A composition containing 1,3,5-triazine,2,4,6-tris[1,1'-biphenyl]-4-yl with a smaller amount of impurities.

Abstract

A composition comprising 1,3,5-triazine,2,4,6-tris[1,1'-biphenyl]-4-yl (TBPT), a first impurity consisting of one or more halogen-containing triazines, and a second impurity consisting of biphenyl, wherein the amount of the first impurity is 900 ppm by weight or less relative to the total weight of the composition, and the amount of the second impurity is 4000 ppm by weight or less relative to the total weight of the composition.

Description

[Technical Field]

[0001] The present invention relates to a composition comprising 1,3,5-triazine,2,4,6-tris[1,1'-biphenyl]-4-yl in a particularly novel crystalline form A having fewer impurities, a process for preparing the same, and the use of the TBPT-containing composition as a cosmetic composition and a UV filter. [Background technology]

[0002] To comply with cosmetic regulations, purity standards are set for the chemical components of cosmetics. These purity standards are particularly relevant to cosmetics containing chemical components that may exhibit impurities that could be detrimental to the user's health. In particular, aromatic hydrocarbon impurities, when present in cosmetics, can cause adverse effects on the human or animal body. To reduce undesirable side effects caused by impurities, the chemical components of cosmetics should be manufactured in a manner that focuses on reducing such impurities.

[0003] A chemical component widely used in cosmetics is 1,3,5-triazine,2,4,6-tris[1,1'-biphenyl]-4-yl (TBPT). Generally, TBPT is used as a highly efficient and photostable filter against UVB and UVA II radiation in cosmetics, such as anti-aging face care products or sunscreen products, to protect human or animal hair or skin from the harmful effects of UV radiation. In addition, TBPT is known from electroluminescent devices (e.g., U.S. Patent No. 6,225,467B1, International Publication No. 2020 / 226300, International Publication No. 2020 / 231197).

[0004] U.S. Patent Application Publication No. 2004 / 0191191A1 describes a synthesis procedure for obtaining TBPT from cyanuryl chloride and 1,1'-biphenyl by a reaction catalyzed with aluminum chloride in 1,2-dichlorobenzene. Without a proper purification step, there is a risk that residual starting materials may remain in the final product and therefore in cosmetics.

[0005] To avoid impurities that may occur during the synthesis of TBPT, which is used in cosmetics and other products, it is necessary to reduce impurities during the synthesis or purification steps.

[0006] Therefore, there is a continuous need for a rapid and efficient manufacturing process for TBPT. In this regard, an object of the present invention was to provide an optimized process for synthesizing, isolating, and purifying TBPT. [Overview of the project] [Problems that the invention aims to solve]

[0007] One object of the present invention is to provide a composition with an increased amount of crystalline TBPT that can be used as a UV filter. In particular, one object of the present invention is to provide a composition having a high content of crystalline TBPT A.

[0008] Another object of the present invention is to provide a process for the synthesis, isolation, and purification of TBPT in crystalline form. Furthermore, another object of the present invention is to provide a process for providing a large amount of TBPT having crystalline form A. [Means for solving the problem]

[0009] In a first aspect, the present invention provides a composition comprising 1,3,5-triazine,2,4,6-tris[1,1'-biphenyl]-4-yl (TBPT), a first impurity consisting of one or more halogen-containing triazines, and a second impurity consisting of biphenyl, wherein the amount of the first impurity is 900 ppm by weight or less relative to the total weight of the composition, and the amount of the second impurity is 4000 ppm by weight or less relative to the total weight of the composition.

[0010] In a second aspect, the present invention provides a crystalline form A of TBPT that exhibits at least three of the following five reflections, indicated by 2θ values, in an X-ray powder diffractogram at room temperature (20°C) using Cu-Kα rays: 11.6±0.2, 17.8±0.2, 21.1±0.2, 23.4±0.2, and 24.4±0.2°θ.

[0011] In a third aspect, the present invention provides a crystalline form B of TBPT that exhibits at least three of the following five reflections, indicated by 2θ values, in an X-ray powder diffractogram at room temperature using Cu-Kα rays: 8.6±0.2, 10.9±0.2, 17.5±0.2, 18.5±0.2, 19.5±0.2, 19.9±0.2, and 20.7±0.2°θ.

[0012] In a fourth aspect, the present invention relates to a process for interconverting crystalline form B of 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (TBPT) to crystalline form A of TBPT, wherein a) a composition C comprising TBPT in crystalline form B B a) providing composition C B a) Mixing in solvent (S1) to obtain a first mixture; a) Stirring the first mixture at temperature T1 for a time t1 to obtain TBPT in crystalline form A, and thereby providing a second mixture; d) Composition C containing TBPT in crystalline form A from the second mixture. A The present invention provides a process that includes the step of isolating the substance.

[0013] In a fifth aspect, the present invention provides a cosmetic comprising the composition according to the first aspect of the present invention, preferably a cosmetic in which more than 80% by weight, preferably 100% by weight, of TBPT is present in crystalline form A in a micronized form.

[0014] In a sixth aspect, the present invention provides the use of the composition according to the first aspect of the present invention as a UV filter in a cosmetic for protecting the hair and / or skin of a subject from the harmful effects of UV radiation, preferably a use in which more than 80% by weight, preferably 100% by weight, of TBPT is present in crystalline form A.

[0015] Although the present invention has been described in relation to specific embodiments and with reference to specific examples, the present invention is not limited thereto and is defined only by the appended claims.

Brief Description of the Drawings

[0016] [Figure 1] The DSC diagram of RE1 is shown. TBPT is indicated by an endothermic peak with ΔH = 39 - 43 J / g at 221 - 256°C. [Figure 2] The PXRD pattern (CuKα radiation) of RE1 is shown. [Figure 3] The PXRD pattern (CuKα radiation) of IE1 is shown. [Figure 4] The PXRD pattern (CuKα radiation) of CE3 is shown. [Figure 5] The PXRD pattern (CuKα radiation) of CE2 is shown. [Figure 6] The PXRD pattern comparison (CuKα radiation) of form A (top) and form B (bottom) is shown. [Figure 7] The comparison of the UV absorption spectra of forms A and B of TBPT is shown.

Modes for Carrying Out the Invention

[0017] Definitions Before explaining exemplary embodiments of the present invention in detail, important definitions for understanding the present invention are shown.

[0018] The terms listed below are generally understood in their common sense unless otherwise specified.

