DOCSLIB.ORG

Flavanthrone – New Ligand with Accessible Radical Anion and Dianion States. Preparation of Zwitter-Ionic {(Cp2v)2(Flavanthrone)} and {(Cp2v)2(Chloranil)} Complexes

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Flavanthrone – New Ligand with Accessible Radical Anion and Dianion States. Preparation of Zwitter-Ionic {(Cp2v)2(Flavanthrone)} and {(Cp2v)2(Chloranil)} Complexes New Journal of Chemistry Flavanthrone – new ligand with accessible radical anion and dianion states. Preparation of zwitter-ionic {(Cp2V)2(Flavanthrone)} and {(Cp2V)2(Chloranil)} complexes Journal: New Journal of Chemistry Manuscript ID NJ-ART-03-2020-001208.R1 Article Type: Paper Date Submitted by the 11-May-2020 Author: Complete List of Authors: Konarev, Dmitri; Institute of Problems of Chemical Physics RAS, Andronov, Mikhail ; Institute of Problems of Chemical Physics RAS, Chernogolovka, Moscow region, 142432 Russia, Kinetics and Catalysis; Moscow State University, Leninskie Gory,119991 Moscow, Russia Batov, Mikhail; Moscow State University, Kuz`min, Alexey; Institute of Solid State Physics RAS, Khasanov, Salavat; Institute of Solid State Physics RAS, Shestakov, Alexander; Institute of Problems of Chemical Physics RAS Otsuka, Akihiro; Kyoto University - Yoshida Campus, Department of Chemistry; Research Center for Low Temperature and Materials Sciences Yamochi, Hideki; Kyoto University, Kitagawa, Hiroshi; Kyoto University, Department of Chemistry Lyubovskaya, Rimma; Institute of Problems of Chemical Physics RAS, Page 1 of 12 PleaseNew doJournal not adjustof Chemistry margins 1 2 3 4 Journal Name 5 6 7 8 ARTICLE 9 10 11 Received 00th January 20xx, 12 Flavanthrone – new ligand with accessible radical anion and 13 dianion states. Preparation of zwitter-ionic 14 15 {(Cp2V)2(Flavanthrone)} and {(Cp2V)2(Chloranil)} complexes Accepted 00th January 20xx 16 17 DOI: 10.1039/x0xx00000x 18 a a,c a,c b www.rsc.org/ Dmitri V. Konarev,* Mikhail G. Andronov, Mikhail S. Batov, Alexey V. Kuzmin, 19 Salavat S. Khasanov,b Alexander F. Shestakov,a,c Akihiro Otsuka,d,e Hideki Yamochi,d,e 20 Hiroshi Kitagawa,d and Rimma N. Lyubovskayaa 21 22 Dye flavanthrone (Vat yellow 1) can be reduced to radical anions and dianions crystallized in form of + + 2 + 2 23 {Crypt(Na )}(Flavanthrone ) 2C6H4Cl2 (1), (Bu4P )2(Flavanthrone ) 0.5C6H4Cl2 (2), and (Bu4P )2(Flavanthrone ) (3) salts, + 24 where {Crypt(Na )} is sodium cryptate[2.2.2]. The reduction of flavanthrone is accompanied by elongation of the carbonyl 25 C=O bonds and shortening of the C-C(O) bonds. Reduction is manifested in optical spectra by essential (more than 200 26 nm) red shift of the intense band of pristine flavanthrone at 440 nm. A new intense band appears for the flavanthrone 27 radical anion at 960 nm in the NIR range but this band decreases in intensity for dianion salts 2 and 3. Salt 1 contains 28 flavanthrone chains of three types in which they are bonded by the C=O H hydrogen bonds of 2.26-2.53 Å length. 29 Although direct - interactions between flavanthrone (S = 1/2) are absent, hydrogen bonds between them provide 2 30 weak antiferromagnetic coupling of spins in the flavanthrone layers with Weiss temperature of -5 K. Flavanthrone 31 dianions are diamagnetic and EPR silent. Interaction of flavanthrone with two equivalents of vanadocene yields zwitter- + 2 32 ionic {(Cp2V )2(Flavanthrone )} 2C6H4Cl2 (4) complex bonded by short V-O(flavanthrone) bonds. These molecules are 2 33 packed in uniform stacks with effective - interaction between flavanthrone units (having the interplanar distance of III 2 34 3.38 Å). Paramagnetic V centers with S = 1 spin state are separated in 4 by diamagnetic flavanthrone dianions and show + 2 35 weak magnetic coupling with Weiss temperature of -5 K. Zwitter-ionic {(Cp2V )2(QCl4 )} complex (5) with smaller 2 36 diamagnetic chloranil spacer shows slightly stronger magnetic coupling with Weiss temperature of -7 K. Modeling of III 37 magnetic behavior of 4 and 5 by the appropriate van Vleck equation indicates stronger magnetic coupling between V in 5 -1 -1 38 (J = -3.3 cm ) in comparison with 4 (J = -2.0 cm ). 