- One-pot efficient synthesis of disulfides from alkyl halides and alkyl tosylates using thiourea and elemental sulfur without contamination by higher polysulfides
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An efficient and odorless synthesis of disulfides from alkyl halides using thiourea and elemental sulfur in the presence of sodium carbonate in wet polyethylene glycol (PEG 200) at 40 C without contamination by higher polysulfides has been developed. This procedure was then extended to preparation of disulfides from alkyl tosylates at 70 C.
- Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Taghavi, Zeinab Khatoon
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- One-pot conversion of alkyl halides to organic disulfides (disulfanes) using thiourea and hexamethyldisilazane (HMDS) in DMSO
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A practical method to synthesize symmetric disulfides from alkyl halides has been developed. Using this procedure primary, secondary, benzylic and allylic disulfides were prepared by treating the corresponding alkyl halides with thiourea and HMDS in DMSO at 50 °C within 10-24 h in high yields.
- Abbasi, Mohammad,Jabbari, Arida
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- A one-pot, efficient, and odorless synthesis of symmetrical disulfides using organic halides and thiourea in the presence of manganese dioxide and wet polyethylene glycol (PEG-200)
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Primary, secondary, tertiary, allylic, and benzylic halides are converted efficiently into symmetric disulfides in high yields using thiourea as the sulfur atom source. The reactions are odorless and are performed at 30-35 °C in wet PEG-200 using MnO2 as an oxidant.
- Firouzabadi, Habib,Iranpoor, Nasser,Abbasi, Mohammad
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- Water effects on SmI2 reductions: A novel method for the synthesis of alkyl thiols by SmI2-promoted reductions of sodium alkyl thiosulfates and alkyl thiocyanates
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Water as a cosolvent has significant improving effect on the reductivity of SmI2 in the reduction of sodium alkyl thiosulfates and alkyl thiocyanates. A new method for synthesis of alkyl thiols by SmI 2/THF/H2O system has been developed.
- Zhan, Zhuang-Ping,Lang, Kai,Liu, Feng,Hu, Li-Ming
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- Molecularly ordered decanethiolate self-assembled monolayers on Au(111) from in situ cleaved decanethioacetate: An NMR and STM study of the efficacy of reagents for thioacetate cleavage
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The cleavage of decanethioacetate (C10SAc) has been studied by 1H nuclear magnetic resonance (NMR) spectroscopy and scanning tunneling microscopy (STM) imaging of in situ prepared decanethiolate self-assembled monolayers (SAMs) on Au(111). Solutions of C10SAc (46 mM) and previously reported cleavage reagents (typically 58 mM) in CD3OD were monitored at 20 °C by NMR spectroscopy. Cleavage by ammonium hydroxide, propylamine, or hydrochloric acid was not complete within 48 h; cleavage by potassium carbonate was complete within 24 h and that by potassium hydroxide or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) within 2 h. Similar cleavage rates were observed for phenylthioacetate. The degree of molecular ordering determined by STM imaging increased with increasing extent of in situ cleavage by these same reagents (2.5 mM C10SAc and 2.5 mM reagent in ethanol for 1 h, then 16 h immersion of Au/mica). Less effective cleavage reagents did not cleave the C10SAc sufficiently to decanethiol (C10SH) and gave mostly disordered SAMs. In contrast, KOH or DBU completely cleaved the C10SAc to C10SH and led to well-ordered SAMs composed of (3 × 3)R30° domains that are indistinguishable from SAMs grown from C10SH. Monolayer formation from thioacetates in the absence of cleavage agents is likely due to thiol or disulfide impurity in the thioacetates. Eliminating disulfide by using Bu 3P as a sacrificial reductant also helped to produce good molecular order in the SAM. The methods presented here allow routine growth of molecularly ordered alkanethiolate SAMs from thioacetates using reagents of ordinary purity under ambient, benchtop conditions.
- Singh, Anuradha,Dahanayaka, Daminda H.,Biswas, Abhijit,Bumm, Lloyd A.,Halterman, Ronald L.
