Classifications

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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0041—Optical brightening agents, organic pigments
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B32—LAYERED PRODUCTS
  • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
  • B32B33/00—Layered products characterised by particular properties or particular surface features, e.g. particular surface coatings; Layered products designed for particular purposes not covered by another single class
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C255/00—Carboxylic acid nitriles
  • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
  • C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C255/00—Carboxylic acid nitriles
  • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
  • C07C255/47—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of rings being part of condensed ring systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/32—One oxygen, sulfur or nitrogen atom
  • C07D239/38—One sulfur atom
  • C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
  • C07D239/52—Two oxygen atoms
  • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
• • 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
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
• • 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
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
  • C08K5/353—Five-membered rings
• • 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

Definitions

• the present invention relates to a composition.
• compositions containing dye compounds are fibers, inks, paints, containers, packaging materials, etc. for the purpose of coloring and transmission or absorption of light of a specific wavelength. It is used for various purposes such as printed matter, optical articles, eyeglasses, and display devices.
• high selective absorption a function of efficiently absorbing desired light and transmitting and not absorbing undesired light
• durability sustainability of the above function
• the cyanine dye can control the wavelength showing maximum absorption in a wide range from the ultraviolet region having a wavelength of 380 nm or less to the near infrared region having a wavelength of 780 nm or more by controlling the number of methine carbon atoms in the polymethine skeleton. Since most of the dyes show relatively high selective absorption, a composition containing a cyanine dye has been often used as a composition containing a dye compound showing high selective absorption (for example, JP-A-58-29803). Publication No. (Patent Document 1)).
• composition containing a cyanine pigment has high selective absorption, many of them are inferior in durability, especially light resistance, and a composition having both high selective absorption and durability is required. rice field.
• the present invention includes the following inventions.
• ring W 1 represents a ring structure which may have a substituent.
• Ring W 2 represents a ring structure having at least one double bond as a constituent of the ring, and ring W 2 may have a substituent.
• the ring W 1 and the ring W 2 have the same meanings as described above.
• R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a monovalent substituent, and R 1 and R 2 may be linked to each other to form a ring structure. 3 and R 4 may be connected to each other to form a ring structure.
• [3] The composition according to [1] or [2], wherein the cation is an inorganic cation.
• [5] The composition according to any one of [1] to [4], further comprising at least one selected from the group consisting of singlet oxygen quenchers and metal complex compounds.
• [6] A molded product molded from the composition according to any one of [1] to [5].
• [7] A laminate containing a layer formed from the composition according to any one of [1] to [5].
• [9] A dyed product dyed with the compound (B) containing an anion and a cation having a partial structure represented by the formula (I).
• ring W 1 represents a ring structure which may have a substituent.
• Ring W 2 represents a ring structure having at least one double bond as a constituent of the ring, and ring W 2 may have a substituent.
• ring W 1 represents a ring structure which may have a substituent.
• Ring W 2 represents a ring structure having at least one double bond as a constituent of the ring, and ring W 2 may have a substituent.
• the present invention provides a composition that exhibits high selective absorption of visible light (wavelength 400 nm to 700 nm, preferably wavelength 450 to 600 nm) and has good light resistance.
• composition of the present invention contains a compound (B) containing an anion and a cation having a partial structure represented by the formula (I) (hereinafter, may be referred to as a compound (B)) and a resin (A).
• the compound (B) is a compound containing an anion and a cation having a partial structure represented by the formula (I).
• ring W 1 represents a ring structure which may have a substituent.
• Ring W 2 represents a ring structure having at least one double bond as a constituent of the ring, and ring W 2 may have a substituent.
• the anion charge contained in the partial structure represented by the formula (I) is delocalized, and the partial structure represented by the formula (I) also includes, for example, the structure described below. Further, the group containing the double bond of the rings W1 and W2 may have an anion charge.
• Ring W 1 may be monocyclic or polycyclic.
• the ring W 1 may be an aromatic ring or a ring having no aromaticity, but a ring having no aromaticity is preferable. By selecting a ring that does not have aromaticity, selective absorption can be further enhanced.
• the ring W 1 may be a heterocycle containing a hetero atom (for example, a nitrogen atom, an oxygen atom, a sulfur atom, etc.) or an aliphatic hydrocarbon ring composed of a carbon atom and a hydrogen atom. good.
• Ring W 1 is preferably a ring made of an aliphatic hydrocarbon.
• the ring W1 preferably has a ring structure of a 3-membered ring to a 20-membered ring, more preferably a 3-membered ring to a 12-membered ring, and even more preferably a 3-membered ring to a 6-membered ring. It is preferably a 4- to 6-membered ring.
• Ring W 2 represents a ring structure having at least one double bond as a component of the ring.
• the ring W 2 has one or more double bonds as a constituent requirement of the ring, but the double bonds contained in the ring W 2 are usually 1 to 4, preferably 1 to 3, and 1 or 2. More preferably, one is more preferable.
• Ring W 2 may be monocyclic or polycyclic.
• the ring W 2 may be an aromatic ring or a ring having no aromaticity, but a ring having no aromaticity is preferable. By selecting a ring that does not have aromaticity, selective absorption can be further enhanced.
• Ring W 2 may be a hetero ring containing a hetero atom (for example, a nitrogen atom, an oxygen atom, a sulfur atom, etc.) or a ring composed of an aliphatic hydrocarbon.
• Ring W 1 is preferably a ring made of an aliphatic hydrocarbon.
• the ring W1 preferably has a ring structure of a 3-membered ring to a 20-membered ring, more preferably a 3-membered ring to a 12-membered ring, and even more preferably a 3-membered ring to a 6-membered ring. It is preferably a 4- to 6-membered ring.
• Ring W 1 and ring W 2 form a fused ring.
