< S 6 6 a as s + = a 9 S (12) INTERNATIONAL APPLICATION PUBLISHED UNDER TH (19) World Intellectual Property Orgai International Bureau Z (43) International Publication Date = 26 June 2014 (26.06.2014) E PATENT COOPERATION TREATY (PCT) ANOKA TE (10) International Publication Number ‘WO 2014/099580 Al WIPO|PCT (1) International Patent Classification C086 18/61 (2006.01) CO8G 18/24 (2006.01) C086 18/65 (2006.01) CO8G 18/32 (2006.01) C086 18/73 (2006.01) CO9D 5/03 (2006.01) C086 18/81 (2006.01) CO9D 175/16 (2006.01) International Application Number: PCT/US2013/074878, en (22) International Filing Date: 12 Devember 2013 (12.12.2013) es, English 26) Publication Language: English (30) Priority Data: 61/738,054 17 December 2012 (17.12.2012) us. (7) Applicant (for US only): AXALTA COATING SYS- TEMS IP CO. LLC [USUSI; The Corporation Trust Company, Corporation Trust Center, 1209 Orange Steet, ‘Wilmington, Delaware 19801 (US). (TD Applicant (for ail designated States except US): COAT- INGS FOREIGN IP CO. LLC [US/US}; The Corporation Trust Company, Corporation Trust Center, 1209 Orange Street, Wilmington, Delaware 19801 (US) Inventors: and Applicants : FLOSBACH, Carmen [DE/DEl; The Cor poration Trust Company, Corporation Trust Center, 1208 ‘Orange Street, Wilmington, Delaware 19801 (US), MAT- TEN, Stefanke [DE/DE], The Comporation Trust Company, Corporation Trust Center, 1209 Orange Street, Wilming ton, Delaware 19801 (US). DONNERMEYER, Jennifer [DEIDE}, The Comporation Trust Company, Cosporation ™ am ‘Trust Conter, 1209 Orange Steet, Wilmington, Delaware 19801 (US). Agent: HENSCHEID, Deborah K.; Ingrassia Fisher & Lorenz, P.C., 7010 E, Cochise Road, Scottsdale, Arizona 85253 (US) 4) (81) Designated States (uriess otherwise indicated, for every Kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, FE, FG, FS, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, 1D! IL, IN, IR, iS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NILNO, NZ, (OM, PA, PE, BG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SDE, SG, mW, Designated States (uriess otherwise indicated, for every ind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, UG, 2M, ZW), Pirasian (AM, AZ, BY, KG, KZ, RU, TI, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK. 1, PS, Fl, FR, GB, GR, HR, HU, IE iS, LU,LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, Sl, SK, SM, TR), OAPI (BE, BI, CF, CG, Ci, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG), Published: with international search report (Art. 21(3)) (84) before the expiration of the tine limit for amending the claims and 1 be republished in the event of receipt of famendiments (Rule 48,2(h (64) Title: POWDER COATING COMPOSITION (57) Abstract: A powder coating composition includes: A) about 30 to about 95 wt ‘of «polyurethane resin as hinder resin which is produced trom an isocyanate component and an alcohol component comprising a 4,o-hydtoxy organo functional polydimethyl siloxane, providing the powder coating composition a silicon content (calculated as elementary silicon with molecular mass 28) in a ‘of about 0.2 to about 5 wi%, the wi% based on the total weight of the powder coating composition, B) 0 to about 70 wi% of a coo-inder (cross-linking agent, hardener), and C) about 05 to about 60 wt% of a pigment, filler andor coating additive, the 1% based on the total weight of the powder coating composition. The powder coating composition provides eoatings with highly im proved aatigraffity properties and can be used to provide additionally a stable self-cleaning effect ofthe coatings.WO 2014/099580 PCT/US2013/074578 POWDER COATING COMPOSITION CROSS-REFERENCE TO RELATED APPLICATION [0001] This application claims the benefit of U.S. Provisional Application No. 61/738,054, filed December 17, 2012. TECHNICAL FIELD [0002] The technical field refers to a powder coating composition useful for the preparation of coatings with anti-graffiti properties. BACKGROUND [0003] The production of polyurethane resins is known to the person skilled in the art; in particular, they may be produced by reacting polyol(s) with polyisocyanate(s). [0004] _Undesired graffiti on buildings and vehicles produced by spraying cannot be eliminated in most cases simply by washing; usually the graffii-bearing walls and substrates have to be repainted, which is laborious and expensive. [0005] Attempts have been made to prepare protective coatings providing a low surface tension and, therefore, dir-repellent properties. Examples are formulations comprising fluorine containing polymers, see US 4929666, and formulations comprising polysiloxane compounds as described in DE-A 2610 372 and US 5426151. Problems arising with these systems are the incompatibility of components: in the coating formulation or insufficient anti-graffiti protection for a long time period. [0006] Coatings with anti-graffiti properties can also be based on powder coating compositions comprising