JP2010059123A - Aromatic compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound that not only can enhance the ultraviolet resistance of a polymeric material wherein the compound is incorporated but also can suppress the decomposition of other unstable compounds by using the polymeric material comprising the compound as an ultraviolet filter, and can be used as an ultraviolet absorbent capable of maintaining the capacity of absorbing long-wave ultraviolet rays for a long period of time. <P>SOLUTION: There is provided an aromatic compound represented by formula (1). In the formula, Ar<SP>1</SP>represents a specific aromatic residue, provided that the aromatic residue may contain a hetero atom; X<SP>1a</SP>and X<SP>1b</SP>each independently represent a hetero atom; Y<SP>1</SP>represents a -SR<SP>1a</SP>group or a -SO<SB>2</SB>R<SP>1b</SP>group; R<SP>1a</SP>and R<SP>1b</SP>each represent a hydrogen atom or a specific monovalent substituent; and n<SP>1</SP>represents an integer of 1 to 4. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to an aromatic compound, and an ultraviolet absorber and a fluorescent brightening agent comprising the compound.

Conventionally, ultraviolet absorbers have been imparted by sharing ultraviolet absorbers with various resins. An inorganic ultraviolet absorber and an organic ultraviolet absorber may be used as the ultraviolet absorber. Inorganic ultraviolet absorbers (see, for example, Patent Documents 1 to 3) are excellent in durability such as weather resistance and heat resistance, but are free to be selected because the absorption wavelength is determined by the band gap of the compound. There is no such thing that can absorb up to 400 nm in the long wave ultraviolet (UV-A) region, and those that absorb long wave ultraviolet light have absorption up to the visible region and are colored.
On the other hand, since the organic ultraviolet absorber has a high degree of freedom in the structural design of the absorbent, it is possible to obtain various absorption wavelengths by devising the structure of the absorbent.

  In the past, systems using various organic ultraviolet absorbers have been studied, and when absorbing up to the long wave ultraviolet region, whether the maximum absorption wavelength is in the long wave ultraviolet region or whether the concentration is increased. There are two possible ways. However, those having the maximum absorption wavelength described in Patent Documents 4 and 5 in the long-wave ultraviolet region have poor light resistance, and the absorption capacity decreases with time.

  In contrast, benzophenone and benzotriazole UV absorbers have relatively good light resistance, and can be cut relatively clearly up to a long wavelength region by increasing the concentration and film thickness (see, for example, Patent Documents 6 and 7). .) A benzoxazinone-based ultraviolet absorber is also known (see, for example, Patent Document 8). However, when these ultraviolet absorbers are usually mixed and applied in a resin or the like, the film thickness is limited to about several tens of μm. With this film thickness, it is necessary to add an ultraviolet absorber at a considerably high concentration in order to cut to a long wavelength region. However, there has been a problem that simply adding to a high concentration causes precipitation of ultraviolet absorbers and bleeding out due to long-term use. In addition, some benzophenone and benzotriazole ultraviolet absorbers have skin irritation properties and accumulation properties in the living body, and careful attention is required for use.

JP-A-5-339033 JP-A-5-345639 JP-A-6-56466 JP-A-6-145387 JP 2003-177235 A JP-A-2005-517787 JP-A-7-285927 JP 62-11744 A

  The object of the present invention is to solve the above-mentioned problems, not only to improve the ultraviolet light durability of the polymer material to be shared, but also to stabilize the other by using the polymer material as an ultraviolet filter. An object of the present invention is to provide a compound that can suppress decomposition of the compound and can be used as an ultraviolet absorber that maintains long-wave ultraviolet absorption ability for a long time.

  As a result of examining the aromatic compounds in detail, the present inventors have found a compound having a conventionally unknown structure that has high light fastness and can absorb ultraviolet rays in a long wavelength region that could not be covered so far. The present invention has been completed.

［式中、Ａｒ¹は、１価の５〜２０員環の芳香族残基を表す。該芳香族残基はヘテロ原子を含有していても良く、置換基を有していても良い。
Ｘ^1a及びＸ^1bは、互いに独立してヘテロ原子を表す。また、Ｘ^1a及びＸ^1bは置換基を有していても良い。
Ｙ¹は、−ＳＲ^1a基、または−ＳＯ₂Ｒ^1b基を表す。また、Ｒ^1aは、−Ｍｅ基と−ＣＮ基を除く、水素原子または１価の置換基を表す。Ｒ^1bは、−Ｍｅ基を除く、水素原子または１価の置換基を表す。
ｎ¹は、１〜４の整数を表す。
Ａｒ¹に結合している環は、任意の位置に二重結合を有していても良い。］
＜２＞前記一般式（１）で表される化合物が下記一般式（２）で表される化合物であることを特徴とする、＜１＞項に記載の芳香族化合物。

［式中、Ａｒ²は、前記一般式（１）のＡｒ¹と同義である。
Ｙ²は、前記一般式（１）のＹ¹と同義である。
ｎ²は、前記一般式（１）のｎ¹と同義である。］
＜３＞前記一般式（２）で表される化合物が下記一般式（３）で表される化合物であることを特徴とする、＜２＞項に記載の芳香族化合物。

［式中、Ａｒ³は、前記一般式（２）のＡｒ²と同義である。
Ｙ³は、前記一般式（２）のＹ²と同義である。］
＜４＞前記一般式（３）で表される化合物が下記一般式（４）で表される化合物であることを特徴とする、＜３＞項に記載の芳香族化合物。

［式中、Ｙ⁴は、前記一般式（３）のＹ³と同義である。］
＜５＞前記一般式（４）で表される化合物が下記一般式（５）で表される化合物であることを特徴とする、請求項４記載の芳香族化合物。

［式中、Ｙ^５は、−ＳＲ^５a基、または−ＳＯ₂Ｒ^５b基を表す。また、Ｒ^５aは、炭素数２〜１０のアルキル基を表す。Ｒ^５bは、置換または無置換のアミノ基を表す。］
＜６＞＜１＞〜＜５＞項のいずれか１項に記載の芳香族化合物からなる紫外線吸収剤。
＜７＞＜１＞〜＜５＞項のいずれか１項に記載の芳香族化合物からなる蛍光増白剤。
＜８＞＜６＞項記載の紫外線吸収剤および／または＜７＞項記載の蛍光増白剤を含む分散物。
＜９＞＜６＞項記載の紫外線吸収剤および／または＜７＞項記載の蛍光増白剤を含む溶液。
＜１０＞＜６＞項記載の紫外線吸収剤および／または＜７＞項記載の蛍光増白剤を含む高分子材料。 The object of the present invention has been achieved by the following means.
<1> An aromatic compound represented by the following general formula (1).

