Compound and cured product

Abstract

The purpose of the present invention is to provide a compound having a high refractive index. The present invention relates to a compound represented by general formula (1). In formula (1), R1 denotes an organic group including an aromatic ring having 10 or more carbon atoms in the structure thereof, an organic group including an aromatic heterocyclic ring, an organic group including a structure in which two or more benzene rings are bonded either directly or via a carbon atom, an oxygen atom, a sulfur atom, -CH-, -C(CH3)2-, -SO- or -SO2-, an organic group represented by general formula (2), or an organic group represented by general formula (3). Z moieties may be the same as, or different from, each other, and each denote -CR2R3-, -O-, -S- or -NH-. R2 and R3 may be the same as, or different from, each other, and each denote a hydrogen atom or a methyl group. n values may be the same as, or different from, each other, and are each an integer between 0 and 20. m denotes an integer between 1 and 3.) (In formula (2), R21 denotes a direct bond or an alkylene group. R22 moieties may be the same as, or different from, each other, and each denote a halogen atom. a denotes an integer between 1 and 3. In formula (3), R31 denotes an unsaturated aliphatic hydrocarbon group. R32 moieties may be the same as, or different from, each other, and each denote a substituent group. b denotes an integer between 0 and 5.

Description

Compound and cured product

[0001] The present invention relates to a compound and a cured product thereof, and more particularly to a compound having a high refractive index and a cured product thereof.

[0002] In recent years, the demand for high refractive index materials has increased due to the trend toward thinner displays and wider viewing angles. Known high refractive index materials include inorganic particles such as titanium and zirconia, and organic materials having a fluorene skeleton. However, these are solids or highly viscous liquids, and require a reactive diluent to be used as a composition.

[0003] A reactive diluent is a polymerizable monomer that has low viscosity and is compatible with various compounds, and can form a viscous liquid substance or a hard solid substance through a polymerization reaction. Various such compounds have been known so far (see, for example, Patent Documents 1 and 2).

[0004] JP 2011-137123 A JP 2015-120681 A

[0005] However, conventional compounds that can be used as reactive diluents still have low refractive indices and do not fully satisfy the recent demand for high refractive indices, so new compounds with high refractive indices have been desired.

[0006] The present invention has been made in view of the above-mentioned current situation, and has an object to provide a compound having a high refractive index.

[0007] The present inventors have conducted extensive research into compounds that can be used as reactive diluents and have found that compounds with a specific structure have a high refractive index, leading to the completion of the present invention.

[0008] That is, the present invention provides the following aspects: <1> A compound represented by the following general formula (1):

[0009]

[0010] (In formula (1), R １ represents an organic group containing an aromatic ring having 10 or more carbon atoms in its structure, an organic group containing an aromatic heterocycle, or two or more benzene rings bonded directly or bonded to a carbon atom, an oxygen atom, a sulfur atom, -CH-, -C(CH３ ) ２ -, -SO- or -SO ２ Z represents an organic group having a structure bonded via -, an organic group represented by the following general formula (2), or an organic group represented by the following general formula (3). ２ R ３ represents -, -O-, -S- or -NH-. ２ and R ３ are the same or different and represent a hydrogen atom or a methyl group; n is the same or different and represents an integer of 0 to 20; and m is an integer of 1 to 3.

[0011]

[0012] (In formula (2), R ２１ represents a direct bond or an alkylene group. ２２ are the same or different and represent a halogen atom; and a represents an integer of 1 to 3.

[0013]

[0014] (In formula (3), R ３１ represents an unsaturated aliphatic hydrocarbon group. ３２ are the same or different and represent a substituent. b represents an integer of 0 to 5. <2> The compound according to the above <1>, having a refractive index calculated according to the Hansen Solubility Parameter of Practice of 1.54 or more. <3> A cured product obtained by curing the compound according to the above <1> or <2>.

[0015] The compound of the present invention has a high refractive index and can be suitably used as a reactive diluent for optical materials and the like.

[0016] The present invention will be described in detail below. Note that a combination of two or more of the individual preferred embodiments of the present invention described below is also a preferred embodiment of the present invention.

[0017] The compound of the present invention is characterized by being represented by the following general formula (1).

[0018]

[0019] (In formula (1), R １represents an organic group containing an aromatic ring having 10 or more carbon atoms in its structure, an organic group containing an aromatic heterocycle, or two or more benzene rings bonded directly or bonded to a carbon atom, an oxygen atom, a sulfur atom, -CH-, -C(CH ３ ) ２ -, -SO- or -SO ２ Z represents an organic group having a structure bonded via -, an organic group represented by the following general formula (2), or an organic group represented by the following general formula (3). ２ R ３ represents -, -O-, -S- or -NH-. ２ and R ３ are the same or different and represent a hydrogen atom or a methyl group; n is the same or different and represents an integer of 0 to 20; and m is an integer of 1 to 3.

[0020] The compound of the present invention has a high refractive index. The high refractive index of the compound is believed to be due to the presence of an aromatic ring or an aromatic heterocycle in the structure.

[0021] Compound The compound of the present invention is represented by the above general formula (1). Hereinafter, in this specification, the compound represented by the above general formula (1) will also be referred to as compound (A).

[0022] In the above general formula (1), R １ represents an organic group selected from the following 1) to 5): 1) an organic group containing an aromatic ring having 10 or more carbon atoms in its structure; 2) an organic group containing an aromatic heterocycle; 3) an organic group in which two or more benzene rings are directly bonded or bonded to one another by a carbon atom, an oxygen atom, a sulfur atom, -CH-, -C(CH ３ ) ２ -, -SO- or -SO ２ 4) An organic group represented by the following general formula (2):

[0023] (In formula (2), R ２１ represents a direct bond or an alkylene group. ２２ are the same or different and represent a halogen atom; a represents an integer of 1 to 3; 5) An organic group represented by the following general formula (3):

[0024] (In formula (3), R ３１represents an unsaturated aliphatic hydrocarbon group. ３２ are the same or different and represent a substituent; and b represents an integer of 0 to 5.

[0025] The organic group 1) above contains an aromatic ring having 10 or more carbon atoms in its structure. In this specification, the term "aromatic ring" refers to an aromatic hydrocarbon ring such as a benzene ring, a condensed ring of a benzene ring, a condensed ring of a benzene ring and an alicyclic ring, or a ring formed by a single bond between the condensed rings.

[0026] Examples of the alicyclic ring include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a norbornene ring, and an adamantane ring.

