CN110546212A - Antifogging coating composition and antifogging transparent sheet using same - Google Patents
Antifogging coating composition and antifogging transparent sheet using same Download PDFInfo
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- CN110546212A CN110546212A CN201880025639.1A CN201880025639A CN110546212A CN 110546212 A CN110546212 A CN 110546212A CN 201880025639 A CN201880025639 A CN 201880025639A CN 110546212 A CN110546212 A CN 110546212A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
Abstract
Providing an antifogging coating composition comprising: (A) a hydrophilic bisphenol A type (meth) acrylate, (B) a reactive nonionic surfactant, (C) a reactive ionic liquid, and (D) a polymerizable initiator. The antifogging coating composition preferably further comprises (E) pentaerythritol (meth) acrylate and (F) urethane (meth) acrylate resin. The antifogging transparent sheet comprises a transparent substrate and an antifogging coating film which is arranged on the surface of the substrate and is composed of the antifogging coating composition.
Description
Technical Field
The present invention relates to an antifogging coating composition and an antifogging transparent sheet using the same. This application is based on and claims the benefit of priority from japanese patent application No. 2017-123300, filed on 23.6.2017, the entire contents of which are incorporated herein by reference.
Background
When the surface temperature of the substrate is lower than the dew point of the ambient air, water droplets adhere to the surface of the substrate, causing fogging. In transparent substrates such as lenses, glass windows, and transparent films, and reflective materials such as mirrors, blurring of the surface occurs, which impairs the visibility of transmitted images or reflected images. For this reason, a method of forming a coating layer for imparting an antifogging effect on the surface of a substrate to prevent fogging has been proposed. For example, the following methods have been disclosed: an antifogging coating is formed on the surface of a transparent substrate to improve the hydrophilicity of the substrate surface or to reduce the contact angle between the lens and water, thereby preventing the formation of water droplets on the substrate surface and preventing the fogging of the substrate (for example, patent documents 1 and 2).
Documents of the prior art
Patent document
Patent document 1: japanese patent application laid-open No. 2004-83846
Patent document 2: japanese patent application laid-open No. 2007-137937.
disclosure of Invention
Problems to be solved by the invention
Antifogging properties are sought in a wide variety of applications. In particular, antifogging properties are required to be exhibited even in an environment accompanied by a rapid change in temperature. Further, an antifogging coating film is demanded which is excellent not only in initial antifogging property immediately after the formation of the antifogging coating film but also in antifogging durability in which an antifogging effect can be sustained for a long time. For example, an antifogging coating film that sustains antifogging properties even in an environment exposed to water or warm water, and an antifogging transparent sheet provided with such an antifogging coating film have been desired.
Accordingly, an object of the present invention is to provide an antifogging coating composition capable of forming an antifogging coating film excellent not only in initial antifogging property but also in antifogging durability in which an antifogging effect can be sustained for a long time, and an antifogging transparent sheet using the same.
Means for solving the problems
The antifogging coating composition according to the first aspect of the present invention comprises: (A) a hydrophilic bisphenol A type (meth) acrylate, (B) a reactive nonionic surfactant, (C) a reactive ionic liquid, and (D) a polymerizable initiator.
Further, an antifogging transparent sheet according to a second aspect of the present invention includes: a transparent substrate and an antifogging coating film which is arranged on the surface of the substrate and is composed of the antifogging coating composition.
effects of the invention
According to the present invention, an antifogging coating composition capable of forming an antifogging coating film excellent not only in initial antifogging property but also in antifogging persistence that an antifogging effect can be continued for a long time, and an antifogging transparent sheet excellent in antifogging property can be provided.
Detailed Description
[ description of embodiments of the invention of the present application ]
embodiments of the invention of the present application are first listed and described. The invention of the present application relates to an antifogging coating composition comprising: (A) a hydrophilic bisphenol A type (meth) acrylate, (B) a reactive nonionic surfactant, (C) a reactive ionic liquid, and (D) a polymerizable initiator.
The antifogging coating composition containing (A) hydrophilic bisphenol A type (methyl) acrylate, (B) reactive nonionic surfactant and (C) reactive ionic liquid has excellent initial antifogging property immediately after an antifogging coating is formed. Among them, the antifogging property (low-temperature antifogging property) is exhibited particularly in a low-temperature environment. In addition, such an antifogging coating composition has an effect of sustaining the hydrophilicity of the surface of the substrate after the antifogging coating film is formed. By imparting such a hydrophilic property (hydrophilicity sustainability) to the base material, an antifogging coating film having excellent antifogging sustainability can be formed.
Further, (B) the reactive nonionic surfactant and (C) the reactive ionic liquid also have an effect of reducing the contact angle of the substrate surface. The antifogging effect is further improved by reducing the contact angle of the substrate surface. Further, by containing the polymerizable initiator (D), an antifogging coating having a large molecular weight and excellent retention on the surface of the substrate can be provided. As a result, an antifogging coating film having an excellent antifogging durability, in which an antifogging effect can be sustained for a long time, can be formed.
By containing the components (a) to (D) in this manner, an antifogging coating composition capable of forming an antifogging coating film excellent in initial antifogging property and also excellent in antifogging durability with which an antifogging effect can be sustained for a long time can be provided.
In the above antifogging coating composition, (C) the reactive ionic liquid may be a liquid composed of a sulfonic acid ammonium salt. By containing such a reactive ionic liquid, an antifogging coating film excellent not only in initial antifogging property but also in antifogging persistence property in which an antifogging effect can be sustained for a long time can be more reliably obtained.
The antifogging coating composition described above may further comprise (E) pentaerythritol (meth) acrylate. By containing the component (E), the water-washing resistance of the antifogging coating film described later can be improved, and softness can be imparted to the antifogging coating film.
The antifogging coating composition may further comprise (F) a urethane (meth) acrylate resin. By containing the component (F), the water-washing resistance of the antifogging coating film described later can be improved, and softness can be imparted to the antifogging coating film.