• the fused ring formed by the ring W1 and the ring W2 is preferably a ring having no aromaticity, more preferably a fused ring of an aliphatic hydrocarbon, and has 6 to 40 carbon atoms. It is more preferably a fused ring of an aliphatic hydrocarbon.
• the fused ring formed from the ring W 1 and the ring W 2 is preferably a fused ring composed of two rings. Examples of the fused ring formed by the ring W 1 and the ring W 2 include rings represented by the following formulas (W 1-1 ) to (W 1-18 ). Further, the condensed ring formed by the ring W 1 and the ring W 2 also includes all the above-mentioned structures in which the anion charge is delocalized.
• Ring W 1 and ring W 2 may each independently have a substituent.
• substituents include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and the like.
• An aliphatic hydrocarbon group having 1 to 25 carbon atoms (preferably an alkyl group having 1 to 12 carbon atoms); a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group, and a 2,2-difluoroethyl group.
• alkoxy group having 1 to 12 carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group; methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group and the like.
• Alkylthio group having 1 to 12 carbon atoms monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group, etc.
• fluorinated alkoxy groups fluorinated alkoxy groups having 1 to 12 carbon atoms such as a trifluoromethanethioalkoxy group; 1 such as an amino group, a methylamino group, an ethylamino group, a dimethylamino group, a diethylamino group and a methylethylamino group.
• Carbamoyl group optionally substituted with 1 to 6 alkyl; alkylcarbonyloxy group having 2 to 12 carbon atoms such as methylcarbonyloxy group and ethylcarbonyloxy group; 1 to 1 to 12 carbon atoms such as methylsulfonyl group and ethylsulfonyl group.
• alkylsulfonyl groups aromatic hydrocarbon groups having 6 to 25 carbon atoms such as phenyl groups, naphthyl groups and diphenyl groups (preferably aryl groups having 6 to 18 hydrocarbons); 6 to 12 carbon atoms such as phenylsulfonyl groups Arylsulfonyl group; alkoxysulfonyl group having 1 to 12 carbon atoms such as methoxysulfonyl group and ethoxysulfonyl group; acyl group having 2 to 12 carbon atoms such as acetyl group and ethylcarbonyl group; aldehyde group; methoxycarbonyl group and ethoxycarbonyl group An alkoxycarbonyl group having 2 to 12 carbon atoms such as a group, a propoxycarbonyl group, and a butyloxycarbonyl group; An alkoxythiocarbonyl group having 2 to 12 carbon atoms such as a xythio
• the anion having the partial structure represented by the formula (I) is preferably the anion represented by the formula (II).
• the ring W 1 and the ring W 2 have the same meanings as described above.
• R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a monovalent substituent, and R 1 and R 2 may be linked to each other to form a ring structure. 3 and R 4 may be connected to each other to form a ring structure.
• the anion represented by the formula (II) also includes all the structures in which electrons are delocalized as shown below.
• the delocalization of electrons may extend to R 1 , R 2 , R 3 and R 4 . do.
• the delocalized structure is used. Is also included in the anion represented by the formula (II).
• the monovalent substituent represented by R 1 , R 2 , R 3 and R 4 is not particularly limited, but is, for example, a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, and electron extraction. Examples thereof include a sex group, an electron donating group, and a heterocyclic group.
• the monovalent aliphatic hydrocarbon group represented by R 1 , R 2 , R 3 and R 4 includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group and a tert-butyl group.
• Examples of the monovalent aromatic hydrocarbon group represented by R 1 , R 2 , R 3 and R 4 include a phenyl group, a naphthyl group, an anthrasenyl group, a tetrasenyl group, a pentasenyl group, a phenanthryl group, a chrysenyl group and a triphenylenyl group.
• An aryl group having 6 to 18 carbon atoms such as a tetraphenyl group, a pyrenyl group, a peryleneyl group, a coronenyl group and a biphenyl group; an aralkyl group having 7 to 18 carbon atoms such as a benzyl group, a phenylethyl group and a naphthylmethyl group; a phenoxyethyl group.
• Phenoxydiethylene glycol group, arylalkoxy group of phenoxypolyalkylene glycol group and the like preferably an aryl group having 6 to 18 carbon atoms, preferably a phenyl group or a benzyl group.
• the electron donating groups represented by R 1 , R 2 , R 3 and R 4 include hydroxyl groups; methoxy groups, ethoxy groups, propoxy groups, butoxy groups, pentyloxy groups, hexyloxy groups, heptyloxy groups and octyloxy groups.
• An alkoxy group having 1 to 12 carbon atoms such as a group; an alkyl group having 1 to 2 carbon atoms such as an amino group, a monomethylamino group, a monoethylamino group, a dimethylamino group, a diethylamino group, and a methylethylamino group.
• Amino group and thiol group which may be substituted with examples thereof include a thioalkyl group having 1 to 12 carbon atoms such as a thiomethyl group, a thioethyl group and a thiopropyl group.
• Examples of the heterocyclic group represented by R 1 , R 2 , R 3 and R 4 include a pyrrolidine ring group, a pyrrolin ring group, an imidazolidine ring group, an imidazoline ring group, an oxazoline ring group, a thiazolin ring group and a piperazine ring group.
• Examples of the electron-attracting group represented by R 1 , R 2 , R 3 and R 4 include a halogen atom, a nitro group, a cyano group, a carboxy group, an alkyl halide group, an aryl halide group and -OCF 3 . , -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, groups represented by the formula (z-1) can be mentioned.
• R222 represents a hydrogen atom, a halogen atom, or a hydrocarbon group which may have a substituent.
• X 1 represents -CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO 2- , -NR 223 CO- or -CONR 224- .
• R223 and R224 independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. * Represents a bond.
• halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
• the alkyl halide groups include trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluorosec-butyl group, perfluorotert-butyl group, perfluoropentyl group, perfluorohexyl group and dichloromethyl group.
