DOCSLIB.ORG

United States Patent Office Patented Oct

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text

Load more

3,213,080 United States Patent Office Patented Oct. 19, 1965 1. 2 from ethyl oxalate and aqueous methylamine solution as 3,213,080 described by O. Wallach Ann. 214, 257 (1882) and then AZO COMPOUNDS FROM AMINOMIDAZOLES reacted with PCls to yield 5-chloro-1-methylimidazole, Melvin S. Bloom and Edmund B. Towne, Kingsport, B.P. 83 C./7 mm. which is treated with nitric acid to Tenn., assignors to Eastman Kodak Company, Roch. yield 5-chloro-1-methylimidazole nitrate M.P. 139-142 ester, N.Y., a corporation of New Jersey C. which is added to conc. sulfuric acid to obtain 5-chloro No Drawing. Filed Nov. 13, 1962, Ser. No. 237,332 1-methyl-4-nitroimidazole by the method of Balaban and 7 Claims. (CI. 260-155) Pyman, J. Chem. Soc. 1564 (1924). The chloro com This invention relates to novel azo compounds obtained pound is then heated with anhydrous ammonia in ethanol by diazotization of aminoimidazoles and coupling with O at 140° C. for 4 hours in a rocking autoclave to obtain coupling components such as aniline coupling compo 76% yield of 5-amino-1-methyl-4-nitroimidazole, M.P. nents. 299 C. (d.) after recrystallization from water. Cal Particular azo compounds of the invention are obtained culated for C4H8ON: C, 33.80; H, 4.23; N, 39.44. by diazotization of 5-amino-4-nitroimidazoles and cou Found: C, 33.98; H, 4.41; N, 39.51. pling the product with aniline, benzomorpholine and 5 tetrahydroquinoline coupling components. EXAMPLE 2. The azo compounds of the invention have the follow (A) Diazotization ing general formula Nitrosylsulfuric acid is prepared by adding 0.90 g. (0.013 mole) of sodium nitrite portionwise to 6 ml. of 20 conc. Sulfonic acid with stirring and allowing the tem perature to rise to 65° C. The solution is then cooled to 5 C., and 10 ml. of a mixture of 1.5 ml. of propionic acid and 8.5 ml. of acetic acid is added dropwise with wherein R= stirring, allowing the temperature to rise to 15° C. and (1) an aniline coupling component residue derived 25 keeping there during the addition. The solution is cooled from, for example, aniline or substituted anilines to 0-5 C. and 1.7 g (0.012 mole) of 5-amino-1-methyl such as m-toluidine, N-methyl-m-toluidine, N,N-di 4-nitroimidazole is added portionwise while stirring, after B-hydroxylethyl-m-chloro-aniline, and other sub which 10 ml. more of the propionic acetic acid mixture is added, keeping the temperature at 0-5 C. The reac stituted anilines described in the examples herein 30 after, or tion mixture is then stirred at 0-5° C. for 2 hours and (2) a benzomorpholine coupling component residue the excess nitrosylsulfuric acid is destroyed by adding 0.1 derived, for example, from N-substituted-2-alkyl and g. of urea. The clear diazonium salt solution is then cou 2,5-dialkylbenzomorpholines described below, or pled as follows: (3) a tetrahydroquinoline coupling component residue (B) Coupling derived, for example, from N-substituted-2-alkyl and To a solution of 0.78 g. (0.004 mole) of N,N-bis(2-hy 2,7-dialkyl-1,2,3,4-tetrahydroquinolines such as de droxyethyl)-m-toluidine in 10 ml. of propionic acid mix scribed below. ture, cooled to 0 C., is added with stirring one-third of R1=a lower alkyl group, including substituted and un the above diazonium salt solution at such a rate that the substituted, straight or branch-chained, alkyl groups 40 temperature remains at 0-5 C. Coupling is allowed to of from 1 to 4 carbon atoms such as methyl, ethyl, proceed for 15 minutes, then the reaction mixture is propyl and butyl. The azo compounds wherein R1 neutralized to Congo Red with anhydrous sodium acetate. is methyl, derived from 5-amino-1-methyl-4-nitro The resulting mixture is taken up in water, filtered and imidazole, comprise a preferred embodiment of our in washed with water yielding 0.64 g. (50%) of an azo dye. vention. 45 The dye gives a red-violet color on cellulose acetate fabric, Representative 5-amino-4-nitroimidazoles useful for violet on nylon and Verel acrylic fabric, and pink on preparing the azo compounds are, for example, 5-amino Kodel polyester fabric. The affinity and fastness of the 1-methyl-4-nitroimidazole, 5-amino-1-propyl-4-nitroimid dye on the various fabrics are satisfactory. The azo dye azole, 5-amino-1-ethyl-4-nitroimidazole and 5-amino-1- has the formula butyl-4-nitroimidazole. 