In the antifogging coating composition, the content of the (B) component may be more than 2 parts by mass and 20 parts by mass or less with respect to 100 parts by mass of the (a) component. When the content of the component (B) is more than 2 parts by mass per 100 parts by mass of the component (a), an antifogging coating composition capable of forming an antifogging coating film having high coating film transparency more stably can be obtained. Even if the content of the component (B) exceeds 20 parts by mass per 100 parts by mass of the component (a), the effect is saturated, and therefore the transparency and the antifogging property are not improved any more, and the cost is increased. Therefore, the content of the component (B) is preferably 20 parts by mass or less with respect to 100 parts by mass of the component (a).
In the antifogging coating composition, the content of the component (C) may be 1 part by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the component (a). If the content of component (C) is 1 part by mass or more, the effect of improving the antifogging property by component (C) can be more clearly exhibited. Even if the content of the component (C) exceeds 5 parts by mass per 100 parts by mass of the component (a), the effect is saturated, and thus the transparency and the antifogging property are not improved any more, and the cost is increased. Therefore, the content of the component (C) is preferably 5 parts by mass or less with respect to 100 parts by mass of the component (a).
(B) The content ratio of the component (B)/(C) to the component (C) may be 1 to 10. By setting the ratio (B)/(C) to 1 or more, an antifogging coating film having more excellent antifogging properties can be provided. Even if the ratio exceeds 10, the effect is saturated and the transparency and the antifogging property are not changed any more, so the upper limit is preferably 10.
The antifogging coating composition may further contain a leveling agent. The leveling agent is contained, whereby the coatability of the antifogging coating composition can be improved. Further, the contact angle between the substrate and water can be reduced, and water droplets are less likely to be generated. Thus contributing to an improvement in the antifogging effect.
In the above antifogging coating composition, the polymerizable initiator may be a photopolymerization initiator. By using a polymerizable initiator as a photopolymerization initiator, curing after application of the antifogging coating composition can be relatively easily performed.
The antifogging transparent sheet according to the present invention comprises: a transparent substrate and an antifogging coating film which is arranged on the surface of the substrate and is composed of the antifogging coating composition. The antifogging transparent sheet provided with the antifogging coating film formed by the antifogging coating composition has excellent transparency and antifogging property.
The substrate may be a substrate made of polyethylene terephthalate. Since polyethylene terephthalate has excellent transparency, an antifogging transparent sheet having high transparency as a whole can be obtained. Further, since polyethylene terephthalate is excellent in processability, an antifogging transparent sheet applicable to various uses can be obtained.
[ detailed description of embodiments of the invention of the present application ]
Next, an embodiment of the antifogging coating composition of the present invention will be described. The antifogging coating composition according to the present embodiment contains: (A) a hydrophilic bisphenol a type (meth) acrylate (also referred to as "component (a)" in the specification and claims of the present application), (B) a reactive nonionic surfactant (also referred to as "component (B)" in the specification and claims of the present application), (C) a reactive ionic liquid (also referred to as "component (C)" in the specification and claims of the present application), and (D) a polymerizable initiator (also referred to as "component (D)" in the specification and claims of the present application). In the present specification, "(meth) acrylate" means either one or both of acrylate and methacrylate.
[ (A) hydrophilic bisphenol A type (meth) acrylate ]
The antifogging coating composition of the present invention contains a hydrophilic bisphenol a type (meth) acrylate as the (a) component. The hydrophilic bisphenol a type (meth) acrylate is a main component of the antifogging coating composition, imparts hydrophilicity to a substrate coated with the antifogging coating composition, and contributes to improvement of an antifogging effect. Further, the antifogging coating composition containing a hydrophilic bisphenol a type (meth) acrylate and an ionic liquid containing an antifogging coating film formed from the antifogging coating composition is excellent in low-temperature antifogging property and hydrophilic durability in particular immediately after the formation of the antifogging coating film. By "hydrophilic" is meant a resin that does not phase separate when added to water and that is dispersible or soluble in water.
The hydrophilic bisphenol a-type (meth) acrylate has a structure in which two hydroxyl groups of bisphenol a are substituted with a reactive group having a (meth) acrylate group. Examples of the hydrophilic bisphenol a-type (meth) acrylate include compounds having a structure represented by the following general formula (1).
[ solution 1]
(wherein R1 and R2 each independently represents a hydrogen atom or a methyl group, m and n each independently represents an integer of 0 or more, and m + n has a value of 0 or more, preferably 4 or more, more preferably 10 or more.)
As shown by the above formula (1), in the present specification, the hydrophilic bisphenol A type (meth) acrylate preferably contains an alkylene oxide-modified bisphenol A type (meth) acrylate. Examples of the alkylene oxide-modified bisphenol a-type (meth) acrylate include ethylene oxide-modified bisphenol a-type (meth) acrylate and propylene oxide-modified bisphenol a-type (meth) acrylate. In the formula (1), the larger the value of m + n, the higher the hydrophilicity of the hydrophilic bisphenol A type (meth) acrylate. As described above, the value of m + n is preferably 4 or more, more preferably 10 or more. Preferable examples of such a compound include a compound represented by the following formula (2).
[ solution 2]
(wherein m and n each independently represent an integer of 0 or more, for example, m + n is 20.)
Examples of commercially available hydrophilic bisphenol a type (meth) acrylates include New Frontier (R) BPE-4 (in formula (1), R1 and R2 are hydrogen atoms, and m + n ═ 4), New Frontier (R) BPE-10 (in formula (1), R1 and R2 are hydrogen atoms, and m + n ═ 10), New Frontier (R) BPE-20 (in formula (1), R1 and R2 are hydrogen atoms, and m + n ═ 20), and New Frontier (R) BPEM-4 (in formula (1), R1 and R2 are methyl groups, and m + n ═ 4), New Frontier (R) BPEM-10 (in formula (1), R1 and R2 are methyl groups, and n ═ 4), and New Frontier (R) BPEM-10 (in formula (1), and R1 and R2 are methyl groups).
