Classifications

• • 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
  • 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

Definitions

• the present invention relates to a thermosetting composition containing an ultraviolet absorber.
• the present invention also relates to a cured product and an optical member using the thermosetting composition.
• Patent Document 1 describes an invention relating to spectacle lenses using a specific benzobisdithiol compound as an ultraviolet absorber.
• ultraviolet absorbers One of the required properties of ultraviolet absorbers is that they have little coloring.
• an object of the present invention is to provide a thermosetting composition, a cured product, and an optical member that can produce a cured product with little coloring and suppressed haze.
• the present invention provides the following. ⁇ 1> An ultraviolet absorber containing at least one compound A selected from the compound represented by formula (1) and the compound represented by formula (2); a thermosetting compound; A thermosetting composition containing at least one thermosetting aid selected from a thermal polymerization initiator and a polymerization catalyst;
• R 1 and R 2 each independently represent a hydrogen atom, an alkyl group, an aryl group, an acyl group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, or an ethylenically unsaturated bond-containing group.
• R 3 and R 4 are each independently a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an aryl Represents a sulfonylamino group, alkylthio group, arylthio group or ethylenically unsaturated bond-containing group
• R 5 and R 6 each independently represent a hydrogen atom, an alkyl group having 2 or more carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, or an ethylenically unsaturated bond-containing group
• R 1 and R 3 may be combined to form a ring
• R 3 and R 4 may be combined to form a ring
• R 2 and R 4 may be combined to form a ring
• Q 1 represents a group represented by formula (Q-1)
• R q1 to R q3 each independently represent a hydrogen atom or a substituent, and R q2 and R q3 bond to each other. may form a ring
• * represents a bond
• R 101 and R 102 each independently represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or an ethylenically unsaturated bond-containing group. represents.
• thermosetting composition according to ⁇ 1> which represents an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group, an arylthio group, or an ethylenically unsaturated bond-containing group.
• the thermosetting compounds include phenol resins, epoxy resins, melamine resins, urea resins, polyester resins, alkyd resins, polyimide resins, polyurethane resins, polythiourethane resins, diallyl phthalate resins, episulfide resins, siloxane resins, and these.
• thermosetting composition according to any one of ⁇ 1> to ⁇ 4> which contains at least one selected from the precursors.
• ⁇ 6> A cured product obtained using the thermosetting composition according to any one of ⁇ 1> to ⁇ 5>.
• An optical member comprising the cured product according to ⁇ 6>.
• the present invention can provide a thermosetting composition, a cured product, and an optical member that can produce a cured product with little coloring and suppressed haze.
• alkyl group includes not only an alkyl group without a substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
• a numerical range expressed using " ⁇ ” means a range that includes the numerical values written before and after " ⁇ " as lower and upper limits.
• the total solid content refers to the total amount of all components of the composition excluding the solvent.
• (meth)acrylate represents acrylate and/or methacrylate
• (meth)acrylic represents both acrylic and/or methacrylic
• (meth)acrylate represents acrylic and/or methacrylate.
• Allyl represents allyl and/or methallyl
• “(meth)acryloyl” represents both acryloyl and methacryloyl, or either one.
• the term “process” does not only mean an independent process; even if the process cannot be clearly distinguished from other processes, if the intended effect of the process is achieved, the term include.
• weight average molecular weight (Mw) and number average molecular weight (Mn) are defined as polystyrene equivalent values measured by gel permeation chromatography (GPC).
• thermosetting composition of the present invention includes: An ultraviolet absorber containing at least one compound A selected from the compound represented by formula (1) and the compound represented by formula (2); a thermosetting compound; It is characterized by containing at least one thermosetting aid selected from a thermal polymerization initiator and a polymerization catalyst.
• thermosetting composition of the present invention Since the compound represented by formula (1) and the compound represented by formula (2) have high solubility in organic solvents, these compounds may be added to the surface of the cured product using the thermosetting composition of the present invention. Precipitation of the compound can be suppressed.
• the compound represented by formula (1) and the compound represented by formula (2) have excellent thermal stability and are highly stable against radicals and peroxides, so they are thermosetting. Decomposition and denaturation during curing of the composition can be suppressed. Therefore, by using the thermosetting composition of the present invention, it is possible to produce a cured product with little coloring and suppressed haze.
• thermosetting composition of the present invention a cured product with excellent solvent resistance can also be obtained.
• the reason why such an effect is obtained is that the compound represented by formula (1) and the compound represented by formula (2) have high compatibility with thermosetting compounds, and they also have high compatibility with thermosetting compounds. It is presumed that this is because it is difficult to inhibit curing.
• the compound represented by formula (1) and the compound represented by formula (2) have excellent absorption performance for light with a wavelength of around 400 nm, and by using the thermosetting composition of the present invention, the compound represented by formula (2) can absorb light with a wavelength of around 400 nm. It is possible to produce a cured product that has excellent shielding properties against nearby light.
• thermosetting composition each component contained in the thermosetting composition will be explained.
• the thermosetting composition of the present invention contains an ultraviolet absorber.
• the ultraviolet absorber contains at least one compound A (hereinafter also referred to as a specific compound) selected from the compound represented by formula (1) and the compound represented by formula (2).
• R 1 and R 2 each independently represent a hydrogen atom, an alkyl group, an aryl group, an acyl group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, or an ethylenically unsaturated bond-containing group.
• R 3 and R 4 are each independently a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an aryl Represents a sulfonylamino group, alkylthio group, arylthio group or ethylenically unsaturated bond-containing group
• R 5 and R 6 each independently represent a hydrogen atom, an alkyl group having 2 or more carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, or an ethylenically unsaturated bond-containing group
• R 1 and R 3 may be combined to form a ring
• R 3 and R 4 may be combined to form a ring
• R 2 and R 4 may be combined to form a ring
• Q 1 represents a group represented by formula (Q-1)
• R q1 to R q3 each independently represent a hydrogen atom or a substituent, and R q2 and R q3 bond to each other. may form a ring
• * represents a bond
• R 101 and R 102 each independently represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or an ethylenically unsaturated bond-containing group. represents.
• R 1 and R 2- R 1 and R 2 in formula (1) each independently represent a hydrogen atom, an alkyl group, an aryl group, an acyl group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, or an ethylenically unsaturated bond-containing group. .
• the alkyl group represented by R 1 and R 2 is preferably an alkyl group having 1 to 30 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, and more preferably an alkyl group having 1 to 15 carbon atoms. More preferably, it is an alkyl group having 1 to 10 carbon atoms.
• the alkyl group may be linear, branched, or cyclic, but is preferably a linear or branched alkyl group.
• the alkyl group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the aryl group represented by R 1 and R 2 is preferably an aryl group having 6 to 30 carbon atoms, more preferably 6 to 10 carbon atoms.
• the aryl group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the acyl group represented by R 1 and R 2 is preferably an acyl group having 2 to 30 carbon atoms.
• the acyl group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the carbamoyl group represented by R 1 and R 2 is preferably a carbamoyl group having 1 to 30 carbon atoms.
• the carbamoyl group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the alkoxycarbonyl group represented by R 1 and R 2 includes an alkoxycarbonyl group having 2 to 30 carbon atoms.
• the alkoxycarbonyl group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the aryloxycarbonyl group represented by R 1 and R 2 includes an aryloxycarbonyl group having 7 to 30 carbon atoms.
• the aryloxycarbonyl group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the ethylenically unsaturated bond-containing groups represented by R 1 and R 2 include a vinyl group, (meth)allyl group, (meth)acryloyl group, (meth)acryloyloxy group, (meth)acryloylamino group, vinylphenyl group, and Examples include a group represented by formula (R100).
• Rx 1 is Represents a hydrogen atom, alkyl group or aryl group
• - *1 represents a bond with Y R1
• Y R1 represents a single bond or a divalent linking group
• Z R1 represents a vinyl group, (meth)allyl group, (meth)acryloyl group, (meth)acryloyloxy group, (meth)acryloylamino group or vinylphenyl group.
• the alkyl group represented by Rx 1 is preferably an alkyl group having 1 to 30 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, and still more preferably an alkyl group having 1 to 15 carbon atoms.
• an alkyl group having 1 to 10 carbon atoms is particularly preferable.
• the alkyl group may be linear, branched, or cyclic, but is preferably a linear or branched alkyl group.
• the aryl group represented by Rx 1 is preferably an aryl group having 6 to 30 carbon atoms, more preferably 6 to 10 carbon atoms.
• the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group, with an aliphatic hydrocarbon group being preferred.
• 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 ring or a condensed ring. Furthermore, the cyclic aliphatic hydrocarbon group may have a crosslinked structure.
• 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. Examples of the substituent include the substituent T described below. For example, examples of the substituent include a hydroxy group.
• the divalent linking group represented by Y R1 is preferably a hydrocarbon group or a group in which two or more hydrocarbon groups are linked via a single bond or a divalent linking group.
• Z R1 is preferably a (meth)acryloyloxy group or a vinylphenyl group, and more preferably a (meth)acryloyloxy group.
• R 1 and R 2 in formula (1) are each independently an alkyl group, an acyl group, a carbamoyl group, or an ethylenically unsaturated bond-containing group.
• R 1 and R 2 are each independently an alkyl group, it is excellent in terms of ultraviolet shielding ability.
• R 1 and R 2 are each independently an acyl group or a carbamoyl group, it is excellent in terms of light resistance.
• R 1 and R 2 are each independently an ethylenically unsaturated bond-containing group, the solvent resistance of the resulting cured product can be further improved.
• R 3 and R 4- R 3 and R 4 in formula (1) each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkyl Represents a sulfonylamino group, arylsulfonylamino group, alkylthio group, arylthio group, or ethylenically unsaturated bond-containing group.
• Examples of the halogen atom represented by R 3 and R 4 include a fluorine atom, a chlorine atom, and a bromine atom.
• the alkyl group represented by R 3 and R 4 is preferably an alkyl group having 1 to 30 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms. is even more preferable, an alkyl group having 1 or 2 carbon atoms is even more preferable, and a methyl group is particularly preferable.
• the alkyl group is preferably a straight-chain or branched alkyl group, more preferably a straight-chain alkyl group.
• the alkyl group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the aryl group represented by R 3 and R 4 is preferably an aryl group having 6 to 30 carbon atoms, more preferably 6 to 10 carbon atoms.
• the aryl group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the alkoxy group represented by R 3 and R 4 is preferably an alkoxy group having 1 to 30 carbon atoms.
• the alkoxy group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the aryloxy group represented by R 3 and R 4 is preferably an aryloxy group having 6 to 30 carbon atoms.
