WO2022138966A1 - フォトクロミック組成物、フォトクロミック物品及び眼鏡 - Google Patents
フォトクロミック組成物、フォトクロミック物品及び眼鏡 Download PDFInfo
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- WO2022138966A1 WO2022138966A1 PCT/JP2021/048399 JP2021048399W WO2022138966A1 WO 2022138966 A1 WO2022138966 A1 WO 2022138966A1 JP 2021048399 W JP2021048399 W JP 2021048399W WO 2022138966 A1 WO2022138966 A1 WO 2022138966A1
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- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- ALWFUNCIDKEZLN-UHFFFAOYSA-J propan-2-ylsulfanyl-propylsulfanyl-bis(thietan-2-ylsulfanyl)stannane Chemical compound C1CSC1S[Sn](SC(C)C)(SCCC)SC1CCS1 ALWFUNCIDKEZLN-UHFFFAOYSA-J 0.000 description 1
- VCKFFVJIHABUGW-UHFFFAOYSA-J propan-2-ylsulfanyl-tris(thietan-2-ylsulfanyl)stannane Chemical compound C1CSC1S[Sn](SC1SCC1)(SC(C)C)SC1CCS1 VCKFFVJIHABUGW-UHFFFAOYSA-J 0.000 description 1
- GTCKESIBYCJUAK-UHFFFAOYSA-J propylsulfanyl-tris(thietan-2-ylsulfanyl)stannane Chemical compound C1CSC1S[Sn](SC1SCC1)(SCCC)SC1CCS1 GTCKESIBYCJUAK-UHFFFAOYSA-J 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- REEUQQPUAUDLTJ-UHFFFAOYSA-N tetrakis(thietan-2-ylsulfanyl)germane Chemical compound S1CCC1S[Ge](SC1SCC1)(SC1SCC1)SC1SCC1 REEUQQPUAUDLTJ-UHFFFAOYSA-N 0.000 description 1
- FNNWECYNSMBBES-UHFFFAOYSA-J tetrakis(thietan-2-ylsulfanyl)stannane Chemical compound S1CCC1S[Sn](SC1SCC1)(SC1SCC1)SC1SCC1 FNNWECYNSMBBES-UHFFFAOYSA-J 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- GCNLVZVHPNRHEB-UHFFFAOYSA-K tris(thietan-2-ylsulfanyl)bismuthane Chemical compound S1CCC1S[Bi](SC1SCC1)SC1SCC1 GCNLVZVHPNRHEB-UHFFFAOYSA-K 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/04—Esters of silicic acids
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1545—Six-membered rings
-
- 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
- C08K5/357—Six-membered rings
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses
- G02C7/102—Photochromic filters
Definitions
- the present invention relates to a photochromic composition, a photochromic article and eyeglasses.
- the photochromic compound is a compound having a property of coloring under irradiation of light in a wavelength range having photoresponsiveness and fading under non-irradiation (photochromic property).
- Patent Document 1 discloses a naphthopyrane-based compound having photochromic properties.
- Examples of the method of imparting photochromic properties to an optical article such as a spectacle lens include a method of incorporating a photochromic compound in a substrate and a method of forming a layer containing the photochromic compound.
- a high coloring density at the time of coloring in the visible region can be mentioned.
- One aspect of the present invention is to provide a photochromic article having a high coloring concentration at the time of coloring in the visible range.
- One aspect of the present invention is one or more compounds represented by the following general formula A, one or more compounds represented by the following general formula B, and one or more compounds represented by the following general formula C.
- photochromic articles including.
- one aspect of the present invention relates to a photochromic composition containing one or more compounds represented by the following general formula A and one or more compounds represented by the following general formula B.
- R 1 to R 6 , B 1 and B 2 each independently represent a hydrogen atom or a substituent.
- R 7 to R 12 , B 3 and B 4 independently represent a hydrogen atom or a substituent, and R 13 and R 14 each independently represent an electron donating group.
- R 15 to R 20 , B 5 and B 6 independently represent a hydrogen atom or a substituent
- R 21 and R 22 represent a hydrogen atom on one side and an electron donating group on the other side, respectively. ..
- the present inventor has combined a compound represented by the general formula A, a compound represented by the general formula B, and a compound represented by the general formula C to color the compound at a high concentration in the visible region.
- a compound represented by the general formula A the compound represented by the general formula B, and the compound represented by the general formula C have different absorption peak positions and / or peak intensities in the visible region, and therefore these compounds are combined. It is presumed that this enables high-concentration coloring in a wide wavelength range.
- the present invention is not limited to the inferences described herein.
- a photochromic compound undergoes an excited state when irradiated with light such as sunlight, and structurally transforms into a colored body.
- the structure after structural conversion through light irradiation can be called a "colored body”.
- the structure before light irradiation can be called a "colorless body”.
- the term "colorless” with respect to a colorless body is not limited to being completely colorless, and includes cases where the color is lighter than that of the colored body.
- the structure of the general formula A, the structure of the general formula B, and the structure of the general formula C are colorless structures, respectively.
- the "photochromic article” means an article containing a photochromic compound.
- the photochromic article according to one aspect of the present invention is, as a photochromic compound, one or more compounds represented by the general formula A, one or more compounds represented by the general formula B, and a compound represented by the general formula C. Includes one or more.
- the photochromic compound can be included in the substrate of the photochromic article and / or can be included in the photochromic layer in the photochromic article having the substrate and the photochromic layer.
- the "photochromic layer” is a layer containing a photochromic compound.
- the "photochromic composition” means a composition containing a photochromic compound.
- the photochromic composition according to one aspect of the present invention is, as a photochromic compound, one or more compounds represented by the general formula A, one or more compounds represented by the general formula B, and a compound represented by the general formula C.
- any of various substituents that is, R 1 , R 2 , B 1 , B 2 in the general formula A, and R 7 to R 12 , B 3 and B 4 in the general formula B.
- the substituents that can be represented by the above, the substituents that can be represented by any of R 15 to R 20 , R 5 and R 6 in the general formula C, and the substituents that will be described later have substituents.
- a linear or branched alkyl group having 1 to 18 carbon atoms such as a hydroxy group, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group and a hexyl group, and a single group having 5 to 18 carbon atoms such as a cyclopentyl group and a cyclohexyl group.
- a linear or branched alkoxy group having 1 to 24 constituent atoms such as a cyclic aliphatic alkyl group, a methoxy group, an ethoxy group, and a butoxy group having a compound ring such as a ring or a bicyclo ring, and a non-aromatic group having 1 to 24 constituent atoms.
- a linear or branched perfluoroalkyl group having 1 to 18 carbon atoms such as a cyclic substituent and a trifluoromethyl group
- a linear or branched perfluoroalkoxy group such as a trifluoromethoxy group, a methyl sulfide group and an ethyl sulfide group.
- a linear or branched alkyl sulfide group having 1 to 24 constituent atoms such as a butyl sulfide group, a phenyl group, a naphthyl group, an anthrasenyl group, a fluoranthenyl group, a phenanthryl group, a pyranyl group, a peryleneyl group, a styryl group, a fluorenyl group, etc.
- Aryl group such as phenyloxy group, aryl sulfide group such as phenyl sulfide group, pyridyl group, furanyl group, thienyl group, pyrrolyl group, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, Heteroaryl groups such as dibenzothiophenyl group, carbazolyl group, diazolyl group, triazolyl group, quinolinyl group, phenothiazine group, phenoxadinyl group, phenazinyl group, thianthryl group, acridinyl group, amino group (-NH 2 ), monomethylamino group and the like.
- Monoalkylamino group dialkylamino group such as dimethylamino group, monoarylamino group such as monophenylamino group, diarylamino group such as diphenylamino group, piperidino group, morpholino group, thiomorpholino group, tetrahydroquinolino group, Cyclic amino groups such as tetrahydroisoquinolino groups, ethynyl groups, mercapto groups, silyl groups, sulfonic acid groups, alkylsulfonyl groups, formyl groups, carboxy groups, cyano groups and fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.
- Substituent Rm selected from the group consisting of halogen atoms; or Substituents in which R m is further substituted with one or more identical or different R m ; Can be.
- R m substituted with one or more identical or different R m an alkoxy group is further substituted with the carbon atom at the end of the alkoxy group, and the carbon atom at the end of the alkoxy group is further substituted.
- examples thereof include structures in which the alkoxy group is substituted.
- the same or different positions are used in two or more of the five replaceable positions of the phenyl group.
- a structure in which R m is substituted can be mentioned. However, the present invention is not limited to this example.
- the "carbon number” and the “constituting atom number” refer to the number including the carbon number or the atom number of the substituent for the group having a substituent.
- substituents that is, R 1 , R 2 , B 1 , B 2 in the general formula A, and R 7 to R 12 , B 3 and B 4 in the general formula B.
- the "solubilizing group” refers to a substituent that can contribute to enhancing compatibility with any liquid or a specific liquid.
- the solubilizing group includes a linear group having 4 to 50 carbon atoms, an alkyl group containing a branched or cyclic structure, a linear group having 4 to 50 constituent atoms, a branched or cyclic alkoxy group, and a linear chain having 4 to 50 constituent atoms.