[Wherein Ar ¹ represents a monovalent 5- to 20-membered aromatic residue. The aromatic residue may contain a hetero atom and may have a substituent.
X ^1a and X ^1b each independently represent a hetero atom. X ^1a and X ^1b may have a substituent.
Y ¹ represents a —SR ^1a group or a —SO ₂ R ^1b group. R ^1a represents a hydrogen atom or a monovalent substituent excluding the —Me group and the —CN group. R ^1b represents a hydrogen atom or a monovalent substituent excluding the -Me group.
n ¹ represents an integer of 1 to 4.
The ring bonded to Ar ¹ may have a double bond at an arbitrary position. ]
<2> The aromatic compound according to <1>, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2).

Wherein, Ar ² has the same meaning as Ar ¹ in the general formula (1).
Y ² has the same meaning as Y ^{1 in the} general formula (1).
n ² has the same meaning as n ^{1 in the} general formula (1). ]
<3> The aromatic compound according to <2>, wherein the compound represented by the general formula (2) is a compound represented by the following general formula (3).

[Wherein Ar ³ has the same meaning as Ar ^{2 in} formula (2).
Y ³ has the same meaning as Y ^{2 in the} general formula (2). ]
<4> The aromatic compound according to <3>, wherein the compound represented by the general formula (3) is a compound represented by the following general formula (4).

[Wherein Y ⁴ has the same meaning as Y ^{3 in} formula (3). ]
<5> The aromatic compound according to claim 4, wherein the compound represented by the general formula (4) is a compound represented by the following general formula (5).

[Wherein Y ⁵ represents a —SR ^5a group or a —SO ₂ R ^5b group. R ^5a represents an alkyl group having 2 to 10 carbon atoms. R ^5b represents a substituted or unsubstituted amino group. ]
<6> An ultraviolet absorber comprising the aromatic compound according to any one of <1> to <5>.
<7> A fluorescent whitening agent comprising the aromatic compound according to any one of <1> to <5>.
<8> A dispersion containing the ultraviolet absorber according to <6> and / or the fluorescent brightener according to <7>.
<9> A solution containing the ultraviolet absorber according to <6> and / or the fluorescent brightener according to <7>.
<10> A polymer material comprising the ultraviolet absorber according to <6> and / or the fluorescent brightener according to <7>.

  The compound of the present invention can be used as an ultraviolet absorber having high light fastness and a fluorescent whitening agent having high whitening property. Moreover, the light stability of a polymer molded product can be enhanced by incorporating the compound of the present invention into a polymer molded product such as plastic or fiber. Furthermore, the polymer material containing the compound of the present invention can be used as a filter or a container for protecting contents vulnerable to ultraviolet rays by utilizing the excellent ultraviolet absorbing ability. The compound of the present invention was able to significantly improve the light resistance by introducing a substituent containing a sulfur atom into the benzoxazinone skeleton, as compared with those having other substituents.

Hereinafter, the present invention will be described in detail.
The compound of the present invention is an aromatic compound represented by the following general formula (1).

In the general formula (1), Ar ¹ represents a monovalent 5- to 20-membered aromatic residue. Moreover, this aromatic residue may contain a hetero atom and may have a substituent.
Examples of the hetero atom include a boron atom, a nitrogen atom, an oxygen atom, a silicon atom, a phosphorus atom, a sulfur atom, a selenium atom, and a tellurium atom. A hetero atom is preferably a nitrogen atom, an oxygen atom, or a sulfur atom. More preferably, they are a nitrogen atom and a sulfur atom. Particularly preferred is a sulfur atom. When two or more hetero atoms are present, they may be the same atom or different atoms.

The aromatic ring constituting Ar ¹ may be a single ring or a condensed ring. In the case of a single ring, Ar ¹ is preferably a 5- to 10-membered ring, more preferably a 5- to 6-membered ring. In the case of a condensed ring, Ar ¹ is preferably a 2-10 cyclic aromatic ring condensed with a 5-10 membered ring, more preferably a 2-5 cyclic aromatic ring condensed with a 5-6 membered ring. preferable.

  Examples of aromatics in which one hydrogen atom is added to a monovalent aromatic residue include benzene, naphthalene, anthracene, indene, azulene, biphenylene, fluorene, phenanthrene, pyrene, triphenylene, tetraphenylene, perylene, pentacene, coronene, chrysene Pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, furan, thiophene, oxazole, isoxazole, thiazole, Examples include isothiazole, 1,2,3-oxadiazole, and 1,3,4-thiadiazole. Preferred aromatics are benzene, naphthalene, pyridine and thiophene. More preferred are benzene and thiophene. Particularly preferred is benzene. Any position may be used for removing the aromatic hydrogen atom. For example, the bonding position of naphthalene is 1 or 2 position. Moreover, as for the bonding position in the hetero 5-membered ring compound pyrrole, the 2- or 3-position can be mentioned. Examples of the bonding position in the hetero 6-membered ring compound pyridine include the 2, 3 or 4 position.

Moreover, the aromatic residue may have a substituent. A monovalent substituent is mentioned as a substituent. Examples of the monovalent substituent (hereinafter referred to as R) include a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom), an alkyl group having 1 to 20 carbon atoms (for example, methyl and ethyl), and a carbon number of 6 ~ 20 aryl group (eg phenyl, naphthyl), cyano group, carboxyl group, C2-C20 alkoxycarbonyl group (eg methoxycarbonyl), C7-20 aryloxycarbonyl group (eg phenoxycarbonyl), substituted Or an unsubstituted carbamoyl group (for example, carbamoyl, N-phenylcarbamoyl, N, N-dimethylcarbamoyl), an alkylcarbonyl group having 2 to 20 carbon atoms (for example, acetyl), an arylcarbonyl group having 7 to 20 carbon atoms (for example, benzoyl) Nitro group, substituted or unsubstituted amino group (eg amino, dimethyl) Mino, anilino), C1-C20 acylamino group (for example, acetamide, ethoxycarbonylamino), sulfonamide group (for example, methanesulfonamide), imide group (for example, succinimide, phthalimide), imino group (for example, benzylideneamino), hydroxy Group, an alkoxy group having 1 to 20 carbon atoms (for example, methoxy), an aryloxy group having 6 to 20 carbon atoms (for example, phenoxy), an acyloxy group having 2 to 20 carbon atoms (for example, acetoxy), and an alkylsulfonyl having 1 to 20 carbon atoms Oxy group (for example, methanesulfonyloxy), arylsulfonyloxy group having 6 to 20 carbon atoms (for example, benzenesulfonyloxy), sulfo group, substituted or unsubstituted sulfamoyl group (for example, sulfamoyl, N-phenylsulfamoyl), carbon number 1-2 Alkylthio group (for example, methylthio), arylthio group having 6 to 20 carbon atoms (for example, phenylthio), alkylsulfonyl group having 1 to 20 carbon atoms (for example, methanesulfonyl), arylsulfonyl group having 6 to 20 carbon atoms (for example, benzenesulfonyl) And a heterocyclic group having 6 to 20 carbon atoms (for example, pyridyl, morpholino) and the like. Further, the substituent may be further substituted, and when there are a plurality of substituents, they may be the same or different. In that case, the above-mentioned monovalent substituent R can be mentioned as an example of a substituent. Moreover, you may combine with substituents and may form a ring.
Preferred examples of the substituent include an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms. More preferred are an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 20 carbon atoms, and particularly preferred is an alkyl group having 1 to 20 carbon atoms.