• the aryloxy group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the acyloxy group represented by R 3 and R 4 is preferably an acyloxy group having 2 to 30 carbon atoms.
• the acyloxy group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the alkylamino group represented by R 3 and R 4 preferably has 1 to 30 carbon atoms.
• the alkylamino group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
• the anilino group represented by R 3 and R 4 is preferably an anilino group having 6 to 40 carbon atoms, more preferably an anilino group having 6 to 30 carbon atoms, and preferably an anilino group having 6 to 20 carbon atoms. More preferably, it is an anilino group having 6 to 15 carbon atoms, and most preferably an anilino group having 6 to 12 carbon atoms.
• the anilino group may have a substituent. Examples of the substituent include the groups described below for substituent T.
• the acylamino group represented by R 3 and R 4 is preferably an acylamino group having 2 to 30 carbon atoms, more preferably an acylamino group having 2 to 20 carbon atoms, and more preferably an acylamino group having 2 to 15 carbon atoms. More preferably, it is an acylamino group having 2 to 10 carbon atoms.
• the acylamino group may have a substituent. Examples of the substituent include the groups described below for substituent T.
• the alkylsulfonylamino group represented by R 3 and R 4 is preferably an alkylsulfonylamino group having 2 to 30 carbon atoms, more preferably an alkylsulfonylamino group having 2 to 20 carbon atoms, and preferably has 2 to 30 carbon atoms. It is more preferably an alkylsulfonylamino group having 15 carbon atoms, and particularly preferably an alkylsulfonylamino group having 2 to 10 carbon atoms.
• the alkylsulfonylamino group may have a substituent. Examples of the substituent include the groups described below for substituent T.
• the arylsulfonylamino group represented by R 3 and R 4 is preferably an arylsulfonylamino group having 6 to 40 carbon atoms, more preferably an arylsulfonylamino group having 6 to 30 carbon atoms, and preferably has 6 to 40 carbon atoms. It is more preferably an arylsulfonylamino group having 20 carbon atoms, particularly preferably an arylsulfonylamino group having 6 to 15 carbon atoms, and most preferably an arylsulfonylamino group having 6 to 12 carbon atoms.
• the arylsulfonylamino group may have a substituent. Examples of the substituent include the groups described below for substituent T.
• the alkylthio group represented by R 3 and R 4 is preferably an alkylthio group having 1 to 30 carbon atoms, more preferably an alkylthio group having 1 to 20 carbon atoms, and an alkylthio group having 1 to 15 carbon atoms. More preferably, it is an alkylthio group having 1 to 10 carbon atoms, and most preferably an alkylthio group having 1 to 8 carbon atoms.
• the alkylthio group may be linear or branched.
• the alkylthio group may have a substituent. Examples of the substituent include the groups described below for substituent T.
• the arylthio group represented by R 3 and R 4 is preferably an arylthio group having 6 to 40 carbon atoms, more preferably an arylthio group having 6 to 30 carbon atoms, and more preferably an arylthio group having 6 to 20 carbon atoms. More preferably, it is an arylthio group having 6 to 15 carbon atoms, and most preferably an arylthio group having 6 to 12 carbon atoms.
• the arylthio group may have a substituent. Examples of the substituent include the groups described below for substituent T.
• Examples of the ethylenically unsaturated bond-containing group represented by R 3 and R 4 include the groups described as the ethylenically unsaturated bond-containing group represented by R 1 and R 2 in formula (1).
• At least one of R 3 and R 4 is a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group.
• a group, an arylthio group, or an ethylenically unsaturated bond-containing group is preferable.
• R 3 and R 4 are a hydrogen atom, and the other is a halogen atom, an alkyl group, an aryl group, an alkoxy group, or an aryl group, from the viewpoint of obtaining high ultraviolet absorption ability and ease of synthesis.
• R 3 and R 4 It is preferably an oxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group, an arylthio group, or a group containing an ethylenically unsaturated bond, R 3 and R 4 It is more preferable that one of R 3 and R 4 is a hydrogen atom and the other is an alkyl group, and it is particularly preferable that one of R 3 and R 4 is a hydrogen atom and the other is a methyl group.
• R 1 and R 3 may be combined to form a ring
• R 3 and R 4 may be combined to form a ring
• R 2 and R 4 may be combined to form a ring. It may form a ring.
• the ring formed by combining these groups is preferably a 5- or 6-membered ring.
• the ring formed may have a substituent. Examples of the substituent include the groups described below for substituent T.
• R 5 and R 6- R 5 and R 6 in formula (1) each independently represent a hydrogen atom, an alkyl group having 2 or more carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, or an ethylenically unsaturated bond-containing group.
• the alkyl group represented by R 5 and R 6 is an alkyl group having 2 or more carbon atoms, preferably an alkyl group having 3 or more carbon atoms, and more preferably an alkyl group having 4 or more carbon atoms.
• the number of carbon atoms in the alkyl group is preferably 30 or less, more preferably 20 or less, even more preferably 15 or less, even more preferably 10 or less, particularly 8 or less.
• the alkyl group may be linear, branched, or cyclic, and preferably linear or branched.
• the alkyl group may have a substituent. Examples of the substituent include the groups described below for substituent T.
• the number of carbon atoms in the alkyl moiety in the aralkyl group represented by R 5 and R 6 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 moiety in 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 described below for substituent T. Specific examples of aralkyl groups include benzyl groups.
• the aryl group represented by R 5 and R 6 is preferably an aryl group having 6 to 40 carbon atoms, more preferably an aryl group having 6 to 30 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms. More preferably, it is an aryl group having 6 to 15 carbon atoms, and most preferably an aryl group having 6 to 12 carbon atoms.
• the aryl group is preferably a phenyl group or a naphthyl group, and more preferably a phenyl group.
• the aryl group may have a substituent. Examples of the substituent include the groups described below for substituent T.
• the heterocycle in the heterocyclic group represented by R 5 and R 6 preferably includes a 5- or 6-membered saturated or unsaturated heterocycle.
• An aliphatic ring, aromatic ring or other heterocycle may be fused to the heterocycle.
• the heteroatoms constituting the heterocyclic ring include B, N, O, S, Se and Te, with N, O and S being preferred.
• the heterocycle has a free valence (monovalence) at its carbon atom (the heterocyclic group is bonded at the carbon atom).
• the heterocyclic group preferably has 1 to 40 carbon atoms, more preferably 1 to 30 carbon atoms, and even more preferably 1 to 20 carbon atoms.
• Examples of saturated heterocycles in the heterocyclic group include pyrrolidine ring, morpholine ring, 2-bora-1,3-dioxolane ring and 1,3-thiazolidine ring.
• Examples of unsaturated heterocycles in the heterocyclic group include imidazole ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzotriazole ring, benzoselenazole ring, pyridine ring, pyrimidine ring and quinoline ring.
• the heterocyclic group may have a substituent. Examples of the substituent include the groups described below for substituent T.
• Examples of the ethylenically unsaturated bond-containing group represented by R 5 and R 6 include the groups described as the ethylenically unsaturated bond-containing group represented by R 1 and R 2 in formula (1).
• R 5 and R 6 in formula (1) may be combined to form a ring.
• the ring formed by combining these groups is preferably a 5- or 6-membered ring. Specific examples of the ring include hexahydropyridazine ring, tetrahydropyridazine ring, and tetrahydrophthalazine ring.
• the ring formed may have a substituent. Examples of the substituent include the groups described below for substituent T.
• R 5 and R 6 in formula (1) are each independently preferably an alkyl group, an aralkyl group, or an aryl group having 2 or more carbon atoms, and are an alkyl group or an aralkyl group having 2 or more carbon atoms. is more preferable, and even more preferably an alkyl group or an aralkyl group having 4 or more carbon atoms.
• R 11 and R 12- R 11 and R 12 in formula (2) each independently represent a hydrogen atom, an alkyl group, an aryl group, an acyl group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, or an ethylenically unsaturated bond-containing group. .
• the alkyl group, aryl group, acyl group, carbamoyl group, alkoxycarbonyl group, aryloxycarbonyl group, and ethylenically unsaturated bond-containing group represented by R 11 and R 12 in formula (2) are R 1 and R 12 in formula (1).
• the groups explained as being represented by R 2 can be mentioned, and the preferred ranges are also the same.
• R 11 and R 12 in formula (2) are each independently an alkyl group, an acyl group, a carbamoyl group, or an ethylenically unsaturated bond-containing group.
• R 11 and R 12 are each independently an alkyl group, it is excellent in terms of ultraviolet shielding ability.
• R 11 and R 12 are each independently an acyl group or a carbamoyl group, it is excellent in terms of light resistance.
• R 11 and R 12 are each independently an ethylenically unsaturated bond-containing group, the solvent resistance of the resulting cured product can be further improved.
• Q1- Q 1 in formula (2) 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 an ethylenically unsaturated bond-containing group.
• the alkyl group represented by R 101 and R 102 preferably has 1 to 30 carbon atoms.
• 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, more preferably 3 or more.
• the alkyl group may be linear, branched, or cyclic, and preferably linear or branched.
• the alkyl group may have a substituent. Examples of the substituent include the groups described below for substituent T.
• the number of carbon atoms in the alkyl moiety in 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 moiety in 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 described below for substituent T.
• the number of carbon atoms in the aryl group represented by R 101 and R 102 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 substituent T.
• the heterocycle in the heterocyclic group represented by R 101 and R 102 preferably includes a 5- or 6-membered saturated or unsaturated heterocycle.
• An aliphatic ring, aromatic ring or other heterocycle may be fused to the heterocycle.
• the heteroatoms constituting the heterocyclic ring include B, N, O, S, Se and Te, with N, O and S being preferred.
• the heterocycle has a free valence (monovalence) at its carbon atom (the heterocyclic group is bonded at the carbon atom).
• the heterocyclic group preferably has 1 to 40 carbon atoms, more preferably 1 to 30 carbon atoms, and even more preferably 1 to 20 carbon atoms.
• Examples of saturated heterocycles in the heterocyclic group include pyrrolidine ring, morpholine ring, 2-bora-1,3-dioxolane ring and 1,3-thiazolidine ring.
• Examples of unsaturated heterocycles in the heterocyclic group include imidazole ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzotriazole ring, benzoselenazole ring, pyridine ring, pyrimidine ring and quinoline ring.
• the heterocyclic group may have a substituent. Examples of the substituent include the groups described below for substituent T.
• Examples of the ethylenically unsaturated bond-containing group represented by R 101 and R 102 include the groups described as the ethylenically unsaturated bond-containing group represented by R 1 and R 2 in formula (1).