[0019] The term "includes" does not exclude other elements. For the purposes of this invention, the term "consisting of" is considered a preferred embodiment of the term "includes". Hereinafter, where a group is defined as including at least a certain number of embodiments, it should also be understood that this preferably means disclosing a group consisting only of these embodiments.

[0020] When an indefinite or definite article, such as "a," "an," or "that," is used to refer to a singular noun, unless otherwise specified, this includes the plural form of that noun.

[0021] The term "at least one" numerically means "one or more." In a preferred embodiment, this term means numerically "one."

[0022] The terms “encompassing” and “including” mean that other components may exist in addition to the component being referred to. These terms are inclusive and therefore include “consisting of.” “Consisting of” is conclusive and means that further components may not exist. In one embodiment, the terms “encompassing” or “containing” mean “consisting of.”

[0023] Terms such as “can be obtained” and “obtained” are used interchangeably. This means, for example, that unless otherwise explicitly indicated by the context, the term “obtained” does not mean that the embodiment must be obtained by a series of steps following the term “obtained,” even though such a restrictive understanding is always included as a preferred embodiment by the term “obtained.”

[0024] Furthermore, terms such as “first,” “second,” “third,” or “(a),” “(b),” “(c),” and “(d)” in this specification and the claims are used to distinguish similar components and do not necessarily describe a continuous or chronological order. Terms used in this manner are interchangeable under appropriate circumstances, and it should be understood that embodiments of the present invention described herein may be carried out in an order other than that described or illustrated herein. Where terms such as “first,” “second,” “third,” or “(a),” “(b),” “(c),” “(d),” “i,” “ii,” etc., relate to a method, use, or step of an assay, unless otherwise specified in this application, there may be no time between steps or inconsistent time intervals; that is, steps may be carried out simultaneously, or there may be time intervals of a few seconds, a few minutes, a few hours, a few days, a few weeks, a few months, or even several years between such steps.

[0025] Please understand that the present invention is not limited to the specific methodologies, procedures, reagents, etc., described herein, as these may vary. Please also understand that the technical terms used herein are for the purpose of describing specific embodiments only and are not intended to limit the scope of the present invention, which is limited solely by the appended claims.

[0026] The terms “about” or “approximately” allow for a deviation of ±20%, preferably ±15%, more preferably ±10%, even more preferably ±5%, and in a very preferred embodiment, ±1% from the given numerical value, and in the most preferred embodiment, “about” and “approximately” mean “exactly.”

[0027] A range defined by numbers, such as "80°C to 120°C," means that the values ​​of the two angles and each value within that range are disclosed individually.

[0028] As used herein, the term "room temperature" refers to 20°C. As used herein, the term "standard pressure" refers to 1013 mbar.

[0029] The organic part, as described in the definition of the variable element above, is a general term for a list that enumerates each individual member of that group, similar to the term halogen. n ~C m The prefix indicates the number of possible carbon atoms in the group in each case.

[0030] The term "halogen" refers in each case to fluorine, bromine, chlorine, or iodine, and in particular to fluorine, chlorine, or bromine.

[0031] The term "crystalline form" in relation to TBPT as used in this disclosure includes, in particular, crystalline form A and crystalline form B. However, the existence of further crystalline forms is not excluded.

[0032] The term "polymorphism" refers to an enantiotropic relationship where each form has a temperature range in which it is stable relative to other forms, and a transition point where these forms are equally stable and, in principle, mutually convertible. Above that temperature, there is a tendency for forms to form that are stable only at thermodynamically higher temperatures. Below the transition temperature, the lower-temperature form is the only form stable relative to the other, but usually the higher-temperature form is more likely to freeze than the lower-temperature form to persist beyond its stability range. Forms outside the stability range are referred to here as metastable.

[0033] As used herein, the term “alkyl” typically refers in each case to a linear or branched alkyl group having 1 to 5 carbon atoms, preferably 1 to 4 carbon atoms. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, and 1,2-dimethylpropyl. Methyl, ethyl, n-propyl, isopropyl, and isobutyl are particularly preferred.

[0034] The term "aryl" preferably refers to a six-membered aromatic carbocyclic ring based on a carbon atom as a ring member. A preferred example is phenyl. Hückel's (4n+2) rule holds for aromatic carbocyclic rings.

[0035] In this context, the term “purity” refers to the purity of a batch obtained by a “manufacturing process,” and the product obtained from the manufacturing process typically contains impurities. The purity of a batch can be determined by quantifying the TBPT content in the batch by HPLC. Further details of experiments on the quantification method are described in the examples below. According to this disclosure, TBPT may exhibit purities of, for example, 95% by weight, 98% by weight, 98.5% by weight, 99.0% by weight, or even 100% by weight. Thus, a purity of 98.5% by weight may represent a mixture of 98.5% by weight of pure TBPT and 1.5% by weight of impurities.

[0036] As used herein, the term “impurities” refers to compounds other than TBPT in batch TBPT obtained in the manufacturing process. Therefore, the term “impurities” relates to both inorganic and organic impurities. In relation to this disclosure, particularly relevant impurities are residual impurities from starting materials, intermediate products, or solvents that may be used or generated during the manufacturing process. Among these impurities, there may be impurities of toxicological concern, such as aromatic hydrocarbons like biphenyl or xylene, or halogenated triazines like 2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (BBCT). The list of “impurities” cannot be understood as a comprehensive or definitive list of impurities. In relation to this disclosure, certain known “impurities” are quantified by GC or HPLC. Further details of the quantification methods are described in the examples below.

[0037] As used herein, the term "xylene" encompasses all xylene isomers and mixtures containing 1,2-dimethylbenzene, 1,3-dimethylbenzene, and 1,4-dimethylbenzene, corresponding to ortho-xylene, meta-xylene, and para-xylene (also known as o-xylene, m-xylene, and p-xylene).

[0038] The term "manufacturing process" refers to a process that may include the steps of synthesis, isolation, and purification. A manufacturing process may consist of only one or two of these steps, and may optionally include additional steps. Therefore, unless otherwise specified, a manufacturing process should not be understood as being limited to these steps or any further order of steps.

