O / W emulsion and its inverted W / O emulsion, and personal care composition containing them

Abstract

This relates to an O / W emulsion that can be inverted to a W / O emulsion and a W / O emulsion inverted from an O / W emulsion, where the O / W emulsion is obtained by radical polymerization of at least one polyorganosiloxane having at least two aliphatically unsaturated carbon-carbon bonds, and an optional organohydrogenpolysiloxane, in the presence of a polyether-modified polysiloxane under emulsion polymerization reaction conditions. It also relates to methods for preparing the O / W emulsion and the W / O emulsion, and to personal care compositions containing the emulsion.

Description

[Technical field]

[0001] The present invention relates to O / W (oil-in-water) emulsions that can be inverted to W / O (water-in-oil) emulsions, and to W / O emulsions inverted from O / W emulsions. The present invention also relates to methods for preparing O / W and W / O emulsions, and to personal care compositions comprising O / W or W / O emulsions. [Background technology]

[0002] Emulsions are widely used in personal care products. Emulsions are generally defined as metastable colloids, which contain two immiscible fluids, namely oil and water, one dispersed (dispersed phase) in the other (continuous phase) in the presence of surfactants. Depending on the type of dispersed and continuous phases, emulsions can be divided into water-in-oil (W / O) emulsions and oil-in-water (O / W) emulsions. The conversion between these two types of emulsions is commonly called phase inversion or emulsion inversion.

[0003] Although W / O emulsions can provide sensory benefits such as silky feel to personal care products, few preparation methods can provide long-term stability to W / O emulsions. Most W / O emulsions are prepared by mechanical emulsification methods, in which the aqueous phase is dispersed into the oil phase at high shear rates. However, W / O emulsions prepared in this way may not be stable, and the content of aqueous phase introduced by this method is relatively low. Therefore, interest in phase inversion methods has increased. A PIT (phase inversion temperature) method has been proposed, in which the temperature of the emulsion is increased above the PIT temperature to initiate phase inversion. However, for stability, W / O emulsions prepared from the PIT method must be stored at a temperature higher than the PIT temperature and cannot be stored at room temperature. Adding an aqueous solution with a concentration of electrolyte or inorganic salt to the emulsion can reduce the PIT temperature, but the amount of reduction in the PIT temperature depends on the concentration of the solution and is limited by the solubility of the inorganic salt. Also, the application of W / O emulsions containing high concentrations of salts may be limited. Therefore, it is desirable to prepare a W / O emulsion from an O / W emulsion without heating or adding inorganic salts.

[0004] Furthermore, although O / W emulsions have been studied more intensively than W / O emulsions, few can be successfully inverted into W / O emulsions. Summary of the Invention

[0005] In one aspect, the present invention relates to an O / W emulsion of a crosslinked silicone, wherein the O / W emulsion is obtained from the radical polymerization under emulsion polymerization reaction conditions of at least one polyorganosiloxane having at least two aliphatically unsaturated carbon-carbon bonds, and an optional organohydrogenpolysiloxane, in the presence of a polyether-modified polysiloxane.

[0006] The O / W emulsion of the present invention is (a) combining a polyorganosiloxane with a polyether-modified polysiloxane and an optional organohydrogenpolysiloxane to obtain a mixture; (b) adding an aqueous medium containing an emulsifier to the mixture with stirring; and (c) subjecting the mixture to radical polymerization.

[0007] In another aspect, the present invention relates to a W / O emulsion obtained from the phase inversion of an O / W emulsion according to the invention by adding an oil to said O / W emulsion.

[0008] In yet another aspect, the present invention relates to a personal care composition comprising a W / O emulsion or an O / W emulsion according to the present invention.

[0009] Surprisingly, it has been found that the O / W emulsion of the present invention can be inverted to a W / O emulsion by increasing the volume fraction of the oil phase, for example, by simply mixing with a common oil or grease, particularly one used in personal care formulations, to increase the volume fraction of the oil phase. After phase inversion, the internally crosslinked silicone formed by emulsion polymerization can enter and occupy the continuous phase by swelling with the oil phase, and function as a rheological additive in the formulation of personal care products. The phase inversion ability of an O / W emulsion is very beneficial. The O / W is compatible with water or aqueous components due to its aqueous continuous phase, and is also compatible with oil or oily components due to phase inversion. Thus, the phase inversion emulsion of the present invention can facilitate the introduction of aqueous components into a W / O emulsion (including water / silicone oil emulsion) or oil-based formulation. Formulations formed from the emulsion of the present invention, particularly cosmetic formulations, can provide excellent stability and excellent usability, with an increased aqueous component and a good cushioning feel without a sticky feel. [Brief description of the drawings]

[0010] [Figure 1]FIG. 1 shows photographs taken of the emulsion prepared in Example 1 before and after mixing with hemisqualane as oil. [Diagram 2] Figures 2a and 2b show micrographs of the emulsion prepared in Example 4 before (2a) and after (2b) phase inversion using Silsoft 034 as the oil. [Diagram 3] 3a and 3b show photographs taken of the emulsions prepared in Example 4 (3a) and Comparative Example 1 (4b) that were demulsified with isopropyl alcohol (IPA). [Figure 4] FIG. 4 shows a photograph taken of the emulsion prepared in Comparative Example 2 after mixing in a 1:1 ratio with hemisqualane as oil. [Diagram 5] 5a and 5b show photographs taken of the emulsion prepared in Comparative Example 2 after mixing with PEG-10 Dimethicone (5a) and further deionized water (5b). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] In the specification and claims, the following terms and expressions are to be understood as indicated.

[0012] The singular forms "a," "an," and "the" include the plurals, and reference to a particular value includes at least that particular value unless the context clearly dictates otherwise.

[0013] All methods described herein can be performed in any suitable order unless otherwise indicated herein or clearly contradicted by context. The use of all examples or exemplary language (e.g., "etc.") provided herein is intended merely to better illustrate the invention and does not limit the scope of the invention unless otherwise claimed.

[0014] No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the invention.

[0015] The terms "comprising," "including," "containing," "characterized by," and their grammatical equivalents are inclusive or open-ended terms that do not exclude additional, unrecited elements or method steps, but will also be understood to include the more restrictive terms "consisting of" and "consisting essentially of."

[0016] Except in the examples or where otherwise indicated, all numbers expressing amounts of materials, temperatures, minutes of time, quantified properties of materials, and the like described in the specification and claims are to be understood as being modified in all instances by the term "about," regardless of whether the term "about" is used in the context.

[0017] Any numerical range recited herein is understood to include all subranges within that range, and any combination of the various endpoints of such range or subrange.

[0018] Any compound, material, or substance explicitly or implicitly disclosed in the specification and / or claimed as belonging to a group of structurally, compositionally, and / or functionally related compounds, materials, or substances will be further understood to include each individual representative of the group and all combinations thereof.