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- Direct synthesis of disulfides from alkyl halides using thiourea and CCl4 in glycerol
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Abstract Dialkyl disulfides were obtained on the basis of the reaction of alkyl halides and thiourea in the presence of CCl4 and Et3N. This procedure enables the odorless and one-pot synthesis of disulfides by employing cheap, easy-to-handle and readily available reagents and substrates in wet glycerol.
- Abbasi, Mohammad,Khalili, Dariush
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- One-pot synthesis of organic disulfides (disulfanes) from alkyl halides using sodium sulfide trihydrate and hexachloroethane or carbon tetrachloride in the poly(ethylene glycol) (PEG-200)
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Abstract Symmetric disulfides are produced by treating their corresponding organic halides including benzylic, allylic, primary and secondary halides with Na2S·3H2O and C2Cl6 or CCl4 in PEG-200 at room temperature in high yields.
- Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Moosavi, Hekmat,Saeedi, Narges
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- The synthesis of symmetrical disulfides by reacting organic halides with Na2S2O3·5H2O in DMSO
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A one-pot, and scalable method to prepare symmetric disulfides from their corresponding primary, secondary, allylic, and benzylic halides has been developed. In this method, a disulfide is synthesized by reacting an alkyl halide with Na2S2O3·5H2O at 60-70 °C in DMSO.
- Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Saeedi, Narges
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- Unexpected reactivity of the Burgess reagent with thiols: Synthesis of symmetrical disulfides
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(Equation Presented) Reaction of the Burgess reagent with a series of aliphatic and aromatic thiols led to the corresponding symmetrical disulfides in high yields. No olefins were detected in the reactions of aliphatic thiols.
- Banfield, Scott C.,Omori, Alvaro Takeo,Leisch, Hannes,Hudlicky, Tomas
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- Graphene Oxide-Assisted One-Pot and Odorless Synthesis of Symmetrical Disulfides Using Primary and Secondary Alkyl Halides (Tosylates) and Thiourea as Sulfur Source Reagent
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Graphene oxide is described as a heterogeneous oxidant for the synthesis of symmetrical disulfides through the in situ generation of thiols from primary and secondary alkyl halides (tosylates) and thiourea in wet acetonitrile. A variety of alkyl halides and alkyl tosylates can be converted to corresponding disulfides in good to excellent yields. This strategy is free of foul-smelling thiols.
- Khalili, Dariush
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- Distinct catalytic effect of micellar solution of sodium dodecyl sulfate (sds) for one-pot conversion of alkyl halides to disulfides via an odourless process using thiourea and mno2
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A novel one-pot odourless synthesis of symmetrical disulfides from their corresponding halides in aqueous mediausing thiourea and MnO2 in the presence of NaHCO3 or Na2CO3 catalyzed by micellar solution of sodium dodecyl sulfate (SDS) is described. By this method, primary, allylic and benzylic halides were converted into their corresponding disulfides in high yields.
- Firouzabadi, Habib,Iranpoor, Nasser,Abbasi, Mohammad
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- Linear Ladder-Type π-Conjugated Polymers Composed of Fused Thiophene Ring Systems
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The study of a linear ladder-type π-conjugated polymers of carbon-sulfur (C2S) analogue of polyacene was presented. The synthesis of ladder-type polymer was achieved via the intramolecular condensation process that resulted in the formation of fused, cross-conjugated thiophene rings. The geometrical relaxation process and various energetic and structural aspects of the convergence behavior of the polaronic and bipolaronic defects on the long chains were also studied. The energetic aspects of doping behavior suggested the possession of polaron as the prevailing charged species by the ladder-type polymer.
- Oyaizu, Kenichi,Iwasaki, Tomokazu,Tsukahara, Yoshiaki,Tsuchida, Eishun
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- Direct synthesis of phosphorotrithioites and phosphorotrithioates from white phosphorus and thiols
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White phosphorus (P4) is still the major commercial P-atom source for the production of organophosphorus compounds. Conventionally, C-S-P bonds were constructed from environmentally questionable P(O)X directly or indirectly. From the green chemistry point of view, formation of C-S-P bonds from inorganic molecule P4 in an easy-to-operate and atom-economical way is essential because it will avoid the hazardous chlorination process. Only five methods for the formation of C-S-P bonds from P4 have been developed over the past 70 years. Here, the first general and high-yielding synthesis of P(SR)3 and P(O)(SR)3 involving P4 and thiols is presented. With the use of KOH or K2CO3 as a base and DMSO-toluene as a solvent, both arythiols and alkylthiols are tolerant in this transformation. The reaction is characterized by a complete conversion of white phosphorus. This operationally simple and environmentally sound reaction shows a broad scope of substrates and good functional group tolerance. Moreover, this method can be easily adapted to large-scale preparation.
