- A PROCESS FOR THE PREPARATION OF UV ABSORBERS
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The presently claimed invention relates to a novel, highly efficient and general process for the preparation of UV absorbers.
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Page/Page column 72-74
(2020/07/25)
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- Method for preparing 2-(2,4-dihydroxyphenyl)-4,6-bisaryl-1,3,5-triazine
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The invention provides a method for preparing 2-(2,4-dihydroxyphenyl)-4,6-bisaryl-1,3,5-triazine. In the existence of a tetrafluoroborate ionic liquid and HCl gas, cyanuric chloride and an aromatic hydrocarbon react to form a compound of a formula I; the compound of the formula I is reacted with resorcinol to form a compound of a formula II. The method avoids the use of aluminum trichloride, and achieves clean production and green chemical industry. A catalyst adopted in the method can be recycled and used for multiple times, thus effectively saving the cost.
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Paragraph 0058-0063
(2019/11/21)
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- Method of recycling catalyst used in Friedel-Crafts process for producing aryl-s-triazine ultraviolet absorber
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The invention discloses a method of recycling a catalyst used in Friedel-Crafts process for producing an aryl-s-triazine ultraviolet absorber. The method includes the following steps: 1) with chlorobenzene as a solvent, performing a Friedel-Crafts reaction to cyanuric chloride and aromatic hydrocarbon under a catalyst, AlCl3, to prepare a reaction solution which contains an intermediate of the aryl-s-triazine ultraviolet absorber; 2) adding a tetrachloroaluminate ionic liquid, as an extract agent, to the reaction solution so as to separate the intermediate of the aryl-s-triazine ultraviolet absorber from the AlCl3 or tetrachloroaluminate ions, and recycling the extracted and separated AlCl3 or tetrachloroaluminate ions as the catalyst or the extract agent for producing the aryl-s-triazineultraviolet absorber via the Friedel-Crafts process. In the method, the tetrachloroaluminate ionic liquid is used as the extract agent to separate the intermediate from the catalyst phase AlCl3, so that the catalyst, AlCl3, used in the Friedel-Crafts process can be recycled. The method eliminates waste water containing the AlCl3 without reduction on product yield, thus significantly improving clean production performance.
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Paragraph 0034; 0035; 0036; 0037; 0038; 0039; 0051; 0052
(2018/04/03)
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- Synthesis, Spectra, and Theoretical Investigations of 1,3,5-Triazines Compounds as Ultraviolet Rays Absorber Based on Time-Dependent Density Functional Calculations and three-Dimensional Quantitative Structure-Property Relationship
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A series of 1,3,5-triazines were synthesized and their UV absorption properties were tested. The computational chemistry methods were used to construct quantitative structure-property relationship (QSPR), which was used to computer aided design of new 1,3,5-triazines ultraviolet rays absorber compounds. The experimental UV absorption data are in good agreement with those predicted data using the Time-dependent density functional theory (TD-DFT) [B3LYP/6–311 + G(d,p)]. A suitable forecasting model (R > 0.8, P 0.0001) was revealed. Predictive three-dimensional quantitative structure-property relationship (3D-QSPR) model was established using multifit molecular alignment rule of Sybyl program, which conclusion is consistent with the TD-DFT calculation. The exceptional photostability mechanism of such ultraviolet rays absorber compounds was studied and confirmed as principally banked upon their ability to undergo excited-state deactivation via an ultrafast excited-state proton transfer (ESIPT). The intramolecular hydrogen bond (IMHB) of 1,3,5-triazines compounds is the basis for the excited state proton transfer, which was explored by IR spectroscopy, UV spectra, structural and energetic aspects of different conformers and frontier molecular orbitals analysis.
- Wang, Xueding,Xu, Yilian,Yang, Lu,Lu, Xiang,Zou, Hao,Yang, Weiqing,Zhang, Yuanyuan,Li, Zicheng,Ma, Menglin
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p. 707 - 723
(2018/05/05)
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- COUMESTAN-LIKE ANTIOXIDANTS AND UV ABSORBANTS
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The present invention relates to derivatives of the 1H-pyrano[4,3-b]benzofuran-1-one structure and their nitrogen analogues which possess powerful antioxidant properties combined with a highly effective UV absorbing functionality in one molecule. These compounds are especially useful in cosmetical and dermatological formulations.
