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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/005—Stabilisers against oxidation, heat, light, ozone
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
  • C08K5/45—Heterocyclic compounds having sulfur in the ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
  • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
  • C07D211/94—Oxygen atom, e.g. piperidine N-oxide
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
  • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
  • C07D307/83—Oxygen atoms
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  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
  • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
  • C07D495/04—Ortho-condensed systems
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  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2/00—Processes of polymerisation
  • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
  • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
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  • C08F20/38—Esters containing sulfur
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  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
  • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
  • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
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  • C08K5/00—Use of organic ingredients
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  • C08K5/13—Phenols; Phenolates
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  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/15—Heterocyclic compounds having oxygen in the ring
  • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
  • C08K5/1535—Five-membered rings
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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
  • C08K5/3432—Six-membered rings
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  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
  • C08K5/3445—Five-membered rings
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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L101/00—Compositions of unspecified macromolecular compounds
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
  • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
• • G—PHYSICS
  • G02—OPTICS
  • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
  • G02C7/00—Optical parts
  • G02C7/02—Lenses; Lens systems ; Methods of designing lenses
• • G—PHYSICS
  • G02—OPTICS
  • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
  • G02C7/00—Optical parts
  • G02C7/02—Lenses; Lens systems ; Methods of designing lenses
  • G02C7/04—Contact lenses for the eyes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K2201/00—Specific properties of additives
  • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K

Definitions

• the present invention relates to a composition containing an ultraviolet absorber.
• the present invention also relates to a cured product and an optical component using a composition containing an ultraviolet absorber.
• Benzobisdithiol compounds have excellent ultraviolet absorption properties and are used as ultraviolet absorbents.
• Patent Document 1 describes the use of specific benzobisdithiols as ultraviolet absorbents.
• UV absorbers One of the required properties of UV absorbers is that they are required to have little coloration. In recent years, there has also been a demand for them to have high absorption capacity for UV rays with longer wavelengths, around 400 nm.
• ultraviolet absorption performance of ultraviolet absorbers can decrease over time due to exposure to light.
• ultraviolet absorbers whose maximum absorption wavelength is on the longer side of the ultraviolet region tend to have poor light resistance and their ultraviolet absorption ability tends to decrease over time. For this reason, there has been a demand in recent years for further improvements in the light resistance of ultraviolet absorbers.
• the object of the present invention is therefore to provide a composition that can be used to produce a cured product that has excellent absorption of ultraviolet light with a wavelength of around 400 nm, is less colored, and has excellent light resistance.
• Another object of the present invention is to provide a cured product and an optical component.
• the present inventors have conducted intensive research into compounds having a skeleton represented by formula (1), and have found that a compound having a structure in which Q1 and Q2 in formula (1) are a specific combination has excellent ultraviolet absorption ability at a wavelength of about 400 nm, is less colored, and is excellent in light resistance. Further research has revealed that by using this compound in combination with a specific discoloration inhibitor, a film with less coloring can be obtained even after long-term light irradiation, and the present invention has been completed. Thus, the present invention provides the following.
• a coating composition comprising an ultraviolet absorber, a curable compound, and a color-fading inhibitor
• the ultraviolet absorber includes at least one selected from a compound represented by formula (1) and a polymer including a structure derived from the compound represented by formula (1), a composition, wherein the discoloration inhibitor comprises at least one selected from an amine compound, a phenol compound, a hydroquinone compound, a catechol compound, an ascorbic acid compound, a carotenoid compound, a metal complex compound, and a benzolactone compound;
• Q 1 represents a group represented by formula (Q-1);
• composition according to ⁇ 1> wherein the compound represented by formula (1) is a compound represented by formula (3);
• Q3 represents a group represented by formula (Q-1) above;
• R a1 to R a4 each independently represent a hydrogen atom, an alkyl group, or an alkenyl group.
• X a11 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an ary
• ⁇ 5> The composition according to any one of ⁇ 1> to ⁇ 4>, wherein the curable compound includes at least one selected from a resin and a polymerizable compound.
• the curable compound contains a resin, and the resin is at least one selected from the group consisting of a (meth)acrylic resin, a polystyrene resin, a polyester resin, a polyurethane resin, a thiourethane resin, a polyimide resin, an epoxy resin, a polycarbonate resin, a phthalate resin, a cellulose acylate resin, and a cyclic olefin resin.
• An optical member comprising the cured product according to ⁇ 7>.
• the present invention can provide a composition that can be used to produce a cured product that has excellent absorption of ultraviolet light with a wavelength of about 400 nm, is less colored, and has excellent light resistance.
• the present invention can also provide a cured product and an optical component.
• alkyl group includes not only alkyl groups without a substituent (unsubstituted alkyl groups) but also alkyl groups with a substituent (substituted alkyl groups).
• a numerical range expressed using "to” means a range that includes the numerical values before and after "to” as the lower and upper limits.
• the total solid content refers to the total amount of all components in the resin composition excluding the solvent.
• (meth)acrylate refers to both or either of acrylate and methacrylate
• (meth)acrylic refers to both or either of acrylic and methacrylic
• (meth)allyl refers to both or either of allyl and methallyl
• (meth)acryloyl refers to both or either of acryloyl and methacryloyl.
• process does not only mean an independent process, but also means that even if a process cannot be clearly distinguished from other processes, the process is included in this term as long as the intended effect of the process is achieved.
• the weight average molecular weight (Mw) and the number average molecular weight (Mn) are defined as values calculated in terms of polystyrene measured by gel permeation chromatography (GPC).
• the composition of the present invention comprises an ultraviolet absorber, a curable compound, and a color-fading inhibitor
• the ultraviolet absorber includes at least one selected from a compound represented by formula (1) and a polymer including a structure derived from the compound represented by formula (1)
• the anti-fading agent is characterized by containing at least one compound selected from an amine compound, a phenol compound, a hydroquinone compound, a catechol compound, an ascorbic acid compound, and a benzolactone compound.
• the compound represented by formula (1) and the polymer containing a structure derived from the compound represented by formula (1) are excellent in absorbing ultraviolet light at a wavelength of about 400 nm, are less colored, and are excellent in light resistance, such as being less susceptible to decomposition due to light irradiation.
• the composition of the present invention which contains at least one selected from the compound represented by formula (1) and the polymer containing a structure derived from the compound represented by formula (1) as an ultraviolet absorber, can produce a cured product having excellent absorbing ability for ultraviolet light at a wavelength of about 400 nm, less colored, and excellent light resistance.
• the composition of the present invention further contains at least one anti-fading agent selected from amine compounds, phenol compounds, hydroquinone compounds, catechol compounds, ascorbic acid compounds, and benzolactone compounds, so that even if a film obtained using the composition is irradiated with light for a long period of time, the decomposition of the compound represented by formula (1) or the polymer containing a structure derived from the compound represented by formula (1) can be suppressed. Therefore, according to the composition of the present invention, a film with little coloring can be obtained even after long-term light irradiation. Therefore, the composition of the present invention has excellent ability to absorb ultraviolet light with a wavelength of about 400 nm, and can produce a cured product with little coloring and excellent light resistance.
• at least one anti-fading agent selected from amine compounds, phenol compounds, hydroquinone compounds, catechol compounds, ascorbic acid compounds, and benzolactone compounds
• the composition of the present invention may be a composition in a solution state containing a solvent.
• the composition of the present invention may also be a kneaded product.
• the kneaded product is obtained by kneading a resin with an ultraviolet absorber containing at least one selected from the compound represented by formula (1) and a polymer containing a structure derived from the compound represented by formula (1).
• the kneaded product in this specification is a product in which an ultraviolet absorber is mixed and dispersed in a resin, and is different from a solution in which an ultraviolet absorber and a resin are dissolved or dispersed in a solvent.
• a curable compound containing a resin is used.
• the kneaded material is preferably in the form of pellets.
• pellets refer to a material obtained by granulating (pelletizing) the kneaded material into a fixed shape such as a sphere, ellipsoid, cylinder, or prism.
• the pellets are also preferably in the form of master pellets (master batches).
• Master pellets (master batches) refer to a material in which a high concentration of additives such as ultraviolet absorbers are dispersed in resin, and are mixed with resin at a specified ratio when forming a molded body.
• the composition of the present invention contains an ultraviolet absorber.
• the ultraviolet absorber contains at least one selected from a compound represented by formula (1) and a polymer containing a structure derived from the compound represented by formula (1).
• the ultraviolet absorber is preferably one containing a compound represented by formula (1).
• the compound represented by formula (1) is also referred to as a specific compound.
• the polymer containing a structure derived from the compound represented by formula (1) is also referred to as a specific polymer.
• the specific compound and the specific polymer are collectively referred to as a specific ultraviolet absorber.
• Q 1 represents a group represented by formula (Q-1);
• R 1 and R 2 each independently represent a hydrogen atom or a substituent;
• X 1 to X 4 each independently represent -S-, -NR X1 -, or -SO 2 -, where R X1 represents a hydrogen atom or an alkyl group;
• * represents a bond
• R 101 and R 102 each independently represent a bond
• R 101 and R 102 each independently represent a bond
• R1 and R2 examples of the substituents represented by R 1 and R 2 in formula (1) include an alkyl group, an aryl group, an aralkyl group, a heterocyclic group, a group containing a polymerizable group having an ethylenically unsaturated bond, -OH, -O-Y 11 , -OC( ⁇ O)-Y 11 , -OC( ⁇ O)O-Y 11 , -OC( ⁇ O)NR y11 -Y 11 , -OSO 2 -Y 11 , a cyano group, a halogen atom, and a nitro group.
• R y11 represents a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group
• Y 11 represents an alkyl group, an aralkyl group, or an aryl group.
• the number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.
• the alkyl group may be linear, branched, or cyclic, and is preferably linear or branched.
• the alkyl group may have a substituent. Examples of the substituent include the groups described below for the substituent T.
• the number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, even more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8.
• the aryl group may have a substituent. Examples of the substituent include the groups described below for the substituent T.
• the number of carbon atoms in the alkyl portion of the aralkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
• the number of carbon atoms in the aryl portion of the aralkyl group is preferably 6 to 30, more preferably 6 to 20, even more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8.
• the aralkyl group may have a substituent. Examples of the substituent include the groups explained in the substituent T described below. Specific examples of aralkyl groups include a benzyl group.
• the heterocycle in the heterocyclic group preferably contains a 5- or 6-membered saturated or unsaturated heterocycle.
• An aliphatic ring, an aromatic ring, or another heterocycle may be condensed to the heterocycle.
• heteroatoms constituting the heterocycle include B, N, O, S, Se, and Te, with N, O, and S being preferred.
• the carbon atom in the heterocycle has a free valence (monovalent) (the heterocyclic group is bonded at a carbon atom).
• the number of carbon atoms in the preferred heterocyclic group is 1 to 40, more preferably 1 to 30, and even more preferably 1 to 20.
• Examples of saturated heterocycles in the heterocyclic group include a pyrrolidine ring, a morpholine ring, a 2-bora-1,3-dioxolane ring, and a 1,3-thiazolidine ring.
• Examples of unsaturated heterocyclic rings in the heterocyclic group include an imidazole ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a benzotriazole ring, a benzoselenazole ring, a pyridine ring, a pyrimidine ring, and a quinoline ring.
• halogen atoms include chlorine atoms, bromine atoms, iodine atoms, etc.
• examples of the polymerizable group having an ethylenically unsaturated bond include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group, and the (meth)acryloyloxy group and the vinylphenyl group are preferred.
• Examples of the group containing a polymerizable group having an ethylenically unsaturated bond include a group represented by the following formula (T1). *-X T1 -Y T1 -Z T1 ...(T1)
• X T1 represents a single bond, —O—, —OC( ⁇ O)—, —OC( ⁇ O)O— or —OC( ⁇ O)NRx 1 —, where Rx 1 represents a hydrogen atom, an alkyl group or an aryl group; Y T1 represents a single bond or a divalent linking group; ZT1 represents a polymerizable group having an ethylenically unsaturated bond.
• the alkyl group represented by Rx1 is preferably an alkyl group having 1 to 30 carbon atoms. Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group.
• the aryl group represented by Rx1 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Specific examples include a phenyl group, a p-tolyl group, and a naphthyl group.
• Rx1 is preferably a hydrogen atom.
• XT1 is preferably --O--, --OC(.dbd.O)-- or --OC(.dbd.O)NH--, and from the viewpoint of synthesis, is more preferably --OC(.dbd.O)--.
• the divalent linking group represented by Y T1 includes a hydrocarbon group and a group in which two or more hydrocarbon groups are linked by a single bond or a linking group.
• the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group, and an aliphatic hydrocarbon group is preferable.
• the number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15.
• the aliphatic hydrocarbon group may be linear, branched, or cyclic.
• the cyclic aliphatic hydrocarbon group may be a monocyclic or condensed ring.
• the cyclic aliphatic hydrocarbon group may have a crosslinked structure.
• the number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10.
• the hydrocarbon group may have a substituent.
• the substituent include the substituent T described below.
• an example of the substituent is a hydroxyl group.
• Examples of the polymerizable group having an ethylenically unsaturated bond represented by ZT1 include a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group, and the (meth)acryloyloxy group and the vinylphenyl group are preferred.
• T1 Specific examples of the group represented by formula (T1) include the groups represented by T-1 to T-32 below.
• Me is a methyl group
• * is a bond.
• R 1 and R 2 in formula (1) are each independently -OH, -O-Y 11 , -OC( ⁇ O)-Y 11 , -OC( ⁇ O)O-Y 11 , -OC( ⁇ O)NR y11 -Y 11 , -OSO 2 -Y 11 or a group containing a polymerizable group having an ethylenically unsaturated bond.
• R 1 and R 2 in formula (1) may be the same group or different groups.
• R y11 is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
• Y 11 is preferably an alkyl group from the viewpoint of excellent solubility, more preferably a linear or branched alkyl group, and even more preferably a branched alkyl group.
• at least one of R 1 and R 2 is a group containing a polymerizable group having an ethylenically unsaturated bond. According to this embodiment, an effect of suppressing bleeding out in the film can be obtained.
• one of R 1 and R 2 is —O—Y 11 , and the other is —OC( ⁇ O)—Y 11 .
• R 1 and R 2 are --O--Y 11 or --OC(.dbd.O)--Y 11 , and the other is a group containing a polymerizable group having an ethylenically unsaturated bond.
• X 1 to X 4 each independently represent -S-, -NR X1 -, or -SO 2 -, and R X1 represents a hydrogen atom or an alkyl group.
• the preferred range of the alkyl group represented by R X1 is the same as the alkyl group described above.
• R X1 is preferably a hydrogen atom.
• X 1 to X 4 in formula (1) are preferably --S-- because the effects of the present invention are more pronounced.
• Q1 - Q1 in formula (1) represents a group represented by formula (Q-1).
• R 101 and R 102 in formula (Q-1) each independently represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group or a group containing a polymerizable group having an ethylenically unsaturated bond.
• R 101 or R 102 when either R 101 or R 102 is a hydrogen atom, the other represents an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond; when either R 101 or R 102 is a methyl group, the other represents a hydrogen atom, an alkyl group having 2 or more carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond; and when either R 101 or R 102 is a phenyl group, the other represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group having a substituent, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.
• the number of carbon atoms in the alkyl group represented by R 101 and R 102 is preferably 1 to 30.
• the upper limit is preferably 20 or less, more preferably 15 or less, even more preferably 10 or less, and even more preferably 8 or less.
• the lower limit is preferably 2 or more, and more preferably 3 or more.
• the alkyl group may be linear, branched, or cyclic, and is preferably linear or branched.
• the alkyl group may have a substituent. Examples of the substituent include the groups explained in the substituent T described below.
• the number of carbon atoms of the aryl group represented by R 101 and R 102 is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8.