- Substituents that may contribute to promoting the thermal motion of the molecules of the compound are preferred.
- a compound having a solubilizing group as a substituent prevents the solute from solidifying by inhibiting the distance between the solute molecules from approaching, and lowers the melting point and / or the glass transition temperature of the solute to reduce the molecular assembly close to that of a liquid. You can make a state.
- the soluble group can liquefy the solute and increase the solubility of the compound having this substituent in the liquid.
- the solubilizing group includes a linear alkyl group such as n-butyl group, n-pentyl group, n-hexyl group, n-octyl group, branched alkyl group tert-butyl group and cyclic alkyl group. Certain cyclopentyl and cyclohexyl groups are preferred.
- the substituent is preferably a methoxy group, an ethoxy group, a phenoxy group, a methyl sulfide group, an ethyl sulfide group, a phenyl sulfide group, a trifluoromethyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group or a dibenzothiophenyl group.
- it can be a methoxy group, a phenoxy group, a methyl sulfide group, a phenyl sulfide group, a trifluoromethyl group, a phenyl group, a dimethyl amino group, a diphenyl amino group, a piperidino group, a morphorylno group, a thiomorpholino group, a cyano group.
- a substituent selected from the group consisting of solubilizing groups.
- the "electron-withdrawing group” refers to a substituent that easily attracts an electron from the bonded atom side as compared with a hydrogen atom. Electron-withdrawing groups can attract electrons as a result of substituent effects such as inductive effects, mesomeric effects (or resonance effects).
- the electron-withdrawing group examples include a halogen atom (fluorine atom: -F, chlorine atom: -Cl, bromine atom: -Br, iodine atom: -I), trifluoromethyl group: -CF 3 , nitro group: -NO 2 , cyano group: -CN, formyl group: -CHO, acyl group: -COR (R is a substituent), alkoxycarbonyl group: -COOR, carboxy group: -COOH, substituted sulfonyl group: -SO 2 R ( R is a substituent), a sulfo group: -SO 3H and the like.
- halogen atom fluorine atom: -F, chlorine atom: -Cl, bromine atom: -Br, iodine atom: -I
- trifluoromethyl group -CF 3
- nitro group: -NO 2 cyano group:
- Suitable electron-withdrawing groups include a fluorine atom, which is an electron-withdrawing group having a high electronegativity, and an electron-withdrawing group having a positive value for the substituent constant ⁇ p at the paraposition based on Hammett's law. can.
- the "electron donating group” refers to a substituent that is more likely to donate an electron to the bonded atom side as compared with a hydrogen atom.
- the electron-donating group can be a substituent that easily donates an electron as a sum of the inductive effect, the mesomeric effect (or the resonance effect), and the like.
- Specific examples of the electron donating group include hydroxy group: -OH, thiol group: -SH, alkoxy group: -OR (R is an alkyl group), alkyl sulfide group: -SR (R is an alkyl group), and aryl sulfide group.
- R 1 to R 6 , B 1 and B 2 each independently represent a hydrogen atom or a substituent.
- R 1 and R 2 each independently preferably represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and each represent a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group or a hexyl group. Is more preferable. It is more preferable that R 1 and R 2 each independently represent a methyl group or an ethyl group, and it is even more preferable that both R 1 and R 2 represent a methyl group or both represent an ethyl group.
- B 1 and B 2 each independently represent a substituted or unsubstituted phenyl group.
- the phenyl group has a plurality of substituents, two or more of these substituents may be bonded to form a ring.
- Specific examples of the formed ring include the rings contained in the exemplary compounds described below.
- the substitution position of the substituent in the substituted phenyl group is preferably a position at the para position with respect to the carbon atom to which B 1 and B 2 are bonded.
- substituent of the substituted phenyl group include a morpholino group, a piperidino group, a halogen atom, an alkoxy group, and a substituent contained in the following exemplary compounds such as the following substituents.
- "*" relating to a partial structure of a compound indicates a bonding position with an atom to which the partial structure is bonded.
- R 3 to R 6 independently represent hydrogen atoms or substituents, respectively. In one form, R 3 to R 6 can all be hydrogen atoms. In another embodiment, R 3 to R 6 each independently represent a hydrogen atom or an electron-withdrawing group, where one or more of R 3 to R 6 represents an electron-withdrawing group.
- a halogen atom a perfluoroalkyl group having 1 to 6 carbon atoms, a perfluorophenyl group, a perfluoroalkylphenyl group or a cyano group is preferable.
- a fluorine atom is preferable as the halogen atom.
- the perfluoroalkyl group having 1 to 6 carbon atoms a trifluoromethyl group is preferable.
- the compound represented by the general formula A can be the following compound.
- R 3 to R 6 only R 4 is an electron-withdrawing group, and R 3 , R 5 and R 6 are hydrogen atoms.
- R 3 to R 6 R 4 and R 6 are the same or different electron-withdrawing groups, and R 3 and R 5 are hydrogen atoms.
- R 3 to R 6 R 3 and R 5 are the same or different electron-withdrawing groups, and R 4 and R 6 are hydrogen atoms.
- Examples of the compound represented by the general formula A include the following compounds. However, the present invention is not limited to the compounds exemplified below.
- R 7 to R 12 , B 3 and B 4 independently represent hydrogen atoms or substituents, respectively.
- R 7 and R 8 each independently preferably represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and each represent a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group or a hexyl group. Is more preferable. It is more preferable that R 7 and R 8 each independently represent a methyl group or an ethyl group, and it is even more preferable that both R 7 and R 8 represent a methyl group or both represent an ethyl group.
- B 3 and B 4 each independently represent a substituted or unsubstituted phenyl group.
- the phenyl group has a plurality of substituents, two or more of these substituents may be bonded to form a ring.
- Specific examples of the formed ring include the rings contained in the exemplary compounds described below.
- the substitution position of the substituent in the substituted phenyl group is preferably a position at the para position with respect to the carbon atom to which B 3 and B 4 are bonded.
- substituent of the substituted phenyl group include a morpholino group, a piperidino group, a halogen atom, an alkoxy group, and a substituent contained in the following exemplary compounds such as the following substituents.
- R 9 to R 12 each independently represent a hydrogen atom or a substituent. In one form, R 9 to R 12 can all be hydrogen atoms. In another embodiment, R 10 can be an electron-withdrawing group and R 9 , R 11 and R 12 can all be hydrogen atoms. Further, in another embodiment, R 9 and R 11 can be independently electron-withdrawing groups, and R 10 and R 12 can be hydrogen atoms.
- As the electron-withdrawing group a halogen atom, a perfluoroalkyl group having 1 to 6 carbon atoms, a perfluorophenyl group, a perfluoroalkylphenyl group or a cyano group is preferable.
- a fluorine atom is preferable as the halogen atom.
- R 10 can be a substituted or unsubstituted phenyl group, preferably R 10 is a substituted or unsubstituted phenyl group, and R 9 , R 11 and R 12 are hydrogen atoms. can.
- a substituted phenyl group a phenyl group substituted with one or more halogen atoms and / or one or more cyano groups, for example, a halogen atom (preferably a fluorine atom) at all five substitution positions of the phenyl group.
- Examples thereof include a phenyl group substituted with a cyano group and a monosubstituted phenyl group substituted with a cyano group at a position at the para position with respect to the carbon atom to which R10 is bonded.
- R 13 and R 14 each independently represent an electron donating group. That is, R 13 and R 14 represent the same or different electron donating groups.
- R 13 and R 14 are independently selected from the group consisting of a methoxy group, an ethoxy group, a phenoxy group, a methyl sulfide group, a phenyl sulfide group, a dimethyl amino group, a pyrrolidino group, a piperidino group, a morpholino group and a thiomorpholino group. It is preferable to represent an electron donating group.
- R 13 and R 14 are a morpholino group and R 14 is an alkoxy group (preferably a methoxy group), R 13 is a morpholino group and R 14 is a methyl sulfide group (-S-). It is preferable that CH 3 ), that both R 13 and R 14 are alkoxy groups (preferably methoxy groups), and that both R 13 and R 14 are methyl sulfide groups.
- Examples of the compound represented by the general formula B include the following compounds. However, the present invention is not limited to the compounds exemplified below.
- R 15 to R 20 , B 5 and B 6 independently represent hydrogen atoms or substituents, respectively.
- One of R 21 and R 22 represents a hydrogen atom and the other represents an electron donating group.
- R 15 and R 16 each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and are preferably a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group or a group. It is more preferable to represent a hexyl group. It is more preferable that R 15 and R 16 each independently represent a methyl group or an ethyl group, and it is even more preferable that both R 15 and R 16 represent a methyl group or both represent an ethyl group.
- B 5 and B 6 each independently represent a substituted or unsubstituted phenyl group.
- the phenyl group has a plurality of substituents, two or more of these substituents may be bonded to form a ring.
- the formed ring include the rings contained in the exemplary compounds described below.
- the substitution position of the substituent in the substituted phenyl group is preferably a position at the para position with respect to the carbon atom to which B 5 and B 6 are bonded.
- Specific examples of the substituent of the substituted phenyl group include a morpholino group, a piperidino group, a halogen atom, an alkoxy group, the following substituents and the like.