- Cao, Yinwei,Huangfu, Xinlei,Lu, Guozhang,Tang, Guo,Wang, Yueqiao,Zhao, Yufen
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supporting information
p. 5303 - 5309
(2020/09/17)
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- Selective, cofactor-mediated catalytic oxidation of alkanethiols in a self-assembled cage host
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A spacious Fe(ii)-iminopyridine self-assembled cage complex can catalyze the oxidative dimerization of alkanethiols, with air as stoichiometric oxidant. The reaction is aided by selective molecular recognition of the reactants, and the active catalyst is derived from the Fe(ii) centers that provide the structural vertices of the host. The host is even capable of size-selective oxidation and can discriminate between alkanethiols of identical reactivity, based solely on size. This journal is
- Da Camara, Bryce,Dietz, Philip C.,Chalek, Kevin R.,Mueller, Leonard J.,Hooley, Richard J.
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supporting information
p. 14263 - 14266
(2020/11/24)
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- Cyclic telluride reagents with remarkable glutathione peroxidase-like activity for purification-free synthesis of highly pure organodisulfides
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Monoamino cyclic tellurides with a five- or six-membered ring structure and their derivatives were developed as a new class of catalyst for the oxidation of organothiols to organodisulfides in a glutathione peroxidase-like catalytic reaction. Quantitative conversion and high reaction rate were achieved by performing the reaction in an organic-aqueous segmented microflow system. Importantly, the process circumvented product purification, which is a major limitation of current organodisulfide synthetic methods.
- Arai, Kenta,Osaka, Yuui,Haneda, Masahiro,Sato, Yuumi
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p. 3647 - 3655
(2019/07/22)
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- Europhtal (8020) efficiently catalyzes the aerobic oxidation of in situ generated thiols to symmetric disulfides (disulfanes)
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Efficient, odorless and scalable synthetic protocols have been introduced for the preparation of symmetric alkyl disulfides by treatment of the corresponding organic halides with thiourea and NaHCO3in the presence of commercially available Europhtal catalyst (8020) in both H2O and poly ethylene glycol (PEG-200) media at 80–90 °C. Structurally diverse primary, secondary, allylic and benzylic halides were examined successfully whereas, the result with tert-butyl bromide was not satisfactory. Also, another procedure has been introduced for achieving symmetric aryl disulfides in high yields by reacting aryl halides, thiourea and NaHCO3in PEG-200 at 115–120 °C using CuI along with Europhtal catalysts. The results showed that the aerobic oxidation of in situ generated thiols proceeded efficiently in the presence of Europhtal catalyst giving the symmetric disulfide without contamination by symmetric sulfide side-product.
- Abbasi, Mohammad,Sabet, Askar,Sabet, Askar
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- Conversion of organic halides to disulfanes using KCN and CS2
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A sulfur transfer reagent was produced in situ upon stirring a mixture of KCN and CS2 in DMF at r.t. for 15 min, which after heating with an alkyl halide or aryl halide and CuI gave the corresponding symmetric dialkyl or diaryl disulfide, respectively, in high to excellent yields.
- Abbasi, Mohammad,Nowrouzi, Najmeh,Borazjani, Saeedeh Ghassab
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p. 4251 - 4254
(2017/10/11)
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- Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H
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We report an operationally simple, metal-free approach for the late-stage introduction of the important lipophilic hydrogen-bond donor motif, SCF2H. This reaction converts diaryl- and dialkyl-disulfides into the corresponding aryl/alkyl-SCF2H through the nucleophilic transfer of a difluoromethyl group with good functional group tolerance. This method is notable for its use of commercially available TMSCF2H, and does not rely on the need for handling of sensitive metal complexes.
