohol ethoxysulfate surfactant of formula I to the at least one additional surfactant in the aqueous personal care rinse-off composition is from 10:1 to 1:10 (preferably, 7:1 to 1:7; more preferably, 5:1 to 1:1; most preferably, 3.5:1 to 1.75:1).Most preferably, the aqueous personal care rinse-off composition of the present invention comprises 0.5 wt. % to 60 wt. % (preferably, 1 wt. % to 50 wt. %; more preferably, 5 wt. % to 30 wt. %; most preferably, 7 wt. % to 20 wt. %) of a dermatologically acceptable cleansing surfactant, based on the weight of the aqueous personal care rinse-off composition; wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of Formula I and at least one additional surfactant; wherein the at least one additional surfactant is a mixture of alkyl polyglucoside and cocamidopropyl betaine; and wherein the weight ratio of the alcohol ethoxysulfate surfactant of Formula I to the at least one additional surfactant in the aqueous personal care rinse-off composition is from 10:1 to 1:10 (preferably, 7:1 to 1:7; more preferably, 5:1 to 1:1; most preferably, 3.5:1 to 1.75:1).

[0041] Preferably, the personal care rinse-off composition of the present invention further comprises at least one optional personal care ingredient. More preferably, the personal care rinse-off composition of the present invention further comprises at least one optional personal care ingredient, wherein the at least one optional personal care ingredient is selected from the group consisting of emollients (e.g., hydrocarbon oils, esters, natural oils), cosmetically acceptable silicone oils (e.g., amodimethicone, cyclomethicone, dimethicone, dimethicone, hexadecylmethicone, hexamethyldisiloxane, methylsiloxane, phenyldimethicone, stearoxydimethicone), waxes, soaps, sensory modifiers, lubricants, preservatives (e.g., benzoic acid, sorbic acid, phenoxyethanol), antioxidants (e.g., butylated hydroxytoluene), chelating agents, antimicrobial agents, pH adjusters / buffers / neutralizers, humectants (e.g., glycerol, sorbitol, monoglycerides, lecithin, glycolipids, fatty alcohols, fatty acids, polyols, Sugars, sorbitan esters, polysorbates (e.g., polysorbate 20, polysorbate 40, polysorbate 60, and polysorbate 80), glycols (e.g., propylene glycol), glycol analogs, triols, triol analogs, polymeric polyols), sunscreen active ingredients, vitamins, proteins / amino acids, plant extracts, natural ingredients, bioactive ingredients, flavors / fragrances, penetration enhancers, polymers / resins / hair fixatives / film formers, surfactants / detergents / emulsifiers / sunscreens, volatile materials / propellants / solvents / carriers, liquid vehicles / solvents / carriers, salts, antistatic agents, anti-frizz agents, anti-dandruff agents, perming / straightening agents, adsorbents, colorants, hard particles, rheology modifiers (e.g., carbomers, acrylates, celluloses, stearates, natural gums), and conditioning agents (e.g., polyquaternium 10, cationic guar gum).

[0042] Preferably, the personal care rinse-off composition of the present invention further comprises a thickening salt. More preferably, the personal care rinse-off composition of the present invention further comprises 0.1 wt % to 20 wt % (preferably 0.2 wt % to 15 wt %; more preferably 0.3 wt % to 10 wt %; most preferably 0.5 wt % to 3 wt %) of a thickening salt, based on the weight of the personal care rinse-off composition, the personal care rinse-off composition of the present invention further comprises 0.1 wt % to 20 wt % (preferably 0.2 wt % to 15 wt %; more preferably 0.3 wt % to 10 wt %; most preferably 0.5 wt % to 3 wt %) of a thickening salt, based on the weight of the personal care rinse-off composition; wherein the thickening salt is selected from the group consisting of sodium chloride, potassium chloride, sodium sulfate, potassium sulfate, magnesium chloride, magnesium sulfate, zinc sulfate, ammonium chloride and monoethanolamine chloride and mixtures thereof. Still more preferably, the personal care rinse-off composition of the present invention further comprises 0.1 wt. % to 20 wt. % (preferably, 0.2 wt. % to 15 wt. %; more preferably, 0.3 wt. % to 10 wt. %; most preferably, 0.5 wt. % to 3 wt. %) of a thickening salt, based on the weight of the personal care rinse-off composition, the personal care rinse-off composition of the present invention further comprises 0.1 wt. % to 20 wt. % (preferably, 0.2 wt. % to 15 wt. %; more preferably, 0.3 wt. % to 10 wt. %; most preferably, 0.5 wt. % to 3 wt. %) of a thickening salt, based on the weight of the personal care rinse-off composition; wherein the thickening salt is selected from the group consisting of sodium chloride, potassium chloride, magnesium chloride and mixtures thereof. Most preferably, the personal care rinse-off composition of the present invention further comprises 0.1 wt. % to 20 wt. % (preferably, 0.2 wt. % to 15 wt. %; more preferably, 0.3 wt. % to 10 wt. %; most preferably, 0.5 wt. % to 3 wt. %) of a thickening salt, based on the weight of the personal care rinse-off composition, and the personal care rinse-off composition of the present invention further comprises 2 wt. % to 35 wt. % (preferably, 4 wt. % to 20 wt. %; more preferably, 5 wt. % to 15 wt. %; most preferably, 6 wt. % to 10 wt. %) of a thickening salt, based on the weight of the personal care rinse-off composition; wherein the thickening salt is sodium chloride.

