JP2013014533A - Urethane (meth)acrylate compound having condensed polycyclic aromatic skeleton, chain transfer agent, and polymer using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an environment-friendly novel type chain transfer agent causing no odor problem, being composed of only carbon, hydrogen and oxygen, and capable of giving a functional group to a polymer; the polymer imparted with the functional group; and a method of producing the polymer.SOLUTION: The chain transfer agent includes a condensed polycyclic aromatic skeleton represented by general formula (1). In the formula: n is an integer of 0-3; R is a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxyalkyl group, a glycidyl group, a hydroxyalkyl group or an aryloxy alkyl group; p is an integer of 1 or 2; q is an integer of 0-4; r is an integer of 1-4; Y and Z are each a hydrogen atom or a methyl group; and X is a hydrogen atom, an alkyl group, or aryl group.

Description

The present invention relates to a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton, a chain transfer agent containing the urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton, and a polymer and a polymer produced using the same It is related with the manufacturing method.

Radical polymerizable compounds are organic compounds that are widely used industrially as raw materials for synthetic resins. Examples of such radical polymerizable compounds include acrylic acid, methacrylic acid and esters thereof, and styrene compounds. A wide variety of compounds are known.

In the polymerization process of these radically polymerizable compounds, it is beneficial to adjust the molecular weight of the produced polymer according to the intended use. In particular, when used for applications such as coating agents, adhesives, pressure-sensitive adhesives, paper strength enhancers, binders, resists, etc., molecular weight adjustment is an important technique.

There are various techniques for adjusting the molecular weight in the polymerization reaction of the radical polymerizable compound, but a method of adding a chain transfer agent to the polymerization system is often used. As the chain transfer agent, conventionally, a halogenated hydrocarbon represented by carbon tetrachloride, an alkyl mercaptan compound represented by t- or n-dodecyl mercaptan, or a sulfide compound has been conventionally used (for example, patent documents). 1-3.).

For example, low molecular weight acrylic polymers have been widely used for applications such as paints, adhesives, and sealing materials. When producing such low molecular weight acrylic polymers, mercapto as a chain transfer agent is used. A compound is used (for example, refer patent documents 4-6).

In the polymerization of styrene, mercaptan chain transfer agents are added to adjust the average molecular weight, molecular weight distribution, melt flow index, and the like (see, for example, Patent Documents 7 and 8).

Also, in the production of polymerized toners used in copiers and printers, mercaptan chain transfer agents are used in order to obtain low molecular weight and sharp molecular weight distribution when polymerizing styrene monomers and acrylic monomers. (For example, refer to Patent Documents 9 and 10).

On the other hand, the chain transfer agent is known not only to adjust the molecular weight as described above, but also to give its own residue to the polymer terminal from the reaction mechanism (see, for example, Non-Patent Documents 1 to 3). ). Utilizing this fact, a technique for imparting a functional group to a polymer terminal by using a chain transfer agent having a functional group has also been proposed (see, for example, Patent Documents 11 and 12, Non-Patent Documents 4 and 5). ).

However, halogenated hydrocarbons such as carbon tetrachloride, which are conventional chain transfer agents, have environmental problems such as destroying the ozone layer of the earth, and sulfur compounds such as alkyl mercaptans and sulfides have a strong odor and are difficult to handle. In addition, there is a problem that the odor derived from the sulfur compound incorporated into the resin remains. In addition, when these chain transfer agents are used, naturally, sulfur and halogen are taken into the polymerization terminal, corroding the container, the resin becomes hygroscopic, and the environment when the resin is disposed of. It becomes a problem. On the other hand, alpha methyl styrene dimer has few environmental problems and is widely used, but still has a problem of having an odor.

On the other hand, as a compound having a structure similar to the urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention, a compound containing a naphthalene ring or an anthracene ring and an acryloyl group or a methacryloyl group is known (patent) References 13-21). A (meth) acrylate compound having a fluorene skeleton is also known (Patent Document 22).

However, the urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention is not known, and the urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention is a chain transfer agent. It is not known to have any effect.

JP 2009-522411 A JP 2008-519137 A JP-A-9-118841 Japanese Patent Publication No.58-455 Japanese Patent Laid-Open No. 55-5950 Japanese Examined Patent Publication No. 46-40693 JP 2002-241413 A JP 2009-197105 A JP-A-7-330912 JP 2004-224840 A Japanese Patent Publication No.57-10850 JP 2010-222285 A JP 2008-1640 A JP 2008-1641 A JP 2008-24694 A JP 2009-138090 A JP 2007-204438 A JP 2008-088132 A JP 2008-169156 A JP 2009-040811 A JP 2010-018746 A JP 2008-285468 A

By AGE Odian PRINCIPLES OF POLYMERISATION (FOURTH Edition) (2004) 238 pages Takatsu Otsu, “Chemistry of Polymer Synthesis” (Chemical Doujin, 1979) p. 93 Edited by Mikiharu Tsunoike “Radical Polymerization Handbook” (NTS, 2010), p. 47 Shima Tanaka, Haruo Nishida, and Takeshi Endo, Macromolecules 2009, 42, pages 293-298 Tetsuo Ogawa, Research on paints, No. 137, Oct, 2001, p. 11

Accordingly, an object of the present invention is to provide a new chain transfer agent that solves the problems of conventional chain transfer agents. That is, to solve the environmental problems of halogenated hydrocarbons such as carbon tetrachloride, which is a conventional chain transfer agent, and odor problems such as sulfur compounds such as alkyl mercaptans and sulfides. In addition, conventionally known chain transfer agents such as corrosion problems of resin containers and the like that incorporate these chain transfer agents into the polymerization terminals, moisture absorption problems of resins, and environmental problems when the resin is disposed of, are known. It is to solve these problems.

In addition, as described above, it has also been proposed to produce a polymer having a functional group at the terminal using a chain transfer agent (see, for example, Patent Documents 11 and 12, Non-Patent Documents 4 and 5). All of the transfer agents are derivatives of the above-mentioned halogenated hydrocarbons, alkyl mercaptans, and alphamethylstyrene dimers, and it must be said that they have the above-mentioned drawbacks as they are.

Therefore, an object of the present invention is to provide a new type of chain transfer agent which is free from problems of odor, corrosivity and hygroscopicity, is environmentally friendly and has a high chain transfer ability. Furthermore, the objective of this invention is providing the polymer provided with the condensed polycyclic aromatic skeleton which has a functional group at the terminal, and its manufacturing method.

In order to solve the above problems, the present inventors have intensively studied radical transfer compound chain transfer agents. In spite of having no halogen atom or sulfur atom in the structure, and having a completely different structure from conventionally known chain transfer agents, it has an excellent chain transfer effect, and the condensed polycyclic ring of the present invention in the molecule. It has been found that a polymer having a residue derived from a urethane (meth) acrylate compound having an aromatic skeleton can be produced, and the present invention has been completed.

That is, the first invention in the present invention resides in a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by the following general formula (1).

(In the formula (1), n represents an integer of 0 to 3, and R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxyalkyl group, a glycidyl group, a hydroxyalkyl group, or an aryloxyalkyl group. , N may be the same or different when n is 2 or 3, p is an integer of 1 or 2, q is an integer of 0 to 4, and r is 1 To p, and when p is 2, the two q and r may be the same or different, and Y and Z are each independently a hydrogen atom or a methyl group. In the case where p is 2, in the plurality of Y and the plurality of Z, Y and Z may be the same or different, and each represents a hydrogen atom or a methyl group. Independently hydrogen atom, alkyl group Represents an aryl group, a set of X Adjacent instead of the substituent, they may form a 6-membered ring bonded to a saturated or unsaturated with one another.)

A second invention resides in the urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton according to the first invention, wherein p and n are 1 in the above formula (1).

A third invention is a urethane (meta) having a condensed polycyclic aromatic skeleton according to the first invention, characterized in that, in the above formula (1), p is 2 and n is 0. ) Acrylate compound.

The fourth invention resides in a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by the following general formula (2).

(In the formula (2), R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxyalkyl group, a glycidyl group, a hydroxyalkyl group, or an aryloxyalkyl group, and q represents an integer of 0 to 4. , R represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, and a plurality of Ys each independently represent a hydrogen atom or a methyl group. Each independently represents a hydrogen atom, an alkyl group or an aryl group, but a pair of adjacent Xs may be bonded to each other to form a saturated or unsaturated 6-membered ring instead of the substituent. .)

The fifth invention resides in a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by the following general formula (3).

(In the formula (3), two q and r may be the same or different, q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z represent Each independently represents a hydrogen atom or a methyl group, and in the plurality of Y and the plurality of Z, Y and Z may be the same or different, and each represents a hydrogen atom or a methyl group, and a plurality of X Each independently represents a hydrogen atom, an alkyl group or an aryl group, but a pair of adjacent Xs may be bonded to each other to form a saturated or unsaturated 6-membered ring instead of the substituent. Good.)

The sixth invention resides in a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by the following general formula (5).

(In the formula (4), two q and r may be the same or different, q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z represent Each independently represents a hydrogen atom or a methyl group, and in the plurality of Y and the plurality of Z, Y and Z may be the same or different, and each represents a hydrogen atom or a methyl group, and a plurality of X Each independently represents a hydrogen atom, an alkyl group or an aryl group.)

The seventh invention resides in a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by the following general formula (4).

(In the formula (5), q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, And each independently represents a hydrogen atom or a methyl group, and a plurality of X's each independently represents a hydrogen atom, an alkyl group or an aryl group.)

The eighth invention relates to a compound having a condensed polycyclic aromatic skeleton represented by general formula (13) and a (meth) acrylate compound having an isocyanate group represented by general formula (14), in the presence of a solvent. The present invention resides in a method for producing a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton according to the first invention, wherein the addition reaction is carried out under or in the absence.

(13) In the formula, n represents an integer of 0 to 3, m represents an integer of 1 or 2, and R represents a hydrogen atom, alkyl group, aryl group, aralkyl group, alkoxyalkyl group, glycidyl group, hydroxyalkyl. A group or an aryloxyalkyl group, and when n is 2 or 3, the plurality of R may be the same or different. Each X independently represents a hydrogen atom, an alkyl group or an aryl group, but a pair of adjacent Xs may be bonded to each other to form a saturated or unsaturated 6-membered ring instead of the substituent. Good.

(14) In the formula, q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, and Y and Z each independently A hydrogen atom or a methyl group is represented, and Y in the case where there are a plurality of them each independently represents a hydrogen atom or a methyl group.

A ninth invention resides in a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton according to any one of the first to seventh inventions.

A tenth invention resides in a radical polymerizable composition containing a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton as described in the ninth invention, and a radical polymerizable compound.

The eleventh invention resides in the radically polymerizable composition according to the tenth invention, wherein the radically polymerizable compound is (meth) acrylic acid, (meth) acrylic acid ester or styrene.

A twelfth invention is a radical polymerization of a radically polymerizable composition containing a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton according to the ninth invention and a radically polymerizable compound. A polymer having a residue derived from a chain transfer agent composed of a urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton at the terminal or part of the main chain of the polymer. .

A thirteenth invention resides in the polymer according to the twelfth invention, wherein the radical polymerizable compound is (meth) acrylic acid, (meth) acrylic acid ester or styrene.

A fourteenth invention is a polymer characterized by radical polymerizing a radical polymerizable compound in the presence of a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton according to the ninth invention. In the method for producing a polymer having a residue derived from a chain transfer agent comprising a urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton at a terminal or a part of the main chain.

In the present invention, (meth) acrylate represents acrylate or methacrylate, (meth) acryloyl represents acryloyl or methacryloyl, and (meth) acryl represents acryl or methacryl.

In the present invention, the urethane (meth) acrylate group refers to a substituent represented by the following general formula (6).

(In the formula (6), q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, And each independently represents a hydrogen atom or a methyl group, and * represents a bonding position of the substituent.)

The chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention has no unpleasant odor derived from a sulfur compound, and is effective in reducing the molecular weight of a desired polymer when used in a radical polymerizable compound. The generation of unpleasant odor in the produced polymer can also be suppressed. Furthermore, a polymer having a condensed polycyclic aromatic skeleton at the terminal is synthesized by polymerizing a radical polymerizable compound using a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention. be able to.

The urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention is a compound obtained by reacting a compound having a condensed polycyclic aromatic skeleton with a (meth) acrylate compound having an isocyanate group. That is, the urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention is a compound in which a naphthalene compound having an hydroxy group, an anthracene compound, and the like and a (meth) acrylate compound are bonded via a urethane bond. is there.

[Urethane (meth) acrylate compounds having a condensed polycyclic aromatic skeleton]
The urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention is a compound represented by the above general formula (1) to general formula (5).

In the general formulas (1) and (2), examples of the alkyl group represented by R include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, and a tert-butyl group. Group, n-pentyl group, n-hexyl group, 2-ethylhexyl group, n-decyl group, n-dodecyl group and the like. As the aryl group, phenyl group, p-tolyl group, o-tolyl group, naphthyl Aralkyl groups include benzyl group, phenethyl group, phenylpropyl group, naphthylmethyl group, naphthylethyl group and the like, and alkoxyalkyl groups include 2-methoxyethyl group, 2-ethoxyethyl group, and the like. , 2-methoxyethoxyethyl group and the like. Examples of the glycidyl group include a glycidyl group and a 2-methylglycidyl group. Examples of the hydroxyalkyl group include a hydroxymethyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 2-hydroxybutyl group, and a 3-hydroxybutyl group. Examples of the aryloxyalkyl group include a phenoxyethyl group and a triloxyethyl group.

Examples of the alkyl group represented by X in the general formulas (1) to (5) include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an amyl group, Examples include 2-ethylhexyl group, 4-methylpentyl group, 4-methyl-3-pentenyl group, and examples of the aryl group include phenyl group, p-tolyl group, o-tolyl group, and naphthyl group.

In the general formulas (1) to (3), as an example in which a pair of adjacent Xs are bonded to each other, X is a CH ₂ CH ₂ group, and adjacent Xs are bonded by a single bond. , X is a CH ₂ CH group, and adjacent Xs are bonded by a double bond, X is a CH═CH group, and adjacent Xs are bonded by a single bond to form an aromatic ring And the like. The 6-membered ring formed by a pair of adjacent Xs may be further substituted with an alkyl group or an aryl group. Furthermore, examples of the substituted alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a tert-butyl group, and the aryl group includes a phenyl group. Group, p-tolyl group, o-tolyl group, naphthyl group and the like.

Next, specific examples of the urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention are shown. Here, a plurality of Rs and Xs each mainly exemplifies the same compound, but each may be a different compound as illustrated in part.

Specific examples of the urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by the general formula (1) include the following.

First, in the general formula (1), a specific example in which the substituent X is a hydrogen atom, an alkyl group or an aryl group, and a pair of adjacent Xs are not bonded to each other to form a 6-membered ring. Indicates.

First, an example in which, in the general formula (1), X is a hydrogen atom, and n = 0 and p = 1 is given. That is, it is a specific example of the compound of the following general formula (7).

(In the formula (7), q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, Each independently represents a hydrogen atom or a methyl group.)

First, an example in which q is 0 and r is 1 is given. Specific examples thereof include 1- (2-acryloyloxyethyl) aminocarbonyloxynaphthalene, 2- (2-acryloyloxyethyl) aminocarbonyloxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxynaphthalene, 2- (2-methacryloyloxyethyl) aminocarbonyloxynaphthalene.

