WO2023190905A1 - 光学物品用重合性組成物および光学物品 - Google Patents

光学物品用重合性組成物および光学物品 Download PDF

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WO2023190905A1
WO2023190905A1 PCT/JP2023/013259 JP2023013259W WO2023190905A1 WO 2023190905 A1 WO2023190905 A1 WO 2023190905A1 JP 2023013259 W JP2023013259 W JP 2023013259W WO 2023190905 A1 WO2023190905 A1 WO 2023190905A1
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meth
acrylate
polymerizable composition
composition
group
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English (en)
French (fr)
Japanese (ja)
Inventor
敬 小林
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Hoya Lens Thailand Ltd
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Hoya Lens Thailand Ltd
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Priority to US18/846,162 priority Critical patent/US20250188342A1/en
Priority to KR1020247030833A priority patent/KR20240150484A/ko
Priority to EP23780913.2A priority patent/EP4502673A1/en
Priority to CN202380028611.4A priority patent/CN119096174A/zh
Priority to JP2024512817A priority patent/JP7805444B2/ja
Publication of WO2023190905A1 publication Critical patent/WO2023190905A1/ja
Anticipated expiration legal-status Critical
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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
    • 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
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/23—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
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • C08F220/1812—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
    • C08F222/106—Esters of polycondensation macromers
    • C08F222/1063—Esters of polycondensation macromers of alcohol terminated polyethers
    • 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
    • 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
    • C08F290/08—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 side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C08F290/148—Polysiloxanes
    • 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
    • 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
    • C09D135/00—Coating compositions based on homopolymers or 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 another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D135/02—Homopolymers or copolymers of esters
    • 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
    • C09D5/29—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for multicolour effects
    • 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
    • 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 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 exhibit a fast discoloration rate after being colored by light irradiation outdoors or the like. Furthermore, the desirable properties of the above-mentioned optical article include excellent weather resistance.
  • the desirable properties of the above-mentioned optical article include excellent weather resistance.
  • 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 fast discoloration rate and excellent weather resistance.
  • composition a polymerizable composition for optical articles (hereinafter also simply referred to as "composition") containing two or more types of (meth)acrylates and a photochromic compound.
  • the two or more types of (meth)acrylates include at least a polyfunctional (meth)acrylate containing a polyalkylene glycol moiety and having a molecular weight of 500 or more (hereinafter also referred to as "component A").
  • component A a polyfunctional (meth)acrylate containing a polyalkylene glycol moiety and having a molecular weight of 500 or more
  • component A the (meth)acryloyl group content in the polymerizable composition for optical articles is 3.50 mmol/g or more.
  • 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 present inventor conjectures that component A can contribute to making the matrix flexible. Specifically, it is thought that the reason why component A can form a flexible matrix is that component A has a molecular weight of 500 or more and component A has a polyalkylene glycol moiety.
  • the (meth)acryloyl group content of 3.50 mmol/g or more in the above composition contributes to the formation of a rigid polymer network between molecules in the matrix formed from the composition.
  • the inventor speculates.
  • the present inventor believes that the reason why it is possible to form a photochromic layer with excellent weather resistance using the above composition is that diffusion of active species that can cause a decrease in weather resistance can be suppressed in a matrix having a rigid polymer network.
  • the present inventor believes that the above composition makes it possible to form a photochromic layer that has a fast discoloration rate and excellent weather resistance.
  • 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 fast color fading rate after color development upon irradiation with light and has excellent weather resistance. Further, according to one aspect of the present invention, it is possible to provide an optical article having a photochromic layer that exhibits a fast discoloration rate after color development upon irradiation with light and excellent weather resistance.
  • a graph is shown in which the value of ⁇ Darkness is plotted against the (meth)acryloyl group content for each polymerizable composition of Examples and Comparative Examples.
  • 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 (meth)acryloyl group content of the composition is 3.50 mmol/g or more, preferably 3.55 mmol/g or more, and 3.60 mmol/g or more from the viewpoint of improving weather resistance. is more preferable, it is still more preferable that it is 3.65 mmol/g or more, it is still more preferable that it is 3.70 mmol/g or more, and it is even more preferable that it is 3.75 mmol/g or more.
  • the (meth)acryloyl group content of the composition can be, for example, 5.00 mmol/g or less, 4.50 mmol/g or less, or 4.00 mmol/g or less, or exceeds the values exemplified herein. It's okay.
  • the "(meth)acryloyl group content" of the polymerizable composition containing (meth)acrylate shall be calculated as follows.
