Polyether phosphate compounds, compositions and uses

Abstract

To provide a polyether phosphate ester that does not contain alkylene oxide by-products that may lead to the formation of undesirable by-products or degradation products, and has an improved environmental profile. [Solution] A composition comprising a polyether phosphate ester compound that does not contain alkylene oxide residues, and the following: i) Polyether phosphate esters; ii) Monoalcohol phosphate esters; and iii) A polyether containing at least two terminal C6-C36 hydrocarbyl groups.

Description

Technical Field

[0001] Cross-reference to Related Applications This application claims priority to U.S. Provisional Application No. 63 / 052,126, filed July 15, 2020, entitled "POLYETHER PHOSPHATE ESTER COMPOUNDS, COMPOSITIONS AND USES", the entire content of which is incorporated herein by reference for all purposes.

[0002] Technical Field to which the Invention pertains The present invention relates to compounds that are polyether phosphate esters, compositions comprising said compounds, formulations comprising said compounds or compositions, and uses and methods of said compounds or compositions.

Background Art

[0003] Alkoxylated phosphate esters have long been used as surface active agents (or surfactants) having emulsifying, dispersing, wetting and / or solubilizing properties in a wide range of applications, such as personal care, home care, health care, and many other applications. In particular, alkoxylated phosphate esters have been used as emulsifiers in personal care applications, such as skin care, sunscreens, toiletry products, decorative cosmetics, perfumes and fragrances.

[0004] Polyether phosphate esters are anionic surfactants conventionally produced by reacting alkoxylates such as, for example, ethoxylated alcohols with polyphosphoric acid or phosphorus pentoxide. Ethoxylates are produced through the use of ethylene oxide. Such polyether phosphate esters have been used as surfactants in personal care applications and other applications.

Summary of the Invention

Problem to be Solved by the Invention

[0005] An object of the present invention is to address at least one of the disadvantages associated with the prior art. [Means for solving the problem]

[0006] The present invention is partly based on the recognition that polyether phosphate esters can be produced by using diols or glycols (e.g., propanediol) while avoiding the use of epoxides or alkylene oxides (e.g., ethylene oxide or propylene oxide). Conveniently, the resulting compounds of the present invention do not contain epoxide or alkylene oxide residues because alkylene oxides are not used in the manufacturing process, nor do they contain unreacted residual alkylene oxides and / or alkylene oxide by-products in compositions containing such compounds. Such compounds and compositions are also advantageous in that they can generally be effective surfactants and / or, in particular, emulsifiers. One specific example of an emulsion in which the compounds or compositions of the present invention are advantageous during preparation is a water-in-oil-in-water (W / O / W) emulsion.

[0007] A further advantage of avoiding the use of alkylene oxides in the production of the compounds of the present invention is that the majority of alkylene oxides originate from petrochemical raw materials. Therefore, polyether phosphate esters produced without the use of alkylene oxides can have an improved environmental profile.

[0008] Therefore, in view of the first aspect, the present invention provides a compound that is a polyether phosphate ester and does not contain alkylene oxide residues.

[0009] In a second aspect, the present invention provides a composition comprising the following: i) Polyether phosphate esters; ii) Monoalcohol phosphate esters; and iii) A polyether containing at least two terminal C6-C36 hydrocarbyl groups.

[0010] In a third aspect, the present invention provides an emulsion comprising the compound of the first aspect or the composition of the second aspect.

[0011] In a fourth aspect, the present invention provides a personal care formulation comprising the compound of the first aspect or the composition of the second aspect.

[0012] In a fifth aspect, the present invention provides the use of the compound of the first aspect or the composition of the second aspect as a surfactant.

[0013] Viewed in a sixth aspect, the present invention includes a method for forming an emulsion using a compound of the first aspect or a composition of the second aspect.

[0014] Any or all of the features described herein may be combined in any combination in any aspect of the present invention. [Brief explanation of the drawing]

[0015] [Figure 1] Figure 1 shows a microscopic image of the emulsion formed when mineral oil was emulsified in water using Product 1 (the composition according to the present invention produced in Example 1). [Figure 2] Figure 2 shows the comparative emulsion from Figure 1, which was created using Crodafos CES (a comparative phosphate emulsifier) ​​to emulsify mineral oil in water. [Figure 3] Figure 3 shows the emulsion obtained when isopropyl myristate is emulsified in water using product 1. [Figure 4] Figure 4 shows a comparative emulsion to Figure 3, using Crodafos CES to emulsify isopropyl myristate in water. [Figure 5] Figure 5 shows the emulsion obtained when product 1 is used to emulsify diisopropyl adipate in water. [Figure 6] Figure 6 shows a comparative emulsion to Figure 5, using Crodafos CES to emulsify diisopropyl adipate in water. [Figure 7]Figure 7 shows the size distribution (diameter in μm) of mineral oil particles emulsified in water using Product 1. [Figure 8] Figure 8 shows the size distribution (diameter in μm) of mineral oil particles emulsified in water with Crodafos CES. MODE FOR CARRYING OUT THE INVENTION

[0016] It will be understood that any upper or lower limit of an amount or range used in the present disclosure can be combined independently.

[0017] It will be understood that when describing the number of carbon atoms in a substituent (e.g., "C1~C6"), that number means the total number of carbon atoms present in the substituent, including those present in any branched groups.

[0018] As used in the present disclosure, the term "alkyl" means an aliphatic, unsubstituted, saturated hydrocarbyl group.

[0019] As used in the present disclosure, the term "alkenyl" means an aliphatic, unsubstituted, unsaturated hydrocarbyl group.

[0020] As used in the present disclosure, the term "end-capping" means a terminal group in the product that is non-reactive. For example, when a diol reacts with a single monoalcohol to form a product compound having one terminal hydroxyl group (reactive) and one terminal hydrocarbyl group (non-reactive end-cap), it will be referred to as a "mono-end-capped" compound. When a diol reacts with two monoalcohols to form a product compound having no terminal hydroxyl groups and two terminal hydrocarbyl groups (non-reactive end-caps), it will be referred to as a "fully end-capped" compound.

[0021] As used in this disclosure, the term "residue" refers to a portion of a reactant molecule that remains in the product compound after a reaction has occurred. For example, an alkylene oxide residue is a portion of an alkylene oxide molecule that remains in the compound after an alkylene oxide reaction has occurred.

[0022] Many of the chemicals that can be used to produce the compounds and compositions of the present invention are obtained from natural sources. Such chemicals typically contain mixtures of chemical species due to their natural origin. Due to the presence of such mixtures, the various parameters defined in this disclosure may be mean values ​​and may not be integers.

[0023] The compound-polyether phosphate ester of the present invention The compounds of the present invention are polyether phosphate esters. These polyether phosphate esters do not contain alkylene oxide residues. This ensures that the polyether phosphate esters are not produced using (or obtained from) alkylene oxide reaction products. Preferably, the polyether phosphate esters do not contain alkylene oxide by-products. Preferably, the polyether phosphate esters do not contain epoxide residues. Preferably, the polyether phosphate esters do not contain propylene oxide residues or propylene oxide by-products. Preferably, the polyether phosphate esters do not contain ethylene oxide residues or ethylene oxide by-products.