- R 17 to R 20 each independently represent a hydrogen atom or a substituent.
- R 17 to R 20 can all be hydrogen atoms.
- R 18 can be an electron-withdrawing group and R 17 , R 19 and R 20 can all be hydrogen atoms.
- R 17 and R 19 can be independently electron-withdrawing groups, and R 18 and R 20 can be hydrogen atoms.
- a halogen atom a perfluoroalkyl group having 1 to 6 carbon atoms, a perfluorophenyl group, a perfluoroalkylphenyl group or a cyano group is preferable.
- a fluorine atom is preferable as the halogen atom.
- the perfluoroalkyl group having 1 to 6 carbon atoms a trifluoromethyl group is preferable.
- R 18 can be a substituted or unsubstituted phenyl group, preferably R 18 is a substituted or unsubstituted phenyl group, and R 17 , R 19 and R 20 are hydrogen atoms. can.
- a substituted phenyl group a phenyl group substituted with one or more halogen atoms and / or one or more cyano groups, for example, a halogen atom (preferably a fluorine atom) at all five substitution positions of the phenyl group.
- Examples thereof include a phenyl group substituted with a cyano group and a monosubstituted phenyl group substituted with a cyano group at a position at the para position with respect to the carbon atom to which R10 is bonded.
- R 21 and R 22 represents a hydrogen atom and the other represents an electron donating group. It is preferable that R 21 is a hydrogen atom and R 22 is an electron donating group.
- the electron donating group represented by R 21 or R 22 (preferably R 22 ) is a methoxy group, an ethoxy group, a phenoxy group, a methyl sulfide group, a phenyl sulfide group, a dimethyl amino group, a pyrrolidino group, a piperidino group or a morpholino group. And more preferably represent an electron donating group selected from the group consisting of thiomorpholino groups.
- Examples of the compound represented by the general formula C include the following compounds. However, the present invention is not limited to the compounds exemplified below.
- the compound represented by the general formula A, the compound represented by the general formula B, and the compound represented by the general formula C can be synthesized by a known method.
- the following documents can be referred to. Japanese Patent No. 4884578, US2006 / 0226402A1, US2006 / 0228557A1, US2008 / 0103301A1, US2011 / 0108781A1, US2011 / 0108781A1, US Pat. No. 7527754, US Pat. No. 7556751, WO2001 / 60811A1, WO2001 / 60811A1 , WO1996 / 014596A1 and WO2001 / 019813A1.
- the photochromic article according to one aspect of the present invention and the photochromic composition according to one aspect of the present invention include one or more compounds represented by the general formula A and one or more compounds represented by the general formula B. Includes one or more of the compounds represented by the general formula C.
- the compound represented by the general formula A contained in the photochromic article and the photochromic composition may be only one kind, and may be two or more kinds (for example, two or more kinds and four kinds or less).
- the compound represented by the general formula B contained in the photochromic article and the photochromic composition may be only one kind, and may be two or more kinds (for example, two or more kinds and four kinds or less).
- the compound represented by the general formula C contained in the photochromic article and the photochromic composition may be only one kind, and may be two or more kinds (for example, two or more kinds and four kinds or less).
- the total content of the compound represented by the general formula B and the compound represented by the general formula C is higher than the content of the compound represented by the general formula A on a mass basis. Is preferable.
- the compound represented by the general formula B and the compound represented by the general formula C are represented by 100% by mass as a total of the compound represented by the general formula A, the compound represented by the general formula B and the compound represented by the general formula C.
- the total content of the compounds is preferably more than 50% by mass, more preferably 60% by mass or more, further preferably 70% by mass or more, still more preferably 80% by mass or more. It is even more preferable that the content is 90% by mass or more.
- the compound represented by the general formula B and the compound represented by the general formula C are used with respect to the total (100% by mass) of the compound represented by the general formula A, the compound represented by the general formula B, and the compound represented by the general formula C.
- the total content of the represented compounds can be less than 100% by weight, 99% by weight or less, 98% by weight or less, 97% by weight or less, 96% by weight or less or 95% by weight or less.
- the total of the compound represented by the general formula B and the compound represented by the general formula C is set to 100% by mass, and the general formula is used.
- the content of the compound represented by B can be 1% by mass or more or 99% by mass or more, and can be 25% by mass or less or 75% by mass or less.
- the content of the compound represented by the general formula B is the total content of the photochromic article and the photochromic composition when two or more compounds represented by the general formula B are contained. This point is the same for the content of various components in the present invention and the present specification.
- the total amount thereof is 100% by mass
- the compound represented by the general formula A, the compound represented by the general formula B and the compound represented by the general formula C are in total, for example, 0.1 to 15. It can contain about 0.0% by mass. However, it is not limited to this range.
- the photochromic article can have at least a substrate.
- the compound represented by the general formula A, the compound represented by the general formula B, and the compound represented by the general formula C can be contained in the base material of the photochromic article.
- the photochromic article can have a base material and a photochromic layer, and the base material and / or the photochromic layer is represented by a compound represented by the general formula A, a compound represented by the general formula B, and a general formula C. Compounds can be included.
- the compound represented by the general formula A, the compound represented by the general formula B, and the compound represented by the general formula C can be contained only in the base material in one form in the base material and the photochromic layer, and other compounds can be contained in the base material. In one form, it can be contained only in the photochromic layer, and in the other form, it can be contained in the base material and the photochromic layer. Further, the base material and the photochromic layer may contain only the compound represented by the general formula A, the compound represented by the general formula B and the compound represented by the general formula C as the photochromic compound, or one or more thereof. Other photochromic compounds can also be included.
- photochromic compounds include azobenzenes, spiropyrans, spiroxazines, naphthopyrans, indenonaphthopyrans, phenanthropyrans, hexaallylbisimidazoles, donor-acceptorstenhouse adducts (DASA). , Salicylidene anilines, dihydropyrenes, anthracene dimers, flugides, diarylethenes, phenoxynaphthasequinones, stilbenes and the like.
- DASA donor-acceptorstenhouse adducts
- the photochromic article can include a substrate selected according to the type of the photochromic article.
- the spectacle lens base material includes a plastic lens base material or a glass lens base material.
- the glass lens base material can be, for example, a lens base material made of inorganic glass.
- the plastic lens base material include styrene resins such as (meth) acrylic resins, polycarbonate resins, allyl resins, allyl carbonate resins such as diethylene glycol bisallyl carbonate resin (CR-39), vinyl resins, polyester resins, and polyether resins.
- Urethane resin obtained by reacting isocyanate compound with hydroxy compound such as diethylene glycol thiourethane resin obtained by reacting isocyanate compound with polythiol compound, (thio) epoxy compound having one or more disulfide bonds in the molecule.
- hydroxy compound such as diethylene glycol
- thiourethane resin obtained by reacting isocyanate compound with polythiol compound thio epoxy compound having one or more disulfide bonds in the molecule.
- examples thereof include a cured product (generally referred to as a transparent resin) obtained by curing the curable composition contained therein.
- a cured product generally referred to as a transparent resin
- the lens base material an undyed lens (colorless lens) may be used, or a dyed lens (dyed lens) may be used.
- the refractive index of the lens substrate can be, for example, about 1.50 to 1.75.
- the refractive index of the lens substrate is not limited to the above range, and may be within the above range or may be vertically separated from the above range.
- the refractive index means the refractive index for light having a wavelength of 500 nm.
- the lens base material may be a lens having a refractive power (so-called prescription lens) or a lens without refractive power (so-called prescription lens).
- the photochromic composition can be a polymerizable composition.
- the "polymerizable composition” is a composition containing one or more kinds of polymerizable compounds.
- a polymerizable composition containing at least, by a known molding method a cured product of such a polymerizable composition can be produced.
- the cured product can be included in the photochromic article as a substrate and / or can be included as a photochromic layer.
- the curing treatment can be light irradiation and / or heat treatment.
- the polymerizable compound is a compound having a polymerizable group, and the polymerizable composition can be cured to form a cured product by advancing the polymerization reaction of the polymerizable compound.
- the polymerizable composition can further contain one or more additives (eg, a polymerization initiator, etc.).
- the spectacle lens can be various lenses such as a single focus lens, a multifocal lens, and a progressive power lens.
- the type of lens is determined by the surface shapes of both sides of the lens base material.
- the surface of the lens substrate may be a convex surface, a concave surface, or a flat surface.
- the surface on the object side is a convex surface and the surface on the eyeball side is a concave surface.
- the photochromic layer can usually be provided on the object-side surface of the lens substrate, but may be provided on the eyeball-side surface.
- the photochromic layer can be a layer provided directly on the surface of the substrate or indirectly via one or more other layers.
- the photochromic layer can be, for example, a cured layer obtained by curing a polymerizable composition.
- a photochromic layer can be formed as a cured layer obtained by curing a polymerizable composition containing at least.
- the polymerizable composition is generally applied directly on the surface of the substrate, or applied to the surface of a layer provided on the substrate, and the applied polymerizable composition is cured.
- a photochromic layer is formed as a cured layer containing one or more compounds represented by the formula A, one or more compounds represented by the general formula B, and one or more compounds represented by the general formula C. can do.