  • the content of each (meth)acrylate is calculated by setting the total amount of (meth)acrylates contained in the polymerizable composition as "1" on a mass basis.
  • For each (meth)acrylate "(meth)acryloyl group content x above content rate” is determined.
  • the sum of the values thus calculated for all (meth)acrylates contained in the polymerizable composition is the (meth)acryloyl group content of the polymerizable composition.
  • the composition contains two or more types of (meth)acrylates as polymerizable compounds, and the two or more types of (meth)acrylates are polyfunctional (meth)acrylates (components) having a molecular weight of 500 or more and containing a polyalkylene glycol moiety. Contains at least A).
  • 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.
  • component A can have the above partial structure in which R represents an ethylene group, ie, a polyethylene glycol moiety.
  • component A can have the above partial structure in which R represents a propylene group, that is, a polypropylene 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.
  • (Monofunctional (meth)acrylate) From the viewpoint of increasing the content of (meth)acryloyl groups in a polymerizable composition containing (meth)acrylate, (meth)acrylates with a high proportion of (meth)acryloyl groups in the molecule are preferred. From this point of view, monofunctional (meth)acrylates with a low molecular weight are preferred, and monofunctional (meth)acrylates with a molecular weight of 150 or less are more preferred.
  • the monofunctional (meth)acrylate having a molecular weight of 150 or less may be a cyclic monofunctional (meth)acrylate or an acyclic monofunctional (meth)acrylate.
  • cyclic monofunctional (meth)acrylates having a molecular weight of 150 or less include glycidyl (meth)acrylate.
  • Specific examples of acyclic monofunctional (meth)acrylates having a molecular weight of 150 or less include n-butyl (meth)acrylate.
  • the molecular weight of the monofunctional (meth)acrylate having a molecular weight of 150 or less can be, for example, 100 or more, but is not limited thereto.
  • (Polyfunctional (meth)acrylate) As described above, from the viewpoint of increasing the (meth)acryloyl group content of a polymerizable composition containing (meth)acrylate, (meth)acrylates with a high proportion of (meth)acryloyl groups in the molecule are preferable. . From this point of view, polyfunctional (meth)acrylates having a smaller molecular weight than component A are also preferable. As such a polyfunctional (meth)acrylate, a polyfunctional (meth)acrylate having a higher functional number than the polyfunctional (meth)acrylate used as component A is also preferable. The molecular weight of such polyfunctional (meth)acrylate is preferably less than 500, 400 or less, 300 or less, or 200 or less.
  • the molecular weight can be, for example, 100 or more, but is not limited thereto.
  • a polyfunctional (meth)acrylate can be, for example, a polyfunctional (meth)acrylate having 10 or more functions (for example, 10 or more and 15 or less).
  • Specific examples include poly[(3-methacryloyloxypropyl)silsesquioxane] derivatives described in the Examples section below.
  • the (meth)acrylates that may be included in the composition include monofunctional (meth)acrylates represented by the following formula 1 (hereinafter also referred to as “component B”) and bifunctional (meth)acrylates represented by the following formula 5 (hereinafter also referred to as “component B”).
  • Meth) acrylate (hereinafter also referred to as “component C”) can also be mentioned.
  • the composition includes one or more (meth)acrylates selected from the group consisting of a monofunctional (meth)acrylate represented by the following formula 1 and a bifunctional (meth)acrylate represented by the following formula 5. It can be a polymerizable composition containing acrylate.
  • the composition includes one or more types of ( The polymerizable composition may be meth)acrylate-free.
  • the composition can also include component B as a monofunctional (meth)acrylate with a molecular weight of 150 or less.
  • 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 straight chain or branched alkyl group represented by R 11 is 3 or more, preferably 4 or more, more preferably 5 or more, 6 or more, 7 or more, 8 or more, 9 The above is more preferable in the order of 10 or more, and 11 or more.
  • the number of carbon atoms is preferably 15 or less, more preferably 14 or less, and even more preferably 13 or less, and 12 or less.
  • the molecular weight of the monofunctional (meth)acrylate represented by Formula 1 can be, for example, 100 or more, and can be, for example, 300 or less. However, it is not limited to the above range. As described above, in one form, the monofunctional (meth)acrylate represented by Formula 1 can be a monofunctional (meth)acrylate having a molecular weight of 150 or less. 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.
  • Component C is represented by the following formula 5: It is a (meth)acrylate represented by
  • R 3 and R 4 each independently represent a hydrogen atom or a methyl group, and m represents an integer of 1 or more. m is 1 or more, and can be, for example, 10 or less, 9 or less, 8 or less, 7 or less, or 6 or less.
