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US20120288675A1 - Optical device with antistatic property - Google Patents

Optical device with antistatic property Download PDF

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Publication number
US20120288675A1
US20120288675A1 US13/504,810 US201013504810A US2012288675A1 US 20120288675 A1 US20120288675 A1 US 20120288675A1 US 201013504810 A US201013504810 A US 201013504810A US 2012288675 A1 US2012288675 A1 US 2012288675A1
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US
United States
Prior art keywords
optical
optical device
optical member
antistatic
coating
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Abandoned
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US13/504,810
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English (en)
Inventor
Thomas P. Klun
Brandt K. Carter
Michael K. Gerlach
Mahfuza B. Ali
Mark J. Pellerite
Thomas M. Snyder
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3M Innovative Properties Co
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Individual
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Priority to US13/504,810 priority Critical patent/US20120288675A1/en
Assigned to 3M INNOVATIVE PROPERTIES COMPANY reassignment 3M INNOVATIVE PROPERTIES COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CARTER, BRANDT K., ALI, MAHFUZA B., SNYDER, THOMAS M., KLUN, THOMAS P., PELLERITE, MARK J., GERLACH, MICHAEL K.
Publication of US20120288675A1 publication Critical patent/US20120288675A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/308—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/16—Anti-static materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/104—Esters of polyhydric alcohols or polyhydric phenols of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/36—Amides or imides
    • C08F222/40—Imides, e.g. cyclic imides
    • C08F222/408—Imides, e.g. cyclic imides substituted imides comprising other heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/04—Antistatic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24355—Continuous and nonuniform or irregular surface on layer or component [e.g., roofing, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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    • Y10T428/269—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension including synthetic resin or polymer layer or component
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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    • Y10T428/31504—Composite [nonstructural laminate]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31609—Particulate metal or metal compound-containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31721—Of polyimide
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31931—Polyene monomer-containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10T428/31935—Ester, halide or nitrile of addition polymer

Definitions

  • the present invention relates to optical devices exhibiting excellent antistatic properties and optical performance.
  • Such devices are commonly used as or in assemblies to increase the sharpness of images produced by displays and to reduce the power consumption necessary to produce a selected brightness.
  • Such assemblies are commonly used in such equipment as computers, televisions, video recorders, mobile communication devices, and vehicle instrument displays, etc.
  • Optical assemblies are typically assembled by laminating or joining in desired arrangement two or more layers or films that were separately acquired or manufactured.
  • static electrical charges may be created.
  • Such charges may interfere with handling properties of the films, e.g., causing them to undesirably cling together, cause dirt to be entrapped in the construction, etc. Accordingly, it is typically desirable to take steps to prevent the creation and buildup of static electricity in the optical construction.
  • the present invention provides novel optical devices incorporating layers exhibiting exceptional antistatic performance.
  • a typical embodiment of the present invention is an optical device comprising a first optical member, a second optical member, and an antistatic layer disposed between the first optical member and the second optical member wherein the antistatic layer comprises the reaction product of a mixture comprising at least one polymerizable onium salt and at least one non-onium polymerizable monomer, oligomer, or polymer.
  • the antistatic layer is disposed intermediate to the two optical members within the optical path of the device.
  • the antistatic layer may be affixed to either or both of the optical members.
  • the antistatic layer may be affixed directly to the optical member(s) or may be affixed through an intervening layer.
  • the antistatic layer is not in direct contact with either optical member.
  • Optical devices of the invention can exhibit a surprising combination of performance including excellent optical performance, e.g., high optical gain, and good antistatic performance evidenced by low static decay times.
  • the invention permits selection and use of a variety of optical members and facilitates easy assembly permitting convenient, cost effective assembly of optical devices configured for desired optical performance.
  • FIG. 1 is a schematic illustration of an illustrative embodiment of the invention
  • FIG. 2 is a schematic cross sectional illustration of another illustrative embodiment of the invention.
  • FIG. 3 is a schematic cross sectional illustration of still another illustrative embodiment of the invention.
  • optical devices of this invention are static dissipative and will dissipate in less than 10 seconds 90% of an electrostatic charge applied to the front surface of the device under an applied voltage of 5 kilovolts, preferably in less then 5 sec, more preferably in less than 2 sec, even more preferably in less than 1 sec, and most preferably in less than 0.1 sec. The test used is described in the Test Methods section.
  • Optical path refers to the path in which light incident to the front surface of the device is reflected, refracted, transmitted, or otherwise passes through the members of the optical device.
  • front refers to the surface of the optical device or component member thereof which in use is presented for incidence of light thereto for desired light management.
  • the invention can be used to make a variety of optical devices.
  • Optical Gain of an optical device or optical stack is defined as the ratio of the axial output luminance of an optical or display system with the optical stack to the axial output luminance of the same optical or display system without the optical stack.
  • Optical constructions of the present invention typically comprise a first optical member, a second optical member, and an antistatic layer disposed between the first optical member and the second optical member within the optical path of the device wherein the antistatic layer comprises at least one polymerizable onium salt having a fluoroorganic anion and at least one non-onium polymerizable monomer, oligomer, or polymer.
  • first optical member, second optical member, and antistatic layer may be disposed in direct contact with one another (or with intervening connecting layers such as adhesives, etc.), (2) the antistatic layer may be in direct contact to either the first optical member or the second optical member (or with intervening connecting layers such as adhesives, etc.) and disposed some defined distance away from the other, or (3) there may be a defined distance or gap between the antistatic layer and the first optical member and between the antistatic layer and the second optical member.
  • optical device 10 comprises first optical member 12 , second optical member 14 , and antistatic layer 16 therebetween.
  • antistatic layer 16 is in direct contact with both first optical member 12 and second optical member 14 .
  • light as shown by ray 18 will be incident to front surface 20 whereupon it will be manipulated as desired by optical device 10 .
  • optical device 210 comprises first optical member 212 , second optical member 214 and antistatic layer 216 which is adhered to back surface 222 of first optical member 212 by optional adhesive layer 224 .
  • Device 210 further comprises optional frame 226 which supports first optical member 212 and second optical member 214 in desired optically effective arrangement to achieve desired optical performance.