- the coating method known coating methods such as a spin coating method, a dip coating method, a spray coating method, an inkjet method, a nozzle coating method, and a slit coating method can be adopted.
- the curing treatment can be light irradiation and / or heat treatment.
- the polymerizable composition can further contain one or more additives (for example, a polymerization initiator) in addition to one or more polymerizable compounds. As the polymerization reaction of the polymerizable compound proceeds, the polymerizable composition can be cured and a cured layer can be formed.
- the thickness of the photochromic layer can be, for example, 5 ⁇ m or more, 10 ⁇ m or more, or 20 ⁇ m or more, and can be, for example, 80 ⁇ m or less, 70 ⁇ m or less, or 50 ⁇ m or less.
- the polymerizable compound means a compound having one or more polymerizable groups in one molecule
- the "polymerizable group” means a reactive group capable of polymerizing. do.
- the polymerizable group include an acryloyl group, a methacryloyl group, a vinyl group, a vinyl ether group, an epoxy group, a thiol group, an oxetane group, a hydroxy group, a carboxy group, an amino group, an isocyanate group and the like.
- Examples of the polymerizable compound that can be used for forming the base material and the photochromic layer include the following compounds.
- An episulfide compound is a compound having two or more episulfide groups in one molecule.
- the episulfide group is a polymerizable group capable of ring-opening polymerization.
- Specific examples of episulfide compounds include bis (1,2-epithioethyl) sulfide, bis (1,2-epioethyl) disulfide, bis (2,3-epiothiopropyl) sulfide, and bis (2,3-epiothiopropyl) sulfide.
- the thietanyl compound is a thietan compound having two or more thietanyl groups in one molecule.
- the thietanyl group is a polymerizable group capable of ring-opening polymerization.
- Some thietanyl compounds have an episulfide group together with a plurality of thietanyl groups. Such compounds are listed as examples of the above episulfide compounds.
- Other thietanyl-based compounds include metal-containing thietan compounds having a metal atom in the molecule and non-metal-based thietan compounds containing no metal.
- non-metallic thietan compound examples include bis (3-thietanyl) disulfide, bis (3-thietanyl) sulfide, bis (3-thietanyl) trisulfide, bis (3-thietanyl) tetrasulfide, and 1,4-bis.
- the metal-containing thietan compound includes 14 group atoms such as Sn atom, Si atom, Ge atom and Pb atom, 4 group elements such as Zr atom and Ti atom, and 13 such as Al atom in the molecule. Examples thereof include group 12 atoms such as group atoms and Zn atoms. Specific examples thereof include alkylthio (thietanylthio) tin, bis (alkylthio) bis (thietanylthio) tin, alkylthio (alkylthio) bis (thietanylthio) tin, bis (thietanylthio) cyclic dithiotin compounds, and alkyl (thietanylthio) tin compounds.
- alkylthio (thietanylthio) tin examples include methylthiotris (thietanylthio) tin, ethylthiotris (thietanylthio) tin, propylthiotris (thietanylthio) tin, isopropylthiotris (thietanylthio) tin and the like.
- bis (alkylthio) bis (thietanylthio) tin include bis (methylthio) bis (thietanylthio) tin, bis (ethylthio) bis (thietanylthio) tin, bis (propylthio) bis (thietanylthio) tin, and bis (isopropylthio). Examples thereof include bis (thietanylthio) tin and the like.
- alkylthio (alkylthio) bis (thietanylthio) tin examples include ethylthio (methylthio) bis (thietanylthio) tin, methylthio (propylthio) bis (thietanylthio) tin, isopropylthio (methylthio) bis (thietanylthio) tin, and ethylthio (propylthio).
- Examples thereof include bis (thietanylthio) tin, ethylthio (isopropylthio) bis (thietanylthio) tin, and isopropylthio (propylthio) bis (thietanylthio) tin.
- bis (thietanilthio) cyclic dithiostin compound examples include bis (thietanilthio) dithiastannetan, bis (thietanilthio) dithiastannolan, bis (thietanilthio) dithiastanninan, and bis (thietanilthio) trithiastannocan. Can be exemplified.
- alkyl (thietanylthio) tin compound examples include methyltris (thietanylthio) tin, dimethylbis (thietanylthio) tin, butyltris (thietanylthio) tin, tetrakis (thietanylthio) tin, tetrakis (thietanylthio) germanium, and tris (thietanylthio) bismuth. It can be exemplified.
- a polyamine compound is a compound having two or more NH groups in one molecule, and can form a urea bond by reaction with polyisocyanate, and can form a thiourea bond by reaction with polyisothiocyanate. ..
- Specific examples of the polyamine compound include ethylenediamine, hexamethylenediamine, isophoronediamine, nonamethylenediamine, undecamethylenediamine, dodecamethylenediamine, metaxylenediamine, 1,3-propanediamine, putresin, and 2- (2-aminoethyl).
- Amino) etanol, diaminetriamine, p-phenylenediamine, m-phenylenediamine, melamine, 1,3,5-benzenetriamine and the like can be mentioned.
- Epoxy compound is a compound having an epoxy group in the molecule.
- the epoxy group is a polymerizable group capable of ring-opening polymerization.
- Epoxy compounds are generally classified into aliphatic epoxy compounds, alicyclic epoxy compounds and aromatic epoxy compounds.
- aliphatic epoxy compound examples include ethylene oxide, 2-ethyloxylan, butyl glycidyl ether, phenyl glycidyl ether, 2,2'-methylenebisoxylane, 1,6-hexanediol diglycidyl ether, and ethylene glycol diglycidyl ether.
- Diethylene glycol diglycidyl ether triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, nonaethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, tetrapropylene glycol di Glycyzyl ether, nonapropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, glycerol triglycidyl ether, diglycerol tetraglycidyl ether, pentaerythritol tetraglycidyl ether, tris (2-hydroxyethyl) isocyanurate Examples thereof include triglycidyl ether and the like.
- alicyclic epoxy compound examples include isophorone diol diglycidyl ether and bis-2,2-hydroxycyclohexylpropane diglycidyl ether.
- aromatic epoxy compound examples include resorcin diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, orthophthalic acid diglycidyl ester, phenol novolac polyglycidyl ether, and cresol novolac poly. Examples thereof include glycidyl ether.
- epoxy compounds having a sulfur atom in the molecule can also be used together with the epoxy group.
- sulfur-containing atomic epoxy compounds include chain aliphatic compounds and cyclic aliphatic compounds.
- chain aliphatic sulfur-containing atomic epoxy compounds include bis (2,3-epylpropyl) sulfide, bis (2,3-epoxypropyl) disulfide, and bis (2,3-epoxypropylthio) methane.
- 1,2-bis (2,3-epoxypropylthio) ethane 1,2-bis (2,3-epoxypropylthio) propane, 1,3-bis (2,3-epoxypropylthio) propane, 1 , 3-bis (2,3-epoxypropylthio) -2-methylpropane, 1,4-bis (2,3-epoxypropylthio) butane, 1,4-bis (2,3-epoxypropylthio)- 2-Methylbutane, 1,3-bis (2,3-epoxypropylthio) butane, 1,5-bis (2,3-epoxypropylthio) pentane, 1,5-bis (2,3-epoxypropylthio) -2-Methylpentane, 1,5-bis (2,3-epoxypropylthio) -3-thiapentane, 1,6-bis (2,3-epoxypropylthio) hexane, 1,6-bis
- cyclic aliphatic sulfur-containing atomic epoxy compound examples include 1,3-bis (2,3-epoxypropylthio) cyclohexane, 1,4-bis (2,3-epoxypropylthio) cyclohexane, and 1, 3-Bis (2,3-epoxypropylthiomethyl) cyclohexane, 1,4-bis (2,3-epoxypropylthiomethyl) cyclohexane, 2,5-bis (2,3-epoxypropylthiomethyl) -1, 4-Dithiane, 2,5-bis [ ⁇ 2- (2,3-epoxypropylthiomethyl) ethyl> thiomethyl] -1,4-dithiane, 2,5-bis (2,3-epoxypropylthiomethyl) -2 , 5-Dimethyl-1,4-dithiane and the like.
- a compound having a radically polymerizable group is a polymerizable group that can be radically polymerized.
- the radically polymerizable group include an acryloyl group, a methacryloyl group, an allyl group, a vinyl group and the like.
- a compound having a polymerizable group selected from the group consisting of an acryloyl group and a methacryloyl group is referred to as a "(meth) acrylate compound".
- the (meth) acrylate compound include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylicate, tetraethylene glycol di (meth) acrylicate, and polyethylene.
- allyl compound examples include allyl glycidyl ether, diallyl phthalate, diallyl terephthalate, diallyl isophthalate, diallyl carbonate, diethylene glycol bisallyl carbonate, methoxypolyethylene glycol allyl ether, and polyethylene glycol allyl ether.
- Methoxypolyethylene glycol-polypropylene glycol allyl ether Methoxypolyethylene glycol-polypropylene glycol allyl ether, butoxypolyethylene glycol-polypropylene glycol allyl ether, methacryloyloxypolyethylene glycol-polypropylene glycol allyl ether, phenoxypolyethylene glycol allyl ether, methacryloyloxypolyethylene glycol allyl ether and the like.