[0024] The use of alkylene oxide reactants to produce compounds may result in the formation of undesirable by-products or degradation products. For example, dioxanes such as 1,4-dioxane can be undesirable by-products or degradation products in compositions containing compounds produced using ethylene oxide. This is particularly true for phosphate esters produced using alkylene oxides, as the low pH of the resulting compound makes the formation of undesirable by-products or degradation products more likely. Preferably, the compounds of the present invention do not contain dioxanes, and more preferably, they do not contain 1,4-dioxane.

[0025] Polyether phosphate esters can preferably be obtained by phosphorylating polyethers produced by reacting a monoalcohol with a diol to produce a polyether. Preferably, the polyether may be a mixture of several species. Preferably, the polyether is a reaction product of a reactant containing a diol and a monoalcohol.

[0026] The polyether preferably contains at least 3, more preferably at least 4, particularly at least 5, and preferably at least 6 ether bonds. The polyether may contain at most 20, more preferably at most 15, and particularly at most 10 ether bonds. Preferably, the compound contains 3 to 15 ether bonds.

[0027] The monoalcohol reaction product used to produce polyethers may contain at least 6, preferably at least 8, preferably at least 10, and in particular at least 12 carbon atoms. The monoalcohol may contain at most 36 carbon atoms, preferably at most 24, more preferably at most 22, even more preferably at most 20, and in particular at most 18 carbon atoms. Preferably, the monoalcohol contains 12 to 20 carbon atoms. The monoalcohol may be a mixture of at least two monoalcohols. Preferably, the monoalcohol contains a C16 monoalcohol and a C18 monoalcohol.

[0028] The monoalcohol is preferably a primary monoalcohol. The monoalcohol can be linear or branched, and can be saturated or unsaturated. The monoalcohol is preferably linear. The monoalcohol is preferably saturated. The monoalcohol may be a fatty alcohol. The monoalcohol preferably contains a hydrocarbyl group bonded to a hydroxyl group. The monoalcohol preferably contains an alkyl or alkenyl group, particularly an alkyl group, bonded to a hydroxyl group.

[0029] Suitable linear monoalcohols can be selected from the group consisting of hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosal, heneicosal, docosanol, tricosanol, and tetracosal.

[0030] Alternatively, the monoalcohol may be a branched, preferably saturated, alcohol. Preferred branched monoalcohols include isopalmityl alcohol and / or isostearyl alcohol. The branched monoalcohol may also be a Guerbet alcohol, i.e., an alcohol formed by the Guerbet reaction. The Guerbet reaction is an organic reaction that converts a primary aliphatic alcohol into its β-alkylated dimer alcohol, in which 1 equivalent of water is lost. Preferred Guerbet alcohols include hexyldecyl alcohol, octyldecyl alcohol, and octyldodecyl alcohol.

[0031] The diol reactant used to produce the polyether may contain at least two carbon atoms, preferably at least three carbon atoms. The diol may contain at most 22 carbon atoms, preferably at most 12, more preferably at most 10, and even more preferably at most 6 carbon atoms. Preferably, the diol contains 2 to 6 carbon atoms, more preferably 3 or 4 carbon atoms, and especially preferably 3 carbon atoms.

[0032] The diol can be primary or secondary. Preferably, the diol is primary. Preferably, the diol contains two primary hydroxyl groups. The diol may be linear, branched, or cyclic. Preferably, the diol is linear or branched, and more preferably linear.

[0033] The diol is preferably a linear diol containing three carbon atoms. The diol is preferably a propanediol, more preferably 1,3-propanediol, and especially a non-epoxide 1,3-propanediol. The non-epoxide 1,3-propanediol can conveniently be derived from renewable resources. Since 1,3-propanediol has two primary hydroxyl groups, the polyether products produced using it are preferably linear and may be more flexible and have lower viscosity than polyethers produced using 1,2-propanediol.

[0034] In contrast, 1,2-propanediols have secondary hydroxyl terminal groups, are branched, and are derived from the reactive epoxide propylene oxide (alkylene oxide).

[0035] The diol can be a mixture of at least two diols. The diol may contain branched species in amounts of less than 20% by mass (wt%), preferably less than 15 wt%, more preferably less than 10 wt%, even more preferably less than 5 wt%, and particularly less than 1 wt%, based on the total amount of diol reactants used. The diol may contain 1,2-propanediol in amounts of less than 20 wt%, preferably less than 15 wt%, more preferably less than 10 wt%, even more preferably less than 5 wt%, and particularly less than 1 wt%, based on the total amount of diol reactants used. Preferably, the diol does not contain 1,2-propanediol. Preferably, the diol does not contain ethanediol.

[0036] The molar ratio of the diol reactant to the monoalcohol reactant used to produce the polyether can be at least 2:1, preferably at least 3:1, and more preferably at least 4:1. The molar ratio of the diol reactant to the monoalcohol reactant used to produce the polyether can be at most 20:1, preferably at most 15:1, more preferably at most 12:1, and particularly at most 10:1. Preferably, the molar ratio of the diol reactant to the monoalcohol reactant used to produce the polyether is 2:1 to 20:1, preferably 3:1 to 12:1, and particularly 4:1 to 10:1.

[0037] The monoalcohol used to produce the polyether reacts to provide at least one terminal hydrocarbyl group (or "end cap") in the polyether. The terminal hydrocarbyl group may have any of the characteristics of the monoalcohol described herein. Preferably, the terminal hydrocarbyl group is a C6-C36, preferably C8-C22 hydrocarbyl group. Preferably, the hydrocarbyl group is an alkyl group or an alkenyl group, and more particularly an alkyl group. Preferably, the monoalcohol provides only one terminal hydrocarbyl group ("single end cap") in the polyether.

[0038] A catalyst can be used in the reaction of a monoalcohol and a diol to produce a polyether. The catalyst can be selected from suitable strong acid catalysts. The catalyst can be a monoprotonic acid. The catalyst may also be an organic acid. Preferably, the catalyst is a sulfonic acid. Preferably, the catalyst is selected from sulfuric acid and trifluic acid (trifluoromethanesulfonic acid / TFMS). Preferably, the catalyst is trifluoromethanesulfonic acid.

[0039] The polyether may consist of a mixture of species having at least one free hydroxyl group and species not having a free hydroxyl group. Some of these polyether species may contain two terminal hydrocarbyl groups, resulting in polyethers without free hydroxyl groups. Such polyether species are sometimes called "fully capped" materials and may not participate in subsequent phosphorylation reactions.

[0040] Preferably, the polyether mixture is then phosphorylated to produce the polyether phosphate ester of the present invention. Preferably, the polyether phosphate ester can be obtained by reacting a polyether with a phosphoric acid, preferably phosphorus pentoxide.

[0041] The polyether phosphate ester preferably contains at least one terminal C6-C36, preferably C8-C22 hydrocarbyl group. The terminal hydrocarbyl group may have any of the characteristics of the monoalcohols described herein. The hydrocarbyl group is preferably an alkyl group or an alkenyl group. Preferably, the polyether phosphate ester does not contain a carboxylic acid ester bond.

[0042] The polyether phosphate ester may contain monoesters (containing one phosphate ester group) and diesters (containing two phosphate ester groups). Preferably, the amount of monoester is at least 10%, more preferably at least 25%, and particularly at least 50% of the total mass of the phosphate ester. Preferably, the amount of monoester is at most 90%, more preferably at most 75%, and particularly at most 50% of the total mass of the phosphate ester. Preferably, the amount of diester is at least 10%, more preferably at least 25%, and particularly at least 50% of the total mass of the phosphate ester. Preferably, the amount of diester is at most 90%, more preferably at most 75%, and particularly at most 50% of the total mass of the phosphate ester.

