WO2024178084A1

WO2024178084A1 - Insoluble sulfur compositions

Info

Publication number: WO2024178084A1
Application number: PCT/US2024/016676
Authority: WO
Inventors: Thomas Richard Floyd; Grayson Lee JACKSON; Ralph D. TRIPLETT II; Hiu Ching WONG
Original assignee: Flexsys America L.P.
Priority date: 2023-02-21
Filing date: 2024-02-21
Publication date: 2024-08-29

Abstract

The present disclosure provides compositions comprising insoluble sulfur, a process oil, and one or more polymers. The present disclosure also provides vulcanized elastomeric articles comprising a composition described herein and vulcanized elastomeric articles prepared using a composition disclosed herein. The present disclosure also provides processes for preparing a vulcanized elastomeric article comprising a composition described herein. The present disclosure also provides kits comprising a composition described herein. The present disclosure also provides sulfur masterbatches comprising a composition described herein and an elastomer.

Description

INSOLUBLE SULFUR COMPOSITIONS

BACKGROUND

Field

[0001] The present disclosure provides insoluble sulfur compositions useful for the vulcanization of rubber for the production of rubber products, e.g., tires.

Background

[0002] Insoluble sulfur (also referred to as polymeric 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.

[0003] The use of 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.

[0004] Insoluble sulfur is a solid powder that is mixed with elastomers to form rubber compounds. A need exists to formulate insoluble sulfur compositions that exhibit enhanced flow and/or dispersability, which would decrease processing and manufacturing costs.

BRIEF SUMMARY

[0005] In one aspect, the present disclosure provides compositions comprising insoluble sulfur, a process oil, one or more polymers, and, optionally, a stabilizer. In some embodiments, 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.

[0006] In another aspect, the present disclosure provides vulcanized elastomeric articles comprising the insoluble sulfur compositions disclosed herein. [0007] In another aspect, the present disclosure provides vulcanized elastomeric articles prepared using the insoluble sulfur compositions described herein.

[0008] In another aspect, the present disclosure provides a process for preparing a vulcanized elastomeric article, the process comprising:

(a) admixing an insoluble sulfur composition disclosed herein with at least one elastomer to form a mixture;

(b) forming the mixture of (a) into a formed shape; and

(c) vulcanizing the formed shape to provide a vulcanized elastomeric article.

[0009] In another aspect, the present disclosure provides kits comprising an insoluble sulfur composition disclosed herein and instructions for using the composition in a vulcanizable elastomeric composition.

[0010] The present disclosure also provides kits comprising a composition disclosed herein and instructions for using the composition to prepare a vulcanized elastomeric article.

[0011] In another aspect, the present disclosure provides sulfur masterbatches comprising an insoluble sulfur composition disclosed herein and at least one elastomer.

[0012] Additional embodiments and advantages of the disclosure will be set forth, in part, in the description that follows, and will flow from the description, or can be learned by practice of the disclosure. The embodiments and advantages of the disclosure will be realized and attained by means of the elements and combinations particularly pointed out in the appended claims.

[0013] It is to be understood that both the foregoing summary and the following detailed description are exemplary and explanatory only, and are not restrictive of the invention as claimed.

BRIEF DESCRIPTION OF THE DRAWINGS

[0014] Fig. l is a scatter plot showing the Carr indices for compositions comprising insoluble sulfur, process oil, and one or more polymers (or insoluble sulfur and process oil only) at various polymer concentrations. [0015] Fig. 2 is a scatter plot showing the Hausner ratios for compositions comprising insoluble sulfur, process oil, and one or more polymers (or insoluble sulfur and process oil only) at various polymer concentrations.

DETAILED DESCRIPTION

1. Definitions

[0016] The use of the terms "a", "an", "the", and similar referents in the context of describing the disclosure (especially in the context of the claims) are to be construed to cover both the singular and the plural, unless otherwise indicated. Recitation of ranges of values herein merely are intended to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. The use of any and all examples, or exemplary language (e.g., "such as") provided herein, is intended to better illustrate the disclosure and is not a limitation on the scope of the disclosure unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the disclosure.

[0017] The term "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

2. In some embodiments, one or more means 1.

[0018] The term "about" as used herein indicates the value of a given quantity varies by ± 5% of the value. For example, "about 100 nm" encompasses a range from 95 nm to 105 nm, inclusive.

[0019] The term "wt%" as used herein 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. For example, the wt% of insoluble sulfur in a composition comprising 8 kg of insoluble sulfur, 1.95 kg of process oil, and 0.05 kg of one or more polymers is 80 wt% (8 kg/(8 kg + 1.95 kg + 0.05 kg) x 100 = 80 wt%). As another example, the wt% of one or more polymers, wherein the one or more polymers are polymer A and polymer B, in a composition comprising 8 kg of insoluble sulfur, 1.95 kg of process oil, 0.025 kg polymer A, and 0.025 kg polymer B is 5 wt% ((0.025 kg + 0.025 kg)/(8 kg + 1.95 kg + 0.025 kg + 0.025 kg) x 100 = 5 wt%).

[0020] The term "average primary particle size" as used herein 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."

[0021] The terms "number average molecular weight" or "Mn" as used herein refer to the statistical average molecular weight of all polymer chains in a polymer sample.

[0022] The terms "weight average molecular weight" or "Mw" as used herein refer to the weight average molecular weight of all polymer chains in a polymer sample.

[0023] The term "terpolymer" as used herein refers to a polymer formed by the polymerization of three different monomers. In some embodiments, the monomers are randomly arranged throughout the polymer chain.

[0024] The term "diene" as used herein refers to a compound containing two double bonds. An example of a diene is ethylidene norbornene (ENB), which has the following structure:

[0025] The term "Mooney viscosity" as used herein 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.

[0026] The terms "melt index," "melt flow index," or "melt flow rate" as used herein refer 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.

[0027] The term "coupling efficiency" as used herein 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). II. Compositions

[0028] The present disclosure provides compositions comprising insoluble sulfur, a process oil, one or more polymers, and, optionally, a stabilizer. In some embodiments, 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.

[0029] In some embodiments, the present disclosure provides compositions comprising insoluble sulfur, a process oil, one polymer, and, optionally, a stabilizer. In some embodiments, 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.

[0030] In some embodiments, the present disclosure provides compositions comprising insoluble sulfur, a process oil, two polymers, and, optionally, a stabilizer. In some embodiments, 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.

[0031] In some embodiments, the present disclosure provides compositions comprising insoluble sulfur, a process oil, three polymers, and, optionally, a stabilizer. In some embodiments, 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.

III. Polymers

[0032] The compositions disclosed herein comprise one or more polymers. In some embodiments, 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.