• alkyl halide group having 1 to 25 carbon atoms such as a group, a bromomethyl group and an iodomethyl group.
• an alkyl halide group having 1 to 12 carbon atoms is preferably an alkyl halide group having 1 to 12 carbon atoms, more preferably a fluoroalkyl group having 1 to 12 carbon atoms, and further preferably a perfluoroalkyl group having 1 to 12 carbon atoms.
• the aryl halide group include an aryl halide group having 6 to 18 carbon atoms such as a fluorophenyl group, a chlorophenyl group and a bromophenyl group, and a fluoroaryl group having 6 to 18 carbon atoms is preferable. It is more preferably a perfluoroaryl group of 6 to 12, and even more preferably a pentafluorophenyl group.
• X 1 is preferably -CO-, -COO- or -SO 2- .
• halogen atom represented by R222 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
• hydrocarbon group represented by R222 include an aliphatic hydrocarbon group having 1 to 25 carbon atoms and an aromatic hydrocarbon group having 6 to 18 carbon atoms.
• Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an n-pentyl group and an n-.
• Linear, branched, cyclic alkyl with 1 to 25 carbon atoms such as hexyl group, 1-methylbutyl group, 3-methylbutyl group, n-octyl group, n-decyl, 2-hexyl-octyl group, cyclohexyl group, etc.
• the group is mentioned, and it is preferable that it is an alkyl group having 1 to 12 carbon atoms.
• the aromatic hydrocarbon group having 6 to 18 carbon atoms include an aryl group having 6 to 18 carbon atoms such as a phenyl group, a naphthyl group, an anthrasenyl group, a biphenyl group and a methylphenyl group; a benzyl group, a phenylethyl group and a naphthylmethyl group. Examples thereof include an aralkyl group having 7 to 18 carbon atoms.
• the substituent that the hydrocarbon group represented by R222 may have include a halogen atom and a hydroxy group.
• Alkyl groups having 1 to 6 carbon atoms represented by R223 and R224 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group and n.
• -A linear or branched alkyl group having 1 to 6 carbon atoms such as a pentyl group, an n-hexyl group and a 1-methylbutyl group can be mentioned.
• the groups represented by the formula (z-1) are -CO-R 1 , -CO-O-R 2 , -CO-NR 3 R 3z , -CO-S-R 4 , -CS-R 5 ,- CS-OR 6 , -CS-S-R 7 , -SO-R 8 , -SO 2 -R 9 (R 1 , R 2 , R 3 , R 3z , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each represent a hydrocarbon group or a halogen atom which may independently have a substituent).
• -CO-R 1 , -CO-O-R 2 , -SO 2 -R 9 are more preferable.
• -SO 2 -R 9 is more preferable, and it is more preferable.
• -SO 2 -R 10 (R 10 is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent), -SO 2 CF 3 , -SO 2 CHF 2 , -SO 2 CH 2 It is even more preferable that it is F.
• R 1 and R 2 may be connected to each other to form a ring structure.
• the ring formed by connecting R 1 and R 2 to each other may be a monocyclic ring or a condensed ring, but a monocyclic ring is preferable.
• the ring formed by connecting R 1 and R 2 to each other may or may not have aromaticity. It may also be a heterocycle.
• the ring formed by bonding R 1 and R 2 to each other is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5-membered ring or a 6-membered ring.
• Examples of the ring formed by connecting R 1 and R 2 to each other include the rings described below. Note that * in the equation represents a bond with the ring W1.
• the rings formed by the coupling of R 1 and R 2 to each other are represented by the formula (w-1), the formula (w-4), the formula (w-5), the formula (w-6), and the formula (w-8).
• Equation (w-9), Equation (w-10), Equation (w-11), Equation (w-13), Equation (w-31), Equation (w-32), Equation (w-35) It is preferably a ring represented by the formula (w-36) or the formula (w-37).
• R 3 and R 4 may be connected to each other to form a ring structure.
• the ring formed by connecting R 3 and R 4 to each other may be a monocyclic ring or a condensed ring, but a monocyclic ring is preferable.
• the ring formed by connecting R 3 and R 4 to each other may or may not have aromaticity. It may also be a heterocycle.
• the ring formed by bonding R 3 and R 4 to each other is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5-membered ring or a 6-membered ring. Examples of the ring formed by connecting R 3 and R 4 to each other include the same ring formed by connecting R 1 and R 2 to each other.
• the rings formed by connecting R 3 and R 4 to each other are represented by the formula (w-1), the formula (w-4), the formula (w-5), the formula (w-6), and the formula (w-8).
• At least one selected from R 1 , R 2 , R 3 and R 4 is preferably an electron-withdrawing group.
• R 1 , R 2 , R 3 and R 4 are independently electron-withdrawing groups. It is preferable that R 1 , R 2 , R 3 and R 4 are all the same group. It is preferable that R 1 , R 2 , R 3 and R 4 are independently electron-withdrawing groups, respectively.
• the anion represented by the formula (II) is preferably an anion represented by the formula (II-A).
• the anion represented by the formula (II-A) also includes all its delocalized structures. [In the formula (II-A), R 1 , R 2 , R 3 and R 4 have the same meanings as described above. ]
• Examples of the anion having a partial structure represented by the formula (I) include the anions described below.
• Me in the formula represents a methyl group.
• Examples of the anion having a partial structure represented by the formula (I) include the formula (I-1), the formula (I-2), the formula (I-3), the formula (I-4), and the formula (I-8). , Formula (I-9), Formula (I-10), Formula (I-13), Formula (I-17), Formula (I-18), Formula (I-19), Formula (I-20), Formula (I-21), formula (I-22), formula (I-24), formula (I-27), formula (I-38), formula (I-39), formula (I-40), formula.
• Compound (B) is composed of an anion having a partial structure represented by the formula (I) and a pair of cations.
