CN116925628A - Antifogging coating, preparation method thereof and product - Google Patents

Antifogging coating, preparation method thereof and product Download PDF

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Publication number
CN116925628A
CN116925628A CN202210319342.4A CN202210319342A CN116925628A CN 116925628 A CN116925628 A CN 116925628A CN 202210319342 A CN202210319342 A CN 202210319342A CN 116925628 A CN116925628 A CN 116925628A
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formula
fog coating
monomer
coating
plasma
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宗坚
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Jiangsu Favored Nanotechnology Co Ltd
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Jiangsu Favored Nanotechnology Co Ltd
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Priority to CN202210319342.4A priority Critical patent/CN116925628A/en
Priority to TW112111262A priority patent/TWI846402B/en
Priority to PCT/CN2023/083655 priority patent/WO2023185672A1/en
Publication of CN116925628A publication Critical patent/CN116925628A/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
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/14—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by electrical means
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/054—Forming anti-misting or drip-proofing coatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/056—Forming hydrophilic coatings
    • 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
    • C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
    • C23C14/06—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material characterised by the coating material
    • C23C14/12—Organic material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2369/00—Characterised by the use of polycarbonates; Derivatives of polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2471/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2477/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Paints Or Removers (AREA)

Abstract

The anti-fog coating of the specific embodiment of the disclosure is formed by plasma polymerization of a saturated chain monomer, wherein the saturated chain monomer at least has hydrophilic groups at two ends, and the hydrophilic groups are hydroxyl groups, amino groups or carboxyl groups; the carbon-carbon connection bond in the saturated chain monomer is provided with or not provided with imino; the saturated chain monomer is provided with or without substituent groups, and the substituent groups are hydroxyl, amino or carboxyl; at most one of amino or hydroxyl groups is attached to the same carbon atom in the saturated chain monomer. The anti-fog coating formed by adopting the saturated chain monomer plasma polymerization has excellent hydrophilic performance, small chromatic aberration, excellent light transmittance and good wear resistance, and meanwhile, the monomer does not contain double bonds, so that adverse effects possibly caused to the coating in the long-term use process due to unstable double bond residues in the coating are avoided. The anti-fog coating of embodiments of the present disclosure is suitable for use in anti-fog coatings of transparent substrate surfaces.

Description

Antifogging coating, preparation method thereof and product
Technical Field
The present disclosure relates to the field of plasma chemistry, and in particular, to an anti-fog coating, a method for preparing the same, and a product.
Background
Transparent materials (e.g., glass, plastic) find wide use in industrial and agricultural production and in the field of everyday life and military applications, such as goggles, laser goggles, telescope lenses and lenses for various camera devices, various mechanical viewing windows, sports goggles, bathroom glass, chemical or biological masks, vehicle windshields and rearview mirrors, blast protection devices, helmets, solar panels, viewing windows for measuring instruments, glass covers, glass walls for greenhouses, and the like. However, in winter, glasses can make us "look flower in fog"; in cold winter, the fog on the surface of the windshield can greatly influence the visibility of people and even cause accidents. The atomization problem brings a plurality of inconveniences to the work and life of people, and the research and development of anti-fog technology and anti-fog materials are focused by scientific and enterprise industries.
The provision of an anti-fog coating on the surface of a transparent material is a common anti-fog means, and the anti-fog coating is generally of two types, one is that a hydrophilic surface is formed on the surface of the transparent material, water drops spread on the hydrophilic surface to form a film, and the other is that a hydrophobic surface is formed on the surface of the transparent material, and the water drops bead and roll on the hydrophobic surface. The latter has the disadvantage that atomization still occurs when a large amount of water vapor is rapidly condensed. The former forms a uniform water film to eliminate the diffuse reflection phenomenon of light rays and achieve the purpose of anti-fog.
At present, the technical improvement of the hydrophilic anti-fog coating is mainly focused on the traditional liquid phase treatment method, including a gel-sol method, a layer-by-layer self-assembly method, a free radical solution polymerization method and the like. These methods generally use spray or spin coating methods to apply glue to the substrate surface and then cure using heat or UV radiation. In the liquid phase treatment method, there is a disadvantage that: the presence of solvents, reaction media, may react with the substrate, destroying the substrate structure, and creating a potential hazard.
