Classifications

• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B60—VEHICLES IN GENERAL
  • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
  • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K2201/00—Specific properties of additives
  • C08K2201/002—Physical properties
  • C08K2201/005—Additives being defined by their particle size in general
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/005—Stabilisers against oxidation, heat, light, ozone

Definitions

• the present disclosure provides insoluble sulfur compositions useful for the vulcanization of rubber for the production of rubber products, e.g., tires.
• Insoluble sulfur also referred to as polymeric sulfur
• Insoluble sulfur is used as a cross-linking (vulcanizing) agent in rubber compound formulations.
• Insoluble sulfur is polymeric in nature, and does not dissolve in carbon disulfide.
• insoluble sulfur rather than soluble sulfur avoids a number of processing issues, the most common being “bloom,” wherein soluble sulfur migrates within a rubber compound and crystallizes at the surface, and “bin scorch,” which is the premature vulcanization of rubber when mixed with soluble sulfur.
• Insoluble sulfur is a solid powder that is mixed with elastomers to form rubber compounds.
• the present disclosure provides compositions comprising insoluble sulfur, a process oil, one or more polymers, and, optionally, a stabilizer.
• the composition comprises from about 50 wt% to about 95 wt% insoluble sulfur, from about 5 wt% to about 50 wt% of a process oil, and from about 0.1 wt% to about 3 wt% of one or more polymers, wherein at least one of the one or more polymers is an ethylene propylene diene (EPDM) polymer, a styrene isoprene styrene (SIS) polymer, an oxygenated polymer, a polyolefin plastomer or elastomer, or an isoprene polymer.
• EPDM ethylene propylene diene
• SIS styrene isoprene styrene
• the present disclosure provides vulcanized elastomeric articles comprising the insoluble sulfur compositions disclosed herein.
• the present disclosure provides vulcanized elastomeric articles prepared using the insoluble sulfur compositions described herein.
• the present disclosure provides a process for preparing a vulcanized elastomeric article, the process comprising:
• kits comprising an insoluble sulfur composition disclosed herein and instructions for using the composition in a vulcanizable elastomeric composition.
• kits comprising a composition disclosed herein and instructions for using the composition to prepare a vulcanized elastomeric article.
• the present disclosure provides sulfur masterbatches comprising an insoluble sulfur composition disclosed herein and at least one elastomer.
• one or more as used herein is intended to mean that at least one component in a relevant category of components, e.g. one or more polymers, is present and, in some embodiments, more than one component is present. In some embodiments, one or more means 1 to 5. In some embodiments, one or more means 1 to 4. In some embodiments, one or more means 1 to 3. In some embodiments, one or more means 1 or
• wt% refers to the mass of one component, or a specific subset of components, in a composition or mixture, e.g., a composition comprising insoluble sulfur, process oil, and one or more polymers, divided by the combined mass of all components in the composition or mixture, times 100.
• average primary particle size refers to the median particle size of unagglomerated, individual particles by volume as measured by static light scattering. This term is also known as "D50.”
• number average molecular weight refers to the statistical average molecular weight of all polymer chains in a polymer sample.
• weight average molecular weight or “Mw” as used herein refer to the weight average molecular weight of all polymer chains in a polymer sample.
• terpolymer refers to a polymer formed by the polymerization of three different monomers. In some embodiments, the monomers are randomly arranged throughout the polymer chain.
• diene refers to a compound containing two double bonds.
• An example of a diene is ethylidene norbornene (ENB), which has the following structure:
• Mooney viscosity refers to the shearing torque resisting rotation of a cylindrical metal disk (or rotor) embedded in rubber within a cylindrical cavity, as fully defined in a standard test method, e.g., ASTM DI 646.
• melt index refers to a measure of the ease of flow of the melt of a thermoplastic polymer, defined as the mass of polymer, in grams, flowing in ten minutes through a capillary of a specific diameter and length by a pressure applied via prescribed alternative gravimetric weights for alternative prescribed temperatures, as described in the standards ASTM DI 238 and ISO 1133.
• Coupled efficiency refers to the percentage of triblock copolymer formed when synthesizing a triblock copolymer, e.g., styrene-isoprene- styrene (SIS), from a diblock copolymer, e.g., styrene-isoprene (SI).
• compositions comprising insoluble sulfur, a process oil, one or more polymers, and, optionally, a stabilizer.
• the composition comprises from about 50 wt% to about 95 wt% of insoluble sulfur, from about 5 wt% to about 50 wt% of a process oil, from about 0.1 wt% to about 3 wt% of one or more polymers, and from 0 wt% to about 1 wt% of a stabilizer.
• the present disclosure provides compositions comprising insoluble sulfur, a process oil, one polymer, and, optionally, a stabilizer.
• the composition comprises from about 50 wt% to about 95 wt% of insoluble sulfur, from about 5 wt% to about 50 wt% of a process oil, from about 0.1 wt% to about 3 wt% of one polymer, and from 0 wt% to about 1 wt% of a stabilizer.
• the present disclosure provides compositions comprising insoluble sulfur, a process oil, two polymers, and, optionally, a stabilizer.
• the composition comprises from about 50 wt% to about 95 wt% of insoluble sulfur, from about 5 wt% to about 50 wt% of a process oil, from about 0.1 wt% to about 3 wt% of two polymers, and from 0 wt% to about 1 wt% of a stabilizer.
• the present disclosure provides compositions comprising insoluble sulfur, a process oil, three polymers, and, optionally, a stabilizer.
• the composition comprises from about 50 wt% to about 95 wt% of insoluble sulfur, from about 5 wt% to about 50 wt% of a process oil, from about 0.1 wt% to about 3 wt% of three polymers, and from 0 wt% to about 1 wt% of a stabilizer.
• compositions disclosed herein comprise one or more polymers.
• at least one of the one or more polymers is an ethylene propylene diene (EPDM) polymer, a styrene isoprene styrene (SIS) polymer, an oxygenated polymer, a polyolefin plastomer or elastomer, or an isoprene polymer.
• EPDM ethylene propylene diene
• SIS styrene isoprene styrene
• oxygenated polymer a polyolefin plastomer or elastomer
• isoprene polymer isoprene polymer.
• ethylene propylene diene polymer or "EPDM polymer” as used herein refers to a terpolymer formed from ethylene, propylene, and diene monomers.
• the diene is dicyclopentadiene (DCPD).
• the diene is vinyl norbornene (VNB).
• the diene is ethylidene norbornene (ENB).
• the EPDM polymer comprises the following structure: wherein n, 1, and p are positive integers.
• ethylene content refers to the wt% of a polymer that derives from ethylene monomer.
• the EPDM polymer has an ethylene content of from about 55 wt% to about 85 wt%.
