Compositions containing 1,3,5-triazine,2,4,6-tris[1,1'-biphenyl]-4-yl having reduced amounts 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 in the range of 1 to 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 particular in the novel crystalline form A, having fewer impurities, a process for its preparation, as well as compositions containing said composition and the use of said composition as a UV filter. [Background technology]

[0002] To comply with cosmetics regulations, purity standards are established for the chemical ingredients of cosmetics. Purity standards may be particularly relevant for cosmetics containing chemical ingredients that may exhibit impurities that may be detrimental to the health of the user. In particular, aromatic hydrocarbon impurities, when present in cosmetics, can cause adverse effects on the human and animal body. To reduce the undesirable side effects of impurities, the chemical ingredients of cosmetics should be manufactured in a manner that emphasizes the reduction of such impurities.

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

[0004] US Patent Application Publication No. 2004 / 0191191 A1 describes a synthetic procedure for obtaining TBPT from cyanuric chloride and 1,1'-biphenyl in 1,2-dichlorobenzene using an aluminum chloride-catalyzed reaction. Without sufficient purification steps, there is a risk that the starting material will remain in the final product and, therefore, ultimately in the cosmetic product.

[0005] To prevent impurities that may occur during the synthesis of TBPT from being contained in, for example, cosmetic products, they must be reduced already during the synthesis or purification steps.

[0006] Therefore, there is a continuing need for a rapid and efficient process for producing TBPT. In this regard, the present invention aims to provide an optimized process for synthesizing, isolating, and purifying TBPT. Summary of the Invention [Problem to be solved by the invention]

[0007] One object of the present disclosure is to provide highly pure TBPT. A particular object of the present disclosure is to provide a crystalline form of TBPT that is highly pure and has low impurity content, making it particularly suitable for cosmetic applications.

[0008] Another object of the present disclosure is to provide a process for synthesizing, isolating, and purifying crystalline forms of TBPT. Another specific object of the present disclosure is to provide a process for synthesizing, isolating, and purifying crystalline forms of TBPT that are highly pure and have low impurity content. [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 or less based on the total weight of the composition, and the amount of the second impurity is 4000 ppm or less based on the total weight of the composition.

[0010] In a second aspect, the present invention provides crystalline form A of TBPT, which exhibits at least three of the following five reflections at 2θ values ​​in an X-ray powder diffractogram at room temperature (20°C) using Cu-Kα radiation: 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 process for purifying a composition comprising 1,3,5-triazine,2,4,6-tris[1,1'-biphenyl]-4-yl (TBPT), the process comprising: a) providing a crude composition comprising TBPT and at least a first impurity consisting of one or more halogen-containing triazines and a second impurity consisting of biphenyl; b) suspending the crude composition in a solvent (S1), thereby providing a first suspension; c) heating the first suspension to a temperature T1, thereby providing a heated first suspension or a first solution of TBPT in the solvent (S1); d) maintaining the heated first suspension or the first solution of TBPT at a temperature T2 of 100 to 235°C and a pressure p1; e) cooling the heated first suspension or the first solution to a temperature T3 to cause crystallization; and f) isolating the crystals from the solution to obtain a purified composition.

[0012] In a fourth aspect, the present invention provides a cosmetic product comprising a composition according to the first aspect of the present invention, preferably wherein TBPT is present in crystalline form A in micronized form.

[0013] In a fifth aspect, the present invention provides the use of a composition according to the first aspect of the invention as a UV filter in a cosmetic product to protect the hair and / or skin of a subject from the harmful effects of UV radiation.

[0014] The present invention will be described in relation to particular embodiments and with reference to particular examples but the invention is not limited thereto but rather defined only by the appended claims. [Brief explanation of the drawings]

[0015] [Figure 1] The DSC curve of RE1 shows TBPT, which is indicated by an endothermic peak at 221-256°C, with ΔH=39-43 J / g. [Figure 2] PXRD pattern (Cu Kα radiation) of RE1 is shown. [Figure 3] PXRD pattern (Cu Kα radiation) of IE1 is shown. [Figure 4] PXRD pattern (Cu Kα radiation) of CE3 is shown. [Figure 5] PXRD pattern (Cu Kα radiation) of CE2 is shown. [Figure 6] A comparison of the PXRD patterns (Cu Kα radiation) of Forms A (top) and B (bottom) is shown. [Figure 7] 1 shows a comparison of the UV absorption spectra of TBPT forms A and B. DETAILED DESCRIPTION OF THE INVENTION

[0016] definition Before describing exemplary embodiments of the present invention in detail, definitions important for understanding the present invention are provided.

[0017] Terms used hereinafter in this specification are to be understood in their general and ordinary sense unless otherwise specified.

[0018] The term "comprising" does not exclude other elements. The term "consisting of" in the context of the present invention is regarded as a preferred embodiment of the term "comprising". If hereinafter a group is defined as comprising at least a certain number of embodiments, this is to be understood as also disclosing a group that preferably consists only of these embodiments.

[0019] Where an indefinite or definite article is used when referring to a singular noun e.g. "a", "an" or "the", this includes the plural of that noun as well, unless otherwise stated.

[0020] The term "at least one" means "one or more" in quantity. In preferred embodiments, the term means "one" in quantity.

[0021] The terms "comprise" and "comprise" mean that other elements may be present in addition to the elements referenced. These terms are used in the inclusive sense and thus include "consisting of." "Consisting of" is used in the definitive sense and means that no additional elements may be present. In one embodiment, the terms "comprise" or "comprising" mean "consisting of."

[0022] Terms such as "obtainable" and "obtained" are used interchangeably. Unless the context clearly dictates otherwise, this does not mean, for example, that the term "obtained" indicates that, for example, an embodiment must be obtained by, for example, the sequence of steps that follow the term "obtained." However, such a restrictive interpretation is always included in the term "obtained," as a preferred embodiment.

