O / W emulsions and W / O emulsions inverted therefrom, and personal care compositions containing the same

Abstract

The present invention relates to an O / W emulsion invertible to a W / O emulsion and a W / O emulsion inverted from said O / W emulsion, wherein said O / W emulsion is obtained from the free radical polymerization under emulsion polymerization conditions of at least one polyorganosiloxane having at least two aliphatically unsaturated carbon-carbon bonds with optionally a hydridocntaining organopolysiloxane in the presence of a polyether-modified polysiloxane. The present invention further relates to a process for the preparation of the O / W emulsion and the W / O emulsion and to a personal care composition comprising said emulsions.

Description

Technical Field

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

[0002] Emulsions are widely used in personal care products. An emulsion is generally defined as a metastable colloid, consisting of two immiscible fluids, oil and water, one dispersed (dispersed phase) in the presence of a surfactant in the other (continuous phase). Depending on the type of dispersed and continuous phases, emulsions can be classified as water-in-oil (W / O) emulsions and oil-in-water (O / W) emulsions. The conversion between these two types of emulsions is commonly referred to as phase inversion or emulsion reversal.

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

[0004] Furthermore, although O / W emulsions have been studied more extensively than W / O emulsions, they are rarely successfully reversed into W / O emulsions. Summary of the Invention

[0005] In one aspect, the present invention relates to an O / W emulsion of crosslinked organosilicon, wherein the O / W emulsion is obtained from the free radical polymerization of at least one polyorganosiloxane having at least two aliphatic unsaturated carbon-carbon bonds and optionally a hydrogen-containing organopolysiloxane (hydrogen-functionalized organopolysiloxane) in the presence of a polyether-modified polysiloxane under emulsion polymerization conditions.

[0006] The O / W emulsion of the present invention can be prepared by a method comprising the following steps:

[0007] (a) Combining the polyorganosiloxane with the polyether-modified polysiloxane and optionally a hydrogen-containing organopolysiloxane to obtain a mixture;

[0008] (b) Adding an aqueous medium containing an emulsifier to the mixture under stirring; and

[0009] (c) subject the mixture to free radical polymerization.

[0010] In another aspect, the present invention relates to W / O emulsions, which are obtained by adding oil to the O / W emulsion of the present invention to reverse the O / W emulsion.

[0011] In another aspect, the present invention relates to personal care compositions comprising an O / W emulsion or a W / O emulsion according to the present invention.

[0012] Surprisingly, it has been found that the O / W emulsion of the present invention can be reversed into a W / O emulsion by increasing the volume fraction of the oil phase, for example, by simply mixing with common oils or fats (especially those commonly used in personal care formulations) to increase the volume fraction of the oil phase. After the phase reversal, the internally cross-linked silicone formed by emulsion polymerization enters and occupies the continuous phase by swelling in the oil phase, and it can act as a rheology modifier in the formulation of personal care products. The phase reversal capability of O / W emulsions is highly advantageous. The O / W emulsion will be compatible with water or aqueous components due to its aqueous continuous phase, and will also be compatible with oil or oily components due to the phase reversal. Therefore, the phase reversal emulsion of the present invention can facilitate the introduction of aqueous components into W / O emulsions (including water / silicone oil emulsions) or oil-based formulations. Formulations formed from the emulsions of the present invention, especially cosmetic formulations, can provide excellent stability and a superior feel in use, and the addition of aqueous components provides a good cushioning feel without any stickiness. Attached Figure Description

[0013] Figure 1 The images shown are photographs taken before and after the emulsion prepared in Example 1 was mixed with hemisqualane as an oil.

[0014] Figure 2a and 2b Micrographs are shown of the emulsion prepared in Example 4 before (2a) and after (2b) phase inversion using Silsoft 034 as oil.

[0015] Figure 3a and 3bThe images show photographs taken of the demulsification of the emulsions prepared in Example 4 (3a) and Comparative Example 1 (3b) using isopropanol (IPA).

[0016] Figure 4 The image shows a photograph of the emulsion prepared in Comparative Example 2 after it was mixed with hemisqualane as an oil at a 1:1 ratio.

[0017] Figure 5a and 5b The images shown are photographs of the emulsion prepared in Comparative Example 2 after being mixed with PEG-10 polydimethylsiloxane (5a) and further mixed with deionized water (5b). Detailed Implementation

[0018] In the specification and claims herein, the following terms and expressions shall be understood as indicated.

[0019] The singular forms “a,” “an,” and “the (said)” cover the plural, and references to a specific numerical value include at least that specific value, unless the context clearly specifies otherwise.

[0020] All methods described herein may be implemented in any suitable order unless otherwise indicated herein or clearly contrary to the context. Any and all instances or exemplary language (such as “for example”) provided herein are intended only to better illustrate the invention and do not impose a limitation on the scope of the invention, unless otherwise claimed.

[0021] Nothing in the specification should be construed as designating any unrequired element as necessary for the practice of the invention.

[0022] The terms “comprising,” “including,” “containing,” “characterized by,” and their grammatical equivalents are inclusive or open-ended terms that do not exclude additional unmentioned elements or methodological steps, but will also be understood to include the more restrictive terms “consisting of” and “substantially consisting of”.

[0023] Except where specified in the working embodiments or elsewhere, all figures representing amounts of material, temperatures, durations, quantitative properties of materials, etc., set forth in the specification and claims shall be understood to be modified by the term “about” in all cases, whether or not the term “about” is used in the description.

[0024] It will be understood that any quantity range referred to herein includes all subranges within that range and any combination of the different endpoints of such ranges or subranges.

[0025] It will also be understood that any compound, material, or substance that is explicitly or implicitly disclosed in the specification and / or referred to in the claims as belonging to a group of compounds, materials, or substances that are related in structure, composition, and / or function includes individual representatives of that group and all combinations thereof.

[0026] The term "hydrocarbon group" means any hydrocarbon that has had one or more hydrogen atoms removed and includes alkyl, alkenyl, ynyl, cycloalkyl, cycloalkenyl, cycloynyl, aryl, aralkyl and alkylaryl groups and includes hydrocarbon groups containing at least one heteroatom.

[0027] The term "alkyl" means any monovalent, saturated, straight-chain, branched, or cyclic hydrocarbon group; the term "alkenyl" means any monovalent, straight-chain, branched, or cyclic hydrocarbon group containing one or more carbon-carbon double bonds, wherein the linkage site of the group may be at a carbon-carbon double bond or other positions thereof; and the term "alkynyl" means any monovalent, straight-chain, branched, or cyclic hydrocarbon group containing one or more carbon-carbon triple bonds and optionally one or more carbon-carbon double bonds, wherein the linkage site of the group may be at a carbon-carbon triple bond, a carbon-carbon double bond, or other positions thereof. Examples of alkyl groups include methyl, ethyl, propyl, and isobutyl. Examples of alkenyl groups include vinyl, propynyl, allyl, methylallyl, ethylidene norbornane, ethylidene norbornyl, ethylidene norbornylene, and ethylidene norbornylene. Examples of alkynyl groups include ethynyl, propynyl, and methylethynyl.

