WO2025057289A1 - Novel triazine derivative and salt thereof, and ultraviolet absorbent, external skin agent, and coating composition using same - Google Patents

Abstract

The present invention relates to providing a novel compound, specifically a 1,3,5-triazine derivative and salt thereof, which has a suitable ultraviolet absorption action, and to an ultraviolet absorbent and external skin agent using the same.　The present invention is the 1,3,5-triazine derivative or salt thereof represented by general formula (I), etc. (In the general formula, G¹, G², and G³ each independently represent hydrogen, a straight or branched chain alkyl group, etc. having 1-12 carbon atoms which may be substituted, or -X-Z-Y. However, at least two of G¹, G², and G³ may be -X-Z-Y, which may be identical or different from each other.　X is O, N, or S.　Y is a sulfonic acid group, a hydroxyl group, or a carboxyl group, etc., or a group corresponding to a salt thereof.　Z is a straight or branched chain alkyl group, etc. having 1-8 carbon atoms.　R¹, R², and R³ each independently represent a straight or branched chain alkyl group, etc. having 1-4 carbon atoms, and l, m, and n each independently represent an integer from 0 to 4.)

Description

Novel triazine derivative and its salt, and ultraviolet absorbent, skin topical preparation, and coating composition using the same

The present invention relates to novel hydrophilic triazine derivatives and salts thereof that have ultraviolet absorbing properties, as well as ultraviolet absorbents, topical skin preparations, and coating compositions that use the same.

Ultraviolet rays are essential for the synthesis of vitamin D, and are used to promote blood circulation and metabolism in the body, as well as for sterilization and disinfection. On the other hand, excessive exposure of the skin to ultraviolet rays can lead to the development of skin cancer, accelerate skin aging, and cause spots, freckles, wrinkles, etc. Furthermore, when various synthetic resins and paints such as polyethylene, polypropylene, PVC, and ABS resin are exposed to excessive ultraviolet rays, they can cause the synthetic resins and paints to deteriorate. Thus, exposure to excessive amounts of ultraviolet rays can cause various adverse effects. To prevent such adverse effects, various ultraviolet absorbers have been developed and are widely used.

Near-ultraviolet rays, commonly known as "ultraviolet rays (UV)," can be broadly divided into UVA (wavelength 315-400 nm), UVB (wavelength 280-315 nm), and UVC (wavelength 200-280 nm) based on their wavelength. Note that UVC is UV that originates from sunlight, but is significantly absorbed by the ozone layer and other elements before it reaches the earth, so it is usually unable to pass through the ozone layer and reach the earth.

　UVA and UVB are believed to be the main causes of skin cancer, skin aging, and the deterioration of synthetic resins and paints. For this reason, ultraviolet absorbers have been developed primarily for the purpose of absorbing UVA or UVB.

As the effects of UV rays on the skin and other skin conditions become clearer, there is an increasing demand for sunscreen cosmetics that have a high UV blocking effect. Generally, UV scattering agents and UV absorbing agents are used in sunscreen cosmetics to block UV rays from reaching the skin.

UV scattering agents block UV rays by scattering them, and inorganic pigments such as zinc oxide, titanium oxide, kaolin, and calcium carbonate have traditionally been used. These can block UV rays over a wide range, and because they are inactive, they are also highly safe for the skin, making them a more useful UV blocking agent.

However, although these inorganic pigments, particularly titanium oxide and zinc oxide, have a high UV shielding effect as mentioned above, they also have a high covering power (concealing power), which causes the cosmetic film to turn white when applied to the skin, resulting in a white cast. For this reason, the use of finely divided titanium oxide and zinc oxide has been proposed (see, for example, Patent Documents 1 to 3). It is known that the finer the particles, the higher the UV shielding effect and the higher the light transmittance in the visible light range, resulting in higher transparency.

Furthermore, these inorganic pigment fine particles generally have a high tendency to aggregate, making it difficult to stably disperse them in a fine particle state in cosmetic formulations and other formulations. As a result, the expected UV shielding effect and transparency are not achieved. Furthermore, because these fine particle pigments have a high refractive index, using large amounts of them increases the hiding power, resulting in a whitish cast and an unnatural cosmetic finish. Furthermore, particle aggregation hinders the spreadability of the cosmetic and causes problems in use, such as a squeaky feeling when applied to the skin. For this reason, the amount of these UV scattering agents that can be used is naturally limited, and cosmetics with the desired UV shielding effect have not been obtained.

Special Publication No. 47-42502 Japanese Unexamined Patent Publication No. 49-00450 Japanese Unexamined Patent Publication No. 64-07941

In light of these circumstances, the present invention aims to provide 1,3,5-triazine derivatives and salts thereof, which are novel compounds that have favorable ultraviolet absorbing properties.

The present invention also aims to provide an ultraviolet absorber, a skin topical preparation, and a coating composition that contain the above-mentioned 1,3,5-triazine derivative and its salt and have a suitable ultraviolet absorbing effect.

As a result of intensive research to solve the above problems, the inventors have succeeded in creating the novel triazine derivatives and salts thereof shown below, and have found that the above objects can be achieved by using the above compounds, thus completing the present invention.

In other words, the present invention provides the compounds or salts thereof shown below (hereinafter, sometimes referred to as "compounds" or "compounds, etc.").

（一般式（Ｉ）～（ＩＶ）中、
　Ｇ^１、Ｇ^２、及び、Ｇ^３は、それぞれ独立して、水素、置換されていてもよい炭素数１～１２の直鎖もしくは分岐鎖のアルキル基、置換されていてもよい炭素数１～１２の直鎖もしくは分岐鎖のアルケニル基、置換されていてもよい炭素数１～１２の直鎖もしくは分岐鎖のアルキニル基、置換されていてもよい１～８個のエチレンオキシド単位を含むポリオキシエチレン基、置換されていてもよい１～８個のプロピレンオキシド単位を含むポリオキシプロピレン基、又は、－Ｘ－Ｚ－Ｙを表す（ここで、ＹはＺ上において１又は複数存在し、複数存在する場合（Ｚに結合するＹが複数個の場合）には、複数存在するＹは互いに同一であっても異なっていてもよい）。ただし、Ｇ^１、Ｇ^２、及び、Ｇ^３のうち、少なくとも２つは、互いに同一であっても異なっていてもよい－Ｘ－Ｚ－Ｙである。
　Ｘは、Ｏ、Ｎ、又は、Ｓである。
　Ｙは、スルホン酸基、水酸基、カルボキシル基、アミノ基、アルキルアミノ基、アンモニウム基、アルキルアンモニウム基、リン酸基、ホスホン酸基、又は、これらの塩にあたる基である。
　Ｚは、炭素数１～８の直鎖もしくは分岐鎖のアルキル基、炭素数１～８の直鎖もしくは分岐鎖のアルケニル基、炭素数１～８の直鎖もしくは分岐鎖のアルキニル基、１～４個のエチレンオキシド単位を含むポリオキシエチレン基、又は、１～４個のプロピレンオキシド単位を含むポリオキシプロピレン基である。
　Ｒ^１、Ｒ^２、及び、Ｒ^３は、それぞれ独立して、炭素数１～４の直鎖もしくは分岐鎖のアルキル基、又は、ヒドロキシル基で置換された炭素数１～４の直鎖もしくは分岐鎖のアルキル基を表し、ｌ、ｍ、及び、ｎは、それぞれ独立して、０～４の整数であり、ｌが２以上の場合には、複数存在するＲ^１は同一でも異なっていてもよく、ｍが２以上の場合には、複数存在するＲ^２は同一でも異なっていてもよく、ｎが２以上の場合には、複数存在するＲ^３は同一でも異なっていてもよい。） [1]
A 1,3,5-triazine derivative or a salt thereof represented by any one of general formulas (I) to (IV):

(In general formulas (I) to (IV),
G ¹ , G ² , and G ³ each independently represent hydrogen, an optionally substituted linear or branched alkyl group having 1 to 12 carbon atoms, an optionally substituted linear or branched alkenyl group having 1 to 12 carbon atoms, an optionally substituted linear or branched alkynyl group having 1 to 12 carbon atoms, an optionally substituted polyoxyethylene group containing 1 to 8 ethylene oxide units, an optionally substituted polyoxypropylene group containing 1 to 8 propylene oxide units, or -X-Z-Y (wherein one or more Ys are present on Z, and when more than one Y is present (when there are more than one Y bonded to Z), the multiple Ys may be the same or different from each other). However, at least two of G ¹ , G ² , and G ³ are -X-Z-Y, which may be the same or different from each other.
X is O, N or S.
Y is a sulfonic acid group, a hydroxyl group, a carboxyl group, an amino group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a salt thereof.
Z is a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkenyl group having 1 to 8 carbon atoms, a linear or branched alkynyl group having 1 to 8 carbon atoms, a polyoxyethylene group containing 1 to 4 ethylene oxide units, or a polyoxypropylene group containing 1 to 4 propylene oxide units.
R ¹ , R ² , and R ³ each independently represent a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkyl group having 1 to 4 carbon atoms substituted with a hydroxyl group; l, m, and n each independently represent an integer from 0 to 4; when l is 2 or more, multiple R ^1s may be the same or different; when m is 2 or more, multiple R ^2s may be the same or different; and when n is 2 or more, multiple R ^3s may be the same or different.

