TW200831523A - Saccharide esters and their use as surfactant - Google Patents

Abstract

A new class of saccharide esters is disclosed consisting of saccharide esters of polyhydroxyalkanoic acids and polyhydroxyalkenoic acids, saccharide esters of hydroxy-alkanoyloxy-and polyhydroxyalkanoyloxy-substituted alkyl carbamic acids, and saccharide esters of hydroxyalkenoyl-oxy-and polyhydroxyalkenoyloxy-substituted alkenyl carbamic acids, their preparation and surface-active properties. Also disclosed are the use of the esters as surfactant, typically as emulsifier/emulsion stabiliser and as dispersant/suspension stabiliser, as well as compositions, in particular emulsions and suspensions, comprising esters of the invention. Preferred esters are composed of a saccharide moiety derived from inulin or dextrin and a polyhydroxyalkanoyl moiety derived from a poly-12-hydroxy-stearic acid (PHS-acid). The saccharide esters are particularly suitable for the preparation of stable W/O emulsions, preferably in the presence of small amounts of an electrolyte.

Description

200831523 IX. INSTRUCTIONS OF THE INVENTION [Technical Field] The present invention relates to a polyhydroxyalkanoic acid and a polyhydroxy enoic acid sugar ester, an alkylamino carboxylic acid substituted with a hydroxyalkyl alkoxy group and a polyhydroxyalkyl alkoxy group. Sugar esters, sugar esters of alkenyl amino acid substituted with hydroxy olefinoxy group and polyhydroxy olefin oxy group, preparation method thereof, use thereof as a surfactant, dispersion containing the same application. [Prior Art] A composition comprising two or more phases, in particular a two-phase and three-phase composition composed of an aqueous phase and an oil phase, or a solid phase consisting of an aqueous phase and/or an oil phase and a particulate form (or The composition of the composition is more or less finely divided. It is technically and economically important because it may have the desired overall properties that result from the use of each phase. Furthermore, the importance of two-phase and three-phase compositions is that they can have oil or an oily component that is partially replaced by an aqueous phase, which will produce satisfactory effects and opportunities (eg, improved personal care and cosmetic products) Sensory properties, such as a more pleasant skin feel) and it is possible to replace oil or oily liquids with more readily available, more environmentally friendly and/or less expensive aqueous phases. In order to obtain as much as possible the technical properties and benefits provided by the phases, the compositions are thoroughly stirred (usually homogenized) before they are made into a dispersion (usually an emulsion or suspension). However, the two phases are tilted apart due to the immiscibility of the oil phase with the aqueous phase, so the emulsion is generally unstable in gravity analysis. Similarly, the suspension is generally unstable in gravity analysis because the fine particles will be highly inclined to sink or float depending on their density. The poor gravitational stability of the emulsions and suspensions is quite disadvantageous, which is very limited in its technical application. Previously, compounds that improved the miscibility of aqueous and oil phases (known as surfactants) have been found to improve the contact between wet and water or oil phases (wetability) or to improve fines in water or oil. Dispersibility in the phase. Emulsions and suspensions with industrially acceptable gravity stability can be made from the availability of effective surfactants and different emulsions and suspensions can be used in a variety of applications. When two-phase and multi-phase compositions (usually in the form of a final blend suitable for a particular application) do not phase separate at the end of the preset storage period (such as coalescence, creaming, sedimentation or flotation) ), which is considered to have an industrially acceptable gravity stability (also referred to herein as acceptable stability or stability). Such stability allows pre-manufactured emulsions and suspensions to provide the same technically advantageous properties as those exhibited by freshly prepared compositions, making the manufacture, storage, sale, sale and use of previously prepared emulsions and suspensions feasible. Typically, the dispersed composition of the oil phase and the aqueous phase is presented as a water-in-oil emulsion (herein W/0 emulsion) or an oil-in-water emulsion (herein 0/w emulsion). Effective emulsifiers for the preparation of o/w emulsions have long been available. Therefore, stable 0/W emulsions are known in the art and are currently widely used in various technical applications. However, stable W/0 emulsions are more difficult to achieve 'due to the dispersion of water droplets -6 - 200831523 degrees tend to coalesce and separate. Emulsifiers have been available for the past two decades that can be used to make W/0 emulsions with acceptable stability, so W/0 emulsions are increasingly being used in different applications. However, although the w/0 emulsion has satisfactory properties, the current w/〇 emulsion is used much less than the 0/w emulsion, in part because of the w/0 emulsion compared to the 0/w emulsion. The stability is quite limited. In particular, w/0 emulsions with high aqueous phase/oil ratios are still difficult to prepare or exhibit poor gravitational stability. This makes φ such w/o emulsions less attractive and very limited in their use. . In the early W/0 blends, conventional surfactants such as oleic acid glyceride or isostearate are used in addition to the use of large amounts of wax or hydrogenated castor oil to achieve acceptable stability. Improved emulsifiers have been available since then, and polymeric esters are currently widely used as emulsifiers in W/0 blends, such as polyethylene glycol esters of polyhydroxyalkanoic acids. A typical emulsifier of this type is polyethylene glycol (PEG)-30 dipolyhydroxystearate, for example: Arlacel P1 35 (trade name, available from ICI). • Early W/0 blends presented the disadvantage of requiring large amounts of hydrazine or hydrogenated oil to achieve acceptable stability. However, for safety and/or environmental reasons, recent W/0 blends using PEG-derived emulsifiers have been compared. unwelcome. Therefore, PEG-free emulsifiers have become popular and many remedies have elicited such emulsifiers. These efforts have produced a class of effective PEG-free emulsifiers, ie, polyglycerol esters of oligomeric alkanoic acids, such as: polyglycol polyhydroxystearate, for example: polyglycerol-2 dimer hydroxy hard The fatty acid ester (trade name DEHYMULS® PGPH, available from Henkel KGaA, Germany). 200831523 Recently, W/Ο Ο 硏 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常 通常Viscosity and/or poor biodegradability. Conventional W/0 blends for personal care and cosmetics often suffer from poor dispersibility and viscous or oily skin feel. Furthermore, stable suspensions (especially hydrophilic fines in the oil phase or suspensions of hydrophobic fine particles in the aqueous phase) are generally not readily prepared or still poor, although different surfactants can be obtained. Stability. Thus, the search for surfactants that can be used to make stable suspensions, especially high load suspensions, continues to be searched. Considering the possibility of different applications, we are inconvenient for replacement or modification of two-phase and multi-phase compositions and for the manufacture of such two-phase and multi-phase compositions without any known composition or surfactant Sexual or shortcoming surfactants, including emulsifiers for w/o emulsions and dispersants for suspensions, are still needed. SUMMARY OF THE INVENTION It is an object of the present invention to provide alternative and/or improved surfactants and methods of making the same. Another object of the present invention is to provide a process for preparing stable two-phase and multi-phase dispersions using the surfactant. Another object is to provide stable two-phase and multi-phase dispersions (usually emulsions and suspensions, especially w/o emulsions) which are present in this form or when used in industrial, household, personal care, beauty Or the final blend of pharmaceutical applications can remain stable. Still another object of the present invention is to provide a surfactant -8-200831523 and a composition containing the surfactant which do not have one or more of the inconveniences or disadvantages of the conventional surfactant and the composition. The above and other objects are attained by the present invention in the light of the details and the scope of the claims. [Embodiment] According to a preferred system, the present invention provides a novel class of sugar esters having interfacial activity properties including emulsification, emulsion stabilization, wetting, dispersion, and/or suspension stability. The sugar esters according to the present invention are sugar esters of alkyl aminocarboxylic acid substituted by a polyhydroxyalkanoic acid and a polyhydroxy enoic acid sugar ester, a hydroxyalkyl alkoxy group and a polyhydroxyalkyl alkoxy group. A class of sugar esters of alkenylaminocarboxylic acid substituted with a hydroxyalkenyloxy group and a polyhydroxyalkenyloxy group. In the sugar ester, the term sugar refers to a cyclic monosaccharide or a chain composed of 2 to 100 cyclic monosaccharide units. In a preferred system, the sugar esters according to the present invention are as follows: (i) a sugar ester of a polyhydroxyalkanoic acid which is covalently linked to a sugar (Sac) moiety of a polyhydroxyalkane moiety Composition, (ii) a polyhydroxy enoic acid sugar ester consisting of a sugar (Sac) moiety covalently linked to a polyhydroxy olefinic moiety, and (iii) a hydroxyalkyl alkoxy- or polyhydroxyalkane a sugar ester of an oxy-substituted alkylaminocarboxylic acid, which is composed of a sugar (Sac) moiety covalently linked to an alkylamine carbonyl moiety substituted with a hydroxyalkyl alkoxy group or a polyhydroxyalkyl alkoxy group, -9 - 200831523 wherein the sugar (Sac) moiety is a hydrogen moiety derived from one or more monohydroxy units of one or more monosaccharide units consisting of 2 to 1 ring monosaccharide units of cyclic monosaccharide units. Substituting the polyhydroxyalkylene moiety and the polyhydroxy olefin oxime with a polycondensed hydroxyalkanoic acid having 6 to 24 carbon atoms and a polycondensed hydroxyenoic acid of the atom and wherein the substituted alkane alkylamine carbonyl group and The substituted hydroxyalkyl alkoxy group or polyhydroxy group is derived from the same hydroxyalkanoic acid having 6 to 24 carbon atoms. In a more preferred system, the sugar esters according to the invention have a structure corresponding to formula I, ie

Sac-(B)s (I) wherein #Sac represents a sugar moiety which is one or more of one or more monosaccharide units consisting of a chain of 2 to 100 cyclic monosaccharide units consisting of a cyclic monosaccharide unit. Substituted by hydrogen of a hydroxyl group; B (also referred to herein as a PHS moiety) represents a sugar or a sugar formed by a poly-12-hydroxystearin group of the formula 0, wherein the atom is separated by the other The alkyl alkoxy group derived from a 6 to 24 carbon amine carbonyl moiety, respectively, is characterized in that it has a sugar or a sugar formed therein, wherein the atom is B moiety-10-200831523

Wherein P represents an integer 1 or a number of oximes in the range of 1 to 10, and when p represents an integer 1, R represents a hydrogen atom or a 12-hydroxystearone group ' or when P represents 1 to 10 The average degree of polycondensation in the range '-0-(R)p represents a polyhydroxystearthoxy group; or φ (Π) of the formula 111 1 1-(12-hydroxystearyloxy)-heptadecane Amino-carbonyl group or 11-(poly-12-hydroxystearyloxy)-heptadecaneamine carbonyl group,