Similarly, specific examples where q is 1 and r is 1 include 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxynaphthalene, 2- [2- (2-acryloyloxyethoxy) ethyl. Aminocarbonyloxynaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxynaphthalene, 2- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxynaphthalene, 1- [2- ( 2-acryloyloxypropoxy) propyl] aminocarbonyloxynaphthalene, 2- [2- (2-acryloyloxypropoxy) propyl] aminocarbonyloxynaphthalene, 1- [2- (2-methacryloyloxypropoxy) propyl] aminocarbonyloxynaphthalene , - [2- (2-methacryloyloxy propoxy) propyl] amino carbonyloxy naphthalene.

Similarly, specific examples where q is 2 and r is 1 include 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxynaphthalene, 2- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxynaphthalene, 1- [2- {2- (2-methacryloyloxyethoxyethoxy}) ethyl] aminocarbonyloxynaphthalene, 2- [2- {2- (2 -Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxynaphthalene, 1- [2- {2- (2-acryloyloxypropoxy) propoxy} propyl] aminocarbonyloxynaphthalene, 2- [2- {2- (2-acryloyl) Oxypropoxy) propoxy} propyl] aminocarbonyloxynaphthale 1- [2- {2- (2-methacryloyloxypropoxypropoxy}) propyl] aminocarbonyloxynaphthalene, 2- [2- {2- (2-methacryloyloxypropoxy) propoxy} propyl] aminocarbonyloxynaphthalene and the like. Can be mentioned.

Next, a specific example in the case of n = 0 and p = 2 is shown. That is, it is a specific example of the compound of the following general formula (8).

(In the formula (8), q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, and a plurality of Y and a plurality of Z Y and Z may be the same or different and each represents a hydrogen atom or a methyl group.)

Here, the thing of the structure which attached the urethane (meth) acrylate group to 1-position and 4-position of the naphthalene ring corresponds to the compound of general formula (3). First, specific examples when q is 0 and r is 1 are 1,4-bis [(2-acryloyloxyethyl) aminocarbonyloxy] naphthalene, 1,4-bis [(2-methacryloyloxyethyl) amino. Carbonyloxy] naphthalene and the like.

Similarly, specific examples of q = 1 and r = 1 are 1,4-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,4-bis [{2 -(2-Methacryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene and the like.

Similarly, specific examples of the case where q is 2 and r is 1 include 1,4-bis [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] naphthalene, 1,4 -Bis [{2- [2- (2-methacryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] naphthalene and the like.

As a specific example of a compound other than those substituted at the 1- and 4-positions, n = 0, p = 2, X is a hydrogen atom, q is 0 and r is 1. , 2-bis [(2-acryloyloxyethyl) aminocarbonyloxy] naphthalene, 1,5-bis [(2-acryloyloxyethyl) aminocarbonyloxy] naphthalene, 1,6-bis [(2-acryloyloxyethyl) Aminocarbonyloxy] naphthalene, 1,7-bis [(2-acryloyloxyethyl) aminocarbonyloxy] naphthalene, 2,6-bis [(2-acryloyloxyethyl) aminocarbonyloxy] naphthalene, 2,7-bis [ (2-acryloyloxyethyl) aminocarbonyloxy] naphthalene, 1,5-bis [(2-methacryloyloxye) L) aminocarbonyloxy] naphthalene, 1,6-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] naphthalene, 1,7-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] naphthalene, 2,6- Examples include bis [(2-methacryloyloxyethyl) aminocarbonyloxy] naphthalene and 2,7-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] naphthalene.

Similarly, specific examples of q = 1 and r = 1 are 1,2-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,5-bis [{2 -(2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,6-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,7-bis [{2- ( 2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 2,6-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 2,7-bis [{2- (2- Acryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,5-bis [{2- (2-metac Royloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,6-bis [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,7-bis [{2- (2-methacryloyloxy) Ethoxy) ethyl} aminocarbonyloxy] naphthalene, 2,6-bis [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 2,7-bis [{2- (2-methacryloyloxyethoxy) Ethyl} aminocarbonyloxy] naphthalene and the like.

Similarly, specific examples when q is 2 and r is 1 include 1,4-bis [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] naphthalene, 1,2 -Bis [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] naphthalene, 1,5-bis [{2- [2- (2-acryloyloxyethoxy] ethoxy) ethyl} amino Carbonyloxy] naphthalene, 1,6-bis [{2- [2- (2-acryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,7-bis [{2- [2- (2-acryloyl) Oxyethoxy] ethoxy) ethyl} aminocarbonyloxy] naphthalene, 2,6-bis [{2- [2- (2-acryloyloxy) Toxi] ethoxy) ethyl} aminocarbonyloxy] naphthalene, 2,7-bis [{2- [2- (2-acryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,5-bis [{2- [2- (2-Methacryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,6-bis [{2- [2- (2-methacryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] naphthalene, 1, , 7-bis [{2- [2- (2-methacryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] naphthalene, 2,6-bis [{2- [2- (2-methacryloyloxyethoxy] ethoxy) ethyl } Aminocarbonyloxy] naphthalene, 2,7-bis [{2- [2 (2-methacryloyloxy ethoxy] ethoxy) ethyl} amino carbonyl oxy] naphthalene.

Next, specific examples when n = 0 and p = 3 are 1,2,4-tris [(2-acryloyloxyethyl) aminocarbonyloxy] naphthalene, wherein q is 0 and r is 1, , 2,4-Tris [(2-methacryloyloxyethyl) aminocarbonyloxy] naphthalene, 1,4,6-tris [(2-acryloyloxyethyl) aminocarbonyloxy] naphthalene, 1,4,6-tris [( 2-methacryloyloxyethyl) aminocarbonyloxy] naphthalene, q = 1 and r = 1, 1,2,4-tris [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 1, 2,4-tris [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,4,6- Lis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,4,6-tris [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, q is 2 1,2,4-tris [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] naphthalene, 1,2,4-tris [{2- [2 -(2-methacryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] naphthalene, 1,4,6-tris [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] naphthalene, , 4,6-Tris [{2- [2- (2-methacryloyloxyethoxy) ethoxy] ethyl Amino carbonyloxy] naphthalene.

Further, specific examples of n = 0 and p = 4 include 1,4,5,8-tetrakis [(2-acryloyloxyethyl) aminocarbonyloxy] naphthalene, wherein q is 0 and r is 1. 1,4,5,8-tetrakis [(2-methacryloyloxyethyl) aminocarbonyloxy] naphthalene, q = 1 and r = 1, 1,4,5,8-tetrakis [{2- (2-acryloyl Oxyethoxy) ethyl} aminocarbonyloxy] naphthalene, 1,4,5,8-tetrakis [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] naphthalene, q is 2 and r is 1 , 4,5,8-tetrakis [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] naphthalene, 1,4, 8- tetrakis [{2- [2- (2-methacryloyloxy) ethoxy] ethyl} amino carbonyl oxy] naphthalene.

Next, a specific example in which X is a hydrogen atom, and n = 1 and p = 1 will be shown. That is, it is a specific example of the compound of the following general formula (9).

(In the formula (9), R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxyalkyl group, a glycidyl group, a hydroxyalkyl group, or an aryloxyalkyl group, q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, and when there are a plurality of Ys, each independently represents a hydrogen atom or a methyl group.

First, specific examples in the case where q is 0 and r is 1 will be described. Here, a structure having a urethane (meth) acrylate group at the 1-position of the naphthalene ring and an alkoxy group at the 4-position has the general formula It corresponds to the compound of (2). Specific examples thereof include 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-hydroxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-hydroxynaphthalene, 1- (2-acryloyloxyethyl). ) Aminocarbonyloxy-4-methoxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-methoxynaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-ethoxynaphthalene, 1- (2 -Methacryloyloxyethyl) aminocarbonyloxy-4-ethoxynaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-phenoxynaphthalene, 1- (2-methacryloyloxyethyl) amino Bonyloxy-4-phenoxynaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-phenethyloxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-phenethyloxynaphthalene, 1- (2- Acryloyloxyethyl) aminocarbonyloxy-4-hydroxyethoxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-hydroxyethoxynaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-glycidyloxy Naphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-glycidyloxynaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4 Methoxyethoxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-methoxyethoxynaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-phenoxyethoxynaphthalene, 1- (2-methacryloyloxyethyl) ) Aminocarbonyloxy-4-phenoxyethoxynaphthalene and the like.

Similarly, specific examples when q is 1 and r is 1 include 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-hydroxynaphthalene, 1- [2- (2-methacryloyl). Oxyethoxy) ethyl] aminocarbonyloxy-4-hydroxynaphthalene, 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-methoxynaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl Aminocarbonyloxy-4-methoxynaphthalene, 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-ethoxynaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy -4-ethoxynaphthalene, 1- [2- 2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-phenoxynaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-phenoxynaphthalene, 1- [2- (2-acryloyloxy) Ethoxy) ethyl] aminocarbonyloxy-4-phenethyloxynaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-phenethyloxynaphthalene, 1- [2- (2-acryloyloxyethoxy) Ethyl] aminocarbonyloxy-4-hydroxyethoxynaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-hydroxyethoxynaphthalene, 1- [2- (2-acryloylio) Ciethoxy) ethyl] aminocarbonyloxy-4-glycidyloxynaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-glycidyloxynaphthalene, 1- [2- (2-acryloyloxyethoxy) Ethyl] aminocarbonyloxy-4-methoxyethoxynaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-methoxyethoxynaphthalene, 1- [2- (2-acryloyloxyethoxy) ethyl] Aminocarbonyloxy-4-phenoxyethoxynaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-phenoxyethoxynaphthalene and the like can be mentioned.

Similarly, as a specific example when q is 2 and r is 1, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-hydroxynaphthalene, 1- [2- {2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-hydroxynaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-methoxynaphthalene 1- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-methoxynaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyl Oxy-4-ethoxynaphthalene, 1- [2- {2- (2-methacryloyl Oxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-ethoxynaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-phenoxynaphthalene, 1- [2- { 2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-phenoxynaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-phenethyloxynaphthalene , 1- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-phenethyloxynaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] amino Carbonyloxy-4 Hydroxyethoxynaphthalene, 1- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-hydroxyethoxynaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} Ethyl] aminocarbonyloxy-4-glycidyloxynaphthalene, 1- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-glycidyloxynaphthalene, 1- [2- {2- ( 2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-methoxyethoxynaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-phenoxyethoxynaphthalene, 1 − [ 2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-phenoxyethoxynaphthalene and the like.

Next, a compound other than those substituted at the 1-position and 4-position, where n = 1, p = 1, q = 0 and r = 1, 5- (2-acryloyloxyethyl) ) Aminocarbonyloxy-1-hydroxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-1-hydroxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy-1-methoxynaphthalene, 5- (2 -Methacryloyloxyethyl) aminocarbonyloxy-1-methoxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy-1-ethoxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-1-ethoxynaphthalene, 5- (2-acryloyloxyethyl) aminocal Nyloxy-1-phenoxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-1-phenoxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy-1-phenethyloxynaphthalene, 5- (2-methacryloyl) Oxyethyl) aminocarbonyloxy-1-phenethyloxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy-1-hydroxyethoxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-1-hydroxyethoxynaphthalene 5- (2-acryloyloxyethyl) aminocarbonyloxy-1-glycidyloxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-1-glycol Zyloxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy-1-methoxyethoxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-1-methoxyethoxynaphthalene, 5- (2-acryloyloxyethyl) ) Aminocarbonyloxy-1-phenoxyethoxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-1-phenoxyethoxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-1-hydroxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-1-hydroxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-1-methoxynaphthalene, 6- (2- Methacryloyloxyethyl) aminocarbonyloxy-1-methoxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-1-ethoxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-1-ethoxynaphthalene, 6 -(2-acryloyloxyethyl) aminocarbonyloxy-1-phenoxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-1-phenoxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-1- Phenethyloxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-1-phenethyloxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy- -Hydroxyethoxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-1-hydroxyethoxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-1-glycidyloxynaphthalene, 6- (2-methacryloyloxy) Ethyl) aminocarbonyloxy-1-glycidyloxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-1-methoxyethoxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-1-methoxyethoxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-1-phenoxyethoxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-1-fe Xylethoxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy-2-hydroxysinaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-2-hydroxynaphthalene, 5- (2-acryloyloxyethyl) Aminocarbonyloxy-2-methoxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-2-methoxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy-2-ethoxynaphthalene, 5- (2- Methacryloyloxyethyl) aminocarbonyloxy-2-ethoxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy-2-phenoxynaphthalene, 5- (2-methacryloyloxyethyl) a Minocarbonyloxy-2-phenoxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy-2-phenethyloxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-2-phenethyloxynaphthalene, 5- ( 2-acryloyloxyethyl) aminocarbonyloxy-2-hydroxyethoxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-2-hydroxyethoxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy-2- Glycidyloxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-2-glycidyloxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy 2-methoxyethoxynaphthalene, 5- (2-methacryloyloxyethyl) aminocarbonyloxy-2-methoxyethoxynaphthalene, 5- (2-acryloyloxyethyl) aminocarbonyloxy-2-phenoxyethoxynaphthalene, 5- (2- Methacryloyloxyethyl) aminocarbonyloxy-2-phenoxyethoxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-2-hydroxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-2-hydroxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-2-methoxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-2-methoxynaphthalene, 6 (2-acryloyloxyethyl) aminocarbonyloxy-2-ethoxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-2-ethoxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-2-phenoxy Naphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-2-phenoxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-2-phenethyloxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyl Oxy-2-phenethyloxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-2-hydroxyethoxynaphthalene, 6- (2-methacryloyloxyethyl) amino Rubonyloxy-2-hydroxyethoxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-2-glycidyloxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-2-glycidyloxynaphthalene, 6- ( 2-acryloyloxyethyl) aminocarbonyloxy-2-methoxyethoxynaphthalene, 6- (2-methacryloyloxyethyl) aminocarbonyloxy-2-methoxyethoxynaphthalene, 6- (2-acryloyloxyethyl) aminocarbonyloxy-2- Examples include phenoxyethoxynaphthalene and 6- (2-methacryloyloxyethyl) aminocarbonyloxy-2-phenoxyethoxynaphthalene.