• the aryl group may have a substituent. Examples of the substituent include the groups explained in the substituent T described later.
• the number of carbon atoms in the alkyl portion of the aralkyl group represented by R 101 and R 102 is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
• the number of carbon atoms in the aryl portion of the aralkyl group is preferably 6 to 30, more preferably 6 to 20, even more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8.
• the aralkyl group may have a substituent. Examples of the substituent include the groups explained in the substituent T described below.
• Examples of the heterocyclic group represented by R 101 and R 102 include the heterocyclic groups described above.
• Examples of the group containing a polymerizable group having an ethylenically unsaturated bond represented by R 101 and R 102 include a group represented by formula (V1). *-X V1 -Y V1 -Z V1 ...(V1)
• the alkyl group and aryl group represented by Rx2 have the same meaning as the alkyl group and aryl group represented by Rx1 in the group represented by formula (T1), and the preferred ranges are also the same.
• Rx2 is preferably a hydrogen atom.
• X V1 is preferably a single bond or —C( ⁇ O)—, and more preferably a single bond.
• Examples of the divalent linking group represented by Y V1 include the groups explained as the divalent linking group represented by Y T1 in the group represented by formula (T1), and the preferred ranges are also the same.
• Examples of the polymerizable group having an ethylenically unsaturated bond represented by ZV1 include a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group, and the (meth)acryloyloxy group and the vinylphenyl group are preferred.
• V1 Specific examples of the group represented by formula (V1) include the groups represented by V-1 to V-12 below.
• * represents a bond.
• R 101 and R 102 each independently represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, or a heterocyclic group;
• R 101 or R 102 is a hydrogen atom
• the other represents an alkyl group, an aralkyl group, an aryl group, or a heterocyclic group;
• R 101 or R 102 is a methyl group
• the other represents a hydrogen atom, an alkyl group having 2 or more carbon atoms, an aralkyl group, an aryl group, or a heterocyclic group;
• R 101 or R 102 is a phenyl group
• the other may be a hydrogen atom, an alkyl group, an aralkyl group, a substituted aryl group, or a heterocyclic group.
• R 101 and R 102 each independently represent preferably an alkyl group or an aralkyl group, and more preferably an aralkyl group.
• R 101 and R 102 are alkyl groups, it is preferable that the alkyl groups represented by R 101 and R 102 are each independently an alkyl group having 2 or more carbon atoms.
• R 101 and R 102 in formula (Q-1) is an embodiment in which at least one of R 101 and R 102 in formula (Q-1) is a group containing a polymerizable group having an ethylenically unsaturated bond, which has the effect of suppressing bleed-out in the film.
• Examples of the substituents represented by R q1 to R q3 include a cyano group, a carbamoyl group, a sulfamoyl group, a nitro group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkyl group, an aryl group, a heterocyclic group, and a group containing a polymerizable group having an ethylenically unsaturated bond. These groups may further have a substituent. Examples of the substituent include the groups listed as the substituent T described below.
• the carbamoyl group may be a carbamoyl group having 1 to 10 carbon atoms, preferably a carbamoyl group having 2 to 8 carbon atoms, and more preferably a carbamoyl group having 2 to 5 carbon atoms.
• sulfamoyl groups include sulfamoyl groups having 0 to 10 carbon atoms, preferably sulfamoyl groups having 2 to 8 carbon atoms, and more preferably sulfamoyl groups having 2 to 5 carbon atoms.
• the acyl group may be an acyl group having 1 to 20 carbon atoms, preferably an acyl group having 1 to 12 carbon atoms, and more preferably an acyl group having 1 to 8 carbon atoms.
• the alkylsulfonyl group may be an alkylsulfonyl group having 1 to 20 carbon atoms, preferably an alkylsulfonyl group having 1 to 10 carbon atoms, and more preferably an alkylsulfonyl group having 1 to 8 carbon atoms.
• the arylsulfonyl group may be an arylsulfonyl group having 6 to 20 carbon atoms, and preferably an arylsulfonyl group having 6 to 10 carbon atoms.
• the alkylsulfinyl group may be an alkylsulfinyl group having 1 to 20 carbon atoms, preferably an alkylsulfinyl group having 1 to 10 carbon atoms, and more preferably an alkylsulfinyl group having 1 to 8 carbon atoms.
• the arylsulfinyl group may be an arylsulfinyl group having 6 to 20 carbon atoms, and preferably an arylsulfinyl group having 6 to 10 carbon atoms.
• alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 20 carbon atoms, preferably alkoxycarbonyl groups having 2 to 12 carbon atoms, and more preferably alkoxycarbonyl groups having 2 to 8 carbon atoms.
• the aryloxycarbonyl group may be an aryloxycarbonyl group having 6 to 20 carbon atoms, preferably an aryloxycarbonyl group having 6 to 12 carbon atoms, and more preferably an aryloxycarbonyl group having 6 to 8 carbon atoms.
• alkyl group examples include alkyl groups having 1 to 18 carbon atoms, preferably alkyl groups having 1 to 10 carbon atoms, and more preferably alkyl groups having 1 to 5 carbon atoms.
• the aryl group may be an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 15 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms.
• the heterocycle in the heterocyclic group preferably contains a 5- or 6-membered saturated or unsaturated heterocycle.
• the heterocycle may be condensed with an aliphatic ring, an aromatic ring, or another heterocycle.
• Heteroatoms constituting the heterocycle include B, N, O, S, Se, and Te, with N, O, and S being preferred.
• the carbon atom in the heterocycle has a free valence (monovalent) (the heterocyclic group is bonded at a carbon atom).
• the number of carbon atoms in the preferred heterocyclic group is 1 to 40, more preferably 1 to 30, and even more preferably 1 to 20.
• Examples of the group containing a polymerizable group having an ethylenically unsaturated bond include a group represented by formula (U1). *-X U1 -Y U1 -Z U1 ...(U1)
• the alkyl group and aryl group represented by Rx3 have the same meaning as the alkyl group and aryl group represented by Rx1 in the group represented by formula (T1), and the preferred ranges are also the same.
• Rx3 is preferably a hydrogen atom.
• X U1 is preferably —C( ⁇ O)O— or —C( ⁇ O)NRx 3 —, and from the viewpoint of synthesis, is more preferably —C( ⁇ O)O—.
• Examples of the divalent linking group represented by Y 1 U1 include the groups explained as the divalent linking group represented by Y 1 T1 in the group represented by formula (T1), and the preferred ranges are also the same.
• Examples of the polymerizable group having an ethylenically unsaturated bond represented by Z include a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group, and the (meth)acryloyloxy group and the vinylphenyl group are preferred.
• At least one of Rq2 and Rq3 is preferably an electron-withdrawing group, and it is more preferable that Rq2 and Rq3 are electron -withdrawing groups.
• At least one of R q2 and R q3 is preferably a group containing a polymerizable group having an ethylenically unsaturated bond.
• it is also preferable that one of R q2 and R q3 is a group containing a polymerizable group having an ethylenically unsaturated bond, and the other is an electron-withdrawing group.
• Electron-withdrawing groups include those with a Hammett's substituent constant ⁇ p value of 0.2 or more.
• the Hammett's substituent constant ⁇ value will be explained.
• the Hammett's rule is an empirical rule proposed by L. P. Hammett in 1935 to quantitatively discuss the effect of substituents on the reaction or equilibrium of benzene derivatives, and its validity is widely recognized today.
• the substituent constants determined by the Hammett's rule include ⁇ p and ⁇ m values, and these values can be found in many general textbooks. For example, see Lange's Handbook of Chemistry, 12th Edition, 1979 (McGraw-Hill), edited by J. A. Dean, and Chemistry Area, special edition, No. 122, pp.
• a substituent having a Hammett's substituent constant ⁇ p value of 0.2 or more indicates an electron-withdrawing group.
• the electron-withdrawing group is preferably a group having a Hammett's substituent constant ⁇ p value of 0.25 or more, more preferably a group having a Hammett's substituent constant ⁇ p value of 0.3 or more, and even more preferably a group having a Hammett's substituent constant ⁇ p value of 0.35 or more.
• Me represents a methyl group
• Ph represents a phenyl group.
• the values in parentheses are the ⁇ p values of representative
• R q2 and R q3 each independently represent a hydrogen atom, a cyano group, a carbamoyl group, a sulfamoyl group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a nitro group, an alkoxycarbonyl group, an aryloxycarbonyl group, or a group containing a polymerizable group having an ethylenically unsaturated bond.
• R q2 and R q3 are each independently a hydrogen atom, a cyano group, a carbamoyl group, a sulfamoyl group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a nitro group, an alkoxycarbonyl group, or an aryloxycarbonyl group.
• R q2 and R q3 are preferably a cyano group, an alkoxycarbonyl group, a nitro group, or an alkylsulfonyl group, and it is more preferable that R q2 and R q3 are each independently a cyano group or an alkoxycarbonyl group.
• R q2 and R q3 are each independently a cyano group or an alkoxycarbonyl group.
• one of R q2 and R q3 is a cyano group, and the other is an alkoxycarbonyl group.
• R q2 and R q3 are a group containing a polymerizable group having an ethylenically unsaturated bond.
• R q2 and R q3 may each independently be a group containing a polymerizable group having an ethylenically unsaturated bond, or one of R q2 and R q3 may be a group containing a polymerizable group having an ethylenically unsaturated bond, and the other may be an electron-withdrawing group.
• the ring formed is preferably a ring other than the structure represented by formula (Q-1) because the effects of the present invention are more pronounced.
• rings other than the structure represented by formula (Q-1) include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a pyrrolidine ring, a tetrahydrofuran ring, a tetrahydrothiophene ring, an oxazoline ring, a thiazoline ring, a pyrroline ring, a pyrazoline ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a piperazine ring, a pyran ring, and an indandione ring. These may have a substituent at any position.
• At least one of R 1 , R 2 , Q 1 and Q 2 in formula (1) preferably contains a group containing a polymerizable group having an ethylenically unsaturated bond, and it is more preferable that one or two of R 1 , R 2 , Q 1 and Q 2 contain a group containing a polymerizable group having an ethylenically unsaturated bond.
• at least one of R1 , R2 , Rq2 , Rq3 , R101 , and R102 is a group containing a polymerizable group having an ethylenically unsaturated bond
• the number of polymerizable groups having an ethylenically unsaturated bond contained in formula (1) is preferably 1 to 2.
• the specific compound is preferably a compound represented by formula (3).
• Q3 represents a group represented by formula (Q-1) above;
• R y11 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group
• Y 11 represents an alkyl group, an aralkyl group or an aryl group.
• Q3 and Q4 in formula (3) have the same definitions as Q1 and Q2 in formula (1), and the preferred ranges are also the same.
• the preferred ranges of Ry11 and Y11 in formula (3) are the same as those of Ry11 and Y11 described in formula (1).
• R 11 and R 12 is a group containing a polymerizable group having an ethylenically unsaturated bond.
• one of R 11 and R 12 is —O—Y 11 , and the other is —OC( ⁇ O)—Y 11 .
• Another embodiment is one in which one of R 11 and R 12 is --O--Y 11 or --OC(.dbd.O)--Y 11 , and the other is a group containing a polymerizable group having an ethylenically unsaturated bond.
• at least one of R11 , R12 , Rq12, Rq13 , R101 , and R102 is a group containing a polymerizable group having an ethylenically unsaturated bond
• the number of polymerizable groups having an ethylenically unsaturated bond contained in formula (3) is preferably 1 or 2.
• the specific compound is preferably a compound represented by formula (6).
• Q5 represents a group represented by formula (Q-1) above.
• Q5 and Q6 in formula (6) have the same definitions as Q1 and Q2 in formula (1), and the preferred ranges are also the same.
• the preferred ranges of Ry61 and Y61 in formula (6) are the same as Ry11 and Y11 described in formula (1).
• R 61 and R 62 may be the same group or different groups.
• bicyclo[1,2,2]heptan-2-yl and bicyclo[2,2,2]octan-3-yl groups), and tricyclo structures having more ring structures are also included.
• the alkyl groups in the substituents described below (for example, the alkyl groups of alkylthio groups) also represent alkyl groups of this concept. ]; Alkenyl groups [linear, branched, and cyclic alkenyl groups.
• linear or branched alkenyl groups preferably linear or branched alkenyl groups having 2 to 30 carbon atoms, such as vinyl, allyl, prenyl, geranyl, and oleyl groups
• cycloalkenyl groups preferably cycloalkenyl groups having 3 to 30 carbon atoms. That is, monovalent groups obtained by removing one hydrogen atom from a cycloalkene having 3 to 30 carbon atoms.
• 2-cyclopenten-1-yl and 2-cyclohexen-1-yl groups and bicycloalkenyl groups (preferably bicycloalkenyl groups having 5 to 30 carbon atoms.
• bicyclo[2,2,1]hept-2-en-1-yl and bicyclo[2,2,2]oct-2-en-4-yl groups) are included.
• An alkynyl group preferably a linear or branched alkynyl group having 2 to 30 carbon atoms, for example, an ethynyl group or a propargyl group
• An aryl group (preferably an aryl group having 6 to 30 carbon atoms, for example, a phenyl group, a p-tolyl group, a naphthyl group, a m-chlorophenyl group, or an o-hexadecanoylaminophenyl group); Heterocyclic groups (preferably monovalent groups obtained by removing one hydrogen atom from a 5- or 6-membered aromatic or non-aromatic heterocyclic compound, more preferably 5- or 6-membered aromatic heterocyclic groups having 3 to 30 carbon atoms, for example, 2-furyl groups, 2-thienyl groups, 2-pyrimidinyl groups, and 2-benzothiazolyl groups); Cyano group; Hydroxy group; Nitro group; Carboxy group; an alkoxy group (preferably a linear or branched alkoxy group having 1 to 30 carbon atoms, for example, a methoxy group, an ethoxy group, an isopropoxy group, a t-
• a carbamoyloxy group (preferably a carbamoyloxy group having 1 to 30 carbon atoms, for example, an N,N-dimethylcarbamoyloxy group, an N,N-diethylcarbamoyloxy group, a morpholinocarbonyloxy group, an N,N-di-n-octylaminocarbonyloxy group, or an N-n-octylcarbamoyloxy group);
• An alkoxycarbonyloxy group (preferably an alkoxycarbonyloxy group having 2 to 30 carbon atoms, for example, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a t-butoxycarbonyloxy group, or an n-octylcarbonyloxy group); an aryloxycarbonyloxy group (preferably an aryloxycarbonyloxy group having 7 to 30 carbon atoms, for example, a phenoxycarbonyloxy group, a
• an aminocarbonylamino group (preferably an aminocarbonylamino group having 1 to 30 carbon atoms, for example, a carbamoylamino group, an N,N-dimethylaminocarbonylamino group, an N,N-diethylaminocarbonylamino group, or a morpholinocarbonylamino group);
• An alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a t-butoxycarbonylamino group, an n-octadecyloxycarbonylamino group, or an N-methylmethoxycarbonylamino group); an aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 30 carbon atoms, for example, a phenoxycarbonylamino group, a p-ch
• Sulfamoyl groups (preferably sulfamoyl groups having 0 to 30 carbon atoms, for example, N-ethylsulfamoyl groups, N-(3-dodecyloxypropyl)sulfamoyl groups, N,N-dimethylsulfamoyl groups, N-acetylsulfamoyl groups, N-benzoylsulfamoyl groups, and N-(N'-phenylcarbamoyl)sulfamoyl groups); Sulfo group; an alkyl or arylsulfinyl group (preferably an alkylsulfinyl group having 1 to 30 carbon atoms, or an arylsulfinyl group having 6 to 30 carbon atoms, for example, a methylsulfinyl group, an ethylsulfinyl group, a phenylsulfinyl group, or a
• acyl groups (preferably formyl groups, alkylcarbonyl groups having 2 to 30 carbon atoms, arylcarbonyl groups having 7 to 30 carbon atoms, and heterocyclic carbonyl groups having 4 to 30 carbon atoms bonded to a carbonyl group at a carbon atom, for example, acetyl groups, pivaloyl groups, 2-chloroacetyl groups, stearoyl groups, benzoyl groups, p-n-octyloxyphenylcarbonyl groups, 2-pyridylcarbonyl groups, and 2-furylcarbonyl groups);
• An aryloxycarbonyl group preferably an aryloxycarbonyl group having 7 to 30 carbon atoms, for example, a phenoxycarbonyl group, an o-chlorophenoxycarbonyl group, an m-nitrophenoxycarbonyl group, or a pt-butylphenoxycarbonyl group
• an alkoxycarbonyl group preferably an
• a phosphinyl group (preferably a phosphinyl group having 2 to 30 carbon atoms, for example, a phosphinyl group, a dioctyloxyphosphinyl group, or a diethoxyphosphinyl group);
• a phosphinyloxy group (preferably a phosphinyloxy group having 2 to 30 carbon atoms, for example, a diphenoxyphosphinyloxy group, a dioctyloxyphosphinyloxy group);
• a phosphinylamino group (preferably a phosphinylamino group having 2 to 30 carbon atoms, for example, a dimethoxyphosphinylamino group, a dimethylaminophosphinylamino group);
• one or more hydrogen atoms may be substituted with the above-mentioned substituent T.