[0027] Examples of the aromatic ring having 10 or more carbon atoms include a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a perylene ring, a fluorene ring, a fluoranthene ring, and a binaphthyl ring.

[0028] The aromatic ring having 10 or more carbon atoms preferably has 10 to 40 carbon atoms, more preferably 10 to 30 carbon atoms, and even more preferably 10 to 25 carbon atoms.

[0029] The number of atoms constituting the aromatic ring is preferably 10 or more, more preferably 10 to 60, and even more preferably 10 to 50.

[0030] The aromatic ring may have a substituent. Examples of the substituent include hydrocarbon groups (e.g., alkyl groups), hydroxy groups, alkoxy groups, carboxyl groups, nitrogen-containing groups (e.g., amino groups, imino groups, nitro groups, nitroso groups), halogen atom-containing substituents (e.g., halogeno groups), sulfur atom-containing substituents (e.g., thiol groups, thioether groups, sulfoxide groups, sulfone groups), etc. Among these, halogen atom-containing substituents and sulfur atom-containing substituents are preferred.

[0031] The number of substituents on the aromatic ring is not particularly limited, but is preferably 0 to 10, more preferably 0 to 8, and even more preferably 0 to 5.

[0032] The organic group containing an aromatic ring having 10 or more carbon atoms in the above structure includes a group consisting of an aromatic ring having 10 or more carbon atoms which may have a substituent, or a group consisting of an aromatic ring having 10 or more carbon atoms which may have a substituent and a hydrocarbon chain, -S- and -SO ２ - and at least one selected from the group consisting of. The group consisting solely of an aromatic ring having 10 or more carbon atoms which may have a substituent includes a monovalent to trivalent group formed by removing 1 to 3 hydrogen atoms from the aromatic ring having 10 or more carbon atoms. The hydrocarbon chain is preferably a divalent aliphatic hydrocarbon group or an aromatic hydrocarbon group. The divalent aliphatic hydrocarbon group is preferably an alkylene group, more preferably an alkylene group having 1 to 5 carbon atoms, and even more preferably an alkylene group having 1 to 3 carbon atoms. The divalent aromatic hydrocarbon group is preferably a phenylene group.

[0033] The organic group of 2) above includes an aromatic heterocycle, for example, an aromatic heterocycle in which one or more carbon atoms constituting the aromatic ring are substituted with an oxygen atom, a nitrogen atom, or a sulfur atom.

[0034] Examples of the aromatic heterocycle include a thiophene ring, a furan ring, a pyrrole ring, a thiopyran ring, a thiazole ring, an imidazole ring, a pyrazole ring, a triazole ring, a tetrazole ring, a thiazole ring, a thiadiazole ring, an oxadiazole ring, an oxazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, an isoindole ring, an indole ring, an indazole ring, a purine ring, an isoquinoline ring, a quinoline ring, a carbazole ring, an acridine ring, a benzofuran ring, a dibenzofuran ring, a naphthofuran ring, a dinaphthofuran ring, a benzothiophene ring, a dibenzothiophene ring, a naphthothiophene ring, a dinaphthothiophene ring, etc. Among these, in terms of a high refractive index, the aromatic heterocycle preferably contains a sulfur atom, and a thiophene ring, a thiazole ring, a thiadiazole ring, a benzothiophene ring, a dibenzothiophene ring, a naphthothiophene ring, or a dinaphthothiophene ring is more preferred.

[0035] The number of atoms constituting the aromatic heterocycle is preferably 5 or more, more preferably 5 to 50, and even more preferably 5 to 40.

[0036] The aromatic heterocycle may have a substituent. Examples of the substituent include an alkyl group, a cycloalkyl group, a hydroxy group, an alkoxy group, a carboxyl group, a nitrogen-containing group (e.g., an amino group, an imino group, a nitro group, a nitroso group), a substituent containing a halogen atom (e.g., a halogeno group), and a substituent containing a sulfur atom (e.g., a thiol group, a thioether group, a sulfoxide group, a sulfone group). Among these, a substituent containing a halogen atom and a substituent containing a sulfur atom are preferred.

[0037] The number of substituents on the aromatic heterocycle is not particularly limited, but is preferably 0 to 10, more preferably 0 to 8, and even more preferably 0 to 5.

[0038] Examples of the organic group containing an aromatic heterocycle include a group consisting of the above-mentioned aromatic heterocycle, which may have a substituent, or a group consisting of the above-mentioned aromatic heterocycle, which may have a substituent, and a hydrocarbon chain. Examples of the group consisting of the above-mentioned aromatic heterocycle, which may have a substituent, include monovalent to trivalent groups formed by removing 1 to 3 hydrogen atoms from the above-mentioned aromatic heterocycle. The hydrocarbon chain is preferably a divalent aliphatic hydrocarbon group, more preferably an alkylene group having 1 to 10 carbon atoms.

[0039] The organic group in 3) above is a group in which two or more benzene rings are directly bonded or bonded to one another through a carbon atom, an oxygen atom, a sulfur atom, -CH-, -C(CH ３ ) ２ -, -SO- or -SO ２ - includes structures bonded via.

[0040] The structure in which two or more benzene rings are directly bonded is preferably a structure in which two to five benzene rings are directly bonded, more preferably a structure in which two to four benzene rings are directly bonded (single bond), and further preferably a biphenyl group or a terphenyl group.

[0041] The two or more benzene rings are each independently selected from the group consisting of a carbon atom, an oxygen atom, a sulfur atom, —CH—, —C(CH ３ ) ２ -, -SO- or -SO ２ The structure in which two or more benzene rings are bonded via - has a higher refractive index and is preferably formed by bonding two or more benzene rings via a carbon atom, a sulfur atom, -SO- or -SO ２ A structure in which the bond is formed via - is preferred, and a sulfur atom, -SO- or -SO ２ A structure in which they are bonded via - is more preferred.

[0042] The two or more benzene rings may have a substituent. Examples of the substituent include an alkyl group, a cycloalkyl group, a hydroxy group, an alkoxy group, a carboxyl group, a nitrogen-containing group (e.g., an amino group, an imino group, a nitro group, a nitroso group), a substituent containing a halogen atom (e.g., a halogeno group), and a substituent containing a sulfur atom (e.g., a thiol group, a thioether group, a sulfoxide group, a sulfone group). Among these, a substituent containing a halogen atom and a substituent containing a sulfur atom are preferred.

