Acceleratorsand Acceleratorsystems
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A Little Book About BIG Chemistry the Story of Man-Made Polymers
SPRINGER BRIEFS IN MATERIALS Jim Massy A Little Book about BIG Chemistry The Story of Man-Made Polymers www.ebook3000.com SpringerBriefs in Materials The SpringerBriefs Series in Materials presents highly relevant, concise mono- graphs on a wide range of topics covering fundamental advances and new applications in the field. Areas of interest include topical information on innovative, structural and functional materials and composites as well as fundamental principles, physical properties, materials theory and design. SpringerBriefs present succinct summaries of cutting-edge research and practical applications across a wide spectrum of fields. Featuring compact volumes of 50 to 125 pages, the series covers a range of content from professional to academic. Typical topics might include: • A timely report of state-of-the-art analytical techniques • A bridge between new research results, as published in journal articles, and a contextual literature review • A snapshot of a hot or emerging topic • An in-depth case study or clinical example • A presentation of core concepts that students must understand in order to make independent contributions Briefs are characterized by fast, global electronic dissemination, standard publishing contracts, standardized manuscript preparation and formatting guide- lines, and expedited production schedules. More information about this series at http://www.springer.com/series/10111 www.ebook3000.com Jim Massy A Little Book about BIG Chemistry The Story of Man-Made Polymers 123 Jim Massy Norwich, Norfolk UK ISSN 2192-1091 ISSN 2192-1105 (electronic) SpringerBriefs in Materials ISBN 978-3-319-54830-2 ISBN 978-3-319-54831-9 (eBook) DOI 10.1007/978-3-319-54831-9 Library of Congress Control Number: 2017934463 © The Author(s) 2017 This work is subject to copyright. -
Vulcanization & Accelerators
Vulcanization & Accelerators Vulcanization is a cross linking process in which individual molecules of rubber (polymer) are converted into a three dimensional network of interconnected (polymer) chains through chemical cross links(of sulfur). The vulcanization process was discovered in 1839 and the individuals responsible for this discovery were Charles Goodyear in USA and Thomas Hancock in England. Both discovered the use of Sulfur and White Lead as a vulcanization system for Natural Rubber. This discovery was a major technological breakthrough for the advancement of the world economy. Vulcanization of rubbers by sulfur alone is an extremely slow and inefficient process. The chemical reaction between sulfur and the Rubber Hydrocarbon occurs mainly at the C = C (double bonds) and each crosslink requires 40 to 55 sulphur atoms (in the absence of accelerator). The process takes around 6 hours at 140°C for completion, which is uneconomical by any production standards. The vulcanizates thus produced are extremely prone to oxidative degradation and do not possess adequate mechanical properties for practical rubber applications. These limitations were overcome through inventions of accelerators which subsequently became a part of rubber compounding formulations as well as subjects of further R&D. Following is the summary of events which led to the progress of ‘Accelerated Sulfur Vulcanization'. Event Year Progress - Discovery of Sulfur Vulcanization: Charles Goodyear. 1839 Vulcanizing Agent - Use of ammonia & aliphatic ammonium derivatives: Rowley. 1881 Acceleration need - Use of aniline as accelerator in USA & Germany: Oenslager. 1906 Accelerated Cure - Use of Piperidine accelerator- Germany. 1911 New Molecules - Use of aldehyde-amine & HMT as accelerators in USA & UK 1914-15 Amine Accelerators - Use of Zn-Alkyl Xanthates accelerators in Russia. -
1,2,4-Triazine Sulfonamides: Synthesis by Sulfenamide Intermediates, in Vitro Anticancer Screening, Structural Characterization, and Molecular Docking Study