Wherein P represents an integer 1 or a number of enthalpies in the range of 丨 to 10' and wherein when P represents an integer 1, R represents a chlorine atom, or when P represents an average degree of polycondensation in the range of 1 to 10 , -〇-(R)p represents a poly-12-hydroxystearyloxy group; and s (representing the degree of substitution, that is, the average number of B groups per sugar unit) is 〇.〇1 To the range of 1.00. The sugar (sac) moiety of the ester according to the invention is derived from a sugar consisting of a cyclic monosaccharide unit or a sugar consisting of a chain of 2 to 10 annular monosaccharide units, wherein one or more The hydrogen atom of one or more of the monosaccharide units is replaced by the other moiety, which is a monosaccharide, or a disaccharide, an oligosaccharide or a polysaccharide, which are respectively composed of the same or different monosaccharide units and any mixtures thereof - 11 - 200831523 Composition. The term oligosaccharide (also referred to herein) refers to a (poly)saccharide consisting of a chain comprising from 2 to 9 units. Further, in the present text, oligosaccharides and polysaccharides refer to polydisperse and monodisperse sugars. The esters according to the invention or the invention and the derivatives according to the invention or of the invention, and the esters of the formula I and the derivatives of the formula I are used interchangeably. φ In a preferred system, the sugar (Sac) moiety contains only fructose units and/or glucose units. In another preferred embodiment, the invention relates to a derivative of formula I, wherein the Sac moiety is derived from fructose, glucose, sucrose, difructose, plant-derived or synthetically derived oligofructose, or polyfructose, preferably from a plant The source of polyfructose, more preferably a plant-derived inulin (which is a polyfructose composed of linear or branched fructose units, possibly with a terminal glucose unit, having a total of 2 to 100 sugar units), Most preferably, the chicory inulin (which is composed of a polyfructose chain having from 2 to about 70 fructose units, possibly with a terminal glucose unit), or derived from any mixture thereof. In this context, the terms polyfructose and inulin also include oligofructose, i.e., (poly)saccharides having from 2 to 9 saccharide units, which are composed of polyfructose chains which may carry a terminal glucose unit. \ Further, the words sugar unit, fructose unit, and glucose unit used to represent the components of disaccharides, oligosaccharides, and polysaccharides (such as polyfructose, inulin, oligofructose, and maltodextrin) are usually used. Also) can be exchanged with fructosyl units and glucosyl units. -12- 200831523 Inulin and oligofructose (both of which are well known in the art) are D-polyfructose products consisting of a fructose-based chain, most or all of which are via the β(2·1) bond to each other. Linked and it may or may not have terminal glucose groups. Inulin and oligofructose may be represented by the formula GFn or Fm, wherein G represents a glucosyl unit, F represents a fructosyl unit, and η and m are integers representing the number of fructose units in the carbohydrate chain. The total number of sugar units in a molecule is called the degree of polymerization and is represented by DP. The product is usually also defined using the parameter (number) - average degree of polymerization (usually in average DPn, average DP or and representative). Inulin is naturally derived from bacteria and plants. In general, plant-derived inulin is a polydisperse mixture of linear and/or slightly branched polysaccharide chains, the DP of which is predominantly in the range of from 2 to about 100, depending on the plant variety. In the industrial scale, inulin is mainly prepared from plant sources, i.e., from the roots of Cichorium intybus, tubers of Helianthus tuberosus, and agave. Inulin can be readily extracted from the plant, purified and selectively fractionated to remove impurities, mono- and disaccharides, and possibly oligosaccharides, according to known techniques, to provide different industrial grade inulin. Inulin from chicory is polydisperse and is linear or slightly (4-5%) branched, DP is usually in the range of 2 to about 70, and commercially available products of various industrial grades, including, for example, Beneo® ST (average DP is 10 to 13 and contains up to 8% by weight of glucose, fructose and sucrose), Beneo® LS (average DP is 10 to 13 and contains less than 1% by weight of glucose, fructose and sucrose) and Beneo ® HP (average DP 23 to 27, usually about 25, containing up to 0.5% glucose 'fructose and sucrose and most -13 - 3,315,315, 5% more DP to 3 to 9 oligofructose) (drying with all carbohydrates) The substance is the basis weight of the calculation) (Beneo8, the trade name of the inulin product available from Belgium ORAFTI). Inulin with a lower degree of polymerization (defined as DP in the range of 2 to 9) is often referred to alternately as oligofructose, fruit-oligosaccharide or chrysanthemum-oligosaccharide. The oligofructose is prepared on an industrial scale according to known techniques, such as partially hydrolyzed inulin and synthesized from sucrose by enzymatic synthesis in a glass tube. • Several industrial grade oligofructose obtained by partial hydrolysis of chicory inulin are available from ORAFTI, Belgium, for example: Beneo8P95, which contains a minimum of 93% by weight of oligofructose (DP in the range of 2 to 9 and average DP) About 4) and all up to 7% by weight of glucose, fructose and sucrose. The fruit-oligosaccharide (FOS) obtained from sucrose by enzymatic synthesis is, for example, ACTILIGHT® 950P (including > 95% DP in the range of 3 to 5) purchased from B0ghin-Meiji Industries (France) Oligo-fructose). The agave inulin is composed of a polyfructose chain, about 15% of which is • branched and may have a terminal glucose unit, such as: Industrias Colibri Azul SA in Mexico, with an average DP of Approximately 14 to 16 GAVEDIET® PR product versions are available. All of these grades of inulin and oligofructose, and any mixtures thereof (also including > industrial grade products) are suitable for use in the preparation of the sugar esters of the present invention.

In another preferred embodiment, the invention is directed to sugar esters, particularly esters of formula I, wherein the sugar (Sac) moiety is derived from glucose, sucrose, lactose, maltose, starch hydrolysate or any mixture thereof. In another preferred embodiment, the starch hydrolysate is comprised of a molecule comprising a glycosyl unit of D-Port 14-200831523, the D-glycosyl unit by 〇t-1,4 glucosyl-glucose The base bonds are linked to each other, thereby forming a straight chain structure, or are linked to each other by a ^-1,4 and α_1,6 glucosyl-polysaccharide bond, thereby forming an α -1,6-glucoin at a branching point. A branched structure of a glycosyl-glucosyl bond, or consists of any mixture thereof. The plant powder, which is a stored carbohydrate form of a natural plant, is separated by industrial specifications from the plant or plant part of the polydisperse mixture which produces polydextrose molecules whose degree of polymerization (DP) may vary greatly. The bond between the glycosyl units is sensitive to hydrolysis and heat, which is used industrially to make different powder hydrolysates, which cover products consisting mainly of glucose, including what is called glucose syrup. The product is known as a product of maltodextrin or dextrin. Starch hydrolysates are well known in the art and exhibit a reducing power generated primarily from the D-glucosyl unit of the molecular terminal. Traditionally, this reducing power is expressed in dextrose equivalent (DE値), which provides an indication of the degree of hydrolysis of the starch and an indication of the average degree of polymerization of the starch hydrolysate molecules. Therefore, starch hydrolysates are usually defined by DE値. The DE system suitable for use in the starch hydrolysate of the present invention is in the range of from 1 to 100 (DE = 100 for D-glucose), which corresponds to a chain length of from 100 to 1. Preferably, the starch hydrolysate has a DE in the range of from 1 to less than 20, and another preferred starch hydrolysate has a DE of from 20 to 100, more preferably from 20 to 98. Hydrolysates having a DE of 20 or higher are commonly referred to as glucose syrups. A DE less than 20 is commonly known as dextrin. The dextrin herein is not limited to the hydrolysate of corn starch (sometimes also referred to as maltodextrin), but refers to the starch hydrolysate obtained from starch of any source having a DE of less than 20. Starch Code -15- 200831523 Sources include corn, rice, tapioca, sorghum, wheat and potatoes. Starch hydrolysates (including glucagon, syrup, and dextrin) are well known in the art and are commercially available from various suppliers. All of the starch hydrolysates, even these industrial grade starch hydrolysates and any mixtures thereof, are suitable for use in the preparation of the sugar esters of the present invention. In an excellent system, the sugar (Sac) moiety of the ester of formula I is derived from chicory inulin with an average DP of 20 to 30 (such as Beneo® HP) or chicory inulin with an average DP of 9 to 14. Such as Beneo® ST), or oligofructose derived from chicory inulin (such as Bene〇® P95, DP is mainly in the 2 to 8' average DP is about 4) (Beneo Zheng, the trade name of Belgium ORAFTI). In another preferred embodiment, the sugar moiety of the ester of formula I is derived from a syrup having a DE of from 20 to 98 (more preferably from 20 to 47 DE). In another preferred embodiment, the sugar moiety of formula I is derived from a dextrin having a DE of from 1 to less than 20. In this context, the term PHS moiety (i.e., part B of formula I) represents a poly-1 2-hydroxystearic acid group according to the above formula, i.e., corresponding to what is conventionally referred to as polyhydroxystearic acid (usually Also known as the alkyl group of PHS-acids, which is obtained by polycondensation of 12-hydroxystearic acid, the degree of polycondensation (this is the number of 12-hydroxystearic acid units per PHS molecule) In the range of 2 to 12, it corresponds to the average 値 of 値 in the formula II or Ρ in the range of 1 to 1 。. In this context, the term PHS moiety (i.e., the moiety in formula I) also represents 11-(12-hydroxystearyloxy)-heptadecaneaminecarbonyl or 11-(poly-12) according to formula III above. -Hydroxystearyloxy)-heptadecanecarbonylcarbonyl group. The substituted heptadecylamine carbonyl group of the formula 111 -16· 200831523 is a group derived from a PHS-acid, which is obtained by converting its free carboxyl group to an isocyanate group and then converting it into an alkylamine carbonyl group, for example. : In the process for producing an ester of the formula I, it is obtained by reacting with a sugar. The degree of polycondensation of a substituted alkylamine carbonyl group of the formula (which is also considered to be a 12-hydroxystearic acid unit) substantially corresponds to the degree of polycondensation of the PHS-acid source and is in the range of 2 to 12. Inside (this corresponds to the average 値 of 1 in the formula III). In a preferred system, the PHS moiety of Formula II and Formula III is derived from an average degree of polycondensation in the range of 5 to 9 (which corresponds to an average enthalpy of 3 to 7 in Formula II and Formula III). The PHS acid was dispersed with an average degree of condensation of 7 (which corresponds to an average enthalpy of 5 in Formula II and Formula III). PHS·acids are known and are typically present in the form of polydisperse polycondensates. For example, a PHS-acid with an average degree of polycondensation of 7 can be purchased from the UK ICI-Uniqema by Hypermer LP1. Other polyhydroxyalkanoic acids other than PHS-acid are also suitable for use in providing the polyhydroxyalkylguanidine moiety of the sugar esters of the present invention or the alkylamine carbonyl moiety substituted with a hydroxyalkyloxy- or polyhydroxyalkyloxy group. Similar to the PHS-acid, it can be obtained from a suitable hydroxyalkanoic acid by polycondensation according to conventional techniques. The degree of substitution of the sugar moiety of the derivative of the formula I of the present invention (represented by the number in the formula I. 値s) corresponds to the average number of the B moiety (PHS moiety) of each sugar unit of the sugar moiety Sac and the number thereof is 〇· It is in the range of 〇1 to 1.00 (preferably in the range of 0.02 to 0.5, more preferably in the range of 0.02 to 0.25). Traditionally, the degree of substitution was determined by NMR spectroscopy. -17- 200831523 In another preferred embodiment, the invention relates to a process for the manufacture of a sugar ester according to the invention, in particular an ester of the formula I as defined above. When the sugar ester is prepared, when the sugar moiety is linked to the polyhydroxyalkylguanidine moiety or the polyhydroxyalkylene moiety, it can be prepared by a conventional method for esterifying/deuterated sugars, when the sugar moiety is linked. When an alkylamine carbonyl moiety substituted with a hydroxyalkyl alkoxy group and a polyhydroxyalkyl alkoxy group or an enamine carbonyl moiety substituted with a hydroxyalkenyloxy group and a polyhydroxyalkenyloxy group can be used for the amine Preparation of Φ carbamic acid sugar by a conventional method. A exemplified description of the sugar derivative of the formula I, wherein the sugar moiety of the present invention in which the sugar moiety is attached to the polyhydroxyalkylguanidine moiety can be obtained by the method for preparing the corresponding polyhydroxyalkane benzotriazole. The designated sugar in an inert solvent is then esterified using it as a deuterating agent to produce the desired sugar ester of the polyhydroxyalkanoic acid. Method for preparing polyhydroxyalkane benzotriazole of formula IV • The preparation method described is as a preparation of PHS-acid poly-12-hydroxystearic acid (Hypermer® LPl from ICI, UK) having an average degree of polycondensation of 7. - an instance of the Uniqema item). Traditionally, the PHS-acid is converted to the benzotriazole of the formula IV, that is, poly-12-hydroxystearin benzotriazole (PHS-Bt), <this is usually 1 equivalent of PHS-acid and 4 equivalents of benzotriazole and 1 when the amount of thiopurine chloride is reacted in dry methylene chloride at room temperature in a humidity-free environment. -18- 200831523