[0043] The organic group of the above 3) is preferably a group in which the two or more benzene rings are directly bonded or bonded to one another through a carbon atom, an oxygen atom, a sulfur atom, —CH—, —C(CH ３ ) ２ -, -SO- or -SO ２ It is an organic group consisting of only a structure bonded via -, or an organic group consisting of a combination of the above structure and an alkylene chain.

[0044] The organic group in 4) above is represented by the general formula (2). In the general formula (2), R ２１ represents a direct bond or an alkylene group. The alkylene group preferably has 1 to 10 carbon atoms, and more preferably has 1 to 5 carbon atoms.

[0045] In the above general formula (2), R ２２ are the same or different and represent a halogen atom. The halogen atom is preferably an iodine atom, which has a higher refractive index.

[0046] In the above general formula (2), a represents an integer of 1 to 3. a is preferably an integer of 2 or more, and more preferably 3.

[0047] The organic group of the above 5) is represented by the above general formula (3). In the above general formula (3), R ３１ represents an unsaturated aliphatic hydrocarbon group. The unsaturated aliphatic hydrocarbon group preferably has 2 to 10 carbon atoms, and more preferably has 2 to 6 carbon atoms.

[0048] In the above general formula (3), R ３２ are the same or different and represent a substituent. ３２ Examples of the substituent represented by the formula (I) include an alkyl group, a cycloalkyl group, a hydroxy group, an alkoxy group, a carboxyl group, a nitrogen-containing group (e.g., an amino group, an imino group, a nitro group, a nitroso group), a substituent containing a halogen atom (e.g., a halogeno group), a substituent containing a sulfur atom (e.g., a thiol group, a thioether group, a sulfoxide group, a sulfone group), etc. Among these, a substituent containing a halogen atom and a substituent containing a sulfur atom are preferred.

[0049] In the above general formula (3), b represents an integer of 0 to 5.

[0050] The molecular weight of the organic groups 1) to 5) above is preferably 140 or more, more preferably 140 to 800, and even more preferably 140 to 700. The molecular weight of the organic group is the total atomic weight of the atoms constituting the organic group.

[0051] In the general formula (1), Z may be the same or different and represent -CR ２ R ３ represents -, -O-, -S- or -NH-. ２ and R ３ are the same or different and represent a hydrogen atom or a methyl group. Among these, Z is preferably —O— or —S—, and more preferably —O—.

[0052] In the general formula (1), n ​​may be the same or different and represents an integer of 0 to 20. n is preferably 0 to 15, more preferably 0 to 10, even more preferably 0 to 5, and particularly preferably 0.

[0053] In the above general formula (1), m represents an integer of 1 to 3.

[0054] The refractive index of compound (A) calculated using the practical Hansen solubility parameters is preferably 1.54 or greater, more preferably 1.55 or greater, even more preferably 1.56 or greater, even more preferably 1.57 or greater, and most preferably 1.58 or greater. The upper limit of the calculated refractive index is not particularly limited, but an example is 1.75. That is, the calculated refractive index is preferably 1.54 to 1.75, more preferably 1.55 to 1.75, even more preferably 1.56 to 1.75, even more preferably 1.57 to 1.75, and most preferably 1.58 to 1.75. The refractive index of compound (A) can be calculated using the practical Hansen solubility parameters. The refractive index according to the practical Hansen solubility parameters can be determined using the practical Hansen Solubility Parameters (HSPiP) software (version 5.3.08, manufactured by Pirika.com). Specifically, it is a value obtained using the refractive index calculation method described in the Examples below.

[0055] The glass transition temperature (hereinafter also referred to as polymer Tg) of the compound (A) as a homopolymer is preferably 25° C. or higher, more preferably 30° C. or higher, in terms of excellent heat resistance. The polymer Tg is a value determined by the method described in the examples below.

[0056] The viscosity of the compound (A) is preferably 5000 mPa·s or less, more preferably 2000 mPa·s or less, even more preferably 1000 mPa·s or less, even more preferably 500 mPa·s or less, and particularly preferably 300 mPa·s or less. The lower limit of the viscosity of the compound (A) is not particularly limited, but an example is 1 mPa·s. That is, the viscosity of the compound (A) is preferably 1 to 5000 mPa·s, more preferably 1 to 2000 mPa·s, even more preferably 1 to 1000 mPa·s, still more preferably 1 to 500 mPa·s, and particularly preferably 1 to 300 mPa·s. The viscosity is a value obtained by measurement at 25°C using a cone-plate viscometer, and specifically, a value obtained by the method described in the Examples below.

[0057] Specific examples of the compound (A) include the compounds shown below. Compound (A) having the organic group 1):

[0058] Compound (A) having an organic group as described in 2):

[0059] Compound (A) having an organic group as described in 3):

[0060] Compound (A) having an organic group as described in 4):

[0061] Compound (A) having an organic group as described in 5):

[0062]

[0063] The method for producing the compound (A) is not particularly limited, and examples thereof include a method of production via an α-halomethylacrylic acid alkyl ester, a method of production via a 2,2'-[oxybis(methylene)]bisacrylic acid alkyl ester, and a method of production utilizing a transesterification reaction from a lower ester of α-allyloxymethylacrylic acid such as methyl α-allyloxymethylacrylate. Among these, a method of production utilizing a transesterification reaction from a lower ester of α-allyloxymethylacrylic acid is preferred. The production method utilizing a transesterification reaction is described below.

[0064] The method for producing the compound (A) preferably includes a step of subjecting an α-allyloxymethyl acrylate ester and an alcohol to a transesterification reaction in the presence of a catalyst.

[0065] Preferred examples of the α-allyloxymethyl acrylic acid ester include lower α-allyloxymethyl acrylic acid ester compounds such as methyl α-allyloxymethyl acrylate, ethyl α-allyloxymethyl acrylate, n-propyl α-allyloxymethyl acrylate, i-propyl α-allyloxymethyl acrylate, n-butyl α-allyloxymethyl acrylate, s-butyl α-allyloxymethyl acrylate, t-butyl α-allyloxymethyl acrylate, n-amyl α-allyloxymethyl acrylate, s-amyl α-allyloxymethyl acrylate, and t-amyl α-allyloxymethyl acrylate. Among these, α-allyloxymethyl acrylic acid ester compounds having an alkyl group having 1 to 3 carbon atoms are more preferred, and methyl α-allyloxymethyl acrylate is even more preferred, in terms of ease of transesterification.