[0039] As used herein, the term "TBPT" refers to the compound name 1,3,5-triazine,2,4,6-tris[1,1'-biphenyl]-4-yl (CAS number: 31274-51-8, also known as 2,4,6-tris([1,1'-biphenyl]-4-yl)-1,3,5-triazine), which is represented by formula (I). [ka]

[0040] TBPT can occur in amorphous or crystalline forms, or mixtures thereof. The compound of formula (I) may exist in at least two crystalline modifiers or a mixture of two or more crystalline states. Polymorph A can be distinguished from polymorph B by powder X-ray diffraction (XRD) and differential scanning calorimetry (DSC). Due to its unique UV absorption properties, only polymorph A is suitable for sunscreen applications (see Figure 7). Furthermore, polymorph B is metastable at room temperature. Methods and data for polymorphs A and B are provided.

[0041] The terms “crude TBPT” or “TBPT raw material” as used in this disclosure refer to TBPT as a crude product. “Crude TBPT” or “TBPT raw material” can be obtained from a manufacturing process that yields a product with higher concentrations of impurities. TBPT raw material may include TBPT in crystalline form A.

[0042] Accordingly, in a first aspect, the present invention relates to a composition comprising TBPT, a first impurity consisting of a triazine containing one or more halogens, and a second impurity consisting of biphenyl, wherein the amount of the first impurity is 900 ppm by weight or less relative to the total weight of the composition, and the amount of the second impurity is 4000 ppm by weight or less relative to the total weight of the composition.

[0043] Both the first and second impurities, particularly the second impurity, namely biphenyl, are by-products of the manufacturing process of commonly used TBPT, as described in U.S. Patent Application Publication No. 2004 / 0191191A1. Both impurities contain aromatic moieties, which are known to increase the risk of diseases such as cancer. Accordingly, a first aspect of the present invention provides a composition containing TBPT with a lower amount of such impurities than those realized in the prior art.

[0044] Therefore, preferably, the halogen-containing triazine of the first impurity in the composition of the first embodiment of the present invention is selected from the group consisting of chlorine-containing triazines, bromine-containing triazines, and mixtures thereof. Examples of halogen-containing triazines, such as chlorine-containing triazines and bromine-containing triazines, include 1,3,5-triazines, particularly phenyl-substituted ones such as 2,4,6-trisphenyl or biphenyl-substituted ones such as 2,4-di([1,1'-biphenyl]-4-yl),1,3,5-triazines, in which one or more hydrogen atoms are substituted with halogen atoms such as chloro or bromo on the 1,3,5-triazine ring or phenyl ring. In various embodiments, the first impurity is more preferably 1,3,5-triazine,2,4,6-tris(4-bromophenyl) and / or 1,3,5-triazine,2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro(BBCT), and most preferably 1,3,5-triazine,2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro(BBCT).

[0045] Particularly preferably, the amount of the first impurity in the composition of the first embodiment of the present invention is 800 ppm by weight or less, more preferably 600 ppm by weight or less, and most preferably 400 ppm by weight or less, relative to the total weight of the composition. This further reduces the risk of disease when the composition is used, i.e., when used in cosmetics.

[0046] In a preferred embodiment of the first aspect of the present invention, the amount of the first impurity in the composition of the present invention is 0.01 ppm by weight or more relative to the total weight of the composition, preferably 0.1 ppm by weight or more, more preferably 1 ppm by weight or more, even more preferably 10 ppm by weight or more, and most preferably 100 ppm by weight or more.

[0047] It is understood that the amount of the first impurity shown above may refer to the total amount of the first impurity, i.e., all compounds that are halogen-containing triazines in the sense of the present invention, or the more specifically defined first impurity as described herein. Thus, in various embodiments, this amount may also refer to one of the more specifically defined first impurities as defined above, such as 1,3,5-triazine,2,4,6-tris(4-bromophenyl) and / or 1,3,5-triazine,2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro(BBCT). However, it would be preferable that the given maximum amount of the first impurity encompasses the total amount of all compounds that qualify as halogen-containing triazines. These amounts may also be combined such that the total amount of halogen-containing triazines is 900 ppm by weight or less relative to the total weight of the composition, and the amount of a specific impurity, such as 1,3,5-triazine,2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro(BBCT), is 400 ppm by weight or less.

[0048] For the same reasons as described above for the first impurity, preferably the amount of the second impurity in the composition of the first embodiment of the present invention is 3000 ppm by weight or less, more preferably 600 ppm by weight or less, and most preferably 300 ppm by weight or less, relative to the total weight of the composition.

[0049] In a more preferred embodiment of the first aspect of the present invention, the amount of the second impurity in the composition is 0.01 ppm by weight or more, more preferably 0.1 ppm by weight or more, even more preferably 1 ppm by weight or more, even more preferably 10 ppm by weight or more, and most preferably 100 ppm by weight or more, relative to the total weight of the composition.

[0050] The manufacturing process for TBPT described in U.S. Patent Application Publication No. 2004 / 0191191A1 typically uses an aromatic solvent. This aromatic solvent may be a condensed aromatic system. Examples of such solvents include benzene, toluene, xylene, ethylbenzene, naphthalene, fluorene, and mixtures thereof. However, such aromatic compounds can also be problematic in terms of diseases caused by applying compositions containing TBPT to cosmetics. Therefore, it is also desirable of the present invention to further reduce the amount of such solvents in compositions containing TBPT.

[0051] Therefore, preferably, the composition according to the first aspect of the present invention further comprises a third impurity, the third impurity comprising, preferably consisting of, an aromatic hydrocarbon, and the third impurity not comprising biphenyl. This means that the third impurity may comprise or consist of an aromatic hydrocarbon. Preferably, one or more aromatic hydrocarbons are selected from the group consisting of monocyclic aromatic hydrocarbons, polycyclic aromatic hydrocarbons (PAHs) and mixtures thereof, preferably from the group consisting of alkyl-substituted benzene compounds (Cn-benzene), condensed aromatic hydrocarbons and mixtures thereof, more preferably from the group consisting of benzene, toluene, xylene, ethylbenzene, naphthalene, fluorene and mixtures thereof, and most preferably xylene.

[0052] In a preferred embodiment of the first aspect of the present invention, the amount of the third impurity in the composition is 4000 ppm by weight or less, preferably 800 ppm by weight or less, and more preferably 400 ppm by weight or less, relative to the total weight of the composition. Preferably, the amount of the third impurity in the composition of the present invention is 5 ppm by weight or more, preferably 10 ppm by weight or more, and more preferably 20 ppm by weight or more, relative to the total weight of the composition.

