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(12) Patent Application Publication (10) Pub. No.: US 2010/0129587 A1 Terauchi (43) Pub US 20100129587A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0129587 A1 Terauchi (43) Pub. Date: May 27, 2010 (54) COMPOSITION, CURED PRODUCT AND Publication Classification ARTICLE (51) Int. Cl. 8 B32B 3/02 (2006.01) (75) Inventor: Makoto Terauchi, Mie (JP) C08G 77/04 (2006.01) COSL 83/04 (2006.01) Correspondence Address: COSL 33/10 (2006.01) OBLON, SPIVAK, MCCLELLAND MAIER & B32B 27/38 (2006.01) NEUSTADT, L.L.P. (52) U.S. Cl. ............ 428/65.1: 528/27: 522/148; 522/77; 194O DUKE STREET 522/111; 428/644; 428/413 ALEXANDRIA, VA 22314 (US) (57) ABSTRACT (73) Assignee: Mitsubishi Chemical Disclosed is a composition capable of imparting high hard Corporation, Minato-ku, Tokyo ness, abrasion resistance, excellent contamination resistance (JP) and durability of Such contamination resistance even in the form of a thin film. Specifically disclosed is a composition including an organic polymer containing 5-30% by mass of a (21) Appl. No.: 11/720.809 radically polymerizable monomer with a perfluoroalkyl group, 0.01-5% by mass of C.O)-dimercaptopolysiloxane, (22) PCT Filed: Dec. 2, 2005 5-40% by mass of a radically polymerizable monomer with a cationically photopolymerizable epoxy group and 25-75% by (86). PCT No.: PCT/UP05/22 150 mass of another radically polymerizable monomer which is copolymerizable with the aforementioned substances. The S371 (c)(1), organic polymer has a structure corresponding to a radically (2), (4) Date: Nov. 19, 2007 polymerized copolymer of the monomer mixture wherein the molar ratio of the mercapto group to the epoxy group is (30) Foreign Application Priority Data 0.0001-0.025 and/or a structure obtained by reacting a (meth) acrylic acid with the epoxy group of the radically polymer Dec. 3, 2004 (JP) ................................. 2004-350658 ized copolymer. US 2010/0129587 A1 May 27, 2010 COMPOSITION, CURED PRODUCT AND that of a second layer of another coating agent. U.S. Pat. No. ARTICLE 6,489,015 (JP-A 2000-214791) also describes that a coated film having hardness is obtained by setting the coefficient of TECHNICAL FIELD elasticity of a first layer coating agent larger than that of a second layer of another coating agent. However, in any of 0001. The present invention relates to a novel organic them, the total thickness of the coated film becomes at least 10 polymer, a composition containing said organic polymer, um, and processability is poor in that two or more layers are having excellent hardness and Scratching resistance, and applied. being usable as an antifouling agent as well as cured products and articles using said composition. In particular, the inven 0008 Furthermore, U.S. Pat. No. 6,846,567 (JP-A 2000 219845) describes that excellent abrasion resistance can be tion relates to the composition which produces coated films realized, while the total thickness of coated films is set to at having Sufficient performance even in thin film thickness. most 10 Jum, when a methacrylic polymer is applied as a first layer, and on the first layer, as a second layer, a coated film, BACKGROUND OF THE INVENTION which is obtained by curing an organosiloxane resin compris 0002 Owing to their lightweights, easy processability, ing a hydrolysis condensate of colloidal silica and a specific impact resistance, etc., the plastic products are used in various silicate, is laminated. However, there is no change the appli applications including containers, automobile instrument cation of two or more layers. panels and outer plates, window materials, roof materials, 0009 Meanwhile, coating agents capable of realizing wrapping materials, various housing materials, optical disc excellent hardness and abrasion resistance even if applied in Substrates, plastic lenses, base materials in display devices a single layer have been investigated. Heretofore, composi Such as liquid crystal displays, plasma displays, projection tions of colloidal silica and multifunctional acrylates, TVs, etc. hydrolysis condensate compositions of colloidal silica and a 0003. Among them, for examples, resin materials such as specific silicate, and curable resin compositions of the above polycarbonates, polymethyl methacrylate, polyethylene and a polyfunctional acrylate, an epoxy resin, a phenoxy resin terephthalate, polybutylene terephthalate, styrene-based res or the like, or compositions of the above compositions and an ins including acrylonitrile-butadiene-styrene copolymer acryl resin, etc. have been widely investigated as organic (ABS), methyl methacrylate-styrene copolymer (MS resin), inorganic composite coating agents. However, they had prob acrylonitrile styrene copolymer (AS resin) etc., vinyl chlo lems of insufficient-hardness and abrasion resistance, poor