WO2017218516A1 - Compositions comprenant des polymères conjugués et leurs utilisations - Google Patents

Compositions comprenant des polymères conjugués et leurs utilisations Download PDF

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WO2017218516A1
WO2017218516A1 PCT/US2017/037227 US2017037227W WO2017218516A1 WO 2017218516 A1 WO2017218516 A1 WO 2017218516A1 US 2017037227 W US2017037227 W US 2017037227W WO 2017218516 A1 WO2017218516 A1 WO 2017218516A1
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polymeric film
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Leah A. THOMPKINS
Volha HRECHKA
Brett A.E. COURTRIGHT
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Polydrop, Llc
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/092—Polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C08K5/42—Sulfonic acids; Derivatives thereof
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124—Intrinsically conductive polymers
    • H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
    • C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/51—Charge transport
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/58—Physical properties corrosion-inhibiting

Definitions

  • Embodiments of the present invention generally relate to compositions comprising conductive polymers and methods of manufacturing and use of the same.
  • plastics and paints are insulators that require additives in order to create electrical conductivity.
  • Applications such as electrostatic dissipation and electrically charging paints for spray coating need to include conductive materials for proper use.
  • Metals have been the most common additives to create electrical conductivity, however, due to regulation, weight and health and safety, nano-particle metals are being phased out of various applications.
  • Metal additives are being replaced with intrinsically conductive, metal-free, materials such as poly(3,4- ethylenedioxythiophene) polystyrene sulfonate (PEDOT:PSS).
  • PEDOT:PSS poly(3,4- ethylenedioxythiophene) polystyrene sulfonate
  • ITO indium tin oxide
  • Embodiments of the present invention are directed to compositions comprising conductive polymers and their use in various applications, such as for conductive films and use in electrostatic discharge applications. Accordingly, in some embodiments is provided a composition comprising a conjugated polymer and one or more compounds of structure (I) or (II):
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , L 1 , L 2 , L 3 , L 4 , L 5 , a, b and n are as defined herein, provided at least two of R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are not H and provided that b is 1 for at least one integral value of n.
  • Polymeric films comprising the disclosed composition, and uses of the same in various applications are also provided.
  • Fig. 1 shows an SEM particle size image for PEDOT:PMVEMA powder.
  • Fig. 2 provides conductivity data for PEDOT:PMVEMA in water.
  • Fig. 3 shows 1H NMR spectra for PEDOT:PMVEMA in methanol.
  • “Amine” refers to a substituent of the formula -N(R) 2 , where each R is independently H, alkyl or aryl as defined herein.
  • Chlorate refers to the C10 3 " anion.
  • Chlorate refers to the C10 2 " anion.
  • Ether refers to a compound of the formula ROR, where each R is independently H, alkyl or aryl as defined herein.
  • a "fluoride” is a compound comprising at least one fluorine atom.
  • Haldroxyl refers to the -OH substituent.
  • Niro refers to the -N0 2 substituent.
  • Alkyl refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, which is saturated or unsaturated (i.e., contains one or more double and/or triple bonds), having from one to twelve carbon atoms (Ci-Ci 2 alkyl), preferably one to eight carbon atoms (Ci-C 8 alkyl) or one to six carbon atoms (Ci-C 6 alkyl), and which is attached to the rest of the molecule by a single bond, e.g., methyl, ethyl, ⁇ -propyl, 1-methylethyl (z ' so-propyl), «-butyl, «-pentyl, 1, 1-dimethylethyl (t-butyl), 3-methylhexyl, 2-methylhexyl, ethenyl, prop-l-enyl, but-l-enyl, pent-l-enyl, penta-l,4-dienyl
  • Alkyl includes alkenyls (one or more carbon-carbon double bonds) and alkynyls (one or more carbon-carbon triple bonds such as ethynyl and the like).
  • Fluoroalkyl refers to an alkyl group comprising at least one fluoro substituent.
  • Aliphatic refers to an alkyl group optionally containing one or more carbon-carbon double bond or carbon-carbon triple bond. Unless stated otherwise specifically in the specification, an alkyl and/or fluoroalkyl group is optionally substituted.
  • Alkylene or “alkylene chain” refers to a straight or branched divalent hydrocarbon chain linking the rest of the molecule to a radical group, consisting solely of carbon and hydrogen, which is saturated or unsaturated (i.e., contains one or more double and/or triple bonds), and having from one to twelve carbon atoms, e.g., methylene, ethylene, propylene, «-butylene, ethenylene, propenylene, «-butenylene, propynylene, «-butynylene, and the like.
  • the alkylene chain is attached to the rest of the molecule through a single or double bond and to the radical group through a single or double bond.
  • the points of attachment of the alkylene chain to the rest of the molecule and to the radical group can be through one carbon or any two carbons within the chain. Unless stated otherwise specifically in the specification, an alkylene chain is optionally substituted.
  • Alkoxy refers to a radical of the formula -OR a where R a is an alkyl radical as defined above containing one to twelve carbon atoms. Unless stated otherwise specifically in the specification, an alkoxy group is optionally substituted.
  • Aryl refers to a carbocyclic ring system radical comprising hydrogen, 6 to 18 carbon atoms and at least one aromatic ring.
  • the aryl radical is a monocyclic, bicyclic, tricyclic or tetracyclic ring system, which may include fused or bridged ring systems.
  • Aryl radicals include, but are not limited to, aryl radicals derived from aceanthrylene, acenaphthylene, acephenanthrylene, anthracene, azulene, benzene, chrysene, fluoranthene, fluorene, as-indacene, s-indacene, indane, indene, naphthalene, phenalene, phenanthrene, pleiadene, pyrene, and triphenylene.
  • “Spray polymer” refers to a composition as disclosed herein and a carrier fluid.
  • spray does not limit the substance to undergo spraying for application.
  • the substance may be applied to a surface through alternative, non-spray techniques such as spin coating and cloth transfer.
  • substituted used herein means any of the above groups (e.g.., alkyl, alkylene, alkoxy and/or aryl) wherein at least one hydrogen atom (e.g., 1, 2, 3 or all hydrogen atoms) is replaced by a bond to a non-hydrogen atom such as, but not limited to: a halogen atom such as F, CI, Br, and I; an oxygen atom in groups such as hydroxyl groups, alkoxy groups, and ester groups; a sulfur atom in groups such as thiol groups, thioalkyl groups, sulfone groups, sulfonyl groups, and sulfoxide groups; a nitrogen atom in groups such as amines, amides, alkylamines, dialkylamines, arylamines, alkylarylamines, diarylamines, N-oxides, imides, and enamines; a silicon atom in groups such as trialkylsily
  • Substituted also means any of the above groups in which one or more hydrogen atoms are replaced by a higher-order bond (e.g., a double- or triple-bond) to a heteroatom such as oxygen in oxo, carbonyl, carboxyl, and ester groups; and nitrogen in groups such as imines, oximes, hydrazones, and nitriles.
  • R g and R h are the same or different and independently hydrogen, alkyl, alkoxy, alkylaminyl, thioalkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, haloalkyl, heterocyclyl, N-heterocyclyl, heterocyclylalkyl, heteroaryl, N-heteroaryl and/or heteroarylalkyl.
  • Substituted further means any of the above groups in which one or more hydrogen atoms are replaced by a bond to an aminyl, cyano, hydroxyl, imino, nitro, oxo, thioxo, halo, alkyl, alkoxy, alkylaminyl, thioalkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, haloalkyl, heterocyclyl, N-heterocyclyl, heterocyclylalkyl, heteroaryl, N-heteroaryl and/or heteroarylalkyl group.
  • each of the foregoing substituents may also be optionally substituted with one or more of the above substituents.