X ^1a and X ^1b each independently represent a hetero atom. Examples of the hetero atom include a boron atom, a nitrogen atom, an oxygen atom, a silicon atom, a phosphorus atom, a sulfur atom, a selenium atom, and a tellurium atom. A hetero atom is preferably a nitrogen atom, an oxygen atom, or a sulfur atom. More preferably, they are a nitrogen atom and an oxygen atom. X ^1a and X ^1b may have a substituent. Examples of the substituent include the examples of the monovalent substituent R described above.

Y ¹ represents a —SR ^1a group or a —SO ₂ R ^1b group. R ^1a represents a hydrogen atom or a monovalent substituent excluding the —Me group and the —CN group. Examples of the substituent include the examples of the monovalent substituent R described above. R ^1a is preferably an alkyl group having 2 to 10 carbon atoms, an aryl group having 20 or less carbon atoms, or a hydrogen atom, and more preferably an alkyl group having 2 to 10 carbon atoms or a hydrogen atom. Particularly preferred is the case of representing an alkyl group having 2 to 10 carbon atoms.
R ^1b represents hydrogen or a monovalent substituent excluding the —Me group. Examples of the substituent include the examples of the monovalent substituent R described above. R ^1b is preferably an alkyl group having 2 to 10 carbon atoms, an alkoxy group having 10 or less carbon atoms, a substituted or unsubstituted amino group, or a hydrogen atom, more preferably an alkyl group having 2 to 10 carbon atoms or carbon. An alkoxy group having several tens or less, a substituted or unsubstituted amino group, more preferably an alkoxy group having 10 or less carbon atoms, or a substituted or unsubstituted amino group, particularly preferably a substituted or unsubstituted amino group. It is.

n ¹ represents an integer of 1 to 4. n ¹ is preferably ¹ , 2 or 3, more preferably 1 or 2, and particularly preferably 1.

  The compound represented by the general formula (1) is preferably a compound represented by the following general formula (2). Hereinafter, the compound represented by the general formula (2) will be described.

Ar ² has the same meaning as Ar ^{1 in the} general formula (1). The same applies to the preferred case.

Y ² has the same meaning as Y ^{1 in the} general formula (1). The same applies to the preferred case.

n ² has the same meaning as n ^{1 in the} general formula (1). The same applies to the preferred case.

  The compound represented by the general formula (2) is preferably a compound represented by the following general formula (3). Hereinafter, the compound represented by the general formula (3) will be described.

Ar ³ has the same meaning as Ar ^{2 in the} general formula (2). The same applies to the preferred case.

Y ³ has the same meaning as Y ^{2 in the} general formula (2). The same applies to the preferred case.

  Furthermore, the compound represented by the general formula (3) is preferably a compound represented by the following general formula (4). Hereinafter, the compound represented by Formula (4) will be described.

Y ⁴ is the same as defined in the Y ⁴ in the general formula (3). The same applies to the preferred case.

  Furthermore, the compound represented by the general formula (4) is preferably a compound represented by the following general formula (5). Hereinafter, the compound represented by Formula (5) will be described.

Y ⁵ represents a —SR ^5a group or a —SO ₂ R ^5b group. R ^5a represents an alkyl group having 2 to 10 carbon atoms. R ^5b represents a substituted or unsubstituted amino group.

  The compound represented by any one of the general formulas (1) to (5) can be synthesized by any method. For example, publicly known patent documents and non-patent documents, for example, an example of page 4 left 43th line to right 8th line of JP-A-2000-264879, page 4 right column 5th line 30 to 30 of JP-A-2003-155375. It can be synthesized with reference to the example of the line, “Bioorganic & Medicinal Chemistry”, 2000, 8, pp. 2095-2103, “Bioorganic & Medicinal Chemistry Letters”, 2003, Vol. 13, pp. 4077-4080. For example, the following exemplary compound (5) can be synthesized by reacting benzoyl chloride with 2-amino-3- (N-methylsulfamoyl) benzoic acid. The following exemplified compound (6) can be synthesized by reacting benzoyl chloride with 2-amino-5- [N, N-bis (2-ethylhexyl) sulfamoyl] benzoic acid. The following exemplified compound (22) can be synthesized by reacting 1-naphthoyl chloride with 2-amino-5- [N, N-bis (2-ethylhexyl) sulfamoyl] benzoic acid. The following exemplified compound (24) can be synthesized by reacting 2-anthracenecarbonyl chloride with 2-amino-5- [N, N-bis (2-ethylhexyl) sulfamoyl] benzoic acid. The following exemplified compound (33) can be synthesized by reacting 2-pyrrolecarbonyl chloride with 2-amino-5- [N, N-bis (2-ethylhexyl) sulfamoyl] benzoic acid. The following exemplified compound (34) can be synthesized by reacting 2-furancarbonyl chloride with 2-amino-5- [N, N-bis (2-ethylhexyl) sulfamoyl] benzoic acid. The following exemplified compound (39) can be synthesized by reacting picolinic acid chloride with 2-amino-5- [N, N-bis (2-ethylhexyl) sulfamoyl] benzoic acid. The following exemplified compound (50) can be synthesized by reacting pyrazinecarbonyl chloride with 2-amino-5- [N, N-bis (2-ethylhexyl) sulfamoyl] benzoic acid.

  Specific examples of the compound represented by any one of the general formulas (1) to (5) are shown below, but the present invention is not limited thereto.