50 N-C-NO2 The azo compounds can be used for dyeing textile ma terials including synthetic polymer fibers, yarns and fabrics H. N/ 8-N-N-O-NCHCH-OH), giving a wide range of shades including red, red-violet and red-blue shades when applied by conventional dyeing 55 ÖH, methods to cellulose ester fibers. The azo compounds dye EXAMPLE 3 polyester fibers and polyamide fibers such as nylon, as One-third of the diazonium salt solution prepared in well as wool and silk fibers. The azo compounds have Example 2A is coupled with 1.09 g. (0.004 mole) of N little affinity for cotton and viscose fibers. When the azo (3,3-difluorobutyl) - N - (2,3-dihydroxypropyl)-m-tolui compounds are used for dyeing such hydrophobic mate 60 dine using the procedure described in Example 2B. There rials they should be free of water-solubilizing groups such is obtained 0.6 g. (35%) of the azo dye. It dyes cellulose as sulfo and carboxyl groups. In general, the dyes have acetate fabric red-violet and nylon fabric violet. The good fastness, for example, to light, washing, gas (atmos affinity and fastness of the dye are satisfactory. pheric fumes) and sublimation. The dyes are useful in application and discharge printing. Example 4 The following examples will serve to illustrate the One-third of the diazonium salt solution prepared in preparation of representative intermediates and azo com Example 2A is coupled with 0.95 g. (0.004 mole) of 2,5- pounds of the invention. dimethyl-1-(2,3-dihydroxypropyl)-benzomorpholine using EXAMPLE. 1 the procedure described in Example 2B. The dye is ob 70 tained in 46% yield (0.7 g.). It dyes cellulose acetate Preparation of 5-amino-1-methyl-4-nitroimidazole fabric violet shades and nylon fabric blue violet shades. N,N-dimethyloxamide M.P. 212-215° C. is prepared The affinity and fastness are satisfactory. 3,213,080 4. 3. depending upon the material being dyed and the formula The azo compounds described in the following fable are of the azo compound. Thus, for example, all the dyes prepared in the manner of the above examples using the will not have the same degree of Eitility for the same indicated nitroimidazole diazonium component and the material. indicated aniline, benzomorpholine and tetrahydroquino Cellulose esters which can be dyed with the azo com line coupling components. The cellulose ester of the dye pounds include cellulose aliphatic carboxylic acid esters ings is a cellulose acetate fabric. having 2 to 4 carbon atoms in the acid groups thereof, by which we mean to include, for example, both partially hydrolyzed and unhydrolyzed cellulose acetate, cellulose Color of Cel IO propionate and cellulose acetate-butyrate. Diazonium Component Coupling Component luloseDyeings Ester Polymeric linear polyester materials of the terephihafate type are illustrative of the linear aromatic polyester textile 5-Amino-1-methyl-4- N-methyl-m-toluidine--------- Red-Wiolet, materials that can be dyed with the new azo compounds nitroimidazole. of our invention. The terephthalate fibers sold under the P0------------------ 6-(N-ethylanilino)ethyl D0. phenyl carbamate. 5 trademarks "Kodel,” “Dacron” and “Terylene,” for ex D0------------------, 6-(N-methyl-m-toluidino)- DO. ample, in the form of filaments, yarn and fabric, for ext ethyl RE carbamate. ample, are illustrative of the polyester textile materials, Do.-----------------, 6-(N-cyangpethyl-m-toluiSinglethyl phenyl carba Do. that can be dyed. Kodel polyester fibers are more particu- - D0------------------ N-Ethyl-N-8-acetyloxyethyl-8: ... D6, larly described in U.S. Patene 2,901,446. Dacron and n-toluidings, s, , , , . 20 Terylene polyester fibers are described, for example, in Do------------------ Ng-cyabethyl-N-benzoyloxyethyl-m-toluidine. Red.. U.S. Patent 2,465,319. The polymeric linear polyester Do------------------ N-6-Cyanoethyl-N-glacétyleoxy-ethyl-m-toluidge. | Red-Violet. materials disclosed in U.S. Patents 2,945,010, 2,957,745 Do------------------ N,N-Dig Hydroxyethyl in- Red. and 2,989,363, for example, can be dyed. The linear aro Do------------------ NNchloroaniline. fig-Hydroxyethyl in. Red Violet.rrr matic polyester materials specifically named have a melt toluidine. i : ing point of at least 200 C. Do------------------ N-8-Hydroxyethyl-N-8-methoxyethylaniline. Ec). Nylon, in fiber, yarn and fabric form is representative D0------------------ N-6-Cyanoethyl-N-hydroxy- Red, of polyamides which can be dyed with the azo com ethylaniline. pounds. D0------------------ N-B-Cyanoethyl-N-ethyl-m- DO. The invention has been described in considerable detail Do------------------ N-(2-Methyl-2,3-dihydroxy-toluidine. Red-Violet.- propyl)aniline. 30 with particular reference to certain preferred embodi Do------------------ N-8-Sulfoethyl-N-phenyl- Do mefs hereof, but it will be understood that variations aniline. and modifications can be effected within the spirit and D0------------------ N-3-Hydroxyethyl-N-6-difluoroethyl-m-toluidine. Red. Scope of the invention as described hereinabove, and as D0------------------ N-Ethyl-N-2,3-dihydroxy- Red-Violet. propyl-m-toluidine. defined in the appended claims. D0------------------ N,N-Di-B-Hydroxyethyl-2- Red-Blue.
Recommended publications
  • Synthesis and in Vitro Antimicrobial and Anthelminthic Evaluation of Naphtholic and Phenolic Azo Dyes

