JP2008001640A - Novel 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound, method for producing the same, and use thereof - Google Patents

Abstract

【選択図】 なしPROBLEM TO BE SOLVED: To provide a novel compound excellent in photopolymerization sensitization performance.
SOLUTION: A 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound represented by the following formula (1). (Wherein R ₁ represents an alkyl group, R ₂ represents a hydrogen atom, an alkyl group, etc., R ₃ represents a hydrogen atom or a methyl group, and X and Y represent a hydrogen atom, an alkyl group, a halogen atom, etc. Show.)

[Selection figure] None

Description

  The present invention relates to a 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound. More specifically, the present invention relates to a 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound useful as a photopolymerization sensitizer, a production method thereof, and a use of this compound.

Conventionally, it is well known that 4-alkoxynaphthol functions as a photopolymerization sensitizer in photocationic polymerization (see Patent Document 1). However, the conventional dihydroxynaphthalene has a high sublimation property and has a drawback of volatilizing in the heating step when the photocurable composition is cured. For this reason, an attempt was made to introduce an acrylic group into the naphthalene skeleton, but the resulting acrylate was poor in photosensitization performance and was not desirable (see Patent Document 2).
JP-A-11-263804 Japanese Patent Laid-Open No. 62-192340

In view of such circumstances, the present inventors have intensively studied to provide a technique that eliminates these drawbacks, and as a result, have completed the present invention. That is, the object of the present invention is as follows.
1. To provide a novel compound excellent in photopolymerization sensitization performance.
2. To provide a photocurable composition containing the above compound as a photopolymerization sensitizer.
3. To provide a photocurable composition that contains the above-mentioned compound as a photopolymerization sensitizer and is less likely to volatilize (sublimate) in the heating step when photocured.

  In order to achieve the above object, the first invention provides a 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound represented by the structural formula (1).

{In the structural formula (1), R ₁ represents any of an alkyl group, a hydroxyalkyl group, an alkoxyalkyl group, an aryloxyalkyl group, and a halogenated alkyl group, and R ₂ represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group. Any one of a methyl group, an allyloxymethyl group, and an aryloxymethyl group, R ₃ represents a hydrogen atom or a methyl group, X and Y may be the same or different, a hydrogen atom, an alkyl group, a halogen atom, A hydroxyl group, an alkoxy group, an alkylthio group, an arylthio group, a carboxyl group, or a sulfonic acid group is shown. }

  In the second invention, an alkylene oxide compound is added to a 4-alkoxy-1- (2-hydroxyalkoxy) naphthalene compound, and then this compound is reacted with acryloyl chloride or methacryloyl chloride. The manufacturing method of the 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound which concerns on 1st invention is provided.

  Furthermore, the third invention provides a photopolymerization sensitizer characterized by containing a 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound according to the first invention as an active ingredient.

  Furthermore, the fourth invention provides a photocurable composition comprising the photopolymerization sensitizer, photopolymerization initiator, and photopolymerizable monomer according to the third invention.

The present invention is as described in detail below, has the following particularly advantageous effects, and its industrial utility value is extremely large.
1. The 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound according to the first invention is a novel compound and exhibits excellent effects as a photopolymerization sensitizer in photoradical polymerization and photocationic polymerization. .
2. According to the production method according to the second invention, the compound according to the first invention can be produced industrially advantageously.
3. The photopolymerization sensitizer according to the third invention is unlikely to volatilize (sublimate) in the heating step when the photocurable composition containing the photopolymerizable composition is cured.
4). The product after photocuring the photocurable composition according to the fourth aspect of the invention is excellent in that residual components are unlikely to elute and volatilize.

Hereinafter, the present invention will be described in detail.
The compound according to the first aspect of the present invention is a 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound represented by the structural formula (1).

In the structural formula (1), examples of the alkyl group represented by R ₁ include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a heptyl group. Examples of the hydroxyalkyl group represented by R ₁ include 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 4-hydroxybutoxy group, and the alkoxyethyl group represented by R ₁ includes 2-methoxyethyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-phenoxyethyl group may be mentioned. Examples of the halogenated alkyl group represented by R ₁ include 2-fluoroethyl group, 2-chloroethyl group, Examples include 2-bromoethyl group, 3-chloropropyl group, 4-chlorobutyl group.

In the structural formula (1), examples of the alkyl group represented by R ₂ include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a heptyl group. The aryl group represented by R _2, a phenyl group, o- tolyl group, m- tolyl group, p- tolyl group, p- methoxyphenyl group, p- ethoxyphenyl group and a naphthyl group, _{R 2} in the alkoxymethyl group represented, methoxymethyl group, butoxymethyl group, 2-ethylhexyl oxymethyl group, 2-octyloxy-methyl group. Examples of allyloxymethyl group represented by R _2, meta Examples include an aryloxymethyl group, and examples of the aryloxymethyl group represented by R ₂ include a phenoxymethyl group. In the structural formula (1), R ₃ represents a hydrogen atom or a methyl group.

  In the structural formula (1), the alkyl group represented by X or Y includes a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, amyl group, 2- Examples thereof include an ethylhexyl group, and examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, a hexyloxy group, and a phenoxy group. Examples of the alkylthio group include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, and a hexylthio group. Examples of the arylthio group include a phenylthio group, an o-tolylthio group, an m-tolylthio group, a p-tolylthio group, and a p-hydroxyphenylthio group.

  Examples of the 4-alkoxy-1- (2- (meth) acryloxyalkoxynaphthalene compound represented by the structural formula (1) include the following: 4-methoxy-1- (2-acryloxyethoxy) Naphthalene, 4-methoxy-1- (2-methacryloxyethoxy) naphthalene, 4-methoxy-1- (2-acryloxypropoxy) naphthalene, 4-methoxy-1- (2-methacryloxypropoxy) naphthalene, 4-methoxy -1- (2-acryloxybutoxy) naphthalene, 4-methoxy-1- (2-methacryloxybutoxy) naphthalene, 4-methoxy-1- (2-acryloxyheptyloxy) naphthalene, 4-methoxy-1- ( 2-methacryloxyheptyloxy) naphthalene, 4-methoxy-1- (2- (Cryloxyoctyloxy) naphthalene, 4-methoxy-1- (2-methacryloxyoctyloxy) naphthalene, 4-methoxy-1- (2-acryloxy-2-phenylethoxy) naphthalene, 4-methoxy-1- (2 -Methacryloxy-2-phenylethoxy) naphthalene, 4-methoxy-1- (2-acryloxy-3-methoxypropoxy) naphthalene, 4-methoxy-1- (2-methacryloxy-3-methoxypropoxy) naphthalene, 4 -Methoxy-1- (2-acryloxy-3-butoxypropoxy) naphthalene, 4-methoxy-1- (2-methacryloxy-3-butoxypropoxy) naphthalene, 4-methoxy-1- (2-acryloxy-3 -Allyloxypropoxy) naphthalene, 4-methoxy-1- 2-methacryloxy-3-allyloxypropoxy) naphthalene, 4-methoxy-1- (2-acryloxy-3- (2-ethylhexyloxy) propoxy) naphthalene, 4-methoxy-1- (2-methacryloxy-3 -(2-Ethyl) hexyloxypropoxy) naphthalene, 4-methoxy-1- (2-acryloxy-3-stearyloxypropoxy) naphthalene, 4-methoxy-1- (2-methacryloxy-3-stearyloxypropoxy) Naphthalene, 4-methoxy-1- (2-acryloxy-3-phenoxypropoxy) naphthalene, 4-methoxy-1- (2-methacryloxy-3-phenoxypropoxy) naphthalene, and the like.

  Furthermore, 4-ethoxy-1- (2-acryloxyethoxy) naphthalene, 4-ethoxy-1- (2-methacryloxyethoxy) naphthalene, 4-ethoxy-1- (2-acryloxypropoxy) naphthalene, 4-ethoxy -1- (2-methacryloxypropoxy) naphthalene, 4-ethoxy-1- (2-acryloxybutoxy) naphthalene, 4-ethoxy-1- (2-methacryloxybutoxy) naphthalene, 4-ethoxy-1- (2 -Acryloxyheptyloxy) naphthalene, 4-ethoxy-1- (2-methacryloxyheptyloxy) naphthalene, 4-ethoxy-1- (2-acryloxyoctyloxy) naphthalene, 4-ethoxy-1- (2-methacrylic) Oxyoctyloxy) naphthalene, 4-ethoxy-1- ( -Acryloxy-2-phenylethoxy) naphthalene, 4-ethoxy-1- (2-methacryloxy-2-phenylethoxy) naphthalene, 4-ethoxy-1- (2-acryloxy-3-methoxypropoxy) naphthalene, 4 -Ethoxy-1- (2-methacryloxy-3-methoxypropoxy) naphthalene, 4-ethoxy-1- (2-acryloxy-3-butoxypropoxy)) naphthalene, 4-ethoxy-1- (2-methacryloxy- 3-butoxypropoxy) naphthalene, 4-ethoxy-1- (2-acryloxy-3-allyloxypropoxy) naphthalene, 4-ethoxy-1- (2-methacryloxy-3-allyloxypropoxy) naphthalene, 4-ethoxy -1- (2-acryloxy-3- (2-ethylhexyl) Xy) propoxy) naphthalene, 4-ethoxy-1- (2-methacryloxy-3- (2-ethyl) hexyloxypropoxy) naphthalene, 4-ethoxy-1- (2-acryloxy-3-stearyloxypropoxy) naphthalene 4-ethoxy-1- (2-methacryloxy-3-stearyloxypropoxy) naphthalene, 4-ethoxy-1- (2-acryloxy-3-phenoxypropoxy) naphthalene, 4-ethoxy-1- (2-methacrylic) And oxy-3-phenoxypropoxy) naphthalene.