The proportion of the hydrophilic bisphenol a-type (meth) acrylate to 100% by mass of the total solid content of the antifogging coating composition is preferably 50% by mass or more, and more preferably 60% by mass or more in terms of solid content. An antifogging coating composition capable of forming an antifogging coating film having excellent antifogging properties, particularly low-temperature antifogging properties and hydrophilic durability can be obtained by containing 50 mass% or more of hydrophilic bisphenol A type (meth) acrylate in terms of solid content. The upper limit of the above proportion is not particularly limited, but is, for example, 90% by mass in terms of solid content.
[ (B) reactive nonionic surfactant ]
The antifogging coating composition of the present invention contains a reactive nonionic surfactant as the (B) component. The reactive nonionic surfactant mainly contributes to improvement of low-temperature antifogging property of the antifogging coating film, improvement of hydrophilic persistence and reduction of contact angle.
The nonionic surfactant (nonionic surfactant) is a surfactant having a hydrophilic group which is not ionized in a state of being dissolved in water. Among them, the "reactive nonionic surfactant" is a nonionic surfactant having a reactive functional group in a molecule. Examples of the reactive functional group include unsaturated bond-containing groups such as a vinyl group and a (meth) acryloyl group, and particularly ethylenically unsaturated bond-containing groups.
Examples of the reactive nonionic surfactant contained in the antifogging coating composition of the present application include compounds having a structure represented by the following formula (3).
[ solution 3]
(wherein R3 represents a monovalent branched aliphatic hydrocarbon group or branched aliphatic acyl group having 8 to 36 carbon atoms and 3 or more methyl groups, AO represents an oxyalkylene group having 2 to 4 carbon atoms, L represents a group represented by the following formula (4), z represents a number of 1 to 10, X represents a hydrogen atom or an anionic hydrophilic group or a cationic hydrophilic group (preferably a hydrogen atom) described below, m represents a number of 0 to 1000, and n represents a number of 0 to 1000.)
[ solution 4]
(wherein R4 and R5 each represents a hydrogen atom or a methyl group, x represents a number of 0 to 12, and y represents a number of 0 or 1.)
Anionic hydrophilic group: -SO3M, -R6-SO3M, -R7-COOM, -PO3M2, -PO3MH or-CO-R8-COOM (wherein M represents a hydrogen atom, an alkali metal atom, an alkaline earth metal atom or ammonium (wherein the alkaline earth metal atom is 1/2), R6 and R7 represent an alkylene group, and R8 represents a residue obtained by removing a carboxyl group from a dibasic acid or an anhydride thereof.)
cationic hydrophilic group: -R9-NR10R11R 12. Y or-Z-NR 10R11R 12. Y (wherein R9 represents an alkylene group, R10 to R12 represent an alkyl group having 1 to 4 carbon atoms, an alkanol group having 2 to 4 carbon atoms or a benzyl group, Y represents a halogen atom or a methylsulfate group, and Z represents a group represented by-CH 2CH (OH) CH 2-or-CH (CH2OH) CH 2-)
The L is preferably a group having a structure represented by the following formula (5).
[ solution 5]
-CH-CH＝CH (5)
Specific examples of the compound having a structure represented by the above formula (3) include compounds having a structure represented by the following formula (6).
[ solution 6]
(wherein EO is ethylene oxide, and m is a number of 0 to 1000.)
Typically, m in formula (6) is an integer of 5 to 50, for example, 10, 20, 30, or 40.
Examples of commercially available nonionic surfactants that are compounds having a structure represented by formula (3) include Adekarea Soap ER-10, Adekarea Soap ER-20, Adekarea Soap ER-30, Adekarea Soap ER-40, Adekarea Soap SR series, and Adekarea Soap SE series (both manufactured by ADEKA Co., Ltd.).
The content of the component (B) is preferably more than 2 parts by mass and 20 parts by mass or less with respect to 100 parts by mass of the component (a). By containing the component (B) in an amount of more than 2 parts by mass per 100 parts by mass of the component (a), an antifogging coating having a high coating transparency can be formed more stably. Even if the content of the component (B) exceeds 20 parts by mass per 100 parts by mass of the component (a), the effect is saturated, and therefore, the transparency and the antifogging property are not improved any more, and the cost is increased. Therefore, the content of the component (B) is preferably 20 parts by mass or less with respect to 100 parts by mass of the component (a). The upper limit of the content of the component (B) is more preferably 18 parts by mass with respect to 100 parts by mass of the component (a).
[ (C) reactive Ionic liquids ]
the antifogging coating composition of the present invention contains a reactive ionic liquid as the (C) component. An ionic liquid is a substance in which ions composed of cations and anions exist as a liquid. The ionic liquid is a salt, and is a substance having a low melting point and being in a liquid state at around room temperature. Further, the "reactive ionic liquid" is a substance containing a cation having a reactive functional group. Examples of the reactive functional group include unsaturated bond-containing groups such as a vinyl group and a (meth) acryloyl group, and particularly ethylenically unsaturated bond-containing groups.
Examples of the reactive ionic liquid of the component (C) include reactive ionic liquids containing ion-binding salts having a reactive group represented by the following chemical formula (7) or the following chemical formula (8).