    Synthesis and in Vitro Antimicrobial and Anthelminthic Evaluation of Naphtholic and Phenolic Azo Dyes

    Hindawi Journal of Tropical Medicine Volume 2020, Article ID 4850492, 8 pages https://doi.org/10.1155/2020/4850492 Research Article Synthesis and In Vitro Antimicrobial and Anthelminthic Evaluation of Naphtholic and Phenolic Azo Dyes Joseph Kwasi Adu ,1 Cedric Dzidzor Kodjo Amengor ,2 Nurudeen Mohammed Ibrahim ,1 Cynthia Amaning-Danquah,3 Charles Owusu Ansah,1 Dorcas Dzifa Gbadago,1 and Joseph Sarpong-Agyapong1 1Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences, College of Health Sciences, Kwame Nkrumah University of Science and Technology (KNUST), Kumasi, Ghana 2Department of Pharmaceutical Chemistry, School of Pharmacy, University of Health and Allied Sciences, Ho, Ghana 3Department of Pharmacology, Faculty of Pharmacy and Pharmaceutical Sciences, College of Health Sciences, Kwame Nkrumah University of Science and Technology (KNUST), Kumasi, Ghana Correspondence should be addressed to Joseph Kwasi Adu; [email protected] Received 29 February 2020; Accepted 11 May 2020; Published 1 June 2020 Academic Editor: Sukla Biswas Copyright © 2020 Joseph Kwasi Adu et al. *is is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. *e antimicrobial activity of 2-naphtholic and phenolic azo compounds was determined against seven microbial species, Staphylococcus aureus (ATCC 25923), Streptococcus pyrogenes (clinical), and Enterococcus faecalis (ATCC 29212), Salmonella typhi (clinical), Pseudomonas aeruginosa (ATCC 27853), Escherichia coli (ATCC 251922), and Candida albicans (ATCC 10231), using the high-throughput spot culture growth inhibition assay (HT-SPOTi). *e minimum inhibitory concentrations (MIC) were determined for the active azo dyes. All the azo compounds (A1–B4) were screened for anthelmintic activity against adult Ghanaian earthworms, Hyperiodrilus spp.
  • Experiment 19: Combinatorial Synthesis of Azo Dyes