[0033] The term "ethylene propylene diene polymer" or "EPDM polymer" as used herein refers to a terpolymer formed from ethylene, propylene, and diene monomers. In some embodiments, the diene is dicyclopentadiene (DCPD). In some embodiments, the diene is vinyl norbornene (VNB). In some embodiments, the diene is ethylidene norbornene (ENB). In some embodiments, the EPDM polymer comprises the following structure:

wherein n, 1, and p are positive integers.

[0034] The term "ethylene content" as used herein refers to the wt% of a polymer that derives from ethylene monomer. In some embodiments, the EPDM polymer has an ethylene content of from about 55 wt% to about 85 wt%. In some embodiments, 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%, from about 45 wt% to about 80 wt%, from about 45 wt% to about 85 wt%, from about 45 wt% to about 90 wt%, 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 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%, from about 55 wt% to about 80 wt%, from about 55 wt% to about 90 wt%, from about 60 wt% to about 65 wt%, from about 60 wt% to about 70 wt%, from about 60 wt% to about 75 wt%, from about 60 wt% to about 80 wt%, from about 60 wt% to about 85 wt%, from about 60 wt% to about 90 wt%, from about 65 wt% to about 70 wt%, from about 65 wt% to about 75 wt%, from about 65 wt% to about 80 wt%, from about 65 wt% to about 85 wt%, from about 65 wt% to about 90 wt%, from about 70 wt% to about 75 wt%, from about 70 wt% to about 80 wt%, from about 70 wt% to about 85 wt%, from about 70 wt% to about 90 wt%, from about 75 wt% to about 80 wt%, from about 75 wt% to about 85 wt%, from about 75 wt% to about 90 wt%, from about 80 wt% to about 85 wt%, from about 80 wt% to about 90 wt%, or from about 90 wt% to about 95 wt%.

[0035] In some embodiments, 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%.

[0036] The term " ethylidene norbornene content" as used herein refers to the wt% of a polymer that derives from ethylidene norbomene monomer. In some embodiments, the EPDM polymer has an ethylidene norbomene content of from about 0 wt% to about 10 wt%. In some embodiments, 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 6 wt%, from about 1 wt% to about 7 wt%, from about 1 wt% to about 8 wt%, from about 1 wt% to about 9 wt%, from about 1 wt% to about 10 wt%, from about 2 wt% to about 3 wt%, from about 2 wt% to about 4 wt%, from about 2 wt% to about 5 wt%, from about 2 wt% to about 6 wt%, from about 2 wt% to about 7 wt%, from about 2 wt% to about 8 wt%, from about 2 wt% to about 9 wt%, from about 2 wt% to about 10 wt%, from about 3 wt% to about 4 wt%, from about 3 wt% to about 5 wt%, from about 3 wt% to about 6 wt%, from about 3 wt% to about 7 wt%, from about 3 wt% to about 8 wt%, from about 3 wt% to about 9 wt%, from about 3 wt% to about 10 wt%, from about 4 wt% to about 5 wt%, from about 4 wt% to about 6 wt%, from about 4 wt% to about 7 wt%, from about 4 wt% to about 8 wt%, from about 4 wt% to about 9 wt%, from about 4 wt% to about 10 wt%, from about 5 wt% to about 6 wt%, from about 5 wt% to about 7 wt%, from about 5 wt% to about 8 wt%, from about 5 wt% to about 9 wt%, from about 5 wt% to about 10 wt%, from about 6 wt% to about 7 wt%, from about 6 wt% to about 8 wt%, from about 6 wt% to about 9 wt%, from about 6 wt% to about 10 wt%, from about 7 wt% to about 8 wt%, from about 7 wt% to about 9 wt%, from about 7 wt% to about 10 wt%, from about 8 wt% to about 9 wt%, from about 8 wt% to about 10 wt%, or from about 9 wt% to about 10 wt%.

[0037] In some embodiments, 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%.

[0038] In some embodiments, 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 40 ML(l+4), from about 20 ML(l+4) to about 50 ML(l+4), from about 20 ML(l+4) to about 60 ML(l+4), from about 20 ML(l+4) to about 70 ML(l+4), from about 20 ML(l+4) to about 80 ML(l+4), from about 20 ML(l+4) to about 90 ML(l+4), from about 30 ML(l+4) to about 40 ML(l+4), from about 30 ML(l+4) to about 50 ML(l+4), from about 30 ML(l+4) to about 60 ML(l+4), from about 30 ML(l+4) to about 70 ML(l+4), from about 30 ML(l+4) to about 80 ML(l+4), from about 30 ML(l+4) to about 90 ML(l+4), from about 40 ML(l+4) to about 50 ML(l+4), from about 40 ML(l+4) to about 60 ML(l+4), from about 40 ML(l+4) to about 70 ML(l+4), from about 40 ML(l+4) to about 80 ML(l+4), from about 40 ML(l+4) to about 90 ML(l+4), from about 50 ML(l+4) to about 60 ML(l+4), from about 50 ML(l+4) to about 70 ML(l+4), from about 50 ML(l+4) to about 80 ML(l+4), from about 50 ML(l+4) to about 90 ML(l+4), from about 60 ML(l+4) to about 70 ML(l+4), from about 60 ML(l+4) to about 80 ML(l+4), from about 60 ML(l+4) to about 90 ML(l+4), from about 70 ML(l+4) to about 80 ML(l+4), from about 70 ML(l+4) to about 90 ML(l+4), or from about 80 ML(l+4) to about 90 ML(l+4), when measured according to the ASTM DI 646 standard.

[0039] In some embodiments, 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. [0040] In some embodiments, 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.

[0041] In some embodiments, the EPDM polymer is a NORDEL™ EPDM polymer. NORDEL™ EPDM polymers are manufactured by The Dow Chemical Company ("Dow"). Exemplary NORDEL™ EPDM polymers and their properties (test method used noted in parentheses) are described in Table 1.

Table 1

[0042] In some embodiments, the EPDM polymer is a VISTALON™ EPDM polymer. VISTALON™ EPDM polymers are manufactured by ExxonMobil. Exemplary VISTALON™ EPDM polymers are described in Table 2.

Table 2

[0043] In some embodiments, 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

(a) Product contains 100 phr (50%) white, hydrotreated paraffinic oil

(b) Product contains 75 phr (43%) white, hydrotreated paraffinic oil.

Table 4

Table 5

Table 6

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.

[0044] In some embodiments, the EPDM polymer is a KELTAN® EPDM polymer.

KELTAN® EPDM polymers are manufactured by ARLANXEO. Exemplary KELTAN® EPDM polymers are described in Table 7.