  • optical device 310 comprises first optical member 312 , second optical member 314 , and intermediately thereto without contact to either optical member antistatic layer 316 which are supported in desired optically effective arrangement by optional frame 326 .
  • Optical members for use in optical devices of the present invention can be readily selected by those skilled in the art, dependent in part upon the optical performance desired of the resultant device.
  • Optical films used herein could be monolayer members, e.g., substantially flat sheet of polyester sometimes referred to as a polyester base film, or multilayer assemblies comprising intricately formed component features that provide more specialized optical performance.
  • the first optical member and the second optical member may be independently selected from the group consisting of optical base films, multilayer optical films, diffuse reflecting polarizer films, prismatic brightness enhancement films, arrays of prismatic optical features, arrays of lenticular optical features, and beaded gain diffuser films.
  • one or both of the optical members will be individually selected from the group consisting of reflective polarizers (e.g., so-called multilayer optical films or “MOFs” having regularly repeating layers of alternating refractive indices), brightness enhancement films, and diffuse reflecting polarizer films (sometimes referred to as “DRPFs” having multiphase structures with domains of differing refractive indices).
  • reflective polarizers e.g., so-called multilayer optical films or “MOFs” having regularly repeating layers of alternating refractive indices
  • DRPFs diffuse reflecting polarizer films
  • DBEF-II Dual Brightness Enhancement Film II
  • Suitable prismatic brightness enhancement films (sometimes referred to as “BEFs”), also commercially available from 3M, are described in, e.g., U.S. Pat. Nos. 5,771,328 (Wortman et al.), 6,280,063 (Fong), and 6,354,709 (Campbell et al.) and U.S. Patent Appln. Publn. No. 20090017256 (Hunt et al.).
  • Illustrative examples of diffuse reflecting polarizer films that can be used as optical members herein include those disclosed in U.S. Pat. No. 5,825,543 (Ouderkirk et al.).
  • Illustrative examples of commercially available optical films suitable for use herein include VIKUITITM Dual Brightness Enhanced Film (DBEF), VIKUITITM Brightness Enhanced Film (BEF), VIKUITITM Diffuse Reflective Polarizer Film (DRPF), VIKUITITM Enhanced Specular Reflector (ESR), and VIKUITITM Advanced Polarizing Film (APF), all available from 3M Company.
  • DBEF Dual Brightness Enhanced Film
  • BEF VIKUITITM Brightness Enhanced Film
  • DRPF Diffuse Reflective Polarizer Film
  • ESR VIKUITITM Enhanced Specular Reflector
  • API Advanced Polarizing Film
  • a microstructure-bearing article e.g. brightness enhancing film
  • a method including the steps of (a) preparing a polymerizable composition; (b) depositing the polymerizable composition onto a master negative microstructured molding surface in an amount barely sufficient to fill the cavities of the master; (c) filling the cavities by moving a bead of the polymerizable composition between a preformed base (such as a PET film) and the master, at least one of which is flexible; and (d) curing the composition.
  • the master can be metallic, such as nickel, nickel-plated copper or brass, or can be a thermoplastic material that is stable under the polymerization conditions, and that preferably has a surface energy that allows clean removal of the polymerized material from the master.
  • Useful base materials include, for example, styrene-acrylonitrile, cellulose acetate butyrate, cellulose acetate propionate, cellulose triacetate, polyether sulfone, polymethyl methacrylate, polyurethane, polyester, polycarbonate, polyvinyl chloride, polystyrene, polyethylene naphthalate, copolymers or blends based on naphthalene dicarboxylic acids, polycyclo-olefins, polyimides, and glass.
  • the base material can contain mixtures or combinations of these materials.
  • the base may be multi-layered or may contain a dispersed component suspended or dispersed in a continuous phase.
  • examples of preferred base materials include polyethylene terephthalate (PET) and polycarbonate.
  • PET polyethylene terephthalate
  • useful PET films include photograde polyethylene terephthalate and MELINEXTM PET available from DuPont Teijin Films of Hopewell, Va.
  • Some base materials can be optically active, and can act as polarizing materials.
  • Polarization of light through a film can be accomplished, for example, by the inclusion of dichroic polarizers in a film material that selectively absorb passing light.
  • Light polarization can also be achieved by including inorganic materials such as aligned mica chips or by a discontinuous phase dispersed within a continuous film, such as droplets of light modulating liquid crystals dispersed within a continuous film.
  • a polarizing film can be prepared from microfine layers of different materials. The materials within the film can be aligned into a polarizing orientation, for example, by employing methods such as stretching the film, applying electric or magnetic fields, and coating techniques.
  • polarizing films examples include those described in U.S. Pat. Nos. 5,825,543 and 5,783,120 (both Ouderkirk et al.). The use of these polarizer films in combination with a brightness enhancement film has been described in U.S. Pat. No. 6,111,696 (Allen et al.). Other examples of polarizing films that can be used as a base are those films described in U.S. Pat. No. 5,882,774 (Jonza et al.).
  • Useful substrates include commercially available optical films marketed as VIKUITITM Dual Brightness Enhancement Film (DBEF), VIKUITITM Brightness Enhancement Film (BEF), VIKUITITM Diffuse Reflective Polarizer Film (DRPF), VIKUITITM Enhanced Specular Reflector (ESR), and VIKUITITM Advanced Polarizing Film (APF), all available from 3M Company.
  • DBEF Dual Brightness Enhancement Film
  • BEF VIKUITITM Brightness Enhancement Film
  • DRPF Diffuse Reflective Polarizer Film
  • ESR VIKUITITM Enhanced Specular Reflector
  • API VIKUITITM Advanced Polarizing Film
  • One or more of the surfaces of the base film material can optionally be primed or otherwise be treated to promote adhesion of the optical member to the base.
  • Primers particularly suitable for polyester base film layers include sulfopolyester primers, such as described in U.S. Pat. No. 5,427,835 (Morrison et al.).
  • the thickness of the primer layer is typically at least 20 nm and generally no greater than 300 nm to 400 nm.
  • the optical member can have any of a number of useful patterns. These include regular or irregular prismatic patterns, which can be an annular prismatic pattern, a cube-corner pattern or any other lenticular microstructure.
  • a useful microstructure is a regular prismatic pattern that can act as a totally internal reflecting film for use as a brightness enhancement film.