• 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, and an aryloxycarbonyl group. group, alkyl group, aryl group, heterocyclic group, etc. These groups may further have a substituent. Examples of the substituent include the groups listed below for substituent T.
• Examples of the carbamoyl group include 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 group examples 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.
• acyl group examples include acyl groups having 1 to 20 carbon atoms, preferably acyl groups having 1 to 12 carbon atoms, and more preferably acyl groups having 1 to 8 carbon atoms.
• alkylsulfonyl group examples include 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.
• arylsulfonyl group examples include arylsulfonyl groups having 6 to 20 carbon atoms, preferably arylsulfonyl groups having 6 to 10 carbon atoms.
• alkylsulfinyl group examples include 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.
• arylsulfinyl group examples include arylsulfinyl groups having 6 to 20 carbon atoms, and preferably arylsulfinyl groups having 6 to 10 carbon atoms.
• alkoxycarbonyl group examples include an alkoxycarbonyl group having 2 to 20 carbon atoms, preferably an alkoxycarbonyl group having 2 to 12 carbon atoms, and more preferably an alkoxycarbonyl group having 2 to 8 carbon atoms.
• aryloxycarbonyl group examples include an aryloxycarbonyl group having 6 to 20 carbon atoms, preferably an aryloxycarbonyl group having 6 to 12 carbon atoms, and an aryloxycarbonyl group having 6 to 8 carbon atoms. is more preferable.
• alkyl group examples include an alkyl group having 1 to 18 carbon atoms, preferably an alkyl group having 1 to 10 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms.
• aryl group examples include aryl groups having 6 to 20 carbon atoms, preferably aryl groups having 6 to 15 carbon atoms, and more preferably aryl groups having 6 to 10 carbon atoms.
• the heterocycle in the heterocyclic group preferably includes a 5- or 6-membered saturated or unsaturated heterocycle.
• An aliphatic ring, aromatic ring or other heterocycle may be fused to the heterocycle.
• the heteroatoms constituting the heterocyclic ring include B, N, O, S, Se and Te, with N, O and S being preferred.
• the heterocycle has a free valence (monovalence) at its carbon atom (the heterocyclic group is bonded at the carbon atom).
• the heterocyclic group preferably has 1 to 40 carbon atoms, more preferably 1 to 30 carbon atoms, and even more preferably 1 to 20 carbon atoms.
• Examples of the electron-withdrawing group include substituents having a Hammett's substituent constant ⁇ p value of 0.2 or more.
• Hammett's substituent constant ⁇ value will be explained.
• Hammett's rule was developed by L. Hammett in 1935 to quantitatively discuss the influence of substituents on the reaction or equilibrium of benzene derivatives. P. This is a rule of thumb proposed by Hammett, and its validity is widely recognized today.
• Substituent constants determined by Hammett's rule include ⁇ p values and ⁇ m values, and these values can be found in many general texts. For example, J. A. Dean, "Lange's Handbook of Chemistry” 12th edition, 1979 (McGraw-Hill), "Region of Chemistry” Special Edition, No.
• a substituent having a Hammett's substituent constant ⁇ p value of 0.2 or more means 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; A group having a substituent constant ⁇ p value of 0.35 or more is more preferable.
• Me represents a methyl group
• Ph represents a phenyl group.
• the values in parentheses are the ⁇ p values of typical substituents as shown in Chem. Rev. ,
• 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, or An aryloxycarbonyl group is preferred.
• R q2 and R q3 are preferably a cyano group, an alkoxycarbonyl group, a nitro group, or an alkylsulfonyl group, and more preferably a cyano group.
• one of R q2 and R q3 is a cyano group, and the other is 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.
• R q2 and R q3 are a cyano group, and the other is a cyano group, a carbamoyl group, a sulfamoyl group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group. , an arylsulfinyl group, an alkoxycarbonyl group, or an aryloxycarbonyl group, and it is even more preferable that one of R q2 and R q3 is a cyano group, and the other is a cyano group or an alkoxycarbonyl group.
• a preferred embodiment includes an embodiment in which R q2 and R q3 are cyano groups.
• Another preferred embodiment includes an embodiment in which one of R q2 or R q3 is a cyano group and the other is an alkoxycarbonyl group.
• substituent T examples include the following groups.
• Halogen atoms e.g. chlorine atom, bromine atom, iodine atom
• Alkyl group straight chain, branched, cyclic alkyl group.
• straight chain or branched alkyl groups preferably straight chain or branched alkyl groups having 1 to 30 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, t-butyl group, n -octyl group, eicosyl group, 2-chloroethyl group, 2-cyanoethyl group, 2-ethylhexyl group), cycloalkyl group (preferably a cycloalkyl group having 3 to 30 carbon atoms, such as cyclohexyl group, cyclopentyl group, 4- n-dodecylcyclohexyl group), bicycloalkyl group (preferably a bicycloalkyl group having 5 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms.
• bicyclo[ 1,2,2]heptane-2-yl group bicyclo[2,2,2]octan-3-yl group
• tricyclo structures with many ring structures For example, bicyclo[ 1,2,2]heptane-2-yl group, bicyclo[2,2,2]octan-3-yl group), and tricyclo structures with many ring structures.
• the alkyl groups in the substituents described below (for example, the alkyl group of an alkylthio group) also represent this concept of an alkyl group. ];
• Alkenyl group [straight chain, branched, cyclic alkenyl group.
• straight-chain or branched alkenyl groups preferably straight-chain or branched alkenyl groups having 2 to 30 carbon atoms, such as vinyl groups, allyl groups, prenyl groups, geranyl groups, oleyl groups
• cycloalkenyl groups Preferably a cycloalkenyl group having 3 to 30 carbon atoms. That is, a monovalent group obtained by removing one hydrogen atom from a cycloalkene having 3 to 30 carbon atoms.
• a 2-cyclopenten-1-yl group, a 2-cycloalkenyl group, -cyclohexen-1-yl group), bicycloalkenyl group (preferably a bicycloalkenyl group having 5 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom from a bicycloalkene having one double bond.
• Alkynyl group preferably a straight or branched alkynyl group having 2 to 30 carbon atoms; for example, ethynyl group, propargyl group);
• Aryl group preferably an aryl group having 6 to 30 carbon atoms; for example, phenyl group, p-tolyl group, naphthyl group, m-chlorophenyl group, o-hexadecanoylaminophenyl group
• Heterocyclic group preferably a monovalent group obtained by removing one hydrogen atom from a 5- or 6-membered aromatic or non-aromatic heterocyclic compound, more preferably a 5- or 6-membered group having 1 to 20 carbon atoms
• Cyano group e.g., 2-furyl group, 2-thienyl group, 2-pyrimidinyl group, 2-benzothiazolyl group
• Cyano group Hydroxy group
• Nitro group carboxyl group
• Alkoxy group preferably a straight or branched alkoxy group having 1 to 30 carbon atoms; for example, methoxy group, ethoxy group, isopropoxy group, t-butoxy group, n-oct
• Carbamoyloxy group (preferably a carbamoyloxy group having 1 to 30 carbon atoms.
• Carbamoyloxy group preferably a carbamoyloxy group having 1 to 30 carbon atoms.
• Alkoxycarbonyloxy group preferably an alkoxycarbonyloxy group having 2 to 30 carbon atoms; for example, methoxycarbonyloxy group, ethoxycarbonyloxy group, t-butoxycarbonyloxy group, n-octylcarbonyloxy group
• Aryloxycarbonyloxy group preferably an aryloxycarbonyloxy group having 7 to 30 carbon atoms; for example,
• Aminocarbonylamino group preferably an aminocarbonylamino group having 1 to 30 carbon atoms; for example, carbamoylamino group, N,N-dimethylaminocarbonylamino group, N,N-diethylaminocarbonylamino group, morpholinocarbonylamino group); Alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms.
• methoxycarbonylamino group methoxycarbonylamino group, ethoxycarbonylamino group, t-butoxycarbonylamino group, n-octadecyloxycarbonylamino group, N-methyl-methoxy carbonylamino group
• Aryloxycarbonylamino group preferably an aryloxycarbonylamino group having 7 to 30 carbon atoms; for example, phenoxycarbonylamino group, p-chlorophenoxycarbonylamino group, m-n-octyloxyphenoxycarbonylamino group
• Sulfamoylamino group preferably a sulfamoylamino group having 0 to 30 carbon atoms; for example, sulfamoylamino group, N,N-dimethylaminosulfonylamino group, Nn-octylaminosulfonylamino group
• Sulfamoyl group (preferably a sulfamoyl group having 0 to 30 carbon atoms; for example, N-ethylsulfamoyl group, N-(3-dodecyloxypropyl)sulfamoyl group, N,N-dimethylsulfamoyl group, N-acetylsulfamoyl group) famoyl group, N-benzoylsulfamoyl group, N-(N'-phenylcarbamoyl)sulfamoyl group); Sulfo group; Alkyl or arylsulfinyl group (preferably an alkylsulfinyl group having 1 to 30 carbon atoms, an arylsulfinyl group having 6 to 30 carbon atoms; for example, a methylsulfinyl group, an ethylsulfinyl group, a phenylsulfin
• An acyl group (preferably a formyl group, an alkylcarbonyl group having 2 to 30 carbon atoms, an arylcarbonyl group having 7 to 30 carbon atoms, a heterocyclic carbonyl group having 4 to 30 carbon atoms bonded to a carbonyl group, e.g.
• Aryloxycarbonyl group preferably an aryloxycarbonyl group having 7 to 30 carbon atoms; for example, phenoxycarbonyl group, o-chlorophenoxycarbonyl group, m-nitrophenoxycarbonyl group, pt-butylphenoxycarbonyl group
• Alkoxycarbonyl group preferably an alkoxycarbonyl group having 2 to 30 carbon atoms; for example, methoxycarbonyl group, ethoxycarbonyl group, t-butoxycarbonyl group, n-octadecyloxycarbonyl group, n-butoxycarbonyl group, 2-ethyl group
• carbamoyl group N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N,N-di-n-octylcarbamoyl group, N-(methylcarbamoyl group) sulfonyl)carbamoyl group);
• Aryl or heterocyclic azo group preferably arylazo group having 6 to 30 carbon atoms, heterocyclic azo group having 3 to 30 carbon atoms; for example, phenylazo group, p-chlorophenylazo group, 5-ethylthio-1,3,4- thiadiazol-2-ylazo group
• Imide group preferably N-succinimide group, N-phthalimide group
• Phosphino group preferably a phosphino group having 2 to 30 carbon atoms; for example, dimethylphosphino group, diphenylphosphino group, methylphenoxyphosphino group
• one or more hydrogen atoms may be substituted with the above substituent T.