[2]
The 1,3,5-triazine derivative or a salt thereof according to [1], represented by general formula (I):

[3]
The 1,3,5-triazine derivative or a salt thereof according to [1], represented by general formula (IV):

[4]
The 1,3,5-triazine derivative or salt thereof according to [1], characterized in that in the above general formulas (I) to (IV), X is N and Y is a sulfonic acid group, a hydroxyl group, an amino group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a group corresponding to a salt thereof.

[5]
The 1,3,5-triazine derivative or salt thereof according to [2], characterized in that, in the above general formula (I), X is N and Y is a sulfonic acid group, a hydroxyl group, an amino group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a group corresponding to a salt thereof.

[6]
The 1,3,5-triazine derivative or salt thereof according to [1], wherein in the above general formulas (I) to (IV), at least one of Y's present on Z is a hydroxyl group, and Z is a linear or branched alkyl group having 3 to 8 carbon atoms, a linear or branched alkenyl group having 1 to 8 carbon atoms, a linear or branched alkynyl group having 1 to 8 carbon atoms, a polyoxyethylene group containing 2 to 4 ethylene oxide units, or a polyoxypropylene group containing 1 to 4 propylene oxide units.

[7]
The 1,3,5-triazine derivative or salt thereof according to [2], wherein in the above general formula (I), at least one of Y's present on Z is a hydroxyl group, and Z is a linear or branched alkyl group having 3 to 8 carbon atoms, a linear or branched alkenyl group having 1 to 8 carbon atoms, a linear or branched alkynyl group having 1 to 8 carbon atoms, a polyoxyethylene group containing 2 to 4 ethylene oxide units, or a polyoxypropylene group containing 1 to 4 propylene oxide units.

[8]
The 1,3,5-triazine derivative or salt thereof according to [1], wherein in the above general formulas (I) to (IV), Y is a sulfonic acid group, a hydroxyl group, a carboxyl group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a salt thereof.

[9]
The 1,3,5-triazine derivative or salt thereof according to [2], wherein in the above general formula (I), Y is a sulfonic acid group, a hydroxyl group, a carboxyl group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a salt thereof.

[10]
The 1,3,5-triazine derivative or a salt thereof according to [1], wherein in the above general formulas (I) to (IV), at least one of Y's present on Z is a group corresponding to a sodium salt, a potassium salt, or a triethanolamine salt.

[11]
The 1,3,5-triazine derivative or a salt thereof according to any one of [2], wherein in the above general formula (I), at least one of Y's present on Z is a group corresponding to a sodium salt, a potassium salt, or a triethanolamine salt.

[12]
The 1,3,5-triazine derivative or salt thereof according to [1], wherein in the above general formulae (I) to (IV), G ¹ , G ² and G ³ are all the same or different -XZY.

[13]
The 1,3,5-triazine derivative or salt thereof according to [2], wherein in the above general formula (I), G ¹ , G ² and G ³ are all the same or different -XZY.

[14]
The 1,3,5-triazine derivative or a salt thereof according to any one of [1] to [13], which is water-soluble.

The present invention also provides the ultraviolet absorbents listed below.

[15]
An ultraviolet absorber comprising the 1,3,5-triazine derivative or a salt thereof according to any one of [1] to [13].

The present invention also provides the following skin topical compositions:

[16]
A composition for external use on skin, comprising the 1,3,5-triazine derivative or a salt thereof according to any one of [1] to [13].

The present invention also provides the coating composition described below.

[17]
A coating composition comprising the 1,3,5-triazine derivative or a salt thereof according to any one of [1] to [13].

[18]
The coating composition according to [17], which is water-soluble.

[19]
The coating composition according to [17], further comprising water.

The present invention also provides the coating layer described below.

[20]
A coating layer formed using the coating composition according to [17].

The present invention also provides the following coated bodies.
[21]
A coated body comprising the coating layer according to [20].

The present invention also provides a method for producing a coating layer as described below.

[22]
A method for producing a coating layer, comprising a step of drying a solvent from the coating composition according to [17].

The 1,3,5-triazine derivative or its salt of the present invention is a novel compound that is hydrophilic and has excellent ultraviolet absorbing properties. It is possible to provide a 1,3,5-triazine derivative or its salt that has strong ultraviolet absorbing properties mainly in the range of 280 to 315 nm.

In addition, the ultraviolet absorbent, skin topical preparation, and coating composition of the present invention contain the above-mentioned novel 1,3,5-triazine derivative or its salt, and therefore have excellent hydrophilicity and ultraviolet absorbing properties, and are useful as an ultraviolet absorbent, skin topical preparation, and coating composition.

The following is a detailed explanation of an embodiment of the present invention.

（一般式（Ｉ）～（ＩＶ）中、
　Ｇ^１、Ｇ^２、及び、Ｇ^３は、それぞれ独立して、水素、置換されていてもよい炭素数１～１２の直鎖もしくは分岐鎖のアルキル基、置換されていてもよい炭素数１～１２の直鎖もしくは分岐鎖のアルケニル基、置換されていてもよい炭素数１～１２の直鎖もしくは分岐鎖のアルキニル基、置換されていてもよい１～８個のエチレンオキシド単位を含むポリオキシエチレン基、置換されていてもよい１～８個のプロピレンオキシド単位を含むポリオキシプロピレン基、又は、－Ｘ－Ｚ－Ｙを表す（ここで、ＹはＺ上において１又は複数存在し、複数存在する場合には、複数存在するＹは互いに同一であっても異なっていてもよい）。ただし、Ｇ^１、Ｇ^２、及び、Ｇ^３のうち、少なくとも２つは、互いに同一であっても異なっていてもよい－Ｘ－Ｚ－Ｙである。
　Ｘは、Ｏ、Ｎ、又は、Ｓである。
　Ｙは、スルホン酸基、水酸基、カルボキシル基、アミノ基、アルキルアミノ基、アンモニウム基、アルキルアンモニウム基、リン酸基、ホスホン酸基、又は、これらの塩にあたる基である。
　Ｚは、炭素数１～８の直鎖もしくは分岐鎖のアルキル基、炭素数１～８の直鎖もしくは分岐鎖のアルケニル基、炭素数１～８の直鎖もしくは分岐鎖のアルキニル基、１～４個のエチレンオキシド単位を含むポリオキシエチレン基、又は、１～４個のプロピレンオキシド単位を含むポリオキシプロピレン基である。
　Ｒ^１、Ｒ^２、及び、Ｒ^３は、それぞれ独立して、炭素数１～４の直鎖もしくは分岐鎖アルキル基、又は、ヒドロキシル基で置換された炭素数１～４の直鎖もしくは分岐鎖のアルキル基を表し、ｌ、ｍ、及び、ｎは、それぞれ独立して、０～４の整数であり、ｌが２以上の場合には、複数存在するＲ^１は同一でも異なっていてもよく、ｍが２以上の場合には、複数存在するＲ^２は同一でも異なっていてもよく、ｎが２以上の場合には、複数存在するＲ^３は同一でも異なっていてもよい。） [1,3,5-triazine derivative or its salt]
The 1,3,5-triazine derivative or a salt thereof of the present invention is characterized by being represented by any one of general formulas (I) to (IV).

(In general formulas (I) to (IV),
G ¹ , G ² , and G ³ each independently represent hydrogen, an optionally substituted linear or branched alkyl group having 1 to 12 carbon atoms, an optionally substituted linear or branched alkenyl group having 1 to 12 carbon atoms, an optionally substituted linear or branched alkynyl group having 1 to 12 carbon atoms, an optionally substituted polyoxyethylene group containing 1 to 8 ethylene oxide units, an optionally substituted polyoxypropylene group containing 1 to 8 propylene oxide units, or -X-Z-Y (wherein one or more Y's are present on Z, and when more than one Y's are present, the multiple Y's may be the same or different from each other). However, at least two of G ¹ , G ² , and G ³ are -X-Z-Y, which may be the same or different from each other.
X is O, N or S.
Y is a sulfonic acid group, a hydroxyl group, a carboxyl group, an amino group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a salt thereof.
Z is a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkenyl group having 1 to 8 carbon atoms, a linear or branched alkynyl group having 1 to 8 carbon atoms, a polyoxyethylene group containing 1 to 4 ethylene oxide units, or a polyoxypropylene group containing 1 to 4 propylene oxide units.
R ¹ , R ² , and R ³ each independently represent a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkyl group having 1 to 4 carbon atoms substituted with a hydroxyl group; l, m, and n each independently represent an integer from 0 to 4; when l is 2 or more, multiple R ^1s may be the same or different; when m is 2 or more, multiple R ^2s may be the same or different; and when n is 2 or more, multiple R ^3s may be the same or different.

As mentioned above, cosmetics etc. with the desired UV shielding effect have not been obtained to date, and the lipophilic UV absorbers used in conventional sunscreens etc. have the property of not coming off even when water comes into contact with the skin (lipophilicity), and basically required a dedicated cleanser to remove them from the skin. In recent years, as damage to the skin caused by UV rays has become clear, sunscreens have come to be used in daily life, and there is a demand for sunscreens to be easily washed off with water. Furthermore, as the amount of lipophilic compounds used increases, the impact on products such as solubility in cosmetics and stability, especially in water-based solvents, has become problematic.