[ solution 7]
[ solution 8]
(wherein R13 and R14 each independently represents a substituted or unsubstituted, linear, branched or cyclic alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted, aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted, aralkyl group having 7 to 31 carbon atoms; A1 and A2 each represent a linear or branched alkylene group having 2 to 4 carbon atoms; n is an integer of 0 to 50; Q1+ and Q2+ each independently represents a substituent selected from the group consisting of an ammonium ion having an ethylenically unsaturated bond, an imidazolium ion having an ethylenically unsaturated bond, a pyridinium ion having an ethylenically unsaturated bond, a pyrrolidinium ion having an ethylenically unsaturated bond, a pyrroline ion having an ethylenically unsaturated bond, a piperidinium ion having an ethylenically unsaturated bond, a pyrazinium ion having an ethylenically unsaturated bond, a pyrimidinium ion having an ethylenically unsaturated bond, a pyrrolidinium ion having an ethylenically unsaturated bond, and a pharmaceutically acceptable salt thereof, At least one member selected from the group consisting of a triazolium ion having an ethylenically unsaturated bond, a triazinium ion having an ethylenically unsaturated bond, a quinolinium ion having an ethylenically unsaturated bond, an isoquinolinium ion having an ethylenically unsaturated bond, an indolium ion having an ethylenically unsaturated bond, a quinoxalinium ion having an ethylenically unsaturated bond, a piperazinium ion having an ethylenically unsaturated bond, an oxazolinium ion having an ethylenically unsaturated bond, a thiazolinium ion having an ethylenically unsaturated bond, and a morpholinium ion having an ethylenically unsaturated bond. )
The content of the component (C) is preferably 1 to 5 parts by mass with respect to 100 parts by mass of the component (a). By containing the component (C) in an amount of 1 part by mass or more per 100 parts by mass of the component (a), the antifogging coating film obtained has a sufficient level of antifogging property and hydrophilic durability. Even if the content of the component (C) exceeds 5 parts by mass per 100 parts by mass of the component (a), the effect is saturated, and thus the transparency and the antifogging property are not improved any more, and the cost is increased. Therefore, the content of the component (C) is preferably 5 parts by mass or less with respect to 100 parts by mass of the component (a). The lower limit of the content of the component (C) is more preferably 1.5 parts by mass with respect to 100 parts by mass of the component (a). The upper limit is more preferably 3 parts by mass.
(B) The content ratio of component (B)/(C) to component (C) is preferably 1 to 10. By setting the content of the component (B) to 1 or more in terms of a mass ratio with respect to the content of the component (C), an antifogging coating composition capable of forming an antifogging coating film excellent in antifogging properties, particularly low-temperature antifogging properties and hydrophilic durability can be obtained more reliably. Even if the mass ratio (B)/(C) exceeds 10, the effect is saturated and the transparency and antifogging property are not changed any more, so that the upper limit is preferably 10.
[ (D) polymerization initiator ]
The antifogging coating composition according to the present embodiment contains a polymerization initiator as the component (D). Examples of the polymerization initiator include thermal polymerization initiators and photopolymerization initiators. Among them, a photopolymerization initiator is preferable because curing after coating with the antifogging coating composition can be easily performed. Further, as the photopolymerization initiator, a photopolymerization initiator curable by ultraviolet rays is preferable. The polymerization initiator may be used alone or in combination of two or more.
The amount of the polymerization initiator can be appropriately set as needed. For example, the amount of the polymerization initiator of the component (D) is preferably set to be in the range of 1 to 50 parts by mass, preferably 5 to 30 parts by mass, relative to 100 parts by mass of the hydrophilic bisphenol a-type (meth) acrylate of the component (a).
[ (E) pentaerythritol (meth) acrylate ]
The antifogging coating composition may contain (E) pentaerythritol (meth) acrylate in addition to the above-mentioned (a) to (D) components.
(E) The pentaerythritol (meth) acrylate of the component contributes to a reduction in the contact angle of the surface of the antifogging coating film. By the synergistic effect of the components (B) and (C), the antifogging property after water is wiped off when the surface of the antifogging coating film is cleaned with hot water and then wiped with a cloth can be improved. Further, the component (E) contributes to improvement of curing reactivity and surface hardness.
Examples of the pentaerythritol (meth) acrylate as the component (E) include pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, hexanediol (meth) acrylate, and the like. Further, the pentaerythritol (meth) acrylate as the component (E) is preferably an alkylene oxide-modified pentaerythritol (meth) acrylate because hydrophilicity can be imparted.
Examples of commercially available (E) pentaerythritol (meth) acrylate include KAYARAD DPHA (a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate), KAYARAD DPEA12 (ethylene oxide-modified dipentaerythritol hexaacrylate), KAYARAD-330 (dipentaerythritol triacrylate), KAYARAD-320 (dipentaerythritol tetraacrylate), and KAYARAD-310 (dipentaerythritol pentaacrylate) (both available from Nippon chemical Co., Ltd.). Of these, KAYARAD DPEA12 modified with alkylene oxide (ethylene oxide-modified dipentaerythritol hexaacrylate) is preferable.
The content of the (E) component is preferably 5 parts by mass or more, and more preferably 10 parts by mass or more, relative to 100 parts by mass of the hydrophilic bisphenol a-type (meth) acrylate of the (a) component. When the component (E) is contained in an amount of 5 parts by mass or more per 100 parts by mass of the hydrophilic bisphenol a-type (meth) acrylate as the component (a), the contact angle can be further reduced, the antifogging property after wiping off water can be improved, and the anti-fog film can be provided with softness. The upper limit is not particularly limited, and is, for example, 30 parts by mass.
[ (F) urethane acrylate resin ]
The antifogging coating composition may further contain a urethane (meth) acrylate resin of the component (F). The urethane acrylate resin can improve the curing reactivity of the antifogging coating composition.
As the urethane (meth) acrylate-based resin, a reaction product of a polyol compound and an organic polyisocyanate is exemplified.
Examples of the polyol compound include polyols such as ethylene glycol, propylene glycol, neopentyl glycol, 1, 6-hexanediol, 3-methyl-1, 5-pentanediol, 1, 9-nonanediol, 2-ethyl-2-butyl-1, 3-propanediol, trimethylolpropane, diethylene glycol, dipropylene glycol, polypropylene glycol, 1, 4-dimethylolcyclohexane, bisphenol a polyethoxy glycol, and polytetramethylene glycol; polyester polyols which are reaction products of the above polyols with polybasic acids such as succinic acid, maleic acid, itaconic acid, adipic acid, hydrogenated dibasic acid, phthalic acid, isophthalic acid, terephthalic acid, and the like, or anhydrides thereof; polycaprolactone polyols as the reaction product of the above polyols with epsilon-caprolactone; a reaction product of the polyhydric alcohol and epsilon-caprolactone derived from the polybasic acid or anhydride thereof; a polycarbonate polyol; polymer polyols, and the like.