[0028] The terms "cycloalkyl," "cycloalkenyl," and "cycloalkynyl" encompass 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, norbornyl, ethylnorbornyl, ethylnorbornyl, cyclohexyl, ethylcyclohexyl, ethylcyclohexenyl, cyclohexylcyclohexyl, and cyclododecanetrienyl.

[0029] 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 have been replaced by an equal number of the same and / or different aryl groups (as defined herein); and the term "alkylaryl" means any aryl group (as defined herein) in which one or more hydrogen atoms have been replaced by an equal number of the same and / or different alkyl groups (as defined herein). Examples of aryl groups include phenyl and naphthyl. Examples of aralkyl groups include benzyl and phenethyl. Examples of alkylaryl groups include tolyl and xylyl.

[0030] The term "heteroatom" refers to any of the elements in groups 13-17 other than carbon, and includes, for example, oxygen, nitrogen, silicon, sulfur, phosphorus, fluorine, chlorine, bromine, and iodine.

[0031] In one embodiment, the hydrocarbon group contains up to 60 carbon atoms if present, in another embodiment up to 30 carbon atoms, and in yet another embodiment up to 20 carbon atoms.

[0032] Available 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 groups, such as n-hexyl; heptyl groups, such as n-heptyl; octyl groups, such as n-octyl, isooctyl, and 2,2,4-trimethylpentyl; nonyl groups, such as n-nonyl; decyl groups, such as n-decyl; and cycloalkyl groups, such as cyclopentyl, cyclohexyl, cycloheptyl, and methylcyclohexyl. Examples of alkenyl groups include vinyl, propynyl, allyl, methylallyl, cyclohexenyl, norbornenyl, ethyl norbornenyl, vinylidene norbornenane, ethyl norbornenyl, vinylidene norbornenene, and ethyl norbornenyl. Examples of alkynyl groups include ethynyl, propynyl, and methylethynyl. Examples of aryl groups include phenyl, naphthyl; o-, meta-, and p-tolyl, xylyl, ethylphenyl, and benzyl.

[0033] The terms and expressions “hydrosilyl,” “hydride,” “organosilicon hydride,” and “SiH” are understood to be used interchangeably in the field of organosiloxanes and refer to polyorganosiloxanes containing one or more hydrogen atoms directly bonded to silicon.

[0034] The term "emulsion" as used herein should also be understood to include "microemulsion".

[0035] As used herein, the term "oil" should also be understood to include, but is not limited to, polysiloxane liquids such as silicone oil.

[0036] The terms or words used in the specification and claims should not be construed as having a general or dictionary meaning, but should be interpreted as having a meaning and concept consistent with the concept of the invention based on the principle that the inventor may appropriately define the concept of the terms to best interpret his own invention.

[0037] The inventors of this invention have surprisingly discovered that a crosslinked organosilicon O / W emulsion can be reversed to a W / O emulsion by increasing the volume fraction of the oil phase, wherein the crosslinked organosilicon O / W emulsion is obtained from the free radical polymerization of at least one polyorganosiloxane having at least two aliphatic unsaturated carbon-carbon bonds and optionally a hydrogen-containing organopolysiloxane in the presence of a polyether-modified polysiloxane under emulsion polymerization conditions.

[0038] The polyorganosiloxane has at least two aliphatic unsaturated carbon-carbon bonds, which can undergo free radical addition polymerization to form crosslinked organosilicon in the inner phase of the O / W emulsion. The number of aliphatic unsaturated carbon-carbon bonds can be, for example, from 2 to about 1000, preferably from 2 to about 500, and more preferably from 2 to about 100.

[0039] In a preferred embodiment, the polyorganosiloxane comprises at least two alkenyl and / or ynyl groups. When a hydrogen-containing organopolysiloxane is present, the radical addition polymerization reaction includes not only the radical polymerization of the alkenyl / ynyl groups in the polyorganosiloxane, but also the hydrosilylation reaction between the Si-H groups in the hydrogen-containing organopolysiloxane and the alkenyl / ynyl groups in the polysiloxane. The polyorganosiloxane may also contain Si-H functional groups.

[0040] In one embodiment, the polyorganosiloxane having at least two aliphatic unsaturated carbon-carbon bonds has the general formula (I):

[0041] 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 General Formula (I)

[0042] in

[0043] M = R 21 R 22 R 23 SiO 1 / 2 ;

[0044] M H =R 24 R 25 HSiO 1 / 2 ;

[0045] M V =R 26 R 27 R 28 SiO 1 / 2 ;

[0046] MF =R 29 R 30 R F SiO 1 / 2 ;

[0047] D = R 31 R 32 SiO 2 / 2 ;

[0048] D H =R 33 HSiO 2 / 2 ;

[0049] D V =R 34 R 35 SiO 2 / 2 ;

[0050] D F =R 36 R F SiO 2 / 2 ;

[0051] T = R 37 SiO 3 / 2 ;

[0052] T H =HSiO 3 / 2 ;

[0053] T V =R 38 SiO 3 / 2 ;

[0054] T F =R F SiO 3 / 2 ;as well as

[0055] Q = SiO 4 / 2

[0056] Where 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 Each is independently a monovalent hydrocarbon group with up to 60 carbon atoms, particularly up to 30 carbon atoms, and even more particularly up to 20 carbon atoms; R 26 R 34 and R 38Each is an olefinic unsaturated group consisting independently of up to 30 carbon atoms, particularly up to 20 carbon atoms, and even more particularly up to 10 carbon atoms; R 29 R 30 and R 36 Each is independently a monovalent hydrocarbon group or R with up to 60 carbon atoms, more particularly up to 30 carbon atoms, and even more particularly up to 20 carbon atoms. F Each R F Independently, it is a monovalent alkoxy or ether group with up to 60 carbon atoms, more particularly up to 30 carbon atoms, and even more particularly 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 an integer from 0 to 1000, provided that i + m + q ≥ 2, for example, an integer from 2 to approximately 500.

