WO2024015316A1 - Coated flexible articles with anti-icing surface - Google Patents

Coated flexible articles with anti-icing surface Download PDF

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Publication number
WO2024015316A1
WO2024015316A1 PCT/US2023/027307 US2023027307W WO2024015316A1 WO 2024015316 A1 WO2024015316 A1 WO 2024015316A1 US 2023027307 W US2023027307 W US 2023027307W WO 2024015316 A1 WO2024015316 A1 WO 2024015316A1
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Prior art keywords
coated article
weight percent
formula
coating composition
alkyl
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Application number
PCT/US2023/027307
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French (fr)
Inventor
Donald P. BROWNING
Maria Elisa CANTU BROWNING
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Phazebreak Coatings, Inc.
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Publication of WO2024015316A1 publication Critical patent/WO2024015316A1/en

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    • 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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • 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
    • C09D133/00—Coating compositions based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers

Definitions

  • This disclosure relates to coated flexible articles.
  • Flexible articles such as powerlines are often used under various weather conditions.
  • a coating can be applied.
  • the coating can crack and peel away from the substrate when the substrate is flexed. Accordingly, a coating suitable for use on a flexible substrate is desired. It would be a further advantage if such a coating can have anti-icing characteristics. There remains a need for improved coated articles with flexibility while also having anti- icing performance.
  • a coated article includes a flexible substrate; and a coating disposed on the flexible substrate, wherein the coating comprises a cured product of a coating composition comprising: an epoxy-silicone; an aminosilane; a silanol-functional silicone; and a fluorinated silane.
  • a coated article comprises a flexible substrate; and a coating disposed on the substrate; wherein the coating contains a cured product of a coating composition containing an acrylic modified silyl-terminated polyether; an epoxy -silicone; an aminosilane; and an organic solvent.
  • the present disclosure relates to a coated article having a flexible substrate, and a coating that can provide anti-icing characteristics.
  • the anti-icing surface of the coated article may repel water, delay ice formation, hindrance ice adhesion, or facilitate the removal of ice, snow, or frozen contaminants from the coated article.
  • the coating as described herein are suitable for use on a flexible substrate with minimized cracking or peeling away even when the substrate is flexed
  • the coated article comprises a flexible substrate; and a coating disposed on the flexible substrate, wherein the coating comprises a cured product of a coating composition comprising: an epoxy -silicone; an aminosilane; a silanol-functional silicone; and a fluorinated silane.
  • the term "flexible substrate” refers to a substrate that can undergo mechanical stresses, such as bending or stretching and the like, without significant irreversible change.
  • Examples of a flexible substrate includes a powerline, a cable, or a wire.
  • the epoxy-silicone in the coating composition can be a polysiloxane having epoxide functional groups.
  • the epoxy equivalent weight of the epoxy -silicone can be at least about 200 grams, about 200 to about 700 grams, about 300 to about 700 grams, or about 400 to about 600 grams.
  • the epoxide or epoxy equivalent weight (EEW) refers to the mass in grams which one mole of epoxy groups contains. EEW can be determined by ASTM D1652.
  • the epoxy- silicone can have a polysiloxane framework.
  • tire polysiloxane framework or a side chain of the polysiloxane framework has OH groups and/or alkoxy groups.
  • the epoxy-silicone used is preferably liquid at 0 to 40 °C. Otherwise the addition of solvents may be needed. It is preferable that the addition of solvents is to be kept as low as possible.
  • the aminosilane in the coating composition can have a structure represented by Formula I or Formula II
  • R is hydrogen, alkyl, cycloalkyl, aryl, or aralkyl; each occurrence of R' is independently hydrogen, alkyl, or cycloalkyl; each occurrence of R" is independently alkyl, cycloalkyl, aryl, or aralkyl; each occurrence of X aiid X’ is independently alkylene, cycloalkylene, or -R 2 -NH-R 3 -, wherein R 2 and R 3 are independently alkylene, or cycloalkylene; x is 0 to 2, y is 0 to 2, n is 0 to 2, m is 0 to 2, and m+n is 2.
  • each of R, R 2 , R 3 , R', R", X, and X' can independently have 1 to 20, 1 to 10, or 1 to 6 carbon atoms.
  • the aminosilane can comprise at least one of a primary aminoalkyialkoxysiiane of Formula I when R is H, and R’ is an alkyl group; a secondary aminoalkylalkoxysilane of Formula I when R is an alkyl group, and R' is an alkyl group; a bisalkoxysilylamine of Formula III; or a diaminosilane of Formula I when X is -R 2 -NH-R 3 -.
  • Examples of the primary aminoalkyialkoxysiiane include 2- aminoethyltrimethoxysilane, 2-aminoethyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3- aminopropyltriethoxysilane, 4-aminobutyltrimethoxysilane, or 4-aminobutyltriethoxysilane.
  • Preferred primary aminoalkyialkoxysiiane is 3-aminopropyltrimethoxysilane or 3- aminopropyl triethoxy silane.
  • Examples of the secondary aminoalkyialkoxysiiane include N-(2- (trimethoxysilyl)ethyl)alkylamines, N-(3-(trimethoxysilyl)propyl)alkylamines, N-(4- (trimethoxysilyl)butyl)alkylamines, N-(2-(triethoxysilyl)ethyl)alkylamines, N-(3- (triethoxysilyl)propyl)alkylamines, or N-(4-(triethoxysilyl)butyl)alkylamines.
  • Preferred secondary aminoalkyialkoxysiiane is N-(3-(trietlroxysilyl)propyl)butylamine or N-(3- (trimethoxysilyDpropyl)butylamine.
  • Examples of the bisalkoxysilylamine include bis(2- ethyltrimethoxysilyl)amine, bis(3-propyltrimethoxysil-yl)amine, bis(4- butyltrimethoxysilyl)amine, bis(2-ethyltriethoxysilyl)amine, bis(3-propyltriethoxy- silyl)amine, or bis(4-butyltriethoxysilyl)amine.