[0043] The composition of the present invention includes the following: i) Polyether phosphate ester. ii) Monoalcohol phosphate esters; and iii) A polyether containing at least two terminal C6-C36 hydrocarbyl groups.

[0044] For example, dioxanes such as 1,4-dioxane can be undesirable by-products or decomposition products in compositions containing compounds produced using ethylene oxide. The compositions of the present invention are conveniently dioxane-free. Conveniently, the compositions of the present invention are produced without the use of ethylene oxide. The compositions may contain undetectable amounts of dioxane. Preferably, the compositions contain less than 1 ppm of dioxane, more preferably less than 0.5 ppm of dioxane, even more preferably less than 100 ppb of dioxane, particularly less than 10 ppb of dioxane, and particularly less than 1 ppb of dioxane. The compositions of the present invention are preferably free of alkylene oxide by-products or decomposition products.

[0045] Preferably, the polyether phosphate ester is a compound according to a first aspect of the present invention. The polyether phosphate ester may contain any of the features described in this disclosure with respect to the compound of the present invention. The polyether phosphate ester can preferably be obtained by phosphorylating a polyether produced by reacting a monoalcohol with a diol to produce a polyether. The polyether may be a mixture of several species.

[0046] The polyether phosphate ester may consist of a monoester (containing one phosphate ester group) and a diester (containing two phosphate ester groups). Preferably, the amount of monoester in the composition is at least 10%, more preferably at least 25%, and particularly at least 50% of the total mass of phosphate esters in the composition. Preferably, the amount of monoester in the composition is at most 90%, more preferably at most 75%, and particularly at most 50% of the total mass of phosphate esters in the composition. Preferably, the amount of diester in the composition is at least 10%, more preferably at least 25%, and particularly at least 50% of the total mass of phosphate esters in the composition. Preferably, the amount of diester in the composition is at most 90%, more preferably at most 75%, and particularly at most 50% of the total mass of phosphate esters in the composition.

[0047] Monoalcohol phosphate esters can preferably be obtained by reacting a monoalcohol with a phosphorus oxide, preferably phosphorus pentoxide. The monoalcohol may contain at most 36 carbon atoms, preferably at most 24 carbon atoms, more preferably at most 22, even more preferably at most 20, and especially at most 18 carbon atoms. Preferably, the monoalcohol contains 12 to 18 carbon atoms. The monoalcohol may be a mixture of at least two monoalcohols. Preferably, the monoalcohol contains C16 and C18 monoalcohols. The monoalcohol is preferably a primary monoalcohol. The monoalcohol can be linear or branched, and saturated or unsaturated. The monoalcohol is preferably linear. The monoalcohol is preferably saturated. The monoalcohol may be a fatty alcohol. The monoalcohol preferably contains a hydrocarbyl group bonded to a hydroxyl group. The monoalcohol preferably contains an alkyl or alkenyl group bonded to a hydroxyl group, especially an alkyl group.

[0048] The polyether contains at least two terminal C6-C36 hydrocarbyl groups. Preferably, the hydrocarbyl groups are alkyl or alkenyl groups. Preferably, the polyether does not have free hydroxyl groups, and in particular, the polyether is a fully terminal-capped polyether. The polyether preferably contains at least three ether bonds, more preferably at least four, particularly at least five, and preferably at least six ether bonds. The polyether may contain at most 20, more preferably at most 15, and particularly at most 10 ether bonds. The polyether can preferably be obtained by reacting a monoalcohol with a diol. The monoalcohol may have any of the characteristics of a monoalcohol described herein. The diol may have any of the characteristics of a diol described herein.

[0049] Preferably, the amount of polyether phosphate ester in the composition is at least 20 wt%, more preferably at least 30 wt%, particularly at least 40 wt%, and preferably at least 50 wt%, based on the total mass of the composition. Preferably, the amount of polyether phosphate ester in the composition is at most 90 wt%, more preferably at most 75 wt%, and particularly at most 60 wt%.

[0050] Preferably, the amount of monoalcohol phosphate ester in the composition is at least 10 wt%, more preferably at least 20 wt%, and particularly at least 30 wt%, based on the total mass of the composition. Preferably, the amount of polyether phosphate ester in the composition is at most 90 wt%, more preferably at most 75 wt%, and particularly at most 50 wt%.

[0051] Preferably, the amount of polyether in the composition is at least 2 wt%, more preferably at least 5 wt%, and particularly at least 10 wt%, based on the total mass of the composition. Preferably, the amount of the second polyether in the composition is at most 20 wt%, more preferably at most 15 wt%, and particularly at most 10 wt%.

[0052] Preferably, the mass ratio of polyether phosphate ester to monoalcohol phosphate ester in the composition is at least 1.2:1, more preferably at least 1.5:1. This mass ratio can be up to 10:1, preferably up to 8:1.

[0053] Preferably, the mass ratio of polyether phosphate ester to polyether in the composition is at least 2:1, more preferably at least 3:1, and particularly at least 4:1. This mass ratio can be up to 20:1, and preferably up to 15:1.

[0054] The composition may further include the following: iv) Unreacted monoalcohol.

[0055] While not strictly theoretical, including unreacted monoalcohols in a composition can advantageously improve its processing properties, such as melting point and / or viscosity. Preferably, including unreacted monoalcohols in a composition lowers its melting point. Preferably, including unreacted monoalcohols in a composition lowers its kinematic viscosity at 25°C.

[0056] A monoalcohol may contain at least 6 carbon atoms, preferably at least 8, preferably at least 10, and particularly at least 12 carbon atoms. A monoalcohol may consist of at most 36 carbon atoms, preferably at most 24, more preferably at most 22, even more preferably at most 20, and particularly at most 18. Preferably, a monoalcohol contains 12 to 18 carbon atoms. A monoalcohol may be a mixture of at least two types of monoalcohols. Preferably, a monoalcohol contains a C16 monoalcohol and a C18 monoalcohol. A monoalcohol is preferably a primary monoalcohol. A monoalcohol can be linear or branched, and can be saturated or unsaturated. A monoalcohol is preferably linear. A monoalcohol is preferably saturated. A monoalcohol can be a fatty alcohol.

[0057] Preferably, the amount of unreacted monoalcohol in the composition is at least 10 wt%, more preferably at least 25 wt%, and particularly at least 40 wt%, based on the total mass of the composition. Preferably, the amount of monoalcohol in the composition is at most 90 wt%, more preferably at most 75 wt%, and particularly at most 50 wt%.

[0058] The compositions of the present invention can be used as surfactants, emulsifiers, dispersants, stabilizers, solubilizers, pigment wetting agents, viscosity stabilizers, and / or rheology modifiers. The present invention also includes the use of the compositions as surfactants, emulsifiers, dispersants, stabilizers, solubilizers, pigment wetting agents, viscosity stabilizers, and / or rheology modifiers, preferably as surfactants and / or emulsifiers, and more preferably as emulsifiers.

[0059] Emulsion The emulsion according to the present invention comprises the compound or composition of the present invention.

