Insoluble sulfur composition

Abstract

The present disclosure provides a composition comprising insoluble sulfur, a processing oil, and one or more polymers. The present disclosure also provides vulcanized elastomer articles comprising the compositions described herein and vulcanized elastomer articles prepared using the compositions disclosed herein. The present disclosure also provides methods for making vulcanized elastomeric articles comprising the compositions described herein. The present disclosure also provides kits comprising the compositions described herein. The present disclosure also provides a sulfur masterbatch comprising the composition described herein and an elastomer.

Description

Background Art Technical Field

[0001] The present disclosure provides insoluble sulfur compositions that can be used to vulcanize rubber to produce rubber products (eg, tires). Background Art

[0002] Insoluble sulfur (also known as polymeric sulfur) is used as a crosslinking (vulcanizing) agent in rubber compound formulations. Insoluble sulfur is polymeric in nature and is insoluble in carbon disulfide.

[0003] The use of insoluble sulfur rather than soluble sulfur avoids a number of processing problems, the most common being "blooming," in which soluble sulfur migrates within the rubber compound and crystallizes on the surface, and "storage scorch," the premature vulcanization of the rubber when mixed with soluble sulfur.

[0004] Insoluble sulfur is a solid powder that is mixed with elastomers to form rubber compounds. It would be desirable to formulate insoluble sulfur compositions that exhibit enhanced flow and / or dispersibility, which would reduce processing and manufacturing costs. Summary of the Invention

[0005] In one aspect, the present disclosure provides a composition comprising insoluble sulfur, a process oil, one or more polymers, and optionally a stabilizer. In some embodiments, the composition comprises from about 50% to about 95% by weight of insoluble sulfur, from about 5% to about 50% by weight of the process oil, and from about 0.1% to about 3% by weight of the one or more polymers, wherein at least one of the one or more polymers is an ethylene propylene diene monomer (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 a vulcanized elastomeric article comprising the insoluble sulfur composition disclosed herein.

[0007] In another aspect, the present disclosure provides a vulcanized elastomeric article prepared using the insoluble sulfur composition described herein.

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

[0009] (a) mixing an insoluble sulfur composition disclosed herein with at least one elastomer to form a mixture;

[0010] (b) forming the mixture of (a) into a shaped shape; and

[0011] (c) Vulcanizing the formed shape

[0012] To provide vulcanized elastomer products.

[0013] In another aspect, the present disclosure provides a kit comprising the insoluble sulfur composition disclosed herein and instructions for using the composition in a vulcanizable elastomeric composition.

[0014] The present disclosure also provides kits comprising the compositions disclosed herein and instructions for using the compositions to prepare vulcanized elastomeric articles.

[0015] In another aspect, the present disclosure provides a sulfur masterbatch comprising the insoluble sulfur composition disclosed herein and at least one elastomer.

[0016] Additional embodiments and advantages of the present disclosure will be set forth in part in the following description and will be derived from the description, or may be learned by practice of the present disclosure. The embodiments and advantages of the present disclosure will be realized and attained by means of the elements and combinations particularly pointed out in the appended claims.

[0017] 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

[0018] Figure 1 is a scatter plot showing the Carr Index for compositions comprising insoluble sulfur, process oil, and one or more polymers (or only insoluble sulfur and process oil) at various polymer concentrations.

[0019] Figure 2 is a scatter plot showing the Hausner Ratio for compositions comprising insoluble sulfur, process oil, and one or more polymers (or only insoluble sulfur and process oil) at various polymer concentrations. DETAILED DESCRIPTION

[0020] I. Definition

[0021] Unless otherwise stated, the use of the terms "a / an," "the," and similar designators in the context of describing the present disclosure (especially in the context of the claims) will be considered to encompass both the singular and the plural. Unless otherwise stated herein, references to ranges of values ​​herein are merely intended to serve as a shorthand method of individually referring to each individual value within the range, and each individual value is incorporated into the specification as if it were individually cited herein. Unless otherwise stated, the use of any and all examples or exemplary language (e.g., "such as") provided herein is intended to better illustrate the present disclosure rather than to limit the scope of the present disclosure. No language in the specification should be construed as indicating that any unclaimed element is necessary to practice the present disclosure.

[0022] As used herein, the term "one or more" is intended to mean the presence of at least one component of the relevant class of components (e.g., one or more polymers), 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.

[0023] As used herein, the term "about" indicates that the value of a given quantity varies by ±5% of the stated value. For example, "about 100 nm" encompasses a range of 95 nm to 105 nm (including endpoints).

[0024] As used herein, the term "wt %" refers to the mass of one component or a particular 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 multiplied by 100. For example, the weight % 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, in a composition comprising 8 kg of insoluble sulfur, 1.95 kg of process oil, 0.025 kg of polymer A, and 0.025 kg of polymer B, the weight percent of the one or more polymers (wherein the one or more polymers are polymer A and polymer B) is 5 weight percent ((0.025 kg + 0.025 kg) / (8 kg + 1.95 kg + 0.025 kg + 0.025 kg) x 100 = 5 weight percent).

[0025] As used herein, the term "average primary particle size" refers to the median particle size of unagglomerated individual particles by volume as measured by static light scattering. This term is also referred to as "D50."

[0026] As used herein, the term "number average molecular weight" or "Mn" refers to the statistical average molecular weight of all polymer chains in a polymer sample.

[0027] As used herein, the term "weight average molecular weight" or "Mw" refers to the weight average molecular weight of all polymer chains in a polymer sample.

[0028] As used herein, the term "terpolymer" refers to a polymer formed by the polymerization of three different monomers. In some embodiments, the monomers are randomly arranged throughout the polymer chain.

[0029] As used herein, the term "diene" refers to a compound containing two double bonds. An example of a diene is ethylidene norbornene (ENB), which has the following structure:

[0030]

[0031] As used herein, the term "Mooney viscosity" refers to the shear torque that resists the rotation of a cylindrical metal disk (or rotor) embedded in rubber within a cylindrical cavity, as fully defined in standard test methods (eg, ASTM D1646).

[0032] As used herein, the terms "melt index," "melt flow index," or "melt flow rate" refer to a measure of the ease with which a thermoplastic polymer melt flows and are defined as the mass of polymer in grams that flows through a capillary of specified diameter and length in ten minutes at a specified temperature and pressure applied by a specified gravimetric weight, as described in standards ASTM D1238 and ISO 1133.

[0033] As used herein, the term "coupling efficiency" refers to the percentage of triblock copolymers formed when synthesizing a triblock copolymer (e.g., styrene-isoprene-styrene (SIS)) from a diblock copolymer (e.g., styrene-isoprene (SI)).

[0034] II. Composition

[0035] The present disclosure provides a composition 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 % process oil, from about 0.1 wt % to about 3 wt % of one or more polymers, and from 0 wt % to about 1 wt % stabilizer.

[0036] In some embodiments, the present disclosure provides a composition comprising insoluble sulfur, a process oil, a polymer, and optionally a stabilizer. In some embodiments, the composition comprises from about 50% to about 95% by weight of insoluble sulfur, from about 5% to about 50% by weight of the process oil, from about 0.1% to about 3% by weight of a polymer, and from 0% to about 1% by weight of the stabilizer.

[0037] In some embodiments, the present disclosure provides a composition comprising insoluble sulfur, a process oil, two polymers, and optionally a stabilizer. In some embodiments, the composition comprises from about 50% to about 95% by weight of insoluble sulfur, from about 5% to about 50% by weight of the process oil, from about 0.1% to about 3% by weight of the two polymers, and from 0% to about 1% by weight of the stabilizer.

[0038] In some embodiments, the present disclosure provides a composition comprising insoluble sulfur, a process oil, three polymers, and optionally a stabilizer. In some embodiments, the composition comprises from about 50% to about 95% by weight of insoluble sulfur, from about 5% to about 50% by weight of the process oil, from about 0.1% to about 3% by weight of the three polymers, and from 0% to about 1% by weight of the stabilizer.

[0039] III. Polymers

[0040] 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 monomer (EPDM) polymer, a styrene isoprene styrene (SIS) polymer, an oxygen-containing polymer, a polyolefin plastomer or elastomer, or an isoprene polymer.

[0041] As used herein, the term "ethylene propylene diene monomer polymer" or "EPDM polymer" refers to a terpolymer formed from ethylene, propylene, and a diene monomer. 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:

[0042]

[0043] Where n, l, and p are positive integers.