  • Another useful microstructure is a corner-cube prismatic pattern that can act as a retro-reflecting film or element for use as reflecting film.
  • Another useful microstructure is a prismatic pattern that can act as an optical turning film or element for use in an optical display.
  • Brightness enhancing films generally enhance on-axis luminance (referred herein as “brightness”) of a lighting device.
  • the microstructured topography can be a plurality of prisms on the film surface such that the films can be used to redirect light through reflection and refraction.
  • the height of the prisms typically ranges from 1 to 75 microns though features outside this range may, of course, be used.
  • the microstructured optical film can increase brightness of an optical display by limiting light escaping from the display to within a pair of planes disposed at desired angles from a normal axis running through the optical display.
  • the microstructured optical member of a brightness enhancing film generally comprises a plurality of parallel longitudinal ridges extending along a length or width of the film. These ridges can be formed from a plurality of prism apexes. Each prism has a first facet and a second facet. The prisms are formed on a base that has a first surface on which the prisms are formed and a second surface that is substantially flat or planar and opposite the first surface. By right prisms it is meant that the apex angle is typically 90°. However, this angle can range from 70° to 120° and may range from 80° to 100°. These apexes can be sharp, rounded or flattened or truncated.
  • the ridges can be rounded to a radius in a range of 4 to 7 to 15 micrometers.
  • the spacing between prism peaks (or pitch) can be 5 to 300 microns.
  • the prisms can be arranged in various patterns such as described in U.S. Pat. No. 7,074,463 (Jones et al.).
  • the pitch of the structures of a brightness enhancing film is typically preferably 1 millimeter or less, more preferably from 10 microns to 100 microns, and still more preferably from 24 microns to 50 microns. A pitch of 50 microns has been found to work quite well. The preferred pitch will depend, in part, on the pixel pitch of a liquid crystal display or the parameters of some other optical application of the film. The prism pitch should be chosen to help minimize moire interference.
  • the pitch is preferably 10 to 36 microns, and more preferably 17 to 24 microns.
  • the prism facets need not be identical, and the prisms may be tilted with respect to each other.
  • the relationship between the total thickness of the optical article, and the height of the prisms, may vary. However, it is typically desirable to use relatively thinner optical members with well-defined prism facets.
  • a typical ratio of prism height to total thickness is generally from 0.2 to 0.4.
  • thicker BEF materials will be used, such as BEF materials having a 50 micron pitch and 25 micron thickness.
  • optical devices of the invention may be made using other kinds of optical members or other embodiments of MOF, BEF, or DRPF materials than those illustrative examples discussed above.
  • the antistatic constructions described herein comprise a polymerized reaction product of a polymerizable resin composition comprising an antistatic agent.
  • antistatic agents can provide static decay times (as measured according to the test method described in the Examples) of 2 to 10 seconds, it has been found that only certain kinds and amounts of antistatic agents can provide static decay times of less than 2 seconds.
  • Preferred antistatic agents provide static decay times of no greater than 2, 1, or 0.1 seconds.
  • the kind and amount of antistatic agent in the antistatic layer is also selected such that the presence thereof in the polymerizable resin does not detract from the adhesion of the polymerized antistatic layer with the base film layer or the microstructures or microstructured member.
  • the entire construction so obtained exhibits a crosshatch peel adhesion (as measured according to the test method described in the Examples) to the base film layer of at least 80%, 85%, or 90%. In most preferred embodiments, the crosshatch adhesion is 95 to 100%.
  • the antistatic layer comprises the reaction product of at least one polymerizable onium salt having an anion and at least one non-onium polymerizable monomer, oligomer, or polymer.
  • Suitable onium salts can be selected from the group consisting of: ammonium salts, sulfonium salts, phosphonium salts, pyridinium salts, and imidazolium salts
  • a preferred onium salt for use in the present invention has the formula:
  • the onium salt has one of the formulas:
  • the onium salt may be present in the layer at a weight percentage of 1 to 99%, preferably 10 to 60%, more preferably 30 to 50%.
  • the acryl functional oniums are preferred over the methacryl oniums because they exhibit a faster and greater degree of cure.
  • Illustrative examples of anions useful herein include alkyl sulfates, methane sulfonates, tosylates, fluoroorganics, fluoroinorganics, and halides.
  • the anion is a fluorochemical anion.
  • Fluoroorganic anions suitable for use herein include those described in U.S. Pat. No. 6,924,329 (Klun et al.), column 8, lines 2 to 65.
  • the fluoroorganic ions provide greater solubility and compatibility of the onium salt with the non-onium polymerizable monomers, oligomers, or polymers. This is important in providing a layer with good clarity, and good ion mobility which can improve the antistatic performance of the resultant layer.
  • Some illustrative examples include —C(SO 2 CF 3 ) 3 , —O 3 SCF 3 , —O 3 SC 4 F 9 , and —N(SO 2 CF 3 ) 2 .
  • —O 3 SCF 3 —O 3 SC 4 F 9 , and —N(SO 2 CF 3 ) 2 .
  • —N(SO 2 CF 3 ) 2 is most preferred because it provides a broader range of solubility than some of the alternatives, making compositions containing it somewhat easier to prepare and use.
  • the non-onium polymerizerable monomers, oligomer, or polymers are key to the performance of the optical film. They, along with the onium salts, control key characteristics of the antistatic optical film including the static decay of the film, its haze and clarity, its cohesive strength, and its interlayer adhesion.
  • the onium salt, polymerizable silicone and/or perfluoropolyether content, and other components, if any, should be compatible in that they will mix and polymerize to form transparent films.
  • the antistatic layer will be formed on the optical layer by the following method: (1) providing a liquid coating composition comprising (a) at least one polymerizable onium salt as described herein, (b) at least one non-onium polymerizable silicone or perfluoropolyether moiety-containing monomer, oligomer, or polymer as described herein, and optionally (c) at least one non-silicone, non-perfluoropolyether monomer, oligomer, or polymer; (2) applying the liquid coating composition to the surface of an optical layer; and (3) curing the liquid coating composition in situ to form the antistatic layer on the surface of the optical layer.
