Optical product

Abstract

To provide an optical product including an antifogging coat film excellent in antifogging and durability.SOLUTION: The optical product comprises a transparent material, and an antifogging coat film arranged on the surface of the transparent material. The antifogging coat film is obtained by drying and / or curing a coating film composed of antifogging coating composition. The antifogging coating composition contains polymer (A), a base material component (B), and surfactant (C). The polymer (A) includes: a constitutional unit derived from a compound (a) containing ethylenically unsaturated group and ionic group; a constitutional unit derived from a compound (b) containing ethylenically unsaturated group and -OH group, and / or -NH2 group; and a constitutional unit derived from a compound (c) represented by a predetermined chemical formula. At least one terminal of a main chain includes a structure derived from a compound (d) containing thiol group and hydrocarbon group with four or more carbon atoms.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an optical product comprising a transparent material and an anti-fog coating film disposed on a surface of the transparent material. [Background technology]

[0002] In humid places, condensation may occur on the surface of an object. In particular, in optical products that include transparent materials such as mirrors, windows, prisms, and lenses, the fog caused by condensation can obstruct the passage of light, preventing users from viewing normally. Therefore, it is preferable that such optical products have a function to prevent fogging.

[0003] In order to solve the above problems, for example, Patent Document 1 proposes a curable composition containing a specific (meth)acrylate compound and a surfactant. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2022-156125 Summary of the Invention [Problem to be solved by the invention]

[0005] The curable composition described in Patent Document 1 gives a cured film with excellent anti-fogging properties. However, if the cured film is exposed to water for a long period of time, the anti-fogging properties of the cured film may be reduced even after drying, resulting in a problem with anti-fogging durability.

[0006] The present invention has been made in view of the above circumstances, and has as its object to provide an optical product provided with an anti-fog coating film having excellent anti-fog durability, an anti-fog coating composition that provides the anti-fog coating film, a cured product thereof, the anti-fog coating film, a polymer used in the anti-fog coating composition, and a method for producing the same. [Means for solving the problem]

[0007] In order to solve the above problems, the present inventors have conducted extensive research and found that the above problems can be solved by obtaining an anti-fog coating film from a composition containing a predetermined polymer (A), a base component (B), and a surfactant (C), and have thus completed the present invention. Specifically, the present invention provides the following.

[0008] A first aspect is an optical product comprising a transparent material and an anti-fogging coating film disposed on a surface of the transparent material, the anti-fog coating film is obtained by drying and / or curing a coating film made of an anti-fog coating composition, the anti-fog coating composition comprises a polymer (A), a substrate component (B), and a surfactant (C); the polymer (A) comprises a structural unit derived from a compound (a), a structural unit derived from a compound (b), and a structural unit derived from a compound (c); the polymer (A) has a structure derived from the compound (d) at at least one end of the main chain, the compound (a) is a compound having an ethylenically unsaturated group and an ionic group, The compound (b) is a compound having an ethylenically unsaturated group and an —OH group and / or an —NH group, The compound (c) is a compound represented by the following formula (c-1): The compound (d) is a compound having a thiol group and a hydrocarbon group having 4 or more carbon atoms, The optical product is one in which the substrate component (B) contains a resin (B1) and / or a polymerizable monomer (B2). [ka] (In formula (c-1), R c1 represents a hydrogen atom or a methyl group, and R c2 represents a hydrocarbon group having 1 to 12 carbon atoms, and R c3 represents a hydrocarbon group having 2 to 4 carbon atoms, and Rc4 represents a hydrocarbon group having 12 or more carbon atoms, cm represents 0 or 1, and cn represents an integer of 1 or more and 500 or less.

[0009] A second embodiment includes a polymer (A), a substrate component (B), and a surfactant (C), the polymer (A) comprises a structural unit derived from a compound (a), a structural unit derived from a compound (b), and a structural unit derived from a compound (c); the polymer (A) has a structure derived from the compound (d) at at least one end of the main chain, the compound (a) is a compound having an ethylenically unsaturated group and an ionic group, The compound (b) is a compound having an ethylenically unsaturated group and an —OH group and / or an —NH group, The compound (c) is a compound represented by the following formula (c-1): The compound (d) is a compound having a thiol group and a hydrocarbon group having 4 or more carbon atoms, The anti-fog coating composition comprises the substrate component (B) containing a resin (B1) and / or a polymerizable monomer (B2). [ka] (In formula (c-1), R c1 represents a hydrogen atom or a methyl group, and R c2 represents a hydrocarbon group having 1 to 12 carbon atoms, and R c3 represents a hydrocarbon group having 2 to 4 carbon atoms, and R c4 represents a hydrocarbon group having 12 or more carbon atoms, cm represents 0 or 1, and cn represents an integer of 1 or more and 500 or less.

[0010] A third aspect is a cured product of the anti-fog coating composition of the second aspect.

[0011] The fourth aspect is an anti-fog coating film obtained by drying and / or curing a coating film made of the anti-fog coating composition of the second aspect.

[0012] A fifth aspect is a polymer comprising a constitutional unit derived from compound (a), a constitutional unit derived from compound (b), and a constitutional unit derived from compound (c), the polymer has a structure derived from compound (d) at at least one end of the main chain, the compound (a) is a compound having an ethylenically unsaturated group and an ionic group, The compound (b) is a compound having an ethylenically unsaturated group and an —OH group and / or an —NH group, The compound (c) is a compound represented by the following formula (c-1): The compound (d) is a polymer, which is a compound having a thiol group and a hydrocarbon group having 4 or more carbon atoms. [ka] (In formula (c-1), R c1 represents a hydrogen atom or a methyl group, and R c2 represents a hydrocarbon group having 1 to 12 carbon atoms, and R c3 represents a hydrocarbon group having 2 to 4 carbon atoms, and R c4 represents a hydrocarbon group having 12 or more carbon atoms, cm represents 0 or 1, and cn represents an integer of 1 or more and 500 or less.

[0013] A sixth aspect is the method for producing a polymer according to the fifth aspect, wherein the compound (a), the compound (b), and the compound (c) are polymerized in the presence of the compound (d). [Effects of the Invention]

[0014] According to the present invention, an optical product having an anti-fog coating film excellent in anti-fog durability can be provided. Also, an anti-fog coating composition that provides the anti-fog coating film, a cured product thereof, the anti-fog coating film, a polymer used in the anti-fog coating composition, and a method for producing the same can be provided. DETAILED DESCRIPTION OF THE INVENTION

[0015] Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to the following embodiments and can be practiced with appropriate modifications within the scope of the object of the present invention.

[0016] ≪Optical products≫ The optical product comprises a transparent material and an anti-fog coating film disposed on the surface of the transparent material. The anti-fog coating film is obtained by drying and / or curing a coating film made of an anti-fog coating composition. The anti-fog coating composition comprises a polymer (A), a substrate component (B), and a surfactant (C). The polymer (A) comprises a structural unit derived from compound (a) (hereinafter also referred to as structural unit (a)), a structural unit derived from compound (b) (hereinafter also referred to as structural unit (b)), and a structural unit derived from compound (c) (hereinafter also referred to as structural unit (c)), and has a structure derived from compound (d) (hereinafter also referred to as structure (d)) at at least one end of the main chain. The substrate component (B) comprises a resin (B1) and / or a polymerizable monomer (B2).