[0019] The term "hydrocarbon group" means any hydrocarbon from which one or more hydrogen atoms have been removed, including alkyl, alkenyl, alkynyl, cyclic alkyl, cyclic alkenyl, cyclic alkynyl, aryl, aralkyl and arenyl groups, and including hydrocarbon groups containing at least one heteroatom.

[0020] The term "alkyl" refers to any monovalent saturated linear, branched, or cyclic hydrocarbon group; the term "alkenyl" refers to any monovalent linear, branched, or cyclic hydrocarbon group containing one or more carbon-carbon double bonds, where the point of attachment of the group may be either the carbon-carbon double bond or elsewhere therein; and the term "alkynyl" refers to any monovalent linear, branched, or cyclic hydrocarbon group containing one or more carbon-carbon triple bonds, and optionally one or more carbon-carbon double bonds, where the point of attachment of the group may be either the carbon-carbon triple bond, the carbon-carbon double bond, or elsewhere therein. Examples of alkyl include methyl, ethyl, propyl, and isobutyl. Examples of alkenyl include vinyl, propenyl, allyl, methallyl, ethylidenylnorbornane, ethylidenenorbornyl, ethylidenylnorbornene, and ethylidenenorbornenyl. Examples of alkynyl include acetylenyl, propargyl, and methylacetylenyl.

[0021] The terms "cyclic alkyl," "cyclic alkenyl," and "cyclic alkynyl" include bicyclic, tricyclic and higher cyclic structures, as well as the aforementioned cyclic structures further substituted with alkyl, alkenyl, and / or alkynyl groups. Representative examples include norbornyl, norbornenyl, ethylnorbornyl, ethylnorbornenyl, cyclohexyl, ethylcyclohexyl, ethylcyclohexenyl, cyclohexylcyclohexyl, and cyclododecatrienyl.

[0022] The term "aryl" means any monovalent aromatic hydrocarbon group; the term "aralkyl" means any alkyl group (as defined herein) in which one or more hydrogen atoms are replaced by an equal number of the same and / or different aryl (as defined herein) groups; and the term "arenyl" means any aryl group (as defined herein) in which one or more hydrogen atoms are replaced by an equal number of the same and / or different alkyl groups (as defined herein). Examples of aryl include phenyl and naphthalenyl. Examples of aralkyl include benzyl and phenethyl. Examples of arenyl include tolyl and xylyl.

[0023] The term "heteroatom" means any of the Groups 13-17 elements except carbon and includes, for example, oxygen, nitrogen, silicon, sulfur, phosphorus, fluorine, chlorine, bromine, and iodine.

[0024] In one embodiment, the one or more hydrocarbon groups, if present, contain up to 60 carbon atoms, in another embodiment up to 30 carbon atoms, and in yet another embodiment up to 20 carbon atoms.

[0025] Useful hydrocarbon groups include alkyl groups, examples of which are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and tert-pentyl; hexyl, such as n-hexyl; heptyl, such as n-heptyl; octyl, such as n-octyl, isooctyl, and 2,2,4-trimethylpentyl; nonyl, such as n-nonyl; decyl, such as n-decyl; and cycloalkyl, such as cyclopentyl, cyclohexyl, cycloheptyl, and methylcyclohexyl. Examples of alkenyl groups include vinyl, propenyl, allyl, methallyl, cyclohexenyl, norbornenyl, ethylnorbornenyl, ethylidenylnorbornane, ethylidenenorbornyl, ethylidenylnorbornene, and ethylidenenorbornenyl. Examples of alkynyl groups include acetylenyl, propargyl, and methylacetylenyl. Examples of the aryl group include phenyl, naphthyl, o-, m- and p-tolyl, xylyl, ethylphenyl, and benzyl.

[0026] The terms and expressions "hydrosilyl," "hydride," "silicone hydride," and "SiH" are used interchangeably in the organosiloxane art and are understood to refer to polyorganosiloxanes containing one or more hydrogen atoms directly bonded to silicon.

[0027] The term "emulsion" as used herein should also be understood to include "microemulsions."

[0028] The term "oil" as used herein should also be understood to include, but is not limited to, polysiloxane fluids such as silicone oils.

[0029] The terms or phrases used in the specification and claims should not be interpreted in a restrictive manner as their ordinary or dictionary meanings, but should be interpreted as meanings and concepts that fit the inventive concept based on the principle that an inventor can appropriately define the concept of a term in order to best describe his or her invention.

[0030] The inventors of the present invention have surprisingly discovered O / W emulsions of crosslinked silicones that can be inverted to W / O emulsions by increasing the volume fraction of the oil phase, where the O / W emulsion is obtained from the radical polymerization under emulsion polymerization reaction conditions of at least one polyorganosiloxane having at least two aliphatically unsaturated carbon-carbon bonds, and an optional organohydrogenpolysiloxane, in the presence of a polyether modified polysiloxane.

[0031] The polyorganosiloxane has at least two aliphatically unsaturated carbon-carbon bonds that can undergo a free radical addition polymerization reaction to form a crosslinked silicone in the internal phase of the O / W emulsion. The number of aliphatically unsaturated carbon-carbon bonds may be, for example, 2 to about 1000, preferably 2 to about 500, and more preferably 2 to about 100.

[0032] In a preferred embodiment, the polyorganosiloxane comprises at least two alkenyl / alkyne groups.When an organohydrogenpolysiloxane is present, the radical addition polymerization reaction includes not only the radical polymerization of the alkenyl / alkynyl groups of the polyorganosiloxane, but also the hydrosilylation reaction between the Si-H of the organohydrogenpolysiloxane and the alkenyl / alkynyl groups of the polysiloxane.The polyorganosiloxane may also comprise Si-H functional groups.

[0033] In one embodiment, the polyorganosiloxane having at least two aliphatically unsaturated carbon-carbon bonds is of the general formula (I): M g M H h M V i M F j D k D H l D V m D F n To T H p T V q T F r Q s formula (1) Here we go M=R 21 R 22 R 23 SiO 1 / 2 ; M H =R 24 R 25 HSiO 1 / 2 ; M V =R 26 R 27 R 28 SiO 1 / 2 ; M F =R 29 R 30 R F SiO 1 / 2 ; D=R 31 R 32 SiO 2 / 2 ; D H =R 33 HSiO 2 / 2 ; D V =R 34 R 35 SiO 2 / 2 ; D F =R 36 R F SiO 2 / 2 ; T=R 37 SiO 3 / 2 ; T H =HSiO 3 / 2 ; T V =R 38 SiO 3 / 2 ; T F =R F SiO 3 / 2 ; Q=SiO 4 / 2 ここでR 21 、R 22, R 23 , R 24 , R 25 , R 27 , R 28 , R 31 , R 32 , R 33 , R 35 and R 37 are each independently a monovalent hydrocarbon radical of up to 60 carbon atoms, specifically up to 30 carbon atoms, more specifically up to 20 carbon atoms; R 26 , R 34 and R 38 are each independently an ethylenically unsaturated group of up to 30 carbon atoms, specifically up to 20 carbon atoms, more specifically up to 10 carbon atoms; R 29 , R 30 and R 36 are each independently a monovalent hydrocarbon radical of up to 60 carbon atoms, more specifically up to 30 carbon atoms, and even more specifically up to 20 carbon atoms, or R F and each R F are independently monovalent alkoxy or ether groups of up to 60 carbon atoms, more specifically up to 30 carbon atoms, and even more specifically up to 20 carbon atoms; and the subscripts g, h, i, j, k, l, m, n, o, p, q, r, and s are each independently limited to be an integer from 0 to 1000, with i+m+q≧2, e.g., an integer from 2 to about 500.

