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WO 2U12/U184U3 Al (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 i 9 February 2012 (09.02.2012) WO 2U12/U184U3ft Al (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C08G 77/50 (2006.01) C08L 83/14 (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/US201 1/001393 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, 4 August 201 1 (04.08.201 1) 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, QA, RO, RS, RU, (26) Publication Language: English SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, (30) Priority Data: ZW. 61/371,079 5 August 2010 (05.08.2010) US (84) Designated States (unless otherwise indicated, for every (71) Applicant (for all designated States except US): kind of regional protection available): ARIPO (BW, GH, BIOFILM IP, LLC [US/US]; 990 Ironwood Drive, Min- GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, den, NV 89423 (US). ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, (72) Inventors; and EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, ΓΓ, LT, LU, (75) Inventors/ Applicants (for US only): WRAY, Daniel, X. LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, [US/US]; P.O. Box 2649, Minden, NV 89423 (US). SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, HALSDORFF, Michael, B. [US/US]; 530 Whitesage GW, ML, MR, NE, SN, TD, TG). Road, San Marcos, CA 92078 (US). DE ARMOND, Robert, L. [US/US]; 42790 Calle Montecillo, Temecula, Declarations under Rule 4.17 : CA 92590 (US). — as to the applicant's entitlement to claim the priority of (74) Agents: SEIDMAN, Stephanie, L. et al; McKenna Long the earlier application (Rule 4.17(Hi)) & Aldridge LLP, 4435 Eastgate Mall, Suite 400, San Published: Diego, CA 92121 (US). — with international search report (Art. 21(3)) o 0 0 (54) Title: CYCLOSILOXANE-SUBSTITUTED POLYSILOXANE COMPOUNDS, COMPOSITIONS CONTAINING THE COMPOUNDS AND METHODS OF USE THEREOF o (57) Abstract: Provided herein are cyclosiloxane-substituted polysiloxane compounds, compositions that include the polysiloxane compounds, and methods for preparation and use of the polysiloxane compounds. Provided are mechanical lubricant composi tions, hydraulic fluid compositions, anti-foam compositions, water repellant agent compositions, release agent compositions, per sonal care compositions, cosmetic compositions and household care compositions that include one or more of the cyclosiloxane- substituted polysiloxane compounds provided herein. CYCLOSILOXANE-SUBSTITUTED POLYSILOXANE COMPOUNDS, COMPOSITIONS CONTAINING THE COMPOUNDS AND METHODS OF USE THEREOF Related Applications Benefit of priority is claimed to U.S. Provisional Application No. 61/371,079 to Daniel X. Wray, Robert L. De Armond and Michael B. Halsdorff, entitled "CYCLOSILOXANE-SUBSTITUTED POLYSILOXANE COMPOUNDS, COMPOSITIONS CONTAINING THE COMPOUNDS AND METHODS OF USE THEREOF," filed August 5, 2010. This application also is related to corresponding U.S. Patent Application No. [Attorney Docket No. 33348.09796.US01 / 9796], filed the same day herewith, entitled "CYCLOSILOXANE-SUBSTITUTED POLYSILOXANE COMPOUNDS, COMPOSITIONS CONTAINING THE COMPOUNDS AND METHODS OF USE THEREOF," which also claims priority to U.S. Provisional Application Serial No. 61/371,079. Where permitted, the subject matter of each of the above-referenced applications is incorporated by reference in its entirety. Field Provided herein are cyclosiloxane-substituted silicone compounds, compositions that include cyclosiloxane-substituted silicone compounds, and methods for use thereof, including in personal care and cosmetic compositions, release agent compositions, anti- foam compositions, personal lubricant compositions, and in lubricant compositions for reduction of friction in mechanical applications, including as silicone lubricant compositions for lubricating hard metal surfaces or soft metal surfaces. Background Organosilicone compounds and their use are well known in the art. Among the uses of organosilicone compounds are as lubricants, anti-foam agents, release agents, and for applications including cosmetics and personal care compositions, household products, in personal lubricant compositions, and as lubricants in mechanical applications and as hydraulic fluids. U.S. Pat. No. 4,514,319 describes alkyl and polyether functional silicones for the reduction of the surface tension of hydrocarbon oils when they are used in connection with organosilicones. U.S. Pat. No. 5,645,842 describes cosmetic and pharmaceutical preparations. Silicone lubricants are well known for hard metal surfaces. Such silicone lubricants usually contain an organopolysiloxane polymer which may be dimethylpolysiloxane polymer, a methyl or chlorophenyl or tetrachlorophenyl substituted polysiloxane polymer. Also, there are silicone lubricants in which the base lubricating fluid is