[0066] Examples of the alcohol include monohydric alcohols and polyhydric alcohols. Examples of the monohydric alcohol include linear or branched saturated alcohols such as methanol, ethanol, propanol, butanol, pentanol, hexanol, sec-hexanol, heptanol, n-octanol, 2-ethylhexanol, nonanol, decanol, undecanol, dodecanol (lauryl alcohol), tridecanol, myristyl alcohol, pentadecanol, cetyl alcohol, heptadecanol, stearyl alcohol, nodecyl alcohol, eicosyl alcohol, and melissyl alcohol. Alcohols having an aliphatic hydrocarbon group; alcohols having an alicyclic hydrocarbon group, such as cyclopentanol, cyclopentylmethanol, cyclohexanol, cyclohexylmethanol, 4-methylcyclohexanol, 4-tert-butylcyclohexanol, 3,3,5-trimethylcyclohexanol, tricyclodecane dimethanol, borneol, isoborneol, adamantanol, dicyclopentanyl alcohol, and dicyclopentenyl alcohol (hydroxydicyclopentadiene); 4-methoxy- Alcohols having a linear or branched ether group-based saturated hydrocarbon group, such as 1-butanol, 2-(2-methoxyethoxy)ethanol, 2-(2-ethoxyethoxy)ethanol, 2-(2-butoxyethoxy)ethanol, 2-(2-hexyloxyethoxy)ethanol, and 2,2-dimethyl-1,3-dioxolane-4-methanol; phenol, methylphenol, dimethylphenol, trimethylphenol, 4-tert-butylphenol, benzyl alcohol, 1-naphthalenemethanol, 3-phenoxyethanol; and alcohols having an aromatic hydrocarbon group or an aromatic heterocyclic group, such as dibenzyl alcohol, 2-(2-biphenylyloxy)ethanol, 4-phenylbenzyl alcohol, 9-fluorenylmethanol, diphenylethanol, cinnamyl alcohol, naphthol, anthrol, orthophenylphenol, 2-(1-naphthyloxy)ethanol, 2-(2-naphthyloxy)ethanol, 8-quinolinol, 2-(9H-carbazol-9-yl)ethanol, and 2-(2-naphthylthio)ethanol.

[0067] Examples of the polyhydric alcohol include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, hexaethylene glycol, heptaethylene glycol, octaethylene glycol, nonaethylene glycol, decaethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, hexapropylene glycol, heptapropylene glycol, octapropylene glycol, nonapropylene glycol, decapropylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-heptanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, polyethylene glycol, polypropylene glycol, hexanediol, neopentyl glycol, 1,4-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexane ... cyclohexanediol, 1,2-cyclohexanediol, 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,3-adamantanediol, tricyclodecane dimethanol, benzenedimethanol, 1,4-bis(2-hydroxyethoxy)-naphthalene, xylylene glycol, hydroquinone, bisphenol A, bisphenol F, bisphenol S, bisphenol fluorene, 3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetrahydrofuran, Examples of the alcohol include dihydric alcohols such as xaspiro[5,5]undecane and bis(hydroxypivalaldehyde) pentaerythritol acetal cyclic acetal; and trihydric or higher alcohols such as glycerin, polyglycerin, compounds in which alkylene glycol is added to glycerin, erythritol, xylitol, sorbitol, trimethylolethane, trimethylolpropane, pentaerythritol, ditrimethylolpropane, dipentaerythritol, and tris(2-hydroxyethyl) isocyanurate.

[0068] Examples of the catalyst include alkali metal hydroxides (e.g., lithium hydroxide, sodium hydroxide, potassium hydroxide, etc.), alkali metal carbonates (e.g., lithium carbonate, sodium carbonate, potassium carbonate, etc.), alkali metal alkoxides (e.g., lithium methoxide, sodium ethoxide, etc.), alkali metal amides (e.g., lithium amide, sodium amide, potassium amide, etc.), titanium alkoxides (e.g., tetraethyl orthotitanate, tetraisopropyl orthotitanate, etc.), organotin compounds (e.g., dibutyltin oxide), etc. Among these, titanium alkoxides are more preferred because the catalyst can be easily removed by washing with water.

[0069] The amount of the catalyst used is not particularly limited, but is preferably 0.1 to 10 mol %, more preferably 0.1 to 5 mol %, and even more preferably 1 to 5 mol %, relative to 100 mol % of the alcohol.

[0070] In the transesterification reaction, it is preferable to use a polymerization inhibitor. The polymerization inhibitor is not particularly limited, and examples thereof include benzoquinone, hydroquinones (e.g., hydroquinone, hydroquinone monomethyl ether, p-tert-butylhydroquinone, p-benzoquinone, etc.), phenols (e.g., 2,6-di-t-butyl-4-methylphenol, 6-t-butyl-2,4-xylenol, 2,2'-methylenebis(4-methyl-6-t-butylphenol), Irganox 245, Irganox Irganox 259, Irganox 565, Irganox 1010, Irganox MD1024, Irganox 1035, Irganox 1076, Irganox 1098, Irganox 1135, Irganox 1222, Irganox 1330, Irganox 3114 (all manufactured by BASF), Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO- 60, Adekastab AO-70, Adekastab AO-80, Adekastab AO-330 (all manufactured by ADEKA Corporation), RIANOX 245, RIANOX 330, RIANOX 1010, RIANOX 1019, RIANOX 1035, RIANOX 1076, RIANOX 1098, RIANOX 1135, RIANOX 1790, RIANOX 3114 (all manufactured by Rianlon Corporation), etc.), catechols (for example, p-tert-butyl ether, Examples of the polymerization inhibitor include known ones such as methyl catechol, amines (for example, N,N-diethylhydroxylamine), 1,1-diphenyl-2-picrylhydrazyl, tri-p-nitrophenylmethyl, phenothiazine, piperidine 1-oxyls (for example, 2,2,6,6-tetramethylpiperidine 1-oxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl), and Polystop 7300P (manufactured by Hakuto Co., Ltd.). One of the polymerization inhibitors may be used alone, or two or more of them may be used in combination.

[0071] The amount of the polymerization inhibitor used is not particularly limited, but is preferably 0.01 to 0.5 parts by mass, more preferably 0.01 to 0.3 parts by mass, and even more preferably 0.01 to 0.2 parts by mass, relative to 100 parts by mass of the α-(allyloxymethyl)acrylic acid ester.