[0023] Furthermore, the terms "first," "second," "third," or "(a)," "(b)," "(c)," "(d)," etc. in the specification and claims are used to distinguish between similar components and do not necessarily describe a sequential or chronological order. It is to be understood that terms so used are interchangeable under appropriate circumstances, and that the embodiments of the invention described herein can be performed in orders other than those described or illustrated herein. When the terms "first," "second," "third," or "(a)," "(b)," "(c)," "(d)," "i," "ii," etc. refer to steps of a method, or use, or assay, unless otherwise specified in this application, as described herein above or below, there is no time interval or consistent time interval between such steps, i.e., the steps may be performed simultaneously, or there may be a time interval of seconds, minutes, hours, days, weeks, months, or even years between such steps.

[0024] It is understood that this invention is not limited to the particular methodology, procedures, reagents, etc. described herein, as these may vary. It is also understood that the terminology used herein is used for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention, which will be limited only by the appended claims.

[0025] The term "about" or "approximately" allows for deviations from the indicated numerical value of ±20%, preferably ±15%, more preferably ±10%, even more preferably ±5%, and in particularly preferred embodiments ±1%, and in the most preferred embodiments, "about" and "approximately" are used to mean "exactly."

[0026] A range delimited by numbers, for example, "80°C to 120°C," means that the boundaries and each value within the range are individually disclosed.

[0027] As used herein, the term "room temperature" relates to 20° C. As used herein, the term "standard pressure" relates to 1013 mbar.

[0028] The organic moieties mentioned in the definitions of the variables above, like the term halogen, are generic terms that encompass the individual listings of each member of that group. The prefixes Cn-Cm in each case indicate the possible number of carbon atoms in the group.

[0029] The term "halogen" designates in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.

[0030] The term "crystalline form" in relation to TBPT according to the present disclosure specifically includes crystalline form A and crystalline form B. However, it does not exclude the possibility that additional crystalline forms may exist.

[0031] The term "polymorphism" refers to a tautomeric relationship in which each crystalline form has a temperature range over which it is stable relative to other crystalline forms, and a transition point above which these crystalline forms are equally stable and, in principle, interconvertible. Above this temperature, there is a thermodynamic tendency for only the crystalline form that is stable at the higher temperature to form. Below the transition temperature, only the low-temperature form is stable relative to other crystalline forms, but the high-temperature form usually has a greater tendency to remain frozen than the low-temperature form does above its stability range. Forms that lie outside of that stability range are referred to herein as "metastable."

[0032] The term "alkyl" as used herein refers in each case to a straight-chain or branched alkyl group typically having 1 to 5 carbon atoms, preferably 1 to 4 carbon atoms. Examples of alkyl groups are 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.

[0033] The term "aryl" preferably includes a 6-membered aromatic carbocyclic ring based on carbon atoms as ring members. A preferred example is phenyl. In aromatic ring systems, the Hückel (4n+2) rule applies.

[0034] In this context, the term "purity" refers to the purity of a batch obtained by a "manufacturing process," and the product obtained from this manufacturing process typically contains impurities. Batch purity can be determined by quantifying the TBPT content of the batch by HPLC. Experimental details of the quantification method are further explained in the Examples below. According to the present disclosure, the purity of TBPT can be, for example, 95%, 98%, 98.5%, 99.0%, or even 100% by weight. Thus, a purity of 98.5% by weight can represent a mixture of 98.5% by weight of pure TBPT and 1.5% by weight of impurities.

[0035] The term "impurities" as used herein refers to compounds that are not TBPT in a batch of TBPT obtained by a manufacturing process. Accordingly, the term "impurities" refers to inorganic and organic impurities. In the context of this disclosure, impurities of particular relevance are those derived from residual starting materials, intermediate products, or solvents that may be used or generated during the manufacturing process. Among these impurities, impurities of concern due to toxicological concerns may exist, such as aromatic hydrocarbons such as biphenyl or xylene, or halogenated triazines such as 2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (BBCT). This list of "impurities" should not be construed as an exhaustive or definitive list of impurities. Within the scope of this disclosure, certain known "impurities" are quantified by GC or HPLC. Experimental details of the quantification methods are further described in the Examples below.

[0036] The term "xylene" referred to herein includes all xylene isomers, including 1,2-dimethylbenzene, 1,3-dimethylbenzene, and 1,4-dimethylbenzene, which are also ortho-xylene, meta-xylene, and para-xylene, and which are also o-xylene, m-xylene, and p-xylene, and mixtures thereof.

[0037] The term "manufacturing process" refers to a process that may include synthesis, isolation, and purification steps. A manufacturing process may consist of only one or two of these steps, and may optionally include additional steps. Thus, a manufacturing process should not be construed as being limited to these steps, or even to the order of these steps, unless otherwise specified.

[0038] The term "TBPT" as used herein shall be understood as an abbreviation for 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]

[0039] TBPT can exist in amorphous or crystalline form and mixtures thereof. The compound of formula (I) can exist in at least two crystalline modifications or a mixture of two or more crystalline states. Polymorph Form A can be distinguished from Polymorph Form B by powder X-ray powder diffraction (XRD) and differential scanning calorimetry (DSC). Only Polymorph Form A, which has specific UV absorption characteristics (see Figure 7), is suitable for sunscreen applications. Furthermore, Polymorph Form B is metastable at room temperature. Methods and data relating to Polymorph Forms A and B are provided.

[0040] "Crude TBPT" or "TBPT raw material" according to the present disclosure refers to TBPT that is a crude product. "Crude TBPT" or "TBPT raw material" may be obtained from a manufacturing process that results in a product containing high levels of impurities. The TBPT raw material may include crystalline Form A of TBPT.

[0041] Accordingly, in a first aspect, the present invention relates to a composition comprising 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 or less, based on the total weight of the composition, and the amount of the second impurity is 4000 ppm or less, based on the total weight of the composition.