[0034] In a preferred embodiment, the polyorganosiloxane is M V i D k D V m M 2-i (I-1) Here, M V , D, D Vand M are as defined above, and the subscripts i, k, and m are integers, subject to the constraints that i is from 0 to 2; k is from 0 to 1000, specifically from 10 to 600, more specifically from 10 to 500; m is from 0 to 100, more specifically from 0 to 50; and R 26 and R 34 are each independently selected from the group consisting of vinyl, allyl, methallyl, acrylate or alkacrylate groups, preferably vinyl or allyl; M V i Q s (I-2) Here, M V and Q are as defined above, and the subscripts i and s are integers, subject to the constraints that i > 1, specifically > 2, more specifically > 3; s > 1, specifically > 2, more specifically > 3; and i + s is from 2 to 50, specifically from 2 to 20, more specifically from 2 to 15; and each R 26 is selected from the group consisting of vinyl, allyl, methallyl, acrylate or alkacrylate groups, preferably vinyl or allyl; and at least one member selected from the group consisting of:

[0035] In one embodiment, the organohydrogenpolysiloxane is present and is of the general formula (I): M g M H h M V i M F j D k D H l D V m D F n T o T H p T V q T F r Q s Formula (I) Here, M, M H , M V , M F , D, D H , D V , D F , T, T H , T V , T F and Q are as defined above, and the subscripts g, h, i, j, k, l, m, n, o, p, q, r and s are each independently an integer from 0 to 500, specifically from 0 to 200, more specifically from 0 to 100, subject to the limitations that (1) h+l+p≧1, specifically ≧2, more specifically ≧8, and (2) when i+m+q≧2, then formula (I) defined for the polyorganosiloxane and the organohydrogenpolysiloxane is different.

[0036] In a preferred embodiment, the organohydrogenpolysiloxane is M H h D k D H l M 2-h (I-3) Here, M H , D, D H and M is as defined above, and h, k, and l are 0 or positive numbers, subject to the constraints that h is 0 to 2; k is 10 to 300, specifically 10 to 200, more specifically 20 to 200; l is 0 to 50, specifically 0 to 20, more specifically 1 to 10; and h+1 is 1 to 100, more specifically 1 to 32, and even more specifically 2 to 12; M H h Q s (I-4) Here, M Hand Q is as defined above, and the subscripts h and s are integers, subject to the constraints that h > 1, specifically > 2, more specifically > 3; s > 1, specifically > 2, more specifically > 3; and i + s is from 2 to 50, specifically from 2 to 20, more specifically from 2 to 15; and at least one member selected from the group consisting of:

[0037] The molar ratio of total ethylenically unsaturated groups (including those present in the polyorganosiloxane and organohydrogenpolysiloxane, if present) to total Si-H functional groups (including those present in the polyorganosiloxane and organohydrogenpolysiloxane, if present) should be at least 1, advantageously at least 2. On a weight basis, the weight ratio of total polyorganosiloxane to total organohydrogenpolysiloxane can vary widely, for example, from 100:0 to 1:99, or from 100:0 to 50:50, or from 100:0 to 80:20.

[0038] The viscosities of polyorganosiloxanes and organohydrogenpolysiloxanes vary widely. For example, polyorganosiloxanes may have a viscosity of 0.0002 to 1000 Pa.s, specifically 0.001 Pa.s to 100 Pa.s, as measured by a Brookfield rotational viscometer. Organohydrogenpolysiloxanes may have a viscosity of 0.001 to 50 Pa.s, specifically 0.002 to 10 Pa.s, as measured by a Brookfield rotational viscometer.

[0039] In most cases, the polyorganosiloxane and organohydrogenpolysiloxane will be present in the O / W emulsion polymerization reaction mixture at the beginning of the polymerization. However, it is possible to initiate polymerization of the polyorganosiloxane alone, and only thereafter, but before polymerization of the polyorganosiloxane is completed, introduce the optional organohydrogenpolysiloxane into the emulsion reaction medium, thereby freeing up any unreacted M2O3 present in the polyorganosiloxane. V , D Vand / or T V The unit is M present in the organohydrogenpolysiloxane. H , D H and / or T H It is within the scope of the present invention that the units will be hydrosilylated. The delayed addition of the organohydrogenpolysiloxane to the polyorganosiloxane can be advantageous when preparing interpenetrating polymer networks (IPNs) or core-shell structures.

[0040] As used herein, "polyether-modified polysiloxane" refers to a polysiloxane in which one or more polyether moieties are bonded directly or via a divalent hydrocarbon group to one or more Si atoms in the polysiloxane backbone. The polyether moiety is composed of one or more alkylene oxide groups. The alkylene oxide group is preferably at least one selected from an ethylene oxide group, a propylene oxide group, and a butylene group. The Si atom to which the polyether moiety is bonded is a M unit (SiO 1 / 2 ), D units (SiO) or T units (SiO 3 / 2 ), preferably at the M and / or D units, more preferably at the D units. The divalent hydrocarbon groups are preferably divalent linear or branched alkylene groups having from 1 to about 20 carbon atoms, more preferably from 2 to about 10 carbon atoms, and even more preferably from 3 to 6 carbon atoms.

[0041] In addition to the polyether moiety, the polyether modified polysiloxane may further comprise other functional groups, such as alkoxy, aryloxy, amino, ester, amide or epoxide groups, which can be bonded to the Si atoms of the polysiloxane backbone either directly or via divalent hydrocarbon groups, such as those listed above for the polyether moiety.