  • PEDOT refers to a polymer comprising poly(3,4- ethylenedioxythiophene). Alternate varieties of PEDOT may be achieved through modification using dopants.
  • Polymer refers to a macromolecule comprising one or more structural repeating units (i.e., monomers).
  • a "polymer terminating group” is any moiety that terminates the polymerization of monomers when reacted with a growing polymer chain.
  • a polymer terminating group may be any moiety that reacts with a polymer free radical to terminate the polymerization reaction.
  • “Monomer” is a molecule that can be combined with itself or other molecules to form a polymer.
  • Dopant is an element, molecule or compound that is inserted into a substance to purposefully modify physical, chemical, or performance characteristics.
  • binding molecule is a chemical or compound that strongly attaches to another chemical or compound.
  • EDOT refers to the compound 3,4-Ethylenedioxythiophene.
  • PEDOT:PSS refers to the polymer PEDOT, namely poly(3,4- Ethylenedioxythiophene), that is associated to the binding polymer molecule polystyrene-sulfonate (PSS).
  • a “salt” is a neutral molecule or compound comprising a positively charged molecular segment and a negatively charged molecular segment.
  • Oxide refers to a molecule or compound comprising an element or molecule that is bound to oxygen.
  • Silane is an alkyl or alkoxy group, wherein at least one hydrogen atom has been replaced with a silicon atom, e.g. Si(CH 3 ) 4 .
  • a “disilane” is a silane dimer comprising a Si-Si bond.
  • an “acid” is a molecule or compound capable of donating a proton to another molecule or compound.
  • the definition can also include molecules or compounds capable of accepting a pair of electrons from another chemical or compound.
  • solvent refers to a substance which dissolves, disperses or suspends materials. The materials may or may not undergo further reaction within the solvent.
  • the present disclosure uses solvents both for the synthesis of the polymer material as well as the dispersion of the polymer for application as a film (i.e. as a carrier fluid).
  • Example solvents include, but are not limited to, acetone, ethanol, water, methanol, isopropanol, toluene, xylene, methyl ethyl ketone and benzene.
  • Carrier Fluid or “CF” refers to the chosen solvent for the application of the spray polymer material (i.e. a composition comprising a polymer and a carrier fluid). The polymer is dispersed within the solvent.
  • Frm or “coating” is a thin layer of material layered onto the surface of another.
  • the material may or may not be chemically adhered to the surface of another.
  • Substrate is a surface to which a coating is applied.
  • the substrate can be modified prior to coating to increase mechanical properties such as adhesion.
  • Dispossion is a mixture comprising a solid or polymer material within a solvent.
  • the solvent can be aqueous or non-aqueous.
  • Anionic refers to a chemical species which has either gained an electron (or pair of electrons) or lost a proton to form a negatively charged ion.
  • a “surfactant” is a substance that reduces the surface tension between two materials and thus allows them to interact more intimately.
  • An “ionic liquid” is a salt wherein the ions are poorly packed and thus the material is a liquid below 100 °C.
  • “Monovalent” refers to an atom or ion that is capable of forming just one chemical bond.
  • polyol is a molecule or compound comprising more than one hydroxyl group; these materials often serve as the precursor monomer of polyol polymers.
  • organic solvent is a compound that contains at least one carbon and is liquid at room temperature (i.e. approximately 25°C).
  • Example organic solvents include, but are not limited to, acetic acid, acetone, acetonitrile, benzene, chloroform, ethanol, methanol, N-methyl-2-pyrrolidinone, pentane, toluene, xylene, and butanol.
  • Organic solvents may be used as either a solvent for spray polymer dispersion or for film removal.
  • An “acidic solution” is solution which has a pH less than 7.
  • a “basic solution” is a solution which has a pH greater than 7.
  • D(50) or “Dv50” or “average particle size” refers to the size of a particle as measured through methods known in the art, such as laser diffraction, wherein 50% of the volume of particles has a smaller particle size.
  • Negtralizing agent is a substance which modifies the pH of a material or solution towards 7. In the instance of a material or solution that is acidic, the substance is basic. In the instance of a material or solution that is basic, the substance is acidic.
  • “Haze” is defined as the percentage of incident light that is scattered away from a normally incident beam by the window.
  • Color rendering index is a measurement of the degree to which light is the same color before and after passing through a medium.
  • U-factor is a measurement of the rate of heat loss through the center of a transparent material. It is not relevant to non-transparent portions of windows, such as sashes and frames.
  • Center of glass refers to the middle of a transparent material.
  • the material does not need to be glass in composition and may include non- glass substances such as polymers.
  • UV ultraviolet
  • the source of ultraviolet radiation may be natural (i.e. sunlight) or synthetically generated (i.e. artificial light source).
  • Infrared refers to radiation with a wavelength greater than 750 nm.
  • the source of infrared radiation may be natural (i.e. sunlight) or synthetically generated (i.e. artificial light source).
  • Visible or “visible light” refers to radiation with a wavelength ranging from 350 nm to 750 nm.
  • the source of infrared radiation may be natural (i.e. sunlight) or synthetically generated (i.e. artificial light source).
  • a “semi-transparent" substrate is one which allows for the transmission of at least 5% of incoming visible light. It only refers to radiation in the visible spectrum.
  • a “transparent” substrate is one which allows for the transmission of at least 50% of incoming visible light. It only refers to radiation in the visible spectrum.
  • the current disclosure is directed towards materials useful as coatings to optimize electrical conductivity or electrostatic discharge.
  • the disclosed materials can be used to coat electrical components and other devices requiring an electrically conductive coating.
  • the electrical conductivity of the disclosed compositions may range between 10 "4 S/cm to 10 8 S/cm.
  • the electronic conductivity of the composition is between 1 S/cm and 10 3 S/cm, 1 S/cm and 10 2 S/cm, 50 S/cm and 100 S/cm.
  • the electronic conductivity of the composition is between 10 "4 S/cm and 10 S/cm, 10 "3 S/cm and 1 S/cm, 10 "2 S/cm and 1 S/cm.
  • the electronic conductivity of the composition in the absence of the carrier fluid ranges from 0.001 to 1000 S/cm, 1 to 10 3 S/cm, 1 to 10 2 S/cm, or 50 to 100 S/cm. In some embodiments the electronic conductivity ranges from 10 "4 to 10 S/cm, 10 "3 to 1 S/cm, or 10 "2 to 1 S/cm.
  • the composition When used to coat substrates, such as electrical components, the composition may be combined with a carrier fluid and applied using any number of art recognized techniques, such as spray or spin coating and the like.
  • the electronic device is a CPU or motherboard.
  • the electronic device is an airplane, automobile, bicycle, or motorcycle.
  • the electronic device is a computer, tablet, or faceplate.
  • the composition is used as a spray polymer coating and an optically transparent film.
  • the disclosed materials represent a significant advancement over currently known methods for protective window coatings.
  • Current methods for protecting windows from UV and IR transmission include solid films in which the user cuts the appropriate shape and applies to the window directly.
  • high area windows, curved or bubble windows, or large number of windows the process can be tedious and may require professional installation.
  • high- energy efficiency windows and glass can be purchased and installed upon building construction. While effective for new construction, replacement windows are not a viable solution for all existing structures.
  • the composition is used for anti-corrosion.
  • the disclosed material can be used either as a direct-to-metal layer, or integrated into primers, paints, and topcoats to prevent metal oxidation.
  • the present invention overcomes limitations of previously described, existing solutions, and provides a number of other improvements.
  • the described composition has a relatively low viscosity when dissolved in a carrier fluid allowing the solution to be applied to windows using common household spray bottles.
  • the film is more effective than present materials at reducing the overall UV and IR transmission while keeping optical transmission high, as it can be applied as a thin uniform coating.