Table 7

CLCB = Controlled long chain branching; N = Narrow molecular weight distribution; M = Medium molecular weight distribution; B = broad molecular weight distribution

[0045] In some embodiments, 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.

Table 8

*ref erred to polymer matrix; **ML (1+4) 100°C

[0046] In some embodiments, at least one of the one or more polymers is an SIS polymer.

[0047] The terms "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. In some embodiments, SIS comprises the following structure:

wherein n, 1, and p are positive integers.

[0048] The term "styrene content" as used herein refers to the wt% of a polymer that derives from styrene monomer.

[0049] In some embodiments, 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%, or from about 25 wt% to about 30 wt%.

[0050] In some embodiments, the 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%.

[0051] In some embodiments, the structure of the SIS polymer is linear, radial, branched, pendant, dendritic, or a combination thereof. [0052] In some embodiments, the SIS polymer is a QUINTAC™ polymer. QUINTAC™ polymers are manufactured by Zeon Corporation. Exemplary QUINTAC™ polymers are described (test methods used in parentheses) in Table 9.

Table 9

[0053] In some embodiments, at least one of the one or more polymers is an oxygenated polymer. The term "oxygenated polymer" as used herein refers to any polymer than contains one or more oxygen atoms.

[0054] In some embodiments, the oxygenated polymer comprises polyethylene glycol. The terms "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.

[0055] The term "ethylene oxide content" as used herein refers to the wt% of a polymer that derives from ethylene oxide monomer, and is a measure of the wt% of -(O-CH2- CH2)- units present in the polymer. In some embodiments, the ethylene oxide content of the oxygenated polymer is from about 60 wt% to about 90 wt%. In some embodiments, 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 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 100 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 100 wt%, from about 60 wt% to about 70 wt%, from about 60 wt% to about 80 wt%, from about 60 wt% to about 100 wt%, from about 70 wt% to about 80 wt%, from about 70 wt% to about 90 wt%, from about 70 wt% to about 100 wt%, from about 80 wt% to about 90 wt%, from about 80 wt% to about 100 wt%, or from about 90 wt% to about 100 wt%.

[0056] In some embodiments, 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%.

[0057] In some embodiments, the oxygenated polymer comprises polypropylene glycol. The terms "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.

[0058] "PEG-PPG-PEG" as used herein refers to a triblock copolymer of polyethylene glycol-polypropylene glycol-polyethylene glycol, where the length of each individual block can vary. In some embodiments, PEG-PPG-PEG comprises an ethylene oxide, propylene oxide, and water content of 84 wt%, 15.6 wt%, and <0.4 wt%, respectively. In some embodiments, the PEG-PPG-PEG has a Mw of about 15,000 g/mol.

[0059] "PEG-PPG" as used herein refers to a diblock copolymer of polyethylene glycolpolypropylene glycol, where the length of each individual block can vary. In some embodiments, PEG-PPG comprises an ethylene oxide, propylene oxide, and water content of 75 wt%, 24.7 wt%, and <0.3 wt%, respectively.

[0060] "PEG-PPG-MBE" as used herein refers to a diblock copolymer of polyethylene glycol-polypropylene glycol, wherein polymerization has been terminated using monobutyl ether, and wherein the length of each individual block can vary. In some embodiments, PEG-PPG-MBE has an ethylene oxide, propylene oxide, and water content of 75 wt%, 24.7 wt%, and <0.3 wt%, respectively.

[0061] The terms "poly(ethylene-co-acrylic acid)" or "PEAA" as used herein refers to a polymer formed from ethylene and acrylic acid monomers. In some embodiments, PEAA comprises the following structure:

wherein n and 1 are positive integers.

[0062] In some embodiments, 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%, from about 45 wt% to about 70 wt%, from about 45 wt% to about 75 wt%, from about 45 wt% to about 80 wt%, from about 45 wt% to about 85 wt%, from about 45 wt% to about 90 wt%, 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 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%, from about 55 wt% to about 80 wt%, from about 55 wt% to about 90 wt%, from about 60 wt% to about 65 wt%, from about 60 wt% to about 70 wt%, from about 60 wt% to about 75 wt%, from about 60 wt% to about 80 wt%, from about 60 wt% to about 85 wt%, from about 60 wt% to about 90 wt%, from about 65 wt% to about 70 wt%, from about 65 wt% to about 75 wt%, from about 65 wt% to about 80 wt%, from about 65 wt% to about 85 wt%, from about 65 wt% to about 90 wt%, from about 70 wt% to about 75 wt%, from about 70 wt% to about 80 wt%, from about 70 wt% to about 85 wt%, from about 70 wt% to about 90 wt%, from about 75 wt% to about 80 wt%, from about 75 wt% to about 85 wt%, from about 75 wt% to about 90 wt%, from about 80 wt% to about 85 wt%, from about 80 wt% to about 90 wt%, or from about 90 wt% to about 95 wt%.

[0063] The term "acrylic acid content" as used herein refers to the wt% of a polymer that derives from acrylic acid monomer. In some embodiments, the PEAA comprises from about 10 wt% to about 20 wt% acrylic acid monomer. In some embodiments, 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% 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%, or from about 25 wt% to about 30 wt% acrylic acid monomer.

[0064] In some embodiments, the oxygenated polymer comprises dicarboxyl-terminated polybutadiene. The terms "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 term "dicarboxyl-terminated polybutadiene" as used herein refers to a polybutadiene polymer that is terminally substituted with carboxyl groups. In some embodiments, the dicarboxyl-terminated polybutadiene has the following structure:

wherein n is a positive integer.

[0065] In some embodiments, 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%.

[0066] In some embodiments, at least one of the one or more polymers is a polyolefin plastomer (POP) or a polyolefin elastomer (POE). The terms "polyolefin plastomer," "POP," "polyolefin elastomer," and "POE" as used herein refer 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. In some embodiments, the polyolefin plastomer is an AFFINITY™ polyolefin plastomer. AFFINITY™ polyolefin plastomers are manufactured by Dow. Exemplary AFFINITY™ polyolefin plastomers are listed in Table 10.

Table 10

[0067] In some embodiments, the polyolefin elastomer is an ENGAGE™ polyolefin elastomer. ENGAGE™ polyolefin elastomers are produced by Dow. Exemplary ENGAGE™ polyolefin elastomers are listed in Tables 11-12.

Table 11. Ethylene Octene Grade ENGAGE™ polyolefin elastomers

Table 12. Ethylene Butene, HM, and XLT Grade ENGAGE™ polyolefin elastomers

[0068] In some embodiments, 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.

Table 13

*ML (1+4) 100°C

[0069] In some embodiments, the polyolefin elastomer is a VISTAMAXX™ polymer.