39 high conductivity at their appropriate packing in a crystal or 40 Introduction participate in magnetic coupling of spins. The dyes having 41 hetero atoms such as carbonyl and/or hydroxy oxygen can Organic dyes can be used not only as colorants for fabrics and 42 coordinate transition metals. Their ability to form radical anion clothes1 but now they find application as new electronic 43 and dianion species as well as in some cases possibility of their materials, materials for rechargeable batteries, and photo- and 44 deprotonation can essentially modify optical and magnetic semiconductors.2 These dyes are capable of redox transitions 45 properties of dye ligands as well as possible ways of and, therefore, unpaired electrons can be introduced into 46 coordination of transition metals to them. As an example, these dyes. Such radical anion species potentially can manifest 47 indigo and thioindigo can form radical anions and dianions in 48 solution3 and solid state4. Recently radical anion salt 49 aInstitute of Problems of Chemical Physics RAS, Chernogolovka, Moscow region, O O O 1 50 142432 Russia; 2 2 bInstitute of Solid State Physics RAS, Chernogolovka, Moscow region, 142432 51 4 Russia; N N N 52 c 3 3 Moscow State University, Leninskie Gory,119991 Moscow, Russia; N N N 53 dDivision of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, 4 Kyoto 606-8502, Japan; 54 2 2 eResearch Center for Low Temperature and Materials Sciences, Kyoto University, 1 O 55 Sakyo-ku, Kyoto 606-8501, Japan. O O 56 Electronic supplementary information (ESI) available: IR spectra of pristine neutral radical anion dianion compounds and compounds 1-5, figures with structure of salts 2 and 3, UV-visible- 57 NIR spectrum of 3, data of SQUID measurements for compounds 1, 4 and 5. CCDC Scheme 1. Molecular structure of neutral flavanthrone and its radical anion 58 numbers are 1985695-1985698 and 1985700. For ESI and crystallographic data in and dianion forms. CIF or other electronic format see DOI: ….. 59 1 60 PleaseNew doJournal not adjustof Chemistry margins Page 2 of 12 1 ARTICLE Journal Name 2 3 {cryptand[2.2.2](K)}6{trans-indigo}75.5C6H4Cl2 of indigo was 4 obtained in a crystalline form, and it was shown that indigo 5 can magnetically interact through short hydrogen bonds.4c Table 1. Composition and charge state of the components in 1-5. Coordination of transition metals to neutral or dianionic indigo 6 1 {Crypt(Na+)}(Flavanthrone)2C H Cl and thioindigo can change conformation from trans to cis.4a, 4b, 6 4 2 7 2 (Bu P+) (Flavanthrone2)0.5C H Cl 5e, 5g In this case metal centers coordinate simultaneously to 4 2 6 4 2 8 3 (Bu P+) (Flavanthrone2) two oxygen atoms of the dyes in the complexes with 4 2 9 4 (Cp V+) (Flavanthrone2)2C H Cl 3a,b 2 2 6 4 2 chromium pentamethylcyclopentadienyl or titanium(IV) and + 2 10 5 (Cp2V )2(QCl4 ) 11 indium(III) phthalocyanines5g. Deprotonation of indigo opens 12 an additional way to the formation of coordination complexes The composition of the obtained compounds is presented in 13 with one or two metal centers.5a-d Some of these complexes Table 1. Suitable reagents for selective reduction of 14 show properties of single molecule magnets,5d intense flavanthrone to the monoanionic radical state are a 15 absorption associated with metal-to-ligand charge transfer or combination of sodium fluorenone ketyl and cryptand[2.2.2]. 16 reversible charge transfer between two ligands coordinated to Starting flavanthrone is only poorly soluble in o- 17 one metal center where one of two ligands is a deprotonated dichlorobenzene but dissolves completely after the reduction 18 cis-indigo dianion.4a forming deep blue-greenish solution. Slow mixing of this 19 However, the number of organic dyes studied under solution with n-hexane provides precipitation of the crystals of + 20 reduction and in coordination complexes with transition {Crypt(Na )}(Flavanthrone )2C6H4Cl2 (1), the composition of 21 metals is still rather limited. As we discussed above they are which was determined from X-ray diffraction on single crystal. 22 limited mainly to the dyes of indigo type4,5 or chemically The reaction of flavanthrone with two equivalents of strong 23 modified molecules based on them (so-called “N-indigo” organometallic reductants NaRe(CO)5 and NaCpCo(CO)2 in the 24 derivatives)6. Nevertheless, it is obvious that vat dyes can be presence of two equivalents of tetrabutylphosphonium 25 reduced to the radical anion and dianion state and potentially bromide was also studied. Organometallic reductants were 26 they can be involved in coordination complexes with transition chosen to coordinate the Re(CO)5 or CpCo(CO)2 fragments to 27 metals and lanthanides due to the presence of carbonyl the oxygen atoms of the dye. Previously it was shown that 28 groups, which can be transferred to terminal ketyls (CO) or flavanthrone can form complexes with iron at 12 29 the O groups under reduction. Such groups can efficiently electroreduction. Crystals obtained in both syntheses have 30 bind to various metal centers.7 different shape and unit cell parameters. However, IR spectra 31 Flavanthrone is well-known vat dye of anthraquinone type and X-ray diffraction analyses