  • the spray polymer or polymer film can be designed to increase adhesion and scratch resistance to a wide range of substrates.
  • compositions and polymer films described herein provide a metal-free composition, which eliminates the need for chromium-based additives.
  • compositions may be added at any step during the coating process, allowing for versatility of materials and methods.
  • a composition comprising a conjugated polymer (Component 1) and one or more second components (Component 2).
  • Component 2 is a compound of structure (I) or (II) as described herein below.
  • the composition further comprises an oxidizing agent (Component 3).
  • the composition comprises a one type of Component 2.
  • the composition comprises more than one unique Component 2, for example two different compounds of structure (I), two different compounds of structure(II) or a compound of structure (I) and a compound of structure (II).
  • the Component 1 is positively charged and
  • Component 2 is negatively charged.
  • the composition comprises a physical mixture of Component 1 and Component 2.
  • the composition comprises a coordinated complex of Component 1 and Component 2.
  • the Component 1 and Component 2 are covalently bound.
  • the conjugated polymer can be chosen from a range of novel materials and those known in the art, for example those disclosed in U.S. Patent No. 7,361,728, the full disclosure of which is hereby incorporated by reference in its entirety.
  • the conjugated polymer comprises a polymer of 3,4- ethylenedioxythiophene (EDOT), carbazole, indole, azepine, p-phenylsulfide, aniline, pyrrole, fluorene, thiophene, or combinations thereof.
  • the conjugated polymer is a polymer comprising EDOT monomers.
  • the conjugated polymer comprises polypyrrole.
  • the molecular weight of the conjugated polymer after polymerization is above 1,000 g/mol, above 2,000 g/mol, above 5,000 g/mol, above 10,000 g/mol, above 20,000 g/mol, above 50,000 g/mol, above 150,000 g/mol, above 400,000 g/mol, above 1,000,000 g/mol, or above 2,000,000 g/mol. In another example the molecular weight of the conjugated polymer after polymerization is below 5,000,000 g/mol.
  • Component 2 can be tailored for increased adhesion, electrical conductivity or other desired properties of the composition. Accordingly, in some embodiments Component 2 comprises at least one compound of structure (I) or (II). In certain embodiments, Component 2 comprises a plurality of compounds that are each independently a compound of structure (I) or (II), for example, each compound comprising the same or different functionalities. In some embodiments, Component 2 comprises two functionalities, Functionality A and Functionality B. Not to be bound by theory, in some embodiments Functionality A is a functional group that complexes with Component 1 while Functionality B is a functional group that interacts with a substrate to which the composition is applied (e.g., a glass-interactive functional group).
  • Functionality A and B are both independently polar functional groups, optionally capable of hydrogen bonding.
  • Functionality A is -SO 3 H and Functionality B is a carboxylic acid, such as maleic acid.
  • the sum of the concentrations of Component 2 in the compositions ranges from 0.01 to 5 wt%.
  • Component 2 comprises a carboxylic acid functional group.
  • the Component 2 comprises an amine.
  • the composition further comprises a doping agent selected from ferric chloride and methyl sulfonic acid, and combinations thereof.
  • a doping agent selected from ferric chloride and methyl sulfonic acid, and combinations thereof.
  • Component 2 comprises polystyrene sulfonic acid-co-maleic acid. In other embodiments, Component 2 comprises polyacrylic acid, polymaleic acid, polystyrene sulfonate, polyacrylic-co-maleic acid, polystyrene sulfonic acid-co-maleic acid, polyacrylic acid-co-polystyrene, polystyrene sulfonate-co- polyethylene oxide, polystyrene sulfonate-co-polypropylene oxide or any combination thereof.
  • composition comprises a conjugated polymer and one or more compounds of structure (I) or (II):
  • R 4 and R 5 are independently H or a polymer terminating group
  • L 1 , L 2 , L 3 , L 4 and L 5 are, at each occurrence, independently a direct bond or an optionally substituted alkylene linker
  • a and b are each independently 0 or 1 for each integral value of n, provided that b is 1 for at least one integral value of n;
  • n is an integer of 1 or greater.
  • the composition comprises a compound of structure (I).
  • a and b are each independently 1 for at least one integral value of n.
  • L 4 and L 5 are each independently methylene or ethylene.
  • L 2 and L 3 are absent.
  • L 1 is absent.
  • R 1 has the following structure:
  • compositions comprise a compound of structure (I) having one of the following structures:
  • component 2 comprises both of the following compounds:
  • compositions comprise a compound of structure (II).
  • at least three of R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are not H.
  • R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently H, -OH, -CO 2 H or -SO 3 H.
  • the compound of structure (II) has th :
  • the conjugated polymer comprises heteroatoms.
  • the conjugated polymer is a polypyrrole, polycarbazole, polyindole, polyazepine, polyaniline, polythiophene or poly(p-phenylsulfide).
  • the conjugated polymer is poly(3,4-ethylenedioxythiophene.
  • the conjugated polymer is a carbocyclic conjugated polymer.
  • the conjugated polymer is a polyfluorine, polyphenylene, polypyrene, polyazulene, polynaphthalene, polyacetylene or polypheneylene vinylene.
  • the composition further comprises a doping agent, such as ferric chloride.
  • the composition is used as a spray polymer solution for coating substrates.
  • the composition further comprises a carrier fluid.
  • the carrier fluid comprises an organic solvent, such as toluene, acetone, xylene, methanol, ethanol or isopropanol.
  • the carrier fluid comprises water.
  • the composition further comprises a surfactant, for example the concentration of the surfactant in some embodiments ranges from 0.05 to 5 wt%.
  • the concentration of the conjugated polymer ranges from 0.5 to 30 percent by weight of the composition.
  • Component 1 will complex with Component 2.
  • the weight ratio between Component 1 and Component 2 may impact the final performance properties of the polymer in addition to altering the reaction kinetics.
  • the weight ratio of Component 1 to Component 2 ranges from 2: 1 to 1 : 1000.
  • the weight ratio of Component 1 to Component 2 ranges from 1 to 1000.
  • the weight ratio of Component 1 to Component 2 ranges from 1 : 1 to 1 :500, 1 :2 to 1 : 100, 1 :3 to 1 :20, or 1 :4 to 1 : 10.
  • the weight ratio of Component 1 to Component 2 ranges from 2: 1 to 1 : 1, 1.8: 1 to 1.1 : 1, or 1 :7 to 1.5: 1. In yet still another embodiment the weight ratio of Component 1 to Component 2 is 1 :4.
  • the molar ratios between Component 1 and Component 2 can be measured using NMR (e.g., 1H MR ), known to those in the art. In one embodiment, the molar ratio between Component 1 and Component 2 ranges between 100: 1 and 1 : 100. In another embodiment, the molar ratio between Component 1 and Component 2 ranges from 100: 1 to 10: 1, from 20: 1 to 5: 1, from 10: 1 to 2: 1, or from 5: 1 to 1 : 1. In still another embodiment, the molar ratio between Component 1 and Component 2 ranges from 1 : 100 to 1 : 10, from 1 :20 to 1 :5, from 1 : 10 to 1 :2, or from 1 : 5 to 1 : 1.
  • NMR e.g., 1H MR
  • the molar ratio between Component 1 and Component 2 as measured by X H NMR is around 1 : 1.
  • the solvent for the reaction can be altered for safety for both the user and the environment.
  • the solvent for synthesis comprises water.
  • the solvents comprise non-aqueous fluids, such as ethanol, acetone, methanol, toluene, isopropanol, benzene, or combinations thereof.
  • the concentration of Component 1 when mixed with Component 2 in solution is chosen to facilitate the reaction with optional Component 3.