molecules Article 1,2,4-Triazine Sulfonamides: Synthesis by Sulfenamide Intermediates, In Vitro Anticancer Screening, Structural Characterization, and Molecular Docking Study Danuta Branowska 1, Zbigniew Karczmarzyk 1,*, Ewa Woli ´nska 1, Waldemar Wysocki 1, Maja Morawiak 2 , Zofia Urba ´nczyk-Lipkowska 2 , Anna Bielawska 3 and Krzysztof Bielawski 3 1 Faculty of Exact and Natural Sciences, Siedlce University of Natural Sciences and Humanities, 3 Maja 54, 08-110 Siedlce, Poland; [email protected] (D.B.); [email protected] (E.W.); [email protected] (W.W.) 2 Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland; [email protected] (M.M.); zofi[email protected] (Z.U.-L.) 3 Medical University of Bialystok, Department of Medicinal Chemistry and Drug Technology, J. Kilinskiego 1, 15-089 Bialystok, Poland; [email protected] (A.B.); [email protected] (K.B.) * Correspondence: [email protected]; Tel.: +48-25-643-1017 Received: 24 March 2020; Accepted: 14 May 2020; Published: 16 May 2020 Abstract: In this study, we synthesized novel sulfonamides with a 1,2,4-triazine moiety according to pharmacophore requirements for biological activity. All the synthesized compounds were tested in vitro to verify whether they exhibited anticancer activity against the human breast cancer cell lines MCF-7 and MDA-MB-231. Among them, two most active ones, having IC50 values of 50 and 42 µM, respectively, were found to show higher anticancer activity than chlorambucil used as the reference in the in vitro tests. In addition, two other compounds, which had IC50 values of 78 and 91 µM, respectively, exhibited a similar level of activity as chlorambucil. -
THE CHEMISTRY of SULFENIMIDES by Barbara Ann Orwig a Thesis
THE CHEMISTRY OF SULFENIMIDES by Barbara Ann Orwig A thesis submitted to the Faculty of Graduate Studies and Research in partial fulfilment of the requirements for the degree of Master of Science Department of Chemistry McGill University Montreal, P.Q. Canada May 1971 @) Barbara Ann Orwig 1972 Dedicated to My Parents Il Thanx Il i ACKNOWLEDGEMENTS 3l MY thanks to Dr. D.F.R. Gilson for the p nmr spectra, to Victor Yu for the A-60 nmr spectra, and to Peter Currie for the mass spectra. For helpful discussions and worthwhile suggestions l thank David Ash 1 Errol Chang 1 and John Gleason. For his guidance and help as my research director l thank Dr. David N. Harpp. And to Elva and Hermann Heyge go special thanks for their help and for "putting up wi th œil. TABLE OF CONTENTS Page ACKNOWLEDGEMENTS i INTRODUcrION 1 EXPERIMENTAL SECTION 22 RESULTS AND DISCUSSION 42 TABLES 1 Preparation of Sulfenyl Chlorides 72 2 Preparation of N-(alkyl/aryl thio)phthalimides 73 3 Desulfurization Reactions of N-(alkyl/aryl thio)phthalimides 76 4 Mass Spectra of N-(alkyl/aryl thio)phthalimides 77 FIGURES (Spectra) 78 - 87 BIBLIOGRAPHY 88 INTRODUcrION AND BACKGROUND Sulfenic acids Cl), in which sulfur exists in its R-S-OH l lcwest oxidation state, are highly lmstable compolmds and only a few l have been isolated. The derivatives of sulfenic acid {~.> however, are generally isolable and usually stable. 2 R-S-Y 2 When Y is -NH ' -~HR, or -NR ' the resulting class of compolmds is 2 2 ter.med sulfenamides. -
United States Patent Office
3,454,590 United States Patent Office Patented July 8, 1969 2 3,454,590 New compounds that can be produced by the process BENZOTHAZO-LE-2-SULFNAMIDES are benzothiazole-2-sulfinamides where R and R in the Alan Jeffrey Neale, Llangollen, Wales, and Terence above formula each represent an aliphatic or cyclo James Rawlings, Penicuik, Scotland, assignors to aliphatic group and the total number of carbon atoms Monsanto Chemicals Limited, London, England, in R and R' is at least four, and sulfinamides where R a British company No Drawing. Filed June 1, 1967, Ser. No. 642,717 and R are linked to form a saturated cyclic system with Claims priority, application Great Britain, June 17, 1966, the nitrogen atom. 27,184/66 The invention includes a process in which a new com nt. C. C07d 91/44, 29/34 pound as defined above is employed as an accelerator U.S. CI. 260-306.6 3 Claims O for the Vulcanization of rubber. Sulfinamides that can be produced by oxidation of the corresponding sulfenamides in the process defined above ABSTRACT OF THE DISCLOSURE can also be obtained by reaction of a benzothiazole-2-sul finyl halide with an appropriate amine. In particular, sul This disclosure is benzothiazole-2-sulfinamides of the 5 finamides in which the sulfinamide grouping is represented formula by the formula: S N R R C-S-N -s-N Né y 20 R. can be obtained by reaction of the sulfinyl halide with where R and R' are each an aliphatic or cycloaliphatic an amine having the formula HNRR. -
Zinc Complexes with 1,3-Diketones As Activators for Sulfur Vulcanization of Styrene-Butadiene Elastomer Filled with Carbon Black