[0017] The anti-fogging coating film provided on optical products has excellent anti-fogging durability. The reason for this effect is not entirely clear, but is thought to be due to the following reasons. The cured film described in Patent Document 1 exhibits anti-fogging properties by forming a water film with low surface tension due to the surfactant dissolved in the absorbed water being eluted onto the surface of the cured film. The reason why the anti-fogging properties of the cured film are reduced is thought to be that the surfactant is excessively eluted due to prolonged contact with water, and even after subsequent drying, the surfactant in the cured film is insufficient to begin with. Polymer (A) is believed to orient on the surface of the anti-fog coating film by combining hydrophilic structural units (a) and structural units (b) with hydrophobic structural units (c) and structure (d). The functional groups of structural units (a) and structural units (b) interact with the surfactant (through hydrogen bonding, etc.), which is believed to prevent excessive surfactant elution. Furthermore, because the hydrophilic functional groups of structural units (a) and structural units (b) orient on the surface side of the anti-fog coating film, the hydrophilicity of the surface of the anti-fog coating film can be improved, and anti-fog properties can be maintained regardless of surfactant elution.

[0018] First, the anti-fog coating composition used to obtain the anti-fog coating film will be described below.

[0019] <Anti-fog coating composition> The anti-fog coating composition comprises a polymer (A), a substrate component (B), and a surfactant (C).

[0020] [Polymer (A)] The polymer (A) contains a structural unit (a) derived from the compound (a), a structural unit (b) derived from the compound (b), and a structural unit (c) derived from the compound (c), and has a structure (d) derived from the compound (d) at least at one end of the main chain.

[0021] (Compound (a)) Compound (a) is a compound having an ethylenically unsaturated group and an ionic group. The ionic group may be a group consisting of an anion and a cation, or may be a group capable of forming a salt by reacting with an electrolyte. The electrolyte is typically an acid or a base according to the Bronsted definition. It is believed that the interaction (e.g., hydrogen bonding) between the ionic group and the surfactant prevents excessive elution of the surfactant, and that the ionic group can improve the hydrophilicity of the surface of the anti-fog coating film.

[0022] The ethylenically unsaturated group is a group containing an ethylenically unsaturated double bond. The ethylenically unsaturated group is not particularly limited, but examples thereof include alkenyl groups such as vinyl, 1-propenyl, 2-n-propenyl (allyl), 1-n-butenyl, 2-n-butenyl, and 3-n-butenyl; (meth)acryloyl group-containing groups such as (meth)acryloyl, (meth)acryloyloxy, and (meth)acryloylamino; and the like. Among these, vinyl, (meth)acryloyl, (meth)acryloyloxy, and (meth)acryloylamino are preferred.

[0023] Examples of the ionic group include a phosphonic acid group, a phosphinic acid group, a phosphoric acid group, a sulfonic acid group, and salts thereof, as well as a quaternary ammonium base and a nitrogen-containing heterocyclic group, etc. Among these, a quaternary ammonium base, a sulfonic acid group, or a sulfonate group is preferred. When the ionic group is a salt of an acidic group such as a sulfonic acid group, the cation constituting the salt of the acidic group may be an organic cation or an inorganic cation. The cation is preferably an inorganic cation, more preferably a metal ion, and even more preferably an alkali metal ion. Examples of the alkali metal ion include a lithium ion, a sodium ion, a potassium ion, and a strontium ion, and preferably a sodium ion and a potassium ion. Examples of the quaternary ammonium group include trialkylammonium bases. Trialkylammonium bases include -N + (R a01 )3·X - It is expressed as R a01 is an alkyl group. a01 may be the same or different. X - is a counter anion to the ammonium cation. The number of carbon atoms in the alkyl group in the trialkylammonium base is preferably 1 or more and 10 or less, more preferably 1 or more and 5 or less, and even more preferably 1 or more and 3 or less. Examples of the alkyl group in the trialkylammonium base include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group. Of these, a methyl group is preferred. The counter anion in the trialkylammonium base is not particularly limited as long as the desired effect is not impaired. The counter anion may be an organic anion or an inorganic anion. The counter anion is preferably a halide ion. Examples of the halide ion include F - , Cl - , Br - , and I - Examples include:

[0024] The compound (a) is preferably a compound represented by the following formula (a1-1). R a1 -R a2 -R a3 (a1-1) (In formula (a1-1), R a1 is a vinyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, or a (meth)acryloylamino group, and R a2 is a hydrocarbon group having 1 to 10 carbon atoms, and R a3 is a quaternary ammonium group, a sulfonic acid group, or a sulfonate group.

[0025] R a1 As the alkyl group, a vinyl group, a (meth)acryloyloxy group, and a (meth)acryloylamino group are preferred, and a vinyl group and a (meth)acryloylamino group are more preferred.

[0026] R a2 The hydrocarbon group preferably has 2 or more and 8 or less carbon atoms. R a2 Examples of the hydrocarbon group include an alkylene group, an aromatic hydrocarbon group, and a combination of an alkylene group and an aromatic hydrocarbon group. The alkylene group may be linear or branched. The alkylene group preferably has 1 or more and 8 or less carbon atoms, more preferably 2 or more and 5 or less carbon atoms. Examples of the aromatic hydrocarbon group include a phenylene group and a naphthalenediyl group, with the phenylene group being preferred.

[0027] Ra3 The quaternary ammonium group as a hydroxyl group is similar to the quaternary ammonium group as an ionic group.

[0028] Preferable specific examples of the compound represented by formula (a1-1) include: ((meth)acryloylaminoalkyl)trialkylammonium salts such as (3-(meth)acryloylaminopropyl)trimethylammonium chloride, (3-(meth)acryloylaminopropyl)trimethylammonium bromide, and (3- and (meth)acryloylaminopropyl)trimethylammonium iodide; ((meth)acryloyloxyalkyl)trialkylammonium salts such as (2-(meth)acryloyloxyethyl)trimethylammonium chloride, (2-(meth)acryloyloxyethyl)trimethylammonium bromide, and (2-(meth)acryloyloxyethyl)trimethylammonium iodide; allyltrialkylammonium salts such as allyltrimethylammonium chloride, allyltrimethylammonium bromide, allyltrimethylammonium iodide, allyltriethylammonium chloride, allyltriethylammonium bromide, and allyltriethylammonium iodide; (Meth)acryloylaminoalkylsulfonic acids such as 2-(meth)acryloylamino-2-methylpropanesulfonic acid, sodium 2-(meth)acryloylamino-2-methylpropanesulfonate, and potassium 2-(meth)acryloylamino-2-methylpropanesulfonate, and salts thereof; Examples thereof include vinylarylsulfonic acids such as p-styrenesulfonic acid, sodium p-styrenesulfonate, potassium p-styrenesulfonate, m-styrenesulfonic acid, sodium m-styrenesulfonate, and sodium m-styrenesulfonate, and salts thereof.

[0029] (Compound (b)) The compound (b) is a compound having an ethylenically unsaturated group and an -OH group and / or an -NH2 group. It is believed that the interaction (hydrogen bonding, etc.) between the -OH group or -NH2 group and the surfactant suppresses excessive elution of the surfactant. It is also believed that the -OH group or -NH2 group can improve the hydrophilicity of the surface of the anti-fog coating film. It is believed that the inclusion of structural unit (b) increases the molecular weight of the polymer, thereby suppressing elution of the polymer itself.

[0030] The ethylenically unsaturated group in the compound (b) is the same as the ethylenically unsaturated group in the compound (a). The ethylenically unsaturated group in the compound (b) is preferably a (meth)acryloyl group.

[0031] The compound (b) is preferably a compound represented by the following formula (b1-1). R b1 -R b2 -R b3 (b1-1) (In formula (b1-1), R b1 is a (meth)acryloyl group, and R b2 is a single bond or a hydrocarbon group having 1 to 10 carbon atoms, and R b3 is an -OH group or an -NH group.

[0032] R b2 is preferably a single bond. R b2 The hydrocarbon group having 1 to 10 carbon atoms as R a2 The same applies to hydrocarbon groups having 1 to 10 carbon atoms as above. R b3 is preferably an —OH group.