  • the concentration of Component 1 when mixed with Component 2 in solution ranges from 0.05 M to 5M.
  • the concentration of Component 1 when mixed with Component 2 in solution ranges from 0.05 M to 1 M, 0.1 M to 0.9 M, 0.5 M to 0.9 M, 1 M to 4 M, or 2 M to 3 M.
  • the concentration of Component 1 when mixed with Component 2 in solution is less than 0.05 M or greater than 5 M.
  • the concentration of Component 1 when mixed with Component 2 in solution is 0.08 M.
  • an oxidization agent (Component 3) may be used.
  • the oxidizing agent comprises a persulfate, a chlorate, an oxide, a chloride, or combinations thereof.
  • the oxidizing agent comprises a material in its elemental form.
  • the oxidizing agent comprises potassium persulfate, ferric chloride, sodium persulfate, or combinations thereof.
  • Oxidizing agents refer to a large class of materials, some of which are listed in Table 2. Table 2 is illustrative list for exemplary purposes and not exhaustive. Oxidizing agents will be apparent to those skilled in the art.
  • the oxidizing agent may be chosen based on its reaction rate, solubility, and cost. In an additional embodiment, no oxidizing agent is used.
  • Oxides Barium peroxide, dibenzoyl peroxide, hydrogen peroxide, magnesium peroxide, nitrogen trioxide, potassium peroxide, sodium peroxide, perchloric acid
  • the ratio between Component 1 and Component 3 may impact the rate and extent of reaction.
  • the molar ratio of Component 1 to Component 3 ranges from 5: 1 to 1 :5, 1 : 1 to 5: 1, 2: 1 to 3 : 1, 1 : 1 to 1 :5, or 1 :2 to 1 :3.
  • the molar ratio of Component 1 to Component 3 is about 1 : 1.
  • the combination of Component 1, Component 2 and optional Component 3 can be heated or cooled to directly impact the rate of reaction.
  • the temperature of Mixture 1 is increased above 30 °C, above 40 °C, above 50 °C, above 60 °C, above 70 °C, above 100 °C, above 150 °C, above 200 °C, or above 300 °C.
  • the temperature of Mixture 1 is decreased below 30 °C, below 20 °C, below 10°C, or below 0 °C.
  • the temperature is held constant throughout the polymerization process.
  • the temperature of Mixture 1 is dynamic.
  • the time allowed for polymerization of Mixture 1 can be controlled to obtain ideal particle size.
  • the time allowed for polymerization of Mixture 1 ranges from 5 minutes to 48 hours.
  • the polymerization time for Mixture 1 ranges from 5 minutes to 10 hours, 30 minutes to 8 hours, 1 hour to 5 hours, or 2 hours to 4 hours.
  • the polymerization time for Mixture 1 is approximately 3 hours.
  • the polymerization time for Mixture 1 ranges from 10 hours to 48 hours, 12 hours to 24 hours, or 16 hours to 20 hours. In still another embodiment the polymerization time for Mixture 1 is greater than 48 hours.
  • Dopant 1 can be included in Mixture 1 prior to or after polymerization in order to supplement the performance characteristics and mechanical properties (e.g. adhesion) of the composition.
  • Dopant 1 is a material with suitable electron withdrawing capacity such as ferric chloride, methyl sulfonic acid, tosylate, or combinations thereof.
  • suitable electron withdrawing capacity such as ferric chloride, methyl sulfonic acid, tosylate, or combinations thereof.
  • Table 3 is illustrative list for exemplary purposes and not exhaustive. Dopants will be apparent to those skilled in the art.
  • Dopant 1 comprises a powder.
  • Dopant 1 is carbon, such as carbon black, carbon nanotubes, activated carbon, graphite, graphene.
  • the dopant comprises a metal oxide, such as zinc oxide, nickel (II) oxide, copper (IV) oxide, or molybdenum (III) oxide.
  • the composition further comprises a particulate, for example, Laponite, Laponite RDS, Laponite EP, or combinations thereof. In more specific embodiments, the composition comprises Laponite RDS.
  • Dopant 1 is typically added into solution after the combination of
  • the concentration of Dopant 1 as a measurement of the total mass of Component 1, Component 2, Component 3, and solvent ranges from 0.001 to 1 wt%, 0.01 to 0.1 wt%, or 0.05 to 0.1 wt%. In other embodiments the concentration of Dopant 1 ranges from 0.1 to 5 wt%, 1 to 10 wt%, 5 to 20 wt%, or 10 to 30 wt%.
  • the total concentration of dopants, as defined by the sum of the mass of all dopants, in Mixture 1 ranges from 0.001 to 1 wt%, 0.01 to 0.1 wt%, or 0.05 to 0.1 wt%. In other embodiments the concentration of Dopant 1 ranges from 0.1 to 5 wt%, 1 to 10 wt%, 5 to 20 wt%, 10 to 30 wt%.
  • the polymerized product after the reaction is acidic.
  • the pH of the composition ranges froml to 6, 2 to 5, 2 to 4, or 6 to 8.
  • a neutral or basic product may be desired.
  • Additive 1 can be used to alter the pH of the final product without harm to the performance characteristics of the polymeric film.
  • Additive 1 can be a strong base comprising sodium hydroxide, potassium hydroxide, lithium hydroxide, calcium hydroxide, barium hydroxide, or combinations thereof.
  • Additive 1 can be a weak base comprising ammonia, ammonium hydroxide, pyridine, trimethyl ammonia, or combinations thereof.
  • the intermediate product may be dried.
  • the intermediate product is dried using vacuum filtration, centrifuged, air dried, oven dried, or freeze dried.
  • the intermediate product may never undergo a drying phase.
  • the polymer composition may undergo a continuous solvent exchange.
  • the conjugated polymer can be commercially purchased or synthesized using methods known to those in the art.
  • the commercially available materials used as the conjugated polymer are PEDOT:PSS, poly(p-phenylene vinylene), poly(3-hexylthiophene), poly(pyrrole), poly(fluorene), poly(aniline), poly(acetylene), or combinations thereof.
  • the commercially available conjugated polymers are further modified using Dopant 1 or Additive 1 to yield a novel material.
  • the composition can be mixed with a carrier fluid (CF) for the creation of the Spray Polymer material.
  • a composition comprising the foregoing composition and a carrier fluid is provided.
  • the carrier fluid is an organic solvent.
  • the CF comprises acetone, ethanol, methanol, isopropanol, toluene, xylene, methyl ethyl ketone, benzene or some combination thereof.
  • the carrier fluid comprises water.
  • the dried composition or the CF may include a surfactant or wetting agent.
  • the composition may comprise a surfactant.
  • the surfactant may be Span 20, Span 40, Span 60, Span 80, Span 83, Span 85, Span 120, Tween 20, Tween 21, Tween 40, Tween 60, Tween 61, Tween 65, Tween 80.
  • the surfactant is nonionic, zwitterionic, containing cationic head groups, anionic.
  • the composition comprises a concentration of the surfactant that ranges from 0.05 to 5 wt%, 0.01 to 50 wt%, 0.01 to 25 wt%, 0.01 to 10 wt%, 0.1 to 5 wt%, 0.1 to 2 wt%, or 0.5 to 2 wt%.
  • the mass percent of Component 2 as a percentage of the total mass of the composition can be varied from 0.01% to 99.9%. In other embodiments, the mass percent of Component 2 as a percentage of the total mass of the composition ranges from 0.1% to 50%, from 0.1% to 10%, from 1% to 10%, from 1% to 5%) or 1%) to 3%). In still other embodiments, the mass percent of Component 2 as a percentage of the total mass of the composition ranges from 50% to 99.9%, from 90% to 99.9% or from 90% to 99%. In another embodiment, the mass percent of Component 2 as a percentage of the total mass of the composition is approximately 50%.