[0057] In a preferred embodiment, the polyorganosiloxane having at least two aliphatic unsaturated carbon-carbon bonds is selected from at least one of the following:

[0058] M V i D k D V m M 2-i (I-1)

[0059] Where M V D, D V Let M be as defined above, and let the subscripts i, k, and m be integers, where i is 0 to 2; k is 0 to 1000, specifically 10 to 600, and even more specifically 10 to 500; m is 0 to 100, and even more specifically 0 to 50; and R 26 and R 34 Each group is independently selected from vinyl, allyl, methallyl, acrylate or alkyl acrylate groups, preferably vinyl or allyl;

[0060] M V i Q s (I-2)

[0061] Where M V Let R and Q be as defined above, with subscripts i and s being integers, provided that i ≥ 1, especially ≥ 2, and more especially ≥ 3; s ≥ 1, especially ≥ 2, and more especially ≥ 3; and i + s are from 2 to 50, especially 2 to 20, and more especially 2 to 15; and each R 26 The group is selected from vinyl, allyl, methyl allyl, acrylate or alkyl acrylate groups, preferably vinyl or allyl.

[0062] In one embodiment, the hydrogen-containing organopolysiloxane is present and has the general formula (I):

[0063] 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)

[0064] Among them M, M H M V M F D, D H D V D F T, T H T V T F Q is 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, particularly from 0 to 200, and more particularly from 0 to 100, provided that (1) h+l+p≥1, particularly ≥2, and more particularly ≥8, and (2) when i+m+q≥2, the formula (I) defined for polyorganosiloxanes is different from the formula (I) defined for hydrogen-containing organopolysiloxanes.

[0065] In a preferred embodiment, the hydrogen-containing organopolysiloxane is selected from at least one of the following:

[0066] M H h D k D H l M 2-h (I-3)

[0067] Where M H D, D HM is as defined above, and h, k, and l are 0 or positive numbers, provided that h is 0 to 2; k is 10 to 300, especially 10 to 200, and even more especially 20 to 200; l is 0 to 50, especially 0 to 20, and even more especially 1 to 10; and h+l is 1 to 100, even more especially 1 to 32, and even more especially 2 to 12;

[0068] M H h Q s (I-4)

[0069] Where M H Q is as defined above, and the subscripts h and s are integers, provided that h ≥ 1, especially ≥ 2 and more especially ≥ 3; s ≥ 1, especially ≥ 2 and more especially ≥ 3; and i + s is 2 to 50, especially 2 to 20, and more especially 2 to 15.

[0070] The ratio of total olefinic unsaturated groups (including olefinic unsaturated groups present in polyorganosiloxanes and hydrogen-containing organopolysiloxanes, if any) to total Si-H functional groups (including Si-H functional groups present in polyorganosiloxanes and hydrogen-containing organopolysiloxanes, if any) should be at least 1 and advantageously at least 2. The weight ratio of total polyorganosiloxanes to total hydrogen-containing organopolysiloxanes 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.

[0071] The viscosity of polyorganosiloxanes and hydrogen-containing organopolysiloxanes can vary widely. For example, the viscosity of polyorganosiloxanes, measured by the Brookfield rotational viscometry, can range from 0.0002 to 1000 Pa·s, particularly from 0.001 Pa·s to 100 Pa·s. The viscosity of hydrogen-containing organopolysiloxanes, measured by the Brookfield rotational viscometry, can range from 0.001 to 50 Pa·s, particularly from 0.002 to 10 Pa·s.

[0072] In most cases, the polyorganosiloxanes having at least two aliphatic unsaturated carbon-carbon bonds and the hydrogen-containing organopolysiloxanes are present in the O / W emulsion polymerization reaction mixture at the start of polymerization. However, the following falls within the scope of the invention: the polyorganosiloxane is initially polymerized alone, and only after this, but before the polymerization of the polyorganosiloxane is complete, is the optional hydrogen-containing organopolysiloxane introduced into the emulsion reaction medium, thus removing the unreacted M present in the polyorganosiloxane. V D V and / or T V The unit will be through M present in hydrogen-containing organopolysiloxanes H D H and / or T HThe unit undergoes a hydrosilylation reaction. In the preparation of interpenetrating polymer networks (IPNs) or core-shell structures, it is advantageous to delay the addition of hydrogen-containing organosiloxanes to the polyorganosiloxane.

[0073] As used herein, "polyether-modified polysiloxane" refers to a polysiloxane in which one or more polyether moieties are directly or via divalent hydrocarbon groups bonded to silicon atoms in the polysiloxane backbone. The polyether moieties consist of one or more olefin oxide groups. Preferably, the olefin oxide groups are selected from at least one of vinyl oxide groups, propylene oxide groups, and butene oxide groups. The silicon atoms bonded to the polyether moieties may be located in the M unit (SiO₂). 1 / 2 ), D unit (SiO) 2 / 2 ) or T unit (SiO) 3 / 2 In any unit of the ) unit, M unit and / or D unit are preferred, and M unit is more preferred. The divalent hydrocarbon group is preferably a divalent straight-chain or branched alkylene group having 1 to about 20 carbon atoms, more preferably 2 to about 10 carbon atoms, and even more preferably 3 to 6 carbon atoms.

[0074] In addition to the polyether moiety, polyether-modified polysiloxanes may also contain other functional groups, such as alkoxy, aryloxy, amino, ester, amide, or epoxy groups, which may be directly or via divalent hydrocarbon groups (such as the divalent hydrocarbon groups listed above for the polyether moiety) bonded to the silicon atoms in the polysiloxane backbone.

[0075] In a preferred embodiment, the polyether-modified polysiloxane has the general formula (II):

[0076] M 1 a M 2 b M 3 c D 1 d D 2 e D 3 f Equation (II)

[0077] in:

[0078] M 1 =R 1 R 2 R 3 SiO 1 / 2

[0079] M 2 =R 4 R 5 R 6 SiO 1 / 2

[0080] M 3 =R 7 R 8 R 9 SiO 1 / 2

[0081] D 1 =R 10 R 11 SiO 2 / 2

[0082] D 2 =R 12 R 13 SiO 2 / 2

[0083] D 3 =R 14 R 15 SiO 2 / 2

[0084] In equation (II),

[0085] R 1 R 2 R 3 R 4 R 5 R 7 R 8 R 10 R 11 R 12 and R 14 Each of the groups is independently a monovalent hydrocarbon group having up to about 60 carbon atoms, preferably an alkyl or aryl group having up to 10 carbon atoms, more preferably an alkyl or phenyl group having 1-4 carbon atoms, and even more preferably a methyl group;

[0086] R 6 and R 13 Each independently is -R 16 -O-(C2H4O) x (C3H6O) y (C4H8O) z -R 17 , where R 16 It is a divalent straight-chain or branched alkylene group having 1 to 20 carbon atoms, preferably 2 to 10 carbon atoms, more preferably about 3 to 6 carbon atoms, optionally containing oxygen or nitrogen atoms; R 17 Selected from hydrogen, and alkyl, acyl (-C(O)R, where R is alkyl) or ester group (-C(O)OR, where R is alkyl) having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, and subscripts x, y and z are each independently integers from 0 to 200, preferably from 1 to 100, and more preferably from 2 to 20, provided that 1≤x+y+z≤200;

[0087] R 9 and R 15 Each is independently a straight-chain or branched alkyl group having 4 to 20 carbon atoms, optionally containing an F atom; a straight-chain or branched alkoxy or aryloxy group having up to 20 carbon atoms; or a divalent alkylene group having 1 to 20 carbon atoms, preferably 3 to 10 carbon atoms, optionally containing an F atom, terminated with an alkoxy, aryloxy, amino, ester, amide, or epoxy group.