[0042] In a preferred embodiment, the polyether-modified polysiloxane is of the general formula (II): M 1 a M 2b M 3 c D 1 d D 2 e D 3 f Formula (II) where M 1 =R 1 R 2 R 3 SiO 1 / 2 M 2 =R 4 R 5 R 6 SiO 1 / 2 M 3 =R 7 R 8 R 9 SiO 1 / 2 D 1 =R 10 R 11 SiO 2 / 2 D 2 =R 12 R 13 SiO 2 / 2 D 3 =R 14 R 15 SiO 2 / 2 In the formula (II), R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 10 , R 11 , R 12 and R 14 are each independently a monovalent hydrocarbon group having up to about 60 carbon atoms, preferably an alkyl or aryl having up to 10 carbon atoms, more preferably an alkyl or phenyl having from 1 to 4 carbon atoms, and even more preferably methyl; R 6 and R 13 are each independently -R16 -O-(C2H4O) x (C3H6O) y (C4H8O) z -R 17 where R 16 is a divalent linear or branched alkylene group optionally containing an oxygen atom or a nitrogen atom and having from 1 to about 20 carbon atoms, preferably from 2 to about 10 carbon atoms, and more preferably from about 3 to 6 carbon atoms; R 17 is selected from hydrogen, alkyl, acyl (-C(O)R, where R is an alkyl group) or ester group (-C(O)OR, where R is an alkyl group) having from 1 to about 20 carbon atoms, preferably from 1 to about 6 carbon atoms; and the subscripts x, y and z are each independently an integer from 0 to about 200, preferably from 1 to about 100, more preferably from 2 to about 20, subject to the limit that 1≦x+y+z≦200; R 9 and R 15 are each independently a linear or branched alkyl group of 4 to about 20 carbon atoms, optionally containing an F atom; a linear or branched alkoxy or aryloxy group of up to about 20 carbon atoms; or a divalent alkylene group terminated with an alkoxy, aryloxy, amino, ester, amide or epoxide group, optionally containing an F atom and having 1 to about 20 carbon atoms, preferably 3 to about 10 carbon atoms; The subscripts a, b, c, d, e, and f are each independently an integer from 0 to 200, subject to the restriction that b+e≧1.

[0043] In a further preferred embodiment, the polyether-modified polysiloxane is M 1 2D 1 d D 2 e (II-1) Here, M 1 , D 1 and D. 2is as defined above for formula (II), d is from 1 to about 200, preferably from 1 to about 100; e is from 1 to about 200, preferably from 1 to about 100; and M 2 b D 1 d D 2 e M 1 2-b (II-2) Here, M 1 , M 2 , D 1 and D. 2 is as defined above for formula (II), b is 1 or 2, d is 1 to 200, preferably 1 to about 100; e is 1 to 200, preferably 1 to about 100; and at least one member selected from the group consisting of:

[0044] Polyether modified silicones can be prepared by hydrosilylation of Si-H functionalized polysiloxanes with vinyl-containing polyethers in the presence of Pt catalysts, which is well known in the art.Polyether modified silicones are also commercially available, such as PEG-3 dimethicone, PEG-6 dimethicone, PEG-7 dimethicone, PEG-8 dimethicone, PEG-9 dimethicone, PEG-10 dimethicone, PEG-12 dimethicone, PEG-14 dimethicone, PEG-17 dimethicone, and PEG / PPG-20 / 15 dimethicone (all from Momentive Performance Materials).

[0045] The polyether-modified polysiloxane is used in an amount of from about 5 to about 50 parts by weight, preferably from about 8 to about 35 parts by weight, and more preferably from 10 to about 30 parts by weight, based on 100 parts by weight of the total of the polyorganosiloxane having at least two aliphatically unsaturated carbon-carbon bonds and the organohydrogenpolysiloxane, if present.

[0046] The free radical initiated polymerization of the polyorganosiloxane and the hydrosilylation of the polyorganosiloxane with the organohydrogenpolysiloxane, if present, can be carried out in an O / W emulsion polymerization reaction medium using conventional or other known emulsion polymerization procedures.

[0047] In such emulsion polymerization procedures, the dispersed oil phase of the emulsion reaction mixture comprises the polyorganosiloxane, polyether modified polysiloxane, optional organohydrogenpolysiloxane, and optional organic solvent and / or swelling agent (compatibilizer). The continuous aqueous phase of the emulsion reaction medium comprises water and water soluble or water miscible components such as emulsifier, free radical initiator, and optional components such as stabilizers, co-stabilizers, chain transfer agents, etc. In general, the oil phase can comprise 1 to 80% by weight of the emulsion polymerization reaction medium, advantageously 30 to 70% by weight, with the aqueous phase comprising the remainder.

[0048] In one embodiment, the O / W emulsion comprises: (a) combining a polyorganosiloxane with a polyether-modified polysiloxane, an optional organohydrogenpolysiloxane, and an optional organic solvent and / or swelling agent (compatibilizer) to obtain a mixture; (b) adding, under agitation, an aqueous medium containing an emulsifier, a free radical initiator, and optional stabilizers and / or co-stabilizers to the mixture; and (c) subjecting the mixture to radical polymerization.

[0049] Solvents and / or swelling agents (compatibilizers) can be incorporated into the oil phase of the emulsion polymerization reaction medium. Suitable solvents / swelling agents include non-reactive polyorganosiloxanes with a viscosity of 0.002 Pa.s to 0.2 Pa.s, such as methicone, alkyl methicones, such as octyl methicone, dimethicone, alkyl dimethicone, phenyl dimethicone, amino dimethicone, trimethylsiloxysilicates, and polymethylsilsesquioxane; hydrocarbons, such as isodecane, hexadecane, and squalane; triglycerides, such as caprylic triglyceride; esters, such as cetyl palmitate and isopropyl myristate; and ethers, such as dipropylene glycol butyl ether. Such solvents / swelling agents can represent up to 95 weight percent of the oil phase of the O / W emulsion reaction medium.

[0050] Suitable emulsifiers include nonionic and anionic types and mixtures thereof. Suitable nonionic emulsifiers include any of those previously used in emulsion polymerization processes, such as alcohol ethoxylates, polyoxyethylene lauryl ether, polyoxyethylene monostearate, etc. Similarly, useful anionic emulsifiers include those known to be useful in emulsion polymerization procedures, such as alkali metal sulfonate, sulfate, phosphate and sulfosuccinate surfactants. Specific examples of these surfactants include alkali metal sulforesorcinates; sulfonated glyceryl esters of fatty acids; salts of sulfonated monohydric alcohol esters; sulfonated aromatic hydrocarbon alkali salts, such as sodium alpha-naphthalene monosulfonate; sulfates, such as sodium lauryl sulfate, sodium cetostearyl sulfate, triethanolamine lauryl sulfate, and sodium lauryl ether sulfate; phosphates, such as the potassium salt of cetyl phosphate; and sulfosuccinates, such as disodium lauryl sulfosuccinate. In a preferred embodiment, a non-ionic emulsifier such as polyoxyethylene lauryl ether, polyoxyethylene monostearate, or a combination thereof is used.