show that metal-containing 32 synthesized in 1903.8 However, later it was practically not fragments are not introduced into these salts and their 33 studied. Its structure, optical properties in solution and difference is only due to different content of solvent 34 photoconductivity are investigated9 and several soluble molecules. Solvent molecules are present in + 2 35 flavanthrone derivatives are obtained for light emitting (Bu4P )2(Flavanthrone )0.5C6H4Cl2 (2) obtained with 2d + 2 36 diods . Based on optical absorption and cyclic voltammetry it NaRe(CO)5 and are absent in (Bu4P )2(Flavanthrone ) (3) 37 was found that flavanthrone has high electron affinity (EA = obtained with NaCpCo(CO)2. Therefore, organometallic 38 3.6 eV) and high oxidation potential (IP = 6.3 eV).10 In this reagents play only a role of reductants in these reactions and 39 study, we demonstrate the reduction of flavanthrone to the affect crystallization of the salts with no inclusion into the 40 radical anions and dianions (Scheme 1) and the isolation of crystals.
Load more

Recommended publications
  • Making Basic Period Pigments at Home
    Making Basic Period Pigments at Home KWHSS – July 2019 Barony of Coeur d’Ennui Kingdom of Calontir Mistress Aidan Cocrinn, O.L., Barony of Forgotten Sea, Kingdom of Calontir Mka Holly Cochran [email protected] Contents Introduction .................................................................................................................................................. 3 Safety Rules: .................................................................................................................................................. 4 Basic References ........................................................................................................................................... 5 Other important references:..................................................................................................................... 6 Blacks ............................................................................................................................................................ 8 Lamp black ................................................................................................................................................ 8 Vine black .................................................................................................................................................. 9 Bone Black ................................................................................................................................................. 9 Whites ........................................................................................................................................................
    [Show full text]
  • Ayesha Altaf Env Sci 2018 LCWU PRR.Pdf
    NATURAL COLORANTS AS PHOTOSENSITIZER FOR DYE-SENSITIZED SOLAR CELLS (DSSCs) FOR GREEN ECONOMY By Ayesha Altaf DEPARTMENT OF ENVIRONMENTAL SCIENCE LAHORE COLLEGE FOR WOMEN UNIVERSITY, LAHORE, PAKISTAN 2018 NATURAL COLORANTS AS PHOTOSENSITIZER FOR DYE-SENSITIZED SOLAR CELLS (DSSCs) FOR GREEN ECONOMY A THESIS SUBMITTED TO LAHORE COLLEGE FOR WOMEN UNIVERSITY IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSPHY IN ENVIRONMENTAL SCIENCE By Ayesha Altaf Registration No. 14-PhD/LCWU-193 Supervisor: Prof. Dr. Tahira Aziz Mughal Co-Supervisor: Dr. Zafar Iqbal DEPARTMENT OF ENVIRONMENTAL SCIENCE LAHORE COLLEGE FOR WOMEN UNIVERSITY, LAHORE, PAKISTAN 2018 Declaration Form This is to certify that the research work described in this thesis submitted by Mrs. Ayesha Altaf to Department of Environmental Sciences, Lahore College for Women University has been carried out under my direct supervision. I have personally gone through the raw data and certify the correctness and authenticity of all results reported herein. I further certify that thesis data have not been use in part or full, in a manuscript already submitted or in the process of submission in Partial/complete fulfillment of the award of any other degree from any other institution or home or abroad. I also certified that the enclosed manuscript, has been to paid under my supervision and I endorse its evaluation for the award of Ph.D degree through the official procedure of University. ________________ __________________ Prof. Dr. Tahira Aziz Mughal Dr. Zafar Iqbal (Supervisor) (Co- Supervisor) Date: ___________ Date: ___________ _________________ Date: ___________ External Examiner ________________ Date: ___________ Chairperson Department of Environmental Science LCWU, Lahore Stamp ______________________ Controller of Examination LCWU, Lahore.