[0060] The compounds or compositions of the present invention are suitable for use in the production of emulsions (and dispersions), i.e., as emulsifiers or as part of an emulsifier system. The emulsion may be a water-in-oil (W / O) emulsion, an oil-in-polyol (e.g., glycerol) emulsion, or an oil-in-water (O / W) emulsion. The emulsion may be a multiple emulsion, for example, a water-in-oil-in-water (W / O / W) emulsion. Preferably, the emulsion is a W / O / W emulsion.

[0061] The emulsion may contain a dispersed phase having a D(v,0.1) particle size of less than 20 μm, preferably less than 15 μm. The D(v,0.1) value is the equivalent spherical diameter of 10% (on a volume basis) of the total particles being smaller than that value. Preferably, the particle size is measured by laser light scattering, as particularly described in this disclosure.

[0062] The emulsion is preferably intended for use in personal care formulations, more preferably in skincare, haircare, hair coloring, sunscreens, cosmetics, antiperspirants, or dermatological products, particularly in skincare, haircare, hair coloring, sunscreen, or antiperspirant products.

[0063] The oil phase of the emulsion preferably contains an emollient oil of the type used in personal care formulations. The emollient is preferably an oily material that is liquid at ambient temperature (i.e., about 23°C). Alternatively, the emollient may be solid at ambient temperature, in which case it is usually a waxy solid in bulk, provided that it is liquid at high temperatures so that it can be emulsified when included in the composition.

[0064] The oil phase of the emulsion may contain one or more of the following: mineral oil, paraffin oil, ester oil, vegetable oil, silicone oil, alcohol, or silicone.

[0065] Suitable oil phase components include nonpolar oils, such as mineral oil or paraffin, especially isoparaffin, oils, such as those sold by Croda as Arlamol® HD; or medium polar oils, such as vegetable ester oils, such as jojoba oil, vegetable glyceride oils, animal glyceride oils, such as those sold by Croda as Crodamol® GTCC (caprylic / capric triglyceride); synthetic oils, such as synthetic ester oils, such as isopropyl palmitate and those sold by Croda as Crodamol IPP and Arlamol DOA; ether oils, especially those having two fatty residues, such as C8-C18 alkyl residues, such as those sold by Croda as Arlamol LFE (dicapryl ether); Guerbet alcohols, such as those sold by Cognis as Eutanol G (octyldodecanol); or silicone oils, such as dimethicone oil, such as those sold by Dow Corning as Xiameter Examples of suitable materials include cyclomethicone oil, such as that sold as PMX-200, or silicones having polyoxyalkylene side chains that improve their own hydrophilicity; or highly polar oils containing alkoxylate emollients, such as fatty alcohol propoxylates, such as those sold by Croda as Arlamol PS15E (propoxylated stearyl alcohol). Suitable emollient materials that are solid at ambient temperature but liquid at the temperatures typically used in the production of the formulations of the present invention include jojoba wax, animal fat, and coconut wax / oil.

[0066] Mixtures of multiple emollients can and often be used, and in some cases, solid emollients may be completely or partially dissolved in liquid emollients, or in combination, the freezing point of the mixture may be appropriately low. When the emollient composition is solid at ambient temperature (e.g., fatty alcohols), the resulting dispersion may not be technically an emulsion (in most cases, the exact phase of the oily dispersion cannot be easily determined), but such dispersion behaves as if it were a true emulsion, and the term emulsion is used in this disclosure to include such compositions.

[0067] The concentration of the oil phase can take on a wide range of values. The amount of oil in the emulsion is preferably in the range of 1 to 90% by mass of the total composition, preferably 3 to 60% by mass, more preferably 5 to 40% by mass, particularly 8 to 20% by mass, and especially 10 to 15% by mass.

[0068] The concentration of the aqueous phase (e.g., water or polyol, e.g., glycerin) present in the emulsion is preferably higher than 5% by mass of the total composition, preferably 30-90% by mass, more preferably 50-90% by mass, particularly 70-85% by mass, and especially 75-80% by mass.

[0069] The amount of the composition of the present invention in the emulsion or personal care formulation according to the present invention may be at least 0.1% by mass, preferably at least 0.5% by mass, and more preferably at least 1% by mass of the total formulation.

[0070] The amount of the composition of the present invention in the emulsion or personal care formulation according to the present invention can be at most 20% by mass, preferably at most 15% by mass, more preferably at most 10% by mass, particularly preferably at most 6% by mass, and especially preferably at most 5.5% by mass of the total formulation.

[0071] The amount of the composition of the present invention in the emulsion or personal care formulation according to the present invention is preferably in the range of 0.1 to 10%, preferably 0.5 to 8%, more preferably 1 to 7%, particularly 1 to 6%, and especially 1 to 5.5%, relative to the total mass of the formulation.

[0072] The emulsion according to the present invention may also contain other additional surfactant materials that form part of the emulsifier system. Other suitable surfactants include relatively hydrophilic surfactants, for example, those having an HLB value greater than 10, preferably greater than 12, and relatively hydrophobic surfactants, for example, those having an HLB value less than 10, preferably less than 8. Relatively hydrophilic surfactants include alkoxylate surfactants having an average of about 10 to about 100 alkylene oxides, particularly ethylene oxide residues, and relatively hydrophobic surfactants preferably include alkoxylate surfactants having an average of about 3 to about 10 alkylene oxides, particularly ethylene oxide residues.

[0073] The personal care formulation according to the present invention preferably has a low shear viscosity of 10,000 mPa·s or less (approximately 0.1 to 10 s, as typically used by Brookfield viscometers). -1 The products can be divided into milks and lotions having a shear viscosity (measured at a shear rate of 100 mPa·s), and creams having a low shear viscosity, preferably exceeding 10,000 mPa·s. The milks and lotions preferably have a low shear viscosity in the range of 100 to 10,000 mPa·s, more preferably 200 to 5,000 mPa·s, and particularly 300 to 1,000 mPa·s. The amount of the composition according to the present invention present in the milk or lotion is preferably in the range of 0.5 to 3% by mass of the total composition.

[0074] The cream preferably has a low shear viscosity in the range of at least 20,000 mPa·s, more preferably 30,000 to 80,000 mPa·s, and particularly 40,000 to 70,000 mPa·s, but even higher viscosities, for example up to about 10 6Those up to mPa·s can also be used. The amount of the composition according to the present invention in the cream is preferably in the range of 1 to 5% by mass of the total composition.

[0075] The emulsion of the present invention can generally be produced by conventional emulsification and mixing methods. For example, the composition of the present invention can be (i) added to an oil phase, and then the aqueous phase can be added to the oil phase; or the composition of the present invention can be (ii) added to both the combined oil and aqueous phases; or the composition of the present invention can be (iii) added to an aqueous phase, and then the aqueous phase can be added to the oil phase. Method (i) is preferred. In all of these methods, the resulting mixture can then be emulsified using standard techniques. It is preferable to heat the aqueous and oil phases to more than about 60°C, for example, about 80-85°C, or to subject the aqueous phase to high-intensity mixing at a lower temperature, for example, approximately ambient temperature (cold process). If desired, a combination of vigorous mixing and the use of moderately high temperatures can be used. Heating and / or high-intensity mixing can be carried out before, during, or after the addition of water to the oil phase.