VISTAMAXX™ polymers are formed from a mixture of polypropylene and/or ethylene monomers and are manufactured by ExxonMobil. Exemplary VISTAMAXX™ polymers are listed in Table 14. Table 14

[0070] In some embodiments, 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.

[0071] In some embodiments, 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.

[0072] In some embodiments, at least one of the one or more polymers is an isoprene polymer. As used herein, the term "isoprene polymer" refers to a polymer formed from isoprene monomers. In some embodiments, 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.

Table 15

[0073] In some embodiments, the isoprene polymer is a Kuraray Liquid Rubber L-IR isoprene polymer. Exemplary Liquid Rubber L-IR isoprene polymers are listed in Table 16.

Table 16

[0074] In some embodiments, 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 0.1 wt% to about 0.25 wt%, from about 0.1 wt% to about 0.75 wt%, from about 0.1 wt% to about 1 wt%, from about 0.1 wt% to about 2 wt%, from about 0.1 wt% to about 3 wt%, from about 0.25 wt% to about 0.75 wt%, from about 0.25 wt% to about 1 wt%, from about 0.25 wt% to about 2 wt%, from about 0.25 wt% to about 3 wt%, from about 0.75 wt% to about 1 wt%, from about 0.75 wt% to about 2 wt%, from about 0.75 wt% to about 3 wt%, from about 1 wt% to about 2 wt%, from about 1 wt% to about 3 wt%, or from about 2 wt% to about 3 wt% of one or more polymers.

[0075] In some embodiments, 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.

[0076] In some embodiments, the composition comprises one polymer. In some embodiments, the composition comprises two polymers. In some embodiments, the composition comprises three polymers.

[0077] In some embodiments, the composition comprises one polymer, wherein the polymer is an EPDM polymer. In some embodiments, the EPDM polymer is a NORDEL™ EPDM polymer. In some embodiments, the NORDEL™ EPDM polymer is NORDEL™ IP 4725P.

[0078] In some embodiments, the composition comprises one polymer, wherein the polymer is a polyolefin elastomer. In some embodiments, the polyolefin elastomer is a VISTAMAXX™ polymer. In some embodiments, the VISTAMAXX™ polymer is VISTAMAXX™ Performance Polymer 6102.

[0079] In some embodiments, the composition comprises two polymers, wherein the polymers are an EPDM polymer and a polyolefin elastomer. In some embodiments, the EPDM polymer is a NORDEL™ EPDM polymer. In some embodiments, the NORDEL™ EPDM polymer is NORDEL™ IP 4725P. In some embodiments, the polyolefin elastomer is a VISTAMAXX™ polymer. In some embodiments, the VISTAMAXX™ polymer is VISTAMAXX™ Performance Polymer 6102.

IV. Insoluble Sulfur

[0080] The compositions described herein comprise insoluble sulfur. The term "insoluble sulfur" as used herein 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).

[0081] In some embodiments, 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%, from about 55 wt% to about 80 wt%, from about 55 wt% to about 85 wt%, from about 55 wt% to about 90 wt%, from about 55 wt% to about 95 wt%, from about 60 wt% to about 65 wt%, from about 60 wt% to about 70 wt%, from about 60 wt% to about 75 wt%, from about 60 wt% to about 80 wt%, from about 60 wt% to about 85 wt%, from about 60 wt% to about 90 wt%, from about 60 wt% to about 95 wt%, from about 65 wt% to about 70 wt%, from about 65 wt% to about 75 wt%, from about 65 wt% to about 80 wt%, from about 65 wt% to about 85 wt%, from about 65 wt% to about 90 wt%, from about 65 wt% to about 95 wt%, from about 70 wt% to about 75 wt%, from about 70 wt% to about 80 wt%, from about 70 wt% to about 85 wt%, from about 70 wt% to about 90 wt%, from about 70 wt% to about 95 wt%, from about 75 wt% to about 80 wt%, from about 75 wt% to about 85 wt%, from about 75 wt% to about 90 wt%, from about 75 wt% to about 95 wt%, from about 80 wt% to about 85 wt%, from about 80 wt% to about 90 wt%, from about 80 wt% to about 95 wt%, from about 85 wt% to about 90 wt%, from about 85 wt% to about 95 wt%, or from about 90 wt% to about 95 wt% insoluble sulfur. [0082] In some embodiments, the composition comprises about 80 wt% insoluble sulfur.

In some embodiments, 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.

[0083] In some embodiments, 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 100 pm, from about 3 pm to about 150 pm, from about 5 pm to about 7 pm, from about 5 pm to about 10 pm, from about 5 pm to about 25 pm, from about 5 pm to about 50 pm, from about 5 pm to about 100 pm, from about 5 pm to about 150 pm, from about 7 pm to about 10 pm, from about 7 pm to about 25 pm, from about 7 pm to about 50 pm, from about 7 pm to about 100 pm, from about 7 pm to about 150 pm, from about 10 pm to about 25 pm, from about 10 pm to about 50 pm, from about 50 pm to about 100 pm, from about 50 pm to about 150 pm, from about 50 pm to about 100 pm, from about 50 pm to about 150 pm, or from about 100 pm to about 150 pm.

[0084] In some embodiments, 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.

[0085] In some embodiments, 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.

V. Process oil

[0086] The compositions disclosed herein comprise a process oil. The term "process oil" as used herein refers to any oil that may be used as a carrier, e.g., as a carrier for insoluble sulfur.

[0087] In some embodiments, the process oil is a mineral oil. In some embodiments, the mineral oil is paraffinic oil, naphthenic oil, aromatic oil, or a combination thereof.

[0088] The term "paraffinic oil" as used herein refers to an oil comprising straight- or branched-chain hydrocarbons.

[0089] The term "naphthenic oil" as used herein refers to an oil comprising hydrocarbons containing a saturated ring. In some embodiments, the naphthenic oil comprises hydrocarbons having the following structure:

wherein n is a positive integer.

[0090] The term "aromatic oil" as used herein refers to an oil comprising compounds containing an aromatic ring. In some embodiments, the aromatic oil comprises compounds having the following structure:

wherein n is a positive integer.

[0091] In some embodiments, the process oil comprises a naturally derived oil, or a hydrogenated derivative thereof. The term "naturally derived oil" as used herein refers to any oil than can be derived from a natural and non-petroleum source, such as plants. In some embodiments, 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.

[0092] In some embodiments, the process oil comprises a pyrolytic oil. The term "pyrolytic oil" as used herein refers to an oil that is obtained by heating dried biomass, including but not limited to wood and algae, in the absence of oxygen. In some embodiments, the pyrolytic oil is prepared according to ASTM D7544-12.