[0051] The free radical initiator can be selected, for example, from azo initiators, inorganic peroxides, organic peroxides and redox initiators. Azo initiators include (2,2'-azobis(2-methylpropionamidine) dihydrochloride. Inorganic peroxides include ammonium persulfate, sodium persulfate and potassium persulfate. Organic peroxides include benzoyl peroxide and dilauroyl peroxide. Redox initiators include ammonium persulfate and 2-hydroxy-2-sulfinatoacetic acid disodium salt, hydrogen peroxide and ascorbic acid and potassium persulfate and tetramethylethylenediamine. The free radical reaction can also be initiated by high energy sources such as ultrasound and radiation according to conventional and other known procedures.

[0052] Suitable stabilizers include polymeric steric stabilizers such as partially hydrolyzed poly(vinyl acetate), thickeners such as guar gum, cellulose and its derivatives, polyacrylates and polyacrylic acid copolymers, etc. Suitable co-stabilizers include polyethers, e.g., ethylene oxide / propylene oxide copolymers, glycols, glycerin, and electrolytes such as potassium chloride and calcium chloride.

[0053] The particle size of the crosslinked silicone in the O / W emulsion of the present specification can be effectively controlled by selecting and / or adjusting the viscosity of the polyorganosiloxane before emulsification, and adjusting the temperature, mixing speed and / or emulsifier used in preparing the emulsion.In one embodiment, the particle size of the silicone gel emulsion can be 10 nm to 100 microns, specifically 100 nm to 30 microns, as measured by a dynamic laser scattering analyzer, such as a laser particle size analyzer LS230.

[0054] The combining step (a) and the adding step (b) can be carried out at room temperature or at an elevated temperature, for example up to 100°C, preferably up to 80°C.

[0055] Depending on the nature of the free radical initiator selected, the radical polymerization step (c) can be carried out at a temperature of from 40° C. to 100° C., preferably from 50° C. to 90° C., for a period of about 1 to 10 hours, preferably from 2 to 5 hours, to result in an O / W emulsion of crosslinked silicone according to the invention.

[0056] The O / W emulsion of the present invention can undergo phase inversion to a W / O emulsion after mixing with a compatible oil. Without being bound by theory, when a compatible oil is added externally to the O / W emulsion, the internal crosslinked silicone formed from the radical polymerization can "bloom" into the oil phase with the help of polyether modified polysiloxane, which can promote the contact between the internal crosslinked silicone and the external oil. And the crosslinked silicone with good compatibility with general organic oils (including silicone oil) is swollen by the external oil in the external phase, and the aqueous phase becomes the internal phase dispersed in the oil phase. Both emulsification and viscosity can be increased from the same component. The crosslinked silicone phase inversion emulsion provides excellent cushioning without sticky feeling after phase inversion of the application formulation.

[0057] In addition to visual observation, a decrease in conductivity may indicate successful phase inversion from an O / W emulsion to a W / O emulsion. When such phase inversion occurs, the conductivity is significantly reduced to less than about 5 μs / cm, and in some embodiments, even less than 1 μs / cm. Any method known for measuring conductivity may be used herein. For example, conductivity may be measured using a SevenExcellence multiparameter (Mettler Toledo).

[0058] The crosslinked silicone O / W emulsions herein, and the W / O emulsions inverted from the O / W emulsions, can be advantageously incorporated into any of many types of personal care compositions, including those having a wide variety of applications, such as deodorants, antiperspirants, antiperspirant / deodorants, stick and roll-on preparations, skin lotions, moisturizers, cosmetic fluids, cleansing preparations, styling gels, hair dyes, hair color preparations, hair straighteners, nail polish, nail polish removers, sunscreens, anti-aging preparations, lipsticks, lip balms, lip glosses, foundations, face powders, eyeliners, eye shadows, blushes, make-up, beauty balms, mascaras, moisturizing preparations, foundations, concealers, body and hand preparations, skin care preparations, face and neck preparations, fragrance preparations, soft focus preparations, day and night skin care preparations, and the like. These include, but are not limited to, topical preparations, tanning preparations, hand liquids, nonwoven preparations for personal care, facial tissues, baby lotions, facial cleansing preparations, hair cuticle coats, gels, foam baths, body washes, scrubbing cleansers, controlled release personal care preparations, hair shampoos, hair conditioners, hair sprays, skin care moisturizing mists, skin wipes, pore skin wipes, pore cleaners, blemish reducers, skin exfoliators, skin exfoliation enhancers, anti-acne preparations, skin towels, skin cloths, hair removal preparations, personal care lubricants, nail color preparations, and drug delivery systems for topically applied therapeutic agents and pharmaceuticals.

[0059] In all embodiments of the O / W gel emulsions herein, the emulsion reaction medium is devoid of precious metal hydrosilylation reaction catalysts, for example of the platinum-containing type, where the resulting crosslinked polyorganosiloxane O / W gel emulsions or crosslinked polyorganosiloxanes isolated therefrom are intended for incorporation into personal care products, given the tendency of such catalysts to cause discoloration or loss of clarity. EXAMPLES

[0060] The present invention will be described in more detail below with reference to examples, but these examples are not to be construed as limiting the scope of the present invention. In the following description, "parts" refers to "parts by weight" unless otherwise specified. Viscosity is measured by an LVDV-II+ viscometer (Brookfield).

[0061] Example 1 The mixture consisted of 40 parts by weight of a vinyl-containing dimethylpolysiloxane (M V D 560 D V 36 M V ), 5 parts by weight of bishydrogen dimethicone (M H D 20 M HThe emulsion was formed by mixing 20 parts by weight of hexafluoropropane (APRINNOVA), 20 parts by weight of hemisqualane (APRINNOVA), 10 parts by weight of PEG9 dimethicone (Momentive Performance Materials), and 2 parts by weight of steareth 21 (Croda). To this mixture, 10 parts by weight of initial water and 0.2 parts by weight of sodium surfactin (Kaneka Corporation) were then added with vigorous stirring to obtain a stable emulsion. Further deionized water was added to obtain a non-volatile content of 50% by weight. The emulsion was then heated to 60°C and adjusted to pH 4, followed by the addition of 0.05 parts by weight of ammonium persulfate to initiate the free radical polymerization of vinyl-containing dimethylpolysiloxane and its hydrosilylation with bishydrogendimethicone. After 4 hours, no SiH was detected in the stable O / W emulsion obtained, as measured by the fermentation tube method described in Luo et al., "Silicone Resin and its Application", Chemical Industry Press, Beijing, pp. 227 228 (2002). The emulsion was adjusted to pH 7 with triethanolamine, and 0.8 parts by weight of phenoxyethanol was added as a preservative. The O / W emulsion thus prepared was stable and had a viscosity of 4600 cps, as measured by an LVDV-II+ viscometer (Brookfield) using an S64 rotor at 60 rpm.

