Crosslinking reaction mechanism of diisopropyl xanthogen polysulfide accelerator in bromobutyl elastomer for medical device applications

Ohbi, D. S.; Purewal, T. S.; Shah, Tahir; Σιώρης, Ηλίας

doi:10.1002/app.27618

Cited by 9 publications

(6 citation statements)

References 16 publications

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“…Isopropylxanthic disulfide (IXDS), an important molecule in vulcanization accelerators, flotation agent, and energy materials, [ 11 ] was chosen to explain the SFE process. Typical synthesis process for IXDS involves two steps (Figure S3 , Supporting Information): 1) a condensation reaction of isopropanol with alkali‐metal hydroxide and carbon disulfide (CS 2 ) to form sodium isobutyl xanthate 2) which was oxidized by oxidizing agents (e.g., H 2 O 2 , K 2 S 2 O 8 , and I 2 ).…”

Section: Resultsmentioning

confidence: 99%

Smart Flow Electrosynthesis and Application of Organodisulfides in Redox Flow Batteries

Chen

Guo

2021

Advanced Science

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Electrochemical techniques have been recognized as an environmentally friendly and sustainable synthetic way to form organodisulfides. However, searching for optimum conditions which suffers from time/material-consuming caused by the uncertainty of reactant consumption has hindered its rapid and large-scale development. Inspired by advanced nonaqueous redox flow batteries (NARFBs) technology, it is proposed a smart flow electrosynthesis (SFE) method of organodisulfides that the voltage curve of NARFBs can be utilized as a precise indicator to reflect the desired information about reactants and distinguish the end point of reaction automatically. This electrochemical method also exhibits certain universality and scalability. Additionally, organodisulfides generated in electrolytes can be used as active species for NARFBs without further purification, and their electrochemical properties are easily adjusted by changing raw materials, which effectively alleviate the waste in complex synthesis steps for optimizing and designing active materials separately. An organodisulfide dervied from isopropyl alcohol and carbon disulfide shows excellent cycling life (1000 cycles) with low capacity fade rate (0.024% per cycle). Taking advantages of the inherent NARFBs, this work not only proves a SFE strategy, but also supplies a green and low-cost molecular engineering scheme for designing electroactive materials for energy storage.

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Section: Resultsmentioning

confidence: 99%

Smart Flow Electrosynthesis and Application of Organodisulfides in Redox Flow Batteries

Chen

Guo

2021

Advanced Science

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“…However, Orbhi et al identified that the activity of DIXP is comparable to MBTS/thiourea system used in the vulcanization of bromobutyl elastomer in medical drug delivery device applications without leaving reaction residues in the network structure. 25,26 In addition, a systematic investigation on the use of DIXP and their combinations for NR compounding has not been carried out and the available information is also very scanty. Further, no studies were reported specifically on the use of DIXP combined with other nitrosamine-safe accelerators in efficient sulfur vulcanization systems to produce vulcanizates from dry rubber-based NR.…”

Section: Introductionmentioning

confidence: 99%

The use of diisopropyl xanthogen polysulfide as a potential accelerator in efficient sulfur vulcanization of natural rubber compounds

Samarasinghe

Walpalage

Edirisinghe

et al. 2021

J of Applied Polymer Sci

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With the emerging concerns on the use of nitrosamine evolving accelerators, safer alternatives are desirable for the rubber industry. In the present study, cure characteristics, physicomechanical properties, crosslink density, aging, dynamic mechanical, and thermal properties of vulcanizates prepared with two nitrosamine safe binary accelerator systems containing diisopropyl xanthogen polysulfide (DIXP) and tetrabenzyl thiuram disulfide (TBzTD), and DIXP and dibenzyl dithiocarbamate (ZBeC) were investigated for efficient sulfur vulcanization of natural rubber (NR) compounds. Synergistic effect in both cure and physicomechanical properties was observed for all the combinations of the two accelerator systems. The composition containing DIXP with a lower loading (0.6 phr) of TBzTD, and ZBeC, demonstrated the highest technological performance. Retention of tensile properties on oxidative aging was highest for the vulcanizate prepared with DIXP/TBzTD (1.4/0.6). Dynamic mechanical and thermogravimetric analysis further confirmed the crosslink density and thermal stability of the network structure of the binary systems. In overall, DIXP shows the potential to be used as a safer accelerator in the manufacture of appropriate dry NR-based rubber products.