• substituents include alkylcarbonylaminosulfonyl groups, arylcarbonylaminosulfonyl groups, alkylsulfonylaminocarbonyl groups, and arylsulfonylaminocarbonyl groups. Specific examples include methylsulfonylaminocarbonyl group, p-methylphenylsulfonylaminocarbonyl group, acetylaminosulfonyl group, and benzoylaminosulfonyl group.
• the sulfo group and the carboxyl group may have hydrogen atoms dissociated to form an anion, or may form a salt.
• Atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K + , etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ , etc.), ammonium ions (tetraalkylammonium ions, trialkyl ions, etc.).
• the maximum absorption wavelength of the specific compound is preferably in the wavelength range of 360 to 430 nm, more preferably in the wavelength range of 370 to 420 nm, even more preferably in the wavelength range of 380 to 420 nm, and even more preferably in the wavelength range of 380 to 420 nm. It is particularly preferred that the wavelength range is from 410 nm to 410 nm.
• the molar extinction coefficient at the maximum absorption wavelength of the specific compound is preferably 10,000 L/mol ⁇ cm or more, more preferably 20,000 L/mol ⁇ cm or more, and even more preferably 30,000 L/mol ⁇ cm or more. Further, the molar extinction coefficient of the specific compound at a wavelength of 400 nm is preferably 1000 L/mol ⁇ cm or more, more preferably 3000 L/mol ⁇ cm or more, and even more preferably 5000 L/mol ⁇ cm or more.
• the maximum absorption wavelength and molar extinction coefficient of a specific compound can be determined by measuring the spectroscopic spectrum of a solution prepared by dissolving the specific compound in ethyl acetate at room temperature (25°C) using a 1 cm quartz cell.
• Examples of the measuring device include UV-1800PC (manufactured by Shimadzu Corporation).
• the specific compound is prepared according to the method described in JP 2009-067984, JP 2009-263616, JP 2009-263617, WO 2009/022736, and WO 2017/122503. can be manufactured.
• Specific examples of the specific compound include compounds with the following structures.
• Me is a methyl group
• Et is an ethyl group
• Pr is a propyl group
• Bu is a butyl group
• tBu is a tert-butyl group
• Ph is a phenyl group.
• the ultraviolet absorber used in the thermosetting composition of the present invention may contain other ultraviolet absorbers whose maximum absorption wavelength is on the shorter wavelength side than the specific compound mentioned above.
• the maximum absorption wavelength of other ultraviolet absorbers is preferably in the wavelength range of 300 to 380 nm, more preferably in the wavelength range of 300 to 370 nm, and even more preferably in the wavelength range of 310 to 360 nm. , it is particularly preferable that the wavelength range is from 310 to 350 nm. According to this aspect, it is possible to form a cured product that can block light with wavelengths in the ultraviolet region over a wide range.
• the difference between the maximum absorption wavelength of the specific compound and the maximum absorption wavelength of other ultraviolet absorbers is preferably 1 to 70 nm, more preferably 10 to 60 nm, and even more preferably 20 to 50 nm. preferable. According to this aspect, it is possible to form a cured product that can block light with wavelengths in the ultraviolet region over a wide range.
• ultraviolet absorbers examples include aminobutadiene compounds, dibenzoylmethane compounds, benzotriazole compounds, benzophenone compounds, salicylic acid compounds, acrylate compounds, and triazine compounds, with benzotriazole compounds, benzophenone compounds, and triazine compounds being preferred. More preferred are benzotriazole compounds and triazine compounds.
• UV absorbers include 2-(2'-hydroxy-5'-t-butylphenyl)benzotriazole, 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl) )-5-chlorobenzotriazole, 2-(4-butoxy-2-hydroxyphenyl)-4,6-di(4-butoxyphenyl)-1,3,5-triazine, 2-[2-hydroxy-4- (2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2,2',4,4'-tetrahydroxybenzophenone, 2 , 2'-dihydroxy-4,4'-dimethoxybenzophenone and the like.
• compounds described in paragraph numbers 0065 to 0070 of JP 2009-263616A and compounds described in paragraph number 0065 of International Publication No. 2017/122503 can also be used.
• the content of the ultraviolet absorber in the total solid content of the thermosetting composition is preferably 0.01 to 30% by mass.
• the lower limit is preferably 0.05% by mass or more, more preferably 0.1% by mass or more.
• the upper limit is preferably 25% by mass or less, more preferably 20% by mass or less.
• the content of the specific compound in the total solid content of the thermosetting composition is preferably 0.01 to 30% by mass.
• the lower limit is preferably 0.05% by mass or more, more preferably 0.1% by mass or more.
• the upper limit is preferably 25% by mass or less, more preferably 20% by mass or less.
• the content of the specific compound in the total solid content of the thermosetting composition can be 0.01 to 30% by mass, 0.01 to 25% by mass, and 0.01 to 25% by mass. It can also be 20% by mass.
• the thermosetting composition may contain only one type of ultraviolet absorber, or may contain two or more types of ultraviolet absorbers. When two or more types of ultraviolet absorbers are included, the total amount thereof is preferably within the above range.
• thermosetting composition of the present invention contains a thermosetting compound.
• a thermosetting compound is a compound that can be cured by a chemical reaction under heating conditions, and unless otherwise specified, includes compounds that form the molecular skeleton of a product (i.e., a cured product) in a thermosetting reaction.
• the thermosetting compound may be a compound that thermosets alone or may be a compound that thermosets by using two or more kinds together, and in the presence of additives such as known curing agents. It may also be a thermosetting compound.
• phenolic resin in the case of phenolic resin, it can be thermally cured by heating in the presence of an amine curing agent, epoxy resin, or the like.
• thermosetting compound is not limited to monomers, and includes, for example, oligomers, prepolymers, and resins.
• thermosetting compound is preferably a compound having a reactive group such as an isocyanate group, isothiocyanate group, epoxy group, methylol group, alkoxysilyl group, hydroxy group, mercapto group, or amino group.
• Thermosetting compounds include phenol resins, epoxy resins, melamine resins, urea resins, polyester resins, alkyd resins, polyimide resins, polyurethane resins, polythiourethane resins, diallyl phthalate resins, episulfide resins, siloxane resins, and precursors thereof.
• Polyurethane resins, polythiourethane resins, diallyl phthalate resins, or their precursors are preferred because they have high refractive index, light weight, and excellent impact resistance, and polythiourethane resins or precursors thereof are preferable. It is more preferable.
• the precursor of the above-mentioned resin in the thermosetting compound refers to a compound from which these resins are produced by a thermosetting reaction.
• the precursor may be a compound that is thermally cured singly to produce the resin, or a compound that is thermally cured to produce the resin when two or more are used in combination. It may be a compound that is thermally cured to produce the above resin in the presence of an additive such as a known curing agent.
• Examples of the precursors of the resins include isocyanate compounds, isothiocyanate compounds, methylol compounds, epoxy compounds, phenol compounds, melamine compounds, diallylphthalate compounds, alkoxysilane compounds, and the like.
• the form of these precursors is not limited to monomers, and includes, for example, oligomers, prepolymers, and resins.
• examples of the precursor of diallyl phthalate resin include diallyl phthalate.
• Diallyl phthalate resin is produced by thermosetting diallyl phthalate.
• Examples of the polythiourethane resin precursor and the polyurethane resin precursor include isocyanate compounds and isothiocyanate compounds.
• a polythiourethane resin is produced by subjecting an isocyanate compound or an isothiocyanate compound to a thermosetting reaction with a polythiol compound.
• a polyurethane resin is produced by subjecting an isocyanate compound or an isothiocyanate compound to a thermosetting reaction with a polyol compound or the like.
• a prepolymer obtained by reacting at least one selected from isocyanate compounds and isothiocyanate compounds with a polythiol compound can also be used as a precursor of the polythiourethane resin.
• a prepolymer obtained by reacting at least one selected from isocyanate compounds and isothiocyanate compounds with a polyol compound can also be used as a precursor of the polyurethane resin.
• Examples of the isocyanate compound include compounds having two or more isocyanate groups in one molecule.
• Examples of the isothiocyanate compound include compounds having two or more isothiocyanate groups in one molecule.
• Specific examples of isocyanate compounds and isothiocyanate compounds include: Hexamethylene diisocyanate, 2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, 1, 6,11-undecane triisocyanate, 1,3,6-hexamethylene triisocyanate, 1,8-diisocyanate 4-isocyanate methyl octane, bis(isocyanate ethyl) carbonate, bis(isocyanate ethyl) ether, lysine diisocyanate methyl ester,
• Cyclic polyisocyanate compound is an aromatic polyisocyanate compound
• Aliphatics such as 1,2-diisothiocyanate ethane and 1,6-diisothiocyanate hexane
• Alicyclic polyisothiocyanate compounds such as cyclohexane diisothiocyanate
• halogen-substituted products such as chlorine-substituted products, bromine-substituted products, alkyl-substituted products, alkoxy-substituted products, nitro-substituted products and prepolymer-type modified products with polyhydric alcohols, carbodiimide-modified products, urea-modified products, and buret-modified products. Dimerization or trimerization reaction products, etc. can also be used.
• commercially available isocyanate compounds and isothiocyanate compounds may be used. Examples of commercially available products include Duranate TPA100 (manufactured by Asahi Kasei Corporation, compound name: polyisocyanurate of hexamethylene diisocyanate).
• Polythiol compounds used when reacting with isocyanate compounds or isothiocyanate compounds to produce polythiourethane resins include: Methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,6-hexanedithiol, 1,2,3 -Propanetrithiol, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane- 2,3-dithiol, 1,1-bis(mercaptomethyl)cyclohexane, thiomalic acid bis(2-mercaptoethyl ester), 2,3-dimercapto-1-propanol (2-
• Heterocyclic compounds containing a sulfur atom in addition to a mercapto group such as 3,4-thiophenedithiol and 2,5-dimercapto-1,3,4-thiadiazole; 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerin di(mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2,4-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 3,4-dimercapto-2-propanol, 1,3-dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1,3-butanediol, pentaerythritol tris(3-mercapto pentaerythritol mono(3-mercaptopropionate), pentaerythritol bis(3-mercaptopropionate), pentaeryth
• the polythiol compound used when producing a polyurethane resin by reacting with an isocyanate compound or an isothiocyanate compound has multiple hydroxy groups, and the number of carbon atoms in the hydroxy group (the number of carbon atoms in the straight chain part connecting the hydroxy groups)
• Examples include polyols (also referred to as long-chain polyols) having carbon chains with a carbon chain of 6 or more.
