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Wo 2010/115782 A2 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date 14 October 2010 (14.10.2010) WO 2010/115782 A2 (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A61K 8/06 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, (21) International Application Number: CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, PCT/EP20 10/054220 DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, 30 March 2010 (30.03.2010) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (25) Filing Language: English NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, (26) Publication Language: English SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 0905502. 1 31 March 2009 (3 1.03.2009) GB (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (71) Applicant (for all designated States except US): DOW GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, CORNING CORPORATION [US/US]; 2200 West ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, Salzburg Road, Midland, Michigan 48686-0994 (US). TM), European (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, (72) Inventors; and MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, SM, (75) Inventors/Applicants (for US only): COUREL, Bene- TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, dicte [FR/BE]; Avenue Fructidor 20, B-1410 Waterloo ML, MR, NE, SN, TD, TG). (BE). DAVIO, Delphine [BE/BE]; Chaussee de Mons 150, B-7070 Le Roeulx (BE). STAMMER, Andreas Declarations under Rule 4.17: [DE/BE]; Rue du Sabotier 9, B-6230 Pont-a-Celles (BE). — of inventorship (Rule 4Λ 7(iv)) STASSEN, Sophie [BE/BE]; Avenue des Eglantiers 2c, B-1 180 Bruxelles (Uccle) (BE). Published: (74) Agents: DONLAN, Andrew et al; Cardiff Road, Barry — without international search report and to be republished South Glamorgan CF63 2YL (GB). upon receipt of that report (Rule 48.2(g)) (54) Title: ORGANOPOLYSILOXANE EMULSIONS AND THEIR PRODUCTION (57) Abstract: This invention relates to aqueous emulsions comprising a polyorganosiloxane and a wax, and to methods of pro - duction of such emulsions. The emulsions are of the type oil-in-water. An organopolysiloxane is polymerized in admixture with a molten wax, thereby forming a blend of the wax with an organopolysiloxane of increased molecular weight, and the said blend of polymer and molten wax is emulsified in water in the presence of a surfactant. The emulsions are useful in personal care applica- tions such as on hair, skin, mucous membrane or teeth. The emulsions are also useful in applications such as paints, water based coatings, textile fibre treatment, leather lubrication, fabric softening, fabric care in laundry applications, homecare, release agents and oil drag reduction. ORGANOPOLYSILOXANE EMULSIONS AND THEIR PRODUCTION [0001] This invention relates to aqueous emulsions comprising a polyorganosiloxane and a wax, and to methods of production of such emulsions. The emulsions are of the type oil-in- water. [0002] Many personal care products such as face, hand and body cremes, shampoos, sunscreen formulations and colour cosmetics such as mascara and foundations are emulsions or other dispersions. High molecular weight polyorganosiloxanes are used in many applications in conjunction with organic (non-silicon-containing) ingredients, for example for use in personal care, often providing synergistic effects. The organic ingredients can be waxes or can be incorporated in organic waxes. However polyorganosiloxanes are not compatible (miscible) with many organic ingredients causing problems in obtaining stable dispersions. [0003] WO-A-2006/1 06362 describes preparing a diluted organopolysiloxane containing polymer by the polycondensation of siloxane containing monomers and/or oligomers which comprise condensable groups in the presence of an organopolysiloxane and/or an organic based diluent material, a suitable catalyst and optionally an end-blocking agent; and where required quenching the polymerisation process. The diluent material is substantially retained within the resulting diluted organopolysiloxane. The diluent needs to be compatible with the organopolysiloxane since otherwise it will exude out of the composition with time. WO- A-2008/045427 describes a method of making a silicone oil-in-water emulsion comprising the further steps of introducing one or more surfactants into the diluted organopolysiloxane to form a homogenous oil phase, adding 0.1 -10 percent by weight water to the homogenous oil phase to form a water-in-oil emulsion, applying shear to the water-in-oil emulsion to cause inversion of the water-in- oil emulsion to an oil-in-water emulsion; and optionally diluting the oil-in-water emulsion by adding more water. US5262087 describes a water-in-oil emulsified composition