• the combination is not limited.
• the cation has a valence of 2 or more, it may have a plurality of anions having a partial structure represented by the formula (I) so as to have the same valence.
• the valence is the same as the valence of the cation, it has an anion having a partial structure represented by the formula (I) and an anion having no partial structure represented by the formula (I). You may.
• the cation may be an organic cation, an inorganic cation, or an inorganic cation, preferably an inorganic cation.
• Examples of the organic cation include N-methylpyridinium, N-ethylpyridinium, N-propylpyridinium, N-ethyl-2-methylpyridinium, N-ethyl-3-methylpyridinium, 1-ethyl-3- (hydroxymethyl) pyridinium, N-butylpyridinium, N-butyl-4-methylpyridinium, N-butyl-3-methylpyridinium, N-hexylpyridinium, N-octylpyridinium, N-octyl-4-methylpyridinium, 1,1'-dimethyl-4 , 4'-Pyridinium, 1,1'-dibenzyl-4,4'-Pyridinium cations such as bipyridinium; Piperidinium cations such as 1-butyl-1-methylpiperidinium and 1-methyl-1-propylpiperidinium; 1-allyl-1-methylpyrrolidinium, 1-butyl
• Examples of the inorganic cation include alkali metal ions such as lithium ion, sodium ion, potassium ion, rubidium ion and cesium ion; monovalent metal ion such as copper (I) ion, silver ion and gold (I) ion; berylium ion, Alkaline earth metal ions such as magnesium ion, calcium ion, strontium ion, barium ion; copper (II) ion, nickel ion, cobalt ion, iron (II) ion, manganese ion, palladium ion, zinc ion, lead (II) Divalent metal ions such as ions, cadmium ions and mercury ions; 3 such as cobalt (III) ion, iron (III) ion, chromium (III) ion, scandium ion, yttrium ion, ruthenium (III) ion and gallium ion.
• Valuable metal ions such as titanium ion, zirconium ion, hafnium ion, germanium (IV) ion, molybdenum (IV) ion and the like can be mentioned.
• the inorganic cation is preferably a heavy metal ion such as the divalent metal ion, the trivalent metal ion, or the tetravalent metal ion.
• the compound (B) examples include the compounds listed in Tables 1 to 4 below.
• the compound (1) is a compound composed of an anion represented by the formula (I-1) and a lithium ion.
• Examples of the compound (B) include compound (1) to compound (5), compound (7), compound (8), compound (9), compound (10), compound (11), compound (13), and compound (14). ), Compound (15), compound (16), compound (17), compound (18), compound (19), compound (20), compound (21), compound (24), compound (25), compound (26). ), Compound (28), compound (29), compound (32), compound (34), compound (35), compound (41), compound (46), compound (47), compound (53), compound (55). ), Compound (57), compound (59), compound (61), compound (66), compound (67), compound (71), compound (72), compound (73), compound (74), compound (75). ), Compound (80), and compound (81) are preferable.
• the compound (B) in which the valence of the counter cation is monovalent and the condensed rings of the rings W 1 and W 2 are of the formula (W 1-1) is, for example, a compound represented by the formula (b- 1 ).
• compound (b-1) a compound represented by the formula (b-2) (hereinafter, may be referred to as compound (b-2)), and the formula (b-3).
• Reacting the represented compound (hereinafter, may be referred to as compound (b-3)) and the compound represented by the formula (b-4) (hereinafter, may be referred to as compound (b-4)).
• R 1 and R 2 have the same meanings as described above, and X 1 represents a divalent linking group.
• R 3 and R 4 have the same meanings as above, and X 2 represents a divalent linking group.
• Ra represents an alkali metal atom.
• the divalent linking group represented by X 1 and X 2 can be independently, for example, an alkanediyl group having 1 to 12 carbon atoms.
• alkali metal atom represented by Ra include lithium, potassium, sodium, rubidium, and cesium.
• compound (b-1), compound (b-2), compound (b-3) and compound (b-4) is as follows: compound (b-1), compound (b-2) and compound (b-). It is carried out by mixing 3) with compound (b-4).
• a mixture of compound (b-1), compound (b-2), compound (b-3) and compound (b-4) is a mixture of compound (b-1) and a part of compound (b-4).
• the compound (b-2) is added to the mixture (1) to obtain a mixture (2), and the resulting mixture (2) is a mixture (3) of the compound (b-3) and the balance of the compound (b-4). ) Is preferably added.
• the reaction of compound (b-1), compound (b-2), compound (b-3) and compound (b-4) may be carried out in the presence of a solvent.
• Solvents include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, methyl isobutyl ketone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N, Examples thereof include N-dimethylacetamide, N, N-dimethylformamide, water and the like. Preferred are acetonitrile, ethanol, methanol, 2-butanone and toluene.
• the solvent is preferably a dehydration solvent.
• the reaction time of the compound (b-1), the compound (b-2), the compound (b-3), and the compound (b-4) is usually 0.05 to 100 hours.
• the reaction temperature between the compound (b-1), the compound (b-2), the compound (b-3) and the compound (b-4) is usually ⁇ 100 to 200 ° C.
• the amount of compound (b-2) used is usually 0.01 to 10 mol equivalents with respect to 1 mol of compound (b-1).
• the amount of compound (b-3) used is usually 0.01 to 10 mol equivalents with respect to 1 mol of compound (b-1).
• the amount of compound (b-4) used is usually 0.01 to 10 mol equivalents with respect to 1 mol of compound (b-1).
• a base other than the compound (b-4) may be used in place of b-4) or in addition to the compound (b-4).
• bases include metal alkoxides (preferably alkali metal alkoxides), metal carbonates (preferably alkaline earth metal carbonates), amine compounds (preferably tertiary amines such as triethylamine and diisopropylethylamine), and metals.