[0042] Both the first and second impurities, particularly the second impurity, i.e., biphenyl, are typically by-products of the TBPT manufacturing process employed, i.e., the manufacturing process described in U.S. Patent Application Publication No. 2004 / 0191191 A1. Both impurities contain aromatic moieties, which are known to potentially increase the risk of diseases such as cancer. Accordingly, a first aspect of the present invention provides a composition comprising TBPT that contains such impurities in amounts lower than those achieved in the prior art.

[0043] Thus, preferably, the halogen-containing triazine of the first impurity in the composition of the first aspect of the present invention is selected from the group consisting of chlorine-containing triazines, bromine-containing triazines, and mixtures thereof. Halogen-containing triazines, such as chlorine- and bromine-containing triazines, include 1,3,5-triazines, particularly phenyl-substituted, e.g., 2,4,6-trisphenyl- or biphenyl-substituted, e.g., 2,4-di([1,1'-biphenyl]-4-yl),1,3,5-triazine, in which one or more hydrogen atoms on the 1,3,5-triazine or phenyl ring are replaced by a halogen atom, such as chloro or bromo. 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).

[0044] Particularly preferably, the amount of the first impurity in the composition according to the first aspect 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, thereby further reducing the risk of disease when the composition is used in cosmetics.

[0045] 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, relative to the total weight of the composition.

[0046] It is understood that the amount of the first impurity indicated above can refer to the total amount of the first impurities, i.e., all compounds that are halogen-containing triazines in the sense of the present invention, or to the more specifically defined first impurities described herein. Thus, in various embodiments, this amount can refer to one of the more specifically defined first impurities 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 for the maximum amount given for the first impurity to encompass the total amount of all compounds that qualify as halogen-containing triazines. These amounts can also be combined so 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.

[0047] For the same reasons as stated above in relation to the first impurity, preferably the amount of the second impurity in the composition of the first aspect 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.

[0048] In a further 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, based on the total weight of the composition.

[0049] As described in U.S. Patent Application Publication No. 2004 / 0191191A1, aromatic solvents are typically used in the production process of TBPT. These aromatic solvents may be condensed aromatics. Examples of such solvents include benzene, toluene, xylene, ethylbenzene, naphthalene, fluorene, and mixtures thereof. However, these aromatic compounds may be problematic in terms of the diseases caused by applying compositions containing TBPT to cosmetics. Therefore, it is desirable to further reduce the amount of such solvents in compositions containing TBPT.

[0050] Therefore, preferably, the composition according to the first aspect of the present invention further comprises a third impurity, and the third impurity comprises, and preferably consists of, an aromatic hydrocarbon, and the third impurity does not comprise biphenyl. This means that the third impurity can comprise or consist of an aromatic hydrocarbon. Preferably, the one or more aromatic hydrocarbons are 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-benzenes), condensed aromatic hydrocarbons, and mixtures thereof, more preferably selected from the group consisting of benzene, toluene, xylene, ethylbenzene, naphthalene, fluorene, and mixtures thereof, and most preferably xylene.

[0051] 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, more preferably 400 ppm by weight or less, based on 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, more preferably 20 ppm by weight or more, based on the total weight of the composition.

[0052] As with the definition of the amount of the first impurity given above, it is understood that the amount of the third impurity can refer to the total amount of compounds considered to be third impurities, i.e., all compounds that are aromatic hydrocarbons in the sense of the present invention, or the more specifically defined third impurities described herein. Thus, in various embodiments, this amount can also refer to one of the more specifically defined third impurities defined above, such as xylene. However, it would be preferable for the maximum amount given for the third impurity to include the total amount of all compounds considered to be aromatic hydrocarbons. These amounts can also be combined so that the total amount of aromatic hydrocarbons is 4000 ppm by weight or less, and the amount of a specific impurity, such as xylene, is 400 ppm by weight or less, relative to the total weight of the composition.

[0053] Preferably, the composition according to the first aspect of the present invention comprises TBPT in an amount ranging from 98.0% to 99.9% by weight, more preferably in the range from 98.5% to 99.9% by weight, relative to the total weight of the composition.

[0054] According to the process of the third aspect of the present invention, which is described in detail below, the composition of the first aspect of the present invention may contain a further compound, for example a solvent (S1). This further compound is added at a pressure p of 5 mbar. B1 The boiling point B1 is at a temperature T B1 More preferably, the further compound is heated at a pressure p B2 The boiling point B2 is at a temperature T B2 Preferably, but not necessarily, the further compound is heated to a temperature T in the range of 100°C to 235°C, preferably in the range of 150°C to 230°C. S In the above, TBPT can be dissolved in an amount of 5% by weight to 50% by weight based on the total weight of the additional compound.

[0055] Preferably, the further compound is selected from the group consisting of esters, triglycerides, vegetable oils, modified vegetable oils, carbonates, hydrocarbons (preferably other than the aromatic hydrocarbons of the third impurity), alcohols, ethers and mixtures thereof, preferably the further compound is a linear or branched, preferably linear, saturated or unsaturated, preferably saturated C6-C 50 Esters of fatty acids, preferably C6-C 25 It is an ester of fatty acids.

[0056] Preferred esters are selected from the group consisting of myristates, palmitates, benzoates, laurates and mixtures thereof.

[0057] A preferred myristate ester is isopropyl myristate.

[0058] A preferred palmitate ester is isopropyl palmitate.

[0059] Preferred benzoic acid esters are alkyl benzoates (C 12 ~C 15 ), dipropylene glycol dibenzoate, methyl benzoate Gluceth-20, and mixtures thereof.