• the EPDM polymer has an ethylene content of from about 40 wt% to about 45 wt%, from about 40 wt% to about 50 wt%, from about 40 wt% to about 55 wt%, from about 40 wt% to about 60 wt%, from about 40 wt% to about 65 wt%, from about 40 wt% to about 70 wt%, from about 40 wt% to about 75 wt%, from about 40 wt% to about 80 wt%, from about 40 wt% to about 85 wt%, from about 40 wt% to about 90 wt%, from about 45 wt% to about 50 wt%, from about 45 wt% to about 55 wt%, from about 45 wt% to about 60 wt%, from about 45 wt% to about 65 wt%, from about 45 wt% to about 70 wt%, from about 45 wt% to about 75 wt%
• the EPDM polymer has an ethylene content of about 70 wt%. In some embodiments, the EPDM polymer has an ethylene content of about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 75 wt%, about 80 wt%, about 85 wt%, or about 90 wt%.
• ethylidene norbornene content refers to the wt% of a polymer that derives from ethylidene norbomene monomer.
• the EPDM polymer has an ethylidene norbomene content of from about 0 wt% to about 10 wt%.
• the EPDM polymer has an ethylidene norbomene content of from about 0 wt% to about 1 wt%, from about 0 wt% to about 2 wt%, from about 0 wt% to about 3 wt%, from about 0 wt% to about 4 wt%, from about 0 wt% to about 5 wt%, from about 0 wt% to about 6 wt%, from about 0 wt% to about 7 wt%, from about 0 wt% to about 8 wt%, from about 0 wt% to about 9 wt%, from about 0 wt% to about 10 wt%, from about 1 wt% to about 2 wt%, from about 1 wt% to about 3 wt%, from about 1 wt% to about 4 wt%, from about 1 wt% to about 5 wt%, from about 1 wt% to about
• the EPDM polymer has an ethylidene norbornene content of about 5 wt%. In some embodiments, the EPDM polymer has an ethylidene norbornene content of about 0 wt%, about 0.5 wt%, about 1 wt%, about 1.5 wt%, about 2 wt%, about 2.5 wt%, about 3 wt%, about 3.5 wt%, about 4 wt%, about 4.5 wt%, about 5.5 wt%, about 6 wt%, about 6.5 wt%, about 7 wt%, about 7.5 wt%, about 8 wt%, about 8.5 wt%, about 9 wt%, about 9.5 wt%, or about 10 wt%.
• the EPDM polymer has a Mooney viscosity of from about 15 ML(l+4) to about 90 ML(l+4) when measured according to the ASTM D1646 standard. In some embodiments, the EPDM polymer has a Mooney viscosity of from about 10 ML(l+4) to about 20 ML(l+4), from about 10 ML(l+4) to about 30 ML(l+4), from about 10 ML(l+4) to about 40 ML(l+4), from about 10 ML(l+4) to about 50 ML(l+4), from about 10 ML(l+4) to about 60 ML(l+4), from about 10 ML(l+4) to about 70 ML(l+4), from about 10 ML(l+4) to about 80 ML(l+4), from about 10 ML(l+4) to about 90 ML(l+4), from about 20 ML(l+4) to about 30 ML(l+4), from about 20 ML(l+4) to about 20 ML(l+4)
• the EPDM polymer has a Mooney viscosity of about 25 ML(l+4) when measured according to the ASTM DI 646 standard. In some embodiments, the EPDM polymer has a Mooney viscosity of about 10 ML(l+4), about 15 ML(l+4), about 20 ML(l+4), about 30 ML(l+4), about 35 ML(l+4), about 40 ML(l+4), about 45 ML(l+4), about 50 ML(l+4), about 55 ML(l+4), about 60 ML(l+4), about 65 ML(l+4), about 70 ML(l+4), about 75 ML(l+4), about 80 ML(l+4), about 85 ML(l+4), or about 90 ML(l+4), when measured according to the ASTM DI 646 standard.
• the Mooney viscosity is measured at a temperature of about 125 °C. In some embodiments, the Mooney viscosity is measured at a temperature of about 100 °C, about 150 °C, or about 175 °C.
• the EPDM polymer is a NORDELTM EPDM polymer.
• NORDELTM EPDM polymers are manufactured by The Dow Chemical Company ("Dow”).
• Exemplary NORDELTM EPDM polymers and their properties (test method used noted in parentheses) are described in Table 1.
• the EPDM polymer is a VISTALONTM EPDM polymer.
• VISTALONTM EPDM polymers are manufactured by ExxonMobil. Exemplary VISTALONTM EPDM polymers are described in Table 2.
• the EPDM polymer is a ROYALENE® EPDM polymer, a ROYALEDGE® EPDM polymer, a ROYAL THERM® EDPM polymer, or a TRILENE® Liquid EPDM polymer.
• ROYALENE® EPDM, ROYALEDGE® EPDM, ROYALTHERM® EDPM, and TRILENE® Liquid EPDM polymers are manufactured by Lion Elastomers.
• Exemplary ROYALENE® EPDM, ROYALEDGE® EPDM, ROYALTHERM® EDPM, and TRILENE® Liquid EPDM polymers are described in Tables 3-6. Table 3
• FF indicates product also available in a free-flowing powder form; Diene (wt%) and Ethyl ene/Propylene Ratio in parentheses indicates values for FF form.
• the EPDM polymer is a KELTAN® EPDM polymer.
• KELTAN® EPDM polymers are manufactured by ARLANXEO. Exemplary KELTAN® EPDM polymers are described in Table 7.
• CLCB Controlled long chain branching
• N Narrow molecular weight distribution
• M Medium molecular weight distribution
• B broad molecular weight distribution
• the EPDM polymer is a DUTRAL® TER EPDM polymer.
• DUTRAL® TER EPDM polymers are manufactured by Versalis. Exemplary DUTRAL® TER EPDM polymers are listed in Table 8.
• At least one of the one or more polymers is an SIS polymer.
• styrene isoprene styrene polymer or "SIS polymer” as used herein refer to a block copolymer formed from styrene and isoprene (2-methyl-l,3-butadiene) monomers.
• SIS comprises the following structure: wherein n, 1, and p are positive integers.
• styrene content refers to the wt% of a polymer that derives from styrene monomer.
• the SIS polymer has a styrene content of from about 5 wt% to about 20 wt%. In some embodiments, the SIS polymer has a styrene content of from about 5 wt% to about 10 wt%, from about 5 wt% to about 15 wt%, from about 5 wt% to about 25 wt%, from about 5 wt% to about 30 wt%, from about 10 wt% to about 15 wt%, from about 10 wt% to about 20 wt%, from about 10 wt% to about 25 wt%, from about 10 wt% to about 30 wt%, from about 15 wt% to about 20 wt%, from about 15 wt% to about 25 wt%, from about 15 wt% to about 30 wt%, from about 20 wt% to about 25 wt%, from about 20 wt% to about 30 wt%, from about 20 wt%
• the styrene content of the SIS polymer is about 14 wt%. In some embodiments, the styrene content of the SIS polymer is about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, or about 30 wt%.
• At least one of the one or more polymers is an oxygenated polymer.
• oxygenated polymer refers to any polymer than contains one or more oxygen atoms.
• the oxygenated polymer comprises polyethylene glycol.
• polyethylene glycol or “PEG” as used herein refer to a polymer, or a block of a block copolymer, comprising the chemical formula -(O-CH2-CH2)n-, wherein n is a positive integer.