[0043] Preferably, the personal care rinse-off composition of the present invention comprises <9 ppm (preferably, <5 ppm; more preferably, <4 ppm; still more preferably, <3 ppm; still more preferably, <2 ppm; yet still more preferably, <1 ppm; still yet more preferably, <0.5 ppm; even more preferably, <0.25 ppm; even still more preferably, <0.15 ppm; most preferably, below the detection limit) of 1,4-dioxane based on the solids weight of the personal care rinse-off composition (preferably, wherein the 1,4-dioxane content is measured by liquid injection cryogenic gas chromatography-mass spectrometry for the organic layer and liquid chromatography-mass spectrometry for the aqueous layer).

[0044] Preferably, the aqueous personal care rinse-off composition of the present invention comprises <1 wt% (preferably, <0.1; more preferably, <0.01 wt%; still more preferably, <0.0015 wt%; still more preferably, <0.001 wt%; most preferably, below the detection limit) of an alcohol sulfate surfactant of Formula II based on the solids weight of the personal care rinse-off composition.

[0045]

[0046] Where R 3 and R 4 Each is independently C 1-16 Alkyl groups (preferably C 1-15 More preferably, C 1-14 Alkyl groups; most preferably, straight chain C 1-13 );where R 1 and R 2 The sum of carbon atoms in the alkylene oxide is 7 to 17 (preferably, 10 to 16; more preferably, 11 to 15; most preferably, 12 to 14) (preferably, wherein R 1 and R 2 is a straight chain alkyl group); and wherein A + It is -SO in the neutralization formula II 3 - Anion negatively charged cation; (preferably, wherein A + is a cation selected from the group consisting of a nitrogen-containing cation (e.g., an ammonium cation), a metal cation (e.g., an alkali metal cation, an alkaline earth metal cation), a boron-containing cation, and a phosphorus-containing cation; more preferably, an ammonium cation, an alkali metal cation, and an alkaline earth metal cation; still more preferably, an ammonium cation, a sodium cation, and a calcium cation; most preferably, a sodium cation).

[0047] Preferably, the personal care rinse-off composition of the present invention has a viscosity of ≥ 3,000 cP as measured according to the method used in the examples herein. More preferably, the personal care rinse-off composition of the present invention has a viscosity of 3,000 cP to 15,000 cP as measured according to the method used in the examples herein. Still more preferably, the personal care rinse-off composition of the present invention has a viscosity of 4,000 cP to 12,000 cP as measured according to the method used in the examples herein. Most preferably, the personal care rinse-off composition of the present invention has a viscosity of 5,000 cP to 9,000 cP as measured according to the method used in the examples herein.

[0048] Preferably, the personal care rinse-off composition of the present invention further comprises a pH adjuster. More preferably, the personal care rinse-off composition of the present invention further comprises a pH adjuster, wherein the personal care rinse-off composition has a pH of 5 to 9 (preferably, 6 to 8; most preferably, 6.25 to 7.75).