The resulting reaction mixture is poured into a suitable dry, non-polar solvent such as diethyl ether, wherein the benzotriazole hydrochloride is formed as the reactant precipitates. The hydrochloride is removed (eg, by filtration) and the solvent is removed from the filtrate (eg, by evaporation under reduced pressure) to produce a crude φ IV poly-12-hydroxystearyl benzene. Triazole (PHS-Bt), which may be unpurified. Directly as a deuteration agent to esterify selected sugars. Alternatively, the resulting crude PHS-Bt can be purified by the addition of dry, cold diethyl ether. The insoluble matter is removed by filtration, and the solvent is removed from the filtrate under reduced pressure (1.3-2.6 kPa [10-20 mmHg] at a water bath temperature of 30 to 50 ° C) to produce a purified PHS. -Bt. Process for the preparation of polyhydroxyalkanoates of formula I φ Traditionally, the action of derivatizing a glycoside with a polyhydroxyalkane benzotriazole of formula IV to produce a derivative of formula I may, for example, be via a solution of a sugar ( For example: chicory in the N-methylpyrrolidone (NMP) or N-ethylpyrrolidone (NEP) in the presence of a catalyst (such as triethylamine, potassium carbonate or sodium bicarbonate) t under anhydrous conditions And polyhydroxyalkane benzotriazole of formula IV (for example: poly-12-hydroxystearyl benzotriazole), reacted in a temperature range of up to 1 l ° C (usually about 80 ° C) It is carried out 4 to 24 hours and is preferably carried out in the presence of a catalyst such as triethylamine, potassium carbonate or sodium bicarbonate. -19 - 200831523 The sugar ester of formula I formed in the deuteration reaction can be isolated and selectively purified by conventional techniques, for example by non-solvent precipitation, ie, the reaction mixture is poured into excess formula I In the non-solvent of the ester (such as acetone, dichloromethane, diethyl ether or petroleum ether), it is preferred to carry out the partial removal of the solvent and triethylamine under reduced pressure. The by-product remains in the solution when the ester of formula I precipitates. Then, the ester was separated by filtration, washed with a non-solvent and dried. # The art is aware of different variations of the above methods. For example, the mercaptotriazole of formula IV can be prepared by reacting a PHS-acid with benzotriazole in the presence of thiopurine chloride (as described above), or the corresponding PHS mercapto chloride with benzotriazole in a base Prepared by the reaction of a catalyst such as triethylamine or an additional equivalent amount of benzotriazole, or by reacting a PHS-acid base salt with 1-methylsulfonyl-1H-benzotriazole . The degree of substitution of the desired sugar can be achieved by varying the molar ratio of the oxime to the sugar unit of Formula IV. The absolute number of moles of a sugar unit is defined as the weight of the input reaction ® sugar (in grams) divided by the molecular weight of the sugar unit that makes up the sugar. Thus, derivatives of the formula I having a degree of substitution in the range from 0.01 to 1.00 can be prepared. Further, conventionally, the deuteration of sugar can also be carried out by other deuteration agents other than alkane benzotriazole, for example, ester exchange with a PHS-acid ester. The sugar ester of the present invention in which the sugar moiety is bonded to an alkylamine carbonyl group substituted with a hydroxyalkyl alkoxy group or a polyhydroxyalkyl alkoxy group can be prepared analogously to a conventional method, for example, by converting a PHS-acid into a corresponding PHS- -20- 200831523 is an isocyanate which is then reacted with a specified sugar to produce the corresponding urethane of formula I. For use in a derivative of formula I wherein the sugar moiety is derived from inulin and the PHS moiety is a heptadecylamine carbonyl group substituted by 1 1-(poly-12-hydroxystearyloxy) according to formula m) The preparation method of the urethane according to the present invention is exemplified below. Method for preparing isocyanate of formula V# Traditionally, a PHS-acid (for example, poly-12-base stearic acid (Hypei*mer® LPl, trade name of ICI_Uniqema) having an average degree of polycondensation of 7) is converted into a corresponding one. An isocyanate derivative (short PHS-isocyanate or PHS-NCO) which is converted to the corresponding thiol azide group by reaction with diphenyl azide to convert the free carboxyl group of the PHS-acid dissolved in dry toluene Then, the reaction mixture is heated at about 110 ° C for about 18 hours to thermally rearrange the sulfhydryl azide to the corresponding isocyanate of formula V. The solvent is removed under reduced pressure to yield the crude PHS-isocyanate of Formula V which is reacted with the sugar without further purification to yield the urethane of Formula I.