  • diaminosilane examples include H 2 N-(CH 2 ) 2 NH(CH 2 ) 2 Si(OCH 3 )3, or H 2 N(CH 2 ) 2 NH(CH 2 )3 S i(OCH 3 ) 2 CH 3 .
  • Diaminosilanes are commercial l y available, for example, under the trade name SILQUEST Al 120, SILQUEST A1120J, or SILQUEST 2120, from Momentive.
  • the silanol-functional silicone in the coating composition can have a structure represented by Formula III
  • each occurrence of R'" is independently alkyl, cycloalkyl, aryl, or aralkyl, and n is 2 to 20 or 3 to 10.
  • R'" can be halogenated.
  • each R'" is independently a C 1-10 or C 1-6 alkyl, or phenyl. More preferably each occurrence of R"' is methyl or phenyl. More preferably each occurrence of R'" is independently methyl, phenyl, or trifluoropropyl.
  • the silanol-functional silicone can comprise at least one of a silanol- terminated polydimethylsiloxane, a silanol-terminated polydiphenylsiloxane, a silanol- terminated diphenylsiloxane-dimethylsiloxane copolymer, or a silanol-terminated polytrifluoropropylmethylsiloxane.
  • a silanol-terminated polydimethylsiloxane is preferred.
  • the silanol-terminated polydimethylsiloxane can have a viscosity of about 45 to about 85 centistokes (cSt) measured at room temperature (23°C).
  • the fluorinated silane in the coating composition can have a structure represented by Formula IV
  • R 1 -Si(OR') 3 Formula IV wherein R 1 is a fluorinated alkyl, and each occurrence of R' is independently hydrogen, alkyl, or cycloalkyl.
  • R 1 is a fluorinated C1-20 alkyl or a fluorinated C 1-10 alkyl
  • R' is a C 1-10 alkyl, C 1-5 alkyl, or C 1-3 alkyl.
  • a specific example of the fluorinated silane is (tridecafluofo- 1,1,2,2-tetrahydrooctyl)trimethoxysilane.
  • the fluorinated silane can react with the silanol-functional silicone during curing to form a phase change material that imparts anti-icing cha r acteristics to the coating surface.
  • the phase change material may have a structure of the Formula V
  • R 1 , R', and R’" are the same as described herein in the context of Formula III and Formula IV.
  • the coating composition can comprise, based on a total weight of the coating composition: about 60 to about 80 weight percent (wt%), or about 65 to about 75 weight percent of the epoxy-silicone; about 10 to about 25 weight percent, or about 15 to about 20 weight percent of the aminosilane; about 1 to about 20 weight percent, or about 5 to about 15 weight percent of the silanol-functional silicone; and about 0.5 to about 10 weight percent, or about 1 to about 5 weight percent of the fluorinated silane.
  • the coating composition can further comprise at least one of a curing catalyst, a surface- active agent, a heat stabilizer, an ultraviolet-light absorber, or a colorant.
  • the curing catalyst can be present in an amount of about 0.05 to about 1 weight percent, based on a total weight of the coating composition.
  • the curing catalyst can comprise at least one of an organotin compound, an organozinc compound, an organotitanium compound, an organozirconium compound, or an organic acid.
  • Organotin compounds tire particularly useful.
  • organotin compound examples include dibutyltin dicarboxylates, such as dibutyltin dilaurate and dibutyltin bis(alkyl maleate); dialkyltin alkoxide derivatives such as dibutyltin dimethoxide and dibutyltin diphenoxide; intramolecular coordination derivatives of dialkyltins, such as dibutyltin diacetylacetonate and dibutyltin acetoacetate; reaction mixtures of dibutyltin oxide with ester compounds; reaction mixtures of dibutyltin oxide with silicate compounds, or tetravalent dialkyltin oxide derivatives such as oxy derivatives of said dialkyltin oxide derivatives as described in U.S. Patent 6,642,309. Two or more of the curing catalyst can be used.
  • dibutyltin dicarboxylates such as dibutyltin dilaurate and dibutyltin bis(alkyl
  • a surface-active agent can modify the interaction of a coating composition with the substrate, in particular, the agent can modify the ability of the composition to wet a substrate.
  • Surface active agents may also include leveling, defoaming, or flow agents, and the like. If used, the surface active agent can be present in an amount of about 0.1 to about 5 wt%, based on the total weight of the coating composition described herein.
  • Surface-active agent is known and can include polysiloxane defoamers such as a methylalkylpolysiloxane commercially available under the trade name BYK-077 or BYK- 500 from Byk Chemie, polymeric defoamers such as that commercially available under the trade name BYK 051, or other surface -active agent such as BYK-053, BYK-055, BYK-057, BYK-020, BYK-065, BYK-066N, BYK-067A, BYK-070, BYK-080A, BYK-088, BYK-141, BYK-019, BYK-021, BYK-022, BYK-023, BYK-024, BYK-025, BYK-028, BYK-011, BYK-031, BYK-032, BYK-033, BYK-034, BYK-035, BYK-036,
  • the light stabilizer can include a hindered amine light stabilizer (HALS).
  • HALS is commercially available, for example, under tire trade name BLS 292 from Mayzo, TINUVIN 123 or UVINUL 4092 from BASF Corp., OMNISTAB LS292 from ICG Specialty Chemicals, OMNISTAB LS944 from ICG Specialty Chemicals, SABOSTAB 119 or SABOSTAB 94 from Sabo S.p.A., or LOWILITE from Addivant.
  • the light stabilizer can be used in an amount of 01 to 1 wt% based on a total weight of tire coating composition.
  • the coating composition can comprise more than one light stabilizer if needed.
  • the ultraviolet- light (UV) absorber that can be useful with the coating composition include avobenzone, 2,5-bis(5-tert-butyl-benzoxazol-2-yl)thiophene (Benetex OB+), disodium 4,4'-bis(2-sulfonatostyryl)biphenyl (Benetex 0B-M1), benzenepropanoic acid (BLS 99-2), 2,3,6,7-tetrahydro-9-methyl-1H,5H-quinolizino(9,l-gh)coumarin (Coumarin 102), Martins Yellow, morin hydrate, nitrofur azone, 2 -nitrophenyl phenyl sulfide (NPS), 5,12-naphthacenequinone (NTAQ), octocrylene, phenazine, 1,4-bis-(2-(5- phenyloxazolyl)) -benzene (POPOP), Quinoline Yellow
  • the components of the coating composition can be mixed shortly before the coating composition is applied to the substrate.