  The compounds of the present invention can take tautomers depending on the structure and the environment in which they are placed. Although the present invention is described in one of the representative forms, tautomers different from those described in the present invention are also included in the compounds of the present invention.

The compound of the present invention may contain isotopes (for example, ² H, ³ H, ¹³ C, ¹⁵ N, ¹⁷ O, ¹⁸ O and the like).

  A polymer containing the structure of the compound represented by any one of the general formulas (1) to (5) in the repeating unit can also be suitably used in the present invention. The polymer may be a homopolymer or a copolymer composed of two or more types of repeating units. Further, it may be a copolymer containing other repeating units. The polymer containing the ultraviolet absorber structure in the repeating unit is described in JP-B-1-53455, JP-A-61-189530, and European Patent 27242. The description of these patents can be referred to for the method of obtaining the polymer.

The compound represented by any one of the general formulas (1) to (5) can be suitably used as an ultraviolet absorber. Hereinafter, the case where the compound represented by any one of the general formulas (1) to (5) is used as an ultraviolet absorber will be described.
The compound represented by any one of the general formulas (1) to (5) can be preferably used as a long wavelength ultraviolet absorber. The maximum absorption wavelength is preferably in the range of 250 to 400 nm, more preferably in the range of 260 to 390 nm, and particularly preferably in the range of 270 to 380 nm.
Any use form of the ultraviolet absorber of the present invention may be used. For example, a liquid dispersion, a solution, a polymer material, etc. are mentioned.

The ultraviolet absorbent comprising the compound represented by any one of the general formulas (1) to (5) of the present invention can be used in the state of a dispersion dispersed in a dispersion medium. Hereinafter, the ultraviolet absorbent dispersion containing the ultraviolet absorbent of the present invention will be described.
Any medium may be used for dispersing the ultraviolet absorbent according to the present invention. For example, water, an organic solvent, a resin, a resin solution, and the like can be given. These may be used alone or in combination.

  Examples of the organic solvent for the dispersion medium used in the present invention include hydrocarbons such as pentane, hexane and octane, aromatics such as benzene, toluene and xylene, ethers such as diethyl ether and methyl t-butyl ether, Alcohols such as methanol, ethanol and isopropanol, esters such as acetone, ethyl acetate and butyl acetate, ketones such as methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethyl Amides such as acetamide and N-methylpyrrolidone, sulfoxides such as dimethyl sulfoxide, amines such as triethylamine and tributylamine, carboxylic acids such as acetic acid and propionic acid, halogens such as methylene chloride and chloroform Tetrahydrofuran, heterocyclic ring system, such as pyridine, and the like. These can be used in combination at any ratio.

  Examples of the resin for the dispersion medium used in the present invention include thermoplastic resins and thermosetting resins conventionally used in the production of various conventionally known molded articles, sheets, films and the like. Examples of thermoplastic resins include polyethylene resins, polypropylene resins, poly (meth) acrylic ester resins, polystyrene resins, styrene-acrylonitrile resins, acrylonitrile-butadiene-styrene resins, polyvinyl chloride resins, Polyvinylidene chloride resin, polyvinyl acetate resin, polyvinyl butyral resin, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol resin, polyethylene terephthalate resin (PET), polybutylene terephthalate resin (PBT), liquid crystal polyester Resin (LCP), polyacetal resin (POM), polyamide resin (PA), polycarbonate resin, polyurethane resin, polyphenylene sulfide resin (PPS), and the like. It is used as a polymer blend or polymer alloy. These resins are also used as thermoplastic molding materials in which natural resins contain fillers such as glass fibers, carbon fibers, semi-carbonized fibers, cellulosic fibers, glass beads, flame retardants, and the like. Moreover, conventionally used additives for resins, for example, polyolefin resin fine powder, polyolefin wax, ethylene bisamide wax, metal soap, etc. can be used alone or in combination as required.

  Examples of the thermosetting resin include epoxy resins, melamine resins, unsaturated polyester resins, and the like. These include natural resins, glass fibers, carbon fibers, semi-carbonized fibers, cellulosic fibers, glass beads, and the like. It can also be used as a thermosetting molding material containing a flame retardant.

  In the dispersion containing the ultraviolet absorbent according to the present invention, a dispersant, an antifoaming agent, a preservative, an antifreezing agent, a surfactant and the like can be used in combination. In addition, any compound may be included. Examples thereof include dyes, pigments, infrared absorbers, fragrances, polymerizable compounds, polymers, inorganic substances, metals, and the like.

  As a device for obtaining a dispersion containing the ultraviolet absorbent according to the present invention, a high-speed stirring disperser having a large shearing force, a disperser giving high-intensity ultrasonic energy, or the like can be used. Specifically, there are a colloid mill, a homogenizer, a capillary emulsifying device, a liquid siren, an electromagnetic distortion ultrasonic generator, an emulsifying device having a Paulman whistle, and the like. A high-speed stirring type disperser preferable for use in the present invention is a high-speed rotation (500 to 15,000 rpm) in a liquid in which a main part that performs a dispersing action, such as a dissolver, polytron, homomixer, homoblender, caddy mill, jet agitator. Preferably, it is a disperser of the type of 2,000 to 4,000 rpm. The high-speed agitation type disperser used in the present invention is also called a dissolver or a high-speed impeller disperser. As described in Japanese Patent Application Laid-Open No. 55-129136, a saw-tooth plate is attached to a shaft that rotates at high speed. A preferred example is one in which impellers that are alternately bent in the vertical direction are mounted.

  In preparing an emulsified dispersion comprising a hydrophobic compound, various processes can be followed. For example, when a hydrophobic compound is dissolved in an organic solvent, one kind arbitrarily selected from a high-boiling organic substance, a water-immiscible low-boiling organic solvent, or a water-miscible organic solvent, or two or more kinds of arbitrary substances Dissolve in the multi-component mixture and then disperse in water or aqueous hydrophilic colloid in the presence of a surface active compound. The mixing method of the water-insoluble phase containing the hydrophobic compound and the aqueous phase may be a so-called forward mixing method in which the water-insoluble phase is added to the aqueous phase with stirring or a reverse mixing method.

Moreover, the ultraviolet absorber of this invention can be used in the state of the solution melt | dissolved in the liquid medium. Hereinafter, the ultraviolet absorbent solution containing the ultraviolet absorbent of the present invention will be described.
Any liquid may be used for dissolving the ultraviolet absorbent according to the present invention. For example, water, an organic solvent, a resin, a resin solution, and the like can be given. Examples of the organic solvent, the resin, and the resin solution include those described as the above dispersion medium. These may be used alone or in combination.