- Examples of the compound having a vinyl group include ⁇ -methylstyrene, ⁇ -methylstyrene dimer, styrene, chlorostyrene, methylstyrene, bromostyrene, dibromostyrene, divinylbenzene, and 3,9-divinylspirobi (m-dioxane). And so on.
- the photochromic article is a photochromic article such as a protective layer for improving the durability of the photochromic article, an antireflection layer, a water-repellent or hydrophilic antifouling layer, an anti-fog layer, and a primer layer for improving the adhesion between layers.
- a photochromic article such as a protective layer for improving the durability of the photochromic article, an antireflection layer, a water-repellent or hydrophilic antifouling layer, an anti-fog layer, and a primer layer for improving the adhesion between layers.
- One or more layers known as functional layers can be included at any position.
- the above photochromic article can be an optical article.
- One form of an optical article is a spectacle lens.
- a spectacle lens can also be referred to as a photochromic lens or a photochromic spectacle lens.
- a lens for goggles, a visor (eaves) portion of a sun visor, a shield member of a helmet, and the like can be mentioned.
- An optical article having an antiglare function is formed by applying the above-mentioned photochromic composition, which is a polymerizable composition, onto a substrate for these optical articles and subjecting the applied composition to a curing treatment to form a photochromic layer. Can be obtained.
- One aspect of the present invention relates to spectacles provided with a spectacle lens, which is a form of the above photochromic article.
- the details of the spectacle lens included in the spectacles are as described above.
- the photochromic compound can exert an antiglare effect like sunglasses by coloring the photochromic compound outdoors by being irradiated with sunlight, and when returning indoors, the photochromic compound can be exhibited. Transparency can be restored by fading.
- a known technique can be applied to the structure of the frame and the like for the above-mentioned eyeglasses.
- compositions containing a plurality of photochromic compounds the mass ratios of the respective photochromic compounds when the total amount of the photochromic compounds is 10 are shown in Table 2 (Tables 2-1 and 2-2).
- a photopolymerization initiator phenylbis (2,4,6-trimethylbenzoyl) phosphine oxide
- an antioxidant bis (3-tert-butyl-4-hydroxy-5-methylphenyl) propionic acid
- ethylene bis (oxyethylene) and a photostabilizer (bis sevacinate (1,2,2,6,6-pentamethyl-4-piperidyl)) and stirring thoroughly, a silane coupling agent ( ⁇ -methacry) Roxypropyltrimethoxysilane) was added dropwise with stirring. After that, defoaming was performed with an automatic revolution type stirring defoaming device.
- a photochromic composition was prepared by the above method.
- a plastic lens base material (HOYA brand name EYAS: center thickness 2.5 mm, diameter 75 mm, spherical lens power-4.00) is immersed in a sodium hydroxide aqueous solution (liquid temperature 60 ° C.) having a concentration of 10% by mass for 5 minutes. It was washed with alkali, then washed with pure water and dried. Then, an aqueous polyurethane resin solution (polycarbonate polyol polyurethane emulsion, viscosity 100 cPs, solid content concentration 38% by mass) was applied to the convex surface of the plastic lens base material in an environment of room temperature and a relative humidity of 40 to 60%, manufactured by Mikasa.
- a primer layer having a thickness of 5.5 ⁇ m was formed by applying a spin coater MS-B150 at a rotation speed of 1500 rpm for 1 minute by a spin coating method and then allowing it to air dry for 15 minutes.
- ⁇ Film formation of photochromic layer The photochromic composition prepared above is dropped onto the primer layer, and the rotation speed is changed in the slope mode from 500 rpm to 1500 rpm for 1 minute using MS-B150 manufactured by Mikasa, and further at 1500 rpm for 5 It was applied by a spin coating method using a program that was rotated for a second. Then, the photochromic composition coated on the primer layer formed on the plastic lens base material is irradiated with ultraviolet rays (main wavelength 405 nm) for 40 seconds in a nitrogen atmosphere (oxygen concentration of 500 ppm or less), and this composition. Was cured to form a photochromic layer. The thickness of the formed photochromic layer was 45 ⁇ m. In this way, a photochromic article (spectacle lens) was produced.
- the fading rate was evaluated by the following method.
- the transmittance (measurement wavelength: 550 nm) of each of the spectacle lenses of Examples and Comparative Examples before light irradiation (uncolored state) was measured by a spectrophotometer manufactured by Otsuka Electronics. The transmittance measured here is called "initial transmittance".
- Each spectacle lens was irradiated with light through an aeromas filter using a xenon lamp as a light source for 15 minutes to color the photochromic layer. This irradiation light was performed so that the irradiance and the tolerance of the irradiance became the values shown in Table 1 as specified in JIS T7333: 2005.
- the transmittance at the time of this coloring was measured in the same manner as the initial transmittance.
- the transmittance measured here is referred to as "coloring transmittance”.
- the time required from the time when the light irradiation was stopped until the transmittance became [(initial transmittance-transmittance at the time of coloring) / 2] was measured. This time is referred to as "half time”. It can be said that the shorter the half time, the faster the fading speed. Table 2 shows the obtained half time.
- one or more of the compounds represented by the general formula A, one or more of the compounds represented by the general formula B, and one or more of the compounds represented by the general formula C are included.
- Photochromic articles and photochromic compositions are provided.
- R 1 and R 2 can independently represent substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.
- R 1 and R 2 can independently represent a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group or a hexyl group, respectively.
- B 1 and B 2 in the general formula A, B 3 and B 4 in the general formula B, and B 5 and B 6 in the general formula C independently have substituted or unsubstituted phenyl groups, respectively.
- the substituents may be bonded to form a ring.
- R 3 to R 6 can independently represent a hydrogen atom or an electron-withdrawing group (however, one or more of R 3 to R 6 represent an electron-withdrawing group). ..
- the electron-withdrawing group can be a halogen atom, a perfluoroalkyl group having 1 to 6 carbon atoms, a perfluorophenyl group, a perfluoroalkylphenyl group or a cyano group.
- the halogen atom can be a fluorine atom.
- the perfluoroalkyl group can be a trifluoromethyl group.
- One or more selected from the group consisting of 5 and B6 can represent a substituent, such a substituent.
- Alkoxy group non-aromatic cyclic substituent having 1 to 24 constituent atoms, linear or branched perfluoroalkyl group having 1 to 18 carbon atoms, linear or branched perfluoroalkoxy group, constituent atoms 1 to 24 Linear or branched alkyl sulfide group, aryl group, aryloxy group, aryl sulfide group, heteroaryl group, amino group, monoalkylamino group, dialkylamino group, monoarylamino group, diarylamino group, piperidino group, morpholino Cyclic amino groups such as groups, thiomorpholino groups, tetrahydroquinolino groups, tetrahydroisoquinolino groups, ethynyl groups, mercapto groups, silyl groups, sulfonic acid groups, alkylsulfonyl groups, formyl groups, carboxy groups, cyano groups and halogen atoms. Substi
- R 7 and R 8 can independently represent substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.
- R 7 and R 8 can independently represent a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group or a hexyl group, respectively.
- R 13 and R 14 are independently methoxy group, ethoxy group, phenoxy group, methyl sulfide group, phenyl sulfide group, dimethyl amino group, pyrrolidino group, piperidino group, morpholino group and It can represent an electron donating group selected from the group consisting of thiomorpholino groups.
- R 15 and R 16 can independently represent substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.
- R 15 and R 16 can independently represent a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group or a hexyl group, respectively.
- the electron donating group represented by R 21 or R 22 in the general formula C is a methoxy group, an ethoxy group, a phenoxy group, a methyl sulfide group, a phenyl sulfide group, a dimethyl amino group, a pyrrolidino group or a piperidino group. It can be an electron donating group selected from the group consisting of a morpholino group and a thiomorpholino group.
- the total content of the compound represented by the general formula B and the compound represented by the general formula C in the photochromic article and the photochromic composition on a mass basis is that of the compound represented by the general formula A.
- the content can be exceeded.
- the photochromic article has a base material and a photochromic layer, and the photochromic layer is generally composed of one or more compounds represented by the general formula A and one or more compounds represented by the general formula B. It can be a photochromic article containing one or more of the compounds represented by the formula C.
- the photochromic layer can be a cured layer obtained by curing the polymerizable composition.
- the photochromic composition can contain a polymerizable compound.
- the photochromic article can be a spectacle lens.
- the photochromic article can be a goggle lens.
- the photochromic article can be the visor portion of a sun visor.
- the photochromic article can be a shield member of a helmet.
- spectacles provided with the above spectacle lens are provided.
- One aspect of the present invention is useful in the technical fields of eyeglasses, goggles, sun visors, helmets and the like.