  Further, 4-butoxy-1- (2-acryloxyethoxy) naphthalene, 4-butoxy-1- (2-methacryloxyethoxy) naphthalene, 4-butoxy-1- (2-acryloxypropoxy) naphthalene, 4-butoxy -1- (2-methacryloxypropoxy) naphthalene, 4-butoxy-1- (2-acryloxybutoxy) naphthalene, 4-butoxy-1- (2-methacryloxybutoxy) naphthalene, 4-butoxy-1- (2 -Acryloxyheptyloxy) naphthalene, 4-butoxy-1- (2-methacryloxyheptyloxy) naphthalene, 4-butoxy-1- (2-acryloxyoctyloxy) naphthalene, 4-butoxy-1- (2-methacrylic) Oxyoctyloxy) naphthalene, 4-butoxy-1- (2 Acrylicoxy-2-phenylethoxy) naphthalene, 4-butoxy-1- (2-methacryloxy-2-phenylethoxy) naphthalene, 4-butoxy-1- (2-acryloxy-3-methoxypropoxy) naphthalene, 4- Butoxy-1- (2-methacryloxy-3-methoxypropoxy) naphthalene, 4-butoxy-1- (2-acryloxy-3-butoxypropoxy)) naphthalene, 4-butoxy-1- (2-methacryloxy-3 -Butoxypropoxy) naphthalene, 4-butoxy-1- (2-acryloxy-3-allyloxypropoxy) naphthalene, 4-butoxy-1- (2-methacryloxy-3-allyloxypropoxy) naphthalene, 4-butoxy- 1- (2-acryloxy-3- (2-ethylhexylo C) propoxy) naphthalene, 4-butoxy-1- (2-methacryloxy-3- (2-ethyl) hexyloxypropoxy) naphthalene, 4-butoxy-1- (2-acryloxy-3-stearyloxypropoxy) naphthalene 4-butoxy-1- (2-methacryloxy-3-stearyloxypropoxy) naphthalene, 4-butoxy-1- (2-acryloxy-3-phenoxypropoxy) naphthalene, 4-butoxy-1- (2-methacrylic) And oxy-3-phenoxypropoxy) naphthalene.

  Furthermore, 4-hexyloxy-1- (2-acryloxyethoxy) naphthalene, 4-hexyloxy-1- (2-methacryloxyethoxy) naphthalene, 4-hexyloxy-1- (2-acryloxypropoxy) naphthalene, 4 -Hexyloxy-1- (2-methacryloxypropoxy) naphthalene, 4-hexyloxy-1- (2-acryloxybutoxy) naphthalene, 4-hexyloxy-1- (2-methacryloxybutoxy) naphthalene, 4-hexyl Oxy-1- (2-acryloxyheptyloxy) naphthalene, 4-hexyloxy-1- (2-methacryloxyheptyloxy) naphthalene, 4-hexyloxy-1- (2-acryloxyoctyloxy) naphthalene, 4- Hexyloxy-1- (2-metac Ruoxyoctyloxy) naphthalene, 4-hexyloxy-1- (2-acryloxy-2-phenylethoxy) naphthalene, 4-hexyloxy-1- (2-methacryloxy-2-phenylethoxy) naphthalene, 4-hexyl Oxy-1- (2-methacryloxy-3-methoxypropoxy) naphthalene, 4-hexyloxy-1- (2-acryloxy-3-butoxypropoxy) naphthalene, 4-hexyloxy-1- (2-methacryloxy- 3-butoxypropoxy) naphthalene, 4-hexyloxy-1- (2-acryloxy-3-allyloxypropoxy) naphthalene, 4-hexyloxy-1- (2-methacryloxy-3-allyloxypropoxy) naphthalene, 4 -Hexyloxy-1- (2-acryloxy) -3- (2-ethylhexyloxy) propoxy) naphthalene, 4-hexyloxy-1- (2-methacryloxy-3- (2-ethylhexyloxy) propoxy) naphthalene, 4-hexyloxy-1- (2-acryloxy -3-stearyloxypropoxy) naphthalene, 4-hexyloxy-1- (2-methacryloxy-3-stearyloxypropoxy) naphthalene, 4-hexyloxy-1- (2-acryloxy-3-phenoxypropoxy) naphthalene, Examples include 4-hexyloxy-1- (2-methacryloxy-3-phenoxypropoxy) naphthalene.

  Furthermore, 4- (2-phenoxyethoxy) -1- (2-acryloxyethoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-methacryloxyethoxy) naphthalene, 4- (2-phenoxyethoxy) ) -1- (2-acryloxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-methacryloxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-acryloxybutoxy) ) Naphthalene, 4- (2-phenoxyethoxy) -1- (2-methacryloxybutoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-acryloxyheptyloxy) naphthalene, 4- (2-phenoxy) Ethoxy) -1- (2-methacryloxyheptyloxy) naphthalene, 4- ( -Phenoxyethoxy) -1- (2-acryloxyoctyloxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-methacryloxyoctyloxy) naphthalene, 4- (2-phenoxyethoxy) -1- ( 2-acryloxy-2-phenylethoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-methacryloxy-2-phenylethoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2- Acrylicoxy-3-methoxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-methacryloxy-3-methoxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-acryloxy -3-butoxypropoxy)) naphthalene, 4- (2-phenoxyethoxy) 1- (2-methacryloxy-3-butoxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-acryloxy-3-allyloxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1 -(2-methacryloxy-3-allyloxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-acryloxy-3- (2-ethylhexyloxy) propoxy) naphthalene, 4- (2-phenoxy) Ethoxy) -1- (2-methacryloxy-3- (2-ethyl) hexyloxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-acryloxy-3-stearyloxypropoxy) naphthalene, 4 -(2-phenoxyethoxy) -1- (2-methacryloxy-3-stearyl Ruoxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-acryloxy-3-phenoxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-methacryloxy-3-phenoxy And propoxy) naphthalene.

  Furthermore, 2-methyl-4-methoxy-1- (2-acryloxyethoxy) naphthalene, 2-methyl-4-methoxy-1- (2-methacryloxyethoxy) naphthalene, 2-methyl-4-methoxy-1 -(2-acryloxypropoxy) naphthalene, 2-methyl-4-methoxy-1- (2-methacryloxypropoxy) naphthalene, 2-methyl-4-methoxy-1- (2-acryloxybutoxy) naphthalene, 2- Methyl-4-methoxy-1- (2-methacryloxybutoxy) naphthalene, 2-methyl-4-methoxy-1- (2-acryloxyheptyloxy) naphthalene, 2-methyl-4-methoxy-1- (2- Methacryloxyheptyloxy) naphthalene, 2-methyl-4-methoxy-1- (2-acryloxyoct Ruoxy) naphthalene, 2-methyl-4-methoxy-1- (2-methacryloxyoctyloxy) naphthalene, 2-methyl-4-methoxy-1- (2-acryloxy-2-phenylethoxy) naphthalene, 2-methyl -4-methoxy-1- (2-methacryloxy-2-phenylethoxy) naphthalene, 2-methyl-4-methoxy-1- (2-acryloxy-3-methoxypropoxy) naphthalene, 2-methyl-4-methoxy -1- (2-methacryloxy-3-methoxypropoxy) naphthalene, 2-methyl-4-methoxy-1- (2-acryloxy-3-butoxypropoxy) naphthalene, 2-methyl-4-methoxy-1- ( 2-methacryloxy-3-butoxypropoxy)) naphthalene, 2-methyl-4-methoxy-1- 2-acryloxy-3-allyloxypropoxy) naphthalene, 2-methyl-4-methoxy-1- (2-methacryloxy-3-allyloxypropoxy) naphthalene, 2-methyl-4-methoxy-1- (2- Acrylicoxy-3- (2-ethyl) hexyloxypropoxy) naphthalene, 2-methyl-4-methoxy-1- (2-methacryloxy-3- (2-ethyl) hexyloxypropoxy) naphthalene, 2-methyl-4 -Methoxy-1- (2-acryloxy-3-stearyloxypropoxy) naphthalene, 2-methyl-4-methoxy-1- (2-methacryloxy-3-stearyloxypropoxy) naphthalene, 2-methyl-4-methoxy -1- (2-acryloxy-3-phenoxypropoxy) naphthalene, 2-methyl Examples include -4-methoxy-1- (2-methacryloxy-3-phenoxypropoxy) naphthalene.