  The solution of the ultraviolet absorber of the present invention may contain any other compound in addition. Examples thereof include dyes, pigments, infrared absorbers, fragrances, polymerizable compounds, polymers, inorganic substances, metals, and the like. Except for the ultraviolet absorbent according to the present invention, it may not necessarily be dissolved.

  The content of the ultraviolet absorber in the solution containing the ultraviolet absorber of the present invention varies depending on the purpose of use and the form of use and cannot be uniquely determined, but may be any concentration depending on the purpose of use. Preferably it is 0.001-30 mass% with respect to the whole quantity of a solution, More preferably, it is 0.01-10 mass%. It is also possible to prepare a solution at a high concentration in advance and dilute it when desired. The dilution solvent can be arbitrarily selected from the above-mentioned solvents.

The polymer composition is used for the preparation of the polymer material containing the ultraviolet absorber of the present invention. The polymer composition used in the present invention is obtained by adding the ultraviolet absorber of the present invention to a polymer material described later.
The ultraviolet absorber of the present invention can be contained in the polymer substance by various methods. When the ultraviolet absorbent of the present invention is compatible with the polymer substance, the ultraviolet absorbent of the present invention can be directly added to the polymer substance. The ultraviolet absorber of the present invention may be dissolved in an auxiliary solvent having compatibility with the polymer material, and the solution may be added to the polymer material. The ultraviolet absorbent of the present invention may be dispersed in a high-boiling organic solvent or polymer, and the dispersion may be added to the polymer substance.

The boiling point of the high-boiling organic solvent is preferably 180 ° C. or higher, and more preferably 200 ° C. or higher. The melting point of the high-boiling organic solvent is preferably 150 ° C. or lower, and more preferably 100 ° C. or lower. Examples of the high boiling point organic solvent include phosphate ester, phosphonate ester, benzoate ester, phthalate ester, fatty acid ester, carbonate ester, amide, ether, halogenated hydrocarbon, alcohol and paraffin. Phosphate esters, phosphonate esters, phthalate esters, benzoate esters and fatty acid esters are preferred.
As for the method of adding the ultraviolet absorber of the present invention, JP-A-58-209735, JP-A-63-264748, JP-A-4-191185, JP-A-8-272058, and British Patent No. 2011017A. Can be helpful.

  The content of the ultraviolet absorber in the solution containing the ultraviolet absorber of the present invention varies depending on the purpose of use and the form of use and cannot be uniquely determined, but may be any concentration depending on the purpose of use. Preferably it is 0.001-10 mass% in a polymeric material, More preferably, it is 0.01-5 mass%.

Moreover, the ultraviolet absorber of the present invention is preferably used for a polymer material. Hereinafter, the polymer material of the present invention will be described.
In the present invention, a sufficient ultraviolet shielding effect can be obtained practically only with the ultraviolet absorber of the present invention, but when more strictness is required, a white pigment having a strong hiding power, such as titanium oxide, is used in combination. Also good. In addition, when the appearance and color tone become problems, or a small amount (0.05% by mass or less) of a colorant can be used in combination depending on the preference. For applications where transparency or white color is important, a fluorescent brightening agent may be used in combination. As the fluorescent brightening agent, in addition to the compound represented by any one of the above general formulas (1) to (5), a commercially available product, the general formula [1] described in JP-A No. 2002-53824, or a specific compound Examples 1-35 etc. are mentioned.

  Subsequently, the polymer substance used in the present invention will be described. The polymer substance may be either a natural or synthetic polymer. Polyolefins (eg, polyethylene, polypropylene, polyisobutylene, poly (1-butene), poly-4-methylpentene, polyvinylcyclohexane, polystyrene, poly (p-methylstyrene), poly (α-methylstyrene), polyisoprene, polybutadiene, Polycyclopentene, polynorbornene, etc.), copolymers of vinyl monomers (eg, ethylene / propylene copolymers, ethylene / methylpentene copolymers, ethylene / heptene copolymers, ethylene / vinylcyclohexane copolymers, ethylene / cycloolefin copolymers (eg, ethylene / norbornene) Such as cycloolefin copolymer (COC), propylene / butadiene copolymer, isobutylene / isoprene copolymer, Ethylene / vinylcyclohexene copolymer, ethylene / alkyl acrylate copolymer, ethylene / alkyl methacrylate copolymer, etc.), acrylic polymer (eg, polymethacrylate, polyacrylate, polyacrylamide, polyacrylonitrile, etc.), polyvinyl chloride, polyvinylidene chloride, polyfluoride Vinyl, polyvinylidene fluoride, vinyl chloride / vinyl acetate copolymer, polyether (eg, polyalkylene glycol, polyethylene oxide, polypropylene oxide, etc.), polyacetal (eg, polyoxymethylene), polyamide, polyimide, polyurethane, polyurea, polyester ( For example, polyethylene terephthalate, polyethylene naphthalate, etc.), polycarbonate, polyketone, polyethylene Sulfone polyether ketone, phenol resin, melamine resin, cellulose ester (eg, diacetyl cellulose, triacetyl cellulose (TAC), propionyl cellulose, butyryl cellulose, acetyl propionyl cellulose, nitrocellulose), polysiloxane, natural polymer (eg, cellulose) , Rubber, gelatin, etc.).

The polymer substance used in the present invention is preferably a synthetic polymer, more preferably a polyolefin, an acrylic polymer, polyester, polycarbonate, or cellulose ester. Among these, polyethylene, polypropylene, poly (4-methylpentene), polymethyl methacrylate, polycarbonate, polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, and triacetyl cellulose are particularly preferable.
The polymer substance used in the present invention is preferably a thermoplastic resin.

  The polymer material containing the ultraviolet absorbent according to the present invention includes an antioxidant, a light stabilizer, a processing stabilizer, an anti-aging agent, a compatibilizing agent, etc., if necessary, in addition to the above-described polymer substance and ultraviolet absorbent. Any additive may be appropriately contained.

The compounds according to the invention are particularly suitable for stabilizing organic materials against damage by light, oxygen or heat. Among them, the compound of the present invention is most suitable for use as a light stabilizer, particularly an ultraviolet absorber. Hereafter, the use as a ultraviolet absorber of the compound of this invention is demonstrated.
What is stabilized by the ultraviolet absorber of the present invention includes dyes, pigments, foods, beverages, body care products, vitamins, pharmaceuticals, inks, oils, fats, waxes, surface coatings, cosmetics, photographic materials, textiles and the like Examples include pigments, plastic materials, rubber, paints, polymer materials, polymer additives, and the like.
When the ultraviolet absorbent according to the present invention is used, the mode thereof may be any method. Although the ultraviolet absorber of the present invention may be used alone or as a composition, it is preferably used as a composition. Especially, it is preferable that it is a polymeric material containing the ultraviolet absorber of this invention. Hereinafter, the polymer material containing the ultraviolet absorbent according to the present invention will be described.