• substituents include an alkylcarbonylaminosulfonyl group, an arylcarbonylaminosulfonyl group, an alkylsulfonylaminocarbonyl group, and an arylsulfonylaminocarbonyl group.
• Specific examples include a methylsulfonylaminocarbonyl group, a p-methylphenylsulfonylaminocarbonyl group, an acetylaminosulfonyl group, and a benzoylaminosulfonyl group.
• Specific examples of the specific compound include compounds having the following structure: In the structural formula shown below, Et is an ethyl group, Me is a methyl group, n Bu is a normal butyl group, t Bu is a tert-butyl group, and Ph is a phenyl group.
• the maximum absorption wavelength of the specific compound is preferably in the wavelength range of 380 to 420 nm, and more preferably in the wavelength range of 390 to 410 nm.
• the ratio of the absorbance at a wavelength of 440 nm to the absorbance at a wavelength of 400 nm taken as 1 for the specific compound is less than 0.02.
• the molar absorption coefficient at the maximum absorption wavelength of the specific compound is preferably 80,000 L/mol ⁇ cm or more, more preferably 85,000 L/mol ⁇ cm or more, and even more preferably 90,000 L/mol ⁇ cm or more.
• the molar absorption coefficient at a wavelength of 400 nm is preferably 30,000 L/mol ⁇ cm or more, more preferably 40,000 L/mol ⁇ cm or more, and even more preferably 50,000 L/mol ⁇ cm or more.
• the molar absorption coefficient at a wavelength of 440 nm is preferably 1000 L/mol ⁇ cm or less, more preferably 800 L/mol ⁇ cm or less, and even more preferably 600 L/mol ⁇ cm or less.
• the absorbance, maximum absorption wavelength, and molar absorption coefficient of a specific compound can be determined by dissolving the specific compound in ethyl acetate, preparing a solution, and measuring the spectrum at room temperature (25°C) using a 1 cm quartz cell.
• Examples of measuring devices include a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation).
• the specific compound can be produced in accordance with the method described in International Publication No. 2009/022736.
• the compound represented by formula (6) can also be produced by reacting a compound represented by formula (4) with a compound represented by formula (5).
• Q5 represents a group represented by formula (Q-1) above.
• R e51 represents a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group;
• R e52 represents -Cl or an alkoxy group;
• Y51 represents an alkyl group, an aralkyl group or an aryl group.
• Q5 and Q6 in formula (4) have the same definition as Q5 and Q6 in formula (6), and the preferred ranges are also the same.
• the number of carbon atoms in the alkyl group represented by Y 51 in formula (5) is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.
• the alkyl group may be linear, branched, or cyclic, and is preferably linear or branched.
• the alkyl group may have a substituent. Examples of the substituent include the groups explained above for the substituent T.
• the number of carbon atoms of the aryl group represented by Y51 in formula (5) is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8.
• the aryl group may have a substituent. Examples of the substituent include the groups explained above for the substituent T.
• the number of carbon atoms in the alkyl portion of the aralkyl group represented by Y51 in formula (5) is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
• the number of carbon atoms in the aryl portion of the aralkyl group is preferably 6 to 30, more preferably 6 to 20, even more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8.
• the aralkyl group may have a substituent. Examples of the substituent include the groups explained above for the substituent T.
• Y 51 is preferably an alkyl group.
• the alkyl group, aralkyl group and aryl group represented by R e51 in E 51 of formula (5) are the same as the groups explained for Y 51 in formula (5).
• the alkoxy group represented by R e52 in E 51 in formula (5) preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, still more preferably 1 to 15 carbon atoms, particularly preferably 1 to 10 carbon atoms, and most preferably 1 to 8 carbon atoms.
• the reaction between the compound represented by formula (4) and the compound represented by formula (5) can be carried out in an organic solvent.
• the organic solvent is not particularly limited, but for example, amide solvents such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, tetrahydrofuran, acetonitrile, toluene, methanol, ethanol, isopropyl alcohol, and mixtures thereof are preferred, and dimethylformamide or dimethylacetamide is particularly preferred.
• the reaction ratio of the compound represented by formula (4) and the compound represented by formula (5) can be appropriately set depending on the structure of the desired compound represented by formula (6).
• the reaction temperature is not particularly limited, but for example, it is preferably 0°C to the boiling point of the reaction solvent.
• the reaction time is not particularly limited, but for example, it can be 1 hour to 48 hours.
• a polymer (specific polymer) containing a structure derived from the compound represented by formula (1) As the ultraviolet absorbent, a polymer (specific polymer) containing a structure derived from the compound represented by formula (1) can also be used.
• the specific polymer is preferably one that contains a structure derived from a compound represented by the above formula (1) in which at least one of R 1 , R 2 , Q 1 and Q 2 is a group containing a polymerizable group having an ethylenically unsaturated bond (hereinafter also referred to as structure (1)), and more preferably one that contains a structure derived from a compound represented by the above formula (3) in which at least one of R 11 , R 12 , Q 3 and Q 4 is a group containing a polymerizable group having an ethylenically unsaturated bond (hereinafter also referred to as structure (3)).
• the specific polymer may contain a structure derived from a compound having an ethylenically unsaturated bond-containing group other than the compound represented by formula (1) (hereinafter, also referred to as other polymerizable compounds). That is, the specific polymer may be a copolymer of a compound represented by formula (1) having a structure in which at least one of R 1 , R 2 , Q 1 and Q 2 is a group containing a polymerizable group having an ethylenically unsaturated bond, and another polymerizable compound. Examples of the other polymerizable compound include the polymerizable compounds described as materials used in the composition of the present invention described later.
• the other polymerizable compound may be an ultraviolet absorber having a polymerizable group other than the compound represented by formula (1) (also referred to as other polymerizable ultraviolet absorber).
• polymerizable UV absorbers have polymerizable groups such as vinyl groups, allyl groups, (meth)acryloyl groups, (meth)acryloyloxy groups, (meth)acryloylamino groups, and vinylphenyl groups.
• Other polymerizable UV absorbers include aminobutadiene compounds, dibenzoylmethane compounds, benzophenone compounds, benzotriazole compounds, and hydroxyphenyltriazine compounds.
• the content of the structure derived from the compound represented by formula (1) in the specific polymer is preferably 0.01 to 100% by mass.
• the upper limit is more preferably 50% by mass or less, and even more preferably 30% by mass or less.
• the lower limit is more preferably 0.02% by mass or more, and even more preferably 0.1% by mass or more.
• the number weight average molecular weight of the specific polymer is preferably 5,000 to 150,000, more preferably 10,000 to 120,000, and even more preferably 20,000 to 100,000.
• the composition of the present invention may contain an ultraviolet absorber other than the specific ultraviolet absorber described above (hereinafter, also referred to as an other ultraviolet absorber). According to this embodiment, it is possible to form a cured product that can block light having a wavelength in the ultraviolet region over a wide range.
• the maximum absorption wavelength of the other UV absorber is preferably in the wavelength range of 300 to 380 nm, more preferably in the wavelength range of 300 to 370 nm, even more preferably in the wavelength range of 310 to 360 nm, and particularly preferably in the wavelength range of 310 to 350 nm.
• the other UV absorbers are also preferably compounds having a polymerizable group.
• the polymerizable group include a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group.
• UV absorbers include aminobutadiene-based UV absorbers, dibenzoylmethane-based UV absorbers, benzotriazole-based UV absorbers, benzophenone-based UV absorbers, salicylic acid-based UV absorbers, acrylate-based UV absorbers, and triazine-based UV absorbers, of which benzotriazole-based UV absorbers, benzophenone-based UV absorbers, and triazine-based UV absorbers are preferred, and benzotriazole-based UV absorbers and triazine-based UV absorbers are more preferred.
• Specific examples of other UV absorbers include the compounds described in the examples below.
• JP 2020-041013 A, JP 5518613 A, JP 5868465 A, JP 6301526 A, JP 6354665 A, JP 2017-503905 A, WO 2015/064674 A, WO 2015/064675 A, WO 2017/102675 A, WO 2018/190281 A, WO 2018/216750 A, WO 2019/087983 A, EP 2379512 B, EP 2951163 B, and the like can be used.
• the content of the ultraviolet absorber in the total solid content of the composition is preferably 0.01 to 95% by mass.
• the lower limit can be 0.05% by mass or more, 0.1% by mass or more, 1% by mass or more, 5% by mass or more, 10% by mass or more, 20% by mass or more, 25% by mass or more, or 30% by mass or more.
• the upper limit can be 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, or 20% by mass or less.
• the content of the specific ultraviolet absorber in the ultraviolet absorber is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 20% by mass or more.
• the upper limit can be 100% by mass or less, 75% by mass or less, or 50% by mass or less.
• the content of the specific UV absorber in the total solid content of the composition is preferably 0.01 to 50% by mass.
• the lower limit is preferably 0.05% by mass or more, and more preferably 0.1% by mass or more.
• the upper limit is preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 20% by mass or less.
• the content of the specific compound in the total solid content of the composition is preferably 0.01 to 50 mass%.
• the lower limit is preferably 0.05 mass% or more, and more preferably 0.1 mass% or more.
• the upper limit is preferably 40 mass% or less, more preferably 30 mass% or less, and even more preferably 20 mass% or less.
• the content of the specific polymer in the total solid content of the composition is preferably 10 to 95 mass%.
• the lower limit is preferably 15 mass% or more, and more preferably 25 mass% or more.
• the upper limit is preferably 90 mass% or less, more preferably 85 mass% or less, and even more preferably 75 mass% or less.
• composition of the present invention may contain only one type of UV absorbent, or may contain two or more types. When two or more types of UV absorbents are contained, it is preferable that the total amount thereof is within the above range.
• the composition of the present invention contains a discoloration inhibitor.
• the discoloration inhibitor is at least one selected from an amine compound, a phenol compound, a hydroquinone compound, a catechol compound, an ascorbic acid compound, a carotenoid compound, a metal complex compound, and a benzolactone compound.
• the amine compound is preferably a hydroxylamine compound, a tertiary amine compound, or an aminooxyl compound, more preferably a tertiary amine compound or an aminooxyl compound.
• the metal complex compound is preferably a Ni complex compound or a Co complex compound, more preferably a Ni complex compound.
• the discoloration inhibitor is preferably at least one selected from an amine compound and a benzolactone compound, more preferably an amine compound.
• the anti-fading agent preferably contains at least one selected from the group consisting of a compound represented by formula (Ao1-1) and a compound represented by formula (Ao2-1), and more preferably contains a compound represented by formula (Ao1-1).
• R a1 to R a4 each independently represent a hydrogen atom, an alkyl group, or an alkenyl group.
• R a1 to R a4 each independently represent preferably an alkyl group or an alkenyl group, and more preferably an alkyl group.
• the number of carbon atoms in the alkyl group is preferably 1 to 5, and more preferably 1 to 3.
• the alkyl group may be linear, branched, or cyclic, but is preferably linear.
• the alkyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.
• the number of carbon atoms in the alkenyl group is preferably 2 to 5, and more preferably 2 or 3.
• the alkenyl group is preferably linear or branched, and more preferably linear.
• the alkenyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.
• R a1 to R a4 each represent a methyl group.
• X a1 in formula (Ao1-1) is preferably a hydrogen atom, an oxy radical group, an alkyl group, an alkoxy group, an alkenyl group, an acyl group or an aryl group, and more preferably an oxy radical group or an alkoxy group.
• the number of carbon atoms in the alkyl group is preferably 1 to 20, and more preferably 1 to 12.
• the alkyl group may be linear, branched, or cyclic, but is preferably linear.
• the alkyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.
• the number of carbon atoms in the alkenyl group is preferably 2 to 20, and more preferably 2 to 12.
• the alkenyl group is preferably linear or branched, and more preferably linear.
• the alkenyl group may have a substituent.
• Examples of the substituent include the groups exemplified for the substituent T above.
• the number of carbon atoms in the alkoxy group is preferably 1 to 20, and more preferably 1 to 12.
• the alkoxy group is preferably linear or branched, and more preferably linear.
• the alkoxy may have a substituent.
• Examples of the substituent include the groups listed above for the substituent T.
• the number of carbon atoms in the acyl group is preferably 2 to 20, and more preferably 2 to 14.
• the acyl group may have a substituent.
• Examples of the substituent include the groups exemplified for the substituent T above.
• the number of carbon atoms in the aryl group is preferably 6 to 20.
• the aryl group may have a substituent. Examples of the substituent include the groups exemplified for the
• the compound represented by formula (Ao1-1) is preferably a compound represented by formula (Ao1-2).
• X a11 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxy group, or an oxy radical group;
• X a11 in formula (Ao1-2) has the same meaning as X a1 in formula (Ao1-1), and the preferred range is also the same.
• Examples of the substituent represented by R a11 in formula (Ao1-2) include the groups exemplified as the substituent T above.
• Examples of the group include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkylsulfonylamino group, an arylsulfonylamino group,
• the compound represented by formula (Ao1-1) is preferably a compound represented by formula (Ao1-3).
• Xa21 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxy group, or an oxy radical group; L
• X a21 in formula (Ao1-3) has the same meaning as X a1 in formula (Ao1-1), and the preferred range is also the same.
• Examples of the divalent linking group represented by L a21 in formula (Ao1-3) include -O-, -CO-, -COO-, -OCO-, -NHCO-, -NHCOO-, -CONH-, -OCONH-, -S-, -SO 2 - and -OSO 2 -.
• L a22 represents an n-valent group.
• the n-valent group represented by L a22 is a monovalent group (when n is 1)
• examples of the n-valent group represented by L a22 include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl group, an aryl
• alkyl group examples include an alkyl group, an aryl group, an arylsulfonylamino group, an arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, a sulfo group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an arylazo group, a heterocyclic azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, and a silyl
• n-valent group represented by L a22 is a divalent or higher group (n is an integer of 2 or greater)
• examples of the n-valent group represented by L a22 include a hydrocarbon group; and a group in which two or more hydrocarbon groups are bonded together via -O-, -CO-, -COO-, -OCO-, -NH-, -S-, or a group in which two or more of these are combined.
• the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group, and an aliphatic hydrocarbon group is preferable.
• the number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15.
• the aliphatic hydrocarbon group may be linear, branched, or cyclic, and is preferably linear or branched.
• the aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group, and is preferably a saturated aliphatic hydrocarbon group.
• the aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 10 carbon atoms.
• the hydrocarbon group may have a substituent, such as a halogen atom, a hydroxyl group, an alkyl group, or an aryl group.
