- BENZOTRIAZOLE DERIVATIVE COMPOUNDS
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PROBLEM TO BE SOLVED: To provide novel compounds that may be wavelength conversion materials exhibiting an excellent wavelength conversion property of efficiently converting ultraviolet light to blue light in solution and film states, and exhibiting excellent light fastness of not deteriorating by irradiation with the ultraviolet light. SOLUTION: The invention provides benzotriazole derivative compounds of the general formula in the figure. [Preferably, R1 is a formyl group or alkylcarbonyl group; R2 is a hydrogen atom, alkyl group, carboxyalkyl group, alkyloxycarbonylalkyl group, hydroxyalkyl group, or alkylcarbonyloxyalkyl group; and R3 is a hydrogen atom or halogen atom.] SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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- Preparation method of ultraviolet light absorber UV-PS
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The invention discloses a preparation method of ultraviolet light absorber UV-PS as indicated in the formula (I). The preparation method comprises the steps of 1, mixing ortho-nitroaniline with hydrochloric acid, then adding sodium nitrite, and conducting a reaction for 1-3 hours with the temperature preserved; adding urea for a reaction, so that a diazonium salt solution is obtained; 2, mixing and dissolving first solvent, an auxiliary agent and tert-butylphenol, lowering the temperature, adding the diazonium salt solution, adding alkali, and preserving the temperature for 1-3 hours; 3, conducting purification for the first time on a mixed solution obtained in step 2, so that azo matter as indicated in the formula (II) is obtained; 4, mixing the azo matter, alkali and second solvent for a reaction, raising the temperature to 60-70 DEG C, adding glucose, conducting backflow for 2-4 hours, and adding acid; 5, conducting purification for the second time on a mixed solution obtained in step 4, so that an intermediate as indicated in the formula (III) is obtained; 6, mixing the intermediate, third solvent and an auxiliary agent for a reaction, raising the temperature to 80-85 DEG C, adding zinc powder, conducting a reaction for 2.5-3 hours, and adding adsorbent; 7, conducting purification for the third time on a mixed solution obtained in step 6, so that the ultraviolet light absorber UV-PS as indicated in the formula (I) is obtained. According to the preparation method of the ultraviolet light absorber UV-PS, a fractional-step method is adopted, reactant in each step can fully react, the yield of products of all steps is guaranteed, and the yield of a final product is remarkably raised.
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Paragraph 0046-0047
(2017/04/11)
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- Preparation of 2-aryl-2H-benzotriazoles by zinc-mediated reductive cyclization of o-nitrophenylazophenols in aqueous media without the use of organic solvents
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Zinc powder-mediated reductive cyclization of o-nitrophenylazophenols in alkaline solution affords the corresponding 2-aryl-2H-benzotriazoles in high yields under mild reaction conditions. No organic solvents are used in the reaction and only minimal amounts in the work-up.
- Liu, Guo-Bin,Zhao, Hong-Yun,Yang, Hong-Jie,Gao, Xiang,Li, Miao-Kui,Thiemann, Thies
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p. 1637 - 1640
(2008/02/11)
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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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- 2-(2′-hydroxyphenyl)benzotriazoles used as U.V. stabilizers
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2-(2′-hydroxyphenyl)benzotriazoles having general formula (I). The above 2-(2′-hydroxyphenyl)benzotriazoles are useful as light stabilizers for organic polymers.
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- 2-(2′-hydroxyphenyl) benzotriazoles containing a 2,4-imidazolidinedione group and process for their preparation
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2-(2′-hydroxyphenyl)benzotriazoles having general formula (I). The above 2-(2′-hydroyzphenyl)benzotriazoles having general formula (I) are useful as heat, oxygen and light stabilizers for organic polymers. In particular they are useful as UV stabilizers for organic polymers.