  Also, 2-chloro-4-methoxy-1- (2-acryloxyethoxy) naphthalene, 2-chloro-4-methoxy-1- (2-methacryloxyethoxy) naphthalene, 2-chloro-4-methoxy-1- (2-acryloxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-methacryloxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-acryloxybutoxy) naphthalene, 2-chloro -4-methoxy-1- (2-methacryloxybutoxy) naphthalene, 2-chloro-4-methoxy-1- (2-acryloxyheptyloxy) naphthalene, 2-chloro-4-methoxy-1- (2-methacrylic) Oxyheptyloxy) naphthalene, 2-chloro-4-methoxy-1- (2-acryloxyoctylo) C) Naphthalene, 2-chloro-4-methoxy-1- (2-methacryloxyoctyloxy) naphthalene, 2-chloro-4-methoxy-1- (2-acryloxy-2-phenylethoxy) naphthalene, 2-chloro -4-methoxy-1- (2-methacryloxy-2-phenylethoxy) naphthalene, 2-chloro-4-methoxy-1- (2-acryloxy-3-methoxypropoxy) naphthalene, 2-chloro-4-methoxy -1- (2-methacryloxy-3-methoxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-acryloxy-3-butoxypropoxy) naphthalene, 2-chloro-4-methoxy-1- ( 2-methacryloxy-3-butoxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-a Ryloxy-3-allyloxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-methacryloxy-3-allyloxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-acryloxy- 3- (2-ethyl) hexyloxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-methacryloxy-3- (2-ethyl) hexyloxypropoxy) naphthalene, 2-chloro-4-methoxy- 1- (2-acryloxy-3-stearyloxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-methacryloxy-3-stearyloxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-acryloxy-3-phenoxypropoxy) naphthalene, 2-chloro-4-me Toxyl-1- (2-methacryloxy-3-phenoxypropoxy) naphthalene and the like can be mentioned.

  Representative examples of the 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound represented by the structural formula (1) are shown as the following structural formula (2) to structural formula (17). It is what

  The 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound according to the first invention is a 4-alkoxy-1-naphthol compound in the presence or absence of a base, in the presence or absence of a solvent. Under the first reaction for adding alkylene oxide, the 4-alkoxy-1- (2-hydroxyalkoxy) naphthalene compound obtained by this first reaction is further added in the presence or absence of a base, in the presence or absence of a solvent. Then, it can be produced by a second reaction in which acryloyl chloride or methacryloyl chloride is reacted.

  Examples of 4-alkoxy-1-naphthol compounds that can be used in the first reaction include the following compounds. That is, 4-methoxy-1-naphthol, 4-ethoxy-1-naphthol, 4-propoxy-1-naphthol, 4- (i-propoxy) -1-naphthol, 4-butoxy-1-naphthol, 4- (i -Butoxy) -1-naphthol, 4-pentyloxy-1-naphthol, 4-hexyloxy-1-naphthol, 4-heptyloxy-1-naphthol, 4- (2-ethylhexyloxy) -1-naphthol, 4- Octyloxy-1-naphthol, 4-decyloxy-1-naphthol, 4-dodecyloxy-1-naphthol, 4- (2-methoxyethoxy) -1-naphthol, 4- (2-ethoxyethoxy) -1-naphthol, 4- (2-hydroxyethoxy) -1-naphthol, 4- (2-phenoxyethoxy) -1-naphthol, 4- 2-chloroethoxy) -1-naphthol, 4- (2-bromoethoxy) -1-naphthol, 4- (3-chloropropoxy) -1-naphthol, 2-methyl-4-methoxy-1-naphthol, 2- Methyl-4-ethoxy-1-naphthol, 2-methyl-4-propoxy-1-naphthol, 2-methyl-4- (i-propoxy) -1-naphthol, 2-methyl-4-butoxy-1-naphthol, 2-chloro-4-methoxy-1-naphthol, 2-chloro-4-ethoxy-1-naphthol, 2-chloro-4-propoxy-1-naphthol, 2-chloro-4- (i-propoxy) -1- Naphthol, 2chloro-4-butoxy-1-naphthol, and the like.

  Examples of the alkylene oxide that can be used for the addition reaction with the 4-alkoxy-1-naphthol compound in the first reaction include ethylene oxide, propylene oxide, butylene oxide, 1-hexene oxide, cyclohexene oxide, methyl glycidyl ether, and allyl glycidyl. Examples include ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, 2-methyloctyl glycidyl ether, and phenyl glycidyl ether.

  In the first reaction, when an alkaline compound is used as the base, for example, an inorganic alkaline compound such as sodium hydroxide, potassium hydroxide, sodium carbonate, or potassium carbonate is suitable. Alkaline compounds are usually used as aqueous solutions. Examples of the solvent in the case of using a solvent include alcohol solvents, ketone solvents, ether solvents, amide solvents, amine solvents, and the like. Specific examples of the alcohol solvent include methanol, ethanol, isopropyl alcohol, and the like. Specific examples of the ketone solvent include acetone, methyl ethyl ketone, acetone, and the like. Specific examples of the ether solvent include tetrahydride. Examples include furan and 1,4-dioxane. Specific examples of the amide solvent include dimethylformamide and dimethylacetamide.

  The amount of alkylene oxide added to the 4-alkoxy-1-naphthol compound is preferably selected in the range of 2 mol times to 10 mol times. If the amount of the latter added relative to the former is 2 mol times or less, the unreacted 4-alkoxy-1-naphthol compound remains and the purity of the product is lowered. On the other hand, if it is 10 mol times or more, it may be difficult to precipitate product crystals from the reaction solution. A more preferable amount of the latter added to the former is in a range of 2.2 mol times to 5 mol times. In the case where an alkali compound is present in the reaction system, it is usually preferably about equimolar with the 4-alkoxy-1-naphthol compound. The first reaction is usually performed at room temperature. When the reaction proceeds slowly, it can be heated to around 50 ° C. As the reaction proceeds, the red color derived from the alkali metal salt of the 4-alkoxy-1-naphthol compound disappears, so the progress of the reaction can be easily confirmed. After completion of the reaction, the reaction solution is cooled, and the precipitated crystals are filtered and dried to obtain the corresponding 4-alkoxy-1- (2-hydroxyalkoxy) naphthalene compound.

  In the second reaction, the 4-alkoxy-1- (2-hydroxyalkoxy) naphthalene compound obtained in the first reaction and acryloyl chloride or methacryloyl chloride are added in the presence or absence of a base or in the presence or absence of a base. By reacting in the absence of (meth) acrylation, the corresponding 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound is obtained.

  What can be used as a raw material in the second reaction is 4-alkoxy-1- (2-hydroxyalkoxy) naphthalene obtained by adding alkylene oxide to a 4-alkoxy-1-naphthol compound in the first reaction. A compound. Specific examples include the following compounds. That is, 4-methoxy-1- (2-hydroxyethoxy) naphthalene, 4-methoxy-1- (2-hydroxypropoxy) naphthalene, 4-methoxy-1- (2-hydroxybutoxy) naphthalene, 4-methoxy-1- (2-hydroxyheptyloxy) naphthalene, 4-methoxy-1- (2-hydroxyoctyloxy) naphthalene, 4-methoxy-1- (2-hydroxy-2-phenylethoxy) naphthalene, 4-methoxy-1- (2 -Hydroxy-3-methoxypropoxy) naphthalene, 4-methoxy-1- (2-hydroxy-3-butoxypropoxy) naphthalene, 4-methoxy-1- (2-hydroxy-3-allyloxypropoxy) naphthalene, 4-methoxy -1- (2-hydroxy-3- (2-ethylhexyloxy) pro Xyl) naphthalene, 4-methoxy-1- (2-hydroxy-3-stearyloxypropoxy) naphthalene, 4-methoxy-1- (2-hydroxy-3-phenoxypropoxy) naphthalene, 4-ethoxy-1- (2- Hydroxyethoxy) naphthalene, 4-ethoxy-1- (2-hydroxypropoxy) naphthalene, 4-ethoxy-1- (2-hydroxybutoxy) naphthalene, 4-ethoxy-1- (2-hydroxyheptyloxy) naphthalene, 4- Ethoxy-1- (2-hydroxyoctyloxy) naphthalene, 4-ethoxy-1- (2-hydroxy-2-phenylethoxy) naphthalene, 4-ethoxy-1- (2-hydroxy-3-methoxypropoxy) naphthalene, 4 -Ethoxy-1- (2-hydroxy-3-butoxypropoxy ) Naphthalene, 4-ethoxy-1- (2-hydroxy-3-allyloxypropoxy) naphthalene, 4-ethoxy-1- (2-hydroxy-3- (2-ethylhexyloxy) propoxy) naphthalene, 4-ethoxy-1 -(2-hydroxy-3-stearyloxypropoxy) naphthalene, 4-ethoxy-1- (2-hydroxy-3-phenoxypropoxy) naphthalene, and the like.