[0093] In some embodiments, 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% to about 45 wt%, from about 10 wt% to about 50 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 15 wt% to about 35 wt%, from about 15 wt% to about 40 wt%, from about 15 wt% to about 45 wt%, from about 15 wt% to about 50 wt%, from about 20 wt% to about 25 wt%, from about 20 wt% to about 30 wt%, from about 20 wt% to about 35 wt%, from about 20 wt% to about 40 wt%, from about 20 wt% to about 45 wt%, from about 20 wt% to about 50 wt%, from about 25 wt% to about 30 wt%, from about 25 wt% to about 35 wt%, from about 25 wt% to about 40 wt%, from about 25 wt% to about 45 wt%, from about 25 wt% to about 50 wt%, from about 30 wt% to about 35 wt%, from about 30 wt% to about 40 wt%, from about 30 wt% to about 45 wt%, from about 30 wt% to about 50 wt%, from about 35 wt% to about 40 wt%, from about 35 wt% to about 45 wt%, from about 35 wt% to about 50 wt%, from about 40 wt% to about 45 wt%, from about 40 wt% to about 50 wt%, or from about 45 wt% to about 50 wt% of a process oil.

[0094] In some embodiments, 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.

VI. Stabilizer

[0095] In some embodiments, the compositions disclosed herein further comprise a stabilizer. As used herein, the term "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.

[0096] In some embodiments, 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. In some embodiments, 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.

[0097] In some embodiments, 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 0.75 wt%, from about 0.1 wt% to about 1 wt%, from about 0.25 wt% to about 0.5 wt%, from about 0.25 wt% to about 0.75 wt%, from about 0.25 wt% to about 1 wt%, from about 0.5 wt% to about 0.75 wt%, from about 0.5 wt% to about 1 wt%, or from about 0.75 wt% to about 1 wt% of a stabilizer.

[0098] In some embodiments, 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.

VII. Properties of the Composition

[0099] In some embodiments, 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. In some embodiments, the composition has a Carr index of less than 28%. In some embodiments, 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%.

[0100] In some embodiments, 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. In some embodiments, 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.

VIII. Vulcanized Elastomeric Articles

[0101] The present disclosure also provides vulcanized elastomeric articles comprising the compositions described herein. The term "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.

[0102] The terms "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. In particular, 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. The term "curing" is also used in the art to describe this process.

[0103] The term "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. The term "natural rubber" as used herein refers to a naturally occurring elastomer that can be obtained from Hevea rubber trees. Non-limiting types of synthetic rubbers include unsaturated rubbers, saturated rubbers, rubbers with fluoro and fluoralkyl or fluoralkoxy substituent groups on the polymer chain (FKM), silicone rubbers (Q), and blends thereof. Non-limiting examples of unsaturated rubbers include polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene butadiene rubber (SBR), nitrile butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), and blends thereof. These unsaturated rubbers undergo cyclization and crosslinking reactions that lead to hardening of the aged part. As oxidation occurs, these vulcanizates harden and eventually become brittle products. Partial oxidation of vulcanizates leads to losses in performance when used in applications such as vehicle tire sidewalls. Saturated rubbers are rubbers that do not contain C=C unsaturation and include, but are not limited to, 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), and blends thereof.

[0104] In some embodiments, 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. In some embodiments, the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion). [0105] In some embodiments, the one or more elastomers further comprises recycled rubber. The term "recycled rubber" as used herein refers to an elastomer that has been reclaimed from scrap materials such as used tires.

[0106] The present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein.

[0107] In some embodiments, the vulcanized elastomeric article is a tire. In some embodiments, 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.

[0108] In some embodiments, the vulcanized elastomeric article is a component of a tire. In some embodiments, the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

[0109] In some embodiments, 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. Processes

[0110] The present disclosure also provides processes for preparing a vulcanized elastomeric article, the process comprising:

(a) admixing a composition described herein with at least one elastomer to form a mixture;

(b) forming the mixture of (a) into a formed shape; and

(c) vulcanizing the formed shape, to provide a vulcanized elastomeric article.

[OHl] In some embodiments, 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 to about 180 °C, from about 140 °C to about 200 °C, from about 160 °C to about 180 °C, from about 160 °C to about 200 °C, or from about 180 °C to about 200 °C.

[0112] In some embodiments, 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

[0113] The present disclosure also provides 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. In some embodiments, the kit comprises a composition described herein and instructions for using the composition in a vulcanizable elastomeric composition. In some embodiments, 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.

IX. Sulfur Masterbatches

[0114] The present disclosure also provides sulfur masterbatches comprising a composition described herein and at least one elastomer.

[0115] In some embodiments, 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.

[0116] In some embodiments, masterbatch comprises from about 60 wt% to about 90 wt% of a composition described herein. In some embodiments, 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 about 60 wt% to about 95 wt%, from about 70 wt% to about 80 wt%, from about 70 wt% to about 90 wt%, from about 70 wt% to about 95 wt%, from about 80 wt% to about 90 wt%, from about 80 wt% to about 95 wt%, or from about 90 wt% to about 95 wt% of a composition described herein.

[0117] In some embodiments, 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.

[0118] In some embodiments, 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 about 10 wt% to about 45 wt%, from about 10 wt% to about 50 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 15 wt% to about 35 wt%, from about 15 wt% to about 40 wt%, from about 15 wt% to about 45 wt%, from about 15 wt% to about 50 wt%, from about 20 wt% to about 25 wt%, from about 20 wt% to about 30 wt%, from about 20 wt% to about 35 wt%, from about 20 wt% to about 40 wt%, from about 20 wt% to about 45 wt%, from about 20 wt% to about 50 wt%, from about 25 wt% to about 30 wt%, from about 25 wt% to about 35 wt%, from about 25 wt% to about 40 wt%, from about 25 wt% to about 45 wt%, from about 25 wt% to about 50 wt%, from about 30 wt% to about 35 wt%, from about 30 wt% to about 40 wt%, from about 30 wt% to about 45 wt%, from about 30 wt% to about 50 wt%, from about 35 wt% to about 40 wt%, from about 35 wt% to about 45 wt%, from about 35 wt% to about 50 wt%, from about 40 wt% to about 45 wt%, from about 40 wt% to about 50 wt%, or from about 45 wt% to about 50 wt% elastomer.

[0119] In some embodiments, 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.

X. Particular Embodiments

[0120] The present disclosure provides the following particular embodiments.

[0121] 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.

[0122] Embodiment II. The composition of Embodiment I, wherein the polymer is an EPDM polymer.

[0123] Embodiment III. The composition of Embodiment II, wherein the EPDM polymer has an ethylene content of from about 55 wt% to about 85 wt%.