[0076] The emulsion can also be produced by inversion emulsification, in which the composition of the present invention is added to either the oil phase or the aqueous phase, and the aqueous phase is mixed with the oil phase to initially form a water-in-oil emulsion. The addition of the aqueous phase is continued until the system is inverted and an oil-in-water emulsion is formed. In short, since a considerable amount of aqueous phase is generally required for inversion, this method would not be used for emulsions with a high oil phase content. If desired, vigorous mixing and the use of moderately high temperatures can be combined. Heating can be performed during or after the addition of the aqueous phase, and before, during, or after inversion. High-intensity mixing can be performed during or after the addition of the aqueous phase, and before or during inversion.

[0077] The emulsion can be, for example, a microemulsion or nanoemulsion having an average droplet size in a wide range, preferably in the range of 10 to 10,000 nm. In one embodiment, the emulsion droplet size can be reduced, for example, by high-pressure homogenization, to a value preferably in the range of 100 to 1,000 nm, more preferably in the range of 300 to 600 nm.

[0078] The emulsion according to the present invention is stable at room temperature (i.e., about 20°C) for preferably more than one month, more preferably more than two months, and particularly more than three months. Stability at higher temperatures may be particularly important, and therefore the emulsion is stable at 50°C for preferably more than one week, preferably more than two weeks, more preferably more than three weeks, and particularly more than one month.

[0079] Personal care formulations The personal care formulation according to the present invention comprises the compound or composition of the present invention.

[0080] Many other ingredients can be included in a formulation to manufacture a personal care or cosmetic formulation or product. These ingredients may be oil-soluble, water-soluble, or water-insoluble. Examples of such materials include: (i) Preservatives based on potassium sorbate, sodium benzoate, parabens (alkyl esters of 4-hydroxybenzoic acid), phenoxyethanol, substituted ureas, and hydantoin derivatives, such as those commercially available under the trade names Germaben II Nipaguard BPX and Nipaguard DMDMH. Such preservatives are preferably used at a concentration in the range of 0.5 to 2% by mass of the total composition. Preservative boosters, such as caprylyl glycol or ethylhexylglycerin, may also be used. (ii) Fragrances, if used, preferably in a concentration of 0.1 to 10% by mass of the total composition, more preferably about 5% by mass or less, and particularly about 2% by mass or less. (iii) If used, humectants or solvents, such as alcohols, polyols, such as glycerol and polyethylene glycol, are preferably used in a concentration of 1 to 10% by mass of the total composition. (iv) Sun filters or sunscreen materials containing organic sunscreens and / or inorganic sunscreens such as those based on titanium dioxide or zinc oxide, if used, preferably in a concentration of 0.1 to 20% by mass, more preferably 1 to 15% by mass, and particularly 2 to 10% by mass of the total composition. (v) Alpha hydroxy acids, such as glycolic acid, citric acid, lactic acid, malic acid, tartaric acid and their esters; self-tanning agents, such as dihydroxyacetone. (vi) Antimicrobial agents, especially anti-acne components, such as salicylic acid. (vii) Vitamins and their precursors, such as (a) vitamin A, for example, as retinyl palmitate and other tretinoin precursor molecules; (b) vitamin B, for example, as panthenol and its derivatives; (c) vitamin C, for example, ascorbic acid and its derivatives; (d) vitamin E, for example, as tocopheryl acetate; and (e) vitamin F, for example, as a polyunsaturated fatty acid ester such as gamma-linolenic acid ester. (viii) as a skincare agent, for example, as a natural material or a functional mimic of natural ceramides, such as ceramides. (ix) Phospholipids, such as synthetic phospholipids or natural phospholipids, such as lecithin. (x) Formulations containing vesicles. (xi) Germanium-containing compound. (xii) Plant extracts with beneficial skincare properties. (xiii) Whitening agents, such as kojic acid, arbutin and similar materials, including Arlatone Dioic DCA (trademark) sold by Croda. (xiv) Skin repair compound active substances, such as allantoin and similar series. (xv) Caffeine and similar compounds. (xvi) Cooling additives, such as menthol or camphor. (xvii) Insect repellents, such as N,N-diethyl-3-methylbenzamide (DEET), and citrus oil or eucalyptus oil. (xviii) Essential oils. (xix) Ethanol. (xx) Particle pigments, especially oxides and silicates, such as iron oxide, especially coated iron oxide, and / or titanium dioxide, and pigments in ceramic materials, such as boron nitride. (xxi) Other solid components, for example, solid components used in makeup and cosmetics to give a suspension emulsion, preferably in an amount ranging from 1 to 15 wt%, more preferably 5 to 15 wt%, based on the total mass of the formulation; and (xxii) Deodorant or antiperspirant compound.

[0081] The compositions and emulsions according to the present invention are suitable for use in a wide range of personal care formulations and end-use applications, including moisturizers, sunscreens, after-sun products, body butters, gel creams, highly fragranced products, perfume creams, baby care products, hair treatments, hair colorants, shampoos, hair conditioners, skin tone and skin whitening products, water-free products, antiperspirants and deodorants, sunscreens, cleansers, 2-in-1 foam emulsions, multi-emulsions, preservative-free products, mild formulations, scrub formulations (e.g., scrub formulations containing solid beads), silicone-in-water formulations, pigment-containing products, sprayable emulsions, cosmetics, color cosmetics, conditioners, shower products, foaming emulsions, makeup removers, eye makeup removers, and wipes.

[0082] The formulation may be a spray, lotion, cream, or ointment. If the formulation is a color cosmetic, it may be a foundation, mascara, eyeshadow, or lipstick. The formulation may be an antiperspirant or deodorant. Preferably, the formulation is a sunscreen.

[0083] The formulation may further include a sun filter or sunscreen material, preferably a UV filter. The sun filter or sunscreen material can be selected from organic sunscreens and inorganic sunscreens, preferably from inorganic sunscreens. The sun filter or sunscreen material may be selected from titanium dioxide and zinc oxide. The compounds or compositions of the present invention can advantageously improve the SPF of sunscreen formulations, as shown in the examples.

[0084] A composition or emulsion containing the present invention can have a wide range of pH values, preferably in the range of 3 to 13, more preferably 4 to 10, and particularly 5 to 8.

[0085] Uses other than personal care The compounds or compositions of the present invention can have uses other than personal care.

[0086] Pharmaceuticals or therapeutic formulations may contain the compounds or compositions of the present invention.

[0087] The hard surface cleaner may contain the compound or composition of the present invention. The hard surface cleaner may also be an alkaline cleaner, an oven cleaner, or a floor cleaner / stripper.

[0088] The laundry detergent may contain the compound or composition of the present invention. The laundry detergent may be a spray-drying laundry detergent, a powder-based laundry detergent, or a liquid laundry detergent.

[0089] The formulation for textile or leather processing may contain the compound or composition of the present invention.

[0090] Rinse aid formulations for automatic tableware and glass washing systems may contain the compounds or compositions of the present invention.

[0091] The pesticide formulation may contain the compounds or compositions of the present invention. For example, many agricultural additives, such as herbicides, are required in aqueous solutions for application to leaves. The compounds and compositions of the present invention can enable emulsification and / or solubilization of additives in water, along with good wetting properties to ensure optimal spread on the leaf surface.

[0092] Oilfield chemicals or well drilling formulations may contain the compounds or compositions of the present invention.

[0093] The emulsion polymerization system may contain the compound or composition of the present invention.

[0094] The emulsion explosive system may contain the compound or composition of the present invention.