[0088] The subscripts a, b, c, d, e, and f are each independent integers from 0 to 200, provided that b + e ≥ 1.

[0089] In a preferred embodiment, the polyether-modified polysiloxane is selected from at least one of the following:

[0090] M 1 2D 1 d D 2 e (II-1)

[0091] Where M 1 D 1 and D 2 As defined above for formula (II), d is 1 to about 200, preferably 1 to about 100; and e is 1 to about 200, preferably 1 to about 100; and

[0092] M 2 b D 1 d D 2 e M 1 2-b (II-2)

[0093] Where M 1 M 2 D 1 and D 2 As defined above for formula (II), b is 1 or 2, d is 1 to 200, preferably 1 to about 100; and e is 1 to 200, preferably 1 to about 100.

[0094] The polyether-modified polysiloxanes are well known in the art to be prepared by hydrosilylation of Si-H functionalized polysiloxanes with vinyl-containing polyethers in the presence of a platinum catalyst. The polyether-modified polysiloxanes are also commercially available, for example, PEG-3 polydimethylsiloxane, PEG-6 polydimethylsiloxane, PEG-7 polydimethylsiloxane, PEG-8 polydimethylsiloxane, PEG-9 polydimethylsiloxane, PEG-10 polydimethylsiloxane, PEG-12 polydimethylsiloxane, PEG-14 polydimethylsiloxane, PEG-17 polydimethylsiloxane, and PEG / PPG-20 / 15 polydimethylsiloxane (all from Momentive Performance Materials).

[0095] Based on a total of 100 parts by weight of the polyorganosiloxane having at least two aliphatic unsaturated carbon-carbon bonds and the hydrogen-containing organopolysiloxane (if present), the polyether-modified polysiloxane is used in an amount of about 5 to about 50 parts by weight, preferably about 8 to about 35 parts by weight, and more preferably about 10 to about 30 parts by weight.

[0096] The radical-initiated polymerization of polyorganosiloxanes and the hydrosilylation of polyorganosiloxanes with hydrogen-containing organopolysiloxanes (if present) can be carried out in an O / W emulsion polymerization reaction medium using conventional or otherwise known emulsion polymerization procedures.

[0097] In such emulsion polymerization processes, the dispersed oil phase of the emulsion reaction mixture comprises a polyorganosiloxane, a polyether-modified polysiloxane, optionally a hydrogen-containing organopolysiloxane, and optionally an organic solvent and / or a swelling agent (compensator). The continuous aqueous phase of the emulsion reaction medium comprises water and water-soluble or water-miscible components, such as emulsifiers, free radical initiators, and optional components such as stabilizers, co-stabilizers, chain transfer agents, etc. Typically, the oil phase may constitute 1-80% by weight, and advantageously 30-70% by weight, of the emulsion polymerization reaction medium, with the balance made up by the aqueous phase.

[0098] In one embodiment, the O / W emulsion is prepared by a method comprising:

[0099] (a) Combining a polyorganosiloxane with a polyether-modified polysiloxane, an optional hydrogen-containing polyorganosiloxane, and an optional organic solvent and / or swelling agent (compensator) to obtain a mixture;

[0100] (b) Adding an aqueous medium containing an emulsifier, a free radical initiator, and optionally a stabilizer and / or a co-stabilizer to the mixture under stirring; and

[0101] (c) Allow the mixture to undergo free radical polymerization.

[0102] Solvents and / or swelling agents (compatibilizers) can be introduced 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 polymethylsiloxanes, alkyl polymethylsiloxanes such as octyl polymethylsiloxane, polydimethylsiloxane, alkyl polydimethylsiloxane, phenyl polydimethylsiloxane, amino polydimethylsiloxane, trimethylsiloxysilicate, and polymethylsilsesquioxane; hydrocarbons such as isodecanene, hexadecane, and squalane; triglycerides such as octyl triglyceride; esters such as cetyl palmitate and isopropyl myristate; and ethers such as dipropylene glycol butyl ether. Such solvents / swelling agents may constitute up to 95% by weight of the oil phase of the O / W emulsion reaction medium.

[0103] Suitable emulsifiers include nonionic and anionic types of emulsifiers, as well as mixtures thereof. Suitable nonionic emulsifiers include any nonionic emulsifiers that have been used to date in emulsion polymerization processes, such as alcohol ethoxylates, polyoxyethylene lauryl ethers, polyoxyethylene monostearates, etc. Similarly, available anionic emulsifiers include those known to be used in emulsion polymerization processes, such as alkali metal sulfonates, sulfates, phosphates, and sulfosuccinate surfactants. Specific examples of these surfactants include alkali metal sulfonylresorcinol salts; sulfonated glycerol esters of fatty acids; salts of sulfonated monovalent alcohol esters; sulfonated alkali metal salts of aromatic hydrocarbons, such as sodium α-naphthalene monosulfonate; sulfates, such as sodium lauryl sulfate, sodium cetearyl sulfate, triethanolamine lauryl sulfate, and sodium lauryl ether sulfate; phosphates, such as potassium cetyl phosphate; and sulfosuccinates, such as disodium lauryl sulfosuccinate. In a preferred embodiment, a nonionic emulsifier such as polyoxyethylene lauryl ether, polyoxyethylene monostearate, or a combination thereof is used.

[0104] Free radical initiators can be selected from, for example, azo initiators, inorganic peroxides, organic peroxides, and redox initiators. Azo initiators include (2,2-azobis(2-methylpropanediamine) dihydrochloride). Inorganic peroxides include ammonium persulfate, sodium persulfate, and potassium persulfate. Organic peroxides include benzoyl peroxide and dilauryl peroxide. Redox initiators include ammonium persulfate and disodium 2-hydroxy-2-sulfinylacetate, hydrogen peroxide and ascorbic acid, and potassium persulfate and tetramethylethylenediamine. Free radical reactions can also be initiated using high-energy sources such as ultrasound and radiation according to conventional and other known procedures.

[0105] 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. Suitable co-stabilizers include polyethers such as ethylene oxide / propylene oxide copolymers, glycols, glycerol, and electrolytes such as potassium chloride and calcium chloride.