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- Liposomogenic UV absorbers
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PCT No. PCT/EP96/00959 Sec. 371 Date Sep. 15, 1997 Sec. 102(e) Date Sep. 15, 1997 PCT Filed Mar. 7, 1996 PCT Pub. No. WO96/29302 PCT Pub. Date Sep. 26, 1996There are described liposomogenic UV absorbers, comprising a hydrophilic head group (=Z), a spacer (=W), a UV chromophore (Q) having an absorption in the range from 285 to 400 nm and at least one hydrophobic tail group (=A) of the formula (1), in which A1 and A2, independently of one another, are a hydrophobic radical, Q is a UV chromophore, W is an organic radical, Z1 and Z2, independently of one another, are a hydrophilic radical, n1 and n2, independently of one another, are a number from 0 to 4, n1=n2=0 not being additionally included, p is 1 or 2, q is a number from 0 to 3, r1 is 1 or 2, r2 is 0 or 1, and s1 is a number from 1 to 3. The liposomogenic UV absorbers according to the invention are preferably used as sunscreen agents in cosmetic preparations. They are capable of self-organization into bimolecular layers, and can thereby penetrate into the stratum corneum to a high extent and behave there in an extremely wash-resistant manner.
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- Method of preparing 2-phenyl benzotriazoles
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A method of preparing 2-phenylbenzotriazoles expressed by Formula I: STR1 (wherein R1 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, a carboxyl group or a sulfonic acid group; R2 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxyl group having 1 to 4 carbon atoms; R3 denotes a hydrogen or chlorine atom, an alkyl group having 1 to 12 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, a phenyl group, a phenyl group substituted by an alkyl group having 1 to 8 carbon atoms, a phenoxy group or a phenylalkyl group with an alkyl part having 1 to 4 carbon atoms; R4 denotes a hydrogen or chlorine atom, a hydroxyl group or an alkoxyl group having 1 to 4 carbon atoms; and R5 denotes a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or a phenylalkyl group with an alkyl part having 1 to 4 carbon atoms) comprises reduction with hydrogen of o-nitroazobenzene derivatives expressed by Formula II: STR2 (wherein R1, R2, R3, R4 and R5 each denote the same as in Formula I), the reduction being effected in a solvent containing water.
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- Fluorenol catalyzed reduction of o-nitroazobenzenes and 2-aryl-2H-benzotriazole-N-oxides
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A process for producing 2-aryl-2H-benzotriazole by reducing an o-nitroazobenzene with a saccharide having an aldehyde group as a reducing agent in the presence of fluorenol as a catalyst and a base in solution. The reaction is conducted at a temperature of from about 60° C. to about 80° C. The reaction time and amount of catalyst is significantly reduced compared to the use of an aromatic ketone catalyst. The invention also provides a method for producing 2-aryl-2H-benzotriazole by reducing a 2-aryl-2H-benzotriazole-N-oxide intermediate with a saccharide having an aldehyde group as a reducing agent, in the presence of fluorenol under similar conditions.
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- SYNTHESIS OF SOME BENZOTRIAZOLES BY DEOXYGENATION OF o-NITROPHENYLAZO COMPOUNDS BY TERTIARY AMINES AND CO
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NEt3 promotes the deoxygenation of specific ortho-nitrophenylazo compounds affording benzotriazoles in good yields and selectivities. The role of the amine is examined in the deoxygenation process with CO as the final oxygen acceptor.
- Pizzotti, Maddalena,Ragaini, Fabio,Cenini, Sergio
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p. 683 - 686
(2007/10/02)
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- Method of preparing 2-phenyl benezothriazoles
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A method of preparing 2-phenylbenzotriazoles expressed by Formula I: STR1 (wherein R1 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, a carboxyl group or a sulfonic acid group; R2 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxyl group having 1 to 4 carbon atoms; R3 denotes a hydrogen or chlorine atom, an alkyl group having 1 to 12 carbon atoms, a lower alkoxy group having 1 to 4 carbon atoms, a phenyl group, a phenyl group substituted by an alkyl group having 1 to 8 carbon atoms, a phenoxy group or a phenylalkyl group with an alkyl part having 1 to 4 carbon atoms; R4 denotes a hydrogen or chlorine atom, a hydroxyl group or an alkoxyl group having 1 to 4 carbon atoms; and R5 denotes a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or a phenylalkyl group with an alkyl part having 1 to 4 carbon atoms) comprises reducing with hydrogen 2-phenylbenzotriazole-N-oxides expressed by Formula II: STR2 (wherein R1, R2, R3, R4 and R5 each denotes the same as in Formula I).