materials Article Zinc Complexes with 1,3-Diketones as Activators for Sulfur Vulcanization of Styrene-Butadiene Elastomer Filled with Carbon Black Magdalena Maciejewska * , Anna Sowi ´nska* and Agata Grocholewicz Department of Chemistry, Institute of Polymer and Dye Technology, Lodz University of Technology, Stefanowskiego Street 12/16, 90-924 Lodz, Poland; [email protected] * Correspondence: [email protected] (M.M.); [email protected] (A.S.) Abstract: Zinc oxide nanoparticles (N-ZnO) and zinc complexes with 1,3-diketones of different structures were applied instead of microsized zinc oxide (M-ZnO) to activate the sulfur vulcanization of styrene-butadiene rubber (SBR). The influence of vulcanization activators on the cure characteristics of rubber compounds, as well as crosslink density and functional properties of SBR vulcanizates, such as tensile properties, hardness, damping behavior, thermal stability and resistance to thermo- oxidative aging was explored. Applying N-ZnO allowed to reduce the content of zinc by 40% compared to M-ZnO without detrimental influence on the cure characteristic and performance of SBR composites. The activity of zinc complexes in vulcanization seems to strongly depend on their structure, i.e., availability of zinc to react with curatives. The lower the steric hindrance of the substituents and thus the better the availability of zinc ions, the greater was the activity of the zinc complex and consequently the higher the crosslink density of the vulcanizates. Zinc complexes had no Citation: Maciejewska, M.; detrimental effect on the time and temperature of SBR vulcanization. Despite lower crosslink density, Sowi´nska,A.; Grocholewicz, A. Zinc most vulcanizates with zinc complexes demonstrated similar or improved functional properties in Complexes with 1,3-Diketones as Activators for Sulfur Vulcanization of comparison with SBR containing M-ZnO. -
UNDERSTANDING SULFUR BASED REDOX BIOLOGY THROUGH ADVANCEMENTS in CHEMICAL BIOLOGY by THOMAS POOLE a Dissertation Submitted to T
UNDERSTANDING SULFUR BASED REDOX BIOLOGY THROUGH ADVANCEMENTS IN CHEMICAL BIOLOGY BY THOMAS POOLE A Dissertation Submitted to the Graduate Faculty of WAKE FOREST UNIVERSITY GRADUATE SCHOOL OF ARTS AND SCIENCES in Partial Fulfillment of the Requirements for the Degree of DOCTOR OF PHILOSOPHY Chemistry May 2017 Winston-Salem, North Carolina Approved By: S. Bruce King, Ph.D., Advisor Leslie B. Poole, Ph.D., Chair Patricia C. Dos Santos, Ph.D. Paul B. Jones, Ph.D. Mark E. Welker, Ph.D. ACKNOWLEDGEMENTS First and foremost I would like to thank professor S. Bruce King. His approach to science makes him an excellent role model that I strive to emulate. He is uniquely masterful at parsing science into important pieces and identifying the gaps and opportunities that others have missed. I thank him for the continued patience and invaluable insight as I’ve progressed through my graduate studies. This work would not have been possible without his insight and guiding suggestions. I would like to thank our collaborators who have proven invaluable in their support. Cristina Furdui has provided the knowledge, context, and biochemical support that allowed our work to be published in esteemed journals. Leslie Poole has provided the insight into redox biology and guidance towards appropriate experiments. I thank my committee members, Mark Welker and Patricia Dos Santos who have guided my graduate work from the beginning. Professor Dos Santos provided the biological perspective to evaluate my redox biology work. In addition, she helped guide the biochemical understanding required to legitimize my independent proposal. Professor Welker provided the scrutinizing eye for my early computational work and suggested validating the computational work with experimental data. -
©2020 Yu Sun All Rights Reserved
©2020 YU SUN ALL RIGHTS RESERVED VULCANIZATION AND DEVULCANIZATION OF RUBBER A Dissertation Presented to The Graduate Faculty of The University of Akron In Partial Fulfillment of the Requirement for the Degree Doctor of Philosophy YU SUN August, 2020 VULCANIZATION AND DEVULCANIZATION OF RUBBER YU SUN Dissertation Approved: Accepted: _____________________________ _____________________________ Advisor Department Chair Dr. Li Jia Dr. Tianbo Liu _____________________________ _____________________________ Committee Chair Interim Dean of the College Dr. Toshikazu Miyoshi Dr. Ali Dhinojwala _____________________________ _____________________________ Committee Member Acting Dean of the Graduate School Dr. Gary R. Hamed Dr. Marnie Saunders _____________________________ _____________________________ Committee Member Date Dr. Junpeng Wang _____________________________ Committee Member Dr. Kevin Cavicchi ii ABSTRACT The research in this dissertation