Similarly, specific examples of q = 1 and r = 1 include 5- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-1-hydroxynaphthalene, 5- [2- (2-methacryloyl). Oxyethoxy) ethyl] aminocarbonyloxy-1-hydroxynaphthalene, 5- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-1-methoxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl Aminocarbonyloxy-1-methoxynaphthalene, 5- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-1-ethoxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy -1-ethoxynaphthalene, 5- [2- 2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-1-phenoxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-phenoxynaphthalene, 5- [2- (2-acryloyloxy) Ethoxy) ethyl] aminocarbonyloxy-1-phenethyloxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-phenethyloxynaphthalene, 5- [2- (2-acryloyloxyethoxy) Ethyl] aminocarbonyloxy-1-hydroxyethoxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-hydroxyethoxynaphthalene, 5- [2- (2-acryloylio) Ciethoxy) ethyl] aminocarbonyloxy-1-glycidyloxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-glycidyloxynaphthalene, 5- [2- (2-acryloyloxyethoxy) Ethyl] aminocarbonyloxy-1-methoxyethoxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-methoxyethoxynaphthalene, 5- [2- (2-acryloyloxyethoxy) ethyl] Aminocarbonyloxy-1-phenoxyethoxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-phenoxyethoxynaphthalene, 6- [2- (2-acryloyloxyethoxy) Si) ethyl] aminocarbonyloxy-1-hydroxynaphthalene, 6- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-hydroxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] Aminocarbonyloxy-1-methoxynaphthalene, 6- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-methoxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy- 1-ethoxynaphthalene, 6- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-ethoxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-1-phenoxynaphtha 6- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-phenoxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-1-phenethyloxynaphthalene, 6 -[2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-phenethyloxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-1-hydroxyethoxynaphthalene, 6- [ 2- (2-Methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-hydroxyethoxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-1-glycidyloxynaphthalene, 6- [2 (2-Methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-glycidyloxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-1-methoxyethoxynaphthalene, 6- [2- (2 -Methacryloyloxyethoxy) ethyl] aminocarbonyloxy-1-methoxyethoxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-1-phenoxyethoxynaphthalene, 6- [2- (2-methacryloyl) Oxyethoxy) ethyl] aminocarbonyloxy-1-phenoxyethoxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-hydroxysinaphthalene, 6- [2- (2-methacrylic) Liloyloxyethoxy) ethyl] aminocarbonyloxy-2-hydroxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-methoxynaphthalene, 6- [2- (2-methacryloyloxyethoxy) ) Ethyl] aminocarbonyloxy-2-methoxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-ethoxynaphthalene, 6- [2- (2-methacryloyloxyethoxy) ethyl] amino Carbonyloxy-2-ethoxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-phenoxynaphthalene, 6- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy- -Phenoxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-phenethyloxynaphthalene, 6- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-phenethyloxy Naphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-hydroxyethoxynaphthalene, 6- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-hydroxyethoxynaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-glycidyloxynaphthalene, 6- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-glycidyl Xinaphthalene, 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-methoxyethoxynaphthalene, 6- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-methoxyethoxynaphthalene , 6- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-phenoxyethoxynaphthalene, 6- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-phenoxyethoxynaphthalene, 5 -[2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-hydroxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-hydroxynaphthalene, 5- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-methoxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-methoxynaphthalene, 5- [2- ( 2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-ethoxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-ethoxynaphthalene, 5- [2- (2-acryloyloxy) Ethoxy) ethyl] aminocarbonyloxy-2-phenoxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-phenoxynaphthalene, 5- [2- (2-acryloyloxyethoxy) ethyl] Aminoca Bonyloxy-2-phenethyloxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-phenethyloxynaphthalene, 5- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy- 2-hydroxyethoxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-hydroxyethoxynaphthalene, 5- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2- Glycidyloxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-glycidyloxynaphthalene, 5- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyl Xyl-2-methoxyethoxynaphthalene, 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-methoxyethoxynaphthalene, 5- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy- Examples include 2-phenoxyethoxynaphthalene and 5- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-2-phenoxyethoxynaphthalene.

Similarly, as a specific example when q is 2 and r is 1, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-hydroxynaphthalene, 6- [2- {2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-hydroxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-methoxynaphthalene , 6- [2- {2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-methoxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyl Oxy-1-ethoxynaphthalene, 6- [2- {2- (2-methacryloyl) Oxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-ethoxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-phenoxynaphthalene, 6- [2- { 2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-phenoxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-phenethyloxynaphthalene , 6- [2- {2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-phenethyloxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] amino Carbonyloxy-1 Hydroxyethoxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-hydroxyethoxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} Ethyl] aminocarbonyloxy-1-glycidyloxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-glycidyloxynaphthalene, 1- [2- {2- ( 2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-methoxyethoxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-methoxyethoxynaphthalene, 6 − [2- {2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-methoxyethoxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-phenoxy Ethoxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-phenoxyethoxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl Aminocarbonyloxy-1-hydroxynaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-hydroxynaphthalene, 5- [2- {2- (2-acryloyl) Oxyethoxy) ethoxy Ethyl] aminocarbonyloxy-1-methoxynaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-methoxynaphthalene, 5- [2- {2- (2- Acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-ethoxynaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-ethoxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-phenoxynaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-phenoxynaphthalene , 5- [2- {2- ( -Acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-phenethyloxynaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-phenethyloxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-hydroxyethoxynaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy- 1-hydroxyethoxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-glycidyloxynaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) Etoki Ci} ethyl] aminocarbonyloxy-1-glycidyloxynaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-methoxyethoxynaphthalene, 5- [2- {2 -(2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-methoxyethoxynaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-methoxyethoxynaphthalene , 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-phenoxyethoxynaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] amino Carbonyloxy-1- Enoxyethoxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-hydroxynaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) ethoxy } Ethyl] aminocarbonyloxy-2-hydroxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-methoxynaphthalene, 5- [2- {2- (2 -Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-methoxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-ethoxynaphthalene, 5- [2 -{2- (2-Methacryloyloxyethoxy) ) Ethoxy} ethyl] aminocarbonyloxy-2-ethoxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-phenoxynaphthalene, 5- [2- {2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-phenoxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-phenethyloxynaphthalene, 5 -[2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-phenethyloxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy 2-Hydroxyeth Xinaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-hydroxyethoxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl Aminocarbonyloxy-2-glycidyloxynaphthalene, 5- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-glycidyloxynaphthalene, 1- [2- {2- (2 -Acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-methoxyethoxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-methoxyethoxynaphthalene, 5- [2- {2- (2-Me Acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-methoxyethoxynaphthalene, 5- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-phenoxyethoxynaphthalene, 5- [2- {2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-phenoxyethoxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy- 2-hydroxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-hydroxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} Ethyl] Ami Carbonyloxy-2-methoxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-methoxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ) Ethoxy} ethyl] aminocarbonyloxy-2-ethoxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-ethoxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-phenoxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-phenoxynaphthalene, 6- [2- {2- (2-acryloyl Oxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-phenethyloxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-phenethyloxynaphthalene, 6- [2 -{2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-hydroxyethoxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2- Hydroxyethoxynaphthalene, 6- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-glycidyloxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} Ethyl] Nocarbonyloxy-2-glycidyloxynaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-methoxyethoxynaphthalene, 6- [2- {2- (2- Acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-methoxyethoxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-methoxyethoxynaphthalene, 6- [ 2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-phenoxyethoxynaphthalene, 6- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2 -Phenoxyeto Shi naphthalene.

Next, a specific example in the case of n = 1 and p = 2 will be shown. That is, it is a specific example of the compound of the following general formula (10).

(In the formula (10), R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxyalkyl group, a glycidyl group, a hydroxyalkyl group, or an aryloxyalkyl group, q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, and in a plurality of Y and a plurality of Z, Y and Z are different even if they are the same. And represents a hydrogen atom or a methyl group.)

First, as specific examples of q = 0 and r = 1, 1,4-bis [(2-acryloyloxyethyl) aminocarbonyloxy] -2-hydroxynaphthalene, 1,4-bis [(2-methacryloyl) Oxyethyl) aminocarbonyloxy] -2-hydroxynaphthalene, 1,4-bis [(2-acryloyloxyethyl) aminocarbonyloxy] -2-methoxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) amino Carbonyloxy] -2-methoxynaphthalene, 1,4-bis [(2-acryloyloxyethyl) aminocarbonyloxy] -2-ethoxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy]- 2-Ethoxynaphthalene, 1,4-bis [(2-acryloyloxy) Ethyl) aminocarbonyloxy] -2-phenoxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2-phenoxynaphthalene, 1,4-bis [(2-acryloyloxyethyl) aminocarbonyl Oxy] -2-phenethyloxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2-phenethyloxynaphthalene, 1,4-bis [(2-acryloyloxyethyl) aminocarbonyloxy] 2-hydroxyethoxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2-hydroxyethoxynaphthalene, 1,4-bis [(2-acryloyloxyethyl) aminocarbonyloxy] -2 -Grease Zyloxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2-glycidyloxynaphthalene, 1,4-bis [(2-acryloyloxyethyl) aminocarbonyloxy] -2-methoxyethoxy Naphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2-methoxyethoxynaphthalene, 1,4-bis [(2-acryloyloxyethyl) aminocarbonyloxy] -2-phenoxyethoxynaphthalene, Examples include 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2-phenoxyethoxynaphthalene.

A specific example when X is a hydrogen atom, q is 1 and r is 1 is 1,4-bis [2- {2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-hydroxynaphtha 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2-hydroxynaphthalene, 1,4-bis [2- {2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-methoxy Naphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2-methoxynaphthalene, 1,4-bis [2- {2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2- Ethoxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy]- -Ethoxynaphthalene, 1,4-bis [2- {2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-phenoxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2 -Phenoxynaphthalene, 1,4-bis [2- {2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-phenethyloxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy]- 2-phenethyloxynaphthalene, 1,4-bis [2- {2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-hydroxyethoxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy ] -2-Hydroxy Ethoxynaphthalene, 1,4-bis [2- {2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-glycidyloxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2 -Glycidyloxynaphthalene, 1,4-bis [2- {2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-methoxyethoxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] 2-methoxyethoxynaphthalene, 1,4-bis [2- {2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-phenoxyethoxynaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyl Oxy] -2- Examples include phenoxyethoxynaphthalene.

Next, a specific example in the case of n = 2 and p = 1 will be shown. That is, it is a specific example of the compound of the following general formula (11).

(In the formula (11), R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxyalkyl group, a glycidyl group, a hydroxyalkyl group, or an aryloxyalkyl group, and a plurality of Rs are the same. Q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, Each independently represents a hydrogen atom or a methyl group.)

First, as specific examples when q is 0 and r is 1, 1- (2-acryloyloxyethyl) aminocarbonyloxy-3,4-dimethoxynaphthalene, 2- (2-acryloyloxyethyl) aminocarbonyloxy-1 , 4-dimethoxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-3,4-dimethoxynaphthalene, 2- (2-methacryloyloxyethyl) aminocarbonyloxy-1,4-dimethoxynaphthalene, 1- (2 -Acryloyloxyethyl) aminocarbonyloxy-3,4-diethoxynaphthalene, 2- (2-acryloyloxyethyl) aminocarbonyloxy-1,4-diethoxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy -3,4-diethoxy Phthalene, 2- (2-methacryloyloxyethyl) aminocarbonyloxy-1,4-diethoxynaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-3,4-diphenoxynaphthalene, 2- (2-acryloyl) Oxyethyl) aminocarbonyloxy-1,4-diphenoxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-3,4-diphenoxynaphthalene, 2- (2-methacryloyloxyethyl) aminocarbonyloxy-1 , 4-Diphenoxynaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-3,4-diphenethyloxynaphthalene, 2- (2-acryloyloxyethyl) aminocarbonyloxy-1,4-diphenethyloxynaphtha 1- (2-methacryloyloxyethyl) aminocarbonyloxy-3,4-diphenethyloxynaphthalene, 2- (2-methacryloyloxyethyl) aminocarbonyloxy-1,4-diphenethyloxynaphthalene, 1- (2 -Acryloyloxyethyl) aminocarbonyloxy-3,4-dihydroxyethoxynaphthalene, 2- (2-acryloyloxyethyl) aminocarbonyloxy-1,4-dihydroxyethoxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy -3,4-dihydroxyethoxynaphthalene, 2- (2-methacryloyloxyethyl) aminocarbonyloxy-1,4-dihydroxyethoxynaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy -3,4-diglycidyloxynaphthalene, 2- (2-acryloyloxyethyl) aminocarbonyloxy-1,4-diglycidyloxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-3,4-di Glycidyloxynaphthalene, 2- (2-methacryloyloxyethyl) aminocarbonyloxy-1,4-diglycidyloxynaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-3,4-dimethoxyethoxynaphthalene, 2- ( 2-acryloyloxyethyl) aminocarbonyloxy-1,4-dimethoxyethoxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-3,4-dimethoxyethoxynaphthalene, 2- (2-methacryloyloxye) L) Aminocarbonyloxy-1,4-dimethoxyethoxynaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-3,4-diphenoxyethoxynaphthalene, 2- (2-acryloyloxyethyl) aminocarbonyloxy-1 , 4-Diphenoxyethoxynaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-3,4-diphenoxyethoxynaphthalene, 2- (2-methacryloyloxyethyl) aminocarbonyloxy-1,4-diphenoxyethoxy And naphthalene.

Next, the case where X is an alkyl group in the general formula (1) is exemplified. Here, a methyl group is given as a representative example of the alkyl group. Specific examples of n = 0, p = 1, q = 0 and r = 1 are 1- (2-acryloyloxyethyl) aminocarbonyloxy-2-methylnaphthalene, 1- (2 -Methacryloyloxyethyl) aminocarbonyloxy-2-methylnaphthalene, 2- (2-acryloyloxyethyl) aminocarbonyloxy-1-methylnaphthalene, 2- (2-methacryloyloxyethyl) aminocarbonyloxy-1-methylnaphthalene, etc. Is mentioned.

Similarly, specific examples when q is 1 and r is 1 include 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-2-methylnaphthalene, 1- [2- (2-methacryloyl). Oxyethoxy) ethyl] aminocarbonyloxy-2-methylnaphthalene, 2- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-1-methylnaphthalene, 2- [2- (2-methacryloyloxyethoxy) ethyl Aminocarbonyloxy-1-methylnaphthalene and the like.

Similarly, specific examples where q is 2 and r is 1 include 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-2-methylnaphthalene, 1- [2 -{2- (2-methacryloyloxyethoxyethoxy}) ethyl] aminocarbonyloxy-2-methylnaphthalene, 2- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-1-methyl And naphthalene, 2- [2- {2- (2-methacryloyloxyethoxyethoxy}) ethyl] aminocarbonyloxy-1-methylnaphthalene, and the like.

Next, a specific example in the case of n = 0 and p = 2 is shown. First, specific examples of q = 0 and r = 1 are 1,4-bis [(2-acryloyloxyethyl) aminocarbonyloxy] -2-methylnaphthalene, 1,5-bis [(2-acryloyl). Oxyethyl) aminocarbonyloxy] -2-methylnaphthalene, 1,6-bis [(2-acryloyloxyethyl) aminocarbonyloxy] -2-methylnaphthalene, 1,7-bis [(2-acryloyloxyethyl) amino Carbonyloxy] -2-methylnaphthalene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2-methylnaphthalene, 1,5-bis [(2-methacryloyloxyethyl) aminocarbonyloxy]- 2-methylnaphthalene, 1,6-bis [(2-methacryloyloxyethyl) amino Ruboniruokishi] -2-methyl-naphthalene, 1,7-bis [(2-methacryloyloxyethyl) amino carbonyloxy] -2-methyl naphthalene.

Similarly, specific examples of q = 1 and r = 1 are 1,4-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-methylnaphthalene, 1,5- Bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-methylnaphthalene, 1,6-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-methyl Naphthalene, 1,7-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-methylnaphthalene, 1,4-bis [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyl Oxy] -2-methylnaphthalene, 1,5-bis [{2- (2-methacryloyloxyethoxy) ethyl} amino Carbonyloxy] -2-methylnaphthalene, 1,6-bis [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] -2-methylnaphthalene, 1,7-bis [{2- (2-methacryloyl) Oxyethoxy) ethyl} aminocarbonyloxy] -2-methylnaphthalene and the like.