[0033] As the compound (b) explained above, (meth)acrylamide and (meth)acrylic acid are preferred, and (meth)acrylic acid is more preferred.

[0034] (Compound (c)) The compound (c) is a compound represented by the following formula (c-1). It is believed that the polymer (A) is oriented on the surface of the anti-fog coating film by having the hydrophobic structural unit (c) in addition to the hydrophilic structural units (a) and (b). [ka] (In formula (c-1), R c1 represents a hydrogen atom or a methyl group, and R c2 represents a hydrocarbon group having 1 to 12 carbon atoms, and R c3 represents a hydrocarbon group having 2 to 4 carbon atoms, and R c4 represents a hydrocarbon group having 12 or more carbon atoms, cm represents 0 or 1, and cn represents an integer of 1 or more and 500 or less.

[0035] R c2 The hydrocarbon group as the alkyl group preferably has 1 or more and 8 or less carbon atoms, more preferably 1 or more and 5 or less carbon atoms. R c2 Examples of the hydrocarbon group include an alkylene group and an aromatic hydrocarbon group. Of these, an alkylene group is preferred. The alkylene group may be linear or branched, but is preferably linear. Preferred alkylene groups are methylene, ethylene, and propane-1,3-diyl, with ethylene being more preferred.

[0036] R c3 The hydrocarbon group as is preferably an alkylene group, more preferably an ethylene group.

[0037] R c4 The number of carbon atoms in the hydrocarbon group is preferably 12 or more and 40 or less, more preferably 12 or more and 30 or less, even more preferably 12 or more and 25 or less, and particularly preferably 15 or more and 20 or less. R c4Examples of the hydrocarbon group include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, and a combination of an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The hydrocarbon group is preferably an aliphatic hydrocarbon group. The aliphatic hydrocarbon group may be a chain aliphatic hydrocarbon group, an alicyclic hydrocarbon group, or a combination of a chain aliphatic hydrocarbon group and an alicyclic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, but is preferably unsaturated. The number of unsaturated bonds in the unsaturated aliphatic hydrocarbon group is preferably 1 to 3, more preferably 1. The position of the unsaturated bond in the unsaturated aliphatic hydrocarbon group is not particularly limited. The aliphatic hydrocarbon group may be either linear or branched, but is preferably linear.

[0038] Examples of saturated aliphatic hydrocarbon groups include alkyl groups such as dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, and triacontyl.

[0039] Examples of the unsaturated aliphatic hydrocarbon group include alkenyl groups such as dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, icosenyl, henicosenyl, docosenyl, tricosenyl, tetracosenyl, pentacosenyl, hexacosenyl, heptacosenyl, octacosenyl, nonacosenyl, and triacontenyl; Examples of alkynyl groups include alkynyl groups such as methyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecinyl, heptadecynyl, octadecynyl, nonadecinyl, icosinyl, henicosinyl, docosinyl, tricosinyl, tetracosinyl, pentacosinyl, hexacosinyl, heptacosinyl, octacosinyl, nonacosinyl, and triacontinyl. The number of carbon atoms in the alkenyl group and the number of carbon atoms in the alkynyl group are preferably 12 to 40, more preferably 12 to 30, even more preferably 12 to 25, and particularly preferably 15 to 20. The alkenyl group and the alkynyl group are preferably linear.

[0040] The aliphatic hydrocarbon group is preferably an alkyl group or an alkenyl group, more preferably an alkenyl group, even more preferably a linear alkenyl group, and most preferably an octadecenyl group.

[0041] The unsaturated aliphatic hydrocarbon group is preferably a group represented by the following formula (c-1a): -R c41 -CH=CH-R c42 (c-1a) (In formula (c-1a), R c41 is an alkylene group, and R c42 is an alkyl group, and R c41 The number of carbon atoms in the alkylene group as R c42 The total number of carbon atoms in the alkyl group is 10 or more. R c41The number of carbon atoms in the alkylene group represented by R is preferably 1 or more and 20 or less, more preferably 4 or more and 15 or less, and even more preferably 6 or more and 10 or less. c41 The alkylene group as R may be linear or branched, but is preferably linear. c41 Examples of the alkylene group include a methylene group, an ethane-1,2-diyl group (ethylene group), an ethane-1,1-diyl group, a propane-1,3-diyl group, a propane-1,2-diyl group, a propane-1,1-diyl group, a propane-2,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, and a nonane-1,9-diyl group. Examples of the alkyl group include decane-1,10-diyl, undecane-1,11-diyl, dodecane-1,12-diyl, tridecane-1,13-diyl, tetradecane-1,14-diyl, pentadecane-1,15-diyl, hexadecane-1,16-diyl, heptadecane-1,17-diyl, octadecane-1,18-diyl, nonadecane-1,19-diyl, and icosane-1,20-diyl groups. R c42 The number of carbon atoms in the alkyl group represented by R is preferably 1 or more and 20 or less, more preferably 4 or more and 15 or less, and even more preferably 6 or more and 10 or less. c42 The alkyl group as R may be linear or branched, but is preferably linear. c42 Examples of the alkyl group as the aryl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, and n-icosyl group. R c41 The number of carbon atoms in the alkylene group as R c42The total number of carbon atoms in the alkyl group as the aryl group is preferably 10 or more and 38 or less, more preferably 10 or more and 28 or less, even more preferably 10 or more and 23 or less, and particularly preferably 13 or more and 18 or less.

[0042] cm is preferably 1. cn is preferably 5 or more and 300 or less, more preferably 5 or more and 100 or less, even more preferably 5 or more and 50 or less, and particularly preferably 5 or more and 30 or less.

[0043] The method for producing the compound represented by formula (c-1) is not particularly limited. For example, the compound represented by formula (c-1) can be obtained by reacting an isocyanate group of a compound represented by formula (c-1a) below with a hydroxy group of a compound represented by formula (c-1b) below. [ka] HO-(R c3 -O) cn -R c4 (c-1b) (In formula (c-1a) and formula (c-1b), R c1 ~R c4 , cm, and cn are R in formula (c-1). c1 ~R c4 , cm, and cn.)

[0044] The molar ratio of the structural unit (a) to all structural units of the polymer (A) is preferably 50 mol% or more and 98 mol% or less, more preferably 60 mol% or more and 95 mol% or less, and even more preferably 70 mol% or more and 92 mol% or less. The molar ratio of the structural unit (b) to all structural units of the polymer (A) is preferably 1 mol % or more and 40 mol % or less, more preferably 2 mol % or more and 30 mol % or less, and even more preferably 3 mol % or more and 25 mol % or less. The molar ratio of the structural unit (c) to all structural units of the polymer (A) is preferably 1 mol % or more and 20 mol % or less, more preferably 1 mol % or more and 12 mol % or less, and even more preferably 2 mol % or more and 6 mol % or less.

[0045] (Compound (d)) Compound (d) is a compound having a thiol group and a hydrocarbon group having 4 or more carbon atoms. Compound (d) acts as a chain transfer agent during polymerization of polymer (A) and modifies the terminal ends of polymer (A). It is believed that polymer (A) is oriented on the surface of the anti-fog coating film by having hydrophobic structure (d) in addition to structural unit (a) and structural unit (b).

[0046] The hydrocarbon group preferably has 4 or more and 30 or less carbon atoms, more preferably 6 or more and 20 or less carbon atoms, and even more preferably 8 or more and 16 or less carbon atoms. Examples of the hydrocarbon group include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, and a combination of an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The hydrocarbon group is preferably an aliphatic hydrocarbon group. The aliphatic hydrocarbon group may be a chain aliphatic hydrocarbon group, an alicyclic hydrocarbon group, or a combination of a chain aliphatic hydrocarbon group and an alicyclic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, but is preferably saturated. The aliphatic hydrocarbon group may be linear or branched, but is preferably linear. The aliphatic hydrocarbon group is preferably an alkyl group, and more preferably a linear alkyl group.