[0053] Similar to the definition of the amount of the first impurity shown above, the amount of the third impurity can be understood to refer to the total amount of compounds that are qualified as the third impurity, that is, all compounds that are aromatic hydrocarbons in the sense of the present invention or the third impurity more specifically defined herein. Thus, in various embodiments, the amount can also refer to one of the more specifically defined third impurities defined above, such as xylene. However, a given maximum amount for the third impurity would preferably encompass the total amount of all compounds that are qualified as aromatic hydrocarbons. These amounts can also be combined such that the total amount of aromatic hydrocarbons is 4000 weight ppm or less based on the total weight of the composition, and the amount of a specific impurity, such as xylene, is 400 weight ppm or less.

[0054] Preferably, the composition according to the first aspect of the present invention contains TBPT in an amount in the range of 98.0% to 99.9% by weight, more preferably in the range of 98.5% to 99.9% by weight, based on the total weight of the composition.

[0055] By the process of the third aspect of the present invention, which will be described in more detail below, the composition of the first aspect of the present invention may contain further compounds, and the further compounds have a boiling point B1 at a temperature T B1 of 235 °C or lower, preferably 230 °C or lower, more preferably 200 °C or lower, 180 °C or lower, 160 °C or lower, and most preferably 140 °C or lower, at a pressure p B1 of 1 bar. Further, preferably, the further compounds have a melting point M2 at a temperature T B2 of 20 °C or lower, at a pressure p B2 of 1 bar.

[0056] Preferably, the further compound is a solvent (S1), preferably a polar solvent, more preferably a polar organic compound or water. Preferably, the polar organic compound is selected from the group consisting of esters, alcohols, ethers, aldehydes, ketones and mixtures thereof. Particularly preferably, the polar organic compound is a methyl ketone or alcohol, most preferably acetone, methyl ethyl ketone or ethanol. Therefore, preferably, the further compound is selected from the list consisting of acetone, methyl ethyl ketone, water, ethanol or mixtures thereof.

[0057] Furthermore, surprisingly, TBPT was found to occur in two crystalline polymorphic forms, referred to herein as polymorphs A and B, or (crystalline) forms A and B. Crystalline form A is distinguished from crystalline form B by X-ray powder diffraction spectroscopy. It was observed that the ratio of the amounts of these two crystalline forms varies depending on the conditions used in the TBPT manufacturing process. Moreover, in particular, crystalline form A was observed to exhibit thermal stability at temperatures around 15°C to 45°C. Thus, although crystalline form B also exhibits a long storage life, TBPT of crystalline form A has improved storage life compared to form B. Furthermore, TBPT of form A is suitable for sunscreen applications due to its unique UV filtering properties, namely the UV absorption spectrum of form A (see Figure 7).

[0058] Accordingly, in a second aspect of the present invention, the composition preferably comprises at least a portion, preferably all, of TBPT in crystalline form A, which exhibits at least three of the following five reflections, indicated by 2θ values, in an X-ray powder diffractogram at room temperature using Cu-Kα rays: 11.6±0.2, 17.8±0.2, 21.1±0.2, 23.4±0.2, and 24.4±0.2°θ. More preferably, crystalline form A exhibits at least three reflections 11.6±0.2, 17.8±0.2, and 21.1±0.2°θ in an X-ray powder diffractogram at room temperature using Cu-Kα rays, preferably at least five reflections 11.6±0.2, 17.8±0.2, 21.1±0.2, 23.4±0.2, and 24.4±0.2°θ.

[0059] Compared to form B, which was found as a metastable polymorph of TBPT, form A was found to provide an optimal UV absorption spectrum for sunscreen applications (see Figure 7). Therefore, it is beneficial that most of the TBPT present in the composition is form A. Accordingly, preferably, the amount of crystalline form A TBPT in the composition is more than 50% by weight, preferably more than 60%, 65%, 70%, 75%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, and most preferably 100% by weight, relative to the total weight of TBPT in the composition.

[0060] Preferably, crystal morphology A exhibits an endothermic peak in the DSC curve between 221°C and 256°C, and the DSC curve is measured by a differential scanning calorimeter at a scan rate of 10°C per minute (see Figure 1). More preferably, in the DSC curve, crystal morphology A exhibiting an endothermic peak between approximately 221°C and 256°C is even more preferably characterized in that the enthalpy ΔH measured at the endothermic peak is in the range of approximately 35 J / g to approximately 50 J / g, and more preferably characterized in that the enthalpy ΔH measured at the endothermic peak is in the range of approximately 38 J / g to approximately 45 J / g.

[0061] It was further discovered that polymorphs A and B are enantiotropic with respect to each other. The transition temperature between these two forms is in the range of 230–250°C. When TBPT is heated to this high temperature, a phase transformation is induced from form A, which is stable at low temperatures, to form B, which is stable at high temperatures. These two forms are presumed to represent an enantiotropic system of polymorphs, but the transformation does not easily revert even when cooled.

[0062] Furthermore, in a third aspect of the present invention, the composition preferably comprises at least a portion of TBPT, and preferably all TBPT is present in the composition in crystalline form B, which exhibits at least three of the following five reflections, indicated by 2θ values, in a powder X-ray diffractogram at room temperature using Cu-Kα rays: 8.6±0.2, 10.9±0.2, 17.5±0.2, 18.5±0.2, 19.5±0.2, 19.9±0.2, and 20.7±0.2°θ.

[0063] Preferably, crystalline form B shows an endothermic peak in the DSC curve between 282°C and 293°C, and the DSC curve is measured by a differential scanning calorimeter at a scan rate of 10°C per minute. Preferably, in some embodiments, TBPT is contained in crystalline form B in a weight ratio of more than 50% by weight, preferably more than 60%, 65%, 70%, 75%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, and most preferably 100% by weight, relative to the total weight of TBPT in the composition.

[0064] Form A is suitable for sunscreen applications due to its unique UV absorption properties. However, biphenyl and xylene in the TBPT raw material are aromatic hydrocarbons that pose toxicological concerns. Because form A is stable at low temperatures and readily incorporates small amounts into almost any solvent, it is impossible to significantly reduce impurities by multiple recrystallizations from xylene or xylene / biphenyl mixtures. However, further purification of the TBPT raw material is essential, at least for therapeutic or personal care applications (e.g., sunscreen applications). Therefore, in addition to purifying the crude TBPT composition, it is necessary to find a process to interconvert TBPT present in form B to form A in such compositions.

