Composition and eyeglass lens

Abstract

The present disclosure addresses the problem of providing a composition capable of forming a layer excellent in interlayer adhesion. A composition according to the present disclosure comprises: a polymer S of a silsesquioxane having a polymerizable group; and a compound X selected from the group consisting of monomers M and polymers P of the monomer M. The monomer M is selected from the group consisting of polyalkylene glycol di(meth)acrylates and urethane (meth)acrylates. In the molecular weight distribution curve of the polymer S obtained by gel permeation chromatography, the peak top molecular weight of the polymer S is 2800 or more. In the molecular weight distribution curve of the polymer P obtained by gel permeation chromatography, the peak top molecular weight of the polymer P is 3500 or more.

Description

Composition, eyeglass lens

[0001] The present disclosure relates to compositions and eyeglass lenses.

[0002] Patent Document 1 discloses a copolymer containing both a segment (A) containing a repeating unit of a silicone structure represented by general formula (1) and a segment (B) containing a repeating unit having a cage silsesquioxane structure in a side chain represented by general formula (2).

[0003] Japanese Patent Application Laid-Open No. 2006-265514

[0004] The present disclosure relates to a composition (hereinafter also referred to as the "composition of the first embodiment") comprising a polymer S of a silsesquioxane having a polymerizable group, a monomer M, and a compound X selected from the group consisting of a polymer P of the monomer M, wherein the monomer M is selected from the group consisting of polyalkylene glycol di(meth)acrylates and urethane (meth)acrylates, and wherein, in a molecular weight distribution curve of the polymer S obtained by gel permeation chromatography, the peak top molecular weight of the polymer S is 2800 or more, and in a molecular weight distribution curve of the polymer P obtained by gel permeation chromatography, the peak top molecular weight of the polymer P is 3500 or more. The present disclosure also relates to a composition (hereinafter also referred to as the "composition of the second embodiment") comprising a silsesquioxane having a polymerizable group and a polymer P of a monomer M selected from the group consisting of polyalkylene glycol di(meth)acrylates and urethane (meth)acrylates, and wherein, in a molecular weight distribution curve of the polymer P obtained by gel permeation chromatography, the peak top molecular weight of the polymer P is 3500 or more.

[0005] 1 is an example showing a cross section of a spectacle lens.

[0006] The composition of the present disclosure will be described in detail below. The composition of the present disclosure is preferably used, for example, to form a hard coat layer of an eyeglass lens. A layer (e.g., a hard coat layer) formed using the composition of the present disclosure has excellent interlayer adhesion. Specifically, interlayer adhesion means that when a hard coat layer is formed on a substrate using the composition of the present disclosure, the hard coat layer is unlikely to peel off from the substrate, or when another layer (e.g., a primer layer) is formed on the substrate and a hard coat layer is further formed on the other layer using the composition of the present disclosure, the hard coat layer is unlikely to peel off from the substrate.

[0007] In this specification, the word "to" means that the numerical values ​​before and after it are included as the lower limit and upper limit. In this specification, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. In this specification, examples of halogenated groups include fluorination, chlorination, bromination, and iodination. In this specification, "(meth)acrylic" is a concept that encompasses both acrylic and methacrylic, "(meth)acryloyl group" is a concept that encompasses both acryloyl groups and methacryloyl groups, and "(meth)acrylate" is a concept that encompasses both acrylate and methacrylate.

[0008] In this specification, the term "solid content" refers to components other than the solvent, and even if the component is liquid at room temperature and normal pressure (25°C, 101.3 kPa), it is still counted as a solid content. The solid content may also be a component that undergoes a chemical change during the curing process. However, when the composition and living polymerization mixture described below contain a specific compound selected from the group consisting of a surfactant that is liquid at room temperature and normal pressure, a living polymerization catalyst that is liquid at room temperature and normal pressure, and a co-catalyst that is liquid at room temperature and normal pressure, the solid content of the composition and living polymerization mixture described below does not include the specific compound. For example, in a composition consisting only of polymer S, monomer X, a surfactant that is liquid at room temperature and normal pressure, and a solvent, only polymer S and monomer X constitute the solid content of the composition.

[0009] The first and second embodiments will be described in detail below.

[0010] [First Embodiment] The composition of the first embodiment comprises a polymer S of a silsesquioxane having a polymerizable group, a monomer M, and a compound X selected from the group consisting of a polymer P of the monomer M, wherein the monomer M is selected from the group consisting of polyalkylene glycol di(meth)acrylate and urethane (meth)acrylate, and in a molecular weight distribution curve of the polymer S obtained by gel permeation chromatography, the peak top molecular weight of the polymer S is 2800 or more, and in a molecular weight distribution curve of the polymer P obtained by gel permeation chromatography, the peak top molecular weight of the polymer P is 3500 or more. In other words, the composition of the first embodiment comprises the polymer S and the monomer M, or comprises the polymer S and the polymer P. Alternatively, the composition of the first embodiment may comprise the polymer S, the monomer M, and the polymer P.

[0011] <Polymer S> The composition of the first embodiment contains polymer S. Polymer S is a polymer of silsesquioxane having a polymerizable group. Polymer S is preferably a polymer obtained by polymerization via the polymerizable group possessed by silsesquioxane. Polymer S is a so-called prepolymer, and is a polymer that can be further cured by a curing treatment such as a light irradiation treatment when forming a hard coat layer. Polymer S preferably has a polymerizable group. Examples of the polymerizable group possessed by polymer S include polymerizable groups that remain when polymer S is formed, among polymerizable groups possessed by silsesquioxane having a polymerizable group.

[0012] In a molecular weight distribution curve of Polymer S obtained by gel permeation chromatography (GPC), the peak top molecular weight of Polymer S is 2,800 or more, preferably 3,000 or more, more preferably 4,000 or more, and even more preferably 5,000 or more. The upper limit is preferably 1,000,000 or less, more preferably 500,000 or less, and even more preferably 10,000 or less. When Polymer S has multiple peak top molecular weights, it is preferable that at least one of the multiple peak top molecular weights falls within the above-mentioned peak top molecular weight range, and it is more preferable that all of the peak top molecular weights fall within the above-mentioned peak top molecular weight range.

[0013] The peak top molecular weight of polymer S can be measured by the following method. First, polymer S is dissolved in a solvent to prepare a measurement solution. Alternatively, the measurement solution may be a solution obtained by living polymerization of a living polymerization mixture described later. The solvent may be any solvent in which polymer S dissolves, and is preferably a solvent that can be contained in a solution obtained by living polymerization of a living polymerization mixture described later. Next, the molecular weight is measured using a GPC analyzer under the following conditions, and the molecular weight at each elution time is calculated from the obtained retention time using the elution curve of monodisperse polystyrene. Thereafter, a molecular weight distribution curve is created, and the peak top molecular weight of polymer S is determined from the obtained molecular weight distribution curve. GPC analyzer: HLC-8420GPC manufactured by Tosoh Corporation Column: Two SuperMultipore HZ-M columns and two guard columns connected in series manufactured by Tosoh Corporation Column temperature: 40°C Mobile phase: chloroform 1.0 mL / min Sample concentration: 0.2% by mass Temperature: oven 40°C, injection port 35°C, detector 35°C Detector: differential refractometer

[0014] In the molecular weight distribution curve of Polymer S obtained by GPC, the molecular weight of Polymer S is preferably in the region of 2,000 or more, more preferably in the region of 3,000 or more, and even more preferably in the region of 4,000 or more. The upper limit is preferably in the region of 70,000,000 or less, more preferably in the region of 2,000,000 or less, even more preferably in the region of 1,000,000 or less, particularly preferably in the region of 30,000 or less, and most preferably in the region of 20,000 or less.