[0072] A solvent may be used in the transesterification reaction. The solvent to be used is not particularly limited as long as it does not affect the reaction, and examples thereof include hydrocarbon solvents such as benzene, toluene, xylene, hexane, heptane, octane, and cyclohexane, and ether solvents such as dioxane and tetrahydrofuran. The above solvents may be used alone or in combination of two or more.

[0073] The reaction conditions for the transesterification reaction are not particularly limited and may be any known reaction conditions, and the reaction temperature is preferably 50 to 120° C., more preferably 50 to 110° C. The transesterification reaction may be carried out under normal pressure or under reduced pressure.

[0074] The method for producing the compound (A) may include a step of washing the reaction product obtained in the transesterification reaction step with water, which can remove unnecessary components such as the catalyst and lower alcohol contained in the reaction product.

[0075] The water washing is not particularly limited and can be carried out by a known method, such as adding an acidic aqueous solution (e.g., an oxalic acid aqueous solution) or water (e.g., distilled water, ion-exchanged water) to the organic phase containing the reaction product, stirring, and allowing to stand to separate the oil and water.

[0076] The method for producing the compound (A) may include a step of purifying the reaction product. The purification method is not particularly limited and can be appropriately selected from known purification methods such as distillation, extraction, and filtration. The purified compound (A) can be obtained by the purification step.

[0077] The method for producing the compound (A) may further include other steps. Examples of the other steps include a dilution step, a drying step, a concentration step, a solvent substitution step, a dissolution step, a solvent evaporation step, a thin film distillation step, and a steam distillation step. These steps can be carried out by known methods.

[0078]

[0033] The present invention also encompasses a cured product obtained by curing the compound (A). The method for curing the compound (A) to obtain the cured product is not particularly limited, and examples include heating, irradiation with active energy rays, and a combination of these.

[0079] Heating can be carried out by a known method. The temperature condition for heat curing is, for example, preferably 30 to 400° C., more preferably 70 to 350° C. The curing by heating may be carried out in one step or in two or more steps, and may be carried out before or after curing by irradiation with active energy rays.

[0080] As the active energy ray, any commonly used ray can be used, including electromagnetic waves such as gamma rays, X-rays, ultraviolet rays, visible light, and infrared rays, and particle rays such as electron beams, neutron beams, and proton beams. Of these, ultraviolet rays are preferred.

[0081] Curable Composition The compound (A) can be used in combination with other components to form a curable composition.

[0082] The content of the compound (A) in the curable composition is not particularly limited and may be appropriately set depending on the purpose and use of the curable composition. However, the content is preferably 0.1 to 90 mass %, and more preferably 0.1 to 80 mass %, relative to 100 mass % of the non-volatile components of the curable composition.

[0083] In addition to the compound (A), the curable composition may contain one or more other components (B) depending on the purpose and application. The other components (B) are not particularly limited, and include, for example, polymerizable compounds other than the compound (A), curing accelerators (radical polymerization initiators, radical polymerization accelerators, photosensitizers, etc.), stabilizers, binder resins, solvents, fillers, colorants, dispersants, adhesion improvers, release agents, plasticizers, UV absorbers, matting agents, antifoaming agents, leveling agents, antistatic agents, slip agents, surface modifiers, coupling agents (silane-based, aluminum-based, titanium-based, etc. coupling agents), acid generators, etc. Among them, the curable composition preferably contains other polymerizable compounds, curing accelerators, stabilizers, or solvents.

[0084] Examples of polymerizable compounds other than the compound (A) include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, i-propyl (meth)acrylate, n-butyl (meth)acrylate, s-butyl (meth)acrylate, t-butyl (meth)acrylate, n-amyl (meth)acrylate, s-amyl (meth)acrylate, t-amyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, and isobol (meth)acrylate. (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, phenoxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, glycidyl (meth)acrylate, (3,4-epoxycyclohexyl)methyl (meth)acrylate, and N,N-dimethylaminoethyl (meth)acrylate; and the like, as well as monofunctional or polyfunctional radically polymerizable monomers described in paragraphs

[0052] to

[0053] of JP-A 2011-137123.

[0085] Examples of the curing accelerator include peroxide-based polymerization initiators such as methyl ethyl ketone peroxide, cyclohexanone peroxide, methylcyclohexanone peroxide, and methyl acetoacetate peroxide; azo-based polymerization initiators such as 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 1-[(1-cyano-1-methylethyl)azo]formamide, 1,1'-azobis(cyclohexane-1-carbonitrile), and 2,2'-azobis(2-methylbutyronitrile); photoradical polymerization initiators such as 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, and 1-hydroxycyclohexyl phenyl ketone; and radical polymerization initiators, radical polymerization accelerators, and photosensitizers described in JP-A-2011-137123.

[0086] Examples of the stabilizer include commonly used polymerization inhibitors and antioxidants, such as phenolic compounds, organic acid copper salts, phenothiazines, phosphites, thioethers, and hindered amine compounds, as well as stabilizers described in JP-A-2011-137123.

[0087] Examples of the solvent include monoalcohols such as methanol, ethanol, isopropanol, n-butanol, and s-butanol; glycols such as ethylene glycol and propylene glycol; cyclic ethers such as tetrahydrofuran and dioxane; glycol monoethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, and diethylene glycol monomethyl ether; and solvents described in JP-A-2011-137123.

[0088] The content of each of the other components (B) can be appropriately set depending on the purpose and application of the curable composition.

[0089] The curable composition can be prepared by mixing the compound (A) with, if necessary, another component (B). The mixing method is not particularly limited, and can be carried out by mixing and dispersing using any of various known mixers or dispersers.

[0090] The method for curing the curable composition to obtain a cured product is not particularly limited, and examples thereof include heating, irradiation with active energy rays, and a combination thereof. These methods may be appropriately selected from known methods depending on the components contained in the curable composition. Examples of the heating and irradiation with active energy rays include the same methods as those described above.

[0091]

[0023] The compound (A) can provide a high refractive index, and therefore can be suitably used as an optical material such as a high refractive index material. Furthermore, the compound (A) has a structure in which an allyloxymethyl group is introduced at the α-position of an alkyl acid ester, and thus can exhibit a lower viscosity than an acrylic acid ester having a substituent of the same structure. Because the compound (A) has such a low viscosity, it can also be used as a reactive diluent, and can be suitably used as a reactive diluent for compositions for optical materials.