[0065] Accordingly, in a fourth aspect, the present disclosure is a process for interconverting crystalline form B of 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (TBPT) to crystalline form A of TBPT, wherein a) a composition C comprising TBPT in crystalline form B (in the TBPT providing step) B a) providing composition C (in the first mixing step) B The steps are: a) mixing in solvent (S1) to obtain a first mixture; c) (in the stirring step) stirring the first mixture at temperature T1 for time t1 to obtain TBPT in crystalline form A, thereby providing a second mixture; and d) (in the isolation step) obtaining composition C containing TBPT in crystalline form A from the second mixture. A The present invention provides a process that includes the step of isolating the substance.

[0066] Without being constrained by theory, the transformation from form B to form A of the present invention is thought to be facilitated by a process called "solvent-interaction transformation."

[0067] Generally, the process of the fourth aspect of the present invention can be used to purify and interconvert any crude TBPT. However, it is preferably carried out using a composition containing TBPT prepared in a process involving biphenyl and / or xylene. Thus, in the process according to the fourth aspect of the present invention, the TBPT providing step preferably further comprises the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl. More preferably, the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl comprises a') reacting cyanuryl chloride with biphenyl in heptane at a temperature in the range of about 90°C to about 120°C, with the addition of hydrochloric acid and aluminum chloride; b') removing heptane from the reaction mixture under reduced pressure; and c') adding water, sodium hydroxide and xylene to the reaction mixture.

[0068] Preferably, the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl is d') Optionally, the organic phase is separated from the aqueous phase, the organic phase is washed with water, the organic phase is separated from the aqueous phase, water is completely removed from the organic phase by azeotropic distillation, and the suspension is heated to a temperature of approximately 130°C to 160°C. e') Optionally, the suspension is filtered at a temperature of approximately 130°C to 160°C, the filtrate is cooled to a temperature of approximately 40°C to 60°C to crystallize TBPT, the product is isolated by filtration, the filtered product is washed with solvent (S2), and the product is dried to obtain crude TBPT. This includes one or more of the following.

[0069] Preferably, in the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl, 2,4,6-trihalogen-1,3,5-triazine is cyanuryl chloride. More preferably, in the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl, a solvent is used in the reaction mixture. In another preferred embodiment, the solvent is a nonpolar solvent. In particular, for example, C1-C3 alkyl groups, alkyl-aryl ethers, and C1-C3 alkyl groups optionally substituted with alkyl-alkyl ethers. 20 Linear, branched, or cyclic aliphatic or aromatic hydrocarbons containing carbon atoms can be optionally substituted with alkoxy, halide, or carbonyl moieties. In preferred embodiments, linear aliphatic hydrocarbons are used, most preferably hexane. The step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl may be carried out in the absence of a solvent such as 1,2-dichlorobenzene.

[0070] In one embodiment, a catalyst is used in the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl. The catalyst can act as a Lewis acid. The catalyst is selected from the group consisting of acidic halides, metal alkyls and alkoxides, protic acids, acidic oxides, cation exchange resins and mixtures thereof, preferably from the group consisting of AlCl3, AlBr3, BF3, BCl3, BBr3, BeCl2, CdCl2, ZnCl2, GaCl3, GaBr3, FeCl3, SbCl3, BiCl3, TiCl4, ZrCl4, SnCl4, UCl4, SbCl5 and mixtures thereof. In preferred embodiments, the catalyst is used in stoichiometric amounts or in excess. As a co-catalyst, alcohols, water, HCl, HF, H2SO4, H2PO4, RCOOH (organic acids), and sulfonic acids such as p-toluenesulfonic acid may be used. Most preferably, gaseous HCl is used as a co-catalyst. The co-catalyst may also be used in stoichiometric or excess amounts. The reaction in the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl proceeds particularly well if gaseous HCl is released into the reaction mixture. Preferably, in the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl, the reaction temperature is in the range of about -10 to about 250°C, more preferably about 5 to about 150°C, and most preferably about 70 to about 130°C.

[0071] Furthermore, the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl can be carried out in ionic fluids such as 1-butyl-pyridinium chloride-aluminum(HI) chloride and 1-butyl-3-methylimidazolium chloride-aluminum(HI) chloride (see, for example, 1-ethyl-3-methylimidazolium halogenoaluminate ionic liquids as solvents for Friedel-Crafts acylation reactions of ferrocene. Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry 1999(1), 63).

[0072] Preferably, in the process according to the fourth aspect of the present invention, the TBPT providing step further comprises a step of treating the unpurified composition with a second solvent (S2) (see step e'). Furthermore, also preferably, the isolation step of the process according to the fourth aspect of the present invention also comprises a step of filtering the crystals and a step of washing the crystals with at least one second solvent (S2).

[0073] In a preferred embodiment of a fourth aspect of the present invention, the second solvent (S2) is immiscible with water, preferably a hydrocarbon solvent, and more preferably selected from the list of toluene, mesitylene, xylene, and mixtures thereof. These additional steps further improve the purity of the product with respect to the first and second impurities present in the unpurified composition.

[0074] More preferably, a process according to a fourth aspect of the present invention is: e) (in the second providing step) providing an unpurified composition comprising TBPT and at least a first impurity, wherein the first impurity consists of one or more halogen-containing triazines, and the amount of the first impurity in the composition is 950 ppm by weight or more relative to the total weight of the composition; and f) (in the heating step) heating the unpurified composition to a transition temperature T in the range of 235°C to 280°C. TThe process further includes the step of heating to a certain temperature. This step ensures that residual solvents and other molecules can be removed from the composition by evaporation. This further facilitates the purification of the composition of the first aspect of the present invention by the process according to the fourth aspect of the present invention.

[0075] Preferably, during the stirring step, the temperature T1 is in the range of 10°C to 180°C, more preferably 50°C to 140°C. Similarly, preferably during the stirring step, the pressure p1 is in the range of 900mbar to 4000mbar, more preferably 950mbar to 3000mbar, and most preferably 970mbar to 2700mbar.

[0076] In a preferred embodiment of the fourth aspect of the present invention, the first mixture of the first mixing step contains a solvent (S1) in an amount ranging from 5% to 50% by weight, preferably 5 to 40% by weight, 5 to 35% by weight, 6 to 34% by weight, 7 to 33% by weight, 8 to 32% by weight, 9 to 31% by weight, or 10 to 30% by weight, relative to the total weight of the first mixture. Preferably, in the stirring step, the time t1 is in the range of 1 to 12 hours, preferably 2 to 11 hours, and most preferably 3 to 10 hours. Preferably, the first mixing step is a mixing step with vigorous mixing, and most preferably, the first mixing step includes, preferably consists of, a kneading step. Therefore, most preferably, the first mixing step is carried out in a kneading reactor. Therefore, most preferably, the process of the fourth aspect of the present invention is carried out in a kneading reactor.