[0015] Examples of methods for adjusting the molecular weight of polymer S include known methods. In the method for performing living polymerization using a mixture for living polymerization described below, it is preferable to set the type and content of the polymerization initiator, the type and content of the catalyst or co-catalyst, the reaction time, and the reaction temperature to preferred modes described below.

[0016] Examples of the polymerizable group contained in the silsesquioxane include a radically polymerizable group and a cationically polymerizable group. A (meth)acryloyl group is preferred as the radically polymerizable group. Examples of the cationically polymerizable group include alicyclic ether groups such as an epoxy group and an oxetanyl group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiro orthoester group, and a vinyloxy group, with an epoxy group or an oxetanyl group being preferred. The number of polymerizable groups contained in the silsesquioxane is preferably 2 or more, more preferably 2 to 10.

[0017] Silsesquioxanes are silane compounds obtained by hydrolysis of trifunctional silane compounds such as alkoxysilanes, chlorosilanes, and silanols. Examples of the structure of silsesquioxanes include irregular structures such as random structures, ladder structures, cage structures (fully condensed cage structures), and incomplete cage structures (partially cleaved cage structures in which some silicon atoms are missing from the cage structure and some silicon-oxygen bonds in the cage structure are broken).

[0018] The silsesquioxane having a polymerizable group is preferably a compound having a basic skeleton represented by formula (Q).

[0019] R Ｑ -SiO ３／２ (Q) In formula (Q), R Ｑ represents a monovalent organic group, at least one of which represents a polymerizable group or a group having a polymerizable group. The group having a polymerizable group is preferably an -alkylene group-O-polymerizable group. The alkylene group preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms. The polymerizable group is preferably a polymerizable group contained in the silsesquioxane described above.

[0020] Examples of silsesquioxanes having a polymerizable group include the SQ series (eg, AC-SQ series and MAC-SQ series, manufactured by Toagosei Co., Ltd.).

[0021] The average particle size of the silsesquioxane having a polymerizable group is preferably 0.5 to 200 nm, more preferably 1 to 50 nm. Methods for measuring the average particle size include, for example, using a scanning electron microscope to measure the particle sizes of any 100 silsesquioxanes having a polymerizable group and calculating the arithmetic average, and using dynamic light scattering under the following conditions. Measuring device: Zeta potential / particle size measuring system ELS-Z2 (manufactured by Otsuka Electronics Co., Ltd.) Measuring cell: Particle size cell unit (scattering angle 165°) Measuring temperature: 25°C Particle size analysis method: Contin method During measurement, a dispersion containing the silsesquioxane having a polymerizable group to be measured is diluted with a dilution solvent as needed. Examples of the dilution solvent include MEK (methyl ethyl ketone). If the use of MEK causes problems such as aggregation of the silsesquioxane having a polymerizable group, another appropriate dilution solvent may be used. Furthermore, in this disclosure, unless otherwise specified, the average particle size refers to the average particle size based on volume distribution.

[0022] The silsesquioxane having a polymerizable group may be used alone or in combination of two or more kinds.

[0023] Examples of methods for producing the polymer S include known polymerization methods such as living polymerization, and living polymerization is preferred. Examples of living polymerization include living radical polymerization such as atom transfer radical polymerization using a mixture for living polymerization.

[0024] (Living Polymerization Mixture) The living polymerization mixture contains a silsesquioxane having a polymerizable group. The living polymerization mixture preferably further contains at least one selected from the group consisting of a living polymerization catalyst, a polymerization initiator, a solvent, and a co-catalyst, and more preferably further contains a living polymerization catalyst, a polymerization initiator, a solvent, and a co-catalyst.

[0025] The silsesquioxane having a polymerizable group is as described above. The content of the silsesquioxane having a polymerizable group is preferably 10 to 90 mass %, more preferably 20 to 70 mass %, based on the total solid content of the living polymerization mixture.

[0026] Examples of living polymerization catalysts include transition metals and transition metal compounds. Examples of the transition metals in the transition metals and transition metal compounds include copper, iron, cobalt, chromium, manganese, molybdenum, silver, zinc, palladium, rhodium, platinum, ruthenium, iridium, ytterbium, samarium, rhenium, and nickel, with copper, iron, or ruthenium being preferred. The transition metal compound may be a transition metal complex comprising the transition metal and a ligand.

[0027] As the living polymerization catalyst, copper, copper compounds such as ferrocenes, iron, or iron compounds such as ferrocenes are preferred. As the living polymerization catalyst, a compound represented by formula (F1) or a compound represented by formula (F2) is preferred. CP １ -M-CP ２ (F1) CP １ -Fe-(R Ｑ ) ３ (F2)

[0028] In formula (F1), M represents copper or iron. １ and CP ２ each independently represents a cyclopentadienyl ring which may have a substituent. The number of substituents on the cyclopentadienyl ring is preferably 0 to 5, and more preferably 1. The substituent that the cyclopentadienyl ring may have is -P(R Ｐ ) ２ The above "-P(R Ｐ ) ２ " P is a phosphorus atom, and two R Ｐ each independently represents a hydrogen atom or a substituent. The substituent is preferably an organic group, more preferably an alkyl group or a phenyl group. The alkyl group may be either linear or branched. The alkyl group preferably has 1 to 3 carbon atoms.

[0029] In formula (F2), CP １ represents a cyclopentadienyl ring which may have a substituent. １ is the CP in formula (F1). １The three R Ｑ are each independently —CO, a halogen atom, or —PPh ３ The above "-PPh ３ " in the formula "P" is a phosphorus atom, and Ph is a phenyl group which may have a substituent. The substituent which the phenyl group may have is preferably an alkyl group. The alkyl group may be either linear or branched, and the number of carbon atoms in the alkyl is preferably 1 to 3. The number of substituents which the phenyl group has is preferably 0 to 5.

[0030] Examples of the copper compound include cuprous chloride, cuprous bromide, cuprous iodide, cuprous cyanide, cuprous oxide, and cuprous perchlorate.

[0031] The living polymerization catalyst may be used alone or in combination of two or more. The content of the living polymerization catalyst is preferably 0.00001 to 5 mass %, more preferably 0.00005 to 2 mass %, based on the total solid content of the mixture for living polymerization.