[0106] The particle size of the crosslinked silicone in the O / W emulsion described herein can be effectively controlled by selecting and / or adjusting the viscosity of the polysiloxane prior to emulsification, as well as by 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–100 μm, and particularly 100 nm–30 μm, as determined by a dynamic laser scattering analyzer such as a laser particle size analyzer LS230.

[0107] The combination step (a) and the addition step (b) can be carried out at room temperature or at an elevated temperature not exceeding, for example, 100°C, preferably not exceeding 80°C.

[0108] Depending on the nature of the selected free radical initiator, the free radical polymerization step (c) can be carried out at a temperature of 40°C to 100°C, preferably 50°C to 90°C, for 1 to 10 hours, preferably 2 to 5 hours, to provide an O / W emulsion of crosslinked organosilicon according to the invention.

[0109] The O / W emulsion of this invention can be reverse-converted to a W / O emulsion after mixing with a compatible oil. Unrestricted by theory, when a compatible oil is externally added to the O / W emulsion, the internally cross-linked silicone, formed by free radical polymerization, can be "bloomed" into the oil phase by means of a polyether-modified polysiloxane, which promotes the contact between the internally cross-linked silicone and the external oil. Then, the cross-linked silicone, which has good compatibility with common organic oils (including silicone oils), swells in the external phase containing the external oil, and the aqueous phase becomes the internal phase dispersed in the oil phase. Both emulsification and viscosity can be improved with the same composition. This reverse-conversion emulsion of cross-linked silicone provides a good cushioning feel without any stickiness when applying formulations after the reversal.

[0110] In addition to visual observation, a decrease in conductivity can also indicate a successful reversal from an O / W emulsion to a W / O emulsion. When this reversal occurs, the conductivity will decrease significantly to below approximately 5 μS / cm and, in some embodiments, even below 1 μS / cm. Any known method for measuring conductivity can be used. For example, conductivity can be measured using a SevenExcellence multiparameter (Mettler Toledo).

[0111] The crosslinked silicone O / W emulsions described herein, as well as W / O emulsions derived from the inversion of such O / W emulsions, can be advantageously incorporated into any of a variety of personal care compositions. Such personal care compositions include, but are not limited to, applications such as: deodorants, antiperspirants, antiperspirant / deodorant, stick and roll-on formulations, lotions, moisturizers, astringents, cleansing formulations, styling gels, hair dyes, hair dye formulations, hair straighteners, nail polish, nail polish remover, sunscreens, anti-aging formulations, lipsticks, lip balms, lip glosses, foundations, face powders, eyeliners, eyeshadows, blushes, cosmetics, whitening creams, mascaras, moisturizing formulations, foundations, concealers, body and hand formulations, skin care formulations, face and neck formulations, fragrance formulations, soft-focus formulations, day and night skin care formulations, sunscreens, etc. Black preparations, hand sanitizers, non-woven preparations for personal care, facial wipes, baby lotions, facial cleansing preparations, hair cuticle protectants, gels, bubble baths, shower gels, scrub cleansers, controlled-release personal care preparations, shampoos, hair conditioners, hair sprays, skin care moisturizing sprays, skin wipes, skin pore wipes, pore cleansers, blemish reducers, skin exfoliants, skin exfoliating enhancers, anti-acne preparations, skin wipes, skin cloths, hair removal preparations, personal care lubricants, nail coloring preparations, and drug delivery systems for the topical application of therapeutic and medical products.

[0112] It is desirable that, in all embodiments of the O / W gel emulsions described herein, the emulsion reaction medium is free of noble metal hydrosilylation reaction catalysts, such as platinum-type catalysts, wherein the resulting crosslinked silicone O / W gel emulsion or the crosslinked silicone isolated therefrom is intended for introduction into personal care products, and such catalysts tend to cause discoloration or reduced transparency.

[0113] Example

[0114] The invention will be described in more detail with reference to the embodiments, but these embodiments should not be construed as limiting the scope of the invention. Furthermore, in the following description, "parts" means "parts by weight" unless otherwise stated. Viscosity was measured using an LVDV-II+ viscometer (Brookfield).

[0115] Example 1

[0116] A mixture is formed by mixing the following substances: 40 parts by weight of vinyl-containing dimethyl polysiloxane (M... V D 560 D V 36 M V 5 parts by weight of dihydropolydimethylsiloxane (M) with a viscosity of approximately 0.02 Pa·s at 25°C. H D 20 M H), 20 parts by weight of hemisqualane (APRINNOVA), 10 parts by weight of PEG 9 polydimethylsiloxane (Momentive Performance Materials, formula (II-1), wherein R 1 R 2 R 3 R 10 R 11 and R 12 For methyl groups, d average 60, e average 4, R 13 The mixture consisted of -C3H6-O-(C2H4O)9-CH3 and 2 parts by weight of stearyl alcohol polyether-21 (Croda). Then, under vigorous stirring, 10 parts by weight of initial water and 0.2 parts by weight of Kaneka Corporation were added to the mixture to obtain a stable emulsion. Further addition of deionized water yielded 50% by weight of non-volatile contents. 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 dimethyl polysiloxane and its hydrosilylation with dihydrodimethylsiloxane. After 4 hours, no SiH was found in the resulting stable O / W emulsion, which was measured using 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 the preservative phenoxyethanol was added. The O / W emulsion thus prepared was stable and had a viscosity of 4600 cps measured at 60 rpm using an LVDV-II+ viscometer (Brookfield) with an S64 rotor.

[0117] Then, the prepared O / W emulsion was mixed with hemisqualane as an oil at a weight ratio of 3:7 at room temperature. The state of the emulsion before and after mixing with the oil is as follows. Figure 1 As shown in the figure. For this emulsion after mixing with hemisqualane, the conductivity was measured at room temperature using a Seven Excellence multi-parameter tester (Mettler Toledo), and the viscosity was measured using an LVDV-II+ viscometer (Brookfield) with an S4 rotor at 60 rpm. The conductivity was 0.2 μS / cm, and the viscosity was 6,500 cPs. The results indicate that the prepared O / W emulsion was reversed into a W / O emulsion after mixing with oil.