[0077] In a preferred embodiment of a fourth aspect of the present invention, the isolation step involves heating the first mixture to a temperature T2 and / or reducing the pressure to p2, thereby removing the solvent (S1) to obtain composition C A This includes obtaining the following. Preferably, the temperature T2 is in the range of 100 to 150°C, more preferably 120 to 140°C. Similarly, the pressure p2 is preferably in the range of 10 to 300 mbar, more preferably 50 to 150 mbar.

[0078] Preferably, the solvent (S1) has a temperature T of 235°C or lower, preferably less than 230°C, more preferably 200°C or lower, 180°C or lower, 160°C or lower, and most preferably 140°C or lower. B1 In this case, the pressure p of 1 bar B1 It has a boiling point B1 at . Furthermore, preferably the solvent (S1) has a temperature T of 20°C or lower. B2 In this case, the pressure p of 1 bar B2 It has a melting point M2. This ensures that no further TBPT of crystal form B is formed during this process.

[0079] Preferably, the solvent (S1) is a polar solvent, more preferably a polar organic compound or water. Preferably, the polar organic compound is selected from the group consisting of esters, alcohols, ethers, aldehydes, ketones and mixtures thereof. Particularly preferably, the polar organic compound is a methyl ketone or alcohol, most preferably acetone, methyl ethyl ketone or ethanol. Therefore, preferably, the solvent (S1) is selected from the list consisting of acetone, methyl ethyl ketone, ethanol, water or mixtures thereof. Surprisingly, TBPT has minimal solubility in these solvents, but such solvents have been found to be suitable for the process of the present invention.

[0080] The solvent residue of halogenated hydrocarbons (U.S. Patent Application Publication No. 2004 / 191191) can be removed by using the process of the fourth aspect of the present invention. When TBPT is synthesized without solvent (U.S. Patent Application Publication No. 2004 / 191191), the biphenyl residue can be removed by using the process of the fourth aspect of the present invention. When TBPT is synthesized without AlCl3, the biphenyl residue can also be removed by using the process of the fourth aspect of the present invention.

[0081] In a fifth aspect, the present invention provides a cosmetic comprising a composition according to the first aspect of the present invention, wherein TBPT is present in crystalline form A in a micronized form.

[0082] In a sixth aspect, the present invention provides the use of a composition according to the first aspect of the present invention as a UV filter in cosmetics for protecting the hair and / or skin of a subject from the harmful effects of UV radiation. [Examples]

[0083] The present invention is further illustrated by the following embodiments.

[0084] List of abbreviations DSC (Differential Scanning Calorimetry) PXRD powder X-ray diffraction method GC Gas Chromatography HPLC (High-Performance Liquid Chromatography) FID (Frame Ionization Detector) DAD Diode Array Detector g grams min h time T temperature Kelvin Celsius (℃) ΔH Enthalpy change J. Jules m meters L (liters) k kilo m millimeter μ (micron) TBPT 1,3,5-triazine,2,4,6-tris[1,1'-biphenyl]-4-yl BBCT 2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine approx. PSD particle size distribution

[0085] method a) Characterization of TBPT polymorphs DSC experiments were performed in an open pan. In this case, volatile solvents and impurities evaporate irreversibly. Scanning speed 10 K / min, 20°C to 300°C, N 250 ml / min. Measurement equipment: DSC3+ module, Mettler-Toledo, or similar measurement equipment. PXRD patterns were recorded using Cu Kα rays in the reflectance configuration (Bragg-Brentano) with a Panalytical X Pert Pro X-ray diffractometer. The sample was placed in a silicon single crystal sample holder with a depth of 0.2 mm and gently and precisely flattened. The tube voltage was 45 kV and the current was 40 mA. PXRD data were collected at room temperature in the range of 2θ = 3.0° to 40.0° in 0.017° increments, with a measurement time of 20 s / step. PXRD data were analyzed using HighScore Plus 4.9 (Malvern Panalytical BV). Peak picking was performed with the following parameters: minimum significance: 7.00, minimum peak width: 0.01°2θ, maximum peak width: 1.00°2θ, peak base width: 2.00°2θ, and smoothed peak apex.

[0086] b) Quantification of impurities GC analysis was used to quantify 2-propanol, xylene (isomer mixture), biphenyl, and isopropyl palmitate. Measuring instrument: Agilent 6850-2 GC. Column: Agilent HP-5, 30m × 320μm × 0.25μm. Oven temperature: 70℃ for 3 minutes, 50K / min → 300℃, 300℃ for 5 minutes. Sample preparation: Sample was completely dissolved in 1,4-dioxane at 80℃ (after cooling to 20℃, the turbid solution was filtered). Detector: FID. Calibration was performed using external standards for xylene (isomer mixture) and biphenyl. HPLC analysis was used to quantify TBPT and BBCT. Measuring instrument: Agilent 1200 HPLC. Column: Phenomenex C18 / 5μm, length 150mm. Oven temperature: 40℃. Injection volume: 5μL. Eluting agent: 900 parts acetonitrile + 50 parts tetrahydrofuran + 50 parts water (isocratic elution). Sample preparation: The sample was completely dissolved in tetrahydrofuran. Detector: DAD. Calibration using external standards for TBPT and BBCT.

[0087] c) UV absorption As described in International Publication No. 2004 / 085412A1 (Example 7: Preparation of Micronized UV Absorber), UV spectra were recorded for micronized TBPT in forms A and B.