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- Method for preparing 2-phenylbenzotriazoles and 2-phenylbenzotriazole-N-oxides
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This invention relates to a method for preparing a 2-phenylbenzotriazole of formula I, STR1 (wherein R1 represents hydrogen or chlorine atom, a lower alkyl group having a carbon number of 1 to 4, a lower alkoxyl group having a carbon number of 1 to 4, carboxyl group, or sulfonic acid group; R2 represents hydrogen or chlorine atom, a lower alkyl group having a carbon number of 1 to 4, or a lower alkoxyl group having a carbon number of 1 to 4; R3 represents hydrogen or chlorine atom, an alkyl group having a carbon number of 1 to 12, a lower alkoxyl group having a carbon number of 1 to 4, phenyl group, a phenyl group substituted with an alkyl group having a carbon number of 1 to 8, phenoxy group, or a phenylalkyl group, the alkyl part of which has a carbon number of 1 to 4; R4 represents hydrogen or chlorine atom, hydroxyl group, or a lower alkoxyl group having a carbon number of 1 to 4; and R5 represents hydrogen atom, an alkyl group having a carbon number of 1 to 12, or a phenylalkyl group, the alkyl part of which has a carbon number of 1 to 4), which comprises reducing an o-nitroazobenzene of formula III, STR2 (wherein R1, R2, R3, R4 and R5 are as defined above) with an aldehyde reducing agent in the presence of an aromatic ketone catalyst and base. This invention further relates to a method for preparing a 2-phenylbenzotriazole of formula I as derfined above, which comprises reducing 1 mole 2-phenylbenzotriazole-N-oxide of formula II, STR3 (wherein R1, R2, R3, R4 and R5 are as defined above) with 1 to 4 mole aldehyde in the presence of an aromatic ketone catalyst and base. This invention still further relates to a method for preparing a 2-phenylbenzotriazole-N-oxide of formula II as defined above, which comprises reducing 1 mole o-nitroazobenzene of formula III as defined above with 1 to 2 mole aldehyde in the presence of an aromatic ketone catalyst and base.
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- Method for preparing 2-phenylbenzotriazoles and 2-phenylbenzotriazole-N-oxides
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A method for preparing a 2-phenylbenzotriazole of formula I wherein R1 is H, Cl, C1-4alkyl, C1-4alkoxy, COOH or SO3H; R2 is H, Cl, C1-4alkyl or C1-4alkoxy; R3 is H, Cl, C1-12alkyl, C1-4alkoxy, phenyl, (C1-8alkyl)phenyl, phenoxy or phenyl(C1-4alkyl); R4 is H, Cl, OH or C1-4alkoxy; and R5 is H, C1-12alkyl or phenyl(C1-4alkyl), comprises reducing a nitroazobenzene of formula III = wherein R1, R2, R3, R4 and R5 are as defined above, with a saccharide in the presence of a hydrogen transfer catalyst and base. This method can be conducted in one or two steps. The individual steps, the first from the nitroazobenzene to a 2-phenylbenzotriazole-N-oxide of formula II and the second (II→I) are independent aspects of the invention.
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- Preparation of 2-(2H-Benzotriazol-2-yl)phenols by the Reduction of 2-phenols with Thiourea S,S-Dioxide
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The reduction of 2-phenols 1 with thiourea S,S-dioxide and sodium hydroxide in a mixture of isopropyl alcohol and water at reflux provides 2-(2H-benzotriazol-2-yl)phenols 3 in excellent yields.
- Tanimoto, Shigeo,Kamano, Takayoshi
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p. 647 - 649
(2007/10/02)
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- Preparation of Some 2-(2' H-Benzotriazol-2'-yl)phenol Ultraviolet Absorbers: Application of the Transalkylation Reaction
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When 2-(2' H-benzotriazol-2'-yl)phenols containing t-alkyl substituents are warmed in toluene solution with an aluminium chloride/nitromethane catalyst, the t-alkyl groups are transferred to the solvent (toluene).This transalkylation reaction has been used to prepare not readily accessible or previously inaccessible 2-(2' H-benzotriazol-2'-yl)phenols, a class of ultraviolet absorbers widely used in industry.
- Rosevear, Judi,Wilshire, John F.K.
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p. 1163 - 1176
(2007/10/02)
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- High molecular weight piperidine derivatives as UV stabilizers
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Substituted high molecular weight hindered spiropiperidine compounds and polymer compositions stabilized by these compounds. The spiropiperidine compounds are prepared by reacting hindered 4-piperidinone hydrochloride with an activated benzene, such as resorcinol, in an acid medium.
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