[0095] Use as a surfactant / emulsifier In a further aspect, the present invention provides the use of the compounds or compositions of the present invention as surfactants. The compounds or compositions of the present invention can be used as emulsifiers.

[0096] The compounds or compositions of the present invention can be used as emulsifiers in the production of water-in-oil (W / O / W) emulsions, preferably in a method comprising a single emulsification step. The compounds or compositions of the present invention can be used as the sole emulsifier in the production of water-in-oil (W / O / W) emulsions.

[0097] Preferably, the present invention provides the use of the compounds or compositions of the present invention for reducing the D(v,0.1) particle size of an emulsion. The compounds or compositions of the present invention can be used to prepare an emulsion having a dispersed phase having a D(v,0.1) particle size of less than 20 μm, preferably less than 15 μm. Preferably, the emulsion is a personal care formulation. Preferably, the particle size is measured by laser light scattering, particularly as described in this disclosure.

[0098] Method for forming an emulsion In a further aspect, the present invention provides a method for forming the following emulsion. a) Compound or composition of the present invention. b) Phase 1 component; and c) Second phase component These can be combined in any order, including simultaneously.

[0099] For example, the compound or composition of the present invention may be (i) added to the oil phase, and then the aqueous phase may be added to the oil phase; or the compound or composition of the present invention may be (ii) added to both the combined oil and aqueous phases; or the compound or composition of the present invention may be (iii) added to the aqueous phase, and then the aqueous phase may be added to the oil phase. Method (i) is preferred. In all of these methods, the resulting mixture can then be emulsified using standard techniques. It is preferable to heat the aqueous and oil phases to typically above about 60°C, for example, about 80-85°C, or to subject the aqueous phase to a lower temperature, for example, approximately ambient temperature, with high-intensity mixing (cold process). If desired, a combination of vigorous mixing and the use of moderately high temperatures may be used. Heating and / or high-intensity mixing may be performed before, during, or after the addition of water to the oil phase.

[0100] The emulsion can also be produced by inversion emulsification, in which the composition of the present invention is added to either the oil phase or the aqueous phase, and the aqueous phase is mixed with the oil phase to initially form a water-in-oil emulsion. The addition of the aqueous phase is continued until the system is inverted and an oil-in-water emulsion is formed. In short, since a considerable amount of aqueous phase is generally required for inversion, this method would not be used for emulsions with a high oil phase content. If desired, vigorous mixing and the use of moderately high temperatures can be combined. Heating can be performed during or after the addition of the aqueous phase, and before, during, or after inversion. High-intensity mixing can be performed during or after the addition of the aqueous phase, and before or during inversion.

[0101] Preferably, the emulsion is a water-in-oil-in-water (W / O / W) emulsion.

[0102] Any or all of the features described herein can be combined in any combination in any aspect of the present invention. [Examples]

[0103] Examples The present invention is illustrated by the following non-limiting embodiments. All parts and percentages are given by mass unless otherwise specified. All tests and physical properties in this disclosure were determined at atmospheric pressure and room temperature (i.e., about 20°C) unless otherwise specified in this disclosure or in the test methods and procedures referenced.

[0104] Test method The following test methods were used in this disclosure. (i) The hydroxyl value was defined as the number of mg of potassium hydroxide equivalent to the hydroxyl value of 1 g of sample, and was measured by hydrolysis of excess acetic anhydride after acetylation. The resulting acetic acid was then titrated with potassium hydroxide ethanol solution.

[0105] (ii) NMR analysis was performed using a Bruker instrument and TopSpin 3.2 processing software. 1H, 13C, and 31P NMR spectra (400 MHz) were obtained in deuterated acetone at 55°C.

[0106] (iii) The microscopic images shown in Figures 1 to 6 were taken using a Dino-Lite Edge 700-900x 5MP digital microscope. Emulsions were prepared under the same conditions (i.e., mixing rate and time). Microscopic images were taken at 933x magnification 24 hours after emulsion preparation.

[0107] (iv) The particle size distributions shown in Figures 7 and 8 were prepared using a Horiba LA-960 laser light scattering particle size analyzer. The measurement method is as follows: - For each sample, two predispersions were prepared in deionized water. - The preliminary dispersion was gently mixed by inversion. - Measurements were taken for three aliquots of each preliminary dispersion. - To minimize potential bubble formation, the circulator was turned off during the measurement.

[0108] (v) The in vitro SPF results for Example 6 were obtained using Labsphere UV-2000S, solar light (16S-300-009s), and PMMA plate. The measurement method was as follows: • 0.03 g of the mixture was applied to the rough surface of a PMMA plate by lightly tapping it over the entire surface. The mixture was then spread horizontally back and forth in a circular motion to ensure a uniform coating. Next, the treated plate was placed in a dark drawer and allowed to dry for 15 minutes. After 15 minutes, initial SPF measurements were obtained, and the plate was then placed under a solar simulator and exposed for a time calculated to correspond to 4 MED exposure. • Five readings were performed per plate, and the procedure was carried out on three plates for each product, following a rule requiring 15 data points.

[0109] (vi) The results of the activator delivery performance in Example 7 were vertical This was produced using a diffusion cell system (Perme Gear) known as a Franz cell and a water bath circulator. The measurement method is as follows: Each Franz cell was filled with phosphate-buffered saline (PBS; pH 7.4). A small stirring rod was added to equilibrate the buffer solution. • To avoid air bubbles, the Strat-M membrane was immersed in PBS buffer placed in a receptor chamber several hours before the test. • The donor compartment was clamped to the receiver compartment. Approximately 1 ml of the formulation was applied to the donor compartment. Samples were collected at various time intervals: 4 hours, 8 hours, and 24 hours after the start of the experiment. • Samples were analyzed at wavelengths of 200–400 nm using a Cary UV-Vis 60, and the mass percentage of the transferred active substance (caffeine) was measured.

[0110] Example 1 A mixed C16 / C18 fatty monoalcohol (Crodacol 1618 from Croda) was reacted with 1,3-propanediol in a molar ratio of 1:8 using trifluic acid as a catalyst. The mixture was stirred and heated to approximately 180°C for several hours until the hydroxyl value was in the range of 60-90 mgKOH / g to produce a polyether intermediate. This intermediate material is a mixture of a hydroxyl-functionalized polyether and a fully capped polyether (i.e., a fully capped polyether contains two terminal C16 / C18 hydrocarbyl groups and does not have a free hydroxyl group). This intermediate material was then neutralized and filtered. This intermediate material was placed in a reactor with an equal mass of mixed C16 / C18 monoalcohol and reacted with phosphorus pentoxide.

[0111] After the phosphorylation reaction was complete, the resulting active product contained i) a polyether phosphate ester, ii) a monoalcohol phosphate ester, and iii) a terminally capped polyether. This active product was blended with a mixed C16 / C18 monoalcohol to obtain a final product containing 25 wt% monoalcohol and 75 wt% active product. This final product composition according to the present invention will be referred to as Product 1.