  • the complex skeletal density of the composition may be assessed using helium pycnometry, as known to those skilled in the art.
  • the complex skeletal density of the composition in some embodiments may range from 0.1 g/cc to 10 g/cc.
  • the skeletal density of the composition is below 0.2 g/cc, below 0.3 g/cc, below 0.4 g/cc, below 0.5 g/cc, below 0.6 g/cc, below 0.7 g/cc, below 0.8 g/cc, below 0.9 g/cc, below 1.0 g/cc, below 1.1 g/cc, below 1.2 g/cc, below 1.3 g/cc, below 1.4 g/cc, below 1.5 g/cc, below 1.6 g/cc, below 1.7 g/cc, below 1.8 g/cc, below 1.9 g/cc, below 2.0 g/cc, below 2.1 g/cc, below
  • the skeletal density of the composition is below 2.5 g/cc, below 3.0 g/cc, below 3.5 g/cc, below 4.0 g/cc, below 5.0 g/cc, below 7 g/cc, below 10 g/cc.
  • the surface area of the composition may be tailored in order to provide increased conductivity. Accordingly, in one embodiment the composition comprises a BET surface area of at least 1 m 2 /g, at least 2
  • the composition comprises a BET surface area of at least 50 m 2 /g, at least 100 m 2 /g, at least 150 m 2 /g, at least 200 m 2 /g, at least 250 m 2 /g, at least 300 m 2 /g, at least 350 m 2 /g, at least 400 m 2 /g, at least 450 m 2 /g, or at least 500 m 2 /g.
  • the composition comprises a BET surface area of at least 1000 m 2 /g.
  • concentration of the conjugated polymer in the composition can impact the film thickness and the ease of application to windows. If the concentration is too high, the composition may be difficult to use in a spray bottle or may apply a film that is undesirably thick.
  • a composition wherein the concentration of the conjugated polymer in the carrier fluid ranges from 0.5 to 30 wt%, 0.1 to 10 wt%, 0.5 to 5 wt%, 1 to 2 wt%, 5 to 9 wt%, and 6 to 8 wt% is provided.
  • the concentration of the conjugated polymer in the carrier fluid is approximately 1.5 wt%.
  • concentration of the conjugated polymer in carrier fluid is greater than 10 wt%.
  • the concentration of the composition can be linked to the viscosity.
  • the viscosity of the composition ranges from 0.5 to 100 cP, 1 to 10 cP, 1 to 5 cP, and 1 to 2 cP. In other embodiments the viscosity of the composition ranges from 10 to 100 cP, 10 to 50 cP, and 20 to 30 cP. In one embodiment the viscosity of the composition is 1.2 cP.
  • the pH of the composition can impact both the adhesion and the safety of the polymer.
  • the pH is approximately 7.
  • the pH of the polymer ranges from 2 to 11, 2 to 7, 3 to 6, 4 to 5, 6 to 8, 7 to 11, or 8 to 10.
  • the diameter of the complex particle which may or may not be dispersed in the CF, will influence the minimum coating thickness allowed. Additionally, the diameter of the complex particle will play a role in the diffraction of light which is directly related to haze.
  • the diameter of a complex particle can be measured using methods known in the art, such as laser scattering techniques.
  • the D(50) of the dried complex particle ranges from 10 to 1000 nm, 10 to 500 nm, 20 to 300 nm, 20 to 50 nm, 50 to 200 nm, or 100 to 150 nm. In another embodiment the D(50) of the dried complex particle is approximately 200 nm.
  • the D(50) of the dried complex particle ranges from 200 to 1000 nm, 200 to 500 nm, 200 to 400 nm, or 250 to 300 nm. In still another embodiments the D(50) of the complex particle is less than 10 nm or greater than 1000 nm.
  • the composition may be purposefully functionalized in order to preferentially bond to various substrates.
  • the conjugated polymer and/or Component 2 functionality may determine, at least in part, the physical and chemical adhesion and reaction to substrate surfaces.
  • the functionality of the conjugated polymer and/or Component 2 can be identified using infrared spectroscopy, or any other methods known to those of skill in the art.
  • the conjugated polymer and/or Component 2 comprises a substituent selected from hydroxyl, carbonyl, aldehyde, carbonate, carboxylate, carboxylic acid, ester, amide, amine, imine and fluoroalkyl, and any combination thereof.
  • the substituent comprises silicon, such as a silyl or disilanyl substituent.
  • the concentration of impurities in the composition ranges from 0 to 1 wt%, 0 to 2 wt%, 0 to 3 wt%, 0 to 4 wt%, or 0 to 5 wt%. In another embodiment the concentration of impurities is approximately 0.5 wt%. In other embodiments the concentration of impurities ranges from 1 to 5 wt%, 2 to 4 wt%, or 2 to 3 wt%. In still another embodiment the concentration of impurities is less than 1 wt% or greater than 5 wt%. In still other embodiments the concentration of impurities ranges from 5 to 30%, 5 to 20%, or 10 to 15%.
  • the amount of individual trace elements can be determined using inductively coupled plasma optical emission spectrometry (ICP- OES), as known to those skilled in the art.
  • ICP- OES inductively coupled plasma optical emission spectrometry
  • the level of scandium present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm.
  • the level of titanium present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm.
  • the level of vanadium present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm.
  • the level of chromium present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm.
  • the level of manganese present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm. In some embodiments, the level of iron present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm.
  • the level of cobalt present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm. In some embodiments, the level of nickel present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm.
  • the level of copper present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm.
  • the level of zinc present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm.
  • the level of silver present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm. In some embodiments, the level of molybdenum present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm.
  • the level of platinum present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm. In some embodiments, the level of cadmium present in the composition is less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 10 ppm, or less than 1 ppm.
  • the sum of all ICP- OES impurities, excluding dopants, present in the composition is less than 100,000 ppm, less than 20,000 ppm, less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, or less than 10 ppm.
  • photospectrometry or any method known by those skilled in the art, may be used.
  • a completed reaction will be evidenced by absorption peaks in the location expected for the polymer.
  • a peak shift of greater than 10 nm suggests that the reaction was not allowed to reach completion and greater time or temperature should be employed.
  • the spray polymer material can be applied to any substrate, including transparent, semi-transparent, and non-transparent surfaces or substrates.
  • the invention provides a method for applying the compositions described herein.
  • Other embodiments of the present invention include the use of the disclosed composition in an electronic device.
  • the electronic device is a CPU or motherboard.
  • the electronic device is an airplane, automobile, bicycle, or motorcycle.
  • the electronic device is a computer, tablet, or faceplate.
  • the invention provides a transparent or semi- transparent substrate comprising the polymeric film described herein.
  • Transparent or semi-transparent substrates comprise silicon-containing glass, plastics, transparent ceramics, polymers, or combinations therein.
  • transparent surfaces or substrates include windows, single pane windows, double pane windows, car windows, residential windows, commercial windows, water bottles, light bulbs, computer screens, and watch or phone faces.
  • the invention provides a method for reducing the
  • UV or IR transmission, or both, of a transparent or semi-transparent substrate the method comprising applying a polymeric film described herein on a surface of the substrate.
  • the composition may be applied directly or indirectly to a transparent or semi-transparent surface or substrate.
  • An embodiment for application of the composition to a surface or substrate is through mechanical spraying.
  • the composition is sprayed using an aerosol canister.
  • the composition is sprayed using a non-aerosol spray bottle.
  • Spray bottles are common household objects used for various cleaning supplies.
  • the spray polymer is filled into a spray bottle.