  • the coating composition can be applied by any of the suitable application methods, such as spraying, knife coating, spreading, pouring, dipping, impregnating, trickling or rolling, for example.
  • the substrate to be coated may itself be at rest, with the application equipment or unit being moved.
  • the substrate to be coated for example a powerline, may be moved, with the application unit being at rest relative to the substrate or being moved appropriately.
  • the applied coating composition can be cured after a certain cure time.
  • the cure time may be tuned by adjusting the cure temperature and/or humidity, provided that this does not entail any damage or alteration to the coating, such as premature complete crosslinking, for instance.
  • a thermal cure can be conducted at a temperature of about 30 to about 200° C., more preferably about 30 to about 150° C., and in particular about 30 to about 100° C for a time of about 1 minute (min) up to about 10 hours (h), more preferably about 2 min up to about 5 h, and in particular about 3 min to about 3 h.
  • a coating composition comprises an acrylic modified silyl-terminated polyether: an epoxy-silicone; an aminosilane: and an organic solvent.
  • the acrylic modified silyl-terminated polyether can be an acrylic modified sily-terminated polyether described in U.S. Patent No. 6,642,309.
  • the acrylic modified silyl- terminated polyether is commercially available under the trade name SILYL MA904 from Kaneka.
  • the epoxy-silicone and the aminosilane can be the same as the epoxy-silicone and the aminosilane described herein above.
  • the aminosilane comprises a primary aminoalkylalkoxysilane and a diaminosilane.
  • the weight ratio of the aminoalkylalkoxy silane to diaminosilane can be about 10:1 to about 2:1 or about 8:1 to about 4:1.
  • the coating composition can comprise an organic solvent useful for dissolving or dispersing components of the coating composition.
  • the organic solvent include aliphatic hydrocarbons, such as, for example, hexane, isododecane, or cyclohexane: aromatic hydrocarbons such as for example, benzene, toluene, or xylene; ketones, such as, for example, acetone, methyl ethyl ketone, or methyl isobutyl ketone; or halogenated hydrocarbon solvents, such as, for example, trichloroethylene, or parachlorobenzotrifluoride.
  • the organic solvent can include a blend of two or more the solvents described herein.
  • the organic solvent comprises parachlorobenzotrifluoride, which is frequently abbreviated as PCBTF.
  • PCBTF is also sold under the trade name OXSOL 100.
  • the coating composition can comprise, based on a total weight of the coating composition: about 20 to about 45 weight percent, or about 25 to about 40 weight percent of the acrylic modified silyl-terminated polyether; about 20 to about 45 weight percent, or about 25 to about 40 weight percent of the epoxy-silicone; about 1 to about 20 weight percent, or about 5 to about 15 weight precent of the aminosilane; and about 10 to about 30 weight percent, or about 15 to about 25 weight percent of the organic solvent.
  • the coating composition can further comprise at least one of an unsaturated silane having an ethylenically unsaturated hydrocarbyl group, a curing catalyst, a surfaceactive agent, a heat stabilizer, an ultraviolet-light absorber, or a colorant.
  • the unsaturated silane can be used in an amount of about 0.1 to about 5 weight percent or about 0.5 to about 3 weight percent based on a total weight of the coating composition.
  • the ethylenically unsaturated hydrocarbyl group in the unsaturated silane can be, for example, vinyl, allyl, isopropenyl, butenyl, cyclohexenyl or gamma-(meth)acryloxy allyl group.
  • the unsaturated silane can also include a hydrolysable group such as, for example, an alkoxy, formyloxy, acetoxy, propionyloxy, or hydrocarbonyloxy.
  • the unsaturated silane is an unsaturated alkoxysilane.
  • unsaturated alkoxysilane examples include an acrylic silane, vinyl trimethoxysilane, vinyl triethoxysilane, or 3- (meth)acryloxypropyl trimethoxysilane.
  • commercially available examples include SILQUEST A174 or S1LQUEST A171 available from Momentive. More than one unsaturated silane can be used in the coating composition.
  • the curing catalyst, the surface-active agent, tire heat stabilizer, and the ultraviolet-light absorber can be the same as described hereinabove.
  • the coating composition can be applied to various substrates such as metallic substrates, polymeric substrates, composite substrates, and the like.
  • the coating composition can be applied to a flexible substrate.
  • the coating composition can be applied and cured as described herein above. Once cured, the coating composition can form a coating that imparts anti-icing characteristics, and the coating can maintain structural integrity with minimized cracking or peeling off with a long service life when used outdoor in low temperature environments.
  • the coated articles according to the disclosure can have up to about 76 wt% less ice accumulation, up to about 57 wt% less ice accumulation, or up to about 38 wt% less ice accumulation as compared to an uncoated substrate when tested under oscillating and impacting conditions.
  • oscillating conditions mean that a tested sample is connected to a motor which generates oscillation movement of the tested sample during testing.
  • Impacting conditions mean that during oscillation, one extremity of the tested sample lightly impacts on the sample after every oscillation to generate additional force on the sample.
  • Oscillation and impacting help to reduce ice accumulation on tire coated articles of the disclosure but do not have any effect on the uncoated substrates. Without wishing to be bound by theory, it is believed that the ice adheres firmly on the uncoated substrates but barely adheres to the coatings as disclosed herein.
  • compositions, methods, and articles can alternatively comprise, consist of, or consist essentially of, any appropriate components or steps herein disclosed.
  • the compositions, methods, and articles can additionally, or alternatively, be formulated so as to be devoid, or substantially free, of any steps, components, materials, ingredients, adjuvants, or species that are otherwise not necessary to the achievement of the function or objectives of the compositions, methods, and articles.