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“…[ 39 ] In addition, Xanthates have been used as vulcanization accelerators by the rubber industry. [ 40 ] This vast range of commercial production capability and application motivates us to study the electrochemical properties of this class of compounds and compels us to promote its further study as a new class of organosulfur materials for high‐energy‐density rechargeable batteries.…”

Section: Introductionmentioning

confidence: 99%

Xanthogen Polysulfides as a New Class of Electrode Material for Rechargeable Batteries

Bhargav

Manthiram

2020

Advanced Energy Materials

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electrochemical reversibility. In addition to their favorable redox behavior, these compounds are also naturally abundant, environmentally friendly, inexpensive, and easy to process into battery electrodes. [12] While sulfur offers a high energy density exceeding 2500 W h kg −1 , it is beleaguered by three major issues. First, the electrical conductivity of sulfur is extremely low, necessitating the addition of a large amount of conductive hosts (e.g., carbon) in the battery electrode. Second, the difference in density between sulfur and its discharge product, Li 2 S, is quite large. This results in a volume change of nearly 80% during cycling, thus requiring a cathode structure to accommodate the large volume fluctuation and the resulting stresses generated. Third, the lithium polysulfides formed during cycling are electrolyte-soluble and thus shuttle between the electrodes. This "shuttle effect" results in a loss of active material, poor Coulombic efficiency, and short cycle life. [8] On the other hand, organic compounds (e.g., carbonyls, organosulfides, imines, and nitriles) present three distinct advantages. First, the functional groups in the organic moieties can alter the physical properties of these materials including their electrical conductivity. [9] Second, the difference in density between the delithiated and the lithiated forms of these compounds is low, resulting in a smaller volume change and stress in the cathode. [13] Finally, the bulkiness and polarity of the organic functional groups can be used to alter their solubility in the electrolyte, thus minimizing parasitic shuttle effects. [12,14] Organosulfur compounds combine the multi-electron, highenergy-density characteristics of sulfur with the distinct advantages of organic compounds. Specifically, the ability to tune the physical and chemical properties of organosulfur materials with various functional groups allows for optimization of their conductivity, solubility, and density. [9,15-17] Recognizing these advantages, various organosulfur compounds have been reported since the late 1980s. [18,19] Early reports of such materials focused on polymers that functioned according to the disulfide-thiolate redox behavior. [19,20] More recently, polymers containing multiple SS bonds that have been synthesized through inverse vulcanization, [21,22] incorporation of covalent frameworks, [22-25] and condensation reactions have been reported. [26-29] In addition to polymers, linear compounds, [15,30,31] cyclics, [32] hybrids, [33,34] and compounds with unique functional groups have also been reported. [35-37] Organosulfides are an emerging class of alternative sulfur-based cathode materials. This work explores a new member in this family of active materials, viz., xanthogen polysulfides. Diisopropyl xanthogen polysulfide (DIXPS) is used as a model compound in a lithium battery to understand the chemical changes and the unique electrochemical behavior of this class of materials by employing various materials characterization methodologies. As a cathode ma...

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Crosslinking reaction mechanism of diisopropyl xanthogen polysulfide accelerator in bromobutyl elastomer for medical device applications

Cited by 9 publications

References 16 publications

Smart Flow Electrosynthesis and Application of Organodisulfides in Redox Flow Batteries

Smart Flow Electrosynthesis and Application of Organodisulfides in Redox Flow Batteries

The use of diisopropyl xanthogen polysulfide as a potential accelerator in efficient sulfur vulcanization of natural rubber compounds

Xanthogen Polysulfides as a New Class of Electrode Material for Rechargeable Batteries

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