    [Show full text]
  • Evaluation of the Dyeability of the New Eco-Friendly Regenerated Cellulose
    Fibers and Polymers 2008, Vol.9, No.2, 152-159 Evaluation of the Dyeability of the New Eco-friendly Regenerated Cellulose Woo Sub Shim*, Joonseok Koh1, Jung Jin Lee2, Ik Soo Kim3, and Jae Pil Kim4 Textile Engineering, Chemistry & Science Department, North Carolina State University, Raleigh, NC 27695-8301, USA 1Department of Textile Engineering, Konkuk University, Seoul 143-701, Korea 2Department of Textile Engineering, Dankook University, Seoul 140-714, Korea 3Chemical R&D Center, SK Chemicals, Suwon 440-745, Korea 4School of Material Science & Engineering, Seoul National University, Seoul 151-742, Korea (Received September 3, 2007; Revised November 7, 2007; Accepted January 12, 2008) Abstract: Three commercial dyes-direct, reactive, and vat dye-were applied to the new regenerated cellulose fiber which was prepared from cellulose acetate fiber through the hydrolysis of acetyl groups with an environmentally friendly manufacturing process. The effect of salt, alkali, liquor ratio, temperature, and leveling agent on the dyeing behavior and fastness were eval- uated and compared with regular viscose rayon. From the results, we found that new regenerated cellulose fiber exhibited bet- ter dyeability and fastness than regular viscose rayon. Keywords: Regenerated cellulose fiber, Dye, Dyeability, Fastness, Viscose rayon Introduction absorption processing [7]. We claim this regenerated cellulose fiber offers environ- Cellulose as a raw material has been used in fiber form as mental advantages over other conventional regenerated a component of paper, textiles, film, and flexible packing fibers because it dose not emit toxic materials such as carbon material. The excellent fiber-forming properties of the cellulose disulfide and heavy metal ions [8].
    [Show full text]
  • Imports of Benzenoid Chemicals and Products
    UNITED STATES TARIFF COMMISSION Washington IMPORTS OF BENZENOID CHEMICALS AND PRODUCTS 1 9 6 5 United States General Imports of Intermediates, Dyes, Medicinals, Flavor and Perfume Materials, and Other Finished Benzenoid Products Entered in 1965 Under Schedule 4, Parts 1B and 1C of The Tariff Schedules of the United States TC Publication 183 Washington, D.C. July 1966 UNITED STATES TARIFF COMMISSION Paul Kaplowitz, Chairman Glenn W. Sutton, Vice Chairman James W. Culliton Dan H. Fenn, Jr. Penelope H. Thunberg Donn N. Bent, Secretary Address all communications to United States Tariff Commission Washington, D. C. 20436 UNITED STATES.TARIFF COMMISSION Washington IMPORTS OF BENZENOID CHEMICALS AND PRODUCTS 1 9 6 5 United States General Imports of Intermediates, Dyes, Medicinals, Flavor and Perfume Materials, and Other Finished Benzenoid Products Entered in 1965 Under Schedule 4, Parts 1B and 1C of The Tariff Schedules of the United States United States Tariff Commission July, 1966 AUG'1, 1966 CONTENTS (Imports under TSUS, Schedule 4, Parts lB and 10) Table N o. Page 1. Benzenoid intermediates: Summary of U.S. general imports entered under Part 1B, TSUS, by competitive status, 1965-- 4 2. Benzenoid intermediates: U.S. general imports e-tered under Part 1B, TSUS, by country of origin, 1965 and 1964-- 4 3. Benzenoid intermediates: U.S. general imports entered under Part 1B, TSUS, showing competitive status, 1965----- 6 4. Finished benzenoid products: Summary of U.S. general im- ports entered under Part 10, TSUS, by competitive status, 23 5. Finished benzenoid products: U.S. general imports entered under Part 10, TSUS, by country of origin, 1965 and 1964-- 24 6.