  • hydrocarbyl and “hydrocarbon” refers broadly to a substituent comprising carbon and hydrogen, optionally with 1 to 3 heteroatoms, for example, oxygen, nitrogen, halogen, silicon, sulfur, or a combination thereof; “alkyl” refers to a straight or branched chain, saturated monovalent hydrocarbon group; “alkylene” refers to a straight or branched chain, saturated, divalent hydrocarbon group; “cycloalkyl” refers to a non- aromatic monovalent monocyclic or multicylic hydrocarbon group having at least three carbon atoms; “aryl” refers to an aromatic monovalent group containing only carbon in the aromatic ring or rings; “arylene” refers to an aromatic divalent group containing only carbon in the aromatic ring or rings; and “arylalkyl” refers to an alkyl group that has been substituted with an aryl group as defined above, with benzyl being an exemplary arylalkyl group.
  • each of the foregoing groups can be unsubstituted or substituted, provided that the substitution does not significantly adversely affect synthesis, stability, or use of the compound.
  • substituted as used herein means that at least one hydrogen on the designated atom or group is replaced with another group, provided that the designated atom’s normal valence is not exceeded.

Abstract

A coated article includes a flexible substrate; and a coating disposed on the flexible substrate, wherien the coating includes a cured product of a coating composition. The coating composition contains an epoxy-silicone; an aminosilane; a silanol-functional silicone; and a fluorinated silane. Alternatively, the coating composition contains an acrylic modified silyl-terminated polyether; an epoxy-silicone: an aminosilane; and an organic solvent.

Description

COATED FLEXIBLE ARTICLES WITH ANTI-ICING SURFACE CROSS-REFERENCE TO RELATED APPLICATION
This application claims priority to and the benefit of U.S. Provisional Application No. 63/389,421, filed on July 15, 2022, the content of which is incorporated herein by reference in its entirely.
BACKGROUND
[0001] This disclosure relates to coated flexible articles. Flexible articles such as powerlines are often used under various weather conditions. To protect the flexible articles, a coating can be applied. However, when a coating suitable for use on a rigid substrate is applied to a flexible substrate, the coating can crack and peel away from the substrate when the substrate is flexed. Accordingly, a coating suitable for use on a flexible substrate is desired. It would be a further advantage if such a coating can have anti-icing characteristics. There remains a need for improved coated articles with flexibility while also having anti- icing performance.
SUMMARY
[0002] In an aspect, a coated article includes a flexible substrate; and a coating disposed on the flexible substrate, wherein the coating comprises a cured product of a coating composition comprising: an epoxy-silicone; an aminosilane; a silanol-functional silicone; and a fluorinated silane.
[0003] In another aspect, a coated article comprises a flexible substrate; and a coating disposed on the substrate; wherein the coating contains a cured product of a coating composition containing an acrylic modified silyl-terminated polyether; an epoxy -silicone; an aminosilane; and an organic solvent.
DETAILED DESCRIPTION
[0001] In an embodiment, the present disclosure relates to a coated article having a flexible substrate, and a coating that can provide anti-icing characteristics. In particular, the anti-icing surface of the coated article may repel water, delay ice formation, hindrance ice adhesion, or facilitate the removal of ice, snow, or frozen contaminants from the coated article.
[0002] In addition, unlike the coating for rigid substrates, the coating as described herein are suitable for use on a flexible substrate with minimized cracking or peeling away even when the substrate is flexed
[0003] The coated article comprises a flexible substrate; and a coating disposed on the flexible substrate, wherein the coating comprises a cured product of a coating composition comprising: an epoxy -silicone; an aminosilane; a silanol-functional silicone; and a fluorinated silane.
[0004] As used herein, the term "flexible substrate" refers to a substrate that can undergo mechanical stresses, such as bending or stretching and the like, without significant irreversible change. Examples of a flexible substrate includes a powerline, a cable, or a wire.
[0005] The epoxy-silicone in the coating composition can be a polysiloxane having epoxide functional groups. The epoxy equivalent weight of the epoxy -silicone can be at least about 200 grams, about 200 to about 700 grams, about 300 to about 700 grams, or about 400 to about 600 grams. The epoxide or epoxy equivalent weight (EEW) refers to the mass in grams which one mole of epoxy groups contains. EEW can be determined by ASTM D1652.
[0006] The epoxy- silicone can have a polysiloxane framework. Optionally tire polysiloxane framework or a side chain of the polysiloxane framework has OH groups and/or alkoxy groups. The epoxy-silicone used is preferably liquid at 0 to 40 °C. Otherwise the addition of solvents may be needed. It is preferable that the addition of solvents is to be kept as low as possible.
[0007] Commercially available epoxy-silicones include SILIKOPON
EF, SILIKOPON EW, SIL1KOFTAL ED, or TEGOMER ESI 2330 from Evonik. Other commercially available epoxy -silicones may also be used.
[0008] The aminosilane in the coating composition can have a structure represented by Formula I or Formula II
HRN-X-SiR"x(OR')3-x Formula I
HN(X-----SiR"x(OR')3-x)n(X'--SiR"y(OR')3.y)m Formula II wherein in Formula I and Formula II
R is hydrogen, alkyl, cycloalkyl, aryl, or aralkyl; each occurrence of R' is independently hydrogen, alkyl, or cycloalkyl; each occurrence of R" is independently alkyl, cycloalkyl, aryl, or aralkyl; each occurrence of X aiid X’ is independently alkylene, cycloalkylene, or -R2-NH-R3-, wherein R2 and R3 are independently alkylene, or cycloalkylene; x is 0 to 2, y is 0 to 2, n is 0 to 2, m is 0 to 2, and m+n is 2.
[0009] Preferably each of R, R2, R3, R', R", X, and X' can independently have 1 to 20, 1 to 10, or 1 to 6 carbon atoms. [0010] The aminosilane can comprise at least one of a primary aminoalkyialkoxysiiane of Formula I when R is H, and R’ is an alkyl group; a secondary aminoalkylalkoxysilane of Formula I when R is an alkyl group, and R' is an alkyl group; a bisalkoxysilylamine of Formula III; or a diaminosilane of Formula I when X is -R2-NH-R3-.
