Classifications

• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
  • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
  • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
  • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
  • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
  • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
  • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
  • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
  • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
  • C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
  • C08F222/10—Esters
  • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
  • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
  • C08F222/10—Esters
  • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
  • C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
  • C08F290/06—Polymers provided for in subclass C08G
  • C08F290/062—Polyethers
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B69/00—Dyes not provided for by a single group of this subclass
  • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B69/00—Dyes not provided for by a single group of this subclass
  • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
  • C09B69/103—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a diaryl- or triarylmethane dye
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
  • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/32—Radiation-absorbing paints
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/60—Additives non-macromolecular
  • C09D7/63—Additives non-macromolecular organic
• • 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
• • 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
  • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
  • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
• • 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
• • G—PHYSICS
  • G02—OPTICS
  • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
  • G02C7/00—Optical parts
  • G02C7/02—Lenses; Lens systems ; Methods of designing lenses
• • G—PHYSICS
  • G02—OPTICS
  • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
  • G02C7/00—Optical parts
  • G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses

Definitions

• the present invention relates to a polymerizable composition for optical articles and an optical article.
• a photochromic compound is a compound that develops color under irradiation with light in a wavelength range that has photoresponsiveness, and has the property (photochromic property) of fading when not irradiated.
• a coating containing a photochromic compound and a polymerizable compound is provided on a base material, and this coating is cured to form a cured layer (photochromic layer) having photochromic properties.
• a cured layer photochromic layer having photochromic properties.
• optical articles having photochromic properties such as those described above it is desirable for optical articles having photochromic properties such as those described above to have a high color density when coloring occurs when exposed to light outdoors or the like. Further, the desired performance of the above-mentioned optical article is that it exhibits a fast rate of fading after being colored by light irradiation.
• the color density and the speed of fading there is a trade-off relationship between the color density and the speed of fading, and conventionally it has been difficult to achieve both a high color density and a fast speed of color fading.
• An object of one aspect of the present invention is to provide a polymerizable composition for optical articles that can form a photochromic layer that has a high color density when colored upon exposure to light and has a fast fading rate.
• composition a polymerizable composition for optical articles (hereinafter also simply referred to as "composition") containing component A, component B, and component C below.
• Component A Polyfunctional (meth)acrylate containing a polyalkylene glycol moiety and having a molecular weight of 500 or more
• Component B Monofunctional (meth)acrylate represented by the following formula 1 (In Formula 1, R 10 represents a hydrogen atom or a methyl group, and R 11 represents a straight chain alkyl group having 3 or more carbon atoms or a branched alkyl group having 3 or more carbon atoms.)
• Component C Photochromic compound
• a photochromic compound changes its structure through an excited state upon being irradiated with light such as sunlight.
• a structure that undergoes a structural change through light irradiation can be called a "colored body.”
• the structure before irradiation with light can be called a “colorless body.”
• colorless with respect to a colorless body is not limited to completely colorless, but includes cases where the color is lighter than that of a colored body.
• the photochromic layer it is considered that the easier the molecular movement of the photochromic compound in the matrix formed by the polymerization reaction of the polymerizable compound is, the faster the speed of the above-mentioned structural change will be. From the viewpoint of increasing such speed, a flexible matrix is considered desirable.
• the color density it is presumed that in order to increase the color density, it is desirable that the intermolecular interaction between the photochromic compound whose structure has changed into a colored body and the matrix be strong.
• the present inventor conjectures that component A can contribute to making the matrix flexible.
• component A can form a flexible matrix
• component A has a molecular weight of 500 or more and component A has a polyalkylene glycol moiety.
• the present inventor believes that the "-CH 2 --R 11 " moiety of component B can exhibit strong intermolecular interaction with the photochromic compound whose structure has changed into a colored body.
• the "-CH 2 --R 11 " moiety is a relatively rigid functional group.
• component B is a monofunctional (meth)acrylate although it has such a rigid functional group, it is thought that the "-CH 2 --R 11 " moiety is likely to move easily in the matrix formed using component B. It will be done.
• component B can ensure the flexibility of the matrix.
• the above composition containing component A and component B as well as the photochromic compound (component C) enables the formation of a photochromic layer that has a high color density when colored by light irradiation and has a fast fading rate.
• the inventor is thinking.
• the present invention is not limited to the speculations described in this specification.
• a polymerizable composition for optical articles that can form a photochromic layer that has a high color density and a fast fading rate when colored upon irradiation with light. Further, according to one aspect of the present invention, it is possible to provide an optical article having a photochromic layer that has a high color density when colored by light irradiation and has a fast fading rate.