Similarly, a specific example where q is 2 and r is 1 is 1,4-bis [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] -2-methylnaphthalene. 1,5-bis [{2- [2- (2-acryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] -2-methylnaphthalene, 1,6-bis [{2- [2- (2-acryloyl) Oxyethoxy] ethoxy) ethyl} aminocarbonyloxy] -2-methylnaphthalene, 1,7-bis [{2- [2- (2-acryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] -2-methylnaphthalene, 1,4-bis [{2- [2- (2-methacryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] -2-methyl Phthalene, 1,5-bis [{2- [2- (2-methacryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] -2-methylnaphthalene, 1,6-bis [{2- [2- (2- Methacryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] -2-methylnaphthalene, 1,7-bis [{2- [2- (2-methacryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] -2-methylnaphthalene Etc.

Next, a specific example in the case of n = 1 and p = 1 will be shown. First, specific examples of q = 0 and r = 1 include 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-hydroxy-2-methylnaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyl. Oxy-4-hydroxy-2-methylnaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-methoxy-2-methylnaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-methoxy- 2-methylnaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-ethoxy-2-methylnaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-ethoxy-2-methylnaphthalene, 1 -(2-acryloyloxyethyl) Minocarbonyloxy-4-phenoxy-2-methylnaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-phenoxy-2-methylnaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4- Phenethyloxy-2-methylnaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-phenethyloxy-2-methylnaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-hydroxyethoxy-2 -Methylnaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-hydroxyethoxy-2-methylnaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-glycidyloxy 2-methylnaphthalene, 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-glycidyloxy-2-methylnaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-methoxyethoxy-2-methylnaphthalene 1- (2-methacryloyloxyethyl) aminocarbonyloxy-4-methoxyethoxy-2-methylnaphthalene, 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-phenoxyethoxy-2-methylnaphthalene, 1- ( 2-methacryloyloxyethyl) aminocarbonyloxy-4-phenoxyethoxy-2-methylnaphthalene and the like.

Similarly, specific examples when q is 1 and r is 1 include 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-hydroxy-2-methylnaphthalene, 1- [2- (2-Methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-hydroxy-2-methylnaphthalene, 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-methoxy-2-methylnaphthalene, 1 -[2- (2-Methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-methoxy-2-methylnaphthalene, 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-ethoxy-2- Methylnaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl Aminocarbonyloxy-4-ethoxy-2-methylnaphthalene, 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-phenoxy-2-methylnaphthalene, 1- [2- (2-methacryloyloxy) Ethoxy) ethyl] aminocarbonyloxy-4-phenoxy-2-methylnaphthalene, 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-phenethyloxy-2-methylnaphthalene, 1- [2- (2-Methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-phenethyloxy-2-methylnaphthalene, 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-hydroxyethoxy-2-methylnaphthalene , 1- [2- 2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-hydroxyethoxy-2-methylnaphthalene, 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-glycidyloxy-2-methylnaphthalene, 1- [2- (2-Methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-glycidyloxy-2-methylnaphthalene, 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-4-methoxyethoxy 2-methylnaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-methoxyethoxy-2-methylnaphthalene, 1- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyl Oh And xyl-4-phenoxyethoxy-2-methylnaphthalene, 1- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-4-phenoxyethoxy-2-methylnaphthalene, and the like.

Similarly, as a specific example when q is 2 and r is 1, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-hydroxy-2-methylnaphthalene, 1 -[2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-hydroxy-2-methylnaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] Aminocarbonyloxy-4-methoxy-2-methylnaphthalene, 1- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-methoxy-2-methylnaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-ethoxy 2-methylnaphthalene, 1- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-ethoxy-2-methylnaphthalene, 1- [2- {2- (2-acryloyl) Oxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-phenoxy-2-methylnaphthalene, 1- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-phenoxy-2-methyl Naphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-phenethyloxy-2-methylnaphthalene, 1- [2- {2- (2-methacryloyloxyethoxy) Ethoxy} ethyl] aminocarbonyloxy-4-phenethyloxy 2-methylnaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-hydroxyethoxy-2-methylnaphthalene, 1- [2- {2- (2- Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-hydroxyethoxy-2-methylnaphthalene, 1- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-glycidyloxy- 2-methylnaphthalene, 1- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-glycidyloxy-2-methylnaphthalene, 1- [2- {2- (2-acryloyl) Oxyethoxy) ethoxy} ethyl] aminocarbonyloxy -4-methoxyethoxy-2-methylnaphthalene, 1- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-methoxyethoxy-2-methylnaphthalene, 1- [2- { 2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-4-phenoxyethoxy-2-methylnaphthalene, 1- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy- 4-phenoxyethoxy-2-methylnaphthalene etc. are mentioned.

A compound having a bifnaphthalene structure represented by the following general formula (12) in which X is not an alkyl group but the naphthalene skeleton is bonded at the 2-position is also exemplified.

(In the formula (12), R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxyalkyl group, a glycidyl group, a hydroxyalkyl group, or an aryloxyalkyl group, and a plurality of Rs are the same. Q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, a plurality of Y, a plurality of Z Y and Z may be the same or different and each represents a hydrogen atom or a methyl group.)

Specific examples of the compound include 4,4′-dimethoxy-1,1′-bis [(2-acryloyloxyethyl) aminocarbonyloxy] -2,2′-binaphthalene, 4,4′-dimethoxy-1, 1'-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2,2'-binaphthalene, 4,4'-diethoxy-1,1'-bis [(2-acryloyloxyethyl) aminocarbonyloxy]- Examples include 2,2′-binaphthalene, 4,4′-diethoxy-1,1′-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -2,2′-binaphthalene.

Next, a specific example in the case where a pair of adjacent Xs are bonded to each other to form a saturated 6-membered ring is shown. First, when n = 0, p = 2, q = 0 and r = 1, 9,10-bis [(2-acryloyloxyethyl) aminocarbonyloxy] -1,2,3 , 4-tetrahydroanthracene, 9,10-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -1,2,3,4-tetrahydroanthracene.

Similarly, when q is 1 and r is 1, a specific example is 9,10-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,2,3,4-tetrahydro Anthracene, 1,5-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,2,3,4-tetrahydroanthracene, 1,6-bis [{2- (2-acryloyloxy) Ethoxy) ethyl} aminocarbonyloxy] -1,2,3,4-tetrahydroanthracene, 1,7-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,2,3,4 -Tetrahydroanthracene, 9,10-bis [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,2 3,4-tetrahydroanthracene, 1,5-bis [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,2,3,4-tetrahydroanthracene, 1,6-bis [{2- (2-Methacryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,2,3,4-tetrahydroanthracene, 1,7-bis [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] -1, 2,3,4-tetrahydroanthracene and the like can be mentioned.

Similarly, when q is 2 and r is 1, a specific example is 9,10-bis [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] -1,2, 3,4-tetrahydroanthracene, 9,10-bis [{2- [2- (2-methacryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] -1,2,3,4-tetrahydroanthracene.

Next, a specific example in the case of n = 1 and p = 1 will be shown. First, specific examples of the case where q is 0 and r is 1 include 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-hydroxy-1,2,3,4-tetrahydroanthracene, 9- (2- Methacryloyloxyethyl) aminocarbonyloxy-10-hydroxy-1,2,3,4-tetrahydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-methoxy-1,2,3,4-tetrahydroanthracene 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-methoxy-1,2,3,4-tetrahydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-ethoxy-1,2, 3,4-tetrahydroanthracene, 9- (2-methacryloyl Xylethyl) aminocarbonyloxy-10-ethoxy-1,2,3,4-tetrahydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-phenoxy-1,2,3,4-tetrahydroanthracene, 9 -(2-Methacryloyloxyethyl) aminocarbonyloxy-10-phenoxy-1,2,3,4-tetrahydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-phenethyloxy-1,2,3 , 4-tetrahydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-phenethyloxy-1,2,3,4-tetrahydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10- Hydro Ethoxy-1,2,3,4-tetrahydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-hydroxyethoxy-1,2,3,4-tetrahydroanthracene, 9- (2-acryloyloxyethyl) ) Aminocarbonyloxy-10-glycidyloxy-1,2,3,4-tetrahydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-glycidyloxy-1,2,3,4-tetrahydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-methoxyethoxy-1,2,3,4-tetrahydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-methoxyethoxy-1,2 , 3,4-Te Trahydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-phenoxyethoxy-1,2,3,4-tetrahydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-phenoxyethoxy -1,2,3,4-tetrahydroanthracene and the like.

Similarly, when q is 1 and r is 1, specific examples of 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-hydroxy-1,2,3,4-tetrahydroanthracene 9- [2- (2-Methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-hydroxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyl Oxy-10-methoxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-methoxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy- 0-ethoxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-ethoxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenoxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10 -Phenoxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenethyloxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-Methacryloyloxyethoxy) ethyl] a Nocarbonyloxy-10-phenethyloxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-hydroxyethoxy-1,2,3,4 -Tetrahydroanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-hydroxyethoxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-acryloyloxyethoxy) Ethyl] aminocarbonyloxy-10-glycidyloxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-glycidyloxy-1,2,3 , 4-tetrahydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-methoxyethoxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy- 10-methoxyethoxy-1,2,3,4-tetrahydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenoxyethoxy-1,2,3,4-tetrahydroanthracene, And 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenoxyethoxy-1,2,3,4-tetrahydroanthracene.

Similarly, as a specific example when q is 2 and r is 1, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-hydroxy-1,2,3 4-tetrahydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-hydroxy-1,2,3,4-tetrahydroanthracene, 9- [2- {2 -(2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-methoxy-1,2,3,4-tetrahydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] Aminocarbonyloxy-10-methoxy-1,2,3,4-tetrahydroanthracene, 9- [2- {2 (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-ethoxy-1,2,3,4-tetrahydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] amino Carbonyloxy-10-ethoxy-1,2,3,4-tetrahydroanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenoxy-1,2,3 , 4-tetrahydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenoxy-1,2,3,4-tetrahydroanthracene, 9- [2- { 2- (2-acryloyloxyethoxy) ethoxy} ethyl] amino Carbonyloxy-10-phenethyloxy-1,2,3,4-tetrahydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenethyloxy-1,2 , 3,4-tetrahydroanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-hydroxyethoxy-1,2,3,4-tetrahydroanthracene, 9- [ 2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-hydroxyethoxy-1,2,3,4-tetrahydroanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ) Ethoxy} ethyl] aminocarbonyloxy-10-g Lysidyloxy-1,2,3,4-tetrahydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-glycidyloxy-1,2,3,4-tetrahydro Anthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-methoxyethoxy-1,2,3,4-tetrahydroanthracene, 9- [2- {2- ( 2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-methoxyethoxy-1,2,3,4-tetrahydroanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] amino Carbonyloxy-10-phenoxyethoxy-1,2,3 - tetrahydrophthalic anthracene, 9- [2- {2- (2-methacryloyloxy) ethoxy} ethyl] amino carbonyloxy-10-phenoxy-ethoxy-1,2,3,4-tetrahydroisoquinoline anthracene, and the like.

Next, a specific example in which a pair of adjacent Xs are bonded to each other to form an unsaturated 6-membered ring and the 6-membered ring is non-aromatic is shown. First, in the case of n = 0, p = 2, q = 0 and r = 1, 9,10-bis [(2-acryloyloxyethyl) aminocarbonyloxy] -1,4- And dihydroanthracene, 9,10-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] -1,4-dihydroanthracene.

Similarly, when q is 1 and r is 1, specific examples of 9,10-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,4-dihydroanthracene, 5-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,4-dihydroanthracene, 1,6-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,4-dihydroanthracene, 1,7-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,4-dihydroanthracene, 9,10-bis [{2- (2- Methacryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,4-dihydroanthracene, 1,5-bis [{2- (2 Methacryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,4-dihydroanthracene, 1,6-bis [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,4-dihydroanthracene, 1, And 7-bis [{2- (2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] -1,4-dihydroanthracene.

Similarly, as a specific example when q is 2 and r is 1, 9,10-bis [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] -1,4- And dihydroanthracene, 9,10-bis [{2- [2- (2-methacryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] -1,4-dihydroanthracene.

Next, a specific example in the case of n = 1 and p = 1 will be shown. First, specific examples of q = 0 and r = 1 are 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-hydroxy-1,4-dihydroanthracene, 9- (2-methacryloyloxyethyl). Aminocarbonyloxy-10-hydroxy-1,4-dihydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-methoxy-1,4-dihydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyl Oxy-10-methoxy-1,4-dihydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-ethoxy-1,4-dihydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy- 10-ethoxy-1,4 Dihydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-phenoxy-1,4-dihydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-phenoxy-1,4-dihydroanthracene 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-phenethyloxy-1,4-dihydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-phenethyloxy-1,4-dihydroanthracene 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-hydroxyethoxy-1,4-dihydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-hydroxy Toxi-1,4-dihydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-glycidyloxy-1,4-dihydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-glycidyl Oxy-1,4-dihydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-methoxyethoxy-1,4-dihydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-methoxy Ethoxy-1,4-dihydroanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-phenoxyethoxy-1,4-dihydroanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyl And ruoxy-10-phenoxyethoxy-1,4-dihydroanthracene.

Similarly, specific examples when q is 1 and r is 1 include 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-hydroxy-1,4-dihydroanthracene, 9- [ 2- (2-Methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-hydroxy-1,4-dihydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-methoxy-1, 4-dihydroanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-methoxy-1,4-dihydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyl Oxy-10-ethoxy-1,4-dihydroanthracene, 9 [2- (2-Methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-ethoxy-1,4-dihydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenoxy-1 , 4-Dihydroanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenoxy-1,4-dihydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] amino Carbonyloxy-10-phenethyloxy-1,4-dihydroanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenethyloxy-1,4-dihydroanthracene, 9- [2- (2-acryloyloki Ethoxy) ethyl] aminocarbonyloxy-10-hydroxyethoxy-1,4-dihydroanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-hydroxyethoxy-1,4-dihydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-glycidyloxy-1,4-dihydroanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10- Glycidyloxy-1,4-dihydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-methoxyethoxy-1,4-dihydroanthracene, 9- [2- (2-methacryloyloxy) Etoki Ii) ethyl] aminocarbonyloxy-10-methoxyethoxy-1,4-dihydroanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenoxyethoxy-1,4-dihydroanthracene, Examples include 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenoxyethoxy-1,4-dihydroanthracene.

Similarly, as a specific example when q is 2 and r is 1, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-hydroxy-1,4-dihydroanthracene 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-hydroxy-1,4-dihydroanthracene, 9- [2- {2- (2-acryloyloxyethoxy) Ethoxy} ethyl] aminocarbonyloxy-10-methoxy-1,4-dihydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-methoxy-1,4- Dihydroanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} e L] aminocarbonyloxy-10-ethoxy-1,4-dihydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-ethoxy-1,4-dihydroanthracene 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenoxy-1,4-dihydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) Ethoxy} ethyl] aminocarbonyloxy-10-phenoxy-1,4-dihydroanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenethyloxy-1,4 -Dihydroanthracene, 9- [2- {2- (2- Tacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenethyloxy-1,4-dihydroanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10- Hydroxyethoxy-1,4-dihydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-hydroxyethoxy-1,4-dihydroanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-glycidyloxy-1,4-dihydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] amino Carbonyloxy-10 Glycidyloxy-1,4-dihydroanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-methoxyethoxy-1,4-dihydroanthracene, 9- [2 -{2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-methoxyethoxy-1,4-dihydroanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] Aminocarbonyloxy-10-phenoxyethoxy-1,4-dihydroanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenoxyethoxy-1,4-dihydroanthracene Etc.