[0011] Examples of the primary aminoalkyialkoxysiiane include 2- aminoethyltrimethoxysilane, 2-aminoethyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3- aminopropyltriethoxysilane, 4-aminobutyltrimethoxysilane, or 4-aminobutyltriethoxysilane. Preferred primary aminoalkyialkoxysiiane is 3-aminopropyltrimethoxysilane or 3- aminopropyl triethoxy silane.
[0012] Examples of the secondary aminoalkyialkoxysiiane include N-(2- (trimethoxysilyl)ethyl)alkylamines, N-(3-(trimethoxysilyl)propyl)alkylamines, N-(4- (trimethoxysilyl)butyl)alkylamines, N-(2-(triethoxysilyl)ethyl)alkylamines, N-(3- (triethoxysilyl)propyl)alkylamines, or N-(4-(triethoxysilyl)butyl)alkylamines. Preferred secondary aminoalkyialkoxysiiane is N-(3-(trietlroxysilyl)propyl)butylamine or N-(3- (trimethoxysilyDpropyl)butylamine.
[0013] Examples of the bisalkoxysilylamine include bis(2- ethyltrimethoxysilyl)amine, bis(3-propyltrimethoxysil-yl)amine, bis(4- butyltrimethoxysilyl)amine, bis(2-ethyltriethoxysilyl)amine, bis(3-propyltriethoxy- silyl)amine, or bis(4-butyltriethoxysilyl)amine.
[0014] Examples of the diaminosilane include H2N-(CH2)2NH(CH2)2Si(OCH3)3, or H2N(CH2)2NH(CH2)3Si(OCH3)2CH3. Diaminosilanes are commercially available, for example, under the trade name SILQUEST Al 120, SILQUEST A1120J, or SILQUEST 2120, from Momentive.
[0015] The silanol-functional silicone in the coating composition can have a structure represented by Formula III
HO-(SiR' ”2 O ) n -SiR ' " 2-O H Formula III wherein each occurrence of R'" is independently alkyl, cycloalkyl, aryl, or aralkyl, and n is 2 to 20 or 3 to 10. R'" can be halogenated. Preferably each R'" is independently a C1-10 or C1-6 alkyl, or phenyl. More preferably each occurrence of R"' is methyl or phenyl. More preferably each occurrence of R'" is independently methyl, phenyl, or trifluoropropyl.
[0016] The silanol-functional silicone can comprise at least one of a silanol- terminated polydimethylsiloxane, a silanol-terminated polydiphenylsiloxane, a silanol- terminated diphenylsiloxane-dimethylsiloxane copolymer, or a silanol-terminated polytrifluoropropylmethylsiloxane. A silanol-terminated polydimethylsiloxane is preferred. The silanol-terminated polydimethylsiloxane can have a viscosity of about 45 to about 85 centistokes (cSt) measured at room temperature (23°C).
[0017] The fluorinated silane in the coating composition can have a structure represented by Formula IV
R1-Si(OR')3 Formula IV wherein R1 is a fluorinated alkyl, and each occurrence of R' is independently hydrogen, alkyl, or cycloalkyl. Preferably R1 is a fluorinated C1-20 alkyl or a fluorinated C1-10 alkyl, and R' is a C1-10 alkyl, C1-5 alkyl, or C1-3 alkyl. A specific example of the fluorinated silane is (tridecafluofo- 1,1,2,2-tetrahydrooctyl)trimethoxysilane.
[0018] Without wishing to be bound by theory, it is believed that the fluorinated silane can react with the silanol-functional silicone during curing to form a phase change material that imparts anti-icing characteristics to the coating surface. The phase change material may have a structure of the Formula V
R1-Si(OR')2-O-(SiR"’2O)n- SiR’2O-Si(OR’)2-R1 Formula V wherein R1, R', and R’" are the same as described herein in the context of Formula III and Formula IV.
[0019] The coating composition can comprise, based on a total weight of the coating composition: about 60 to about 80 weight percent (wt%), or about 65 to about 75 weight percent of the epoxy-silicone; about 10 to about 25 weight percent, or about 15 to about 20 weight percent of the aminosilane; about 1 to about 20 weight percent, or about 5 to about 15 weight percent of the silanol-functional silicone; and about 0.5 to about 10 weight percent, or about 1 to about 5 weight percent of the fluorinated silane.
[0020] The coating composition can further comprise at least one of a curing catalyst, a surface- active agent, a heat stabilizer, an ultraviolet-light absorber, or a colorant.
[0021 ] The curing catalyst can be present in an amount of about 0.05 to about 1 weight percent, based on a total weight of the coating composition. The curing catalyst can comprise at least one of an organotin compound, an organozinc compound, an organotitanium compound, an organozirconium compound, or an organic acid. Organotin compounds tire particularly useful. Examples of the organotin compound include dibutyltin dicarboxylates, such as dibutyltin dilaurate and dibutyltin bis(alkyl maleate); dialkyltin alkoxide derivatives such as dibutyltin dimethoxide and dibutyltin diphenoxide; intramolecular coordination derivatives of dialkyltins, such as dibutyltin diacetylacetonate and dibutyltin acetoacetate; reaction mixtures of dibutyltin oxide with ester compounds; reaction mixtures of dibutyltin oxide with silicate compounds, or tetravalent dialkyltin oxide derivatives such as oxy derivatives of said dialkyltin oxide derivatives as described in U.S. Patent 6,642,309. Two or more of the curing catalyst can be used.
[0022] As described in US 7,923,513, a surface-active agent can modify the interaction of a coating composition with the substrate, in particular, the agent can modify the ability of the composition to wet a substrate. Surface active agents may also include leveling, defoaming, or flow agents, and the like. If used, the surface active agent can be present in an amount of about 0.1 to about 5 wt%, based on the total weight of the coating composition described herein.