Examples of the organic polyisocyanate include tolylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, diphenylmethane-4, 4 ' -diisocyanate, dicyclopentyl diisocyanate, hexamethylene diisocyanate, 2,4,4 ' -trimethylhexamethylene diisocyanate, and 2,2 ' -4-trimethylhexamethylene diisocyanate.
The urethane (meth) acrylate resin preferably contains a urethane (meth) acrylate oligomer. The weight average molecular weight of the urethane (meth) acrylate oligomer is preferably 300 to 5000, and more preferably 300 to 3000.
As commercially available urethane (meth) acrylate resins as the component (F), art resins (Artressin) series (available from Kokusan Kogyo Co., Ltd.) can be mentioned.
The content of the (F) component is preferably 2 parts by mass or more, and more preferably 3 parts by mass or more, relative to 100 parts by mass of the hydrophilic bisphenol a-type (meth) acrylate of the (a) component. By containing the component (F) in an amount of 2 parts by mass or more per 100 parts by mass of the hydrophilic bisphenol a-type (meth) acrylate as the component (a), it is possible to contribute greatly to imparting the scratch resistance (hard coat property) to the antifogging coating film and to improving the reactivity of the antifogging coating composition. The upper limit is not particularly limited, and is, for example, 10 parts by mass. Further, the component (F) is more preferably used in combination with the component (E).
[ leveling agent ]
The antifogging coating composition according to the present embodiment may further contain other additive components within a range not to impair the effects of the present invention. For example, the antifogging coating composition according to the present embodiment may further contain a leveling agent. The leveling agent is contained, whereby the coatability of the antifogging coating composition can be improved. Further, the contact angle between the antifogging coating and water can be reduced, and water droplets are less likely to be generated. Thus contributing to an improvement in the antifogging effect.
Examples of the leveling agent include silicon leveling agents, fluorine leveling agents, acrylic leveling agents, ethylene leveling agents, and fluorine and acrylic composite leveling agents. The leveling agent may be used alone or in combination of two or more.
The amount of the leveling agent may be appropriately set as needed. For example, the amount of the leveling agent is suitably set to be in the range of 1 to 50 parts by mass, preferably 5 to 30 parts by mass, relative to 100 parts by mass of the hydrophilic bisphenol a-type (meth) acrylate of the component (a).
[ compatibilizing agent ]
The antifogging coating composition may contain a compatibilizing agent as needed. The compatibilizer may be appropriately selected depending on the compatibility of the components. Examples of the compatibilizing agent include aliphatic (meth) acrylates, alicyclic (meth) acrylates, and aromatic (meth) acrylates. The aliphatic (meth) acrylate, the alicyclic (meth) acrylate, and the aromatic (meth) acrylate may contain a functional group such as a hydroxyl group, an amino group, a glycidyl group, a carboxylic acid group (carboxyl group), or a phosphate group, or a modifying group such as a polyethylene glycol chain. As commercially available compatibilizers, Light-Ester series, Light-Acrylate series (both of them are available from Kyoeisha chemical Co., Ltd.) and the like can be cited. The amount of the compatibilizing agent may be appropriately adjusted in consideration of the solubility of each component.
[ solvent ]
The antifogging coating composition according to the present embodiment may contain a solvent as necessary. Examples of the solvent include ketone solvents such as methyl ethyl ketone and acetone; an ester solvent; glycol ether solvents such as PGM (propylene glycol monomethyl ether); organic solvents such as alcohol solvents, and water. These solvents may be appropriately selected in consideration of the solubility of the added component.
The ratio of the solvent of the antifogging coating composition is set in consideration of the solubility of each component, the coating property of the composition, and the like. In particular, when the amount of the solvent is too large, curing of the coating film tends to be insufficient. When the amount of the solvent is too small, the transparency of the antifogging coating film tends to be lowered. The proportion of the solvent in the antifogging coating composition is not particularly limited, and is typically 50 mass% or more and 80 mass% or less, preferably 50 mass% or more and 70 mass% or less, and more preferably 55 mass% or more and 65 mass% or less of the total amount of the antifogging coating composition.
[ other additional Components ]
Furthermore, the antifogging coating composition according to the present embodiment may further contain known additives such as a film forming aid, a foam inhibitor, a stabilizer, a filler, an adhesion promoter, a curing agent, a curing promoter, a plasticizer, a thixotropic agent, a pigment, an antioxidant and the like in addition to the above components according to desired characteristics.
[ anti-fog coating composition ]
The antifogging coating composition according to the present embodiment may be prepared by: to a solvent such as Methyl Ethyl Ketone (MEK) are added (a) hydrophilic bisphenol a type (meth) acrylate, (B) a reactive nonionic surfactant, (C) a reactive ionic liquid, (D) a polymerization initiator, (E) ethylene oxide-modified dipentaerythritol hexaacrylate if necessary, (F) a urethane (meth) acrylate resin, a leveling agent, and other necessary components, and the mixture is put into a stirrer and stirred. The order of addition of the components is not particularly limited, and can be arbitrarily adjusted by those skilled in the art in accordance with the general knowledge of the art.
In the present embodiment, a preferable antifogging coating composition contains, per 100 parts by mass of (a) a hydrophilic bisphenol a type (meth) acrylate: 1 to 20 parts by mass, preferably 1.5 to 18 parts by mass of (B) a reactive nonionic surfactant; 1 to 5 parts by mass, preferably 1.5 to 3 parts by mass, of (C) a reactive ionic liquid; and 1 to 50 parts by mass, preferably 5 to 30 parts by mass of (D) a polymerizable initiator. (B) The content ratio of component (B) to component (C), (B)/(C), is more preferably 1 to 10.