[0112] Example 2 451.75 g of 1,3-propanediol was placed in a glass reaction vessel equipped with a stirrer, thermometer, condenser, and nitrogen spag. At a temperature of 60-70°C, 198.25 g of C16 / C18 mixed fatty alcohol and 1.30 g of trifluoromethanesulfonic acid were placed in the glass reaction vessel. This batch was reacted at 150-180°C until it was indicated that 1 mole of 1,3-propanediol with a hydroxyl value of 5 moles had reacted with 1 mole of mixed C16 / C18 fatty alcohol. 245.52 g of the resulting polyether preparation and 245.52 g of mixed C16 / C18 fatty alcohol were placed in a glass reaction vessel equipped with a stirrer, thermometer, condenser, and nitrogen spag. The temperature of the vessel was raised to 70°C. 58.86 g of phosphorus pentoxide was added to the vessel over 2 hours. The mixture was stirred for 4 hours. This final product composition according to the present invention will be referred to as Product 2.

[0113] Example 3 Two samples of the active product from Example 1 (i.e., the active product described before the final blending step with the mixed C16 / C18 monoalcohol to form product 1) were analyzed using NMR as described in the test method above to determine the distribution of component species in the samples. The results of the NMR analysis are shown in Table 1.

[0114] [Table 1]

[0115] The distribution in Table 1 was calculated using the ideal molecular weight of the components. Both monophosphate and diphosphate components include polyether phosphates and monoalcohol phosphates. These polyether species include single-terminated and fully-terminated polyethers. Fully-terminated polyethers are understood to be present in the range of approximately 6–10 wt%.

[0116] Example 4 To demonstrate the improved emulsifying properties of Product 1 in Example 1, an oil-in-water emulsion was prepared using Product 1 and compared with a comparative phosphate ester emulsifier, Crodafos CES (INCI: cetearyl alcohol and dicetyl phosphate and ceteth-10 phosphate), available from Croda. Crodafos CES is a polyether phosphate ester produced using ceteth-10, which is obtained by reacting cetyl alcohol with 10 moles of ethylene oxide. Therefore, Crodafos CES contains alkylene oxide residues. Microscopic images shown in Figures 1 to 6 were generated using a Dino-Lite Edge 700-900x 5MP digital microscope as described in the test method above. From these images, the particle size of oil micelles produced by each emulsifier for nonpolar, medium-polar, and highly polar oils can be compared. The specific formulations used are shown in Tables 2, 3, and 4. The formulations used to prepare each emulsion were adjusted to use 1 wt% of the active product (from Product 1 or Crodafos CES) in each formulation.

[0117] [Table 2]

[0118] [Table 3]

[0119] [Table 4]

[0120] Emulsion formulation procedure: Heat the components of Part A in the main beaker to 75°C while mixing at 360 rpm with a propeller blade. Heat the components of Part B in a separate beaker to 75°C. Once both phases have reached the temperature, add Part B to Part A. Mix at the temperature for 5 minutes, then cool. When the temperature reaches approximately 46°C, switch to a side-sweep blade and reduce the mixing speed to 30 rpm. Add Part C at 40°C. Adjust the pH to between 5 and 6 with a 10% NaOH solution. All emulsions were prepared on the same day using the above procedure.

[0121] The microscopic images shown in Figures 1 to 6 were taken as described in the test method above. By comparing the emulsions shown in Figure 1 (using Product 1) and Figure 2 (Crodafos CES), it can be seen that for the mineral oil in water (non-polar oil) type emulsion shown in Table 2, Product 1 produced much smaller and more densely packed oil micelle particles than Crodafos CES. On the other hand, the micelles produced by Crodafos CES were not very uniform in size, and the emulsion appeared to contain more air bubbles. As can be seen from Figure 3 (Product 1) and Figure 4 (Crodafos CES), in the isopropyl myristate in water (medium-polar oil) type emulsion, Product 1 produced densely packed oil micelle particles with small particle sizes visible to the naked eye. The emulsion containing Crodafos CES had many air bubbles and heterogeneous particles, and it was found that the particles were scattered and not cohesive. As can be seen from Figures 5 (Product 1) and 6 (Crodafos CES), in the diisopropyl adipate (highly polar oil) emulsion in water, Product 1 produced densely packed oil micelle particles, albeit with slight variations in size. Crodafos CES produced large, scattered particles that were not uniform. Therefore, from Figures 1 to 6, it can be seen that Product 1 produces an emulsion with visually smaller and more uniform particle sizes than Crodafos CES. While not bound by theory, this can advantageously improve the stability or homogeneity of the emulsion.

[0122] The particle size distribution of mineral oil droplets (nonpolar oil) in the emulsion formulations shown in Table 2 was also measured as described in the test method above, and the results are shown in Figure 7 (Product 1) and Figure 8 (Crodafos CES). There is a large difference in the shape of the distribution peaks on the left side (smaller side). In Figure 7, Product 1 shows that a considerable amount of particles with a diameter of less than 10 μm were produced in the emulsion, whereas in Figure 8, no particles with a diameter of less than 10 μm were detected. This is reflected in the D(v,0.1) value calculated for the distributions in Figures 7 and 8. The D(v,0.1) value is the equivalent spherical diameter at which 10% of all particles (volume basis) are below this value. The D(v,0.1) value is 11.2 μm for Product 1 and 26.9 μm for Crodafos CES, indicating that Product 1 produces more small particles in the emulsion. This is supported by comparing the images in Figure 1 and Figure 2.

[0123] Example 5 The following formulations are presented to illustrate different ways in which Product 1 can be used.

[0124] [Table 5]

[0125] procedure: Measure and mix water and 25% sodium hydroxide solution into the main beaker. Prepare a slurry by combining glycerin and xanthan gum in a measuring boat and add it to the water. Heat Part A to 75°C while mixing. Combine the components of Part B in a separate beaker and heat to 75°C. When both have reached 75°C, add Part B to Part A and mix for 10 minutes. Cool to 40°C and add Part C. Adjust the pH to 6-6.5 as needed.

[0126] [Table 6]

[0127] procedure: Add water, AHA, citric acid, and sodium citrate to the main beaker and mix until all are completely dissolved and homogeneous. Prepare a slurry by combining glycerin, Zemea, and xanthan gum and add it to the acid mixture. Add the remaining components and heat to 70°C. Combine the components of Part B in a separate beaker, heat to 70°C, and mix. Add Part B to Part A while mixing, and mix for 10 minutes while maintaining the temperature. Begin cooling to 55-60°C using a propeller blade, and switch to a side sweep at 60°C. Cool to 40°C and add Part C. Check the pH and ensure it is between 3.5 and 4.0.

[0128] [Table 7]

[0129] procedure: Combine the components of Part A and heat to 75-80°C while mixing in an overhead mixer. Heat Part B to 75°C in a separate beaker. Add Part B to Part A and mix at 75°C for 10 minutes, or until homogenized. Combine the components of Part C in a separate beaker and heat to 75°C while mixing. Add Part C to Part A / B and homogenize for 3-5 minutes, or until uniform. Cool the batch to 45°C using a side sweep and add Part D. Continue mixing the batch until it cools to room temperature.

[0130] [Table 8]

[0131] procedure Combine the components of Part A and heat to 75-80°C while mixing in an overhead mixer. Heat Part B to 75°C in a separate beaker. Add Part B to Part A and mix at 75°C for 10 minutes, or until homogenized. Combine the components of Part C in a separate beaker and heat to 75°C while mixing. Add Part C to Parts A / B and homogenize for 3-5 minutes, or until uniform. Cool the batch to 45°C and add Part D. Continue mixing until the batch cools to room temperature.

[0132] [Table 9]

[0133] procedure: Add water to the main beaker, add NaOH solution to adjust the pH to 4, and heat Part A to 75°C. Combine the components of Part B and heat to 75°C or dissolve completely. Add Part B to Part A and continue mixing at a low to medium speed while cooling. Check the pH and adjust it if necessary.