[0047] The compound (d) is preferably a compound represented by the following formula (d1-1). R d1 -SH (d1-1) (In formula (d1-1), R d1 is a hydrocarbon group having 4 or more carbon atoms.

[0048] R d1 The hydrocarbon group having 4 or more carbon atoms as is the same as the hydrocarbon group having 4 or more carbon atoms contained in compound (d).

[0049] The structure (d) is preferably a structure represented by the following formula (d1-2). -SR d1 (d1-2) (In formula (d1-2), R d1 is R in formula (d1-1) d1 is the same as

[0050] The weight average molecular weight of the polymer (A) is preferably 50,000 or more and 2,000,000 or less, more preferably 70,000 or more and 1,200,000 or less. In this specification, the weight average molecular weight of the polymer (A) means the weight average molecular weight calculated in terms of standard polystyrene as determined by gel permeation chromatography (GPC).

[0051] The content of the polymer (A) is preferably 0.05 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, and even more preferably 0.5 to 3 parts by mass, relative to 100 parts by mass of the base component (B). Within the above range, excellent anti-fogging properties and anti-fogging durability are likely to be obtained.

[0052] The method for producing the polymer (A) is not particularly limited. For example, the polymer (A) can be obtained by polymerizing the compound (a), the compound (b), and the compound (c) in the presence of the compound (d) as a chain transfer agent. The polymerization can be carried out by a conventionally known method using an appropriate polymerization initiator and solvent.

[0053] [Base material component (B)] The base component (B) contains a resin (B1) and / or a polymerizable monomer (B2). As the base component (B), the polymerizable monomer (B2) is preferred.

[0054] (Resin (B1)) The resin (B1) is not particularly limited as long as it is a non-curable resin material that imparts shaping properties such as film-forming properties to the anti-fog coating composition. Specific examples of such resins include polyacetal resins, polyamide resins, polycarbonate resins, polyester resins (such as polybutylene terephthalate, polyethylene terephthalate, and polyarylate), FR-AS resins, FR-ABS resins, AS resins, ABS resins, polyphenylene oxide resins, polyphenylene sulfide resins, polysulfone resins, polyethersulfone resins, polyetheretherketone resins, fluorine-containing resins, polyimide resins, polyamideimide resins, polyamide bismaleimide resins, polyetherimide resins, polybenzoxazole resins, polybenzothiazole resins, polybenzimidazole resins, silicone resins, BT resins, polymethylpentene, ultra-high molecular weight polyethylene, FR-polypropylene, (meth)acrylic resins (such as polymethyl methacrylate), and polystyrene. These resin materials may be used in combination of two or more.

[0055] (Polymerizable monomer (B2)) The polymerizable monomer (B2) is a compound that is cured by application of energy such as heating or exposure to light, or by the action of a curing agent or an initiator (D) described below. Examples of the polymerizable monomer (B2) include compounds having an ethylenically unsaturated group such as (meth)acrylic monomers, and cationically polymerizable positive compounds such as epoxy compounds, oxetane compounds, and vinyl ether compounds. As the polymerizable monomer (B2), a compound having an ethylenically unsaturated group as a polymerizable group is preferred in terms of the stability over time of the anti-fog coating composition. As the compound having an ethylenically unsaturated group, a compound having a (meth)acryloyl group, such as a (meth)acrylate compound or a (meth)acrylamide compound, is preferred, and a (meth)acrylate compound is more preferred. The polymerizable monomer (B2) may be a monofunctional polymerizable monomer or a polyfunctional polymerizable monomer. In terms of the strength of the cured product and polymerization reactivity, the polymerizable monomer (B2) preferably contains a polyfunctional polymerizable monomer.

[0056] The polymerizable monomer (B2) is preferably a (meth)acrylate compound (B2-1) having an HLB value of 15.2 or more, whereby the resulting anti-fog coating film is likely to exhibit anti-fog properties by adhering to and absorbing moisture on the film surface.

[0057] The HLB value of the (meth)acrylate compound (B2-1) is preferably 15.5 or more, more preferably 16.0 or more. The upper limit of the HLB value is not particularly limited, but is, for example, 19.0 or less, or 18.0 or less.

[0058] In this specification, the HLB value of the (meth)acrylate compound (B2-1) is a value determined by the following formula based on the Griffin method. HLB value = 20 x total formula weight of hydrophilic functional groups / molecular weight In this specification, hydrophilic functional groups include sulfone groups (-SO3-), phosphono groups (-PO3-), carboxy groups (-COOH), amide groups (-CONH-), imide groups (-CON-), aldehyde groups (-CHO), hydroxy groups (-OH), amino groups (-NH2), acetyl groups (-COCH3), ethyleneamine groups (-CH2CH2NH-), ethyleneoxy groups (-CH2CHO-), alkali metal ions, alkaline earth metal ions, ammonium ions, halide ions, acetate ions, and the like.

[0059] Examples of the (meth)acrylate compound (B2-1) include polyfunctional (meth)acrylate compounds having an alkyleneoxy group with 2 to 4 carbon atoms, specifically polyfunctional (meth)acrylate compounds having an ethyleneoxy group.

[0060] The (meth)acrylate compound (B2-1) is preferably a polyfunctional (meth)acrylate compound represented by the following formula (b2-1a) and / or a bifunctional (meth)acrylate compound represented by the following formula (b2-1b), and more preferably a polyfunctional (meth)acrylate compound represented by the following formula (b2-1a). [ka] (In formula (b2-1a), n is an integer of 4 or more. A 1 are each independently an alkylene group having 2 to 4 carbon atoms. k, l, and m are each independently an integer of 0 or greater, and their sum is an integer of 50 or greater. R 1 are each independently a hydrogen atom or a (meth)acryloyl group, and at least three are (meth)acryloyl groups. [ka] (In formula (b2-1b), A 2 is an alkylene group having 2 to 4 carbon atoms. p is an integer of 10 or more. R 2 are each independently a (meth)acryloyl group.

[0061] In formula (b2-1a), n is preferably 4 or more and 10 or less, and more preferably 4 or more and 6 or less. A 1 The alkylene group in A may be linear or branched. 1 is preferably an ethylene group. k, l and m are preferably 1 or more and 40 or less, more preferably 1 or more and 30 or less. The sum of k, l and m is preferably 50 or more and 100 or less, more preferably 55 or more and 80 or less. R 1 Preferably, at least four of these are (meth)acryloyl groups, and more preferably, at least six of these are (meth)acryloyl groups.

[0062] In formula (b2-1b), A 2 The alkylene group in A may be linear or branched.2 is preferably an ethylene group. p is preferably 10 or more and 30 or less, and more preferably 12 or more and 20 or less.

[0063] The content of the (meth)acrylate compound (B2-1) in 100% by mass of the base component (B) is preferably 35% by mass or more and 99% by mass or less, more preferably 40% by mass or more and 90% by mass or less, and even more preferably 50% by mass or more and 80% by mass or less. When it is within the above numerical range, good anti-fogging properties and anti-fogging durability are likely to be obtained.

[0064] The polymerizable monomer (B2) preferably contains a polyfunctional (meth)acrylate compound (B2-2) other than the (meth)acrylate compound (B2-1), which makes it easier to improve the curability of the anti-fog coating film.

[0065] Examples of the polyfunctional (meth)acrylate compound (B2-2) include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexane glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerin di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol dimethacrylate, methylpropane tri(meth)acrylate, methylpropane dimeth ... Examples of the glycerin-based copolymer include erythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, ethylene glycol diglycidyl ether di(meth)acrylate, diethylene glycol diglycidyl ether di(meth)acrylate, phthalic acid diglycidyl ester di(meth)acrylate, glycerin tri(meth)acrylate, and glycerin polyglycidyl ether poly(meth)acrylate.