    Experiment 19: Combinatorial Synthesis of Azo Dyes

    1 Experiment 19: Combinatorial Synthesis of Azo Dyes When a new pharmaceutical is needed to treat a medical condition, modern chemists sometimes utilize a research technique known as combinatorial chemistry to find molecules that have the necessary biological activity. In combinatorial chemistry, a large number of structurally related compounds, called a library, is generated using a single common reaction. The diversity of the compounds in the library can arise from varying the substituents of the molecule, the functional groups or both. For instance, a library of esters can be generated by reacting a variety of different alcohols and carboxylic acids together. Once a library has been generated, the compounds must be screened for the desired activity. An example of a class of drugs that was explored using combinatorial methods are the benzodiazepines, which are used to treat anxiety disorders. Two approaches to combinatorial syntheses are employed. In a parallel synthesis, each compound is prepared individually, and the tests are performed separately on each compound. In a split synthesis, the library of compounds is both prepared and tested in mixtures of the compounds. In the latter case, the results of the tests are complex and usually require deconvolution, although a savings is realized in terms of time and materials. In either case, combinatorial chemistry allows the researcher to draw conclusions about the relationship between structure and function in molecules. The technique has been so successfully exploited that it is now utilized in other areas of chemistry besides pharmaceutical research, including catalysis and materials research. In this experiment, your lab section will generate a library of dye compounds using a parallel synthesis.
  • United States Patent Office 2,083,691 Method of Producing a Kama, Perg)

    United States Patent Office 2,083,691 Method of Producing a Kama, Perg)

    Patented June 15, 1937 2,083,691 UNITED STATES PATENT OFFICE 2,083,691 METHOD OF PRODUCING A KAMA, PERG). Ot - George Lewis Cunningham, Niagara Falls, N. Y. assignor to The Mathieson Alkali Works, no, New York, N. Y., a corporation of Virginia No Drawing. Application 29, 1988 serial No. 105,103 6 Claims. (C123-184) This invention relates to the production of than about 2:1 and the proportion of benzene anhydrous sodium peroxide, Na2O. The inven being sufficient to maintain the hydrazo and azo tion provides a process for manufacturing an compounds in solution. The alcohols and alco hydrous sodium peroxide producing a product of. holates of the alcohols having not more than 4 5 high purity with good economy, with respect both carbon atoms are useful in the process of the to material costs and operating costs. - invention. The oxidation reaction may be typi The generally practiced processes for the pro fled as follows: duction of sodium peroxide all involve the use of metallic sodium and the use of rather high 10 temperatures, and consequently involve high 0. The process is made cyclic by regenerating the costs in both of these respects. The process of hydrazo benzene by reducing the azo benzene re temperaturesthis invention, unnecessary however, makes and, theinstead use ofof high re sulting from the oxidation with a sodium amal quiring metallic sodium, is applicable to the sodi gam, this reaction also producing the sodium . 5 um amalgam produced in conventional mercury alcoholate consumed in the oxidation. This re 5 cathode electrolytic cells. duction reaction may be typified as follows: Manchot & Herzog have hitherto described the production of sodium peroxide by reaction be tween oxygen and a methyl alcohol solution of 20 hydrazo benzene and sodium methylate (Anna For the complete cylic process, the reaction ma 20 len, 1901, 316, 331).
  • Synthesis of New Azo Compounds Based on N-(4- Hydroxypheneyl)Maleimide and N-(4-Methylpheneyl)Maleimide

    Synthesis of New Azo Compounds Based on N-(4- Hydroxypheneyl)Maleimide and N-(4-Methylpheneyl)Maleimide