- Howard, Joseph L.,Schotten, Christiane,Alston, Stephen T.,Browne, Duncan L.
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supporting information
p. 8448 - 8451
(2016/07/07)
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- A two in one approach: Renewable support and enhanced catalysis for sweetening using chicken feather bound cobalt(II) phthalocyanine under alkali free environment
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Poultry waste chicken feathers, an inexpensive and abundantly available material has been used as a renewable support for immobilizing a cobalt phthalocyanine catalyst. The synthesized heterogeneous cobalt(ii) phthalocyanine catalyst was used for the aerobic oxidation of mercaptans to the corresponding disulfides using ultrasonic irradiation under alkali free conditions. The significantly higher catalytic activity of the heterogeneous catalyst as compared to a homogeneous one can be attributed to the synergistic effect of the support matrix. In addition, the catalyst could easily be recovered and recycled for several runs without loss of activity, which makes the process greener and more cost-effective.
- Chauhan, Deepak K.,Patnam, Padma L.,Ganguly, Sudip K.,Jain, Suman L.
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p. 51983 - 51988
(2016/06/13)
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- Disulfide-based metal-free α-sulfanylation of ketones
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An eco-friendly methodology for the direct α-sulfanylation of ketones, has been developed. The procedure, based on the use of functionalized diaryldisulfides and catalyzed by d,l-proline, represents a mild and efficient approach for the preparation of α-arylthio-ketones.
- Vaquer, Andrea F.,Frongia, Angelo,Secci, Francesco,Tuveri, Enrica
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p. 96695 - 96704
(2015/11/24)
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- Simple, chemoselective hydrogenation with thermodynamic stereocontrol
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Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.
- Iwasaki, Kotaro,Wan, Kanny K.,Oppedisano, Alberto,Crossley, Steven W. M.,Shenvi, Ryan A.
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p. 1300 - 1303
(2014/02/14)
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- CuCl-catalyzed cleavage of S-triphenylmethyl thioether: a new detritylation method for thio group
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A new method for the deprotection of trityl thioethers using CuCl as the catalyst under ultrasonic conditions is described.
- Ma, Ming,Zhang, Xiu,Peng, Lingling,Wang, Jianbo
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p. 1095 - 1097
(2008/01/27)
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- Synthesis of disulfides containing a corrinoid head group for preparation of self-assembled monolayers
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The synthesis of three novel alkane disulfides with head-groups derived from vitamin B12, 14a, 14b and 15, is described. Self-assembled monolayers on gold are prepared from the symmetrical disulfide 15, bearing two cobyrinate head groups. The coating of the gold surface is analyzed by TOF-SIMS and ESCA measurements. Georg Thieme Verlag Stuttgart.
- Mendon?a, Joana,Luginbühl, Reto,Siegenthaler, Hans,Keese, Reinhart
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p. 1901 - 1904
(2007/10/03)
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- A novel reduction of sodium alkyl thiosulfates with InCl 3(cat.)/Sm(0) system in aqueous media: Facile synthesis of disulfides
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A novel reduction of sodium alkyl thiosulfates. with InCl 3(cat.)/Sm(0) system in aqueous media has been developed, which generates the corresponding disulfides in good yields.
- Li, Pinhua,Wang, Lei,Yang, Yaner,Sun, Xinhua,Wang, Min,Yan, Jincan
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p. 376 - 379
(2007/10/03)
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- A novel reduction of sodium alkyl thiosulfates using samarium metal without an activating agent in water
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A novel metallic samarium promoted reduction of sodium alkyl thiosulfates in the absence of an activating agent occurs to afford the corresponding disulfides with good yields in water at 90°C.
- Wang, Lei,Li, Pinhua,Zhou, Li
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p. 8141 - 8143
(2007/10/03)
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- Cobalt phthalocyanine mediated aerobic oxidation of thiols: A simple and convenient preparation of disulphides
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Cobalt phthalocyaninetetrasulphonamide/tetrasodium salt of cobalt tetrasulphophthalocyanine catalyzed oxidation with molecular oxygen form a simple, efficient and environmentally acceptable synthetic tool for the oxidation of thiols to disulphides in excellent yields, under mild conditions and without any side reactions.