• a polymerizable composition refers to a composition containing a polymerizable compound.
• a polymerizable compound is a compound having a polymerizable group.
• the polymerizable composition for optical articles according to one aspect of the present invention is a polymerizable composition used for manufacturing optical articles, and can be a coating composition for optical articles, and more specifically, it can be a coating composition for optical articles. It can be a coating composition for forming a photochromic layer on an article.
• the coating composition for optical articles refers to a composition that is applied to a substrate or the like for the production of optical articles. Examples of optical articles include various lenses such as eyeglass lenses and goggle lenses, visor portions of sun visors, and shield members for helmets. For example, a spectacle lens produced by applying the above composition onto a lens base material has a photochromic layer and can exhibit photochromic properties.
• (meth)acrylate is used to include acrylate and methacrylate.
• “Acrylate” is a compound having one or more acryloyl groups in one molecule.
• “Methacrylate” is a compound having one or more methacryloyl groups in one molecule.
• the functional number is the number of groups selected from the group consisting of acryloyl groups and methacryloyl groups contained in one molecule.
• methacrylate refers to a substance containing only a methacryloyl group as a (meth)acryloyl group, and a substance containing both an acryloyl group and a methacryloyl group as a (meth)acryloyl group is referred to as an acrylate. call.
• Acryloyl groups may be included in the form of acryloyloxy groups, and methacryloyl groups may be included in the form of methacryloyloxy groups.
• the "(meth)acryloyl group” described below is used to include an acryloyl group and a methacryloyl group, and the "(meth)acryloyloxy group” includes an acryloyloxy group and a methacryloyloxy group. used in meaning. Further, unless otherwise specified, the groups described may have a substituent or may be unsubstituted.
• examples of the substituent include an alkyl group (for example, a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 1 to 6 carbon atoms), a hydroxyl group, an alkoxy group (for example, a straight chain alkyl group having 1 to 6 carbon atoms), a hydroxyl group, and an alkoxy group (for example, 6), a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom), a cyano group, an amino group, a nitro group, an acyl group, a carboxy group, an aryl group, a polyether group, and the like.
• an alkyl group for example, a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 1 to 6 carbon atoms
• a hydroxyl group for example, a straight chain alkyl group having 1 to 6 carbon atoms
• the "number of carbon atoms” means the number of carbon atoms in a portion that does not contain a substituent.
• the term "straight-chain alkyl group or branched alkyl group" in the present invention and this specification does not include a cycloalkyl group.
• the straight chain alkyl group or branched alkyl group may be unsubstituted or may have a substituent. It is permissible for the straight-chain alkyl group or the branched alkyl group to have a cycloalkyl group (for example, a cyclohexyl group) as a substituent. In one form, the straight-chain alkyl group or branched alkyl group preferably does not have a cycloalkyl group as a substituent.
• the composition includes at least component A and component B as polymerizable compounds.
• component A and component B will be explained below.
• Component A is a polyfunctional (meth)acrylate containing a polyalkylene glycol moiety and having a molecular weight of 500 or more.
• the "polyalkylene glycol moiety" refers to the following formula 2: Let us refer to the partial structure represented by .
• R represents an alkylene group
• n represents the number of repeats of the alkoxy group represented by RO, which is 2 or more. * indicates a bonding position where the partial structure represented by Formula 2 is bonded to an adjacent atom.
• the number of carbon atoms in the alkylene group represented by R can be 1 or more or 2 or more, and can be, for example, 5 or less or 4 or less.
• alkylene group represented by R examples include ethylene group, propylene group, and tetramethylene group.
• n is 2 or more, and can be, for example, 30 or less, 25 or less, or 20 or less.
• component A can have the above partial structure in which R represents an ethylene group, ie, a polyethylene glycol moiety.
• the molecular weight of component A is 500 or more.
• the molecular weight of a multimer shall be the theoretical molecular weight calculated from the structural formula determined by structural analysis of the compound or the raw material charging ratio during production.
• the molecular weight of component A is 500 or more, preferably 510 or more, more preferably 520 or more, preferably 550 or more, more preferably 570 or more, and 600 or more. is more preferable, more preferably 630 or more, even more preferably 650 or more.
• the molecular weight of component A is preferably, for example, 2000 or less, 1500 or less, 1200 or less, 1000 or less, or 800 or less.