The polymer material containing the ultraviolet absorbent according to the present invention uses the polymer material. The polymer material containing the ultraviolet absorbent according to the present invention may be formed only from the polymer substance, or may be formed by dissolving the polymer substance in an arbitrary solvent.
The polymer material containing the ultraviolet absorbent according to the present invention can be used for all applications in which a synthetic resin is used, but can be particularly suitably used for applications that may be exposed to sunlight or light including ultraviolet rays. . Specific examples include, for example, glass substitutes and surface coating materials thereof, housing, facilities, window glass for transportation equipment, coating materials for daylighting glass and light source protection glass, housing, facilities, window films for transportation equipment, housing, Inner and outer coating materials for interior and exterior facilities and transportation equipment, coating films formed by the coating, alkyd resin lacquer coating and coating formed by the coating, acrylic lacquer coating and coating formed by the coating, Components for light sources that emit ultraviolet rays such as fluorescent lamps and mercury lamps, precision machinery, components for electronic and electrical equipment, materials for shielding electromagnetic waves generated from various displays, containers or packaging materials for food, chemicals, chemicals, bottles, boxes, Blister, cup, special packaging, compact disc coat, agricultural or industrial sheet or film material, printed matter, dyed matter, dyeing Anti-fading agents such as coating materials, protective films for polymer supports (eg for plastic parts such as machinery and automotive parts), printed overcoats, inkjet media coatings, laminated matte, optical light films, safety glass / front Glass interlayers, electrochromic / photochromic applications, overlaminate films, solar thermal control films, sunscreen creams, shampoos, rinses, hairdressing cosmetics, sportswear, stockings, hats and other clothing textiles and fibers, curtains, carpets Interior products for home use such as wallpaper, plastic lenses, contact lenses, medical devices such as artificial eyes, optical filters, backlight display films, prisms, mirrors, optical materials such as photographic materials, mold films, transfer stickers, graffiti Statements such as prevention film, tape, ink Examples include a utensil, a sign plate, a sign device, and a surface coating material thereof.

  Examples of the shape of the polymer material containing the ultraviolet absorbent according to the present invention include a film shape, a powder shape, a spherical particle, a crushed particle, a massive continuous body, a fiber shape, a tubular shape, a hollow fiber shape, a granular shape, a plate shape, and a porous shape. Any shape may be sufficient.

  Since the polymer material containing the ultraviolet absorber of the present invention contains the ultraviolet absorber of the present invention, it has excellent light resistance (fastness to ultraviolet light), and precipitation of the ultraviolet absorber and long-term use No bleed out occurs. In addition, since the polymer material of the present invention has an excellent long-wave ultraviolet absorbing ability, it can be used as an ultraviolet absorbing filter or a container, and can protect compounds that are sensitive to ultraviolet rays. For example, a molded product (such as a container) made of the polymer material of the present invention can be obtained by molding the polymer substance by any method such as extrusion molding or injection molding. In addition, a molded article coated with the ultraviolet absorbing film made of the polymer material of the present invention can be obtained by applying and drying the polymer substance solution to a separately produced molded article.

  When the polymer material containing the ultraviolet absorber of the present invention is used as an ultraviolet absorption filter or an ultraviolet absorption film, the polymer substance is preferably transparent. Examples of transparent polymer materials include cellulose esters (eg, diacetylcellulose, triacetylcellulose (TAC), propionylcellulose, butyrylcellulose, acetylpropionylcellulose, nitrocellulose), polyamides, polycarbonates, polyesters (eg, polyethylene terephthalate, Polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4′-dicarboxylate, polybutylene terephthalate), polystyrene (eg, syndiotactic) Polystyrene), polyolefin (eg, polyethylene, polypropylene, polymethylpentene), polymethyl methacrylate, syndiotactic polystyrene Emissions, polysulfone, polyether sulfone, polyether ketone, polyether imides, polyoxyethylene, and the like. Preferred are cellulose ester, polycarbonate, polyester, polyolefin, and acrylic resin, and more preferred are polycarbonate and polyester. Further preferred is polyester, and particularly preferred is polyethylene terephthalate. The polymer material containing the ultraviolet absorber of the present invention can also be used as a transparent support, and the transmittance of the transparent support is preferably 80% or more, and more preferably 86% or more.

  In the present invention, two or more compounds represented by any one of the general formulas (1) to (5) having different structures may be used in combination, or any one of the general formulas (1) to (5). A compound represented by the above formula and one or more ultraviolet absorbers having other structures may be used in combination. When two types (preferably three types) of ultraviolet absorbers are used in combination, ultraviolet rays in a wide wavelength region can be absorbed. In addition, when two or more kinds of ultraviolet absorbers are used in combination, the dispersion state of the ultraviolet absorber is also stabilized. Any ultraviolet absorber having a structure other than one of the general formulas (1) to (5) can be used. Examples of the structure of the ultraviolet absorber include triazine, benzotriazole, benzophenone, merocyanine, cyanine, dibenzoylmethane, cinnamic acid, cyanoacrylate, and benzoate. For example, Fine Chemical, May 2004 issue, pages 28-38, published by Toray Research Center, Research Division, “New Development of Functional Additives for Polymers” (Toray Research Center, 1999), pages 96-140, Junichi Okachi Examples include ultraviolet absorbers described in the supervision of “Development of polymer additives and environmental measures” (CMC Publishing Co., Ltd., 2003), pages 54 to 64.

  Preferably, the ultraviolet absorber having a structure other than any one of the general formulas (1) to (5) is a benzotriazole, benzophenone, salicylic acid, cyanoacrylate, or triazine compound. More preferred are benzotriazole, benzophenone and triazine compounds. Particularly preferred are benzotriazole compounds.