Plasma Enhanced Chemical Vapor Deposition (PECVD) is a chemical vapor deposition process in which monomers are activated by using plasma generated by glow discharge at low pressure to generate high-activity monomer free radicals or ion fragments, and the high-activity monomer free radicals or ion fragments are deposited on the surface of a substrate to react to form a film. The PECVD has: the method has the advantages of high deposition rate, good film forming quality, fewer pinholes and difficult cracking, does not need liquid phase solvent in the reaction process, and can not damage the base material. Thus, the use of PECVD techniques provides a better choice for the preparation of hydrophilic anti-fog coatings, which the inventors have previously studied, as disclosed in CN111501023a, by preparing hydrophilic coatings by PECVD using acrylic monomers, it is possible to prepare hydrophilic anti-fog coatings, which on the one hand have to be improved in their hydrophilic properties; on the other hand, the monomer of the coating contains double bonds, unstable double bond residues are unavoidable after the reaction, and the performance of the coating can be influenced in the long-term use process.
Disclosure of Invention
Embodiments of the present disclosure provide an anti-fog coating, which has no residual double bond, and simultaneously has excellent hydrophilic performance, light transmittance, and good abrasion resistance, and the specific scheme is as follows:
an anti-fog coating formed from a substrate contacted with a plasma comprising a monomer of formula (1);
X 2 -R-X 1
(1)
in the formula (1), R is C 1 -C 30 Alkylene or C of (2) 1 -C 30 Substituted alkylene of X 1 And X 2 Each independently selected from hydroxy, amino or carboxyl; the substituent of the substituted alkylene is hydroxyl, amino or carboxyl; the C is 1 -C 30 Alkylene or C of (2) 1 -C 30 With or without-NH-'s between the carbon-carbon linkages of the substituted alkylene groups; and in formula (1), at most one of an amino group and a hydroxyl group is bonded to the same carbon atom.
Alternatively, the monomer of formula (1) has a structure represented by formula (2),
in the formula (2), R 1 And R is 2 Independently selected from C 1 -C 10 Alkylene or C of (2) 1 -C 10 Substituted alkylene of (a).
Alternatively, the monomer of formula (1) has a structure represented by formula (3),
in the formula (3), X 3 And X 4 Each independently selected from the group consisting of hydrogen, methyl, hydroxy, hydroxymethyl, amino, and carboxyl; n is n 1 0, 1, 2, 3, 4, 5, 6, 7 or 8; n is n 2 0, 1, 2, 3, 4, 5, 6, 7 or 8.
Alternatively, X 3 And X 4 Are all hydrogen atoms, X 1 And X 2 Are the same groups.
Optionally, R is C 1 -C 16 Alkylene or substituted alkylene of (a).
Alternatively, the monomer of formula (1) has a structure represented by formula (4),
in the formula (4), X 5 And X 6 Each independently selected from the group consisting of hydrogen, methyl, hydroxy, hydroxymethyl, amino, and carboxyl; n is n 3 0, 1, 2, 3, 4, 5, 6, 7 or 8.
Alternatively, X 5 And X 6 Are all hydrogen atoms, X 1 And X 2 Are the same groups.
Alternatively, the monomer of formula (1) is selected from the monomers of the structures shown in formulas (1-1) to (1-48),
optionally, the substrate is an optical instrument, metal, ceramic, plastic, glass or electronic device.
Optionally, the optical instrument is a lens, a reflector or a lens.
Optionally, the substrate is a transparent material.
Optionally, the anti-fog coating has a light transmittance of 90% or more.
Optionally, the anti-fog coating has a measured water contact angle of 10 ° or less.
Alternatively, the anti-fog coating is rubbed with a dust-free cloth for 500 times under a load of 1N, and the measured water contact angle is less than 10 degrees.
The specific embodiment of the disclosure also provides a preparation method of the anti-fog coating, which is used for preparing the anti-fog coating, and comprises the following steps: providing a substrate, placing the substrate in a plasma reactor, introducing the monomer vapor of the formula (1) into the plasma reactor, discharging plasma, and polymerizing the plasma on the surface of the substrate to form the anti-fog coating.
Optionally, before the monomer vapor of formula (1) is introduced into the plasma reactor, introducing a plasma source gas, starting a plasma device to discharge continuously, and pretreating the surface of the substrate.
Optionally, the plasma source gas is one or a mixture of a plurality of helium, argon, nitrogen, oxygen and hydrogen.