[0044] As used herein, the term "ethylene content" refers to the weight percent of a polymer derived from ethylene monomers. In some embodiments, the EPDM polymer has an ethylene content of about 55 weight percent to about 85 weight percent. In some embodiments, the EPDM polymer has an ethylene content of about 40 weight percent to about 45 weight percent, about 40 weight percent to about 50 weight percent, about 40 weight percent to about 55 weight percent, about 40 weight percent to about 60 weight percent, about 40 weight percent to about 65 weight percent, about 40 weight percent to about 70 weight percent, about 40 weight percent to about 75 weight percent, about 40 weight percent to about 80 weight percent, about 40 weight percent to about 85 weight percent, about 40 weight percent to about 90 weight percent, about 45 weight percent to about 50 weight percent, about 45 weight percent to about 55 weight percent, about % to about 60% by weight, about 45% to about 65% by weight, about 45% to about 70% by weight, about 45% to about 75% by weight, about 45% to about 80% by weight, about 45% to about 85% by weight, about 45% to about 90% by weight, about 50% to about 55% by weight, about 50% to about 60% by weight, about 50% to about 65% by weight, about 50% to about 70% by weight, about 50% to about 75% by weight, about 50% to about 80% by weight, about 50% to about 85% by weight, about 50% to about 90% by weight, about 55% to about 60% by weight, about 55% to about 65% by weight, about 55% to about 70% by weight, about 55% to about 75% by weight, about 55% to about 80% by weight, about 55% to about 90% by weight, about 60% to about 65% by weight, about 60% to about 70% by weight, about 60% to about 75% by weight, about 60% to about 80% by weight, about 60% to about 85% by weight, about 60% to about 90% by weight, about 65% to about 70% by weight, about % to about 80% by weight, about 65% to about 85% by weight, about 65% to about 90% by weight, about 70% to about 75% by weight, about 70% to about 80% by weight, about 70% to about 85% by weight, about 70% to about 90% by weight, about 75% to about 80% by weight, about 75% to about 85% by weight, about 75% to about 90% by weight, about 80% to about 85% by weight, about 80% to about 90% by weight, or about 90% to about 95% by weight.

[0045] In some embodiments, the EPDM polymer has an ethylene content of about 70% by weight. In some embodiments, the EPDM polymer has an ethylene content of about 45%, about 50%, about 55%, about 60%, about 65%, about 75%, about 80%, about 85%, or about 90% by weight.

[0046] As used herein, the term "ethylidene norbornene content" refers to the weight percent of a polymer derived from ethylidene norbornene monomers. In some embodiments, the EPDM polymer has an ethylidene norbornene content of from about 0 weight percent to about 10 weight percent. In some embodiments, the EPDM polymer has an ethylidene norbornene content of from about 0 weight percent to about 1 weight percent, from about 0 weight percent to about 2 weight percent, from about 0 weight percent to about 3 weight percent, from about 0 weight percent to about 4 weight percent, from about 0 weight percent to about 5 weight percent, from about 0 weight percent to about 6 weight percent, from about 0 weight percent to about 7 weight percent, from about 0 weight percent to about 8 weight percent, from about 0 weight percent to about 9 weight percent, from about 0 weight percent to about 10 weight percent, from about 1 weight percent to about 2 weight percent, from about 1 weight percent to about 3 weight percent , about 1 wt % to about 4 wt %, about 1 wt % to about 5 wt %, about 1 wt % to about 6 wt %, about 1 wt % to about 7 wt %, about 1 wt % to about 8 wt %, about 1 wt % to about 9 wt %, about 1 wt % to about 10 wt %, about 2 wt % to about 3 wt %, about 2 wt % to about 4 wt %, about 2 wt % to about 5 wt %, about 2 wt % to about 6 wt %, about 2 wt % to about 7 wt %, about 2 wt % to about 8 wt %, about 2 wt % to about 9 wt %, about 2 wt % to about % to about 10 wt %, about 3 wt % to about 4 wt %, about 3 wt % to about 5 wt %, about 3 wt % to about 6 wt %, about 3 wt % to about 7 wt %, about 3 wt % to about 8 wt %, about 3 wt % to about 9 wt %, about 3 wt % to about 10 wt %, about 4 wt % to about 5 wt %, about 4 wt % to about 6 wt %, about 4 wt % to about 7 wt %, about 4 wt % to about 8 wt %, about 4 wt % to about 9 wt %, about 4 wt % to about 10 wt %, about 5 wt % to about 6 wt %. % by weight, about 5 wt % to about 7 wt %, about 5 wt % to about 8 wt %, about 5 wt % to about 9 wt %, about 5 wt % to about 10 wt %, about 6 wt % to about 7 wt %, about 6 wt % to about 8 wt %, about 6 wt % to about 9 wt %, about 6 wt % to about 10 wt %, about 7 wt % to about 8 wt %, about 7 wt % to about 9 wt %, about 7 wt % to about 10 wt %, about 8 wt % to about 9 wt %, about 8 wt % to about 10 wt %, or about 9 wt % to about 10 wt %.

[0047] 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%.

[0048] In some embodiments, the EPDM polymer has a Mooney viscosity of about 15 ML (1 + 4) to about 90 ML (1 + 4) when measured according to ASTM D1646. In some embodiments, the EPDM polymer has a Mooney viscosity of about 10 ML (1 + 4) to about 20 ML (1 + 4), about 10 ML (1 + 4) to about 30 ML (1 + 4), about 10 ML (1 + 4) to about 40 ML (1 + 4), about 10 ML (1 + 4) to about 50 ML (1 + 4), about 10 ML (1 + 4) to about 60 ML (1 + 4), about 10 ML (1 + 4) to about 70 ML (1 + 4), about 10 ML (1 + 4) to about 80 ML (1 + 4), about 10 ML (1 + 4) to about 90 ML (1 + 4), about 20ML (1+4) to about 30ML (1+4), about 20ML (1+4) to about 40ML (1+4), about 20ML (1+4) to about 50ML (1+4), about 20ML (1+4) to about 60ML (1+4), about 20ML (1+4) to about 70ML (1+4), about 20ML (1+4) to about 80ML (1+4), about 20ML (1+4) to about 90ML (1+4), about 30ML (1+4) to about 40ML (1+4), about 30ML (1+4) to about 50ML (1+4), about 30ML (1+4) to about 4) to about 60ML (1+4), about 30ML (1+4) to about 70ML (1+4), about 30ML (1+4) to about 80ML (1+4), about 30ML (1+4) to about 90ML (1+4), about 40ML (1+4) to about 50ML (1+4), about 40ML (1+4) to about 60ML (1+4), about 40ML (1+4) to about 70ML (1+4), about 40ML (1+4) to about 80ML (1+4), about 40ML (1+4) to about 90ML (1+4), about 50ML (1+4) to about 60ML L(1+4), about 50ML(1+4) to about 70ML(1+4), about 50ML(1+4) to about 80ML(1+4), about 50ML(1+4) to about 90ML(1+4), about 60ML(1+4) to about 70ML(1+4), about 60ML(1+4) to about 80ML(1+4), about 60ML(1+4) to about 90ML(1+4), about 70ML(1+4) to about 80ML(1+4), about 70ML(1+4) to about 90ML(1+4), or about 80ML(1+4) to about 90ML(1+4).

[0049] In some embodiments, the EPDM polymer has a Mooney viscosity of about 25 ML (1+4) when measured according to ASTM D 1646. In some embodiments, the EPDM polymer has a Mooney viscosity of about 10 ML (1+4), about 15 ML (1+4), about 20 ML (1+4), about 30 ML (1+4), about 35 ML (1+4), about 40 ML (1+4), about 45 ML (1+4), about 50 ML (1+4), about 55 ML (1+4), about 60 ML (1+4), about 65 ML (1+4), about 70 ML (1+4), about 75 ML (1+4), about 80 ML (1+4), about 85 ML (1+4), or about 90 ML (1+4) when measured according to ASTM D 1646.

[0050] 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.

[0051] In some embodiments, the EPDM polymer is NORDEL TM EPDM polymer. NORDEL TM EPDM polymers are manufactured by The Dow Chemical Company ("Dow"). Exemplary NORDEL TM The EPDM polymers and their properties (test methods used are noted in parentheses) are described in Table 1.

[0052] Table 1

[0053]

[0054] In some embodiments, the EPDM polymer is VISTALON TM EPDM polymer. VISTALON TM EPDM polymer is manufactured by ExxonMobil. TM The EPDM polymers are described in Table 2.

[0055] Table 2

[0056]

[0057]

[0058] In some embodiments, the EPDM polymer is EPDM polymer, EPDM polymer, EDPM polymer or Liquid EPDM polymer. EPDM, ROYA EPDM, EDPM and Liquid EPDM polymer is manufactured by Lion Elastomers. EPDM, EPDM, EDPM and The liquid EPDM polymers are described in Tables 3-6.

[0059] Table 3

[0060]

[0061]

[0062] (a) The product contains 100 phr (50%) of white hydrogenated paraffin oil. (b) The product contains 75 phr (43%) of white hydrogenated paraffin oil.

[0063] Table 4

[0064]

[0065] Table 5

[0066]

[0067] Table 6

[0068]

[0069] FF indicates that the product is also available in the form of a free-flowing powder; the diene (wt%) and ethylene / propylene ratio in brackets indicate the values ​​for the FF form.

[0070] In some embodiments, the EPDM polymer is EPDM polymer. EPDM polymer is manufactured by ARLANXEO. The EPDM polymers are described in Table 7.

[0071] Table 7

[0072]

[0073]

[0074]

[0075] CLCB = controlled long chain branching; N = narrow molecular weight distribution; M = medium molecular weight distribution; B = broad molecular weight distribution

[0076] In some embodiments, the EPDM polymer is TER EPDM polymer. TEREPDM polymer is manufactured by Versalis. TER EPDM polymers are listed in Table 8.

[0077] Table 8

[0078]

[0079] * refers to polymer matrix; **ML(1+4)100℃

[0080] In some embodiments, at least one of the one or more polymers is a SIS polymer.

[0081] As used herein, the term "styrene isoprene styrene polymer" or "SIS polymer" refers to a block copolymer formed from styrene and isoprene (2-methyl-1,3-butadiene) monomers. In some embodiments, SIS comprises the following structure:

[0082]

[0083] Where n, l, and p are positive integers.