[0023] Surface-active agent is known and can include polysiloxane defoamers such as a methylalkylpolysiloxane commercially available under the trade name BYK-077 or BYK- 500 from Byk Chemie, polymeric defoamers such as that commercially available under the trade name BYK 051, or other surface -active agent such as BYK-053, BYK-055, BYK-057, BYK-020, BYK-065, BYK-066N, BYK-067A, BYK-070, BYK-080A, BYK-088, BYK-141, BYK-019, BYK-021, BYK-022, BYK-023, BYK-024, BYK-025, BYK-028, BYK-011, BYK-031, BYK-032, BYK-033, BYK-034, BYK-035, BYK-036, BYK-037, BYK-038, BYK-045, BYK-A530, BYK-A555, BYK-071, BYK-060, BYK-018, BYK-044, BYK-094, BYK 333, BYK A530, or BYKUMEN, commercially available from Byk Chemie. In an aspect, the coating composition comprises two or more, for example two to six or two to five different surface- active agents.
[0024] The light stabilizer can include a hindered amine light stabilizer (HALS). HALS is commercially available, for example, under tire trade name BLS 292 from Mayzo, TINUVIN 123 or UVINUL 4092 from BASF Corp., OMNISTAB LS292 from ICG Specialty Chemicals, OMNISTAB LS944 from ICG Specialty Chemicals, SABOSTAB 119 or SABOSTAB 94 from Sabo S.p.A., or LOWILITE from Addivant. If present, the light stabilizer can be used in an amount of 01 to 1 wt% based on a total weight of tire coating composition. The coating composition can comprise more than one light stabilizer if needed.
[0025] The ultraviolet- light (UV) absorber that can be useful with the coating composition include avobenzone, 2,5-bis(5-tert-butyl-benzoxazol-2-yl)thiophene (Benetex OB+), disodium 4,4'-bis(2-sulfonatostyryl)biphenyl (Benetex 0B-M1), benzenepropanoic acid (BLS 99-2), 2,3,6,7-tetrahydro-9-methyl-1H,5H-quinolizino(9,l-gh)coumarin (Coumarin 102), Martins Yellow, morin hydrate, nitrofur azone, 2 -nitrophenyl phenyl sulfide (NPS), 5,12-naphthacenequinone (NTAQ), octocrylene, phenazine, 1,4-bis-(2-(5- phenyloxazolyl)) -benzene (POPOP), Quinoline Yellow, 3,3',4',5,6-pentahydroxyflavone (Quercetin), salicylaldehyde, Sudan I, triamterene, UV386A, or 9, 10-diethoxy anthracene (UVS-1101). Other known UV absorbers can also be used. UV absorbers can be used in an amount of 0.05 to 1 wt% based on a total weight of the coating composition. The coating composition can comprise more than one UV absorber.
[0026] The components of the coating composition can be mixed shortly before the coating composition is applied to the substrate. The coating composition can be applied by any of the suitable application methods, such as spraying, knife coating, spreading, pouring, dipping, impregnating, trickling or rolling, for example. In the course of such application, the substrate to be coated may itself be at rest, with the application equipment or unit being moved. Alternatively the substrate to be coated, for example a powerline, may be moved, with the application unit being at rest relative to the substrate or being moved appropriately.
[0027] The applied coating composition can be cured after a certain cure time. The cure time may be tuned by adjusting the cure temperature and/or humidity, provided that this does not entail any damage or alteration to the coating, such as premature complete crosslinking, for instance.
[0028] A thermal cure can be conducted at a temperature of about 30 to about 200° C., more preferably about 30 to about 150° C., and in particular about 30 to about 100° C for a time of about 1 minute (min) up to about 10 hours (h), more preferably about 2 min up to about 5 h, and in particular about 3 min to about 3 h.
[0029] In another embodiment, a coating composition comprises an acrylic modified silyl-terminated polyether: an epoxy-silicone; an aminosilane: and an organic solvent.
[0030] The acrylic modified silyl-terminated polyether can be an acrylic modified sily-terminated polyether described in U.S. Patent No. 6,642,309. The acrylic modified silyl- terminated polyether is commercially available under the trade name SILYL MA904 from Kaneka.
[0031] The epoxy-silicone and the aminosilane can be the same as the epoxy-silicone and the aminosilane described herein above. In an aspect, the aminosilane comprises a primary aminoalkylalkoxysilane and a diaminosilane. The weight ratio of the aminoalkylalkoxy silane to diaminosilane can be about 10:1 to about 2:1 or about 8:1 to about 4:1.
[0032] The coating composition can comprise an organic solvent useful for dissolving or dispersing components of the coating composition. Examples of the organic solvent include aliphatic hydrocarbons, such as, for example, hexane, isododecane, or cyclohexane: aromatic hydrocarbons such as for example, benzene, toluene, or xylene; ketones, such as, for example, acetone, methyl ethyl ketone, or methyl isobutyl ketone; or halogenated hydrocarbon solvents, such as, for example, trichloroethylene, or parachlorobenzotrifluoride. The organic solvent can include a blend of two or more the solvents described herein. Preferably, the organic solvent comprises parachlorobenzotrifluoride, which is frequently abbreviated as PCBTF. PCBTF is also sold under the trade name OXSOL 100.
[0033] The coating composition can comprise, based on a total weight of the coating composition: about 20 to about 45 weight percent, or about 25 to about 40 weight percent of the acrylic modified silyl-terminated polyether; about 20 to about 45 weight percent, or about 25 to about 40 weight percent of the epoxy-silicone; about 1 to about 20 weight percent, or about 5 to about 15 weight precent of the aminosilane; and about 10 to about 30 weight percent, or about 15 to about 25 weight percent of the organic solvent.
[0034] The coating composition can further comprise at least one of an unsaturated silane having an ethylenically unsaturated hydrocarbyl group, a curing catalyst, a surfaceactive agent, a heat stabilizer, an ultraviolet-light absorber, or a colorant.
[0035] If present, the unsaturated silane can be used in an amount of about 0.1 to about 5 weight percent or about 0.5 to about 3 weight percent based on a total weight of the coating composition.