  • a liquid coating composition comprising (a) at least one polymerizable onium salt as described herein, (b) at least one non-onium polymerizable silicone or perfluoropolyether moiety-containing monomer, oligomer, or polymer as described herein, and optionally (c) at least one non-silicone, non-perfluoropolyether
  • the antistatic layer will be formed on one side of a substrate film, e.g., a polyester film, the other side of which is subsequently positioned on the surface of an optical film, e.g., adhered by lamination or with adhesive, or held in place with mechanical means.
  • a substrate film e.g., a polyester film
  • an optical film e.g., adhered by lamination or with adhesive, or held in place with mechanical means.
  • the T g of the cured antistatic layer is preferably less than 50° C., more preferably less than 40° C., even more preferably less than 30° C., even more preferably less than 20° C., even more preferably less than 10° C., and most preferably less than 0° C. While not wishing to be bound by this theory, it is believed that ionic mobility is needed to provide desired antistatic performance.
  • non-onium polymerizerable monomers, oligomers, or polymers must be carefully chosen to be compatible with the onium salts so as to provide for clear, homogeneous solutions that are amenable to processing and coating. If the intended coating formulations are significantly incompatible, then the constituents wan stratify into two liquid phases or can also form solid precipitates so as to render the mixtures inappropriate for handling in a coating process and/or can yield hazy and inhomogeneous cured coatings.
  • the material choices for the antistat layer affect the adhesion of the antistat layer to the first optical member and the second optical member in those cases where the layers are in intimate contact. This adhesion requirement is particularly acute in optical display films wherein the construction needs to survive the durability requirements of the backlight industry without adhesion failure between optical members and the interstitial antistatic coating.
  • the non-onium polymizerable monomers, oligomer, or polymers must be carefully chosen to provide a layer with sufficient cohesive strength of the cured antistatic layer.
  • the cohesive strength is not only important for the durability of the finished optical construction as described above but is also critical to the successful coating and curing of the antistatic formulation. For example, if the antistatic formulation of choice is cast and cured against tooling for development of microtexture (as described below) then the effective and comprehensive release of the cured coating from the replication surface is strongly dependent on the cohesive strength of the coating. This is particularly challenging for the lower T g (mechanically softer) formulations required for premium charge decay and attendant antistatic performance.
  • Useful non-onium polymizerable monomers, oligomers, or polymers may include, for example, poly (meth)acryl monomers selected from the group consisting of:
  • the onium salt and polymerizable non-onium content should be compatible in that they will mix and polymerize to form transparent films.
  • the antistatic coatings of the current invention is such a way that at least one surface of the resulting cured coating layer is not perfectly smooth, but rather, has a microtextured surface and/or a matte finish.
  • the antistatic layer may also serve the additional purpose of, for example, optically masking and/or eliminating physical defects such as scratches, and undesirable optical effects such as moiré and color mura.
  • One method of producing such a surface involves forming the antistatic layer against microstructured tooling.
  • Illustrative examples are disclosed PCT Application Nos. US2010/036018 (Aronson et al.) and US2010/045118 (Yapel et al.). Microstructures which have been machined into the tooling are replicated on the surface of the final cured coating which has been cast against the tooling.
  • Microstructures can be any type microstructures that may be desirable in an application.
  • microstructures can be recessions or depressions.
  • microstructures can be protrusions.
  • microstructures form a regular pattern.
  • microstructures form an irregular pattern.
  • microstructures form a pseudo-random pattern that appears to be random.
  • microstructures can have any height and any height distribution.
  • Another method of producing such a surface involves forming the antistatic layer against tooling that has been subjected to electrodeposition of metal to form a fine structure on the tooling, as taught in PCT Application No. WO2009/079275 (Aronson et al.).
  • the tooling may or may not have a microstructure of some kind already machined upon it prior to the electrodeposition. This deposition process creates raised areas on the tooling, which in turn create recesses in a cured coating that had been cast against the tooling.
  • the shapes and sizes of the recesses vary depending upon the type of metal that is electroplated onto a roll mold.
  • the shapes and sizes of the recesses are the reverse of the shapes and sizes of the metal structures plated onto the roll. Such shapes include those that resemble pores, semi-hemispheres, “jagged” valleys, “craters,” and the surface of cauliflower. Recesses may overlap, be within one another, or be isolated from one another.
  • the size, that is, largest diameter, of the recesses can range from 0.5 micrometers to 125 micrometers at their largest diameter. A typical range is from 0.5 to 15 micrometers. Areas of the recesses can range from 0.01 to 1100 square micrometers. Depths can range from 0.2 to 20 micrometers.
  • a microstructured roll is subjected to an electroplating process.
  • Metal accretes inhomogeneously on the microstructured surface of the roll, forming protuberances.
  • the microstructured surface of the optical film replicates with pores or pits, etc., relative to the microstructured surface of the roll.
  • the size and density of the metal structures deposited onto the microstructured roll via the electroplating process is determined by the current density, the roll face speed, and the plating time.
  • the type of metal salt used in the electroplating process determines the geometry of the deposited metal structures, and thus, determines the shape of the recesses on the microstructured surface.
  • the location and disposition of the deposited metal structures on the microstructured roll is random.
  • Yet another method of producing such a surface involves manipulating the process of curing the coating, after it has been applied smooth, in such a way that texture can be simply imposed upon the coating and cured in place, as taught in US Patent Appln. Publn. No. 2009/0029054 (Yapel et al.).
  • a coated substrate comprising a coatable material disposed on a substrate is treated in such a way as to change the viscosity of the coatable material from the initial viscosity to a second viscosity, and then the surface of the coating is contacted with at least one face-side roller to impart a matte finish and the coatable material is optionally further hardened to provide the finished coating film.
  • a coatable material is applied to (e.g., coated on) a substrate to provide the coated substrate.
  • Coatable material is carried on the substrate and is treated to change the viscosity of the coatable material from a first or initial viscosity to a second viscosity.
  • the first viscosity is lower than the second viscosity so that the coatable material is changed by being thickened or partially cured.
  • the coatable material may have an initial viscosity that is higher than the second viscosity so that changing the viscosity of the coatable material may require at least some softening of the coatable material.
  • the material is then subjected to face-side pressure to impart a matte finish thereon.
  • the coatable material may optionally be further hardened, cured or solidified and the resulting film may be conveyed to another processing station such as a cutting station, or to a wind-up roll, for example. Expensive tooling is not required to impart a matte finish.