Process for the preparation of alkylaminoglycosyl sugar esters of formula I substituted by polyhydroxyalkyl hydroxy groups The reaction between the sugars and the PHS-isocyanate and the separation and purification of the formed urethanes can be carried out according to WO 99/, respectively. A detailed description of 64549 and WO 0 1 /44303 -21 - 200831523 is prepared by a conventional reaction similar to the reaction between an alkyl isocyanate and an inulin sugar or a starch hydrolysate. Thus, the PHS-isocyanate of formula V is reacted with a specified sugar in an inert solvent (this is usually, but not necessarily, carried out under conditions of humidity exclusion) to yield a crude sugar ester of formula I, which may be according to known techniques ( Such as: the following) isolated and optionally purified. The sugar is dissolved in a solvent inert to the PHS-isocyanate (such as N-methylpyrrolidone), if necessary, under heating and removal of the remaining water (for example, by filtration), and then, The PHS-isocyanate of formula V (optionally dissolved in the same or another inert solvent (preferably compatible with the solvent of the preceding paragraph)) is slowly added to the dissolved sugar while stirring. This reaction can be carried out at room temperature to ll 〇 ° C (preferably 60-80 ° C), and is preferably carried out in the presence of a catalyst such as triethylamine, potassium carbonate or sodium bicarbonate. Then, the mixture is allowed to react under stirring until the reaction is complete, which is preferably carried out under heating (usually 75 t to 95 ° C, preferably about 80 Torr for 4 to 24 hours. Then, the reaction mixture is treated according to a conventional method ( For example, via non-solvent precipitation), this is done by pouring the reaction mixture into an excess of a non-solvent, a solvent that is miscible with the solvent used in the reactants and the remaining reagents therein. And the by-product may remain dissolved, but the sugar derivative of the formula I formed is almost insoluble. Then, the crude derivative of the formula I is isolated by, for example, filtration, optionally washed with a non-solvent and dried. The degree of substitution required for the I derivative (within the range of 〇·〇1 to 1 · )) can be obtained by using the molar ratio of the appropriate isocyanate/sugar unit. The absolute number of moles of the sugar unit-22-200831523 It is defined as the weight of the sugar in the reaction (in grams) divided by the molecular weight of the sugar unit constituting the sugar. Typically, the crude derivative of formula I is formed by the precipitation reaction from the reaction mixture of the deuteration reaction and the formation of the urethane. anti- It should be isolated from the reaction mixture and optionally washed with a suitable non-solvent for the derivative of formula I. It can be used directly as a surfactant without further purification. Alternatively, crude derivative of formula I The product can be purified by, for example, a conventional non-solvent precipitation method. To achieve this, the crude ester of the formula I is selectively dissolved under mild conditions in a suitable inert solvent (eg N-methylpyrrolidone). Or N-ethylpyrrolidone. After filtering the mixture to remove possible insoluble contaminants, the ester of formula I can be poured into an excess of a non-solvent of a derivative of formula I (such as acetone, dichloromethane, two) Precipitate from diethyl ether or petroleum ether. The precipitated ester of formula I is then isolated, washed with a non-solvent and dried. Other esters of formula I (such as having different sugar moieties and/or different The polyhydroxyalkyl hydrazine moiety, the polyhydroxy olefin oxime moiety or the different substituted alkylamine carbonyl moiety) may be from a suitable monosaccharide, disaccharide, oligofructose, polyfructose, starch hydrolysate or any thereof in a similar manner as described above. mixture PHS-acid poly-12-hydroxystearic acid, PHS-acid with other average degree of polycondensation, and other polyhydroxyalkanoic acids other than poly-12-hydroxystearic acid Or polyhydroxy enoic acid begins to be prepared. The sugar esters of the present invention exhibit interfacial activity properties, which make these derivatives suitable as surfactants, including as dispersants, emulsifiers, wetting agents, and/or dispersion stabilizers, including : Emulsion Stabilizers and Suspensions Stabilizing -23- 200831523. The esters of the invention (especially the sugar esters of formula I) are particularly suitable for use as preparations for stabilizing dispersions and/or stabilizing dispersions (such as emulsions, especially a surfactant for W/0 emulsions and suspensions, especially suspensions of particles in the oil phase and/or the aqueous phase. Thus, in another preferred system, the invention relates to compositions, especially Dispersions (including emulsions and suspensions) of sugar esters (especially sugar esters of formula I) are invented. Still another preferred system of the invention relates to the sugar esters of the invention (especially the sugar esters of formula I) as an interface for the preparation of stable dispersions and/or stable dispersions (including emulsions and suspensions) Use on the active agent. Another preferred system of the invention is a mixture of an ester of formula I, an ester of formula I or a mixture of one or more esters of formula I and one or more other surfactants as a stable dispersion for the preparation of a different dispersion And/or stabilizing surfactants or interfacial activities of different dispersions (especially suspensions and emulsions, including W/0 emulsions, 0/W emulsions, 0/W/0* emulsions and W/0/W* emulsions) Use on a mixture of agents (* ·· o/w/o = oil-in-water; w/o/w = water-in-oil). The term "stable emulsion, emulsion with acceptable gravitational stability, and emulsion with acceptable stability" means storage at room temperature (20 ° C to • 2 5 ° C) for at least 6 months or After storage at 4 5 °c or 50 °c for 1 month, the inspection does not show agglomerated emulsions (especially W/0-, 〇/W-, 0/W/0- and W/0/W - emulsion). Similarly, the term stable suspension as used herein refers to storage at room temperature (20 ° C to 25 ° C) for at least 6 months or at 45 ° C or 50 ° C for 1 month -24-200831523. The inspection does not present a suspension of particles deposited or floating. Here, the W/0- and 0/W-emulsions are considered to be stable even if they are creamy when stored, because in the case of cream formation, the emulsion is not broken (when the dispersed phase is coalesced, the emulsion) It is considered to be broken) and only becomes heterogeneous (homogeneous phase sinks or floats), and it is possible to recover the homogeneous emulsion by stirring the mixture. Similar standards apply to w/0/w- and 0/W/0-emulsions. Further, creaming can be easily overcome by the use of one or more conventional emulsion ingredients (e.g., thickeners and density modifiers), which are commonly used for what is referred to as the final blend or final product. As used herein, creaming refers to the occurrence of a continuous phase (i.e., an oil phase in the case of a W/0-emulsion, and an aqueous phase in the case of a 0/W-emulsion) floating or sinking. The term coalescing as used herein refers to the coalescence of small droplets of a dispersed phase, thereby forming larger droplets which are further formed by dispersion, and the homogeneous liquid group formed is clearly separated from the emulsion. A very convenient and industrially important feature of the sugar esters of the present invention is the elasticity provided by the chemical construction of the ester which can thereby determine the surface active nature of the ester. That is, the structural flexibility allows the preparation of a sugar having the desired hydrophilic-lipophilic balance (HLB) oxime with the desired interfacial activity properties by selecting a suitable sugar moiety and a suitable PHS moiety. Esters. The elasticity is derived from changes in the parameters determining the chemical structure of the esters of the invention (especially the esters of formula I), which are the nature and length of the sugar of the Sac moiety (defined by DP or DE), B (PHS) Partial nature and length (degree of polycondensation), using formula I with a moiety B (having a polyhydroxyalkane-25 of the formula II or a structure of an alkylamine carbonyl substituted by a polyhydroxyalkylhydrazine group of formula III) The possibility of the derivative, the degree of polycondensation of the PHS group of Part B, and the degree of substitution of the sugar moiety. Thus, a combination of a sugar moiety having a particular hydrophilic character and a PHS moiety having a particular lipophilic character can be used to prepare a sugar ester of the invention having the desired HLB (especially an ester of formula I). These sugar esters are suitable for special needs. Thus, for example, it is particularly suitable as a surfactant for the preparation and/or stabilization of W/0 emulsions or 0/W emulsions, or particularly suitable for use in the preparation and/or stabilization of oily or aqueous phases. The sugar ester of the present invention as a surfactant for the suspension. Those skilled in the art can perform routine experimentation without undue work to determine the appropriate combination of different parameters to produce the appropriate combination of a particular sugar portion and a particular PHS portion to achieve the desired functionality for a given application. Interesters of the invention having interfacial activity properties. Furthermore, those skilled in the art can also carry out routine experimentation without undue work to select an ester suitable for use in the preparation and/or stabilization of a specified dispersion from a plurality of esters of the present invention. The tendency of the different esters of the invention (especially the esters of formula I) to follow the interface activity properties can indeed be readily performed by routine experimentation (for example: evaluation of emulsions or suspensions prepared with the surfactant) Stability) to determine. The tendency of interfacial activity properties (especially as a dispersant) may be, for example, determined as a function of the nature of the sugar, or, in the case of a specified sugar, as a function of the length of the sugar chain (expressed as mean DP or DE) Measure -26- 200831523. For a given portion of the sugar, the tendency of this property can also be determined by altering the nature of Part B or the degree of polycondensation of the PHS group of the PHS moiety. The tendency of this property of a derivative of the formula I having a predetermined sugar moiety and a predetermined PHS moiety can be determined by a function of the degree of substitution. Thus, based on the results of routine experimentation, one skilled in the art can select esters of the invention that are particularly suitable for use in preparing and/or stabilizing dispersions (W/〇 emulsions, 0/W emulsions and suspensions, respectively), In particular, a mixture of an ester of the formula or an ester of the formula I, or a mixture of one or more esters of the formula I with one or more other surfactants. The effectiveness of the esters of the invention as surfactants can be readily assessed by routine experimentation. Therefore, in order to evaluate the effectiveness of the sugar ester of the present invention as a surfactant in a particular dispersion, a test dispersion is prepared (for example: only the aqueous phase, the oil phase and the ester, especially the ester of formula I or the ester of formula I) The stability of the emulsion consisting of a mixture of the mixture or the surfactant comprising the ester of the invention. Similarly, the use of hydrophilic or hydrophobic fine solid particles, an aqueous phase and/or an oil phase, an ester of the invention, In particular, a test suspension consisting of a mixture of an ester of formula I or an ester of formula I, or a mixture of surfactants comprising an ester of the invention. Different test emulsions are described in the following Tables 2 to 4. Test suspensions are described in In the following Example D. As described above and below, the use of the sugar esters of the present invention (especially a mixture of an ester of Formula I or an ester of Formula I, or one or more esters of the present invention, -27-200831523) The mixture of agents can be used as a surfactant to prepare and/or stabilize emulsions, especially stabilized W/0 emulsions, 0/W emulsions and W/0/W emulsions, and suspensions. In addition, the inventors have surprisingly discovered Including this hair The W/0 emulsion of the ester, especially the mixture of the ester of formula I or the ester of formula I, has a specific concentration in the aqueous phase (ie, the concentration is in the range of 0.4% to 4%, preferably 0.5% to 2%). The electrolyte (based on the weight of the total emulsion) can exhibit greatly improved stability. Obviously, when using the esters of the invention (especially the ester of formula I or a mixture of esters of formula I) As a surfactant for the preparation of W/O emulsions, the presence of electrolytes in the specific concentration range in the aqueous phase can (1) improve the possibility of preparing W/0 emulsions, and (Π) significantly contribute to the preparation of stable W/0. The emulsion and / or (iii) significantly improve the stability of the W / 0 emulsion. This finding is quite surprising, because the presence of electrolyte in the aqueous phase of the emulsion or the addition of electrolyte to the emulsion is generally considered to be unstable and irritating the emulsion. Coalescence, which in turn causes the emulsion to break. According to this finding, it is preferred to have an electrolyte (usually NaCl or a concentration of 0.4% to 4% (preferably 0.5% to 2% by weight) based on the weight of the total emulsion). MgS04, 7H20) is added to the W/0 milk comprising the ester of the invention (especially the ester of formula I) In the aqueous phase of the agent, a W/0 emulsion having acceptable or improved stability is prepared and obtained. Further, the electrolyte is added to the aqueous phase as compared with the corresponding emulsion containing no electrolyte in the aqueous phase. It can be used to prepare a stable W/0 emulsion from a specified oil phase and in a specified aqueous phase/oil ratio, the W/0 emulsion having a reduced amount of the ester or ester mixture of the invention of -28-200831523 (which serves as an interface) An active agent or a mixture thereof for use in a surfactant. Containing an ester of the invention (especially an ester of formula I) as a surfactant, and comprising a concentration of from 0.4% to 4% (preferably 0.5% to the aqueous phase) Another benefit of this improved stability of the 2.0%) electrolyte W/0 emulsion is that it can be used to prepare stable W/0 emulsions having low concentrations of the inventive esters and/or high aqueous phase/oil. The concentration of the sugar ester or sugar ester mixture of the present invention required to provide a stable dispersion (especially a stable emulsion or suspension) is based on the configuration of the ester, for example, in the case of the ester of formula I, based on the sugar moiety The nature, the degree of substitution and the nature of the substituted PHS moiety, the nature of the oil, the presence or absence of electrolytes in the aqueous phase, and the ratio of water to oil phase. The desired concentration can be readily determined by routine experimentation by a person skilled in the art without undue manipulation, for example, as described below for the experimental portion of W/0 emulsion, 0/W emulsion and suspension. ® In general, stable emulsions (especially stable w/0 emulsions) can be used at a total concentration of 0.01% to 15% (preferably 0.05% to 15%, usually 0.10% to 10%, Typically from 0.20% to 5% by weight (% by weight of all esters of the invention based on total dispersion) of the invention. Ester or ester mixtures (especially ester or ester mixtures of formula I) are prepared. β Further, 'preferably, an electrolyte having a concentration of 0.4% to 4% (preferably 0.5% to 2.0%) (% by weight based on the total emulsion) is added to the aqueous phase (usually MgS04.7H20 or NaCl). ) to improve the stability of the W/0 emulsion. -29- 200831523 Generally, in order to prepare a stable w/o emulsion, it can be prepared using an ester of the formula I in a concentration of from 0.25% to 5% by weight based on the total emulsion, wherein the sugar moiety is derived from An average DP of about 25 inulin, the PHS moiety is derived from a heptamer of PHS-acid, the degree of substitution s is in the range of 0.02 to 0.25, and the aqueous phase contains 0.5 to 2.0% (preferably 0.8 to 1.5%). ) MgS04 > 7H20 (% by weight based on the total emulsion). • Furthermore, a mixture of a derivative of formula I or a derivative of formula I can be prepared in an aqueous phase/oil ratio (weight/weight ratio) usually between 10/90 and 85/15 (especially 3 0/70 to 80) /20, more specifically a stable W/Ο emulsion in the range of 40/60 to 7 5/2 5). The sugar esters of the present invention (especially the esters of formula I) are useful in the preparation of stable W/Ο emulsions which generally exhibit low viscosity and good coatability. These characteristics result in a pleasant, non-tacky, non-skin feel when the emulsion is applied to the skin, which makes the emulsion very suitable for use in the preparation of final blends for personal care and cosmetic applications. Furthermore, the sugar derivatives of the present invention are very suitable for the preparation of stable W/o emulsions of oils having different properties, such as oils of natural and modified vegetable, animal or mineral origin. , synthetic oils and conventional oils, saturated esters and ethers for personal care and cosmetic compositions, and any mixtures thereof. Typical oils which can be used in the preparation of the stable w/o emulsions and suspensions according to the invention include: sphagnum oils (such as liquid paraffin and distilled petroleum jelly (eg Vasiline®, trademark); isoparaffin oil, such as : C13-C14 isoparaffin oil; fully hydrogenated squalene; solution of microcrystalline wax in oil from -30 to 200831523; animal and vegetable oils such as: oil, hawaiian soybean oil, jojoba oil and sunflower Oil; saturated, such as: C12-C15 alkyl benzoate, isopropyl palmitate [octyl] / triglyceride citrate and hydrogenated castor oil; and ethers, ethers. In addition, the esters of the present invention, In particular, the esters of formula I are suitable for use in stable W/0 emulsions containing an oil phase comprising a large amount of eucalyptus oil. This is a very advantageous property of esters, as it is known in the art that when the oil phase consists of oils or contains a large amount of eucalyptus oil It is more difficult, and sometimes complete, to prepare an acceptable dispersion (especially an emulsion) with acceptable stability. Furthermore, the esters of the invention, especially the esters of formula I and mixtures of formulas ( Optionally having an auxiliary surfactant) is also suitable for use in oil phases and / or a boundary agent for the suspension of finely divided particles in the aqueous phase. The sugar esters according to the invention comprising the sugar esters of the invention (especially formula I; as surfactants and suspensions thereof) can be prepared by cold treatment (eg cold treatment) And semi-cold treatment to prepare. For example: according to the method of preparing at room temperature or micro temperature, a typical method of the emulsion, the aqueous phase and the oil phase are separately prepared and the ester is dispersed in the oil phase. Adding water under vigorous stirring, then homogenizing the mixture (for example, by a high-speed stirrer). Alternatively, the sugar ester of the present invention may be dispersed in the aqueous phase instead of in the water phase, or may be in the aqueous phase. Before the homogenization of the mixture with the oil phase, the sweet almond and the ester of the present invention, the octanoic acid such as dioctane to prepare the surface-active ester of the large amount of the sand-qualified all-unesterified ester of the present invention, the method of knowing the method W/0 The oil phase or homogenization is added to the oil phase sugar ester plus -31 - 200831523. Only the water containing the electrolyte, the oil phase and one or more of the sugar esters of the invention or the surfactant comprising the ester of the invention are included. Emulsion composed of a mixture And a suspension consisting solely of granules and an aqueous phase and/or an oil phase containing one or more sugar esters of the invention or a surfactant mixture comprising an ester of the invention may also be used to evaluate surfactants And herein referred to as a brewing agent, such as: efficacy in a particular application. However, the milk φ agent and suspension will primarily constitute a component of the composite composition, and the composite composition also contains A conventional component selected from the use of (generally referred to as the final blend or final product). The particularly advantageous properties of the esters of the invention are their dispersion with a variety of other surfactants and most commonly used in the preparation and/or stabilization of conventional practices. Both the liquid and the final blend are compatible. This compatibility makes the sugar esters of the present invention (especially the esters of Formula I or the esters of Formula I) very suitable for use in the preparation of compositions for a variety of different applications, Includes dispersion and final blend. Φ Thus, in addition to the ester or ester mixture of the invention, the compositions according to the invention (especially dispersions) and the final blends thereof may be applied according to the composition, dispersion and final product (such as The special properties required for industrial, household, personal care, cosmetic and pharmaceutical applications include many different conventional ingredients. In the case of dispersions, especially emulsions, the conventional ingredients may be present in the aqueous phase, in the oil phase or in both phases. Such conventional ingredients include, for example, (auxiliary-) emulsifiers, (auxiliary) surfactants, softeners, dyes, viscosity modifiers, thickeners, pigments, emollients, perfumes, bactericides, UV Protectants, insecticides, insects-32- 4. 200831523 Agents, pesticides and agricultural chemicals. Thus, for example, in order to prepare a W/0 emulsion, suspension and final blend, conventional (auxiliary) emulsifiers, (auxiliary-) surfactants and/or softeners, and sugar esters of the invention may be used, and The desired W/0 emulsion or suspension can optionally be obtained by injecting a viscous modifier. Typical applications of the esters of the invention, especially esters of formula I, include use as surfactants, including as emulsifiers, dispersants, emulsion stabilizers, suspension stabilizers, pigments in non-aqueous liquids and waxes Dispersants and dye dispersants, as well as solvent additives for dry cleaning. Typical applications for dispersions containing the esters of the invention as their surfactants (especially suspensions and emulsions, more particularly W/0 emulsions, 0/W emulsions and final blends thereof) include industrial applications such as Coatings, paints, inks, cutting oils, making polymers, making polymer emulsions, polymer emulsions, products for oil field operations (eg for the preparation of crude oil emulsion products with improved pumpability) , polishing powder; household applications, such as: 蠘 candle and different polishes, such as: shoe polish; personal care applications such as: shampoo, soap, insect displacing stick, antiperspirant balm; cosmetics applications, Such as skin care products, skin creams, hydrating skin creams, lipsticks, lip glosses, mascaras, sunscreen compositions, such as: sunscreen creams and sunscreens; and pharmaceutical applications such as: lotions, creams, oils Cream and sesame oil. Another advantage of the sugar esters of the present invention is that it is insignificant or very low %. It has good biodegradability and the sugar portion and the PHS portion of the material are commercially available or readily available and sourced.自可更-33- 200831523 The new source. Experimental Section The present invention is further illustrated by the following detailed description and examples. EXAMPLE A: Process for the preparation of sugar esters of formula I Example A.1: Sugar esters of the formula Sac-(B)s(I) wherein the PHS moiety is a poly-12-hydroxystearin group of formula II Preparation method Ala: Preparation method of poly-12-hydroxystearyl benzotriazole (PHS-Bt) The PHS-acid (Hypermer LP1 from ICI-Uniqema, average degree of polycondensation of 7) is converted into the formula IV Poly-12-hydroxystearate benzotriazine (PHS-Bt).