[0134] [Table 10]

[0135] procedure: Combine the first five components of Part B, heat to 80-85°C, and mix moderately until everything is dissolved. Add the dye intermediate and mix for 20 minutes until completely dissolved. Heat Part A to 80-85°C in a separate beaker and mix. Add Part A to Part B and mix for 20 minutes. Cool to 40°C before adding Part D, and continue mixing for another 10 minutes.

[0136] [Table 11]

[0137] procedure: Heat the water in the main container, add the next two components of Part A, and mix moderately until completely dissolved. Continue mixing, adding the remaining components of Part A one after another, and heat to 70-75°C. Mix for 10 minutes, then cool to 40°C. Add Part B and mix for 15 minutes. Adjust the pH to 2.5-3.5.

[0138] [Table 12]

[0139] procedure: Combine the components of Part A and heat to 80-85°C. Add the first two components of Part B. Once dissolved, add the remaining components of Part B all at once. Stir until uniform and cool to 60-65°C. Maintain this temperature, add Part C, and mix well. Cool to 55°C while stirring, then pour into the mold.

[0140] [Table 13]

[0141] procedure: Combine the components of Part C and weigh out 210% increased mass of each component. Mix thoroughly, then pass through a three-roller mill three times on setting 3 (loosest setting). Combine the components of Part B and heat to 70°C while mixing. Add Part C to Part B while mixing. For Part A, add aluminum magnesium silicate to water and heat to 70°C while mixing. Prepare a slurry by combining glycerin and xanthan gum, then add it to Part A. When the temperature reaches 70°C, add Solaveil XT-40W to Part A. Maintain the temperature and mix until homogenized. Add Part B / C to Part A while stirring vigorously and stir for 5 minutes. Place the batch under a homogenizer and mill for 3 minutes. Cool to 45°C while stirring. Adjust the pH to 4.10 with lactic acid while stirring, and add the preservatives sodium benzoate (and potassium sorbate) (Part D). Add Venuceane (Part E) and mix until uniform.

[0142] [Table 14]

[0143] procedure: Premix xanthan gum, veegum ultra, and glycerin. Add water and EDTA while stirring, and heat to 70-75°C. Combine all components of Part B except Solaveil XT-300 and heat to 70-75°C. Add Solaveil XT-300 to Part B while stirring, and reheat to 70-75°C. Add Part B to Part A while stirring, and homogenize for 2 minutes. Cool to 40°C using a side-sweep blade, and add Part C. Adjust pH as needed.

[0144] Example 6 The SPF (Sun Protection Factor) performance of Product 1 in Example 1 was compared with that of Crodafos CES, which is available from Croda. The in vitro SPF performance of inorganic sunscreen formulations containing Product 1 or Crodafos CES was tested as described in the test method above. Formulations A and B shown in Table 15 were prepared to use 1 wt% of the active product (from Product 1 or Crodafos CES) in each formulation.

[0145] [Table 15]

[0146] Formulations A and B in Table 15 were tested for in vitro SPF performance as described in the test method above. The results are shown in Table 16.

[0147] [Table 16]

[0148] Table 16 shows that product 1 in formulation A resulted in a significant improvement (higher value) in in vitro SPF performance compared to Crodafos CES in the corresponding formulation B. This improvement was observed in two batches of formulation A, both before and after UV exposure.

[0149] Example 7 Product 1 of Example 1 was compared to a known combination of emulsifiers available from Crodafos CES and Croda (Arlacel 2121 and Cithrol DPHS) to improve the delivery and / or transfer of caffeine, an active skincare component, from the formulation to the skin. The delivery of the activator was tested as described in the test method. Formulations A, B, and C shown in Table 17 were prepared to contain 1 wt% of the active product in each formulation.

[0150] [Table 17]

[0151] For formulations A, B, and C in Table 17, the activator delivery performance was tested as described in the test method. The results are shown in Table 18.

[0152] [Table 18]

[0153] Table 18 shows that product 1 in formulation A resulted in an improvement in the amount of active ingredient (caffeine) transferred compared to both formulations B and C.

[0154] It will be understood that the present invention is not limited to the details of the embodiments described above, which are merely illustrative. Many modifications are possible.

Claims

1. A polyether phosphate ester compound that does not contain alkylene oxide residues.

2. The compound according to claim 1, comprising at least one terminal C6-C36 hydrocarbyl group, preferably a terminal C8-C22 hydrocarbyl group.

3. The compound according to claim 2, wherein the hydrocarbyl group is an alkyl or alkenyl group.

4. A compound according to any one of claims 1 to 3, having 3 to 15 ether bonds.

5. A compound according to any one of claims 1 to 4 that does not have a carboxylic acid ester bond.

6. A compound according to any one of claims 1 to 5, obtained by reacting a polyether with a phosphorus oxide, preferably phosphorus pentoxide.

7. The compound according to claim 6, wherein the polyether is a reaction product of a reaction product containing a diol and a monoalcohol.

8. The compound according to claim 7, wherein the diol contains 2 to 6 carbon atoms.

9. The compound according to claim 7 or 8, wherein the monoalcohol contains 12 to 20 carbon atoms.

10. The compound according to any one of claims 7 to 9, wherein the molar ratio of the diol to the monoalcohol is 2:1 to 20:1, preferably 3:1 to 12:1, and particularly 4:1 to 10:

1.

11. i) Polyether phosphate esters; ii) Monoalcohol phosphate esters; and iii) Polyethers containing at least two terminal C6-C36 hydrocarbyl groups; A composition containing the following:

12. The composition according to claim 11, wherein the hydrocarbyl group of the polyether is an alkyl or alkenyl group.

13. The composition according to claim 11 or 12, wherein the polyether phosphate ester is a compound according to any one of claims 1 to 10.

14. The composition according to any one of claims 11 to 13, wherein the amount of the polyether phosphate ester in the composition is at least 20% by mass based on the total mass of the composition.

15. The composition according to any one of claims 11 to 14, wherein the amount of the monoalcohol phosphate ester in the composition is at least 10% by mass based on the total mass of the composition.

16. The composition according to any one of claims 11 to 15, wherein the amount of polyether containing at least two terminal C6-C36 hydrocarbyl groups in the composition is at least 2% by mass based on the total mass of the composition.

17. An emulsion comprising the compound according to any one of claims 1 to 10 or the composition according to any one of claims 11 to 16.

18. A personal care formulation comprising the compound described in any one of claims 1 to 10 or the composition described in any one of claims 11 to 16.

19. Furthermore, the personal care formulation according to claim 18, further comprising a sun filter or sunscreen material.

20. Use of the compound according to any one of claims 1 to 10 or the composition according to any one of claims 11 to 16 as a surfactant.

21. Use of a compound according to any one of claims 1 to 10 or a composition according to any one of claims 11 to 16 to reduce the D(v,0.1) particle size of the emulsion, preferably as measured as described in this disclosure.

22. A method for forming an emulsion, a) The compound according to any one of claims 1 to 10 or the composition according to any one of claims 11 to 16; b) Phase 1 component; and c) second phase component; A method in which these are combined in any order, including simultaneously.

23. The method according to claim 22, wherein the emulsion is an oil-in-water-in-water (W / O / W) type emulsion.

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