  • a multiphase coating can have a matte surface structure generated from immiscible materials incorporated in the coating at the surface or within the bulk of the coating, e.g., entrainment of particles such as polymethyl methacrylate beads in the coating.
  • particles with different refractive index from the bulk of the coating can be used to impart desired haze properties without necessarily yielding a matte surface.
  • useful particles can be of any shape, typically preferred particle shapes are often in the form of spherical or oblong beads. Preferable particle sizes are generally 0.1 microns to 20 microns average diameter. Particles can be made from any material that is compatible with the coating.
  • suitable materials for particles include polymethylmethacrylate, polybutylmethacrylate, polystyrene, polyurethane, polyamide, polysilicone, and silica.
  • Useful particles can be obtained from Ganz Chemical, Sekisui Plastics Co., Ltd., and Soken Chemical & Engineering Co., Ltd, all of Japan.
  • Average static decay was determined for film samples using the following method. Sheets of test materials were cut into 12 cm by 15 cm samples and conditioned at relative humidity (“RH”) of 44% to 50% at nominal room temperature (“RT”) of 23° C. to 27° C. for at least 12 hours. The static charge dissipation time was measured under the same conditions of temperature and humidity as used for the 12 hour preconditioning according to MIL-STD 3010, Method 4046, formerly known as the Federal Test Method Standard 10113, Method 4046, “Antistatic Properties of Materials”, using an ETSTM Model 406D Static Decay Test Unit (manufactured by Electro-Tech Systems, Inc., Glenside, Pa.).
  • This apparatus was used to induce an initial static charge (Average Induced Electrostatic Charge) on the surface of the flat test material by using high voltage (5000 volts), and a field meter was used to observe the charge decay. The actual charge induced by the imposition of the 5000 volt induction was noted. Then the time required for the charge to decay to 10 percent of the initial induced charge was recorded. This is the static charge dissipation time. The lower the static charge dissipation time, the better are the antistatic properties of the test material. All reported values of the static charge dissipation times in this specification were determined by taking the average of at least 6 separate determinations (Average Charge Decay).
  • At least three of these determinations were measured using a positive +5 KV applied charge and at least three of these determinations were measured using a negative ⁇ 5 KV applied charge.
  • a sample being tested did not accept a charge of at least 80% of the imposed 5 KV potential (i.e., 4000 volts) it was deemed not to be antistatic and assigned the designation of “wnc” (would not charge).
  • T g glass transition temperatures
  • the sample was scanned at an overall heating rate of 2.5° C./min, with superimposed modulation amplitude of 0.5° C. and modulation period of 60 seconds, to a final temperature of 100° C.
  • the reversible component of heat flow was recorded by the instrument and analyzed using software provided by TA Instruments to determine the T g as the midpoint of the characteristic inflection associated with the glass transition as seen in reversible heat flow thermograms.
  • Adhesion of the BEF prism coat and antistatic under coat to a base film were determined using ASTM D3359-02, with minor modifications as detailed here. First, the specimen coatings were scored in a selected test area with a cross hatch pattern. Next, adhesive tape was adhered to the test area. Finally, the tape was peeled from the test area in a prescribed manner. The adhesion was evaluated based upon the extent of removal of cross hatch scored coating from the specimen.
  • the device for scoring the specimen had 6 sharp scoring blades arranged in parallel array with equal blade-to-blade spacing of approximately 1 mm. The scoring device was dragged across the test area with an applied load of 1000 grams.
  • This force was chosen as adequate to penetrate the two stacked coatings such that each blade penetrated at least to the surface of the film underlying the coatings, and possibly slightly beyond and into the film.
  • the six lanes of score were applied to a length of 2 to 3 inches (5 to 7.5 cm) at an angle of 45 degrees to the BEF prism axis. Scoring to similar length was then performed approximately orthogonally to the first scoring direction to form a cross hatch such that the second scoring was at an angle of ( ⁇ )45 degrees to the BEF prism axis. This provided a 5 by 5 array of scored squares at a final cross hatch area of 25 mm 2 . One diagonal of the cross hatch square lay parallel to the BEF prism axis.
  • a piece of 3MTM #610 tape (a cellophane tape with a high tack, rubber resin adhesive) was then applied by hand to the test area such that the long axis of the tape was coincident with the BEF prism axis.
  • the tape was pressed firmly onto the test specimen using firm hand pressure with a soft plastic squeegee.
  • the test specimen was then allowed to relax undisturbed for three to four minutes to allow the adhesion to build to a steady state.
  • the tape was then removed by hand as quickly and aggressively as possible, such that the tape end was pulled straight up in the direction normal to the coated surface.
  • the evaluation of adhesion was based on how much of the cross hatched area was removed (transferred to tape adhesive) after the tape peel according to the following ranking system:
  • cross hatch adhesion was measured four times on a given material and performance was reported as an average of the rankings determined for each of the four peel tests.
  • the same operator performed all cross hatch peel adhesion tests reported herein, so as to eliminate the possibility of operator variability.
  • the lower layer (2656.5 g) was again separated from the aqueous layer and placed in a dry 5 L, 3-necked round bottom equipped with overhead stirrer and stillhead, and air bubbler.
  • To the flask was added 2000 g acetone and the reaction was distilled at atmospheric pressure over 6 hour with an air sparge to azeotropically dry the product, yielding 2591 g of a clear liquid which slowly crystallized to a solid.
  • the reaction was diluted with 1329 g of t-butyl methyl ether, and washed with 443 g water containing 25.47 g (0.424 mol) acetic acid. The layers were separated and the upper organic layer was washed with 4443 g of saturated aqueous sodium carbonate. The layers were separated, and the organic layer dried over magnesium sulfate, filtered, and concentrated on a rotary evaporator to provide the intermediate N-(acryloyloxyethyl)-N,N-diethyl amine.
  • a cylindrical reactor under an air atmosphere equipped with overhead stirrer and reflux condenser was charged with 600 g (3.49 mol) N-(acryloyloxyethyl)-N,N-diethyl amine, 24.74 g (0.21 mol) sodium carbonate, 0.15 g MEHQ, and 0.03 g phenothiazine at 23° C.
  • 462.7 g (3.67 mol) dimethyl sulfate was added via dropping funnel over 5 hours with the reaction reaching a maximum temperature without added heating of 60.4° C.