[0066] The content of the polyfunctional (meth)acrylate compound (B2-2) in 100% by mass of the base material component (B) is preferably 1% by mass or more and 65% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 50% by mass or less. Within the above numerical range, it is easy to achieve both improved hardness and anti-fogging properties of the anti-fogging coating film.

[0067] The content of the base component (B) is preferably 40% by mass or more, more preferably 60% by mass or more, and even more preferably 80% by mass or more, based on 100% by mass of the anti-fog coating composition (total solid content) excluding the mass of the solvent (E) described below. The content is preferably 99% by mass or less. Within the above numerical range, good anti-fog properties and anti-fog durability are likely to be obtained.

[0068] [Surfactant (C)] The anti-fog coating composition contains a surfactant (C), which dissolves in the absorbed water and dissolves on the surface of the anti-fog coating film, forming a water film with low surface tension.

[0069] The surfactant (C) is preferably a water-soluble surfactant. The water-soluble surfactant is not particularly limited, but preferably has a solubility of 0.01% by mass or more in water at room temperature. Any of nonionic surfactants, cationic surfactants, anionic surfactants, and amphoteric surfactants can be used as the surfactant (C). The surfactant may be silicone-based. These surfactants may be used alone or in combination of two or more.

[0070] Examples of nonionic surfactants include polyoxyethylene octyl ether, polyoxyethylene decyl ether, polyoxyethylene lauryl ether, polyoxyethylene laurylamine, polyoxyethylene oleylamine, polyoxyethylene polystyrylphenyl ether, polyoxyalkylene polystyrylphenyl ether, polyoxyalkylene primary alkyl ether, and polyoxyalkylene secondary alkyl ether. Examples of cationic surfactants include oleylamine acetate, laurylpyridinium chloride, cetylpyridinium chloride, lauryltrimethylammonium chloride, stearyltrimethylammonium chloride, behenyltrimethylammonium chloride, didecyldimethylammonium chloride, and didecyldimethylammonium bromide. Examples of anionic surfactants include coconut fatty acid salts, castor sulfated oil salts, lauryl sulfate salts, polyoxyalkylene allyl phenyl ether sulfate salts, alkyl benzene sulfonic acid, alkyl benzene sulfonate salts, alkyl diphenyl ether disulfonate salts, alkyl naphthalene sulfonate salts, dialkyl sulfosuccinate salts, isopropyl phosphate, polyoxyethylene alkyl ether phosphate salts, polyoxyethylene allyl phenyl ether phosphate salts, and dialkyl sulfosuccinate salts. Examples of amphoteric surfactants include coconut alkyl dimethylamine oxide, fatty acid amidopropyl dimethylamine oxide, alkyl polyaminoethyl glycine hydrochloride, amido betaine type surfactants, alanine type surfactants, and lauryliminodipropionic acid.

[0071] The content of the surfactant (C) is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, and even more preferably 1 to 10 parts by mass, relative to 100 parts by mass of the base component (B). When the content is within the above range, good anti-fogging properties and anti-fogging durability are likely to be obtained.

[0072] [Initiator (D)] When the anti-fog coating composition contains the polymerizable monomer (B2), it preferably contains an initiator (D). The initiator (D) is not particularly limited, and conventionally known photopolymerization initiators, thermal polymerization initiators, etc. can be used. However, photopolymerization initiators are preferred because they can easily cure the anti-fog coating composition well in a short time.

[0073] Specific examples of the photopolymerization initiator include 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, and 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one. ion, 2,2-dimethoxy-1,2-diphenylethan-1-one, bis(4-dimethylaminophenyl)ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, 1,2-octanedione, 1-[4-(phenylthio)phenyl]-, 2-(O-benzoyloxime) (Irgacure OXE01), ethanone-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime) (Irgacure OXE02), 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Omnirad TPO H), bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (Omnirad 819), 4-benzoyl-4'-methyldimethyl sulfide, 4-dimethylaminobenzoic acid, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, butyl 4-dimethylaminobenzoate, 4-dimethylamino-2-ethylhexylbenzoic acid, 4-dimethylamino-2-isoamylbenzoic acid, benzyl-β-methoxyethyl acetal, benzyl dimethyl ketal, 1-phenyl-1,2-propanedione-2-(O-ethoxy) carbonyl) oxime, methyl O-benzoylbenzoate, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 1-chloro-4-propoxythioxanthone, thioxanthene, 2-chlorothioxanthene, 2,4-diethylthioxanthene, 2-methylthioxanthene, 2-isopropylthioxanthene, 2-ethylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone, 2,3-Diphenylanthraquinone, azobisisobutyronitrile, benzoyl peroxide, cumene hydroperoxide, 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, 2-(O-chlorophenyl)-4,5-di(m-methoxyphenyl)-imidazolyl dimer, benzophenone, 2-chlorobenzophenone, p,p'-bisdimethylaminobenzophenone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3-dimethyl-4-methoxybenzophenone Benzophenone, benzil, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ether, benzoin butyl ether, acetophenone, 2,2-diethoxyacetophenone, p-dimethylacetophenone, p-dimethylaminopropiophenone, dichloroacetophenone, trichloroacetophenone, p-tert-butylacetophenone, p-dimethylaminoacetophenone, p-tert-butyltrichloroacetophenone acetophenone, p-tert-butyldichloroacetophenone, α,α-dichloro-4-phenoxyacetophenone, thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, dibenzosuberone, pentyl-4-dimethylaminobenzoate, 9-phenylacridine, 1,7-bis-(9-acridinyl)heptane, 1,5-bis-(9-acridinyl)pentane, 1,3-bis-(9-acridinyl)propane, p-methoxytriazine, 2,4,6-tris(trichloromethyl)-s-triazine, 2-methyl-4,6- Bis(trichloromethyl)-s-triazine, 2-[2-(5-methylfuran-2-yl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(furan-2-yl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(4-diethylamino-2-methylphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxyphenyl)-4,Examples of suitable photopolymerization initiators include 6-bis(trichloromethyl)-s-triazine, 2-(4-ethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-n-butoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis-trichloromethyl-6-(3-bromo-4-methoxy)phenyl-s-triazine, 2,4-bis-trichloromethyl-6-(2-bromo-4-methoxy)phenyl-s-triazine, 2,4-bis-trichloromethyl-6-(3-bromo-4-methoxy)styrylphenyl-s-triazine, and 2,4-bis-trichloromethyl-6-(2-bromo-4-methoxy)styrylphenyl-s-triazine. These photopolymerization initiators can be used alone or in combination of two or more.

[0074] Specific examples of the thermal polymerization initiator include ketone peroxides (methyl ethyl ketone peroxide, cyclohexanone peroxide, etc.), peroxyketals (2,2-bis(tert-butylperoxy)butane, 1,1-bis(tert-butylperoxy)cyclohexane, etc.), hydroperoxides (tert-butyl hydroperoxide, cumene hydroperoxide, etc.), dialkyl peroxides (di-tert-butyl peroxide (Perbutyl (registered trademark) D (manufactured by NOF Corporation) and di-tert-hexyl peroxide (Perhexyl (registered trademark) D (manufactured by NOF Corporation))), diacyl peroxides (isobutyryl peroxide, lauroyl peroxide, benzoyl peroxide, etc.), peroxydicarbonates (diisopropyl peroxydicarbonate, etc.), peroxyesters (tert-butylperoxyisobutyrate and 2,5-dimethylbenzyl peroxide), and the like. Organic peroxides such as 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile), 2,2'-azobis(2-methylpropionamidine) dihydrochloride, 2,2'-azobis[2-methyl-N-(2-propenyl)propionamidine]dihydrochloride, etc. Examples of suitable thermal polymerization initiators include azo compounds such as dimethyl 2,2'-azobis(2-methylpropionamide), 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 2,2'-azobis(2-methylpropane), 2,2'-azobis(2,4,4-trimethylpentane), and dimethyl 2,2'-azobis(2-methylpropionate). These thermal polymerization initiators can be used alone or in combination of two or more.