Optionally, the plasma discharge is pulse plasma discharge, wherein the pulse power is 10-300W, the pulse duty ratio is 20-90%, and the discharge time of the pulse output is 30-36000 s.
Alternatively, the monomer of formula (1) is first added to an alcohol solvent to prepare a solution, and then vaporized and passed into a plasma reactor.
Optionally, the alcohol is one or more of methanol, ethanol or propanol.
A product having an anti-fog coating as described above on at least part of its surface.
Compared with the prior art, the technical scheme of the embodiment of the disclosure has the following beneficial effects:
the anti-fog coating of the specific embodiment of the disclosure is formed by plasma polymerization of a saturated chain monomer shown in a substrate contact formula (1) and having hydroxyl groups, amino groups or carboxyl groups at least at two ends, and the anti-fog coating formed by the monomer plasma polymerization of the structure has excellent hydrophilic performance, small color difference, excellent light transmittance and good wear resistance, and meanwhile, the monomer does not contain double bonds, so that adverse effects on the anti-fog coating performance possibly caused in a long-term use process due to unstable double bond residues in the anti-fog coating are avoided. The anti-fog coating of embodiments of the present disclosure is particularly suitable for use in hydrophilic anti-fog coatings of transparent substrate surfaces.
Detailed Description
The inventor researches find that the anti-fog coating formed by adopting the saturated chain monomer shown in the formula (1) to polymerize in a plasma manner has excellent hydrophilic performance, light transmittance and good wear resistance, and meanwhile, the monomer does not contain double bonds, so that adverse effects on the performance of the anti-fog coating in a long-term use process, which are possibly caused by unstable double bond residues in the anti-fog coating, are avoided. The anti-fog coating of embodiments of the present disclosure is particularly suitable for use in hydrophilic anti-fog coatings of transparent substrate surfaces.
The present disclosure provides an anti-fog coating of a plasma polymerized coating formed from a substrate contacted with a plasma comprising a monomer of formula (1),
X 2 -R-X 1
(1)
in the formula (1), R is C 1 -C 30 Alkylene or substituted alkylene, X 1 And X 2 Each independently selected from hydroxy, amino or carboxyl; the substituent of the substituted alkylene is hydroxyl, amino or carboxyl; the C is 1 -C 30 With or without-NH-'s between carbon-carbon linkages of the alkylene or substituted alkylene; and in formula (1), at most one of an amino group and a hydroxyl group is bonded to the same carbon atom.
Anti-fog coatings, X, of embodiments of the present disclosure 1 And X 2 Independent of each other, X 1 And X 2 May be the same group, e.g. X 1 And X 2 Are all hydroxyl, carboxyl or amino; x is X 1 And X 2 May also be a different group, e.g. X 1 Is hydroxy, X 2 Carboxyl groups, e.g. X 1 Is hydroxy, X 2 Is amino.
The anti-fog coating of embodiments of the present disclosure, having at most one of an amino group or a hydroxyl group attached to the same carbon atom, refers to: the same carbon atom is bonded to only one hydroxyl group, the same carbon atom is bonded to only one amino group, or the same carbon atom has neither hydroxyl nor amino group.
Anti-fog coatings of embodiments of the present disclosure, the C 1 -C 30 Alkylene or C of (2) 1 -C 30 The substituted alkylene of (a) may be a linear or branched alkylene, but in some embodiments, the C is selected from the group consisting of better abrasion resistance and hydrophilicity 1 -C 30 Alkylene or C of (2) 1 -C 30 C wherein the substituted alkylene group is linear 1 -C 30 Alkylene or substituted alkylene of (a).
Anti-fog coatings of embodiments of the present disclosure, in some specific examples, the C 1 -C 30 has-NH-between carbon-carbon linkages of the alkylene or substituted alkylene.
In some specific examples, the monomer of formula (1) has a structure represented by formula (2),
in the formula (2), R 1 And R is 2 Independently selected from C 1 -C 10 Alkylene or substituted alkylene of (a).
In some specific examples, the monomer of formula (1) has a structure represented by formula (3),
in the formula (3), X 3 And X 4 Each independently selected from the group consisting of hydrogen, methyl, hydroxy, hydroxymethyl, amino, and carboxyl; n is n 1 0, 1, 2, 3, 4, 5, 6, 7 or 8; n is n 2 0, 1, 2, 3, 4, 5, 6, 7 or 8.