  • a cylindrical reactor under an air atmosphere, equipped with overhead stirrer and reflux condenser was charged with 500 g (2.69 mol) AGEFLEXTM FM2*PTZ, 19.06 g (0.16 mol) sodium carbonate, 0.10 g MEHQ, and 0.02 g phenothiazine, and heated to 39.5° C.
  • 356.5 g (2.83 mol) dimethyl sulfate was added via dropping funnel over 2.25 hour with the reaction reaching a maximum temperature without added heating of 76.3° C. After 3.25 hour a sample was taken for 1 H NMR analysis, and at 4.25 hour the reaction was heated to 50° C.
  • This intermediate (with no filtration) (816.3 g (2.31 mol)) was dissolved in 612.2 g deionized water and reacted with 804.3 g (82.3% solids in water, 2.31 mol) HQ-115, to form a lower organic layer which was washed with an additional 612 g deionized water, separated, diluted with 600 g acetone, dried over magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield 1164.6 g POS-4 as a brownish oil.
  • the aqueous layer was re-extracted with another 150 g of dichloromethane.
  • the two dichloromethane extracts were combined, along with 30 g of additional dichloromethane used for washing glassware containing the dichloromethane layers, and were washed with 100 g of deionized water.
  • the organic layers were dried over magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield 97.59 g of POS-6 as a light tan solid.
  • a three neck 3 L round bottom reaction flask equipped with overhead stirrer, condenser, and temperature probe was charged with 234 weight parts of AGEFLEXTM FA 1, 617 parts of acetone, 500 parts of 1-bromohexadecane, and 0.5 parts of BHT (butylhydroxytoluene, antioxidant added as inhibitor to prevent premature polymerization).
  • the mixture was heated to 35° C. by using two IR lamps with stirring at 150 rpm. After 24 hours of heating the reaction mixture was cooled to room temperature.
  • the clear reaction solution was transferred to a round bottom flask and acetone was removed by rotary evaporation under vacuum at 40° C. The resulting solid residue was mixed with 1 L cold ethyl acetate and mixed for 10 min.
  • the resultant aqueous phase was combined with the first aqueous phase and distilled at 80° C. with an air bubbler and a slight aspirator vacuum to yield 53 g POS-10 as a thick white liquid which solidified into a flaky white wax.
  • a 1 L, 3-neck round bottom flask equipped with overhead stirring was charged with 100.00 g (100% solids, 0.4390 mol) of acryloxyethyl-N,N-dibutylamine. This solution was set to stirring at 45° C., and 56.46 g (1.02 eq., 0.4477 mol) dimethylsulfate was added dropwise over 1 hr, under air. After approximately 25% of the DMS was added, 123 g acetone was added to solubilize the product, which is a tan-colored solid; the temperature was lowered to 40° C. Reaction progressed for a total of 4 hours, whereupon the acetone was distilled off at 56° C.
  • a 250 mL round bottom flask equipped with an overhead stirrer and fitted with a reflux condenser was charged with 50 g (0.349 mol) dimethylaminoethyl acrylate.
  • the flask was placed in an oil bath at room temperature under dry air, and a pressure equalizing addition funnel charged with 44.03 g (0.349 mol) dimethyl sulfate was added over 5.5 h.
  • the oil bath temperature was raised to 30° C. at 2 h with 50% of the dimethyl sulfate addition complete.
  • the bath temperature was raised to 40° C., at 3 h with 75% of the dimethyl sulfate addition complete.
  • the bath temperature was raised to 60° C., at 3.5 h with 80% of the dimethyl sulfate addition complete.
  • the bath was heated to 80° C., and POS-13 was isolated as a brown-yellow liquid.
  • POS-14 was prepared as described in Preparation of Antistatic Agent C in U.S. Patent Appln. Publn. No. 2007141329.
  • a 250 mL, 3-necked round bottom flask with overhead stirrer was charged with 40 g (0.0706 mol) C 12 H 25 N(CH 3 )(CH 2 CH 2 OH) 2 + ⁇ N(SO 2 CF 3 ) 2 , 17.14 g (0.1694 mol) triethylamine, and 71.84 g dichloromethane.
  • the flask was cooled in an ice bath and 14.70 g (0.1624 mol) acryloyl chloride was added over 45 min.
  • liquid UV-curable antistatic coating compositions were prepared by mixing 40 parts by weight of the polymerizable onium salt POS-1, with 35 parts of a monofunctional acrylate, 25 parts of a multifunctional acrylate, and 0.5 parts of IRGACURETM 819 as photoinitiator.
  • the monofunctional acrylates used were selected as indicated from the following: SR 339 (2-phenoxy ethyl acrylate), EBECRYLTM 110 (ethoxylated 2 phenol acrylate), CD 9087 (ethoxylated 3 phenol acrylate), and CD 9088 (ethoxylated 6 phenol acrylate).
  • the multifunctional acrylates used were selected as indicated from the following: EBECRYLTM 8402 (aliphatic urethane diacrylate), SR 494 (ethoxylated trimethylolpropane triacrylate), and SR 9035 (ethoxylated 4 pentaerythritol tetraacrylate).
  • the specific antistatic coating formulations are shown in Table 1 below. Each mixture was heated to 60° C. for 30 minutes in a sealed sample bottle, shaken vigorously by hand to mix, and then allowed to cool at ambient conditions. At room temperature all the solutions were homogeneous, clear, slightly yellow due to the photoinitiator, and of modest viscosity.
  • a laboratory scale coating device was used to fabricate coated film samples.
  • the coating apparatus as well as the coating procedures that were followed are described in detail in U.S. Pat. No. 6,899,922.
  • the apparatus was used to precisely apply continuous, void-free, and uniform coatings of liquid UV-curable antistatic coating compositions onto rectangular pieces of VIKUITITM DBEF II film (3M).
  • the film specimens for coating were circumferentially wrapped around the mounting roll of the apparatus such that the ends of the film met nearly flush with no gap and minimal overlap.
  • the mounting roll was then placed atop the primary and secondary pick-and-place rolls such that the film was nipped between the mounting roll and each of these two supporting auxiliary rolls.
  • Coating thickness was controlled by the precise dispensing of a known volume of coating formulation via syringe pump, model FUSIONTM 200 (Chemyx, Inc., Stafford, Tex.).