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Abstract
Description
ヒドロキシ基、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基等の炭素数1~18の直鎖若しくは分岐のアルキル基、シクロペンチル基、シクロヘキシル基等の炭素数5~18の単環若しくはビシクロ環等の複環の環状脂肪族アルキル基、メトキシ基、エトキシ基、ブトキシ基等の構成原子数1~24の直鎖若しくは分岐のアルコキシ基、構成原子数1~24の非芳香族環状置換基、トリフルオロメチル基等の炭素数1~18の直鎖若しくは分岐のパーフルオロアルキル基、トリフルオロメトキシ基等の直鎖若しくは分岐のパーフルオロアルコキシ基、メチルスルフィド基、エチルスルフィド基、ブチルスルフィド基等の構成原子数1~24の直鎖若しくは分岐のアルキルスルフィド基、フェニル基、ナフチル基、アントラセニル基、フルオランテニル基、フェナントリル基、ピラニル基、ペリレニル基、スチリル基、フルオレニル基等のアリール基、フェニルオキシ基等のアリールオキシ基、フェニルスルフィド基等のアリールスルフィド基、ピリジル基、フラニル基、チエニル基、ピロリル基、ベンゾフラニル基、ベンゾチオフェニル基、インドリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、カルバゾリル基、ジアゾリル基、トリアゾリル基、キノリニル基、フェノチアジニル基、フェノキサジニル基、フェナジニル基、チアンスリル基、アクリジニル基等のヘテロアリール基、アミノ基(-NH2)、モノメチルアミノ基等のモノアルキルアミノ基、ジメチルアミノ基等のジアルキルアミノ基、モノフェニルアミノ基等のモノアリールアミノ基、ジフェニルアミノ基等のジアリールアミノ基、ピペリジノ基、モルホリノ基、チオモルホリノ基、テトラヒドロキノリノ基、テトラヒドロイソキノリノ基等の環状アミノ基、エチニル基、メルカプト基、シリル基、スルホン酸基、アルキルスルホニル基、ホルミル基、カルボキシ基、シアノ基及びフッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子からなる群から選ばれる置換基Rm;又は、
Rmに更に1つ以上の同一若しくは異なるRmが置換した置換基;
であることができる。
-N(CH3)2:-0.83
-OCH3:-0.27
-t-C4H9:-0.20
-CH3:-0.17
-C2H5:-0.15
-C6H5:-0.01
(-H:0)
-F:+0.06
-Cl:+0.27
-Br:+0.23
-CO2C2H5:+0.45
-CF3:+0.54
-CN:+0.66
-SO2CH3:+0.72
-NO2:+0.78
R3~R6の中で、R4のみが電子吸引性基であって、R3、R5及びR6は水素原子である化合物。
R3~R6の中で、R4及びR6は同一又は異なる電子吸引性基であって、R3及びR5は水素原子である化合物。
R3~R6の中で、R3及びR5は同一又は異なる電子吸引性基であって、R4及びR6は水素原子である化合物。
R21及びR22は、一方が水素原子を表し他方が電子供与性基を表す。
上記フォトクロミック物品及び上記フォトクロミック組成物に含まれる一般式Aで表される化合物は、1種のみであることができ、2種以上(例えば2種以上4種以下)であることもできる。
上記フォトクロミック物品及び上記フォトクロミック組成物に含まれる一般式Bで表される化合物は、1種のみであることができ、2種以上(例えば2種以上4種以下)であることもできる。
上記フォトクロミック物品及び上記フォトクロミック組成物に含まれる一般式Cで表される化合物は、1種のみであることができ、2種以上(例えば2種以上4種以下)であることもできる。
上記フォトクロミック物品及び上記フォトクロミック組成物において、質量基準で、一般式Bで表される化合物及び一般式Cで表される化合物の合計含有率は、一般式Aで表される化合物の含有率より多いことが好ましい。一般式Aで表される化合物、一般式Bで表される化合物及び一般式Cで表される化合物の合計を100質量%として、一般式Bで表される化合物及び一般式Cで表される化合物の合計含有率は、50質量%超であることが好ましく、60質量%以上であることがより好ましく、70質量%以上であることが更に好ましく、80質量%以上であることが一層好ましく、90質量%以上であることがより一層好ましい。一般式Aで表される化合物、一般式Bで表される化合物及び一般式Cで表される化合物の合計(100質量%)に対して、一般式Bで表される化合物及び一般式Cで表される化合物の合計含有率は、100質量%未満であることができ、99質量%以下、98質量%以下、97質量%以下、96質量%以下又は95質量%以下であることができる。
一般式Bで表される化合物と一般式Cで表される化合物の混合比については、一般式Bで表される化合物と一般式Cで表される化合物の合計を100質量%として、一般式Bで表される化合物の含有率は、1質量%以上若しくは99質量%以上であることができ、また、25質量%以下若しくは75質量%以下であることができる。上記の一般式Bで表される化合物の含有率は、上記フォトクロミック物品及び上記フォトクロミック組成物に一般式Bで表される化合物が2種以上含まれる場合には、それらの合計含有率である。この点は、本発明及び本明細書における各種成分の含有率についても同様である。
上記フォトクロミック物品及び上記フォトクロミック組成物は、それらの全量を100質量%として、一般式Aで表される化合物、一般式B及び一般式Cで表される化合物を合計で、例えば0.1~15.0質量%程度含むことができる。ただし、この範囲に限定されるものではない。
上記フォトクロミック物品は、少なくとも基材を有することができる。一形態では、一般式Aで表される化合物、一般式Bで表される化合物及び一般式Cで表される化合物は、上記フォトクロミック物品の基材に含まれることができる。上記フォトクロミック物品は、基材とフォトクロミック層とを有することができ、基材及び/又はフォトクロミック層に、一般式Aで表される化合物、一般式Bで表される化合物及び一般式Cで表される化合物を含むことができる。一般式Aで表される化合物、一般式Bで表される化合物及び一般式Cで表される化合物は、基材及びフォトクロミック層において、一形態では基材のみに含まれることができ、他の一形態ではフォトクロミック層のみに含まれることができ、また他の一形態では基材とフォトクロミック層とに含まれることができる。また、基材及びフォトクロミック層は、フォトクロミック化合物として、一般式Aで表される化合物、一般式Bで表される化合物及び一般式Cで表される化合物のみを含むことができ、又は1種以上の他のフォトクロミック化合物を含むこともできる。他のフォトクロミック化合物としては、アゾベンゼン類、スピロピラン類、スピロオキサジン類、ナフトピラン類、インデノナフトピラン類、フェナントロピラン類、ヘキサアリルビスイミダゾール類、ドナー-アクセプターステンハウス付加物(DASA)類、サリシリデンアニリン類、ジヒドロピレン類、アントラセンダイマー類、フルギド類、ジアリールエテン類、フェノキシナフタセンキノン類、スチルベン類等を挙げることができる。
上記フォトクロミック物品は、フォトクロミック物品の種類に応じて選択された基材を含むことができる。基材の一例として、眼鏡レンズ基材としては、プラスチックレンズ基材又はガラスレンズ基材が挙げられる。ガラスレンズ基材は、例えば無機ガラス製のレンズ基材であることができる。プラスチックレンズ基材としては、(メタ)アクリル樹脂をはじめとするスチレン樹脂、ポリカーボネート樹脂、アリル樹脂、ジエチレングリコールビスアリルカーボネート樹脂(CR-39)等のアリルカーボネート樹脂、ビニル樹脂、ポリエステル樹脂、ポリエーテル樹脂、イソシアネート化合物とジエチレングリコール等のヒドロキシ化合物との反応で得られたウレタン樹脂、イソシアネート化合物とポリチオール化合物とを反応させたチオウレタン樹脂、分子内に1つ以上のジスルフィド結合を有する(チオ)エポキシ化合物を含有する硬化性組成物を硬化した硬化物(一般に透明樹脂と呼ばれる。)を挙げることができる。レンズ基材としては、染色されていないもの(無色レンズ)を用いてもよく、染色されているもの(染色レンズ)を用いてもよい。レンズ基材の屈折率は、例えば、1.50~1.75程度であることができる。ただしレンズ基材の屈折率は、上記範囲に限定されるものではなく、上記の範囲内でも、上記の範囲から上下に離れていてもよい。ここで屈折率とは、波長500nmの光に対する屈折率をいうものとする。また、レンズ基材は、屈折力を有するレンズ(いわゆる度付レンズ)であってもよく、屈折力なしのレンズ(いわゆる度なしレンズ)であってもよい。