[0118] Example 2

[0119] A mixture is formed by mixing the following substances at 50°C: 50 parts by weight of vinyl-containing dimethyl polysiloxane (M... V D 200 M V ), 10 parts by weight of an organosilicon resin with hydrogen groups (M) H 8Q4), 5 parts by weight of cetearyl polymethylsiloxane (Momentive Performance Materials), 3 parts by weight of PEG 8 polydimethylsiloxane (Momentive Performance Materials, Formula (II-2), wherein R 4 R 5 R 10 and R 11 For methyl groups, d averages 40, b averages 2, e averages 0, R averages 0. 6 The mixture consisted of 8 parts by weight of the PEG 9 polydimethylsiloxane (C3H6-O-(C2H4O)8-CH3), 2 parts by weight of the C30-45 alkyl polydimethylsiloxane (C3H6-O-(C2H4O)8-CH3), and 80 parts by weight of polydimethylsiloxane (C3H6-O-(C2H4O)8-CH3) with a viscosity of about 0.01 Pa·s at 25°C. A stable emulsion was then obtained by adding a premix of the following substances to the mixture under vigorous stirring: 1.5 parts by weight of sodium cetearyl sulfate, 6 parts by weight of polyoxyethylene lauryl ether, 8 parts by weight of polyoxyethylene monostearate, and 20 parts by weight of deionized water. Further addition of deionized water yielded 50% by weight of non-volatile contents. The emulsion was adjusted to 40°C and pH 4, and then 0.1 parts by weight of hydrogen peroxide and 0.1 parts by weight of ascorbic acid were added to initiate the free radical polymerization of vinyl-containing dimethyl polysiloxane and its reaction with M. H Hydrosilylation of the hydrogen groups in 8Q4. After 4 hours, the absence of SiH in the emulsion was confirmed by a fermentation tube method. After adjusting the pH to 5.5 with citric acid, 0.5 parts by weight of sodium benzoate preservative was added to the emulsion. The O / W emulsion thus prepared was stable, and its viscosity was 4800 cps as measured by an LVDV-II+ viscometer (Brookfield) using an S64 rotor at 60 rpm.

[0120] Example 3

[0121] A mixture is formed by mixing the following substances at 80°C: 100 parts by weight of a vinyl-containing silicone resin (M...) with a viscosity of about 0.5 Pa·s at 25°C. V8Q4), 15 parts by weight of the PEG 9 polydimethylsiloxane (MomentivePerformance Materials), 2 parts by weight of PEG / PPG-20 / 15 polydimethylsiloxane (MomentivePerformance Materials, Formula (II-1), wherein R 1 R 2 R 3 R 10 R 11 R 12 For methyl groups, d average 80, e average 15, R 13 It is -C3H6-O-(C2H4O) 20 (C3H6O) 15 -CH3), 10 parts by weight of methylhydropolysiloxane (M) with a viscosity of about 0.2 Pa·s at 25°C. H D 200 M H The mixture consisted of 40 parts by weight of isopropyl myristate and 0.5 parts by weight of lauroyl peroxide. Then, a premix of the following substances was added to the mixture under vigorous stirring to obtain a stable emulsion: 4 parts by weight of stearyl alcohol polyether 2 / 21 (Croda), 4 parts by weight of polyoxyethylene monostearate, and 20 parts by weight of deionized water. Further addition of deionized water yielded 50% by weight of non-volatile contents. The emulsion was then heated to 80°C to initiate free radical polymerization and free radical hydrosilylation. After 4 hours, the unreacted SiH in the emulsion, measured by the fermentation tube method, was less than 0.1 cc / g. After adjusting the pH to 6.5 with triethanolamine, 0.8 parts by weight of the preservative phenoxyethanol was added to the emulsion. The O / W emulsion thus prepared was stable, and its viscosity, measured by an LVDV-II+ viscometer (Brookfield) using an S64 rotor at 60 rpm, was 3200 cps.

[0122] Example 4

[0123] A mixture is formed by mixing the following substances: 40 parts by weight of vinyl-containing dimethyl polysiloxane (M... V D 560 D V 36 M VThe mixture consisted of 20 parts by weight of hemisqualane (APRINNOVA), 10 parts by weight of the aforementioned PEG9 polydimethylsiloxane (Momentive Performance Materials), and 2 parts by weight of stearyl alcohol polyether-21 (Croda). Then, under vigorous stirring, 10 parts by weight of initial water and 0.2 parts by weight of sodium subtilis lipopeptide (Kaneka Corporation) were added to the mixture to obtain a stable emulsion. Further addition of deionized water yielded 50% by weight of non-volatile contents. The emulsion was then heated to 80°C to initiate free radical polymerization, which was completed within 4 hours. Then, 0.8 parts by weight of the preservative phenoxyethanol and 0.2 parts by weight of the thickener guar gum were added to the emulsion. The O / W emulsion thus prepared was stable, and its viscosity was 4000 cps as measured by an LVDV-II+ viscometer (Brookfield) using an S64 rotor at 60 rpm.

[0124] The prepared O / W emulsion was then mixed with Silsoft 034 (Momentive Performance Materials) as an oil at a ratio of 1:1.2 at room temperature. Micrographs of the emulsion before and after mixing with the oil are shown below. Figure 2a and Figure 2b For the emulsions before and after mixing with oil, conductivity was measured at room temperature using a Seven Excellence multi-parameter tester (Mettler Toledo), and viscosity was measured using an LVDV-II+ viscometer (Brookfield) with an S64 (before) or S4 (after) rotor at 60 rpm. Conductivity decreased from 36.8 μS / cm to 1.6 μS / cm, and viscosity increased from 4000 cPs to 112,000 cPs. The results indicate that the prepared O / W emulsion reverts to a W / O emulsion after mixing with oil.

[0125] The contents of D4 (octamethylcyclotetrasiloxane), D5 (decamethylcyclopentasiloxane), and D6 (dodecylmethylcyclohexasiloxane) in the O / W emulsions of Examples 1-4 were measured by conventional gas chromatography (GC). The measurement results are shown in Table 1 below. Generally, it is advantageous to provide O / W emulsions in which the total content of D4, D5, and D6 is controlled to less than 1,000 ppm, especially for personal care products.

[0126] Table 1: Properties of Emulsions

[0127] serial number D4％ D5％ D6％ Example 1 0.02 0.03 0.03 Example 2 0.02 0.03 0.03 Example 3 0.02 0.03 0.03 Example 4 0.02 0.02 0.02

[0128] Comparative Example 1

[0129] A mixture is formed by mixing the following substances: 40 parts by weight of vinyl-containing dimethyl polysiloxane (M... V D 560 D V 36 M V The mixture consisted of 20 parts by weight of hemisqualane (APRINNOVA), 10 parts by weight of PEG 9 polydimethylsiloxane (Momentive Performance Materials), and 2 parts by weight of stearyl alcohol polyether-21 (Croda). Then, under vigorous stirring, 10 parts by weight of initial water and 0.2 parts by weight of sodium subtilis lipopeptide (Kaneka Corporation) were added to the mixture to obtain a stable emulsion. After adding 0.1 parts by weight of 0.33% by weight H2PtCl6 in ethanol, deionized water was further added to obtain 50% by weight of non-volatile contents. The emulsion was then heated to 80°C to begin polymerization. After 4 hours, 0.8 parts by weight of the preservative phenoxyethanol and 0.2 parts by weight of the thickener guar gum were added to the emulsion. The viscosity of the O / W emulsion thus prepared was 4200 cps, measured using an LVDV-II+ viscometer (Brookfield) with an S64 rotor at 60 rpm.