    Molecules 2010, 15, 7498-7508; doi:10.3390/molecules15107498 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Synthesis of New Azo Compounds Based on N-(4- Hydroxypheneyl)maleimide and N-(4-Methylpheneyl)maleimide Issam Ahmed Mohammed * and Asniza Mustapha School of Industrial Technology, Universiti Sains Malaysia, 11800 Penang, Malaysia Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +604-6533888; Fax: +604-6573678. Received: 1 October 2010; in revised form: 14 October 2010 / Accepted: 18 October 2010 / Published: 25 October 2010 Abstract: Maleic anhydride was reacted with p-aminophenol and p-toluidine in the presence of di-phosphorus pentoxide (P2O5) as a catalyst to produce two compounds: N-(4-hydroxy- phenyl)maleimide (I) and N-(4-methylphenyl)maleimide (II). The new azo compounds I(a-c) and II(a-c) were prepared by the reaction of I and II with three different aromatic amines, namely aniline, p-aminophenol and p-toluidine. The structures of these compounds were confirmed by CHN, FT-IR, 1H-NMR, 13C-NMR, mass spectrum and UV/Vis spectroscopy. Keywords: synthesis; azo compounds; aromatic amines; N-(4-hydroxylpheneyl)maleimide 1. Introduction Small molecules and macromolecules containing imide groups exhibit great electrical properties, good solubility in polar media, resistance to hydrolysis and high thermal stability [1-8]. Due to their excellent properties many efforts have been made to produce different compounds containing imide groups consisting of two carbonyl groups bound to nitrogen. The most common unsubstituted cyclic imides were prepared by heating dicarboxylic acids or their anhydrides with reactants including ammonia, urea, formamide lithium nitride or primary amines [9-12], but the reaction needs to be carried out at high temperatures for efficient ring closure.
  • Reduction of Nitro to Azo Compounds

    Reduction of Nitro to Azo Compounds

    Singh, V. P. , Gates, P., & Engman, L. (2017). Nitro-, Azo- and Amino Derivatives of Ebselen: Synthesis, Structure and Cytoprotective Effects. Journal of Organic Chemistry, 82(1), 313. https://doi.org/10.1021/acs.joc.6b02418 Peer reviewed version Link to published version (if available): 10.1021/acs.joc.6b02418 Link to publication record in Explore Bristol Research PDF-document This is the accepted author manuscript (AAM). The final published version (version of record) is available online via American Chemical Society at http://doi.org/10.1021/acs.joc.6b02418. Please refer to any applicable terms of use of the publisher. University of Bristol - Explore Bristol Research General rights This document is made available in accordance with publisher policies. Please cite only the published version using the reference above. Full terms of use are available: http://www.bristol.ac.uk/red/research-policy/pure/user-guides/ebr-terms/ Nitro-, Azo- and Amino Derivatives of Ebselen: Synthesis, Structure and Cytoprotective Effects Vijay P. Singh,*,† Jia-fei Poon,† Jiajie Yan,† Xi Lu,‡ Marjam Karlsson Ott,‡ Ray J. Butcher,§ Paul J. Gates¶ and Lars Engman*,† †Department of Chemistry – BMC, Uppsala University, Box 576, SE-751 23 Uppsala, Sweden ‡Division of Applied Materials Science, Department of Engineering Sciences, Uppsala University, Sweden §Department of Chemistry, Howard University, Washington D.C. 20059, United States ¶University of Bristol, School of Chemistry, Bristol, BS8 1TS, United Kingdom Abstract: Novel azo-bis-ebselen compounds 7 were prepared by reduction of 7-nitro-2-aryl-1,2- benzisoselenazol-3(2H)-ones 3 and 6 with sodium benzenetellurolate, NaTeC6H5, and by reaction of 2-bromo-3-nitrobenzamides with Na2Se2.
  • Azo Polymerization Initiators Comprehensive Catalog