composed of a trifluoropropyl substituted organopolysiloxane polymer. U.S. Pat. 2,837,482 describes dimethyl-polysiloxanes with various chlorinated additives for lubricating hard metal surfaces. Although methyl- and di-methylpolysiloxanes can be used as lubricants, it often is necessary to also add a chlorinated additive. Conventional chloride additives also are added to methyl tetrachlorophenyl substituted polysiloxanes to form ferrous chloride hydrate compounds at the surface of the hard metal which is being lubricated so that the oxy chloride will shear off under stress and prevent undue wear against the hard metal surface (e.g., see U.S. Pat. No. 4,138,349). Accordingly, a need exists for a polysiloxane that does not require a chlorine additive in order to function as an effective lubricant for hard or soft metals. Silicone fluids also are known to be beneficial in release coatings (e.g., see U.S. Pat. Nos. 3,933,702, 4,256,870 and 4,413,086). Silicone based release coatings are useful in applications where relatively non-adhesive surfaces are required. Single sided liners, for example, backing papers for pressure sensitive adhesive labels, are usually adapted to temporarily retain the labels without affecting the adhesive properties of the labels. Double sided liners, for example, interleaving papers for double sided and transfer tapes, are used to ensure the protection and desired unwind characteristics of a double sided self-adhesive tape or adhesive film. Improvements in the performance of release coatings are continuously being sought with respect to, for example, ease of cure, i.e. the decrease in cure times at relatively low temperatures, release performance and anchorage of coatings to various substrates, including polypropylene, polyethylene and polyester as well as paper and metals. Accordingly, a need exists for a silicone based release coating with improved release performance. Silicone fluids also are used in hydraulic fluids (e.g., see U.S. Pat. Nos 3,759,827 and 5,130,041). Hydraulic systems, in which power is transferred from one place to another, are used extensively in industrial equipment, farm equipment, and transportation equipment. Examples of such equipment are lifters, jacks, elevators, mills, presses, and braking and power steering systems for vehicles. High pressures and temperatures, which are frequently present in hydraulic systems, place high demands on the thermal and oxidative stability of the fluid used as the hydraulic medium. In addition, the lubricity of the hydraulic fluid is especially important with hydraulic systems where a pump is used to pressurize or move the hydraulic fluid from one place to another. Polyorganosiloxanes have been recognized as having exceptional thermal and oxidative stability, compatibility with seal materials, and high viscosity indices, and properties make polyorganosiloxanes useful as hydraulic fluids. Many of the polyorganosiloxanes known in the art generally exhibit low surface tension, which tends to cause them to have marginal lubricity on metals. Many applications of hydraulic fluids require that the viscosity of the fluid change as little as possible over the intended operating temperature range. Many of the known polyorganosiloxanes exhibit viscosity variation as a function of temperature relative to organic oils. This property makes many of the polyorganosiloxanes unsuitable for use as hydraulic fluids. Accordingly, a need exists for a polysiloxanes that exhibit low viscosity variation as a function of temperature and good thermal and oxidative stability for use as a hydraulic fluid. Silicones are widely used as anti-foaming agents. Examples of silicone anti- foaming compositions are for instance to be found in U. S. Pat. Nos. 2,894,913; 3,423,340; 3,076,768 and 3,856,701. Dimethylpolysiloxane polymers are widely known in the silicone industry for use as anti-foam agents. The chemical, food, petroleum, textile and pharmaceutical industries in many cases during the processing of material experience the undesirable formation of foam in some parts of its processes. A foam is formed when the rate of decay of foam is slower than the creation of new foam bubbles. Accordingly, when you have such a condition in a chemical or mechanical process there results the creation of an ever increasing foam, which is so stabilized that it does not decay very rapidly. It is desirable to remove or reduce the foaming in many processes, since the unwanted foam may create a hazard, such as fires hazard, or the foam can take up a considerable amount of space, thus requiring more space in which to carry out the process. Further, the presence of foam may make the process itself difficult to operate efficiently. In such cases, it is desirable to use some means of reducing or completely removing the foam.
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