• the carbon chain having 6 or more carbon atoms in the long chain polyol refers to a chain having 6 or more carbon atoms in the straight chain portion connecting hydroxy groups.
• a long-chain polyol in which the hydroxy group is present through a carbon chain having 6 or more carbon atoms is -[CO(CH 2 ) n1O ] n2 -H (where n1 is 1 or more and 10 or less (preferably 3 or more and 6 or less, more preferably 3 or more and 6 or less). 5), and n2 preferably has a structure of 1 or more and 50 or less (preferably 1 or more and 35 or less, more preferably 1 or more and 10 or less).
• long-chain polyols examples include bifunctional polycaprolactone diol, trifunctional polycaprolactone triol, and tetrafunctional or higher functional polycaprolactone polyol.
• the difunctional polycaprolactone diol is, for example, -[CO(CH 2 ) n11 O] n12 -H (where n11 represents 1 or more and 10 or less (preferably 3 or more and 6 or less, more preferably 5), and n12 represents 1 or more and 50 or less (preferably 4 or more and 35 or less), and includes a compound having two groups having a hydroxyl group at the terminal.
• trifunctional polycaprolactone diol for example, -[CO(CH 2 ) n21 O] n22 -H (where n21 represents 1 or more and 10 or less (preferably 3 or more and 6 or less, more preferably 5), and n22 represents 1 or more and 50 or less (preferably 1 or more and 28 or less), and includes a compound having three groups having a hydroxyl group at the terminal.
• polystyrene resin examples include Plaxel 308 (manufactured by Daicel Corporation).
• the hydroxyl value of the long chain polyol is preferably 30 to 300 mgKOH/g, more preferably 50 to 250 mgKOH/g.
• the said hydroxyl value represents the number of mg of potassium hydroxide required in order to acetylate the hydroxyl group (hydroxyl group) in 1g of samples.
• the above-mentioned hydroxyl value in this specification is measured according to the method (potentiometric titration method) defined in JIS K0070-1992. However, if the sample does not dissolve, a solvent such as dioxane or tetrahydrofuran is used. A commercially available product may be used as the polythiourethane resin precursor.
• polythiourethane resin precursors include MR-6, MR-7, MR-8, MR-8Plus, MR-60, MR-10, MR-20 (manufactured by Mitsui Chemicals, Inc.), Examples include EYAS1.60 (manufactured by HOYA Corporation).
• methylol compounds, epoxy compounds, phenol compounds, melamine compounds, alkoxysilane compounds, etc. can be used as precursors for the resins.
• methylol compound examples include compounds having two or more methylol groups in one molecule.
• Specific examples of methylol compounds include alkoxymethylated melamine, methylolated melamine, alkoxymethylated benzoguanamine, methylolated benzoguanamine, alkoxymethylated glycoluril, methylolated glycoluril, alkoxymethylated urea, methylolated urea, and tolylene diisocyanate.
• examples include trimethylolpropane-imparted bodies.
• the epoxy compound examples include compounds having two or more epoxy groups in two molecules.
• the epoxy compound may be either a low molecular compound (for example, molecular weight less than 1000) or a macromolecule (for example, molecular weight 1000 or more, in the case of a polymer, weight average molecular weight 1000 or more).
• the weight average molecular weight of the epoxy compound is preferably 2,000 to 100,000.
• the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less.
• epoxy compounds include Celoxide 2021P (trade name, 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexane carboxylate) manufactured by Daicel Corporation, and Recaresin DME-100 manufactured by Shinnihon Chemical Co., Ltd. (trade name, contains 1,4-cyclohexanedimethanol diglycidyl ether as a main component) and other polyfunctional epoxy compounds.
• the epoxy compound compounds described in paragraph numbers 0006 to 0011 of JP-A No. 2008-013759 and compounds described in paragraph numbers 0032 to 0100 of JP-A No. 2013-227451 can also be used.
• alkoxysilane compounds include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-i-propoxysilane, tetra-n-butoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, Ethyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, ⁇ -glycidyloxypropyltrimethoxysilane, ⁇ -glycidyloxypropyltriethoxysilane, ⁇ -glycidyl Oxypropylmethyldimethoxysilane, ⁇ -glycidyloxypropylmethyldiethoxysilane, ⁇ -methoxy
• thermosetting resin can also be used as the thermosetting compound.
• thermosetting resin include phenol resin, epoxy resin, melamine resin, urea resin, polyester resin, alkyd resin, polyimide resin, polyurethane resin, polythiourethane resin, diallylphthalate resin, episulfide resin, and siloxane resin.
• epoxy resin examples include bisphenol A epoxy resin, bisphenol F epoxy resin, phenol novolac epoxy resin, cresol novolac epoxy resin, aliphatic epoxy resin, and the like.
• a commercially available epoxy resin may be used.
• Commercially available epoxy resins include the following.
• Examples of commercially available bisphenol A epoxy resins include jER152, jER154, jER157S70, jER157S65, jER806, jER807, jER825, jER827, jER828, jER834, and jER1001.
• EPICLON N-660 EPICLON N-665, EPICLON N-670, EPICLON N-673, EPICLON N- 680, EPICLON N-690, EPICLON N -695, EPICLON N-740, EPICLON N-770, EPICLON N-775, EPICLON860, EPICLON1050, EPICLON1051, EPICLON1055, EPICLON830, and EPICLON83 5 (manufactured by DIC Corporation), NC-2000, NC-3000, NC- ADEKA RESIN EP series (e.g.
• EP- 4080S, EP-4085S, and EP-4088S manufactured by ADEKA Co., Ltd.
• Celoxide 2021P Celoxide 2081, Celoxide 2083, Celoxide 2085, EHPE3150, EPOLEAD PB 3600, and EPOLEAD PB 4700 (the above, manufactured by Daicel Corporation), Denacol EX-212L, EX-214L, EX-216L, EX-321L, and EX-850L (manufactured by Nagase ChemteX Corporation), Marproof G-0150M, G-0105SA, G-0130SP, G-0250SP , G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (epoxy group-containing polymers manufactured by NOF Corporation), Epotote ZX-1059 (Nippon Steel Chemical & (manufactured by Material Co., Ltd.).
• the content of the thermosetting compound in the total solid content of the thermosetting composition is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more. preferable.
• the upper limit can be 99% by mass or less.
• the thermosetting composition may contain only one kind of thermosetting compound, or may contain two or more kinds of thermosetting compounds. When two or more types of thermosetting compounds are included, the total amount thereof is preferably within the above range.
• thermosetting composition of the present invention contains at least one thermosetting aid selected from a thermal polymerization initiator and a polymerization catalyst.
• the type of thermosetting aid can be appropriately selected depending on the thermosetting compound.
• thermal polymerization initiators include compounds that generate active species such as radicals and cations when heated. Specific examples include thermal radical polymerization initiators and thermal cationic polymerization initiators.
• thermal radical polymerization initiator is a compound that generates radicals when heated.
• thermal radical polymerization initiators include aromatic ketone compounds, onium salt compounds, organic peroxides, azo compounds, thio compounds, hexaarylbiimidazole compounds, ketoxime ester compounds, borate compounds, azinium compounds, metallocene compounds, and active esters. Examples include compounds having a carbon-halogen bond, and the like.
• azo compounds examples include 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), and dimethyl-2,2'-azobis( 2-methylpropionate), 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis[N-(2- propenyl)2-methylpropionamide], 1-[(1-cyano-1-methylethyl)azo]formamide, 2,2'-azobis(N-butyl-2-methylpropionamide), 2,2'-azobis (N-cyclohexyl-2-methylpropionamide) and the like.
• azo compounds include V-70, V-65, V-60, V-59, V-40, V-30, V-501, V-601, VE-073, VA-080, VA- 086, VF-096, VAm-110, VAm-111, VA-044, VA-046B, VA-060, VA-061, V-50, VA-057, VA-067, VR-110 (the above, Wako Pure (manufactured by Yaku Kogyo Co., Ltd.), etc.
• organic peroxides examples include methyl ethyl ketone peroxide, cyclohexanone peroxide, 3,3,5-trimethylcyclohexanone peroxide, methylcyclohexanone peroxide, acetylacetone peroxide, 1,1-bis(tert-butylperoxy)-3, 3,5-trimethylcyclohexane, 1,1-bis(tert-butylperoxy)cyclohexane, 2,2-bis(tert-butylperoxy)butane, tert-butyl hydroperoxide, cumene hydroperoxide, diisopropylbenzene hydro Peroxide, paramethane hydroperoxide, 2,5-dimethylhexane-2,5-dihydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, tert-butylcumyl peroxide, dicumyl peroxide oxide, bis(tert-butylperoxyisopropy
• organic peroxides include: Pertetra A, Perhexa HC, Perhexa C, Perhexa V, Perhexa 22, Perbutyl H, Permil H, Permil P, Permenta H, Perocta H, Perbutyl C, Perbutyl D, Perhexyl D, Perloyl IB, Perloyl 355, Perloyl L, Perloil SA , Niper BW, Niper BMT-K40, Niper BMT-M, Perloil IPP, Perloil NPP, Perloil TCP, Perloil OPP, Perloil SBP, Perloil ND, Perocta ND, Perhexyl ND, Perbutyl ND, Perhexyl PV, Perbutyl PV, Perhexa 25O, Perocta O, Perhexyl O, Perbutyl O, Perbutyl L, Perbutyl 355, Perhexyl
• a thermal cationic polymerization initiator is a compound that generates cations when heated.
• Examples of the thermal cationic polymerization initiator include diazomethane compounds, sulfonic acid ester compounds, carboxylic acid ester compounds, phosphoric acid ester compounds, sulfonimide compounds, sulfonebenzotriazole compounds, organic onium salt compounds, and the like.
• Examples of the organic onium salt compound include organic onium salt compounds in which a cation component and an anion component are paired.
• Examples of the cationic component include organic sulfonium, organic oxonium, organic ammonium, organic phosphonium, and organic iodonium.
• examples of the anion components include BF 4 ⁇ , B(C 6 F 5 ) 4 ⁇ , SbF 6 ⁇ , AsF 6 ⁇ , PF 6 ⁇ , CF 3 SO 3 ⁇ , C 4 F 9 SO 3 ⁇ , (CF 3 SO 2 ) 3 C - is mentioned.
• organic onium salt compounds include diphenyl(methyl)sulfonium tetrafluoroborate, benzyl(4-hydroxyphenyl)methylsulfonium hexafluoroantimonate, (4-hydroxyphenyl)methyl(2-methylbenzyl)sulfonium hexafluoroantimonate, Examples include (4-hydroxyphenyl)dimethylsulfonium hexafluorophosphate.