[0092] The curable composition containing the compound (A) has a low viscosity and a high refractive index, and is therefore suitable for use in applications where a low viscosity and a high refractive index are required.

[0093] The compound (A) and the curable composition can be suitably used for applications such as coating materials, adhesives, sealants, pressure-sensitive adhesives, primers, paints, inks, dental materials, resists, optical materials such as lenses, molding materials, etc. The curable composition is preferably used for optical materials because it gives a cured product with a high refractive index.

[0094] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, "%" means "% by mass."

[0095] The evaluation methods used in the examples are as follows: <Viscosity> The viscosity of the compound was measured at a temperature of 25°C using a cone-plate viscometer (DV1MRVCJ0, manufactured by Brookfield).

[0096] <Refractive Index> (Calculated Values) The refractive indexes of compounds (A-1) to (A-40) in Examples 1 to 40 and compounds (B-1) to (B-14) in Comparative Examples 1 to 14 were determined using Hansen Solubility Parameter in Practice (HSPiP) software (version 5.3.08, manufactured by Pirika.com). (Measured Values) The refractive indexes of compounds (A-1) to (A-5) in Examples 1 to 5 and compounds (B-1) and (B-14) in Comparative Examples 1 and 14 were measured using a multi-wavelength Abbe refractometer DR-M4 manufactured by ATAGO (measurement temperature 25°C, interference filter wavelength 589(D) nm). The refractive indexes of the compounds (B-2) to (B-4) of Comparative Examples 2 to 4 were measured using an Abbe refractometer NAR-1T LIQUID type manufactured by ATAGO (measurement temperature 25°C, wavelength 589 (D) nm).

[0097] <Polymer Tg> (Evaluation Sample) 100 g of each monomer was mixed with 3 g of a photopolymerization initiator (Omnirad 184, manufactured by IGM Resins) to prepare a curable composition. The curable composition was poured into a glass mold and then heated in a belt conveyor-type UV irradiation device (high-pressure mercury lamp, illuminance 150 mW / cm). ２ , under atmospheric conditions) with an integrated light dose of 4 J / cm ２ An evaluation sample (thickness 1.5 mm x width 4.0 mm x length 40 mm) was obtained by irradiating with UV light so that the temperature reached a value of 1.5 mm. (Evaluation method) The dynamic viscoelasticity of the obtained cured product was measured under the following conditions, and the storage modulus and loss modulus were measured at each temperature. The temperature at which the value (tan δ) obtained by dividing the loss modulus by the storage modulus reached a maximum was defined as the polymer Tg. Apparatus: RSA-G2 (manufactured by TA instruments) Measurement mode: Flexure Frequency: 10 Hz Heating rate: 5°C / min

[0098] Example 1 Synthesis Example 1 Production of Compound (A-1) A stirrer bar, 80.00 g (362 mmol) of 2-(2-biphenylyloxy)ethanol (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 85.70 g (543 mmol) of methyl α-allyloxymethylacrylate, 86 mg of a polymerization inhibitor (6-t-butyl-2,4-xylenol, manufactured by Tokyo Chemical Industry Co., Ltd.) (an amount that was 1000 ppm relative to the methyl α-allyloxymethylacrylate), 86 mg of a polymerization inhibitor (Polystop 7300P, manufactured by Hakuto Co., Ltd.) (an amount that was 1000 ppm relative to the methyl α-allyloxymethylacrylate), and 34.4 g of heptane were weighed into a 300 mL separable flask. 5.7 g of heptane was collected in a holder, and while the system was reduced in pressure to 300 Torr, the mixture was heated and stirred at 90-100°C for 1 hour. The water and heptane accumulated in the holder were recovered, and the water in the system was removed. Subsequently, heptane was collected in the holder, and a titanium solution containing 2.06 g (7.2 mmol) of titanium tetraisopropoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 2.06 g of heptane was added to a separable flask, and a transesterification reaction was carried out. While appropriately removing the lower phase accumulated in the holder, heating was continued until analysis by gas chromatography showed that the area ratio of the target product to 2-(2-biphenylyloxy)ethanol was >94%. The internal temperature was adjusted to 70°C, and 39.5 g of a 7% aqueous oxalic acid solution was added and heated and stirred for 30 minutes. After standing for 30 minutes, the aqueous phase was removed. Next, 39.5 g of water was used, and the above water washing procedure was performed a total of two times. This water washing operation removed the titanium tetraisopropoxide used as a catalyst. The system was depressurized to 300 Torr, the internal temperature was raised to 110°C, and heptane and water were removed. The system was then depressurized to 50 Torr while maintaining the internal temperature at 100-105°C. When the internal temperature reached 50 Torr, the internal temperature was raised to 110°C to remove traces of remaining heptane. The internal temperature was then lowered to around 50°C, and when it reached 50°C, the system was depressurized to 3-5 Torr. After reaching 3-5 Torr, the internal temperature was raised to 110°C, and methyl α-allyloxymethylacrylate was distilled off, completing the removal of light-boiling components. The resulting liquid was filtered through a 0.8 μm PTFE membrane filter to obtain the target product.The target product obtained contained 3.2% of methyl α-allyloxymethylacrylate. The viscosity, refractive index, and polymer Tg of the obtained compound (A-1) were evaluated. The results are shown in Table 1. The substituent moiety is equivalent to that of the comparative compound (B-1), and the compound is characterized by low viscosity.