The anti-fog coating of embodiments of the present disclosure, in some specific examples, in formula (3), n, in view of better hydrophilic properties 1 Is 0, 1 or 2, n 2 0, 1 or 2.
In particular embodiments of the present disclosure, the anti-fog coating, in view of better hydrophilic properties, in some particular embodiments, in formula (3), X 3 And X 4 Are all hydrogen atoms, X 1 And X 2 And is hydroxy, amino, or carboxyl.
In particular embodiments of the present disclosure, the anti-fog coating, in view of better hydrophilic properties, in some particular embodiments, in formula (1), R is C 1 -C 16 Alkylene or substituted alkylene of (a).
Anti-fog coatings of embodiments of the present disclosure, in some specific examples, the C 1 -C 30 Has no-NH-between carbon-carbon linkages of the alkylene or substituted alkylene group.
In some specific examples, the monomer of formula (1) has a structure represented by formula (4),
in the formula (4), X 5 And X 6 Each independently selected from the group consisting of hydrogen, methyl, hydroxy, hydroxymethyl, amino, and carboxyl; n is n 3 0, 1, 2, 3, 4, 5, 6, 7 or 8.
The anti-fog coating of embodiments of the present disclosure, in view of better hydrophilic properties, in some specific examples, in formula (4), n 3 0, 1, 2, 3 or 4.
In particular embodiments of the present disclosure, the anti-fog coating, in view of better hydrophilic properties, in some particular embodiments, in formula (4), X 5 And X 6 Are all hydrogen atoms, X 1 And X 2 And is hydroxy, amino, or carboxyl.
In some embodiments, the monomer of formula (1) is selected from the group consisting of monomers of structures represented by formulas (1-1) through (1-48),
in some specific examples, the substituent of the substituted alkylene is hydroxy, amino, or carboxyl.
In some specific examples, the substrate is an optical instrument, metal, ceramic, plastic, glass, or electronic device, etc.
In some embodiments, the anti-fog coating of the present disclosure has a water contact angle of less than 10 ° measured according to GB/T30047-2013, and a relatively uniform water film is formed on the surface of the anti-fog coating, so that diffuse reflection of light is reduced to perform an anti-fog function, and thus, in some embodiments, the anti-fog coating is particularly suitable for an anti-fog coating as a transparent material, for example, in some embodiments, the substrate is a lens of glasses, goggles, laser goggles, lenses of telescopes and various camera devices, various mechanical viewing windows, moving goggles, bathroom glasses, chemical or biological masks, vehicle windshields and rear-view mirrors, explosion-proof treatment protection devices, helmets, solar panels, viewing windows of measuring instruments, glass covers, glass walls of greenhouses, and the like.
In some embodiments, the anti-fog coating of embodiments of the present disclosure has excellent abrasion resistance and hydrophilicity, and the anti-fog coating has a water contact angle of 10 ° or less, measured according to GB/T30047-2013, after 500 rubs with a dust-free cloth under a load of 1N.
In some embodiments, the anti-fog coating of embodiments of the present disclosure has a light transmittance of greater than 90% so as not to have excessive impact on the light transmittance properties of the transparent substrate.
In some embodiments, the anti-fog coating is a plasma polymerized coating formed from a plasma of a monomer of the structure of formula (1), and in other embodiments, the anti-fog coating is a plasma polymerized coating formed from a plasma of a monomer of the structure of formula (1) and other monomers, as specifically desired.
The anti-fog coating of embodiments of the present disclosure, in some embodiments, has a thickness of from 1 to 1000nm. In some embodiments, the anti-fog coating has a thickness of 1-100nm, specifically, for example, 49nm, 54nm, 56nm, 61nm, 73nm, 79nm, 82nm, 87nm, 92nm, 93nm, 96nm, or 98nm, as an ultra-thin transparent nano-coating.
The specific embodiment of the disclosure also provides a preparation method of the anti-fog coating, which comprises the following steps: providing a substrate, placing the substrate in a plasma reactor, introducing the monomer vapor of the formula (1) into the plasma reactor, discharging plasma, and polymerizing the plasma on the surface of the substrate to form the anti-fog coating.
The preparation method of the antifogging coating according to the specific embodiment of the present disclosure is as described above for the monomer and the substrate.