[0032] Examples of the polymerization initiator include 1-chloroethylbenzene, 1-phenylethyl bromide, chloroform, carbon tetrachloride, 2-chloropropionitrile, α,α'-dichloroxylene, α,α'-dibromoxylene, hexakis(α-bromomethyl)benzene, and alkyl ester compounds of halogenated carboxylic acids (for example, diethylchloromalonic acid, 2-chloropropionic acid, 2-bromopropionic acid, 2-chloroisobutyric acid, and 2-bromoisobutyric acid).

[0033] The polymerization initiator may be used alone or in combination of two or more. The content of the polymerization initiator is preferably 0.01 to 1 mass % based on the total mass of the monomers (for example, silsesquioxane having a polymerizable group and monomer M).

[0034] Examples of the solvent include organic solvents such as tetrahydrofuran, ethyl acetate, toluene, acetone, dimethylformamide, ketones, and alcohols, as well as water.

[0035] The solvent may be used alone or in combination of two or more. The content of the solvent is preferably from 0 to 95% by mass, more preferably from 10 to 90% by mass, based on the total mass of the mixture for living polymerization.

[0036] Examples of the co-catalyst include triamine compounds such as pentamethyldiethylenetriamine, phosphine compounds such as diphenylphosphine oxide, triazine compounds having at least one triazine ring, benzotriazole compounds having at least one benzotriazole ring, and imidazole compounds having at least one imidazole ring (for example, 1-methylimidazole). Preferred co-catalysts are phosphine compounds such as diphenylphosphine oxide, tri(m-tolyl)phosphine, and tri(o-tolyl)phosphine, or triamine compounds such as N,N,N',N",N"-pentamethyldiethylenetriamine, tripropylamine, and tris(2-pyridylmethyl)amine. Examples of the promoter include Tinuvin 400, Tinuvin 384-2, and Tinuvin 477 (all manufactured by BASF).

[0037] The co-catalyst may be used alone or in combination of two or more. The content of the co-catalyst is preferably 0.000001 to 10% by mass, more preferably 0.00001 to 5% by mass, based on the total solid content of the mixture for living polymerization. The content of the co-catalyst is preferably 0.1 to 1000% by mass, based on the total mass of the catalyst.

[0038] The reaction time of the living polymerization is preferably 0.5 to 24 hours, more preferably 1 to 10 hours, and the reaction temperature of the living polymerization is preferably 25 to 100°C, more preferably 25 to 60°C.

[0039] One or more kinds of polymers S may be used alone or in combination. The content of polymer S is preferably 10 to 90 mass %, more preferably 20 to 80 mass %, and still more preferably 30 to 60 mass %, based on the total solid content of the composition.

[0040] <Compound X> The composition of the first embodiment contains a compound X. The compound X is a compound selected from the group consisting of a monomer M and a polymer P of the monomer M.

[0041] (Monomer M) The composition of the first embodiment may contain a monomer M. The monomer M is a monomer selected from the group consisting of polyalkylene glycol di(meth)acrylates and urethane (meth)acrylates.

[0042] The polyalkylene glycol di(meth)acrylate is a monomer having (meth)acryloyl groups at both ends of the polyalkylene glycol chain. The urethane (meth)acrylate may be an oligomer. The polyalkylene glycol di(meth)acrylate is preferably a compound represented by formula (II):

[0043]

[0044] In formula (II), n represents a number from 0 to 30. ３ and R ４ each independently represents a hydrogen atom or a methyl group. ３ may be the same or different. ４ If there is a plurality of R ４ may be the same or different. n is preferably a number from 1 to 25, more preferably a number from 4 to 25, and even more preferably a number from 9 to 20.

[0045] Examples of polyalkylene glycol di(meth)acrylates include NK ester bifunctional polyethylene glycol acrylates (A-200, A-400, A-600, A-1000, etc., manufactured by Shin-Nakamura Chemical Co., Ltd.), Light Acrylate 4EG-A, Light Acrylate 9EG-A, and Light Acrylate 14EG-A (all manufactured by Kyoeisha Chemical Co., Ltd.).

[0046] The molecular weight of the polyalkylene glycol di(meth)acrylate is preferably less than 3000, more preferably 2000 or less, and even more preferably 1500 or less. The lower limit is preferably 400 or more, and more preferably 600 or more.

[0047] The urethane (meth)acrylate is a monomer having a urethane bond and a (meth)acryloyl group. The urethane (meth)acrylate may also be an oligomer. The number of (meth)acryloyl groups in the urethane (meth)acrylate is preferably 1 or 2 or more, more preferably 2 or 3. In other words, for example, the urethane (meth)acrylate may be either a urethane di(meth)acrylate or a urethane tri(meth)acrylate. The number of urethane bonds in the urethane (meth)acrylate is preferably 1 or 2 or more, more preferably 2 or more, and even more preferably 3 or more. The upper limit is preferably 100 or less, more preferably 50 or less.

[0048] The urethane (meth)acrylate is preferably obtained by reacting a polyol, a diisocyanate, and a (meth)acrylate having a hydroxyl group. Examples of polyols include 1,6-hexane diglycidyl ether, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polycaprolactone diol, polycarbonate diol, polybutadiene polyol, and polyester diol. Examples of diisocyanates include toluene diisocyanate, xylene diisocyanate, diphenylmethane diisocyanate, tetramethylxylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and dicyclohexylmethane diisocyanate. Examples of the (meth)acrylate having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, pentaerythritol (meth)acrylate, and caprolactone-modified 2-hydroxyethyl (meth)acrylate.

[0049] The urethane (meth)acrylate is preferably a compound represented by formula (I).

[0050]

[0051] In formula (I), m represents a number from 0 to 9. R represents a bifunctional polyester polyol residue or a bifunctional polyether polyol residue. １ represents a hydrogen atom or a methyl group. ２ represents an alkylene group having 2 to 4 carbon atoms. L represents a group represented by any one of formulas (I-1) to (I-3).

[0052] In formula (I), R represents a bifunctional polyester polyol residue or a bifunctional polyether polyol residue. The bifunctional polyester polyol residue is a group obtained by removing two hydroxyl groups (OH) from a polyester polyol having two hydroxyl groups. Examples of the polyester polyol include polyester polyols obtained by dehydration condensation of adipic acid or phthalic acid with a glycol having 2 to 6 carbon atoms. The bifunctional polyether polyol residue is a group obtained by removing two hydroxyl groups (OH) from a polyether polyol having two hydroxyl groups. Examples of the polyether polyol include polyethylene glycol and polypropylene glycol.

[0053] In formula (I), R ２ represents an alkylene group having 2 to 4 carbon atoms. The alkylene group may be either linear or branched.

[0054] L represents a group represented by any one of formulas (I-1) to (I-3), in which * represents a bonding position.

[0055] When a plurality of groups represented by the same symbol are present in formula (I), the plurality of groups represented by the same symbol may be the same or different.