• the n-valent linking group represented by L a22 is preferably a group containing a saturated aliphatic hydrocarbon group having 1 to 20 carbon atoms (preferably having 2 to 15 carbon atoms, more preferably having 2 to 10 carbon atoms).
• n represents an integer of 1 or more, preferably an integer of 2 or more, more preferably an integer of 2 to 6, and even more preferably an integer of 2 to 4.
• R p1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, or -Si(R p101 ) (R p102 ) (R p103 ), and R p101 to R p103 each independently represent an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group, or an aryloxy group.
• R p1 is preferably a hydrogen atom, an alkyl group or an acyl group, more preferably an alkyl group or an acyl group.
• Examples of the substituents represented by R p2 to R p6 include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, a mercapto group, an alkylthio group
• alkyl group examples include an alkyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an arylazo group, a heterocyclic azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, and a silyl group.
• an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkoxycarbonyl group, an aryloxy group, an aryloxycarbonyl group, an alkylsulfonyl group, and an arylsulfonyl group are preferred, an alkyl group or an alkenyl group is more preferred, and an alkyl group is even more preferred.
• the number of carbon atoms in the alkyl group is preferably 1 to 10, and more preferably 1 to 5.
• the alkyl group may be linear, branched, or cyclic, and is preferably linear or branched, and more preferably branched.
• the alkyl group may have a substituent.
• substituents examples include the groups listed above for the substituent T.
• the number of carbon atoms in the alkenyl group is preferably 2 to 10, and more preferably 2 to 5.
• the alkenyl group is preferably linear or branched, and more preferably branched.
• the alkenyl group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T above.
• At least one of R p2 to R p6 is preferably a substituent, and two or more are more preferably substituents.
• two adjacent groups among R p1 to R p6 may be bonded to each other to form a ring.
• the ring formed is preferably a 5-membered or 6-membered ring.
• the ring formed may further have a substituent.
• the substituent include the groups exemplified above for the substituent T and ethylenically unsaturated bond-containing groups.
• the ethylenically unsaturated bond-containing groups include a vinyl group.
• a preferred embodiment of formula (Ao2-1) is one in which R p1 and R p2 are bonded together to form a ring.
• the ring formed is preferably a 5-membered or 6-membered ring.
• the ring formed preferably further has a substituent.
• the substituent include an aryl group, a heteroaryl group, and an ethylenically unsaturated bond-containing group, and the aryl group and the ethylenically unsaturated bond-containing group are preferred, and the aryl group is more preferred.
• the aryl group and the heteroaryl group may further have a substituent.
• Examples of the further substituent include an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group, an aryloxy group, an acyl group, and a hydroxy group.
• R p1 to R p6 are not hydrogen atoms.
• the total number of carbon atoms of R p1 to R p6 is preferably 10 or more, and more preferably 16 or more.
• the compound represented by formula (Ao2-1) is preferably a compound represented by formula (Ao2-2).
• R p11 to R p14 each independently represent a hydrogen atom, an alkyl group, or an alkenyl group;
• Y p11 represents an aryl group, a heteroaryl group or an ethylenically unsaturated bond-containing group.
• the number of carbon atoms in the alkyl group represented by R p11 to R p14 is preferably 1 to 10, and more preferably 1 to 5.
• the alkyl group may be linear, branched, or cyclic, and is preferably linear or branched, and more preferably branched.
• the alkyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.
• the number of carbon atoms of the alkenyl group represented by R p11 to R p14 is preferably 2 to 10, and more preferably 2 to 5.
• the alkenyl group is preferably linear or branched, and more preferably branched.
• the alkenyl group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T described above.
• R p11 to R p14 is an alkyl group or an alkenyl group, and more preferable that two or more of them are alkyl groups or alkenyl groups. Of these, it is preferable that at least one of R p11 to R p14 is an alkyl group, and more preferable that two or more of them are alkyl groups.
• Y p11 represents an aryl group, a heteroaryl group or an ethylenically unsaturated bond-containing group, and is preferably an aryl group.
• the aryl group and the heteroaryl group may further have a substituent.
• the further substituent includes an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group, an aryloxy group, an acyl group, and a hydroxy group.
• the ethylenically unsaturated bond-containing group includes a vinyl group.
• the compound represented by formula (Ao2-1) is preferably a compound represented by formula (Ao2-3).
• R p21 to R p24 each independently represent a hydrogen atom, an alkyl group, or an alkenyl group.
• R p25 represents an alkyl group, an alkenyl group, or a hydroxy group;
• L p21 represents an s-valent group;
• r represents an integer of 0 to 4;
• s represents an integer of 1 or more;
• r R p25 may be the same or different.
• R p21 to R p24 in formula (Ao2-3) have the same definitions as R p11 to R p14 in formula (Ao2-2), and the preferred ranges are also the same. It is preferable that at least one of R p21 to R p24 is an alkyl group or an alkenyl group, and more preferable that two or more of them are alkyl groups or alkenyl groups. Of these, it is preferable that at least one of R p21 to R p24 is an alkyl group, and more preferable that two or more of them are alkyl groups.
• R p25 in formula (Ao2-3) is preferably an alkyl group or an alkenyl group, and more preferably an alkyl group.
• the number of carbon atoms in the alkyl group is preferably 1 to 10, and more preferably 1 to 5.
• the alkyl group may be linear, branched, or cyclic, and is preferably linear or branched, and more preferably branched.
• the alkyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.
• the number of carbon atoms in the alkenyl group is preferably 2 to 10, and more preferably 2 to 5.
• the alkenyl group is preferably linear or branched, and more preferably branched.
• the alkenyl group may have a substituent.
• L p21 represents an s-valent group.
• the s-valent group represented by L p21 is a monovalent group
• examples of the s-valent group represented by L p21 include an alkyl group, an alkenyl group, an alkoxy group, and an alkynyl group, and is preferably an alkyl group or an alkoxy group.
• examples of the s-valent group represented by L p21 include a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NHCOO-, -NHCOO-, -CONH-, -OCONH-, -S-, -SO 2 -, -OSO 2 -, and a combination of two or more of these groups.
• the above-mentioned hydrocarbon group includes an aliphatic hydrocarbon group and an aromatic hydrocarbon group.
• the number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15.
• the aliphatic hydrocarbon group may be linear, branched, or cyclic, but is preferably linear or branched.
• the aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group, but is preferably a saturated aliphatic hydrocarbon group.
• the aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 10 carbon atoms.
• the hydrocarbon group may have a substituent, such as a halogen atom, a hydroxyl group, an alkyl group, or an aryl group.
• r represents an integer of 0 to 4, and preferably an integer of 0 to 2.
• s represents an integer of 1 or more, preferably an integer of 1 to 4, and more preferably 1 or 2.
• anti-fading agent examples include the compounds described in the Examples described later, the compounds described in paragraphs [0157] to [0171] of JP-A-2009-067984, and compounds having the structures shown below.
• the content of the anti-fading agent in the total solid content of the composition is preferably 0.01 to 50% by mass.
• the lower limit is preferably 0.05% by mass or more, and more preferably 0.1% by mass or more.
• the upper limit is preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 20% by mass or less.
• the content of the anti-fading agent is preferably 0.1 to 500 parts by mass per 100 parts by mass of the UV absorber.
• the upper limit is preferably 300 parts by mass or less, and more preferably 200 parts by mass or less.
• the lower limit is preferably 1 part by mass or more, and more preferably 10 parts by mass or more.
• the content of the anti-fading agent is preferably 0.1 to 500 parts by mass per 100 parts by mass of the specific UV absorber described above.
• the upper limit is preferably 300 parts by mass or less, and more preferably 200 parts by mass or less.
• the lower limit is preferably 1 part by mass or more, and more preferably 10 parts by mass or more.
• composition of the present invention may contain only one type of anti-fading agent, or may contain two or more types. When two or more types of anti-fading agents are contained, it is preferable that the total amount of the anti-fading agents is within the above range.
• the composition of the present invention contains a curable compound.
• the curable compound include a polymerizable compound and a resin.
• the resin is a non-polymerizable resin (a resin having no polymerizable group).
• the polymerizable resin may be a resin having a polymerizable group, or may be a polymerizable resin (a resin having a polymerizable group).
• the polymerizable group include an ethylenically unsaturated bond-containing group and a cyclic ether group.
• alkyl group examples include a vinyl group, a vinylphenyl group, a (meth)allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, and a (meth)acryloylamide group. Preferred are an acryloyloxy group and a (meth)acryloyloxy group, and more preferred is a (meth)acryloyloxy group.
• the cyclic ether group examples include an epoxy group and an oxetanyl group, and preferred is an epoxy group.
• the curable compound contained in the composition of the present invention preferably contains at least one selected from a resin and a polymerizable compound.
• the curable compound may be a combination of a resin and a polymerizable compound.
• Polymerizable compound As the polymerizable compound, any compound that can be polymerized and cured by the application of energy can be used without limitation.
• the polymerizable compound may be a radical polymerizable compound or a cationically polymerizable compound.
• the polymerizable compound may be any of a monomer, a prepolymer (i.e., a dimer, trimer, or oligomer), a mixture thereof, and a (co)polymer of a compound selected from a monomer and a prepolymer, but is preferably a monomer.
• the molecular weight of the polymerizable compound is preferably 100 to 3000.
• the upper limit is preferably 2000 or less, and more preferably 1500 or less.
• the lower limit is preferably 150 or more, and more preferably 250 or more.
• the radical polymerizable compound may include a compound having an ethylenically unsaturated bond-containing group.
• the radical polymerizable compound may include an unsaturated carboxylic acid (e.g., acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), an ester of an unsaturated carboxylic acid, an amide of an unsaturated carboxylic acid, and a (co)polymer of an unsaturated carboxylic acid or its ester or amide.
• an ester of an unsaturated carboxylic acid and an aliphatic polyhydric alcohol, an amide of an unsaturated carboxylic acid and an aliphatic polyamine, and a homopolymer or copolymer thereof are preferred.
• the radical polymerizable compound may be an addition reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having a nucleophilic substituent (e.g., a hydroxy group, an amino group, a mercapto group, etc.) with a monofunctional or polyfunctional isocyanate compound or an epoxy compound; a dehydration condensation reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having a nucleophilic substituent and a monofunctional or polyfunctional carboxylic acid; an addition reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having an electrophilic substituent (e.g., an isocyanate group, an epoxy group, etc.) with a monofunctional or polyfunctional alcohol, amine, or thiol; a substitution reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having a leaving substituent (e.g., a halogen
• the radical polymerizable compound may be used in combination with multiple compounds having different functionalities or multiple compounds having different types of polymerizable groups (e.g., acrylic acid esters, methacrylic acid esters, styrene compounds, vinyl ether compounds, etc.).
• polymerizable groups e.g., acrylic acid esters, methacrylic acid esters, styrene compounds, vinyl ether compounds, etc.
• the radically polymerizable compound is preferably a (meth)acrylate compound, more preferably a di- or higher functional (meth)acrylate compound, even more preferably a di- to 15-functional (meth)acrylate compound, even more preferably a di- to 10-functional (meth)acrylate compound, and particularly preferably a di- to 6-functional (meth)acrylate compound.
• radically polymerizable compounds include pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tri((meth)acryloyloxyethyl)isocyanurate, pentaerythritol tetra(meth)acrylate ethylene oxide EO (ethylene oxide) modified product, dipentaerythritol hexa(meth)acrylate EO (ethylene oxide) modified product, and benzyl (meth)acrylate.
• pentaerythritol tri(meth)acrylate pentaerythritol tetra(meth)acrylate
• pentaerythritol tetra(meth)acrylate dipentaerythritol penta(meth)acrylate
• radically polymerizable compounds include the KAYARAD series (e.g., D-330, D-320, D-310, PET-30, TPA-330, DPHA, etc.) from Nippon Kayaku Co., Ltd., the NK Ester series (e.g., A-DPH-12E, A-TMMT, A-TMM-3, etc.) from Shin-Nakamura Chemical Co., Ltd., the Light Acrylate series (e.g., DCP-A, etc.) from Kyoeisha Chemical Co., Ltd., the Aronix series (e.g., M-305, M-306, M-309, M-450, M-402, TO-1382, etc.) from Toagosei Co., Ltd., and the Viscoat series (e.g., V#802, etc.) from Osaka Organic Chemical Industry Co., Ltd., as well as polyfunctional (meth)acrylate compounds.
• KAYARAD series e.g., D-330, D-320, D
• the radically polymerizable compound may be the (meth)acrylate compounds described in JP-A-48-064183, JP-B-49-043191, or JP-B-52-030490, or the compounds introduced as photocurable monomers and oligomers in the Journal of the Japan Adhesion Association, Vol. 20, No. 7, pp. 300-308 (1984).
• the cationic polymerizable compound may be a compound having a cationic polymerizable group.
• the cationic polymerizable group may be a cyclic ether group such as an epoxy group and an oxetanyl group, or a vinyl ether group, and is preferably a cyclic ether group.
• the cationic polymerizable compound may be a polyfunctional cationic polymerizable compound having two or more cationic polymerizable groups.
• Cationically polymerizable compounds include polyfunctional alicyclic epoxy compounds, polyfunctional heterocyclic epoxy compounds, polyfunctional oxetane compounds, alkylene glycol diglycidyl ethers, and alkylene glycol monovinyl monoglycidyl ethers.
• cationic polymerizable compounds include 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol, xylylene bisoxetane, 3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3- ⁇ [(3-ethyloxetane-3-yl)methoxy]methyl ⁇ oxetane, cyclohexanedimethanol divinyl ether, 2-ethylhexyl vinyl ether, cyclohexanedimethanol monovinyl ether, 4-
• a (meth)acrylate compound having a cationic polymerizable group can also be used.
• a specific example of a (meth)acrylate compound having a cationic polymerizable group is 3,4-epoxycyclohexylmethyl methacrylate.
• An example of a commercially available product is Cyclomer M100 manufactured by Daicel Corporation.
• Cationically polymerizable compounds that can be used include the Aron Oxetane series (OXT-101, OXT-121, OXT-221, etc.) manufactured by Toagosei Co., Ltd., the Celloxide series (2021P) manufactured by Daicel Corporation, and alkyl divinyl ether CHDVE, alkyl monovinyl ether EHVE, hydroxyalkyl vinyl ether CHMVE, and hydroxyalkyl vinyl ether HBVE manufactured by Nippon Carbide Industries Co., Ltd.
• the specific examples of epoxy resins given below can also be used.
• the resin examples include (meth)acrylic resins, ene-thiol resins, polyester resins, polycarbonate resins, vinyl polymers [e.g., polydiene resins, polyalkene resins, polystyrene resins, polyvinyl ether resins, polyvinyl alcohol resins, polyvinyl ketone resins, polyfluorovinyl resins, and polyvinyl bromide resins], polythioether resins, polyphenylene resins, polyurethane resins, polysulfonate resins, nitrosopolymer resins, polysiloxane resins, polysulfide resins, polythioester resins, polysulfone resins, polysulfonamide resins, polyamide resins, polyimine resins, polyurea resins, polyphosphazene resins, polysilane resins, polysilazane resins, polyfuran resins, polybenzoxazo Examples of the resin include (me
• (Meth)acrylic resins include polymers containing structural units derived from (meth)acrylic acid and/or its esters. Specifically, they include polymers obtained by polymerizing at least one compound selected from the group consisting of (meth)acrylic acid, (meth)acrylic acid esters, (meth)acrylamide, and (meth)acrylonitrile.