In the general formula (1), a specific example in which a pair of adjacent Xs are bonded to each other to form an unsaturated 6-membered ring and the 6-membered ring is aromatic is shown. Among the compounds, a pair of adjacent Xs in the 2nd and 3rd positions and n = 0 and p = 1 corresponds to the compound of the general formula (5). Specific examples of the compound in which q is 0 and r is 1 include 9- (2-acryloyloxyethyl) aminocarbonyloxyanthracene and 9- (2-methacryloyloxyethyl) aminocarbonyloxyanthracene.

Similarly, specific examples when q is 1 and r is 1 include 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxyanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl. And aminocarbonyloxyanthracene, 9- [2- (2-methacryloyloxypropoxy) propyl] aminocarbonyloxyanthracene.

Similarly, specific examples when q is 2 and r is 1 include 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxyanthracene, 9- [2- {2- (2-Methacryloyloxyethoxyethoxy}) ethyl] aminocarbonyloxyanthracene, 9- [2- {2- (2-acryloyloxypropoxy) propoxy} propyl] aminocarbonyloxyanthracene, 9- [2- {2- (2 -Methacryloyloxypropoxypropoxy}) propyl] aminocarbonyloxyanthracene and the like.

Next, when a pair of adjacent Xs are bonded to each other to form an unsaturated 6-membered ring and the 6-membered ring is aromatic, n = 0 and p = 2 An example is shown. Among the compounds, a pair of adjacent Xs in the 2nd and 3rd positions corresponds to the compound of the general formula (4). Among these compounds, specific examples of q = 0 and r = 1 are 9,10-bis [(2-acryloyloxyethyl) aminocarbonyloxy] anthracene, 9,10-bis [(2 -Methacryloyloxyethyl) aminocarbonyloxy] anthracene.

Similarly, specific examples of q = 1 and r = 1 are 9,10-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] anthracene, 9,10-bis [{2 -(2-Methacryloyloxyethoxy) ethyl} aminocarbonyloxy] anthracene and the like.

Similarly, when q is 2 and r is 1, specific examples of 9,10-bis [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] anthracene, -Bis [{2- [2- (2-methacryloyloxyethoxy] ethoxy) ethyl} aminocarbonyloxy] anthracene and the like.

As an example of a pair of adjacent X other than the 2nd and 3rd positions, first, as a specific example when q is 0 and r is 1, 1,4-bis [(2-acryloyloxyethyl) aminocarbonyl Oxy] anthracene, 1,4-bis [(2-methacryloyloxyethyl) aminocarbonyloxy] anthracene, 9,10-bis [(2-acryloyloxyethyl) aminocarbonyloxy] phenanthrene, 9,10-bis [(2 -Methacryloyloxyethyl) aminocarbonyloxy] phenanthrene and the like. As specific examples of q = 1 and r = 1, 1,4-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] anthracene, 1,4-bis [{2- ( 2-methacryloyloxyethoxy) ethyl} aminocarbonyloxy] anthracene, 9,10-bis [{2- (2-acryloyloxyethoxy) ethyl} aminocarbonyloxy] phenanthrene, 9,10-bis [{2- (2- Methacryloyloxyethoxy) ethyl} aminocarbonyloxy] phenanthrene and the like. As a specific example when q is 2 and r is 1, 1,4-bis [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] anthracene, 1,4-bis [{2- [2- (2-methacryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] anthracene, 9,10-bis [{2- [2- (2-acryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy ] Phenanthrene, 9,10-bis [{2- [2- (2-methacryloyloxyethoxy) ethoxy] ethyl} aminocarbonyloxy] phenanthrene, and the like.

Next, a specific example in the case of n = 1 and p = 1 is shown. First, specific examples when q is 0 and r is 1 include 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-hydroxy-anthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10. -Hydroxy-anthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-methoxy-anthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-methoxy-anthracene, 9- (2-acryloyloxy) Ethyl) aminocarbonyloxy-10-ethoxy-anthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-ethoxy-anthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-pheno Cy-anthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-phenoxy-anthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-phenethyloxy-anthracene, 9- (2-methacryloyloxy) Ethyl) aminocarbonyloxy-10-phenethyloxy-anthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-hydroxyethoxy-anthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-hydroxyethoxy Anthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-glycidyloxyanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy -10-glycidyloxyanthracene, 9- (2-acryloyloxyethyl) aminocarbonyloxy-10-methoxyethoxyanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-methoxyethoxyanthracene, 9- (2- And acryloyloxyethyl) aminocarbonyloxy-10-phenoxyethoxyanthracene, 9- (2-methacryloyloxyethyl) aminocarbonyloxy-10-phenoxyethoxyanthracene, and the like.

Similarly, specific examples when q is 1 and r is 1 include 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-hydroxyanthracene, 9- [2- (2-methacryloyl). Oxyethoxy) ethyl] aminocarbonyloxy-10-hydroxyanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-methoxyanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl Aminocarbonyloxy-10-methoxyanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-ethoxyanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy -10-ethoxy 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenoxyanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenoxyanthracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenethyloxyanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenethyloxyanthracene, 9- [2 -(2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-hydroxyethoxyanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-hydroxyeth Cyantracene, 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-glycidyloxyanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-glycidyloxyanthracene 9- [2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-methoxyethoxyanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10-methoxyethoxyanthracene, 9 -[2- (2-acryloyloxyethoxy) ethyl] aminocarbonyloxy-10-phenoxyethoxyanthracene, 9- [2- (2-methacryloyloxyethoxy) ethyl] aminocarbonyloxy-10- Examples include phenoxyethoxyanthracene.

Similarly, as a specific example when q is 2 and r is 1, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-hydroxyanthracene, 9- [2- {2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-hydroxyanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-methoxyanthracene 9- [2- {2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-methoxyanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyl Oxy-10-ethoxyanthracene, 9- [2- {2 (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-ethoxyanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenoxyanthracene, 9- [2- {2- (2-Methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenoxyanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10 -Phenethyloxyanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenethyloxyanthracene, 9- [2- {2- (2-acryloyloxyethoxy) eth Ci} ethyl] aminocarbonyloxy-10-hydroxyethoxyanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-hydroxyethoxyanthracene, 9- [2- {2 -(2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-glycidyloxyanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-glycidyloxyanthracene 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-methoxyethoxyanthracene, 9- [2- {2- (2-methacryloyloxyethoxy) ethoxy} ethyl] amino Nocarbonyloxy-10-methoxyethoxyanthracene, 9- [2- {2- (2-acryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenoxyethoxyanthracene, 9- [2- {2- (2- And methacryloyloxyethoxy) ethoxy} ethyl] aminocarbonyloxy-10-phenoxyethoxyanthracene.

Among the compounds represented by the general formula (1), a compound in which X is a hydrogen atom, p and n are 1, and a compound in which p is 2 and n is 0 are easy to produce. At the same time, the chain transfer ability is high, which is preferable. Further, regarding r and q, a compound in which r is 1 and q is 0 or 1 is preferable because it is easy to produce. Further, in the case of a compound in which p and n are 1, a compound in which a urethane (meth) acrylate group and an alkoxy group are substituted at the 1st and 4th positions of the naphthalene ring and a compound in which p is 2 and n is 0 Then, it is preferable that the urethane (meth) acrylate group is substituted at the 1-position and 4-position of the naphthalene ring because the production is easier and the chain transfer ability is high.

In the compound having an alkoxy group, the alkyl group represented by R is preferably an alkyl group having 1 to 8 carbon atoms, and specifically includes a methyl group, an ethyl group, a propyl group, a butyl group, and the like. . The propyl group includes n-propyl group, i-propyl group, and the butyl group includes isomers such as n-butyl group, i-butyl group, and tert-butyl group. Among these alkyl groups, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, and an n-butyl group are preferable because of high chain transfer ability and easy synthesis.

In the case of a compound having an anthracene skeleton, a compound in which urethane (meth) acrylate groups are substituted at the 9 and 10 positions represented by the general formula (4) and X is a hydrogen atom is easy to produce. Therefore, it is preferable. A compound in which a urethane (meth) acrylate group is substituted at the 9-position represented by the general formula (5) and X is a hydrogen atom is also preferable because it is easy to produce.

[Method for producing urethane (meth) acrylate compound having condensed polycyclic aromatic skeleton]
The urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by general formulas (1) to (5) of the present invention has a condensed polycyclic aromatic skeleton represented by the following general formula (13). It can manufacture by making a compound and the (meth) acrylate compound which has an isocyanate group represented by following General formula (14) react.

(13) In the formula, n represents an integer of 0 to 3, m represents an integer of 1 or 2, and R represents a hydrogen atom, alkyl group, aryl group, aralkyl group, alkoxyalkyl group, glycidyl group, hydroxyalkyl. A group or an aryloxyalkyl group, and when n is 2 or 3, the plurality of R may be the same or different. Each X independently represents a hydrogen atom, an alkyl group or an aryl group, but a pair of adjacent Xs may be bonded to each other to form a saturated or unsaturated 6-membered ring instead of the substituent. Good.

(14) In the formula, q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, and Y and Z each independently A hydrogen atom or a methyl group is represented, and Y in the case where there are a plurality of them each independently represents a hydrogen atom or a methyl group.

In the general formula (13), examples of the alkyl group represented by R include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, tert-butyl group, n- A pentyl group, an n-hexyl group, a 2-ethylhexyl group, an n-decyl group, an n-dodecyl group, and the like can be given. Examples of the aryl group include a phenyl group, a p-tolyl group, an o-tolyl group, and a naphthyl group. Examples of the aralkyl group include a benzyl group, a phenethyl group, a phenylpropyl group, a naphthylmethyl group, and a naphthylethyl group. Examples of the alkoxyalkyl group include a 2-methoxyethyl group, a 2-ethoxyethyl group, and a 2-methoxy group. An ethoxyethyl group etc. are mentioned. Examples of the glycidyl group include a glycidyl group and a 2-methylglycidyl group. Examples of the hydroxyalkyl group include a hydroxymethyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 2-hydroxybutyl group, and a 3-hydroxybutyl group. Examples of the aryloxyalkyl group include a phenoxyethyl group and a triloxyethyl group.

Examples of the alkyl group represented by X in the general formula (13) include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an amyl group, and a 2-ethylhexyl group. 4-methylpentyl group, 4-methyl-3-pentenyl group and the like, and examples of the aryl group include phenyl group, p-tolyl group, o-tolyl group, naphthyl group and the like.

In the general formula (13), as an example in which a pair of adjacent Xs are bonded to each other, X is a CH ₂ CH ₂ group, and adjacent Xs are bonded by a single bond, X is CH ₂ CH groups in which adjacent Xs are bonded by a double bond, X is a CH═CH group, and adjacent Xs are bonded by a single bond to form an aromatic ring Etc. The 6-membered ring formed by a pair of adjacent Xs may be further substituted with an alkyl group or an aryl group. Furthermore, examples of the substituted alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a tert-butyl group, and the aryl group includes a phenyl group. Group, p-tolyl group, o-tolyl group, naphthyl group and the like.

[Compound having a condensed polycyclic aromatic skeleton as a raw material]
Specific examples of the compound represented by the general formula (13) include the following compounds. First, an example in which X is a hydrogen atom is given. First, specific examples of the compound in which n is 0 and m is 1 include 1-naphthol and 2-naphthol.

Next, specific examples of the compound in which n is 0 and m is 2 include 1,2-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1, Examples include 7-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, and 2,7-didihydroxynaphthalene.

Next, specific examples of the compound in which n is 1 and m is 1 include 4-methoxy-1-naphthol, 4-ethoxy-1-naphthol, 4-phenoxy-1-naphthol, 4-phenethyloxy-1 -Naphthol, 4-hydroxyethoxy-1-naphthol, 4-glycidyloxy-1-naphthol, 4-methoxyethoxy-1-naphthol, 4-phenoxyethoxy-1-naphthol, 4-methoxy-2-naphthol, 4-ethoxy 2-naphthol, 4-phenoxy-2-naphthol, 4-phenethyloxy-2-naphthol, 4-hydroxyethoxy-2-naphthol, 4-glycidyloxy-2-naphthol, 4-methoxyethoxy-2-naphthol, 4 -Phenoxyethoxy-2-naphthol etc. are mentioned.

The compounds listed as specific examples of the compound where n is 1 and m is 1 may be commercially available, but the dihydroxynaphthalene compounds listed as specific examples of the compound where n is 0 and m is 2 More synthesis is possible. For example, the method described in JP-A-5-58938.

For example, by heating an alcohol solution of a dihydroxynaphthalene compound under an acid catalyst, one of the hydroxyl groups is etherified to obtain a monoalkoxynaphthol compound. Examples of the alcohol include methanol, ethanol, n-propyl alcohol, i-propyl alcohol, n-butyl alcohol, i-butyl alcohol, 2-ethylhexanol and the like. The reaction temperature is preferably 20 ° C. or higher and 180 ° C. or lower, more preferably 60 ° C. or higher and 120 ° C. or lower. Although the reaction time depends on the reaction temperature, it is usually 30 minutes or longer and 2 hours or shorter. After the completion of the reaction, if it is put into an alcohol-immiscible solvent, a monoalkoxynaphthol compound precipitate is formed, and it is filtered and dried to obtain a monoalkoxynaphthol compound.

Next, specific examples of the compound in which n is 1 and m is 2 include 2-methoxy-1,4-dihydroxynaphthalene, 2-ethoxy-1,4-dihydroxynaphthalene, 2-phenoxy-1,4- Dihydroxynaphthalene, 2-phenethyloxy-1,4-dihydroxynaphthalene, 2-hydroxyethoxy-1,4-dihydroxynaphthalene, 2-glycidyloxy-1,4-dihydroxynaphthalene, 2-methoxyethoxy-1,4-dihydroxynaphthalene 2-phenoxyethoxy-1,4-dihydroxynaphthalene, 2-methoxy-1,5-dihydroxynaphthalene, 2-methoxy-1,6-dihydroxynaphthalene, 2-methoxy-1,7-dihydroxynaphthalene, 2-methoxy- 1,8-dihydroxynaphthalene and the like can be mentioned.

The compounds mentioned as specific examples of the compound in which n is 1 and m is 2 can be synthesized, for example, by catalytic hydrogenation of 2-alkoxy-1,4-naphthoquinone or the like.

Next, specific examples of compounds in which n is 0 and m is 2 or more include 1,2,4-trihydroxynaphthalene, 1,2,5,6-tetrahydroxynaphthalene, 2,3,6,7 -Tetrahydroxynaphthalene etc. are mentioned.

Next, examples in which X is other than a hydrogen atom will be given. Some specific examples are given, but the present invention is not limited to these compounds. For example, specific examples where X is an alkyl group include 2-methyl-1-naphthol, 1-methyl-2-naphthol, 1,2-dihydroxy-4-methylnaphthalene, 2-methyl-1,4-dihydroxynaphthalene. 2-methyl-1,5-dihydroxynaphthalene, 2-methyl-1,6-dihydroxynaphthalene, 2-methyl-1,7-dihydroxynaphthalene, 1-methyl-2,6-dihydroxynaphthalene, 1-methyl-2 , 7-didihydroxynaphthalene and the like.

Specific examples of the case where a pair of adjacent Xs are bonded to each other to form a saturated 6-membered ring include, for example, 1,2,3,4-tetrahydro-9,10-dihydroxyanthracene, 2 -Methyl-1,2,3,4-tetrahydro-9,10-dihydroxyanthracene and the like.