which comprises a wax composition formed by radical polymerisation of polysiloxanes and wax. Such radical polymerisation will lead to random grafting and crosslinking. JP 2000-026726 describes an emulsion obtained by polymerizing a specified organic silicon compound in the presence of a solvent in an ionic surfactant system. US5914362 describes an emulsion prepared from the reaction of (A) a primary silicone composition and (B) a polydiorganosiloxane having condensable terminal groups in a non polar organic medium selected from polyisobutylene and mineral oil. EP0802231 describes a silicone composition prepared by reacting a mixture comprising (i) mineral oil, (ii) a polyorganosiloxane, (iii) a silicon compound and (iv) a catalytic amount of a catalyst. US4990556 describes a cured silicone rubber containing entrapped mineral oil. Compositions containing organopolysiloxanes and waxes are described in US4404035 and US5503755. [0004] In a method according to the present invention for producing an aqueous emulsion of a polyorganosiloxane and a wax, an organopolysiloxane is polymerized in admixture with a molten wax, thereby forming a blend of the wax with an organopolysiloxane of increased molecular weight, and the said blend of polymer and molten wax is emulsified in water in the presence of a surfactant. [0005] In one preferred procedure the blend of the wax with an organopolysiloxane of increased molecular weight produced in the polymerization reaction is emulsified before the reaction product has cooled to a paste or solid. Alternatively the blend of the wax with an organopolysiloxane of increased molecular weight produced in the polymerization reaction is cooled to a paste or solid and is subsequently heated to melt the wax and emulsified at a temperature above the melting point of the wax. [0006] The blend of wax with organopolysiloxane of increased molecular weight produced in the polymerization reaction is a very intimate dispersion of wax in organopolysiloxane or vice versa. It is of course preferred that this blend is emulsified before any macroscopic phase separation has occurred. [0007] A silicone oil-in-water emulsion according to the invention is characterized in that the disperse phase is a blend of a wax with an organopolysiloxane which has been formed by polymerization in the presence of the wax. [0008] We have found that by emulsifying the blend of wax with high molecular weight organopolysiloxane formed by polymerization in admixture with the wax, stable emulsions of high molecular weight polyorganosiloxanes in conjunction with organic ingredients can more readily be formed. [0009] The organopolysiloxane starting material is preferably an organopolysiloxane containing at least one hydroxyl or hydrolysable group bonded to silicon and is preferably polymerized by a process comprising siloxane condensation. The organopolysiloxane starting material can for example be a substantially linear organopolysiloxane containing on average more than one hydroxyl or hydrolysable group bonded to silicon, preferably terminal hydroxyl or hydrolysable groups. The organopolysiloxane can for example have the general formula X1-A'-X 2 ( 1 ) where X1 and X2 are independently selected from silicon containing groups which contain hydroxyl or hydrolysable substituents and A' represents a polymer chain. Examples of X1 or X2 groups incorporating hydroxyl and/or hydrolysable substituents include groups terminating as described below: a b b a b [0010] -Si(OH) 3, -(FT)Si(OH)2, -(FT)2SiOH, -R Si(OR )2, -Si(OR )3, -R 2SiOR or a Si c dp(ORb a - R 2 -R -SiR )3-p where each R independently represents a monovalent hydrocarbyl group, for example, an alkyl group, in particular having from 1 to 8 carbon atoms, (and is preferably methyl); each Rb and Rd group is independently an alkyl or alkoxy group in which the alkyl groups suitably have up to 6 carbon atoms; Rc is a divalent hydrocarbon group which may be interrupted by one or more siloxane spacers having up to six silicon atoms; and p has the value 0 , 1 or 2 . Endblocking groups are of the formula - a (R )2SiOH may be particularly preferred. The linear organopolysiloxane can include a small amount, for example less than 20%, of unreactive endblocking groups of the formula [0011] The polymer chain A' is preferably a polydiorganosiloxane chain comprising siloxane units of formula (2) 2 -(R 2Si0)- (2) in which each R2 is independently an organic group such as a hydrocarbon group having from 1 to 18 carbon atoms, a substituted hydrocarbon group having from 1 to 18 carbon atoms or a hydrocarbonoxy group having up to 18 carbon atoms. [0012] Examples of hydrocarbon groups R2 include methyl, ethyl, propyl, butyl, vinyl, cyclohexyl, phenyl and tolyl groups.
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