In contrast, the 1,3,5-triazine derivatives (s-triazine derivatives) or salts thereof of the present invention have structures represented by the above general formulas (I) to (IV), and therefore have excellent water solubility, strong ultraviolet absorbing properties, and excellent ultraviolet absorbing properties.

In the above 1,3,5-triazine derivative or salt thereof, in the general formulas (I) to (IV), G ¹ , G ² , and G ³ each independently represent hydrogen, an optionally substituted linear or branched alkyl group having 1 to 12 carbon atoms, an optionally substituted linear or branched alkenyl group having 1 to 12 carbon atoms, an optionally substituted linear or branched alkynyl group having 1 to 12 carbon atoms, an optionally substituted polyoxyethylene group containing 1 to 8 ethylene oxide units, an optionally substituted polyoxypropylene group containing 1 to 8 propylene oxide units, or -X-Z-Y (wherein one or more Ys are present on Z, and when more than one Y is present, the multiple Ys may be the same or different from each other). However, at least two of G ¹ , G ² , and G ³ are -X-Z-Y, which may be the same or different from each other. By having the above configuration, it has excellent ultraviolet absorbing action and is more excellent in hydrophilicity.

Examples of the optionally substituted straight or branched alkyl group having 1 to 12 carbon atoms in G ¹ , G ² , and G ³ include a methyl group, an ethyl group, a 1-propyl group, a 1-methyl-1-ethyl group, a 1-butyl group, a 1-methyl-1-propyl group, a 1,1-dimethyl-1-ethyl group, a 2-methyl-1-propyl group, a 1-pentyl group, a 2-pentyl group, a 1-hexyl group, a 2-hexyl group, a 1-heptyl group, a 2-heptyl group, a 1-octyl group, a 2-octyl group, a 1-nonyl group, a 2-nonyl group, a 1-decyl group, a 2-decyl group, a 1-undecyl group, a 2-undecyl group, a 1-dodecyl group, a 2-dodecyl group, a 1-tridecyl group, a 2-tridecyl group, a 1-tetradecyl group, and a 2-tetradecyl group. From the viewpoint of being able to exert a higher absorbance (ultraviolet light absorbance per mass), the number of carbon atoms in the alkyl group is preferably an integer of 1 to 8, and more preferably an integer of 1 to 4.

Examples of the optionally substituted linear or branched alkenyl group having 1 to 12 carbon atoms in G ¹ , G ² , and G ³ include ethenyl (ethene), allyl (propene), 1-methyl-vinyl, 1-butenyl, 2-butenyl, 2-pentenyl, etc. From the viewpoint of exhibiting higher absorbance (ultraviolet light absorbance per mass), the number of carbon atoms in the alkenyl group is preferably an integer from 1 to 8, and more preferably an integer from 1 to 4.

Examples of the optionally substituted linear or branched alkynyl group having 1 to 12 carbon atoms in G ¹ , G ² , and G ³ include an ethynyl group, a propynyl group, a butynyl group, etc. From the viewpoint of being able to exhibit higher absorbance (ultraviolet light absorbance per mass), the number of carbon atoms in the alkynyl group is preferably an integer from 1 to 8, and more preferably an integer from 1 to 4.

Examples of the polyoxyethylene group containing 1 to 8 ethylene oxide units which may be substituted in G ¹ , G ² , and G ³ above include -(CH ₂ CH ₂ O) _p -H, -(CH ₂ CH ₂ O) _p -CH ₂ CH ₃ , -O-(CH ₂ CH ₂ O) _p -H, and O-(CH ₂ CH ₂ O) _p -CH ₂ CH _3. Here, p is an integer of 1 to 8. From the viewpoint of being able to exert a higher absorbance (ultraviolet light absorbance per mass), p is preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.

Examples of the polyoxypropylene group containing 1 to 8 propylene oxide units which may be substituted in G ¹ , G ² and G ³ above include -(CH(CH 3 )CH ₂ O) _q -H, -(CH(CH ₃ )CH ₂ O) _q -CH(CH ₃ )CH ₃ , -O-(CH(CH ₃ )CH ₂ O) _q -H, O-(CH(CH ₃ )CH ₂ O) _q -CH(CH ₃ )CH ₃ , -(CH ₂ CH(CH _{3 )} O) _q -H, -(CH ₂ CH(CH ₃ )O) _q -CH(CH ₃ )CH ₃ , -O-(CH ₂ CH(CH ₃ )O) _q -H, O-(CH ₂ CH(CH ₃ )O) _{q -H,} Examples include —CH(CH ₃ )CH ₃ , where q is an integer of 1 to 8. From the viewpoint of exhibiting higher absorbance (ultraviolet light absorbance per mass), q is preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.

In addition, at least two of G ¹ , G ² and G ³ are -XZY which may be the same or different.

In addition, G ¹ , G ² and G ³ may all be the same or different -XZY.

In the above -X-Z-Y, X is O, N, or S. In multiple -X-Z-Y chains, X may be the same or different.

In the above -X-Z-Y, Y is a sulfonic acid group, a hydroxyl group, a carboxyl group, an amino group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a salt thereof. In multiple -X-Z-Y chains, the Ys may be the same or different.

Furthermore, a plurality of Y's may be present on Z. Examples of the case where a plurality of Y's are present on Z include the case where two or three hydroxyl groups (or ^-O- groups or alkoxide terminal groups) are bonded (present) on the same Z chain, and the case where a hydroxyl group and a sulfonic acid group (or a sulfonate salt group) are bonded on the same Z chain.

More specifically, examples of Y include _-SO3H , ^-OH , -COOH, -NH2, _-NR4R5 , ^-PO3H _as well as alkyl phosphate groups, phosphonic acid groups, and salts thereof such as -OA, _-SO3A , ^-COOA , ^-NR6R7R8B , ^etc.

The above A is a counter cation, and examples of such cations include monovalent cations and divalent cations. Representative examples of A that can be used as appropriate include alkali metal salts such as sodium and potassium, and triethanolammonium cations.

The above B is a counter anion, and for example, a monovalent cation or a divalent cation can be used as appropriate. Representative examples of the above B include hydroxide ion and chloro anion.

In the above -NR ⁴ R ⁵ , R ⁴ and R ⁵ are, for example, hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms. When R ⁴ and R ⁵ are all hydrogen, they are amino groups, and otherwise they are alkylamino groups. Examples of the linear or branched alkyl group having 1 to 4 carbon atoms in R ⁴ and R ⁵ include a methyl group, an ethyl group, a 1-propyl group, a 1-methyl-1-ethyl group, a 1-butyl group, a 1-methyl-1-propyl group, a 1,1-dimethyl-1-ethyl group, and a 2-methyl-1-propyl group. From the viewpoint of being able to exhibit higher absorbance (ultraviolet light absorbance per mass), R ⁴ and R ⁵ are preferably hydrogen, or the number of carbon atoms of the alkyl group is preferably an integer of 1 to 3, and more preferably an integer of 1 to 2. R ⁴ and R ⁵ may be the same or different from each other.

In the above-mentioned -NR ⁶ R ⁷ R ⁸ B, R ⁶ , R ⁷ and R ⁸ are, for example, hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms. When R ⁶ , R ⁷ and R ⁸ are all hydrogen, it is an ammonium group, otherwise it is an alkylammonium group. Examples of the linear or branched alkyl group having 1 to 4 carbon atoms in R ⁶ , R ⁷ and R ⁸ include a methyl group, an ethyl group, a 1-propyl group, a 1-methyl-1-ethyl group, a 1-butyl group, a 1-methyl-1-propyl group, a 1,1-dimethyl-1-ethyl group and a 2-methyl-1-propyl group. From the viewpoint of being able to exert a higher absorbance (ultraviolet light absorbance per mass), R ⁶ , R ⁷ and R ⁸ are preferably hydrogen, or the number of carbon atoms of the alkyl group is an integer of 1 to 3, more preferably an integer of 1 to 2. R ⁶ , R ⁷ and R ⁸ may be the same or different.

In the above -X-Z-Y, Z is a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkenyl group having 1 to 8 carbon atoms, a linear or branched alkynyl group having 1 to 8 carbon atoms, a polyoxyethylene group containing 1 to 4 ethylene oxide units, or a polyoxypropylene group containing 1 to 4 propylene oxide units. In multiple -X-Z-Y chains, Z may be the same or different.

In the above Z, examples of the linear or branched alkyl group having 1 to 8 carbon atoms include methyl, ethyl, 1-propyl, 1-methyl-1-ethyl, 1-butyl, 1-methyl-1-propyl, 1,1-dimethyl-1-ethyl, 2-methyl-1-propyl, 1-pentyl, 2-pentyl, 1-hexyl, 2-hexyl, 1-heptyl, 2-heptyl, 1-octyl, and 2-octyl groups. From the viewpoint of exhibiting higher absorbance (ultraviolet light absorbance per mass), the number of carbon atoms in the alkyl group is preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.

Examples of the linear or branched alkenyl group having 1 to 8 carbon atoms in Z include ethenyl (ethene), allyl (propene), 1-methyl-vinyl, 1-butenyl, 2-butenyl, and 2-pentenyl groups. From the viewpoint of exhibiting higher absorbance (ultraviolet light absorbance per mass), the number of carbon atoms in the alkenyl group is preferably an integer from 1 to 4, and more preferably an integer from 1 to 3.