• sulfonic acid ester compounds include cyclohexyl p-toluenesulfonate, tetraethylene glycol bis(p-toluenesulfonate), butyl p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium trifluoromethanesulfonate, benzyl-4-hydroxy Phenylmethylsulfonium trifluoromethanesulfonate, 2-methylbenzyl-4-hydroxyphenylmethylsulfonium trifluoromethanesulfonate, 4-acetoxyphenyldimethylsulfonium trifluoromethanesulfonate, 4-acetoxyphenylbenzylmethylsulfonium trifluoromethanesulfonate, 4-(methoxycarbonyloxy) Examples include phenyldimethylsulfonium trifluoromethanesulfonate and benzyl-4-(methoxy
• sulfonimide compound examples include N-(trifluoromethylsulfonyloxy)succinimide (trade name "SI-105", Midori Chemical Co., Ltd.), N-(camphorsulfonyloxy)succinimide (trade name "SI-106", Midori Chemical Co., Ltd.), N-(2-trifluoromethylphenylsulfonyloxy)succinimide, N-(4-fluorophenyl) sulfonyloxy)succinimide, N-(trifluoromethylsulfonyloxy)phthalimide, N-(camphorsulfonyloxy)phthalimide, N-(2-trifluoromethylphenylsulfonyloxy)phthalimide, N-(2-fluorophenylsulfonyloxy)phthalimide , N-(trifluoromethylsulfonyloxy)diphenylmaleimide (trade name "PI-105",
• Hept-5-ene-2,3-dicarboxylimide (trade name "NDI-100", Midori Kagaku Co., Ltd.), N-(4-methylphenylsulfonyloxy)bicyclo[2.2.1]hept-5 -ene-2,3-dicarboxylimide (trade name "NDI-101", Midori Kagaku Co., Ltd.), N-(trifluoromethanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3- Dicarboxylimide (trade name "NDI-105", Midori Kagakusha), N-(nonafluorobutanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylimide (trade name "NDI-109", Midori Kagaku Co., Ltd.), N-(camphorsulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylimide (trade
• thermal cationic polymerization initiators include Sanaid SI-45, SI-47, SI-60, SI-60L, SI-80, SI-80L, SI-100, SI-100L, SI-110, SI- 110L, SI-145, I-150, SI-160, SI-180L, SI-B3, SI-B2A, SI-B3A, SI-B4, SI-300 (manufactured by Sanshin Chemical Industry Co., Ltd.), CI- 2921, CI-2920, CI-2946, CI-3128, CI-2624, CI-2639, CI-2064 (manufactured by Nippon Soda Co., Ltd.), CP-66, CP-77 (manufactured by ADEKA Co., Ltd.), FC -520 (manufactured by 3M) K-PURE TAG-2396, TAG-2713S, TAG-2713, TAG-2172, TAG-2179, TAG-2168E, TAG-27
• Tertiary amine compounds and salts thereof such as diazabicycloundecene, diazabicyclononene, tris(dimethylaminomethyl)phenol; Phosphine compounds such as tobutylphosphine, tricyclohexylphosphine, triphenylphosphine, tri(o-tolyl)phosphine, 1,3,5-triaza-7-phosphaadamantane; Phosphonium salts such as ethyltriphenylphosphonium chloride, tetrabutylphosphonium bromide, ethyltriphenylphosphonium bromide, tetrabutylphosphonium iodide, ethyltriphenylphosphonium iodide, tetraphenylphosphonium/tetraphenylborate; Imidazole compounds such as 1-cyanoethyl-2-ethyl-4-methylimidazo
• Neostan series for example, Neostan U-600, etc.
• K-KAT series manufactured by KING INDUSTRIES.
• the content of the thermosetting aid is preferably 0.001 to 10 parts by mass based on 100 parts by mass of the thermosetting compound.
• the upper limit is preferably 8 parts by mass or less, more preferably 5 parts by mass or less.
• the lower limit is preferably 0.002 parts by mass or more, more preferably 0.005 parts by mass or more.
• the thermosetting composition may contain only one type of thermosetting auxiliary agent, or may contain two or more types. When two or more types of thermosetting aids are included, the total amount thereof is preferably within the above range.
• the thermosetting composition of the present invention can further contain a curing agent.
• a curing agent By containing a curing agent, a cured product with better properties such as solvent resistance can be formed.
• the curing agent can be appropriately selected depending on the type of thermosetting compound.
• the curing agent include polythiol compounds, polyol compounds, amine compounds, phenol compounds, guanidine compounds, imidazole compounds, naphthol compounds, acrylic compounds, acid anhydrides, active ester compounds, benzoxazine compounds, and cyanate ester compounds.
• the thiol compound and polyol compound include the materials mentioned above.
• commercially available phenolic curing agents include KAYAHARD GPH-65 (Nippon Kayaku Co., Ltd.).
• the content of the curing agent is preferably 5 to 90 parts by weight based on 100 parts by weight of the thermosetting compound.
• the upper limit is preferably 85 parts by mass or less, more preferably 80 parts by mass or less.
• the lower limit is preferably 8 parts by mass or more, more preferably 10 parts by mass or more.
• the thermosetting composition may contain only one type of curing agent, or may contain two or more types. When two or more types of curing agents are included, the total amount thereof is preferably within the above range.
• the thermosetting composition of the present invention can further contain a resin other than the thermosetting compound.
• resins 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 resin and polyvinyl bromide resin], polythioether resin, polyphenylene resin, polyurethane resin, polysulfonate resin, nitrosopolymer resin, polysiloxane resin, polysulfide resin, polythioester resin, polysulfone resin, polysulfonamide resin, polyamide Resin, polyimine resin, polyurea resin, polyphosphazene resin, polysilane resin, polysilazane resin, polyfuran resin, polybenz
• the other resin may be an alkali-soluble resin.
• the alkali-soluble resin include resins having acid groups.
• the acid group include a carboxyl group, a phosphoric acid group, a sulfonic acid group, and a phenolic hydroxy group.
• the number of acid groups may be one, or two or more.
• the alkali-soluble resin is preferably one that is soluble in an organic solvent and can be developed with a weak alkaline aqueous solution.
• Such alkali-soluble resins include polymers having a carboxyl group in the side chain, such as those disclosed in JP-A No. 59-044615, JP-A No. 54-034327, JP-A No. 58-012577, and JP-B No. 54-025957.
• Examples include acidic cellulose derivatives having a carboxyl group in a side chain, such as a polymerized maleic acid copolymer, a partially esterified maleic acid copolymer, and the like.
• alkali-soluble resin resins made by adding acid anhydrides to polymers having hydroxyl groups are also useful.
• the alkali-soluble resin may be a resin copolymerized with a hydrophilic monomer.
• hydrophilic monomers include alkoxyalkyl (meth)acrylate, hydroxyalkyl (meth)acrylate, glycerol (meth)acrylate, (meth)acrylamide, N-methylolacrylamide, secondary or tertiary alkyl acrylamide, dialkylaminoalkyl (meth)acrylate, morpholine (meth)acrylate, N-vinylpyrrolidone, N-vinylcaprolactam, vinylimidazole, vinyltriazole, methyl (meth)acrylate, ethyl (meth)acrylate, branched or linear propyl (meth)acrylate, Branched or linear butyl (meth)acrylate, phenoxyhydroxypropyl (meth)acrylate, and the like can be mentioned.
• hydrophilic monomers include tetrahydrofurfuryl group, phosphoric acid group, phosphate ester group, quaternary ammonium base, ethyleneoxy chain, propyleneoxy chain, sulfonic acid group and groups derived from its salts, and morpholinoethyl group. Monomers including the like are also useful.
• the weight average molecular weight of the alkali-soluble resin is preferably 3,000 to 200,000, more preferably 5,000 to 50,000.
• the acid value of the alkali-soluble resin is preferably 30 to 200 mgKOH/g.
• the lower limit of the acid value is preferably 50 mgKOH/g or more, more preferably 70 mgKOH/g or more.
• the upper limit of the acid value is preferably 150 mgKOH/g or less, more preferably 120 mgKOH/g or less.
• the content of other resins in the total solid content of the thermosetting composition is preferably 80% by mass or less, more preferably 60% by mass or less, and even more preferably 50% by mass or less.
• the lower limit can also be 1% by mass or more.
• the thermosetting composition may contain only one type of other resin, or may contain two or more types of other resins. When two or more types of other resins are included, the total amount thereof is preferably within the above range. It is also preferred that the thermosetting composition of the present invention does not contain other resins.
• thermosetting composition of the present invention can contain a surfactant.
• the surfactant include the surfactants described in paragraph number 0017 of Japanese Patent No. 4502784 and paragraph numbers 0060 to 0071 of JP-A-2009-237362.
• the surfactant is preferably a nonionic surfactant, a fluorine surfactant, or a silicone 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 (manufactured by DIC Corporation), Florado FC430, FC431, FC171 (manufactured by Sumitomo 3M Ltd.), Surflon S-382, SC-101, SC-103, SC-104, SC-
• Suitable fluorine-based surfactants include acrylic compounds, which have a molecular structure with a functional group containing a fluorine atom, and when heat is applied, the functional group containing the fluorine atom is severed and the fluorine atom evaporates.
• fluorine-based surfactants include the Megafac DS series manufactured by DIC Corporation (Kagaku Kogyo Nippo (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), An example is DS-21.
• fluorine-based surfactant 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.
• a block polymer can also be used as the fluorosurfactant.
• the fluorine-based surfactant includes a repeating unit derived from a (meth)acrylate compound having a fluorine atom and a (meth) having 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy group, propyleneoxy group). )
• a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be used.
• fluorine-based surfactant a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in its side chain can also be used.
• Commercially available products include Megafac RS-101, RS-102, RS-718K, and RS-72-K (manufactured by DIC Corporation).
• PFOA perfluorooctanoic acid
• PFOS perfluorooctane sulfonic acid
• silicone surfactants include linear polymers consisting of siloxane bonds and modified siloxane polymers with organic groups introduced into side chains or terminals.
• Commercially available silicone surfactants include DOWSIL 8032 ADDITIVE, Tore Silicone DC3PA, Tore Silicone SH7PA, Tore Silicone DC11PA, Tore Silicone SH21PA, Tore Silicone SH28PA, Tore Silicone SH29PA, Tore Silicone SH30PA, Tore Silicone SH8400 (more than that, Toray ⁇ Manufactured by Dow Corning Co., Ltd.), -643, X-22-6191, X-22-4515, KF-6004, KP-341, KF-6001, KF-6002 (manufactured by Shin-Etsu Silicone Co., Ltd.), F-4440, TSF-4300, TSF- 4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials), BYK307, BYK323, BYK330 (manu
• nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane, and their ethoxylates and propoxylates (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, Examples include polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, and sorbitan fatty acid ester.