[0084] As used herein, the term "styrene content" refers to the weight percent of a polymer derived from styrene monomer.

[0085] 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%.

[0086] In some embodiments, the SIS polymer has a styrene content of about 14 wt %. In some embodiments, the SIS polymer has a styrene content of about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, or about 30 wt %.

[0087] In some embodiments, the structure of the SIS polymer is linear, radial, branched, pendant, dendritic, or a combination thereof.

[0088] In some embodiments, the SIS polymer is QUINTAC TM Polymer. QUINTAC TM The polymer is manufactured by Zeon Corporation. Exemplary QUINTAC TM The polymers are described in Table 9 (test methods used are in parentheses).

[0089] Table 9

[0090]

[0091]

[0092] In some embodiments, at least one of the one or more polymers is an oxygen-containing polymer.As used herein, the term "oxy-containing polymer" refers to any polymer containing one or more oxygen atoms.

[0093] In some embodiments, the oxygen-containing polymer comprises polyethylene glycol. As used herein, the term "polyethylene glycol" or "PEG" refers to a polymer comprising the chemical formula -(O-CH2-CH2) n - a polymer or block copolymer of wherein n is a positive integer.

[0094] As used herein, the term "ethylene oxide content" refers to the weight percent of a polymer derived from ethylene oxide monomers and is a measure of the weight percent of -(O-CH2-CH2)- units present in the polymer. In some embodiments, the ethylene oxide content of the oxygen-containing polymer is from about 60 weight percent to about 90 weight percent. In some embodiments, the ethylene oxide content of the oxygen-containing polymer is from about 20% to about 30% by weight, from about 20% to about 40% by weight, from about 20% to about 50% by weight, from about 20% to about 60% by weight, from about 20% to about 70% by weight, from about 20% to about 80% by weight, from about 20% to about 90% by weight, from about 20% to about 100% by weight, from about 30% to about 40% by weight, from about 30% to about 50% by weight, from about 30% to about 60% by weight, from about 30% to about 70% by weight, from about 30% to about 80% by weight, from about 20% to about 90% by weight, from about 30% to about 100% by weight, from about 40% to about 50% by weight, from about 40% to about 60% by weight. %, about 40% to about 70% by weight, about 40% to about 80% by weight, about 40% to about 90% by weight, about 40% to about 100% by weight, about 50% to about 60% by weight, about 50% to about 70% by weight, about 50% to about 80% by weight, about 50% to about 90% by weight, about 50% to about 100% by weight, about 60% to about 70% by weight, about 60% to about 80% by weight, about 60% to about 100% by weight, about 70% to about 80% by weight, about 70% to about 90% by weight, about 70% to about 100% by weight, about 80% to about 90% by weight, about 80% to about 100% by weight, or about 90% to about 100% by weight.

[0095] In some embodiments, the ethylene oxide content of the oxygen-containing polymer is about 70% by weight. In some embodiments, the ethylene oxide content of the oxygen-containing polymer is about 20% by weight, about 30% by weight, about 40% by weight, about 50% by weight, about 60% by weight, about 80% by weight, about 90% by weight, or about 100% by weight.

[0096] In some embodiments, the oxygen-containing polymer comprises polypropylene glycol. As used herein, the term "polypropylene glycol" or "PPG" refers to a polymer having the chemical formula -(OCH(CH3)-CH2) n - a polymer or block copolymer of wherein n is a positive integer.

[0097] As used herein, "PEG-PPG-PEG" refers to a triblock copolymer of polyethylene glycol, polypropylene glycol, and polyethylene glycol, wherein the length of each individual block can vary. In some embodiments, the PEG-PPG-PEG comprises 84 wt%, 15.6 wt%, and <0.4 wt% ethylene oxide, propylene oxide, and water, respectively. In some embodiments, the PEG-PPG-PEG has an Mw of about 15,000 g / mol.

[0098] As used herein, "PEG-PPG" refers to a diblock copolymer of polyethylene glycol and polypropylene glycol, wherein the length of each individual block can vary. In some embodiments, the PEG-PPG comprises 75 wt%, 24.7 wt%, and <0.3 wt% ethylene oxide, propylene oxide, and water content, respectively.

[0099] As used herein, "PEG-PPG-MBE" refers to a diblock copolymer of polyethylene glycol and polypropylene glycol in which the polymerization has been terminated using monobutyl ether and in which the length of each individual block can vary. In some embodiments, the PEG-PPG-MBE has ethylene oxide, propylene oxide, and water contents of 75 wt%, 24.7 wt%, and <0.3 wt%, respectively.

[0100] As used herein, the term "poly(ethylene-co-acrylic acid)" or "PEAA" refers to a polymer formed from ethylene and acrylic acid monomers. In some embodiments, PEAA comprises the following structure:

[0101]

[0102] Where n and l are positive integers.

[0103] In some embodiments, the PEAA has an ethylene content of about 55% to about 85% by weight. In some embodiments, the PEAA has an ethylene content of about 40% to about 45% by weight, about 40% to about 50% by weight, about 40% to about 55% by weight, about 40% to about 60% by weight, about 40% to about 65% by weight, about 40% to about 70% by weight, about 40% to about 75% by weight, about 40% to about 80% by weight, about 40% to about 85% by weight, about 40% to about 90% by weight, about 45% to about 5 ... % to about 60% by weight, about 45% to about 65% by weight, about 45% to about 70% by weight, about 45% to about 75% by weight, about 45% to about 80% by weight, about 45% to about 85% by weight, about 45% to about 90% by weight, about 50% to about 55% by weight, about 50% to about 60% by weight, about 50% to about 65% by weight, about 50% to about 70% by weight, about 50% to about 75% by weight, about 50% to about 80% by weight, about 50% to about 85% by weight, about 5 0 wt % to about 90 wt %, about 55 wt % to about 60 wt %, about 55 wt % to about 65 wt %, about 55 wt % to about 70 wt %, about 55 wt % to about 75 wt %, about 55 wt % to about 80 wt %, about 55 wt % to about 90 wt %, about 60 wt % to about 65 wt %, about 60 wt % to about 70 wt %, about 60 wt % to about 75 wt %, about 60 wt % to about 80 wt %, about 60 wt % to about 85 wt %, about 60 wt % to about 90 wt %, about 65 wt % to about 70 wt %, about % to about 80 wt %, about 65 wt % to about 85 wt %, about 65 wt % to about 90 wt %, about 70 wt % to about 75 wt %, about 70 wt % to about 80 wt %, about 70 wt % to about 85 wt %, about 70 wt % to about 90 wt %, about 75 wt % to about 80 wt %, about 75 wt % to about 85 wt %, about 75 wt % to about 90 wt %, about 80 wt % to about 85 wt %, about 80 wt % to about 90 wt %, or about 90 wt % to about 95 wt %.

[0104] As used herein, the term "acrylic acid content" refers to the weight percent of the polymer derived from acrylic acid monomers. In some embodiments, the PEAA comprises from about 10 weight percent to about 20 weight percent acrylic acid monomers. In some embodiments, the PEAA comprises about 1 wt % to about 5 wt %, about 1 wt % to about 10 wt %, about 1 wt % to about 15 wt %, about 1 wt % to about 20 wt %, about 1 wt % to about 25 wt %, about 1 wt % to about 30 wt %, about 5 wt % to about 10 wt %, about 5 wt % to about 15 wt %, about 5 wt % to about 20 wt %, about 5 wt % to about 25 wt %, about 5 wt % to about 30 wt %, about 10 wt % to about 15 wt %, about 10 wt % to about 20 wt %, about 10 wt % to about 25 wt %, about 10 wt % to about 30 wt %, about 15 wt % to about 20 wt %, about 15 wt % to about 25 wt %, about 15 wt % to about 30 wt %, about 20 wt % to about 25 wt %, about 20 wt % to about 30 wt %, or about 25 wt % to about 30 wt % of acrylic acid monomer.

[0105] In some embodiments, the oxygen-containing polymer comprises dicarboxyl-terminated polybutadiene. As used herein, the term "polybutadiene" or "BR" refers to a polymer formed from substituted or unsubstituted 1,3-butadiene monomers. Non-limiting examples of substituents include halogen, hydroxyl, cyano, carboxyl, or a combination thereof. The stereochemistry of 1,3-butadiene monomers can result in polymers with cis-, trans-, and branched vinyl orientations. As used herein, the term "dicarboxyl-terminated polybutadiene" refers to a polybutadiene polymer whose termini are substituted with carboxyl groups. In some embodiments, the dicarboxyl-terminated polybutadiene has the following structure:

[0106]

[0107] Where n is a positive integer.

[0108] In some embodiments, the oxygen-containing polymer comprises water. In some embodiments, the water content of the oxygen-containing polymer is less than 0.2 wt %. In some embodiments, the water content of the oxygen-containing 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 %.

[0109] In some embodiments, at least one of the one or more polymers is a polyolefin plastomer (POP) or a polyolefin elastomer (POE). As used herein, the terms "polyolefin plastomer," "POP," "polyolefin elastomer," and "POE" refer to a polymer having the formula -(CH2-CH(R)) n-polymers wherein R is an alkyl chain of variable length and n is the number of monomer units. In some embodiments, the polyolefin plastomer is AFFINITY TM Polyolefin plastomer. AFFINITY TM Polyolefin plastomers are manufactured by Dow. Exemplary AFFINITY TM The polyolefin plastomers are listed in Table 10.