[0060] Particularly preferred esters are alkyl benzoates (C 12 ~C 15), Caprylyl Caprylate / Caprate, Cetearyl Ethylhexanoate, Cetearyl Isononanoate, Cetyl Palmitate, Coco-Caprylate, Coco-Caprylate / Caprate, Coco-Caprylate / Caprate, Decyl Oleate, Oleyl Oleate, Dibutyl Adipate, Ethylhexyl Palmitate, Ethylhexyl Stearate, Hexyl Laurate, Hexyldecyl Stearate, Isopropyl Stearate, Octyl Stearate, Isopropyl Myristate, Isopropyl Palmitate, Myristyl Myristate, Oleyl Erucate, Propylene Glycol Dicaprylate / Caprate, Propylheptyl Caprylate, PEG-7 Glyceryl Cocoate, Cetearyl Isononanoate, and mixtures thereof.

[0061] Preferred ethers are dicaprylyl ether and PPG-15 stearyl.

[0062] Preferred alcohols are selected from the group consisting of octyldodecanol, hexyldecanol, oleyl alcohol, and mixtures thereof.

[0063] Preferably, the hydrocarbon is selected from the group consisting of hydrogenated polyisobutene, undecane, tridecane, dioctylcyclohexane, and mixtures thereof.

[0064] Preferred triglycerides are selected from the list consisting of caprylic / capric triglyceride, caprylic / capric triglyceride, cocoglyceride and mixtures thereof.

[0065] Preferred vegetable oils are shea butter, oil of the palm of the hand, passionflower seed oil, Shorea sthenoptera butter, and mixtures thereof.

[0066] Preferably, the modified plant oil is selected from the group consisting of shea butter and vegetable oil.

[0067] Most preferably, the further compound is isopropyl palmitate (IPP).

[0068] Furthermore, it has surprisingly been found that TBPT exists in two crystalline polymorphs, referred to herein as polymorphs A and B or (crystalline) forms A and B. Crystalline form A can be distinguished from crystalline form B by X-ray powder crystal diffraction measurements. It has been observed that the ratio of the amounts of these two crystalline forms varies depending on the conditions used in the TBPT manufacturing process. In addition, it has been observed that crystalline form A, in particular, exhibits thermal stability at temperatures around 15°C to 45°C. Therefore, although crystalline form B can also be stored for long periods, crystalline form A of TBPT exhibits a longer shelf life than form B. Furthermore, form A of TBPT possesses the specific UV-blocking properties, i.e., UV absorption spectrum, of form A, making it suitable for sunscreen applications (see FIG. 7).

[0069] Thus, in the second aspect of the invention, the composition preferably comprises at least a portion of TBPT, preferably all of TBPT, in crystalline form A, which exhibits at least three of the following five reflections in an X-ray powder diffractogram at room temperature using Cu-Kα radiation: 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 the following three reflections, 11.6±0.2, 17.8±0.2, and 21.1±0.2°θ, and preferably at least the following five reflections, 11.6±0.2, 17.8±0.2, 21.1±0.2, 23.4±0.2, and 24.4±0.2°θ, in an X-ray powder diffractogram at room temperature using Cu-Kα radiation.

[0070] Compared to Form B, which also exists as a metastable polymorph of TBPT, Form A has also been found to exhibit an optimal UV absorption spectrum for sunscreen applications (see FIG. 7). Therefore, it is advantageous for the majority of TBPT present in a composition to be Form A. Thus, preferably, the amount of crystalline Form A TBPT in the composition is greater than 50% by weight, preferably greater 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, based on the total weight of TBPT in the composition.

[0071] Preferably, crystalline form A exhibits an endothermic peak at 221°C to 256°C in a DSC curve. The DSC curve is measured using a differential scanning calorimeter at a scanning rate of 10°C per minute (see FIG. 1). More preferably, crystalline form A exhibiting an endothermic peak at about 221°C to 256°C in a DSC curve has a measured enthalpy ΔH of the endothermic peak in the range of about 35 J / g to about 50 J / g, and more preferably, a measured enthalpy ΔH of the endothermic peak in the range of about 38 J / g to about 45 J / g.

[0072] Polymorphs A and B were further found to be tautomeric. The transition temperature between the two forms is in the range of 230-250°C. Heating TBPT to this high temperature induces a phase transition from Form A, which is stable at lower temperatures, to Form B, which is stable at higher temperatures. The two forms appear to represent a polymorphic tautomeric system, but this transition is not readily reversed upon cooling.

[0073] Form A has specific UV absorption characteristics, making it suitable for sunscreen applications. However, biphenyl and xylene in the TBPT raw material are aromatic hydrocarbons that raise toxicological concerns. Multiple recrystallizations from xylene or from a xylene / biphenyl mixture cannot significantly reduce impurities, as Form A, which is stable at low temperatures, readily incorporates small amounts in almost any solvent. However, further purification of the TBPT raw material is essential, at least for therapeutic or personal care applications (e.g., sunscreen applications).

[0074] Accordingly, in a third aspect, the present disclosure provides a process for purifying a composition comprising 1,3,5-triazine,2,4,6-tris[1,1′-biphenyl]-4-yl (TBPT), the process comprising: a) providing a crude composition (in a TBPT-providing step), the crude composition comprising TBPT and at least a first impurity consisting of one or more halogen-containing triazines and a second impurity consisting of biphenyl; b) suspending the crude composition in a solvent (S1) (in a suspending step), thereby providing a first suspension; and c) suspending the crude composition in a solvent (S1), thereby providing a first suspension. a) (in a heating step) heating the first suspension to a temperature T1, thereby providing a heated first suspension or a first solution of TBPT in a solvent (S1); d) (in a temperature maintaining step) maintaining the heated first suspension or the first solution of TBPT at a temperature T2 of 100 to 235°C and a pressure p1; e) (in a cooling step) cooling the heated first suspension or the first solution to a temperature T3 to cause crystallization; and f) (in a isolation step) isolating the crystals from the solution to obtain a purified composition.