Examples of the linear or branched alkynyl group having 1 to 8 carbon atoms in Z include ethynyl, propynyl, and butynyl groups. From the viewpoint of being able to exhibit higher absorbance (ultraviolet light absorbance per mass), the number of carbon atoms in the alkynyl group is preferably an integer from 1 to 4, and more preferably an integer from 1 to 3.

Examples of the polyoxyethylene group containing 1 to 4 ethylene oxide units in Z include -( _CH2CH2O ) _p'- H, - _{( CH2CH2O} ) _{p'- CH2CH3} , -O-( _CH2CH2O ) _{p' -} H, O-( _{CH2CH2O ) p'} - _CH2CH3 , _etc. , where p' is an integer of 1 to 4. From _the viewpoint of being able to exert _a higher absorbance (ultraviolet light absorbance per mass), p' is preferably an integer of 1 to 3, and more preferably an integer of 1 or 2.

Examples of the polyoxypropylene group containing 1 to 4 propylene oxide units in Z above include, for example, -(CH( _CH3 ) _CH2O ) _q' -H, -(CH( _CH3 ) _CH2O ) _q' -CH( _CH3 ) _CH3 , -O-(CH( _CH3 ) _CH2O ) _q'- H, O-(CH( _CH3 ) _CH2O ) _q'- CH( _CH3 ) _CH3 , -( _CH2CH ( _CH3 )O) _q' -H, -( _CH2CH ( _CH3 )O) _q' -CH( _CH3 ) _CH3 , -O-( _CH2CH ( _CH3 )O) _q'- H, O-( _CH2CH ( _CH3 )O) _q' -CH( _CH3 )CH ₃ , etc. Here, q' is an integer of 1 to 4. From the viewpoint of exhibiting higher absorbance (ultraviolet light absorbance per mass), q' is preferably an integer of 1 to 3, and more preferably an integer of 1 or 2.

In the above G ¹ , G ² , and G ³ , R ¹ , R ² , and R ³ each independently represent a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkyl group having 1 to 4 carbon atoms substituted with a hydroxyl group, l, m, and n each independently represent an integer of 0 to 4, and when l is 2 or more, multiple R ^1s may be the same or different, when m is 2 or more, multiple R ^2s may be the same or different, and when n is 2 or more, multiple R ^3s may be the same or different.

Examples of the linear or branched alkyl group having 1 to 4 carbon atoms in R ¹ , R ² , and R ³ include a methyl group, an ethyl group, a 1-propyl group, a 1-methyl-1-ethyl group, a 1-butyl group, a 1-methyl-1-propyl group, a 1,1-dimethyl-1-ethyl group, etc. From the viewpoint of being able to exhibit higher absorbance (ultraviolet light absorbance per mass), the number of carbon atoms in the alkyl group is preferably an integer of 1 to 3, and more preferably an integer of 1 to 2.

Examples of the linear or branched alkyl group having 1 to 4 carbon atoms substituted with a hydroxyl group in R ¹ , R ² , and R ³ include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 2,2-dihydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1,2-dihydroxypropyl group, a 1,3-dihydroxypropyl group, a 2,3-dihydroxypropyl group, a 1,1-dihydroxypropyl group, a 2,2-dihydroxypropyl group, a 3,3-dihydroxypropyl group, a 1-methyl-1-hydroxyethyl group, a 1-methyl-2-hydroxyethyl group, a 1,1-dimethyl-1-hydroxymethyl group, a 1-hydroxybutyl group, a 2 ... Examples of the alkyl group include a butyl group, a 3-hydroxybutyl group, a 4-hydroxybutyl group, a 1,2-dihydroxybutyl group, a 1,3-dihydroxybutyl group, a 1,4-dihydroxybutyl group, a 2,3-dihydroxybutyl group, a 2,4-dihydroxybutyl group, a 1,1-dihydroxybutyl group, a 2,2-dihydroxybutyl group, a 3,3-dihydroxybutyl group, a 1-hydroxy-1-methylpropyl group, a 2-hydroxy-1-methylpropyl group, a 3-hydroxy-1-methylpropyl group, a 1-hydroxymethylpropyl group, a 1,1-dimethyl-2-hydroxyethyl group, a 2-methyl-1-hydroxypropyl group, a 2-methyl-2-hydroxypropyl group, and a 2-methyl-3-hydroxypropyl group. From the viewpoint of being able to exert a higher absorbance (ultraviolet light absorbance per mass), the number of carbon atoms in the alkyl group is preferably an integer of 1 to 2.

In the present invention, examples of the substituents that may be "substituted" include halogens (fluoro, chloro, bromo, iodo), cyano groups, hydroxyl groups, amino groups, alkoxy groups having 1 to 4 carbon atoms, alkyl groups having 1 to 4 carbon atoms, alkenyl groups having 1 to 4 carbon atoms, alkynyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, heteroalkyl groups having 1 to 4 carbon atoms, heterocycloalkyl groups having 3 to 6 carbon atoms, aryl groups, aryloxy groups, arylalkyl groups, heteroaryl groups, etc. These may be substituted alone or in combination of two or more.

In addition, in the above general formulas (I) to (IV), X is N, and at least one of the Ys present on Z can be a sulfonic acid group, a hydroxyl group, an amino group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a group corresponding to a salt thereof. By having the above configuration, it is possible to obtain a 1,3,5-triazine derivative or a salt thereof that is hydrophilic, has strong ultraviolet absorbing properties mainly in the vicinity of 280 to 315 nm, and has excellent ultraviolet absorbing properties.

In addition, in the above general formulas (I) to (IV), at least one of the Ys present on Z is a hydroxyl group, and Z can be a linear or branched alkyl group having 3 to 8 carbon atoms, a linear or branched alkenyl group having 1 to 8 carbon atoms, a linear or branched alkynyl group having 1 to 8 carbon atoms, a polyoxyethylene group containing 2 to 4 ethylene oxide units, or a polyoxypropylene group containing 1 to 4 propylene oxide units. With the above configuration, it is possible to obtain a 1,3,5-triazine derivative or a salt thereof that is hydrophilic, has strong ultraviolet absorbing properties mainly in the vicinity of 280 to 315 nm, and has excellent ultraviolet absorbing properties.

In addition, in the above general formulas (I) to (IV), at least one of the Ys present on Z, which may be one or more, may be a sulfonic acid group, a hydroxyl group, a carboxyl group, an amino group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a group corresponding to a salt thereof. By having the above configuration, it is possible to more reliably obtain a 1,3,5-triazine derivative or a salt thereof that is hydrophilic, has strong ultraviolet absorbing properties mainly in the vicinity of 280 to 315 nm, and has excellent ultraviolet absorbing properties.

In addition, in the above general formulas (I) to (IV), at least one of the Ys present on Z is preferably a group corresponding to a sodium salt, a potassium salt, or a triethanolamine salt from the viewpoints of synthesis and safety to the skin. By having the above configuration, it is possible to more reliably obtain a 1,3,5-triazine derivative or a salt thereof that is hydrophilic, has strong ultraviolet absorbing properties mainly in the vicinity of 280 to 315 nm, and has excellent ultraviolet absorbing properties.

Furthermore, the 1,3,5-triazine derivative of the present invention, particularly when Y has an acidic group, may, depending on the pH conditions, dissociate a proton to form an anion (-SO ₃ ^- , -COO ^- , PO ₃ ^- , etc.), which may take a salt structure in which a counter cation such as a sodium ion, potassium ion, lithium ion, calcium ion, magnesium ion, aluminum ion, triethanolammonium ion, diethanolammonium ion, etc. is bound to the anion. These counter cations may be used alone or in combination of two or more. The present invention also includes acid addition salts of the above 1,3,5-triazine derivatives.

The 1,3,5-triazine derivative of the present invention, particularly when Y has a basic nitrogen atom, may have a salt structure with an acid added thereto. Examples of the acid include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and hydrobromic acid, and organic acids such as acetic acid, citric acid, gluconic acid, tartaric acid, lactic acid, maleic acid, fumaric acid, methanesulfonic acid, p-toluenesulfonic acid, and nitrobenzenesulfonic acid. These acids may be used alone or in combination of two or more. The present invention also includes acid addition salts of the 1,3,5-triazine derivatives.

In addition, in the present invention, the absorbance (measured at a concentration of 5 ppm using a quartz cell with an optical path length of 1 cm) of the 1,3,5-triazine derivative or its salt mainly in the UVB region is usually 0.02 or more, and more preferably 0.2 to 1.

In addition, even if the above 1,3,5-triazine derivative or its salt has absorption ability in the UVA (wavelength 315 to 400 nm) region, it can be used as an ultraviolet absorbent, topical skin preparation, coating composition, etc., as appropriate.

The molecular weight of the 1,3,5-triazine derivative or salt thereof of the present invention is usually about 450 to 1200, and preferably 450 to 1000. As the molecular weight increases, the UV absorption capacity per unit weight tends to decrease, and it becomes necessary to add a larger amount when using it as an ultraviolet absorber, topical skin preparation, coating composition, etc.