• nonionic surfactants include Pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (all manufactured by BASF), Tetronic 304, 701, 704, 901, 904, 150R1 (all manufactured by BASF) ), Solsperse 20000 (manufactured by Japan Lubrizol Co., Ltd.), NCW-101, NCW-1001, NCW-1002 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), Pionin D-6112, D- 6112-W, D-6315 (manufactured by Takemoto Yushi Co., Ltd.), Olfin E1010, Surfynol 104, 400, 440 (all manufactured by Nissin Chemical Industry Co., Ltd.), and the like.
• the content of the surfactant in the total solid content of the thermosetting composition is preferably 0.001% by mass to 5.0% by mass.
• the lower limit is preferably 0.005% by mass or more, more preferably 0.01% by mass or more, even more preferably 0.05% by mass or more, and 0.10% by mass or more. is particularly preferred.
• the upper limit is preferably 3.0% by mass or less, more preferably 1.0% by mass or less, and even more preferably 0.80% by mass or less.
• the number of surfactants may be one, or two or more. In the case of two or more types, it is preferable that the total amount falls within the above range.
• the thermosetting composition of the present invention can contain an organic solvent.
• the organic solvent include alcohol solvents, ester solvents, ether solvents, ketone solvents, amide solvents, hydrocarbon solvents, and halogen solvents.
• Specific examples of alcoholic solvents include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 1-methoxy-2-propanol, 2-ethoxyethanol, Examples include 2-butoxyethanol, ethylene glycol, propylene glycol, and glycerin.
• ester 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, and lactic acid.
• Ethyl, alkyl acetate esters e.g.
• methyl alkoxy acetate, ethyl alkoxy acetate, butyl alkoxy acetate (specifically, methyl methoxy acetate, ethyl methoxy acetate, butyl methoxy acetate, methyl ethoxy acetate, ethyl ethoxy acetate, etc.) )
• 3-oxypropionic acid alkyl esters 2-oxypropionic acid alkyl esters, methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, methyl pyruvate, pyruvic acid Ethyl, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glyco
• ether 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, and polypropylene.
• examples include 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 solvents include N-methylpyrrolidone, dimethylformamide, dimethylacetamide, and the like.
• ketone solvents include methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, and 3-heptanone.
• hydrocarbon solvents include toluene, xylene, and the like.
• halogenated solvents include chloroform, methylene chloride, and the like. Two or more of these organic solvents may be used in combination.
• the organic solvents include methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, cyclopentanone, and ethyl carbide. It preferably contains at least one selected from toll acetate, butyl carbitol acetate, propylene glycol monomethyl ether, and propylene glycol monomethyl ether acetate.
• the content of the organic solvent in the thermosetting composition is preferably 95% by mass or less.
• One preferred embodiment is an embodiment in which the content of the organic solvent in the thermosetting composition is 10 to 95% by mass.
• the content of the organic solvent in the thermosetting composition is preferably 30 to 95% by mass, more preferably 50 to 95% by mass.
• Another preferred embodiment is an embodiment in which the content of the organic solvent in the thermosetting composition is 10% by mass or less.
• the content of the organic solvent in the thermosetting composition is preferably 5% by mass or less, more preferably 1% by mass or less. Further, it may be substantially free of organic solvents.
• thermosetting composition does not substantially contain an organic solvent
• the content of the organic solvent in the thermosetting composition is 0.1% by mass or less, and 0.01% by mass or less. It is preferable that it is, and it is more preferable that it does not contain an organic solvent.
• thermosetting composition of the present invention may contain optional additives such as antioxidants, light stabilizers, processing stabilizers, anti-aging agents, polymerization inhibitors, flame retardants, and antistatic agents, as necessary. You may.
• thermosetting composition ⁇ Method for producing thermosetting composition>
• it can be manufactured by mixing an ultraviolet absorber, a thermosetting compound, a thermosetting aid, and optional components as needed.
• thermosetting composition When producing a thermosetting composition, each component contained in the thermosetting composition may be blended all at once, or each component may be dissolved and dispersed in a solvent and then blended sequentially. Furthermore, there are no particular restrictions on the order of addition or working conditions when blending.
• a thermosetting composition may be manufactured by dissolving and dispersing all components in a solvent at the same time, or, if necessary, each component may be prepared as two or more solutions or dispersions, and then These may be mixed (at the time of application) to prepare a thermosetting composition.
• thermosetting composition When producing a thermosetting composition, it is preferable to mix each component and then filter it with a filter for the purpose of removing foreign substances and reducing defects.
• Filters that have been conventionally used for filtration and the like can be used without particular limitation.
• examples include fluororesins such as PTFE (polytetrafluoroethylene), polyamide resins such as nylon-6 and nylon-6,6, and polyolefin resins (high density, ultra-high density, etc.) such as polyethylene and polypropylene (PP). (including molecular weight filters).
• PTFE polytetrafluoroethylene
• polyamide resins such as nylon-6 and nylon-6,6, and polyolefin resins (high density, ultra-high density, etc.)
• PP polyethylene and polypropylene
• polyamide resins such as nylon-6 and nylon-6,6, and polypropylene (including high-density polypropylene) are preferred.
• the pore diameter of the filter is preferably 0.01 to 7.0 ⁇ m, more preferably 0.01 to 2.5 ⁇ m, and even more preferably 0.01 to 2.0 ⁇ m.
• various filters provided by Nippon Pole Co., Ltd. DFA4201NXEY, DFA4201NAEY, DFA4201J006P, etc.
• Advantech Toyo Co., Ltd. Nippon Entegris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), Kitz Microfilter Co., Ltd., etc.
• Kitz Microfilter Co., Ltd. etc.
• filters When using filters, different filters (for example, a first filter and a second filter, etc.) may be combined. At that time, filtration with each filter may be performed only once, or may be performed two or more times. Further, filters having different pore diameters within the above-mentioned range may be combined.
• thermosetting 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 houses, facilities, transportation equipment, etc.; interior and exterior materials and paints for houses, facilities, transportation equipment, etc.; materials for light sources that emit ultraviolet rays, such as fluorescent lamps and mercury lamps.
• thermosetting composition of the present invention can be preferably used for optical members and the like.
• it is preferably used as a thermosetting composition for ultraviolet 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 thermosetting composition of the present invention can also be used as a pressure-sensitive adhesive, an adhesive, or the like.
• thermosetting composition of the present invention can also be used for various members of display devices.
• a liquid crystal display device it can be used for each member constituting the liquid crystal display device, such as an antireflection film, a polarizing plate protective film, an optical film, a retardation film, a pressure-sensitive adhesive, and an adhesive.
• the organic electroluminescent display device may include an optical film, a polarizing plate protective film in a circularly polarizing plate, a retardation film such as a quarter-wave plate, an adhesive or a pressure-sensitive adhesive, etc. It can be used for each member.
• the cured product of the present invention is obtained using the thermosetting composition of the present invention described above.
• the cured product of the present invention may be a molded product obtained by molding a thermosetting composition into a desired shape and thermosetting it.
• the shape of the molded body can be appropriately selected depending on the use and purpose. Examples include a coating film, a film, a sheet, a plate, a lens, a tube, and a fiber.
• the cured product of the present invention is preferably used as an optical member.
• optical members include ultraviolet cut filters, lenses, and protective materials. It can also be used for polarizing plates and the like.
• the ultraviolet cut filter can be used, for example, in articles such as optical filters, display devices, solar cells, and window glass.
• the type of display device is not particularly limited, but examples thereof include liquid crystal display devices, organic electroluminescence display devices, and the like.
• 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. Furthermore, the cured product of the present invention may be used as a coating film on the surface of a lens, an intermediate layer (adhesive layer) of a cemented lens, or the like. Examples of cemented lenses include those described in paragraph numbers 0094 to 0102 of International Publication No. 2019/131572, the contents of which are incorporated herein.
• the type of protective material is not particularly limited, but includes protective materials for display devices, protective materials for solar cells, protective materials for window glass, organic electroluminescent display devices, and the like.
• the shape of the protective material is not particularly limited, but examples include a coating film shape, a film shape, and a sheet shape.
• the optical member of the present invention includes a cured product obtained using the above-described thermosetting composition of the present invention.
• the cured product of the present invention may be a molded product obtained by molding the above-described thermosetting composition of the present invention into a desired shape and thermosetting it.
• the shape of the molded body can be appropriately selected depending on the use and purpose. Examples include a coating film, a film, a sheet, a plate, a lens, a tube, and a fiber.
• Types of optical members include ultraviolet cut filters, lenses, protective materials, etc.
• the ultraviolet cut filter can be used, for example, in articles such as optical filters, display devices, solar cells, and window glass.
• the type of display device is not particularly limited, but examples thereof include liquid crystal display devices, organic electroluminescence display devices, and the like.
• Lenses include those in which the cured product of the present invention itself is formed into a lens shape; those in which the cured product of the present invention is used for a coating film on the lens surface or an intermediate layer (adhesive layer or adhesive layer) of a cemented lens, etc. It will be done.
• the type of protective material is 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 a coating film shape, a film shape, and a sheet shape.
• optical member having a laminate of a support and a resin layer.
• this optical member at least one of the support and the resin layer contains the above-mentioned cured product of the present invention.
• the thickness of the resin layer in the laminate is preferably 1 ⁇ m to 2500 ⁇ m, more preferably 10 ⁇ m to 500 ⁇ m.
• the support in the laminate is preferably a material that has transparency within a range that does not impair optical performance.
• transparent it means that it is optically transparent, and specifically, it 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, more preferably 95% or more.
• a suitable example of the support is a resin film.
• resins constituting 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., Examples include polypropylene (PP), polyethylene (PE), etc.), polyvinyl chloride (PVA), tricellulose acetate (TAC), and the like.
• PET is preferred in terms of versatility.
• the thickness of the support can be appropriately selected depending on the use or purpose. Generally, the thickness is preferably 5 ⁇ m to 2500 ⁇ m, more preferably 20 ⁇ m to 500 ⁇ m.
• a removable support can also be used as the support.
• Such a laminate is preferably used for polarizing plates and the like.
• the releasable support is 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, More preferably, it is 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 determined by a tensile test after the surface of the laminate cut to a width of 25 mm and a length of 80 mm was bonded and fixed to a glass substrate via an acrylic adhesive sheet.
• a machine RTF-1210 manufactured by A&D Co., Ltd.
• the removable support one containing polyethylene terephthalate (PET) as a main component (among the components constituting the support, the component having the highest content on a mass basis) is preferable.