• the ethylene oxide content of the oxygenated polymer is from about 20 wt% to about 30 wt%, from about 20 wt% to about 40 wt%, from about 20 wt% to about 50 wt%, from about 20 wt% to about 60 wt%, from about 20 wt% to about 70 wt%, from about 20 wt% to about 80 wt%, from about 20 wt% to about 90 wt%, from about 20 wt% to about 100 wt%, from about 30 wt% to about 40 wt%, from about 30 wt% to about 50 wt%, from about 30 wt% to about 60 wt%, from about 30 wt% to about 70 wt%, from about 30 wt% to about 80 wt%, from about 30 wt% to about 90 wt%, from about 30 wt% to about 100 wt%, from about 40 wt% to about 50 wt%, from about
• the ethylene oxide content of the oxygenated polymer is about 70 wt%. In some embodiments, the ethylene oxide content of the oxygenated polymer is about 20 wt%, about 30 wt%, about 40 wt%, about 50 wt%, about 60 wt%, about 80 wt%, about 90 wt%, or about 100 wt%.
• the oxygenated polymer comprises polypropylene glycol.
• polypropylene glycol or "PPG” as used herein refer to a polymer, or a block of a block copolymer, having the chemical formula -(OCH(CH3)-CH2)n-, wherein n is a positive integer.
• PEG-PPG-PEG refers to a triblock copolymer of polyethylene glycol-polypropylene glycol-polyethylene glycol, where the length of each individual block can vary.
• PEG-PPG-PEG comprises an ethylene oxide, propylene oxide, and water content of 84 wt%, 15.6 wt%, and ⁇ 0.4 wt%, respectively.
• the PEG-PPG-PEG has a Mw of about 15,000 g/mol.
• PEG-PPG refers to a diblock copolymer of polyethylene glycolpolypropylene glycol, where the length of each individual block can vary.
• PEG-PPG comprises an ethylene oxide, propylene oxide, and water content of 75 wt%, 24.7 wt%, and ⁇ 0.3 wt%, respectively.
• PEAA poly(ethylene-co-acrylic acid)
• n and 1 are positive integers.
• the PEAA has an ethylene content of from about 55 wt% to about 85 wt%. In some embodiments, the PEAA has an ethylene content of from about 40 wt% to about 45 wt%, from about 40 wt% to about 50 wt%, from about 40 wt% to about 55 wt%, from about 40 wt% to about 60 wt%, from about 40 wt% to about 65 wt%, from about 40 wt% to about 70 wt%, from about 40 wt% to about 75 wt%, from about 40 wt% to about 80 wt%, from about 40 wt% to about 85 wt%, from about 40 wt% to about 90 wt%, from about 45 wt% to about 50 wt%, from about 45 wt% to about 55 wt%, from about 45 wt% to about 60 wt%, from about 45 wt% to about 65 wt%.
• acrylic acid content refers to the wt% of a polymer that derives from acrylic acid monomer.
• the PEAA comprises from about 10 wt% to about 20 wt% acrylic acid monomer.
• the PEAA comprises from about 1 wt% to about 5 wt%, from about 1 wt% to about 10 wt%, from about 1 wt% to about 15 wt%, from about 1 wt% to about 20 wt%, from about 1 wt% to about 25 wt%, from about 1 wt% to about 30 wt%, from about 5 wt% to about 10 wt%, from about 5 wt% to about 15 wt%, from about 5 wt% to about 20 wt%, from about 5 wt% to about 25 wt%, from about 5 wt% to about 30 wt%, from about 10 wt% to about 15 wt%, from about 10 wt% to about 20 wt%, from about 10 wt% to about 25 wt%, from about 10 wt% to about 30 wt%, from about 15 wt% to about 20 wt%, from about 15 wt%, from about
• the oxygenated polymer comprises dicarboxyl-terminated polybutadiene.
• polybutadiene or "BR” as used herein refer to a polymer formed from substituted or unsubstituted 1,3-butadiene monomers. Non-limiting examples of substituents include halogen, hydroxy, cyano, carboxyl, or combinations thereof. The stereochemistry of the 1,3-butadiene monomers can lead to polymers of cis-, trans-, and branched chain vinyl- orientations.
• the dicarboxyl-terminated polybutadiene has the following structure: wherein n is a positive integer.
• the oxygenated polymer comprises water. In some embodiments, the water content of the oxygenated polymer is less than 0.2 wt%. In some embodiments, the water content of the oxygenated polymer is less than 5 wt%, less than 4 wt%, less than 3 wt%, less than 2 wt%, less than 1 wt%, less than 0.8 wt%, less than 0.6 wt%, less than 0.4 wt%, or less than 0.1 wt%.
• At least one of the one or more polymers is a polyolefin plastomer (POP) or a polyolefin elastomer (POE).
• POP polyolefin plastomer
• POE polyolefin elastomer
• polyolefin plastomer refers to a polymer having the formula -(CH2-CH(R)) n -, wherein R is an alkyl chain of variable length and n is the number of monomer units.
• the polyolefin plastomer is an AFFINITYTM polyolefin plastomer. AFFINITYTM polyolefin plastomers are manufactured by Dow. Exemplary AFFINITYTM polyolefin plastomers are listed in Table 10.
• the polyolefin elastomer is an ENGAGETM polyolefin elastomer.
• ENGAGETM polyolefin elastomers are produced by Dow.
• Exemplary ENGAGETM polyolefin elastomers are listed in Tables 11-12.
• the polyolefin elastomer is a DUTRAL® polyolefin elastomer.
• DUTRAL® polyolefin elastomers comprise ethylene and propylene and are manufactured by Versalis.
• Exemplary DUTRAL® polyolefin elastomers are listed in Table 13.
• the polyolefin elastomer is a VISTAMAXXTM polymer.
• VISTAMAXXTM polymers are formed from a mixture of polypropylene and/or ethylene monomers and are manufactured by ExxonMobil. Exemplary VISTAMAXXTM polymers are listed in Table 14. Table 14
• the polyolefin plastomer or elastomer has a melt index of from about 500 g/10 min to about 1300 g/10 min as measured by ASTM D1238. In some embodiments, the polyolefin plastomer or elastomer has a melt index of from about 500 g/10 min to about 700 g/10 min, from about 700 g/10 min to about 1000 g/10 min, from about 700 g/10 min to about 1200 g/10 min, or from about 1100 g/10 min to about 1500 g/10 min, as measured by ASTM DI 238.
• the polyolefin plastomer or elastomer has a melt index of about 500 g/10 min as measured by ASTM D1238. In some embodiments, the polyolefin plastomer has a melt index of about 600 g/10 min, about 700 g/10 min, about 800 g/10 min, about 900 g/10 min, about 1000 g/10 min, about 1100 g/10 min, about 1200 g/10 min, about 1300 g/10 min, about 1400 g/10 min, or about 1500 g/10 min, as measured by ASTM D1238.
• At least one of the one or more polymers is an isoprene polymer.
• isoprene polymer refers to a polymer formed from isoprene monomers.