[0110] Table 10

[0111]

[0112]

[0113] In some embodiments, the polyolefin elastomer is ENGAGE TM Polyolefin elastomer. ENGAGE TM Polyolefin elastomers are produced by Dow. TM The polyolefin elastomers are listed in Tables 11-12.

[0114] Table 11. Ethylene Octene Grade ENGAGE TM polyolefin elastomers

[0115]

[0116] Table 12. Ethylene Butene, HM and XLT Grades ENGAGE TM polyolefin elastomers

[0117]

[0118] *Measured at 150°C

[0119] In some embodiments, the polyolefin elastomer is Polyolefin elastomer. The polyolefin elastomer comprises ethylene and propylene and is manufactured by Wessels Corporation. The polyolefin elastomers are listed in Table 13.

[0120] Table 13

[0121]

[0122] *ML(1+4)100℃

[0123] In some embodiments, the polyolefin elastomer is VISTAMAXX TM Polymer. VISTAMAXX TMThe polymer is formed from a mixture of polypropylene and / or ethylene monomers and is manufactured by ExxonMobil Corporation. TM The polymers are listed in Table 14.

[0124] Table 14

[0125]

[0126]

[0127] In some embodiments, the polyolefin plastomer or elastomer has a melt index of about 500 g / 10 min to about 1300 g / 10 min as measured by ASTM D 1238. In some embodiments, the polyolefin plastomer or elastomer has a melt index of about 500 g / 10 min to about 700 g / 10 min, about 700 g / 10 min to about 1000 g / 10 min, about 700 g / 10 min to about 1200 g / 10 min, or about 1100 g / 10 min to about 1500 g / 10 min, as measured by ASTM D 1238.

[0128] In some embodiments, the polyolefin plastomer or elastomer has a melt index of about 500 g / 10 min as measured by ASTM D 1238. 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 D 1238.

[0129] 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 polymer. The polymer is manufactured by The Goodyear Tire & Rubber Company. The polymers are listed in Table 15.

[0130] Table 15

[0131]

[0132] In some embodiments, the isoprene polymer is Kuraray liquid rubber L-IR isoprene polymer. Exemplary liquid rubber L-IR isoprene polymers are listed in Table 16.

[0133] Table 16

[0134]

[0135] In some embodiments, the composition comprises from about 0.1% to about 3% by weight of one or more polymers. In some embodiments, the composition comprises from about 0.01% to about 0.05% by weight, from about 0.01% to about 0.1% by weight, from about 0.01% to about 0.25% by weight, from about 0.01% to about 0.75% by weight, from about 0.01% to about 1% by weight, from about 0.01% to about 2% by weight, from about 0.01% to about 3% by weight, from about 0.05% to about 0.1% by weight, from about 0.05% to about 0.25% by weight, from about 0.05% to about 0.75% by weight, from about 0.05% to about 1% by weight, from about 0.05% to about 2% by weight, from about 0.05% to about 3% by weight, from about % to about 2 wt %, about 0.1 wt % to about 3 wt %, about 0.25 wt % to about 0.75 wt %, about 0.25 wt % to about 1 wt %, about 0.25 wt % to about 2 wt %, about 0.25 wt % to about 3 wt %, about 0.75 wt % to about 1 wt %, about 0.75 wt % to about 2 wt %, about 0.75 wt % to about 3 wt %, about 1 wt % to about 2 wt %, about 1 wt % to about 3 wt %, or about 2 wt % to about 3 wt % of one or more polymers.

[0136] In some embodiments, the composition comprises about 2% by weight of one or more polymers. In some embodiments, the composition comprises about 0.01%, about 0.05%, about 0.1%, about 0.25%, about 0.75%, about 0.8%, about 0.84%, about 1%, about 2%, or about 3% by weight of one or more polymers.

[0137] In some embodiments, the composition comprises one polymer. In some embodiments, the composition comprises two polymers. In some embodiments, the composition comprises three polymers.

[0138] In some embodiments, the composition comprises a polymer, wherein the polymer is an EPDM polymer. In some embodiments, the EPDM polymer is a NORDEL TMEPDM polymer. In some embodiments, NORDEL TM EPDM polymer is NORDEL TM IP 4725P.

[0139] In some embodiments, the composition comprises a polymer, wherein the polymer is a polyolefin elastomer. In some embodiments, the polyolefin elastomer is VISTAMAXX TM In some embodiments, VISTAMAXX TM The polymer is VISTAMAXX TM High performance polymer 6102.

[0140] 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 TM EPDM polymer. In some embodiments, NORDEL TM EPDM polymer is NORDEL TM IP 4725P. In some embodiments, the polyolefin elastomer is VISTAMAXX TM In some embodiments, VISTAMAXX TM The polymer is VISTAMAXX TM High performance polymer 6102.

[0141] IV. Insoluble Sulfur

[0142] The compositions described herein contain insoluble sulfur. As used herein, the term "insoluble sulfur" refers to a product that is primarily insoluble sulfur but can and typically does contain some soluble sulfur (typically less than 10%). This form of sulfur is polymeric in nature and is insoluble in elastomers (e.g., natural rubber) or carbon disulfide (CS2).

[0143] In some embodiments, the composition comprises from about 50% to about 95% by weight of insoluble sulfur, for example, from 70% to about 90% by weight of insoluble sulfur. In some embodiments, the composition comprises from about 50% to about 55% by weight, from about 50% to about 60% by weight, from about 50% to about 65% by weight, from about 50% to about 70% by weight, from about 50% to about 75% by weight, from about 50% to about 80% by weight, from about 50% to about 85% by weight, from about 50% to about 90% by weight, from about 50% to about 95% by weight, from about 55% to about 60% by weight, from about 55% to about % to about 65% by weight, about 55% to about 70% by weight, about 55% to about 75% by weight, about 55% to about 80% by weight, about 55% to about 85% by weight, about 55% to about 90% by weight, about 55% to about 95% by weight, about 60% to about 65% by weight, about 60% to about 70% by weight, about 60% to about 75% by weight, about 60% to about 80% by weight, about 60% to about 85% by weight, about 60% to about % to about 90% by weight, about 60% to about 95% by weight, about 65% to about 70% by weight, about 65% to about 75% by weight, about 65% to about 80% by weight, about 65% to about 85% by weight, about 65% to about 90% by weight, about 65% to about 95% by weight, about 70% to about 75% by weight, about 70% to about 80% by weight, about 70% to about 85% by weight, about 70% to about 90% by weight %, about 70% to about 95% by weight, about 75% to about 80% by weight, about 75% to about 85% by weight, about 75% to about 90% by weight, about 75% to about 95% by weight, about 80% to about 85% by weight, about 80% to about 90% by weight, about 80% to about 95% by weight, about 85% to about 90% by weight, about 85% to about 95% by weight, or about 90% to about 95% by weight of insoluble sulfur.

[0144] In some embodiments, the composition comprises about 80% by weight insoluble sulfur. In some embodiments, the composition comprises about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 85%, about 90%, or about 95% by weight insoluble sulfur.

[0145] In some embodiments, the insoluble sulfur has an average primary particle size of about 3 μm to about 50 μm. In some embodiments, the insoluble sulfur has an average primary particle size of about 0.5 μm to about 1 μm, about 0.5 μm to about 3 μm, about 0.5 μm to about 5 μm, about 0.5 μm to about 7 μm, about 0.5 μm to about 10 μm, about 0.5 μm to about 25 μm, about 0.5 μm to about 50 μm, about 0.5 μm to about 100 μm, about 0.5 μm to about 150 μm, about 1 μm to about 3 μm, about 1 μm to about 5 μm, about 1 μm to about 7 μm, about 1 μm to about 10 μm, about 1 μm to about 25 μm, about 1 μm to about 50 μm, about 1 μm to about 100 μm, about 1 μm to about 150 μm, about 1 μm to about 3 μm, about 1 μm to about 5 μm, about 1 μm to about 7 μm, about 1 μm to about 10 μm, about 10 μm to about 25 μm, about 3 μm to about 50 μm, about 3 μm to about 100 μm, about 3 μm to about 150 μm, about 5 μm to about 7 μm, about 5 μm to about 10 μm, about 5 μm to about 25 μm, about 5 μm to about 50 μm, about 5 μm to about 100 μm, about 5 μm to about 150 μm, about 7 μm to about 10 μm, about 7 μm to about 25 μm, about 7 μm to about 50 μm, about 7 μm to about 100 μm, about 7 μm to about 150 μm, about 10 μm to about 25 μm, about 10 μm to about 50 μm, about 50 μm to about 100 μm, about 50 μm to about 150 μm, about 50 μm to about 100 μm, about 50 μm to about 150 μm, or about 100 μm to about 150 μm.

[0146] In some embodiments, the insoluble sulfur has an average primary particle size of about 10 μm. In some embodiments, the insoluble sulfur has an average primary particle size of about 50 μm. In some embodiments, the insoluble sulfur has an average primary particle size of about 150 μm, about 125 μm, about 100 μm, about 75 μm, about 25 μm, about 15 μm, about 7.5 μm, about 5 μm, about 2.5 μm, about 1 μm, or about 0.5 μm.