The compound can be obtained, for example, by isomerizing a compound synthesized by a Diels-Alder reaction of a 1,4-naphthoquinone compound and a butadiene compound and then catalytic hydrogenation.

Further, as a specific example of a case where a pair of adjacent Xs are bonded to each other to form an unsaturated 6-membered ring and the 6-membered ring is non-aromatic, for example, 1,4-dihydro Examples include -9,10-dihydroxyanthracene and 2-methyl-1,4-dihydro-9,10-dihydroxyanthracene.

The compound can be obtained, for example, by a Diels-Alder reaction between a 1,4-naphthoquinone compound and a butadiene compound.

Further, as a specific example of a case where a pair of adjacent Xs are bonded to each other to form an unsaturated 6-membered ring and the 6-membered ring is non-aromatic, for example, 9,10-dihydroxy Anthracene, 1,4-dihydroxyanthracene, 9,10-dihydroxyphenanthrene, 9-anthranol and the like can be mentioned.

[(Meth) acrylic compound having isocyanate group as raw material]
The (meth) acrylic compound having an isocyanate group used in the present invention may be a compound having an isocyanate group and a (meth) acryloyl group in the molecule. In such a compound, the number of isocyanate groups should just be 1 or more, and 1 or more and 4 or less are preferable.

Monofunctional (meth) acrylic compounds having an isocyanate group include (meth) acryloyl isocyanate, 2- (meth) acryloyloxyethyl isocyanate, 2- (meth) acryloyloxypropyl isocyanate, and 2- (2- (meth) acryloyl. Oxyethoxy) ethyl isocyanate, 2- (2- (meth) acryloyloxypropoxy) propyl isocyanate, 4- (meth) acryloyloxy-3-methyl-2-isocyanate butane, 4- (meth) acryloyloxycyclohexyl isocyanate, etc. It is done.

Examples of the polyfunctional (meth) acrylic compound having an isocyanate group include 1,1-bis ((meth) acryloyloxymethyl) ethyl isocyanate and 1,1-bis ((meth) acryloyloxyethyl) ethyl isocyanate. Can be mentioned.

These (meth) acrylic compounds having an isocyanate group may be used alone or in combination of two or more.

Examples of the (meth) acrylic compound having an isocyanate group include 2- (meth) acryloyloxyethyl isocyanate, 2- (meth) acryloyloxypropyl isocyanate, 2- (2- (meth) acryloyloxyethoxy) ethyl isocyanate, 2- ( 2- (Meth) acryloyloxypropoxy) propyl isocyanate and the like are preferable because they are highly reactive, easily available, and easy to handle.

[Production method]
The urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention comprises a compound having the condensed polycyclic aromatic skeleton and a (meth) acrylic compound having an isocyanate group in the presence of a solvent or a non-reactive compound. It can manufacture by making it react in presence.

The solvent that can be used is not particularly limited as long as it is an inert solvent for the (meth) acrylate compound having an isocyanate group. For example, ethers such as diethyl ether and dipropyl ether; 1,4- Cyclic ethers such as dioxane, dioxolane, and tetrahydrofuran; Ketones such as acetone, methyl ethyl ketone, diisopropyl ketone, and isobutyl methyl ketone; Esters such as methyl acetate, ethyl acetate, and butyl acetate; Aromatic hydrocarbons such as toluene, xylene, and ethylbenzene A halogen-based solvent such as methylene chloride, chloroform, carbon tetrachloride, tetrachloroethane, trichloroethane; and nitriles such as acetonitrile. These solvents may be used alone or in combination of two or more.

In the method for producing a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention, an esterification catalyst may be used. Examples of the esterification catalyst include organic tin compounds such as tin octylate, dibutyltin diacetate, dibutyltin dioctoate, and dibutyltin dilaurate; naphthenic acid metal salts such as copper naphthenate, zinc naphthenate, and cobalt naphthenate; triethylamine, Tertiary amines such as benzyldimethylamine, N, N, N ′, N′-tetraalkylethylenediamine; cyclic tertiary amines such as pyridine, methylpyridine, N, N-dimethylpiperazine, triethylenediamine, and the like. . These esterification catalysts may be used alone or in combination of two or more.

The amount of the esterification catalyst used is 0.001 to 3 parts by weight, preferably 0.005 to 100 parts by weight based on the total amount of the compound having a condensed polycyclic aromatic skeleton and the (meth) acrylate compound having an isocyanate group. It is used within the range of 2 parts by weight, more preferably 0.01 to 1 part by weight. If it is less than 0.001 part by weight, it takes too much time for the esterification reaction. On the other hand, if it is used in an amount of more than 3 parts by weight, the corresponding effect of shortening the reaction time cannot be obtained, which is unsuitable.

In the method for producing a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention, the reaction may be performed in the presence of a polymerization inhibitor in order to prevent polymerization of the (meth) acrylate compound having an isocyanate group. preferable. Examples of polymerization inhibitors that can be used include hydroquinone, hydroquinone monomethyl ether, methoquinone, 2-t-butylhydroquinone, 4-methoxyphenol, 2,6-di-t-butyl-4-methylphenol and the like. Inhibitors; phenothiazines; heavy metal compounds such as copper chloride, copper naphthoate, cobalt naphthoate, and the like. These polymerization inhibitors may be used alone or in combination of two or more. These polymerization inhibitors may be added to the raw material before synthesizing the urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton, may be added during the reaction, or the condensed poly after the completion of the reaction. You may add to the urethane (meth) acrylate compound which has a ring aromatic skeleton.

In the method for producing a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention, the reaction is usually carried out at 40 to 150 ° C., preferably 50 to 120 ° C., more preferably about 60 to 100 ° C. . Note that the reaction is preferably performed in an atmosphere of an inert gas such as nitrogen, helium, or argon (an atmosphere such as nitrogen, helium, or argon).

In the method for producing a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention, a condensation obtained by reacting a compound having a condensed polycyclic aromatic skeleton with a (meth) acrylate compound having an isocyanate group The urethane (meth) acrylate compound having a polycyclic aromatic skeleton can be separated and purified by filtration and drying. When a solvent is used, the solvent component can be separated from the product after completion of the reaction by vacuum distillation or the like.

The urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention has a function as a chain transfer agent and at the same time is a compound having a high refractive index, and is also a compound having its own polymerizability, It can also be used as a macromonomer described later.

[Radically polymerizable composition]
By using the chain transfer agent composed of the urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton of the present invention, the polymerization degree of the radical polymerizable compound can be adjusted in the polymerization reaction of the radical polymerizable compound. The chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention can be used as a radical polymerizable composition by adding it to a radical polymerizable compound.

The radical polymerizable composition containing a chain transfer agent composed of a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention as an essential component is optionally added with a radical polymerization initiator for initiating a radical reaction. Is done. A polymer having a molecular weight adjusted can be produced by applying initiation energy such as heat and light necessary for initiating the polymerization and initiating the polymerization.

The blending amount of the chain transfer agent comprising the urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton of the present invention is usually 0 with respect to the radical polymerizable compound from the viewpoint of sufficient chain transfer effect and economy. 0.01 to 5% by weight is preferable, and 0.05 to 3% by weight is more preferable.

The number average molecular weight of the polymer depends on the concentration of the radically polymerizable compound generally used, the concentration of the chain transfer agent comprising the urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton of the present invention, and the concentration of the radical polymerization initiator. Can be adjusted. The number average molecular weight increases as the concentration of the radical polymerizable compound increases, and conversely decreases as the concentration of the chain transfer agent composed of a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton increases. In view of this, the number average molecular weight can be adjusted by appropriately changing the concentration within the range of the chain transfer agent comprising the urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton of the present invention.

As a method for adding a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention to a radical polymerizable compound, known addition such as batch addition, batch addition, continuous addition, or a combination thereof The method is used. For example, a chain transfer agent is added batchwise in each step, a monomer mixture and a chain transfer agent are continuously added in each step, a chain transfer agent is added in combination with batch addition and continuous addition in each step, etc. There is an addition method. Alternatively, the chain transfer agent may be added directly as a solid or powder, or the chain transfer agent may be dissolved in an appropriate organic solvent and added.

[Radically polymerizable compound]
The radically polymerizable compound in the present invention is not particularly limited as long as it is a compound having a polymerizable double bond in the molecule. Examples of such radically polymerizable compounds include α, β-unsaturated carboxylic acid compounds such as acrylic acid and methacrylic acid; methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, Α-, β-unsaturated carboxylic acid ester compounds such as 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, methyl methacrylate, butyl methacrylate; vinyl ester compounds such as vinyl acetate; acrylonitrile, acrylamide, etc. Acrylic compounds; aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene and divinylbenzene; substituted ethylene compounds such as vinyl chloride and vinylidene chloride; ethylene, propylene, butene, butadiene, isoprene, cyclopentadiene, and pinet And unsaturated organic silane compounds such as 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, and vinyltrimethoxysilane.

Among the radical polymerizable compounds, α, β-unsaturated carboxylic acid compounds, α, β-unsaturated carboxylic acid ester compounds, aromatic vinyl compounds, and vinyl ester compounds are preferable.

Among these compounds, (meth) acrylic acid which is an α, β-unsaturated carboxylic acid compound, (meth) acrylic acid ester which is an α, β-unsaturated carboxylic acid ester, and styrene which is an aromatic vinyl compound are preferable. . In particular, (meth) acrylic acid which is an α, β-unsaturated carboxylic acid compound from the point that the effect of a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention is remarkable. A (meth) acrylic acid ester which is an α, β-unsaturated carboxylic acid ester is preferred.

The form and content of the radical polymerizable compound contained in the radical polymerizable composition are not particularly limited. For example, a radical polymerizable compound itself or a solution of a radical polymerizable compound can be used.

[Radical polymerization initiator]
The radical polymerization initiator is not particularly limited as long as it gives energy and generates an active radical for the radical polymerizable compound. Generally, so-called radical polymerization initiators that are commercially available can be used. For convenience, what is used with thermal energy applied is called a thermal radical polymerization initiator, and what gives light energy is called a photo radical polymerization initiator. In the present invention, both a thermal radical polymerization initiator and a photo radical polymerization initiator can be used.

It does not specifically limit as a thermal radical polymerization initiator, A well-known compound can be used. For example, a peroxide, a hydroperoxide, and an azo compound are mentioned. Specifically, benzoyl peroxide, di-t-amyl peroxide, t-butyl peroxybenzoate, 2,5-dimethyl-2,5 di- (t-butylperoxy) hexane, 2,5-dimethyl-2,5- Di- (t-butylperoxy) hexyne-3, and peroxides such as di-cumyl peroxide, hydroperoxides such as t-amyl hydroperoxide, t-butyl hydroperoxide, and hydrogen peroxide, (2,2′-azobis (2,4-dimethylpentanenitrile)), (2,2′-azobis (2-methylpropanenitrile)), (2,2′-azobis (2-methylbutanenitrile)), (2,2′-azobis) (Cyclohexanecarbonitrile)) and the like.

In addition, in order to use a thermal radical polymerization initiator at a relatively low temperature, a so-called redox initiator system is used in which a reducing agent such as a transition metal or an amine is combined with an oxidizing initiator such as peroxide, hydroperoxide, or ascorbic acid You can also

It does not specifically limit as radical photopolymerization initiator, A well-known compound can be used. For example, benzoin compounds, acetophenones, benzophenones, thioxanthones, α-acyloxime esters, phenylglyoxylates, benzyls, azo compounds, diphenyl sulfide compounds, acylphosphine oxide compounds, organic dye compounds , Iron-phthalocyanine series, benzoins, benzoin ethers, anthraquinones. Specifically, benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isobutyl ether; acetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 2-hydroxy- Acetophenones such as 2-methyl-phenylpropan-1-one, diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one; Anthraquinones such as 2-ethylanthraquinone, 2-t-butylanthraquinone, 2-chloroanthraquinone, 2-amylanthraquinone; 2,4-diethylthioxanthone, 2-isopropylthioxanthate Thioxanthones such as 2-chlorothioxanthone; ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenones such as benzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 4,4′-bismethylaminobenzophenone; 2 , 4,6-trimethylbenzoyldiphenylphosphine oxide, phosphine oxides such as bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, and the like. Photo radical polymerization initiators introduced in known literature such as Journal of Synthetic Organic Chemistry 66, 458 (2008) can also be used.

Further, as a photo radical polymerization initiator available from the market, 1-hydroxycyclohexyl phenyl ketone (Irgacure 184 manufactured by Ciba Specialty Chemicals, Inc., Irgacure is a registered trademark of Ciba Specialty Chemicals), (2-methyl-1- ( Acylphosphines such as 4- (methylthio) phenyl) -2- (4-morpholinyl) -1-propanone) (Irgacure 907) and bis (2,4,6-trimethylbenzoyl) -diphenyl-phosphine oxide (Irgacure 819) Oxide compounds; titanocenes such as bis (η ⁵ -2,4-cyclopentadien-1-yl) -bis (2,6-difluoro-3- (1H-pyrrol-1-yl) -phenyl) titanium (Irgacure 784) Compound; 6,12-bis (trimethylsilane And naphthacene quinone compounds such as ryloxy) -1,11 naphthacene quinone.

These radical polymerization initiators may be used alone or in combination of two or more. The amount of radical polymerization initiator added depends on the radical polymerizable compound and chain transfer agent used, but within a range of 0.0001 parts by mass to 10 parts by mass with respect to 100 parts by mass of the total amount of radical polymerizable compounds. Preferably there is.

[Starting energy]
The starting energy may be any energy that can generate radicals from the added radical initiator. In general, thermal energy and ionization wave energy are appropriately selected. Specific examples of the energy source include heat, light, electron beam (EB), microwave, radiation and other electromagnetic rays. Depending on the energy source used, thermal polymerization, electromagnetic ray polymerization (photopolymerization, electron beam polymerization, Microwave polymerization, radiation polymerization) and the like.

In the case of thermal polymerization, although it depends on the polymerizable compound used and its mode, the temperature range used for the polymerization is usually -20 to 200 ° C, preferably 0 to 150 ° C, more preferably 10 to 120 ° C.

Furthermore, redox polymerization using a redox (redox) initiator (described later) is one type of thermal polymerization. Under the present circumstances, the temperature range used is lower than normal thermal polymerization, is -40-100 degreeC, Preferably it is -20-80 degreeC, More preferably, it is 0-60 degreeC.

In photopolymerization, ultraviolet light, visible light, infrared light, or the like can be used as light to be irradiated. A radical photopolymerization initiator or a sensitizer can also be used. In the case of ultraviolet rays and visible rays, specifically, for example, rays in the wavelength range of 300 to 800 nm. As the light source, an LED (light emitting diode) or a lamp that can irradiate light having a wavelength in the range of 300 to 800 nm is used. Examples of the LED include a UV-LED, a blue LED, and a white LED. Examples of the lamp include a high-pressure mercury lamp, an ultra-high pressure mercury lamp, a halogen lamp, and a metal halide lamp.