• bases include metal alkoxides (preferably alkali metal alkoxides), metal carbonates (preferably alkaline earth metal carbonates), amine compounds (preferably tertiary amines such as triethylamine and diisopropylethylamine), and metals.
• amide compounds preferably alkali metal amides).
• a compound (B) having a Ra + cation (more specifically, a compound (B) having a potassium cation) is produced, and then salt exchange is performed to produce a compound (B) having a desired cation.
• the compound (B) having a Ra + cation is mixed with a sulfate or chloride containing a cation to be exchanged, and the compound (B) having a desired cation is separated to have a desired cation.
• Compound (B) can be obtained.
• the compound (B) preferably exhibits maximum absorption at a wavelength of 400 nm to 700 nm.
• the preferred wavelength varies depending on the application and purpose, but the structure such as the substituent (for example, the substituent represented by R1 to R4 above) contained in the anion having the partial structure represented by the formula (I) is adjusted. By doing so, the absorption wavelength can also be adjusted.
• the gram absorption coefficient ⁇ at the maximum absorption wavelength ( ⁇ max) of the compound (B) is preferably 50 [L / (g ⁇ cm)] or more, more preferably 100 [L / (g ⁇ cm)] or more, especially. It is preferably 150 [L / (g ⁇ cm)] or more.
• the upper limit is not particularly limited, but is generally 100,000 [L / (g ⁇ cm)] or less.
• thermoplastic resin examples include olefin resins such as polyethylene resins, polypropylene resins, and polycycloolefin resins; poly (meth) acrylic acid ester resins; polystyrene resins; styrene-acrylonitrile resins; acrylonitrile-butadiene-styrene resins.
• thermosetting resin examples include epoxy resin, melamine resin, unsaturated polyester resin, phenol resin, urea resin, alkyd resin, thermosetting polyimide resin and the like.
• the resin (A) is preferably a transparent resin.
• composition of the present invention preferably further comprises at least one selected from the group consisting of singlet oxygen quenchers and metal complex compounds.
• Singlet oxygen quenchers include diimonium compounds; tocopherols; carotenoid compounds such as astaxanthin, ⁇ -carotene, lycopene, lutein, and zeaxanthin; hindered amines; 1,4-diazabicyclo [2,2,2] octane ( DABCO); ascorbic acid; ⁇ -lipoic acid; lutein; catechin; resveratrol; sesamine; edarabon and the like.
• the metal species of the metal complex compound is preferably a heavy metal, more preferably at least one selected from a transition metal, zinc, cadmium and mercury, and a metal selected from nickel, cobalt, copper and platinum. It is even more preferable, and nickel is particularly preferable.
• the ligand of the metal complex dithiol, disulfonic acid, diimine and the like are preferable, and dithiol is more preferable.
• the metal complex a nickel-dithiol metal complex is particularly preferable.
• the content thereof is usually 0.001 to 50 parts by mass, preferably 0.001 to 50 parts by mass, based on 100 parts by mass of the resin (A). Is 0.01 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, still more preferably 0.5 to 5 parts by mass. If the content of at least one compound selected from the group consisting of the singlet oxygen quencher and the metal complex compound is too high, the optical properties are impaired due to the coloring of the singlet oxygen quencher or the metal complex compound, and if it is too low, the optical resistance is impaired. The improvement effect of is not obtained. When a plurality of singlet oxygen quenchers and metal complex compounds are contained, the total amount thereof may be within the above range.
• composition of the present invention can be used for various purposes, but is particularly preferably used for applications that may be exposed to light including sunlight or ultraviolet rays.
• Specific examples include, for example, glass substitutes and their surface coating materials; coating materials for window glass of dwellings, facilities, transportation equipment, etc., light-collecting glass and light source protection glass; window films of dwellings, facilities, transportation equipment, etc.; dwellings, Interior / exterior materials and interior / exterior paints for facilities, transportation equipment, etc.
• alkyd resin lacquer coatings and coatings formed by the coatings alkyd resin lacquer coatings and coatings formed by the coatings; acrylic lacquer coatings and coatings formed by the coatings; Materials for light sources that emit ultraviolet rays such as fluorescent lamps and mercury lamps; Materials for precision machinery, electronic and electrical equipment, materials for blocking electromagnetic waves generated from various displays; Containers or packaging materials for foods, chemicals, chemicals, etc .; Bottles, boxes, Blister, cups, special packaging, compact disc coats, agricultural and industrial sheets or film materials; anti-fading agents for printed matter, dyes, dyes, etc .; for polymer supports (eg, plastic parts such as machine and automotive parts) Protective film; printed matter overcoat; inkjet medium film; laminated matte; optical light film; safety glass / front glass intermediate layer; electrochromic / photochromic applications; overlaminated film; solar heat control film; sunscreen cream, shampoo, Cosmetics such as rinses and hairdressing; textile products and textiles for clothing such as sportswear, stockings and hats
• the shape of the molded body formed from the composition of the present invention is flat film-like, powder-like, spherical particle-like, crushed particle-like, needle-like, columnar, massive continuous body, fibrous, tubular, hollow thread-like, granular, plate-like. , Porous, or any other shape may be used.
• the composition of the present invention When the composition of the present invention is used for an optical article such as an optical filter, it can be applied to, for example, an optical display device.
• the layer formed from the resin composition of the present invention may be applied to any of a film layer, an adhesive layer, a coat layer and the like, and the adhesive layer may be applied. , It is preferable that it is a coat layer.
• a laminate containing a layer formed from the composition of the present invention is also included in the present invention.
• the laminate containing the layer formed from the composition of the present invention may contain other layers, and is preferably a laminate containing a wavelength conversion layer and a layer formed from the composition of the present invention. ..