[0099] Example 2 Synthesis Example 2 Production of Compound (A-2) A stir bar, 70.00 g (339 mmol) of 3-phenoxybenzyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.), 80.24 g (509 mmol) of methyl α-allyloxymethylacrylate, 80 mg of a polymerization inhibitor (6-t-butyl-2,4-xylenol, manufactured by Tokyo Chemical Industry Co., Ltd.) (amount equivalent to 1000 ppm relative to the methyl α-allyloxymethylacrylate), 80 mg of a polymerization inhibitor (Polystop 7300P, manufactured by Hakuto Co., Ltd.) (amount equivalent to 1000 ppm relative to the methyl α-allyloxymethylacrylate), and 31.2 g of heptane were weighed into a 300 mL separable flask. 6.1 g of heptane was collected in a holder, and the system was heated and stirred at 90 to 100°C for 1 hour while reducing the pressure inside the system to 300 Torr. The water collected in the holder and the heptane were recovered, and the water in the system was removed. Heptane was then collected in a holder, and a titanium solution containing 1.93 g (6.8 mmol) of titanium tetraisopropoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 1.93 g of heptane was added to a separable flask, where a transesterification reaction was carried out. While appropriately removing the lower phase that had accumulated in the holder, heating was continued until analysis by gas chromatography showed that the area ratio of the target product to 3-phenoxybenzyl alcohol was >95%. The internal temperature was adjusted to 70°C, and 35.9 g of a 7% aqueous oxalic acid solution was added, followed by heating and stirring for 30 minutes. After allowing to stand for 30 minutes, the aqueous phase was removed. Next, 35.9 g of water was used, and the above water washing procedure was performed twice in total. This water washing procedure removed the titanium tetraisopropoxide used as a catalyst. The pressure inside the system was reduced to 300 Torr, and the internal temperature was raised to 110°C, and heptane and water were removed. Thereafter, while maintaining the internal temperature at 100-105°C, the pressure inside the system was reduced to 50 Torr, and when it reached 50 Torr, the internal temperature was raised to 110°C, and traces of remaining heptane were removed. The internal temperature was then lowered to around 50°C, and when it reached 50°C, the pressure inside the system was reduced to 3-5 Torr. After reaching 3-5 Torr, the internal temperature was raised to 110°C, and methyl α-allyloxymethyl acrylate was distilled off, completing the removal of light boiling points. The resulting liquid was filtered through a 0.8 μm PTFE membrane filter to obtain the target product. The target product contained 3.4% methyl α-allyloxymethyl acrylate.The viscosity, refractive index, and polymer Tg of the resulting compound (A-2) were evaluated, and the results are shown in Table 1.

[0100] Example 3 Synthesis Example 3 Production of Compound (A-3) A stir bar, 75.00 g (450 mmol) of 1-naphthalenemethanol (manufactured by Tokyo Chemical Industry Co., Ltd.), 106.58 g (676 mmol) of methyl α-allyloxymethylacrylate, 107 mg of a polymerization inhibitor (6-t-butyl-2,4-xylenol, manufactured by Tokyo Chemical Industry Co., Ltd.) (amount equivalent to 1000 ppm relative to methyl α-allyloxymethylacrylate), 107 mg of a polymerization inhibitor (Polystop 7300P, manufactured by Hakuto Co., Ltd.) (amount equivalent to 1000 ppm relative to methyl α-allyloxymethylacrylate), and 37.7 g of heptane were weighed into a 300 mL separable flask. 5.7 g of heptane was collected in a holder, and the system was heated and stirred at 90 to 100°C for 1 hour while reducing the pressure inside the system to 300 Torr. The water collected in the holder and the heptane were recovered, and the water in the system was removed. Heptane was then collected in a holder, and a titanium solution containing 2.56 g (9.0 mmol) of titanium tetraisopropoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 2.56 g of heptane was added to a separable flask, where a transesterification reaction was carried out. While appropriately removing the lower phase that had accumulated in the holder, heating was continued until analysis by gas chromatography showed that the area ratio of the target product to 1-naphthalenemethanol was >96%. The internal temperature was adjusted to 70°C, and 43.5 g of a 7% aqueous oxalic acid solution was added, followed by heating and stirring for 30 minutes. After allowing to stand for 30 minutes, the aqueous phase was removed. Next, 43.5 g of water was used, and the above water washing operation was performed a total of two times. This water washing operation removed the titanium tetraisopropoxide used as a catalyst. The pressure inside the system was reduced to 300 Torr, and the internal temperature was raised to 110°C, and heptane and water were removed. Thereafter, while maintaining the internal temperature at 100-105°C, the pressure inside the system was reduced to 50 Torr, and when it reached 50 Torr, the internal temperature was raised to 110°C, and traces of remaining heptane were removed. The internal temperature was then lowered to around 50°C, and when it reached 50°C, the pressure inside the system was reduced to 2-5 Torr. After reaching 2-5 Torr, the internal temperature was raised to 110°C, and methyl α-allyloxymethyl acrylate was distilled off, completing the removal of light boiling points. The resulting liquid was filtered through a 0.8 μm PTFE membrane filter to obtain the target product. The target product contained 3.4% methyl α-allyloxymethyl acrylate.The viscosity, refractive index, and polymer Tg of the obtained compound (A-3) were evaluated, and the results are shown in Table 1.

[0101] Example 4 Synthesis Example 4 Production of Compound (A-4) A stir bar, 70.00 g (376 mmol) of 4-hydroxymethylbiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 89.01 g (574 mmol) of methyl α-allyloxymethylacrylate, 89 mg of a polymerization inhibitor (6-t-butyl-2,4-xylenol, manufactured by Tokyo Chemical Industry Co., Ltd.) (amount equivalent to 1000 ppm relative to methyl α-allyloxymethylacrylate), 89 mg of a polymerization inhibitor (Polystop 7300P, manufactured by Hakuto Co., Ltd.) (amount equivalent to 1000 ppm relative to methyl α-allyloxymethylacrylate), and 33.1 g of heptane were weighed into a 300 mL separable flask. 5.5 g of heptane was collected in a holder, and the system was heated and stirred at 90 to 100°C for 1 hour while reducing the pressure inside the system to 300 Torr. The water collected in the holder and the heptane were recovered, and the water in the system was removed. Heptane was then collected in a holder, and a titanium solution containing 2.14 g (7.5 mmol) of titanium tetraisopropoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 2.14 g of heptane was added to a separable flask, where a transesterification reaction was carried out. While appropriately removing the lower phase that had accumulated in the holder, heating was continued until analysis by gas chromatography showed that the area ratio of the target product to 4-hydroxymethylbiphenyl was >96%. The internal temperature was adjusted to 70°C, and 34.7 g of a 7% aqueous oxalic acid solution was added, followed by heating and stirring for 30 minutes. After allowing to stand for 30 minutes, the aqueous phase was removed. Next, 34.7 g of water was used, and the above water washing procedure was performed twice in total. This water washing procedure removed the titanium tetraisopropoxide used as a catalyst. The pressure inside the system was reduced to 300 Torr, and the internal temperature was raised to 110°C, and heptane and water were removed. Thereafter, while maintaining the internal temperature at 100-105°C, the pressure inside the system was reduced to 50 Torr, and when it reached 50 Torr, the internal temperature was raised to 110°C, and traces of remaining heptane were removed. The internal temperature was then lowered to around 50°C, and when it reached 50°C, the pressure inside the system was reduced to 4-5 Torr. After reaching 4-5 Torr, the internal temperature was raised to 110°C, and methyl α-allyloxymethyl acrylate was distilled off, completing the removal of light boiling points. The resulting liquid was filtered through a 0.8 μm PTFE membrane filter to obtain the target product. The target product contained 4.7% methyl α-allyloxymethyl acrylate.The viscosity, refractive index, and polymer Tg of the resulting compound (A-4) were evaluated, and the results are shown in Table 1.