[0056] Examples of urethane (meth)acrylates include CN9002, CN910A70, CN9167, CN9170A86, CN9200, CN963B80, CN964A85, CN965, CN966H90, CN9761, CN9761A75, CN981, CN991, and CN996 (all manufactured by Sartomer Arkema); UF8001G, UF8002G, UF8003G, and DAUA-167 (all manufactured by Kyoei Chemical Co., Ltd.); SC2404, SC2565, PU-2560, and UA-5210 (all manufactured by Miwon Chemical Co., Ltd.); and UA-122P and UA-232P (all manufactured by Shin-Nakamura Chemical Co., Ltd.).

[0057] The weight average molecular weight of the urethane (meth)acrylate is preferably less than 4000, more preferably 3800 or less, and even more preferably 3500 or less. The lower limit is preferably 300 or more, and more preferably 500 or more.

[0058] The monomer M may be used alone or in combination of two or more kinds. The content of the monomer M is preferably from 1 to 99 mass %, more preferably from 5 to 90 mass %, and still more preferably from 10 to 70 mass %, based on the total solid content of the composition.

[0059] (Polymer P) The composition of the first embodiment may contain polymer P. Polymer P is a polymer of monomer M. Polymer P is preferably a polymer obtained by polymerization via a polymerizable group (e.g., a (meth)acryloyl group) possessed by monomer M. Polymer P is a so-called prepolymer, and is a polymer that can be further cured by a curing treatment such as a light irradiation treatment when forming a hard coat layer. Polymer P preferably has a polymerizable group. Examples of the polymerizable group possessed by polymer P include the polymerizable group of the polymerizable group possessed by monomer M that remains when polymer P is formed. Monomer M is as described above.

[0060] In the molecular weight distribution curve of polymer P obtained by GPC, the peak top molecular weight of polymer P is 3,500 or more, preferably 4,000 or more. The upper limit is preferably 600,000 or less, more preferably 45,000 or less, and even more preferably 25,000 or less. When polymer P has multiple peak top molecular weights, it is preferable that at least one of the multiple peak top molecular weights falls within the above-mentioned peak top molecular weight range, and it is more preferable that all of the peak top molecular weights fall within the above-mentioned peak top molecular weight range.

[0061] In the molecular weight distribution curve of polymer P obtained by GPC, the molecular weight of polymer P is preferably in the region of 2,000 or more, more preferably in the region of 4,000 or more, even more preferably in the region of 4,500 or more, and particularly preferably in the region of 5,000 or more. The upper limit is preferably in the region of 2,000,000 or less, more preferably in the region of 400,000 or less, even more preferably in the region of 50,000 or less, and particularly preferably in the region of 30,000 or less. The peak top molecular weight of polymer P and the molecular weight of polymer P can be measured by the same method as the measurement method for polymer S described above.

[0062] As a method for producing the polymer P, for example, there can be mentioned a method in which, in the above-mentioned method for producing the polymer S, the monomer M is used instead of the silsesquioxane having a polymerizable group.

[0063] The polymer P may be used alone or in combination of two or more. The content of the polymer P is preferably from 1 to 99% by mass, more preferably from 5 to 90% by mass, and still more preferably from 10 to 70% by mass, based on the total solid content of the composition.

[0064] <Polymerization initiator> The composition of the first embodiment may contain a polymerization initiator. Examples of the polymerization initiator include a photopolymerization initiator and a thermal polymerization initiator, and a photopolymerization initiator is preferred. Examples of the polymerization initiator include Omnirad 127, 184, 907, 651, 1700, 1800, 819, 369, and TPO (manufactured by IGM Resins B.V.); DAROCUR 1173 (manufactured by Sigma-Aldrich); Ezacure KIP 150 and TZT (manufactured by Nippon SiberHegner Co., Ltd.); Kayacure BMS and Kayacure DMBI (manufactured by Nippon Kayaku Co., Ltd.); Tinuvin 400, Tinuvin 405, Tinuvin 460, Tinuvin 477, Tinuvin 479, and Tinuvin 1577 (manufactured by BASF). Examples of the cationic polymerization initiator include a polymerizable monomer containing one or more cations selected from the group consisting of aromatic sulfonium, aromatic iodonium, aromatic diazonium, and pyridinium, and BF ４ － , P.F. ６－ , SbF ６－ , AsF ６－ , C.F. ３ SO ３－ , (CF ３ SO ２ ) ２ N － and B(C ６ F ５ ) ４－ and one or more anions selected from the group consisting of: and a thermal cationic polymerization initiator such as an onium salt composed of: and an aluminum complex such as aluminum chloride. The polymerization initiator may be used alone or in combination of two or more. The content of the polymerization initiator is preferably 0.001 to 5 mass %, more preferably 0.01 to 5 mass %, based on the total solid content of the composition.

[0065] <Sensitizer> The composition of the first embodiment may contain a sensitizer. When the composition contains a polymerization initiator, it is preferable that the composition further contains a sensitizer. Examples of sensitizers include the Anthracure series (manufactured by Kawasaki Chemical Industries, Ltd.). One type of sensitizer may be used alone, or two or more types may be used in combination. The content of the sensitizer is preferably 0.001 to 5 mass %, and more preferably 0.05 to 2 mass %, based on the total solid content of the composition.

[0066] <Surfactant> The composition of the first embodiment may contain a surfactant. Examples of the surfactant include silicone compounds such as silicone oil. Examples of the surfactant include the DOWSIL series (manufactured by Dow Chemical). One type of surfactant may be used alone, or two or more types may be used in combination. The content of the surfactant is preferably 0.001 to 5 mass %, more preferably 0.01 to 0.5 mass %, based on the total solid content of the composition.

[0067] <UV Absorber> The composition of the first embodiment may contain an UV absorber. Examples of UV absorbers include triazine compounds and benzotriazole compounds. Examples of triazine compounds and benzotriazole compounds include the triazine compounds and benzotriazole compounds that can be contained in the living polymerization mixture described above. Therefore, when a living polymerization mixture is used to prepare the composition of the first embodiment, the triazine compounds and benzotriazole compounds contained in the living polymerization mixture may be used as UV absorbers in the composition of the first embodiment. One UV absorber may be used alone, or two or more UV absorbers may be used in combination. The content of the UV absorber is preferably 0.01 to 5 mass %, more preferably 0.1 to 3 mass %, based on the total solid content of the composition.

[0068] <Solvent> The composition of the first embodiment may contain a solvent. Examples of the solvent include water and organic solvents. Examples of the organic solvent include alcohol-based solvents, ketone-based solvents such as methyl ethyl ketone, ether-based solvents such as tetrahydrofuran, ester-based solvents, hydrocarbon-based solvents, halogenated hydrocarbon-based solvents, amide-based solvents, sulfone-based solvents, and sulfoxide-based solvents. The solvent may be used alone or in combination of two or more. The content of the solvent is preferably 10 to 90% by mass, more preferably 30 to 80% by mass, relative to the total mass of the composition.