[0075] The content of the initiator (D) is preferably 0.1 to 20 parts by mass, more preferably 1 to 15 parts by mass, and even more preferably 3 to 12 parts by mass, per 100 parts by mass of the base component (B). When the content is within the above range, good anti-fogging properties and anti-fogging durability are likely to be obtained.

[0076] [Solvent (E)] The anti-fog coating composition preferably contains a solvent (E) for the purpose of adjusting the coating property and viscosity. The type of solvent (E) is not particularly limited, but is typically an organic solvent. The type of organic solvent is not particularly limited as long as it can uniformly dissolve or disperse the components contained in the anti-fog coating composition.

[0077] Examples of organic solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol (Poly)alkylene glycol monoalkyl ethers such as glycol monomethyl ether and tripropylene glycol monoethyl ether; (poly)alkylene glycol monoalkyl ether acetates such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate; other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone; alkyl lactate esters such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate;Ethyl 2-hydroxy-2-methylpropionate, Methyl 3-methoxypropionate, Ethyl 3-methoxypropionate, Methyl 3-ethoxypropionate, Ethyl 3-ethoxypropionate, Ethoxyethyl acetate, Ethyl hydroxyacetate, Methyl 2-hydroxy-3-methylbutanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutylpropionate, Ethyl acetate, n-propyl acetate, Isopropyl acetate, n-butyl acetate, Isobutyl acetate, n-pentyl formate Examples of suitable esters include butyl acetate, isopentyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, and ethyl 2-oxobutanoate; aromatic hydrocarbons such as toluene and xylene; amides such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; and alcohols such as ethanol, isopropyl alcohol, and butanol. These may be used alone or in combination of two or more.

[0078] The content of the solvent (E) is not particularly limited. From the viewpoint of film-forming properties, the solvent is used so that the solid content concentration is preferably 0.1% by mass or more and 99% by mass or less, more preferably 1% by mass or more and 50% by mass or less, when the mass of the anti-fog coating composition excluding the mass of the solvent (E) is taken as the solid content.

[0079] [Other ingredients] In addition to the components described above, the anti-fog coating composition may contain various additives that have conventionally been incorporated into anti-fog coating compositions. Preferred additives include dispersants, adhesion promoters such as silane coupling agents, antioxidants, anti-aggregating agents, and anti-foaming agents.

[0080] <Anti-fogging coating film> The anti-fog coating film can be obtained by drying and / or curing a coating film made of an anti-fog coating composition.

[0081] The method for forming a coating film made of the anti-fog coating composition is not particularly limited. For example, a coating film can be formed by applying the anti-fog coating composition to the surface of a transparent material of an optical product to a desired film thickness using a contact transfer coating device such as a roll coater, reverse coater, bar coater, or slit coater, or a non-contact coating device such as a spinner (rotary coating device) or curtain flow coater. Alternatively, a coating film can be formed by a method such as dip coating or various printing methods such as inkjet printing or gravure printing.

[0082] The method for drying the coating film is not particularly limited, and conventionally known methods such as natural drying and heat drying can be used.

[0083] The method for curing the coating film is not particularly limited. If the anti-fog coating composition is photocurable, the coating film can be exposed to light. If the anti-fog coating composition is thermocurable, the coating film can be heated to obtain a cured anti-fog coating film. The conditions for exposing the coating film are not particularly limited as long as the curing proceeds well. The exposure is carried out by irradiating with active energy rays such as ultraviolet light or excimer laser light. The amount of energy radiation to be irradiated is not particularly limited, but may be, for example, 30 mJ / cm. 2 More than 5000mJ / cm 2 The following are included:

[0084] The anti-fog coating film is disposed on the surface of the transparent material included in the optical product. The anti-fog coating film may be disposed on a part of the surface of the transparent material, or may be disposed on the entire surface.

[0085] The transparent material is not particularly limited, and examples thereof include transparent plastic, glass (including the glass that forms the front surface of a mirror), etc. The transparent material may be completely transparent or semi-transparent.

[0086] The optical product is not particularly limited as long as it comprises a transparent material that, when cloudy, interferes with the user's normal field of vision or interferes with the normal transmission or reflection of light in an optical device. Specific examples of optical products include mirrors such as vehicle rearview mirrors, bathroom mirrors, washroom mirrors, dental mirrors, and road mirrors; windows of buildings, watchtowers, automobiles, railroad vehicles, aircraft, ships, submarines, snowmobiles, ropeway gondolas, amusement park gondolas, and spaceships; prisms; lenses such as eyeglass lenses, optical lenses, camera lenses, endoscope lenses, lighting lenses, semiconductor lenses, and copier lenses; and goggles such as protective goggles and sports goggles.

[0087] As described above, the present inventors provide the following (1) to (10). (1) An optical product comprising a transparent material and an anti-fogging coating film disposed on a surface of the transparent material, the anti-fog coating film is obtained by drying and / or curing a coating film made of an anti-fog coating composition, the anti-fog coating composition comprises a polymer (A), a substrate component (B), and a surfactant (C); the polymer (A) comprises a structural unit derived from a compound (a), a structural unit derived from a compound (b), and a structural unit derived from a compound (c); the polymer (A) has a structure derived from the compound (d) at at least one end of the main chain, the compound (a) is a compound having an ethylenically unsaturated group and an ionic group, The compound (b) is a compound having an ethylenically unsaturated group and an —OH group and / or an —NH group, The compound (c) is a compound represented by the following formula (c-1): The compound (d) is a compound having a thiol group and a hydrocarbon group having 4 or more carbon atoms, An optical product, wherein the substrate component (B) comprises a resin (B1) and / or a polymerizable monomer (B2). [ka] (In formula (c-1), R c1 represents a hydrogen atom or a methyl group, and R c2 represents a hydrocarbon group having 1 to 12 carbon atoms, and R c3 represents a hydrocarbon group having 2 to 4 carbon atoms, and R c4 represents a hydrocarbon group having 12 or more carbon atoms, cm represents 0 or 1, and cn represents an integer of 1 or more and 500 or less. (2) The optical product according to (1), which is a mirror, a window, a prism, a lens, or goggles. (3) A composition comprising a polymer (A), a base component (B), and a surfactant (C), the polymer (A) comprises a structural unit derived from a compound (a), a structural unit derived from a compound (b), and a structural unit derived from a compound (c); the polymer (A) has a structure derived from the compound (d) at at least one end of the main chain, the compound (a) is a compound having an ethylenically unsaturated group and an ionic group, The compound (b) is a compound having an ethylenically unsaturated group and an —OH group and / or an —NH group, The compound (c) is a compound represented by the following formula (c-1): The compound (d) is a compound having a thiol group and a hydrocarbon group having 4 or more carbon atoms, An anti-fog coating composition, wherein the base material component (B) comprises a resin (B1) and / or a polymerizable monomer (B2). [ka] (In formula (c-1), R c1 represents a hydrogen atom or a methyl group, and R c2 represents a hydrocarbon group having 1 to 12 carbon atoms, and R c3 represents a hydrocarbon group having 2 to 4 carbon atoms, and R c4 represents a hydrocarbon group having 12 or more carbon atoms, cm represents 0 or 1, and cn represents an integer of 1 or more and 500 or less. (4) relative to all structural units of the polymer (A), the molar ratio of the structural unit derived from the compound (a) is 50 mol % or more and 98 mol % or less, the molar ratio of the structural unit derived from the compound (b) is 1 mol % or more and 40 mol % or less, The anti-fog coating composition according to (3), wherein the molar ratio of the structural units derived from the compound (c) is 1 mol % or more and 20 mol % or less. (5) The anti-fog coating composition according to (3) or (4), wherein the mass of the polymer (A) is 0.05 parts by mass or more and 10 parts by mass or less per 100 parts by mass of the base component (B). (6) The anti-fog coating composition according to any one of (3) to (5), wherein the base component (B) contains the polymerizable monomer (B2). (7) A cured product of the anti-fog coating composition according to any one of (3) to (6). (8) An anti-fog coating film obtained by drying and / or curing a coating film made of the anti-fog coating composition according to any one of (3) to (6). (9) A polymer comprising a structural unit derived from compound (a), a structural unit derived from compound (b), and a structural unit derived from compound (c), the polymer has a structure derived from compound (d) at at least one end of the main chain, the compound (a) is a compound having an ethylenically unsaturated group and an ionic group, The compound (b) is a compound having an ethylenically unsaturated group and an —OH group and / or an —NH group, The compound (c) is a compound represented by the following formula (c-1): The compound (d) is a polymer, which is a compound having a thiol group and a hydrocarbon group having 4 or more carbon atoms. [ka] (In formula (c-1), R c1 represents a hydrogen atom or a methyl group, and R c2 represents a hydrocarbon group having 1 to 12 carbon atoms, and R c3 represents a hydrocarbon group having 2 to 4 carbon atoms, and Rc4 represents a hydrocarbon group having 12 or more carbon atoms, cm represents 0 or 1, and cn represents an integer of 1 or more and 500 or less. (10) The method for producing a polymer according to (9), wherein the compound (a), the compound (b), and the compound (c) are polymerized in the presence of the compound (d). [Example]