In order to further enhance the bonding force between the plasma coating and the substrate, in some embodiments, the substrate is pretreated with a continuous plasma source gas before introducing the monomer vapor, for example, in an atmosphere of the plasma source gas, the specific pretreatment mode is that the plasma discharge power is 20-500W, the discharge mode is continuous, and the continuous discharge time is 10 s-3600 s.
In some embodiments, the method for preparing the anti-fog coating of the embodiments of the disclosure comprises introducing a plasma source gas and simultaneously introducing a monomer vapor for pretreatment and coating pre-deposition.
In some embodiments, the introduced plasma source gas is one or a mixture of several of helium, argon, nitrogen, oxygen and hydrogen.
In some embodiments, the plasma of the monomer is plasma excited in a pulse mode, and the monomer flow is 10 to 500 μL/min, and specifically may be, for example, 10 μL/min, 50 μL/min, 100 μL/min, 150 μL/min, 200 μL/min, 300 μL/min, 400 μL/min, or the like.
In some embodiments, the temperature in the cavity is controlled at 20-80 ℃, and specifically, for example, 20 ℃, 25 ℃, 30 ℃, 35 ℃, 40 ℃, 45 ℃, 50 ℃, 55 ℃, 60 ℃, 65 ℃, 70 ℃, 75 ℃, 80 ℃ or the like; the pressure in the chamber is 1000 millitorr or less, more preferably 500 millitorr or less, and still more preferably 100 millitorr or less.
In particular embodiments, the monomer vaporization temperature is 50 ℃ to 200 ℃, and may be, for example, 50 ℃, 60 ℃, 70 ℃, 80 ℃, 90 ℃, 100 ℃, 110 ℃, 120 ℃, 130 ℃, 140 ℃, 150 ℃, 160 ℃, 170 ℃, 180 ℃, 190 ℃, 200 ℃ and the like, and the pulse plasma is generated by applying a pulse voltage discharge under vacuum conditions, wherein the pulse power is 10W to 300W, and may be, for example, 10W, 20W, 30W, 40W, 50W, 70W, 80W, 100W, 120W, 140W, 160W, 180W, 190W, 200W, 210W, 220W, 230W, 240W, 250W, 260W, 270W, 280W, 290W or 300W and the like, and in particular embodiments, the pulse power is 30W to 100W; the pulse duty cycle is 0.1% to 90%, specifically, for example, may be 0.1%, 0.5%, 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85% or 90%, etc., and in some embodiments, the pulse duty cycle is 20% to 90%, further the pulse duty cycle is 40% to 80%, further the pulse duty cycle is 45% to 75% in view of better hydrophilicity; the plasma discharge time of the pulse output is 30s to 36000s, specifically, for example, 100s, 500s, 1000s, 1800s, 2000s, 1000s, 2000s, 3000s, 3600s, 4000s, 5000s, 6000s, 7000s, 7200s, 10800s, 14400s, 18000s, 21600s, 25200s, 28800s, 32400s, 36000s, or the like may be used.
In some embodiments, the plasma discharge mode may be any of various existing discharge modes, for example, electrodeless discharge (such as rf inductively coupled discharge, microwave discharge), single electrode discharge (such as corona discharge, plasma jet formed by unipolar discharge), double electrode discharge (such as dielectric barrier discharge, bare electrode rf glow discharge), and multi-electrode discharge (such as discharge using a floating electrode as a third electrode).
In some embodiments, the monomer of formula (1) is first added to an alcohol solvent to prepare a solution, and then vaporized into a plasma reactor, by which means the vaporization temperature of the monomer can be reduced, which is more beneficial to the vaporization of the monomer. In some embodiments, the alcohol is one or more of methanol, ethanol, or propanol.
Embodiments of the present disclosure also provide a product having at least a portion of the surface of the product having any of the anti-fog coatings described above, and in some embodiments, a portion of or all of the surface of the device has the anti-fog coating described above deposited thereon.
The present disclosure is further illustrated by the following specific examples.
Examples
Description of the test methods
Coating thickness test: detection was performed using a Filmetrics F20-UV-film thickness gauge.
Coating water contact angle: the test was performed according to the GB/T3047-2013 standard.