• Component A is a polyfunctional (meth)acrylate, which can be, for example, a difunctional, trifunctional, tetrafunctional or pentafunctional (meth)acrylate, and can be a difunctional or trifunctional (meth)acrylate.
• Component A may contain only an acryloyl group, only a methacryloyl group, or may contain an acryloyl group and a methacryloyl group as the (meth)acryloyl group. That is, component A can be an acrylate or a methacrylate.
• component A can be an acyclic polyfunctional (meth)acrylate.
• acyclic means not containing a cyclic structure.
• cyclic means including a cyclic structure.
• the non-cyclic polyfunctional (meth)acrylate refers to a bifunctional or higher functional (meth)acrylate that does not contain a cyclic structure.
• a specific example of such component A is polyalkylene glycol di(meth)acrylate represented by the following formula 3.
• R 1 and R 2 each independently represent a hydrogen atom or a methyl group
• R represents an alkylene group
• n represents the number of repeats of the alkoxy group represented by RO, which is 2 or more.
• R and n are as described above for the partial structure represented by Formula 2.
• the polyalkylene glycol di(meth)acrylate represented by Formula 3 may contain only an acryloyl group, only a methacryloyl group, or may contain an acryloyl group and a methacryloyl group.
• polyalkylene glycol di(meth)acrylate represented by formula 3 examples include polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, etc. can.
• tri(meth)acrylate represented by the following formula 4 can also be mentioned.
• the tri(meth)acrylate represented by Formula 4 may contain only an acryloyl group, only a methacryloyl group, or may contain an acryloyl group and a methacryloyl group.
• R 40 , R 41 , R 44 , R 45 , R 47 and R 48 each independently represent an alkylene group
• R 43 represents an alkyl group
• R 42 , R 46 and R 49 each Independently represents a hydrogen atom or a methyl group.
• n1 indicates the number of repeats of the alkoxy group represented by OR 41 , and is 2 or more.
• n2 indicates the number of repeats of the alkoxy group represented by OR 45 , and is 2 or more.
• n3 indicates the number of repeats of the alkoxy group represented by OR 48 , and is 2 or more.
• Equation 4 Equation 4 will be explained in more detail.
• R 41 , R 45 and R 48 in Formula 4 are as described above for R in Formula 2.
• n1, n2, and n3 in Formula 4 are as described above for n in Formula 2.
• R 41 , R 45 and R 48 may be the same or two or three different. This point also applies to n1, n2, and n3.
• R 42 , R 46 and R 49 each independently represent a hydrogen atom or a methyl group.
• the tri(meth)acrylate represented by Formula 4 may contain only an acryloyl group, only a methacryloyl group, or may contain an acryloyl group and a methacryloyl group.
• the number of carbon atoms in the alkyl group represented by R 43 can be 1 or more or 2 or more, and can also be, for example, 5 or less or 4 or less.
• the alkyl group represented by R 43 can be a straight chain alkyl group or a branched alkyl group. Specific examples of the alkyl group represented by R 43 include a methyl group and an ethyl group.
• R 40 , R 44 and R 47 each independently represent an alkylene group.
• the number of carbon atoms in such an alkylene group can be 1 or more or 2 or more, and can also be, for example, 5 or less or 4 or less. Specific examples thereof include ethylene group, propylene group, and tetramethylene group.
• tri(meth)acrylate represented by formula 4 examples include trimethylolpropane polyoxyethylene ether tri(meth)acrylate.
• Component B is a monofunctional (meth)acrylate represented by Formula 1 below.
• Equation 1 Equation 1 will be explained in more detail.
• R 10 represents a hydrogen atom or a methyl group.
• the monofunctional (meth)acrylate represented by Formula 1 may be an acrylate or a methacrylate.
• R 11 represents a straight chain alkyl group having 3 or more carbon atoms or a branched alkyl group having 3 or more carbon atoms. These alkyl groups may be unsubstituted or may have a substituent.
• the substituents are not particularly limited, and include, for example, the various substituents described above.
• the number of carbon atoms in the linear or branched alkyl group represented by R 11 is 3 or more, and from the viewpoint of increasing the fading rate, it is preferably 4 or more, more preferably 5 or more, More preferred in the order of 6 or more, 7 or more, 8 or more, 9 or more, 10 or more, and 11 or more.
• the number of carbon atoms is preferably 15 or less, more preferably 14 or less, 13 or less, then 12 or less. More preferred.
• the molecular weight of the monofunctional (meth)acrylate represented by Formula 1 can be, for example, in the range of 100 to 300, but is not limited to this range.