[0124] Embodiment IV. The composition of Embodiment III, wherein the EPDM polymer has an ethylene content of about 70 wt%.

[0125] 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%.

[0126] Embodiment VI. The composition of Embodiment V, wherein the EPDM polymer has an ethylidene norbornene content of about 4.9 wt%.

[0127] 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.

[0128] 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.

[0129] Embodiment IX. The composition of Embodiment I, wherein the polymer is an SIS polymer. [0130] Embodiment X. The composition of Embodiment IX, wherein the styrene content of the SIS polymer is from about 5 wt% to about 20 wt%.

[0131] Embodiment XI. The composition of Embodiment X, wherein the styrene content of the SIS polymer is about 14 wt%.

[0132] 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.

[0133] Embodiment XIII. The composition of Embodiment XII, wherein the structure of the SIS polymer is linear.

[0134] Embodiment XIV. The composition of Embodiment XII, wherein the structure of the SIS polymer is a combination of linear and radial.

[0135] Embodiment XV. The composition of Embodiment I, wherein the polymer is an oxygenated polymer.

[0136] Embodiment XVI. The composition of Embodiment XV, wherein the oxygenated polymer comprises polyethylene glycol, polypropylene glycol, or a combination thereof.

[0137] Embodiment XVII. The composition of Embodiment XVI, wherein the ethylene oxide content of the oxygenated polymer is from about 60 wt% to about 90 wt%.

[0138] Embodiment XVIII. The composition of Embodiment XV, wherein the oxygenated polymer comprises poly(ethylene-co-acrylic acid).

[0139] Embodiment XIX. The composition of Embodiment XV, wherein the oxygenated polymer comprises dicarboxyl-terminated polybutadiene.

[0140] Embodiment XX. The composition of any one of Embodiments XV-XIX, wherein the water content of the oxygenated polymer is less than 0.2 wt%.

[0141] Embodiment XXI. The composition of Embodiment I, wherein the polymer is a polyolefin plastomer or elastomer.

[0142] 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.

[0143] 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. [0144] Embodiment XXIV. The composition of Embodiment I, wherein the polymer is an isoprene polymer.

[0145] 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.

[0146] Embodiment XXVI. The composition of Embodiment XXV, wherein the stabilizer is an ionic liquid.

[0147] Embodiment XXVII. The composition of Embodiment XXV, wherein the stabilizer is a unsaturated olefin.

[0148] Embodiment XXVIII. The composition of Embodiment XXV, wherein the stabilizer is a carbonium ion.

[0149] Embodiment XXIX. The composition of Embodiment XXV, wherein the stabilizer is alpha-methyl styrene, pinene, terpene, ammonium sulfate, ethyl sodium xanthate, camphene, benzothiazole, or limonene.

[0150] Embodiment XXX. The composition of any one of Embodiments I-XXIX, wherein the composition comprises about 80 wt% insoluble sulfur.

[0151] 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.

[0152] Embodiment XXXII. The composition of Embodiment XXXI, wherein the insoluble sulfur has an average primary particle size of 10 pm ± 5 pm.

[0153] Embodiment XXXIII. The composition of Embodiment XXXI, wherein the insoluble sulfur has an average primary particle size of 50 pm ± 15 pm.

[0154] Embodiment XXXIV. The composition of any one of Embodiments I-XXXIII, wherein the composition comprises about 19.2 wt% process oil.

[0155] 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.

[0156] Embodiment XXXVI. The composition of Embodiment XXXV, wherein the process oil comprises a mineral oil.

[0157] Embodiment XXXVII. The composition of Embodiment XXXVI, wherein the mineral oil is paraffinic oil, naphthenic oil, aromatic oil, or a combination thereof.

[0158] Embodiment XXXVIII. The composition of Embodiment XXXVII, wherein the mineral oil is naphthenic oil. [0159] Embodiment XXXIX. The composition of Embodiment XXXV, wherein the process oil comprises a naturally derived oil, or a hydrogenated derivative thereof.

[0160] 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.

[0161] Embodiment XLI. The composition of any one of Embodiments I-XL, wherein the composition comprises about 0.8 wt% polymer.

[0162] Embodiment XLII. The composition of any one of Embodiments I-XLI, wherein the composition has a Carr index of less than 28%.

[0163] Embodiment XLIII. The composition of any one of Embodiments I-XLII, wherein the composition has a Hausner ratio of less than 1.40.

[0164] Embodiment XLIV. A vulcanized elastomeric article comprising the composition of any one of Embodiments I-XLII.

[0165] Embodiment XLV. A vulcanized elastomeric article prepared using the composition of any one of Embodiments I-XLII.

[0166] Embodiment XL VI. The vulcanized elastomeric article of Embodiment XLIV or

XLV, wherein the vulcanized elastomeric article is a tire.

[0167] Embodiment XL VII. A process for preparing a vulcanized elastomeric article, the process comprising:

(a) admixing the composition of any one of Embodiments I-XLIII with at least one elastomer to form a mixture;

(b) forming the mixture of (a) into a formed shape; and

(c) vulcanizing the formed shape to provide a vulcanized elastomeric article.

[0168] 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.

[0169] 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.

[0170] Embodiment L. A sulfur masterbatch comprising the composition of any one of Embodiments I-XLIII and at least one elastomer. [0171] 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 copolymer (EVM), rubbers with fluoro and fluoralkyl or fluoralkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q), or a combination thereof.

[0172] Embodiment LIL The masterbatch of Embodiment LI, wherein the masterbatch comprises from about 60 wt% to about 90 wt% of the composition of any one of Embodiments I-XLIII.

[0173] Embodiment LIII. The masterbatch of Embodiment LII, wherein the masterbatch comprises about 80 wt% of the composition of any one of Embodiments I- XLIII.

[0174] Embodiment LIV. The masterbatch of any one of Embodiments L-LIII, wherein the masterbatch comprises from about 10 wt% to about 40 wt% elastomer.

[0175] Embodiment LV. The masterbatch of Embodiment LIV, wherein the masterbatch comprises about 20 wt% elastomer.

[0176] The present disclosure provides the following particular embodiments.

[0177] 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.

[0178] Embodiment 2. The composition of Embodiment 1, wherein at least one of the one or more polymers is an EPDM polymer.

[0179] Embodiment 3. The composition of Embodiment 2, wherein the EPDM polymer has an ethylene content of from about 55 wt% to about 85 wt%.

[0180] Embodiment 4. The composition of Embodiment 3, wherein the EPDM polymer has an ethylene content of about 70 wt%. [0181] Embodiment 5. The composition of any one of Embodiments 2-4, wherein the EPDM polymer has an ethylidene norbornene content of from about 0 wt% to about 10 wt%.