[0147] In some embodiments, the insoluble sulfur has an average primary particle size of 10 μm ± 5 μm. In some embodiments, the insoluble sulfur has an average primary particle size of 50 μm ± 15 μm. In some embodiments, the insoluble sulfur has an average primary particle size of 100 μm ± 10 μm, 75 μm ± 5 μm, 25 μm ± 2.5 μm, 5 μm ± 2.5 μm, or 2 μm ± 0.5 μm.

[0148] V.Processing oil

[0149] The compositions disclosed herein include a process oil.As used herein, the term "process oil" refers to any oil that can be used as a carrier (eg, as a carrier for insoluble sulfur).

[0150] In some embodiments, the process oil is a mineral oil. In some embodiments, the mineral oil is a paraffinic oil, a naphthenic oil, an aromatic oil, or a combination thereof.

[0151] As used herein, the term "paraffinic oil" refers to an oil comprising straight-chain or branched-chain hydrocarbons.

[0152] As used herein, the term "naphthenic oil" refers to an oil comprising hydrocarbons containing saturated rings. In some embodiments, the naphthenic oil comprises hydrocarbons having the following structure:

[0153]

[0154] Where n is a positive integer.

[0155] As used herein, the term "aromatic oil" refers to an oil that contains compounds containing aromatic rings. In some embodiments, the aromatic oil comprises a compound having the following structure:

[0156]

[0157] Where n is a positive integer.

[0158] In some embodiments, process oil comprises naturally derived oil or its hydrogenated derivative.As used herein, term " naturally derived oil " refers to any oil that can be derived from natural and non-petroleum source (such as plant).In some embodiments, naturally derived oil is soybean oil, vegetable oil, orange oil, low-methylene rapeseed oil, castor oil, palm oil, sunflower seed oil or its combination.As used herein, term " hydrogenated derivative " refers to the derivative of the oil that has been for example treated with hydrogen and catalyst to saturate some or all of the double bonds present in one or more compounds constituting oil.

[0159] In some embodiments, the process oil comprises pyrolysis oil. As used herein, the term "pyrolysis oil" refers to an oil obtained by heating dry biomass (including but not limited to wood and algae) in the absence of oxygen. In some embodiments, pyrolysis oil is prepared according to ASTM D7544-12.

[0160] In some embodiments, the composition comprises from about 5% to about 50% by weight process oil. In some embodiments, the composition comprises from about 5% to about 10% by weight, from about 5% to about 15% by weight, from about 5% to about 20% by weight, from about 5% to about 25% by weight, from about 5% to about 30% by weight, from about 5% to about 35% by weight, from about 5% to about 40% by weight, from about 5% to about 45% by weight, from about 10% to about 15% by weight, from about 10% to about 20% by weight, from about 10% to about 25% by weight, from about 10% to about 30% by weight, from about 10% to about 35% by weight, from about 10% to about 40% by weight, from about 10% to about 45% by weight, from about 10% to about 50% by weight, from about 15% to about 20% by weight, from about 15% to about 25% by weight, from about 15% to about 30% by weight, from about 15% to about 35% by weight, from about 15% to about 40% by weight, from about 15% to about 45% by weight %, about 15% to about 50% by weight, about 20% to about 25% by weight, about 20% to about 30% by weight, about 20% to about 35% by weight, about 20% to about 40% by weight, about 20% to about 45% by weight, about 20% to about 50% by weight, about 25% to about 30% by weight, about 25% to about 35% by weight, about 25% to about 40% by weight, about 25% to about 45% by weight, about % to about 40 wt %, about 30 wt % to about 45 wt %, about 30 wt % to about 50 wt %, about 35 wt % to about 40 wt %, about 35 wt % to about 45 wt %, about 35 wt % to about 50 wt %, about 40 wt % to about 45 wt %, about 40 wt % to about 50 wt %, or about 45 wt % to about 50 wt % process oil.

[0161] In some embodiments, the composition comprises about 20% by weight of process oil. In some embodiments, the composition comprises about 5% by weight, about 10% by weight, about 15% by weight, about 25% by weight, about 30% by weight, about 35% by weight, about 40% by weight, about 45% by weight, or about 50% by weight of process oil.

[0162] VI. Stabilizer

[0163] 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 the insoluble sulfur to directly affect the thermal stability or storage stability of the product. The material, chemical, or combination thereof can be added at any stage of the insoluble sulfur production process.

[0164] 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 carbocation. In some embodiments, the stabilizer is α-methylstyrene, pinene, terpene, ammonium sulfate, sodium ethylxanthate, camphene, benzothiazole, or limonene. In some embodiments, the stabilizer is pine tar, turpentine, pine oil, or rosin acid. In some embodiments, the stabilizer is dodecene, tetradecene, octadecene, indene, vinyltoluene, allylbenzene, dicyclopentadiene, styrene, chloroprene, divinylbenzene, 1-vinyl-3-cyclohexane, 2,5-dichlorostyrene, p-vinylbiphenyl, or p-methylstyrene.

[0165] In some embodiments, the composition comprises from about 0.01% to about 1% by weight of a stabilizer. In some embodiments, the composition comprises from about 0.01% to about 0.05% by weight, from about 0.01% to about 0.1% by weight, from about 0.01% to about 0.25% by weight, from about 0.01% to about 0.5% by weight, from about 0.01% to about 0.75% by weight, from about 0.05% to about 0.1% by weight, from about 0.05% to about 0.25% by weight, from about 0.05% to about 0.5% by weight, from about 0.05% to about 0.75% by weight, from about 0.05% to about 0.1% by weight, from about 0.05% to about 0.25% by weight, from about 0.05% to about 0.5% by weight, from about 0.05% to about 0.75% by weight, from about 0.05% to about 0.1% by weight. % to about 0.75 wt %, about 0.1 wt % to about 1 wt %, about 0.25 wt % to about 0.5 wt %, about 0.25 wt % to about 0.75 wt %, about 0.25 wt % to about 1 wt %, about 0.5 wt % to about 0.75 wt %, about 0.5 wt % to about 1 wt %, or about 0.75 wt % to about 1 wt % of a stabilizer.

[0166] In some embodiments, the composition comprises about 0.5% by weight of a stabilizer. In some embodiments, the composition comprises about 0.01%, about 0.05%, about 0.1%, about 0.25%, about 0.75%, or about 1% by weight of a stabilizer.

[0167] VII. Properties of the Composition

[0168] In some embodiments, the compositions disclosed herein have a Carr's Index of less than 28%. The Carr's Index is a measure of the flowability of a powder. See Example 2. In some embodiments, the compositions have a Carr's Index of less than 28%. In some embodiments, the compositions have a Carr's 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%.

[0169] In some embodiments, the composition has a Hausner Ratio of less than 1.40. The Hausner Ratio is a measure of the flowability of a powder. 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.

[0170] VIII. Vulcanized Elastomer Products

[0171] The present disclosure also provides a vulcanized elastomeric article comprising the composition described herein.The term "vulcanized elastomeric article" refers to an article prepared by forming a composition comprising an elastomer into a specific shape and vulcanizing the composition to provide the article.

[0172] As used herein, the term "vulcanization" refers to a process in which crosslinks are formed between elastomers to achieve changes in the material properties of the elastomer. In particular, vulcanization typically increases the rigidity and durability of the elastomer. Vulcanization is carried out at room temperature or elevated temperature, depending on the properties of the elastomer(s), filler(s), and rubber chemicals(s) used. The term "curing" is also used in the art to describe this process.

[0173] As used herein, the term "elastomer" refers to a polymer with viscoelastic properties (i.e., viscosity and elasticity), typically having 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 known as curing or vulcanization. Rubber is a type of elastomer. The non-restrictive type of rubber includes natural rubber (NR), synthetic rubber, and blends thereof. As used herein, the term "natural rubber" refers to the naturally occurring elastomer that can be obtained from Hevea brasiliensis. The non-restrictive type of synthetic rubber includes unsaturated rubber, saturated rubber, rubber (FKM), silicone rubber (Q), and blends thereof, with fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain. The limiting examples of unsaturated rubber comprises polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene-butadiene rubber (SBR), acrylonitrile-butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene monomer rubber (EPDM) and blend thereof. Cyclization and cross-linking reaction occur in these unsaturated rubbers, cause aging parts to harden. Along with the generation of oxidation, these vulcanized rubbers harden and finally become brittle products. When vulcanized rubber is used for applications such as vehicle tire sidewalls, partial oxidation can cause performance loss. 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), polychloromethyl ethylene oxide (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), rubbers with fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q), and blends thereof.

[0174] In some embodiments, the natural rubber comprises rubber derived from an alternative rubber plant. As used herein, the term "natural rubber comprises rubber derived from an alternative rubber plant" refers to naturally occurring elastomers that can be obtained from "non-Hevea brasiliensis" sources. In some embodiments, the alternative rubber plant is Guayule (Guayule) or Rubber Grass (Russian Taraxacum).

[0175] In some embodiments, the one or more elastomers further comprise recycled rubber.As used herein, the term "recycled rubber" refers to an elastomer that has been recovered from waste materials, such as scrap tires.

[0176] The present disclosure also provides vulcanized elastomeric articles prepared using the compositions described herein.

[0177] In some embodiments, the vulcanized elastomeric article is a tire. In some embodiments, the tire is a passenger car tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, a bulldozer tire, an aircraft tire, or a racing tire.

[0178] In some embodiments, the vulcanized elastomeric article is a component of a tire. In some embodiments, the component is a bead, a belt, a carcass ply, an inner liner, a sidewall, an undertread, or a tread.