• Specific examples of the monofunctional (meth)acrylate represented by Formula 1 include n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, n-lauryl (meth)acrylate, etc. be able to.
• the content of component A is preferably 50% by mass or more, more preferably 55% by mass or more, and 60% by mass or more, based on the total amount of polymerizable compounds contained in the composition as 100% by mass. More preferably, it is at least % by mass.
• component A can be the component that occupies the largest proportion of the plurality of polymerizable compounds contained in the composition. Further, the content of component A can be 90% by mass or less, 85% by mass or less, or 80% by mass or less, with the total amount of polymerizable compounds contained in the composition being 100% by mass.
• the above composition may contain only one type of component A in one form, and may contain two or more types of component A in another form. When two or more types of components A are included, the content rate of the above-mentioned component A is the total content rate of the two or more types. This point also applies to the content rates of other components.
• the content of component B is preferably 5% by mass or more, more preferably 10% by mass or more, and 15% by mass or more, based on the total amount of polymerizable compounds contained in the composition as 100% by mass. It is more preferable. Further, the content of component B is preferably 30% by mass or less, more preferably 25% by mass or less, based on 100% by mass of the total amount of polymerizable compounds contained in the composition.
• the above composition may contain only component A and component B as polymerizable compounds, and in another form, it may contain one or more other polymerizable compounds in addition to component A and component B.
• the content of the polymerizable compound in the composition i.e., the total content of a plurality of polymerizable compounds
• the content of the polymerizable compound in the composition is, for example, 80% by mass or more, 85% by mass or more, or 90% by mass or more, with the total amount of the composition being 100% by mass. can be.
• the content of the polymerizable compound in the composition can be, for example, 99% by mass or less, 95% by mass or less, 90% by mass or less, or 85% by mass or less, with the total amount of the composition being 100% by mass. .
• the total amount of the composition refers to the total amount of all components excluding the solvent in the case of a composition containing a solvent.
• the above composition may or may not contain a solvent.
• any solvent can be used in any amount as long as it does not inhibit the progress of the polymerization reaction of the polymerizable composition.
• the composition contains a photochromic compound (component C) together with the polymerizable compound.
• a photochromic compound contained in the above composition, known compounds exhibiting photochromic properties can be used.
• a photochromic compound can exhibit photochromic properties against ultraviolet light, for example.
• photochromic compounds include azobenzenes, spiropyrans, spirooxazines, naphthopyrans, indenonaphthopyrans, phenanthropyrans, hexaallylbisimidazoles, and donor-acceptor Stenhouse adducts (DASA).
• photochromic compounds include fulgimide compounds, spirooxazine compounds, chromene compounds, indeno-fused naphthopyran compounds, and the like.
• the photochromic compound is selected from the group consisting of a photochromic compound represented by general formula A, a photochromic compound represented by general formula B, and a photochromic compound represented by general formula C described in WO2022/138966.
• Photochromic compounds can be used alone or in combination of two or more.
• the content of the photochromic compound in the composition can be, for example, about 0.1 to 15% by mass, based on the total amount of the composition as 100% by mass, but is not limited to this range.
• the above composition can contain one or more types of various additives that can be normally included in the polymerizable composition at any content rate.
• additives that may be included in the composition include a polymerization initiator for advancing the polymerization reaction.
• any known polymerization initiator can be used, preferably a radical polymerization initiator, and more preferably only a radical polymerization initiator.
• a photopolymerization initiator or a thermal polymerization initiator can be used, and a photopolymerization initiator is preferable from the viewpoint of allowing the polymerization reaction to proceed in a short time.
• the photoradical polymerization initiator include benzoin ketals such as 2,2-dimethoxy-1,2-diphenylethan-1-one; 1-hydroxycyclohexylphenyl ketone, and 2-hydroxy-2-methyl-1-phenylpropane.
• ⁇ -hydroxyketones such as 1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one; 2-benzyl-2-dimethylamino-1 ⁇ -aminoketones such as -(4-morpholinophenyl)-butan-1-one, 1,2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one; 1-[ Oxime esters such as (4-phenylthio)phenyl]-1,2-octadione-2-(benzoyl)oxime; bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)- Phosphine oxides such as 2,4,4-trimethylpentylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide; 2-(o-chlorophenyl)-4,5-diphenylimid
• the substituents of the aryl groups at the two triarylimidazole moieties may be the same and give a symmetrical compound, or they may be different and give an asymmetrical compound.