[0088] The present invention will be described in more detail based on examples, but the present invention is not limited to these examples.

[0089] The various chemicals used in the synthesis of the polymer will be explained below.

[0090] Compound a1: a compound represented by the following formula [ka] Compound a2: a compound represented by the following formula [ka] Compound b1: acrylic acid Compound B2: Acrylamide Compound c1: A compound synthesized by the method described below and represented by the following formula: In the following formula, the double bond contained in the alkenyl group having 18 carbon atoms is a cis double bond. [ka] Compound d1: 1-dodecanethiol

[0091] <Synthesis of compound c1> In a 50 mL glass container, add polyethylene glycol monooleyl ether (HO(CHCHO) n C 18 H 3525.12 g (approximately 35 mmol) of 2-acryloyloxyethyl isocyanate (n=approximately 10, manufactured by Tokyo Chemical Industry Co., Ltd.) was mixed with 5 g of 2-acryloyloxyethyl isocyanate (Karenz AOI manufactured by Resonac Corporation). The mixture was stirred at 60°C for 3 hours to obtain compound c1.

[0092] <Polymer synthesis> [Polymer (a-1)] Into a 50 mL glass container were added 12.5 g (approximately 12.1 mmol) of a 20 mass % aqueous solution of compound a1 as compound (a), 6.87 g (approximately 1.9 mmol) of a 2 mass % aqueous solution of compound b1 as compound (b), 0.54 g (approximately 0.6 mmol) of compound c1 as compound (c), 0.26 g of a 1 mass % propylene glycol monomethyl ether solution of compound d1 as compound (d), and 0.02 g of an azo polymerization initiator (VA-061 manufactured by Tokyo Chemical Industry Co., Ltd.), and water was added so that the solids concentration became 10 mass %. After nitrogen substitution, the mixture was heated to 80°C with stirring and reacted at 80°C for 4 hours to obtain an approximately 10% by mass aqueous solution of polymer (a-1). The weight average molecular weight of polymer (a-1) was 651,700 and the dispersity was 52. The repeating structure and terminal end structure of polymer (a-1) are shown in the following formula: The numbers to the right of [ ] are the molar ratios of each structural unit to all structural units. [ka]

[0093] [Polymer (a-2)] Polymer (a-2) was synthesized in the same manner as polymer (a-1), except that compound (a2) was used instead of compound (a1), the amounts of each compound were changed, and water was added to make the solid content 5% by mass. Polymer (a-2) had a weight-average molecular weight of 78,600 and a dispersity of 29.8. The repeating structure and terminal end structure of polymer (a-2) are shown in the following formula: The numbers to the right of [ ] are the molar ratios of each structural unit to all structural units. [ka]

[0094] [Polymer (a-3)] Polymer (a-3) was synthesized in the same manner as polymer (a-1), except that compound (a1) was used in addition to compound (a2) and the amounts of each compound were changed. The weight-average molecular weight of polymer (a-3) was 122,800, and the polydispersity was 19.1. The repeating structure and terminal end structure of polymer (a-3) are shown in the following formula: The numbers to the right of [ ] are the molar ratios of each structural unit to all structural units. [ka]

[0095] [Polymer (a-4) to Polymer (a-8)] Polymers (a-4) to (a-8) were synthesized in the same manner as polymer (a-1), except that the amounts of each compound were changed. The weight-average molecular weight of polymer (a-4) was 776,700, with a dispersity of 65.8. The weight-average molecular weight of polymer (a-5) was 560,100, with a dispersity of 41.8. The weight-average molecular weight of polymer (a-6) was 700,700, with a dispersity of 44.1. The weight-average molecular weight of polymer (a-7) was 941,300, with a dispersity of 55.5. The weight-average molecular weight of polymer (a-8) was 1,022,700, with a dispersity of 73.5.

[0096] [Polymer (a-9)] Polymer (a-9) was synthesized in the same manner as polymer (a-1), except that compound (b2) was used instead of compound (b1) and the amounts of each compound were changed. The weight-average molecular weight of polymer (a-9) was 563,400 and the polydispersity was 39.2. The repeating structure and terminal end structure of polymer (a-9) are shown in the following formula: The numbers to the right of [ ] are the molar ratios of each structural unit to all structural units. [ka]

[0097] [Polymer (a-10)] Polymer (a-10) was synthesized in the same manner as polymer (a-1), except that compound (a) was not added and the amounts of each compound were changed. The weight-average molecular weight of polymer (a-10) was 402,000 and the polydispersity was 33.1. The repeating structure and terminal end structure of polymer (a-10) are shown in the following formula: The numbers to the right of [ ] are the molar ratios of each structural unit to all structural units. [ka]

[0098] [Polymer (a-11)] Polymer (a-11) was synthesized in the same manner as polymer (a-1), except that compound (b) was not added and the amounts of each compound were changed. The weight-average molecular weight of polymer (a-11) was 385,400 and the polydispersity was 34.7. The repeating unit and terminal end unit structure of polymer (a-11) are shown in the following formula: The numbers to the right of [ ] are the molar ratios of each unit to all units. [ka]

[0099] [Polymer (a-12)] Polymer (a-12) was synthesized in the same manner as polymer (a-1), except that compound (c) was not added and the amounts of each compound were changed. The weight-average molecular weight of polymer (a-12) was 423,000 and the polydispersity was 40.1. The repeating unit and terminal end unit structure of polymer (a-12) are shown in the following formula: The numbers to the right of [ ] are the molar ratios of each unit to all units. [ka]

[0100] [Polymer (a-13)] Polymer (a-13) was synthesized in the same manner as polymer (a-1), except that the 1% by mass propylene glycol monomethyl ether solution of compound d1 was not added. The weight-average molecular weight of polymer (a-13) was 986,000, and the polydispersity was 51.8. The repeating unit and terminal end unit structure of polymer (a-13) are shown in the following formula: The numbers to the right of [ ] are the molar ratios of each unit to all units. [ka]

[0101] The molar ratio of each structural unit structure to all structural units of polymer (a-1) to polymer (a-14) is shown in Table 1. Table 1 also shows whether or not structure (d) is present in polymer (a-1) to polymer (a-14).

