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(AD). Ali. 2322232 12 Patent Application Publication Aug US 20080187678A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/0187678 A1 FLEMING et al. (43) Pub. Date: Aug. 7, 2008 (54) MCROSTRUCTURED SUBSTRATES WITH ation of application No. 10/268,119, filed on Oct. 10, PROFILE-PRESERVING 2002, now Pat. No. 6,815,043, which is a division of ORGANOMETALLIC COATINGS application No. 09/259,487, filed on Feb. 26, 1999, now Pat. No. 6,503,564. (75) Inventors: Robert J. FLEMING, Lake Elmo, MN (US); Joseph M. McGrath, Publication Classification Lake Elmo, MN (US); Christopher S. Lyons, St. Paul, MN (US) (51) Int. Cl. C08F 2/246 (2006.01) Correspondence Address: C23C I6/44 (2006.01) 3M INNOVATIVE PROPERTIES COMPANY (52) U.S. Cl. ...................................... 427/488; 427/255.6 PO BOX 33427 ST. PAUL, MN 55133-3427 (57) ABSTRACT (73) Assignee: 3M Innovative Properties A method of making a polymer coating on a microstructured Company substrate. The method may be performed by vaporizing a liquid monomer or other pre-polymer composition and con (21) Appl. No.: 11/868,014 densing the vaporized material onto a microstructured Sub strate, followed by curing. The resulting article may possess (22) Filed: Oct. 5, 2007 a coating that preserves the underlying microstructural fea ture profile. Such a profile-preserving polymer coating can be Related U.S. Application Data used to change or enhance the Surface properties of the micro (60) Division of application No. 10/949,898, filed on Sep. structured substrate while maintaining the function of the 24, 2004, now Pat. No. 7,288,309, which is a continu Structure. (AD). Ali. 2322232 12 Patent Application Publication Aug. 7, 2008 Sheet 1 of 5 US 2008/O187678A1 106 Fig. 1 7.25ay Z23222. W 12 Patent Application Publication Aug. 7, 2008 Sheet 2 of 5 US 2008/O187678A1 Patent Application Publication Aug. 7, 2008 Sheet 3 of 5 US 2008/O187678A1 6 WsSea Eys S32 E. Sé % &aya By E. Se2 2. 29.2% ve 34 35 Patent Application Publication Aug. 7, 2008 Sheet 4 of 5 US 2008/O187678A1 Patent Application Publication Aug. 7, 2008 Sheet 5 of 5 US 2008/O187678A1 sex'', & YA 2. .. e'o a st fi, . X re: US 2008/O 187678 A1 Aug. 7, 2008 MICROSTRUCTURED SUBSTRATES WITH and a partially fluorinated mercaptain (namely, CF (CH2) PROFILE-PRESERVING SH) from a solvent onto a surface that has small surface ORGANOMETALLIC COATINGS feature profiles. CROSS REFERENCE TO RELATED Gas-Phase Coating Methods APPLICATIONS 0006 Gas-phase coating techniques generally include the 0001. This application is a divisional of U.S. Ser. No. methods commonly known as physical vapor deposition 10/949,898 filed Sep. 24, 2004, now allowed; which is a (PVD), chemical vapor deposition (CVD), and plasma depo continuation of U.S. Ser. No. 10/268,119, filed Oct. 10, 2002, sition. These techniques commonly involve generating a gas now U.S. Pat. No. 6,815,043; which is a divisional of U.S. Ser. phase coating material that condenses onto or reacts with a No. 09/259,487, filed Feb. 26, 1999, now U.S. Pat. No. 6,503, substrate surface. The methods are typically suitable for coat 564 B1, the disclosures of which are herein incorporated by ing films, foils, and papers in roll form, as well as coating reference. three-dimensional objects. Various gas-phase deposition methods are described in “Thin Films: Film Formation Tech FIELD OF THE INVENTION niques.” Encyclopedia of Chemical Technology, 4" ed., Vol. 23 (New York, 1997), pp. 1040-76. PVD is a vacuum process 0002 The present invention pertains to (i) a method of where the coating material is vaporized by evaporation, by making an article that has a polymer coating disposed on a sublimation, or by bombardment with energetic ions from a microstructured Substrate, and to (ii) an article that possesses plasma (sputtering). The vaporized material condenses to a microstructured surface and that has a profile-preserving form a solid film on the substrate. The deposited material, polymer coating disposed on the Surface. however, is generally metallic or ceramic in nature (see Ency clopedia of Chemical Technology as cited above). U.S. Pat. BACKGROUND No. 5,342,477 discloses using a PVD process to deposit a 0003 Various techniques are known for coating substrates metal on a Substrate that has Small Surface feature profiles. A with thin layers of polymeric materials. In general, the known PVD process has also been used to sublimate and deposit techniques can be predominantly divided into three groups, organic materials such as perylene dye molecules onto Sub (1) liquid coating methods, (2) gas-phase coating methods, strates that have small surface features, as disclosed in U.S. and (3) monomer vapor coating methods. As discussed below, Pat. No. 5,879,828. some of these methods have been used to coat articles that 0007 CVD processes involve reacting two or more gas have very small surface feature profiles. phase species (precursors) to form solid metallic and/or ceramic coatings on a Surface (see Encyclopedia of Chemical