0.01 mA (1·19 g = 0.73 ml) of S0C12 and 0.04 mol (4·77 g) of benzotriazole (Bt) were added to 5 〇 ml of room temperature under anhydrous conditions and nitrogen atmosphere. In methyl chloride. After half an hour of mixing, 0.01 mol (17 g) of PHS-acid (Hypermer LP1 from ICI-Uniqema) having an average degree of polycondensation of 7 was added thereto dropwise. After reacting at room temperature (20-25 ° C) for 18 hours with stirring, by reducing the pressure (at 40 to 6 〇 -34 - 200831523 ° C, 1.3-2.6 kPa [10-20 mm Hg ]) Evaporation to concentrate the reaction mixture. The concentrated reaction mixture was cooled and poured into 200 ml of dry and cold diethyl ether. The precipitated benzotriazole hydrochloride was removed via filtration. The solvent is removed by reducing the solvent under reduced pressure (at 30 to 50 ° C, 1.3-2.6 kPa [10-20 mmHg]) to produce a crude poly(1-2-hydroxystearate) of formula IV. Benzotriazole (PHS-Bt), which is a yellow scorpion solid. This crude PHS-φ Bt (approximately 95% yield of PHS-acid) is suitable for the deuteration of sugar without further purification. The effect of conversion of PHS-acid to the corresponding PHS-benzotriazole has been confirmed by spectroscopy (H^NMR spectrum: see Figure 1; C13-NMR spectrum: see Figure 2). Alb: preparation method of poly-12-hydroxystearic acid sugar of formula I Al, bl: method for preparing poly-12-hydroxystearic acid orange by PHS-Bt deuterated orange sugar φ according to the following Example A. 1 .a obtained PHS-benzotriazole (PHS-