• a thioxanthone compound and a tertiary amine may be combined, such as a combination of diethylthioxanthone and dimethylaminobenzoic acid.
• ⁇ -hydroxyketone and phosphine oxide are preferred from the viewpoint of curability, transparency and heat resistance.
• the content of the polymerization initiator can be, for example, in the range of 0.1 to 5% by weight, with the total amount of the composition being 100% by weight.
• compositions containing photochromic compounds such as surfactants, antioxidants, radical scavengers, light stabilizers, ultraviolet absorbers, and color inhibitors.
• additives such as surfactants, antioxidants, radical scavengers, light stabilizers, ultraviolet absorbers, and color inhibitors.
• antistatic agents fluorescent dyes, dyes, pigments, fragrances, plasticizers, silane coupling agents, and other additives can be added in arbitrary amounts.
• known additives can be used as these additives.
• the above composition can be prepared by mixing the various components described above simultaneously or sequentially in any order.
• optical articles One aspect of the present invention relates to an optical article having a base material and a photochromic layer formed by curing the composition described above.
• the above optical article can have a photochromic layer on a substrate selected depending on the type of optical article.
• the spectacle lens substrate can be a plastic lens substrate or a glass lens substrate.
• the glass lens base material can be, for example, a lens base material made of inorganic glass.
• a plastic lens base material is preferable because it is lightweight, hard to break, and easy to handle.
• Plastic lens base materials include (meth)acrylic resins, styrene resins, polycarbonate resins, allyl resins, allyl carbonate resins such as diethylene glycol bisallyl carbonate resin (CR-39), vinyl resins, polyester resins, polyether resins, and isocyanate compounds.
• urethane resin obtained by reacting with a hydroxy compound such as diethylene glycol, thiourethane resin obtained by reacting an isocyanate compound with a polythiol compound, and a cured resin containing a (thio)epoxy compound having one or more disulfide bonds in the molecule.
• a cured product obtained by curing a transparent composition (generally called a transparent resin) can be mentioned.
• the lens base material one that is not dyed (colorless lens) may be used, or one that is dyed (dyed lens) may be used.
• the refractive index of the lens base material can be, for example, about 1.50 to 1.75.
• the refractive index of the lens base material is not limited to the above range, and may be within the above range or may be vertically apart from the above range.
• the refractive index refers to the refractive index for light with a wavelength of 500 nm.
• the lens base material may be a lens having refractive power (so-called prescription lens) or a lens without refractive power (so-called non-prescription lens).
• Spectacle lenses can be various lenses such as single-focal lenses, multifocal lenses, and progressive-power lenses.
• the type of lens is determined by the surface shapes of both surfaces of the lens base material.
• the lens base material surface may be any of a convex surface, a concave surface, and a flat surface.
• the object-side surface is convex and the eyeball-side surface is concave.
• the photochromic layer can usually be provided on the object-side surface of the lens base material, but may also be provided on the eyeball-side surface.
• the photochromic layer of the optical article may be formed by applying the composition directly or indirectly through one or more other layers onto the surface of the base material, and subjecting the applied composition to a curing treatment. I can do it.
• Other layers include a primer layer for improving the adhesion between the photochromic layer and the base material.
• primer layers are known.
• a coating method a known coating method such as a spin coating method or a dip coating method can be employed, and the spin coating method is preferable from the viewpoint of uniformity of coating.
• the curing treatment can be light irradiation and/or heat treatment, and light irradiation is preferred from the viewpoint of advancing the curing reaction in a short time.
• the curing treatment conditions may be determined depending on the types of various components (the polymerizable compound, polymerization initiator, etc. described above) contained in the composition and the composition of the composition.
• the thickness of the photochromic layer thus formed is, for example, preferably in the range of 5 to 80 ⁇ m, more preferably in the range of 20 to 60 ⁇ m.
• the above optical article having a photochromic layer may or may not have one or more functional layers in addition to the photochromic layer.
• the functional layer include layers known as functional layers for optical articles, such as a protective layer for improving the durability of optical articles, an antireflection layer, a water-repellent or hydrophilic antifouling layer, and an antifogging layer. Can be done.
• optical article is a spectacle lens.
• optical article include lenses for goggles, visor portions of sun visors, shield members for helmets, and the like.
• An optical article having an anti-glare function can be obtained by coating the above-mentioned composition on a substrate for these optical articles and subjecting the coated composition to a curing treatment to form a photochromic layer.