  Furthermore, 4-propoxy-1- (2-hydroxyethoxy) naphthalene, 4-propoxy-1- (2-hydroxypropoxy) naphthalene, 4-propoxy-1- (2-hydroxybutoxy) naphthalene, 4-propoxy-1- (2-hydroxyheptyloxy) naphthalene, 4-propoxy-1- (2-hydroxyoctyloxy) naphthalene, 4-propoxy-1- (2-hydroxy-2-phenylethoxy) naphthalene, 4-propoxy-1- (2 -Hydroxy-3-methoxypropoxy) naphthalene, 4-propoxy-1- (2-hydroxy-3-butoxypropoxy) naphthalene, 4-propoxy-1- (2-hydroxy-3-allyloxypropoxy) naphthalene, 4-propoxy -1- (2-hydroxy-3- (2-ethyl Siloxy) propoxy) naphthalene, 4-propoxy-1- (2-hydroxy-3-stearyloxypropoxy) naphthalene, 4-propoxy-1- (2-hydroxy-3-phenoxypropoxy) naphthalene, 4- (i-propoxy) -1- (2-hydroxyethoxy) naphthalene, 4- (i-propoxy) -1- (2-hydroxypropoxy) naphthalene, 4- (i-propoxy) -1- (2-hydroxybutoxy) naphthalene, 4- ( i-propoxy) -1- (2-hydroxyheptyloxy) naphthalene, 4- (i-propoxy) -1- (2-hydroxyoctyloxy) naphthalene, 4- (i-propoxy) -1- (2-hydroxy- 2-Phenylethoxy) naphthalene, 4- (i-propoxy) -1- (2-hydroxy- -Methoxypropoxy) naphthalene, 4- (i-propoxy) -1- (2-hydroxy-3-butoxypropoxy) naphthalene, 4- (i-propoxy) -1- (2-hydroxy-3-allyloxypropoxy) naphthalene 4- (i-propoxy) -1- (2-hydroxy-3- (2-ethylhexyloxy) propoxy) naphthalene, 4- (i-propoxy) -1- (2-hydroxy-3-stearyloxypropoxy) naphthalene 4- (i-propoxy) -1- (2-hydroxy-3-phenoxypropoxy) naphthalene, 4-butoxy-1- (2-hydroxyethoxy) naphthalene, 4-butoxy-1- (2-hydroxypropoxy) naphthalene 4-butoxy-1- (2-hydroxybutoxy) naphthalene, 4-butoxy-1- (2-hydroxyheptyloxy) naphthalene, 4-butoxy-1- (2-hydroxyoctyloxy) naphthalene, 4-butoxy-1- (2-hydroxy-2-phenylethoxy) naphthalene, 4-butoxy-1- (2 -Hydroxy-3-methoxypropoxy) naphthalene, 4-butoxy-1- (2-hydroxy-3-butoxypropoxy) naphthalene, 4-butoxy-1- (2-hydroxy-3-allyloxypropoxy) naphthalene, 4-butoxy -1- (2-hydroxy-3- (2-ethylhexyloxy) propoxy) naphthalene, 4-butoxy-1- (2-hydroxy-3-stearyloxypropoxy) naphthalene, 4-butoxy-1- (2-hydroxy- And 3-phenoxypropoxy) naphthalene.

  Further, 4- (2-ethylhexyloxy) -1- (2-hydroxyethoxy) naphthalene, 4- (2-ethylhexyloxy) -1- (2-hydroxypropoxy) naphthalene, 4- (2-ethylhexyloxy) -1 -(2-hydroxybutoxy) naphthalene, 4- (2-ethylhexyloxy) -1- (2-hydroxyheptyloxy) naphthalene, 4- (2-ethylhexyloxy) -1- (2-hydroxyoctyloxy) naphthalene, 4 -(2-ethylhexyloxy) -1- (2-hydroxy-2-phenylethoxy) naphthalene, 4- (2-ethylhexyloxy) -1- (2-hydroxy-3-methoxypropoxy) naphthalene, 4- (2- Ethylhexyloxy) -1- (2-hydroxy-3-butoxypropoxy) naphth Len, 4- (2-ethylhexyloxy) -1- (2-hydroxy-3-allyloxypropoxy) naphthalene, 4- (2-ethylhexyloxy) -1- (2-hydroxy-3- (2-ethylhexyloxy) Propoxy) naphthalene, 4- (2-ethylhexyloxy) -1- (2-hydroxy-3-stearyloxypropoxy) naphthalene, 4- (2-ethylhexyloxy) -1- (2-hydroxy-3-phenoxypropoxy) naphthalene 4- (2-methoxyethoxy) -1- (2-hydroxyethoxy) naphthalene, 4- (2-methoxyethoxy) -1- (2-hydroxypropoxy) naphthalene, 4- (2-methoxyethoxy) -1- (2-hydroxybutoxy) naphthalene, 4- (2-methoxyethoxy) -1- (2 Hydroxyheptyloxy) naphthalene, 4- (2-methoxyethoxy) -1- (2-hydroxyoctyloxy) naphthalene, 4- (2-methoxyethoxy) -1- (2-hydroxy-2-phenylethoxy) naphthalene, 4 -(2-methoxyethoxy) -1- (2-hydroxy-3-methoxypropoxy) naphthalene, 4- (2-methoxyethoxy) -1- (2-hydroxy-3-butoxypropoxy) naphthalene, 4- (2- Methoxyethoxy) -1- (2-hydroxy-3-allyloxypropoxy) naphthalene, 4- (2-methoxyethoxy) -1- (2-hydroxy-3- (2-ethylhexyloxy) propoxy) naphthalene, 4- ( 2-Methoxyethoxy) -1- (2-hydroxy-3-stearyloxypropoxy) naphth Also included are thalene and 4- (2-methoxyethoxy) -1- (2-hydroxy-3-phenoxypropoxy) naphthalene.

  Furthermore, 4- (2-phenoxyethoxy) -1- (2-hydroxyethoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-hydroxypropoxy) naphthalene, 4- (2-phenoxyethoxy)- 1- (2-hydroxybutoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-hydroxyheptyloxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-hydroxyoctyloxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-hydroxy-2-phenylethoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-hydroxy-3-methoxypropoxy) naphthalene, 4- (2 -Phenoxyethoxy) -1- (2-hydroxy-3-butoxypropoxy) naphthalene, 4 (2-phenoxyethoxy) -1- (2-hydroxy-3-allyloxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-hydroxy-3- (2-ethylhexyloxy) propoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-hydroxy-3-stearyloxypropoxy) naphthalene, 4- (2-phenoxyethoxy) -1- (2-hydroxy-3-phenoxypropoxy) naphthalene, 4- ( 2-chloroethoxy) -1- (2-hydroxyethoxy) naphthalene, 4- (2-chloroethoxy) -1- (2-hydroxypropoxy) naphthalene, 4- (2-chloroethoxy) -1- (2-hydroxy Butoxy) naphthalene, 4- (2-chloroethoxy) -1- (2-hydroxyheptyloxy) Naphthalene, 4- (2-chloroethoxy) -1- (2-hydroxyoctyloxy) naphthalene, 4- (2-chloroethoxy) -1- (2-hydroxy-2-phenylethoxy) naphthalene, 4- (2- Chloroethoxy) -1- (2-hydroxy-3-methoxypropoxy) naphthalene, 4- (2-chloroethoxy) -1- (2-hydroxy-3-butoxypropoxy) naphthalene, 4- (2-chloroethoxy)- 1- (2-hydroxy-3-allyloxypropoxy) naphthalene, 4- (2-chloroethoxy) -1- (2-hydroxy-3- (2-ethylhexyloxy) propoxy) naphthalene, 4- (2-chloroethoxy) ) -1- (2-hydroxy-3-stearyloxypropoxy) naphthalene, 4- (2-chloroethoxy) -1- (2-Hydroxy-3-phenoxypropoxy) naphthalene and the like can also be mentioned.

  Furthermore, 2-methyl-4-methoxy-1- (2-hydroxyethoxy) naphthalene, 2-methyl-4-methoxy-1- (2-hydroxypropoxy) naphthalene, 2-methyl-4-methoxy-1- ( 2-hydroxybutoxy) naphthalene, 2-methyl-4-methoxy-1- (2-hydroxyheptyloxy) naphthalene, 2-methyl-4-methoxy-1- (2-hydroxyoctyloxy) naphthalene, 2-methyl-4 -Methoxy-1- (2-hydroxy-2-phenylethoxy) naphthalene, 2-methyl-4-methoxy-1- (2-hydroxy-3-methoxypropoxy) naphthalene, 2-methyl-4-methoxy-1- ( 2-hydroxy-3-butoxypropoxy) naphthalene, 2-methyl-4-methoxy-1- (2-hydroxy-3- Ryloxypropoxy) naphthalene, 2-methyl-4-methoxy-1- (2-hydroxy-3- (2-ethyl) hexyloxypropoxy) naphthalene, 2-methyl-4-methoxy-1- (2-hydroxy-3) -Stearyloxypropoxy) naphthalene, 2-methyl-4-methoxy-1- (2-hydroxy-3-phenoxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-hydroxyethoxy) naphthalene, 2-chloro -4-methoxy-1- (2-hydroxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-hydroxybutoxy) naphthalene, 2-chloro-4-methoxy-1- (2-hydroxyheptyloxy) Naphthalene, 2-chloro-4-methoxy-1- (2-hydroxyoctyloxy) naphtha 2-chloro-4-methoxy-1- (2-hydroxy-2-phenylethoxy) naphthalene, 2-chloro-4-methoxy-1- (2-hydroxy-3-methoxypropoxy) naphthalene, 2-chloro- 4-methoxy-1- (2-hydroxy-3-butoxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-hydroxy-3-allyloxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-hydroxy-3- (2-ethyl) hexyloxypropoxy) naphthalene, 2-chloro-4-methoxy-1- (2-hydroxy-3-stearyloxypropoxy) naphthalene, 2-chloro-4-methoxy-1 There may also be mentioned-(2-hydroxy-3-phenoxypropoxy) naphthalene.