  • An oscillating delivery system was used to distribute the metered coating volume via a 1/16 inch (1.6 mm) ID piece of flexible TYGONTM tubing across the operating width of the primary transfer roll, as the three rolls of the apparatus were driven to rotate. This effectively delivered the coating as multiple beads, in helix patterns of opposite hand, on the operating width of the primary roll thus providing cross wise coating uniformity. Rotation of the rolls was maintained after the full complement of coating volume had been dispensed onto the primary roll such that the wetted surfaces of the primary and secondary rolls continuously contacted the film surface on the mounting roll.
  • the coating formulation was thus picked up from and placed back on to the film substrate, randomly and repeatedly, by the auxiliary rolls.
  • the rolls of the coating device were rotated for a plurality of revolutions until the coating was evenly distributed in the direction of roll rotation. In this way, uniform coverage was achieved over the test coating area on the VIKUITITM DBEF II film piece, with that area being defined by the operating width of the primary and secondary transfer rolls and the circumference of the mounting roll.
  • the syringe delivery volumes were set to achieve coating thicknesses of 1, 2, 3, and 4 microns for each of the formulations in Table 1. All antistatic coatings were carried out at room temperature. This apparatus is hereafter referred to as the laboratory scale multi-roll coater.
  • This assembly was preheated to 140° F. (60° C.) on a thermally controlled hot plate set at this target temperature.
  • a caulk-sized bead of optical acrylate resin was applied to the top 14 inch (36 cm) edge of the tool.
  • a specimen of antistatic coated VIKUITITM DBEF II was laminated to the tool with the cured antistatic coated surface facing the tool.
  • a laboratory roll lamination machine (model Catena 35 available from General Binding Corporation of Northbrook, Ill.) was then used for the BEF prism coating procedure.
  • the lab scale laminator was run at a gap setting of 3/16 inch (4.8 mm), a roll temperature of 140° F. (60° C.), and speed setting of 3.
  • the bead of optical grade acrylate was spread in a thin layer down the long axis of the tool such that the uncured optical acrylate resin evenly wetted the antistatic coating and concomitantly filled the prism geometry of the tooling.
  • the specimen was cured on the tool using a laboratory scale UV processor outfitted with a FUSIONTM UV D bulb, from Fusion UV Systems Inc.
  • the laminate was processed with the VIKUITITM DBEF II film facing the UV source such that the sandwiched optical resin was cured by UV light passing through the DBEF II film and proceeding through the resin toward the tooling.
  • the line speed of the UV processor was 30 ft/min (9.1 m/min) and the UV power was set at 100%. Nitrogen purge was not used during the cure.
  • the finished prototype specimen was removed from the tool immediately after curing for characterization. This provided a continuous cured BEF prism coat over the antistatic coating, with overall continuous prism structure thickness of 26 to 28 microns.
  • Example 5 wherein the T g of the cured formulation is 36.6° C. and associated charge decay of coated VIKUITITM DBEF II was in excess of 17 seconds for coating thicknesses from 1 to 4 microns.
  • the antistatic performance did not suffer from over-coating with BEF prisms and in many cases actually improved (charge decay decreased) after over-coating with BEF prisms.
  • the formulation of Example 7 as coated and cured onto VIKUITITM DBEF II to a final thickness of approximately 1 micron had a charge decay of 1.98 seconds.
  • the final construction had a charge decay of 0.59 seconds. This charge decay time is sufficiently low as to dissipate charge on a time scale of significance for preventing defects in the assembly of brightness enhancement films into backlight assemblies.
  • Coating compositions for Comparative Examples C15 to C20 were designed to be analogous to Examples 1 to 5 and Example 12, respectively, but without the polymerizable onium salt. Formulations are indicated in Table 3.
  • Multifunctional Acrylate Monofunctional Acrylates Aliphatic Ethoxylated Ethoxylated 4 2-Phenoxy Ethoxylated 2 Ethoxylated 3 Ethoxylated 6 Exam- Urethane Trimethylolpropane Pentaerythritol Ethyl Phenol Phenol Phenol Onium Salt Photo- ple Diacrylate Triacrylate Tetraacrylate Acrylate Acrylate Acrylate — initiator C15 41.7 0 0 58.3 0 0 0 0 0 0.5 C16 41.7 0 0 0 0 58.3 0 0 0 0.5 C17 41.7 0 0 0 0 0 58.3 0 0.5 C18 41.7 0 0 0 0 0 0 58.3 0 0.5 C19 0 41.7 58.3 0 0 0 0 58.3 0 0 0.5 C20 0 0 41.7 0 0 0 0 58
  • Table 5 documents a series of antistatic coating formulations that were prepared using various charges of the polymerizable onium acryloyloxyethyl-N,N,N-trimethylammonium bis(trifluoromethanesulfonyl)imide.
  • the amount of polymerizable onium salt in these formulations ranges from 0.5 wt % to 90 wt %, with composition determined as a weight percent of the total acrylate charged.
  • the same multifunctional and mono-functional acrylate pair was used with the polymerizable onium salt in each of these formulations.
  • the multifunctional acrylate used was EBECRYLTM 8402.
  • the monofunctional acrylate used was SR 339.
  • compositions were formulated such that the mass ratio of the EBECRYLTM 8402 to the SR 339 was constant at 0.714.
  • the photoinitiator used was IRGACURETM 819.
  • the specific antistatic coating formulations for Examples 21 to 33 are shown in Table 5. As in previous examples, these mixtures were each heated to 60° C. for 30 minutes in sealed sample bottles, shaken vigorously by hand to mix, and finally allowed to cool at ambient conditions. At room temperature all the solutions were homogeneous, clear, slightly yellow due to the photoinitiator, and of modest viscosity.
  • Formulations of Examples 21 to 33 were coated and cured onto VIKUITITM DBEF II using the same procedures and apparatus as outlined above with the exception that these examples were limited to a single antistatic coating thickness of 3 microns. Overcoat of the 3 micron antistatic coatings with 90°, 50 pitch BEF prisms was also similarly completed. Table 6 documents the glass transition temperature of each cured antistatic formulation, the charge decay of the 3 micron coating formulations on VIKUITITM DBEF II, and the charge decay of the specimens of the 3 micron coatings on VIKUITITM DBEF II after overcoating with the BEF prism structure, performed as in previous Examples. In addition, the cross hatch peel adhesion of the prism over-coated constructions was measured four times for each, with the average peel adhesion rating also documented in Table 6.