[0182] Embodiment 6. The composition of Embodiment 5, wherein the EPDM polymer has an ethylidene norbornene content of about 4.9 wt%.

[0183] 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.

[0184] Embodiment 8. The composition of Embodiment 7, wherein the EPDM polymer has a Mooney viscosity of about 25 ML(l+4) when measured according to the ASTM DI 646 standard.

[0185] 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.

[0186] Embodiment 10. The composition of Embodiment 9, wherein the styrene content of the SIS polymer is from about 5 wt% to about 20 wt%.

[0187] Embodiment 11. The composition of Embodiment 10, wherein the styrene content of the SIS polymer is about 14 wt%.

[0188] 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.

[0189] Embodiment 13. The composition of Embodiment 12, wherein the structure of the SIS polymer is linear.

[0190] Embodiment 14. The composition of Embodiment 12, wherein the structure of the SIS polymer is a combination of linear and radial.

[0191] Embodiment 15. The composition any one of Embodiments 1-14, wherein at least one of the one or more polymers is an oxygenated polymer.

[0192] Embodiment 16. The composition of Embodiment 15, wherein the oxygenated polymer comprises polyethylene glycol, polypropylene glycol, or a combination thereof.

[0193] 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%.

[0194] Embodiment 18. The composition of Embodiment 15, wherein the oxygenated polymer comprises poly(ethylene-co-acrylic acid). [0195] Embodiment 19. The composition of Embodiment 15, wherein the oxygenated polymer comprises dicarboxyl-terminated polybutadiene.

[0196] 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%.

[0197] 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.

[0198] 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.

[0199] 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.

[0200] 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.

[0201] 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.

[0202] Embodiment 26. The composition of Embodiment 25, wherein the stabilizer is an ionic liquid.

[0203] Embodiment 27. The composition of Embodiment 25, wherein the stabilizer is a unsaturated olefin.

[0204] Embodiment 28. The composition of Embodiment 25, wherein the stabilizer is a carbonium ion.

[0205] 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.

[0206] Embodiment 30. The composition of any one of Embodiments 1-29, wherein the composition comprises about 80 wt% insoluble sulfur.

[0207] 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.

[0208] Embodiment 32. The composition of Embodiment 31, wherein the insoluble sulfur has an average primary particle size of 10 pm ± 5 pm. [0209] Embodiment 33. The composition of Embodiment 31, wherein the insoluble sulfur has an average primary particle size of 50 pm ± 15 pm.

[0210] Embodiment 34. The composition of any one of Embodiments 1-33, wherein the composition comprises about 19.2 wt% process oil.

[0211] Embodiment 35. The composition of any one of Embodiments 1-33, wherein the composition comprises about 10 wt% process oil.

[0212] 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.

[0213] Embodiment 37. The composition of Embodiment 36, wherein the process oil comprises a mineral oil.

[0214] Embodiment 38. The composition of Embodiment 37, wherein the mineral oil is paraffinic oil, naphthenic oil, aromatic oil, or a combination thereof.

[0215] Embodiment 39. The composition of Embodiment 38, wherein the mineral oil is naphthenic oil.

[0216] Embodiment 40. The composition of Embodiment 36, wherein the process oil comprises a naturally derived oil, or a hydrogenated derivative thereof.

[0217] 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.

[0218] 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.

[0219] 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.

[0220] 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.

[0221] 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.

[0222] Embodiment 46. 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 0.01 wt% to about 0.07 wt% of a polyolefin plastomer or elastomer, and from about 0.4 wt% to about 1 wt% of an EPDM polymer.

[0223] 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/cm³ and an ethylene content of about 16.

[0224] Embodiment 48. The composition of Embodiment 47, wherein the polyolefin plastomer or elastomer is VISTAMAXX™ Performance Polymer 6102.

[0225] 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.

[0226] Embodiment 50. The composition of Embodiment 49, wherein the EPDM polymer is NORDEL™ IP 4725P.

[0227] Embodiment 51. The composition of any one of Embodiments 1-50, wherein the composition has a Carr index of less than 28%.

[0228] Embodiment 52. The composition of any one of Embodiments 1-51, wherein the composition has a Hausner ratio of less than 1.40.

[0229] Embodiment 53. A vulcanized elastomeric article comprising the composition of any one of Embodiments 1-52.

[0230] Embodiment 54. A vulcanized elastomeric article prepared using the composition of any one of Embodiments 1-52.

[0231] Embodiment 55. The vulcanized elastomeric article of Embodiment 53 or 54, wherein the vulcanized elastomeric article is a tire.

[0232] Embodiment 56. A process for preparing a vulcanized elastomeric article, the process comprising:

(a) admixing the composition of any one of Embodiments 1-52 with at least one elastomer to form a mixture;

(b) forming the mixture of (a) into a formed shape; and

(c) vulcanizing the formed shape to provide a vulcanized elastomeric article.

[0233] 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.

[0234] 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.

[0235] Embodiment 59. A sulfur masterbatch comprising the composition of any one of Embodiments 1-52 and at least one elastomer.

[0236] 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), or a combination thereof.

[0237] 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.

[0238] Embodiment 62. The masterbatch of Embodiment 61, wherein the masterbatch comprises about 80 wt% of the composition of any one of Embodiments 1- 52.

[0239] Embodiment 63. The masterbatch of any one of Embodiments 59-62, wherein the masterbatch comprises from about 10 wt% to about 40 wt% elastomer.

[0240] Embodiment 64. The masterbatch of Embodiment 63, wherein the masterbatch comprises about 20 wt% elastomer. EXAMPLES

EXAMPLE 1 Preparation of Insoluble Sulfur Compositions

[0241] 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) or a process oil (Hyprene 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.

EXAMPLE 2

Measurement of Carr Index and Hausner Ratio of Insoluble Sulfur Compositions [0242] The Carr index of insoluble sulfur compositions prepared using the procedure described in Example 1 were measured using the ASTM Standard Test Method for Bulk Solids Characterization by Carr Indices, e.g., as described in ASTM D6393-14, published by ASTM International, which is incorporated herein by reference. The Carr index is defined as follows:

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.

[0243] 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.

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.

[0244] Having now fully described the methods, compounds, and compositions herein, it will be understood by those of skill in the art that the same can be performed within a wide and equivalent range of conditions, formulations, and other parameters without affecting the scope of the methods, compounds, and compositions provided herein or any embodiment thereof. All patents, patent applications, and publications cited herein are fully incorporated by reference herein in their entirety.

Claims

WHAT IS CLAIMED IS:

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.