[0179] In some embodiments, the vulcanized elastomeric article is a rubber overshoe, a weatherstrip, an acoustic panel, an air spring, a bellows, a membrane, a tactile sensor, a crash pad, a hose, a conveyor belt, or a flooring.

[0180] method

[0181] The present disclosure also provides a method for preparing a vulcanized elastomeric article, the method comprising:

[0182] (a) mixing a composition as described herein with at least one elastomer to form a mixture;

[0183] (b) forming the mixture of (a) into a shaped shape; and

[0184] (c) vulcanizing the formed shape,

[0185] To provide vulcanized elastomer products.

[0186] In some embodiments, vulcanization is conducted at an average temperature of about 140°C to about 160°C. In some embodiments, vulcanization is carried out at an average temperature of about 80°C to about 100°C, about 80°C to about 120°C, about 80°C to about 140°C, about 80°C to about 160°C, about 80°C to about 180°C, about 80°C to about 200°C, about 100°C to about 120°C, about 100°C to about 140°C, about 100°C to about 160°C, about 100°C to about 180°C, about 100°C to about 200°C, about 120°C to about 140°C, about 120°C to about 160°C, about 120°C to about 180°C, about 120°C to about 200°C, about 140°C to about 180°C, about 140°C to about 200°C, about 160°C to about 180°C, about 160°C to about 200°C, or about 180°C to about 200°C.

[0187] In some embodiments, vulcanization is carried out at an average temperature of about 150° C. In some embodiments, vulcanization is carried out 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.

[0188] Reagent test kit

[0189] The present disclosure also provides a kit comprising a composition as described herein, the composition being packaged in, for example, a container in a manner that promotes the composition to be used in practicing the process and / or method of the present disclosure. In some embodiments, the kit comprises a composition as described herein and instructions for using the composition in a vulcanizable elastomeric composition. In some embodiments, the kit comprises a composition as described herein and instructions for preparing a vulcanized elastomeric article using the composition. The composition can be packaged in any suitable container, such as a sealed bottle or container, with a label affixed to the container or included in a kit describing the composition and its proper use.

[0190] IX. Sulfur masterbatch

[0191] The present disclosure also provides a sulfur masterbatch comprising the composition described herein and at least one elastomer.

[0192] In some embodiments, 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 rubber (NBR), chloroprene rubber (CR), ethylene propylene diene monomer rubber (EPDM), acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyl ethylene oxide (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), rubber having fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q), or a combination thereof.

[0193] In some embodiments, a masterbatch comprises from about 60% to about 90% by weight of a composition described herein. In some embodiments, the masterbatch comprises from about 40% to about 50% by weight, from about 40% to about 60% by weight, from about 40% to about 70% by weight, from about 40% to about 80% by weight, from about 40% to about 90% by weight, from about 40% to about 95% by weight, from about 50% to about 60% by weight, from about 50% to about 70% by weight, from about 50% to about 80% by weight, from about 50% to about 90% by weight, from about 50% to about 95% by weight, from about 60% to about 70% by weight, from about 60% to about 80% by weight, from about 60% to about 90% by weight, from about 60% to about 95% by weight, from about 70% to about 80% by weight, from about 70% to about 90% by weight, from about 70% to about 95% by weight, from about 80% to about 90% by weight, from about 80% to about 95% by weight, or from about 90% to about 95% by weight of a composition described herein.

[0194] In some embodiments, the masterbatch comprises about 80% by weight of a composition as described herein. In some embodiments, the masterbatch comprises about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 85%, about 90%, or about 95% by weight of a composition as described herein.

[0195] In some embodiments, the masterbatch comprises from about 10% to about 40% by weight of the 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 %, about 15% to about 50% by weight, about 20% to about 25% by weight, about 20% to about 30% by weight, about 20% to about 35% by weight, about 20% to about 40% by weight, about 20% to about 45% by weight, about 20% to about 50% by weight, about 25% to about 30% by weight, about 25% to about 35% by weight, about 25% to about 40% by weight, about 25% to about 45% by weight, about 2 % to about 40 wt %, about 30 wt % to about 45 wt %, about 30 wt % to about 50 wt %, about 35 wt % to about 40 wt %, about 35 wt % to about 45 wt %, about 35 wt % to about 50 wt %, about 40 wt % to about 45 wt %, about 40 wt % to about 50 wt %, or about 45 wt % to about 50 wt % elastomer.

[0196] In some embodiments, the masterbatch comprises about 20% by weight of the elastomer. In some embodiments, the masterbatch comprises about 5%, about 10%, about 15%, about 25%, about 30%, about 35%, about 40%, about 45%, or about 50% by weight of the elastomer.

[0197] X. Specific Implementations

[0198] The present disclosure provides the following specific embodiments.

[0199] Embodiment 1. A composition comprising from about 50 wt% to about 95 wt% insoluble sulfur, from about 5 wt% to about 50 wt% process oil, and from about 0.1 wt% to about 3 wt% polymer, wherein the polymer is an ethylene propylene diene monomer (EPDM) polymer, a styrene isoprene styrene (SIS) polymer, an oxygen-containing polymer, a polyolefin plastomer or elastomer, or an isoprene polymer.

[0200] Embodiment II. The composition of Embodiment I, wherein the polymer is an EPDM polymer.

[0201] Embodiment III. The composition of Embodiment II, wherein the EPDM polymer has an ethylene content of about 55 wt% to about 85 wt%.

[0202] Embodiment IV. The composition of Embodiment III, wherein the EPDM polymer has an ethylene content of about 70 wt%.

[0203] Embodiment V. The composition of any of Embodiments II-IV, wherein the EPDM polymer has an ethylidene norbornene content of from about 0 wt % to about 10 wt %.

[0204] Embodiment VI. The composition of Embodiment V, wherein the EPDM polymer has an ethylidene norbornene content of about 4.9 wt%.

[0205] Embodiment VII. The composition of any one of Embodiments II-VI, wherein the EPDM polymer has a Mooney viscosity of about 15 ML (1+4) to about 90 ML (1+4) when measured according to ASTM D1646.

[0206] Embodiment VIII. The composition of Embodiment VII, wherein the EPDM polymer has a Mooney viscosity of about 25 ML (1+4) when measured according to the ASTM D1646 standard.

[0207] Embodiment IX. The composition of Embodiment I, wherein the polymer is a SIS polymer.

[0208] Embodiment X. The composition of Embodiment IX, wherein the SIS polymer has a styrene content of from about 5 wt% to about 20 wt%.

[0209] Embodiment XI. The composition of Embodiment X, wherein the SIS polymer has a styrene content of about 14 wt%.

[0210] Embodiment XII. The composition of any of Embodiments IX-XI, wherein the structure of the SIS polymer is linear, radial, branched, pendant, dendritic, or a combination thereof.

[0211] Embodiment XIII. The composition of embodiment XII, wherein the structure of the SIS polymer is linear.

[0212] Embodiment XIV. The composition of embodiment XII, wherein the structure of the SIS polymer is a combination of linear and radial.

[0213] Embodiment XV. A composition according to Embodiment I, wherein the polymer is an oxygen-containing polymer.

[0214] Embodiment XVI. The composition of embodiment XV, wherein the oxygen-containing polymer comprises polyethylene glycol, polypropylene glycol, or a combination thereof.

[0215] Embodiment XVII. The composition of embodiment XVI, wherein the ethylene oxide content of the oxygen-containing polymer is from about 60 wt % to about 90 wt %.

[0216] Embodiment XVIII. The composition of Embodiment XV, wherein the oxygen-containing polymer comprises poly(ethylene-co-acrylic acid).

[0217] Embodiment XIX. The composition of Embodiment XV, wherein the oxygen-containing polymer comprises dicarboxyl-terminated polybutadiene.

[0218] Embodiment XX. The composition of any of Embodiments XV-XIX, wherein the oxygen-containing polymer has a water content of less than 0.2 wt%.

[0219] Embodiment XXI. The composition of Embodiment I, wherein the polymer is a polyolefin plastomer or elastomer.

[0220] Embodiment XXII. The composition of Embodiment XXI, wherein the polyolefin plastomer or elastomer has a melt index of about 500 g / 10 min to about 1300 g / 10 min as measured by ASTM D1238.

[0221] Embodiment XXIII. The composition of Embodiment XXI or XXII, wherein the polyolefin plastomer or elastomer has a density of about 0.850 g / cc to about 0.950 g / cc as measured by ASTM D792.

[0222] Embodiment XXIV. The composition of Embodiment I, wherein the polymer is an isoprene polymer.

[0223] 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.

[0224] Embodiment XXVI. The composition of embodiment XXV, wherein the stabilizer is an ionic liquid.

[0225] Embodiment XXVII. The composition of Embodiment XXV, wherein the stabilizer is an unsaturated olefin.

[0226] Embodiment XXVIII. The composition of embodiment XXV, wherein the stabilizer is a carbocation.

[0227] Embodiment XXIX. The composition of embodiment XXV, wherein the stabilizer is α-methylstyrene, pinene, a terpene, ammonium sulfate, sodium ethylxanthate, camphene, benzothiazole, or limonene.

[0228] Embodiment XXX. The composition of any one of Embodiments I-XXIX, wherein the composition comprises about 80% by weight insoluble sulfur.

[0229] Embodiment XXXI. The composition of any of Embodiments I-XXX, wherein the insoluble sulfur has an average primary particle size of about 3 μm to about 65 μm.