• the isoprene polymer is a NATSYN® polymer.
• NATSYN® polymers are manufactured by The Goodyear Tire & Rubber Company.
• Exemplary NATSYN® polymers are listed in Table 15.
• the isoprene polymer is a Kuraray Liquid Rubber L-IR isoprene polymer.
• Exemplary Liquid Rubber L-IR isoprene polymers are listed in Table 16.
• the composition comprises from about 0.1 wt% to about 3 wt% of one or more polymers. In some embodiments, the composition comprises from about 0.01 wt% to about 0.05 wt%, from about 0.01 wt% to about 0.1 wt%, from about 0.01 wt% to about 0.25 wt%, from about 0.01 wt% to about 0.75 wt%, from about 0.01 wt% to about 1 wt%, from about 0.01 wt% to about 2 wt%, from about 0.01 wt% to about 3 wt%, from about 0.05 wt% to about 0.1 wt%, from about 0.05 wt% to about 0.25 wt%, from about 0.05 wt% to about 0.75 wt%, from about 0.05 wt% to about 1 wt%, from about 0.05 wt% to about 2 wt%, from about 0.05 wt% to about 3 wt%, from about 0.01 w
• the composition comprises about 2 wt% of one or more polymers. In some embodiments, the composition comprises about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.25 wt%, about 0.75 wt%, about 0.8 wt%, about 0.84 wt%, about 1 wt%, about 2 wt%, or about 3 wt% of one or more polymers.
• the composition comprises one polymer. In some embodiments, the composition comprises two polymers. In some embodiments, the composition comprises three polymers.
• the composition comprises one polymer, wherein the polymer is an EPDM polymer.
• the EPDM polymer is a NORDELTM EPDM polymer.
• the NORDELTM EPDM polymer is NORDELTM IP 4725P.
• the composition comprises one polymer, wherein the polymer is a polyolefin elastomer.
• the polyolefin elastomer is a VISTAMAXXTM polymer.
• the VISTAMAXXTM polymer is VISTAMAXXTM Performance Polymer 6102.
• the composition comprises two polymers, wherein the polymers are an EPDM polymer and a polyolefin elastomer.
• the EPDM polymer is a NORDELTM EPDM polymer.
• the NORDELTM EPDM polymer is NORDELTM IP 4725P.
• the polyolefin elastomer is a VISTAMAXXTM polymer.
• the VISTAMAXXTM polymer is VISTAMAXXTM Performance Polymer 6102.
• compositions described herein comprise insoluble sulfur.
• insoluble sulfur refers to a product which is predominantly insoluble sulfur, but which may and usually does contain some soluble sulfur (usually at less than 10%). This form of sulfur is polymeric by nature and does not dissolve in an elastomer, e.g., natural rubber, or in carbon disulfide (CS2).
• CS2 carbon disulfide
• the composition comprises from about 50 wt% to about 95 wt% insoluble sulfur, e.g., 70 wt% to about 90 wt% insoluble sulfur. In some embodiments, the composition comprises from about 50 wt% to about 55 wt%, from about 50 wt% to about 60 wt%, from about 50 wt% to about 65 wt%, from about 50 wt% to about 70 wt%, from about 50 wt% to about 75 wt%, from about 50 wt% to about 80 wt%, from about 50 wt% to about 85 wt%, from about 50 wt% to about 90 wt%, from about 50 wt% to about 95 wt%, from about 55 wt% to about 60 wt%, from about 55 wt% to about 65 wt%, from about 55 wt% to about 70 wt%, from about 55 wt% to about 75 wt%,
• the composition comprises about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 85 wt%, about 90 wt%, or about 95 wt% insoluble sulfur.
• the insoluble sulfur has an average primary particle size of from about 3 pm to about 50 pm. In some embodiments, the insoluble sulfur has an average primary particle size of from about 0.5 pm to about 1 pm, from about 0.5 pm to about 3 pm, from about 0.5 pm to about 5 pm, from about 0.5 pm to about 7 pm, from about 0.5 pm to about 10 pm, from about 0.5 pm to about 25 pm, from about 0.5 pm to about 50 pm, from about 0.5 pm to about 100 pm, from about 0.5 pm to about 150 pm, from about 1 pm to about 3 pm, from about 1 pm to about 5 pm, from about 1 pm to about 7 pm, from about 1 pm to about 10 pm, from about 1 pm to about 25 pm, from about 1 pm to about 50 pm, from about 1 pm to about 100 pm, from about 1 pm to about 150 pm, from about 3 pm to about 5 pm, from about 3 pm to about 7 pm, from about 3 pm to about 10 pm, from about 3 pm to about 25 pm, from about 3 pm to about 50 pm, from about 3 pm to about 35 pm, from about
• the insoluble sulfur has an average primary particle size of about 10 pm. In some embodiments, the insoluble sulfur has an average primary particle size of about 50 pm. In some embodiments, the insoluble sulfur has an average primary particle size of about 150 pm, about 125 pm, about 100 pm, about 75 pm, about 25 pm, about 15 pm, about 7.5 pm, about 5 pm, about 2.5 pm, about 1 pm, or about 0.5 pm.
• the insoluble sulfur has an average primary particle size of 10 pm ⁇ 5 pm. In some embodiments, the insoluble sulfur has an average primary particle size of 50 pm ⁇ 15 pm. In some embodiments, the insoluble sulfur has an average primary particle size of 100 pm ⁇ 10 pm, 75 pm ⁇ 5 pm, 25 pm ⁇ 2.5 pm, 5 pm ⁇ 2.5 pm, or 2 pm ⁇ 0.5 pm.
• compositions disclosed herein comprise a process oil.
• process oil refers to any oil that may be used as a carrier, e.g., as a carrier for insoluble sulfur.
• the process oil is a mineral oil.
• the mineral oil is paraffinic oil, naphthenic oil, aromatic oil, or a combination thereof.
• paraffinic oil refers to an oil comprising straight- or branched-chain hydrocarbons.
• naphthenic oil refers to an oil comprising hydrocarbons containing a saturated ring.
• the naphthenic oil comprises hydrocarbons having the following structure: wherein n is a positive integer.
• aromatic oil refers to an oil comprising compounds containing an aromatic ring.
• the aromatic oil comprises compounds having the following structure: wherein n is a positive integer.
• the process oil comprises a naturally derived oil, or a hydrogenated derivative thereof.
• naturally derived oil refers to any oil than can be derived from a natural and non-petroleum source, such as plants.
• the naturally derived oil is soybean oil, vegetable oil, orange oil, canola oil, castor oil, palm oil, sunflower oil, or a combination thereof.
• the "term hydrogenated derivative” as used herein refers to a derivative of oil that has been treated, e.g., with hydrogen gas and a catalyst, to saturate some or all of the double bonds present in the compound(s) comprising the oil.
• the process oil comprises a pyrolytic oil.
• pyrolytic oil refers to an oil that is obtained by heating dried biomass, including but not limited to wood and algae, in the absence of oxygen.
• the pyrolytic oil is prepared according to ASTM D7544-12.