  In carrying out the second reaction, the molar ratio of the 4-alkoxy- (2-hydroxyalkoxy) naphthalene compound and acryloyl chloride or methacryloyl chloride is preferably selected in the range of 2.0 to 10.0. If the addition molar ratio of the latter to the former is less than 2.0, unreacted naphthalene compound remains, and if the addition ratio exceeds 10.0, the acryloyl chloride or methacryloyl chloride itself used in the second reaction is polymerized. The 4-alkoxy- (2-hydroxyalkoxy) naphthalene compound, which is the target product, is difficult to separate, and the purity of the target product is lowered, which is not preferable. The addition molar ratio is more preferably in the range of 2.2 to 6.0.

When the second reaction is carried out in the presence of a base, examples of the base that can be used include trimethylamine, triethylamine, tripropylamine, tributylamine, diethylamine, dibutylamine, piperidine, pyridine, α-picoline, and γ-picoline. And organic bases such as inorganic bases such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. The molar ratio of addition of these bases to acryloyl chloride or methacryloyl chloride is preferably 1.0 to 1,5. If the addition molar ratio is less than 1.0, the naphthalene compound remains unreacted, and if it exceeds 1,5, the solubility of the product in the reaction solution becomes high and crystallization is not preferable. The addition molar ratio is more preferably 1.1 to 1.2.

  When the second reaction is carried out in the presence of a solvent, the reaction solvent that can be used is not particularly limited as long as it does not react with acryloyl chloride or methacryloyl chloride. Specifically, aromatic solvents such as benzene, toluene, o-xylene, m-xylene, ethylbenzene, i-propylbenzene, chlorobenzene, o-dichlorobenzene, methylnaphthalene, chloronaphthalene, methylene chloride, chloroform, Halogenated hydrocarbon solvents such as 1,2-dichloroethane and 1,2-dichloroethylene, amide solvents such as methylpyrrolidone, dimethylformamide, and dimethylacetamide, ether solvents such as tetrahydrofuran and 1,4-dioxane, acetone, Examples thereof include ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone. The reaction temperature is preferably selected in the range of 0 ° C to 80 ° C. When the reaction temperature is 0 ° C. or lower, the reaction rate is too slow and takes too much time. When the reaction temperature is 80 ° C. or higher, polymerization of acryloyl chloride or methacryloyl chloride itself proceeds to lower the purity of the product, which is not preferable. A more preferable reaction temperature is in the range of 20 ° C to 50 ° C. The concentration of the reactant with respect to the solvent is not particularly limited, and when it is difficult to dissolve in the solvent, the reactant can be dispersed in a slurry state and reacted.

The obtained reaction product is confirmed to be a bis (2- (meth) acryloxyalkoxy) naphthalene compound by an infrared spectrum analysis method, a mass spectrum analysis method, a ¹ H-NMR spectrum analysis method, or the like. Can be confirmed. Both compounds show strong CO stretching vibration attributed to the ester group in the vicinity of 1720 cm ⁻¹ in the infrared spectrum analysis method, and the ¹ H-NMR spectrum analysis shows a spectrum unique to the AMX type acrylic group. Can be easily confirmed.

<Uses of compounds>
The compound according to the first invention obtained by the above reaction, that is, the 4-alkoxy- (2- (meth) acryloxyalkoxy) naphthalene compound is a novel compound. The compound according to the first invention can be used as a photosensitizer of a photopolymerizable monomer, and a photocurable composition can be prepared by blending this compound.

When using the compound which concerns on 1st invention as a photosensitizer, the compound which concerns on 1st invention is mix | blended with a photopolymerizable monomer and a photoinitiator, and a photocurable composition is prepared. This photocurable composition can be easily cured by irradiation with light.

  The photopolymerizable monomer may be a cationic polymerizable monomer, a radical polymerizable monomer, or a mixture thereof. Examples of the photopolymerizable cationic polymerizable monomer include epoxy compounds and vinyl ethers. Common epoxy compounds include alicyclic epoxy compounds, epoxy-modified silicones, aromatic glycidyl ethers, and the like. Examples of the alicyclic epoxy compound include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate and bis (3,4-epoxycyclohexyl) adipate. Examples of commercially available products include those manufactured by Dow Chemical Company, trade names: UVR6105, UVR6110, and the like. Examples of the epoxy-modified silicone include Toshiba GE Silicone, trade name: UV-9300, and the like. Examples of the aromatic glycidyl compound include 2,2′-bis (4-glycidyloxyphenyl) propane, and examples of the vinyl ether include methyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, and 2-ethylhexyl vinyl ether.

  Examples of the photopolymerizable radical polymerizable monomer include styrene, vinyl acetate, acrylic acid, methacrylic acid, acrylonitrile, methacrylonitrile, acrylamide, acrylic ester, and methacrylic ester. Specific examples of (meth) acrylic acid esters include methyl acrylate, butyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, 2-hydroxyethyl acrylate, methyl methacrylate, butyl methacrylate, and cyclohexyl methacrylate. , Tetraethylene glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, epoxy acrylate, urethane acrylate, polyester acrylate, polybutadiene acrylate, polyol acrylate, polyether acrylate, silicone resin acrylate, imide acrylate, and the like. These radical polymerizable monomers may be one kind or a mixture of two or more kinds.

  The blending amount when the compound according to the first invention is used as a photosensitizer is preferably in the range of 0.01 to 2.0% by weight with respect to the photopolymerizable monomer. If the blending amount of the photosensitizer is too small, the curing rate of the photocurable composition will be slow, and if the blending amount of the photosensitizer is too large, the physical properties of the cured product will deteriorate. . A more preferable blending amount of the photosensitizer is in the range of 0.1 to 1.0% by weight.

  As the photopolymerization initiator, an onium salt can be used. As the onium salt, a sulfonium salt or an iodonium salt is usually used. Examples of the sulfonium salt include S, S, S ′, S′-tetraphenyl-S, S ′-(4,4′-thiodiphenyl) disulfonium, bishexafluorophosphate, diphenyl-4-phenylthiophenylsulfonium hexa Examples thereof include fluorophosphate and triphenylsulfonium hexafluorophosphate. As a product marketed, the Dow Chemical company make and brand name: UVI6992 are mentioned, for example. On the other hand, examples of the iodonium salt include 4-isobutylphenyl-4′-methylphenyliodonium hexafluorophosphate, bis (dodecylphenyl) iodonium hexafluoroantimonate, 4-isopropylphenyl-4′-methylphenyliodonium tetrakispentafluorophenylborate. Is mentioned. Examples of commercially available products include Ciba Specialty Chemicals, trade name: Irgacure 250, Rhodia, trade name: 2074, and the like. The addition amount of the initiator to the photopolymerizable monomer is preferably in the range of 0.01 to 5.0% by weight, and more preferably in the range of 0.05 to 2.0% by weight.

  The photocurable composition according to the fourth invention of the present invention is composed of a photopolymerizable monomer and the compound according to the first invention from a photosensitizer and a photopolymerization initiator, and further does not impair the effects of the present invention. Addition of various resins such as diluents, colorants, organic or inorganic fillers, leveling agents, surfactants, antifoaming agents, thickeners, flame retardants, antioxidants, stabilizers, lubricants, plasticizers, etc. An agent can be mix | blended in a normal use range.

  Diluents include epoxy-based diluents such as epoxy acrylate, oxetane-based diluents such as oxacyclobutane, vinyl ether-based diluents, (meth) acrylic monomer-based diluents, and the like. Examples of the colorant include a blue pigment, a red pigment, a white pigment, and a black pigment. Examples of the black pigment include carbon black, acetylene black, lamp black, and aniline black. Examples of yellow pigments include yellow lead, zinc yellow, cadmium yellow, yellow iron oxide, mineral fast yellow, nickel titanium yellow, navel yellow, naphthol yellow S, Hansa Yellow G, Hansa Yellow 10G, Benzidine Yellow G, and Benzidine Yellow. GR, quinoline yellow lake, permanent yellow NCG, tartrazine lake and the like.

  Examples of red pigments include bengara, cadmium red, red lead, mercury cadmium sulfide, permanent red 4R, risor red, lake red D brilliant carmine 6B, eosin lake, rhodamine lake B, alizarin lake, brilliant carmine 3B, and the like. . Examples of the blue pigment include bitumen, cobalt blue, alkali blue lake, Victoria blue lake, phthalocyanine blue, metal-free phthalocyanine blue, phthalocyanine blue partial chloride, first sky blue, and induslen blue BC. Examples of white pigments include zinc white, titanium oxide, antimony white, and zinc sulfide. Examples of other pigments include barite powder, barium carbonate, clay, silica, white carbon, talc, and alumina white.

  The photocurable composition according to the fourth invention of the present invention can be cured by irradiating the coating film with light in the ultraviolet region after coating it on a substrate. The application method is not particularly limited as long as it can apply the photocurable composition onto the substrate, and can be performed by a bar coating method, a spray coating method, or the like. The base material may be any of a steel plate, a printing plate, a film, paper, an aluminum foil or the like that has a flat appearance, a curved surface, or a lump. The photocurable composition applied on the substrate can be quickly cured, particularly by irradiating light in the wavelength region of 300 to 400 nm. The light source in this case is not particularly limited as long as it is a light source capable of emitting light in the wavelength region of 300 to 400 nm. For example, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a halogen lamp, sunlight, a metal halide lamp, a xenon lamp UV (UV) LED lamps, H lamps manufactured by Fusion, D lamps, and the like.