• Polyester resins include polymers obtained by the reaction of polyols (e.g., ethylene glycol, propylene glycol, glycerin, and trimethylolpropane) with polybasic acids (e.g., aromatic dicarboxylic acids (e.g., terephthalic acid, isophthalic acid, and naphthalenedicarboxylic acid, and dicarboxylic acids in which the hydrogen atoms of the aromatic rings are substituted with methyl groups, ethyl groups, or phenyl groups), aliphatic dicarboxylic acids having 2 to 20 carbon atoms (e.g., adipic acid, sebacic acid, and dodecanedicarboxylic acid), or alicyclic dicarboxylic acids (e.g., cyclohexanedicarboxylic acid), etc.), as well as polymers obtained by ring-opening polymerization of cyclic ester compounds such as caprolactone monomers (e.g.,
• epoxy resins examples include bisphenol A type epoxy resins, bisphenol F type epoxy resins, phenol novolac type epoxy resins, cresol novolac type epoxy resins, aliphatic epoxy resins, etc.
• Commercially available epoxy resins may be used, and examples of commercially available products include the following:
• bisphenol A type epoxy resins include jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, and jER1010 (all manufactured by Mitsubishi Chemical Corporation), as well as EPICLON 860, EPICLON 1050, EPICLON 1051, and EPICLON 1055 (all manufactured by DIC Corporation).
• bisphenol F type epoxy resins include jER806, jER807, jER4004, jER4005, jER4007, and jER4010 (all manufactured by Mitsubishi Chemical Corporation), EPICLON830 and EPICLON835 (all manufactured by DIC Corporation), and LCE-21 and RE-602S (all manufactured by Nippon Kayaku Co., Ltd.).
• phenol novolac type epoxy resins include jER152, jER154, jER157S70, and jER157S65 (all manufactured by Mitsubishi Chemical Corporation), and EPICLON N-740, EPICLON N-770, and EPICLON N-775 (all manufactured by DIC Corporation).
• cresol novolac type epoxy resins include EPICLON N-660, EPICLON N-665, EPICLON N-670, EPICLON N-673, EPICLON N-680, EPICLON N-690, and EPICLON N-695 (all manufactured by DIC Corporation), and EOCN-1020 (manufactured by Nippon Kayaku Co., Ltd.).
• Examples of commercially available aliphatic epoxy resins include the ADEKA RESIN EP series (e.g., EP-4080S, EP-4085S, and EP-4088S; manufactured by ADEKA Corporation), CELLOXIDE 2021P, CELLOXIDE 2081, CELLOXIDE 2083, CELLOXIDE 2085, EHPE3150, EPOLEAD PB 3600, and EPOLEAD PB 4700 (all manufactured by Daicel Corporation), DENACOL EX-212L, EX-214L, EX-215L, EX-216L, EX-217L, EX-218L, EX-219L, EX-220L, EX-221L, EX-222L, EX-223L, EX-224L, EX-225L, EX-226L, EX-227L, EX-228L, EX-229L, EX-300L, EX-301L, EX-302L, EX-303L, EX-304L, EX-305
• epoxy resins include Marproof G-0150M, G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (all manufactured by NOF Corporation, epoxy group-containing polymers).
• the cellulose acylate resin As the cellulose acylate resin, the cellulose acylate described in paragraphs 0016 to 0021 of JP 2012-215689 A is preferably used.
• the polyester resin a commercially available product such as the Vylon series (e.g., Vylon 500) manufactured by Toyobo Co., Ltd. can also be used.
• the SK Dyne series As a commercially available (meth)acrylic resin, the SK Dyne series (e.g., SK Dyne-SF2147, etc.) manufactured by Soken Chemical & Engineering Co., Ltd. can also be used.
• the polystyrene resin is preferably a resin containing 50% by mass or more of repeating units derived from styrene-based monomers, more preferably a resin containing 70% by mass or more of repeating units derived from styrene-based monomers, and even more preferably a resin containing 85% by mass or more of repeating units derived from styrene-based monomers.
• styrene-based monomers include styrene and its derivatives.
• Styrene derivatives are compounds in which other groups are bonded to styrene, such as alkylstyrenes such as o-methylstyrene, m-methylstyrene, p-methylstyrene, 2,4-dimethylstyrene, o-ethylstyrene, and p-ethylstyrene, and substituted styrenes in which a hydroxyl group, alkoxy group, carboxyl group, halogen, or the like has been introduced into the benzene nucleus of styrene, such as hydroxystyrene, tert-butoxystyrene, vinylbenzoic acid, o-chlorostyrene, and p-chlorostyrene.
• Polystyrene resins may also contain repeating units derived from monomers other than styrene-based monomers.
• examples of other monomers include alkyl (meth)acrylates such as methyl (meth)acrylate, cyclohexyl (meth)acrylate, methylphenyl (meth)acrylate, and isopropyl (meth)acrylate; unsaturated carboxylic acid monomers such as methacrylic acid, acrylic acid, itaconic acid, maleic acid, fumaric acid, and cinnamic acid; unsaturated dicarboxylic acid anhydride monomers such as maleic anhydride, itaconic acid, ethyl maleic acid, methyl itaconic acid, and chloromaleic acid; unsaturated nitrile monomers such as acrylonitrile and methacrylonitrile; and conjugated dienes such as 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-
• polystyrene resins include AS-70 (acrylonitrile-styrene copolymer resin) manufactured by Nippon Steel & Sumikin Chemical Co., Ltd., SMA2000P (styrene-maleic acid copolymer) manufactured by Kawahara Oil Chemical Co., Ltd., Clearen 530L and Clearen 730L manufactured by Denka Co., Ltd., Tufprene 126S and Asaprene T411 manufactured by Asahi Kasei Co., Ltd., Kraton D1102A and Clayton Polymer Japan Co., Ltd.
• hydrogenated polystyrene resins examples include TON D1116A, Styrolux S and Styrolux T manufactured by Styrolution, Asaflex 840 and Asaflex 860 manufactured by Asahi Kasei Corporation, 679, HF77, SGP-10, 475D, H0103, and HT478 manufactured by PS Japan, and DIC Styrene XC-515, DIC Styrene XC-535, and DIC Styrene GH-8300-5 manufactured by DIC Corporation.
• Examples of commercially available hydrogenated polystyrene resins include the Tuftec H series manufactured by Asahi Kasei Corporation, the Kraton G series manufactured by Shell Japan, Dynaron (hydrogenated styrene-butadiene random copolymer) manufactured by JSR Corporation, and Septon manufactured by Kuraray Co., Ltd.
• Commercially available modified polystyrene resins include the Tuftec M series manufactured by Asahi Kasei Corporation, Epofriend manufactured by Daicel Corporation, polar group-modified Dynaron manufactured by JSR Corporation, and Reseda manufactured by Toagosei Co., Ltd.
• Cyclic olefin resins include (R1) polymers containing structural units derived from norbornene compounds, (R2) polymers containing structural units derived from monocyclic cyclic olefin compounds other than norbornene compounds, (R3) polymers containing structural units derived from cyclic conjugated diene compounds, (R4) polymers containing structural units derived from vinyl alicyclic hydrocarbon compounds, and hydrogenated polymers containing structural units derived from each of the compounds (R1) to (R4).
• polymers containing structural units derived from norbornene compounds and polymers containing structural units derived from monocyclic cyclic olefin compounds include ring-opened polymers of each compound.
• the cyclic olefin resin is not particularly limited, but is preferably a polymer having a structural unit derived from a norbornene compound, as represented by formula (A-II) or formula (A-III).
• a polymer having a structural unit represented by formula (A-II) is an addition polymer of a norbornene compound
• a polymer having a structural unit represented by formula (A-III) is a ring-opening polymer of a norbornene compound.
• m is an integer of 0 to 4, and is preferably 0 or 1.
• R 3 to R 6 in formula (A-II) and formula (A-III) each independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms. Examples of the hydrocarbon group represented by R 3 to R 6 include an alkyl group, an alkenyl group, an alkynyl group, and an aryl group, and an alkyl group or an aryl group is preferable.
• X 2 and X 3 , Y 2 and Y 3 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms substituted with a halogen atom, -(CH 2 ) n COOR 11 , -(CH 2 ) n OCOR 12 , -(CH 2 ) n NCO, -(CH 2 ) n NO 2 , -(CH 2 ) n CN, -(CH 2 ) n CONR 13 R 14 , -(CH 2 ) n NR 13 R 14 , -(CH 2 ) n OZ 1 , -(CH 2 ) n W 1 , or (-CO) 2 O or (-CO) 2 formed by X 2 and Y 2 or X 3 and Y 3 bonding together.
• R 11 to R 15 in the above groups which can be taken as X 2 , X 3 , Y 2 and Y 3 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms
• Z 1 represents a hydrocarbon group or a hydrocarbon group substituted with a halogen
• W 1 represents Si(R 16 ) p D (3-p)
• R 16 represents a hydrocarbon group having 1 to 10 carbon atoms
• D represents a halogen atom
• -OCOR 17 or -OR 17 R 17 is a hydrocarbon group having 1 to 10 carbon atoms
• p is an integer of 0 to 3
• n represents an integer of 0 to 10, preferably 0 to 8, and more preferably 0 to 6.
• R 3 to R 6 are each preferably independently a hydrogen atom or —CH 3 , and from the viewpoint of moisture permeability, more preferably a hydrogen atom.
• X2 and X3 are each preferably a hydrogen atom, --CH.sub.3 , or --C.sub.2H.sub.5 , and from the viewpoint of moisture permeability, a hydrogen atom is more preferable.
• Y2 and Y3 each independently represent preferably a hydrogen atom, a halogen atom (particularly a chlorine atom) or --( CH2 ) nCOOR11 ( particularly --COOCH3 ), and more preferably a hydrogen atom in terms of moisture permeability.
• the other groups are selected appropriately.
• a polymer having a structural unit represented by formula (A-II) or formula (A-III) may further contain one or more structural units represented by formula (A-I).
• R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms
• X 1 and Y 1 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms substituted with a halogen atom, -(CH 2 ) n COOR 11 , -(CH 2 ) n OCOR 12 , -(CH 2 ) n NCO, -(CH 2 ) n NO 2 , -(CH 2 ) n CN, -(CH 2 ) n CONR 13 R 14 , -(CH 2 ) n NR 13 R 14 , -(CH 2 ) n OZ 1 , -(CH 2 ) n W 1 , or X 2 and Y 2 or X 1 independently represent a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms
• R11 to R15 in the above groups which can be taken as X1 and Y1 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms
• Z1 represents a hydrocarbon group or a hydrocarbon group substituted with a halogen
• W1 represents Si( R16 ) pD (3-p)
• R16 represents a hydrocarbon group having 1 to 10 carbon atoms
• D represents a halogen atom
• -OCOR17 or -OR17 R17 is a hydrocarbon group having 1 to 10 carbon atoms
• p is an integer of 0 to 3
• n represents an integer of 0 to 10.
• the content of the structural unit represented by formula (A-II) or formula (A-III) in the cyclic polyolefin resin is preferably 90% by mass or less, more preferably 30 to 85% by mass, even more preferably 50 to 79% by mass, and even more preferably 60 to 75% by mass.
• Cyclic olefin resins are described in JP-A-10-007732, JP-T-2002-504184, WO-2004/070463, etc., and the contents of these documents may be referred to as appropriate.
• Cyclic olefin resins are obtained by addition polymerization of norbornene compounds (e.g., polycyclic unsaturated compounds of norbornene).
• cyclic olefin resins include the Arton series (e.g., Arton G, F, RX4500) manufactured by JSR Corporation, and Zeonor ZF14, ZF16, Zeonex 250, 280 manufactured by Zeon Corporation.
• Arton series e.g., Arton G, F, RX4500
• Zeonor ZF14, ZF16, Zeonex 250, 280 manufactured by Zeon Corporation.
• cyclic olefin resins include copolymers obtained by addition copolymerization of norbornene compounds with olefins such as ethylene, propylene, and butene, conjugated dienes such as butadiene and isoprene, non-conjugated dienes such as ethylidene norbornene, and ethylenically unsaturated compounds such as acrylonitrile, acrylic acid, methacrylic acid, maleic anhydride, acrylic acid esters, methacrylic acid esters, maleimide, vinyl acetate, and vinyl chloride.
• copolymers with ethylene are preferred.
• Examples of such addition (co)polymers of norbornene compounds are sold by Mitsui Chemicals under the trade name APEL, and include products with different glass transition temperatures (Tg), such as APL8008T (Tg 70°C), APL6011T (Tg 105°C), APL6013T (Tg 125°C), and APL6015T (Tg 145°C).
• Tg glass transition temperatures
• Polyplastics Co., Ltd. sells pellets such as TOPAS 8007, 6013, and 6015. Ferrania also sells Appear 3000.
• hydrogenated cyclic olefin resins can be synthesized by subjecting norbornene compounds, etc., to addition polymerization or metathesis ring-opening polymerization, followed by hydrogenation. Synthesis methods are described, for example, in JP-A-01-240517, JP-A-07-196736, JP-A-60-026024, JP-A-62-019801, JP-A-2003-159767, and JP-A-2004-309979.
• the weight molecular weight of the cyclic olefin resin is preferably 5,000 to 500,000, more preferably 8,000 to 200,000, and even more preferably 10,000 to 100,000.
• polycarbonate resins include reaction products of polyhydric phenol compounds with phosgene or carbonate compounds.
• Polyhydric phenol compounds include hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bisphenol A, bisphenol C, bisphenol E, bisphenol F, bisphenol M, bisphenol P, bisphenol S, bisphenol Z, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 2,2-bis(3-phenyl-4-hydroxyphenyl)propane, 2,2-bis( 3-isopropyl-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane, 4,4'-d
• carbonate ester compounds examples include phosgene, diphenyl carbonate, bis(chlorophenyl) carbonate, dinaphthyl carbonate, bis(diphenyl) carbonate, dimethyl carbonate, diethyl carbonate, and dibutyl carbonate, with bis(diphenyl) carbonate, dimethyl carbonate, and diethyl carbonate being preferred.
• polycarbonate resins include Panlite L-1250WP and Panlite SP-1516 manufactured by Teijin Limited, Iupizeta EP-5000 and Iupizeta EP-4000 manufactured by Mitsubishi Gas Chemical Co., Ltd., and Caliber 301-30 manufactured by Sumika Polycarbonate Co., Ltd.
• Thiourethane resins include the reaction product of an isocyanate compound and a polythiol compound, and the reaction product of a thiourethane resin precursor.
• Commercially available thiourethane resin precursors include MR-7, MR-8, MR-10, and MR-174 manufactured by Mitsui Chemicals, Inc.
• Polyamide resins include aliphatic polyamide resins and aromatic polyamide resins.
• Aliphatic polyamide resins include nylon 6, nylon 11, nylon 12, nylon 46, nylon 66, nylon 666, nylon 610, nylon 612, etc.
• Aromatic polyamide resins include resins polymerized by dehydration condensation of diamines and dicarboxylic acids, in which at least one of the diamines and dicarboxylic acids contains an aromatic ring.
• Specific examples of aromatic polyamide resins include condensation polymers of metaxylylenediamine and adipic acid or adipic acid halide.
• the resin may have an acid group.
• the acid group include a carboxy group, a phosphoric acid group, a sulfonic acid group, and a phenolic hydroxy group.
• the acid group may be of only one type, or of two or more types.
• a resin having an acid group can be used as an alkali-soluble resin, and can also be used as a dispersant.
• the acid value of the resin having acid groups is preferably 30 to 200 mgKOH/g.
• the lower limit of the acid value is preferably 50 mgKOH/g or more, and more preferably 70 mgKOH/g or more.
• the upper limit of the acid value is preferably 150 mgKOH/g or less, and more preferably 120 mgKOH/g or less.
• the resin may have a polymerizable group.
• the polymerizable group include an ethylenically unsaturated bond-containing group and a cyclic ether group.
• the ethylenically unsaturated bond-containing group include a vinyl group, a styrene group, an allyl group, a methallyl group, and a (meth)acryloyl group.
• the cyclic ether group include an epoxy group and an oxetanyl group.