• the composition comprises from about 5 wt% to about 50 wt% of a process oil. In some embodiments, the composition comprises from about 5 wt% to about 10 wt%, from about 5 wt% to about 15 wt%, from about 5 wt% to about 20 wt%, from about 5 wt% to about 25 wt%, from about 5 wt% to about 30 wt%, from about 5 wt% to about 35 wt%, from about 5 wt% to about 40 wt%, from about 5 wt% to about 45 wt%, from about 10 wt% to about 15 wt%, from about 10 wt% to about 20 wt%, from about 10 wt% to about 25 wt%, from about 10 wt% to about 30 wt%, from about 10 wt% to about 35 wt%, from about 10 wt% to about 40 wt%, from about 10 wt%, from about 10 w
• the composition comprises about 20 wt% of a process oil. In some embodiments, the composition comprises about 5 wt%, about 10 wt%, about 15 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, or about 50 wt% of a process oil.
• compositions disclosed herein further comprise a stabilizer.
• stabilizer refers to any material, chemical, or combination thereof that is added to insoluble sulfur to directly influence the thermal stability or storage stability of the product. The material, chemical, or combination thereof may be added at any stage of the insoluble sulfur production process.
• the stabilizer is an ionic liquid. In some embodiments, the stabilizer is an unsaturated olefin. In some embodiments, the unsaturated olefin is butadiene or isoprene. In some embodiments, the stabilizer is a carbonium ion. In some embodiments, the stabilizer is alpha-methyl styrene, pinene, terpene, ammonium sulfate, ethyl sodium xanthate, camphene, benzothiazole, or limonene. In some embodiments, the stabilizer is pine tar, gum turpentine, pine oil, or abietic acid.
• the stabilizer is dodecene, tetradecene, octadecene, indene, vinyl toluene, allyl benzene, dicyclopentadiene, styrene, chloroprene, divinyl benzene, 1 -vinyl-3 -cyclohexane, 2,5- dichlorostyrene, p-vinyl biphenyl, or p-methyl styrene.
• the composition comprises from about 0.01 wt% to about 1 wt% of a stabilizer. In some embodiments, the composition comprises from about 0.01 wt% to about 0.05 wt%, from about 0.01 wt% to about 0.1 wt%, from about 0.01 wt% to about 0.25 wt%, from about 0.01 wt% to about 0.5 wt%, from about 0.01 wt% to about 0.75 wt%, from about 0.05 wt% to about 0.1 wt%, from about 0.05 wt% to about 0.25 wt%, from about 0.05 wt% to about 0.5 wt%, from about 0.05 wt% to about 0.75 wt%, from about 0.05 wt% to about 1 wt%, from about 0.1 wt% to about 0.25 wt%, from about 0.1 wt% to about 0.5 wt%, from about 0.1 wt% to about 0. 0.
• the composition comprises about 0.5 wt% of a stabilizer. In some embodiments, the composition comprises about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.25 wt%, about 0.75 wt%, or about 1 wt% of a stabilizer.
• the compositions disclosed herein have a Carr index of less than 28%.
• the Carr index is a measure of the ability of a powder to flow. See EXAMPLE 2.
• the composition has a Carr index of less than 28%.
• the composition has a Carr index of less than 26%, less than 24%, less than 22%, less than 20%, less than 18%, less than 16%, less than 14%, less than 12%, or less than 10%.
• the composition has a Hausner ratio of less than 1.40.
• the Hausner ratio is a measure of the ability of a powder to flow. See EXAMPLE 2.
• the composition has a Hausner ratio of less than 1.60, less than 1.55, less than 1.50, less than 1.45, less than 1.35, less than 1.30, less than 1.25, less than 1.20, less than 1.15, or less than 1.10.
• vulcanized elastomeric articles comprising the compositions described herein.
• vulcanized elastomeric article refers to an article that is made by forming a composition comprising an elastomer into a specific shape and vulcanizing the composition to provide the article.
• vulcanization or "vulcanizing” as used herein refer to a process wherein cross-links are formed between elastomers to effect changes in the material properties of elastomers.
• vulcanization typically increases the rigidity and durability of elastomers. Vulcanization is carried out at room temperature or at elevated temperatures, depending on the nature of the elastomer(s), filler(s), and rubber chemical(s) being used.
• curing is also used in the art to describe this process.
• elastomer as used herein is a polymer with viscoelasticity (i.e., having both viscosity and elasticity) that typically has low intermolecular forces, low Young's modulus, and high failure strain. Elastomers can typically be cross-linked by heating in the presence of one or more cross-linking agents, a process called curing or vulcanization. Rubber is one type of elastomer. Non-limiting types of rubber include natural rubber (NR), synthetic rubber, and blends thereof.
• natural rubber as used herein refers to a naturally occurring elastomer that can be obtained from Hevea rubber trees.
• ACM acrylic rubber
• CM chlorinated polyethylene
• CSM chlorosulfonated polyethylene
• CO poly chloromethyloxiran
• EAM ethylene-ethyl acrylate copolymer
• ECO epichlorohydrin rubber
• EPM ethylene propylene rubber
• EVM ethylenevinylacetate copolymer
• the natural rubber comprises rubber derived from an alternative rubber plant.
• the term "natural rubber comprises rubber derived from an alternative rubber plant” as used herein refers to a naturally occurring elastomer that can be obtained from “non-Hevea” sources.
• the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz ( Russian dandelion).
• the one or more elastomers further comprises recycled rubber.
• recycled rubber refers to an elastomer that has been reclaimed from scrap materials such as used tires.
• the present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein.
• the vulcanized elastomeric article is a tire.
• the tire is a passenger vehicle tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agriculture tire, an earthmover tire, an airplane tire, or a racing tire.
• the vulcanized elastomeric article is a component of a tire.
• the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.
• the vulcanized elastomeric article is a rubber overshoe, a sealing strip, an acoustic panel, an air spring, a bellow, a membrane, a tactile sensor, a crash pad, a hose, a conveyor belt, or a flooring.
• the present disclosure also provides processes for preparing a vulcanized elastomeric article, the process comprising:
• the vulcanizing is performed at an average temperature of from about 140 °C to about 160 °C. In some embodiments, the vulcanizing is performed at an average temperature of from about 80 °C to about 100 °C, from about 80 °C to about 120 °C, from about 80 °C to about 140 °C, from about 80 °C to about 160 °C, from about 80 °C to about 180 °C, from about 80 °C to about 200 °C, from about 100 °C to about 120 °C, from about 100 °C to about 140 °C, from about 100 °C to about 160 °C, from about 100 °C to about 180 °C, from about 100 °C to about 200 °C, from about 120 °C to about 140 °C, from about 120 °C to about 160 °C, from about 120 °C to about 180 °C, from about 120 °C to about 200 °C, from about 140 °C, from about 120 °C to about 160
• the vulcanizing is performed at an average temperature of about 150 °C. In some embodiments, the vulcanizing is performed at an average temperature of about 80 °C, about 100 °C, about 120 °C, about 140 °C, about 160 °C, about 180 °C, or about 200 °C.