[0230] Embodiment XXXII. The composition of Embodiment XXXI, wherein the insoluble sulfur has an average primary particle size of 10 μm ± 5 μm.

[0231] Embodiment XXXIII. The composition of Embodiment XXXI, wherein the insoluble sulfur has an average primary particle size of 50 μm ± 15 μm.

[0232] Embodiment XXXIV. The composition of any one of Embodiments I-XXXIII, wherein the composition comprises about 19.2 wt% process oil.

[0233] Embodiment XXXV. The composition of any one of Embodiments I-XXXIV, wherein the process oil comprises mineral oil, naturally derived oil, pyrolysis oil, or a combination thereof.

[0234] Embodiment XXXVI. The composition of Embodiment XXXV, wherein the process oil comprises mineral oil.

[0235] Embodiment XXXVII. The composition of embodiment XXXVI, wherein the mineral oil is a paraffinic oil, a naphthenic oil, an aromatic oil, or a combination thereof.

[0236] Embodiment XXXVIII. The composition of embodiment XXXVII, wherein the mineral oil is a naphthenic oil.

[0237] Embodiment XXXIX. The composition of Embodiment XXXV, wherein the process oil comprises a naturally derived oil or a hydrogenated derivative thereof.

[0238] Embodiment XL. The composition of embodiment XXXIX, wherein the naturally derived oil is soybean oil, vegetable oil, orange oil, low-methylene rapeseed oil, castor oil, palm oil, sunflower oil, or a combination thereof.

[0239] Embodiment XLI. The composition of any one of Embodiments I-XL, wherein the composition comprises about 0.8 wt% polymer.

[0240] Embodiment XLII. The composition of any one of Embodiments I-XLI, wherein the composition has a Carr's Index of less than 28%.

[0241] Embodiment XLIII. The composition of any one of Embodiments I-XLII, wherein the composition has a Hausner Ratio of less than 1.40.

[0242] Embodiment XLIV. A vulcanized elastomeric article comprising the composition of any one of Embodiments I-XLII.

[0243] Embodiment XLV. A vulcanized elastomeric article prepared using the composition of any one of Embodiments I-XLII.

[0244] Embodiment XLVI. The vulcanized elastomeric article of Embodiment XLIV or XLV, wherein the vulcanized elastomeric article is a tire.

[0245] Embodiment XLVII. A method for preparing a vulcanized elastomeric article, the method comprising:

[0246] (a) mixing the composition according to any one of Embodiments I to XLIII with at least one elastomer to form a mixture;

[0247] (b) forming the mixture of (a) into a shaped shape; and

[0248] (c) Vulcanizing the formed shape

[0249] To provide vulcanized elastomer products.

[0250] Embodiment XLVIII. A kit comprising the composition according to any one of Embodiments I to XLIII and instructions for using the composition in a vulcanizable elastomeric composition.

[0251] 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.

[0252] Embodiment L. A sulfur masterbatch comprising the composition of any one of Embodiments I-XLIII and at least one elastomer.

[0253] Embodiment LI. The masterbatch according to embodiment L, 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 rubber (NBR), chloroprene rubber (CR), ethylene propylene diene monomer rubber (EPDM), acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyl ethylene oxide (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), rubber having fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q), or a combination thereof.

[0254] Embodiment LII. The masterbatch of Embodiment LI, wherein the masterbatch comprises from about 60% to about 90% by weight of the composition of any one of Embodiments I-XLIII.

[0255] Embodiment LIII. The masterbatch of Embodiment LII, wherein the masterbatch comprises about 80% by weight of the composition of any one of Embodiments I-XLIII.

[0256] Embodiment LIV. The masterbatch of any of Embodiments L-LIII, wherein the masterbatch comprises from about 10% to about 40% by weight of the elastomer.

[0257] Embodiment LV. The masterbatch of Embodiment LIV, wherein the masterbatch comprises about 20% by weight of the elastomer.

[0258] The present disclosure provides the following specific embodiments.

[0259] Embodiment 1. A composition comprising from about 50 wt% to about 95 wt% insoluble sulfur, from about 5 wt% to about 50 wt% 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 monomer (EPDM) polymer, a styrene isoprene styrene (SIS) polymer, an oxygen-containing polymer, a polyolefin plastomer or elastomer, or an isoprene polymer.

[0260] Embodiment 2. The composition of embodiment 1, wherein at least one of the one or more polymers is an EPDM polymer.

[0261] Embodiment 3. The composition of embodiment 2, wherein the EPDM polymer has an ethylene content of about 55 wt% to about 85 wt%.

[0262] Embodiment 4. The composition of embodiment 3, wherein the EPDM polymer has an ethylene content of about 70% by weight.

[0263] Embodiment 5. The composition of any of Embodiments 2-4, wherein the EPDM polymer has an ethylidene norbornene content of from about 0 wt% to about 10 wt%.

[0264] Embodiment 6. The composition of embodiment 5, wherein the EPDM polymer has an ethylidene norbornene content of about 4.9 wt%.

[0265] Embodiment 7. The composition of any one of Embodiments 2-6, wherein the EPDM polymer has a Mooney viscosity of about 15 ML (1+4) to about 90 ML (1+4) when measured according to ASTM D1646.

[0266] Embodiment 8. The composition of embodiment 7, wherein the EPDM polymer has a Mooney viscosity of about 25 ML (1+4) when measured according to the ASTM D1646 standard.

[0267] Embodiment 9. The composition of any one of embodiments 1-8, wherein at least one of the one or more polymers is a SIS polymer.

[0268] Embodiment 10. The composition of embodiment 9, wherein the SIS polymer has a styrene content of about 5 wt% to about 20 wt%.

[0269] Embodiment 11. The composition of embodiment 10, wherein the SIS polymer has a styrene content of about 14 wt%.

[0270] 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.

[0271] Embodiment 13. The composition of embodiment 12, wherein the structure of the SIS polymer is linear.

[0272] Embodiment 14. The composition of embodiment 12, wherein the structure of the SIS polymer is a combination of linear and radial.

[0273] Embodiment 15. The composition of any one of Embodiments 1-14, wherein at least one of the one or more polymers is an oxygen-containing polymer.

[0274] Embodiment 16. The composition of embodiment 15, wherein the oxygen-containing polymer comprises polyethylene glycol, polypropylene glycol, or a combination thereof.

[0275] Embodiment 17. The composition of embodiment 16, wherein the ethylene oxide content of the oxygen-containing polymer is from about 60 wt% to about 90 wt%.

[0276] Embodiment 18. The composition of embodiment 15, wherein the oxygen-containing polymer comprises poly(ethylene-co-acrylic acid).

[0277] Embodiment 19. The composition of embodiment 15, wherein the oxygen-containing polymer comprises dicarboxyl-terminated polybutadiene.

[0278] Embodiment 20. The composition of any one of embodiments 15-19, wherein the oxygen-containing polymer has a water content of less than 0.2 wt%.

[0279] Embodiment 21. The composition of any of Embodiments 1-20, wherein at least one of the one or more polymers is a polyolefin plastomer or elastomer.

[0280] Embodiment 22. The composition of embodiment 21, wherein the polyolefin plastomer or elastomer has a melt index of about 500 g / 10 min to about 1300 g / 10 min as measured by ASTM D1238.

[0281] Embodiment 23. The composition of embodiment 21 or 22, wherein the polyolefin plastomer or elastomer has a density of about 0.850 g / cc to about 0.950 g / cc as measured by ASTM D792.

[0282] 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.

[0283] 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.

[0284] Embodiment 26. The composition of embodiment 25, wherein the stabilizer is an ionic liquid.

[0285] Embodiment 27. The composition of embodiment 25, wherein the stabilizer is an unsaturated olefin.

[0286] Embodiment 28. The composition of embodiment 25, wherein the stabilizer is a carbocation.

[0287] Embodiment 29. The composition of embodiment 25, wherein the stabilizer is α-methylstyrene, pinene, a terpene, ammonium sulfate, sodium ethylxanthate, camphene, benzothiazole, or limonene.

[0288] Embodiment 30. The composition of any one of Embodiments 1-29, wherein the composition comprises about 80% by weight insoluble sulfur.

[0289] Embodiment 31. The composition of any of Embodiments 1-30, wherein the insoluble sulfur has an average primary particle size of about 3 μm to about 65 μm.

[0290] Embodiment 32. The composition of embodiment 31, wherein the insoluble sulfur has an average primary particle size of 10 μm ± 5 μm.

[0291] Embodiment 33. The composition of embodiment 31, wherein the insoluble sulfur has an average primary particle size of 50 μm ± 15 μm.

[0292] Embodiment 34. The composition of any one of Embodiments 1-33, wherein the composition comprises about 19.2 wt% process oil.

[0293] Embodiment 35. The composition of any one of Embodiments 1-33, wherein the composition comprises about 10% by weight of process oil.

[0294] Embodiment 36. The composition of any one of Embodiments 1-35, wherein the process oil comprises mineral oil, naturally derived oil, pyrolysis oil, or a combination thereof.

[0295] Embodiment 37. The composition of embodiment 36, wherein the process oil comprises mineral oil.

[0296] Embodiment 38. The composition of embodiment 37, wherein the mineral oil is a paraffinic oil, a naphthenic oil, an aromatic oil, or a combination thereof.

[0297] Embodiment 39. The composition of embodiment 38, wherein the mineral oil is a naphthenic oil.