  The effective absorption wavelength of the benzotriazole compound is about 270 to 380 nm, and representative examples include 2- (2′-hydroxy-5′-methylphenyl) benzotriazole and 2- (2′-hydroxy-5′-t-butyl). Phenyl) benzotriazole, 2- (2′-hydroxy-3′-t-butyl-5′-methylphenyl) -5-chlorobenzotriazole, 2- (2′-hydroxy-3 ′, 5′-di-t) -Butylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-3'-t-butyl-5 '-(2- (octyloxycarbonyl) ethyl) phenyl) -5-chlorobenzotriazole, 2- (2′-hydroxy-3′-dodecyl-5′-methylphenyl) -5-chlorobenzotriazole, 2- (2′-hydroxy-3 ′, 5′- -T-amylphenyl) benzotriazole, 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole, 2- (2'-hydroxy-3 ', 5'-di- (dimethylbenzyl) phenyl) Benzotriazole, 2- (2′-hydroxy-4′-octyloxyphenyl) benzotriazole, 2,2′-methylene-bis (2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole) 2 -(2'-hydroxy-3 '-(3,4,5,6-tetrahydrophthalimidylmethyl) -5'-methylbenzyl) phenyl) benzotriazole and the like.

  The effective absorption wavelength of the benzophenone compound is about 270 to 380 nm, and representative examples include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octyloxybenzophenone, 2-hydroxy-4- Dodecyloxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone, 2-hydroxy-4- (2-hydroxy-3-methacryloxypropoxy) benzophenone, 2-hydroxy-4-methoxy-5-sulfobenzophenone, 2-hydroxy- 4-methoxy-5-sulfobenzophenone trihydrate, 2-hydroxy-4-methoxy-2'-carboxybenzophenone, 2-hydroxy-4-octadecyloxybenzophenone, 2-hydroxy-4-diethylamino 2′-hexyloxycarbonylbenzophenone, 2,2′-dihydroxy-4-methoxybenzophenone, 2,2 ′, 4,4′-tetrahydroxybenzophenone, 2,2′-dihydroxy-4,4′-dimethoxybenzophenone, 1 , 4-bis (4-benzyloxy-3-hydroxyphenoxy) butane and the like.

  The effective absorption wavelength of the salicylic acid compound is about 290 to 330 nm, and representative examples include phenyl salicylate, pt-butylphenyl salicylate, p-octylphenyl salicylate, and the like.

  The effective absorption wavelength of the cyanoacrylate compound is about 270 to 350 nm, and representative examples include 2-ethylhexyl 2-cyano-3, 3-diphenyl acrylate, ethyl 2-cyano-3, 3-diphenyl acrylate, hexadecyl 2-cyano- 3- (4-methylphenyl) acrylate, 2-cyano-3- (4-methylphenyl) acrylate, 1,3-bis (2′-cyano-3,3′-diphenylacryloyl) oxy) -2, And 2-bis (((2′-cyano-3,3′-diphenylacryloyl) oxy) methyl) propane.

  The effective absorption wavelength of the triazine compound is about 270 to 380 nm, and representative examples include 2- (4-hexyloxy-2-hydroxyphenyl) -4,6-diphenyl-1,3,5-triazine, 2- (4- Octyloxy-2-hydroxyphenyl) -4,6-di (2,5-dimethylphenyl) -1,3,5-triazine, 2- (4-butoxy-2-hydroxyphenyl) -4,6-di (4 -Butoxyphenyl) -1,3,5-triazine, 2- (4-butoxy-2-hydroxyphenyl) -4,6-di (2,4-dibutoxyphenyl) -1,3,5-triazine, 2 -(4- (3- (2-ethylhexyloxy) -2-hydroxypropoxy) -2-hydroxyphenyl) -4,6-di (2,4-dimethylphenyl) -1,3,5-triazine, 2 − ( -(3-dodecyloxy-2-hydroxypropoxy) -2-hydroxyphenyl) -4,6-di (2,4-dimethylphenyl) -1,3,5-triazine, 2,4-di (4-butoxy- 2-hydroxyphenyl) -6- (4-butoxyphenyl) -1,3,5-triazine, 2,4-di (4-butoxy-2-hydroxyphenyl) -6- (2,4-dibutoxyphenyl) -1,3,5-triazine and the like.

  Moreover, the compound represented by any one of the general formulas (1) to (5) can be suitably used as a fluorescent brightening agent. In general, the optical brightener comprises a compound having the property of absorbing light having a wavelength of about 320 to about 410 nm and emitting light having a wavelength of about 410 to about 500 nm. In addition to the original yellow reflected light, the fabric dyed with these fluorescent whitening agents is added with blue light having a wavelength of about 410 to about 500 nm, which is newly emitted by the fluorescent whitening agent, so that the reflected light is white. And the energy of visible light is increased by the amount due to the fluorescence effect, resulting in whitening.

  Hereinafter, the fluorescent whitening agent comprising the compound represented by any one of the general formulas (1) to (5) will be described. Any use form of the optical brightener of the present invention may be used. For example, a liquid dispersion, a solution, a polymer material, and the like can be given.

  The optical brightener of the present invention can be used in the state of a dispersion dispersed in a dispersion medium. The dispersion medium of the dispersion containing the optical brightener of the present invention, the adjustment process, the content of the optical brightener and the dispersing apparatus are the same as those of the above-described ultraviolet absorber.

  The fluorescent brightener of the present invention can be used in the state of a solution dissolved in a liquid medium. The addition method, content, and solution of the fluorescent whitening agent in the solution containing the fluorescent whitening agent of the present invention are the same as those of the above-described ultraviolet absorber.

  Moreover, the optical brightener of the present invention is preferably used for a polymer material. The polymer material, additive, shape, and use of the polymer material containing the fluorescent brightener of the present invention are the same as those of the above-described ultraviolet absorber.

When the short wavelength region cannot be sufficiently cut with the fluorescent brightener of the present invention alone, it is preferable to use an ultraviolet absorber in combination.
Any ultraviolet absorber can be used in combination. As an example, the ultraviolet absorber represented by either of the said general formula (1)-(5) and the example of the above-mentioned ultraviolet absorber can be mentioned. These ultraviolet absorbers can be used alone or in combination of two or more.

  The present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.

Example 1
(Preparation of exemplary compound (8))
20.0 g of 2-amino-5- (N-methylsulfamoyl) benzoic acid was dissolved in 60 ml of N, N-dimethylacetamide, and 12.2 g of benzoyl chloride was added dropwise to the solution under ice cooling at room temperature. The reaction was performed for 2 hours. 40 ml of acetic anhydride was added to the mixture and reacted for 2 hours under reflux. After cooling to room temperature, 25.8 g of Exemplified Compound (8) was obtained by filtration and washing with acetone (yield 94%).