フォトクロミック層は、基材の表面上に直接又は一層以上の他の層を介して間接的に設けられた層であることができる。フォトクロミック層は、例えば、重合性組成物を硬化した硬化層であることができる。一般式Aで表される化合物の1種以上と、一般式Bで表される化合物の1種以上と、一般式Cで表される化合物の1種以上と、重合性化合物の1種以上と、を少なくとも含む重合性組成物を硬化した硬化層として、フォトクロミック層を形成することができる。例えば、かかる重合性組成物を基材の表面上に直接塗布するか、又は基材上に設けられた層の表面に塗布し、塗布された重合性組成物に硬化処理を施すことによって、一般式Aで表される化合物の1種以上と一般式Bで表される化合物の1種以上と、一般式Cで表される化合物の1種以上と、を含む硬化層として、フォトクロミック層を形成することができる。塗布方法としては、スピンコート法、ディップコート法、スプレーコート法、インクジェット法、ノズルコート法、スリットコート法等の公知の塗布方法を採用することができる。硬化処理は、光照射及び/又は加熱処理であることができる。重合性組成物は、1種以上の重合性化合物に加えて、1種以上の添加剤(例えば重合開始剤等)を更に含むことができる。重合性化合物の重合反応が進行することによって重合性組成物が硬化し硬化層が形成され得る。
本発明及び本明細書において、重合性化合物とは、1分子中に1つ以上の重合性基を有する化合物をいい、「重合性基」とは、重合反応し得る反応性基をいうものとする。重合性基としては、例えば、アクリロイル基、メタクリロイル基、ビニル基、ビニルエーテル基、エポキシ基、チオール基、オキセタン基、ヒドロキシ基、カルボキシ基、アミノ基、イソシアネート基等を挙げることができる。
エピスルフィド系化合物は、1分子内に2個以上のエピスルフィド基を有する化合物である。エピスルフィド基は、開環重合し得る重合性基である。エピスルフィド系化合物の具体例としては、ビス(1,2-エピチオエチル)スルフィド、ビス(1,2-エピチオエチル)ジスルフィド、ビス(2,3-エピチオプロピル)スルフィド、ビス(2,3-エピチオプロピルチオ)メタン、ビス(2,3-エピチオプロピル)ジスルフィド、ビス(2,3-エピチオプロピルジチオ)メタン、ビス(2,3-エピチオプロピルジチオ)エタン、ビス(6,7-エピチオ-3,4-ジチアヘプチル)スルフィド、ビス(6,7-エピチオ-3,4-ジチアヘプチル)ジスルフィド、1,4-ジチアン-2,5-ビス(2,3-エピチオプロピルジチオメチル)、1,3-ビス(2,3-エピチオプロピルジチオメチル)ベンゼン、1,6-ビス(2,3-エピチオプロピルジチオメチル)-2-(2,3-エピチオプロピルジチオエチルチオ)-4-チアヘキサン、1,2,3-トリス(2,3-エピチオプロピルジチオ)プロパン、1,1,1,1-テトラキス(2,3-エピチオプロピルジチオメチル)メタン、1,3-ビス(2,3-エピチオプロピルジチオ)-2-チアプロパン、1,4-ビス(2,3-エピチオプロピルジチオ)-2,3-ジチアブタン、1,1,1-トリス(2,3-エピチオプロピルジチオ)メタン、1,1,1-トリス(2,3-エピチオプロピルジチオメチルチオ)メタン、1,1,2,2-テトラキス(2,3-エピチオプロピルジチオ)エタン、1,1,2,2-テトラキス(2,3-エピチオプロピルジチオメチルチオ)エタン、1,1,3,3-テトラキス(2,3-エピチオプロピルジチオ)プロパン、1,1,3,3-テトラキス(2,3-エピチオプロピルジチオメチルチオ)プロパン、2-[1,1-ビス(2,3-エピチオプロピルジチオ)メチル]-1,3-ジチエタン、2-[1,1-ビス(2,3-エピチオプロピルジチオメチルチオ)メチル]-1,3-ジチエタン等を挙げることができる。
チエタニル系化合物は、1分子内に2個以上のチエタニル基を有するチエタン化合物である。チエタニル基は、開環重合し得る重合性基である。チエタニル系化合物の中には、複数のチエタニル基と共にエピスルフィド基を有するものがある。かかる化合物は、上記のエピスルフィド系化合物の例に挙げられている。その他のチエタニル系化合物には、分子内に金属原子を有している含金属チエタン化合物と、金属を含んでいない非金属系チエタン化合物とがある。
ポリアミン化合物は、一分子中にNH2基を2つ以上有する化合物であり、ポリイソシアネートとの反応でウレア結合を形成することができ、ポリイソチオシアネートとの反応でチオウレア結合を形成することができる。ポリアミン化合物の具体例としては、エチレンジアミン、ヘキサメチレンジアミン、イソホロンジアミン、ノナメチレンジアミン、ウンデカメチレンジアミン、ドデカメチレンジアミン、メタキシレンジアミン、1,3-プロパンジアミン、プトレシン、2-(2-アミノエチルアミノ)エタノ-ル、ジエチレントリアミン、p-フェニレンジアミン、m-フェニレンジアミン、メラミン、1,3,5-ベンゼントリアミン等が挙げられる。
エポキシ系化合物は、分子内にエポキシ基を有する化合物である。エポキシ基は、開環重合し得る重合性基である。エポキシ系化合物は、一般に、脂肪族エポキシ化合物、脂環族エポキシ化合物及び芳香族エポキシ化合物に分類される。
ラジカル重合性基を有する化合物は、ラジカル重合し得る重合性基である。ラジカル重合性基としては、アクリロイル基、メタクリロイル基、アリル基、ビニル基等が挙げられる。
本発明の一態様は、上記フォトクロミック物品の一形態である眼鏡レンズを備えた眼鏡に関する。この眼鏡に含まれる眼鏡レンズの詳細については、先に記載した通りである。上記眼鏡は、かかる眼鏡レンズを備えることにより、例えば屋外ではフォトクロミック化合物が太陽光の照射を受けて着色することでサングラスのように防眩効果を発揮することができ、屋内に戻るとフォトクロミック化合物が退色することで透過性を回復することができる。上記眼鏡について、フレーム等の構成については、公知技術を適用することができる。
化合物の合成方法に関して先に示した参照文献を参考に、以下に示す化合物1~15を合成した。参照公報に記載の方法と同様に化合物の同定を行い、以下に示す化合物が合成されたことを確認した。化合物1~7は一般式Aで表される化合物であり、化合物8~15は一般式Bで表される化合物であり、化合物16~23は一般式Cで表される化合物である。
<フォトクロミック組成物(重合性組成物)の調製>
プラスチック製容器内で、(メタ)アクリレートの合計100質量部に対して、68質量部のポリエチレングリコールジアクリレート、12質量部のトリメチロールプロパントリメタクリレート、20質量部のネオペンチルグリコールジメタクリレートを混合し、(メタ)アクリレート混合物を調製した。この(メタ)アクリレート混合物100質量部に対して、2.5質量部となるようにフォトクロミック化合物を混合した。複数のフォトクロミック化合物を含む組成物については、フォトクロミック化合物の全量を10とした場合のそれぞれのフォトクロミック化合物の質量比を表2(表2-1及び表2-2)に示した。更に、光重合開始剤(フェニルビス(2,4,6-トリメチルベンゾイル)ホスフィンオキシド)、酸化防止剤[ビス(3-tert-ブチル-4-ヒドロキシ-5-メチルフェニル)プロピオン酸)][エチレンビス(オキシエチレン)及び光安定化剤(セバシン酸ビス(1,2,2,6,6-ペンタメチル-4-ピペリジル))を混合し、十分に攪拌した後、シランカップリング剤(γ-メタクリロキシプロピルトリメトキシシラン)を攪拌しながら滴下した。その後、自動公転方式攪拌脱泡装置で脱泡した。
以上の方法により、フォトクロミック組成物を調製した。
プラスチックレンズ基材(HOYA社製商品名EYAS:中心厚2.5mm、直径75mm、球面レンズ度数-4.00)を濃度10質量%の水酸化ナトリウム水溶液(液温60℃)に5分間浸漬処理することでアルカリ洗浄し、更に純水で洗浄し乾燥させた。その後、このプラスチックレンズ基材の凸面に対して、水系ポリウレタン樹脂液(ポリカーボネートポリオール系ポリウレタンエマルジョン、粘度100cPs、固形分濃度38質量%)を室温且つ相対湿度40~60%の環境において、ミカサ社製スピンコーターMS-B150を用い、回転数1500rpmで1分間スピンコート法により塗布した後、15分間自然乾燥させることにより、厚さ5.5μmのプライマー層を形成した。
上記で調製したフォトクロミック組成物を、上記プライマー層の上に滴下し、ミカサ社製MS-B150を用い、回転数500rpmから1500rpmまで1分間かけてスロープモードで回転数を変化させ、更に1500rpmで5秒間回転させるプログラムを用いたスピンコート法により塗布した。その後、プラスチックレンズ基材上に形成されたプライマー層上に塗布された上記フォトクロミック組成物に対し、窒素雰囲気中(酸素濃度500ppm以下)で紫外線(主波長405nm)を40秒間照射し、この組成物を硬化させてフォトクロミック層を形成した。形成されたフォトクロミック層の厚さは45μmであった。
こうして、フォトクロミック物品(眼鏡レンズ)を作製した。
<着色濃度の評価>
JIS T7333:2005に準じた以下の方法によって視感反射率を求めた。
実施例及び比較例の各眼鏡レンズの凸面に向けて、キセノンランプを光源に用いてエアロマスフィルターを介した光を15分間照射し、フォトクロミック層を着色させた。この照射光はJIS T7333:2005に規定されているように放射照度及び放射照度の許容差が表1に示す値となるように行った。この着色時の透過率を大塚電子製分光光度計により測定した。波長範囲380nmから780nmの範囲での測定結果から求めた視感透過率T(%)を表2に示す。T(%)の値が小さいほど、フォトクロミック化合物が高濃度に着色していることを意味する。
退色速度は以下の方法により評価した。