    [Show full text]
  • Colour Chemistry 2Nd Edition
    Colour Chemistry 2nd edition Robert M Christie School of Textiles & Design, Heriot-Watt University, UK and Department of Chemistry, King Abdulaziz University, Saudi Arabia Email: [email protected] Print ISBN: 978-1-84973-328-1 A catalogue record for this book is available from the British Library r R M Christie 2015 All rights reserved Apart from fair dealing for the purposes of research for non-commercial purposes or for private study, criticism or review, as permitted under the Copyright, Designs and Patents Act 1988 and the Copyright and Related Rights Regulations 2003, this publication may not be reproduced, stored or transmitted, in any form or by any means, without the prior permission in writing of The Royal Society of Chemistry or the copyright owner, or in the case of reproduction in accordance with the terms of licences issued by the Copyright Licensing Agency in the UK, or in accordance with the terms of the licences issued by the appropriate Reproduction Rights Organization outside the UK. Enquiries concerning reproduction outside the terms stated here should be sent to The Royal Society of Chemistry at the address printed on this page. The RSC is not responsible for individual opinions expressed in this work. Published by The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge CB4 0WF, UK Registered Charity Number 207890 Visit our website at www.rsc.org/books Preface I was pleased to receive the invitation from the RSC to write this second edition of Colour Chemistry following the success of the first edition published in 2001.
    [Show full text]
  • Removal of Dyes from Contaminated Water Using Low Cost Adsorbents Thesis
    REMOVAL OF DYES FROM CONTAMINATED WATER USING LOW COST ADSORBENTS THESIS SUBMITTED FOR THE AWARD OF THE DEGREE OF Doctor of Philosophy IN APPLIED CHEMISTRY BY SADIA SHAKOOR UNDER THE SUPERVISION OF DR ABU NASAR DEPARTMENT OF APPLIED CHEMISTRY ZAKIR HUSSAIN COLLEGE OF ENGINEERING AND TECHNOLOGY ALIGARH MUSLIM UNIVERSITY ALIGARH (INDIA) 2016 DEPARTMENT OF APPLIED CHEMISTRY FACULTY OF ENGINEERING AND TECHNOLOGY ALIGARH MUSLIM UNIVERSITY, ALIGARH-202002 (U.P.) INDIA Dr. Abu Nasar Telephones Off. : (0571) 2700920-23 Ext: 3002 Ph.D University Fax : (0571) 2700528 Associate Professor E-mail : [email protected] Mob. : +91-9415842475 CERTIFICATE This is to certify that the thesis entitled “Removal of dyes from contaminated water using low cost adsorbents” is the original contribution of Ms. Sadia Shakoor carried out under my supervision and is suitable for the award of the degree of Doctor of Philosophy in Applied Chemistry from Aligarh Muslim University, Aligarh. This work has neither been submitted nor is being submitted for any other degree. Dr. Abu Nasar (Supervisor) I Annexure I CANDIDATE’S DECLARATION I, Sadia Shakoor, Department of Applied Chemistry certify that the work embodied in this Ph.D thesis is my own bonafide work carried out by me under the supervision of Dr. Abu Nasar at Department of Applied Chemistry, Aligarh Muslim University, Aligarh. The matter embodied in this Ph.D thesis has not been submitted for the award of any other degree. I declare that I have faithfully acknowledged, given credit to and referred to the research workers wherever their works have been cited in the text and the body of the thesis.