[0102] Example 5 Synthesis Example 5 Production of Compound (A-5) A stir bar, 50.00 g (250 mmol) of 9-fluorenylmethanol (manufactured by Tokyo Chemical Industry Co., Ltd.), 118.17 g (574 mmol) of methyl α-allyloxymethylacrylate, 118 mg of a polymerization inhibitor (6-t-butyl-2,4-xylenol, manufactured by Tokyo Chemical Industry Co., Ltd.) (amount equivalent to 1000 ppm relative to the methyl α-allyloxymethylacrylate), 118 mg of a polymerization inhibitor (Polystop 7300P, manufactured by Hakuto Co., Ltd.) (amount equivalent to 1000 ppm relative to the methyl α-allyloxymethylacrylate), and 35.0 g of heptane were weighed into a 300 mL separable flask. 5.8 g of heptane was collected in a holder, and the system was heated and stirred at 90 to 100°C for 1 hour while reducing the pressure inside the system to 300 Torr. The water collected in the holder and the heptane were recovered, and the water in the system was removed. Heptane was then collected in a holder, and a titanium solution containing 1.42 g (5.0 mmol) of titanium tetraisopropoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 1.42 g of heptane was added to a separable flask, where a transesterification reaction was carried out. While appropriately removing the lower phase that had accumulated in the holder, heating was continued until analysis by gas chromatography showed that the area ratio of the target product to 9-fluorenylmethanol was >97%. The internal temperature was adjusted to 70°C, and 41.0 g of a 7% aqueous oxalic acid solution was added, followed by heating and stirring for 30 minutes. After allowing to stand for 30 minutes, the aqueous phase was removed. Next, 41.0 g of water was used, and the above water washing operation was performed a total of two times. This water washing operation removed the titanium tetraisopropoxide used as a catalyst. The pressure inside the system was reduced to 300 Torr, and the internal temperature was raised to 110°C, and heptane and water were removed. Thereafter, while maintaining the internal temperature at 100-105°C, the pressure inside the system was reduced to 50 Torr, and when it reached 50 Torr, the internal temperature was raised to 110°C, and traces of remaining heptane were removed. The internal temperature was then lowered to around 50°C, and when it reached 50°C, the pressure inside the system was reduced to 4-5 Torr. After reaching 3-5 Torr, the internal temperature was raised to 110°C, and methyl α-allyloxymethyl acrylate was distilled off, completing the removal of light boiling points. The resulting liquid was filtered through a 0.8 μm PTFE membrane filter to obtain the target product. The target product contained 3.7% methyl α-allyloxymethyl acrylate.The viscosity and refractive index of the resulting compound (A-5) were evaluated, and the results are shown in Table 1.

[0103] Comparative Example 1 The viscosity, refractive index, and polymer Tg of compound (B-1) (manufactured by Nisshoku Techno Fine Chemical Co., Ltd.) were evaluated. The results are shown in Table 2.

[0104] Comparative Example 2 The viscosity, refractive index, and polymer Tg of compound (B-2) (manufactured by Nippon Shokubai Co., Ltd.) were evaluated. The results are shown in Table 2.

[0105] <Comparative Example 3> Compound (B-3) was obtained by using cyclohexanol and methyl α-allyloxymethylacrylate as raw materials and by carrying out a method similar to that of Synthesis Example 1. The viscosity, refractive index, and polymer Tg of the obtained compound (B-3) were evaluated. The results are shown in Table 2.

[0106] <Comparative Example 4> Compound (B-4) was obtained by using tripropylene glycol and methyl α-allyloxymethylacrylate as raw materials and by carrying out a method similar to that of Synthesis Example 1. The viscosity, refractive index, and polymer Tg of the obtained compound (B-4) were evaluated. The results are shown in Table 2.

[0107] Examples 6 to 40, Comparative Examples 5 to 13 The refractive indexes (calculated values) of compounds (A-6) to (A-40) and compounds (B-5) to (B-13) were evaluated. The results are shown in Tables 1 and 2.

[0108] <Comparative Example 14> Compound (B-14) was obtained using benzyl alcohol and methyl α-allyloxymethylacrylate by a method similar to that of Synthesis Example 1. The viscosity, refractive index, and polymer Tg of the obtained compound (B-14) were evaluated. The results are shown in Table 2.

[0109] The structures of the compounds (A-1) to (A-40) and (B-1) to (B-14) of the examples and comparative examples are as follows:

[0110]

[0111]

[0112]

[0113] Tables 1 and 2 show that the compounds of the Examples (A-1) to (A-40), all of which have an α-allyloxymethylacryloyl group, have a higher refractive index than the compounds of the Comparative Examples (B-2) to (B-14). Furthermore, the compound of Example 1 (A-1) has a lower viscosity and a higher polymer Tg than the compound of Comparative Example 1 (B-1), which has an acryloyl group.

Claims

1. A compound represented by the following general formula (1): (In formula (1), R １ represents an organic group containing an aromatic ring having 10 or more carbon atoms in its structure, an organic group containing an aromatic heterocycle, or two or more benzene rings bonded directly or bonded to a carbon atom, an oxygen atom, a sulfur atom, -CH-, -C(CH ３ ) ２ -, -SO- or -SO ２ Z represents an organic group containing a structure bonded via -, an organic group represented by the following general formula (2), or an organic group represented by the following general formula (3). ２ R ３ represents -, -O-, -S- or -NH-. ２ and R ３ are the same or different and represent a hydrogen atom or a methyl group; n is the same or different and represents an integer of 0 to 20; and m is an integer of 1 to 3. (In formula (2), R ２１ represents a direct bond or an alkylene group. ２２ are the same or different and represent a halogen atom; and a represents an integer of 1 to 3. (In formula (3), R ３１ represents an unsaturated aliphatic hydrocarbon group. ３２ are the same or different and represent a substituent; and b represents an integer of 0 to 5.

2. The compound according to claim 1, having a refractive index calculated according to practical Hansen solubility parameters of 1.54 or more.

3. A cured product obtained by curing the compound according to claim 1 or 2.

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