• kits comprising a composition described herein, packaged in a manner, e.g., in a container, that facilitates use of the composition to practice the processes and/or methods of the present disclosure.
• the kit comprises a composition described herein and instructions for using the composition in a vulcanizable elastomeric composition.
• the kit comprises a composition described herein and instructions for using the composition to prepare a vulcanized elastomeric article.
• the composition may be packaged in any suitable container, such as a sealed bottle or vessel, with a label affixed to the container or included in the kit that describes the composition and proper use thereof.
• the present disclosure also provides sulfur masterbatches comprising a composition described herein and at least one elastomer.
• the elastomer is natural rubber (NR), polyisoprene rubber (IR), butyl rubber (HR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene butadiene rubber (SBR), nitrile butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyloxiran (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylenevinylacetate copolymer (EVM), rubbers with fluoro and fluoralkyl or fluoralkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q), or a combination thereof.
• NR natural rubber
• IR polyisoprene
• masterbatch comprises from about 60 wt% to about 90 wt% of a composition described herein.
• masterbatch comprises from about 40 wt% to about 50 wt%, from about 40 wt% to about 60 wt%, from about 40 wt% to about 70 wt%, from about 40 wt% to about 80 wt%, from about 40 wt% to about 90 wt%, from about 40 wt% to about 95 wt%, from about 50 wt% to about 60 wt%, from about 50 wt% to about 70 wt%, from about 50 wt% to about 80 wt%, from about 50 wt% to about 90 wt%, from about 50 wt% to about 95 wt%, from about 60 wt% to about 70 wt%, from about 60 wt% to about 80 wt%, from about 60 wt% to about 90 wt%, from
• masterbatch comprises about 80 wt% of a composition described herein. In some embodiments, masterbatch comprises about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 85 wt%, about 90 wt%, or about 95 wt% of a composition described herein.
• the masterbatch comprises from about 10 wt% to about 40 wt% elastomer. In some embodiments, the masterbatch comprises from about 5 wt% to about 10 wt%, from about 5 wt% to about 15 wt%, from about 5 wt% to about 20 wt%, from about 5 wt% to about 25 wt%, from about 5 wt% to about 30 wt%, from about 5 wt% to about 35 wt%, from about 5 wt% to about 40 wt%, from about 5 wt% to about 45 wt%, from about 5 wt% to about 50 wt%, from about 10 wt% to about 15 wt%, from about 10 wt% to about 20 wt%, from about 10 wt% to about 25 wt%, from about 10 wt% to about 30 wt%, from about 10 wt% to about 35 wt%, from
• the masterbatch comprises about 20 wt% elastomer. In some embodiments, the masterbatch comprises about 5 wt%, about 10 wt%, about 15 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, or about 50 wt% elastomer.
• Embodiment I A composition comprising from about 50 wt% to about 95 wt% insoluble sulfur, from about 5 wt% to about 50 wt% of a process oil, and from about 0.1 wt% to about 3 wt% of a polymer, wherein the polymer is an ethylene propylene diene (EPDM) polymer, a styrene isoprene styrene (SIS) polymer, an oxygenated polymer, a polyolefin plastomer or elastomer, or an isoprene polymer.
• EPDM ethylene propylene diene
• SIS styrene isoprene styrene
• oxygenated polymer a polyolefin plastomer or elastomer
• isoprene polymer an isoprene polymer.
• Embodiment II The composition of Embodiment I, wherein the polymer is an EPDM polymer.
• Embodiment III The composition of Embodiment II, wherein the EPDM polymer has an ethylene content of from about 55 wt% to about 85 wt%.
• Embodiment IV The composition of Embodiment III, wherein the EPDM polymer has an ethylene content of about 70 wt%.
• Embodiment V The composition of any one of Embodiments II-IV, wherein the EPDM polymer has an ethylidene norbomene content of from about 0 wt% to about 10 wt%.
• Embodiment VI The composition of Embodiment V, wherein the EPDM polymer has an ethylidene norbornene content of about 4.9 wt%.
• Embodiment VII The composition of any one of Embodiments II- VI, wherein the EPDM polymer has a Mooney viscosity of from about 15 ML(l+4) to about 90 ML(l+4) when measured according to the ASTM D1646 standard.
• Embodiment VIII The composition of Embodiment VII, wherein the EPDM polymer has a Mooney viscosity of about 25 ML(l+4) when measured according to the ASTM DI 646 standard.
• Embodiment IX The composition of Embodiment I, wherein the polymer is an SIS polymer.
• Embodiment X The composition of Embodiment IX, wherein the styrene content of the SIS polymer is from about 5 wt% to about 20 wt%.
• Embodiment XI The composition of Embodiment X, wherein the styrene content of the SIS polymer is about 14 wt%.
• Embodiment XII The composition of any one of Embodiments IX-XI, wherein the structure of the SIS polymer is linear, radial, branched, pendant, dendritic, or a combination thereof.
• Embodiment XIII The composition of Embodiment XII, wherein the structure of the SIS polymer is linear.
• Embodiment XIV The composition of Embodiment XII, wherein the structure of the SIS polymer is a combination of linear and radial.
• Embodiment XVI The composition of Embodiment XV, wherein the oxygenated polymer comprises polyethylene glycol, polypropylene glycol, or a combination thereof.
• Embodiment XVIII The composition of Embodiment XV, wherein the oxygenated polymer comprises poly(ethylene-co-acrylic acid).
• Embodiment XIX The composition of Embodiment XV, wherein the oxygenated polymer comprises dicarboxyl-terminated polybutadiene.
• Embodiment XXI The composition of Embodiment I, wherein the polymer is a polyolefin plastomer or elastomer.
• Embodiment XXII The composition of Embodiment XXI, wherein the polyolefin plastomer or elastomer has a melt index of from about 500 g/10 min to about 1300 g/10 min as measured by ASTM D1238.
• Embodiment XXIII The composition of Embodiment XXI or XXII, wherein the polyolefin plastomer or elastomer has a density of from about 0.850 g/cc to about 0.950 g/cc as measured by ASTM D792.
• Embodiment XXIV The composition of Embodiment I, wherein the polymer is an isoprene polymer.
• Embodiment XXV The composition of any one of Embodiments I-XXIV, further comprising from about 0.01 wt% to about 1 wt% of a stabilizer.
• Embodiment XXVI The composition of Embodiment XXV, wherein the stabilizer is an ionic liquid.
• Embodiment XXVII The composition of Embodiment XXV, wherein the stabilizer is a unsaturated olefin.
• Embodiment XXVIII The composition of Embodiment XXV, wherein the stabilizer is a carbonium ion.
• Embodiment XXX The composition of any one of Embodiments I-XXIX, wherein the composition comprises about 80 wt% insoluble sulfur.
• Embodiment XXXI The composition of any one of Embodiments I-XXX, wherein the insoluble sulfur has an average primary particle size of from about 3 pm to about 65 pm.
• Embodiment XXXII The composition of Embodiment XXXI, wherein the insoluble sulfur has an average primary particle size of 10 pm ⁇ 5 pm.