    [Show full text]
  • Industrial Chemicals, Ashfords Dictionary, Chemical Name Index
    2 Chemical name index A A ACA 4-AA ACA AA ACAC AA acamprosate calcium AAA acarbose AABA ACB AADMC 7-ACCA AAEM ACE AAMX acebutolol AAOA aceclidine AAOC aceclofenac AAOT acemetacin AAPP acenaphthene AAPT acenocoumarol 4-ABA acephate ABA acepromazine abacavir acequinocyl ABAH acesulfame-K abamectin acetaldehyde ABFA acetaldehyde ethyl phenethyl diacetal ABL acetaldehyde oxime ABPA acetaldehyde n-propyl phenethyl diacetal ABS acetaldoxime ABS acetal resins O-ABTF acetal resins P-ABTF acetamide ACN acetamidine hydrochloride 7-ACA 5-acetamido-2-aminobenzenesulfonic acid 7-ANCA 6-acetamido-2-aminophenol-4-sulfonic acid Name Index: Ashford’s Dictionary of Industrial Chemicals 3-acetamidoaniline 3-acetamidoaniline acetic acid, s-butyl ester 4-acetamidoaniline acetic acid, calcium salt p-acetamidoanisole acetic acid, chromium salt 4-acetamidobenzenesulfonyl chloride acetic acid, cinnamyl ester 2-acetamidocinnamic acid acetic acid, citronellyl ester 3-acetamido-2-hydroxyaniline-5-sulfonic acid acetic acid, cobalt salt 1-acetamido-7-hydroxynaphthalene acetic acid, decahydro-β-naphthyl ester 8-acetamido-1-hydroxynaphthalene-3,6-disulfonic acid acetic acid, dicyclopentenyl ester 1-acetamido-7-naphthol acetic acid, diethylene glycol monobutyl ether ester 4-acetamidonitrobenzene acetic acid, 2-ethoxyethyl ester p-acetamidophenol acetic acid, ethoxypropyl ester 3-acetamidopropylsulfonic acid, calcium salt acetic acid, ethyl diglycol ester 5-acetamido-2,4,6-triiodo-N-methylisophthalamic acid acetic acid, ethylene glycol diester 4-acetamido-2-ethoxybenzoic
    [Show full text]
  • Vat Dye - Wikipedia Page 1 of 7
    Vat dye - Wikipedia Page 1 of 7 Vat dye From Wikipedia, the free encyclopedia Vat dyes are a class of dyes that are classified as such because of the method by which they are applied. Vat dyeing is a process that refers to dyeing that takes place in a bucket or vat. Almost any dye, including fiber-reactive dyes, direct dyes, and acid dyes, can be used in a vat dye. Cotton, wool, and other fibers can be all dyed with vat dyes. The original vat dye is indigo, once obtained from plants but now produced synthetically.[1] Contents ◾ 1 Materials suited for vat dying ◾ 2 Dyeing process ◾ 2.1 Properties ◾ 3 Light-oxidized vat dyes ◾ 4 Chemical structures ◾ 5 References ◾ 6 External links Materials suited for vat dying Although almost all dyeing can be done in a vat, the term vat dye is used to describe a chemical class of dyes that are applied to cellulosic fibre (i.e.. cotton) using a redox reaction as described below. Because of the use of caustic soda, and the very high pH of the dye bath in the dyeing process, wool cannot be dyed using vat dyestuffs. Wool is soluble in caustic soda solutions. It is possible to dye wool at room temperatures with indigo (vat blue 1) and other low substantive vat dyes using soda ash as the alkali source with very little strength loss. Vat red 10, vat violet 13 and vat orange 1 can be applied in this manner as well.[2] Dyeing process Vat dyes characteristically require a reducing agent to solubilize them.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 6,332,943 B1 Herrmann Et Al
    USOO6332943B1 (12) United States Patent (10) Patent No.: US 6,332,943 B1 Herrmann et al. (45) Date of Patent: Dec. 25, 2001 (54) METHOD OF INK-JET PRINTING WITH (56) References Cited PGMENT PREPARATIONS HAVING A DSPERSANT U.S. PATENT DOCUMENTS 2.979,528 4/1961 Lundated. (75) Inventors: Manfred Herrmann, Ludwigshafen; 4,204,010 5/1980 Kramm et al. ....................... 427/508 Ginther König, Maxdorf; Ridiger 4,218.218 8/1980 Daubach et al. Sens, Ludwigshafen; Bernd Siegel, 4,287,039 9/1981 Buethe et al. Otterstadt; Karl Siemensmeyer, 5,186.846 2/1993 Brueckmann et al. Frankenthal, all of (DE) 5,538,549 7/1996 Kato et al. (73) Assignee: BASF Aktiengesellschaft, Ludwigshafen (DE) FOREIGN PATENT DOCUMENTS 2185245 10/1995 (CA). (*) Notice: Subject to any disclaimer, the term of this 36 41677 6/1988 (DE). patent is extended or adjusted under 35 44 13 242 10/1995 (DE). 0 012339 6/1980 (EP). U.S.C. 154(b) by 0 days. O 279 303 8/1988 (EP). (21) Appl. No.: 09/446,894 O 412 548 2/1991 (EP). O 518 621 12/1992 (EP). (22) PCT Filed: Jun. 18, 1998 O 542 052 5/1993 (EP). O 658 607 6/1995 (EP). (86) PCT No.: PCT/EP98/03708 0 704 469 4/1996 (EP). 0 753 552 1/1997 (EP). S371 Date: Mar. 31, 2000 1551829 9/1979 (GB). S 102(e) Date: Mar. 31, 2000 8-48922 2/1996 (JP). (87) PCT Pub. No.: WO99/01516 * cited by examiner PCT Pub. Date:Jan. 14, 1999 (30) Foreign Application Priority Data Primary Examiner Michael A.