2. The composition of claim 1, wherein at least one of the one or more polymers is an EPDM polymer.

3. The composition of claim 2, wherein the EPDM polymer has an ethylene content of from about 55 wt% to about 85 wt%.

4. The composition of claim 3, wherein the EPDM polymer has an ethylene content of about 70 wt%.

5. The composition of any one of claims 2-4, wherein the EPDM polymer has an ethylidene norbomene content of from about 0 wt% to about 10 wt%.

6. The composition of claim 5, wherein the EPDM polymer has an ethylidene norbomene content of about 4.9 wt%.

7. The composition of any one of claims 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.

8. The composition of claim 7, wherein the EPDM polymer has a Mooney viscosity of about 25 ML(l+4) when measured according to the ASTM D1646 standard.

9. The composition of any one of claims 1-8, wherein at least one of the one or more polymers is an SIS polymer.

10. The composition of claim 9, wherein the styrene content of the SIS polymer is from about 5 wt% to about 20 wt%.

11. The composition of claim 10, wherein the styrene content of the SIS polymer is about 14 wt%.

12. The composition of any one of claims 9-11, wherein the structure of the SIS polymer is linear, radial, branched, pendant, dendritic, or a combination thereof.

13. The composition of claim 12, wherein the structure of the SIS polymer is linear.

14. The composition of claim 12, wherein the structure of the SIS polymer is a combination of linear and radial.

15. The composition any one of claims 1-14, wherein at least one of the one or more polymers is an oxygenated polymer.

16. The composition of claim 15, wherein the oxygenated polymer comprises polyethylene glycol, polypropylene glycol, or a combination thereof.

17. The composition of claim 16, wherein the ethylene oxide content of the oxygenated polymer is from about 60 wt% to about 90 wt%.

18. The composition of claim 15, wherein the oxygenated polymer comprises poly(ethylene- co-acrylic acid).

19. The composition of claim 15, wherein the oxygenated polymer comprises dicarboxyl- terminated polybutadiene.

20. The composition of any one of claims 15-19, wherein the water content of the oxygenated polymer is less than 0.2 wt%.

21. The composition of any one of claims 1-20, wherein at least one of the one or more polymers is a polyolefin plastomer or elastomer.

22. The composition of claim 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 D1238.

23. The composition of claim 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.

24. The composition of any one of claims 1-23, wherein at least one of the one or more polymers is an isoprene polymer.

25. The composition of any one of claims 1-24, further comprising from about 0.01 wt% to about 1 wt% of a stabilizer.

26. The composition of claim 25, wherein the stabilizer is an ionic liquid.

27. The composition of claim 25, wherein the stabilizer is a unsaturated olefin.

28. The composition of claim 25, wherein the stabilizer is a carbonium ion.

29. The composition of claim 25, wherein the stabilizer is alpha-methyl styrene, pinene, terpene, ammonium sulfate, ethyl sodium xanthate, camphene, benzothiazole, or limonene.

30. The composition of any one of claims 1-29, wherein the composition comprises about 80 wt% insoluble sulfur.

31. The composition of any one of claims 1-30, wherein the insoluble sulfur has an average primary particle size of from about 3 pm to about 65 pm.

32. The composition of claim 31, wherein the insoluble sulfur has an average primary particle size of 10 pm ± 5 pm.

33. The composition of claim 31, wherein the insoluble sulfur has an average primary particle size of 50 pm ± 15 pm.

34. The composition of any one of claims 1-33, wherein the composition comprises about 19.2 wt% process oil.

35. The composition of any one of claims 1-33, wherein the composition comprises about 10 wt% process oil.

36. The composition of any one of claims 1-35, wherein the process oil comprises a mineral oil, a naturally derived oil, a pyrolytic oil, or a combination thereof.

37. The composition of claim 36, wherein the process oil comprises a mineral oil.

38. The composition of claim 37, wherein the mineral oil is paraffinic oil, naphthenic oil, aromatic oil, or a combination thereof.

39. The composition of claim 38, wherein the mineral oil is naphthenic oil.

40. The composition of claim 36, wherein the process oil comprises a naturally derived oil, or a hydrogenated derivative thereof.

41. The composition of claim 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.

42. The composition of any one of claims 1-41, wherein the composition comprises about 0.8 wt% of the one or more polymers.

43. The composition of claim 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.

44. The composition of claim 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.

45. The composition of claim 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.

46. The composition of claim 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 0.01 wt% to about 0.07 wt% of a polyolefin plastomer or elastomer, and from about 0.4 wt% to about 1 wt% of an EPDM polymer.

47. The composition of any one of claims 43, 45, or 46, wherein the polyolefin plastomer or elastomer has a density of about 0.862 g/cm³ and an ethylene content of about 16.

48. The composition of claim 47, wherein the polyolefin plastomer or elastomer is VISTAMAXX™ Performance Polymer 6102.

49. The composition of any one of claims 44-46, wherein the EPDM polymer has an ethylene content of about 70 and an ethylidene norbomene (ENB) content of about 4.9.

50. The composition of claim 49, wherein the EPDM polymer is NORDEL™ IP 4725P.

51. The composition of any one of claims 1-50, wherein the composition has a Carr index of less than 28%.

52. The composition of any one of claims 1-51, wherein the composition has a Hausner ratio of less than 1.40.

53. A vulcanized elastomeric article comprising the composition of any one of claims 1-52.

54. A vulcanized elastomeric article prepared using the composition of any one of claims 1- 52.

55. The vulcanized elastomeric article of claim 53 or 54, wherein the vulcanized elastomeric article is a tire.

56. A process for preparing a vulcanized elastomeric article, the process comprising:

(a) admixing the composition of any one of claims 1-52 with at least one elastomer to form a mixture;

(b) forming the mixture of (a) into a formed shape; and

(c) vulcanizing the formed shape to provide a vulcanized elastomeric article.

57. A kit comprising the composition of any one of claims 1-52 and instructions for using the composition in a vulcanizable elastomeric composition.

58. A kit comprising the composition of any one of claims 1-52 and instructions for using the composition to prepare a vulcanized elastomeric article.

59. A sulfur masterbatch comprising the composition of any one of claims 1-52 and at least one elastomer.

60. The masterbatch of claim 59, wherein the elastomer is natural rubber (NR), polyisoprene rubber (IR), butyl rubber (IIR), 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.

61. The masterbatch of claim 60, wherein the masterbatch comprises from about 60 wt% to about 90 wt% of the composition of any one of claims 1-52.

62. The masterbatch of claim 61, wherein the masterbatch comprises about 80 wt% of the composition of any one of claims 1-52.

63. The masterbatch of any one of claims 59-62, wherein the masterbatch comprises from about 10 wt% to about 40 wt% elastomer.

64. The masterbatch of claim 63, wherein the masterbatch comprises about 20 wt% elastomer.