  • the molecular weight of component C can be, for example, 400 or less, and from the viewpoint of further increasing the coloring density of the photochromic layer, it is preferably 350 or less, more preferably 300 or less, and preferably 250 or less. More preferred. Further, the molecular weight of component C can be, for example, 100 or more, 150 or more, or 200 or more.
  • Component C 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.
  • Specific examples of component C include 1,9-nonanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, and 1,10-decanediol di(meth)acrylate.
  • 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 above composition can contain the various (meth)acrylates described above in an amount such that the content of (meth)acryloyl groups in the composition is 3.50 mmol/g or more.
  • the above composition preferably contains 5% by mass or more, and preferably contains 10% by mass or more of a monofunctional (meth)acrylate with a molecular weight of 150 or less, based on the total amount of polymerizable compounds contained in the composition as 100% by mass. is more preferable, and more preferably 15% by mass or more.
  • the content of monofunctional (meth)acrylate with a molecular weight of 150 or less is preferably 30% by mass or less, and preferably 25% by mass or less, based on the total amount of polymerizable compounds contained in the composition as 100% by mass. is more preferable.
  • 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. Further, 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" with respect to content rate 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. When a solvent is included, 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 includes a photochromic compound 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 preferably in the range of 5 to 80 ⁇ m, for example, and from the viewpoint of exhibiting better photochromic properties, it is more preferably in the range of 20 to 60 ⁇ m, and 20 to 60 ⁇ m. It is more preferably in the range of 50 ⁇ m, even more preferably in the range of 25 to 45 ⁇ m.
  • the viscosity at a temperature of 25°C is preferably 20 mPa ⁇ s or more.
  • the viscosity at a temperature of 25° C. can be, for example, 50 mPa ⁇ s or less or 40 mPa ⁇ s or less.
  • the viscosity of the composition may exceed the values exemplified here.
  • 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. I can do it.
  • 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.
  • 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.
  • each photochromic layer forming composition of Examples 1 and 2 and Comparative Examples 1 and 2 was measured by the following method. Using a viscometer (VM-100A manufactured by Sekonic Co., Ltd.), the liquid level of the sample was adjusted and fixed at about 2 to 3 mm from the end of the detection terminal, and the viscosity at a liquid temperature of 25° C. was measured. The measured viscosities were 34 mPa ⁇ s in Example 1, 30 mPa ⁇ s in Example 2, 25 mPa ⁇ s in Comparative Example 1, and 23 mPa ⁇ s in Comparative Example 2.
  • VM-100A manufactured by Sekonic Co., Ltd.
  • 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. Each photochromic layer forming composition having the above-mentioned viscosity made it possible to form a photochromic layer with excellent uniformity of film thickness. In this way, a spectacle lens having a photochromic layer was produced.
  • fading 60s transmittance The transmittance was measured 60 seconds after the light irradiation was stopped (hereinafter referred to as "fading 60s transmittance").
  • FIG. 1 shows a graph in which the value of ⁇ Darkness is plotted against the (meth)acryloyl group content for each of the polymerizable compositions of Examples and Comparative Examples.
  • a straight line approximated by the least squares method is also shown.
  • the (meth)acryloyl group content of the composition and ⁇ Darkness are correlated, and by setting the (meth)acryloyl group content of the composition to 3.50 mmol/g or more, It can be confirmed that ⁇ Darkness can be reduced to 6.0% or less.
  • optical article comprising a base material and a photochromic layer obtained by curing the polymerizable composition for optical articles according to any one of [1] to [5].
  • the optical article according to [6] which is a spectacle lens.
  • Eyeglasses comprising the eyeglass lens according to [7].
  • the present invention is useful in the technical fields of glasses, goggles, sun visors, helmets, etc.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Eyeglasses (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
PCT/JP2023/013259 2022-03-31 2023-03-30 光学物品用重合性組成物および光学物品 Ceased WO2023190905A1 (ja)

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EP23780913.2A EP4502673A1 (en) 2022-03-31 2023-03-30 Polymerizable composition for optical article and optical article
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WO2025182863A1 (ja) * 2024-02-28 2025-09-04 株式会社トクヤマ 硬化性組成物、硬化体、積層体、光学物品、レンズ、及び眼鏡

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WO2003011967A1 (en) * 2001-07-27 2003-02-13 Tokuyama Corporation Curable composition, cured article obtained therefrom, and photochromic optical material and process for producing the same
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