- Venkateshwar Rao,Narasimha Rao,Jain, Suman L.,Sain, Bir
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p. 1151 - 1157
(2007/10/03)
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- Liquid-phase oxidation of thiols with chlorine dioxide
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The products and kinetics of the liquid-phase oxidation of 11 aliphatic and aromatic thiols with chlorine dioxide were studied at -10-+70 °C in organic media. The rate constants and activation parameters of the reaction were determined. The influence of the thiol structure on its reactivity was studied. A strong solvent effect on the reaction rate constant was found, and the reaction mechanism was proposed.
- Yakupov,Shereshovets,Imashev,Ismagilov
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p. 2352 - 2355
(2007/10/03)
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- Water accelerated Sm/TMSCl reductive system: Debromination of vic- dibromides and reduction of sodium alkyl thiosulfates
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A simple and efficient method for the debromination of vic-dibromides to (E)-alkenes and reduction of sodium alkyl thiosulfates to disulfides promoted by Sm/TMSCl/H2O (trace) has been described.
- Xu, Xiaoliang,Lu, Ping,Zhang, Yongmin
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p. 1917 - 1925
(2007/10/03)
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- Metallic samarium promoted reductive dimerization cyclization of gem- diactivated alkenes, reductive debromination of vic-dibromides, and reduction of sodium alkyl thiosulfates in aqueous media
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In saturated NH4Cl (aq.)-THF solution at room temperature, metallic samarium promoted reductive dimerization cyclization of gem-diactivated alkenes, reductive debromination of vic-dibromides, and reduction of sodium alkyl thiosulfates occur to afford corresponding functionalized cyclopentenes, (E)-alkenes, and disulfides. respectively in good yield. Only sub-stoichiometric quantities of samarium are employed in the former reactions and the trans- or trans,trans-form isomer is the majority product of the polysubstituted cyclopentene products.
- Wang, Lei,Zhang, Yongmin
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p. 10695 - 10712
(2007/10/03)
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- Hydrotalcite clay-catalysed air oxidation of thiols
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Hydrotalcite is an efficient catalyst for air oxidation of a variety of aromatic, aliphatic and alicyclic thiols in hexane, affording the corresponding disulfides in excellent to quantitative yields under mild and neutral conditions.
- Hirano, Masao,Monobe, Hiroyuki,Yakabe, Sigetaka,Morimoto, Takashi
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p. 374 - 375
(2007/10/03)
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- Preparation and characterization of long-chain di-n-alkyl disulfides
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The preparation of long-chain symmetric di-n-alkyl disulfides based on the reaction of BUNTE SALTS (RS2O3Na) with iodine is reported. 1H-NMR, FT-IR, and FT-RAMAN spectra of the solid and liquid/molten aliphatic title disulfides were recorded. An assignment of the vibrational frequencies is proposed especially in regard to the S-S and C-S vibrations. Distinct spectral differences are determined between the solid and liquid state, as well as between disulfides with even and those with odd numbered alkyl substituents, respectively. The observed phenomena are ascribed to different species in the solids and liquids/melts and their respective VAN DER WAALS interactions. In addition, mass spectra, GC-MS studies, as well as the thermal behaviour of the disulfides, based on investigations by DSC and TGA, are reported.
- Steinfatt, Ingeborg,Hoffmann, Gerhard G.,Brouwer, Ludwig,Menzel, Frank,Brockner, Wolfgang
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- Simple Oxidation of Thiols with Sodium lodate under Solid-Solution Biphasic Conditions
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A variety of aromatic, aliphatic, and alicyclic thiols were readily oxidised with a combination of sodium iodate and Chromatographic neutral alumina in hexane to afford the corresponding disulfides in excellent yields under mild and neutral conditions.