In the present embodiment, another preferable antifogging coating composition contains, per 100 parts by mass of (a) a hydrophilic bisphenol a type (meth) acrylate: 1 part by mass or more, preferably 1.5 parts by mass or more and 18 parts by mass or less of (B) a reactive nonionic surfactant; 1 to 5 parts by mass, preferably 1.5 to 3 parts by mass, of (C) a reactive ionic liquid; 1 to 50 parts by mass, preferably 5 to 30 parts by mass of (D) a polymerizable initiator; 5 parts by mass or more, more preferably 10 parts by mass or more and 30 parts by mass or less of (E) an ethylene oxide-modified dipentaerythritol hexaacrylate; and 2 parts by mass or more, more preferably 3 parts by mass or more and 10 parts by mass or less of (F) a urethane (meth) acrylate resin. (B) The content ratio of component (B) to component (C), (B)/(C), is more preferably 1 to 10.
[ antifogging transparent sheet ]
Next, the antifogging transparent sheet according to the present embodiment will be described. The antifogging transparent sheet of the present embodiment includes: a transparent substrate and an antifogging coating film which is arranged on the surface of the substrate and is composed of the antifogging coating composition.
The antifogging transparent antifogging coating can be formed by coating the coating composition on a substrate and drying the coating film. When the antifogging coating composition contains a photopolymerization initiator, curing of each component can be promoted by irradiation with light such as ultraviolet rays after coating, and an antifogging coating film can be formed.
The substrate is preferably a transparent substrate such as a glass or resin (plastic) sheet or film. Examples of the transparent substrate include a transparent sheet or a transparent film made of a resin selected from transparent resins such as polyethylene terephthalate (PET), polycarbonate, and poly (meth) acrylate.
Further, the antifogging coating has excellent high-temperature antifogging property and low-temperature antifogging property. Therefore, the antifogging effect can be exerted in a wide range of temperature environment. Further, since the film is also excellent in transparency, it can be used as a film which does not impair the appearance of the base material and the visibility of an external image transmitted through the base material.
[ use ]
The anti-fogging coating agent according to the present embodiment can exhibit an anti-fogging effect in a wide temperature range environment, and is excellent in the durability of the anti-fogging effect and the transparency of the coating film. Therefore, an antifogging coating film having high adhesion to plastic molded articles, plastic films, and particularly to PET-made materials can be formed.
Further, the antifogging transparent sheet having an antifogging coating film composed of the antifogging coating agent can be used as an antifogging material having a base material such as an inorganic glass lens, a window of a building, a window of a bathroom, a mirror, a window of a vehicle such as an automobile, a train, an airplane, or a ship, a goggle for skiing, swimming, or the like, a visor for a face mask, a motorcycle helmet, or the like.
Examples
The present invention will be described more specifically with reference to examples. The scope of the present invention is not limited to the description of these examples.
the components to be blended in the following examples and comparative examples are as follows.
(A) Hydrophilic bisphenol A type (meth) acrylate (trade name New Frontier BPE20G, first Industrial pharmaceutical Co., Ltd.)
(B) Reactive nonionic surfactant (trade name Adekarea Soap ER10, manufactured by ADEKA K.K.)
(C) Reactive ionic liquid (trade name JI62C01, manufactured by Nippon emulsifier Co., Ltd.)
(D) Polymerization initiator (trade name DAROCUR (R)) 4265 (a mixture of 50 mass% of 2,4, 6-trimethylbenzoyldiphenylphosphine oxide and 50 mass% of 2-hydroxy-2-methyl-1-phenyl-1-propanone, manufactured by BASF JAPAN Co., Ltd.)
(E) Pentaerythritol (meth) acrylate
Ethylene Oxide (EO) -modified dipentaerythritol hexaacrylate (KAYARAD DPEA12, manufactured by japan chemicals).
(F) Urethane (meth) acrylic resin
Urethane acrylate oligomer, reactive urethane polymer mixture (trade name Artressin H135, available from Kokusan Kogyo Co., Ltd.)
-a compatibilising agent
2-hydroxyethyl methacrylate (trade name Light-Ester HO250N, product of Kyoeisha chemical Co., Ltd.)
-a solvent
MEK (methyl ethyl ketone)
-leveling agent A
BYK3560 (polyether macromonomer (macromonomer) -modified acrylate, BYK Chemie JAPAN K)
-leveling agent B
DOW CORNING (R)67 ADDITIVE (3- (polyoxyethylene) propylheptamethyltrisiloxane having a solid content of 70 to 80 mass%, manufactured by Torredo Corning Co., Ltd.)
[ preparation of antifogging coating composition and formation of antifogging coating film ]
Predetermined amounts of the above-mentioned respective components were put into a kneader in accordance with the compounding shown in tables 1 to 2, and kneaded to obtain an antifogging coating composition. The obtained antifogging coating composition was applied to a transparent polyethylene terephthalate (PET) sheet as a substrate so that the film thickness after drying was approximately 10 μm, and was dried by heating at 80 ℃ for 10 minutes to form a coating film. The coating film formed at a position of 12cm under a light source was irradiated with ultraviolet rays at a cumulative light amount of 1000mJ/cm2 using a high-pressure mercury lamp having an output density of 120W/cm to cure the coating film, thereby forming an antifogging coating film. The formulation shown in table 2 is different from the formulation shown in table 1 in that it further contains (E) pentaerythritol (meth) acrylate and (F) urethane (meth) acrylate resin.
[ evaluation of antifogging coating film ]
The sheet having the antifogging coating film formed thereon was evaluated according to the following evaluation items. The evaluation items and the evaluation procedure are as follows.
(1) Transparency of coating film
The sheet having the antifogging coating film formed thereon was evaluated for transparency by visual observation. In the evaluation, the transparency and the presence or absence of haze were visually observed. In tables 1 and 2, the transparent coating is denoted by "+" and the hazy coating is denoted by "-".