    Azo Polymerization Initiators Comprehensive Catalog

    Azo Polymerization Initiators Comprehensive Catalog FUJIFILM Wako Pure Chemical Corporation 4-1 Nihonbashi Honcho 2-Chome, Japan Chuo-Ku, Tokyo 103-0023, Japan TEL+81-3-3244-0305 FUJIFILM Wako Chemicals U.S.A. Corporation 1600 Bellwood Road Richmond, USA VA 23237, U.S.A. TEL+1-804-271-7677 FUJIFILM Wako Chemicals Europe GmbH Fuggerstrasse 12 D-41468 Neuss GERMANY Germany TEL+49-2131-311-0 Wako Chemicals (Shanghai) Co., Ltd. C1-C2, 26F, Junyao International Plaza, China 789 Zhaojiabang Road, Shanghai 200032, China TEL+86-21-6407-0511 Specialty Chemicals Web Site http://www.wako-chem.co.jp/kaseihin_en/ 180401 K2 SI 01 Introduction/What is Radical Polymerization? What is Azo Polymerization Initiator? Radical Formation Mechanism 01 INDEX 01 Introduction/What is Radical Polymerization? P1 07 Detailed Explanations 1. Azo Nitrile P11-14 What are Azo Polymerization Initiator? What are Azo Polymerization Initiator? Radical Formation Mechanism P2 2. Azo Ester P15-16 An azo polymerization initiator is a compound having an azo group (R-N=N-R’), which decomposes with heat 3. Azo Amide P17-18 Characteristics of Azo Polymerization Initiators and Comparison with Peroxides P3 02 4. Azo Imidazoline P19-20 and/or light, and forms carbon radical. The formed carbon radical is excellent in reactivity, and progresses polym- Examples of radical reactions using Azo Polymerization Initiators P4 5. Azo Amidine P21-22 erization and halogenation reactions of different types of vinyl monomers. 03 Selection Guide P5-6 6. Macro Azo Initiator P23-26 04 Decomposition
  • Aromatic Amines from Azo Dye Reduction: Status Review with Emphasis on Direct UV Spectrophotometric Detection in Textile Industry Wastewaters

    Aromatic Amines from Azo Dye Reduction: Status Review with Emphasis on Direct UV Spectrophotometric Detection in Textile Industry Wastewaters

    Dyes and Pigments 61 (2004) 121–139 www.elsevier.com/locate/dyepig Aromatic amines from azo dye reduction: status review with emphasis on direct UV spectrophotometric detection in textile industry wastewaters H.M. Pinheiroa, E. Touraudb,*, O. Thomasb aCentro de Engenharia Biolo´gica e Quı´mica, Instituto Superior Te´cnico, Avenida Rovisco Pais, 1049-001 Lisboa, Portugal bLaboratoire de Ge´nie de l’Environnement Industriel, Ecole des Mines d’Ale`s, 6 Avenue de Clavie`res, 30319 Ale`s Cedex, France Received 28 July 2003; received in revised form 10 October 2003; accepted 17 October 2003 Abstract The present status of origins, known hazards, release restrictions and environmental fate of aromatic amines is reviewed. The specific case of aromatic amines arising from the reduction of the azo bond of azo colorants is addressed, with emphasis on the recalcitrance of azo dyes, their demonstrated vulnerability to azo bond reduction through dif- ferent mechanisms and the lack of data on the biodegradability of the resulting amines. The evolution and present array of analysis methods for aromatic amines in water samples is reviewed, highlighting the increased sophistication and sensitivity attained, and referring a few efforts towards fast analysis methodologies. The case for the application of direct ultraviolet spectral analysis with advanced deconvolution techniques for the monitoring of aromatic amines in textile effluent treatment is presented. # 2003 Elsevier Ltd. All rights reserved. Keywords: Aromatic amines; Azo dyes; Hazards; Textile wastewater; Analysis; UV spectra 1. Origin and types of aromatic amines in the some examples of environmentally or health-rela- environment ted important amines together with their major origins and potential impact.
  • Wo 2008/056828 A2

    Wo 2008/056828 A2

    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date PCT 15 May 2008 (15.05.2008) WO 2008/056828 A2 (51) International Patent Classification: (74) Agents: TAKAMATSU, Takeshi et al; Koh-Ei Patent C07D 231/38 (2006.01) Firm, Kawabe Bldg., 7-9, Shimbashi 3-chome, Minato-ku, Tokyo 1050004 (JP). (21) International Application Number: PCT/JP2007/072240 (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (22) International Filing Date: AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, 9 November 2007 (09.1 1.2007) CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, (25) Filing Language: English IN, IS, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, (26) Publication Language: English RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW (30) Priority Data: 2006-304998 10 November 2006 (10.11.2006) JP (84) Designated States (unless otherwise indicated, for every 2006-304999 10 November 2006 (10.11.2006) JP kind of regional protection available): ARIPO (BW, GH, 2007-211816 15 August 2007 (15.08.2007) JP GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), (71) Applicant (for all designated States except US): FUJI- European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FILM Corporation [JP/JP]; 26-30, Nishiazabu 2-chome, FR, GB, GR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, PL, Minato-ku, Tokyo, 1060031 (JP).
  • Synthesis, Antibacterial and Antifungal Activities of Some New Azo Anils Containing Pyrazole Moiety