ride-based resins, cellulose acetate including triacetyl cellu stability in the form of a coating liquid, or insufficient envi lose are Suitable for the above applications, because they are ronmental properties (moisture resistance, heat resistance, excellent particularly in lightweights, easy processability, etc.) of cured films, etc. As compared with them, an active impact resistances, etc. energy ray-curable coating agent including a compound 0004. However, these plastic products are easily damaged obtained by reacting a polyfunctional acrylate with a colloi due to low Surface hardness. Transparent resins such as a dal silica as disclosed in U.S. Pat. No. 5,378,735 (JP-A polycarbonate and polyethylene terephthalate have a defect 5-287215) and U.S. Pat. No. 6,160,067 (JP-A9-100111) has that their inherent transparency or appearance is conspicu more excellent hardness and abrasion resistance, even if ously damaged. Thus, this makes it difficult for the plastic coated in a single layer, than conventional organic-inorganic products to be used in fields requiring abrasion resistance. composite coating agents. However, since they had low anti 0005 Under the circumstances, active energy ray-curable fouling property and weatherability, and further sufficient hard coat materials (coating materials) giving abrasion resis Surface curing cannot be realized when they are applied in the tance to the Surfaces of the plastic products have been sought. form of a thin film, it was difficult to realize the physical However, since cured layers of commercially available, properties that should essentially appear. active energy ray-curable hard coat materials are largely (0010. Further, for example, as shown in JP-A 10-316864, shrunk to cause warping, peeling off or cracking, it is difficult a method for using a polymerized UV curable resin is pro to coat them thick. Consequently, there was a limit on the posed to decrease shrinkage. However, although shrinkage is attainable hardness and Scratching resistance. largely reduced on curing, it has a limit in the case that it is 0006. In order to solve such problems, various active adopted in applications requiring further reduction in shrink energy ray-curable coating materials have been recently pro age or applications requiring higher hardness and scratching posed, which would realize hardness and abrasion resistance resistance, in addition, the resin is Susceptible to interruption that exceed those in the conventional methods. For example, on curing with oxygen, and particularly has a problem in JP-A 11-309814 discloses that abrasion resistance is largely curing a thin film (for example, film thickness: at most 2 um). improved by coating two or more layers of coating agents, Furthermore, since a cured degree in a surface portion is low while using an inorganic coating agent having a coated film even in the case that the film is not thin, there are many formability, such as polysilaxane, for the outermost layer. problems in the durability of the physical properties. However, since the coating agent is inorganic, it is difficult to 0011 Moreover, in order to further lower the shrinkage or form a thick film. Thus, since it is Substantially necessary to improve the cured degree of the Surface, there are proposed a apply two or more layers, there is a problem of poor process method using a cationic polymerizable resin as a (polymer ability. ized) UV curable resin (JP-A2001-40205, etc.), and a method 0007. On the other hand, a trial is made, in which hardness using a colloidal silica to which a cationic polymerizable low and abrasion resistance are improved by coating two or more molecular-weight organic component is suggested (JP-A layers of coating agents having different coefficients of elas 2002-53659, etc.), and a method using these components and ticity. For example, JP-A 2000-52472 describes that a coated an ordinary radical polymerizable UV curable resin (includ film having high hardness is obtained by making the coeffi ing both organic and organic-inorganic hybrid resins) in com cient of elasticity of a first layer of a coating agent larger than bination (For example, JP-A 9-278935, JP-A 2002-128887, US 2010/0129587 A1 May 27, 2010 JP-A 2002-322430, U.S. Pat. No. 6,777,102 (JP-A 2003 organic Substance like a fingerprint causes a problem that 147017, etc.). Although they have the characteristics of once it attaches, it is difficult to be removed. reduced shrinkage, increased film thickness or enhanced Sur 0019. As methods to solve such problems, for example, face curing, there is still a limit in application to usages JP-A 10-110118 proposes that a non-crosslinking type fluo requiring further increased hardness and scratching resis rine-based Surface active agent is added into a coated film of tance. Further, there
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