• resins containing polymerizable groups include the Dianarl BR series (polymethyl methacrylate (PMMA), e.g., Dianarl BR-80, BR-83, and BR-87; manufactured by Mitsubishi Chemical Corporation), Photomer 6173 (COOH-containing polyurethane acrylic oligomer; manufactured by Diamond Shamrock Co., Ltd.), Viscoat R-264, and KS Resist 106 (all manufactured by Osaka Organic Chemical Industry Co., Ltd.), Cyclomer P series (e.g., ACA230AA), Plaxel CF200 series (all manufactured by Daicel Corporation), and Ebecryl 3800 (manufactured by Daicel UCB Corporation), as well as Acryl Cure RD-F8 (manufactured by Nippon Shokubai Co., Ltd.).
• PMMA polymethyl methacrylate
• PMMA polymethyl methacrylate
• BR-80 polymethyl methacrylate
• BR-83 BR-87
• BR-87 manufactured
• the resin is preferably a thermoplastic resin such as a carbonate resin or a (meth)acrylic resin, or a thermosetting resin such as a urethane resin.
• An adhesive or a bonding agent can be used for the resin.
• adhesives include acrylic adhesives, rubber adhesives, and silicone adhesives.
• An acrylic adhesive is an adhesive that contains a polymer of a (meth)acrylic monomer ((meth)acrylic polymer).
• adhesives include urethane resin adhesives, polyester adhesives, acrylic resin adhesives, ethylene vinyl acetate resin adhesives, polyvinyl alcohol adhesives, polyamide adhesives, and silicone adhesives. Among them, urethane resin adhesives and silicone adhesives are preferred because of their high adhesive strength.
• Commercially available adhesives may be used, and examples of commercially available products include a urethane resin adhesive (LIS-073-50U: product name) from Toyo Ink Co., Ltd. and an acrylic adhesive (SK Dyne-SF2147: product name) from Soken Chemical & Engineering Co., Ltd.
• the resin is preferably at least one selected from (meth)acrylic resin, polystyrene resin, polyester resin, polyurethane resin, thiourethane resin, polyimide resin, polyamide resin, epoxy resin, polycarbonate resin, phthalate resin, cellulose acylate resin, and cyclic olefin resin, and more preferably at least one selected from (meth)acrylic resin, polystyrene resin, polyester resin, polyurethane resin, and cyclic olefin resin, because it has good compatibility with the specific compound and is easy to obtain a cured product with reduced surface unevenness.
• the weight average molecular weight (Mw) of the resin is preferably 2,000 to 2,000,000.
• the lower limit of the Mw of the resin is preferably 5,000 or more, more preferably 10,000 or more, and even more preferably 50,000 or more.
• the upper limit of the Mw of the resin is preferably 1,000,000 or less, more preferably 500,000 or less, and even more preferably 200,000 or less.
• the weight average molecular weight (Mw) of the epoxy resin is preferably 100 or more, and more preferably 200 to 2,000,000.
• the upper limit of the Mw of the epoxy resin is preferably 1,000,000 or less, and more preferably 500,000 or less.
• the lower limit of the Mw of the epoxy resin is preferably 2,000 or more.
• the weight average molecular weight (Mw) is a value measured by gel permeation chromatography (GPC). Measurements by GPC are performed using an HLC (registered trademark)-8020GPC (manufactured by Tosoh Corporation) measuring device, three TSKgel (registered trademark) Super Multipore HZ-H columns (4.6 mm ID x 15 cm, manufactured by Tosoh Corporation) and THF (tetrahydrofuran) as the eluent. Measurement conditions are a sample concentration of 0.45% by mass, a flow rate of 0.35 ml/min, a sample injection amount of 10 ⁇ l, and a measurement temperature of 40°C, and an RI detector.
• HLC registered trademark
• 8020GPC manufactured by Tosoh Corporation
• TSKgel registered trademark
• THF tetrahydrofuran
• the calibration curve will be created from eight samples of "Standard sample TSK standard, polystyrene" from Tosoh Corporation: "F-40", “F-20”, “F-4", "F-1", "A-5000”, “A-2500”, "A-1000", and "n-propylbenzene”.
• the total light transmittance of the resin is preferably 80% or more, more preferably 85% or more, and even more preferably 90% or more.
• the total light transmittance of the resin is a value measured based on the contents described on pages 225-232 of "4th Edition Experimental Chemistry Lectures 29: Polymer Material Media” (Maruzen, 1992), edited by the Chemical Society of Japan.
• the content of the curable compound in the total solid content of the composition is preferably 1 to 99.9 mass%.
• the lower limit is preferably 30 mass% or more, more preferably 50 mass% or more, and even more preferably 70 mass% or more.
• the upper limit is preferably 95 mass% or less, more preferably 90 mass% or less, and even more preferably 80 mass% or less.
• the composition may contain only one type of curable compound, or may contain two or more types. When two or more types of curable compounds are contained, it is preferable that the total amount thereof is within the above range.
• the content of the resin in the total solid content of the composition is preferably 1 to 99.9 mass%.
• the lower limit is preferably 30 mass% or more, more preferably 50 mass% or more, and even more preferably 70 mass% or more.
• the upper limit is preferably 95 mass% or less, more preferably 90 mass% or less, and even more preferably 80 mass% or less.
• the composition may contain only one type of resin, or may contain two or more types. When two or more types of resins are contained, it is preferable that the total amount thereof is within the above range.
• the content of the polymerizable compound in the total solid content of the composition is preferably 0.1 to 90 mass%.
• the lower limit is preferably 1 mass% or more, and more preferably 5 mass% or more.
• the upper limit is preferably 80 mass% or less, and more preferably 70 mass% or less.
• the composition of the present invention may contain only one type of polymerizable compound, or may contain two or more types. When two or more types of polymerizable compounds are contained, it is preferable that the total amount thereof is in the above range.
• the composition of the present invention may contain a polymerization initiator.
• the polymerization initiator may be a compound capable of generating an initiating species required for a polymerization reaction by the application of energy.
• examples of the polymerization initiator include radical polymerization initiators and cationic polymerization initiators.
• the polymerization initiator is preferably a radical polymerization initiator.
• the polymerization initiator is preferably a cationic polymerization initiator.
• the polymerization initiator can be appropriately selected from, for example, a photopolymerization initiator and a thermal polymerization initiator, and a photopolymerization initiator is preferred.
• the photopolymerization initiator is a compound that is sensitized by exposure light and initiates or promotes polymerization of a polymerizable compound.
• the photopolymerization initiator includes a photoradical polymerization initiator and a photocationic polymerization initiator, and a photoradical polymerization initiator is preferred.
• the photoradical polymerization initiator is preferably a compound that generates radicals in response to active light having a wavelength of 300 nm or more.
• Photoradical polymerization initiator examples include oxime compounds, halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), oxydiazole compounds, carbonyl compounds, ketal compounds, benzoin compounds, acridine compounds, organic peroxides, azo compounds, coumarin compounds, azide compounds, metallocene compounds, hexaarylbiimidazole compounds, organic boric acid compounds, disulfonic acid compounds, onium salt compounds, acetophenone compounds, acylphosphine compounds, and benzophenone compounds.
• oxime compounds e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.
• halogenated hydrocarbon derivatives e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.
• Acetophenone compounds include aminoacetophenone compounds and hydroxyacetophenone compounds. Acetophenone compounds include those described in JP-A-2009-191179 and JP-A-10-291969. Commercially available aminoacetophenone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, and Omnirad 379EG (all manufactured by IGM Resins B.V.). Commercially available hydroxyacetophenone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, and Omnirad 127 (all manufactured by IGM Resins B.V.).
• acylphosphine compound examples include the acylphosphine compounds described in Japanese Patent No. 4225898.
• Commercially available acylphosphine compounds include Omnirad 819 and Omnirad TPO (both manufactured by IGM Resins B.V.).
• benzophenone compounds include benzophenone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methylbenzophenone, 4-methoxybenzophenone, 2-chlorobenzophenone, 4-chlorobenzophenone, 4-bromobenzophenone, 2-carboxybenzophenone, 2-ethoxycarbonylbenzophenone, benzophenonetetracarboxylic acid or its tetramethyl ester, 4,4'-bis(dialkylamino)benzophenones (e.g., 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(dicyclohexylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dihydroxyethylamino)benzophenone), 4-methoxy-4'-dimethylaminobenzophenone, 4,4'-dimethoxybenzophenone, 4-dimethylaminobenzophen
• oxime compounds examples include those described in JP 2001-233842 A, JP 2000-080068 A, JP 2006-342166 A, and JP 2016-006475 A, paragraphs 0073 to 0075.
• oxime ester compounds are preferred.
• Commercially available oxime compounds include Irgacure OXE01, Irgacure OXE02 (manufactured by BASF), and Irgacure OXE03 (manufactured by BASF).
• Halogenated hydrocarbon derivatives are described in Wakabayashi et al., Bull Chem. Soc. Japan vol. 42, pp. 2924 (1969), U.S. Pat. No. 3,905,815, JP-B-46-004605, JP-A-48-036281, JP-A-55-032070, JP-A-60-239736, JP-A-61-169835, JP-A-61-169837, JP-A-62-058241, JP-A-62-212401, JP-A-63-070243, JP-A-63-298339, M. P.
• Examples of the compounds include those described in Hutt, Journal of Heterocyclic Chemistry, Vol. 1 (No. 3), (1970), and are preferably oxazole compounds or triazine compounds substituted with a trihalomethyl group.
• hexaarylbiimidazole compounds include those described in JP-B-06-029285, U.S. Pat. No. 3,479,185, U.S. Pat. No. 4,311,783, and U.S. Pat. No. 4,622,286.
• Specific examples include 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-bromophenyl))-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o,p-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetra(m-methoxyphenyl)biimidazole.
• the photocationic polymerization initiator is not particularly limited as long as it is a compound that generates a protonic acid or a Lewis acid upon irradiation with light.
• the photoacid generator is preferably a compound that responds to actinic rays having a wavelength of 300 nm or more, more preferably 300 to 450 nm, and generates an acid.
• the photoacid generator is preferably a compound that generates an acid having a pKa of 4 or less upon irradiation with light, more preferably a compound that generates an acid having a pKa of 3 or less, and even more preferably a compound that generates an acid having a pKa of 2 or less.
• photocationic polymerization initiators include oxime sulfonate compounds, triazine compounds, sulfonium salts, iodonium salts, quaternary ammonium salts, diazomethane compounds, sulfone compounds, sulfonic acid ester compounds, iminosulfonic acid ester compounds, carboxylic acid ester compounds, and sulfonimide compounds.
• photocationic polymerization initiators include the compounds described in paragraphs 0061 to 0108 of JP 2012-046577 A and paragraphs 0029 to 0030 of JP 2002-122994 A, the compounds described in paragraphs 0037 to 0063 of JP 2002-122994 A, and the oxime sulfonate compounds described in paragraphs 0081 to 0108 of JP 2013-210616 A.
• photocationic polymerization initiators include WPAG-469 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), CPI-100P (manufactured by San-Apro Co., Ltd.), CPI-210S (manufactured by San-Apro Co., Ltd.), and Irgacure 290 (BASF Japan Co., Ltd.).
• the thermal polymerization initiator is not particularly limited, and known thermal polymerization initiators can be used.
• thermal polymerization initiators such as 2,2'-azobis(isobutyrate)dimethyl, 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), dimethyl-2,2'-azobis(2-methylpropionate), 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis(N-butyl-2-methylpropionamide), dimethyl 1,1'-azobis(1-cyclohexanecarboxylate), and 2,2'-azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride; organic peroxides such as 1,1-di(t)-2-butyronitrile,
• the content of the polymerization initiator in the total solid content of the composition is preferably 0.1 to 20 mass%.
• the lower limit is preferably 0.3 mass% or more, and more preferably 0.4 mass% or more.
• the upper limit is preferably 15 mass% or less, and more preferably 10 mass% or less.
• the composition of the present invention may contain only one type of polymerization initiator, or may contain two or more types. When two or more types of polymerization initiators are contained, it is preferable that the total amount thereof is in the above range.
• the composition of the present invention may contain a catalyst.
• the catalyst include acid catalysts such as hydrochloric acid, sulfuric acid, acetic acid, and propionic acid, and base catalysts such as sodium hydroxide, potassium hydroxide, and triethylamine.
• the content of the catalyst is preferably 0.1 to 100 parts by mass, more preferably 0.1 to 50 parts by mass, and even more preferably 0.1 to 20 parts by mass, per 100 parts by mass of the resin.
• the composition of the present invention may contain only one type of catalyst, or may contain two or more types. When two or more types of catalysts are contained, the total amount thereof is preferably within the above range.
• the composition of the present invention may contain a silane coupling agent.
• the adhesion of the obtained film to the support can be further improved.
• the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
• the hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can generate a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, and an acyloxy group, and an alkoxy group is preferable.
• the silane coupling agent is preferably a compound having an alkoxysilyl group.
• functional groups other than the hydrolyzable group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group, an isocyanate group, and a phenyl group, and an amino group, a (meth)acryloyl group, and an epoxy group are preferable.
• silane coupling agent examples include compounds described in paragraphs 0018 to 0036 of JP-A-2009-288703 and compounds described in paragraphs 0056 to 0066 of JP-A-2009-242604, the contents of which are incorporated herein by reference.
• Commercially available silane coupling agents include A-50 (organosilane) from Soken Chemical Industries, Ltd.
• the content of the silane coupling agent in the total solid content of the composition of the present invention is preferably 0.1 to 5% by mass.
• the upper limit is preferably 3% by mass or less, more preferably 2% by mass or less.
• the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more.
• the silane coupling agent may be one type or two or more types. In the case of two or more types, the total amount is preferably within the above range.
• the composition of the present invention may contain a surfactant.
• the surfactant include those described in paragraph 0017 of Japanese Patent No. 4,502,784 and paragraphs 0060 to 0071 of JP-A-2009-237362.
• the surfactant is preferably a nonionic surfactant, a fluorine-based surfactant, or a silicone-based surfactant.
• fluorosurfactants include Megafac F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143, F-144, F-437, F-475, F-477, F-479, F-482, F-551-A, F-552, F-554, F-555-A, F-556, F-557, F-558, F-559, F-560, F-561, F-565, F-563, F-568, F-575, F-780, EXP, MFS-330, R-41, R-41-LM, R-01, R-40, R-40-LM, RS-43, TF-1956, RS-90, R-94, RS-72-K, DS-21 (all manufactured by DIC Corporation), Flo Lard FC430, FC431, FC171 (all manufactured by Sumitomo 3M Limited), Surflon S-382, SC-101, SC-103, SC-104, SC-105, SC-1068, SC-381
• Acrylic compounds that have a molecular structure with a functional group containing fluorine atoms and that volatilize the fluorine atoms when heated by cleaving the functional group containing fluorine atoms can also be used suitably as fluorosurfactants.
• fluorosurfactants include the Megafac DS series manufactured by DIC Corporation (The Chemical Daily (February 22, 2016), Nikkei Business Daily (February 23, 2016)), such as Megafac DS-21.
• fluorosurfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound.
• Block polymers can also be used as fluorosurfactants.
• the fluorosurfactant may be a fluorine-containing polymer compound that contains a repeating unit derived from a (meth)acrylate compound having a fluorine atom and a repeating unit derived from a (meth)acrylate compound having two or more (preferably five or more) alkyleneoxy groups (preferably ethyleneoxy groups, propyleneoxy groups).
• Fluoropolymers with ethylenically unsaturated bond-containing groups in the side chains can also be used as fluorosurfactants.
• Commercially available products include Megafac RS-101, RS-102, RS-718K, and RS-72-K (all manufactured by DIC Corporation).
• fluorosurfactants that use alternative materials to perfluorooctanoic acid (PFOA) or perfluorooctanesulfonic acid (PFOS).