[0088] Therefore, d(50) is the average particle size. For UV absorbers for cosmetics, the spectral range of 290 nm to 400 nm is of most interest. The wavelength of maximum absorption can be searched, and the absorbance value at this wavelength is used to characterize the absorbance of the substance. Using the Lambert-Beer law, the molar extinction coefficient at any of the following wavelengths can be obtained.

number

number

[0089] Reference Example: Preparation of RE1 - 1,3,5-triazine,2,4,6-tris[1,1'-biphenyl]-4-yl (TBPT) Suitable materials for the reactor / vessel are, for example, Hastelloy C, enameled steel, or glass. Place 207 kg of cyanuryl chloride, 2080 kg of molten biphenyl, and 340 kg of heptane into the vessel (T=105~110°C). Add 21 kg of gaseous hydrochloric acid subsurface to the stirred mixture (T=105~110°C). At 110°C, add 300 kg of aluminum chloride in small increments depending on the temperature. After approximately 4 hours of aluminum chloride addition, stir the reaction mixture at 110~114°C for about 1 hour until the reaction is complete. Then remove the heptane by distillation under vacuum (100 mbar or higher). Carefully add the reaction mixture to a mixture of 2500 kg of water, 135 kg of sodium hydroxide, and 1670 kg of xylene at 85°C to hydrolyze. Stir the mixture at 85~90°C for about 30 minutes until hydrolysis is complete. The lower aqueous phase is separated from the organic product suspension at 90°C. Next, the organic phase (suspension) is washed with 1000 kg of water at 90°C. After separation of the aqueous phase, the organic phase (suspension) is dried by azeotropic distillation under vacuum. The water is completely removed from the suspension. When the yellow suspension is heated to 143-150°C, the product dissolves, and a turbid solution is obtained. The solution is filtered to remove trace amounts of insoluble impurities. Within 4 hours, the orange to brown solution is cooled to 40°C to obtain crystalline TBPT. The product is isolated by filtration, washed with 2000 kg of xylene, and dried under vacuum at 100-140°C.

[0090] Comparative Examples CE1-3: Conventional Purification of TBPT The TBPT raw material was purified using a Buechi Glass Oven Kugelrohr (BUECHI Labortechnik AG, 9230 Flawil, Switzerland).

[0091] 1-5 g of TBPT raw material, synthesized according to the CE1:RE1 synthesis procedure, is heated under reduced pressure (less than 100 mbar, 1-22 hours) until it becomes liquid (melting point approximately 285°C). Volatile impurities are removed, and the product is allowed to solidify until it cools to room temperature. The longer it is heated, the darker the product becomes.

[0092] 1-5 g of TBPT raw material, synthesized according to the CE2:RE1 synthesis procedure, is heated under reduced pressure (less than 100 mbar, 8-24 hours) without melting until it reaches 245-255°C. Volatile impurities are removed.

[0093] CE3: Heat 1-5 g of TBPT raw material synthesized according to the synthesis procedure of Example 1 to 240°C under reduced pressure (less than 10 mbar, 22 hours) without melting. Remove volatile impurities.

[0094] Example of invention: Purification of TBPT Experiment setup: 8-liter stainless steel (Hastelloy) kneading reactor with counter hook, filled to 70% capacity (approximately 1.9 kg of TBPT), rotation speed 20 / min. Heat the kneader with an oil thermostat. Draw off the gas from the kneader, and the gas stream condenses in a spiral cooler. Ensure the product is cooled before opening the apparatus to prevent contact with high-temperature oxygen, which may affect the color.

[0095] Example of Invention IE1 (Solvent: Methyl Ethyl Ketone) IE1_A: Transformation from polymorph A to polymorph B The TBPT raw materials are introduced into the mixing reactor. The mixing reactor is evacuated and purged with nitrogen for inactivation. A constant nitrogen purge of 10 L / hour is performed throughout the process. T de t T The kneader is heated with a heating medium over time to raise the product temperature above 243°C. The temperature distribution of the product is observed, and the temperature of the product is measured with several PT sensors along the kneader to control the temperature to be above 243°C as the minimum temperature of the finished product. The vacuum is kept constant at 100-600 mbar.

[0096] Temperature (T TThe temperature must not exceed 255°C. The higher the temperature, the darker the product's color becomes, and the closer the product approaches its melting point of 280°C, which must be avoided. When the temperature approaches the melting point, the product may become sticky. Further insulation of the machine is necessary to prevent the formation of low-temperature zones. Good mixing of the materials is necessary for a consistent temperature distribution and removal of impurities.

[0097] [Table 1]

[0098] The products of IE1_A_a, IE1_A_b, IE1_A_c, and IE1_A_d are removed from the reactor, mixed, and homogenized to obtain IE1_A_x.

[0099] IE1_B: Transformation from polymorph B to polymorph A A portion of the TBPT mixture IE1_A_x obtained in Example IE1_A is added to the kneading reactor. The kneading reactor is evacuated and purged with nitrogen for inactivation. The pressure is adjusted to p1 and the temperature to T1. 10-30% by mass of solvent, based on the total mass of TBPT added, is added to the kneading reactor. The solid product is moistened with the solvent in the apparatus until it becomes a slurry. The temperature is p T The solvent should be kept below its boiling point. The solvent should remain in the product mixture. The mixing time (t1 at T1) and the type of solvent should be varied as process parameters for different experiments. The solvent should then be dried at 140°C under a vacuum of 100 mbar (1-6 hours). The product should be cooled before opening the apparatus to prevent contact with high-temperature oxygen, which may affect the color. Analyze the purified TBPT.

[0100] [Table 2]

[0101] Example of Invention IE2 (Solvent: Acetone) IE2_A: Transformation from polymorph A to polymorph B This process step is carried out as described in Example IE1_A. The kneading reactor is opened and a sample of the TBPT product is obtained for analysis. The product remains in the reactor.

[0102] [Table 3]

[0103] IE2_B: Transformation from polymorph B to polymorph A This process step is carried out as described in Example IE1_B, except that acetone is used as the solvent.

[0104] [Table 4]

[0105] Example of Invention IE3 (Solvent: Ethanol) IE3_A: Transformation from Polymorph A to Polymorph B This process step is carried out as described in Example IE1_A. The kneading reactor is opened and a sample of the TBPT product is obtained for analysis. The product remains in the reactor.

[0106] [Table 5]

[0107] IE3_B: Transformation from polymorph B to polymorph A This process step is carried out as described in Example IE1_B, except that ethanol is used as the solvent.

[0108] [Table 6]

[0109] Example of Invention IE4 (Solvent: Water) IE4_A: Transformation from Polymorph A to Polymorph B This process step is carried out as described in Example IE1_A. The kneading reactor is opened and a sample of the TBPT product is obtained for analysis. The product remains in the reactor.

[0110] [Table 7]

[0111] IE4_B: Conversion from Polymorph B to Polymorph A This process step is carried out as described in Example IE1_A, except that water is used as the solvent.

[0112] [Table 8]

[0113] Quantification of impurities

[0114] [Table 9]

[0115] The concentrations of impurities such as xylene, toluene, 1,1'-biphenyl, and BBCT are reduced after purification.