[0075] Generally, the process of the third aspect of the present invention can be used to purify any crude TBPT. However, it is preferably carried out using a TBPT-containing composition prepared using a process involving biphenyl and / or xylene. Accordingly, in a process according to the third aspect of the present invention, the step of providing TBPT preferably further comprises 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 cyanuric chloride with biphenyl in heptane with the addition of hydrochloric acid and aluminum chloride at a temperature ranging from about 90°C to about 120°C; b') removing heptane from the reaction mixture under reduced pressure; and c') adding water, sodium hydroxide, and xylene to the reaction mixture.

[0076] Preferably, the reaction of 2,4,6-trihalogen-1,3,5-triazine with biphenyl further comprises one or more of the following optional steps: d') optionally separating the organic phase from the aqueous phase, washing the organic phase with water, separating the organic phase from the aqueous phase, completely removing water from the organic phase by azeotropic distillation, and heating the suspension to a temperature of about 130°C to about 160°C; e') Optionally, filtering the suspension at a temperature of about 130°C to about 160°C, cooling the filtrate to a temperature of about 40°C to about 60°C to crystallize TBPT, isolating the product by filtration, washing the filtered product with solvent (S2), and drying the product to obtain crude TBPT.

[0077] Preferably, in the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl, the 2,4,6-trihalogen-1,3,5-triazine is cyanuric 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 non-polar solvent. In particular, a C1-C 20Straight-chain, branched, or alicyclic hydrocarbons or aromatic hydrocarbons containing carbon atoms and optionally substituted with, for example, C1-C3 alkyl groups, alkyl-aryl ethers, alkyl-alkyl ethers, and optionally substituted with alkoxy, halide, or carbonyl moieties can be used. In a preferred embodiment, straight-chain aliphatic hydrocarbons are used, most preferably hexane. The step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl can be carried out in the absence of a solvent such as 1,2-dichlorobenzene.

[0078] In one embodiment, a catalyst is used in the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl. The catalyst may act as a Lewis acid. The catalyst is selected from the group consisting of acidic halides, metal alkyls and alkoxides, protonic acids, acidic oxides, cation exchange resins, and mixtures thereof, preferably AlCl3, AlBr3, BF3, BCl3, BBr3, BeCl2, CdCl2, ZnCl2, GaCl3, GaBr3, FeCl3, SbCl3, BiCl3, TiCl4, ZrCl4, SnCl4, UCl4, SbCl5, and mixtures thereof. In a preferred embodiment, the catalyst is used in a stoichiometric amount or in excess. Examples of cocatalysts that can be used include alcohols, water, HCl, HF, H2SO4, H2PO4, RCOOH (organic acids), and sulfonic acids such as p-toluenesulfonic acid. Most preferably, gaseous HCl is used as the cocatalyst. The cocatalyst may be used in a stoichiometric amount or in excess. The reaction of the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl proceeds more smoothly when HCl gas is introduced into the reaction mixture. Preferably, the reaction temperature of the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl is about -10 to about 250°C, more preferably about 5 to about 150°C, and most preferably about 70 to about 130°C.

[0079] Furthermore, the step of reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl can be carried out in an ionic liquid such as 1-butyl-pyridinium chloride-aluminum chloride (HI) and 1-butyl-3-methylimidazolium chloride-aluminum chloride (HI) (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).

[0080] Preferably, in the process according to the third aspect of the present invention, the TBPT providing step further comprises treating the crude composition with a second solvent (S2) (see step e'). Also preferably, the isolating step of the process of the third aspect of the present invention also comprises filtering and washing the crystals with at least one second solvent (S2).

[0081] In a preferred embodiment of the third aspect of the present invention, the second solvent (S2) is immiscible with water and is preferably a hydrocarbon solvent, more preferably selected from the group consisting of toluene, mesitylene, xylene and mixtures thereof. These additional steps further improve the purity of the product in terms of the first and second impurities contained in the crude composition.

[0082] In the process according to the third aspect of the present invention, the suspending step preferably comprises adding to the suspension an amount of the unpurified composition in the range of 5% to 50% by weight relative to the total weight of the first suspension.

[0083] In another preferred embodiment of the heating step of the third aspect of the present invention, the temperature T1 is in the range of 100° C. to 235° C., preferably in the range of 150° C. to 230° C. Similarly, preferably in the temperature maintaining step of the third aspect of the present invention, the pressure p1 is in the range of 5 mbar to standard pressure, preferably 900 mbar to standard pressure.

[0084] Preferably, in the process according to the third aspect of the invention, the temperature T3 is in the range of 40° C. to 60° C. This ensures optimal crystallization conditions for TBPT.

[0085] As already further indicated above, processes known from the prior art do not allow the low-temperature stable Form A to be significantly reduced in impurities even after multiple recrystallization from xylene or a xylene / biphenyl mixture, since Form A readily incorporates small amounts of solvent in almost any solvent. This small amount of solvent cannot be removed from the crystals by other means, such as evaporation. However, it has now been found that in the process of the third aspect of the present invention, the problematic compounds, i.e., the first, second and optionally third impurities, can be removed by displacing them with solvent (S1).

[0086] Preferably, the solvent (S1) is heated at a pressure p B1 The boiling point B1 is at a temperature T B1 More preferably, the solvent (S1) is heated at a pressure p B2 The boiling point B2 is at a temperature T B2 Preferably, but not necessarily, the solvent (S1) is heated to a temperature T in the range of 100°C to 235°C, preferably in the range of 150°C to 230°C. S In this case, TBPT can be dissolved in an amount of 5% by weight to 50% by weight based on the total weight of the solvent (S1).

[0087] Instead, preferably, the solvent (S1) complies with the Cosmetics Regulations: it is a liquid that is listed as an "emollient" and / or "solvent" in the International Cosmetic Ingredient Dictionary and Handbook (INCI, International Nomenclature Cosmetic Ingredient).

[0088] The solvent (S1) is preferably selected from the group consisting of esters, triglycerides, vegetable oils, modified vegetable oils, carbonates, hydrocarbons (preferably other than the aromatic hydrocarbons of the third impurity), alcohols, ethers and mixtures thereof, and preferably the solvent (S1) is a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, C6-C 50 Esters of fatty acids, preferably C6-C 25 It is an ester of fatty acids.