Coating light transmittance and color difference: calculation is carried out according to the GB11186.3-1989 standard, a spectrocolorimeter is used for detection, delta E in the test result represents chromatic aberration,t represents light transmittance; l, a and b represent three color channels in the Lab color model, L represents brightness, and the value range is [0, 100 ]]Representing from pure black to pure white; a represents a range from red to green, and the value range is [127, -128 ]]The method comprises the steps of carrying out a first treatment on the surface of the b represents a range from yellow to blue, and the value range is [127, -128 ]]。
Friction performance test: the water contact angle change before and after rubbing was measured by rubbing 500 times with a dust-free cloth under a load of 1N using a reciprocating type abrader.
Example 1
Placing a substrate transparent glass plate (length: 75mm, width: 26mm, thickness: 1 mm) in a 500L plasma vacuum reaction cavity, continuously vacuumizing the reaction cavity to enable the vacuum degree to reach 80 millitorr, introducing helium gas at the temperature of 45 ℃ in the cavity, and enabling the flow to be 40sccm;
the air pressure of the cavity is kept at 80 millitorr, the helium flow is kept at 40sccm, the radio frequency plasma discharge is started, the radio frequency energy output mode is continuous discharge, the discharge time is 30s, and the discharge power is 300w.
Then, introducing a monomer with a structure shown in the formula (1-6), wherein the monomer flow is 50 mu L/min, the monomer gasification temperature is 90 ℃, the cavity air pressure is 80 millitorr, the helium flow is 40sccm, starting the radio frequency plasma discharge, the radio frequency energy output mode is pulse, the discharge power is 40w, the pulse duty ratio is 75%, the pulse frequency is 50Hz, the discharge time is 3600s, and a coating is formed on the surface of the transparent glass plate;
after the coating preparation was completed, air was introduced to restore the reaction chamber to normal pressure, the chamber was opened, and the transparent glass plate was taken out to perform the thickness, light transmittance, chromaticity value, water contact angle and abrasion resistance test of the coating, and the test results are shown in table 1 below.
Example 2
The monomer of the structure shown in the formula (1-6) in example 1 was replaced with the monomer of the structure shown in the following formula (1-4), the vaporization temperature of the monomer of the structure shown in the formula (1-4) was 90 ℃, and the other processes were the same as those in example 1, and the thickness, light transmittance, chromaticity value, water contact angle and abrasion resistance of the obtained coating were tested, and the test results are shown in the following table 1.
Example 3
The monomer of the structure shown in the formula (1-6) in example 1 was replaced with the monomer of the structure shown in the following formula (1-19), the vaporization temperature of the monomer of the structure shown in the formula (1-19) was 110 ℃, and the other processes were the same as those in example 1, and the thickness, light transmittance, chromaticity value, water contact angle and abrasion resistance of the obtained coating were tested, and the test results are shown in the following table 1.
Example 4
The transparent glass plate substrate in example 1 was replaced with a transparent PC (polycarbonate) plate substrate, and the resulting coating was subjected to thickness, light transmittance, chromaticity value, water contact angle and abrasion resistance test in accordance with example 1, and the test results are shown in table 1 below.
Example 5
The transparent glass plate substrate in example 2 was replaced with a transparent PC (polycarbonate) plate substrate, and the resulting coating was subjected to thickness, light transmittance, chromaticity value, water contact angle and abrasion resistance test in accordance with example 2, and the test results are shown in table 1 below.
Example 6
The transparent glass plate substrate in example 3 was replaced with a transparent PC (polycarbonate) plate substrate, and the resulting coating was subjected to thickness, light transmittance, chromaticity value, water contact angle and abrasion resistance test in accordance with example 3, and the test results are shown in table 1 below.
Example 7
Placing a substrate transparent glass plate (length: 75mm, width: 26mm, thickness: 1 mm) in a 500L plasma vacuum reaction cavity, continuously vacuumizing the reaction cavity to enable the vacuum degree to reach 80 millitorr, introducing helium gas at the temperature of 45 ℃ in the cavity, and enabling the flow to be 40sccm;
maintaining the air pressure of the cavity at 80 millitorr, maintaining the helium flow at 40sccm, starting the radio frequency plasma discharge, and continuously discharging the energy output mode of the radio frequency for 30s and the discharge power at 300w;
then preparing 20g of monomer with a structure shown in the following formula (1-43) and 100mL of ethanol into a solution, introducing the solution into a reaction cavity at a flow rate of 150 mu L/min after the solution is gasified at 150 ℃, keeping the cavity air pressure at 80 millitorr, keeping the helium flow rate at 160sccm, starting the radio frequency plasma discharge, and forming a coating on the surface of a transparent glass plate, wherein the radio frequency energy output mode is pulse, the discharge power is 40w, the pulse frequency is 50Hz, the pulse duty ratio is 45%, and the discharge time is 3600 s;
after the coating preparation is finished, air is introduced to restore the reaction cavity to normal pressure, the cavity is opened, and the transparent glass plate is taken out to test the thickness, the light transmittance, the chromaticity value, the water contact angle and the friction resistance of the coating, and the test results are listed in table 1.