実施例及び比較例の各眼鏡レンズの光照射前(未着色状態)の透過率(測定波長:550nm)を大塚電子製分光光度計により測定した。ここで測定された透過率を「初期透過率」と呼ぶ。
各眼鏡レンズに対し、キセノンランプを光源に用いてエアロマスフィルターを介した光を15分間照射し、フォトクロミック層を着色させた。この照射光はJIS T7333:2005に規定されているように放射照度及び放射照度の許容差が表1に示す値となるように行った。この着色時の透過率を初期透過率と同様に測定した。ここで測定された透過率を「着色時透過率」と呼ぶ。
その後、光照射を止めた時間から透過率が、[(初期透過率-着色時透過率)/2]となるまでに要する時間を測定した。この時間を「半減時間」とする。半減時間が短いほど退色速度が速いということができる。求められた半減時間を表2に示す。
ヒドロキシ基、炭素数1~18の直鎖若しくは分岐のアルキル基、炭素数5~18の単環若しくはビシクロ環等の複環の環状脂肪族アルキル基、構成原子数1~24の直鎖若しくは分岐のアルコキシ基、構成原子数1~24の非芳香族環状置換基、炭素数1~18の直鎖若しくは分岐のパーフルオロアルキル基、直鎖若しくは分岐のパーフルオロアルコキシ基、構成原子数1~24の直鎖若しくは分岐のアルキルスルフィド基、アリール基、アリールオキシ基、アリールスルフィド基、ヘテロアリール基、アミノ基、モノアルキルアミノ基、ジアルキルアミノ基、モノアリールアミノ基、ジアリールアミノ基、ピペリジノ基、モルホリノ基、チオモルホリノ基、テトラヒドロキノリノ基、テトラヒドロイソキノリノ基等の環状アミノ基、エチニル基、メルカプト基、シリル基、スルホン酸基、アルキルスルホニル基、ホルミル基、カルボキシ基、シアノ基及びハロゲン原子からなる群から選ばれる置換基Rm;
Rmに更に1つ以上の同一若しくは異なるRmが置換した置換基;又は
可溶化基
であることができる。
Claims (24)
- 一般式A中、R1及びR2は、それぞれ独立に、炭素数1~20の置換又は無置換のアルキル基を表す、請求項1に記載のフォトクロミック組成物。
- 一般式A中、R1及びR2は、それぞれ独立に、メチル基、エチル基、プロピル基、ブチル基、ペンチル基又はヘキシル基を表す、請求項1又は2に記載のフォトクロミック組成物。
- 一般式A中のB1及びB2、一般式B中のB3及びB4並びに一般式C中のB5及びB6は、それぞれ独立に、置換又は無置換のフェニル基を表し、フェニル基が置換基を複数有する場合、当該置換基が結合して環を形成してもよい、請求項1~3のいずれか1項に記載のフォトクロミック組成物。
- 一般式A中、R3~R6は、それぞれ独立に水素原子又は電子吸引性基を表し、ただしR3~R6の1つ以上は電子吸引性基を表す、請求項1~4のいずれか1項に記載のフォトクロミック組成物。
- 前記電子吸引性基は、ハロゲン原子、炭素数1~6のパーフルオロアルキル基、パーフルオロフェニル基、パーフルオロアルキルフェニル基又はシアノ基である、請求項5に記載のフォトクロミック組成物。
- 前記ハロゲン原子はフッ素原子である、請求項6に記載のフォトクロミック組成物。
- 前記パーフルオロアルキル基はトリフルオロメチル基である、請求項6に記載のフォトクロミック組成物。
- 一般式A中のR1~R6、B1、B2、一般式B中のR7~R12、B3、B4、一般式C中のR15~R20、B5及びB6からなる群から選ばれる1つ以上は置換基を表し、該置換基は、
ヒドロキシ基、炭素数1~18の直鎖若しくは分岐のアルキル基、炭素数5~18の単環若しくはビシクロ環等の複環の環状脂肪族アルキル基、構成原子数1~24の直鎖若しくは分岐のアルコキシ基、構成原子数1~24の非芳香族環状置換基、炭素数1~18の直鎖若しくは分岐のパーフルオロアルキル基、直鎖若しくは分岐のパーフルオロアルコキシ基、構成原子数1~24の直鎖若しくは分岐のアルキルスルフィド基、アリール基、アリールオキシ基、アリールスルフィド基、ヘテロアリール基、アミノ基、モノアルキルアミノ基、ジアルキルアミノ基、モノアリールアミノ基、ジアリールアミノ基、ピペリジノ基、モルホリノ基、チオモルホリノ基、テトラヒドロキノリノ基、テトラヒドロイソキノリノ基等の環状アミノ基、エチニル基、メルカプト基、シリル基、スルホン酸基、アルキルスルホニル基、ホルミル基、カルボキシ基、シアノ基及びハロゲン原子からなる群から選ばれる置換基Rm;
Rmに更に1つ以上の同一若しくは異なるRmが置換した置換基;又は
可溶化基
である、請求項1~8のいずれか1項に記載のフォトクロミック組成物。 - 一般式B中、R7及びR8は、それぞれ独立に、炭素数1~20の置換又は無置換のアルキル基を表す、請求項1~9のいずれか1項に記載のフォトクロミック組成物。
- 一般式B中、R7及びR8は、それぞれ独立に、メチル基、エチル基、プロピル基、ブチル基、ペンチル基又はヘキシル基を表す、請求項1~10のいずれか1項に記載のフォトクロミック組成物。
- 一般式B中、R13及びR14は、それぞれ独立に、メトキシ基、エトキシ基、フェノキシ基、メチルスルフィド基、フェニルスルフィド基、ジメチルアミノ基、ピロリジノ基、ピペリジノ基、モルホリノ基及びチオモルホリノ基からなる群から選択される電子供与性基を表す、請求項1~11のいずれか1項に記載のフォトクロミック組成物。
- 一般式C中、R15及びR16は、それぞれ独立に、炭素数1~20の置換又は無置換のアルキル基を表す、請求項1~12のいずれか1項に記載のフォトクロミック組成物。
- 一般式C中、R15及びR16は、それぞれ独立に、メチル基、エチル基、プロピル基、ブチル基、ペンチル基又はヘキシル基を表す、請求項1~13のいずれか1項に記載のフォトクロミック組成物。
- 一般式C中、R21又はR22で表される電子供与性基は、メトキシ基、エトキシ基、フェノキシ基、メチルスルフィド基、フェニルスルフィド基、ジメチルアミノ基、ピロリジノ基、ピペリジノ基、モルホリノ基及びチオモルホリノ基からなる群から選択される電子供与性基である、請求項1~14のいずれか1項に記載のフォトクロミック組成物。
- 質量基準で、一般式Bで表される化合物及び一般式Cで表される化合物の合計含有率が、一般式Aで表される化合物の含有率より多い、請求項1~15のいずれか1項に記載のフォトクロミック組成物。
- 重合性化合物を更に含む、請求項1~16のいずれか1項に記載のフォトクロミック組成物。
- 請求項17に記載のフォトクロミック組成物を硬化した硬化物を含むフォトクロミック物品。
- 基材と、前記硬化物であるフォトクロミック層とを有する、請求項18に記載のフォトクロミック物品。
- 眼鏡レンズである、請求項18又は19に記載のフォトクロミック物品。
- ゴーグル用レンズである、請求項18又は19に記載のフォトクロミック物品。
- サンバイザーのバイザー部分である、請求項18又は19に記載のフォトクロミック物品。
- ヘルメットのシールド部材である、請求項18又は19に記載のフォトクロミック物品。
- 請求項20に記載の眼鏡レンズを備えた眼鏡。
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JPWO2022138968A1 (ja) | 2022-06-30 |
EP4198583A1 (en) | 2023-06-21 |
JPWO2022138967A1 (ja) | 2022-06-30 |
US20240059959A1 (en) | 2024-02-22 |
US20230340318A1 (en) | 2023-10-26 |
EP4270067A1 (en) | 2023-11-01 |
WO2022138967A1 (ja) | 2022-06-30 |
JPWO2022138965A1 (ja) | 2022-06-30 |
KR20230052949A (ko) | 2023-04-20 |
WO2022138965A1 (ja) | 2022-06-30 |
KR20230116835A (ko) | 2023-08-04 |
EP4198102A4 (en) | 2024-04-24 |
EP4269532A1 (en) | 2023-11-01 |
CN116323577A (zh) | 2023-06-23 |
JP2023116564A (ja) | 2023-08-22 |
JP7290809B2 (ja) | 2023-06-13 |
US20230227717A1 (en) | 2023-07-20 |
JPWO2022138966A1 (ja) | 2022-06-30 |
US20240103200A1 (en) | 2024-03-28 |
JP2023175687A (ja) | 2023-12-12 |
JP7334368B2 (ja) | 2023-08-28 |
EP4198583A4 (en) | 2024-05-29 |
KR20230052950A (ko) | 2023-04-20 |
CN116323857A (zh) | 2023-06-23 |
EP4198102A1 (en) | 2023-06-21 |
KR20230118115A (ko) | 2023-08-10 |
WO2022138968A1 (ja) | 2022-06-30 |
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