• Silicone surfactants include linear polymers consisting of siloxane bonds, and modified siloxane polymers with organic groups introduced into the side chains or ends.
• Commercially available silicone surfactants include DOWSIL 8032 ADDITIVE, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (all manufactured by Dow Corning Toray Co., Ltd.), X-22-4952, X-22-4272, X-22-6266, KF-351A, and K35.
• Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane and their ethoxylates and propoxylates (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid esters, etc.
• nonionic surfactants include Pluronic L10, L31, L61, L62, 10R5, 17R2, and 25R2 (all manufactured by BASF), Tetronic 304, 701, 704, 901, 904, and 150R1 (all manufactured by BASF), Solsperse 20000 (all manufactured by Lubrizol Japan), NCW-101, NCW-1001, and NCW-1002 (all manufactured by Fujifilm Wako Pure Chemical Industries), Paionin D-6112, D-6112-W, and D-6315 (all manufactured by Takemoto Oil Co., Ltd.), Olfin E1010, Surfynol 104, 400, and 440 (all manufactured by Nissin Chemical Industry Co., Ltd.), and the like.
• the content of the surfactant in the total solid content of the composition of the present invention is preferably 0.01 to 3.0 mass%, more preferably 0.05 to 1.0 mass%, and even more preferably 0.10 to 0.80 mass%.
• the surfactant may be one type or two or more types. When two or more types are used, it is preferable that the total amount is within the above range.
• the composition of the present invention preferably further contains a solvent.
• the solvent is not particularly limited, and examples thereof include water and organic solvents.
• the solvent is preferably an organic solvent.
• organic solvent examples include alcohol-based solvents, ester-based solvents, ether-based solvents, ketone-based solvents, amide-based solvents, hydrocarbon-based solvents, and halogen-based solvents.
• alcohol-based solvents include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 1-methoxy-2-propanol, 2-ethoxyethanol, 2-butoxyethanol, ethylene glycol, propylene glycol, and glycerin.
• ester-based solvents include methyl acetate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, alkoxyacetic acid alkyl esters (e.g., alkoxyacetic acid methyl, alkoxyacetic acid ethyl ester, alkoxyacetic acid butyl (specific examples include methoxyacetic acid methyl, methoxyacetic acid ethyl ester, methoxyacetic acid butyl, ethoxyacetic acid methyl, ethoxyacetic acid ethyl ester, etc.)), 3-oxypropionic acid alkyl esters, and 2-oxypropionic acid alkyl esters.
• ether-based solvents include diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, polyethylene glycol monoalkyl ether, polypropylene glycol monoalkyl ether, polyethylene glycol, polypropylene glycol, ethylene glycol dialkyl ether, propylene glycol dialkyl ether, polyethylene glycol dialkyl ether, polypropylene glycol dialkyl ether, and dioxane.
• amide solvent examples include N-methylpyrrolidone, dimethylformamide, and dimethylacetamide.
• ketone solvent include methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, and 3-heptanone.
• hydrocarbon solvent examples include toluene and xylene.
• halogen-based solvents include chloroform and methylene chloride. These organic solvents may be used in combination of two or more kinds.
• the organic solvent preferably contains at least one selected from methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, and propylene glycol monomethyl ether acetate.
• the content of the solvent in the composition of the present invention is preferably 10 to 90% by mass, more preferably 30 to 90% by mass, and even more preferably 50 to 90% by mass.
• the composition of the present invention may contain only one type of solvent, or may contain two or more types. When two or more types of solvents are contained, the total amount thereof is preferably within the above range.
• the content of the organic solvent in the composition is preferably 0.1% by mass or less, and more preferably 0.01% by mass or less.
• the composition of the present invention may contain a plasticizer.
• the plasticizer include phthalate ester plasticizers, phosphate ester plasticizers, trimellitate ester plasticizers, fatty acid ester plasticizers, polyester plasticizers, glycerin plasticizers, and polyalkylene glycol plasticizers, and phthalate ester plasticizers and phosphate ester plasticizers are preferred.
• phthalate plasticizers include dimethyl phthalate, diethyl phthalate, diisopropyl phthalate, dibutyl phthalate, diisobutyl phthalate, dihexyl phthalate, dicyclohexyl phthalate, diphenyl phthalate, bis(2-ethylhexyl) phthalate, diisononyl phthalate, diisodecyl phthalate, and diundecyl phthalate.
• the phosphate plasticizer include trimethyl phosphate, triethyl phosphate, tributyl phosphate, triphenyl phosphate, and tricresyl phosphate.
• trimellitic acid ester plasticizers include tributyl trimellitate and tris(2-ethylhexyl) trimellitate.
• fatty acid ester plasticizer examples include dimethyl adipate, diethyl adipate, dipropyl adipate, diisopropyl adipate, dibutyl adipate, diisobutyl adipate, dimethyl dodecanoate, dibutyl maleate, and ethyl oleate.
• polyester-based plasticizers include polyesters composed of an acid component such as adipic acid, sebacic acid, terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid, diphenyldicarboxylic acid, or rosin, and a diol component such as propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, ethylene glycol, or diethylene glycol, and polyesters with hydroxycarboxylic acids such as polycaprolactone, etc. These polyesters may be end-blocked with a monofunctional carboxylic acid or a monofunctional alcohol, or may be end-blocked with an epoxy compound or the like.
• an acid component such as adipic acid, sebacic acid, terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid, diphenyldicarboxylic acid, or rosin
• diol component such
• glycerin-based plasticizer examples include glycerin monoacetomonolaurate, glycerin diacetomonolaurate, glycerin monoacetomonostearate, glycerin diacetomonooleate, and glycerin monoacetomonomonoacetate.
• polyalkylene glycol plasticizer examples include polyalkylene glycols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, ethylene oxide addition polymers of bisphenols, propylene oxide addition polymers of bisphenols, and tetrahydrofuran addition polymers of bisphenols, as well as terminal epoxy-modified compounds, terminal ester-modified compounds, and terminal ether-modified compounds thereof.
• polyalkylene glycols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, ethylene oxide addition polymers of bisphenols, propylene oxide addition polymers of bisphenols, and tetrahydrofuran addition polymers of bisphenols, as well as terminal epoxy-modified compounds, terminal ester-modified compounds, and terminal ether-modified compounds thereof.
• the molecular weight of the plasticizer is preferably less than 3000, more preferably 2000 or less, and even more preferably 1500 or less.
• the content of the plasticizer in the composition of the present invention is preferably 0.001 to 30% by mass.
• the lower limit is preferably 0.005% by mass or more, and more preferably 0.01% by mass or more.
• the upper limit is preferably 20% by mass or less, and more preferably 10% by mass or less.
• the kneaded product may contain only one type of plasticizer, or may contain two or more types. When two or more types of plasticizers are contained, the total amount thereof is preferably within the above range.
• composition of the present invention may contain, as necessary, any additives such as a processing stabilizer, an antiaging agent, a compatibilizer, etc. By appropriately adding these components, various properties of the obtained cured product can be appropriately adjusted.
• composition of the present invention can also be suitably used in applications where it may be exposed to sunlight or light including ultraviolet light.
• Specific examples include coating materials or films for window glass of residences, facilities, transport equipment, etc.; interior and exterior materials and interior and exterior paints for residences, facilities, transport equipment, etc.; light source members that emit ultraviolet light, such as fluorescent lamps and mercury lamps; members for solar cells, precision machinery, electronic and electrical equipment, and display devices; containers or packaging materials for food, chemicals, medicines, etc.; agricultural and industrial sheets; clothing textile products and fibers, such as sportswear, stockings, and hats; lenses such as plastic lenses, contact lenses, glasses, and artificial eyes, or coating materials thereof; optical products, such as optical filters, prisms, mirrors, and photographic materials; stationery, such as tapes and inks; sign plates, indicators, and surface coating materials thereof.
• the composition of the present invention can be preferably used for optical components, etc.
• it is preferably used as a composition for ultraviolet ray cut filters, lenses, or protective materials.
• the form of the protective material is not particularly limited, but examples include a coating film, a film, and a sheet.
• the composition of the present invention can also be used as a pressure sensitive adhesive or a bonding agent.
• composition of the present invention can also be used in various components of display devices.
• a liquid crystal display device it can be used in each component constituting the liquid crystal display device, such as an anti-reflection film, a polarizing plate protective film, an optical film, a retardation film, a pressure sensitive adhesive, or an adhesive.
• an organic electroluminescence display device it can be used in each component constituting the organic electroluminescence display device, such as an optical film, a polarizing plate protective film in a circular polarizing plate, a retardation film such as a quarter wave plate, an adhesive or a pressure sensitive adhesive.
• the cured product of the present invention is obtained by using the above-mentioned composition of the present invention.
• the term "cured product” includes a dried product obtained by drying and solidifying the composition, and, in the case where the composition undergoes a curing reaction, a cured product obtained by curing the composition.
• the cured product of the present invention may be obtained as a molded product obtained by molding the composition into a desired shape.
• the shape of the molded product can be appropriately selected depending on the application and purpose. Examples include coating membrane, film, sheet, plate, lens, tube, fiber, etc.
• the cured product of the present invention is preferably used as an optical component.
• optical components include ultraviolet ray filters, lenses, and protective materials. It can also be used as a polarizing plate.
• the ultraviolet ray cut filter can be used in products such as optical filters, display devices, solar cells, and window glass.
• products such as optical filters, display devices, solar cells, and window glass.
• display devices There are no particular limitations on the type of display device, but examples include liquid crystal display devices and organic electroluminescence display devices.
• the cured product of the present invention When the cured product of the present invention is used for a lens, the cured product of the present invention itself may be formed into a lens shape and used.
• the cured product of the present invention may also be used as a coating film on the lens surface or as an intermediate layer (adhesive layer) of a cemented lens.
• cemented lenses include those described in paragraphs 0094 to 0102 of WO 2019/131572, the contents of which are incorporated herein by reference.
• the types of protective materials are not particularly limited, but examples include protective materials for display devices, protective materials for solar cells, protective materials for window glass, organic electroluminescence display devices, etc.
• the shape of the protective material is not particularly limited, but examples include coating membranes, films, sheets, etc.
• the optical member of the present invention includes a cured product obtained by using the above-mentioned composition of the present invention.
• the cured product of the present invention may be obtained as a molded product obtained by molding the above-mentioned composition of the present invention into a desired shape.
• the shape of the molded product can be appropriately selected according to the application and purpose. For example, it may be a coating film, a film, a sheet, a plate, a lens, a tube, a fiber, etc.
• Types of optical components include UV filters, lenses, and protective materials.
• the ultraviolet ray cut filter can be used in products such as optical filters, display devices, solar cells, and window glass.
• products such as optical filters, display devices, solar cells, and window glass.
• display devices There are no particular limitations on the type of display device, but examples include liquid crystal display devices and organic electroluminescence display devices.
• lenses include the cured product of the present invention itself formed into a lens shape; and the cured product of the present invention is used as a coating film on the surface of a lens or as an intermediate layer (adhesive layer or pressure-sensitive adhesive layer) of a cemented lens.
• the types of protective materials are not particularly limited, but examples include protective materials for display devices, protective materials for solar cells, and protective materials for window glass.
• the shape of the protective material is not particularly limited, but examples include coating membranes, films, and sheets.
• the resin film can be formed using the composition of the present invention, which uses a resin as a curable compound.
• resins used in the composition for forming a resin film include the resins described above, and (meth)acrylic resins, polyester fibers, cyclic olefin resins, and cellulose acylate resins are preferred, with cellulose acylate resin being more preferred.
• the composition for forming a resin film can contain additives described in paragraphs 0022 to 0067 of JP-A-2012-215689. Examples of such additives include sugar esters.
• a sugar ester compound By adding a sugar ester compound to a composition for forming a resin film containing a cellulose acylate resin, it is possible to reduce the total haze and internal haze without impairing the expression of optical properties and even if no heat treatment is performed before the stretching process.
• a resin film (cellulose acylate film) using a composition containing a cellulose acylate resin can be produced by the method described in paragraphs 0068 to 0096 of JP-A-2012-215689.
• the resin film may further be laminated with a hard coat layer as described in paragraphs 0097 to 0113 of JP2012-215689A.
• optical component having a laminate of a support and a resin layer.
• this optical component at least one of the support and the resin layer contains the cured product of the present invention described above.
• the thickness of the resin layer in the laminate is preferably 1 ⁇ m to 2500 ⁇ m, and more preferably 10 ⁇ m to 500 ⁇ m.
• the support in the laminate is preferably a material that has transparency to the extent that the optical performance is not impaired.
• the support being transparent means that it is optically transparent, and specifically means that the total light transmittance of the support is 85% or more.
• the total light transmittance of the support is preferably 90% or more, and more preferably 95% or more.
• a suitable example of the support is a resin film.
• resins that can be used to form the resin film include ester resins (e.g., polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polybutylene terephthalate (PBT), polycyclohexane dimethylene terephthalate (PCT), etc.), olefin resins (e.g., polypropylene (PP), polyethylene (PE), etc.), polyvinyl chloride (PVA), tricellulose acetate (TAC), etc.
• PET is preferred in terms of versatility.
• the thickness of the support can be appropriately selected depending on the application or purpose. In general, the thickness is preferably 5 ⁇ m to 2500 ⁇ m, and more preferably 20 ⁇ m to 500 ⁇ m.
• a peelable support can also be used as the support.
• Such a laminate is preferably used for polarizing plates and the like.
• a peelable support refers to a support that can be peeled off from the resin film.
• the stress when peeling the support from the resin film is preferably 0.05 N/25 mm or more and 2.00 N/25 mm or less, more preferably 0.08 N/25 mm or more and 0.50 N/25 mm or less, and even more preferably 0.11 N/25 mm or more and 0.20 N/25 mm or less.
• the stress when peeling the support from the resin film was evaluated by first pasting and fixing the surface of the laminate cut to a width of 25 mm and a length of 80 mm to a glass substrate via an acrylic adhesive sheet, and then using a tensile tester (RTF-1210 manufactured by A&D Co., Ltd.) to grip one end of the length direction of the test piece (one side of the 25 mm width) and carry out a 90° peel test (in accordance with Japan Industrial Standards (JIS) K 6854-1:1999 "Adhesives - Test method for peel adhesion strength - Part 1: 90° peel") at a crosshead speed (gripping speed) of 200 mm/min in an atmosphere of 23°C and 60% relative humidity.
• JIS Japan Industrial Standards
• the peelable support preferably contains polyethylene terephthalate (PET) as the main component (the component that has the largest content by mass among the components that make up the support).
• PET polyethylene terephthalate
• the weight average molecular weight of PET is preferably 20,000 or more, more preferably 30,000 or more, and even more preferably 40,000 or more.
• the weight average molecular weight of PET can be determined by dissolving the support in hexafluoroisopropanol (HFIP) and using the GPC method described above.
• the thickness of the support is not particularly limited, but is preferably 0.1 to 100 ⁇ m, more preferably 0.1 to 75 ⁇ m, even more preferably 0.1 to 55 ⁇ m, and particularly preferably 0.1 to 10 ⁇ m.
• the support may also be subjected to known surface treatments such as corona treatment, glow discharge treatment, and undercoating.
• optical component is a laminate having a hard coat layer, a transparent support, and an adhesive layer or bonding layer laminated in this order.
• a laminate is preferably used as an ultraviolet cut filter or a protective material (protective film, protective sheet).
• any one of the support, the hard coat layer, and the adhesive layer or bonding layer may contain the cured product of the present invention described above.
• the hard coat layer for example, JP 2013-045045 A, JP 2013-043352 A, JP 2012-232459 A, JP 2012-128157 A, JP 2011-131409 A, JP 2011-131404 A, JP 2011-126162 A, JP 2011-075705 A, JP 2009-286981 A, JP 2009-263567 A, JP 200
• the hard coat layers described in JP-A-9-075248, JP-A-2007-164206, JP-A-2006-096811, JP-A-2004-075970, JP-A-2002-156505, JP-A-2001-272503, WO-2012/018087, WO-2012/098967, WO-2012/086659, and WO-2011/105594 can be applied.