[0102] The various chemicals used in the examples and comparative examples will be collectively described below. a-1 to a-14: Polymers (a-1) to (a-14) synthesized by the above method b-1: Acrylate compound represented by the following formula (total of m: 60, n: 4, HLB value: 16.11) [ka] b-2: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd., a mixture of dipentaerythritol hexaacrylate (a=6, b=0) / dipentaerythritol pentaacrylate (a=5, b=1) represented by the following formula, HLB value: 0.65 or less) [ka] c-1: sodium di-2-ethylhexyl sulfosuccinate (manufactured by Tokyo Chemical Industry Co., Ltd., anionic surfactant, compound represented by the following formula) [ka] d-1: IRGACURE 651 (manufactured by IGM Resins, a compound represented by the following formula (Ph represents a phenyl group)) Ph-C(=O)-C(OCH3)2-Ph e-1: Propylene glycol monomethyl ether (PGME) e-2: Isopropyl alcohol (IPA)

[0103] <Examples and Comparative Examples> The types and amounts (parts by mass) of polymers listed in Table 1, 70 parts by mass of compound b-1, 30 parts by mass of compound b-2, 1 part by mass of compound c-1, 5 parts by mass of compound d-1, 112 parts by mass of compound e-1, and 4 parts by mass of e-2 were uniformly mixed to obtain anti-fog coating compositions for the Examples and Comparative Examples. Each of the obtained anti-fog coating compositions was applied to a 5 cm x 5 cm polycarbonate (PC) plate using a spin coater, and the coating film was heated at 80°C for 1 minute. Thereafter, the coating film was heated at 1000 mJ / cm using an ultra-high pressure mercury lamp. 2 A PC board (anti-fogging PC board) having an anti-fogging coating film with a thickness of 5 μm was produced.

[0104] <Anti-fog durability> An anti-fog PC panel was immersed in 1 L of pure water in a tray for 2 hours. The panel was then removed and dried at room temperature for 18 hours. 700 mL of 50°C water was added to a 1000 mL beaker, and the anti-fog coating film on the dried anti-fog PC panel was exposed to the water 7 cm above the water surface for 3 minutes. The degree of fogging of the anti-fog PC panel was then visually evaluated according to the following criteria. The results are shown in Table 1. A: It's not cloudy B: Cloudy

[0105] In the following Table 1, (a) to (d) respectively represent compounds (a) to (d). The column (d) indicates whether or not the polymer contains a structure (d) derived from compound (d). [Table 1]

[0106] As shown in Table 1, the anti-fogging durability of the Examples in which the specified polymer (A) was added was good, whereas the anti-fogging durability was poor in Comparative Example 1 in which the specified polymer (A) was not added and Comparative Examples 2 to 5 in which polymers other than the specified polymer (A) were added. Therefore, it was confirmed that the anti-fogging coating composition according to the present invention provides an anti-fogging coating film with excellent anti-fogging durability.

Claims

1. An optical product comprising a transparent material and an anti-fog coating film disposed on a surface of the transparent material, the anti-fog coating film is obtained by drying and / or curing a coating film made of an anti-fog coating composition, the anti-fog coating composition comprises a polymer (A), a substrate component (B), and a surfactant (C); the polymer (A) comprises a structural unit derived from a compound (a), a structural unit derived from a compound (b), and a structural unit derived from a compound (c), The polymer (A) has a structure derived from the compound (d) at at least one end of the main chain, The compound (a) is a compound having an ethylenically unsaturated group and an ionic group, The compound (b) represents an ethylenically unsaturated group and an —OH group and / or —NH ２ and a compound having a group, The compound (c) is a compound represented by the following formula (c-1): The compound (d) is a compound having a thiol group and a hydrocarbon group having 4 or more carbon atoms, An optical product, wherein the substrate component (B) comprises a resin (B1) and / or a polymerizable monomer (B2). 【Chemistry 1】 (In formula (c-1), R ｃ１ represents a hydrogen atom or a methyl group, R ｃ２ represents a hydrocarbon group having 1 to 12 carbon atoms, R ｃ３ represents a hydrocarbon group having 2 to 4 carbon atoms, and R ｃ４ represents a hydrocarbon group having 12 or more carbon atoms, cm represents 0 or 1, and cn represents an integer of 1 or more and 500 or less.

2. 10. The optical product of claim 1, which is a mirror, a window, a prism, a lens, or a goggle.

3. A composition comprising a polymer (A), a base component (B), and a surfactant (C), the polymer (A) comprises a structural unit derived from a compound (a), a structural unit derived from a compound (b), and a structural unit derived from a compound (c), The polymer (A) has a structure derived from the compound (d) at at least one end of the main chain, The compound (a) is a compound having an ethylenically unsaturated group and an ionic group, The compound (b) has an ethylenically unsaturated group and an —OH group and / or —NH ２ and a compound having a group, The compound (c) is a compound represented by the following formula (c-1): The compound (d) is a compound having a thiol group and a hydrocarbon group having 4 or more carbon atoms, The anti-fog coating composition, wherein the base material component (B) comprises a resin (B1) and / or a polymerizable monomer (B2). 【Chemistry 2】 (In formula (c-1), R ｃ１ represents a hydrogen atom or a methyl group, R ｃ２ represents a hydrocarbon group having 1 to 12 carbon atoms, R ｃ３ represents a hydrocarbon group having 2 to 4 carbon atoms, and R ｃ４ represents a hydrocarbon group having 12 or more carbon atoms, cm represents 0 or 1, and cn represents an integer of 1 or more and 500 or less.

4. With respect to all structural units of the polymer (A), the molar ratio of the structural unit derived from the compound (a) is 50 mol % or more and 98 mol % or less, the molar ratio of the structural unit derived from the compound (b) is 1 mol % or more and 40 mol % or less, The anti-fog coating composition according to claim 3 , wherein the molar ratio of the structural unit derived from the compound (c) is 1 mol % or more and 20 mol % or less.

5. 5. The anti-fog coating composition according to claim 3, wherein the mass of the polymer (A) is 0.05 parts by mass or more and 10 parts by mass or less relative to 100 parts by mass of the base component (B).

6. The anti-fog coating composition according to claim 3 or 4, wherein the base component (B) comprises the polymerizable monomer (B2).

7. A cured product of the anti-fog coating composition according to claim 6.

8. An anti-fog coating film obtained by drying and / or curing a coating film made of the anti-fog coating composition according to claim 3.

9. A polymer comprising a structural unit derived from a compound (a), a structural unit derived from a compound (b), and a structural unit derived from a compound (c), the polymer has a structure derived from compound (d) at at least one end of the main chain, The compound (a) is a compound having an ethylenically unsaturated group and an ionic group, The compound (b) has an ethylenically unsaturated group and an —OH group and / or —NH ２ and a compound having a group, The compound (c) is a compound represented by the following formula (c-1): The compound (d) is a polymer, which is a compound having a thiol group and a hydrocarbon group having 4 or more carbon atoms. 【Transformation 3】 (In formula (c-1), R ｃ１ represents a hydrogen atom or a methyl group, R ｃ２ represents a hydrocarbon group having 1 to 12 carbon atoms, R ｃ３ represents a hydrocarbon group having 2 to 4 carbon atoms, and R ｃ４ represents a hydrocarbon group having 12 or more carbon atoms, cm represents 0 or 1, and cn represents an integer of 1 or more and 500 or less.

10. The method for producing a polymer according to claim 9 , wherein the compound (a), the compound (b), and the compound (c) are polymerized in the presence of the compound (d).

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