[0049] Preferably, the pH adjusting agent is selected from the group consisting of: citric acid, lactic acid, hydrochloric acid, aminoethylpropylene glycol, triethanolamine, monoethanolamine, sodium hydroxide, potassium hydroxide, amino-2-methyl-1-propanol. More preferably, the pH adjusting agent is selected from the group consisting of: citric acid, lactic acid, sodium hydroxide, potassium hydroxide, triethanolamine, amino-2-methyl-1-propanol. Most preferably, the pH adjusting agent is selected from the group consisting of: citric acid and sodium hydroxide.

[0050] Preferably, the method of the present invention for cleaning at least one of mammalian skin and hair (preferably, at least one of human skin and hair) comprises: applying the aqueous personal care rinse-off composition of the present invention to the skin or hair of a mammal (preferably a human); and rinsing the aqueous personal care rinse-off composition from the skin or hair with rinse water.

[0051] Some embodiments of the present invention will now be described in detail in the following examples.

[0052] Experimental Materials

[0053]

[0054]

[0055] Synthesis S1:C 12 EO

[0056] When using the catalyst to etherify 1-dodecene and monoethylene glycol, a 3 liter (L) three-necked glass round-bottom flask equipped with an overhead stirrer for stirring through the center neck, a reflux condenser, and a heating jacket was used. To ensure good mixing, a paddle impeller was used for stirring. A reaction mixture of 551.7 grams (g) of ethylene glycol and 505.8 g of 1-dodecene was prepared and charged into the reactor at 23° C. together with 61 g of powdered catalyst. The impeller stirring rate was set to 400 revolutions per minute (“rpm”). The reactor was heated to 135° C. in 30 minutes, maintained at 135° C. for 18 hours, and then the reactor was cooled to 23° C. by turning off the heater. The reaction mixture was separated into monoethylene glycol and catalyst phases and olefin phases using a separatory funnel.

[0057] The distillation apparatus consisted of a 1-liter round-bottom flask connected to a short-path still head with a thermometer connection and a condenser with a vacuum connection at the outlet. The distillation flask was heated in an aluminum block by an IKA heated stirring plate. The combined olefin phases were charged to the distillation pot, which was then stirred and evacuated. Obvious boiling was observed, but no condensate was observed or collected. The temperature of the heating block was increased to 75°C, and the unreacted dodecane was collected at a distillation head temperature of 25°C to 50°C and a pressure of 13.3 Pascals to 40 Pascals (Pa). The temperature of the heating block was gradually increased to 140°C, and an intermediate fraction containing both monoether alcohol ethoxylate and dodecene was recovered at a pressure of 13 Pa when the head temperature was increased from 50°C to 75°C. C was collected at a head temperature of 70°C to 115°C and a pressure of 6 Pa to 33 Pa. 12 The heating block temperature was gradually raised to 200°C. At a pressure of 6 Pa, when the head temperature increased from 115°C to 130°C, an intermediate fraction containing both monoether alcohol ethoxylate and diether was collected. The distillation was stopped and the diether retained in the tank was collected. 12 The EO is sent to the next sulfation process to prepare sulfate anionic surfactant.

[0058] Synthesis of S2:C 14 EO

[0059] A 300 mL Parr reactor with a heating jacket and controller was used for the etherification of 1-tetradecene and monoethylene glycol using the catalyst. To ensure good mixing, a paddle impeller was used for stirring.

[0060] A reaction mixture of 100.0 g of monoethylene glycol and 100.0 g of 1-tetradecene was prepared and loaded into a reactor at 23 ° C with 10.0 g of a powdered catalyst. The impeller stirring rate was set to at least 600 rpm. The reactor was heated to 135 ° C in 30 minutes, kept at 135 ° C for 6 hours, and then cooled to room temperature by turning off the heater. The reaction mixture was separated with a separatory funnel. The reaction mixture was separated into monoethylene glycol and catalyst phases and olefin phases using a separatory funnel. 15 batches were produced, and the olefin phases were collected and combined for distillation.

[0061] C was distilled using the same distillation apparatus as used in Synthesis S1. 14 EO. The distillation tank was charged with the product of the olefin phase produced by the operation of multiple batch reactors, then stirred and evacuated. Obvious boiling was observed, but no condensate was observed or collected. The temperature of the heating block was increased to 95°C, and the unreacted 1-tetradecene was collected under the conditions of a distillation head temperature of 30°C to 60°C and a pressure of 27Pa to 5Pa. The temperature of the heating block was gradually increased to 170°C, and at a pressure of 7Pa to 5Pa, when the head temperature was increased from 60°C to 85°C, an intermediate fraction containing both monoether and tetradecene was recovered. C was collected under the conditions of a head temperature of 80°C to 115°C and a pressure of 8Pa to 5Pa. 14 EO. When the temperature of the distillation pot was set to 170°C, the distillation was stopped when no more material was distilled out.