• a pressure-sensitive adhesive composition containing a resin (A), a compound (B), a cross-linking agent (C) and a silane compound (D) (hereinafter, a pressure-sensitive adhesive). It may be referred to as the composition (i)).
• the pressure-sensitive adhesive composition (i) is further referred to as a light-absorbing compound (G) other than the radical-curable component (E), the initiator (F), and the compound (B) (hereinafter referred to as a light-selective absorbing compound (G)).
• Antistatic agent and the like may be contained.
• the resin (A) is not particularly limited as long as it is a resin used in the pressure-sensitive adhesive composition. It is preferable that the resin (A) does not exhibit maximum absorption in the wavelength range of 380 nm to 780 nm.
• the resin (A) is preferably a resin having a glass transition temperature (Tg) of 40 ° C. or lower.
• the glass transition temperature (Tg) of the resin (A) is more preferably 20 ° C. or lower, further preferably 10 ° C. or lower, and particularly preferably 0 ° C. or lower.
• the glass transition temperature of the resin (A) is usually ⁇ 80 ° C. or higher, preferably ⁇ 70 ° C. or higher, more preferably ⁇ 60 ° C.
• the glass transition temperature of the resin (A) is 40 ° C. or lower, it is advantageous to improve the adhesion of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition (i) to the adherend. Further, when the glass transition temperature of the resin (A) is ⁇ 80 ° C. or higher, it is advantageous to improve the durability of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition (i).
• the glass transition temperature can be measured by a differential scanning calorimeter (DSC).
• Examples of the resin (A) include (meth) acrylic resin, silicone resin, rubber resin, urethane resin and the like, and (meth) acrylic resin is preferable.
• the (meth) acrylic resin is preferably a polymer containing a structural unit derived from the (meth) acrylic acid ester as a main component (preferably containing 50% by mass or more).
• the structural unit derived from the (meth) acrylic acid ester is a simple structural unit derived from a monomer other than one or more (meth) acrylic acid esters (for example, having a polar functional group such as a hydroxyl group, a carboxyl group, or an amino group). It may contain a structural unit derived from a metric).
• the content of the resin (A) is usually 50% by mass to 99.9% by mass, preferably 60% by mass to 95% by mass, based on 100% by mass of the solid content of the pressure-sensitive adhesive composition (i). It is preferably 70% by mass to 90% by mass.
• the content of the compound (B) is usually 0.001 to 50 parts by mass, preferably 0.01 to 40 parts by mass, and more preferably 0.1 to 100 parts by mass with respect to 100 parts by mass of the resin (A). It is 30 parts by mass, and particularly preferably 0.2 to 15 parts by mass.
• cross-linking agent (C) examples include isocyanate-based cross-linking agents, epoxy-based cross-linking agents, aziridine-based cross-linking agents, metal chelate-based cross-linking agents, and the like, and in particular, the pot life of the pressure-sensitive adhesive composition and the durability and cross-linking of the pressure-sensitive adhesive layer. From the viewpoint of speed and the like, an isocyanate-based cross-linking agent is preferable.
• the content of the cross-linking agent (C) is usually 0.01 to 25 parts by mass, preferably 0.1 to 15 parts by mass, and more preferably 0.15 parts by mass with respect to 100 parts by mass of the resin (A). It is about 7 parts by mass, more preferably 0.2 to 5 parts by mass, and particularly preferably 0.25 to 2 parts by mass.
• silane compound (D) examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, and 3.
• the silane compound (D) may be a silicone oligomer.
• the content of the silane compound (D) is usually 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, and more preferably 0.15 with respect to 100 parts by mass of the resin (A). It is about 7 parts by mass, more preferably 0.2 to 5 parts by mass, and particularly preferably 0.25 to 2 parts by mass.
• radical curable component (E) examples include radical curable components such as compounds or oligomers that are cured by a radical polymerization reaction.
• examples of the radically polymerizable component (E) include (meth) acrylate-based compounds, styrene-based compounds, vinyl-based compounds and the like.
• the pressure-sensitive adhesive composition (i) may contain two or more radical curable components (E).
• Examples of the (meth) acrylate-based compound include a (meth) acrylate monomer having at least one (meth) acryloyloxy group in the molecule, a (meth) acrylamide monomer, and at least two (meth) acryloyl groups in the molecule.
• Examples thereof include (meth) acryloyl group-containing compounds such as (meth) acrylic oligomers having.
• the (meth) acrylic oligomer is preferably a (meth) acrylate oligomer having at least two (meth) acryloyloxy groups in the molecule.
• As the (meth) acrylate compound only one kind may be used alone, or two or more kinds may be used in combination.
• the (meth) acrylate monomer includes a monofunctional (meth) acrylate monomer having one (meth) acryloyloxy group in the molecule and a bifunctional (meth) acrylate having two (meth) acryloyloxy groups in the molecule.
• Examples thereof include a monomer and a polyfunctional (meth) acrylate monomer having three or more (meth) acryloyloxy groups in the molecule. It is preferably a (meth) acrylate compound, and more preferably a polyfunctional (meth) acrylate compound.
• the polyfunctional (meth) acrylate compound is preferably trifunctional or higher.
• the content of the radical curable component (E) is usually 0.5 to 100 parts by mass, preferably 1 to 70 parts by mass, and 3 to 50 parts by mass with respect to 100 parts by mass of the resin (A). It is more preferably 5 to 30 parts by mass, and particularly preferably 7.5 to 25 parts by mass.
• the initiator (F) is either a compound that causes a polymerization reaction by absorbing heat energy (thermal polymerization initiator) or a compound that causes a polymerization reaction by absorbing light energy (photopolymerization initiator). May be good.
• the light is preferably an active energy ray such as visible light, ultraviolet light, X-ray, or electron beam.
• thermal polymerization initiator examples include compounds that generate radicals by heating (thermal radical generators), compounds that generate acids by heating (thermal acid generators), and compounds that generate bases by heating (thermal base generators). ) Etc. can be mentioned.