[0062] The prepared O / W emulsion was then mixed with hemisqualane as oil at room temperature in a weight ratio of 3:7. The state of the emulsion before and after mixing with oil is shown in Figure 1. The conductivity of the emulsion after mixing with hemisqualane was measured by SevenExcellence multiparameter (Mettler Toledo) at room temperature, and the viscosity was measured by LVDV-II+ viscometer (Brookfield) using S4 rotor at 60 rpm. The conductivity is 0.2 μs / cm, and the viscosity is 6,500 cPs. The results show that the prepared O / W emulsion was inverted to a W / O emulsion after mixing with oil.

[0063] Example 2 The mixture was prepared by dissolving 50 parts by weight of a vinyl-containing dimethylpolysiloxane (M V D 200 M V ), 10 parts by weight of hydrogen group-containing silicone resin (M H A mixture of 1.5 parts by weight of sodium cetostearyl sulfate, 6 parts by weight of polyoxyethylene lauryl ether, 8 parts by weight of polyoxyethylene monostearate, and 20 parts by weight of deionized water was then added to the mixture with vigorous stirring to obtain a stable emulsion. Further deionized water was added to obtain a non-volatile content of 50% by weight. The emulsion was adjusted to a temperature of 40°C and a pH of 4, and 0.1 parts by weight each of hydrogen peroxide and ascorbic acid were added to cause free radical polymerization of vinyl-containing dimethylpolysiloxane and M H Its hydrosilylation with the hydrogen group of 8Q4 was initiated. After 4 hours, no SiH was detected in the emulsion as measured by the fermentation tube method. After adjusting the pH to 5.5 with citric acid, 0.5 parts by weight of sodium benzoate was added to the emulsion as a preservative. The O / W emulsion thus prepared was stable and had a viscosity of 4800 cps as measured by an LVDV-II+ viscometer (Brookfield) using an S64 rotor at 60 rpm.

[0064] Example 3 The mixture contained 100 parts by weight of a vinyl-containing silicone resin (MV 8Q4), 15 parts by weight of PEG9 dimethicone (Momentive Performance Materials), 2 parts by weight of PEG / PPG-20 / 15 dimethicone (Momentive Performance Materials), 10 parts by weight of methylhydrogenpolysiloxane (M H D 200 M H The emulsion was formed by mixing 40 parts by weight of ethylhexyl ether (Ethyl ether), 40 parts by weight of isopropyl myristate, and 0.5 parts by weight of lauroyl peroxide at 80°C. A mixture of 4 parts by weight of steareth 2 / 21 (Croda), 4 parts by weight of polyoxyethylene monostearate, and 20 parts by weight of deionized water was then charged to the mixture with vigorous stirring to obtain a stable emulsion. Further deionized water was added to obtain a non-volatile content of 50% by weight. The emulsion was then adjusted to a temperature of 80°C to initiate free radical polymerization and free radical hydrosilylation. After 4 hours, the emulsion was found to have less than 0.1 cc / g of unreacted SiH as measured by the fermentation tube method. After adjusting the pH to 6.5 with triethanolamine, 0.8 parts by weight of phenoxyethanol was added to the emulsion as a preservative. The O / W emulsion thus prepared was stable and had a viscosity of 3200 cps as measured by an LVDV-II+ viscometer (Brookfield) using an S64 rotor at 60 rpm.

[0065] Example 4 The mixture consisted of 40 parts by weight of vinyl-containing dimethylpolysiloxane (M V D 560 D V 36 M VA 100% O / W emulsion was formed by mixing 20 parts by weight of hemisqualane (APRINNOVA), 10 parts by weight of PEG9 dimethicone (Momentive Performance Materials), and 2 parts by weight of steareth 21 (Croda). Then, 10 parts by weight of initial water and 0.2 parts by weight of sodium surfactin (Kaneka Corporation) were charged to the mixture under vigorous stirring to obtain a stable emulsion. Further deionized water was added to obtain a non-volatile content of 50% by weight. The emulsion was then thermostated at 80°C to initiate free radical polymerization, which was completed in 4 hours. Then, 0.8 parts by weight of phenoxyethanol as a preservative and 0.2 parts by weight of guar gum as a thickener were added. The O / W emulsion thus prepared was stable and had a viscosity of 4000 cps as measured by an LVDV-II+ viscometer (Brookfield) using an S64 rotor at 60 rpm.

[0066] The prepared O / W emulsion was then mixed with Silsoft 034 (Momentive Performance Materials) as oil at a ratio of 1:1.2 at room temperature. Micrographs of the emulsion before and after mixing with oil are shown in Figures 2a and 2b, respectively. The emulsion before and after mixing with oil were measured for conductivity with a SevenExcellence multiparameter (Mettler Toledo) at room temperature and for viscosity with an LVDV-II+ viscometer (Brookfield) using an S64 (front) or S4 (back) rotor at 60 rpm. The conductivity is reduced from 36.8 μs / cm to 1.6 μs / cm, and the viscosity is increased from 4,000 cPs to 112,000 cPs. The results show that the prepared O / W emulsion was inverted to W / O after mixing with oil.

[0067] The D4 (octamethylcyclotetrasiloxane), D5 (decamethylcyclopentasiloxane) and D6 (dodecamethylcyclohexasiloxane) contents of the O / W emulsions of Examples 1-4 were measured by conventional gas chromatography (GC). The measurement results are shown in Table 1 below. In general, it is advantageous to provide an O / W emulsion in which the total content of D4, D5 and D6 is controlled to less than 1,000 ppm, especially in personal care products. [Table 1]

[0068] Comparative Example 1 The mixture consisted of 40 parts by weight of a vinyl-containing dimethylpolysiloxane (M V D 560 D V 36 M V A 0.1 part by weight solution of 0.33 wt% H2PtCl6 in ethanol was added, followed by further deionized water to bring the non-volatile content to 50 wt%. The emulsion was then thermostated to 80°C to initiate polymerization. After 4 hours, 0.8 parts by weight of phenoxyethanol as a preservative and 0.2 parts by weight of guar gum as a thickener were added to the emulsion. The O / W emulsion thus prepared had a viscosity of 4200 cps as measured by an LVDV-II+ viscometer (Brookfield) using an S64 rotor at 60 rpm.

[0069] The emulsions from Example 4 and Comparative Example 1 were each demulsified with isopropyl alcohol (IPA). Photographs showing the results of demulsification are shown in Figures 3a (Example 4) and 3b (Comparative Example 1), respectively. The demulsified O / W emulsion of Example 4 showed small size gels, while no such gels were present in the demulsified emulsion of Comparative Example 1, which means that the internal phase of Comparative Example 1 was hardly cross-linked (if any).