[0062] Synthesis of S3:C 12 EO Sulfate

[0063] All chemical manipulations were performed under a dry nitrogen atmosphere. Prior to the experiment, all glassware was heated in a laboratory oven to remove residual moisture. A 2 L three-necked round-bottom flask was charged with dichloromethane (500 mL) and C prepared according to Synthesis S1. 12EO (40g, 0.173mol, 1.0 equivalent). The reaction flask was equipped with an overhead mechanical stirrer, a charging funnel and a thermocouple. Then, chlorosulfonic acid (12.7mL, 0.191mol, 1.1 equivalents) was carefully loaded into the charging funnel. The reaction flask was then immersed in an ice bath and cooled for 20 minutes to 0°C. After the reaction was cooled, chlorosulfonic acid was added dropwise to the reaction flask at a rate of about 1.0mL / min in about 20 minutes. During the addition of chlorosulfonic acid, the reaction temperature did not exceed 5°C. After addition, the reactants were reacted and the temperature was maintained between 0°C and 5°C for 3 hours. At this point, the reaction was neutralized by slowly adding a NaOH aqueous solution (500mL aqueous solution of 18.0g NaOH, 0.9 moles) dropwise. The addition rate was slow enough not to exceed 5°C during the addition process. After adding about 300mL 0.9 molar NaOH solution, the solution became alkaline. The dichloromethane was then carefully removed from the two phase reaction in vacuo. During the dichloromethane removal, a large amount of foaming was observed. After the dichloromethane was removed, the remaining aqueous solution was placed in a freeze dryer / lyophilizer to obtain the secondary alcohol ethoxylate sulfate product, C 12 EO sulfate as a white solid (61.9 g).

[0064] Synthesis of S4:C 14 EO Sulfate

[0065] All chemical manipulations were performed under a dry nitrogen atmosphere. Prior to the experiment, all glassware was heated in a laboratory oven to remove residual moisture. A 2 L three-necked round bottom flask was charged with dichloromethane (500 mL) and C prepared according to Synthesis S2. 14 EO (50g, 0.193mol, 1.0 equivalent). The reaction flask was equipped with an overhead mechanical stirrer, a charging funnel and a thermocouple. Then, chlorosulfonic acid (14.2mL, 0.213mol, 1.1 equivalents) was carefully loaded into the charging funnel. The reaction flask was then immersed in an ice bath and cooled for 20 minutes to 0°C. After the reaction was cooled, chlorosulfonic acid was added dropwise to the reaction flask at a rate of about 1.0mL / min in about 20 minutes. During the addition of chlorosulfonic acid, the reaction temperature did not exceed 5°C. After addition, the reactants were reacted and the temperature was maintained between 0°C and 5°C for 3 hours. At this point, the reaction was neutralized by slowly adding a NaOH aqueous solution (500mL aqueous solution of 18.0g NaOH, 0.9 moles) dropwise. The addition rate was slow enough not to exceed 5°C during the addition process. After adding about 400mL 0.9 molar NaOH solution, the solution became alkaline. The dichloromethane was then carefully removed from the two phase reaction in vacuo. During the removal of DCM, a large amount of foaming was observed. After the DCM was removed, the remaining aqueous solution was placed in a freeze dryer / lyophilizer to give the secondary alcohol ethoxylate sulfate product (68.6 g).

[0066] Synthetic S5: ALEO1 Sulfate

[0067] ALEO1 sulfate was prepared from ALEO1 in the same manner as described in the synthesis of S3.

[0068] Synthetic S6: SA3EO sulfate

[0069] SA3EO sulfate was prepared from SA3EO in the same manner as described in the synthesis of S3.

[0070] EO distribution of surfactants

[0071] The distribution of EO adducts in the surfactants listed in Table 1 is determined by NMR or UHPLC-MS. The specific method is as follows. The results are shown in Table 1.