• Photopolymerization initiators include compounds that generate radicals by absorbing light energy (photoradical generators), compounds that generate acid by absorbing light energy (photoacid generators), and light energy. Examples thereof include compounds that generate a base by absorbing the energy (photobase generator).
• the initiator (F) it is preferable to select one suitable for the polymerization reaction of the radical curable component (E) described above, preferably a radical polymerization initiator, and more preferably a photoradical polymerization initiator.
• the radical polymerization initiator include an alkylphenone compound, a benzoin compound, a benzophenone compound, an oxime ester compound, a phosphine compound and the like.
• the radical polymerization initiator is preferably a photoradical polymerization initiator, and more preferably an oxime ester-based photoradical polymerization initiator from the viewpoint of the reactivity of the polymerization reaction.
• the reaction rate of the radical curing component (E) can be increased even under curing conditions where the illuminance or the amount of light is weak.
• the content of the initiator (F) is usually 0.01 to 20 parts by mass, preferably 0.3 to 10 parts by mass, and 0.5 to 5 parts by mass with respect to 100 parts by mass of the resin (A). It is more preferably parts by mass, more preferably 0.75 to 4 parts by mass, and particularly preferably 1 to 3 parts by mass.
• the light selective absorption compound (G) is a light-absorbing compound other than the compound (B), and is, for example, a compound (ultraviolet absorber) that absorbs light having a wavelength of 250 nm to 380 nm (preferably a wavelength of 250 nm or more and less than 360 nm). Further, it is a compound (dye) that absorbs a wavelength of 380 to 780 nm and a compound (infrared absorber) that absorbs a wavelength of 780 to 1500 nm.
• a compound (ultraviolet absorber) that absorbs light having a wavelength of 250 nm to 380 nm (preferably a wavelength of 250 nm or more and less than 360 nm).
• a compound (dye) that absorbs a wavelength of 380 to 780 nm
• a compound (infrared absorber) that absorbs a wavelength of 780 to 1500 nm.
• the structure of the ultraviolet absorber is not particularly limited as long as it is a compound that absorbs light having a wavelength of 250 nm to 380 nm, but a benzotriazole-based compound, a benzophenone-based compound, a triazine-based compound, a salicylate-based compound, and a cyanoacrylate-based compound. Compounds such as benzoxazine-based compounds are preferable.
• the content of the light selective absorption compound (G) is usually 0.01 to 50 parts by mass, preferably 0.1 to 40 parts by mass, and more preferably 0 with respect to 100 parts by mass of the resin (A). It is .2 to 30 parts by mass, more preferably 0.3 to 25 parts by mass, and particularly preferably 0.5 to 20 parts by mass.
• the pressure-sensitive adhesive composition (i) may further contain at least one selected from the group consisting of the singlet oxygen citrate and the metal complex compound described above.
• the content thereof is usually 0.01 with respect to 100 parts by mass of the resin (A). It is about 50 parts by mass, preferably 0.1 to 20 parts by mass.
• the present invention includes dyed products (eg, textiles, films, resins, etc.) dyed with compound (B).
• Dyeing with compound (B) is carried out, for example, by immersing an article such as a fiber, a film, or a resin in a solution prepared by dissolving compound (B) in a solvent.
• Example 1 Synthesis of compound represented by formula (1) 13 parts of malononitrile was dissolved in 100 parts of ethanol to obtain a solution (1).
• the inside of a 100 mL-four-necked flask equipped with a Dimroth condenser and a thermometer has a nitrogen atmosphere, and the compound represented by the formula (b-1) (4,4a, 5,6-tetrahydro-7-hydroxy-2 (3H)).
• b-Naphthalenone 15 parts, ethanol 120 parts, potassium hydroxide 13 parts were mixed, and the temperature of the obtained mixture was raised to 80 ° C.
• the solution (1) was added dropwise to the mixture, and the mixture was heated and stirred for 30 minutes.
• ⁇ Maximum absorption wavelength and gram absorption coefficient ⁇ measurement> A 2-butanone solution (0.0006 g / L) of the obtained compound represented by the formula (1) is placed in a 1 cm quartz cell, and the quartz cell is set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation). Then, the absorbance in the wavelength range of 300 to 800 nm was measured every 1 nm step by the double beam method. The gram absorption coefficient for each wavelength was calculated from the obtained absorbance value, the concentration of the compound represented by the formula (1) in the solution, and the optical path length of the quartz cell.
• ⁇ ( ⁇ ) A ( ⁇ ) / CL
• ⁇ ( ⁇ ) represents the gram extinction coefficient (L / (g ⁇ cm)) of the compound represented by the formula (1) at the wavelength ⁇ nm
• a ( ⁇ ) represents the absorbance at the wavelength ⁇ nm
• C represents the concentration (g / L)
• L represents the optical path length (cm) of the quartz cell.
• the maximum absorption wavelength of the obtained compound represented by the formula (1) was 547 nm, and the gram absorption coefficient ( ⁇ ( ⁇ max)) at the maximum absorption wavelength was 772 L / (g ⁇ cm).
• Example 2 Synthesis of compound represented by formula (2)
• 1 part of the compound represented by the formula (1) and 100 parts of water were mixed and vigorously stirred.
• 100 parts of a saturated copper sulfate aqueous solution was added dropwise to the obtained mixture little by little, and the mixture was stirred at room temperature for 1 hour.
• the obtained mixture was purified to obtain 0.6 parts of the compound represented by the formula (2).
• Example 3 Synthesis of compound represented by formula (3)
• 1 part of the compound represented by the formula (1) and 100 parts of water were mixed and vigorously stirred.
• 100 parts of a saturated aqueous solution of barium chloride was added dropwise to the obtained mixture little by little, and the mixture was stirred at room temperature for 1 hour.