[0116] result DSC measurement

[0117] [Table 10]

[0118] PXRD measurement

[0119] [Table 11]

[0120] In CE1-3, due to the high temperature, polymorph A is converted to polymorph B. Because of its unique UV absorption properties, only polymorph A is suitable for sunscreen applications (see Figure 7). Furthermore, polymorph B is metastable at room temperature.

[0121] XRD Peak

[0122] [Table 12]

[0123] [Table 13]

[0124] [Table 14]

[0125] [Table 15]

Claims

1. 1,3,5-triazine,2,4,6-tris[1,1'-biphenyl]-4-yl (TBPT), A first impurity consisting of one or more halogen-containing triazines, A second impurity consisting of biphenyl and A composition comprising, The amount of the first impurity is 900 ppm by weight or less relative to the total weight of the composition. A composition in which the amount of the second impurity is 4000 ppm by weight or less relative to the total weight of the composition.

2. (1) The amount of the first impurity in the composition is 800 ppm by weight or less, more preferably 600 ppm by weight or less, most preferably 400 ppm by weight or less, and / or (2) The composition according to claim 1, wherein the halogen-containing triazine is selected from chlorine-containing triazine, bromine-containing triazine and mixtures thereof, preferably 1,3,5-triazine,2,4,6-tris(4-bromophenyl) and / or 1,3,5-triazine,2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro(BBCT), and most preferably 1,3,5-triazine,2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro(BBCT).

3. The composition according to claim 1 or 2, wherein the amount of the second impurity in the composition is 3,000 ppm by weight or less, more preferably 600 ppm by weight or less, and most preferably 300 ppm by weight or less, based on the total weight of the composition.

4. The composition according to any one of claims 1 to 3, further comprising a third impurity, wherein the third impurity comprises, preferably, an aromatic hydrocarbon, the third impurity does not contain biphenyl, and the amount of the third impurity in the composition is 4000 ppm by weight or less, preferably 800 ppm by weight or less, and more preferably 400 ppm by weight or less, based on the total weight of the composition.

5. The composition according to claim 4, wherein the aromatic hydrocarbon is selected from the group consisting of monocyclic aromatic hydrocarbons, polycyclic aromatic hydrocarbons (PAHs) and mixtures thereof, preferably selected from the group consisting of alkyl-substituted benzene compounds (Cn-benzene), condensed aromatic hydrocarbons and mixtures thereof, more preferably selected from the group consisting of benzene, toluene, xylene, ethylbenzene, naphthalene and mixtures thereof, and most preferably xylene.

6. The composition according to any one of claims 1 to 5, wherein at least a portion of the TBPT, preferably more than 80% by weight, preferably more than 90% by weight, more preferably more than 95% by weight, and most preferably 100% by weight of the TBPT, is contained in the composition in crystalline form A, which shows at least three of the following five reflections indicated by 2θ values ​​in an X-ray powder diffractogram at room temperature using Cu-Kα rays: 11.6±0.2, 17.8±0.2, 21.1±0.2, 23.4±0.2, and 24.4±0.2°θ.

7. The composition according to any one of claims 1 to 6, wherein at least a portion of the TBPT, preferably more than 80% by weight, preferably more than 90% by weight, more preferably more than 95% by weight, and most preferably 100% by weight of the TBPT, is contained in the composition in crystalline form B, which shows at least three of the following five reflections indicated by 2θ values ​​in an X-ray powder diffractogram at room temperature using Cu-Kα rays: 8.6±0.2, 10.9±0.2, 17.5±0.2, 18.5±0.2, 19.5±0.2, 19.9±0.2 and 20.7±0.2°θ.

8. The further compound comprises a solvent (S1) and a temperature T of 235°C or lower, preferably 230°C or lower, more preferably 200°C or lower, 180°C or lower, 160°C or lower, and most preferably 140°C or lower. Ｂ１ In this case, the pressure p of 1 bar Ｂ１ Boiling point B １ A composition according to any one of claims 1 to 7, having the following characteristics.

9. The further compound is prepared at a temperature of 20°C or lower T Ｂ２ In this case, the pressure p of 1 bar Ｂ２ Melting point M ２ The composition according to claim 8, having the following characteristics.

10. The composition according to claim 8 or 9, wherein the further compound is selected from the list consisting of acetone, methyl ethyl ketone, ethanol, water, and mixtures thereof.

11. A process for interconverting crystalline form B of 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (TBPT) to crystalline form A of TBPT, a) Composition C containing TBPT in crystalline form B Ｂ The steps to provide, b) The composition C Ｂ The steps include mixing the two in a solvent (S1) to obtain a first mixture, c) maintaining the first mixture at a temperature T １ for a time t １ with stirring to thereby obtain TBPT in crystalline form A and thereby provide a second mixture d) Composition C comprising TBPT in crystalline form A from the second mixture. Ａ The steps to isolate and A process that includes this.

12. The aforementioned TBPT provision step is, a1) In the second provisioning step, provide an unpurified composition containing TBPT and at least a first impurity, wherein the first impurity consists of one or more halogen-containing triazines, and the amount of the first impurity in the composition is preferably 950 ppm by weight or more relative to the total weight of the composition. a2) In the heating step, the unpurified composition is heated to a transition temperature T of 235°C to 280°C. Ｔ Heat to within the specified range. The process according to claim 11, including the process described in claim 11.

13. The heating step is performed at a pressure p １ The process according to claim 12, comprising maintaining the pressure in the range of 5 mbar to standard pressure, preferably 900 mbar to standard pressure.

14. A cosmetic comprising the composition according to any one of claims 1 to 6 or 8 to 10, wherein more than 80% by weight, preferably 100% by weight, of the TBPT exists in crystalline form A in a micronized form, exhibiting at least three of the following five reflectances indicated by 2θ values ​​in an X-ray powder diffractogram at room temperature using Cu-Kα rays: 11.6±0.2, 17.8±0.2, 21.1±0.2, 23.4±0.2, and 24.4±0.2°θ.

15. Use of the composition according to any one of claims 1 to 6 or 8 to 10 as a UV filter in cosmetics for protecting the hair and / or skin of a subject from the harmful effects of UV radiation, wherein preferably more than 80% by weight, preferably 100% by weight of the TBPT, exists in crystalline form A, which shows at least three of the following five reflectances indicated by 2θ values ​​in an X-ray powder diffractogram at room temperature using Cu-Kα rays: 11.6±0.2, 17.8±0.2, 21.1±0.2, 23.4±0.2 and 24.4±0.2°θ.

Images