- Hirano, Masao,Yakabe, Sigetaka,Ando, Ken-Ichiro,Morimoto, Takashi
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p. 816 - 817
(2007/10/03)
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- Alumina: An Efficient and Reusable Catalyst for the Oxidative Coupling of Thiols with DMSO
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An inexpensive combination of common laboratory reagents, dimethyl sulfoxide (DMSO) and Chromatographic neutral alumina, gives an efficient, selective, and high-yielding oxidation of aromatic, aliphatic and alicyclic thiols to the corresponding disulfides in excellent yields under relatively mild conditions.
- Hirano, Masao,Yakabe, Sigetaka,Monobe, Hiroyuki,Morimoto, Takashi
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p. 472 - 473
(2007/10/03)
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- Oxidation by Chemical Manganese Dioxide. Part 2.1 Simple and High-yielding Synthesis of Symmetrical Disulfides via the Oxidative Coupling of Thiols
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Aromatic, aliphatic, and alicyclic thiols readily underwent oxidative coupling with chemical manganese dioxide in hexane to afford the corresponding disulfides in essentially quantitative yields under relatively mild conditions.
- Hirano, Masao,Yakabe, Sigetaka,Chikamori, Hideki,Clark, James H.,Morimoto, Takashi
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p. 310 - 311
(2007/10/03)
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- Preparation of disulfides by reduction of sodium alkyl thiosulfates with metallic samarium and catalytic amount of iodine
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Sm/I2 reduces sodium alkyl thiosulfates to the corresponding disulfides in good to excellent yields in THF at room temperature.
- Huang, You,Zhang, Yongmin,Wang, Yulu
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p. 1043 - 1047
(2007/10/03)
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- Preparation of dialkyl disulfides via reduction of alkylthiocyanates with TiCl4/Sm system
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Dialkyl disulfides can be readily prepared in moderate to good yields via reduction of alkylthiocyanates with TiCl4/Sm system in THF at 0°C.
- Guo, Hongyun,Zhan, Zhuangping,Zhang, Yongmin
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p. 2721 - 2724
(2007/10/03)
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- An environmentally friendly oxidation of thiols to disulfides by calcium hypochlorite and montmorillonite K10 in hexane
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Aromatic, aliphatic, and alicyclic thiols can be readily oxidized to the disulfides quantitatively by calcium hypochlorite and moist Montmorillonite K10 under mild and neutral conditions.
- Hirano, Masao,Yakabe, Shigetaka,Fukami, Masataka,Morimoto, Takashi
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p. 2783 - 2788
(2007/10/03)
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- Preparation of disulfides by the oxidation of thiols using bromine
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Medium length aliphatic disulfides are easily synthesized via the bromine-oxidation of thiols in the absence of solvent. Bromine can also oxidize long aliphatic and aromatic thiols to disulfides in solution. All yields are quantitative.
- Wu, Xiaoming,Rieke, Reuben D.,Zhu, Lishan
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p. 191 - 196
(2007/10/03)
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- Reductive cleavage of S-S bond by samarium diiodide: A novel method for the synthesis of disulfides
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Samarium diiodide reductively cleaves the S-S bond of sodium alkyl thiosulfates to give the corresponding disulfides in moderate to good yields under mild and neutral conditions.
- Jia,Zhang,Zhou
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p. 2893 - 2898
(2007/10/02)
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- Reductive cleavage of C - S bond by samarium diiodide: A novel method for the synthesis of disulfides and thiolesters
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Disulfides were obtained by the reaction of thiocyanates with equivalent SmI2. Smarium thiolates were generated by the reaction of an equivalent of thiocyanates with two equivalents of SmI2, and then reacted smoothly with acyl chlorides to give thiolesters.
- Jia, Xueshun,Zhang, Yongmin,Zhou, Zunjun
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p. 8833 - 8834
(2007/10/02)
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- Autoxidation of 1-Decanethiol Catalyzed by Cobalt Phthalocyaninetetrasulfonate on Cationic Latexes
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Cationic latexes 60 nm in diameter have been prepared by emulsion copolymerization of 2percent of quaternary ammonium ion surfactant monomers and 1-5percent of divinylbenzene with styrene.All of the surfactant monomers were bound to the product latexes, w
- Hassanein, M.,Ford, Warren T.
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p. 3106 - 3113
(2007/10/02)
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