[0089] Preferred esters are selected from the group consisting of myristates, palmitates, benzoates, laurates and mixtures thereof.

[0090] A preferred myristate ester is isopropyl myristate.

[0091] A preferred palmitate ester is isopropyl palmitate.

[0092] Preferred benzoic acid esters are alkyl benzoates (C 12 ~C 15 ), dipropylene glycol dibenzoate, methyl benzoate Gluceth-20, and mixtures thereof.

[0093] Particularly preferred esters are alkyl benzoates (C 12 ~C 15), Caprylyl Caprylate / Caprate, Cetearyl Ethylhexanoate, Cetearyl Isononanoate, Cetyl Palmitate, Coco-Caprylate, Coco-Caprylate / Caprate, Coco-Caprylate / Caprate, Decyl Oleate, Oleyl Oleate, Dibutyl Adipate, Ethylhexyl Palmitate, Ethylhexyl Stearate, Hexyl Laurate, Hexyldecyl Stearate, Isopropyl Stearate, Octyl Stearate, Isopropyl Myristate, Isopropyl Palmitate, Myristyl Myristate, Oleyl Erucate, Propylene Glycol Dicaprylate / Caprate, Propylheptyl Caprylate, PEG-7 Glyceryl Cocoate, Cetearyl Isononanoate, and mixtures thereof.

[0094] Preferred ethers are dicaprylyl ether and PPG-15 stearyl.

[0095] Preferred alcohols are selected from the group consisting of octyldodecanol, hexyldecanol, oleyl alcohol, and mixtures thereof.

[0096] Preferably, the hydrocarbon is selected from the group consisting of hydrogenated polyisobutene, undecane, tridecane, dioctylcyclohexane, and mixtures thereof.

[0097] Preferred triglycerides are selected from the list consisting of caprylic / capric triglyceride, caprylic / capric triglyceride, cocoglyceride and mixtures thereof.

[0098] Preferred vegetable oils are shea butter, oil of the palm of the hand, passionflower seed oil, Shorea sthenoptera butter, and mixtures thereof.

[0099] Preferably, the modified plant oil is selected from the group consisting of shea butter and vegetable oil.

[0100] Most preferably, the solvent (S1) is isopropyl palmitate (IPP).

[0101] The isopropyl palmitate filtrate can be reused several times before regeneration. Regeneration methods include: (1) distillation, (2) washing with aqueous base or acid, or (3) adsorption of impurities using specific adsorbents such as charcoal, silica gel, zeolite, activated carbon, cellulose, diatomaceous earth, kieselgur, or other siliceous sedimentary rocks, or a combination of (1), (2), and (3). Adsorbents can be used in the form of spherical pellets, rods, extrusions, or monoliths with a hydrodynamic radius of 0.25 to 5 mm. They should have high abrasion resistance, high thermal stability, and small pore size, resulting in a higher exposed surface area and therefore a higher adsorption capacity.

[0102] This treatment can also be carried out at higher concentrations using a TBPT suspension (TBPT 14-50%).

[0103] Halogenated hydrocarbon solvent residues (US 2004 / 191191) can be removed using the process of the third aspect of the present invention. If the synthesis of TBPT is carried out without a solvent (US 2004 / 191191), biphenyl residues can be removed using the process of the third aspect of the present invention. Similarly, if the synthesis of TBPT is carried out without the use of AlCl, biphenyl residues can be removed using the process of the third aspect of the present invention.

[0104] The particle size distribution (PSD) of TBPT crystals is controlled by the nucleation and growth rates during crystallization, which are therefore affected by the degree of supersaturation in the crystallizer. Therefore, it is essential to consider the supersaturation, nucleation rate, and growth rate in the crystallizer to manage the PSD and impurities in the crystallization process. Further control of the PSD can be achieved by adding seed crystals. Finally, the PSD of TBPT can be easily adjusted by milling the product or by Ostwald ripening of the TBPT suspension.

[0105] In a fourth aspect, the present invention provides a cosmetic product comprising a composition according to the first aspect of the present invention, preferably wherein TBPT is present in crystalline form A in micronized form.

[0106] In a fifth aspect, the present invention provides the use of a composition according to the first aspect of the invention as a UV filter in a cosmetic product to protect the hair and / or skin of a subject from the harmful effects of UV radiation. [Example]

[0107] The present invention is further illustrated by the following examples.

[0108] List of Abbreviations DSC Differential Scanning Calorimetry PXRD Powder X-ray Diffraction Spectroscopy GC Gas Chromatography HPLC High Performance Liquid Chromatography FID Flame ionization detector (FID) DAD Diode Array Detector g grams min h time T temperature K Kelvin ℃ Celsius ΔH enthalpy change J Jules m meters L liters k kilo m millimeter μ Micro 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

[0109] method a) Characterization of TBPT polymorphs DSC experiments were performed in open pans, where volatile solvents and impurities evaporate irreversibly. Scan rate: 10 K / min, 20°C to 300°C, N 250 ml / min. Apparatus: Mettler-Toledo DSC3+ Module or similar. PXRD patterns were recorded using a PANalytical X Pert Pro X-ray diffractometer in Bragg-Brentano reflection geometry with Cu Kα radiation. Samples were mounted on a silicon single crystal sample holder with a depth of 0.2 mm and gently and precisely leveled. The tube voltage was 45 kV and the current was 40 mA. PXRD data were collected at room temperature over the 2θ range of 3.0° to 40.0° with a step width of 0.017° and a measurement time of 20 s per step. PXRD data were analyzed using HighScore Plus 4.9 (Malvern Panalytical BV). Peak picking was performed using the following parameters: minimum significance: 7.00, minimum tip width: 0.01°2θ, maximum tip width: 1.00°2θ, peak base width: 2.00°2θ, smoothed peak top.