    [Show full text]
  • Index of Dyes
    Index of Dyes This is an index of Colour Index dyes discussed in the book. CI Acid Black I, 20 CI Acid Yellow 23, 207 CI Acid Black 60, 216 CI Acid Yellow 29, 209, 226 synthesis, 233 CI Acid Yellow 54, 214 CI Acid Black 63, 227 CI Acid Yellow 76, synthesis, 231 CI Acid Blue 25, 219 CI Acid Yellow 99, 215 CI Acid Blue 40, 226 CI Azoic Diazo Component 2, 311 CI Acid Blue 45, 21S CI Azoic Diazo Component 4, 311 CI Acid Blue 92, 20S CI Acid Blue 113, 209 CI Basic Blue 3, 41 CI Acid Blue 129, 219 synthesis, 197 synthesis, 234 CI Basic Blue 9, 41 CI Acid Blue 159, 214 CI Basic Blue 22, 367 CI Acid Brown 24S, 222 synthesis, 194 CI Acid Green I, 45 CI Basic Blue 119, 173 CI Acid Green 25, 21S CI Basic Green 4, 41 synthesis, 234 CI Basic Orange 30, 172 CI Acid Green 27, 21S CI Basic Red 14, synthesis, 196 CI Acid Green 75, 33 CI Basic Red IS: I, synthesis, 193 CI Acid Orange 3, 222 CI Basic Red 22, 367 synthesis, 231 synthesis, 197 CI Acid Orange 19, 210 CI Basic Violet 14, 367 CI Acid Orange 67, 209 CI Basic Yellow 11, synthesis, 194 synthesis, 230 CI Basic Yellow 2S, 367 CI Acid Orange 92, 227 synthesis, 195 CI Acid Orange 14S, 216 CI Acid Red I, 207 CI Coupling Component 5, 310 CI Acid Red 37, 20S CI Coupling Component 36, 310 CI Acid Red 57, 209, 226 synthesis, 230 CI Direct Black 3, 67 CI Acid Red 114, 210 CI Direct Black 9, 279 CI Acid Red 119, 210 CI Direct Black 19, 20, 279 CI Acid Red 13S, 211 CI Direct Black 3S, 20 CI Acid Red 249, 210 CI Direct Blue I, 67 synthesis, 233 CI Direct Blue 15, 20 CI Acid Red 30S, 216 CI Direct Blue 67, 66
    [Show full text]
  • DYETEC VISION 163Th 2
    ISSN 2288-9728 DYETEC VISION 163th 2 Technology Evolution Leader 기술정보지 다이텍 비전 163th 2020. 5 May DYETEC VISION 기술과 인재로 미래를 펼쳐갑니다 다이텍연구원은 인재와 기술을 바탕으로 미래의 산업을 발굴하고 정보의 장 차별화 된 섬유소재 기술 개발 및 원천기술 확보를 주도하며, 04 티트리 오일 / 에틸 셀룰로오스 마이크로캡슐 탑재 항균 직물 관련기업의 기술 성장을 리드하여 10 초고분자량 폴리에틸렌 3축 브레이드의 기계적 열적 거동 : 구조 파라미터의 영향 20 유한요소법을 이용한 브레이드 관 구조의 팽창 거동에 대한 기계적 분석 인류와 사회에 공헌하는 일류연구원이 되도록 34 다양한 Apocynum venetum 폴리락틱산 / 나노 셀룰로오스 나노섬유 필름의 형태, 구조 및 항균 특성 비교 46 백색 면 / 천연 갈색 면 혼합 직물의 항균 특성 노력하겠습니다. 