Bt) The orange sugar is deuterated to produce the poly-12-hydroxystearic acid orange of formula I. A portion of 6 g (0.037 mol) of orange sugar (Beneo® HP, trade name of Orafti, Belgium) was partially added to 24 g of N-methylpyrrolidone (NMP). The temperature was raised to 65 ° C and the mixture was stirred until all the orange sugar was dissolved. Therefore, the solution is stripped under reduced pressure (at 1.3 ° C, 1.3-6.6 Pa [〇·〇1 to 0.05 mm Hg]) to remove the remaining water until 35 to 40% by weight is obtained. A solution of orange sugar. Then, 〇·2 molar equivalent of triethylamine (0.8 ml) (based on orange sugar-equivalent) -35-200831523 was added as a catalyst and the mixture was stirred for 15 minutes to obtain a homogeneous mixture. Then, 0.2 molar (13.45 grams) equivalent of PHS-benzotriazole (obtained in Ala·) was added under stirring and allowed to react at 70 to 11 ° C (preferably at about 8 ° C). Up to 24 hours (usually about 24 hours). Then, the obtained reaction product (i.e., poly-12-hydroxystearic acid orange of the formula I) was separated by pouring the reaction mixture into 200 ml of dry acetone or dry dichloromethane. The reaction product was precipitated, removed by filtration, washed with dry acetone or dry methylene chloride and dried to give a pale white crude product of formula I (yield: > 9 5%). The crude sugar derivative of formula I can be used, for example, as a surfactant. The formation of the sugar ester of formula I was confirmed by NMR spectroscopy (see Figure 3). A.l.b.2: Typical sugars that have been refined according to this general method include: sucrose 'average DP 25 orange sugar (from Beraft, Orafti, Belgium) and dextrin DE 2 (Glucidex 2 from Roquette, France). The degree of substitution is determined by the PHS-BT/sugar molar ratio and is conventionally analyzed by NMR spectroscopy. Figure 3 shows the H^NMR spectrum of poly-12-hydroxystearic acid orange of the formula I as a typical example (average DP 25 orange sugar [Beneo® HP from Belgium, Orafti]; poly-12-hydroxyl The stearic acid is derived from a PHS-acid having an average degree of polycondensation of 7 [Hypermer LP1; trade name from ICI-Uniqema; degree of substitution: 0. 〇3). The sugar derivative of formula I is prepared by the above procedure (wherein the PHS moiety is a poly-12-hydroxystearthenyl group of the formula (indicated by "intermediate PHS-Bt"). -36- 200831523 Examples Α·2.: Sugar esters of the formula Sac-(B)s(I) (wherein the PHS moiety is 11-(poly-12-hydroxystearoxy)-- Preparation method of alkylamine carbonyl group) Example A.2.a: Preparation method of PHS-acid isocyanate derivative of formula V (PHS·NCO) PHS-acid (Hypermer LP1 from ICI-Uniqema, The average degree of polycondensation is 7) an isocyanate derivative (PHS-NCO) converted to the PHS-acid of formula V.

17 g of PHS-acid (0.01 mol) having an average degree of polycondensation of 7 was dissolved in 80 ml of toluene at room temperature under anhydrous conditions and a nitrogen atmosphere. Therefore, 1.4 ml of triethylamine (〇·〇1 mol) was added and stirring was continued for 10 minutes at room temperature. Then, the temperature was raised, and when it reached 50 ° C, 2.2 ml (0.01 mol) of diphenylphosphoryl azide (DPPA) was added dropwise thereto. After the addition of all DPPA, the temperature was raised to ii 〇 ° C and the reaction mixture was allowed to boil for 18 hours. The solvent is then removed under reduced pressure (70 to 8 (TC, 1.3-6.6 kPa [10-50 mm Hg]) to produce crude PHS isocyanate (PHS-NCO), which is suitable for sugar amines. Metforminization without further purification. The effect of PHS-acid conversion to the corresponding PHS-NCO has been confirmed by NMR spectroscopy (see Figure 4). A.2,b·: Isocyanate of formula V and designated Method for preparing a sugar derivative of the formula Sac-(B)s(I) by a sugar reaction-37-200831523 The orange sugar is reacted with a PHS-isocyanate (PHS-NCO) obtained from the sample A.2.a as follows. To produce a urethane of formula I. 6 g (0.037 mol) of an average of DP 25 orange sugar (Beneo® HP, Belgium, Orafti trade name) is partially added to 24 g of N-methylpyrrolidone (NMP). Raise the temperature to 65 t: and stir the mixture until all the orange sugar is dissolved. Therefore, by reducing the pressure of the solution (at 70 ° C, 1.3-6.6 Pa [0.01 to 0.05 mm Hg] Stripping to remove the remaining water until a solution of 35 to 40% by weight of orange sugar is obtained. Then, 0.1 molar equivalent of triethylamine (with orange sugar - when added) As a catalyst, the mixture was stirred for 15 minutes to obtain a homogeneous mixture. Then, while stirring was continued, 0.2 mol equivalent (15.5 g) of PHS-NC0 (acquired in A, 2.a·) was added. And reacting it at 75 to 95 ° C (preferably at about 80 ° C) for 4 to 24 hours (usually about 24 hours). Then, the reaction mixture is poured into 200 ml of dry acetone or dry dichloromethane. The reaction product (i.e., 11-(poly-12-hydroxystearyloxy)-heptadecylamine formate) of the formula I is isolated. The reaction product is precipitated and separated by filtration to dry. The acetone or dry dichloromethane was washed and dried to give a dark white crude product (yield: > 75%). The structure of the ester of formula I was confirmed by NMR spectroscopy (see Figure 5). The crude glycosyl carbamate of I can be used as a surfactant' without further purification. The sugar ester of the formula I prepared by the above method (wherein the pHS moiety is 11-(poly-12-hydroxystearin) of the formula II The oxy)-heptadecane carbonyl group and the sugar moiety is derived from the average DP 25 orange sugar is presented in Table 1 below. Interface Active Agent No. 386. -38- 200831523

··S Ling NI笊_ Ϊ撇 Substitution degree (s in formula I) 0.05 0.03 0.02 0.22 0.08 0.81 0.12 0.05 \ 4 ci ! 0.05 0.08 0.02 0.02 0.02 Intermediate formula (3) (II or IIII) hH HH (b) |-| ^-1 Hj |—| HH : K HH |-1 |-1 Type (3) PHS-NCO PHS- Bt PHS- Bt PHS- Bt PHS- Bt PHS- Bt PHS- Bt PHS- Bt PHS- Bt PHS- Bt PHS- Bt PHS- Bt PHS- Bt PHS- Bt Type I B-part source (2) PHS PHS PHS PHS PHS PHS PHS PHS PHS ! PHS PHS PHS PHS PHS Type I Sac-part source (I) Beneo® HP Beneo®HP _I Beneo®HP Beneo®HP Beneo®P95 Sucrose Beneo®HP Maltodextrin DE2 Maltodextrin DE2 Beneo®HP Beneo®HP Beneo®HP Maltodextrin DE2 Maltodextrin DE2 Μ ^ 虼 amam dad • VO oo cn 364b s cn CNl inch 428b ii cn cn inch 5 VO CO inch δ oo cn inch ON cn inch inch: 舄 III shift III , II , i1^(e) (03m(Db | τι β 二 OI ·图锨:^nglEsM.SHdNAF^M鼷继/dzrdl SUIJSdxH : SHd ((N) :wng boat< disk fvs-qq :©03u3g _HK« ^t^da^dz~6,CNs:s6d®ssg:s_M®^w(Nda4JPidz:dH®slI9g (l) __ Helmet-39 - 200831523 Example B: Milk prepared from the ester of formula I EXAMPLES B. 1 : Preparation and Stability of W/0 Emulsions A predetermined concentration of the sugar derivative of Formula I is dispersed in a specified oil at room temperature or slightly warmed to about 50 ° C to form "Phase A". In addition, an aqueous phase containing an electrolyte (usually 0.8% by weight of MgS04*7H20 (% based on total emulsion)) is prepared to form "Phase B." Therefore, a high-speed stirring device (for example: from Staufen, Germany) , M. Zipperer's CATX 620) phase B was added to phase A under agitation and the mixture was homogenized for 5 minutes to produce the desired emulsion. In terms of stability testing, the preparation of the emulsion is usually 50 ml. In order to evaluate the stability, the emulsion was visually inspected after the emulsion was prepared, and the emulsion was stored at a predetermined temperature and then periodically observed for possible coalescence. According to the general procedure described above, different W/0 emulsions were prepared at different concentrations of different sugar derivatives of Formula I and different ratios of aqueous/oily phases and their stability was evaluated. Experimental details regarding derivatives and emulsions of Formula I are reported in Table 2 below. Different biphasic and multi-phase emulsions were prepared in a similar manner, including W/0, 0/W and W/0/W emulsions, and different concentrations of surfactants, not containing and compared with different oil phases/water. An emulsion containing different concentrations of electrolytic hydrazine, oil phases of different properties, and a mixture of surfactants was evaluated for stability. Details are summarized in Tables 3 and 4 below. -40- 200831523 Table 2: Esters containing Formula I f | E is the surfactant / 〇 emulsion The ester surfactant of Formula I is the ratio of the continuous phase w/o phase of the emulsion w/o emulsion (weight / weight) Thunder %% surfactant in water phase with total emulsion 386 Isopar M(2) 50/50 2 1 364b Isopar M 50/50 2 1 364b Isopar M 50/50 4 2 364b sarcophagus oil (3) 50 /50 4 2 ArlacelP135(4)* Isopar M 50/50 4 2 420 Isopar M 50/50 2 1 420 Isopar M 50/50 4 2 422 Isopar M 50/50 2 1 423 Isopar M 50/50 2 1 428b Isopar M 50/50 2 1 421 Isopar M 50/50 2 1 433 Isopar M 50/50 2 1 434 Isopar M 50/50 2 1 436 Isopar M 50/50 2 1 437 Isopar M 50/50 2 1 438 Isopar M 50 /50 2 1 439 Isopar M 50/50 2 1 440 Isopar M 50/50 2 1

Description of Table 2 (1): aqueous phase containing 0.8% MgS04JH20 (based on total emulsion) (2): Isopar Μ: trade name of C13-14 iso-stone oil from Exxon-Mobil Chemical, Available from Brenntag, Belgium (3): Dendrobium MED15, available from Brenntag, Belgium (4) : Arlaxel P135: Trade name for polyethylene glycol dipolyhydroxystearate, available from ICI*: Comparative test - 41 - 200831523

^ SI 9, & Sa S 53⁄4 {g . 5 ιΐ du 鬯_总荖I«1 g (M) 0.8 (M) 0.96 (M) 1.12 (M) 1.28 (M) 1.44 (M) 0.8 (M) 0.8 (M) 0.8 (M) 0.8 (N) 1 mol, in the aqueous phase 〇·〇 (= no electrolyte) wt% surfactant in total emulsion r _ Η CN r-l VO ri cn CN ii 0.25 CN ii CN with water phase meter CN csi CO Csl m CO inch CSJ t-H CSI inch 孽A ugly _ W side TM m Q w _ w 50/50 60/40 70/30 80/20 85/15 50/50 50/50 50/50 50/50 60/40 50/50 w/〇 Continuous phase of the emulsion_1 Isopar M(l) Isopar M Isopar M Isopar M Isopar M Isopar M Isopar M Isopar M Isopar M Isopar M Isopar Μ @监 赖 si si cn cn CSJ inch CO csi inch cn csi inch csi Csl inch CN csi inch CNJ CNI inch csi csi inch cn csi inch § butterfly light § 3 uu 9 jg disk rffi-qq dish t? · 姊唣船盈« Lai 屯辄 inch 1, £13 ^ trace ^ 钋撇 - 镤 tilt ^ dish embedded: 2 ^ two 081: (1) -42- 200831523 蘅 H: K- #d } Ossscs) ss_s_/__) 窍_寐寐虼%__ ifes^ Insert K1 fc^«^ {WM/W_} ^w^iytf