Electron beam polymerization is performed by electron beam irradiation. For the electron beam irradiation, any method that can act on the electron beam polymerization compound and cause polymerization of the polymerizable substance can be used without particular limitation. The electron dose to be irradiated is preferably adjusted in the range of about 1 to 300 kGy as an absorbed dose. If it is less than 1 kGy, sufficient irradiation effect cannot be obtained, and irradiation exceeding 300 kGy is not preferable because there is a possibility of deteriorating the substrate. As an electron beam irradiation method, for example, a scanning method, a curtain beam method, a broad beam method, or the like is used, and the acceleration voltage when irradiating the electron beam needs to be controlled by the thickness of the substrate on the irradiation side. However, about 20 to 100 kV is appropriate.

For the microwave polymerization, a known method of Strauss et al. (Aust. J. Chem., 48, 1665-1692 (1995)) can be used. Microwaves can be generated by any of a variety of methods known in the microwave arts. In general, these methods rely on a klystron or magnetron acting as a microwave source. In general, the frequency of occurrence is in the range of about 300 MHz to 30 GHz and the corresponding wavelength is about 1 m to 1 mm. Theoretically, any frequency in this range can be used effectively, but it is preferred to use a commercially available range of frequencies, including about 850-950 MHz or about 2300-2600 MHz. .

Radiation polymerization is carried out by irradiating γ rays, X rays, α rays, and β rays. Usually, γ-ray irradiation of cobalt 60 is often used.

Furthermore, an energy source for initiating polymerization can be used in combination. For example, an electron beam and infrared rays are used together.

In addition to the thermal polymerization, the polymerization is usually carried out at around room temperature, but it can also be carried out while heating. In this case, acceleration of polymerization can be expected.

[Other ingredients]
In radical polymerization of a radical polymerizable composition containing a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention and a radical polymerizable compound, the condensed polycyclic aromatic of the present invention is used. In addition to a chain transfer agent composed of a urethane (meth) acrylate compound having a skeleton, a radical polymerizable compound, and a radical polymerization initiator, other components may be contained within a range that does not impair the effects of the present invention. It is also possible to add colorants, plasticizers, tackifiers, antioxidants, various stabilizers, fillers, antistatic agents, ultraviolet absorbers and the like.

Moreover, in the range which does not impair the effect of this invention, it may contain components, such as chain transfer agents other than the chain transfer agent which consists of a urethane (meth) acrylate compound which has the condensed polycyclic aromatic skeleton of this invention. Good. Such other chain transfer agents are not particularly limited, and examples include known compounds as chain transfer agents.

For example, mercaptans such as n-butyl mercaptan, t-butyl mercaptan, t-dodecyl mercaptan, n-octyl mercaptan, n-lauryl mercaptan, disulfides such as tetramethylthiudium disulfide, tetraethylthuradium disulfide, carbon tetrachloride, Examples thereof include halogen compounds such as carbon tetrabromide, and olefins such as 2-methyl-1-butene and α-methylstyrene dimer.

These other components can be used alone or in combination of two or more at the same time with respect to the chain transfer agent comprising the urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton of the present invention. These other components can be appropriately selected according to the type and application of the radical polymerizable compound to be applied.

[Production mode]
By radical polymerization of a radical polymerizable composition containing a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention and a radical polymerizable compound, at the end of the polymer to be generated, Alternatively, in the case of a bi- or higher functional chain transfer agent, a polymer having a residue derived from a chain transfer agent composed of a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton is produced in a part of the main chain. be able to.

As a production mode of a polymer having a residue derived from a chain transfer agent composed of a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton at a polymer terminal or a part of the main chain, bulk polymerization, solution polymerization, emulsification A method such as polymerization, suspension polymerization, or slurry polymerization can be used. Moreover, it can be used even when polymerizing batchwise or continuously.

The atmosphere during the polymerization preferably removes molecular oxygen and is generally used under reduced pressure or in the presence of an inert gas. Examples of the inert gas include nitrogen, argon, helium, carbon dioxide and the like.

<Polymer having condensed polycyclic aromatic skeleton at terminal>
As described above, the polymer produced by the above polymerization method using the chain transfer agent of the present invention is a residue derived from the chain transfer agent comprising the urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton of the present invention at the terminal. It is possible to give a condensed polycyclic aromatic skeleton and a functional group as a group. That is, the chain transfer agent comprising the urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention is added to the polymer growth terminal and chain-transferred, and therefore has a terminal structure derived from the chain transfer agent. Become. Therefore, it is possible to synthesize a polymer having a residue derived from a chain transfer agent comprising a urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton of the present invention at the terminal, and further the condensed polycyclic aromatic skeleton of the present invention. A functional group possessed by a chain transfer agent composed of a urethane (meth) acrylate compound having a hydrogen atom can be imparted to the polymer. Generates the chemical and physical properties of the condensed polycyclic aromatic skeleton and functional groups, such as affinity, reactivity, heat resistance, optical properties, and chemical stability, derived from the condensed polycyclic aromatic skeleton and functional groups It can be applied to a polymer and used as a functional polymer.

That is, the chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention can provide a terminal functionalized polymer having a reactive group.

For example, by using a chain transfer agent comprising a (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention, the condensed polycyclic aromatic skeleton and functional group are introduced into the polymer. The polymer can be imparted with physical properties such as ultraviolet absorptivity, fluorescence properties, high refractive index, and sensitization derived from the optical properties of the group skeleton. In addition, chemical properties such as charge transfer, redox, ionization, energy transfer, substitution reactivity due to delocalized pi-electrons possessed by condensed polycyclic aromatics, as well as stacking, aggregation, physical crosslinking, heat resistance due to planarity Functions such as granting can also be expected.

Further, the chain transfer agent comprising a (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention can give a (meth) acrylate skeleton as a reactive group to the obtained polymer. A so-called macromonomer (or macromer) having the properties of a polymerizable monomer (Principles of Pollymerization (FOURTH)
Edition) (2004), p. 752, edited by Mikiharu Tsunoike, "Radical Polymerization Handbook" (NTS, 2010), p. 385, p. 807, HANDBOOK by Krzysztof Matyjazewski
OF RADICAL POLYMERIZATION (2002), page 583, etc.) can be obtained. This macromonomer is extremely useful as a raw material for graft polymers and block polymers known as functional polymers. Conventionally, a macromonomer has been obtained through a complicated process, but can be obtained relatively easily by using the chain transfer agent of the present invention. Alternatively, by selecting the polymerization conditions, it is possible to synthesize the graft polymer or block polymer in-situ or in one pot through the macromonomer production step.

In general, it is well known that radicals are generated through a decomposition reaction by applying heat, light, mechanical energy, etc. to a polymer (Takayuki Otsu, “Chemistry of Polymer Synthesis” (Chemical Doujin, 1979), page 245, 250, 260). At that time, by applying the chain transfer agent of the present invention, it is possible to prevent gelation of the polymer or to graft a functional group. For example, methods described in JP-A-54-100449, JP-A-6-256430 and the like can be used. Specifically, a thermoplastic polymer is melt-kneaded to give thermal energy and mechanical energy, and while cutting the polymer chain, the chain transfer agent of the present invention is applied as an additive to prevent polymer gelation. , Functional groups can be grafted.

Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited to these examples. All parts and percentages are by weight unless otherwise specified.

The product was confirmed by measurement using the following equipment.
(1) Melting point: Melting point measuring device manufactured by Gelen Camp, model MFB-595 (conforms to JIS K0064)
(2) Refractive index: Abbe refractometer: manufactured by Elmer, model ER-7MW-H
(3) Infrared (IR) spectrophotometer: manufactured by JASCO Corporation, model IR-810
(4) Nuclear magnetic resonance apparatus (NMR): manufactured by JEOL Ltd., model GSX FT NMR Spectrometer

(Example 1) In a 100 ml three-necked flask equipped with a compound thermometer of the general formula (2) and a stirrer, 3.48 g (20 mmol) of 1-hydroxy-4-methoxynaphthalene, 3.1 g (22 mmol) of 2-isocyanatoethyl acrylate ) In 30 g of acetone was added, and then a solution of 2.0 g (20 mmol) of triethylamine in 10 g of tetrahydrofuran was added while cooling with ice water. The resulting pale solution was stirred at room temperature for 1 hour and concentrated under reduced pressure to give 6.3 g of a gray powder. The powder was recrystallized from toluene / hexane to obtain 4.1 g (13 mmol) of grayish white crystals of 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-methoxynaphthalene. The yield based on the raw material 1-hydroxy-4-methoxynaphthalene was 65 mol%.

(1) Melting point: 78-80 ° C
(2) Refractive index: n _D = 1.587
(3) IR (KBr, cm ⁻¹ ): 3370, 3010, 2960, 2940, 1726, 1708, 1630, 1624, 1588, 1460, 1390, 1260, 1204, 1158, 1092, 1025, 990, 812, 761, 640.
(4) ¹ H-NMR (CDCl ₃ , 400 MHz): δ = 8.26 (1H, d, J = 8 Hz), 7.84 (1H, d, J = 8 Hz), 7.44-7.56 ( 2H, m), 7.17 (1H, d, J = 8 Hz), 6.76 (1H, d, J = 8 Hz), 6.49 (1H, d.J = 17 Hz), 6.18 (1H, dd, J ₁ = 17 Hz, J ₂ = 9 Hz), 5.91 (1 H, d, J = 9 Hz), 5.48-5.60 (1 H, bs), 4.36 (2 H, t, J = 7 Hz) ), 3.66 (2H, dt, J ₁ = J ₂ = 7 Hz).

(Example 2) Compound thermometer of general formula (2), 3.46 g (10 mmol) of 4,4'-dimethoxy-1,1'-dihydroxy-2,2'-binaphthalene in a 100 ml three-necked flask equipped with a stirrer Then, a gray slurry of 3.12 g (22 mmol) of 2-isocyanatoethyl acrylate in 30 g of acetone was added, and then a solution of 10 g of tetrahydrofuran in 2.0 g (20 mmol) of triethylamine was added while cooling with ice water. With the addition of triethylamine, the mixture was uniformly dissolved once, but a large amount of white precipitate was formed after 1 minute. The slurry is stirred at room temperature for 1 hour, filtered with suction, washed with acetone, dried, and 4,4′-dimethoxy-1,1′-bis [2- (acryloyloxyethyl) aminocarbonyloxy] -2,2 ′. -6.0 g (9.5 mmol) of white powder of binaphthalene was obtained. The yield based on the raw material 4,4′-dimethoxy-1,1′-dihydroxy-2,2′-binaphthalene was 95 mol%.

(1) Melting point: 194-196 ° C
(2) Refractive index: n _D = 1.621
(3) IR (KBr, cm ⁻¹ ): 3300, 3080, 3010, 2940, 1728, 1704, 1548, 1460, 1368, 1258, 1200, 1160, 1120, 1084, 810, 764.
(4) ¹ H-NMR (CDCl ₃ , 400 MHz): δ = 8.29 (2H, d, J = 8 Hz), 7.85 (2H, d, J = 8 Hz), 7.49-7.61 ( 4H, m), 6.81 (2H, s), 6.29 (2H, d.J = 17 Hz), 5.92 (2H, dd, J ₁ = 17 Hz, J ₂ = 9 Hz), 5.75 ( 2H, d, J = 9 Hz), 5.65 (2H, t, J = 7 Hz), 4.00-4.15 (4H, bs), 3.30-3.48 (4H, bs).

(Example 3) In a 100 ml three-necked flask equipped with a compound thermometer of the general formula (3) and a stirrer, 3.2 g (20 mmol) of 1,4-dihydroxynaphthalene and 6.48 g (46 mmol) of 2-isocyanatoethyl acrylate were added. A light brown solution of 40 g of acetone was added, and then a solution of 4.04 g (40 mmol) of triethylamine in 10 g of tetrahydrofuran was added while cooling with ice water. A large amount of white precipitate was formed with the addition of triethylamine. The slurry was stirred at room temperature for 1 hour, suction filtered, washed with acetone, dried and 5.90 g (13.3 mmol) of white powder of 1,4-bis [2- (acryloyloxyethyl) aminocarbonyloxy] naphthalene. ) The yield based on the raw material 1,4-dihydroxynaphthalene was 67 mol%.

(1) Melting point: 139-140 ° C
(2) Refractive index: n _D = 1.605
(3) IR (KBr, cm ⁻¹ ): 3350, 3020, 2970, 1728, 1714, 1539, 1523, 1446, 1414, 1392, 1300, 1280, 1250, 1222, 1182, 1160, 1126, 1068, 1000, 980, 816, 770, 670.
(4) ¹ H-NMR (CDCl ₃ , 400 MHz): δ = 7.86-7.97 (2H, m), 7.48-7.59 (2H, m), 7.26 (2H, s) 6.49 (2H, d.J = 17 Hz), 6.18 (2H, dd, J ₁ = 17 Hz, J ₂ = 9 Hz), 5.91 (2H, d, J = 9 Hz), 5.57 ( 2H, t, J = 7 Hz), 4.37 (4H, t, J = 7 Hz), 3.66 (4H, dt, J ₁ = J ₂ = 7 Hz)

Example 4 Compound thermometer of general formula (5), 9-anthrone 3.88 g (10 mmol), 2-isocyanatoethyl acrylate 3.12 g (22 mmol) acetone 20 g in a 100 ml three-necked flask equipped with a stirrer A pale slurry was added and then a solution of 2.0 g (20 mmol) triethylamine in 10 g acetone was added while cooling with ice water. With the addition of triethylamine, the mixture was uniformly dissolved once, but a large amount of white precipitate was formed after 1 minute. The slurry was stirred at room temperature for 1 hour, suction filtered, washed with acetone, and dried to give 3.35 g (5.0 mmol) of 9- [2- (acryloyloxyethyl) aminocarbonyloxy] anthracene as a white powder. It was. The yield based on the raw material anthrone was 50 mol%.

(1) Melting point: 148-151 ° C
(2) Refractive index: n _D = 1.675
(3) IR (KBr, cm ⁻¹ ): 3295, 3070, 2940, 1723, 1720, 1540, 1412, 1356, 1280.1252, 1240, 1160, 1118, 1073, 980, 890, 820, 770, 740.
(4) ¹ H-NMR (CDCl ₃ , 400 MHz): δ = 8.38 (1H, s), 7.95-8.10 (4H, m), 7.42-7.57 (4H, m) _{, 6.53 (1H, d.J = 17Hz} ), 6.22 (1H, dd, J 1 = 17Hz, J 2 = 9Hz), 5.94 (1H, d, J = 9Hz), 5.78 ( 1H, t, J = 7 Hz), 4.42 (2H, t, J = 7 Hz), 3.71 (2H, dt, J ₁ = J ₂ = 7 Hz)

(Example 5) Compound 10 of the general formula (3), in which adjacent Xs are bonded to each other to form a saturated 6-membered ring, 9,10-dihydroxy- in a 100 ml three-necked flask equipped with a stirrer A pale brown solution of 0.85 g (4 mmol) of 1,2,3,4-tetrahydroanthracene, 1.82 g (11.5 mmol) of 2-isocyanatoethyl acrylate in 8 g of acetone and then cooled with ice water, A solution of 0.404 g (4 mmol) of triethylamine in 2 g of acetone was added. A large amount of white precipitate was formed with the addition of triethylamine. The slurry was stirred at room temperature for 1 hour, filtered with suction, washed with acetone, and dried to give 9,10-bis [2- (acryloyloxyethyl) aminocarbonyloxy] -1,2,3,4-tetrahydroanthracene white. 1.60 g (3 mmol) of powder was obtained. The yield based on the raw material 9,10-dihydroxy-1,2,3,4-tetrahydroanthracene was 75 mol%.