[0072] Nuclear Magnetic Resonance (NMR) Characterization of EO Distribution

[0073] The surfactant samples to be tested were prepared by dissolving the surfactant in deuterated dimethyl sulfoxide containing 0.025 M chromium (III) acetylacetonate. The NMR spectra of the samples were then collected using a Bruker AVANCE 400 MHz NMR spectrometer equipped with a 10 mm cryogenic probe (set temperature 25 °C). 13 C NMR) with the following parameters: 90° pulse, anti-gated decoupling, 1.38 sec acquisition time, 6.4 sec recycle delay. 2048 scans were collected. Data were processed in MNOVA with chemical shifts based on the solvent peak at 39.52 ppm. DEPT-135 experiments were also collected with the same parameters, but with a recycle delay of 2.0 sec and 2048 scans. The ratios of different EO adducts were calculated by accumulating and comparing the oxirane alcohol end group intensity of about 60 ppm to 61 ppm, the oxirane main chain group intensity of about 69 ppm to 70 ppm, the oxirane end group ether peak intensity of about 71 ppm to 72 ppm, the unreacted primary alcohol peak intensity of about 60 ppm to 61 ppm, and the unreacted secondary alcohol peak intensity of about 65 ppm to 66 ppm.

[0074] Analysis of Sodium Lauryl Ether Sulfate by UHPLC-MS

[0075] Ultra-high performance liquid chromatography-mass spectrometry (UHPLC-MS) conditions:

[0076]

[0077] step: Compositions containing commercially available surfactants were analyzed using an ultra-high performance liquid chromatography-mass spectrometry (UHPLC-MS) instrument equipped with electrospray ionization (ESI). For analysis, a stock solution with a concentration of 25 ppm was prepared in a 50 / 50 methanol / water mixture. Alcohol ethoxylate samples were diluted 1:100 with 50 / 50 methanol / water (in duplicate) and vortexed for a few seconds. They were then diluted 1:10 in 50 / 50 methanol / water to give a final dilution of 1:1,000. LA-4 was used as a commercially available 1 mol sodium lauryl sulfate standard, and LA-7 was used as a commercially available 3 molar sodium laureth sulfate standard. Calibration standards were prepared in 50 / 50 methanol / water at concentrations of 10 ppm, 5 ppm, 2 ppm, and 1 ppm.

[0078] Alkyl sulfate was diluted from a 1:1,000 preparation with 50 / 50 methanol / water to give a final solution of 1:20,000. BN-5 was used as the standard for alkyl sulfate analysis. Standards were prepared in 50 / 50 methanol / water at concentrations of 5 ppm, 2 ppm, 1 ppm and 0.5 ppm.

[0079] A Waters BEH C18 1.7 μm 1×50 mm column was used. The samples were analyzed by UPLC system. Mass spectrometry analysis was performed using a Waters LCT Premier TOF mass spectrometer equipped with ESI. Measurements were performed in positive and negative ion modes. Each sample preparation solution was injected three times for analysis. The ratios of different EO adducts were calculated by peak area, and the results are recorded in Table 1.

[0080] Table 1

[0081]

[0082] In the products of synthesizing S4 and S5, at least 95 mol% of the oligomers have n ≥ 1, and no more than 5 mol% of the oligomers have n ≥ 2. Specifically, in the products of synthesizing S4 and S5, ≥ 98 mol% of the oligomers have n ≥ 1, and ≤ 2 mol% of the oligomers have n ≥ 2.

[0083] 1,4-Dioxane content of surfactant

[0084] The 1,4-dioxane content of the surfactants listed in Table 2 was measured by liquid injection low-temperature gas chromatography-mass spectrometry (GC-MS) for the organic layer and liquid chromatography-mass spectrometry (LC-MS) for the aqueous layer. The specific method is as follows and the results are shown in Table 2.

[0085] For determination of 1,4-dioxane in organic layer Gas chromatography-mass spectrometry (GC-MS) conditions :

[0086] GC System Agilent 7890GC System Analytical columns DB-1, 30m×0.32mm×5μm Inlet Type Shunt / No Shunt Inlet pressure 10.95psi Total flow rate 17.2mL / min Diaphragm purge flow rate 4mL / min Split Ratio 10:1 Inlet temperature 110℃ Injection volume 1μL Column flow rate 1.2mL / min, constant flow rate GC Column Oven 35℃ for 2.00min, 10℃ / min to 300℃ for 5.00min GC running time 33.50 minutes MS System Agilent 5977A MSD MS parameters model EI Transfer line temperature 250℃ MS Source 230℃ MS Quadrupole 150℃ Acquisition Mode SIM SIM Ion 88.00m / z Holding time 250 Quality range 33m / z-750m / z able 70eV Emission current 34.6mA Solvent delay none

[0087] Standards were prepared by adding a solution of dioxane in tetrahydrofuran ("THF") and diluting to 0.1 ppm to 100 ppm.