• One aspect of the present invention relates to eyeglasses equipped with eyeglass lenses, which are one form of the above-mentioned optical article.
• the details of the eyeglass lenses included in these eyeglasses are as described above.
• the above-mentioned glasses can exhibit an anti-glare effect like sunglasses when used outdoors, for example, when the photochromic compound contained in the photochromic layer develops color when exposed to sunlight, and when used indoors. When it returns, the photochromic compound fades and the transparency can be restored.
• known techniques can be applied to the configuration of frames and the like.
• Example 1 ⁇ Preparation of polymerizable composition for optical articles (coating composition for forming photochromic layer)>
• the mixture of polymerizable compounds thus obtained was added with the following photochromic compound (an indeno-fused naphthopyran compound represented by the structural formula described in US Pat. No.
• a photoradical polymerization initiator bis(2,4,6- trimethylbenzoyl)phenylphosphine oxide (Omnirad 819 manufactured by IGM Resin B.V.)
• antioxidant bis[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionic acid][ethylenebis( oxyethylene)]
• a light stabilizer bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate
• the content of the above components, with the total amount of the composition being 100% by mass, is 94.9% by mass for the mixture of the polymerizable compounds, 3% by mass for the photochromic compound, 0.3% by mass for the photoradical polymerization initiator, and 0.3% by mass for the photoradical polymerization initiator.
• the inhibitor is 0.9% by weight and the light stabilizer is 0.9% by weight.
• the content of component A is 80% by mass and the content of component B is 20% by mass, with the total amount of polymerizable compounds being 100% by mass.
• a plastic lens base material (product name HI-LUX manufactured by HOYA; center wall thickness 2.2 mm, radius 70 mm, S0.00) was washed with pure water and dried. Thereafter, the photochromic layer-forming coating composition prepared above was applied to the convex surface (object-side surface) of this plastic lens base material by a spin coating method. Spin coating was performed by the method described in JP-A-2005-218994. Thereafter, the composition coated on the plastic lens base material was irradiated with ultraviolet rays (wavelength 405 nm) in a nitrogen atmosphere (oxygen concentration 500 ppm or less) to cure the composition and form a photochromic layer. The thickness of the photochromic layer formed was 40 ⁇ m. In this way, a spectacle lens having a photochromic layer was produced.
• Example 2 to 4 Comparative Examples 1 to 3
• Spectacle lenses were prepared as described for Example 1, except that the monofunctional (meth)acrylate was changed to those shown in Table 2.
• a spectacle lens was prepared as described for Example 1, except that 100 parts by mass of the same component A as in Example 1 was used without using the monofunctional (meth)acrylate.
• transmittance during coloring means that the photochromic compound is coloring at a higher concentration.
• the monofunctional (meth)acrylate used in Examples 1 to 4 is a monofunctional (meth)acrylate represented by Formula 1.
• the monofunctional (meth)acrylates used in Comparative Examples 1 to 3 are monofunctional (meth)acrylates that do not have the structure of Formula 1.
• Table 2 in Comparative Examples 1 to 3, compared to Reference Example 1, the color density increased due to the addition of monofunctional (meth)acrylate, but the rate of color fading was slowed.
• Examples 1 to 4 compared to Reference Example 1, the addition of monofunctional (meth)acrylate increased the color density and accelerated the rate of color fading. From the above results, it can be confirmed that the polymerizable composition containing components A to C makes it possible to form a photochromic layer that has a high color density when colored by light irradiation and has a fast fading rate.
• Component A Polyfunctional (meth)acrylate containing a polyalkylene glycol moiety and having a molecular weight of 500 or more
• Component B Monofunctional (meth)acrylate represented by the following formula 1 (In Formula 1, R 10 represents a hydrogen atom or a methyl group, and R 11 represents a straight chain alkyl group having 3 or more carbon atoms or a branched alkyl group having 3 or more carbon atoms.)
• Component C Photochromic compound [2] The polymerizable composition for optical articles according to [1], wherein the polyalkylene glycol moiety that component A has is a polyethylene glycol moiety.
• the present invention is useful in the technical fields of glasses, goggles, sun visors, helmets, etc.

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• Organic Chemistry (AREA)
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• 2023
  • 2023-03-30 JP JP2024512816A patent/JP7805443B2/ja active Active
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  • 2023-03-30 CN CN202380028610.XA patent/CN118984957A/zh active Pending
  • 2023-03-30 US US18/845,578 patent/US20250189825A1/en active Pending
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