• 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 0.1 to 55 ⁇ m. It is particularly preferred that the thickness is 10 ⁇ m.
• the support may be subjected to known surface treatments such as corona treatment, glow discharge treatment, and undercoating.
• optical member examples include a laminate having a hard coat layer, a transparent support, and an adhesive layer or adhesive 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 adhesive layer may contain the above-described cured product of the present invention.
• a hard coat layer for example, JP 2013-045045, JP 2013-043352, JP 2012-232459, JP 2012-128157, JP 2011-131409, JP 2011 -131404, 2011-126162, 2011-075705, 2009-286981, 2009-263567, 2009-075248, 2007-164206 No. 2006-096811, 2004-075970, 2002-156505, 2001-272503, International Publication No. 2012/018087, International Publication No. 2012/098967 , International Publication No. 2012/086659, and International Publication No. 2011/105594 can be applied.
• the thickness of the hard coat layer is preferably 5 to 100 ⁇ m in terms of further improving scratch resistance.
• the optical member of this form has an adhesive layer or adhesive layer on the side opposite to the side having the hard coat layer of the supporting base material.
• the type of adhesive or adhesive used for the adhesive layer or adhesive layer is not particularly limited, and any known adhesive or adhesive may be used.
• the pressure-sensitive adhesive or adhesive includes an acrylic resin described in paragraph numbers 0056 to 0076 of JP2017-142412A and a crosslinking agent described in paragraphs 0077 to 0082 of JP2017-142412A. It is also preferable to use
• the adhesive or the adhesive may include adhesion improvers (silane compounds) described in paragraph numbers 0088 to 0097 of JP-A No. 2017-142412, and additions described in paragraph number 0098 of JP-A-2017-142412.
• the adhesive layer or adhesive layer can be formed by the method described in paragraph numbers 0099 to 0100 of JP 2017-142412A.
• the thickness of the adhesive layer or adhesive layer is preferably 5 ⁇ m to 100 ⁇ m from the viewpoint of achieving both adhesion and handling properties.
• the optical member of the present invention can be preferably used as a component of a display such as a liquid crystal display (LCD) or an organic electroluminescent display (OLED).
• a display such as a liquid crystal display (LCD) or an organic electroluminescent display (OLED).
• LCD liquid crystal display
• OLED organic electroluminescent display
• liquid crystal display devices include those containing the cured product of the present invention in members such as antireflection films, polarizing plate protective films, optical films, retardation films, pressure-sensitive adhesives, and adhesives.
• the optical member containing the cured product of the present invention may be placed on either the viewer side (front side) or the backlight side with respect to the liquid crystal cell, or on the side far from the liquid crystal cell with respect to the polarizer (outer side). ), it can be placed either on the near side (inner).
• Organic electroluminescence display devices include organic materials containing the cured product of the present invention in optical films, polarizing plate protective films in circularly polarizing plates, retardation films such as quarter-wave plates, adhesives, pressure-sensitive adhesives, etc. Examples include electroluminescent display devices.
• Example 1 60 parts by mass of dicyclohexylmethane diisocyanate, 0.05 parts by mass of dimethyltin dichloride, and 0.10 parts by mass of acidic phosphoric acid ester (manufactured by Stepan, trade name: Zerec UN) were mixed and dissolved at 10 to 15°C. Furthermore, 40 parts by mass of polythiol containing 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane as a main component was mixed, defoamed for 1 hour under reduced pressure, and then filtered. Urethane resin precursor 1 was produced.
• thermosetting resin precursor 1 10 g
• thiourethane resin precursor 1 3 mg of the above-mentioned compound 1-5 as an ultraviolet absorber
• dibutyltin dichloride which is a polymerization catalyst as a thermosetting aid
• thermosetting composition and a molded article were produced in the same manner as in Example 1-1, except that the type and amount of the ultraviolet absorber were changed as shown in the table below. The amount of the ultraviolet absorber added was adjusted so that the cured product had an absorbance of 1 at a wavelength of 400 nm.
• thermosetting composition 10 g of diallyl phthalate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), which is a precursor monomer of diallyl phthalate resin, 6 mg of the above-mentioned compound 1-5 as an ultraviolet absorber, and organic peroxide perbutyl O (as a thermosetting aid).
• a thermosetting composition was produced by mixing 0.2 g of NOF Corporation). The amount of ultraviolet absorber added was adjusted so that the absorbance of the cured product at a wavelength of 400 nm was 1. did. After filling the obtained thermosetting composition into a mold, it was heated at 100°C for 4 hours, 120°C for 2 hours, and 150°C for 2 hours to cure, resulting in a cured molded product with a thickness of 1 mm. manufactured something.
• thermosetting composition and a molded article were produced in the same manner as in Example 2-1, except that the type and amount of the ultraviolet absorber added were changed as shown in the table below. The amount of the ultraviolet absorber added was adjusted so that the cured product had an absorbance of 1 at a wavelength of 400 nm.
• Example 3-1 Polymerizable monomers n-butyl methacrylate (nBMA) and hydroxyethyl methacrylate (HEMA) were mixed at a molar ratio of 3:3. Furthermore, a polymerizable monomer solution was prepared by adding a polymerization initiator (azobisisobutyronitrile (AIBN)) with a ratio of 2% by mass to the polymerizable monomer and methyl ethyl ketone (MEK) with a ratio of 40% by mass to the polymerizable monomer. . This polymerizable monomer solution was placed in a dropping funnel, and added dropwise to MEK with a ratio of 50% by mass of polymerizable monomers heated to 80° C.
• a polymerization initiator azobisisobutyronitrile (AIBN)
• MEK methyl ethyl ketone
• thermosetting aid 4.0 g of a solution of acrylic resin prepolymer 1 (solid content 50% by mass) and a long chain polyol (polycaprolactone triol, Plaxel 308, manufactured by Daicel Corporation, molecular weight 850, hydroxyl value 190 to 200 mgKOH/g) 3.6 g of polyfunctional isocyanate (Duranate TPA100, manufactured by Asahi Kasei Corporation, compound name: polyisocyanurate of hexamethylene diisocyanate), and Neostane U-600 (Nitto Kasei Co., Ltd.) as a thermosetting aid.
• Duranate TPA100 manufactured by Asahi Kasei Corporation, compound name: polyisocyanurate of hexamethylene diisocyanate
• Neostane U-600 Neitto Kasei Co., Ltd.
• thermosetting material 0.02 g of Dibutyltin Co., Ltd., 7.5 g of methyl ethyl ketone, and 100 mg of Compound 1-5 described above as an ultraviolet absorber were mixed and degassed under reduced pressure for 10 minutes to form a thermosetting material. A composition was produced. The amount of the ultraviolet absorber added was adjusted so that the cured product had an absorbance of 1 at a wavelength of 400 nm. The obtained thermosetting composition was coated with a bar coater on a 125 ⁇ m thick black polyethylene terephthalate film (Lumirror Manufactured.
• thermosetting composition and a resin film were produced in the same manner as in Example 3-1, except that the type and amount of the ultraviolet absorber were changed as shown in the table below. The amount of the ultraviolet absorber added was adjusted so that the cured product had an absorbance of 1 at a wavelength of 400 nm.
• Example 4-1 36 mg of Compound 1-5 mentioned above as an ultraviolet absorber, 3.0 g of epoxy resin (EPPN-201 (manufactured by Nippon Kayaku Co., Ltd.), and epoxy resin (Epotote ZX-1059, Nippon Steel Chemical & Material Co., Ltd.) ), 4 g of a phenol compound (KAYAHARD GPH-65, manufactured by Nippon Kayaku Co., Ltd.), 0.06 g of triphenylphosphine, which is a polymerization catalyst as a thermosetting aid, and 8 g of cyclohexanone.
• thermosetting composition The amount of ultraviolet absorber added was adjusted so that the absorbance of the cured product at a wavelength of 400 nm was 1.Thickness of the coating film after drying
• the obtained thermosetting composition was applied onto a substrate so that the thickness was 0.5 mm, and a coating film was formed by drying at 140° C. for 10 minutes. , vacuum pressing (pressure: 5 MPa, temperature: 140° C., time: 20 minutes) was performed, and further heating was performed at 150° C. for 20 minutes to produce a sheet-shaped molded product.
• thermosetting composition and a molded article were produced in the same manner as in Example 4-1, except that the type and amount of the ultraviolet absorber were changed as shown in the table below. The amount of the ultraviolet absorber added was adjusted so that the cured product had an absorbance of 1 at a wavelength of 400 nm.
• Absorbance maintenance rate (%) (Absorbance at the maximum absorption wavelength of the cured product after immersion in PGMEA/Absorbance at the maximum absorption wavelength of the cured product before immersion in PGMEA) x 100 AA: Absorbance maintenance rate is 95% or more A: Absorbance maintenance rate is 85% or more and less than 95% B: Absorbance maintenance rate is 70% or more and less than 85% C: Absorbance maintenance rate is less than 70%
• compounds 1-5, 1-46, 1-52, 1-69, 1-72, A-1, A-6, A-18, A-232, A-259 used as ultraviolet absorbers are: Compounds 1-5, 1-46, 1-52, 1-69, 1-72, A-1, A-6, A-18, A-232, A-259 shown as specific examples of the above-mentioned specific compounds It is.
• Compounds C-1 and C-2 used as ultraviolet absorbers in comparative examples have the following structures.
• thermosetting composition and a molded article were produced in the same manner as in Example 3-1, except that the type and amount of the ultraviolet absorber were changed as shown in the table below, and haze and molded bodies were produced in the same manner as in Test Example 1. Solvent resistance was evaluated.
• the amount of ultraviolet absorber added in Examples 5-1 to 5-10 was twice that of Examples 3-1 to 3-10, but in all Examples, the haze was small and the solvent resistance was excellent. It was possible to produce a cured product.
• thermosetting compositions of Examples 2-1 to 2-10, Comparative Example 2-1, and Comparative Example 2-2 changes in colorability before and after thermosetting were confirmed.
• each thermosetting composition was injected into a 1 mm thick spectroscopic measurement cell, the absorption spectrum was measured, and the absorbance (A 400 ) at a wavelength of 400 nm was determined.
• the value of the absorbance ratio (A 400 /A 430 ) of the absorbance at a wavelength of 430 nm (A 430 ) was calculated.
• the value of the absorbance ratio (A 400 /A 430 ) of the absorbance at a wavelength of 400 nm (A 400 ) and the absorbance at a wavelength of 430 nm (A 430 ) of the cured product was determined in the same manner as in Test Example 1. Calculated. The results are shown in the table below.

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