[0088] The sample was prepared by mixing 3.3 g of the crude mixture organic (DCM) layer with 6.7 g THF, and then the solution was shaken for about 20 minutes. The solid was then centrifuged to the bottom and the supernatant was placed in an autosampler vial. The spiked samples were prepared by spiking a THF solution of dioxane standards into individual samples at 5 ppm to 10 ppm.

[0089] For the determination of 1,4-dioxane content in the water layer Liquid chromatography-mass spectrometry (LC-MS) conditions :

[0090]

[0091] Samples were injected neat or diluted 1:4 with water. Standards were prepared by preparing a stock solution of dioxane in THF and diluting with water to 0.1 ppm to 100 ppm.

[0092] Calculation of dioxane content relative to solids

[0093] The ppm value of dioxane content relative to the solid content in the sample was calculated according to Equation 1.

[0094]

[0095] Table 2

[0096]

[0097]

[0098] The GC results of the SA3EO sulfate surfactant showed that the secondary alcohol containing an average of 3 moles of ethylene oxide per molecule contained 2 ppm of 1,4-dioxane in the organic phase at 110°C and indicated that materials with n≥2 structures may generate 1,4-dioxane. Interestingly, when the inlet temperature was increased to 280°C, the 1,4-dioxane content of the SA3EO sulfate in the organic phase increased from 2 ppm to 1,471 ppm. This result indicates that sulfated surfactants with n≥2 may produce observable 1,4-dioxane at 110°C and that such surfactants may be unstable at high temperatures of 280°C, resulting in significant 1,4-dioxane generation. Similar to the SA3EO sulfate, the GC results of the ALEO1 sulfate surfactant showed that >9 ppm of 1,4-dioxane was generated relative to the solid at 110°C. In addition, the ALEO1 sulfate surfactant also generated a large amount of 1,4-dioxane (259 ppm) at 280°C, indicating that the ALEO1 sulfate surfactant lacked stability at high temperatures. The present invention C 12 EO sulfate surfactants (≥95 mol % of n is 1 and ≤5 mol % of n≥2) show lower 1,4-dioxane content. 12 The EO sulfate surfactant has a very low 1,4-dioxane content, below the limit of detection (LOD) of the GC and LC methods. Based on the LOD, this indicates that at 110°C, C 12 The dioxane content of EO sulfate is <1.6 ppm. Interestingly, when the inlet temperature is increased to 280°C, the C 12 The 1,4-dioxane content of EO sulfate is still less than 1 ppm (i.e., 0.58 ppm), indicating that compared with the control material, the C 12 EO sulfate has higher thermal stability.

[0099] Comparative Examples CF1-CF5 and Examples F1-F4

[0100] Personal Care Cleansing Preparations

[0101] The personal care cleaning formulations of Comparative Examples CF1-CF5 and Examples F1-F4 as shown in Table 3 were prepared as follows (scale 15 g): anionic surfactant was added first, followed by cocamidopropyl betaine surfactant, and then C 8-14 Alkyl polyglucoside surfactant, then water was added. The formulation was heated to 60°C until completely dissolved. The pH of the formulation was then adjusted to 5.5-6.0 using 10 wt% citric acid prior to testing.

[0102] Table 3

[0103]

[0104] Foam performance

[0105] The foam performance of the personal care cleaning formulations of Comparative Examples CF1-CF5 and Examples F1-F2 was evaluated by loading 50 mL of an aqueous sample of a 3% formulation dilution into a Kruss Dynamic Foam Analyzer Instrument. Foam was generated at a mixing speed of 4,000 rpm for 10 seconds with an oscillation period of 5 seconds. After mixing, the foam height and bubble size were continuously monitored for five minutes. The results of the foam analysis are shown in Table 4.