[0070] Comparative Example 2 The mixture was prepared by mixing 100 parts by weight of a silicone resin having vinyl groups (M V D 560 D V 36 M V ), 10 parts by weight of methylhydrogenpolysiloxane (M H D 200 M H ), 40 parts by weight of isopropyl myristate, and 0.5 parts by weight of lauroyl peroxide at 80°C. A mixture of 4 parts by weight of steareth 2 / 21 (Croda), 4 parts by weight of polyoxyethylene monostearate, and 20 parts by weight of deionized water was then charged to the mixture under vigorous stirring to obtain a stable emulsion. Further deionized water was added to obtain a non-volatile content of 50% by weight. The emulsion was then adjusted to a temperature of 80°C to initiate free radical polymerization and free radical hydrosilylation. After 4 hours, the unreacted SiH in the emulsion was found to be 0.1 cc / g as measured by the fermentation tube method. After adjusting the pH to 7, 0.8 parts by weight of phenoxyethanol was added to the emulsion as a preservative. The O / W emulsion thus prepared had a viscosity of 4500 cps as measured by an LVDV-II+ viscometer (Brookfield) using an S64 rotor at 60 rpm.

[0071] Test A (Phase inversion test) The emulsion prepared in Comparative Example 2 was mixed with hemisqualane as oil in a 1:1 ratio. However, the emulsion could not invert phase after mixing with oil. As shown in Figure 4, the white emulsion was at the bottom and the hemisqualane oil was on the surface.

[0072] Test B (Water Compatibility Test) When a 30 g quantity of the emulsion prepared in Comparative Example 2 was mixed with 5 g of PEG-10 Dimethicone, the resultant changed into a thick paste. Then, 50 g of deionized water was added to the resultant while stirring, and the thick paste thinned out and had many small chips on the surface, as shown in Figure 5, indicating undesirable dilution of the water.

[0073] The results of Comparative Example 2 compared to Examples 1-4 show the function of polyether silicone for phase inversion. If no polyether silicone is used during emulsion polymerization, the prepared O / W emulsion cannot be inverted to W / O emulsion by mixing with oil. If polyether silicone is introduced after emulsion polymerization, the emulsion becomes a thick paste and has poor compatibility with water.

[0074] Examples 5-10 illustrate various personal care compositions formulated with phase inversion emulsions initiated from the O / W emulsions of the present invention, with Examples 5-9 illustrating oil-based formulations and Example 10 illustrating water-based formulations.

[0075] Example 5: Avocado cream [Table 2] procedure 1. Mix the Part A ingredients. 2. Premix Part B ingredients. 3. Slowly add Part B directly into Part A while stirring. 4. Stir at high speed for 3 to 5 minutes.

[0076] Example 6: HD Foundation [Table 3] procedure 1. Mix the Part A ingredients. 2. Premix Part B ingredients. 3. Premix Part C ingredients. 4. Slowly add Part B directly into Part A while stirring, then stir the mixture at high speed for 3 to 5 minutes. 5. Blend the A / B mixture with the premixed Part C.

[0077] Example 7: Concealer balm [Table 4] procedure 1. Mix all ingredients of Part A and heat to 80°C. 2. Premix Part B ingredients. 3. After cooling to 65°C, add Part A to Part B with stirring.

[0078] Example 8: Lip balm [Table 5] procedure 1. Mix all ingredients of Part A and heat to 80°C. 2. Premix Part B ingredients. 3. After cooling to 65°C, add Part A to Part B with stirring.

[0079] Example 9: Silky Cream [Table 6] procedure 1. Mix all ingredients of Part A and heat Part A to about 80°C. 2. Dissolve the ingredients of Part B in water and heat Part B to approximately 80°C. 3. Add Part A to Part B while stirring and homogenize for a few minutes. 4. Add Part C to Part A / B while stirring. 5. Add Part D to Parts A / B / C while stirring.

[0080] Example 10: Dual layer hairspray [Table 7] procedure 1. Add Part C to Part B while stirring. 2. Mix Part A ingredients. 3. Add Part A to the Part B / C mixture.

[0081] Each of the resulting formulations from Examples 5-10 was tested for stability for one week in an oven at 50° C. The formulations remained unchanged.

[0082] Although the present disclosure has been described with reference to preferred embodiments, those skilled in the art will recognize that various changes can be made and equivalents substituted for elements thereof without departing from the scope of the present disclosure. In addition, many modifications can be made to adapt a particular situation or material to the teachings of the present disclosure without departing from the essential scope of the present disclosure. Therefore, it is not intended that the disclosure be limited to the particular embodiment disclosed as the best mode contemplated for carrying out the disclosure, but the disclosure is intended to include all embodiments falling within the scope of the appended claims.

Claims

1. A method for producing an oil-in-water emulsion of a crosslinked silicone, comprising radically polymerizing, under emulsion polymerization reaction conditions, at least one polyorganosiloxane having at least two aliphatically unsaturated carbon-carbon bonds, and optionally an organohydrogenpolysiloxane, in the presence of a polyether-modified polysiloxane; wherein at least one polyorganosiloxane is of general formula (I) M ｇ M Ｈ ｈ M Ｖ ｉ M Ｆ ｊ D ｋ D Ｈ ｌ D Ｖ ｍ D Ｆ ｎ T ｏ T Ｈ ｐ T Ｖ ｑ T Ｆ ｒ Q ｓ Formula (I) where M=R ２１ R ２２ R ２３ SiO １／２ ; M Ｈ =R ２４ R ２５ HSiO １／２ ; M Ｖ =R ２６ R ２７ R ２８ SiO １／２ ; M Ｆ =R ２９ R ３０ R Ｆ SiO １／２ ; D=R ３１ R ３２ SiO ２／２ ; D Ｈ =R ３３ HSiO ２／２ ; D Ｖ =R ３４ R ３５ SiO ２／２ ; D Ｆ =R ３６ R Ｆ SiO ２／２ ; T=R ３７ SiO ３／２ ; T Ｈ =HSiO ３／２ ; T Ｖ =R ３８ SiO ３／２ ; T Ｆ = R Ｆ SiO ３／２ and Q=SiO ４／２ Here, R ２１ , R ２２ , R ２３ , R ２４ , R ２５ , R ２７ , R ２８ , R ３１ , R ３２ , R ３３ , R ３５ and R ３７ are each independently a monovalent hydrocarbon radical of up to 60 carbon atoms; R ２６ , R ３４ and R ３８ are each independently a vinyl, allyl or methallyl group; R ２９ , R ３０ and R ３６ are each independently a monovalent hydrocarbon group of up to 60 carbon atoms or R Ｆ and each R Ｆ are independently a monovalent alkoxy or ether group of up to 60 carbon atoms; and the subscripts g, h, i, j, k, l, m, n, o, p, q, r, and s are each independently integers from 0 to 1000, subject to the limit that i+m+q≧2; A method for producing an O / W emulsion.