a mixture of polyester binder resins having different hydroxyl numbers and number-average molar masses (Mn), see for example EP-A 2214917. [0007] Easy-to-clean powder coating compositions are known providing coatings having a self-cleaning effect. For example, WO 2007059133 discloses a powder coating composition containing hydrophobic agents such as functional alkyl silanes, alkyl siloxanes, fluorine alkyl silanes and fluorine alkyl siloxanes, and perfluorinated hydro carbons. EP-A 772 514 describes surfaces having specific structure consisting of elevations and depths with specific distances, the elevations are made ofWoO 2014/099580 PCT/US2013/074578 hydrophobic polymers providing a self-cleaning surface. WO 02/064266 describes coatings providing a particle-based surface structure wherein the particles have an average diameter lower 100 nm, and wherein the coating is at least partially hydrophobic. Unfortunately, the self-cleaning ability of the coatings of prior art often is not stable during the time of exposure of the coated surface to weather. [0008] Accordingly, it is desirable to provide a powder coating composition having anti-graffity properties. In addition, it desirable to provide powder coating compositions with stable self-cleaning effects. In addition, other objects, desirable features and characteristics will become apparent from the subsequent summary and detailed description, and the appended claims, taken in conjunction with the accompanying drawings and this background, SUMMARY [0009] The exemplary embodiments herein relate to a powder coating composition comprising: A) about 30 to about 99.5 wt% of at least one polyurethane resin as binder resin which is produced from an isocyanate component and an alcohol component comprising at least one a,u-hydroxy organo functional polydimethylsiloxane, providing the powder coating composition a silicon content (calculated as elementary silicon with molecular mass 28) in a range of about 0.2 to about 5 wt%, the wt% based on the total weight of the powder coating composition, B) 0 to about 70 wt% of at least one co-binder (cross-linking agent, hardener), and C) about 0.5 to about 60 wt% of at least one pigment, filler and/or coating additive, [00010] the wt% based on the total weight of the powder coating composition. [00011] The powder coating composition according to the invention based on the at least such polyurethane resin provides coatings with highly improved anti-graffity properties, and can be used to provide additionally a stable self-cleaning effect of the coatings.WoO 2014/099580 PCT/US2013/074578 DETAILED DESCRIPTION [00012] The following detailed description is merely exemplary in nature and is not intended to limit the embodiments herein or the application and uses thereof. Furthermore, there is no intention to be bound by any theory presented in the preceding background or the following detailed description [00013] The features and advantages of the present invention will be more readily understood, by those of ordinary skill in the art, from reading the following detailed description. It is to be appreciated that those certain features of the invention which are, for clarity, described above and below in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features of the invention that are, for brevity, described in the context of a single embodiment, may also be provided separately or in any sub-combination. In addition, references in the singular may also include the plural (for example, “a” and ‘an" may refer to one, or one or more) unless the context specifically states otherwise. [00014] The disclosure of value ranges is intended as a continuous range of values including every value between the minimum and maximum values. [00015] The various embodiments refer to a powder coating composition comprising as component A) about 30 to about 99.5 wi%, based on the total weight of the powder coating composition, of at least one polyurethane resin as binder resin Which is produced from an isocyanate component and an alechol component comprising at least one a,u-hydroxy organo functional polydimethylsiloxane, providing the powder coating composition a silicon content (calculated as elementary silicon with molecular mass 28) in a range of about 0.2 to about 5 wt%, the wi% based on the total weight of the powder coating composition. [00016] Preferably, the powder coating composition comprises as component A) about 50 to about 99.5 wt%, more preferably about 80 to about 99.5 wt%, of the at least one polyurethane resin, the wt% based on the total weight of the powder coating composition, particularly in case the powder coating composition of the invention is cured by high energy radiation, for example, ultra violet (UV) irradiation. [00017] Preferably, the powder coating composition bcomprises as component A) about 30 to about 90 wt%, more preferably about 50 to about 80 wt%, of the at least