    Synthesis, Antibacterial and Antifungal Activities of Some New Azo Anils Containing Pyrazole Moiety

    Indian Journal of Chemistry Vol. 53B, February 2014, pp 227-237 Synthesis, antibacterial and antifungal activities of some new azo anils containing pyrazole moiety S Sharma*a, Jasvir Kaurb, Sandeep Kaurb & Poonam Sharmaa aDepartment of Plant Breeding & Genetics, Punjab Agricultural University, Ludhiana 141 004, India bDepartment of Chemistry, Punjab Agricultural University, Ludhiana 141 004, India E-mail: [email protected] Received 11 February 2013; accepted (revised) 31 October 2013 A series of azo compounds namely 3-(Phenylazo) benzaldehyde 1a-f, 3-(4-Nitrophenylazo) benzaldehyde 3a-f and 3- (1,5-Dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl-azo) benzaldehyde 6 were synthesized and then azo anils viz. 3-(Phenylazo)-1,5 dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H pyrazol-4-yl imino methyl benzene 2a-f, 4a-f and 7-9 have been synthesized from azo compounds by reacting with corresponding amines. All the compounds synthesized by conventional method are also prepared by using microwave irradiation method and are characterized by spectroscopic techniques (UV, FTIR and 1H NMR). The synthesized compounds have been screened for antimicrobial activity against bacteria viz. Mesorhizobium sp., Bacillus sp. and Pseudomonas sp., fungus (Ascochyta blight) and yeast (Sacchromycis cerevisiae). The azo anils show minor to moderate activity against bacteria and no activity against fungus and yeast. The activity shown by some compounds is due to substitution of chloro, methoxy or nitro group on phenyl ring or due to some heterocyclic moiety. Keywords: Azo anils, azo compounds, microwave irradiation, Mesorhizobium sp., Bacillus sp., Pseudomonas sp. Azo anil formation is of major importance in and pharmaceutical chemistry with several biological biological processes as many of these involve the applications.
  • Characterising Particulate Organic Nitrogen at a Savannah-Grassland Region in South Africa

    Characterising Particulate Organic Nitrogen at a Savannah-Grassland Region in South Africa

    atmosphere Article Characterising Particulate Organic Nitrogen at A Savannah-Grassland Region in South Africa Wanda Booyens 1, Pieter G. Van Zyl 1,* , Johan P. Beukes 1, Jose Ruiz-Jimenez 2, Matias Kopperi 2, Marja-Liisa Riekkola 2 , Ville Vakkari 1,3, Miroslav Josipovic 1, Markku Kulmala 4 and Lauri Laakso 1,3 1 Unit for Environmental Science and Management, North-West University, Private Bag X6001, Potchefstroom 2520, South Africa 2 Department of Chemistry, University of Helsinki, PO Box 55, 00014 Helsinki, Finland 3 Finnish Meteorological Institute, PO Box 503, 00101 Helsinki, Finland 4 Department of Physical Sciences, University of Helsinki, P.O. Box 64, 00014 Helsinki, Finland * Correspondence: [email protected]; Tel.: +27-18-299-2353 Received: 29 July 2019; Accepted: 20 August 2019; Published: 26 August 2019 Abstract: Although atmospheric organic N compounds are considered to be important, especially in new particle formation and their contribution to brown carbon, these species are not that well understood. This can be partially attributed to their chemical complexity. Therefore, the aim of this study was to assess the characteristics of organic N compounds utilising comprehensive two-dimensional gas chromatography coupled with a time-of-flight mass spectrometer (GCxGC-TOFMS) in aerosol samples that were collected at a savanna-grassland background region and to determine the possible sources. 135 atmospheric organic N compounds were tentatively characterised and semi-quantified, which included amines, nitriles, amides, urea, pyridine derivatives, amino acids, nitro-and nitroso compounds, imines, cyanates and isocyanates, and azo compounds. Amines contributed to 51% of the semi-quantified concentrations, while nitriles, pyridine derivatives, and amides comprised 20%, 11%, and 8%, respectively, of the semi-quantified concentrations.
  • Synthesis and Characterization of Azo Compounds and Study of the Effect of Substituents on Their Liquid Crystalline Behavior