[0069] <Other Components> The composition of the first embodiment may contain other components in addition to the various components described above. Examples of other components include various components that may be contained in a living polymerization mixture, their reaction products and decomposition products, silsesquioxanes having no polymerizable groups, inorganic oxide particles (excluding silsesquioxanes having polymerizable groups and silsesquioxanes having no polymerizable groups), antioxidants, coating film modifiers, light stabilizers, antioxidants, color inhibitors, dyes, fillers, and internal mold release agents.

[0070] <Preferred Aspects> The composition of the first embodiment preferably contains a silsesquioxane having a polymerizable group and satisfies Requirement A1, or does not contain a silsesquioxane having a polymerizable group and satisfies Requirement B1. Requirement A1 is preferably Requirement A2 or Requirement A3, and more preferably Requirement A4. Requirement B1 is preferably Requirement B2 or Requirement B3, and more preferably Requirement B4.

[0071] Requirement A1: The total content of the polymer S and the silsesquioxane having a polymerizable group is 30% by mass or more relative to the total content of the polymer S, the silsesquioxane having a polymerizable group, and the compound X. Requirement A2: The total content of the polymer S and the silsesquioxane having a polymerizable group is 50% by mass or more relative to the total content of the polymer S, the silsesquioxane having a polymerizable group, and the compound X. Requirement A3: The total content of the polymer S and the silsesquioxane having a polymerizable group is 30 to 90% by mass relative to the total content of the polymer S, the silsesquioxane having a polymerizable group, and the compound X. Requirement A4: The total content of the polymer S and the silsesquioxane having a polymerizable group is 50 to 70% by mass relative to the total content of the polymer S, the silsesquioxane having a polymerizable group, and the compound X.

[0072] Requirement B1: The content of polymer S is 5% by mass or more, based on the total content of polymer S and compound X. Requirement B2: The content of polymer S is 10% by mass or more, based on the total content of polymer S and compound X. Requirement B3: The content of polymer S is 5 to 20% by mass, based on the total content of polymer S and compound X. Requirement B4: The content of polymer S is 10 to 15% by mass, based on the total content of polymer S and compound X.

[0073] When the composition of the first embodiment contains a silsesquioxane having a polymerizable group, the total content of polymer S, silsesquioxane having a polymerizable group, and compound X is preferably 80 to 100 mass%, more preferably 95 to 100 mass%, and even more preferably 98 to 100 mass%, based on the total solid content of the composition. When the composition of the first embodiment does not contain a silsesquioxane having a polymerizable group, the total content of polymer S and compound X is preferably 80 to 100 mass%, more preferably 95 to 100 mass%, and even more preferably 98 to 100 mass%, based on the total solid content of the composition.

[0074] [Second embodiment] The composition of the second embodiment comprises a silsesquioxane having a polymerizable group, and a polymer P of a monomer M selected from the group consisting of polyalkylene glycol di(meth)acrylate and urethane (meth)acrylate, wherein the polymer P has a peak top molecular weight of 3500 or more in a molecular weight distribution curve of the polymer P obtained by gel permeation chromatography. In other words, the composition of the second embodiment comprises a silsesquioxane having a polymerizable group and the polymer P.

[0075] The silsesquioxane having a polymerizable group, the monomer M, and the polymer P are as described in the first embodiment.

[0076] In the second embodiment, in addition to the various components described above, a component selected from the group consisting of a polymerization initiator, a sensitizer, a surfactant, an ultraviolet absorber, a solvent, and other components described in the first embodiment may be included.

[0077] <Preferred Aspect> The composition of the second embodiment preferably further contains a monomer M selected from the group consisting of polyalkylene glycol di(meth)acrylates and urethane (meth)acrylates and satisfies requirement C1, or further does not contain a monomer M selected from the group consisting of polyalkylene glycol di(meth)acrylates and urethane (meth)acrylates and satisfies requirement D1. Requirement C1 is preferably requirement C2 or requirement C3, and requirement C4 is more preferred. Requirement D1 is preferably requirement D2 or requirement D3, and requirement D4 is more preferred.

[0078] Requirement C1: The total content of the polymer P and the monomer M is 30% by mass or more, based on the total content of the polymer P, the monomer M, and the silsesquioxane having a polymerizable group. Requirement C2: The total content of the polymer P and the monomer M is 50% by mass or more, based on the total content of the polymer P, the monomer M, and the silsesquioxane having a polymerizable group. Requirement C3: The total content of the polymer P and the monomer M is 30 to 90% by mass, based on the total content of the polymer P, the monomer M, and the silsesquioxane having a polymerizable group. Requirement C4: The total content of the polymer P and the monomer M is 50 to 70% by mass, based on the total content of the polymer P, the monomer M, and the silsesquioxane having a polymerizable group.

[0079] Requirement D1: The content of polymer P is 10% by mass or more, based on the total content of polymer P and silsesquioxane having a polymerizable group. Requirement D2: The content of polymer P is 20% by mass or more, based on the total content of polymer P and silsesquioxane having a polymerizable group. Requirement D3: The content of polymer P is 10 to 80% by mass, based on the total content of polymer P and silsesquioxane having a polymerizable group. Requirement D4: The content of polymer P is 20 to 70% by mass, based on the total content of polymer P and silsesquioxane having a polymerizable group.

[0080] When the composition of the second embodiment contains monomer M, the total content of polymer P, monomer M, and silsesquioxane having a polymerizable group is preferably 80 to 100 mass%, more preferably 95 to 100 mass%, and even more preferably 98 to 100 mass%, based on the total solid content of the composition. When the composition of the second embodiment does not contain monomer M, the total content of polymer P and silsesquioxane having a polymerizable group is preferably 80 to 100 mass%, more preferably 95 to 100 mass%, and even more preferably 98 to 100 mass%, based on the total solid content of the composition.

[0081] [Method for Producing Composition] Examples of methods for producing the compositions of the first and second embodiments include a method in which the various components that may be contained in the composition of the first or second embodiment described above are mixed all at once, and a method in which the various components are mixed in stages in portions. The composition of the first or second embodiment may also be prepared using a solution obtained by living polymerization of a mixture for living polymerization. In other words, when the above liquid is used, the various components contained in the above liquid are carried over into the composition of the first or second embodiment.

[0082] The compositions of the first and second embodiments are preferably used as compositions for forming a hard coat layer on a substrate (compositions for forming a hard coat layer). The substrate is preferably a spectacle lens substrate, which will be described later.

[0083] [Eyeglass Lens] The hard coat layer formed using the composition of the first embodiment or the second embodiment may be used for an eyeglass lens. The eyeglass lens is preferably an eyeglass lens including an eyeglass lens substrate (for example, an eyeglass lens substrate, etc.) and a hard coat layer formed using the composition of the first embodiment or the second embodiment, which is disposed on the eyeglass lens substrate.