[0036] The ethylenically unsaturated hydrocarbyl group in the unsaturated silane can be, for example, vinyl, allyl, isopropenyl, butenyl, cyclohexenyl or gamma-(meth)acryloxy allyl group. The unsaturated silane can also include a hydrolysable group such as, for example, an alkoxy, formyloxy, acetoxy, propionyloxy, or hydrocarbonyloxy. In an aspect, the unsaturated silane is an unsaturated alkoxysilane. Examples of the unsaturated alkoxysilane include an acrylic silane, vinyl trimethoxysilane, vinyl triethoxysilane, or 3- (meth)acryloxypropyl trimethoxysilane. Commercially available examples include SILQUEST A174 or S1LQUEST A171 available from Momentive. More than one unsaturated silane can be used in the coating composition.
[0037] The curing catalyst, the surface-active agent, tire heat stabilizer, and the ultraviolet-light absorber can be the same as described hereinabove.
[0038] The coating composition can be applied to various substrates such as metallic substrates, polymeric substrates, composite substrates, and the like. Advantageously, the coating composition can be applied to a flexible substrate. The coating composition can be applied and cured as described herein above. Once cured, the coating composition can form a coating that imparts anti-icing characteristics, and the coating can maintain structural integrity with minimized cracking or peeling off with a long service life when used outdoor in low temperature environments. [0039] In an aspect, after exposing to a freezing rain at an icing rate of about 4 millimeters per hour for 60 minutes at -10°C, the coated articles according to the disclosure can have up to about 76 wt% less ice accumulation, up to about 57 wt% less ice accumulation, or up to about 38 wt% less ice accumulation as compared to an uncoated substrate when tested under oscillating and impacting conditions. As used herein, oscillating conditions mean that a tested sample is connected to a motor which generates oscillation movement of the tested sample during testing. Impacting conditions mean that during oscillation, one extremity of the tested sample lightly impacts on the sample after every oscillation to generate additional force on the sample. Oscillation and impacting help to reduce ice accumulation on tire coated articles of the disclosure but do not have any effect on the uncoated substrates. Without wishing to be bound by theory, it is believed that the ice adheres firmly on the uncoated substrates but barely adheres to the coatings as disclosed herein.
[0040] The compositions, methods, and articles can alternatively comprise, consist of, or consist essentially of, any appropriate components or steps herein disclosed. The compositions, methods, and articles can additionally, or alternatively, be formulated so as to be devoid, or substantially free, of any steps, components, materials, ingredients, adjuvants, or species that are otherwise not necessary to the achievement of the function or objectives of the compositions, methods, and articles.
[0041] The singular forms “a,” “an,” and “the” include plural referents unless the context clearly dictates otherwise. “Or” means “and/or” unless clearly indicated otherwise by context. The modifier “about” used in connection with a quantity is inclusive of the stated value (e.g., “about 25-50 wt%” is a disclosure of “25-50 wt.%”) and has the meaning dictated by the context (e.g., includes the degree of error associated with measurement of the particular quantity). “Optional” or “optionally” means that the subsequently described event or circumstance can or cannot occur, and that the description includes instances where the event occurs and instances where it does not. A “combination” is inclusive of blends, mixhires, alloys, reaction products, and the like.
[0042] As used herein, the term “hydrocarbyl” and “hydrocarbon” refers broadly to a substituent comprising carbon and hydrogen, optionally with 1 to 3 heteroatoms, for example, oxygen, nitrogen, halogen, silicon, sulfur, or a combination thereof; “alkyl” refers to a straight or branched chain, saturated monovalent hydrocarbon group; “alkylene” refers to a straight or branched chain, saturated, divalent hydrocarbon group; “cycloalkyl” refers to a non- aromatic monovalent monocyclic or multicylic hydrocarbon group having at least three carbon atoms; “aryl” refers to an aromatic monovalent group containing only carbon in the aromatic ring or rings; “arylene” refers to an aromatic divalent group containing only carbon in the aromatic ring or rings; and “arylalkyl” refers to an alkyl group that has been substituted with an aryl group as defined above, with benzyl being an exemplary arylalkyl group.
[0043] Unless otherwise indicated, each of the foregoing groups can be unsubstituted or substituted, provided that the substitution does not significantly adversely affect synthesis, stability, or use of the compound. The term “substituted” as used herein means that at least one hydrogen on the designated atom or group is replaced with another group, provided that the designated atom’s normal valence is not exceeded.
[0044] All cited patents, patent applications, and other references are incorporated herein by reference in their entirety. If a term in the present application contradicts or conflicts with a term in an incorporated reference, the term from the present application takes precedence over tire conflicting term from the incorporated reference.
[0045] While embodiments have been set forth for the purpose of illustration, the foregoing descriptions should not be deemed a limitation on the scope herein. Accordingly, various modifications, adaptations, and alternatives can occur to one skilled in the art without departing from the spirit and scope herein.

Claims

CLAIMS We claim:
1. A coated article comprising: a flexible substrate; and a coating disposed on the flexible substrate, wherein the coating comprises a cured product of a coating composition comprising: an epoxy-silicone; an aminosilane; a silanol- functional silicone; and a fluorinated silane.
2. The coated article of claim 1, wherein the coating composition comprises, based on a total weight of the coating composition: about 60 to about 80 weight percent, or about 65 to about 75 weight percent of the epoxy-silicone; about 10 to about 25 weight percent, or about 15 to about 20 weight percent of the aminosilane; about 1 to about 20 weight percent, or about 5 to about 15 weight percent of the silanol-functional silicone; and about 0.5 to about 10 weight percent, or about 1 to about 5 weight percent of the fluorinated silane.
3. The coated article of claim 1 or claim 2, wherein the epoxy- silicone has an epoxy equivalent weight of about 200 to about 700 grams, about 300 to about 700 grams, or about 400 to about 600 grams.