  • the bottle material is chosen to prevent chemical reactions between the spray polymer and bottle.
  • Example bottle materials comprise polypropylene and silicon-containing glasses.
  • the user mechanically wipes the composition across the transparent or semi-transparent surface or substrate. In yet another embodiment no additional wiping or spreading is required.
  • the spray polymer is applied directly to a rag, cloth, or brush and applied through mechanical transfer. In other embodiments, the composition is applied through a doctor blade, painting method, mechanical spreading technique, or extrusion process. In some embodiments, the composition is applied using a dip coating process.
  • the spray polymer film may need to undergo additional processing steps in order to reach desired performance properties.
  • the spray polymer may need to dry to remove excess carrier fluid.
  • the method of applying the composition further comprises a drying step.
  • the carrier fluid is removed through ambient temperature air dry.
  • the carrier fluid is removed through forced air or elevated temperature drying.
  • the spray polymer may also require additional curing for proper adhesion and flexibility. Curing may occur before or after carrier fluid removal.
  • the spray polymer is cured using thermal assistance or UV assistance.
  • the spray polymer is designed to be removed using common solvents and removal techniques.
  • the film can be removed when exposed to an acidic solution, a basic solution, organic solvents, or water.
  • the film can be removed by common commercially available cleaning supplies, such as Windex.
  • the film is removed through mechanical wiping of the film using a rag or cloth containing the appropriate solvent (e.g., ethanol).
  • Embodiments of the present invention provides a polymeric film comprising the composition according to the composition or methods described herein. Once applied to a window or semi-transparent surface the spray polymer substance can be further characterized as a thin film. For all measurements the film thickness is assumed to be uniform and constant at 200 nm thick. All values of performance are normalized to the semi-transparent to transparent substrate. For example, the transmission in the visible spectra is at 80% indicates a 20% reduction in visible light through the substrate.
  • the goal for an effective coating is to allow for the highest percentage of visible light to be transmitted through the film.
  • the wavelength of visible light is defined to fall between the ranges of 350 and 750 nm, as known in the art.
  • the transmission of visible light through the film is between 70 and 100%.
  • the transmission of visible light through the film ranges from 80 to 100%, 80 to 90%, 90 to 95%, or 70 to 80%.
  • the polymeric film, wherein the transmission of visible light through the polymeric film ranges from 80 to 100% when the polymeric film is measured at 200 nm thick, is provided.
  • the transmission of visible light is below 70%.
  • UV radiation ultraviolet
  • the wavelength of UV radiation is defined as below 350 nm.
  • the absorption of UV radiation by the polymeric film ranges from 25 to 100%.
  • the absorption of UV radiation by the polymeric film ranges from 30 to 90%, 35 to 80%, 40 to 60%, or 45 to 55%.
  • the absorption of UV radiation by the film is 50% or below 25%.
  • IR radiation infrared
  • the wavelength of IR radiation is defined as above 750 nm.
  • the absorption of IR radiation by the film is between 25 and 100%).
  • the absorption of IR radiation by the film is between 30 and 90%, 35 and 80%, 35 and 60%, 35 and 50%.
  • the absorption of IR radiation by the film is 40%.
  • IR radiation infrared
  • the reflection of IR radiation by the film is between 20 and 100%.
  • the reflection of IR radiation by the film is between 20 and 90%, 20 and 80%, 20 and 60%, 20 and 50%.
  • the reflection of IR radiation by the film is 30%.
  • the transmission figure of merit is defined as the integral of the transmission spectrum from 350 to 750 nm (visible) divided by the integral of the transmission spectrum from 750 to 2500 nm (infrared). A larger transmission figure of merit corresponds to better performance.
  • the polymeric film has a FOM T ranging from 0.1 to 1, 0.2 to 1, 0.5 to 1, 0.8 to 0.9, or 0.25 to 0.9. In another embodiment the FOM T is between 0.2 and 0.3, 0.25 and 0.29. In other embodiments the FOM T ranging from 0.7 to 0.95, 0.75 to 0.9, or 0.8 to 0.85.
  • the absorption figure of merit is defined as the integral of the absorption spectrum from 750 to 2500 nm divided by the integral of the absorption spectrum from 350 to 750 nm. A larger absorption figure of merit corresponds to better performance.
  • the polymeric film has a FOMA ranging from 1 to 20, 2 to 15, 5 to 10, 8 to 9, 8 to 12, or 9 to 10. In another embodiment the polymeric film has a FOM A ranging from 10 to 12, 10 to 15, or 10 to 20.
  • the reflection figure of merit is defined as the integral of the reflection spectrum from 750 to 2500 nm divided by the integral of the reflection spectrum from 350 to 750 nm. A larger reflection figure of merit corresponds to better performance.
  • the polymeric film has a FOM R ranging from 1 to
  • the polymeric film has a FOM R ranging from 10 to 12, 10 to 15, or 10 to 20.
  • the complete transmission, absorption and reflection of the film can be assessed through the product of the three components.
  • the polymeric film has a TAR ranging from 5 to 20, 20 to 50, 50 to 70, 70 to 100, 100 to 150, 150 to 200, 200 to 280. In another embodiment, the TAR is approximately 75.
  • a material may have a high TAR value, wherein the absorption value is low due to a high reflection.
  • the ratio between reflection and the absorption can be defined using the following equation:
  • the polymeric film has an R/A ranging from 0 to 5. In other embodiments the R/A ranges from 0.01 to 0.5, 0.1 to 0.4, or 0.2 to 0.3. In yet another embodiment the polymeric film has an R/A greater than 0.5. In still another embodiment the polymeric film has an R/A that is approximately 0.
  • Haze is an important measurement of the film's diffractive qualities and is known to those familiar with the art. An undesired high value for haze will make images blurry or deformed. A low value for haze is preferred in some embodiments for optimal coatings.
  • the haze of the film is between 0 and 5%.
  • the haze of the film is between 0 and 4%, 0 and 3%, 0 and 2%, 0 and 1%, 0 and 0.5%.
  • the haze of the film is approximately 0.5%.
  • the haze of the film is higher than 5% but lower than 20%.
  • the color rendering index of the film is between 0.5 and 1. In another embodiment the color rendering index of the film is between 0.6 and 1, 0.7 and 1, 0.8 and 1, 0.9 and 1. In still another embodiment the color rendering index of the film is greater than 0.9. In yet another embodiment the color rendering index of the film is approximately 0.95.
  • the film will also provide thermal insulating effects.
  • the thermal impacts can be measured using metrics known to those in the art.
  • the ⁇ /-factor describes the ability for the window or film to prevent heat from escaping. It is a measurement of the rate of heat transfer.
  • the polymeric film can be designed to allow for high heat transfer (high ⁇ /-factor) or high heat retention and low transfer (low ⁇ /-factor).
  • the polymeric film has a ⁇ /-factor of the film ranging from 0.05 to 1.5 BTU/sf/hr/°F.
  • the polymeric film has a ⁇ /-factor ranging from 0.1 to 0.8 BTU/sf/hr/°F, 0.1 to 0.5 BTU/sf/hr/°F, 0.2 to 0.6 BTU/sf/hr/°F, 0.3 to 0.8 BTU/sf/hr/°F, or 0.3 to 0.5 BTU/sf/hr/°F.
  • the polymeric film has a ⁇ /-factor that is approximately 0.4 BTU/sf/hr/°F.
  • the polymeric film has a ⁇ /-factor that allows for high heat transfer and ranges from 0.8 to 1.5 BTU/sf/hr/°F, 1 to 1.4 BTU/sf/hr/°F, or 1.2 to 1.3 BTU/sf/hr/°F.
  • Yet another thermal property of the film is the temperature of the outside of the window wherein condensation is formed on the inside of the window.