  The light irradiation is preferably performed in the absence of oxygen. When irradiated in the presence of oxygen, the progress of the photopolymerization reaction is inhibited by oxygen, and the surface of the cured film cannot be made sticky (tack), and it is necessary to add a large amount of initiator. Examples of the photocuring method in the absence of oxygen include a method performed in an inert gas atmosphere such as nitrogen gas and helium gas. It is also possible to employ a method of covering with an oxygen-impermeable film and irradiating light from above the film. In addition, confirmation of completion of photocuring can be performed by a tack (stickiness) free test (a finger touch test). In this tack-free test, the cured film on the surface of the substrate such as a film is touched with a fingertip, the tack is confirmed, and the time until tack of the cured film disappears is called “tack-free time” (light irradiation time). The slowness of the curing reaction can be determined by the length of time. A shorter “tack free time” means a faster cure rate.

  In order to apply and cure the photocurable composition according to the fourth invention of the present invention on, for example, a film surface, the following procedure is performed. That is, the photocurable composition is applied to the film surface by a bar coating method. When the base material is a film, it is applied using a bar number coater with a rod number such that the thickness of the coating film is usually several μm to several tens of μm. The photopolymerizable composition containing the photopolymerizable monomer can be rapidly cured by irradiating the light of the above-described light source onto the coated product thus obtained.

  EXAMPLES Hereinafter, although this invention is demonstrated in detail based on an Example, this invention is not limited to the following description examples, unless the meaning is exceeded.

[Example 1]
<Production of 4-methoxy-1- (2-acryloxypropoxy) naphthalene {compound represented by Structural Formula (4)}
(First reaction)
A three-necked flask equipped with a stirrer and a thermometer and having a capacity of 100 ml was charged as a solution in which 3.5 g (20 mmol) of 4-methoxy-1-naphthol was dissolved in 15 ml of methanol under a nitrogen atmosphere, and then 4 g (70 mmol) of propylene oxide. ). Next, an aqueous solution in which 0.8 g (20 mmol) of sodium hydroxide was dissolved in 3 ml of water was added, and stirring was continued at room temperature. Two days later, crystals were precipitated. The reaction solution was concentrated to further precipitate crystals, and then filtered and dried to obtain 2.8 g (12 mmol) of pale blue white powder. The yield of the product based on 4-methoxy-1-naphthol was 60 mol%, and the melting point was 97-98 ° C.

(Second reaction)
In a three-neck flask having a capacity of 30 ml equipped with a stirrer and a thermometer, 464 mg (2 mmol) of 4-methoxy-1- (2-hydroxypropoxy) naphthalene obtained in the first reaction was dissolved in 5 ml of acetone. I prepared. Then, 400 mg (4.5 mmol) of acryloyl chloride was added, and then an acetone solution of 450 mg (4.5 mmol) of triethylamine was added while the three-necked flask was cooled with water. The reaction solution generated weak heat (approx. 3 ° C.), and a large amount of white precipitate immediately formed in the reaction solution. After stirring for 10 minutes, 1.5 g of water was added, and all the white precipitate dissolved. . When 2.5 g of water was further added and the reaction solution became slightly cloudy, vacuum was applied to the reaction solution to scatter acetone, and a light red oily substance precipitated. To this, 4 g of methylene chloride was added to dissolve the oil, washed well with water, and then applied to a silica gel column. The distilled methylene chloride solution was concentrated to obtain a pale red oil (220 mg). The yield of the product based on 4-methoxy-1- (2-hydroxypropoxy) naphthalene was 37 mol%.

About the obtained product, (1) Refractive index (refractive index measuring device based on JIS K0062, manufactured by Atago Co., Ltd., model: IT), (2) infrared (IR) spectrophotometer (manufactured by JASCO Corporation, model: IR spectrum by IR-810), (3) Nuclear magnetic resonance apparatus (NMR) (manufactured by JEOL Ltd., model: GSX FT NMR Spectrometer), ¹ H-NMR, (4) Mass spectrum (manufactured by Shimadzu Corporation, mass spectrometry) Meter, model: GCMS-QP5000) and the like.

The measurement results are as follows, and it was confirmed that the product was 4-methoxy-1- (2-acryloxypropoxy) naphthalene.
(1) Melting point: liquid at room temperature (2) Refractive index: 1.586
(3) Infrared (IR) absorption spectrum (KBr, cm ⁻¹ ): absorption at wavelengths such as 1718, 1621, 1588, 1458, 1380, 1265, 1234, 1190, 1154, 1096, 800, 760, 660, etc. It was.
(4) ¹ H-NMR (CDCl ₃ , 270 MHz) δ: 1.50 (d, J = 9 Hz, 3H), 3.97 (s, 3H), 4.14 (d, J = 5 Hz, 1H), 4.19 (d, J = 5 Hz, 1H), 5.50 (m, 1H), 5.85 (d, J = 11 Hz, 1H), 6.17 (dd, J ₁ = 11 Hz, J ₂ = 17 Hz) , 1H), 6.45 (d, J = 17 Hz, 1H), 6.68 (s, 1H), 6.70 (s, 1H), 7.50 (m, 2H), 8.20 (m, 2H).
(5) Mass spectrum: (EI-MS) m / z = 286 (M ⁺ )

[Example 2]
<Production of 4-butoxy-1- (2-acryloxypropoxy) naphthalene {compound represented by the structural formula (12)}
(First reaction)
A 100 ml three-necked flask equipped with a stirrer and a thermometer was charged with a solution of 4.3 g (20 mmol) of 4-butoxy-1-naphthol in 16 ml of methanol under a nitrogen atmosphere, and then 4 g (70 mmol) of propylene oxide. ). Next, an aqueous solution in which 0.8 g (20 mmol) of sodium hydroxide was dissolved in 3 ml of water was added, and stirring was continued at room temperature. Two days later, crystals were precipitated, and the reaction solution was concentrated to further precipitate crystals, followed by filtration and drying to obtain 3.1 g (11 mmol) of a white powder. The yield of the product based on 4-butoxy-1-naphthol was 55 mol%, and the melting point was 92-93 ° C.

(Second reaction)
A solution obtained by dissolving 548 mg (2 mmol) of 4-butoxy-1- (2-hydroxypropoxy) naphthalene obtained in the first reaction in 4 ml of acetone in a three-neck flask equipped with a stirrer and a thermometer and having a capacity of 30 ml. Then, 400 mg (4.5 mmol) of acryloyl chloride was charged. Next, a solution prepared by dissolving 450 mg (4.5 mmol) of triethylamine in 1 ml of acetone was added while cooling the three-necked flask with water. The reaction solution was weak and exothermic, and a large amount of white precipitate immediately formed in the reaction solution. After stirring the reaction solution for 10 minutes, when 1.5 g of water was added, all of the white precipitate was dissolved. An additional 2.5 g of water was added to the reaction solution, and when it was slightly cloudy, it was stored overnight in a refrigerator. As a result, a pale yellow oily substance was precipitated at the bottom of the reaction solution. When the reaction solution was concentrated under reduced pressure and acetone was scattered, the amount of oil increased. Therefore, the supernatant was discarded and washed well with water to obtain 340 mg of a colorless oil. The yield of the product based on 4-butoxy-1- (2-hydroxypropoxy) naphthalene was 52 mol%.

The obtained pale yellow oily product was analyzed in the same procedure as in Example 1, and the result was as follows. The product was confirmed to be 4-butoxy-1- (2-acryloxypropoxy) naphthalene. .
(1) Melting point: liquid at room temperature (2) Refractive index: n _D = 1.553
(3) Infrared (IR) absorption spectrum (KBr, cm ⁻¹ ): 2950, 2920, 2860, 1720, 1621, 1592, 1456, 1400, 1378, 1270, 1254, 1192, 1156, 1096, 800, 760, etc. Absorption was observed at the wavelength.
(4) ¹ H-NMR (CDCl ₃ , 270 MHz) δ: 1.02 (t, J = 9 Hz, 3H), 1.50 (d, J = 9 Hz, 3H), 1.60 (m, 2H), 1.90 (m, 2H), 4.06 (t, J = 3 Hz, 2H), 4.13 (d, J = 5 Hz, 1H), 4.17 (d, J = 5 Hz, 1H), 5. 50 (m, 1H), 5.84 (d, J = 11 Hz, 1H), 6.17 (dd, J ₁ = 11 Hz, J ₂ = 17 Hz, 1H), 6.45 (d, J = 17 Hz, 1H) ), 6.69 (s, 1H), 6.70 (s, 1H), 7.50 (m, 2H), 8.20 (m, 2H)
(5) Mass spectrum: (EI-MS) m / z = 328 (M ⁺ )

[Example 3]
<Synthesis of 4- (2-phenoxyethoxy) -1- (2-acryloxypropoxy) naphthalene>
(First reaction)
A 100 ml three-necked flask equipped with a stirrer and a thermometer was charged with 5.6 g (20 mmol) of 4- (2-phenoxyethoxy) -1-naphthol dissolved in 25 ml of methanol under a nitrogen atmosphere, and then oxidized. 4 g (70 mmol) of propylene was added. Next, an aqueous solution in which 0.8 g (20 mmol) of sodium hydroxide was dissolved in 3 ml of water was added, and stirring was continued at room temperature. Two days later, crystals were precipitated. The reaction solution was concentrated to further precipitate crystals, and then filtered and dried to obtain 5.1 g (15 mmol) of a white powder. The yield of the product based on 4- (2-phenoxyethoxy) -1-naphthol was 75 mol%, and the melting point was 76 to 77 ° C.

