Sulfur Radical Transfer and Coupling Reaction to Benzoxazine Groups: A New Reaction Route for Preparation of Polymeric Materials Using Elemental Sulfur as a Feedstock

Two novel polyurethanes (PU) with alternating and random block architectures, hydroxyl-terminated polybutadiene (HTPB)/polyethylene glycol (PEG) block copolymers, HTPB-alt-PEG and HTPB-co-PEG, were synthesized via a coupling reaction route between hydroxyl groups and isocyanate groups. The structural and crystal characterization was conducted by means of FTIR, and phase behavior was examined by SEM and DSC. The biodegradation in a simulated human body fluid was investigated through mass loss and SEM. The experimental results indicate that all polyurethane samples form the microphase separation structure, and the separation degree depended on their sequence structure and the molecular weight (MW) of PEG, and further affecte their in-vitro degradation.

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A sulfur–eugenol allyl ether copolymer: a material synthesized via inverse vulcanization from renewable resources and its application in Li–S batteries

Materials Chemistry Frontiers ◽

10.1039/c7qm00083a ◽

2017 ◽

Vol 1 (9) ◽

pp. 1818-1822 ◽

Cited By ~ 29

Author(s):

Alexander Hoefling ◽

Dan Thien Nguyen ◽

Young Joo Lee ◽

Seung-Wan Song ◽

Patrick Theato

Keyword(s):

Cathode Materials ◽

Renewable Resources ◽

Elemental Sulfur ◽

Polymeric Materials ◽

Allyl Ether

Polymeric materials based on abundant elemental sulfur and renewable eugenol show enhanced cyclability as cathode materials in Li–S batteries.

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Self‐Coupling Reaction of Benzylamine to Form Thioamides and Amides by Elemental Sulfur

ChemistrySelect ◽

10.1002/slct.201903512 ◽

2019 ◽

Vol 4 (45) ◽

pp. 13388-13391

Author(s):

Zhenzhen Zhan ◽

Nan Luo ◽

Haojie Ma ◽

Jianping He ◽

Guoqiang Lu ◽

...

Keyword(s):

Elemental Sulfur ◽

Coupling Reaction

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Polymerizations with Elemental Sulfur: From Petroleum Refining to Polymeric Materials

Journal of the American Chemical Society ◽

10.1021/jacs.1c09329 ◽

2021 ◽

Author(s):

Taeheon Lee ◽

Philip T. Dirlam ◽

Jon T. Njardarson ◽

Richard S. Glass ◽

Jeffrey Pyun

Keyword(s):

Elemental Sulfur ◽

Petroleum Refining ◽

Polymeric Materials

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Spectroscopical characterization of carbonaceous matter prepared through the Glaser coupling reaction route

Carbon ◽

10.1016/s0008-6223(98)90106-3 ◽

1999 ◽

Vol 37 (1) ◽

pp. 161-163 ◽

Cited By ~ 31

Author(s):

Franco Cataldo

Keyword(s):

Coupling Reaction ◽

Carbonaceous Matter ◽

Reaction Route ◽

Glaser Coupling

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The use of elemental sulfur as an alternative feedstock for polymeric materials

Nature Chemistry ◽

10.1038/nchem.1624 ◽

2013 ◽

Vol 5 (6) ◽

pp. 518-524 ◽

Cited By ~ 551

Author(s):

Woo Jin Chung ◽

Jared J. Griebel ◽

Eui Tae Kim ◽

Hyunsik Yoon ◽

Adam G. Simmonds ◽

...

Keyword(s):

Elemental Sulfur ◽

Polymeric Materials ◽

Alternative Feedstock

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Sulfur/Organic Copolymers as Curing Agents for Rubber

Polymers ◽

10.3390/polym10080870 ◽

2018 ◽

Vol 10 (8) ◽

pp. 870 ◽

Cited By ~ 7

Author(s):

Jakub Wręczycki ◽

Dariusz Bieliński ◽

Rafał Anyszka

Keyword(s):

Mechanical Properties ◽

Crosslink Density ◽

Elemental Sulfur ◽

Freezing Point ◽

Petroleum Industry ◽

Polymeric Materials ◽

Mechanical Analysis ◽

Radical Copolymerization ◽

Scanning Calorimetry ◽

Free Radical Copolymerization

It is widely acknowledged that waste sulfur generated from the petroleum industry creates huge storage and ecological problems. Therefore, the various methods of utilization are becoming increasingly attractive research topics worldwide. The thermal ability of elemental sulfur to homolytic cleavage of S8 rings enables its free radical copolymerization with unsaturated organic species and the obtaining of chemically stable polymeric materials. Here we report a novel possibility to use sulfur/organic copolymers obtained via “inverse vulcanization” as curatives for rubber. For this purpose, several various sulfur/organic copolymers were synthesized and analyzed from the point of view of their performance as rubber crosslinking agents. Solvent extraction was used to purify sulfur/organic copolymers from unreacted (elemental) sulfur. Thermal properties of the prepared copolymers were characterized by thermogravimetric analysis and differential scanning calorimetry (TGA–DSC). Crosslink density and structure of cured elastomers was studied by equilibrium swelling, thiol-amine analysis and freezing point depression. Mechanical properties of the vulcanizates were determined under static and dynamic conditions (DMA—dynamic mechanical analysis). It is proved that the utilization of sulfur/organic copolymers as curatives enables an effective crosslinking process of rubbers. Taking into account the results of a crosslink density analysis and mechanical properties of the vulcanizates cured with purified copolymers, it is evident that relatively long copolymer macromolecules are also involved in the formation of chemical bonds between unsaturated rubber macromolecules.

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