[0298] Embodiment 40. The composition of embodiment 36, wherein the process oil comprises a naturally derived oil or a hydrogenated derivative thereof.

[0299] Embodiment 41. The composition of embodiment 40, wherein the naturally derived oil is soybean oil, vegetable oil, orange oil, low-methylene rapeseed oil, castor oil, palm oil, sunflower oil, or a combination thereof.

[0300] Embodiment 42. The composition of any one of Embodiments 1-41, wherein the composition comprises about 0.8% by weight of the one or more polymers.

[0301] 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% process oil, and from about 0.4 wt% to about 1 wt% polyolefin plastomer or elastomer.

[0302] 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% process oil, and from about 0.4 wt% to about 1 wt% EPDM polymer.

[0303] 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% process oil, from about 0.4 wt% to about 1 wt% polyolefin plastomer or elastomer, and from about 0.01 wt% to about 0.07 wt% EPDM polymer.

[0304] 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% process oil, from about 0.01 wt% to about 0.07 wt% polyolefin plastomer or elastomer, and from about 0.4 wt% to about 1 wt% EPDM polymer.

[0305] Embodiment 47. The composition of any one of embodiments 43, 45, or 46, wherein the polyolefin plastomer or elastomer has a viscosity of about 0.862 g / cm 3 density and an ethylene content of approximately 16.

[0306] Embodiment 48. The composition of embodiment 47, wherein the polyolefin plastomer or elastomer is VISTAMAXX TM High performance polymer 6102.

[0307] 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 norbornene (ENB) content of about 4.9.

[0308] Embodiment 50. The composition of embodiment 49, wherein the EPDM polymer is NORDEL TM IP4725P.

[0309] Embodiment 51. The composition of any one of embodiments 1-50, wherein the composition has a Carr's Index of less than 28%.

[0310] Embodiment 52. The composition of any one of Embodiments 1-51, wherein the composition has a Hausner Ratio of less than 1.40.

[0311] Embodiment 53. A vulcanized elastomeric article comprising the composition of any one of Embodiments 1-52.

[0312] Embodiment 54. A vulcanized elastomeric article prepared using the composition of any one of Embodiments 1-52.

[0313] Embodiment 55. The vulcanized elastomeric article of Embodiment 53 or 54, wherein the vulcanized elastomeric article is a tire.

[0314] Embodiment 56. A method for preparing a vulcanized elastomeric article, the method comprising:

[0315] (a) mixing the composition according to any one of embodiments 1-52 with at least one elastomer to form a mixture;

[0316] (b) forming the mixture of (a) into a shaped shape; and

[0317] (c) Vulcanizing the formed shape

[0318] To provide vulcanized elastomer products.

[0319] 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.

[0320] 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.

[0321] Embodiment 59. A sulfur masterbatch comprising the composition of any of Embodiments 1-52 and at least one elastomer.

[0322] Embodiment 60. The masterbatch of embodiment 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 rubber (NBR), chloroprene rubber (CR), ethylene propylene diene monomer rubber (EPDM), acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyl ethylene oxide (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), rubber having fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q), or a combination thereof.

[0323] Embodiment 61. The masterbatch of embodiment 60, wherein the masterbatch comprises from about 60% to about 90% by weight of the composition of any one of embodiments 1-52.

[0324] Embodiment 62. The masterbatch of embodiment 61, wherein the masterbatch comprises about 80% by weight of the composition of any one of embodiments 1-52.

[0325] Embodiment 63. The masterbatch of any of Embodiments 59-62, wherein the masterbatch comprises from about 10% to about 40% by weight of the elastomer.

[0326] Embodiment 64. The masterbatch of Embodiment 63, wherein the masterbatch comprises about 20% by weight of the elastomer.

[0327] Example

[0328] Example 1

[0329] Preparation of insoluble sulfur compositions

[0330] A 2L plastic container with 5 steel ball bearings was filled with approximately 500g of dry insoluble sulfur. Independent process oil (Hyprene P300N paraffin process oil or Hyprene 100 naphthenic process oil) or process oil (Hyprene 100 naphthenic process oil) / polymer mixture was preheated to 70°C and poured into the insoluble sulfur to achieve a final concentration of 20% by weight process oil in the mixture. The container was quickly capped and loaded into a BioEngineering Inversina 2L tumbling mixer. The mixture was tumbled at 60rpm for 15 minutes, stopped, and any part of the mixture that adhered to the container wall or top was scraped off with a spatula. The container was resealed and reinstalled on the Inversina mixer for another 45 minutes at 60rpm. The mixture was taken out from the mixer and used for subsequent characterization.

[0331] Example 2

[0332] Measurement of Carr's Index and Hausner Ratio of Insoluble Sulfur Composition

[0333] The Carr Index of the insoluble sulfur composition prepared using the procedure described in Example 1 is measured using the ASTM standard test method for characterizing bulk materials by the Carr Index, for example, as described in ASTM D6393-14 published by ASTM International, which is incorporated herein by reference. The Carr Index is defined as follows:

[0334] Carr index = 100*(ρPBD–ρUBD) / ρPBD

[0335] Where ρPBD is the packed bulk density and ρUBD is the unpacked bulk density. A lower Carr's Index indicates better powder flow. The Carr's Index for various insoluble sulfur compositions containing different polymers or no polymer is plotted on Figure 1 and are listed in Table 17.

[0336] The Hausner ratio also describes powder flow by expressing the ratio between filled and unfilled bulk density and is defined as follows:

[0337] Hausner ratio = ρPBD / ρUBD

[0338] Where ρPBD is the packed bulk density and ρUBD is the unpacked bulk density. A lower Hausner ratio indicates better powder flow. The Hausner ratios of various insoluble sulfur compositions containing different polymers or no polymer, prepared using the procedure described in Example 1, are plotted on Figure 2 and are listed in Table 17.

[0339] Table 17

[0340]

[0341]

[0342]

[0343] 1 OT10 indicates that the sample contains approximately 10 wt% process oil.

[0344] 2 OT20 indicates that the sample contains approximately 20 wt% process oil.

[0345] Now that the methods, compounds, and compositions herein have been fully described, it will be understood by those skilled in the art that a wide and equivalent range of conditions, formulations, and other parameters may be employed 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 herein by reference in their entirety.

Claims

1. A composition comprising from about 50 wt % to about 95 wt % insoluble sulfur, from about 5 wt % to about 50 wt % 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 monomer (EPDM) polymer, a styrene isoprene styrene (SIS) polymer, an oxygen-containing 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 about 55 wt% to about 85 wt%.

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

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

6. The composition of claim 5, wherein the EPDM polymer has an ethylidene norbornene 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 about 15 ML (1+4) to about 90 ML (1+4) when measured according to ASTM D1646 standard.

8. The composition of claim 7, wherein the EPDM polymer has a Mooney viscosity of about 25 ML (1+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 a SIS polymer.

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

11. The composition of claim 10, wherein the SIS polymer has a styrene content of 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 types.

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

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

17. The composition of claim 16, wherein the ethylene oxide content of the oxygen-containing polymer is from about 60% to about 90% by weight.

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

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

20. The composition of any one of claims 15-19, wherein the oxygen-containing polymer has a water content of 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 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 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% to about 1% by weight 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 an unsaturated olefin.

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

29. The composition of claim 25, wherein the stabilizer is alpha-methylstyrene, pinene, a terpene, ammonium sulfate, sodium ethylxanthate, camphene, benzothiazole, or limonene.

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

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

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

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

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

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

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

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

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

39. The composition of claim 38, wherein the mineral oil is a 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, low-methylene rapeseed 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% by weight of the one or more polymers.

43. The composition of claim 1, wherein the composition comprises from about 80% to about 90% by weight insoluble sulfur, from about 10% to about 20% by weight process oil, and from about 0.4% to about 1% by weight 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% process oil, and from about 0.4 wt% to about 1 wt% 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% process oil, from about 0.4 wt% to about 1 wt% polyolefin plastomer or elastomer, and from about 0.01 wt% to about 0.07 wt% 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% process oil, from about 0.01 wt% to about 0.07 wt% polyolefin plastomer or elastomer, and from about 0.4 wt% to about 1 wt% EPDM polymer.

47. according to the composition described in any one of claim 43,45 or 46, wherein said polyolefin plastomer or elastomer has about 0.862g / cm 3 density and an ethylene content of approximately 16.

48. The composition of claim 47, wherein the polyolefin plastomer or elastomer is VISTAMAXX TM High 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 norbornene (ENB) content of about 4.

9.

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

51. The composition of any one of claims 1-50, wherein the composition has a Carr's 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 to 52.

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

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

56. A method for preparing a vulcanized elastomeric article, the method comprising: (a) mixing the composition according to any one of claims 1 to 52 with at least one elastomer to form a mixture; (b) forming the mixture of (a) into a shaped shape; as well as (c) Vulcanizing the formed shape To provide vulcanized elastomer products.

57. A kit comprising the composition of any one of claims 1 to 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 to 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 rubber (NBR), chloroprene rubber (CR), ethylene propylene diene monomer (EPDM), acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyl ethylene oxide (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), rubber having fluorine and fluoroalkyl or fluoroalkoxy 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% to about 90% by weight of the composition of any one of claims 1-52.

62. The masterbatch of claim 61 , wherein the masterbatch comprises about 80% by weight 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% to about 40% by weight of the elastomer.

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

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