[0110] b) Quantitative determination of impurities GC analysis was used to quantify 2-propanol, xylene (isomeric mixture), biphenyl, and isopropyl palmitate. Apparatus: Agilent 6850-2 GC column: Agilent HP-5, 30 m x 320 μm x 0.25 μm. Oven temperature: 70 °C for 3 min, 50 K / min → 300 °C, 300 °C for 5 min. Sample preparation: The sample was completely dissolved in 1,4-dioxane at 80 °C (after cooling to 20 °C, the cloudy solution was filtered). Detector: FID. Calibration was performed using external standards of 2-propanol, xylene (isomeric mixture), biphenyl, and isopropyl palmitate. HPLC analysis was used to quantify TBPT and BBCT. Apparatus: Agilent 1200 HPLC column: Phenomenex C18 / 5 μm, 150 mm length. Oven temperature: 40 °C. Injection volume: 5 μL. Eluent: 900 parts acetonitrile + 50 parts tetrahydrofuran + 50 parts water (isocratic elution). Sample preparation: The sample was completely dissolved in tetrahydrofuran. Detector: DAD. Calibrated using external standards of TBPT and BBCT.

[0111] c) UV absorption UV spectra were recorded for Forms A and B of micronized TBPT as described in WO 2004 / 085412 A1 (Example 7: Preparation of micronized UV absorber).

[0112] Therefore, d(50) is the average particle size. For cosmetic UV absorbers, the spectral range of 290 nm to 400 nm is of most interest. The absorption maximum wavelength can be determined and the absorbance value at that wavelength can be used to characterize the absorption power of the substance. Using the Beer-Lambert law,

number

[0113] The specific absorption coefficient E1,1(λ) of each is calculated using the following formula:

number

[0114] d) Solubility of TBPT The measurements were carried out in a three-neck flask equipped with a stirrer and reflux condenser. The solvent was heated to a predetermined temperature under an inert atmosphere. At the predetermined temperature, TBPT was added to the solvent in small portions. After that, if the crystals dissolved within 10 minutes, more product was added until no more product dissolved within 10 minutes. The solubility was calculated from the amount of solvent and the amount of TBPT that could be dissolved at the predetermined temperature. The mixture was then heated to the next test temperature point, and this process was repeated until the temperature endpoint of interest was reached.

[0115] Reference Example RE1 - Preparation of 1,3,5-triazine, 2,4,6-tris[1,1'-biphenyl]-4-yl (TBPT) Suitable materials for the reactor / vessel include, for example, Hastelloy C, enameled steel, or glass. 207 kg of cyanuric chloride, 2080 kg of biphenyl (molten), and 340 kg of heptane are added to the vessel (T = 105-110 °C). While stirring the mixture, 21 kg of gaseous hydrochloric acid is introduced below the surface (T = 105-110 °C). At 110 °C, 300 kg of aluminum chloride is added in small portions as the temperature progresses. After the aluminum chloride addition is completed over approximately 4 hours, the reaction mass is stirred at 110-114 °C for approximately 1 hour until the reaction is complete. The heptane is then removed by distillation under reduced pressure (≥ 100 mbar). A mixture of 2500 kg of water, 135 kg of sodium hydroxide, and 1670 kg of xylene is carefully added to the reaction mixture at 85 °C to hydrolyze the mixture. The mixture is stirred at 85-90 °C for approximately 30 minutes until the hydrolysis is complete. The lower aqueous phase is separated from the organic product suspension at 90°C. The organic phase (suspension) is then washed with 1,000 kg of water at 90°C. After separation of the aqueous phase, the organic phase (suspension) is dried by azeotropic distillation under reduced pressure. Water is completely removed from the suspension. The yellow suspension is heated to 143-150°C to dissolve the product, resulting in a cloudy solution. Hot filtration is performed to remove traces of insoluble impurities. The orange-brown solution is cooled to 40°C within 4 hours to obtain TBPT crystals. The product is isolated by filtration, washed with 2,000 kg of xylene, and vacuum dried at 100-140°C.

[0116] Comparative Examples CE1-3: Conventional Purification of TBPT The TBPT raw material was refined in a Büchi glass oven, Kugelrohr (Büchi Labortechnik AG, 9230 Flawil, Switzerland).

[0117] 1-5 g of TBPT starting material, synthesized according to the synthesis procedure for CE1:RE1, is heated under reduced pressure (<100 mbar, 1-22 h) until liquid (melting point approximately 285 °C). Volatile impurities are removed. The product solidifies upon cooling to room temperature. The product becomes darker the longer it is heated.

[0118] CE2: 1–5 g of TBPT raw material synthesized according to the synthesis procedure of RE1 is heated under reduced pressure (<100 mbar, 8–24 h) to 245–255°C without melting. Volatile impurities are removed.

[0119] CE3: 1-5 g of the TBPT raw material synthesized according to the synthesis procedure in Example 1 was heated to 240°C under reduced pressure (<10 mbar, 22 h) without melting. Volatile impurities were removed.

[0120] Inventive Example IE1: Purification of TBPT The TBPT raw material, synthesized according to the RE1 synthesis procedure, is mixed with isopropyl palmitate (approximately 13% TBPT). The suspension is heated to 220°C under reduced pressure (approximately 10 mbar). Xylene and biphenyl are removed during this process. The isopropyl palmitate is distilled off at 220-223°C, raising the TBPT concentration to approximately 15%. The solution is slowly cooled to 50°C with stirring, and the product crystallizes. The product is filtered at 50°C, washed with isopropanol, and dried at 100-140°C.

[0121] Inventive Example IE2: Solubility (w / w%) of TBPT in Solvent (S1) The solubility of TBPT at various temperatures was investigated in several solvents (S1) according to the test method described above, and the results are shown in Tables 8 to 13.