  • the threshold exterior temperature for interior condensation is typically desired to be as low as possible, allowing for windows to be more effective in cold climates.
  • the threshold exterior temperature for interior condensation is between -30 to 20 °C.
  • the threshold exterior temperature for interior condensation is between -20 to 10 °C, -10 to 0 °C.
  • the threshold exterior temperature for interior condensation is approximately -5 °C.
  • Thin coatings and films can be further characterized by the adhesion testing using ASTM D3359 method for measuring adhesion by scoring and tape test.
  • ASTM D3359 The methods and classification using ASTM D3359 is well known to those in the art.
  • the film is classified as 5B (0% removed), 4B (less than 5% removed), 3B (between 5 and 15% removed), 2B (between 15 and 35% removed), IB (between 35 and 65% removed), or 0B (greater than 65% removed).
  • the end user may choose to apply the coating to the exterior of a window to block UV and IR energy from entering conditioned spaces.
  • Extreme outdoor conditions may contribute to the degradation of the film and result in decreased performance.
  • accelerated environmental stability tests may be conducted according to ISO 4892. After subjecting films to these accelerated stresses, the above characterizations may be repeated to determine the effect on performance. In one embodiment, performance of the film is decreased by 10%, in another by 15% and in another by 30%. In yet still another embodiment, the performance after simulated environmental stress fell by 8%.
  • the coating may be applied to transparent surfaces, such as windows in high traffic areas, there is the chance that the coating may be inadvertently scratched.
  • the scratch/abrasion resistance of the coating can be evaluated with a scratch apparatus as described in ISO 1518. Not wanting to be bound by theory, from this test, the minimum force to penetrate the coating through to the underlying substrate is determined. In one embodiment, the minimum load to scratch the coating is 2 N, in another it is 10 N and in another it is 20 N. In yet still another embodiment, the minimum load to penetrate the coating through to the substrate is 12 N.
  • the coating may be exposed to extreme condition, such as elevated temperatures.
  • the film needs to undergo minimal degradation or material loss when exposed to high temperature.
  • the thermal degradation onset is defined as the temperature at which 5% of the film is removed by thermo gravimetric analysis in nitrogen.
  • the thermal degradation onset temperature of the film is between 100 °C and 500 °C.
  • the thermal degradation onset temperature of the film is between 100 °C and 400 °C, 125 °C and 400 °C, 150 °C and 350 °C, 200 °C and 300 °C.
  • the thermal degradation onset temperature of the film is between 250 °C and 350 °C, 275 °C and 350 °C, 300 °C and 325 °C. In yet another embodiment the thermal degradation onset temperature of the film is between 400 °C and 500 °C.
  • the material can also be designed to be safe for children and pets in the case of inadvertent ingestion.
  • Lethal Dose, 50% is a measurement of the amount of a substance required to skill 50% of a test population.
  • the test population is adult rats.
  • the LD50 for the spray polymer material is between 0.0001 g/kg and 1000 g/kg.
  • the LD50 for the spray polymer material is between 0.01 g/kg and 50 g/kg, 0.1 g/kg and 5 g/kg, 0.5 g/kg and 2 g/kg.
  • the LD50 for the spray polymer material is between 5 g/kg and 1000 g/kg, 10 g/kg and 100 g/kg, 10 and 50 g/kg, 20 and 40 g/kg.
  • the polymeric film has an electronic conductivity ranging from 10 "4 to 10 3 S/cm. In one embodiment the polymeric film has an electronic conductivity ranging from 0.001 to 1000 S/cm, 1 to 10 3 S/cm, 1 to 10 2 S/cm, or 50 to 100 S/cm. In another embodiment the polymeric film has an electronic conductivity ranging from 10 " 4 to 10 S/cm, 10 "3 to 1 S/cm, or 10 "2 to 1 S/cm.
  • the composition can be used to inhibit the oxidation of metallic surfaces.
  • the composition can be added to the surface of bare metal as a pre-treatment, it can be mixed into a primer and coated on the surface, it can be mixed into a paint or combined with pigments to achieve a desired color, or it can be mixed into a top coat.
  • the composition is coated either using powder coating techniques or using a diluted spray, as previous described. The coating may undergo heating or post-treatment, such as curing, in order to achieve performance.
  • the composition may be combined with other materials or coating layers, including but not limited to primers and top-coats.
  • a composition as described herein further comprises a matrix material.
  • the matrix material can have any form factor.
  • the matrix material may be a resin, paint or a liquid solvent, such as water.
  • the matrix comprises a solid, such as a powder.
  • the matrix material comprises water, benzene, xylene, toluene, ethanol, methanol, methyl-ethyl-ketone, isopropanol, acetone or combination thereof.
  • the matrix material comprises a surfactant such as Span 20, Span 40, Span 60, Span 80, Span 83, Span 85, Span 120, Tween 20, Tween 21, Tween 40, Tween 60, Tween 61, Tween 65, Tween 80.
  • a surfactant such as Span 20, Span 40, Span 60, Span 80, Span 83, Span 85, Span 120, Tween 20, Tween 21, Tween 40, Tween 60, Tween 61, Tween 65, Tween 80.
  • the matrix material (e.g., paint or resin) comprises phenolics (e.g., phenol, polyphenol), esters (e.g., polyesters), epoxy, polyethylene terephthalate, acrylonitrile butadiene styrene, polystyrene, polypropylene, polyethylene, polycarbonate, nylon, polyurethane, hydrocarbon resins, acrylics (e.g., acrylate polymers, polyacrylic acid), chlorinated rubbers, vinyl, thermoplastic polyester, okra gum, pitch, galbanum, amino resins or combinations thereof.
  • the matrix material is a polymer comprising a gum resin, a synthetic resin, a thermoplastic resin, or a thermoset resin.
  • the matrix material comprises zinc, aluminum, titanium, silver, nickel, chromium, copper, tin, or combinations thereof.
  • the matrix material comprises a combination of substances listed above.
  • the matrix material is a powder.
  • the diameter, or D(50), of the matrix powder material can be measured using methods known in the art, such as laser scattering techniques.
  • the D(50) of matrix powder material is between 10 and 1000 nm, 10 and 500 nm, 20 and 300 nm, 20 and 50 nm, 50 and 200 nm, 100 and 150 nm.
  • the D(50) of matrix powder material is approximately 200 nm.
  • the D(50) of matrix powder material is between 200 and 1000 nm, 200 and 500 nm, 200 and 400 nm, 250 and 300 nm.
  • the D(50) of matrix powder material is less than 10 nm or greater than 1000 nm.
  • the percentage of the composition to the matrix material may determine the performance properties of the coating, such as adhesion, transparency, color, metal oxidation rate, and hardness.
  • the composition added ranges between 0.1 wt.% and 99 wt.%. In some embodiments the composition added ranges between 0.1 wt% and 50%, between 0.5% and 10%, between 1% and 2%, between 1% and 5%. In yet other embodiments the composition added to matrix material is greater than 50% by weight.
  • the electronic conductivity of the matrix material may range between 10 "4 S/cm to 10 3 S/cm. In one embodiment the electronic conductivity of the matrix material is between 1 S/cm and 10 3 S/cm, 1 S/cm and 10 2 S/cm, 50 S/cm and 100 S/cm. In another embodiment the electronic conductivity of the matrix material is between 10 " 4 S/cm and 10 S/cm, 10 "3 S/cm and 1 S/cm, 10 "2 S/cm and 1 S/cm.
  • the matrix material may be doped with an additive to further improve the performance characteristics. This secondary or tertiary dopant may be added either during the synthesis stage or mixed post-synthesis.