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Qooz inch Zhao S9IZIU -43- 200831523 Description of Table 4 (1) : Oyster sauce: cyclopentaoxane D3 45 from Dow Corning Corporation (2): Paraffin oil MED68, available from Brenntag, Belgium (3) : Sisterna PS750-C : Palmitic acid sucrose, HLB 16, Sisterna Company (4) : C1815: sucrose stearate, HLB 15, Mitsubishi-Kagaku Food Company φ (5) : C1216: sucrose laurate, HLB 16, Mitsubishi-

Kagaku Food Company (6): W/0/W Emulsion: Confirmed by Microscopy (7): W/0/W Emulsions obtained by homogenizing 0/W 20/80 mixture are indicated in Tables 2, 3 and 4 W/0, 0/W and W/0/W emulsions containing a mixture of esters or esters of formula 1 as a surfactant or a surfactant mixture comprising an ester of formula I are generally at room temperature below room temperature (even down to 5 ° C) and elevated temperatures (even up to 45 or 50 ° C) are also acceptable. Example c: Final Blends Containing Formula I Esters The esters of the present invention are suitable for use in the preparation of different final r blends (e.g., personal care and cosmetic finals, as exemplified below). Surfactant for emulsions. Example C.1: Water-in-oil (W/0) hydrated milk composition -44- 200831523 Phase A component % by weight of ester of formula I (No. 428b) 2.0 Isohexadecane 10.0 Paraffin oil 4.0 Isopropyl palmitate 3.0 Acetic acid Vitamin E 1.0 Magnesium stearate 0.3 Phase B Ingredient Weight demineralized water 75.3 Glycerin 3.0 MgS04*7H20 0.7 Antiseptic! i (Germaben® II)* 0.6 Allantoin 0.1 * Germaben® : International Professional Products ( The commercial name program of International Speciality Products disperses the surfactant (No. 428b) in the oil phase to form phase A upon heating to about 60 °C. The ingredients were mixed at room temperature to prepare phase B. The final blend was prepared by applying a high-speed stirring device (CATX620 from M. Zipperer, Staufen, Germany), adding phase B to phase A in 2 minutes at a stirring speed of 9500 rpm, and continuing to mix for 3 minutes at high speed. Product -45- 200831523 The desired w/ο hydrated milk composition. This composition is stable, exhibits good dispersibility and a pleasant, non-sticky and non-oily skin feel. Example C.2: Water-in-oil (W/0) composition phase A component % by weight derivative of formula I _ (dirty 428b) 3.0 dioctyl ether 6.0 isononanoic acid oxime ester 7.0 palmitic acid isopropyl ester 6.0 different ten Hexane 3.0 Magnesium Stearate. 5 Phase B Ingredient Weight ^ To Face Water 57.9 Glycerin 5.0 Ethanol 10.0

MgS04 · 7H20 1.0 Anti-corrosion! f(Germaben® II)* 0.6 * Germaben®: The international name for the professional product is to disperse the surfactant (No. 428b) at -60 - 200831523 by heating to about 60 °C. In order to produce phase A. The ingredients were mixed at room temperature to prepare phase B. The composition (final blend) was prepared by adding a high-speed stirring device (CATX620 from Staufen, Germany, Zipperer) to phase A in 2 minutes at a stirring speed of 9500 rpm and continuing to mix at high speed. 3 minutes to produce the desired W/0 hydrated milk composition. This composition is stable, exhibits good dispersibility and a pleasant, non-sticky and non-oily skin feel. Example C.3: Water-in-oil (W/O) skin cream composition phase A component % by weight derivative of formula I (No. 428b) 3.0 Dioctyl ether 3·0 Coconut caprylate / phthalate 6.0 octanoic acid / Triglyceride citrate 8·0 Sweet almond oil 8. 〇 • vinegar noodle Ε 1. 〇 beeswax 2.0 magnesium stearate 1-0 relative ingredients % weight demineralized water 61.4 • glycerol 5.0

MgS04 · 7H20 1.0 Anti-corrosion! l (Germaben® II)* 〇·6 * Germaben®: trade name for international professional products • 47- 200831523 Procedure Disperse surfactant (No. 428b) at 75-80 °C In the oil phase, to produce phase A. The ingredients (except the preservative) were mixed at room temperature and heated to 75 t: to prepare phase B. The preservative is added to the aqueous phase B a few seconds before the phases A and B are mixed. The preparation of the composition (final blend) was carried out using a high-speed stirring device (CATX620 from M. Zipperer, Staufen, Germany). • Phase B was added to phase A in 2 minutes at a stirring speed of 95 0 rpm and continued at high speed. The mixture was mixed for 3 minutes to produce the desired W/0 cream composition which was stable, exhibited good dispersibility and a pleasant, non-sticky and non-oily skin feel. Example D: Suspension prepared from esters of formula I Example Dla: suspension with hydrophobic particles • 2.5 g of a derivative of formula I (surfactant number 428b; polystearate sucrose) was added to 22.5 g of octanoic acid / Oil of triglyceride citrate (Neoderm 8TCC, trade name of CONMED company). 25 grams of hydrophobically modified Ti02 (Kimira Pigments 芬兰y uv • Titan Ml 70) was slowly added to the mixture using a high speed fixed-rotor system with vigorous stirring from 15,000 to 20,000 i*pm to stabilize Suspension. This suspension is suitable for different applications and can be, for example, according to the following and A sunscreen blends. -48- 200831523 Example Dlb: Preparation of sunscreen composition ί Method component amount (% by weight/weight) Hydrogenated vegetable oil (Cremeol HF-52, trade name of Aarhus) 15.0 Vegetable oil (Cegesoft PS-6, Cognis product Name) 63.0 Canddilla wax (Keyser & Mackay) 8.0 Dispersion from Example Dla 14.0 Preparation Method All ingredients were mixed together and heated to 75 °C with mixing until they melted. The mixture was then cooled with stirring and poured into the mold at about 60 tons. The mixture is allowed to cool further to room temperature to produce a final blend suitable as a sunscreen. Example D.2.a: suspension with hydrophobic particles # 3 g of orange sugar - a PHS derivative of formula I (surfactant number 42 8b) was weighed into 27 g of polydecene. 20 grams of hydrophobically modified Ti02 (UV Titan M262 from Kemira Pigments Oy, Finland) was slowly added to the mixture using a high speed fixed-rotor system with vigorous stirring at 15,000 to 20,000 rpm to produce a stable suspension. ^ This suspension is suitable for different applications and can be, for example, incorporated into W/0 sunscreen blends as follows. •49· 200831523 Example D.2.b: Preparation method of sunscreen final blend phase A component amount (% halo/weight) cetyl dimethyl decane copolyol (AbilEM%, trade name of Degussa) 2.0 Polyglycerol-4 isostearate (Isolan GI-34, trade name of Degussa) 1.0 Isohexadecane (Creasill HCG, trade name of Creation Couleurs) 8.0 Whale-based dimethyl oxane (Abil 鱲 984 〇, Degussa Product name) 2.0 Oyster sauce (350cSt) (:l methyl sand oxide DC200; Dow Corning's trade name) 4.0 Dispersion from the above D.2.a 12.5 Phase B component (% weight / military halo) Deionized water 67.0 Sodium Chloride 0.5 Butane Glycol 2.0 Glycerol 1.0 Preparation Method The ingredients of Phase A were mixed until homogenization. Mix the ingredients of Phase B until a clear solution is obtained. Phase B is then slowly added to Phase A and the mixture is homogenized to produce the desired sunscreen final blend suitable as a UV sunscreen lotion. The suspensions prepared as the dispersants using the esters of formula I as indicated in Examples D 1 a and D 2a exhibited acceptable stability and, as shown in Examples D 1 b and D 2b, were suitable for use in the preparation of final blends. For example, for a blend of -50-200831523 human care and makeup applications. GENERAL CONCLUSIONS ON EXAMPLES The above examples illustrate: (i) a process for the preparation of esters according to the invention, (ii) generally comprising an ester or ester mixture according to the invention (especially an ester of formula I) as an interface The emulsion of the active agent (especially the W/0 emulsion) and the suspension exhibit acceptable stability, and (iii) the stable W/0 emulsion can be obtained even in the presence of a low concentration of the ester of the invention, φ, especially in the presence of an electrolyte. (1) The esters are suitable for the preparation of different compositions, especially stable dispersions (such as emulsions and suspensions), which are suitable as final blends or suitable for use in preparation for different applications. The final blend. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 shows the H^NMR spectrum (PHS: heptamer) of poly-12-hydroxystearate benzotriazole (PHS-Bt). #Fig. 2 represents a C13-NMR spectrum (PHS: heptamer) of poly-12-hydroxystearyl benzotriazole (PHS-Bt). Figure 3 represents an H1-NMR spectrum of poly-12-hydroxystearic acid orange (PHS-orange sugar) (PHS: heptamer; orange sugar: average DP 25). Figure 4 represents a C13-NMR spectrum (PHS: heptamer) of 11-(poly-12-hydroxystearyloxy)-heptadecyl isocyanate (PHS-NCO). t Figure 5 represents the H^NMR spectrum of 11-(poly-12-hydroxystearyloxy)-heptadecylcarbamic acid orange (derived from PHS heptamer; orange sugar: average DP 25). -51 -

Claims (1)