[0084] FIG. 1 is a cross-sectional view of one embodiment of a spectacle lens. The spectacle lens 10 shown in FIG. 1 includes a spectacle lens substrate 12, primer layers 14 disposed on both sides of the spectacle lens substrate 12, and hard coat layers 16 disposed on both sides of the primer layer 14. The hard coat layers 16 are layers formed using the composition of the first or second embodiment. The spectacle lens 10 includes the primer layer 14, but is not limited to this form and may not include the primer layer 14. Furthermore, the spectacle lens 10 includes the primer layer 14 on both sides of the spectacle lens substrate 12, but the primer layer 14 may be disposed on only one side of the spectacle lens substrate 12. Furthermore, the spectacle lens 10 includes the hard coat layers 16 on both sides of the primer layer 14, but the hard coat layer 16 may be disposed on only one side of the primer layer 14. Each component that may be included in the spectacle lens 10 is described in detail below.

[0085] <Eyeglass Lens Substrate> Examples of types of eyeglass lens substrates include finished lenses in which both the convex and concave surfaces are optically finished and molded to the desired power. Examples of types of resins that make up the eyeglass lens substrate include (meth)acrylic resins, thiourethane resins, allyl resins, episulfide resins, polycarbonate resins, polyurethane resins, polyester resins, polystyrene resins, polyethersulfone resins, poly-4-methylpentene-1 resins, diethylene glycol bisallyl carbonate resins (CR-39), and polyvinyl chloride resins.

[0086] The thickness of the spectacle lens substrate is preferably 1 to 30 mm from the viewpoint of ease of handling. The refractive index of the spectacle lens substrate is not particularly limited. The spectacle lens substrate may be opaque or colored as long as it has light-transmitting properties.

[0087] <Hard Coat Layer> The hard coat layer is a layer disposed on a spectacle lens substrate, and is a layer that imparts scratch resistance to the spectacle lens substrate. The hard coat layer is a layer formed from the composition of the first embodiment or the second embodiment.

[0088] Examples of methods for forming the hard coat layer include a method in which the composition of the first or second embodiment is applied to a spectacle lens substrate to form a coating film, and the coating film is subjected to a curing treatment such as light irradiation treatment and heat treatment. After the coating film is formed, a drying treatment such as heat treatment may be performed, if necessary, to remove the solvent from the coating film.

[0089] The method for applying the composition of the first or second embodiment to the spectacle lens substrate includes known methods (e.g., dipping coating, spin coating, spray coating, inkjet coating, flow coating, etc.). For example, when using the dipping coating method, the spectacle lens substrate is immersed in the composition of the first or second embodiment, and then the spectacle lens substrate is pulled up and dried, thereby forming a coating film of a predetermined thickness on the spectacle lens substrate. The thickness of the coating film formed on the spectacle lens substrate can be adjusted as appropriate.

[0090] The conditions for the light irradiation treatment can be selected appropriately depending on the type of polymerization initiator used. The type of light used for light irradiation can be, for example, ultraviolet light or visible light. The light source can be, for example, a high-pressure mercury lamp. The cumulative light amount used for light irradiation can be 100 to 3000 mJ / cm from the viewpoints of productivity and curability of the coating film. ２ is preferred, and 100 to 1500 mJ / cm ２ is more preferred.

[0091] The thickness of the hard coat layer is preferably 1 μm or more, more preferably 5 μm or more, and even more preferably 10 μm or more. The upper limit is preferably 30 μm or less. The thickness is an average thickness, and is measured by measuring the thickness at any five points on the hard coat layer and calculating the arithmetic average.

[0092] <Primer Layer> The spectacle lens may further include a primer layer disposed between the substrate and the hard coat layer. The primer layer is a layer that improves the adhesion of the hard coat layer to the substrate. Examples of materials that constitute the primer layer include resins. Specific examples include urethane-based resins, epoxy-based resins, phenol-based resins, polyimide-based resins, polyester-based resins, bismaleimide-based resins, and polyolefin-based resins.

[0093] The primer layer may be formed by any known method, such as applying a resin-containing composition for forming a primer layer onto a substrate and optionally curing the composition to form a primer layer.

[0094] When manufacturing a spectacle lens having a spectacle lens substrate, a primer layer, and a hard coat layer in this order, it is preferable to apply a primer layer-forming composition to the spectacle lens substrate to form a first coating film, apply the composition of the first or second embodiment to the first coating film to form a second coating film, and then perform a curing treatment on the first and second coating films to form the primer layer and hard coat layer on the spectacle lens substrate in this order. The above method tends to provide excellent adhesion between the primer layer and the hard coat layer. Furthermore, if necessary, heat treatment may be performed during the formation of the first coating film and the formation of the second coating film. The curing treatment is preferably the curing treatment for the hard coat layer described above. In particular, heat treatment is preferred for the first coating film.

[0095] The thickness of the primer layer may be from 0.3 to 2 μm.

[0096] <Anti-Reflection Layer> The spectacle lens may include an anti-reflection layer. The anti-reflection layer is a layer that functions to prevent reflection of incident light. Specifically, it has low reflection characteristics (broadband low reflection characteristics) across the entire visible range from 400 to 700 nm. The anti-reflection layer may have a single-layer structure or a multi-layer structure. The anti-reflection layer is preferably an inorganic anti-reflection layer. An inorganic anti-reflection layer refers to an anti-reflection layer composed of an inorganic compound. A multi-layer anti-reflection layer may have a structure in which low-refractive-index layers and high-refractive-index layers are alternately stacked. Examples of materials that can be used for the high-refractive-index layer include titanium, zirconium, aluminum, niobium, tantalum, and lanthanum oxide. Examples of materials that can be used for the low-refractive-index layer include silica oxide. Examples of methods for manufacturing the anti-reflection layer include dry methods such as vacuum deposition, sputtering, ion plating, ion-beam assisted deposition, and CVD.

[0097] The composition of the present disclosure will be described in more detail below with reference to examples and comparative examples, but the composition of the present disclosure is not limited by these examples in any way.

[0098] Example 1 Primer Layer Preparation of Primer Layer-Forming Composition Pure water (83 parts by mass), UW-1013D-C1 (manufactured by UBE, solids content 34% by mass) (113.4 parts by mass) as an aqueous urethane dispersion, Carbodilite V-02 (manufactured by Nisshinbo Chemical Inc., solids content 39.9%) (2.0 parts by mass), and a 10% by mass aqueous solution of DOWSIL 501W Additive (0.8 parts by mass) and a 10% by mass aqueous solution of DOWSIL L-7604 (0.8 parts by mass) as surfactants were mixed and stirred to prepare a primer layer-forming composition with a solids concentration of 20% by mass.

[0099] - 10% DOWSIL 501W Additive Aqueous Solution - Pure water (9 parts by mass) and DOWSIL 501W Additive (manufactured by Dow Corp.) (1 part by mass) were added and stirred to prepare a 10% by mass aqueous solution of DOWSIL 501W Additive.

[0100] - 10% DOWSIL L-7604 Aqueous Solution - Pure water (9 parts by mass) and DOWSIL L-7604 (manufactured by Dow Corp.) (1 part by mass) were added and stirred to prepare a 10% by mass aqueous solution of DOWSIL L-7604.