• the thickness of the hard coat layer is preferably 5 to 100 ⁇ m in order to further improve scratch resistance.
• the optical member of this form has an adhesive layer or a bonding layer on the side opposite to the side having the hard coat layer of the supporting substrate.
• the type of adhesive or bonding agent used in the adhesive layer or bonding layer is not particularly limited, and any known adhesive or bonding agent can be used. It is also preferable to use an adhesive or bonding agent containing the acrylic resin described in paragraphs 0056 to 0076 of JP 2017-142412 A and the crosslinking agent described in paragraphs 0077 to 0082 of JP 2017-142412 A.
• the adhesive or bonding agent may also contain an adhesion improver (silane compound) described in paragraphs 0088 to 0097 of JP 2017-142412 A, and an additive described in paragraph 0098 of JP 2017-142412 A.
• the adhesive layer or the bonding layer can be formed by the method described in paragraphs 0099 to 0100 of JP 2017-142412 A.
• the thickness of the adhesive layer or the bonding layer is preferably 5 ⁇ m to 100 ⁇ m in terms of achieving both adhesive strength and handling properties.
• the optical member of the present invention can be preferably used as a component of displays such as liquid crystal displays (LCDs) and organic electroluminescent displays (OLEDs).
• LCDs liquid crystal displays
• OLEDs organic electroluminescent displays
• Liquid crystal display devices include those that contain the cured product of the present invention in components such as anti-reflection films, polarizing plate protective films, optical films, retardation films, pressure sensitive adhesives, and adhesives.
• Optical components containing the cured product of the present invention may be disposed on either the viewer side (front side) or the backlight side of the liquid crystal cell, and may also be disposed on either the side of the polarizer that is farther from the liquid crystal cell (outer side) or the side that is closer to the liquid crystal cell (inner side).
• organic electroluminescent display devices include those that contain the cured product of the present invention in components such as optical films, polarizing plate protective films in circular polarizing plates, retardation films such as quarter-wave plates, adhesives, and pressure-sensitive adhesives.
• components such as optical films, polarizing plate protective films in circular polarizing plates, retardation films such as quarter-wave plates, adhesives, and pressure-sensitive adhesives.
• intermediate 1-2 was synthesized according to the following synthesis scheme. 50 g of intermediate 1-1, 24.5 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone, and 500 ml of tetrahydrofuran were added and mixed, and then stirred at 20° C. for 1 hour. After the reaction was completed, 500 mL of hexane was added, and the precipitated solid was collected by filtration and washed with 150 ml of hexane, thereby obtaining 42 g (yield 84%) of intermediate 1-2.
• intermediate 1-3 was synthesized according to the following synthesis scheme. 30 g of intermediate 1-2, 8 g of piperidinium pentamethylene dithiocarbamate, 360 mL of N-methyl-2-pyrrolidone, 160 mL of acetic acid, and 54 mL of acetone were mixed and stirred at 60° C. for 1 hour. The precipitated solid was collected by filtration and washed with 300 ml of acetone, yielding 8.0 g of intermediate 1-3 (yield 36%).
• Synthesis Example 3 Synthesis of Compound A-1
• Compound A-1 was synthesized according to the following synthesis scheme. 1.5 g of compound A-104, 0.76 g of triethylamine, 1.0 g of 2-ethylhexanoyl chloride, and 30 ml of dimethylacetamide were added and mixed, and then stirred at 20° C. for 1 hour. After completion of the reaction, 30 ml of water was added and stirred for 30 minutes. The precipitated solid was filtered and washed with 30 ml of methanol, and then purified by silica gel column chromatography to obtain 1.6 g of compound A-1 (yield 75%).
• UV absorber compounds shown in the table below (exemplary compounds (1) to (21), comparative compounds (1) to (2))
• exemplary compounds (1) to (21), comparative compounds (1) to (2) exemplary compounds shown in the table below
• exemplary compounds (1) to (21), comparative compounds (1) to (2) exemplary compounds shown in the table below
• exemplary compounds (1) to (21), comparative compounds (1) to (2) exemplary compounds shown in the table below
• exemplary compounds (1) to (21), comparative compounds (1) to (2) exemplary compounds shown in the table below (exemplary compounds (1) to (21), comparative compounds (1) to (2))
• 1.1 parts by mass Resin Dianal BR-80, manufactured by Mitsubishi Chemical Corporation, containing 60% or more by mass of methyl methacrylate as monomer units, weight average molecular weight 95,000).
• Discoloration inhibitor compounds shown in the table below
• Solvent chloroform
• compositions were spin-coated onto a glass substrate and then dried at 110°C for 2 minutes to produce a film.
• the absorbance of the obtained film was measured using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation), and the ratio of the absorbance at a wavelength of 440 nm to the absorbance at a wavelength of 400 nm taken as 1 (absorbance ratio A 440 ) was calculated to evaluate the colorability (colorability 1) according to the following criteria: The smaller the absorbance ratio A 440 value, the less coloring there was.
• the obtained film was subjected to a light resistance test under the following condition 1, and the absorbance of the film after the light resistance test was measured using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation).
• the ratio of the absorbance at a wavelength of 440 nm to the absorbance at a wavelength of 400 nm taken as 1 (absorbance ratio A 440 ) was calculated to evaluate the colorability according to the following criteria.
• the value in parentheses in the colorability column is the absorbance ratio A 440 value.
• C Absorbance ratio A 440 is greater than 0.02.
• Examples 101 to 166 were excellent in long-wavelength ultraviolet ray absorption ability.
• the absorbance ratio A440 was small both before and after the light fastness test, and the evaluation of colorability was excellent.
• the absorbance retention rate after the light fastness test was high, and the evaluation of light fastness was also excellent.
• UV absorber (compounds listed in the table below) 0.6 parts by weight Polymerizable compound (KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd., compound having two or more ethylenically unsaturated bond-containing groups) 10.9 parts by weight Resin (DIANAL BR-80 (manufactured by Mitsubishi Chemical Corporation)) 13.4 parts by weight Photopolymerization initiator (compounds listed in the table below) 0.6 parts by weight Discoloration inhibitor (compounds listed in the table below) 0.8 parts by weight Solvent (propylene glycol monomethyl ether acetate) 73.7 parts by weight
• V-1 Irgacure OXE01 (manufactured by BASF, oxime compound, photoradical polymerization initiator)
• V-2 Omnirad 2959 (manufactured by IGM Resins B.V., hydroxyacetophenone compound, photoradical polymerization initiator)
• V-3 Omnirad TPO (manufactured by IGM Resins B.V., acylphosphine compound, photoradical polymerization initiator)
• composition layer was spin-coated onto a 50 mm x 50 mm glass substrate (1737, Corning) so that the film thickness after film formation was 1.5 ⁇ m, and dried at 120 ° C for 5 minutes to form a composition layer. Thereafter, the composition layer was exposed to an i-line stepper exposure device (UX-1000SM-EH04, Ushio Inc.) at an exposure dose of 1000 mJ / cm 2 on the entire surface to produce a film.
• UX-1000SM-EH04 Ushio Inc.
• the change in transmittance at the maximum absorption wavelength ( ⁇ max) of the composition layer before and after exposure was 5% or less.
• the obtained film was subjected to a light resistance test under the following condition 2, and the retention rate of absorbance at the maximum absorption wavelength ( ⁇ max) of the film before and after the light resistance test was obtained in the same manner as in the evaluation of light resistance in Test Example 1, and the light resistance was evaluated according to the following evaluation criteria.
• Absorbency maintenance rate is 80% or more.
• Examples 201 to 253 had small absorbance ratio A440 values both before and after the light fastness test, and were excellent in the evaluation of colorability. Furthermore, the absorbance retention rate after the light fastness test was high, and the evaluation of light fastness was also excellent.
• Synthesis of Polymer P-1 In a 200 mL three-neck flask, 100 mg of compound A-142 (maximum absorption wavelength (in ethyl acetate solution): 394 nm), 9.9 g of methyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate were added and stirred at 80 ° C. for 30 minutes under a nitrogen stream. 200 mg of 2,2'-azobis(isobutyrate)dimethyl (V-601, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. (hereinafter referred to as V-601)) was added to this solution, stirred at 80 ° C.
• V-601 2,2'-azobis(isobutyrate)dimethyl
• the number average molecular weight of the obtained polymer P-1 was 27,500 (polystyrene equivalent). 100 mg of the obtained polymer P-1 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelength of the polymer P-1 was 399 nm (absorbance 1.61). The polymer P-1 was capable of sufficiently blocking light having a wavelength in the vicinity of 400 nm, and was less colored.
• Synthesis Example 102 Synthesis of Polymer P-2 In a 200 mL three-neck flask, 100 mg of compound A-142 (maximum absorption wavelength (in ethyl acetate solution): 394 nm), 100 mg of 2-[2-hydroxy-5-(2-methacryloyloxyethyl)phenyl]2H-benzo[d][1,2,3]triazole (maximum absorption wavelength (in ethyl acetate solution): 338 nm) as an ultraviolet absorber, 9.8 g of methyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate were added, and the mixture was stirred at 80° C.
• the number average molecular weight of the obtained polymer P-2 was 33,400 (polystyrene equivalent). 150 mg of the obtained polymer P-2 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelengths of the polymer P-2 were 399 nm (absorbance 1.45) and 343 nm (absorbance 0.83). The polymer P-2 was capable of sufficiently shielding light with a wavelength in the vicinity of 400 nm. Furthermore, the polymer P-2 was also excellent in shielding light with a wavelength shorter than 350 nm. Moreover, the polymer P-2 was less colored.
• the resulting reaction mixture was slowly added to a mixture of 200 mL of methanol and left overnight.
• the precipitate was collected by filtration and washed with a mixture of chloroform and methanol.
• 20 mL of chloroform and 200 mL of methanol were added to the obtained powder, stirred at room temperature for 1 hour, and then left at room temperature overnight.
• the precipitate was collected by filtration, washed with a mixture of chloroform and methanol, and dried at 50° C. to obtain 5.2 g of the target polymer P-3.
• the number average molecular weight of the obtained polymer P-3 was 96,000 (polystyrene equivalent).
• the polymer P-3 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured.
• the maximum absorption wavelength of the polymer P-3 was 399 nm (absorbance 1.56).
• the polymer P-3 was capable of sufficiently blocking light having a wavelength in the vicinity of 400 nm.
• the polymer P-3 was also little colored.
• Synthesis Example 104 Synthesis of Polymer P-4 In a 200 mL three-neck flask, 100 mg of compound A-232 (maximum absorption wavelength (in ethyl acetate solution): 391 nm), 9.9 g of methyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate were added and stirred at 80 ° C. for 30 minutes under a nitrogen stream. 200 mg of 2,2'-azobis(isobutyrate)dimethyl (V-601, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. (hereinafter referred to as V-601)) was added to this solution, stirred at 80 ° C. for 6 hours, and then cooled to room temperature.
• V-601 2,2'-azobis(isobutyrate)dimethyl
• the resulting reaction mixture was slowly added to a mixture of 140 mL of hexane and 60 mL of isopropyl alcohol and left overnight.
• the precipitate was collected by filtration and washed with a mixture of hexane and isopropyl alcohol.
• 140 mL of hexane and 60 mL of isopropyl alcohol were added to the obtained powder, stirred at room temperature for 1 hour, and then left at room temperature overnight.
• the precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50° C. to obtain 7.4 g of the target polymer P-4.
• the number average molecular weight of the obtained polymer P-4 was 29,500 (polystyrene equivalent). 100 mg of the obtained polymer P-4 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelength of the polymer P-4 was 397 nm (absorbance 1.57). The polymer P-4 was capable of sufficiently blocking light having a wavelength in the vicinity of 400 nm. The polymer P-4 was also little colored.
• Synthesis Example 105 Synthesis of Polymer P-5
• 100 mg of compound A-352 maximal absorption wavelength (in ethyl acetate solution): 392 nm
• 9.9 g of methyl methacrylate 9.9 g
• 40.0 g of propylene glycol monomethyl ether acetate were added and stirred at 80° C. for 30 minutes under a nitrogen stream.
• 200 mg of 2,2'-azobis(isobutyrate)dimethyl V-601, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. (hereinafter referred to as V-601) was added to this solution, stirred at 80° C. for 6 hours, and then cooled to room temperature.
• V-601 2,2'-azobis(isobutyrate)dimethyl
• the resulting reaction mixture was slowly added to a mixture of 140 mL of hexane and 60 mL of isopropyl alcohol and left overnight.
• the precipitate was collected by filtration and washed with a mixture of hexane and isopropyl alcohol.
• 140 mL of hexane and 60 mL of isopropyl alcohol were added to the obtained powder, stirred at room temperature for 1 hour, and then left at room temperature overnight.
• the precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50° C. to obtain 7.8 g of the target polymer P-5.
• the number average molecular weight of the obtained polymer P-5 was 45,000 (polystyrene equivalent). 100 mg of the obtained polymer P-5 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelength of the polymer P-5 was 397 nm (absorbance 1.47). Polymer P-5 was able to sufficiently block light having a wavelength in the vicinity of 400 nm, and was less colored.
• the resulting reaction mixture was slowly added to a mixture of 140 mL of hexane and 60 mL of isopropyl alcohol.
• the precipitate was collected by filtration and washed with a mixture of hexane and isopropyl alcohol.
• 140 mL of hexane and 60 mL of isopropyl alcohol were added to the obtained powder, and the mixture was stirred at room temperature for 3 hours.
• the precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50° C. to obtain 8.1 g of the target polymer P-6.
• the number average molecular weight of the obtained polymer P-6 was 14,100 (polystyrene equivalent).
• the polymer P-6 had low shielding properties for light with wavelengths of 380 to 400 nm.
• Example 3 (Examples 301 to 310, Comparative Examples 301 and 302) A composition (resin composition (resin solution)) was prepared by dissolving 500 mg of the polymer shown in the table below, 5.1 mg of the anti-fading agent shown in the table below, 7.6 g of chloroform, and 1.1 g of polymethyl methacrylate resin (Dianal BR-80 (containing 60% by mass or more of methyl methacrylate as a monomer unit, weight average molecular weight: 95,000, acid value: 0 mgKOH/g, manufactured by Mitsubishi Chemical Corporation)). The obtained composition was spin-coated on a glass substrate, and the coating film was dried at 60° C.
• resin composition resin solution
• Examples 301 to 310 had small absorbance ratio A440 values both before and after the light fastness test, and were excellent in the evaluation of colorability. Furthermore, the absorbance retention rate after the light fastness test was high, and the evaluation of light fastness was also excellent.
• Irgacure OXE01 manufactured by BASF, oxime compound, photoradical polymerization initiator
• a (meth)acrylic resin Dianal BR-80, manufactured by
• composition layer was spin-coated onto a 50 mm x 50 mm glass substrate (1737, Corning) so that the film thickness after film formation was 1.5 ⁇ m, and dried at 120 ° C for 5 minutes to form a composition layer. Thereafter, the composition layer was exposed to an i-line stepper exposure device (UX-1000SM-EH04, Ushio Inc.) at an exposure dose of 1000 mJ / cm 2 on the entire surface to produce a film.
• UX-1000SM-EH04 Ushio Inc.
• the change in transmittance at the maximum absorption wavelength ( ⁇ max) of the composition layer before and after exposure was 5% or less.
• Examples 401 to 436 had small absorbance ratio A440 values both before and after the light fastness test, and were excellent in the evaluation of colorability. Furthermore, the absorbance retention rate after the light fastness test was high, and the evaluation of light fastness was also excellent.

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