Example 2
(Preparation of Exemplified Compound (10))
20.0 g of 2-amino-5- (methoxysulfonyl) benzoic acid is dissolved in 60 ml of N, N-dimethylacetamide, and 12.2 g of benzoyl chloride is added dropwise to the solution under ice-cooling and reacted at room temperature for 2 hours. It was. 40 ml of acetic anhydride was added to the mixture and reacted for 2 hours under reflux. After cooling to room temperature, 26.1 g of Exemplified Compound (10) was obtained by filtration and washing with acetone (yield 95%).

Example 3
(Preparation of Exemplified Compound (12))
20.0 g of 2-amino-5- (2-ethylhexylthio) benzoic acid was dissolved in 60 ml of N, N-dimethylacetamide, 10.0 g of benzoyl chloride was added dropwise to the solution under ice cooling, and the mixture was stirred at room temperature for 2 hours. Reacted. 40 ml of acetic anhydride was added to the mixture and reacted for 2 hours under reflux. After cooling to room temperature, 24.8 g of Exemplified Compound (12) was obtained by filtration and washing with acetone (yield 95%).

Example 4
(Preparation of Exemplified Compound (23))
20.0 g of 2-amino-5- [N, N-bis (2-ethylhexyl) sulfamoyl] benzoic acid was dissolved in 60 ml of N, N-dimethylacetamide, and 8.7 g of 2-naphthoyl chloride was added to ice. The solution was added dropwise under cooling and reacted at room temperature for 2 hours. 40 ml of acetic anhydride was added to the mixture and reacted for 2 hours under reflux. After cooling to room temperature, 24.4 g of Exemplified Compound (23) was obtained by filtration and washing with acetone (yield 93%).

Example 5
(Preparation of exemplary compound (32))
20.0 g of 2-amino-5- [N, N-bis (2-ethylhexyl) sulfamoyl] benzoic acid was dissolved in 60 ml of N, N-dimethylacetamide, and 6.7 g of 2-thenoyl chloride was added to ice. The solution was added dropwise under cooling and reacted at room temperature for 2 hours. 40 ml of acetic anhydride was added to the mixture and reacted for 2 hours under reflux. After cooling to room temperature, 22.7 g of Exemplified Compound (32) was obtained by filtration and washing with acetone (yield 94%).

<Preparation of sample solution and light resistance evaluation>
1 mg of Exemplified Compound (8) was dissolved in 100 ml of ethyl acetate to prepare a sample solution. Similarly, sample solutions were prepared for the exemplified compound (10), the exemplified compound (12), the exemplified compound (23), the exemplified compound (32), and the comparative compounds A and B. The absorbance of each sample solution was measured in a 1 cm quartz cell using a spectrophotometer UV-3600 (trade name) manufactured by Shimadzu Corporation. The cell in which this sample solution was sealed was irradiated with a xenon lamp from which the UV filter had been removed so that the illuminance was 170,000 lux, and the residual amount of each compound after irradiation for 2 days was measured. The remaining amount was calculated according to the following formula.
Residual amount (%) = 100 × (100−transmittance after irradiation) / (100−transmittance before irradiation)
The transmittance is a value measured at the maximum absorption wavelength of each compound. The results are shown in Table 1.

  As is clear from the results in Table 1, the compound of the present invention was compared with the comparative compounds A and B (existing ultraviolet absorbers having absorption in the UV-A region) due to the steric effect of the substituent. It was found that the residual ratio was high and it was difficult to decompose by light irradiation.

<Film creation and light resistance evaluation>
10 g of polyethylene terephthalate pellets having an intrinsic viscosity of 0.78 dried at 170 ° C. for 6 hours and 1 g of Exemplified Compound (8) were mixed and charged into an extruder. After melt-kneading at a melting temperature of 280 ° C., a film was formed to obtain a film having a thickness of 100 μm. Similarly, a film was prepared using Exemplified Compound (10), Exemplified Compound (12), Exemplified Compound (23), Exemplified Compound (32), and Comparative Compounds A and B. About each produced film, when it irradiated with light so that it might become an illuminance of 170,000 lux with a xenon lamp, and the surface shape of each film after 1000 hours irradiation was confirmed, exemplary compound (8) of this invention, exemplary compound (10 ), The compound containing Exemplified Compound (12), Exemplified Compound (23), or Exemplified Compound (32) had no bleed out and had a good surface shape, but the film containing Comparative Compound A or B bleeded out. It was white and dirty.

Claims (10)

An aromatic compound represented by the following general formula (1).

[Wherein Ar ¹ represents a monovalent 5- to 20-membered aromatic residue. The aromatic residue may contain a hetero atom and may have a substituent.
X ^1a and X ^1b each independently represent a hetero atom. X ^1a and X ^1b may have a substituent.
Y ¹ represents a —SR ^1a group or a —SO ₂ R ^1b group. R ^1a represents a hydrogen atom or a monovalent substituent excluding the —Me group and the —CN group. R ^1b represents a hydrogen atom or a monovalent substituent excluding the -Me group.
n ¹ represents an integer of 1 to 4.
The ring bonded to Ar ¹ may have a double bond at an arbitrary position. ] The aromatic compound according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2).

[Wherein Ar ² has the same meaning as Ar ^{1 in} formula (1).
Y ² has the same meaning as Y ^{1 in the} general formula (1).
n ² has the same meaning as n ^{1 in the} general formula (1). ] The aromatic compound according to claim 2, wherein the compound represented by the general formula (2) is a compound represented by the following general formula (3).

[Wherein Ar ³ has the same meaning as Ar ^{2 in} formula (2).
Y ³ has the same meaning as Y ^{2 in the} general formula (2). ] The aromatic compound according to claim 3, wherein the compound represented by the general formula (3) is a compound represented by the following general formula (4).

[Wherein Y ⁴ has the same meaning as Y ^{3 in} formula (3). ] The aromatic compound according to claim 4, wherein the compound represented by the general formula (4) is a compound represented by the following general formula (5).

[Wherein Y ⁵ represents a —SR ^5a group or a —SO ₂ R ^5b group. R ^5a represents an alkyl group having 2 to 10 carbon atoms. R ^5b represents a substituted or unsubstituted amino group. ]   The ultraviolet absorber which consists of an aromatic compound of any one of Claims 1-5.   A fluorescent whitening agent comprising the aromatic compound according to any one of claims 1 to 5.   A dispersion comprising the ultraviolet absorber according to claim 6 and / or the optical brightener according to claim 7.   A solution containing the ultraviolet absorber according to claim 6 and / or the fluorescent brightener according to claim 7.   A polymer material comprising the ultraviolet absorber according to claim 6 and / or the fluorescent brightener according to claim 7.