Example 8
The thickness, light transmittance, chromaticity value, water contact angle and abrasion resistance of the obtained coating were tested in the same manner as in example 7 except that the monomer having the structure represented by the following formulas (1-21) was replaced with the monomer having the structure represented by the following formulas (1-21) in example 7, and the test results are shown in Table 1 below.
Example 9
The transparent glass plate substrate in example 7 was replaced with a transparent PC (polycarbonate) plate substrate, and the resulting coating was subjected to thickness, light transmittance, chromaticity value, water contact angle and abrasion resistance test in accordance with example 7, and the test results are shown in table 1 below.
Example 10
The transparent glass plate substrate in example 8 was replaced with a transparent PC (polycarbonate) plate substrate, and the resulting coating was subjected to thickness, light transmittance, chromaticity value, water contact angle and abrasion resistance test in accordance with example 8, and the test results are shown in table 1 below.
Comparative example 1
The monomer of the structure shown in the formulas (1-6) in example 1 was replaced with the hexanol monomer of the structure shown in the following formula (5), the vaporization temperature of the hexanol monomer of the structure shown in the formula (5) was 110 ℃, and the other processes were identical to those of example 1, and the thickness, light transmittance, chromaticity value, water contact angle and abrasion resistance of the obtained coating were tested, and the test results are shown in table 1.
Comparative example 2
The monomer of the structure shown in the formulas (1-6) in example 4 was replaced with a caproic acid monomer of the structure shown in the following formula (6), the vaporization temperature of the caproic acid monomer of the structure shown in the formula (6) was 110 ℃, and the other processes were the same as those in example 5, and the thickness, light transmittance, chromaticity value, water contact angle and abrasion resistance of the obtained coating were tested, and the test results are shown in table 1.
TABLE 1 results of Performance test of examples 1-10 and comparative examples 1-2
From the results in table 1, it is seen that the pre-friction coatings of examples 1 to 10 all have water contact angles of 5 ° to 6 °, which are much lower than the water contact angles of 77 ° and 72 ° of the coatings of comparative examples 1 and 2, thereby further indicating that the coatings of examples 1 to 10, which are formed by plasma polymerization of monomers having two hydrophilic groups, have better hydrophilic properties and antifogging properties than the monomers of comparative examples 1 and 2, which have one hydrophilic group.
Meanwhile, as can be seen from the results of table 1, the coatings of examples 1 to 10 formed by plasma polymerization of saturated chain monomers having hydroxyl groups, amino groups or carboxyl groups at both ends have good abrasion resistance, the change of the water contact angle is not more than 4 ° after rubbing 500 times with a dust-free cloth under a load of 1N using a reciprocating type abrasion machine, the color difference of the coatings is very small, between 0.5 and 0.6, and the coating light transmittance is very good, and the transparent glass plates and PC plates having higher light transmittance than those of comparative example 1, comparative example 2 and the non-deposited coatings, but also have an antireflective effect to some extent.
In addition, as is clear from examples 7 to 10, for the monomer having a higher boiling point, the boiling point of the monomer can be reduced by adding ethanol, and the finally obtained coating also has excellent hydrophilicity, abrasion resistance, small chromatic aberration and excellent light transmittance.
Although the present disclosure is described above, the present disclosure is not limited thereto. Various changes and modifications may be made by one skilled in the art without departing from the spirit and scope of the disclosure, and the scope of the disclosure should be assessed accordingly to that of the appended claims.