[Method for producing 1,3,5-triazine derivative or its salt]
The 1,3,5-triazine derivatives or salts thereof represented by (I) to (IV) of the present invention can be produced by known reactions using readily available raw materials. The schemes (Schemes 1 to 3) of synthesis examples of the 1,3,5-triazine derivatives or salts thereof are shown above, but they are merely examples, and the 1,3,5-triazine derivatives or salts thereof represented by (I) to (IV) of the present invention are not limited to those obtained by the synthesis examples below.

(Scheme 1)

The 1,3,5-triazine derivatives or salts thereof represented by (I) to (IV) of the present invention can be obtained, for example, by reacting a triazine chloride such as cyanuric chloride with a compound containing G ¹ to G ³ groups or the like corresponding to a side chain through a nucleophilic substitution reaction or the like.

For example, as shown in the above scheme 1, a compound (A) containing a leaving group L and a compound (B) having a G ¹ group are reacted by a nucleophilic substitution reaction or the like to obtain a compound (C) containing a nitro group. In the above reaction, for example, a halogen group such as chlorine can be used as L, and an amine such as diglycolamine can be used as G ¹ H. The above reaction can be carried out in an organic solvent such as methylene chloride or chloroform in the presence of a base such as triethylamine. In addition, in the above reaction, when a hydroxyl group or the like is present in G ¹ , the hydroxyl group or the like can be appropriately protected with an acetyl group, a benzyl group, or the like.

The leaving group L of the compound (A) in the above scheme 1 may be, for example, a functional group that can be substituted or eliminated by nucleophilic attack. Examples of L include fluoro, chloro, bromo, iodo, and sulfonate groups such as methanesulfonyl, p-toluenesulfonyl, nitrobenzenesulfonyl, and trifluoromethanesulfonyl. Among these, from the viewpoint of reaction yield and the like, chloro, bromo, iodo, methanesulfonyl, p-toluenesulfonyl, and trifluoromethanesulfonyl are preferred as L.

In addition, a known base can be appropriately used as the base used in the reaction of Scheme 1 above. Examples of the base include tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, pyrrolidine, and piperidine, and aromatic amines with low nucleophilicity such as pyridine and 4-dimethylaminopyridine. These bases may be used alone or in combination of two or more. In particular, a method may be used in which the above-mentioned tertiary amines or aromatic amines with low nucleophilicity are added in an equal or excess amount as acceptors for chloride ions derived from leaving groups to shift the equilibrium of the reaction (to increase the reaction conversion rate).

In the reaction of Scheme 1, for ^G1 of compound (B) and the like, a compound having a structure corresponding to compound (F), which is the target product, can be appropriately used.

In the reaction in Scheme 1 above, the molar ratio of compound (B) to compound (A) (mol of compound (B)/mol of compound (A)) can be, for example, 0.5 to 2.0 (mol/mol), or may be 0.8 to 1.3 (mol/mol).

In the reaction in Scheme 1, the reaction may be carried out in a suitable solution of each raw material (and catalyst, etc.), or when the raw materials serve as a solvent, only the raw materials may be mixed and used as a reaction solution. As the solvent for the solution, a known solvent may be used as appropriate. Examples of the solvent include benzene, toluene, xylene, nitrobenzene, chlorobenzene, dichloroethane, trichloroethane, tetrachloroethane, etc. These solvents may be used alone or in a mixture of two or more.

In addition, the reaction in Scheme 1 above can be carried out at a reaction temperature of, for example, 0°C to 80°C.

In addition, in the reaction in Scheme 1 above, the reaction time can be, for example, 1 to 24 hours.

(Scheme 2)

Also, as shown in Scheme 2 above, compound (C) containing a nitro group can be reduced by hydrogenation to obtain compound (D) containing an amino group.

In the reduction reaction in Scheme 2 above, a reagent capable of reducing a nitro group without reacting with a carbonyl group or the like can be used as appropriate. The reduction method may be hydrogenation using palladium on carbon or the like, or reduction using a metal with a reducing action such as iron in an acetic acid/water system.

In the reaction in Scheme 2 above, the molar ratio of the reducing agent (reagent for reduction reaction) to compound (C) (mol of reducing agent/mol of compound (C)) can be, for example, 1.0 to 5.0 (mol/mol), or may be 1.0 to 2.0 (mol/mol).

In the reaction in Scheme 2, the reaction may be carried out in a suitable solution of each raw material (and catalyst, etc.). When preparing the solution, a known solvent may be used as appropriate. As the solvent, for example, ethers such as diethyl ether and tetrahydrofuran, alcohols, halogen-based solvents such as dichloroethane, trichloroethane, and tetrachloroethane, etc., which are not subject to reduction themselves, may be used. These solvents may be used alone, or two or more of them may be mixed and used.

In addition, the reaction temperature in the above Scheme 2 can be, for example, 0°C to 80°C, or 15°C to 25°C.

In addition, in the reaction in Scheme 2 above, the reaction time can be, for example, 1 to 24 hours.

(Scheme 3)

As shown in Scheme 3, the obtained compound (D) containing an amino group can be reacted with 3 equivalents of cyanuric chloride (E) by a nucleophilic substitution reaction or the like to obtain the compound. Next, when a hydroxyl group or the like in the G ¹ group or the like is protected, a deprotection reaction is appropriately carried out. When the compound is obtained as a salt, a desired salt can be obtained by appropriately carrying out a neutralization reaction as a post-step. The deprotection reaction or neutralization reaction may be appropriately carried out in conjunction with the substitution reaction in Scheme 3 above. In this way, the 1,3,5-triazine derivatives or salts thereof represented by (I) to (IV) of the present invention can be obtained.

In the reaction in Scheme 3 above, the molar ratio of compound (D) to compound (E) (mol of compound (D)/mol of compound (E)) can be, for example, 3.0 to 5.0 (mol/mol), or may be 3.0 to 3.5 (mol/mol).

In the reaction in Scheme 3, the reaction may be carried out in a suitable solution of each raw material (and catalyst, etc.), or when the raw materials serve as a solvent, only the raw materials may be mixed and used as a reaction solution. As the solvent for the solution, a known solvent may be used as appropriate. Examples of the solvent include N-methylpyrrolidone, dimethylsulfoxide, γ-butyrolactone, dimethylformamide, benzene, toluene, xylene, nitrobenzene, chlorobenzene, dichloroethane, trichloroethane, tetrachloroethane, etc. These solvents may be used alone or in a mixture of two or more.

In addition, the reaction in Scheme 3 above can be carried out at a reaction temperature of, for example, 0°C to 80°C.

In addition, in the reaction in Scheme 3 above, the reaction time can be, for example, 1 to 24 hours.

In addition, the above schemes 1 to 3 are examples of when X in the -X-Z-Y group in general formula (I) is N, but when X is O or S, the 1,3,5-triazine derivative or its salt represented by the general formulas (I) to (IV) of the present invention can be obtained in the same manner as above.

The deprotection reaction can be carried out by any known method. For example, a reduction reaction using hydrogen or the like, or a hydrolysis reaction using an acid or base or an ion exchange membrane or the like can be used as appropriate.

The above reduction reaction can be carried out using any suitable reagent or method that can reduce the nitro group without reacting with the carbonyl group, etc. The reduction method can be hydrogenation using palladium carbon, etc., or reduction using a metal with a reducing effect, such as iron, in an acetic acid/water system, etc.

　Any known acid catalyst can be used as appropriate as the acid catalyst in the hydrolysis reaction. Examples of the acid catalyst include hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, oxalic acid, maleic acid, fumaric acid, benzoic acid, salicylic acid, phthalic acid, and p-toluenesulfonic acid. These acid catalysts can be used alone or in combination of two or more.

Any known basic catalyst can be used as appropriate as the basic catalyst in the hydrolysis reaction. Examples of the basic catalyst include sodium hydroxide, sodium carbonate, sodium hydrogen carbonate, and organic amines such as triethylamine and pyridine. These basic catalysts can be used alone or in combination of two or more.

In addition, in each reaction in the above schemes 1 to 3 of the present invention, a known purification method can be appropriately used to generate the reaction product. Examples of the purification method include silica gel column chromatography, high performance liquid chromatography, gas chromatography, gel permeation chromatography, recrystallization, reprecipitation, solvent extraction, distillation, and reduced pressure distillation. These purification methods may be used alone or in combination of two or more.

[Uses of 1,3,5-triazine derivatives or salts thereof]
(Ultraviolet absorber)
The ultraviolet absorbent of the present invention is characterized by containing the above 1,3,5-triazine derivative or a salt thereof as an essential component. Therefore, the ultraviolet absorbent of the present invention has excellent hydrophilicity and also has excellent ultraviolet (mainly ultraviolet B) absorbing properties. In particular, it can be suitably used in aqueous compositions (such as aqueous solutions and emulsions). Furthermore, the above ultraviolet absorbents may each contain optional components as necessary. Furthermore, the above 1,3,5-triazine derivative or a salt thereof may be used alone or in a mixture of two or more kinds.

In the ultraviolet absorber, the content of the 1,3,5-triazine derivative (and its salt) relative to the ultraviolet absorber (total amount) can be, for example, 0.001 to 100% by mass, more preferably 0.1 to 10% by mass, and even more preferably 0.1 to 1% by mass.