[0130] The emulsions of Example 4 and Comparative Example 1 were demulsified with isopropanol (IPA), respectively. Photographs showing the demulsification results are shown below. Figure 3a In (Example 4) and 3b (Comparative Example 1), the demulsified O / W emulsion of Example 4 showed small-sized gels, while no such gels were present in the demulsified emulsion of Comparative Example 1. This means that the internal phase in Comparative Example 1, even if cross-linked, was very minimal.

[0131] Comparative Example 2

[0132] A mixture is formed by mixing the following substances at 80°C: 100 parts by weight of an organosilicon resin (M...) with a viscosity of about 5 Pa·s at 25°C. V D 560 D V 36 M V ), 10 parts by weight of methylhydropolysiloxane (M) with a viscosity of approximately 0.2 Pa·s at 25°C. H D 200 M HThe mixture consisted of 40 parts by weight of isopropyl myristate and 0.5 parts by weight of lauroyl peroxide. Then, a premix of the following substances was added to the mixture under vigorous stirring to obtain a stable emulsion: 4 parts by weight of stearyl alcohol polyether 2 / 21 (Croda), 4 parts by weight of polyoxyethylene monostearate, and 20 parts by weight of deionized water. Further addition of deionized water yielded 50% by weight of non-volatile contents. The emulsion was then heated to 80°C to initiate free radical polymerization and free radical hydrosilylation. After 4 hours, the unreacted SiH in the emulsion, measured by the fermentation tube method, was 0.1 cc / g. After adjusting the pH to 7, 0.8 parts by weight of the preservative phenoxyethanol was added to the emulsion. The viscosity of the O / W emulsion thus prepared was 4500 cps, measured using an LVDV-II+ viscometer (Brookfield) with an S64 rotor at 60 rpm.

[0133] Test A (Reverse Inversion Test)

[0134] The emulsion prepared in Comparative Example 2 was mixed with hemisqualane as an oil at a 1:1 ratio. However, the emulsion could not be reversed after mixing with the oil. Figure 4 As shown, the white emulsion is at the bottom, while the semi-squalane oil is on the surface.

[0135] Test B (Water Compatibility Test)

[0136] The emulsion prepared in Comparative Example 2 was mixed with 5 g of PEG-10 polydimethylsiloxane in a quantity of 30 g, resulting in a thick paste. Then, 50 g of deionized water was added to the result while stirring, and the paste became thinner with many small fragments on the surface, as shown in Figure 5, indicating that it had poor water dilution properties.

[0137] The comparison between Comparative Example 2 and Examples 1-4 demonstrates the effect of polyether-modified polysiloxanes on phase inversion. If the polyether-modified polysiloxane is not used during emulsion polymerization, the prepared O / W emulsion cannot be phase-converted to a W / O emulsion by mixing with oil. If the polyether-modified polysiloxane is introduced after emulsion polymerization, the resulting emulsion will become a thick paste with poor compatibility with water.

[0138] Examples 5-10 illustrate various personal care compositions formulated using the O / W emulsion of the present invention. Examples 5 to 9 illustrate oil-based formulations, and Example 10 illustrates a water-based formulation.

[0139] Example 5: Avocado Cream

[0140]

[0141] program:

[0142] 1. Blend the components of Part A together.

[0143] 2. The components of premixed part B.

[0144] 3. While stirring, slowly add part B directly to part A.

[0145] 4. Stir at high speed for 3-5 minutes.

[0146] Example 6 HD Foundation

[0147]

[0148]

[0149] program:

[0150] 1. Blend the components of Part A together.

[0151] 2. The components of premixed part B.

[0152] 3. The components of premixed part C.

[0153] 4. While stirring, slowly add part B directly to part A, and then stir the mixture at high speed for 3 to 5 minutes.

[0154] 5. Blend the A / B mixture with the premixed C portion.

[0155] Example 7 Concealer

[0156]

[0157]

[0158] program:

[0159] 1. Mix all the components in Part A and heat to 80°C.

[0160] 2. The components of premixed part B.

[0161] 3. After cooling to 65°C, add part A to part B while stirring.

[0162] Example 8: Lipstick

[0163]

[0164] program:

[0165] 1. Mix all the components in Part A and heat to 80°C.

[0166] 2. The components of premixed part B.

[0167] 3. After cooling to 65°C, add part A to part B while stirring.

[0168] Example 9: Silky Cream

[0169] Components supplier Number of copies Part A 1 TEGO Alkanol 1618 (Cetearyl Alcohol) Evonik 1.5 2 Silsoft 034 Fluid Momentive 3 3 TEGOSOFT CT (Caprylic / Capric Triglycerides) Evonik 5 4 SIMMONDSIA CHINENSIS (Jojoba) Seed Oil Ecooil 2 Part B 5 glycerin Collinslab 5 6 Keltrol CG-T (Xanthan Gum) CP Kelco 0.1 7 TEGO Care SE 121 (Sucrose Stearate) Evonik 3 8 Carbopol Ultrez 30 polymer Lubrizol 0.25 9 Deionized water 74.3 Part C 10 Triethanolamine Collinslab 0.25 Part D 11 Example 2 5 12 Phenoxyethanol 0.5

[0170] program:

[0171] 1. Mix all the components of part A and heat part A to about 80°C.

[0172] 2. Dissolve the components of Part B in water and heat Part B to approximately 80°C.

[0173] 3. Add part A to part B while stirring, and homogenize for a few minutes.

[0174] 4. Add part C to part A / B while stirring.

[0175] 5. Add part D to parts A / B / C while stirring.

[0176] Example 10: Double-Layer Hair Spray

[0177]

[0178]

[0179] program:

[0180] 1. Add part C to part B while stirring.

[0181] 2. Mix the components in Part A.

[0182] 3. Add part A to the mixture of parts B and C.

[0183] The stability of each formulation obtained from Examples 5-10 was tested in a 50°C oven for 1 week. All formulations remained unchanged.

[0184] Although this disclosure has been described with reference to preferred embodiments, those skilled in the art will understand that various changes can be made and equivalents substituted for elements thereof without departing from the scope of this disclosure. Furthermore, many modifications can be made without departing from its essential scope to adapt a particular occasion or material to the teachings of this disclosure. Therefore, it is intended that this disclosure be limited to the specific embodiments disclosed as the best mode contemplated for carrying out this disclosure, but rather that this disclosure cover all embodiments falling within the appended claims.