4. The coated article of any one of claims 1 to 3, wherein the aminosilane has a structure represented by Formula I or Formula II:
HRN-X-SiR"x(OR')3-x Formula I
HN(X------SiR"x(OR')3-x)n(X'--SiR"y(OR')3.y)m Formula II wherein in Formula I and Formula II
R is hydrogen, alkyl, cycloalkyl, aryl, or aralkyl; each occurrence of R' is independently hydrogen, alkyl, or cycloalkyl; each occurrence of R" is independently alkyl, cycloalkyl, aryl, or aralkyl; each occurrence of X and X' is independently an alkyl, cycloalkyl, or -R2-NH-R3-, wherein R2 and R3 are independently alkylene, or cycloalkylene; x is 0 to 2, y is 0 to 2, n is 0 to 2, m is 0 to 2, and m+n is 2.
5. The coated article of any one of claims 1 to 4, wherein the silano-functional silicone has a structure represented by Formula III
HO-(SiR'"2O)n-SlR'"2-OH Formula III wherein each occurrence of R"’ is independently alkyl, cycloalkyl, aryl or aralkyl, and n is 2 to 20.
6. The coated article of any one of claims 1 to 5, wherein the silanol-functional silicone comprises at least one of a silanol-terminated polydiniethylsiloxane, a silanol- terminated polydiphenylsiloxane, a silanol -terminated diphenylsiloxane-dimethylsiloxane copolymer, or a silanol-terminated polytrifluoropropylmethylsiloxane.
7. The coated article of any one of claims 1 to 6, wherein the fluorinated silane has a structure represented by Formula IV
R1 - Si(OR'h Formula IV wherein
R1 is a fluorinated alkyl, and each occurrence of R' is independently hydrogen, alkyl, or cycloalkyl.
8. The coated article of any one of claims 1 to 7, wherein the coating composition further comprises at least one of a curing catalyst, a surface-active agent, a heat stabilizer, an ultraviolet-light absorber, or a colorant.
9. A coated article comprising: a substrate; and a coating disposed on the substrate; wherein the coating comprises a cured product of a coating composition comprising: an acrylic modified silyl- terminated polyether; an epoxy-silicone; an aminosilane; and an organic solvent.
10. The coated article of claim 9, wherein the coating compsition comprises, based on a total weight of the coating composition: about 20 to about 45 weight percent, or about 25 to about 40 weight percent of the acrylic modified silyl-terminated polyether; about 20 to about 45 weight percent, or about 25 to about 40 weight percent of the epoxy-silicone; about 1 to about 20 weight percent, or about 5 to about 15 weight precent of the aminosilane; and about 10 to about 30 weight percent, or about 15 to about 25 weight percent of the organic solvent.
11. The coated article of claim 9 or claim 10, wherein the epoxy-silicone has an epoxy equivalent weight of about 200 to about 700 grams, about 300 to about 700 grams, or about 400 to about 600 grams.
12. The coated article of any one of claims 9 to 11, wherein the aminosilane comprises at least a silane having a structure represented by Formula I or Formula II:
HRN-X-SiR"x(OR')3.x Formula I
HN(X---SiR'x(OR')3 x)n(X'---SiR''y(OR')3-y)m Formula II wherein in Formula I and Formula II
R is hydrogen, alkyl, cycloalkyl, aryl, or aralkyl; each occurrence of R' is independently hydrogen, alkyl, or cycloalkyl; each occurrence of R" is independently alkyl, cycloalkyl, aryl, or aralkyl; each occurrence of X and X' is independently an alkyl, cycloalkyl, or -R2~NH-R3-, wherein R3 and R3 are independently alkylene, or cycloalkylene; x is 0 to 2, y is 0 to 2, n is 0 to 2, m is 0 to 2, and m+n is 2.
13. The coated article of any one of claims 9 to 12, wherein the aminosilane comprises a primary aminoalkylalkoxysilane and a diaminosilane.
14. The coated article of any one of claims 9 to 13, wherein the organic solvent comprises parachlorobenzotrifluoride.
15. The coated article of claims 9 to 14, further comprising at least one of an unsaturated silane having an ethylenically unsaturated hydrocarbyl group, a curing catalyst, a surface-active agent, a heat stabilizer, an ultraviolet-light absorber, or a colorant.
16. The coated article of any one of claims 9 to 15, wherein the coating composition further comprises the unsaturated silane in an amount of about 0.1 to about 5 weight percent or about 0.5 to about 3 weight percent based on a total weight of the coating composition.
17. The coated article of any one of claims 9 to 16, wherein the unsaturated silane comprises an unsaturated alkoxy silane.
18. The coated article of any one of claims 1 to 17, wherein the substrate is a powerline, a wire, or a cable.
19. The coated article of any one of claims 1 to 18, wherein after exposing to a freezing rain at an icing rate of about 4 millimeters per hour for 60 minutes at -10°C, the coated article has up to about 76 wt% less ice accumulation, up to about 57 wt% less ice accumulation, or up to about 38 wt% less ice accumulation as compared to an uncoated substrate when tested under oscillating and impacting conditions.
PCT/US2023/027307 2022-07-15 2023-07-11 Coated flexible articles with anti-icing surface WO2024015316A1 (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060205861A1 (en) * 2003-07-16 2006-09-14 Glenn Gordon Coating compositions comprising epoxy resins and aminofunctional silicone resins
WO2009029435A1 (en) * 2007-08-27 2009-03-05 3M Innovative Properties Company Silicone mold and use thereof
WO2014126599A1 (en) * 2013-02-15 2014-08-21 Momentive Performance Materials Inc. Antifouling system comprising silicone hydrogel
US20140303284A1 (en) * 2013-03-15 2014-10-09 The Sherwin-Williams Company Expoxyfluorosilicones and modified polyacrylic resins for coating compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060205861A1 (en) * 2003-07-16 2006-09-14 Glenn Gordon Coating compositions comprising epoxy resins and aminofunctional silicone resins
WO2009029435A1 (en) * 2007-08-27 2009-03-05 3M Innovative Properties Company Silicone mold and use thereof
WO2014126599A1 (en) * 2013-02-15 2014-08-21 Momentive Performance Materials Inc. Antifouling system comprising silicone hydrogel
US20140303284A1 (en) * 2013-03-15 2014-10-09 The Sherwin-Williams Company Expoxyfluorosilicones and modified polyacrylic resins for coating compositions

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