The optional components may be, for example, known organic ultraviolet absorbers and inorganic powder ultraviolet shielding agents other than the 1,3,5-triazine derivatives or salts thereof. In addition, the optional components may be added as appropriate to the composition, or may be added to other optional components, to form an ultraviolet absorbing composition.

Other UV absorbers include, for example, benzophenone-based UV absorbers, cyanoacrylate-based UV absorbers, triazine-based (particularly hydroxyphenyltriazine-based) UV absorbers, benzotriazole-based UV absorbers, etc. These compounds may be used alone or in combination of two or more.

(External skin preparations)
The skin topical preparation of the present invention is characterized by containing the above-mentioned 1,3,5-triazine derivative or its salt as an essential component. Therefore, it has excellent hydrophilicity and excellent ultraviolet (mainly ultraviolet B) absorbing action, and can reduce damage caused by UV exposure, particularly at the application site of human and animal hair and skin. In addition, it can be suitably used in aqueous skin topical compositions (aqueous solution type or emulsion type skin topical compositions), and can exhibit high cleansing properties that allow the 1,3,5-triazine derivative or its salt to be easily removed from the application site by washing with water without using a special cleanser when washing the application site of the skin topical preparation. The skin topical preparation can be used, for example, as a cosmetic, a sunscreen composition, etc. In addition, the skin topical preparation may each contain an optional component as necessary. In addition, the above-mentioned 1,3,5-triazine derivative or its salt may be used alone, or two or more types may be mixed and used.

In the above topical skin preparation, the content of the above 1,3,5-triazine derivative (and its salt) relative to the total amount of the above topical skin preparation can be, for example, 0.1 to 100% by mass, more preferably 0.5 to 20% by mass, and even more preferably 1 to 10% by mass.

The above-mentioned aqueous skin composition for topical application refers to a skin composition for topical application, such as a lotion, that contains water in an amount of, for example, 30 to 99% by mass per 100% by mass of the composition.

In addition, the above topical skin preparations can contain known ingredients without any particular restrictions.

The above topical skin preparations can be used as sunscreen compositions, etc., that meet current needs, particularly those used in daily life, where good cleansing properties are required.

The skin topical preparation of the present invention may contain, for example, the above-mentioned organic UV absorbers and inorganic powder-based UV screeners, liquid oils and fats, solid oils and fats, waxes, hydrocarbons, higher fatty acids, higher alcohols, esters, silicones, anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants, moisturizers, water-soluble polymeric compounds, thickeners, coating agents, sequestering agents, lower alcohols, polyhydric alcohols, sugars, amino acids, organic amines, pH adjusters, skin nutrients, vitamins, antioxidants, fragrances, powders, coloring materials, water, etc. These optional components may be used alone or in combination of two or more.

(Coating composition, coating layer)
The coating composition of the present invention is characterized by containing the above-mentioned 1,3,5-triazine derivative or a salt thereof as an essential component. Therefore, the coating composition has excellent hydrophilicity and excellent ultraviolet (mainly ultraviolet B) absorbing properties, and can be suitably used as a composition containing a water-soluble or environmentally friendly resin, for example, a water-soluble paint, a water-soluble adhesive, a fabric mist for clothing, etc. Furthermore, the above-mentioned coating composition may contain optional components as necessary. Furthermore, the above-mentioned 1,3,5-triazine derivative or a salt thereof may be used alone, or two or more kinds may be mixed and used.

The coating composition is preferably water-soluble.

The coating composition preferably contains water. Depending on the purpose and application, other organic solvents, for example alcohols such as ethanol, may also be used in combination.

In the above water-soluble coating composition (water-soluble coating composition, water-based coating composition), the aqueous coating composition solution or the like preferably contains water in an amount of, for example, 0.001 to 99% by mass per 100% by mass of the composition, and may be 0.01 to 90% by mass, 0.1 to 50% by mass, 1 to 50% by mass, 3 to 30% by mass, 5 to 20% by mass, 8 to 10% by mass, etc.

In the coating composition, the content of the 1,3,5-triazine derivative (and its salt) relative to the total amount of the coating composition can be, for example, 0.001 to 100% by mass, 0.01 to 80% by mass, 0.05 to 60% by mass, 0.1 to 50% by mass, 0.5 to 40% by mass, 1 to 30% by mass, 2 to 15% by mass, 3 to 10% by mass, 4 to 5% by mass, etc., depending on the intended use and application.

In the above coating composition, the solid content concentration can be, for example, 0.001 to 80 mass%, 0.01 to 60 mass%, 0.05 to 50 mass%, 0.1 to 40 mass%, 1 to 20 mass%, 2 to 10 mass%, 3 to 5 mass%, etc., depending on the purpose and application, from the viewpoint of coating workability and the coating film stability of the formed coating layer.

In the above coating composition, from the viewpoint of coating workability and the film stability of the coating layer formed, depending on the purpose and application, for example, the viscosity of the coating composition at 20°C can be 0.1 to 100,000 mPa·s, 1 to 10,000 mPa·s, 2 to 1,000 mPa·s, 10 to 1,000 mPa·s, etc.

The pH of the coating composition can be, for example, 5 to 11, or 6 to 10, 7 to 8, etc., depending on the intended use and application.

The above-mentioned coating composition can be used as a sunscreen composition that meets current needs, particularly in everyday life, where good washability is required.

The coating composition may contain known components without any particular limitations. The coating composition of the present invention may contain, for example, the organic UV absorbers and inorganic powder UV shielding agents described above, plasticizers, pigments, dyes, fillers, antioxidants, conductive materials, light stabilizers, release regulators, softeners, solvents, emulsifiers, liquid oils and fats, solid oils and fats, waxes, hydrocarbons, higher fatty acids, higher alcohols, esters, silicones, anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants, moisturizers, water-soluble polymer compounds, thickeners, coating agents, sequestering agents, lower alcohols, polyhydric alcohols, sugars, amino acids, organic amines, pH adjusters, flame retardants, antioxidants, catalysts, powders, coloring materials, water, and the like. These optional components may be used alone or in combination of two or more.

The coating layer of the present invention is formed using the above coating composition. The coating layer of the present invention is characterized by containing the above 1,3,5-triazine derivative or a salt thereof as an essential component. This results in an excellent ultraviolet (mainly ultraviolet B) absorption effect.

The thickness of the coating layer can be 10 nm to 3 mm, or it may be 10 μm to 2 mm, 30 μm to 1.5 mm, 60 μm to 1.2 mm, or 100 μm to 1 mm, depending on the purpose and application.

The coated body of the present invention also includes the above-mentioned coating layer. The coating form of the coating layer is not particularly limited, but may be, for example, a form in which a part or the whole of the coated body is coated with the coating layer, or the surface or back surface of a glass layer or a plastic layer, and/or an intermediate layer, etc.

The above-mentioned covering body can be applied without any particular restriction, but since it has the above-mentioned excellent ultraviolet absorbing effect, it is preferable to use it for articles that may be used outdoors, especially for applications where the articles are exposed to ultraviolet rays such as sunlight. For example, vehicle parts such as automobiles, aircraft, trains, bicycles, etc., more specifically, each glass such as front, rear, front door, rear door, rear quarter, sunroof, etc., front bumper, rear bumper, front grill, spoiler, door mirror, emblem cover, body, etc. exterior parts, interior parts such as center panel, instrument panel, center console, door panel, etc., lamp parts such as headlamp and rear lamp, lens parts for in-vehicle cameras, lighting covers, decorative films, and various glass substitute parts, etc.; window glass of construction machinery, window glass of buildings, houses, greenhouses, etc., roofs of garages and arcades, lighting fixtures, traffic lights, etc., signs, Examples include wallpaper coverings, sanitary products such as bathtubs and washbasins, building materials for kitchens, exterior wall materials, flooring materials, cork materials, tiles, cushion flooring, and interior flooring materials such as linoleum; electronic devices and electrical products such as mobile phones, mobile information terminals, personal computers, office equipment, solar cells, portable game consoles, flat panel displays, touch panels, optical discs such as DVDs and Blu-ray discs, lenses, optical components such as polarizing plates, optical filters, prisms, optical fibers, anti-reflective films, oriented films, polarizing films, and optical films such as retardation films; textile products such as clothing and curtains; machine parts, agricultural materials, fishing materials, transport containers, packaging containers, toys, play equipment, and miscellaneous goods.

The method for producing a coating layer of the present invention also includes a step of drying the solvent of the coating composition.

In the above process, the solvent can be dried using any known means. For example, the coating layer can be formed by heat treatment at room temperature (e.g., 25°C) to 250°C or 40°C to 150°C, or by irradiating with ultraviolet or infrared rays. Furthermore, the coating layer can be formed not only on an already molded substrate, but also by coating the coating composition on the covered body before molding, as in a precoat process.

The coating composition can be applied (coated) by a method that depends on the intended purpose and application, such as spray coating, squeegee coating, flow coating, bar coating, spin coating, dip coating, die coating, inkjet coating, curtain coating, screen printing, gravure printing, or a method using a brush or spatula.

(Other uses)
The 1,3,5-triazine derivative or a salt thereof of the present invention can be incorporated into products other than skin external preparations and coating compositions, for example, various resins, synthetic rubbers, latexes, packaging materials (films, synthetic resin containers, etc.), contact lenses, fibers, etc. to form various compositions or products, and can protect these paints, etc. from ultraviolet rays.