• Embodiment XXXIII The composition of Embodiment XXXI, wherein the insoluble sulfur has an average primary particle size of 50 pm ⁇ 15 pm.
• Embodiment XXXIV The composition of any one of Embodiments I-XXXIII, wherein the composition comprises about 19.2 wt% process oil.
• Embodiment XXXV The composition of any one of Embodiments I-XXXIV, wherein the process oil comprises a mineral oil, a naturally derived oil, a pyrolytic oil, or a combination thereof.
• Embodiment XXXVI The composition of Embodiment XXXV, wherein the process oil comprises a mineral oil.
• Embodiment XXXVIII The composition of Embodiment XXXVII, wherein the mineral oil is naphthenic oil.
• Embodiment XXXIX The composition of Embodiment XXXV, wherein the process oil comprises a naturally derived oil, or a hydrogenated derivative thereof.
• Embodiment XL The composition of Embodiment XXXIX, wherein the naturally derived oil is soybean oil, vegetable oil, orange oil, canola oil, castor oil, palm oil, sunflower oil, or a combination thereof.
• Embodiment XLI The composition of any one of Embodiments I-XL, wherein the composition comprises about 0.8 wt% polymer.
• Embodiment XLII The composition of any one of Embodiments I-XLI, wherein the composition has a Carr index of less than 28%.
• Embodiment XLIII The composition of any one of Embodiments I-XLII, wherein the composition has a Hausner ratio of less than 1.40.
• Embodiment XLIV A vulcanized elastomeric article comprising the composition of any one of Embodiments I-XLII.
• Embodiment XLV A vulcanized elastomeric article prepared using the composition of any one of Embodiments I-XLII.
• Embodiment XL VI The vulcanized elastomeric article of Embodiment XLIV or
• Embodiment XL VII A process for preparing a vulcanized elastomeric article, the process comprising:
• Embodiment XL VIII A kit comprising the composition of any one of
• Embodiments I-XLIII and instructions for using the composition in a vulcanizable elastomeric composition are provided.
• Embodiment XLIX A kit comprising the composition of any one of Embodiments I-XLIII and instructions for using the composition to prepare a vulcanized elastomeric article.
• Embodiment L A sulfur masterbatch comprising the composition of any one of Embodiments I-XLIII and at least one elastomer.
• Embodiment LI The masterbatch of Embodiment L, wherein the elastomer is natural rubber (NR), polyisoprene rubber (IR), butyl rubber (HR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene butadiene rubber (SBR), nitrile butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), poly chloromethyloxiran (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylenevinylacetate
• NR natural rubber
• Embodiment LIV The masterbatch of any one of Embodiments L-LIII, wherein the masterbatch comprises from about 10 wt% to about 40 wt% elastomer.
• Embodiment LV The masterbatch of Embodiment LIV, wherein the masterbatch comprises about 20 wt% elastomer.
• Embodiment 1 A composition comprising from about 50 wt% to about 95 wt% insoluble sulfur, from about 5 wt% to about 50 wt% of a process oil, and from about 0.1 wt% to about 3 wt% of one or more polymers, wherein at least one of the one or more polymers is an ethylene propylene diene (EPDM) polymer, a styrene isoprene styrene (SIS) polymer, an oxygenated polymer, a polyolefin plastomer or elastomer, or an isoprene polymer.
• EPDM ethylene propylene diene
• SIS styrene isoprene styrene
• oxygenated polymer a polyolefin plastomer or elastomer
• isoprene polymer an isoprene polymer.
• Embodiment 2 The composition of Embodiment 1, wherein at least one of the one or more polymers is an EPDM polymer.
• Embodiment 3 The composition of Embodiment 2, wherein the EPDM polymer has an ethylene content of from about 55 wt% to about 85 wt%.
• Embodiment 6 The composition of Embodiment 5, wherein the EPDM polymer has an ethylidene norbornene content of about 4.9 wt%.
• Embodiment 7 The composition of any one of Embodiments 2-6, wherein the EPDM polymer has a Mooney viscosity of from about 15 ML(l+4) to about 90 ML(l+4) when measured according to the ASTM DI 646 standard.
• Embodiment 9 The composition of any one of Embodiments 1-8, wherein at least one of the one or more polymers is an SIS polymer.
• Embodiment 10 The composition of Embodiment 9, wherein the styrene content of the SIS polymer is from about 5 wt% to about 20 wt%.
• Embodiment 11 The composition of Embodiment 10, wherein the styrene content of the SIS polymer is about 14 wt%.
• Embodiment 12 The composition of any one of Embodiments 9-11, wherein the structure of the SIS polymer is linear, radial, branched, pendant, dendritic, or a combination thereof.
• Embodiment 13 The composition of Embodiment 12, wherein the structure of the SIS polymer is linear.
• Embodiment 14 The composition of Embodiment 12, wherein the structure of the SIS polymer is a combination of linear and radial.
• Embodiment 15 The composition any one of Embodiments 1-14, wherein at least one of the one or more polymers is an oxygenated polymer.
• Embodiment 16 The composition of Embodiment 15, wherein the oxygenated polymer comprises polyethylene glycol, polypropylene glycol, or a combination thereof.
• Embodiment 17 The composition of Embodiment 16, wherein the ethylene oxide content of the oxygenated polymer is from about 60 wt% to about 90 wt%.
• Embodiment 18 The composition of Embodiment 15, wherein the oxygenated polymer comprises poly(ethylene-co-acrylic acid).
• Embodiment 19 The composition of Embodiment 15, wherein the oxygenated polymer comprises dicarboxyl-terminated polybutadiene.
• Embodiment 20 The composition of any one of Embodiments 15-19, wherein the water content of the oxygenated polymer is less than 0.2 wt%.
• Embodiment 21 The composition of any one of Embodiments 1-20, wherein at least one of the one or more polymers is a polyolefin plastomer or elastomer.
• Embodiment 22 The composition of Embodiment 21, wherein the polyolefin plastomer or elastomer has a melt index of from about 500 g/10 min to about 1300 g/10 min as measured by ASTM DI 238.
• Embodiment 23 The composition of Embodiment 21 or 22, wherein the polyolefin plastomer or elastomer has a density of from about 0.850 g/cc to about 0.950 g/cc as measured by ASTM D792.
• Embodiment 24 The composition of any one of Embodiments 1-23, wherein at least one of the one or more polymers is an isoprene polymer.
• Embodiment 25 The composition of any one of Embodiments 1-24, further comprising from about 0.01 wt% to about 1 wt% of a stabilizer.
• Embodiment 26 The composition of Embodiment 25, wherein the stabilizer is an ionic liquid.
• Embodiment 27 The composition of Embodiment 25, wherein the stabilizer is a unsaturated olefin.
• Embodiment 28 The composition of Embodiment 25, wherein the stabilizer is a carbonium ion.
• Embodiment 29 The composition of Embodiment 25, wherein the stabilizer is alpha-methyl styrene, pinene, terpene, ammonium sulfate, ethyl sodium xanthate, camphene, benzothiazole, or limonene.