(2) evaluation of antifogging Properties
(2-1) evaluation of antifogging Properties under ordinary conditions
A container with the top open is prepared, and warm water of 50 ℃ to 60 ℃ is poured. A composite sheet to be evaluated was prepared, and the open surface of the container was covered with the composite sheet with the antifogging coating film side facing downward. In this case, the distance between the surface of the antifogging coating and the surface of the warm water is 100 mm. + -.5 mm. The film was left standing, and the change in the film surface after 2 minutes was visually observed. In tables 1 and 2, the composite sheet was entirely transparent as a result of visual observation, and the exterior on the opposite side of the sheet was visible through the sheet and indicated by "+"; the sheet was blurred and the exterior scene on the opposite side of the sheet was not visible through the sheet and was identified as "-".
(2-2) evaluation of Low-temperature antifogging Property
The composite sheet to be evaluated was left at-15 ℃ for 10 minutes and then taken out to an environment of 20 ℃. + -. 5 at room temperature. The surface of the antifogging coating was observed to be blurred after 60 seconds from the room temperature environment. In tables 1 and 2, the composite sheet was entirely transparent as a result of visual observation, and the exterior on the opposite side of the sheet was visible through the sheet and indicated by "+"; the sheet was blurred and the exterior scene on the opposite side of the sheet was not visible through the sheet and was identified as "-".
(2-3) evaluation of high-temperature antifogging Property
(i) Standard of merit
A container with the upper side open was prepared, and warm water of 80. + -. 5 ℃ was poured. A composite sheet to be evaluated was prepared, and the open surface of the container was covered with the composite sheet with the antifogging coating film side facing downward. In this case, the distance between the surface of the antifogging coating and the surface of the warm water is 100 mm. + -.5 mm. The film was left standing and observed for changes in the film surface after 2 minutes. In tables 1 and 2, the composite sheet was transparent as a whole and the mark of the external view on the opposite side of the sheet was "+" when observed visually, and the mark of the external view on the opposite side of the sheet was "-" when the sheet was blurred and invisible (the same applies to (ii) and (iii) below).
(ii) Evaluation of high-temperature antifogging Property in Water resistance test 1
The composite sheet to be evaluated was immersed in room-temperature water at 20 to 30 ℃ and allowed to stand for 2 hours. The sheet was taken out from the room temperature water and dried. After drying, the sheet was evaluated for high-temperature antifogging property in the order shown in "(i) standard" above.
(iii) Evaluation of high-temperature antifogging Property in Water resistance test 2
The composite sheet to be evaluated was immersed in warm water at 75 to 85 ℃ and allowed to stand for 2 hours. The sheet was taken out of the warm water and dried. After drying, the sheet was evaluated for high-temperature antifogging property in the order shown in "(i) standard" above.
The formulations of comparative examples 1 and 2 and examples 1 to 14, and the evaluation results of the coating transparency and antifogging property are shown in tables 1 and 2. The numbers shown in the column of blending indicate parts by mass.
TABLE 1
B 1) is a permissible range, but is somewhat blurred
TABLE 2
As shown in the evaluation results of table 1, in comparative example 1 in which neither of (B) the reactive nonionic surfactant and (C) the reactive ionic liquid was contained, the coating transparency was evaluated as transparent, but as shown in the evaluation results of the antifogging property, the antifogging effect was hardly seen.
Further, in comparative example 2 in which (C) a reactive ionic liquid and a compatibilizing agent for promoting the compatibility of the respective components were further contained in comparison with the compounding of comparative example 1, the antifogging effect was hardly seen.
On the other hand, in examples 1 to 14 containing both (B) a reactive nonionic surfactant and (C) a reactive ionic liquid, good antifogging properties were exhibited for the evaluation of each antifogging property.
In examples 1 to 14, in example 1 (example in which the amount of (B) the reactive nonionic surfactant is 2 parts by mass relative to 100 parts by mass of (a) the hydrophilic bisphenol a type (meth) acrylate), the haze of the coating film was observed to some extent in the evaluation of the transparency of the coating film. In the other examples (examples 2 to 14), all the coating films were transparent. When the amount of the (B) reactive nonionic surfactant is 2 parts by mass as described above, an antifogging coating film having insufficient coating film transparency may be obtained. From these results, it is found that in order to exhibit high antifogging property and to form an antifogging coating film having a high film transparency more stably, the amount of the (B) reactive nonionic surfactant is preferably more than 2 parts by mass, more preferably 4 parts by mass or more, per 100 parts by mass of the (a) hydrophilic bisphenol a type (meth) acrylate.
As described above, it is found that the antifogging coating film obtained from the antifogging coating composition of the present invention and the antifogging transparent sheet provided with the antifogging coating film have excellent antifogging properties (antifogging properties at all of normal temperature, low temperature, and high temperature). Further, when the amount of the reactive nonionic surfactant (B) exceeds 2 parts by mass, an antifogging coating film having a high coating film transparency can be formed more stably.
(3) Evaluation of Wash resistance
a composite sheet to be evaluated was prepared, and the surface of the antifogging coating film was washed 10 times with hands in warm water at 30 to 40 ℃ while rubbing, and then the sheet was dried by wiping off moisture with a cloth. Next, a container with the top open is prepared, and warm water of 50 ℃ to 60 ℃ is poured. The dried sheet was prepared, and the open surface of the container was covered with the composite sheet with the antifogging coating film side facing downward. In this case, the distance between the surface of the antifogging coating and the surface of the warm water is 100 mm. + -.5 mm. The film was left standing, and the change in the film surface after 2 minutes was visually observed. Antifogging properties were evaluated in 4 stages (level a → B → C → D) in order of less blur. Levels a to C are allowed levels. Level D is a level at which the sheet cannot withstand practical use because the sheet is opaque due to blurring. The evaluation results are shown in tables 3 and 4. The formulation shown in Table 3 is the same as in Table 1. The formulation shown in table 4 is the same as table 2.
TABLE 3
TABLE 4
As shown in the evaluation results in table 3, in comparative example 1 in which neither (B) a reactive nonionic surfactant nor (C) a reactive ionic liquid was contained, or comparative example 2 in which (B) a reactive nonionic surfactant was not contained, the water washability was not sufficient in the D-class. In contrast, in examples 1 to 7 containing both (B) a reactive nonionic surfactant and (C) a reactive ionic liquid, the wash resistance was improved to a C to B class.