Below, we will explain examples that specifically demonstrate the configuration and effects of the present invention. The evaluation items in the examples were measured as follows.

<UV spectrum measurement>
The UV spectrum was measured using a spectrophotometer (Shimadzu Corporation, UV-4250). More specifically, the UV spectrum was measured using ethanol or purified water as a solvent, a sample solution concentration of 5 ppm, and a quartz cell with an optical path length of 1 cm. The absorbance was calculated according to the Lambert-Beer law as absorbance = -log ₁₀ (I/I ₀ ), where Io is the transmitted light intensity of an empty cell and I is the transmitted light intensity of a sample cell. The wavelength at which the absorbance in the obtained UV spectrum is maximum was defined as λmax (nm).

<Measurement of ^1H -NMR spectrum>
The measurement of ¹ H-NMR spectrum was carried out using a nuclear magnetic resonance spectrometer (JNM-ECP500, manufactured by JEOL Ltd.) More specifically, the measurement of each ¹ H-NMR spectrum was carried out using DMSO- _d6 as a solvent and tetramethylsilane as an internal standard.

<Evaluation of hydrophilicity>
The solubility of the sample compound in 100 g of the following test solvent (g/100 g test solvent) was measured. Note that, when dissolving, the solution was heated to 60° C., and then allowed to stand at 25° C. for 12 hours, after which the state of the solution was confirmed.

(Test Solvent)
A mixed solvent containing dipropylene glycol, ethanol, and purified water in amounts of 10 mass%, 10 mass%, and 80 mass%, respectively, was used as the test solvent, with the total amount of dipropylene glycol, ethanol, and purified water being 100 mass%.

(Evaluation Method)
If the measured solubility was 1.0 (g/100 g test solvent) or more, the sample compound was evaluated as having hydrophilicity, whereas if the measured solubility was less than 1.0 (g/100 g test solvent), the sample compound was evaluated as not having hydrophilicity.

Example 1
<Synthesis of 1,3,5-trianilino-p-(carbo-(2-(2-hydroxyethoxy)ethyl)-1-amino)-s-triazine (compound (1))>

In a 10 L four-neck flask, 4 L of dichloromethane, 200.0 g (1.90 mol) of diglycolamine, and 202.9 g (2.01 mol) of triethylamine were added under a nitrogen stream at an internal temperature of 5°C, and then a solution of 353.4 g (1.90 mol) of 4-nitrobenzoyl chloride in 2 L of dichloromethane was added dropwise at an internal temperature of 15-20°C and stirred at room temperature for 1 hour. After that, 2 L of saturated sodium bicarbonate water was added to the reaction solution and stirred, and the organic layer was separated, and 1 L of ethyl acetate was added to the aqueous layer for further re-extraction. The organic layers were combined and washed with 2 L of saturated saline, and then the organic layer was distilled under reduced pressure to obtain 465.0 g (yield 96%) of p-(carbo-(2-(2-hydroxyethoxy)ethyl)-1-amino)nitrobenzene as pale yellow crystals.

In a 5L four-neck flask, 88.5g (348.1mmol) of the obtained p-(carbo-(2-(2-hydroxyethoxy)ethyl)-1-amino)nitrobenzene, 880mL of tetrahydrofuran, and 14.6g (366.7mmol) of sodium hydride (60% dispersion) were added under a nitrogen stream and stirred at room temperature for 1 hour. Then, 40.0g (377.4mmol) of benzyl bromide was added dropwise and stirred at 40°C for 5 hours. Then, 900mL of saturated sodium bicarbonate water was added to the reaction liquid and stirred. The organic layer was then separated and washed with 1L of saturated sodium bicarbonate water, after which the organic layer was distilled off under reduced pressure. The resulting residue was purified using silica gel column chromatography (developing solvent: ethyl acetate/hexane = 1/1 → 2/1) to obtain 37.6g (yield 31%) of p-(carbo-(2-(2-benzyloxyethoxy)ethyl)-1-amino)nitrobenzene as a slightly yellow oily substance.

36.1 g (104.8 mmol) of the obtained p-(carbo-(2-(2-benzyloxyethoxy)ethyl)-1-amino)nitrobenzene, 217 mL of acetic acid, 110 mL of regular water, and 17.0 g of reduced iron were added to a 500 mL four-neck flask and stirred at 55°C for 1.5 hours. Insoluble matter was then removed by filtration using Celite and washed with 100 mL of ethyl acetate and 100 mL of regular water. The filtrates were then combined and concentrated under reduced pressure, after which 200 mL of regular water and 42.1 g of potassium carbonate were added and the pH was adjusted to 9. The mixture was then extracted three times with 200 mL of ethyl acetate, the organic layers were combined and washed with 200 mL of regular water, and the organic layers were distilled under reduced pressure to obtain 30.5 g (yield 83%) of p-(carbo-(2-(2-benzyloxyethoxy)ethyl)-1-amino)aniline as a yellow oily substance.

In a 1 L three-neck flask, 27.6 g (87.8 mmol) of the obtained p-(carbo-(2-(2-benzyloxyethoxy)ethyl)-1-amino)aniline and 200 mL of N-methylpyrrolidone were added, and a solution of 4.6 g (24.9 mmol) of cyanuric chloride in 40 mL of N-methylpyrrolidone was added dropwise and stirred at 50°C for 1.5 hours. The mixture was further stirred at 110°C for 1 hour, and after the reaction mixture had cooled to room temperature, 350 mL of ordinary water was added. It was then extracted twice with 350 mL of ethyl acetate, and the organic layers were combined and evaporated under reduced pressure. The resulting residue was purified using silica gel column chromatography (eluent: ethyl acetate/acetone = 4/1 → 1/1) to obtain 23.5 g (yield 93%) of 1,3,5-trianilino-p-(carbo-(2-(2-benzyloxyethoxy)ethyl)-1-amino)-s-triazine as a colorless oily substance.

In a 200 mL three-neck flask, 6.5 g (6.4 mmol) of the obtained 1,3,5-trianilino-p-(carbo-(2-(2-benzyloxyethoxy)ethyl)-1-amino)-s-triazine, 65 mL of tetrahydrofuran, 32.5 mL of ethanol, and 1.3 g of palladium-activated carbon were added, the atmosphere in the flask was replaced with hydrogen gas, and the mixture was stirred at 40°C for 3 hours. Insoluble matter was removed by filtration using Celite, and the insoluble matter was washed with 10 mL of purified water and 100 mL of ethanol, after which the filtrate was distilled under reduced pressure. 50 mL of acetone was added to the obtained residue and stirred, and the precipitated white crystals were collected. The mixture was washed with purified water-acetone to form a slurry, and 3.0 g (yield 63%) of 1,3,5-trianilino-p-(carbo-(2-(2-hydroxyethoxy)ethyl)-1-amino)-s-triazine was obtained.

(Spectral data of compound (1))
UV spectrum: λmax; 306 nm, absorbance; 0.70 (ethanol)
¹ H-NMR spectrum: δ [ppm, DMSO-d ₆ ] = 3.40-3.60 (m, 24H), 4.62 (s, 3H), 7.84 (d, 6H), 7.94 (d, 6H), 8.39 (t, 3H), 9.67 (s, 3H).
Solubility: 1.2 (g/100 g test solvent)...hydrophilic.

Example 2
<Synthesis of 1,3,5-trianilino-p-(carbo-2-hydroxy-1,1-bis(hydroxymethyl)ethyl-1-amino)-s-triazine (compound (2))>

In a 2L three-neck flask, 400mL of N,N-dimethylacetamide, 39.2g (324mmol) of tris(hydroxymethyl)aminomethane, and 54.5g (539mmol) of triethylamine were added under a nitrogen stream at an internal temperature of 25°C, and then a solution of 20.0g (108mmol) of 4-nitrobenzoyl chloride in 200mL of N,N-dimethylacetamide was added dropwise at an internal temperature of 2-6°C, and the mixture was stirred for 2 hours while maintaining the internal temperature at 2-6°C. Furthermore, 110.0g (1078mmol) of acetic anhydride was added dropwise, and the mixture was stirred at room temperature for 48 hours. After that, 1.2L of regular water was added, and the mixture was extracted twice with 600mL of ethyl acetate, the organic layers were combined and washed three times with 600mL of regular water, and the organic layers were then distilled off under reduced pressure. 100 mL of methanol was added to the resulting residue and the mixture was distilled off twice. 200 mL of n-hexane/ethyl acetate (=9/1) was added to the resulting residue and stirred to obtain 40.9 g (70% yield) of p-(carbo-2-acetoxy-1,1-bis(acetoxymethyl)ethyl-1-amino)nitrobenzene as pale yellow crystals.

39.0 g (98.4 mmol) of the obtained p-(carbo-2-acetoxy-1,1-bis(acetoxymethyl)ethyl-1-amino)nitrobenzene, 390 mL of methanol, and 3.9 g of palladium-activated carbon were added to a 500 mL three-neck flask, the atmosphere in the flask was replaced with hydrogen gas, and the mixture was stirred at room temperature for 2 hours. Insoluble matter was removed by filtration using Celite, and the insoluble matter was washed with 39 mL of purified water, and the filtrate was distilled under reduced pressure. 390 mL of ethyl acetate was added to the obtained residue, which was then washed with 390 mL of 0.1 mol/L aqueous sodium hydroxide solution and 390 mL of ordinary water. The mixture was then dried over magnesium sulfate, and the organic layer was distilled under reduced pressure to obtain 25.8 g of p-(carbo-2-acetoxy-1,1-bis(acetoxymethyl)ethyl-1-amino)aniline (yield 72%).