includes two parts: vulcanization of isobutylene- isoprene rubber (IIR) containing geminal vinylidene-acrylate groups and surface devulcanization of ground rubber particles (GRPs) for rubber recycling. In Chapter 2, EIIR was synthesized by grafting ethyl propiolate to IIR via EtAlCl2- catalyzed Alder-ene reaction. Methods for crosslinking EIIR using dicumyl peroxide (DCP) with m-Phenylene-N,N’-bismaleimide (BMI) as a coagent were investigated. The strength, extensibility, and overall toughness of the peroxide-cured EIIR significantly exceed those of previously reported peroxide-cured IIR derivatives. A wide range of stiffness can be realized without sacrificing the strength. The crosslinking density achieved using such curatives is indexed as a function of DCP/BMI ratio, and the curing efficiency of peroxide as a function of DCP/BMI ratio and DCP loading. The role of the geminal vinylidene-acrylate moiety in curing was studied by model reactions, which suggest that the geminal vinylidene-acrylate moiety undergoes both radical addition and hydrogen abstraction. -
Recent Advances in Sulfur–Nitrogen Bond Formation Via Cross-Dehydrogenative Coupling Cite This: RSC Adv.,2018,8, 18456 Reactions
RSC Advances View Article Online REVIEW View Journal | View Issue Recent advances in sulfur–nitrogen bond formation via cross-dehydrogenative coupling Cite this: RSC Adv.,2018,8, 18456 reactions Fatemeh Alsadat Hosseini Nasab,a Leila Zare Fekri,b Aazam Monfared,b *c b Received 12th January 2018 Akram Hosseinian and Esmail Vessally Accepted 12th April 2018 This focus-review surveys literature methods for the construction of sulfur–nitrogen bonds through cross- DOI: 10.1039/c8ra00356d dehydrogenative coupling reactions between thiols and N–H compounds with a particular emphasis on the rsc.li/rsc-advances mechanistic aspects of the reactions. The literature has been surveyed until the end of 2017. 1. Introduction 2 with trade name Topamax is a promising anticonvulsant medicine available in a number of countries worldwide. The 8 Needless to say, organosulfur compounds play a very important drug is also used for migraine prevention in adults. Folpet 3 is Creative Commons Attribution-NonCommercial 3.0 Unported Licence. role in various elds such as organic synthesis, materials a fungicide used for broad-spectrum control of fungal patho- 9 science, agriculture, and medicinal chemistry.1–4 Among them, gens. Sulfoxaor 4 is an insecticide with a sulfoximine motif, compounds bearing sulfur–nitrogen bonds are important this compound is very active against a wide range of sap-feeding 10 building blocks in a variety of biologically active substances. For insect pests and widely used around the world. Thus, instance, sultiame 1 (Fig. 1) with brand name Ospolot is construction of biologically and synthetically important sulfur– a synthetic sulfa-based drug marketed worldwide for the treat- nitrogen bonds is one of the essential transformations in ment of epilepsy.5,6 The drug works by reducing the activity of organic synthesis. -
Reactive Sintering of Ground Tire Rubber (GTR) Modified by a Trans-Polyoctenamer Rubber and Curing Additives
polymers Article Reactive Sintering of Ground Tire Rubber (GTR) Modified by a Trans-Polyoctenamer Rubber and Curing Additives Łukasz Zedler 1,* , Daria Kowalkowska-Zedler 2 , Xavier Colom 3 , Javier Cañavate 3 , Mohammad Reza Saeb 4 and Krzysztof Formela 1,* 1 Department of Polymer Technology, Faculty of Chemistry, Gda´nskUniversity of Technology, Gabriela, Narutowicza 11/12, 80–233 Gda´nsk,Poland 2 Department of Inorganic Chemistry, Faculty of Chemistry, Gda´nskUniversity of Technology, Gabriela, Narutowicza 11/12, 80–233 Gda´nsk,Poland; [email protected] 3 Department of Chemical Engineering, Universitat Politècnica de Catalunya Barcelona Tech, Carrer de Colom, 1, 08222 Terrassa, Barcelona, Spain; [email protected] (X.C.); [email protected] (J.C.) 4 Center of Excellence in Electrochemistry, School of Chemistry, College of Science, University of Tehran, Tehran 11155-4563, Iran; [email protected] * Correspondence: [email protected] (Ł.Z.); [email protected] (K.F.) Received: 17 November 2020; Accepted: 14 December 2020; Published: 17 December 2020 Abstract: The proposed method of ground tire rubber (GTR) utilization involves the application of trans-polyoctenamer rubber (TOR), a commercially available waste rubber modifier. The idea was to investigate the influence of various curing additives (sulfur, N-cyclohexyl-2-benzothiazole sulfenamide (CBS), dibenzothiazole disulfide (MBTS) and di-(2-ethyl)hexylphosphorylpolysulfide (SDT)) on curing characteristics, physico-mechanical, thermal, acoustic properties as well as the morphology of modified GTR, in order to evaluate the possibility of reclaiming GTR and the co-cross-linking between applied components. The results showed that the presence of the modifier without the addition of curing additives hinders the physico-mechanical properties of revulcanized GTR. -