  • compositions for the antistatic coating in this type of optical film construction which effectively balances the antistatic performance with durability of coating/prism adhesion may be from 2 wt % and 50 wt % for this particular selection of polymerizable onium salt chemistry and coupled with these choices for the co-acrylates in the coating formulation.
  • Examples 34 to 39 and 41 as well as in Comparative Examples C40 and C42 to C47 a number of polymerizable onium salt candidates were tested for compatibility with a specific but representative acrylate coating formulation.
  • the acrylate coating mixtures in this test protocol were all based on 40 parts by weight of polymerizable onium salt combined with the acrylate mixture composed of 35 parts of SR 339, 25 parts of EBECRYLTM 8402, and 0.5 parts of the photoinitiator IRGACURETM 819.
  • the various polymerizable onium salt chemistries tested are listed in Table 7.
  • each polymerizable onium salt described in Table 7 was combined with the acrylate formulation into a sample bottle, sealed with a screw cap, and subsequently heated to 60° C. for 30 minutes in a convection oven. Each sample was vigorously shaken intermittently by hand during the course of the 30 minute heating cycle. After heating and shaking each sample was allowed to cool at ambient conditions. Samples were held quiescently at RT conditions for up to 2 days and then evaluated visually for homogeneity.
  • An antistatic coating formulation was prepared by mixing 40 parts by weight of polymerizable onium salt acryloyloxyethyl-N,N,N-trimethylammonium bis(trifluoromethanesulfonyl)imide (POS-1), 35 parts by weight of SR 339, 25 parts by weight of EBECRYLTM 8402, and 0.5 parts by weight of IRGACURETM 819 photoinitiator.
  • This formulation was coated and cured onto conventional 5 mil (127 micron) biaxially oriented adhesion-primed PET film MELINEXTM 618, from DuPont Teijin Films (Hopewell, Va.).
  • One specimen was prepared at each of the four coat thicknesses of 1, 2, 3, and 4 microns.
  • a series of antistatic coating formulations were prepared by mixing 40 parts of polymerizable onium acryloyloxyethyl-N,N,N-trimethylammonium bis(trifluoromethanesulfonyl)imide, with 60 parts of selected multi-functional acrylates.
  • Each formulation featured a single multifunctional acrylate as listed in Table 9 and 0.5 parts of IRGACURETM 819 photoinitiator (no non-onium monofunctional acrylates were used).
  • these mixtures were each heated to 60° C. for approximately 30 minutes in sealed sample bottles, shaken vigorously by hand to mix, and finally allowed to cool at ambient conditions. At room temperature all the solutions were homogeneous, clear, slightly yellow due to the photoinitiator.
  • Formulations of Examples 49 to 54 were coated and cured onto VIKUITITM DBEF II using the same procedures and apparatus as outlined above with the exception that the formulation of Example 49 was diluted with 20 parts by weight of isopropyl alcohol (IPA) in order to decrease the viscosity and facilitate coating at room temperature.
  • IPA isopropyl alcohol
  • the IPA was dried from the coated specimen of Example 49 during the standard 30 second preheat on the 140° F. (60° C.) platen just prior to cure.
  • Coating thickness for each formulation of Examples 49 to 54 was 3 microns. Overcoat of the cured 3 micron antistatic coatings with 90 degree 50 pitch BEF prisms was completed under the same experimental protocol previously described.
  • Table 9 documents the glass transition temperatures of the cured antistatic formulations.
  • the glass transition temperatures of formulations of Examples 50 and 51 could not be determined with the standard DSC technique described previously, as the transition was too broad and diffuse to be distinguished from the specimen thermogram.
  • the glass transition of the constituent commercial acrylates as published by their manufacturers is also documented in Table 9.
  • the charge decay of the 3 micron coating formulations on VIKUITITM DBEF II, and the charge decay of the specimens after overcoating with the BEF prism structure were measured and documented.
  • the peel adhesion ratings of the prism over-coated constructions were each measured four times with the average peel adhesion rating also documented in Table 9.
  • An antistatic coating formulation was prepared by mixing 40 parts of polymerizable onium salt acryloyloxyethyl-N,N,N-trimethylammonium bis(trifluoromethanesulfonyl)imide, 35 parts SR 339, 25 parts EBECRYLTM 8402, and 0.5 parts by weight of IRGACURETM 819 photoinitiator using standard mixing protocol described above. This formulation was then diluted with an equal portion of isopropanol (IPA) to form a 50% solids solution for coating. This recipe was then coated onto VIKUITITM DBEF II using the laboratory scale multi-roll coater as described above. Just after coating each specimen was immediately heated in a 140° F.
  • IPA isopropanol

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US10227426B2 (en) 2014-12-16 2019-03-12 3M Innovative Properties Company Antistatic polymers and methods of making the same
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JP5885459B2 (ja) * 2011-10-21 2016-03-15 Ｋｊケミカルズ株式会社 非水溶性イオン性ビニルモノマーの製造方法及びそれからなる帯電防止剤と帯電防止組成物
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US10113023B2 (en) 2014-12-16 2018-10-30 3M Innovative Properties Company Antistatic polymers and methods of making the same
US10227426B2 (en) 2014-12-16 2019-03-12 3M Innovative Properties Company Antistatic polymers and methods of making the same
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WO2017034870A1 (fr) 2015-08-21 2017-03-02 3M Innovative Properties Company Conducteurs transparents comprenant des métaux à l'état de traces et leurs procédés de fabrication
US20180217697A1 (en) * 2015-08-21 2018-08-02 3M Innovative Properties Company Transparent conductors including metal traces and methods of making same
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JP2020057011A (ja) 2020-04-09
TWI557194B (zh) 2016-11-11
KR20120088761A (ko) 2012-08-08
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JP2016197246A (ja) 2016-11-24
JP2013509619A (ja) 2013-03-14
JP2018132774A (ja) 2018-08-23
KR101831997B1 (ko) 2018-04-04
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WO2011053709A2 (fr) 2011-05-05
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