Claims

1. An O / W emulsion of crosslinked organosilicon, wherein the O / W emulsion is obtained from the free radical polymerization of at least one polyorganosiloxane having at least two aliphatic unsaturated carbon-carbon bonds and optionally a hydrogen-containing organopolysiloxane in the presence of a polyether-modified polysiloxane under emulsion polymerization conditions, wherein the polyether-modified polysiloxane has the general formula (II): M 1 a M 2 b M 3 c D 1 d D 2 e D 3 f formula (II) in: 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 equation (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 alkyl or aryl having up to 60 carbon atoms; R 6 and R 13 each independently is -R 16 -O-(C2H4O) x (C3H6O) y (C4H8O) z -R 17 wherein R 16 is a divalent alkylene radical having 1 to 20 carbon atoms, R 17 is selected from hydrogen, and an alkyl, acyl or ester group having 1 to 20 carbon atoms, and the indices x, y and z each independently are integers from 0 to 200, with the proviso that 1 < x + y + z < 200; R 9 and R 15 each independently is a linear or branched alkyl group of 4 to 20 carbon atoms; a monovalent alkoxy or aryloxy group of up to 20 carbon atoms; or a divalent alkylene group of 1 to 20 carbon atoms terminated with alkoxy, aryloxy, amino, ester, amide, or epoxy groups; The subscripts a, b, c, d, e, and f are each independent integers from 0 to 200, provided that b + e ≥ 1, and The polyether-modified polysiloxane is used in an amount of 5 to 50 parts by weight, based on a total of 100 parts by weight of the polyorganosiloxane having at least two aliphatic unsaturated carbon-carbon bonds and the hydrogen-containing organopolysiloxane present. The at least one polyorganosiloxane wherein said polyorganosiloxane has 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 General Formula (I) in 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 ; as well as Q = SiO 4 / 2 wherein 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 group of up to 60 carbon atoms; R 26 , R 34 , and R 38 are each independently an olefinically unsaturated group of up to 30 carbon atoms; R 29 , R 30 , and R 36 are each independently a monovalent hydrocarbon group of up to 60 carbon atoms or R F ; each R F is independently a monovalent alkoxy group or ether group of up to 60 carbon atoms; and subscripts g, h, i, j, k, l, m, n, o, p, q, r, and s are each independently an integer from 0 to 1000, with the proviso that i+m+q ≥ 2, And the hydrogen-containing organopolysiloxane described therein has 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) wherein 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 independent integers from 0 to 500, provided that h + l + p ≥ 1, and where i + m + q ≥ 2, the formula (I) defined for polyorganosiloxanes is different from the formula (I) defined for hydrogen-containing organopolysiloxanes.

2. The O / W emulsion according to claim 1, wherein the polyorganosiloxane is selected from at least one of the following: M V i D k D V m M 2-i (I-1) wherein M V , D, D V and M are as defined previously and the indices i, k and m are integers, with the proviso that i is from 0 to 2, k is from 0 to 600, m is from 0 to 100, and R 26 and R 34 are each independently selected from a vinyl, an allyl, a methallyl, an acrylate or an alkyl acrylate group; M V i Q s (I-2) wherein M V and Q are as defined previously and the subscripts i and s are integers with the proviso that i > 2, s > 1 and i + s is 2 to 50, and each R 26 is selected from a vinyl, an allyl, a methallyl, an acrylate or an alkyl acrylate group.

3. The O / W emulsion according to claim 1 or 2, wherein the hydrogen-containing organopolysiloxane is selected from at least one of the following: M H h D k D H l M 2-h (I-3) wherein M H , D, D H and M are as defined previously and h, k and I are 0 or positive integers, with the proviso that k is from 10 to 300, I is from 0 to 50, h is from 0 to 2 and h + I is from 1 to 100; M H h Q s (I-4) wherein M H and Q are as previously defined and the subscripts h and s are integers, with the proviso that h > 1, s > 1 and i + s is 2 to 50.

4. The O / W emulsion according to claim 1 or 2, wherein the polyether-modified polysiloxane is selected from at least one of the following: M 1 2 D 1 d D 2 e (II-1) wherein M 1 , D 1 and D 2 are as defined above, 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) wherein M 1 , M 2 , D 1 and D 2 are as defined above. b is 1 or 2, d is 1 to 200, and e is 0 to 200.

5. The O / W emulsion according to claim 1 or 2, prepared by a method comprising: (a) Combining the polyorganosiloxane with the polyether-modified polysiloxane and optionally a hydrogen-containing organopolysiloxane to obtain a mixture; (b) Adding an aqueous medium containing an emulsifier to the mixture under stirring; and (c) Allow the mixture to undergo free radical polymerization.

6. A W / O emulsion, which is obtained by adding oil to an O / W emulsion according to any one of claims 1-5 to reverse the O / W emulsion.

7. A personal care composition comprising an O / W emulsion according to any one of claims 1-5 or a W / O emulsion according to claim 6.

8. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is selected from: hair dyes, hair straighteners, nail polish, nail polish removers, lipsticks, foundations, eyeliners, eyeshadows, mascaras, and drug delivery systems for the topical application of therapeutic and medical products.

9. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a deodorant.

10. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is an antiperspirant.

11. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a stick and roll-on formulation.

12. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a lotion.

13. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a moisturizing cream.

14. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a toner.

15. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a cleansing formulation.

16. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a styling gel.

17. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a sunscreen.

18. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is an anti-aging formulation.

19. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a lipstick.

20. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a lip gloss.

21. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a face powder.

22. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a blush.

23. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a make-up.

24. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a fairness cream.

25. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a moisturizing formulation.

26. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a concealer.

27. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a body and hand formulation.

28. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a skin care formulation.

29. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a face and neck formulation.

30. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a fragrance formulation.

31. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a soft focus preparation.

32. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a daily and nightly skin care preparation.

33. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a tanning preparation.

34. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a hand sanitizer.

35. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a nonwoven preparation for personal care.

36. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a facial tissue.

37. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a baby lotion.

38. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a facial wash preparation.

39. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a hair cuticle coat.

40. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a gel.

41. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a bubble bath.

42. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a body wash.

43. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a scrubbing cleanser.

44. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a controlled release personal care preparation.

45. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a shampoo.

46. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a hair conditioner.

47. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a hair spray.

48. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a skin care moisturizing spray.

49. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a skin wipe.

50. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a skin pore wipe.

51. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a pore cleanser.

52. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a blemish reducer.

53. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a skin exfoliant.

54. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a skin desquamation enhancer.

55. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is an anti-acne preparation.

56. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a skin wet wipe.

57. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a skin cloth.

58. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a hair removal preparation.

59. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a personal care lubricant.

60. A personal care application comprising the personal care composition of claim 7, wherein the personal care application is a nail coloring preparation.

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