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- Process for isolation of monophenolic-bisaryl triazines
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This invention relates to a novel, efficient, economic and general-purpose process for isolating monophenolic-bisaryl triazine compounds from polyphenolic-triazines compounds and other impurities. More specifically, this invention relates to a process for isolating the monophenolic-bisaryl triazine compounds by contacting it with a base, an alcohol or a hydrocarbon solvent.
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- 4-Formyl amino-n-methylpiperidine derivatives, the use thereof as stabilisers and organic material stabilised therewith
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The present invention relates to 4-formylamino-N-methylpiperidine derivatives of the formula (I) where the variables are as defined in the Description, to a process for preparing these piperidine derivatives, to the use of these piperidine derivatives of the invention, or prepared according to the invention, for stabilizing organic material, in particular for stabilizing plastics or coating materials, and also to the use of these piperidine derivatives of the invention, or prepared according to the invention, as light stabilizers or stabilizers for wood surfaces. The present invention further relates to stabilized organic material which comprises these piperidine derivatives of the invention or prepared according to the invention.
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- Process for making 2-hydroxy-4-alkoxyphenyl or 2,4-dihydroxyphenyl substituted 1,3,5-triazine UV absorbers
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The invention provides new processes for preparing compositions containing at least one triazine compound, including new compounds for use in these processes to form the compositions and the new compositions that are formed.
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- Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith
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Hindered amines substituted on the N-atom with an hydroxy-substituted alkoxy moiety are particularly effective in stabilizing organic polymer compositions against the deleterious effects of oxidative, thermal and actinic radiation where the presence of the OH group on the compounds adds important properties not otherwise attainable.
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- Substituted 5-heteroaryl-2-(2-hydroxyphenyl)-2h-benzotriazole UV absorbers, a process for preparation thereof and compositions stabilized therewith
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Compounds of formula I or II where R is a heteroaryl moiety, such as 3-pyridyl, or T is a heteroaryl moiety, such as thien-2,5-diyl, and E1and E2are independently hydrogen, alkyl, aralkyl and the like, are prepared by reaction of a benzotriazole substituted on the 5-position of the benzo ring by a halogen atom with a heteroarylboronic acid or ester in the presence of a transition-metal catalyst, such as palladium (II) diacetate. The benzotriazole compounds of formula I are particularly efficacious as stabilizers for automotive coatings and candle wax.
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- Process for making triazine UV absorbers using lewis acids and reaction promoters
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It has been now surprisingly discovered after extensive research that 2-halo-4,6-bisaryl-1,3,5-triazine can be prepared with unprecedented selectivity, efficiency, mild conditions, and in high yield by the reaction of cyanuric halide with aromatics in the presence of at least one Lewis acid and at least one reaction promoter. This reaction is also unprecedently general as a variety of aromatics can be used to produce a wide selection of 2-halo-4,6-bisaryl-1,3,5-triazines. The novel approach includes the use of the reaction promoters in combination with at least one Lewis acid under certain reaction conditions to promote the formation of 2-halo-4,6-bisaryl-1,3,5-triazine compounds from cyanuric halide. Preferably, the Lewis acids and reaction promoters are combined to form a complex. 2-Halo-4,6-bisaryl-1,3,5-triazines are key intermediates for making 2-(2-oxyaryl)-4,6-bisaryl-1,3,5-triazine class of UV absorbers.
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- Methods for the preparation of tris-aryl-o-hydroxyphenyl-s-triazines
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A process for preparing 2-(2,4-dihydroxyphenyl)-4.6-diaryl-s-triazines in three steps starting with cyanuric chloride is described. Step1involves the nucleophilic (basic) displacement of one chlorine atom with a phenolic moiety. Step2involves a Friedel-Crafts reaction using a Lewis acid catalyst (preferably aluminum chloride) to replace the remaining two chlorine atoms with aryl groups such as xylyl. Finally, step3involves replacing the phenolic moiety with resorcinol using either a Lewis acid or protic acid catalyst or combinations thereof. Some additional processes only peripherally related to the three-step process outlined above are also described for the preparation of various s-triazine compounds. The s-triazines prepared are useful as UV absorbers for the stabilization of organic substrates against the adverse effects of actinic light.