As shown in table 4, the water washing resistance was improved by further including (E) pentaerythritol (meth) acrylate and (F) urethane (meth) acrylate resin. In particular, the composition comprises, based on 100 parts by mass of (A) a hydrophilic bisphenol A type (meth) acrylate: the excellent washing resistance of class a was shown when (B) the reactive nonionic surfactant was 6 to 10 parts by mass, 2 parts by mass of (C) the reactive ionic liquid, 8 parts by mass of (D) the polymerizable initiator, 10 parts by mass of (E) the pentaerythritol (meth) acrylate, and 4 parts by mass of (F) the urethane (meth) acrylate resin (examples 10 to 12). That is, it is clear that, in addition to the components (a) to (D), it is preferable to further contain the components (E) and (F) in order to improve the wash-out resistance.
(4) Hardness of antifogging coating
With respect to the antifogging coating compositions of examples 8 to 14 containing the above-mentioned component (E) and component (F), the surface hardness of the antifogging coating film further formed from the antifogging coating composition was evaluated. For evaluation, the pencil hardness of the antifogging coating surface was measured. The results are shown in table 5.
TABLE 5
As shown in table 5, when the amount of the reactive nonionic surfactant (B) was increased in a state where the components (E) and (F) were contained, the surface of the antifogging coating film was gradually softened. From the viewpoint of surface hardness of the antifogging coating film, it is particularly preferable to include 4 parts by mass or more and 8 parts by mass or less of (B) a reactive nonionic surfactant, 2 parts by mass or less of (C) a reactive ionic liquid, 8 parts by mass of (D) a polymerization initiator, 10 parts by mass of (E) pentaerythritol (meth) acrylate, and 4 parts by mass of (F) a urethane (meth) acrylate resin, with respect to 100 parts by mass of (a) a hydrophilic bisphenol a (meth) acrylate (examples 9 to 11).
(conclusion)
From the above results, it is understood that an antifogging coating film having an excellent initial antifogging property (for example, high-temperature antifogging property and low-temperature antifogging property) immediately after the formation of an antifogging coating film and an excellent antifogging durability in which an antifogging effect can be maintained for a long time can be formed by the antifogging coating composition having a specific composition according to the present invention. Further, by containing the components (E) and (F) in addition to the components (a) to (D), an antifogging coating film having excellent washing resistance and softness can be obtained.
the embodiments and examples disclosed in the present application are all examples, and it should be understood that the scope of the invention is not limited in any way. The scope of the present invention is not limited to the above-described meaning, and encompasses meanings equivalent to those of the claims and all changes within the scope.
Industrial applicability
The antifogging coating composition and antifogging transparent sheet of the present application can be advantageously applied particularly in various fields in which an antifogging effect that can be sustained for a long time is sought.
Claims (11)
1. An antifogging coating composition characterized by comprising:
(A) Hydrophilic bisphenol a type (meth) acrylate;
(B) A reactive nonionic surfactant;
(C) A reactive ionic liquid; and
(D) A polymerizable initiator.
2. The anti-fog coating composition of claim 1,
And the (C) reactive ionic liquid is a liquid consisting of sulfonic acid ammonium salt.
3. The anti-fog coating composition according to claim 1 or 2, characterized in that,
Further comprising (E) pentaerythritol (meth) acrylate.
4. The anti-fog coating composition according to any one of claims 1 to 3, characterized by further comprising (F) a urethane (meth) acrylate resin.
5. The antifogging coating composition according to any one of claims 1 to 4, characterized in that the content of the (B) component is more than 2 parts by mass and 20 parts by mass or less with respect to 100 parts by mass of the (A) component.
6. The antifogging coating composition according to any one of claims 1 to 5, characterized in that the content of the component (C) is 1 part by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the component (A).
7. The antifogging coating composition according to any one of claims 1 to 6, wherein a content mass ratio of the (B) component to the (C) component (B)/(C) is 1 or more and 10 or less.
8. The anti-fog coating composition according to any one of claims 1 to 7, characterized in that,
Further comprising a leveling agent.
9. The anti-fog coating composition according to any one of claims 1 to 8 wherein the polymerizable initiator is a photopolymerization initiator.
10. An antifogging transparent sheet, comprising:
A transparent substrate; and
An antifogging coating film comprising the antifogging coating composition according to any one of claims 1 to 9 disposed on the surface of the substrate.
11. The antifogging transparent sheet according to claim 10,
The substrate is a substrate made of polyethylene terephthalate.
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| JP2017123300A JP2019006891A (en) | 2017-06-23 | 2017-06-23 | Antifogging coating composition and antifogging transparent sheet using the same |
| JP2017-123300 | 2017-06-23 | ||
| PCT/JP2018/018592 WO2018235456A1 (en) | 2017-06-23 | 2018-05-14 | Antifogging coating composition and antifogging transparent sheet using same |
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| CN110546212A true CN110546212A (en) | 2019-12-06 |
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| JP (1) | JP2019006891A (en) |
| CN (1) | CN110546212A (en) |
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| CN112708161A (en) * | 2020-12-28 | 2021-04-27 | 江苏双星彩塑新材料股份有限公司 | Magnetic control heat insulation antifogging base film |
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| JP2020158680A (en) * | 2019-03-27 | 2020-10-01 | 中国塗料株式会社 | Active energy ray-curable resin composition and use therefor |
| TW202104156A (en) * | 2019-04-23 | 2021-02-01 | 日商東亞合成股份有限公司 | Curable-type composition |
| CN112409987B (en) * | 2020-11-24 | 2022-08-16 | 中电保力（北京）科技有限公司 | Hydrophilic antifogging agent |
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2019006891A (en) | 2019-01-17 |
| TW201905159A (en) | 2019-02-01 |
| WO2018235456A1 (en) | 2018-12-27 |
| TWI696691B (en) | 2020-06-21 |
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