Combining Curatives Combining Curatives in Sulfur Cure Systems for Tires Reduces Excessive Use of These Chemicals and Improves the Cure Efficiency
Combining curatives Combining curatives in sulfur cure systems for tires reduces excessive use of these chemicals and improves the cure efficiency by Saad H Sheikh, Ali Ansarifar (Department of Materials), Jonathan Dushyanthan, George W Weaver and Kahagala Gamage Upul Wijayantha (Department of Chemistry), Loughborough University, UK ccelerators and Figure 1: Cure traces (torque [dNm] versus activators are time [min]) of the indispensable rubber compounds chemicals in the with an increasing loading of the powder. sulfur vulcanization a) compound with of tires. Accelerators 0.63phr powder; b) control onset, rate and extent compound with 2.5phr A powder; c) compound of cross-linking and hence final with 5.6phr powder properties of rubber vulcanizates. Activators are ingredients used to activate accelerators and improve their effectiveness.1 Sulfenamide accelerators, and zinc oxide (ZnO) and stearic acid activators are used extensively to cure a wide range of industrial articles.2 For example, in tire belt skim compound, the cure system consists of 5phr sulfur; 0.7phr N,N’-dicyclohexyl-2-benzothiazole sulfenamide (DCBS) accelerator; 2phr hexamethoxy methyl 1a melamine (HMMM) accelerator; 7phr ZnO; and 1phr stearic acid.3 ZnO and stearic acid can be harmful to health, safety and the environment. According to the European Directive 2004/73/ EC, ZnO is very toxic to aquatic organisms. Stearic acid causes skin and eye irritation and is classified as highly flammable.4 DCBS and HMMM accelerators may cause eye, skin and respiratory irritation and are harmful to aquatic life.5,6 Previously we reported a new method for measuring the chemical curatives in sulfur cure systems for rubber, which eliminated stearic acid entirely and reduced the ZnO requirement to less than 1phr.7 This extended work functionalized ZnO with a sulfenamide accelerator in an organic solvent and examined its effect on the cure properties of natural rubber (NR). -
2-Nitrophenylsulfenyl Chloride Into New Compounds with Potential Pesticidal Activity
Synthesis and transformation of 4-dichloromethylsulfonyl-2-nitrophenylsulfenyl... 5 Pestycydy/Pesticides, 2009, (1-4), 5-14. ISSN 0208-8703 Synthesis and transformation of 4-dichloromethylsulfonyl- 2-nitrophenylsulfenyl chloride into new compounds with potential pesticidal activity Zbigniew OCHAL, Wojciech BIAŁKOWSKI and Łukasz BANACH Warsaw University of Technology, Faculty of Chemistry, 3 Noakowskiego St., 00-664 Warsaw, Poland e-mail: [email protected] Abstract: The synthesis of 4-dichloromethylsulfonyl-2-nitrophenylsulfenyl chloride and its transformation into new compounds with promising pesticidal activity is reported. The title compounds were obtained by a three-step synthesis, starting from 4-dichloromethylchlorophenyl sulfone. It was nitrated and then subjected to the SNAr reaction with sodium disulfide to give proper diphenyl disulfide, which was next chlorinated by chlorine. The obtained phenylsulfenyl chloride was transformed into sulfenamide derivatives by reactions with amines. Keywords: 4-chlorophenyldichloromethyl sulfone, sulfenyl chloride, sulfenamides, pesticides INTRODUCTION Some sulfenamide derivatives are known as the non-systemic fungicides widely used to control foliage and fruit diseases of tomatoes, coffee berry, potato and many other fruits and vegetables [1, 2]. Galactofuranosyl-N,N-dialkyl sulfenamides displayed an antimycobacterial activity [3]. Some N-sulfenyl heterocycles are effective sulfenylating agents of aromatic amines [4]. In addition, they are the important intermediates in many reactions, promising in the prodrug technologies [5, 6]. On the other hand, it is well known that chemical compounds with chloromethyl groups show an interesting biological activity [1]. We have proved in our previous investigations that chloro- and dichloromethylsulfonyl 6 Z. Ochal, W. Białkowski, Ł. Banach groups in aromatic compounds were favorable to pesticidal activities [7-11].