[0101] (Formation of Primer Layer) A spectacle lens substrate with a refractive index of 1.74 (S-7.00D, manufactured by Nikon-Essilor) was used as the spectacle lens substrate. A primer layer-forming composition (1.0 mL) was dropped onto one side of the spectacle lens substrate and spin-coated. In the spin-coating, the spectacle lens substrate coated with the primer layer-forming composition was rotated in this order at 500 rpm for 10 seconds, at 2000 rpm for 0.5 seconds, and finally at 0 rpm over 1 second. Next, the obtained substrate was heated at 90°C for 20 minutes to form a first coating film. In addition, a first coating film was formed on the other side of the spectacle lens substrate of the obtained substrate using the same procedure as above. The obtained substrate was used as a spectacle lens substrate with a first coating film.

[0102] <Hard Coating Layer> (Preparation of Prepolymer Solution) The copper complex solution (4.5 parts by mass), AC-SQ TA-100 (manufactured by Toagosei Co., Ltd., 20 parts by mass), N,N,N',N'',N''-pentamethyldiethylenetriamine (manufactured by Tokyo Chemical Industry Co., Ltd., 0.61 parts by mass), and ethyl 2-chloropropionate (manufactured by Tokyo Chemical Industry Co., Ltd., 0.017 parts by mass) were mixed and stirred (stirring time: 1 hour) to prepare prepolymer solution 1-1.

[0103] - Copper Complex Solution - Tetrahydrofuran (89 parts by mass), copper(I) bromide (manufactured by Tokyo Chemical Industry Co., Ltd., 0.05 parts by mass), and diphenylphosphine oxide (manufactured by Tokyo Chemical Industry Co., Ltd., 5.28 parts by mass) were added and stirred to prepare a copper complex solution.

[0104] —10% by mass Ominirad 127 Solution— Methyl ethyl ketone (18.0 parts by mass) and Ominirad 127 solution (manufactured by IGM Resins BV, 2.0 parts by mass) were added and stirred to prepare a 10% by mass Ominirad 127 solution.

[0105] - 10 mass % L7001 Solution - Methyl ethyl ketone (9 parts by mass) and DOWSIL L-7001 (manufactured by Dow Chemical, 1 part by mass) were added and stirred to prepare a 10 mass % L7001 solution.

[0106] (Preparation of hard coat layer-forming composition) Prepolymer solution 1-1 (12.6 parts by mass), methyl ethyl ketone (0.58 parts by mass), tetrahydrofuran (6.5 parts by mass), NK Ester A-600 (manufactured by Shin-Nakamura Chemical Co., Ltd.) (10 parts by mass), 10% by mass Ominirad 127 solution (manufactured by IGM Resins B.V., 0.202 parts by mass), and 10% by mass L7001 solution (0.11 parts by mass) were mixed to prepare hard coat layer-forming composition J1.

[0107] (Formation of hard coat layer) A hard coat layer-forming composition J1 (2.0 mL) was dropped onto one of the first coating films of the obtained eyeglass lens substrate with a first coating film, and spin-coated to form a second coating film. The spin-coating was performed by rotating the lens at 500 rpm for 10 seconds, at 2000 rpm for 0.5 seconds, and finally at 0 rpm over 1 second, in this order. Thereafter, the first coating film and the second coating film were irradiated with ultraviolet light (cumulative light dose: 0.8 J / cm) using a high-pressure mercury lamp (Fusion UV, LIGHT HAMMER 6, manufactured by Heraeus) as a light source. ２ ) was applied. Next, the hard coat layer-forming composition J1 was dropped onto the surface of the obtained substrate opposite to the side on which the hard coat layer-forming composition J1 was applied, and spin coating and ultraviolet irradiation were carried out under the same conditions as for the side on which the hard coat layer-forming composition J1 was applied. The obtained substrate was heated at 100°C for 20 minutes to obtain the eyeglass lens of Example 1 having, in this order, a hard coat layer, a primer layer, an eyeglass lens substrate, a primer layer, and a hard coat layer.

[0108] [Examples 2 to 4, 8 to 10, Comparative Examples 1 to 3] In Examples 2 to 4, 8 to 10 and Comparative Examples 1 to 3, each spectacle lens was obtained in the same manner as in Example 1, except that the various components and their contents were changed as shown in the table below.

[0109] Examples 5 to 7 Each spectacle lens was obtained in the same manner as in Example 1, except that prepolymer liquid 2-1 or 2-2 was prepared in the following manner and used instead of prepolymer liquid 1-1.

[0110] <Preparation of Prepolymer Solution 2-1> Tetrahydrofuran (634.1 parts by mass), copper(I) bromide (manufactured by Tokyo Chemical Industry Co., Ltd., 0.0052 parts by mass), diphenylphosphine oxide (manufactured by Tokyo Chemical Industry Co., Ltd., 0.54 parts by mass), NK Ester A-600 (manufactured by Shin-Nakamura Chemical Co., Ltd., 71.3 parts by mass), and N,N,N',N",N"-pentamethyldiethylenetriamine (manufactured by Tokyo Chemical Industry Co., Ltd., 1.25 parts by mass) were added and stirred for 16 hours. Next, 581.1 parts by mass of tetrahydrofuran was removed from the resulting solution using an evaporator (NE-1101, manufactured by Tokyo Rikakikai Co., Ltd.), to prepare prepolymer solution 2-1.

[0111] <Preparation of Prepolymer Liquid 2-2> Prepolymer liquid 2-2 was obtained in the same manner as prepolymer liquid 2-1, except that the components and their contents were changed as shown in the table below.

[0112] [Molecular Weight Analysis of Polymer S and Polymer P] Molecular weight distribution curves of polymer S and polymer P in each prepolymer liquid were prepared by the method described above, and the peak-top molecular weight and molecular weight distribution were measured. When the prepolymer liquid contained polymer S, the prepolymer liquid contained polymer S:silsesquioxane having a polymerizable group at a molar ratio of 30:70 to 80:20. When the prepolymer liquid contained polymer P, the prepolymer liquid contained polymer P:monomer X at a molar ratio of 30:70 to 40:60. The molecular weights of polymer S and polymer P were adjusted by adjusting the various components contained in each prepolymer liquid and their contents, as well as the stirring time and amount of solvent removed when preparing each prepolymer.

[0113] [Interlayer Adhesion] The interlayer adhesion of the hard coat layer in each spectacle lens was evaluated using a cross-cut tape test according to the following procedure. Using a knife, slits were made in the obtained spectacle lens at 1 mm intervals from the concave side of the sample, reaching down to the spectacle lens substrate, forming 25 grids. Next, Scotch tape (manufactured by 3M) was firmly pressed onto the slit hard coat layer, and the Scotch tape was quickly pulled once at a 45° angle from the tape-attached surface with a load of 4 kg to peel it off. The total number of grids remaining on the substrate (the total number of grids consisting of the substrate, primer layer, and hard coat layer) was then counted, and the interlayer adhesion of the hard coat layer was evaluated according to the following evaluation criteria: A: The number of remaining grids was 11 or more; B: The number of remaining grids was 10 or less.