[0106] Table 4

[0107]

[0108]

[0109] Salt Thickening

[0110] By preparing the diluent of the stock solution preparation on a scale of 700 μL in a 1mL vial, the final preparation is made to contain 10 wt % or 5 wt % of the surfactant active ingredient, and adding 0 wt %, 0.25 wt %, 0.5 wt %, 0.7 wt %, 1 wt % and 1.5 wt % of sodium chloride salt, the salt thickening performance of the personal care cleaning preparations of Comparative Examples CF1-CF5 and Examples F1-F4 is evaluated. After dilution and salt addition, the preparation is mixed by inverting and vortexing the vial until the solution is uniform. The recorded viscosity is obtained by a high-throughput method based on pipetting tip pressure measurement, which utilizes the total aspiration and distribution monitoring (Total Aspiration and Dispense Monitoring, TADM) system function of Hamilton (Hamilton) liquid dispensing robot, and the pressure change generated when the sample is sucked by the tip is measured for viscosity. The details of the method used are shown in ACS Comb.Sci.2016,18,405-414. The results are shown in Table 5.

[0111] Table 5

[0112]

Claims

1. An aqueous personal care rinse-off composition comprising: a dermatologically acceptable aqueous carrier; and Dermatologically acceptable cleansing surfactant, wherein the dermatologically acceptable cleansing surfactant comprises an alcohol ethoxysulfate surfactant of formula I Where R 1 and R 2 Each is independently C 1-16 Alkyl groups; Where R 1 and R 2 The total number of carbon atoms in the molecule is 7 to 17; Among them, M + It is -SO of neutralization formula I 3- anion is a negatively charged cation; and Wherein n is 1 in 95 mol % to 100 mol % of the alcohol ethoxy sulfate surfactant of formula I.

2. The aqueous personal care rinse-off composition of claim 1, wherein the alcohol ethoxysulfate surfactant of formula I contains <9 ppm of 1,4-dioxane.

3. The aqueous personal care rinse-off composition of claim 2, wherein the alcohol ethoxysulfate surfactant of formula I has improved thermal stability (preferably, enhanced thermal stability).

4. The aqueous personal care rinse-off composition according to claim 2, wherein: The aqueous personal care rinse-off composition contains <1 wt % of an alcohol sulfate surfactant of Formula II based on the solids weight of the aqueous personal care rinse-off composition. Where R 3 and R 4 Each independently is C 1-16 Alkyl group; wherein R 3 and R 4 The total number of carbon atoms in the + It is -SO3 in the neutralization formula II - Anions are negatively charged cations.

5. The aqueous personal care rinse-off composition of claim 4, wherein the aqueous personal care rinse-off composition is selected from the group consisting of a shampoo, a conditioning shampoo, a body wash formulation, an exfoliating body wash formulation, a facial cleanser formulation, an exfoliating facial cleanser formulation, and a liquid hand soap formulation.

6. The aqueous personal care rinse-off composition of claim 5, wherein said dermatologically acceptable aqueous carrier comprises water.

7. The aqueous personal care rinse-off composition of claim 6, wherein the dermatologically acceptable cleansing surfactant further comprises an additional surfactant selected from the group consisting of alkyl polyglucosides, alkyl polypentosides, glycinates, betaines, taurates, glutamates, sarcosinates, isethionates, sulfoacetates, alaninates, amphoacetates, sulfonates, sulfates, succinates, sophorolipids, rhamnolipids, and mixtures thereof; and wherein the weight ratio of the alcohol ethoxysulfate surfactant of formula I to the additional surfactant in the aqueous personal care rinse-off composition is from 10:1 to 1:

10.

8. The aqueous personal care rinse-off composition of claim 7 further comprising a thickening salt.

9. The aqueous personal care rinse-off composition of claim 7, wherein the additional surfactant comprises a mixture of betaine and alkyl polyglucoside; wherein the thickening salt is sodium chloride; and wherein the aqueous personal care rinse-off composition comprises from 0.1 wt. % to 20 wt. % of sodium chloride, based on the weight of the aqueous personal care rinse-off composition.

10. A method of cleaning at least one of mammalian skin and hair, the method comprising: (a) applying the aqueous personal care rinse-off composition according to claim 1 to the skin or hair of a mammal; as well as (b) rinsing the aqueous personal care rinse-off composition from the skin or hair with rinse water.