(Second reaction)
Into a 30 ml three-necked flask equipped with a stirrer and a thermometer, 676 mg (2 mmol) of 4- (2-phenoxyethoxy) -1- (2-hydroxypropoxy) naphthalene obtained in the first reaction was added to 5 ml. A solution dissolved in acetone was charged. Then 400 mg (4.5 mmol) of acryloyl chloride was added. Next, a solution obtained by dissolving 460 mg (4.5 mmol) of triethylamine in 1 ml of acetone was added while the three-necked flask was cooled with water. The reaction solution was weak and exothermic, and a large amount of white precipitate immediately formed in the reaction solution. After stirring the reaction solution for 10 minutes, when 1.5 g of water was added, all of the white precipitate was dissolved. When 2.5 g of water was further added and the mixture was kept in a refrigerator overnight when it became slightly cloudy, crystals were precipitated at the bottom of the reaction solution. The crystals were separated by suction filtration, washed well with water, and dried to obtain 260 mg of white powder. The yield of the product with respect to 4- (2-phenoxyethoxy) -1- (2-hydroxypropoxy) naphthalene was 35 mol%.

The result of analyzing the product in the same procedure as in Example 1 was as follows, and the product was confirmed to be 4- (2-phenoxyethoxy) -1- (2-acryloxypropoxy) naphthalene.
(1) Melting point: 93-94 ° C
(2) IR (KBr, cm ⁻¹ ): 2980, 2926, 2860, 1724, 1620, 1590, 1492, 1454, 1400, 1380, 1362, 1265, 1250, 1230, 1190, 1150, 1094, 1080, 1070, Absorption was observed at wavelengths such as 1020, 970, 930, 900, 768, 744, and 682.
(3) ¹ H-NMR (CDCl ₃ , 270 MHz) δ: 1.49 (d, J = 9 Hz, 3H) 4.13 (d, J = 5 Hz, 1H), 4.18 (d, J = 5 Hz, 1H), 4.60 (s, 4H), 5.50 (m, 1H), 5.83 (d, J = 11 Hz, 1H), 6.17 (dd, J ₁ = 11 Hz, J ₂ = 17 Hz, 1H), 6.44 (d, J = 17 Hz, 1H), 6.69 (d, J = 8 Hz, 1H), 6.75 (d, J = 8 Hz, 1H), 6.95 (t, J = 8 Hz, 1 H), 7.0 (d, J = 8 Hz, 2 H), 7.30 (t, J = 8 Hz, 2 H), 7.50 (m, 2 H), 8.20 (m, 2 H)
(4) Mass spectrum: (EI-MS) m / z = 392 (M ⁺ )

[Example 4]
<Synthesis of 4-methoxy-1- (2-methacryloxyethoxy) naphthalene>
(First reaction)
An autoclave equipped with a thermometer and a stirrer and having a capacity of 100 ml was charged with 5.2 g (30 mmol) of 4-methoxy-1-naphthol dissolved in 30 ml of methanol, and then 1.2 g (30 mmol) of sodium hydroxide. An aqueous solution dissolved in 6 ml of water was added. Subsequently, 4.4 g (100 mmol) of ethylene oxide was injected over 15 minutes so that the pressure did not exceed 0.3 MPa. Thereafter, stirring was continued at room temperature, and stirring was continued for 2 days. Then, 20 ml of water was added to the resulting slurry-like reaction mixture, and the mixture was thoroughly stirred and filtered with suction. After thoroughly washing the reaction product with water and drying, 4.4 g (20 mmol) of white powder was obtained. The yield of the product based on 4-methoxy-1-naphthol was 67 mol%, and the melting point was 98-99 ° C.

(Second reaction)
A solution of 436 mg (2 mmol) of 4-methoxy-1- (2-hydroxyethoxy) naphthalene obtained in the first reaction dissolved in 4 ml of acetone was charged into a 30-ml three-necked flask equipped with a stirrer and a thermometer. It is. Next, 240 mg (2.4 mmol) of methacryloyl chloride was added. Then, a solution of 202 mg (2 mmol) of triethylamine dissolved in 1 ml of acetone was added while cooling the three-necked flask with ice water. The reaction solution was weak and exothermic, and a white precipitate immediately formed in the reaction solution. After stirring the reaction solution for 10 minutes, 1.5 g of water was added to dissolve all the white precipitate. When 2 g of water was further added and stored in a refrigerator overnight when it became slightly cloudy, crystals were precipitated. The crystals were separated by suction filtration, washed well with water, and then dried to obtain 160 mg of white crystals. The yield of the product based on 4-methoxy-1- (2-hydroxyethoxy) naphthalene was 30 mol%.

The result of analyzing the product in the same procedure as in Example 1 was as follows, and the product was confirmed to be 4-methoxy-1- (2-methacryloxyethoxy) naphthalene.
(1) Melting point: 69-70 ° C
(2) IR (KBr, cm ⁻¹ ) 2945, 1713, 1688, 1464, 1440, 1380, 1318, 1268, 1164, 1100, 1084, 940, 760
(3) ¹ H-NMR (CDCl ₃ , 270 MHz) δ: 1.99 (s, 3H), 3.99 (s, 3H), 4.37 (t, J = 8 Hz, 2H), 4.65 ( t, J = 8 Hz, 2H), 5.60 (d, J = 2 Hz, 1H), 6.19 (d, J = 2 Hz, 1H), 6.69 (d, J = 9.5 Hz, 1H), 6.74 (d, J =). 5Hz, 1H), 7.50 (m, 2H), 8.21 (m, 2H)
(4) Mass spectrum: (EI-MS) m / z = 286 (M ⁺ )

[Evaluation Test-1 as Photopolymerization Sensitizer]
The method described in Example 1 in 100 parts by weight of trimethylolpropane triacrylate as a monomer, 2 parts by weight of tolyl-i-butylphenyliodonium hexafluorophosphate (Ciba Specialty, trade name: Irgacure 250, the same shall apply hereinafter) 1.0 part of 4-methoxy-1- (2-acryloxypropoxy) naphthalene {compound represented by the structural formula (2)} prepared in Step 1 was added to obtain a uniform photocurable composition. This photocurable composition was applied to the surface of a polyester film (trade name: Lumirror, manufactured by Toray Industries, Inc.) having a thickness of 100 μm with a bar coater so as to have a film thickness of 12 μm. Then, under a nitrogen atmosphere, a UV-LED lamp (light source having a wavelength of 395 nm and the light source having the strongest light, Thunder Corp., model: SDL-10M3CUV, hereinafter the same) was used, and the irradiation intensity was 3 mw / cm ² . The light irradiation time “tack free time” until stickiness disappears was 2.8 minutes.

[Evaluation Test-2 as Photopolymerization Sensitizer]
4-Butoxy-1- (2-) prepared by the method described in Example 2 with 2 parts by weight of tolyl-i-butylphenyliodonium hexafluorophosphate (same as above) to 100 parts by weight of trimethylolpropane triacrylate as a monomer. Acrylicoxypropoxy) naphthalene {compound represented by the structural formula (10)} (1.0 part by weight) was added to obtain a uniform photocurable composition. This photocurable composition was applied to the surface of a polyester film (trade name: Lumirror, manufactured by Toray Industries, Inc.) having a thickness of 100 μm with a bar coater so as to have a film thickness of 12 μm. Then, under a nitrogen atmosphere, a high pressure mercury lamp (the same as above) was used, and the irradiation intensity was 3 mw / cm ² . The light irradiation time “tack free time” until tackiness disappears was 1.1 minutes.

[Evaluation Test-3 as a Photopolymerization Sensitizer]
4- (2-phenoxyethoxy)-produced by the method described in Example 3 with 100 parts by weight of trimethylolpropane triacrylate as a monomer and 2 parts by weight of tolyl-i-butylphenyliodonium hexafluorophosphate (same as above) 1.0 part by weight of 1- (2-acryloxypropoxy) naphthalene was added to obtain a uniform photocurable composition. This photocurable composition was applied to a surface of a polyester film (same as above) having a thickness of 100 μm by a bar coater so as to have a film thickness of 12 μm. Then, under a nitrogen atmosphere, a UV-LED lamp (same as above) was used, and irradiation was performed with an irradiation intensity of 3 mw / cm ² . The light irradiation time “tack free time” until stickiness disappears was 2.4 minutes.

[Evaluation Test 4 as Photopolymerization Sensitizer]
4-Methoxy-1- (2-methacrylic acid) produced by the method described in Example 4 using 100 parts by weight of trimethylolpropane triacrylate as a monomer and 2 parts by weight of tolyl-i-butylphenyliodonium hexafluorophosphate (same as above). Oxyethoxy) naphthalene (1.0 part by weight) was added to obtain a uniform photocurable composition. This photocurable composition was applied to the surface of a 100 μm thick polyester film (same as above) with a bar coater so that the film thickness was 12 microns. Then, under a nitrogen atmosphere, irradiation was performed using a UV-LED lamp (same as above) with an irradiation intensity of 3 mW / cm ² . The light irradiation time “tack free time” until tackiness disappears was 45 seconds.