    Synthesis and Characterization of Azo Compounds and Study of the Effect of Substituents on Their Liquid Crystalline Behavior

    Molecules 2010, 15, 5620-5628; doi:10.3390/molecules15085620 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Synthesis and Characterization of Azo Compounds and Study of the Effect of Substituents on Their Liquid Crystalline Behavior Uhood J. Al-Hamdani *, Tarik E. Gassim and Howraa H. Radhy Department of Chemistry, College of Education, Basrah University, Basrah, Iraq ∗ Author to whom correspondence should be addressed; E-Mail:[email protected]; Tel.: +9647712616545. Received: 1 July 2010; in revised form: 4 August 2010 / Accepted: 12 August 2010 / Published: 13 August 2010 Abstract: In this paper we present six select mesomorphic azo compounds distinguished by the presence of diverse substituents on a central benzene nucleus. All the synthesized compounds exhibit enantiotropic mesophases. The mesomorphic properties of the substituted compounds were compared with those of the unsubstituted parent compound to evaluate the effect of the nature and position of the substituents on mesomorphism. Keywords: azo; lateral group; liquid crystal Introduction Until 1983 it was generally accepted that substituents diminish the mesogenic properties of a compound, with the extent of the effect depending on their size. Cox et al. [1] synthesized nematogens in which a phenyl side group was attached without a spacer. Mesogens with aromatic substituents have been prepared [2-7]. Recently a homologous series of mesogenic azo compounds containing three rings in the main core and substituted with aromatic or hydroxyl groups on the central benzene nucleus was reported [8,9]. The mesogenic homologous series with hydroxyl group substituents exhibited nematic mesomorphism, whereas the homologous series with aromatic branches exhibited smectogenic tendencies.
  • Azo Compound, Aqueous Solution, Ink Composition, Ink for Inkjet Recording, Inkjet Recording Method, Ink Cartridge for Inkjet Recording, and Inkjet Recorded Material

    Azo Compound, Aqueous Solution, Ink Composition, Ink for Inkjet Recording, Inkjet Recording Method, Ink Cartridge for Inkjet Recording, and Inkjet Recorded Material

    (19) TZZ _ _T (11) EP 2 712 894 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 02.04.2014 Bulletin 2014/14 C09B 31/153 (2006.01) C09D 11/00 (2014.01) (21) Application number: 13185960.5 (22) Date of filing: 25.09.2013 (84) Designated Contracting States: • Hayashi, Shinya AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Kanagawa 258-8577 (JP) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • Iizumi, Takashi PL PT RO RS SE SI SK SM TR Kanagawa 258-8577 (JP) Designated Extension States: • Yamada, Hiroshi BA ME Kanagawa 258-8577 (JP) • Norizuki, Yutaro (30) Priority: 26.09.2012 JP 2012212754 Kanagawa 258-8577 (JP) 14.03.2013 JP 2013051807 • Amasaki, Ichiro 20.09.2013 JP 2013196181 Kanagawa 258-8577 (JP) • Tanaka, Shigeaki (71) Applicant: Fujifilm Corporation Kanagawa 258-8577 (JP) Minato-ku Tokyo (JP) (74) Representative: Morpeth, Fraser Forrest Fujifilm Imaging Colorants Limited (72) Inventors: Intellectual Property Group • Yagi, Kazunari P.O. Box 42 Kanagawa 258-8577 (JP) Hexagon Tower Blackley, Manchester M9 8ZS (GB) (54) Azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording, and inkjet recorded material (57) There is provided a compound represented by the following formula (1): wherein each of R1a to R1k independently represents a hydrogen atom or a monovalent substituent, the substituents may combine with each other to form a ring, each of M1a and M1b independently represents a hydrogen atom or a monovalent counter cation, Y1 represents a nitrogen atom or a carbon atom having a hydrogen atom or monovalent substituent,1 A represents an aromatic group, and the aromatic group represented by A 1 may contain a heteroatom or may have a substituent.