[0122] [Table 1]

[0123] [Table 2]

[0124] [Table 3]

[0125] [Table 4]

[0126] [Table 5]

[0127] [Table 6]

[0128] result Impurity quantification

[0129] [Table 7]

[0130] The concentrations of impurities such as xylene, toluene, 1,1'-biphenyl, and BBCT in CE1-3 and IE1 decrease after purification. IE1 has the highest purity.

[0131] Characterization of TBPT polymorphs DSC measurement

[0132] [Table 8]

[0133] PXRD measurement

[0134] [Table 9]

[0135] Polymorph A in CE1-3 transforms to polymorph B at high temperature. Only polymorph A has specific UV absorption properties (see Figure 7), making it suitable for sunscreen applications. Furthermore, polymorph B is metastable at room temperature.

[0136] XRD Peaks

[0137] Table 10

[0138] Table 11

[0139] Table 12

[0140] Table 13

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; A composition comprising: the amount of the first impurity is 900 ppm by weight or less based on the total weight of the composition; the amount of the second impurity is 4000 ppm by weight or less based on the total weight of the composition; Optionally, more than 80 wt.%, preferably more than 90 wt.%, more preferably more than 95 wt.%, and most preferably 100 wt.% of the TBPT is in crystalline form A, exhibiting at least three of the following five reflections at 2θ values: 11.6±0.2, 17.8±0.2, 21.1±0.2, 23.4±0.2, and 24.4±0.2°θ, preferably at least the following three reflections: 11.6±0.2, 17.8±0.2, and 21.1±0.2°θ, more preferably at least the following five reflections: 11.6±0.2, 17.8±0.2, 21.1±0.2, 23.4±0.2, and 24.4±0.2°θ, in an X-ray powder diffractogram at room temperature (20°C) using Cu-Kα radiation.

2. (1) the amount of the first impurity is 800 ppm by weight or less, preferably 600 ppm by weight or less, more preferably 400 ppm by weight or less, based on the total weight of the composition; and / or (2) The composition of claim 1, wherein the halogen-containing triazine is selected from chlorine-containing triazines, bromine-containing triazines, 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. 3. The composition according to claim 1, wherein the amount of the second impurity in the composition is 3000 ppm by weight or less, preferably 600 ppm by weight or less, more preferably 300 ppm by weight or less, relative to the total weight of the composition.

4. 4. The composition according to claim 1, further comprising a third impurity, wherein the third impurity comprises, and preferably consists of, an aromatic hydrocarbon, and the third impurity does not comprise 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, more preferably 400 ppm by weight or less, based on the total weight of the composition.

5. 5. The composition of 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-benzenes), condensed aromatic hydrocarbons, and mixtures thereof, more preferably selected from the group consisting of benzene, toluene, xylene, ethylbenzene, naphthalene, fluorene, and mixtures thereof, and most preferably xylene.

6. Further comprising an additional compound, said additional compound being Temperature T below 230℃ Ｂ１ At a pressure of 5 mbar Ｂ１ and / or Temperature T above 230°C Ｂ２ At 1 bar pressure p Ｂ２ and / or at a temperature Ts ranging from 150°C to 230°C, 5% to 50% by weight of TBPT can be dissolved relative to the total weight of said further compounds, The additional compounds are preferably esters, triglycerides, vegetable oils, modified vegetable oils, carbonates, hydrocarbons other than the aromatic hydrocarbons of the third impurity, alcohols, ethers and mixtures thereof, more preferably linear or branched, preferably linear, saturated or unsaturated, preferably saturated C ６ ~C ５０ The composition according to any one of claims 1 to 5, wherein the solvent (S1) is chosen from esters of fatty acids.

7. 7. The composition according to claim 1, wherein at least a portion of the TBPT, preferably all of the TBPT, is contained in the composition in crystalline form A, which exhibits at least three of the following five reflections at 2θ values ​​in an X-ray powder diffractogram at room temperature using Cu-Kα radiation: 11.6±0.2, 17.8±0.2, 21.1±0.2, 23.4±0.2, and 24.4±0.2°θ.

8. 1. A process for purifying a composition comprising 1,3,5-triazine,2,4,6-tris[1,1′-biphenyl]-4-yl (TBPT), comprising: a) providing an unpurified composition comprising TBPT and at least a first impurity consisting of one or more halogen-containing triazines and a second impurity consisting of biphenyl; b) suspending said crude composition in a solvent (S1), thereby providing a first suspension; c) heating the first suspension to a temperature T １ to thereby provide a heated first suspension or a first solution of TBPT in said solvent (S1); d) The heated first suspension or the first solution of TBPT is heated to a temperature T ２ and pressure p １ and e) heating the heated first suspension or the first solution to a temperature T ３ cooling to crystallize; f) isolating the crystals from the solution to obtain a purified composition. A process involving:

9. 9. The process of claim 8, wherein step a) comprises reacting 2,4,6-trihalogen-1,3,5-triazine with biphenyl.

10. 10. The process of claim 8 or 9, wherein step a) further comprises treating the unpurified composition with a second solvent (S2).

11. In step d), the pressure p １ The process according to any one of claims 8 to 10, wherein the pressure is maintained in the range of 5 mbar to atmospheric pressure, preferably 900 mbar to atmospheric pressure.

12. The solvent (S1) is heated at a temperature T Ｂ１ At a pressure of 5 mbar Ｂ１ and / or a temperature T Ｂ２ At 1 bar pressure p Ｂ２ and / or has a boiling point at a temperature T in the range of 100°C to 235°C, preferably in the range of 150°C to 230°C Ｓ 12. The process according to claim 8, wherein 5% to 50% by weight of TBPT can be dissolved in the further compound.

13. A cosmetic product comprising a composition according to any one of claims 1 to 7, wherein preferably the TBPT is present in crystalline form A in micronized form.

14. Use of a composition according to any one of claims 1 to 7 as a UV filter in cosmetic products to protect the hair and / or skin of a subject from the harmful effects of UV radiation.

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