[Evaluation Test as Photopolymerization Sensitizer-Comparative Example 1]
In the example described in Evaluation Test-1 as a photopolymerization sensitizer, photocurable composition was prepared in the same procedure as in the same example except that 4-methoxy-1- (2-acryloxyethoxy) naphthalene was not added. The product was prepared and applied to the surface of the polyester film, and then irradiated under a nitrogen atmosphere using a UV-LED lamp (same as above) with an irradiation intensity of 3 mw / cm ² , but it cured even when irradiated for 25 minutes. There wasn't.

[Evaluation Test-5 as a Photopolymerization Sensitizer]
For the alicyclic epoxy compound (manufactured by DOW, UVR-6105) as a monomer, 2 parts by weight of 4-isobutylphenyl-4′-methylphenyliodonium hexafluorophosphate (same as above) was prepared by the method described in Example 1. A photocurable composition was prepared by mixing 0.5 parts by weight of 4-methoxy-1- (2-acryloxypropoxy) naphthalene {compound represented by Structural Formula (2)}. This photocurable composition was applied to a surface of a polyester film (same as above) having a thickness of 100 μm by a bar coater so as to have a film thickness of 12 μm. Then, irradiation was performed from the surface using a UV-LED lamp (same as above) with an irradiation intensity of 3 mw / cm ² . The light irradiation time “tack free time” until stickiness disappears was 2.7 minutes.

[Evaluation Test-6 as a Photopolymerization Sensitizer]
4-Butoxy-1-produced by the method described in Example 2, 2 parts by weight of 4-isobutylphenyl-4′-methylphenyliodonium hexafluorophosphate (same as above) with respect to the alicyclic epoxy compound (same as above) as a monomer 0.5 part of (2-acryloxypropoxy) naphthalene {compound represented by Structural Formula (10)} was mixed to prepare a photocuring composition. This photocurable composition was applied to a surface of a polyester film (same as above) having a thickness of 100 μm by a bar coater so as to have a film thickness of 12 μm. Then, a UV-LED lamp (the same as above) was used from the surface, and the irradiation intensity was 3 mw / cm ² . The light irradiation time “tack free time” until stickiness disappears was 4.2 minutes.

[Evaluation Test-7 as Photopolymerization Sensitizer]
4- (2-phenoxy) produced by the method described in Example 3, 2 parts by weight of 4-isobutylphenyl-4′-methylphenyliodonium hexafluorophosphate (same as above) with respect to the alicyclic epoxy compound (same as above) as a monomer Ethoxy) -1- (2-acryloxypropoxy) naphthalene 0.5 part was mixed to prepare a photocuring composition. This photocurable composition was applied to a surface of a polyester film (same as above) having a thickness of 100 μm by a bar coater so as to have a film thickness of 12 μm. Next, a UV-LED lamp (same as above) was used from the surface, and the irradiation intensity was 3 mw / cm ² . The light irradiation time “tack free time” until stickiness disappears was 4.2 minutes.

[Evaluation Test as Photopolymerization Sensitizer-Comparative Example 2]
In the example described in Evaluation Test-5 as a photopolymerization sensitizer, a photocurable composition was prepared in the same procedure as in the same example except that 4-methoxy-1- (2-acryloxypropoxy) naphthalene was not added. A product was prepared, applied to the surface of a polyester film (same as above), and then irradiated under a nitrogen atmosphere using a UV-LED lamp (same as above) with an irradiation intensity of 3 mw / cm ² . It did not cure even after 35 minutes of irradiation.

[Sublimation Test Example 1 of Curable Composition]
A polyester film (same as above) coated with the photocurable composition prepared by the method described in Evaluation Test-1 as a photopolymerization sensitizer was heated in an oven adjusted to a temperature of 180 ° C. The polyester film is taken out of the oven at regular intervals, and the UV absorption peak in the vicinity of a wavelength of 331 nm out of the UV spectrum caused by 4-methoxy-1- (2-acryloxypropoxy) naphthalene is obtained by an ultraviolet / visible spectrophotometer. (Shimadzu Corporation make, model: UV2200). 1 and 2 show the UV spectra measured in this example. The absorbance peak height at a wavelength of 331 nm was compared between before heating (FIG. 1) and after heating (FIG. 2), and the rate of decrease in absorbance peak after heating was examined. 4-methoxy-1- (2-acrylic The degree of sublimation of oxypropoxy) naphthalene was determined. As a result, the peak height of the absorbance was about 17% lower than that before heating after 10 minutes of overheating, so it was determined that the sublimation was about 17%.

[Sublimation test example 2 of curable composition]
The photocurable composition prepared by the method described in Evaluation Test-2 as a photopolymerization sensitizer was applied to a polyester film (same as above) in the same manner as in the sublimation test example-1 of the curable composition, The polyester film was heated in an oven adjusted to a temperature of 180 ° C. The polyester film was removed from the oven at regular intervals and the UV spectrum was measured (measurement apparatus is the same as above). FIG. 3 and FIG. 4 show UV absorbance spectra having a wavelength of around 331 nm due to 4-butoxy-1- (2-acryloxypropoxy) naphthalene. The UV absorbance peak height at a wavelength of 331 nm was compared between before heating (FIG. 3) and after heating (FIG. 4), and the rate of decrease in absorbance peak after heating was examined to determine 4-butoxy-1- (2- The degree of sublimation of (acryloxypropoxy) naphthalene was determined. The UV spectrum at a wavelength of 331 nm after heating for 10 minutes (FIG. 4) showed little change in absorbance compared to that before heating (FIG. 3), and only 4% sublimated after heating for 10 minutes. .

[Sublimation test example 3 of curable composition]
The photocurable composition prepared by the method described in Evaluation Test-4 as a photopolymerization sensitizer was applied to a polyester film (same as above), and the temperature was adjusted to 180 ° C. in the same manner as in Sublimation Test Example-1. Heated in a controlled oven. The polyester film was removed from the oven at regular intervals and the UV spectrum was measured. FIG. 5 and FIG. 6 show the UV spectrum measured in this example, with respect to the absorbance spectrum having a wavelength of around 331 nm, which is caused by 4-methoxy-1- (2-methacryloxyethoxy) naphthalene. The reduction rate of the absorbance peak at a wavelength of 331 nm was examined to determine the degree of sublimation of 4-methoxy-1- (2-methacryloxyethoxy) naphthalene. The UV spectrum at a wavelength of 331 nm after heating for 10 minutes (FIG. 6) showed little change in absorbance compared to that before heating (FIG. 5), and only 5% sublimated after heating for 10 minutes. .

[Sublimation Test Example 4 of Curable Composition (Comparative Example)]
In the example described in Evaluation Test 1 as a photopolymerization sensitizer, except that 4-methoxy-1-ethoxynaphthalene was used instead of 4-methoxy-1- (2-acryloxypropoxy) naphthalene, the same example A photocurable composition was prepared in the same procedure as in. This photocurable composition was applied to a polyester film (same as above) and heated in an oven adjusted to a temperature of 180 ° C. in the same manner as in sublimation test example-1. The polyester film was removed from the oven at regular intervals and the UV spectrum was measured. The measurement results are shown in FIGS. The absorbance at a wavelength of 335 nm caused by 4-methoxy-1-ethoxynaphthalene after heating for 10 minutes (FIG. 8) is significantly lower than that before heating (FIG. 7), and sublimates about 70%. Turned out to be.

The 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound according to the first invention of the present invention is a novel compound, and this compound is a light comprising a photopolymerizable monomer and a photopolymerization initiator. It can mix | blend with a curable composition and can utilize as a photoinitiator.

It is a UV spectrum of the sample before a heating in sublimation test example-1. It is a UV spectrum of the sample after a heating in sublimation test example-1. It is a UV spectrum of the sample before a heating in sublimation test example-2. It is a UV spectrum of the sample after a heating in sublimation test example-2. It is a UV spectrum of the sample before a heating in sublimation test example-3. It is a UV spectrum of the sample after a heating in sublimation test example-3. It is a UV spectrum of the sample before a heating in sublimation test example-4. It is a UV spectrum of the sample after a heating in sublimation test example-4.

Claims (6)

A 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound represented by the structural formula (1).

{In Structural Formula (1), R ₁ represents any _one of an alkyl group, a hydroxyalkyl group, an alkoxyalkyl group, an aryloxyalkyl group, and a halogenated alkyl group, and R ₂ represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group. Any one of a methyl group, an allyloxymethyl group, and an aryloxymethyl group, R ₃ represents a hydrogen atom or a methyl group, X and Y may be the same or different, a hydrogen atom, an alkyl group, a halogen atom, A hydroxyl group, an alkoxy group, an alkylthio group, an arylthio group, a carboxyl group, or a sulfonic acid group is shown. }   The 4-alkoxy-1- (2-hydroxyalkoxy) naphthalene compound is subjected to an addition reaction with an alkylene oxide compound, and then the compound is reacted with acryloyl chloride or methacryloyl chloride. Of 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound.   The method for producing a 1,4-bis (2- (meth) acryloxyalkoxy) naphthalene compound according to claim 2, wherein the alkylene oxide is ethylene oxide or propylene oxide.   A photopolymerization sensitizer comprising the 4-alkoxy-1- (2- (meth) acryloxyalkoxy) naphthalene compound according to claim 1 as an active ingredient.   A photocurable composition comprising the photopolymerization sensitizer according to claim 4, a photopolymerization initiator, and a photopolymerizable monomer. The photocurable composition according to claim 5, wherein the photopolymerization initiator is an onium salt.

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