200831523 X. Patent application scope 1 · A sugar ester characterized by its class: a sugar ester of polyhydroxyalkanoic acid, a polyhydroxyalkyl alkoxy group and a polyhydroxyalkyl decyloxy sugar ester, and a sugar ester of a hydroxy olefinic oxy group and a polyhydroxyl hydroxy carboxylic acid, wherein the sugar is composed of a chain of 5 10,000 cyclic monosaccharide units. The group consisting of: (i) a sugar ester of polyhydroxyalkanoic acid, which is composed of a sugar (Sac) moiety of a hydrazine moiety, a sugar ester of a polyhydroxy enoic acid, and a sugar of an olefin moiety (Sac). a portion consisting of, and (iii) a sugar ester of a hydroxyalkyl alkoxy group or a polyhydroxyaminocarboxylic acid, which is formed by an alkylamine carbonyl moiety substituted by a covalently bonded #hydroxyalkaneoxy group, wherein the sugar The Sac) portion is composed of 2 to 1 ring-shaped monosaccharide units consisting of a ring-shaped unit. The one or more light-segment units are replaced by one or more monosaccharide units, wherein the polyhydroxyalkylene moiety is a polycondensation hydroxy enoic acid having a polyhydroxy group having from 6 to 24 carbon atoms; a olefin-substituted monosaccharide substituted with a saccharide ester of a hydroxy enoic acid, a olefinic oxy group substituted with an alkylamino carboxylic acid, or a 2- to oxime ester, which is substituted by A sugar or chain consisting of a group of sugar units consisting of a covalently bonded polyhydroxyalkane group substituted by a polyvalent alkyl alkoxy group, a hydroxyalkyl alkoxy group or a polysaccharide (Sac) moiety. a sugar composed of a sulfhydryl group in which the hydrazine group is derived; an olefin moiety derived from an acid and an alkylamine having 6 to 24 carbon atoms: an alkylamine carbonyl moiety, and a substituted hydroxyalkane The decyloxy or polyhydroxyalkaneoxy group is derived from the same hydroxyalkanoic acid having 6 to 24 carbon atoms. 3. The sugar ester of claim 1, wherein the sugar ester has a structure corresponding to formula I, Sac-(B)s (I) wherein Sac represents a sugar moiety which is a sugar consisting of a cyclic monosaccharide unit or a sugar consisting of a chain of 2 to 1 ring-shaped monosaccharide units, wherein a hydrogen atom derived from one or more hydroxyl groups of one or more monosaccharide units is replaced by a B moiety, and the sugar is a single a sugar, or a disaccharide, an oligosaccharide or a polysaccharide, which respectively consists of the same or different monosaccharide units and any mixture thereof; B (also referred to herein as the PHS moiety) represents the poly-I2- of the formula (i) Hydroxystearyl group Wherein p represents the average degree of polycondensation of the integer i or number 〗 in the range of 〖to 1 ,, and when p represents the integer 1, R represents a hydrogen atom or a 12-hydroxystearone group, or when p represents 1 to -0-(R)p represents a poly-12-hydroxystearyloxy group; or (ii) an H-P2-hydroxystearyloxy group of the formula 111) Heptadecylamino-carbonyl group or 11-(poly-12-hydroxystearyloxy)-heptadecyl-amine carbonyl group, -53- 200831523 Wherein P represents an integer 1 or an average degree of polycondensation of a number 1 in the range of 1 to 10 and wherein when P represents an integer, R represents a hydrogen atom, or when P represents an average degree of polycondensation in the range of 1 to 10 , -〇-(R)p-generation g-poly-1 2 -hydroxystearyloxy group; and s (representing the degree of substitution, that is, the average number of b groups per sugar unit) is 〇 . Within the range of 01 to 1.00. 4. A sugar ester according to claim 3, wherein the Sac moiety is derived from fructose, glucose, sucrose, difructose, oligofructose of plant or synthetic origin, or polyfructose, or any mixture thereof. 5. The sugar ester of claim 4, wherein the polyfructose is chicory inulin. • 6. The sugar ester of claim 3, wherein the Sac moiety is derived from glucose, sucrose, lactose, maltose, starch hydrolysate or any mixture thereof. 7. The sugar ester of claim 3, wherein the Sac moiety is derived from a starch hydrolysate having a DE ranging from 1 to less than 20. 8. The sugar ester of claim 3, wherein the PHS moiety is a poly-12-hydroxystearin group of formula II derived from an average degree of polycondensation in the range of 5 to 9 (equivalent to formula II) Poly-12-hydroxystearic acid (PHS-acid) having an average enthalpy of 3 to 7). -54- 200831523 9. A sugar ester according to item 3 of the patent application, wherein the PHS moiety is a 1W12-hydroxystearyloxy)-heptadecaneaminecarbonyl group of formula III or 11-(poly-12-hydroxyl group) a stearyloxy)-heptadecane carbonyl group and is derived from poly-12-hydroxystearate having an average degree of polycondensation in the range of 5 to 9 (corresponding to an average enthalpy of 3 in the formula III of 3 to 7) Acid (PHS-acid). 10. The sugar ester of claim 8 or 9, wherein the PHS moiety is derived from poly-12-hydroxy-stearic acid (PHS- _ acid) having an average degree of polycondensation of 7. i i. The sugar ester of claim 3, wherein the degree of substitution (s in formula I) is in the range of 0.02 to 0.5. 12. The sugar ester of claim 3, wherein the Sac moiety is derived from sucrose, a chitosan in an average DP of 25, or a starch hydrolysate having a DE of 2, wherein the PHS moiety is a poly-type of formula II - The 12-hydroxystearin group and the poly-12-hydroxystearic acid (PHS-acid) have an average degree of polycondensation of 7, and the degree of substitution s is in the range of 0.02 to 0.5. A method for producing a sugar ester as defined in any one of claims 1 to 3, wherein the sugar moiety is linked to a polyhydroxyalkylguanidine moiety or a polyhydroxyalkylene moiety, characterized in that a sugar consisting of a cyclic monosaccharide unit or a chain of 2 to 100 cyclic monosaccharide units (the sugar is a monosaccharide, or a disaccharide, an oligosaccharide or a polysaccharide, respectively, which are identical or different The sugar unit and any mixture thereof are esterified by a deuterating agent derived from polyhydroxyalkanoic acid or polyhydroxy acid, and the molar ratio of the deuterating agent to the sugar unit used can be 0.01 to The ratio of the degree of substitution of 1.00, whereby polyhydroxyalkanoate or polyhydroxyenoic acid sugar can be separately produced, and the obtained sugar ester is separated from the reaction mixture -55-200831523. 14. The method of claim 13, wherein the oximation agent is poly-12 hydroxystearyl benzotriazole. The method of claim 14, wherein the oximation agent is poly-12-hydroxystearyl benzotriazole derived from poly-12-hydroxystearic acid having an average degree of polycondensation of 7 and The sugar is selected from the group consisting of fructose, glucose, sucrose, difructose, oligofructose, chicory inulin, starch hydrolysate or any mixture thereof. A method for producing a sugar ester as defined in any one of claims 1 to 3, wherein the sugar moiety is linked to an alkyl group substituted with a hydroxyalkyl alkoxy group or a polyhydroxyalkyl alkoxy group. An amine carbonyl group characterized by a sugar consisting of a cyclic monosaccharide unit or a chain of 2 to 100 cyclic monosaccharide units (the sugar is a monosaccharide, or a disaccharide, an oligosaccharide or a polysaccharide) , which consists of the same or different monosaccharide units and any mixture thereof, and isocyanate substituted with (hydroxyalkylhydrazinyl)-oxy- or (polyhydroxyalkylhydrazine decyloxy) The ester reaction, the molar ratio of the isocyanate to the sugar unit used is a ratio of the desired degree of substitution of 0.01 to 1.00, thereby producing an alkyl group substituted with a hydroxyalkyl alkoxy group or a polyhydroxyalkyl alkoxy group, respectively. The sugar ester of carbamic acid is further separated from the reaction mixture to obtain the resulting sugar ester. A method for producing a sugar ester as defined in any one of claims 1 to 3, wherein the (hydroxyalkylhydrazinyl)-oxy group- And (polyhydroxyalkyl fluorenyl methoxy) substituted isocyanate are 11-(12-hydroxystearyloxy)-heptadecane isocyanate and 11-(poly-12) -Hydroxystearyloxy)-heptadecane ester, the reaction product of -56-200831523 is 1 1-(12-hydroxystearyloxy)-heptadecylaminocarbamic acid and 11-( A sugar ester of poly-12-hydroxystearyloxy)-heptadecylamidocarboxylic acid. A method of using a mixture of a sugar ester or a sugar ester as defined in any one of claims 1 to 3 as a surfactant. 1 9. The method of use of claim 18, which uses the total concentration of 0.01% to 15% (% by weight of all sugars and esters based on the total dispersion) A mixture of a sugar ester or a sugar ester as defined in any one of the three items as a surfactant to prepare a dispersion. 20. The method of use of claim 19, wherein the dispersion is an emulsion, and the surfactant is a mixture of sugar esters or esters as defined in claim 3 of the scope of the patent application. 2 1. The method of use of claim 20, wherein the emulsion is a W/0 emulsion having an aqueous/oil phase ratio (weight/weight ratio) in the range of 10/90 to 85/15. • 22. The method of use of claim 21, wherein the emulsion is a W/0 emulsion and the aqueous phase comprises an electrolyte having a concentration of from 0.4% to 4% by weight based on the total emulsion. The method of any one of claims 20 to 22, wherein the oil phase of the emulsion comprises eucalyptus oil. > 24. The method of use of claim 18 or 19, wherein the sugar ester or sugar ester mixture as defined in claim 3 (optionally included with other surfactants) The mixture is used to prepare a 0/W emulsion. -57- 200831523 25. The method of use of claim 19, wherein the dispersion is a W/0 emulsion at a concentration of from 〇2% to 5% (% by weight based on the total emulsion) The sugar ester of formula I as defined in claim 3, wherein the sugar moiety is derived from inulin having an average DP of about 25, the PHS moiety being derived from heptameric poly-12-hydroxystearic acid (PHS-acid) and the degree of substitution s is in the range of 0.02 to 0.25, and the aqueous phase contains 0.8 to 1.5% of MgS04.7H20 (% by weight based on the total emulsion). 26. The method of claim 19, wherein the dispersion is a suspension. 27. A composition comprising a sugar ester as defined in any one of claims 1 to 3. 28. The composition of claim 27, which is a dispersion. 29. The composition of claim 28, wherein the dispersion is a W/0 emulsion, a 〇/w emulsion, a W/0/W emulsion, a 0/W/0 emulsion or a suspension. 30. A dispersion as defined in claim 29, which is a H winter blend or a method for preparing a final blend. 3 1 · The method of application of claim 30, wherein the final blend is for industrial, household, personal care, cosmetic or pharmaceutical applications. ° -58-