Claims (21)

1. An anti-fog coating, characterized in that the anti-fog coating is formed by contacting a substrate with a plasma comprising a monomer of formula (1);
X 2 -R-X 1
(1)
in the formula (1), R is C 1 -C 30 Alkylene or C of (2) 1 -C 30 Substituted alkylene of X 1 And X 2 Each independently selected from hydroxy, amino or carboxyl;
the substituent of the substituted alkylene is hydroxyl, amino or carboxyl;
the C is 1 -C 30 Alkylene or C of (2) 1 -C 30 With or without-NH-'s between the carbon-carbon linkages of the substituted alkylene groups;
and in formula (1), at most one of an amino group and a hydroxyl group is bonded to the same carbon atom.
2. The antifogging coating according to claim 1, wherein the monomer of formula (1) has a structure represented by formula (2),
in the formula (2), R 1 And R is 2 Independently selected from C 1 -C 10 Alkylene or C of (2) 1 -C 10 Substituted alkylene of (a).
3. The antifogging coating according to claim 2, wherein the monomer of formula (1) has a structure represented by formula (3),
in the formula (3), X 3 And X 4 Each independently selected from the group consisting of hydrogen, methyl, hydroxy, hydroxymethyl, amino, and carboxyl; n is n 1 0, 1, 2, 3, 4, 5, 6, 7 or 8; n is n 2 0, 1, 2, 3, 4, 5, 6, 7 or 8.
4. An anti-fog coating according to claim 3, wherein X is 3 And X 4 Are all hydrogen atoms, X 1 And X 2 Are the same groups.
5. The anti-fog coating of claim 1 wherein R is C 1 -C 16 Alkylene or substituted alkylene of (a).
6. The antifogging coating according to claim 5, wherein the monomer of formula (1) has a structure represented by formula (4),
in the formula (4), X 5 And X 6 Each independently selected from the group consisting of hydrogen, methyl, hydroxy, hydroxymethyl, amino, and carboxyl; n is n 3 0, 1, 2, 3, 4, 5, 6, 7 or 8.
7. The anti-fog coating of claim 6, wherein X is 5 And X 6 Are all hydrogen atoms, X 1 And X 2 Are the same groups.
8. The antifogging coating according to claim 1, wherein the monomer of formula (1) is selected from the group consisting of monomers having structures represented by formulas (1-1) to (1-48),
9. the anti-fog coating of claim 1, wherein the substrate is an optical instrument, metal, ceramic, plastic, glass, or electronic device.
10. The anti-fog coating of claim 9, wherein the optical instrument is a lens, mirror, or lens.
11. The anti-fog coating of claim 9, wherein the substrate is a transparent material.
12. The anti-fog coating of claim 1, wherein the anti-fog coating has a light transmittance of greater than 90%.
13. The anti-fog coating of claim 1, wherein the anti-fog coating has a measured water contact angle of 10 ° or less.
14. The anti-fog coating of claim 13, wherein the anti-fog coating has a measured water contact angle of 10 ° or less after being rubbed 500 times with a dust-free cloth under a 1N load.
15. A method of producing an anti-fog coating as claimed in any one of claims 1 to 14, comprising the steps of:
providing a substrate, placing the substrate in a plasma reactor, introducing the monomer vapor of the formula (1) into the plasma reactor, discharging plasma, and polymerizing the plasma on the surface of the substrate to form the anti-fog coating.
16. The method for producing an antifogging coating according to claim 15, wherein the surface of the substrate is pretreated by introducing a plasma source gas and starting a plasma apparatus to continuously discharge before introducing the monomer vapor of formula (1) into the plasma reactor.
17. The method of claim 16, wherein the plasma source gas is one or a mixture of helium, argon, nitrogen, oxygen, and hydrogen.
18. The method of claim 15, wherein the plasma discharge is a pulsed plasma discharge, wherein the pulse power is 10W to 300W, the pulse duty cycle is 20% to 90%, and the discharge time of the pulse output is 30s to 36000s.
19. The method of preparing an anti-fog coating according to claim 15, wherein the monomer of formula (1) is first added to an alcohol solvent to prepare a solution, and then vaporized and passed into a plasma reactor.
20. The method of claim 19, wherein the alcohol is one or more of methanol, ethanol, and propanol.
21. A product, characterized in that at least part of the surface of the product is provided with an anti-fog coating as claimed in any one of claims 1-14.
CN202210319342.4A 2022-03-29 2022-03-29 Antifogging coating, preparation method thereof and product Pending CN116925628A (en)

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