2. The polyorganosiloxane is M Ｖ ｉ D ｋ D Ｖ ｍ M ２－ｉ (I-1) Here, M Ｖ , D, D Ｖ and M are as defined in claim 1, and the subscripts i, k, and m are integers, subject to the limitations that i is 0 to 2, k is 0 to 600, and m is 0 to 100; and R ２６ and R ３４ are each independently selected from the group consisting of vinyl, allyl, or methallyl groups; M Ｖ ｉ Q ｓ (I-2) Here, M Ｖ and Q are as defined in claim 1, and the subscripts i and s are integers, subject to the limitations that i > 1, s > 1, and i + s is from 2 to 50, and each R ２６ is selected from the group consisting of vinyl, allyl or methallyl groups; 2. The method for producing an O / W emulsion according to claim 1, wherein the emulsion is at least one member selected from the group consisting of:

3. The organohydrogenpolysiloxane is of the general formula (I): M ｇ M Ｈ ｈ M Ｖ ｉ M Ｆ ｊ D ｋ D Ｈ ｌ D Ｖ ｍ D Ｆ ｎ T ｏ T Ｈ ｐ T Ｖ ｑ T Ｆ ｒ Q ｓ Formula (I) Here, M, M Ｈ , M. Ｖ , M. Ｆ , D, D Ｈ , D Ｖ , D Ｆ , T, T Ｈ , T Ｖ , T Ｆ and Q are as defined in claim 1, and the subscripts g, h, i, j, k, l, m, n, o, p, q, r, and s are each independently an integer from 0 to 500, with the limitations that h+l+p≧1 and i+m+q≧2, the formula (I) defined for the polyorganosiloxane and the organohydrogenpolysiloxane is different. A method for producing an O / W emulsion according to claim 1 or 2.

4. Organohydrogenpolysiloxane, M Ｈ ｈ D ｋ D Ｈ ｌ M ２－ｈ (I-3) Here, M Ｈ , D, D Ｈ and M are as defined in claim 1, and h, k, and l are 0 or positive numbers, subject to the limitations that k is 10 to 300, l is 0 to 50, h is 0 to 2, and h+l is 1 to 100; M Ｈ ｈ Q ｓ (I-4) Here, M Ｈ and Q is as defined in claim 1, and the subscripts h and s are integers, subject to the limitations that h > 1, s > 1, and i + s is from 2 to 50; 4. The method for producing an O / W emulsion according to claim 1, wherein the emulsion is at least one member selected from the group consisting of:

5. The polyether-modified polysiloxane is represented by the general formula (II): M １ ａ M ２ ｂ M ３ ｃ D １ ｄ D ２ ｅ D ３ ｆ Formula (II) where M １ =R １ R ２ R ３ SiO １／２ M ２ =R ４ R ５ R ６ SiO １／２ M ３ =R ７ R ８ R ９ SiO １／２ D １ =R １０ R １１ SiO ２／２ D ２ =R １２ R １３ SiO ２／２ D ３ =R １４ R １５ SiO ２／２ In the formula (II), R １ , R ２ , R ３ , R ４ , R ５ , R ７ , R ８ , R １０ , R １１ , R １２ and R １４ are each independently an alkyl or aryl group having up to about 60 carbon atoms; R ６ and R １３ Each independently represents -R １６ -O-(C ２ H ４ O) ｘ (C ３ H ６ O) ｙ (C ４ H ８ O) ｚ -R １７ where R １６ is a divalent alkylene group of 1 to about 20 carbon atoms; R １７ is selected from hydrogen, an alkyl, acyl, or ester group having from 1 to about 20 carbon atoms, and the subscripts x, y, and z are each independently integers from 0 to 200, subject to the limit that 1≦x+y+z≦200; R ９ and R １５ are each independently a straight or branched chain alkyl group of from 4 to about 20 carbon atoms; a monovalent alkoxy or aryloxy group of up to about 20 carbon atoms; or a divalent alkylene group having from 1 to about 20 carbon atoms terminated with an alkoxy, aryloxy, amino, ester, amide, or epoxide group; 5. The method for producing an O / W emulsion according to claim 1, wherein the subscripts a, b, c, d, e, and f are each independently an integer from 0 to 200, subject to the restriction that b+e≧1.

6. The polyether-modified polysiloxane is M １ ２ D １ ｄ D ２ ｅ (II-1) Here, M １ , D １ and D. ２ is as defined in claim 5, d is 1 to 200, and e is 1 to 200; and M ２ ｂ D １ ｄ D ２ ｅ M １ ２－ｂ (II-2) Here, M １ , M. ２ , D １ , and D ２ is as defined in claim 5, b is 1 or 2, d is 1 to 200, and e is 1 to 200.

6. The method for producing an O / W emulsion according to claim 1, wherein the emulsion is at least one member selected from the group consisting of:

7. The polyether-modified polysiloxane is used in an amount of about 5 to about 50 parts by weight based on 100 parts by weight of the total amount of the polyorganosiloxane having at least two aliphatically unsaturated carbon-carbon bonds and the organohydrogenpolysiloxane, if present. The method for producing an O / W emulsion according to any one of claims 1 to 6.

8. (a) combining a polyorganosiloxane with a polyether-modified polysiloxane and an optional organohydrogenpolysiloxane to obtain a mixture; (b) adding an aqueous medium containing an emulsifier to the mixture with stirring; and 8. The method for producing the O / W emulsion according to claim 1, which comprises (c) subjecting the mixture to radical polymerization.

9. 9. A method for producing a W / O emulsion by phase inversion of an O / W emulsion obtained by the method according to any one of claims 1 to 8, by adding oil to said O / W emulsion.

10. A personal care composition comprising an O / W emulsion obtained by the process according to any one of claims 1 to 8 or a W / O emulsion obtained by the process according to claim 9.

11. 11. A personal care application comprising the personal care composition of claim 10, comprising deodorants, antiperspirants, antiperspirants / deodorants, stick and roll-on preparations, skin lotions, moisturizers, cosmetic liquids, cleansing preparations, styling gels, hair dyes, hair color preparations, hair straighteners, nail polish, nail polish removers, sunscreens, anti-aging preparations, lipsticks, lip balms, lip glosses, foundations, face powders, eyeliners, eye shadows, blushes, make-up, beauty balms, mascaras, moisturizing preparations, foundations, concealers, body and hand preparations, skin care preparations, face and neck preparations, fragrance preparations, soft focus preparations, day and night skin care. personal care applications selected from the group consisting of topical formulations, tanning preparations, hand liquids, personal care nonwoven preparations, facial tissues, baby lotions, facial cleansing preparations, hair cuticle coats, gels, foam baths, body washes, scrubbing cleansers, controlled release personal care preparations, hair shampoos, hair conditioners, hair sprays, skin care moisturizing mists, skin wipes, pore skin wipes, pore cleansers, blemish reducers, skin exfoliators, skin exfoliation enhancers, anti-acne preparations, skin towels, skin cloths, hair removal preparations, personal care lubricants, nail coloring preparations, and topically applied therapeutic agents and drug delivery systems for pharmaceuticals.

Images