  • the level of nickel doped into the matrix material is greater than 1 wt. %, greater than 2 wt.%, greater than 5 wt.%, greater than 10 wt.%, greater than 20 wt.%, or greater than 30 wt.%).
  • the level of nickel doped into the matrix material is between 3 wt.% and 7 wt.%.
  • the level of nickel doped into the matrix material is ⁇ 6 wt.%.
  • the level of aluminum doped into the matrix material is greater than 1 wt. %, greater than 2 wt.%, greater than 5 wt.%), greater than 10 wt.%, greater than 20 wt.%, or greater than 30 wt.%.
  • the level of titanium doped into the matrix material is greater than 1 wt. %, greater than 2 wt.%, greater than 5 wt.%, greater than 10 wt.%, greater than 20 wt.%), or greater than 30 wt.%.
  • the level of silver doped into the matrix material is greater than 1 wt.
  • the level of silver doped into the matrix material is between 1 wt.% and 5 wt.%. In yet another embodiment, the level of silver doped into the matrix material is ⁇ 3 wt.%. In another embodiment, the dopant comprises a powder form.
  • the dopant is carbon, such as carbon black, carbon nanotubes, activated carbon, graphite, graphene,
  • the dopant comprises a metal oxide, such as zinc oxide, nickel (II) oxide, copper (IV) oxide, or molybdenum (III) oxide.
  • the metal surfaces which may be protected from corrosion and oxidation using the composition include copper, aluminum, steel, silver, and brass. Other metals or mixed metals may be coated to offset corrosive behavior.
  • the composition may be used in conjunction with other known anti-corrosive materials and additives for enhanced performance.
  • the anti-corrosive properties may be used in a variety of applications including, but not limited to, gas or storage tanks, ships and boat hulls and parts, shipping containers, cars, trucks, busses, airplanes and aerospace, bridges, and construction equipment and supplies. Anti-corrosion performance can be measured using ASTM D 1654-05.
  • compositions disclosed herein are made according to the general methods described above the specific Examples which follow. Chemicals were obtained through commercial sources and were used without further processing unless otherwise stated. The following examples are provided for purposes of illustration and not limitation.
  • the conjugated polymer composition is synthesized by mixing poly(4- styrenesulfonic acid-co-maleic acid), PSSA-co-MA, and water to create a 4.8 wt% solution.
  • EDOT 3,4-ethylenedioxythiophene monomer
  • PSSA-co-MA:EDOT weight ratio of 4: 1
  • KPS Potassium persulfate
  • the mixture is heated to 50 °C and allowed to polymerize to completion (approximately 3-24 hours). The polymerization is deemed complete by a drastic change in color to dark blue.
  • Table 4 shows various combinations of Component 1, Component 2 and Component 3 to prepare the composition.
  • the PEDOT composition is further modified through additional dopants.
  • Ferric chloride FeCl 3
  • the composition and dopant are allowed to mix for 4 hours.
  • the pH of the composition from Example 2 is measured, typically falling between 2 and 4.
  • aqueous sodium hydroxide is slowly titrated into the composition while constantly stirring until the pH is between 6 and 8.
  • other strong and weak bases can be used to achieve a similar outcome.
  • composition from Examples 1-3 can be further post-processed into the spray polymer solution product.
  • 500 mL of composition is poured onto a vacuum filtration system using Whatman 602 H paper. The vacuum filtration is allowed to continue until complete solvent removal. Further drying is performed in air on a hot plate or oven at 50 °C.
  • the powder is then dispersed in ethanol at 1.5 wt% using a mechanical mixer.
  • the composition is filtered with a Whatman syringe filter of appropriate pore size.
  • Example pore sizes include 220 nm and 450 nm.
  • the spray polymer solution is prepared through a solvent exchange.
  • the water is exchanged with ethanol using a centrifugal extractor or mix- settler. Additional ethanol is added to the composition in order to reach the target concentration of 1.5 wt%.
  • the spray polymer solution can be prepared through the manipulation of a commercially available polymer product.
  • An aqueous dispersion of PEDOT:PSS may be obtained from Heraeus and modified as in Examples 2-4.
  • a transparent substrate 3 inches by 3 inches, is cut from commercially available 1/8" thick glass, obtained from Gardner Glass Products.
  • the substrate is mounted into a spin coater.
  • the spin speed is set to 1000 rpm and 1 mL of spray polymer composition is dropped into the center of the substrate. With the composition on the substrate, rotation is begun and allowed to continue for 30 seconds. Once the rotation is complete, the substrate is removed from the spin coater and allowed to dry.
  • the film is allowed to air dry for at least 2 hours.
  • the resultant film is removed using mechanical wiping and ethanol as a solvent.
  • Exemplary films were prepared according to Examples 1-6 and tested to determine physical characteristics for visible wavelengths (i.e., 350-750 nm) and infrared (i.e., 750-2500 nm). The results are shown below in Table 5.
  • a composition comprising the conjugated polymer poly(3,4- ethylenedioxythiophene) (PEDOT) and poly(methylvinyl ether-alt-maleic acid) (PMVEMA) as Component 2 (structures below, where n is an integer greater than 1) was prepared as follows:
  • reaction vessel was filled with 400 mL of DI water and a stir bar was added to stir at moderate speed.
  • NaPS sodium persulfate
  • a uniform particle size (Sample A93) can be achieved, as shown in Figure 1.
  • the small particles are porous in nature and semi -spherical.
  • PEDOT:PMVEMA composition can be dried from the reaction mixture and re- dispersed very easily in water.
  • the conductivity of these aqueous dispersions depends on concentration, as shown in Figure 2.
  • concentration of the reaction to produce PEDOT:PMVEMA can play a role in the resistivity (i.e. conductivity) and dispersibility of the final dried product, as evidenced in Table 7.
  • composition comprising PEDOT as the conjugated polymer and poly(styrenesulfonic acid-co-maleic acid) (PSSAMA, structure below where x and y are independently integers of 1 or greater) as Component 2 was prepared.
  • PSSAMA poly(styrenesulfonic acid-co-maleic acid)
  • compositions comprising PEDOT as the conjugated polymer and 5-sulfosalicylic acid (5-SSA, see below) were also prepared.
  • compositions using two different poly(maleic acid)-derivatives were synthesized in the presence of a nanostructured backbone, Laponite RDS.
  • the poly(maleic acid)-derivatives were added dropwise to two premixed reaction solutions containing water, Laponite RDS, and FeCl 3 . Reaction mixtures were allowed to stir for 2 hours prior to the addition of 3,4-ethylenedioxythiophene (EDOT).
  • EDOT 3,4-ethylenedioxythiophene
  • reaction mixtures described in Example 9 were coated on polyethylene terephthalate and sheet resistivity was measured. Samples were prepared by concentrating the samples and removing unreacted compounds using centrifugation and re-suspending in water. A wetting agent, AFCONA-3585, was added to provide enhanced spreading and surface leveling. Films were coated at 2 mil wet film thickness and cured at 80 °C for 2 minutes. Sheet resistivity and appearance observations are provided below in Table 12.

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Abstract

L'invention concerne des compositions comprenant un polymère conjugué et un ou plusieurs composés de structure (I) ou (II), ou un sel ou un stéréoisomère de ceux-ci, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, L1, L2, L3, L4, L5, a, b et n étant tels que définis dans la description, à condition qu'au moins deux parmi R6, R7, R8, R9, R10 et R11 ne soient pas H et à condition que b soit égal à 1 pour au moins une valeur entière de n. Des films polymères comprenant la composition divulguée et leurs utilisations dans diverses applications sont également décrits.
PCT/US2017/037227 2016-06-13 2017-06-13 Compositions comprenant des polymères conjugués et leurs utilisations WO2017218516A1 (fr)

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