(1) Melting point: 198-200 ° C
(2) Refractive index: n _D = 1.622
(3) IR (KBr, cm ⁻¹ ): 3340, 3080, 2945, 2870, 1724, 1716, 1640, 1540, 1460, 1414, 1370, 1303, 126, 1210, 1181, 1141, 1122, 1062, 970, 942, 810, 736, 680.
(4) ¹ H-NMR (CDCl ₃ , 400 MHz): δ = 7.72-7.82 (2H, m), 7.39-7.49 (2H, m), 6.50 (2H, d. J = 17 Hz), 6.19 (2H, dd, J ₁ = 17 Hz, J ₂ = 9 Hz), 5.93 (2H, d, J = 9 Hz), 5.56 (2H, t, J = 7 Hz), 4.38 (4H, t, J = 7 Hz), 3.66 (4H, dt, J ₁ = J ₂ = 7 Hz), 2.73-2.88 (4H, bs), 1.74-1.88 (4H, bs).

(Example 6) A compound thermometer in which adjacent X's are bonded to each other to form an unsaturated 6-membered ring in the compound of the general formula (3), and 1,4-dihydrocarbon in a 100 ml three-necked flask equipped with a stirrer A solution of anthracene-9,10-diol (4.24 g, 20 mmol), 2-isocyanatoethyl acrylate (7.0 g, 50 mmol) in 30 g of acetone in a pale reddish purple solution was added, followed by cooling with ice water while adding 2.0 g of triethylamine. A solution of (4 mmol) in 10 g of acetone was added. A large amount of white precipitate was formed with the addition of triethylamine. The slurry is stirred at room temperature for 1 hour, suction filtered, washed with acetone and dried to give a white powder of 9,10-bis [2- (acryloyloxyethyl) aminocarbonyloxy] -1,4-dihydroanthracene. 60 g (17.4 mmol) were obtained. The yield based on the raw material 9,10-dihydroxy-1,4-dihydroanthracene was 87 mol%.

(1) Melting point: 221-222 ° C
(2) Refractive index: n _D = 1.631
(3) IR (KBr, cm ⁻¹ ): 3325, 3070, 3045, 2940, 1728, 1718, 1541, 1412, 1368, 1308, 1260, 1210, 1180, 1140, 1120, 1060, 984, 810, 762 700,677.
(4) ¹ H-NMR (CDCl ₃ , 400 MHz): δ = 7.74-7.84 (2H, m), 7.40-7.50 (2H, m), 6.51 (2H, d. J = 17 Hz), 6.20 (2H, dd, J ₁ = 17 Hz, J ₂ = 9 Hz), 5.93 (2H, d, J = 9 Hz), 5.82 (2H, s), 5.59 ( 2H, t, J = 7 Hz), 4.38 (4H, t, J = 7 Hz), 3.67 (4H, dt, J ₁ = J ₂ = 7 Hz), 3.43 (4H, s).

(Example 7) Compound of general formula (4) In a 100 ml three-necked flask equipped with a thermometer and a stirrer, 9,20-dihydroxyanthracene 4.20 g (20 mmol), 2-isocyanatoethyl acrylate 7.0 g (50 mmol) A pale yellow solution of 60 g of tetrahydrofuran was added, and then a solution of 10 g of tetrahydrofuran in an amount of 2.0 g (4 mmol) of triethylamine was added while cooling with ice water. A large amount of pale yellow precipitate was formed with the addition of triethylamine. The slurry was stirred at room temperature for 1 hour, filtered with suction, washed with tetrahydrofuran and dried to give 6.60 g (13.4 mmol) of a white powder of 9,10-bis [2- (acryloyloxyethyl) aminocarbonyloxy] anthracene. ) The yield based on the starting material 9,10-dihydroxyanthracene was 68 mol%.

(1) Melting point: 214-216 ° C
(2) Refractive index: n _D = 1.648
(3) IR (KBr, cm ⁻¹ ): 3355, 3110, 3060, 1724, 1721, 1640, 1534, 1420, 1378, 1306, 1260, 1220, 1170, 1122, 1058, 982, 816, 772, 724 650.
(4) ¹ H-NMR (CDCl ₃ , 400 MHz): δ = 7.9-9.08 (4H, m), 7.46-7.57 (4H, m), 6.52 (2H, d. J = 17 Hz), 6.22 (2H, dd, J ₁ = 17 Hz, J ₂ = 9 Hz), 5.94 (2H, d, J = 9 Hz), 5.80 (2H, t, J = 7 Hz), 4.42 (4H, t, J = 7 Hz), 3.72 (4H, dt, J ₁ = J ₂ = 7 Hz).

(Example 8) Compound of general formula (4) In a 100 ml three-necked flask equipped with a thermometer and a stirrer, 4,20 g (20 mmol) of 9,10-dihydroxyanthracene and 7.75 g (50 mmol) of 2-isocyanatoethyl methacrylate were added. A pale yellow solution of 60 g of tetrahydrofuran was added, and then a solution of 2.0 g (4 mmol) of triethylamine in 10 g of tetrahydrofuran was added while cooling with ice water. A large amount of yellow precipitate was formed with the addition of triethylamine. The slurry was stirred at room temperature for 1 hour, suction filtered, washed with tetrahydrofuran, dried and 7.60 g (14.6 mmol) of a white powder of 9,10-bis [2- (methacryloyloxyethyl) aminocarbonyloxy] anthracene. ) The yield based on the raw material 9,10-dihydroxyanthracene was 76 mol%.

(1) Melting point: 222-223 ° C
(2) IR (KBr, cm ⁻¹ ): 3330, 3060, 2950, 1722, 1715, 1640, 1538, 1430, 1378, 1321, 1300, 1250, 1234, 1168, 1164, 1140, 1118, 1058, 960, 946, 820, 768, 721, 660, 600, 410.
(3) ¹ H-NMR (CDCl ₃ , 400 MHz): δ = 8.13-8.22 (4H, m), 7.70 (2H, t, J = 7 Hz), 7.58-7.67 ( 4H, m), 6.26 (2H, s), 5.75 (2H, s), 4.47 (4H, t, J = 7 Hz), 3.76 (4H, dt, J ₁ = J ₂ = 7 Hz).

Example 9 Compound of General Formula (4) with q = 1 Thermometer, 4.20 g (20 mmol) of 9,10-dihydroxyanthracene, 2- (2-isocyanato) in a 100 ml three-necked flask equipped with a stirrer A solution of 9.15 g (50 mmol) of ethoxy) ethyl methacrylate in 60 g of tetrahydrofuran was added, and then a solution of 10 g of tetrahydrofuran in 2.0 g (20 mmol) of triethylamine was added while cooling with ice water. The resulting pale solution was stirred at room temperature for 1 hour, concentrated under reduced pressure, and then 40 ml of methanol was added to form a precipitate. The slurry was suction filtered, washed with methanol and dried, and 4.3 g (7.4 mmol) of a light yellow powder of 9,10-bis [2- {2- (acryloyloxyethoxy) ethyl} aminocarbonyloxy] anthracene was obtained. Obtained. The yield based on the starting material 9,10-dihydroxyanthracene was 37 mol%.

(1) Melting point: 109-111 ° C
(2) IR (KBr, cm ⁻¹ ): 3330, 3075, 2940, 2880, 1720, 1716, 1660, 1530, 1372, 1300, 1290, 1250, 1172, 1130, 1048, 940, 810, 770, 694.
(3) ¹ H-NMR (CDCl ₃ , 400 MHz: δ = 8.00-8.12 (4H, m), 7.43-7.58 (4H, m), 6.21 (2H, s), 5.95 (2H, t, J = 7 Hz)), 5.60 (2H, s), 4.39 (4H, t, J = 7 Hz), 3.86 (4H, dt, J ₁ = J ₂ = 7 Hz). 3.69-3.79 (4H, m), 3.55-3.64 (4H, m) 7.70 (2H, t, J = 7 Hz).

(Example 10)
4 g of commercially available methyl methacrylate (Wako special grade) as a radical polymerizable compound is put in a test tube, and 2 mass% of azobisisobutyronitrile (Wako special grade), chain transfer as an initiator for this radical polymerizable compound. As the agent, 5000 ppm by mass of 1- (2-acryloyloxyethyl) aminocarbonyloxy-4-methoxynaphthalene was added to obtain a radically polymerizable composition. The test tube containing the radical polymerizable composition was capped with a septum, and nitrogen was bubbled through the composition at a rate of 15 mL / min for 20 minutes. Then, the test tube was immersed in a heated oil bath while nitrogen was passed, and the solution temperature in the test tube was kept at 60 ° C. for 60 minutes to obtain a polymerization time. The product is dissolved in tetrahydrofuran (Wako Special Grade) at a predetermined concentration, and a refractometer (RI) (manufactured by JASCO RI-2031), a multiwavelength ultraviolet spectrometer (manufactured by JASCO MD-2010), and GPC are used as detectors. The produced polymer was characterized using gel permeation chromatography (manufactured by JASCO) equipped with a column (Showex DPC Shodex GPC KF-806L). Among these, a refractometer was used as a detector, and the polymerization rate was measured from the average molecular weight of the produced polymer, its distribution and its peak area. Furthermore, using a multi-wavelength ultraviolet spectrometer as a detector, the ultraviolet absorption spectrum of the produced polymer was measured, and the presence or absence of absorption at a wavelength of 350 to 500 nm derived from the condensed polycyclic aromatic skeleton was measured. These measurement results are shown in Table 1.

(Examples 11-17, Comparative Examples 1-3)
The same operation as in Example 1 was performed except that the type of chain transfer agent to be added, the addition amount of the chain transfer agent, and the polymerization time were changed as shown in Table 1, and the measurement results are shown in Table 1.

From the comparison between Example 10 to Example 17 and Comparative Example 1, it can be seen that the chain transfer agent comprising the urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention has excellent chain transfer ability. Further, from comparison between Example 1 and Comparative Examples 2 and 3 using a conventionally known chain transfer agent, chain transfer comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention is also possible. It can be seen that the agent has excellent chain transfer ability.

Moreover, in the ultraviolet absorption spectrum of the produced | generated polymer, although the absorption in wavelength 350-500nm is not observed in Comparative Examples 1-3, it is from the urethane (meth) acrylate compound which has the condensed polycyclic aromatic skeleton of this invention. Therefore, when a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton of the present invention is used, the present invention is incorporated into the produced polymer. It can be seen that a condensed polycyclic aromatic skeleton derived from a chain transfer agent composed of a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton is introduced.

Claims (14)

A urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by the following general formula (1).

(In the formula (1), n represents an integer of 0 to 3, and R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxyalkyl group, a glycidyl group, a hydroxyalkyl group, or an aryloxyalkyl group. , N may be the same or different when n is 2 or 3, p is an integer of 1 or 2, q is an integer of 0 to 4, and r is 1 To p, and when p is 2, the two q and r may be the same or different, and Y and Z are each independently a hydrogen atom or a methyl group. In the case where p is 2, in the plurality of Y and the plurality of Z, Y and Z may be the same or different, and each represents a hydrogen atom or a methyl group. Independently hydrogen atom, alkyl group Represents an aryl group, a set of X Adjacent instead of the substituent, they may form a 6-membered ring bonded to a saturated or unsaturated with one another.) The urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton according to claim 1, wherein p and n are 1 in the general formula (1). The urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton according to claim 1, wherein p is 2 and n is 0 in the general formula (1). A urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by the following general formula (2).

(In the formula (2), R represents an alkyl group, an aryl group, an aralkyl group, an alkoxyalkyl group, a glycidyl group, a hydroxyalkyl group, or an aryloxyalkyl group, q represents an integer of 0 to 4, and r represents 1) And Y and Z each independently represent a hydrogen atom or a methyl group, and when there are a plurality of Ys, each Y also independently represents a hydrogen atom or a methyl group. Represents a hydrogen atom, an alkyl group or an aryl group, but a pair of adjacent Xs may be bonded to each other to form a saturated or unsaturated 6-membered ring instead of the substituent. A urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by the following general formula (3).

(In the formula (3), two q and r may be the same or different, q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z represent Each independently represents a hydrogen atom or a methyl group, and in the plurality of Y and the plurality of Z, Y and Z may be the same or different, and each represents a hydrogen atom or a methyl group, and a plurality of X Each independently represents a hydrogen atom, an alkyl group or an aryl group, but a pair of adjacent Xs may be bonded to each other to form a saturated or unsaturated 6-membered ring instead of the substituent. Good.) A urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by the following general formula (4).

(In the formula (4), two q and r may be the same or different, q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z represent , Each independently represents a hydrogen atom or a methyl group, and when p is 2, in a plurality of Y and a plurality of Z, Y and Z may be the same or different, and a hydrogen atom or a methyl group And a plurality of X's independently represent a hydrogen atom, an alkyl group or an aryl group.) A urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton represented by the following general formula (5).


(In the formula (5), q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, And each independently represents a hydrogen atom or a methyl group, and a plurality of X's each independently represents a hydrogen atom, an alkyl group or an aryl group.) Addition of a compound having a condensed polycyclic aromatic skeleton represented by general formula (13) and a (meth) acrylate compound having an isocyanate group represented by general formula (14) in the presence or absence of a solvent The method for producing a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton according to claim 1, wherein the reaction is performed.

(In the formula (13), n represents an integer of 0 to 3, m represents an integer of 1 or 2, and R represents a hydrogen atom, alkyl group, aryl group, aralkyl group, alkoxyalkyl group, glycidyl group, hydroxy group. Represents an alkyl group or an aryloxyalkyl group, and when n is 2 or 3, a plurality of Rs may be the same or different from each other, and a plurality of Xs independently represent a hydrogen atom, an alkyl group or an aryl Represents a group, but a pair of adjacent Xs may be bonded to each other to form a saturated or unsaturated 6-membered ring instead of the substituent.

(In the formula (14), q represents an integer of 0 to 4, r represents an integer of 1 to 4, Y and Z each independently represent a hydrogen atom or a methyl group, and Y and Z each independently Represents a hydrogen atom or a methyl group, and when there are a plurality of Ys, each independently represents a hydrogen atom or a methyl group.) A chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton according to any one of claims 1 to 7. The radically polymerizable composition containing the chain transfer agent which consists of a urethane (meth) acrylate compound which has a condensed polycyclic aromatic skeleton of Claim 9, and a radically polymerizable compound. The radically polymerizable composition according to claim 10, wherein the radically polymerizable compound is (meth) acrylic acid, (meth) acrylic acid ester or styrene. A polymer obtained by radical polymerization of a radically polymerizable composition comprising a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton according to claim 9 and a radically polymerizable compound. A polymer having a residue derived from a chain transfer agent composed of a urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton at the end of the polymer or part of the main chain. The polymer according to claim 12, wherein the radical polymerizable compound is (meth) acrylic acid, (meth) acrylic ester or styrene. A radical polymerizable compound is radically polymerized in the presence of a chain transfer agent comprising a urethane (meth) acrylate compound having a condensed polycyclic aromatic skeleton according to claim 9, A method for producing a polymer having, in part, a residue derived from a chain transfer agent comprising a urethane (meth) acrylate compound having the condensed polycyclic aromatic skeleton.