[0114] In Table 1, the units of the contents of the various components are parts by mass.

[0115]

[0116] Copper complex solution: As described above. AC-SQ TA-100: Silsesquioxane having a polymerizable group, manufactured by Toagosei Co., Ltd. NK Ester A-600: Polyalkylene glycol di(meth)acrylate, manufactured by Shin-Nakamura Chemical Co., Ltd. NK Oligo UA-232P: Mixture of urethane (meth)acrylate and AMP-20GY (phenoxydiethylene glycol acrylate) (70:30 (mass ratio), manufactured by Shin-Nakamura Chemical Co., Ltd.)

[0117] The meaning of each description in Table 2 is as follows. The content of each component indicates the value (% by mass) relative to the total solid content of the composition. The column "Polymer S + TA100" indicates the total content (% by mass) of Polymer S and AC-SQ TA-100 relative to the total solid content of the composition. The column "Polymer P + A600" indicates the total content (% by mass) of Polymer P and NK Ester A-600 relative to the total solid content of the composition. In each example, when the composition contains a silsesquioxane having a polymerizable group, the column "Requirement A or Requirement B" indicates the value of the total content of Polymer S and silsesquioxane having a polymerizable group relative to the total content of Polymer S, silsesquioxane having a polymerizable group, and Compound X (the value of any one of Requirements A1 to A4). Furthermore, when the composition does not contain a silsesquioxane having a polymerizable group, the column indicates the value of the content of Polymer S relative to the total content of Polymer S and Compound X (the value of any one of Requirements B1 to B4). The column "Requirement C or Requirement D" indicates, in each example, the value of the total content of polymer P and monomer M relative to the total content of polymer P, monomer M, and silsesquioxane having a polymerizable group when the composition contains monomer M (the value of any of requirements C1 to C4). Furthermore, when the composition does not contain monomer M, the value of the content of polymer P relative to the total content of polymer P and silsesquioxane having a polymerizable group (the value of any of requirements D1 to D4). The column "Mp" indicates the peak top molecular weight of each compound. TA100 had two peak top molecular weights, and the components other than TA100 each had one peak top molecular weight. The column "Mw" indicates the weight average molecular weight of each compound. Note that the Mp and molecular weight distribution for "UA232P (urethane (meth)acrylate)" in the table are values ​​for only the urethane (meth)acrylate contained in UA232P, and do not include AMP-20GY (phenoxydiethylene glycol acrylate). The "molecular weight distribution" column indicates the region (molecular weight range) in which the molecular weight of each polymer exists in the molecular weight distribution curve of each polymer obtained by GPC.

[0118]

[0119]

[0120] As shown in Table 2, it was confirmed that the composition of the present disclosure can form a hard coat layer having excellent interlayer adhesion.

[0121] 10 eyeglass lens 12 eyeglass lens substrate 14 primer layer 16 hard coat layer

Claims

1. Polymer S of silsesquioxane having polymerizable groups, A compound X selected from the group consisting of monomer M and polymer P of the monomer M, The monomer M is selected from the group consisting of polyalkylene glycol di(meth)acrylate and urethane(meth)acrylate. In the molecular weight distribution curve of the polymer S obtained by gel permeation chromatography, the peak top molecular weight of the polymer S is 2800 or more. A composition in which, in the molecular weight distribution curve of the polymer P obtained by gel permeation chromatography, the peak top molecular weight of the polymer P is 3500 or more.

2. The composition contains a silsesquioxane having a polymerizable group and satisfies requirement A1, or The composition according to claim 1, wherein the composition does not contain a silsesquioxane having a polymerizable group and satisfies requirement B1. Requirement A1: The total content of the polymer S and the silsesquioxane having polymerizable groups is 30% by mass or more relative to the total content of the polymer S, the silsesquioxane having polymerizable groups, and the compound X. Requirement B1: The content of the polymer S is 5% by mass or more of the total content of the polymer S and the compound X.

3. The composition contains a silsesquioxane having a polymerizable group and satisfies requirement A3, or The composition according to claim 1 or 2, wherein the composition does not contain a silsesquioxane having a polymerizable group and satisfies requirement B3. Requirement A3: The total content of the polymer S and the silsesquioxane having polymerizable groups is 30 to 90% by mass relative to the total content of the polymer S, the silsesquioxane having polymerizable groups, and the compound X. Requirement B3: The content of polymer S is 5 to 65% by mass relative to the total content of polymer S and compound X.

4. A silsesquioxane having a polymerizable group, The polymer P comprises a monomer M selected from the group consisting of polyalkylene glycol di(meth)acrylate and urethane (meth)acrylate, A composition in which, in the molecular weight distribution curve of the polymer P obtained by gel permeation chromatography, the peak top molecular weight of the polymer P is 3500 or more.

5. The composition comprises a monomer M selected from the group consisting of polyalkylene glycol di(meth)acrylate and urethane(meth)acrylate, and satisfies requirement C1, or The composition according to claim 4, wherein the composition does not contain monomer M selected from the group consisting of polyalkylene glycol di(meth)acrylate and urethane(meth)acrylate, and satisfies requirement D1. Requirement C1: The total content of polymer P and monomer M is 30% by mass or more relative to the total content of polymer P, monomer M, and silsesquioxane having polymerizable groups. Requirement D1: The content of polymer P is 10% by mass or more relative to the total content of polymer P and the silsesquioxane having polymerizable groups.

6. The composition comprises a monomer M selected from the group consisting of polyalkylene glycol di(meth)acrylate and urethane(meth)acrylate, and satisfies requirement C3, or The composition according to claim 4 or 5, wherein the composition does not contain monomer M selected from the group consisting of polyalkylene glycol di(meth)acrylate and urethane (meth)acrylate, and satisfies requirement D3. Requirement C3: The total content of polymer P and monomer M is 30 to 90% by mass relative to the total content of polymer P, monomer M, and silsesquioxane having polymerizable groups. Requirement D3: The content of polymer P is 10 to 80% by mass relative to the total content of polymer P and the silsesquioxane having polymerizable groups.

7. The polyalkylene glycol di(meth)acrylate is a compound represented by formula (II), The composition according to claim 1 or 4, wherein the urethane (meth)acrylate is a compound represented by formula (I). 【Chemistry 1】 In formula (II), n represents a number between 0 and 30. R ３ and R ４ Each of these independently represents either a hydrogen atom or a methyl group. 【Chemistry 2】 In formula (I), m represents a number from 0 to 9. R represents a bifunctional polyester polyol residue or a bifunctional polyether polyol residue. １ R represents a hydrogen atom or a methyl group. ２ represents an alkylene group having 2 to 4 carbon atoms. L represents a group represented by any of formulas (I-1) to (I-3).

8. Eyeglass lens base material, An eyeglass lens comprising a hard coat layer formed using the composition described in claim 1 or 4, which is disposed on the eyeglass lens substrate.

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