Liquid Coating Methods Technology as cited above). In a high-temperature CVD 0004 Liquid coating methods generally involve applying method, the reactions occur on Surfaces that can be heated at a solution or dispersion of a polymer onto a Substrate or 300° C. to 1000° C. or more, and thus the substrates are involve applying a liquid reactive material onto the Substrate. limited to materials that can withstand relatively high tem Polymer or pre-polymer application is generally followed by peratures. In a plasma-enhanced CVD method, the reactions evaporating the solvent (in the case of materials applied from are activated by a plasma, and therefore the Substrate tem a solution or dispersion) and/or hardening or curing to form a perature can be significantly lower. CVD processing can be polymer coating. Liquid coating methods include the tech used to form inorganic coatings on structured Surfaces. For niques commonly known as knife, bar, slot, slide, die, roll, or example, U.S. Pat. No. 5,559,634 teaches the use of CVD gravure coating. Coating quality generally depends on mix processing to form thin, transparent coatings of ceramic ture uniformity, the quality of the deposited liquid layer, and materials on structured Surfaces for optical applications. the process used to dry or cure the liquid layer. If a solvent is 0008 Plasma deposition, also known as plasma polymer used, it can be evaporated from the mixture to form a solid coating. The evaporation step, however, commonly requires ization, is analogous to plasma-enhanced CVD, except that significant energy and process time to ensure that the solvent the precursor materials and the deposited coatings are typi is disposed of in an environmentally-sound manner. During cally organic in nature. The plasma significantly breaks up the the evaporation step, localized factors—which include vis precursor molecules into a distribution of molecular frag cosity, Surface tension, compositional uniformity, and diffu ments and atoms that randomly recombine on a Surface to sion coefficients—can affect the quality of the final polymer generate a solid coating (see Encyclopedia of Chemical Tech coating. nology as cited above). A characteristic of a plasma-deposited 0005 Liquid coating techniques can be used to coat mate coating is the presence of a wide range of functional groups, rials onto substrates that have small surface feature profiles. including many types of functional groups not contained in For example, U.S. Pat. No. 5,812.31 discloses applying a the precursor molecules. Plasma-deposited coatings gener Solution of prepolymer components and a silane coupling ally lack the repeat-unit structure of conventional polymers, agent onto the protruding portions of partially embedded and they generally do not resemble linear, branched, or con microspheres. And U.S. Pat. No. 4,648,932 discloses extrud ventional crosslinked polymers and copolymers. Plasma ing a liquid resin onto partially embedded microspheres. As deposition techniques can be used to coat structured Surfaces. another example, U.S. Pat. No. 5,674,592 discloses forming a For example, U.S. Pat. No. 5,116,460 teaches the use of self-assembled-monolayer coating of octadecyl mercaptain plasma deposition to form coatings of plasma-polymerized US 2008/O 187678 A1 Aug. 7, 2008 fluorocarbon gases onto etched silicon dioxide Surfaces dur curable coating that is cured on the microstructured surface. ing semiconductor device fabrication. The method is capable of producing polymeric coatings that preserve the microstructured profile of the underlying sub Monomer Vapor Coating Methods strate. Known methods of coating microstructured articles 0009 Monomer vapor coating methods may be described involved coating reactive liquid materials from a solution or as a hybrid of the liquid and gas phase coating methods. dispersion, Sublimating whole molecules, or depositing Monomer vapor coating methods generally involve condens atoms and/or molecular fragments. These known techniques ing a liquid coating out of a gas-phase and Subsequently were not known to provide polymer coatings that preserved Solidifying or curing it on the Substrate. The liquid coating the profile of the underlying microstructured substrate and generally can be deposited with high uniformity and can be quickly polymerized to form a high quality solid coating. The that had controlled chemical composition. coating material is often comprised of radiation-curable 0014) A product that can be produced from the inventive monomers. Electron-beam or ultraviolet irradiation is fre method thus is different from known microstructured articles. quently used in the curing (see, for example, U.S. Pat. No. The present invention accordingly also provides an article 5,395,644). The liquid nature of the initial deposit makes that has a microstructured Surface that has a profile-preserv monomer vapor coatings generally Smoother than the Sub ing polymer coating disposed on the microstructured surface.
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