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- Process for making 2-(2,4,-dihydroxyphenyl) or 2-(2,4-dialkoxyphenyl)-4,6-bisaryl-1,3,5-triazines
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Provided is a new process for the preparation of compositions containing at least one triazine ultraviolet light absorber.
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- Hydroxyphenyltriazines
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A description is given of compounds of the formula wherein R and R' independently are H, methyl or ethyl. The novel compounds are effective as stabilizers for organic material against the damaging effect of light, oxygen and heat; they are also suitable for use in skin or hair protection preparations.
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- Acylphosphine oxides
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Compounds of formula (I), in which X is oxygen or sulfur, R1, R2 and R3 independently of one another are a group (a), C2 -C8 alkenyl, phenyl which is unsubstituted or is substituted from one to four times with C1 -C12 alkyl, C1 -C12 alkoxy, C1 -C6 alkylthio and/or halogen, or are naphthyl which is unsubstituted or is substituted from one to four times with C1 -C12 alkyl, C1 -C12 alkoxy, C1 -C6 alkylthio and/or halogen, or are biphenyl which is unsubstituted or is substituted from one to four times with C1 -C12 alkyl, C1 -C12 alkoxy, C1 -C6 -alkylthio and/or halogen, or R1, R2 and R3 independently of one another are an O-, S- or N-containing 5- or 6-membered heterocyclic ring, R1 is in addition a group of formula (II), or R1 and R2 are linked to form a ring containing 4 to 10 carbon atoms which is unsubstituted or substituted by 1 to 6 C1 -C4 alkyl groups, R4, R5 and R6 independently of one another are hydrogen or C1 -C18 alkyl, or R5 and R6, together with the carbon atom to which they are attached, form a cyclopropyl, cyclopentyl or cyclohexyl ring, and R7, R8, R9 and R10 independently of one another are hydrogen, C1 -C4 alkyl, C1 -C4 alkoxy or halogen, are suitable as photoinitiators for the photopolymerization of ethylenically unsatured systems. STR1
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- Process for the preparation of 2-(2,4-dihydroxylphenyl)-4,6-bis(2,4-dimehylphenyl)-s-triazine
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2-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-s-triazine is prepared by reacting cyanuric chloride with m-xylene at a temperature of 0°-110° C. in the presence of a Lewis acid and at least one inert chlorinated aromatic solvent to give the intermediate 2-chloro-4,6-bis(2,4-dimethylphenyl)-s-triazine. This intermediate, without being isolated, is then reacted with resorcinol to give the final desired product 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-s-triazine in good yield.
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- α-carbonylphenylacetonitrile derivatives as stabilizers for organic materials
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Compositions comprising an organic material liable to oxidative, thermal and/or actinic degradation and at least one compound of the formula I STR1 are described in which n is 1-6, R, R 1, R 2, R 3 and R 4 are preferably hydrogen and A is a monovalent radical or polyvalent linking moiety.Some of the compounds of the formula I are novel. They are particularly suitable for the stabilization of lubricating oils, metal processing fluids and hydraulic fluids, and of thermoplastics and elastomers.
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- Piperidine-triazine compounds for use as stabilizers for organic materials
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The present invention relates to novel piperidine-triazine compounds of the general formula (I) STR1 in which R1 is e.g. methyl, acetyl or (C1 -C2 alkoxy)carbonyl, A is e.g. a group of the formula (IIa), STR2 in which R3 is e.g. hydrogen, methyl, 2,2,6,6-tetramethyl-4-piperidyl, 1,2,2,6,6-pentamethyl-4-piperidyl or 1-acetyl-2,2,6,6-tetramethyl-4-piperidyl, R4 is e.g. C3 -C6 alkylene, R2 is e.g. a group R1 -A- and n is e.g. a number from 1 to 5. The said compounds are effective as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials.
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- Compounds containing both UV-absorber and 1-hydrocarbyloxy hindered amine moieties and stabilized compositions
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Compounds containing both a UV-absorbing moiety and a 1-hydrocarbyloxy hindered amine moiety are effective stabilizers for protecting polymer compositions against the deleterious effects of actinic light. The UV-absorbing moieties include the substituted 2H-benzotriazoles, s-triazines, acrylates, benzophenones, oxanilides and oxamides.
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