• the obtained mixture was purified to obtain 0.5 part of the compound represented by the formula (3).
• Example 4 Synthesis of compound represented by formula (4)
• 1 part of the compound represented by the formula (1) and 100 parts of water were mixed and vigorously stirred.
• 100 parts of a saturated aqueous solution of calcium chloride was added dropwise to the obtained mixture little by little, and the mixture was stirred at room temperature for 1 hour.
• the obtained mixture was purified to obtain 0.4 parts of the compound represented by the formula (4).
• Example 5 Synthesis of the compound represented by the formula (5)
• 1 part of the compound represented by the formula (1) and 100 parts of water were mixed and vigorously stirred.
• 100 parts of a saturated magnesium chloride aqueous solution was added dropwise to the obtained mixture little by little, and the mixture was stirred at room temperature for 1 hour.
• the obtained mixture was purified to obtain 0.6 parts of the compound represented by the formula (5).
• Example 6 Synthesis of the compound represented by the formula (6)
• 1 part of the compound represented by the formula (1) and 100 parts of acetonitrile were mixed and stirred.
• 1 mol equivalent of tetraphenylphosphonium chloride was added to the compound represented by the formula (1), and the mixture was stirred for 1 hour.
• the obtained mixture was purified to obtain 1.1 parts of the compound represented by the formula (6).
• composition (1) (adhesive composition (1))
• Polymerization example 1 Preparation of acrylic resin (A) In a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirrer. , 81.8 parts of ethyl acetate, 96 parts of butyl acrylate, 3 parts of 2-hydroxyethylmethyl acrylate, and 1 part of acrylic acid were charged as a solvent, and the air in the device was replaced with nitrogen gas to eliminate oxygen. The internal temperature was raised to 55 ° C while including it.
• acrylic resin (A) was referred to as acrylic resin (A).
• composition (1) (adhesive composition (1))>
• a cross-linking agent (manufactured by Toso Co., Ltd .: trade name "Coronate L", isocyanate compound, solid content 75%) is 0 with respect to 100 parts of the solid content of the ethyl acetate solution (resin concentration: 20%) of the acrylic resin (A). .5 parts, silane compound (manufactured by Shin-Etsu Chemical Industry Co., Ltd .: trade name "KBM3066") 0.28 parts, 1 part of the compound represented by the formula (1) are mixed, and the solid content concentration becomes 14%. Ethyl acetate was added to the composition (1) (adhesive composition (1)).
• the blending amount of the cross-linking agent is the number of parts by mass as the active ingredient.
• compositions (2) to (9) The composition was the same as in Example 7 except that each component and the content of each component were changed as shown in Table 5.
• (2) (Adhesive composition (2)) to composition (9) (adhesive composition (9)) were prepared.
• the blending amount of the cross-linking agent is the number of parts by mass as the active ingredient, and the resin (A) is the number of parts by mass of the solid content.
• Acrylic resin (A) Acrylic resin (A) synthesized in Polymerization Example 1
• Formula (1) Compound represented by the formula (1) synthesized in Example 1.
• Coronate L manufactured by Tosoh Corporation, trade name: coronate L, isocyanate-based cross-linking agent KBM3066: manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM3066, Silane Coupling Agent
• Q-1 [Bis (4-morpholinosulfonyl-1,2-dithiophenolate) copper-tetra-n-butylammonium]
• Q-2 Bis (dithiobenzyl) nickel
• Q-3 Tetrabutylphosphonium bis (1,3-dithiol-2-thion-4,5-dithiorat) Nickel
• Q-4 Tetrabutylammonium bis (maleonitrile dithiolate) nickel (III)
• Q-5 Nickel diethyldithiocarbamate Q
• a polarizing plate having a 13 ⁇ m cycloolefin film bonded to one side of an 8 ⁇ m polarizing element using an adhesive layer was prepared. After the resin molded body (1) is bonded to the polarizing element side by a laminator, it is cured under the conditions of a temperature of 23 ° C. and a relative humidity of 65% for 7 days, and then cured for 7 days. Was obtained.
• the obtained laminate is cut into a size of 30 cm ⁇ 30 cm, the separate film is peeled off, and the resin molded body (1) and the non-alkali glass [trade name “EAGLE XG” manufactured by Corning Co., Ltd.] are bonded together.
• Cycloolefin film / Alkali / Resin molded body (1) / Laminated body (1-1) having a laminated structure of glass was obtained.
• the obtained laminate (1-1) was put into a sunshine weather meter (manufactured by Suga Test Instruments Co., Ltd.) under the conditions of a temperature of 63 ° C. and a relative humidity of 50% RH for 75 hours, and a weather resistance test was carried out.
• the same evaluation was performed using the compositions (2) to (8) instead of the composition (1).
• the results are shown in Table 6.
• the same evaluation was performed using the composition (9) instead of the composition (1).
• the absorbance retention rate when the composition (9) was used was confirmed at a wavelength of 510 nm.
• the absorption wavelength for evaluating the absorbance retention rate a wavelength having an absorbance of 1 to 1.5 on the long wave side of the maximum absorption wavelength is selected from the measured absorbances. This is because it is the most sensitive absorbance region in terms of the measurement accuracy of the spectroscopic measuring device.
• composition of the present invention has a small full width at half maximum and high absorption selectivity.
• composition of the present invention has a high absorbance retention rate even after the weather resistance test, and has good weather resistance.
• a 2-butanone solution (0.0006 g / L) of the obtained compound represented by the formula (7) was prepared, and the maximum absorption wavelength and the gram extinction coefficient were measured in the same manner as described above.
• the maximum absorption wavelength of the represented compound was 643 nm, and the gram extinction coefficient ( ⁇ ( ⁇ max)) at the maximum absorption wavelength was 247 L / (g ⁇ cm).

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