• Embodiment 30 The composition of any one of Embodiments 1-29, wherein the composition comprises about 80 wt% insoluble sulfur.
• Embodiment 31 The composition of any one of Embodiments 1-30, wherein the insoluble sulfur has an average primary particle size of from about 3 pm to about 65 pm.
• Embodiment 32 The composition of Embodiment 31, wherein the insoluble sulfur has an average primary particle size of 10 pm ⁇ 5 pm.
• Embodiment 33 The composition of Embodiment 31, wherein the insoluble sulfur has an average primary particle size of 50 pm ⁇ 15 pm.
• Embodiment 34 The composition of any one of Embodiments 1-33, wherein the composition comprises about 19.2 wt% process oil.
• Embodiment 35 The composition of any one of Embodiments 1-33, wherein the composition comprises about 10 wt% process oil.
• Embodiment 36 The composition of any one of Embodiments 1-35, wherein the process oil comprises a mineral oil, a naturally derived oil, a pyrolytic oil, or a combination thereof.
• Embodiment 37 The composition of Embodiment 36, wherein the process oil comprises a mineral oil.
• Embodiment 38 The composition of Embodiment 37, wherein the mineral oil is paraffinic oil, naphthenic oil, aromatic oil, or a combination thereof.
• Embodiment 39 The composition of Embodiment 38, wherein the mineral oil is naphthenic oil.
• Embodiment 40 The composition of Embodiment 36, wherein the process oil comprises a naturally derived oil, or a hydrogenated derivative thereof.
• Embodiment 41 The composition of Embodiment 40, wherein the naturally derived oil is soybean oil, vegetable oil, orange oil, canola oil, castor oil, palm oil, sunflower oil, or a combination thereof.
• Embodiment 42 The composition of any one of Embodiments 1-41, wherein the composition comprises about 0.8 wt% of the one or more polymers.
• Embodiment 43 The composition of Embodiment 1, wherein the composition comprises from about 80 wt% to about 90 wt% insoluble sulfur, from about 10 wt% to about 20 wt% of a process oil, and from about 0.4 wt% to about 1 wt% of a polyolefin plastomer or elastomer.
• Embodiment 44 The composition of Embodiment 1, wherein the composition comprises from about 80 wt% to about 90 wt% insoluble sulfur, from about 10 wt% to about 20 wt% of a process oil, and from about 0.4 wt% to about 1 wt% of an EPDM polymer.
• Embodiment 45 The composition of Embodiment 1, wherein the composition comprises from about 80 wt% to about 90 wt% insoluble sulfur, from about 10 wt% to about 20 wt% of a process oil, from about 0.4 wt% to about 1 wt% of a polyolefin plastomer or elastomer, and from about 0.01 wt% to about 0.07 wt% of an EPDM polymer.
• Embodiment 47 The composition of any one of Embodiments 43, 45, or 46, wherein the polyolefin plastomer or elastomer has a density of about 0.862 g/cm 3 and an ethylene content of about 16.
• Embodiment 48 The composition of Embodiment 47, wherein the polyolefin plastomer or elastomer is VISTAMAXXTM Performance Polymer 6102.
• Embodiment 49 The composition of any one of Embodiments 44-46, wherein the EPDM polymer has an ethylene content of about 70 and an ethylidene norbomene (ENB) content of about 4.9.
• EPDM polymer has an ethylene content of about 70 and an ethylidene norbomene (ENB) content of about 4.9.
• Embodiment 50 The composition of Embodiment 49, wherein the EPDM polymer is NORDELTM IP 4725P.
• Embodiment 53 A vulcanized elastomeric article comprising the composition of any one of Embodiments 1-52.
• Embodiment 55 The vulcanized elastomeric article of Embodiment 53 or 54, wherein the vulcanized elastomeric article is a tire.
• Embodiment 56 A process for preparing a vulcanized elastomeric article, the process comprising:
• Embodiment 57 A kit comprising the composition of any one of Embodiments 1-52 and instructions for using the composition in a vulcanizable elastomeric composition.
• Embodiment 58 A kit comprising the composition of any one of Embodiments 1-52 and instructions for using the composition to prepare a vulcanized elastomeric article.
• Embodiment 59 A sulfur masterbatch comprising the composition of any one of Embodiments 1-52 and at least one elastomer.
• Embodiment 60 The masterbatch of Embodiment 59, wherein the elastomer is natural rubber (NR), polyisoprene rubber (IR), butyl rubber (HR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene butadiene rubber (SBR), nitrile butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), poly chloromethyloxiran (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylenevinylacetate copolymer (EVM), rubbers with fluoro and fluoralkyl or fluoralkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q),
• NR
• Embodiment 61 The masterbatch of Embodiment 60, wherein the masterbatch comprises from about 60 wt% to about 90 wt% of the composition of any one of Embodiments 1-52.
• Embodiment 62 The masterbatch of Embodiment 61, wherein the masterbatch comprises about 80 wt% of the composition of any one of Embodiments 1- 52.
• Embodiment 63 The masterbatch of any one of Embodiments 59-62, wherein the masterbatch comprises from about 10 wt% to about 40 wt% elastomer.
• Embodiment 64 The masterbatch of Embodiment 63, wherein the masterbatch comprises about 20 wt% elastomer.
• a 2 L plastic container with 5 steel ball bearings was loaded with approximately 500 g of dry insoluble sulfur.
• Process oil alone Hyprene P300N paraffinic process oil or Hyprene 100 naphthenic process oil
• a process oil Hydroprene 100 naphthenic process oil
• Polymer mixture was pre-heated to 70 °C and poured into the insoluble sulfur to achieve a final concentration of 20 wt% process oil in the mixture.
• the container was quickly capped and loaded into to a BioEngineering Inversina 2L tumbling mixer. The mixture was tumbled for 15 minutes at 60 rpm, stopped, and any parts of the mixture which had adhered to the walls or top of the container were scraped off with a spatula.
• the container was re-sealed and re-loaded onto the Inversina mixer for another 45 minutes at 60 rpm. The mixtures were removed from the mixer and used in subsequent characterization.
• Carr index 100*(pPBD - pUBD)/pPBD wherein pPBD is the packed bulk density and pUBD is the unpacked bulk density. A lower Carr index is indicative of better powder flow.
• the Carr indices for various insoluble sulfur compositions comprising different polymers or no polymer are plotted in Fig. 1 and tabulated in Table 17.
• the Hausner Ratio also describes powder flow by expressing the ratio between packed and unpacked bulk density, and is defined as follows:
• Hausner ratio pPBD/pUBD wherein pPBD is the packed bulk density and pUBD is the unpacked bulk density. A lower Hausner ratio is indicative of better powder flow.
• the Hausner ratios for various insoluble sulfur compositions prepared using the procedure described in Example 1 comprising different polymers or no polymer are plotted in Fig. 2 and tabulated in Table 17.
• 1 OTIO indicates that the sample comprises about 10 wt% process oil.
• 2 OT20 indicates that the sample comprises about 20 wt% process oil.

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