In a 300 mL three-neck flask, 10.0 g (27.3 mmol) of the resulting p-(carbo-2-acetoxy-1,1-bis(acetoxymethyl)ethyl-1-amino)aniline and 60 mL of N-methylpyrrolidone were added, and a solution of 1.36 g (7.4 mmol) of cyanuric chloride in 10 mL of N-methylpyrrolidone was added dropwise and stirred at 25°C for 1 hour. This was then stirred at 50°C for a further 0.5 hour and then at 70°C for a further 1 hour. After the reaction mixture had cooled to room temperature, 140 mL of ordinary water was added, and the mixture was extracted twice with 70 mL of ethyl acetate. The organic layers were combined and evaporated under reduced pressure. The resulting residue was purified using silica gel column chromatography (eluent: ethyl acetate/n-hexane = 10/1) to obtain 4.2 g (yield 48%) of 1,3,5-trianilino-p-(carbo-2-acetoxy-1,1-bis(acetoxymethyl)ethyl-1-amino)-s-triazine as white crystals.

4.0 g (34.1 mmol) of the obtained 1,3,5-trianilino-p-(carbo-2-acetoxy-1,1-bis(acetoxymethyl)ethyl-1-amino)-s-triazine and 67 mL of 0.5 mol/L aqueous methanol solution of potassium carbonate were added to a 100 mL three-neck flask and stirred at room temperature for 1 hour. The reaction mixture was distilled under reduced pressure, 4 mL of ordinary water was added to the resulting residue, and white crystals were collected and then slurry washed with methanol. Further, recrystallization was performed using isopropanol and purified water to obtain 0.12 g (yield 6.9%) of 1,3,5-trianilino-p-(carbo-2-hydroxy-1,1-bis(hydroxymethyl)ethyl-1-amino)-s-triazine.

(Spectral data of compound (2))
UV spectrum: λmax; 307 nm, absorbance; 0.73 (ethanol)
¹ H-NMR spectrum: δ [ppm, DMSO-d ₆ ]=3.69 (s, 18H), 7.79 (d, 6H), 7.93 (d, 6H).
Solubility: 1.5 (g/100 g test solvent)...hydrophilic.

Example 3
<Synthesis of 1,3,5-trianilino-p-(carbo-3-sulfopropyl-1-oxy)-s-triazine trisodium (compound (3))>

2.14 g (4.4 mmol) of 1,3,5-trianilino-p-hydroxycarbonyl-s-triazine and 15 mL of N,N-dimethylformamide were added to a 100 mL three-neck flask and dissolved by heating to 110°C. 1.77 g (14.5 mmol) of 1,3-propane sultone and 1.54 g (14.5 mmol) of sodium carbonate were then added and stirred at 110°C for 24 hours. 1.77 g (14.5 mmol) of 1,3-propane sultone and 1.54 g (14.5 mmol) of sodium carbonate were then added and stirred at 110°C for 1 hour. 1.77 g (14.5 mmol) of 1,3-propane sultone was then added and stirred at 110°C for 1 hour. After the reaction mixture had cooled to room temperature, the solvent was distilled off under reduced pressure. Purified water was added to the resulting residue, and the mixture was purified using HP20 (developing solvent: purified water, acetonitrile) to obtain 1.46 g (yield 36%) of 1,3,5-trianilino-p-(carbo-3-sulfopropyl-1-oxy)-s-triazine trisodium as white crystals.

(Spectral data of compound (3))
UV spectrum: λmax: 307 nm, absorbance: 0.42 (purified water)
¹ H-NMR spectrum: δ [ppm, DMSO-d ₆ ] = 1.99-2.05 (m, 6H), 2.62 (t, 6H), 4.31 (t, 6H), 7.91 (d, 6H), 7.95-8.15 (br, 6H), 9.93 (s, 3H).
Solubility: 5.0 (g/100 g test solvent)...hydrophilic.

Claims (18)

A 1,3,5-triazine derivative or a salt thereof represented by any one of general formulas (I) to (IV):

(In general formulas (I) to (IV),
G ¹ , G ² and G ³ each independently represent hydrogen, an optionally substituted linear or branched alkyl group having 1 to 12 carbon atoms, an optionally substituted linear or branched alkenyl group having 1 to 12 carbon atoms, an optionally substituted linear or branched alkynyl group having 1 to 12 carbon atoms, an optionally substituted polyoxyethylene group containing 1 to 8 ethylene oxide units, an optionally substituted polyoxypropylene group containing 1 to 8 propylene oxide units, or -X-Z-Y (wherein one or more Y's are present on Z, and when more than one Y's are present, the multiple Y's present are the same or different from each other), provided that at least two of G ¹ , G ² and G ³ are the same or different from each other -X-Z-Y.
X is O, N or S.
Y is a sulfonic acid group, a hydroxyl group, a carboxyl group, an amino group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a salt thereof.
Z is a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkenyl group having 1 to 8 carbon atoms, a linear or branched alkynyl group having 1 to 8 carbon atoms, a polyoxyethylene group containing 1 to 4 ethylene oxide units, or a polyoxypropylene group containing 1 to 4 propylene oxide units.
R ¹ , R ² and R ³ each independently represent a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkyl group having 1 to 4 carbon atoms substituted with a hydroxyl group.
l, m, and n are each independently an integer of 0 to 4. When l is 2 or more, the multiple R ^1s are the same or different. When m is 2 or more, the multiple R ^2s are the same or different. When n is 2 or more, the multiple R ^3s are the same or different. The 1,3,5-triazine derivative or salt thereof according to claim 1, represented by general formula (I). The 1,3,5-triazine derivative or its salt according to claim 1, represented by general formula (IV). The 1,3,5-triazine derivative or its salt according to claim 1, characterized in that in the general formulas (I) to (IV), X is N and Y is a sulfonic acid group, a hydroxyl group, an amino group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a group corresponding to a salt thereof. The 1,3,5-triazine derivative or its salt according to claim 2, characterized in that in the general formula (I), X is N and Y is a sulfonic acid group, a hydroxyl group, an amino group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a group corresponding to a salt thereof. The 1,3,5-triazine derivative or salt thereof according to claim 1, characterized in that in the general formulas (I) to (IV), at least one of the Ys present on Z is a hydroxyl group, and Z is a linear or branched alkyl group having 3 to 8 carbon atoms, a linear or branched alkenyl group having 1 to 8 carbon atoms, a linear or branched alkynyl group having 1 to 8 carbon atoms, a polyoxyethylene group containing 2 to 4 ethylene oxide units, or a polyoxypropylene group containing 1 to 4 propylene oxide units. The 1,3,5-triazine derivative or salt thereof according to claim 2, characterized in that in the general formula (I), at least one of the Y's present on Z is a hydroxyl group, and Z is a linear or branched alkyl group having 3 to 8 carbon atoms, a linear or branched alkenyl group having 1 to 8 carbon atoms, a linear or branched alkynyl group having 1 to 8 carbon atoms, a polyoxyethylene group containing 2 to 4 ethylene oxide units, or a polyoxypropylene group containing 1 to 4 propylene oxide units. The 1,3,5-triazine derivative or its salt according to claim 1, characterized in that in the general formulas (I) to (IV), Y is a sulfonic acid group, a hydroxyl group, a carboxyl group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a group corresponding to a salt thereof. The 1,3,5-triazine derivative or salt thereof according to claim 2, characterized in that in the general formula (I), Y is a sulfonic acid group, a hydroxyl group, a carboxyl group, an alkylamino group, an ammonium group, an alkylammonium group, a phosphoric acid group, a phosphonic acid group, or a group corresponding to a salt thereof. The 1,3,5-triazine derivative or salt thereof according to claim 1, characterized in that in the general formulas (I) to (IV), at least one of the Y's present on Z is a group corresponding to a sodium salt, a potassium salt, or a triethanolamine salt. The 1,3,5-triazine derivative or salt thereof according to any one of claims 2, characterized in that in the general formula (I), at least one of the Y's present on Z is a group corresponding to a sodium salt, a potassium salt, or a triethanolamine salt. 2. The 1,3,5-triazine derivative or salt thereof according to claim 1, wherein in the general formulae (I) to (IV), G ¹ , G ² and G ³ are all the same or different -XZY. 3. The 1,3,5-triazine derivative or salt thereof according to claim 2, wherein in the general formula (I), G ¹ , G ² and G ³ are all the same or different -XZY. The 1,3,5-triazine derivative or salt thereof according to any one of claims 1 to 13, which is water-soluble. An ultraviolet absorber comprising the 1,3,5-triazine derivative or its salt according to any one of claims 1 to 13. A composition for external use on the skin, comprising a 1,3,5-triazine derivative or a salt thereof according to any one of claims 1 to 13. A coating composition comprising the 1,3,5-triazine derivative or its salt according to any one of claims 1 to 13. The coating composition according to claim 17, which is water-soluble.