테마기획 53 퍼포먼스 향상을 위한 경영 수영복의 개발 59 반응성 N-Halamine 전구체로 배트 염색한 면직물의 항균 처리 66 변형된 질화붕소 나노시트 면직물의 난연 특성 78 호흡수 감지를 위한 개폐 구조를 가진 3차원 섬유 센서의 감지 효율 95 탄소포집 및 저장(BECCS) 잠재력을 지닌 바이오 에너지: 다양한 금속 촉매 활용 가스상 탄화수소 재생산과 열화학 처리를 통한 셀룰로오스 내 고순도 수소생산 기타동향 106 N3P3환망목(環網目)형태의 폴리포스파젠 생성과 그 용도(II) 113 천연 강황 염료를 사용한 면직물의 초음파 지속 초 저액비 염색 연구 124 4-Hydroxybenzophenone 기반 Mono Azo계 자외선 차단 산성염료의 합성, 특성 및 염색 성능에 대한 연구 133 액체 화염 스프레이를 통한 항균 직물의 고속 생산 142 연구원 소식 144 교육안내 DYETECVISION기술정보지 2020년 5월호 통권 제 163호 발행일 2020년 5월 1일 발행처 DYETEC연구원 발행인 최진환 편집 김상용 전화 053)350-3700 홈페이지 www.dyetec.or.kr 디자인・인쇄 디자인 집 070-8915-5996 대구시 서구 달서천로 92(평리동) | TEL : 053)350-3700(代) | FAX : 053)350-3888 2 3 4 소개 최근에는 에센셜 오일이 항균제, 항진균제, 항바이러스제, 보습제, 재생제 등의 성능뿐만 아니라 방향제 성분으로 인해 건강 관리 제품으로서의 개발에 더욱 많은 관심을 받고 있다.
    [Show full text]
  • Industrial Chemicals, Ashfords Dictionary, Formula Index
    Formula index Ag1 Ag1 Al1C6H16Na1O4 silver sodium bis(2-methoxyethoxy)aluminium hydride Ag1Br1 Al1C6H18O9P3 silver bromide fosetyl-aluminium Ag1C1N1 Al1C8H19 silver cyanide diisobutylaluminium hydride Ag1Cl1 Al1C9H21O3 silver chloride aluminium isopropoxide Ag1N1O3 Al1C12H27 silver nitrate triisobutylaluminium Ag1O1 tri-n-butylaluminium silver peroxide Al1C18H37O4 Al1 aluminium monostearate aluminium Al1C24H45O6 Al1C2Cl2H5 aluminium octoate ethylaluminium dichloride Al1C24H51 Al1C2H3O5 tri-n-octylaluminium aluminium formate, basic Al1C27H18N3O3 Al1C4Cl1H10 tris(8-hydroxyquinoline)aluminium diethylaluminium chloride Al1C36H71O5 Al1C4H7N4O5 aluminium distearate aldioxa Al1C54H105O6 Al1C4H7O5 aluminium tristearate aluminium acetate, basic Al1Cl3 Al1C6H9O6 aluminium chloride, anhydrous aluminium acetate Al1Cl3H12O6 Al1C6H15 aluminium chloride, hexahydrate triethylaluminium Al1F3 Formula Index: Ashford’s Dictionary of Industrial Chemicals Al1F6Na3 aluminium fluoride cobalt blue Al1F6Na3 Al2H2O4 cryolite alumina trihydrate Al1H4Li1 Al2O3 lithium aluminium hydride alumina, activated Al1H4N1O8S2 alumina, calcined ammonium alum alumina, fused Al1H6O12P3 aluminium hydroxide gel aluminium phosphate, monobasic Al2O5Si1 Al1K1O8S2 aluminium silicate, precipitated aluminium potassium sulfate Al2O5Ti1 Al1N1 aluminium titanate aluminium nitride Al2O12S3 Al1N3O9 aluminium sulfate aluminium nitrate Al3H14Na1O32P8 Al1Na1O2 sodium aluminium phosphate, acidic sodium aluminate Al16C12H54O75S8 Al1Na1O8S2 sucralfate sodium alum Ar1 Al1P1 argon aluminium phosphide
    [Show full text]