Sulfur stabilizer for use in epoxy-functional and phospholipid-containing compositions for asphalt applications

Abstract

The present technology provides an asphalt additive comprising a phospholipid material, an epoxidized renewable oil or fat, and a sulfurized renewable oil stabilizer, wherein the epoxidized renewable oil or fat has an oxirane content of about 1.0% to about 15.0%, and the sulfurized renewable oil stabilizer has a polymer distribution having an oligomer content of about 2 weight percent (wt%) to about 80 wt%, optionally a polydispersity index (PDI) ranging from about 1.0 to about 5.0, and a sulfur content ranging from about 0.001 wt% to about 8 wt%. The present technology also provides uses of the asphalt additive in asphalt applications and methods for producing the same.

Description

[Technical Field]

[0001] (CROSS-REFERENCE TO RELATED APPLICATIONS) This application claims the benefit of U.S. Provisional Patent Application No. 63 / 382,331, filed November 4, 2022, which is incorporated herein by reference in its entirety.

[0002] The present technology relates to asphalt additives for use in asphalt applications. In particular, the present technology relates to asphalt additives including an epoxidized renewable oil or fat, a phospholipid material, and a sulfurized renewable oil stabilizer for use as a warm mix asphalt additive or to improve anti-stripping properties in asphalt applications, and methods of making and using the same. Summary of the Invention

[0003] In one aspect, the present technology provides an asphalt additive comprising a phospholipid material, an epoxidized renewable oil or fat having an oxirane content of about 1.0% to about 15.0%, and a sulfurized renewable oil stabilizer, the sulfurized renewable oil stabilizer having a polymer distribution with an oligomer content of 2 wt% to about 80 wt% and a sulfur content of about 0.001 wt% to about 8 wt%, based on the total weight of the sulfurized renewable oil stabilizer, and the sulfurized renewable oil stabilizer is a polymerized oil obtained by sulfurization. The sulfurized renewable oil stabilizer may further have a PDI of about 1.0 to about 5.0. For example, the asphalt additive may include a phospholipid material, an epoxidized renewable oil or fat having an oxirane content of from about 1.0% to about 15.0%, and a sulfurized renewable oil stabilizer, the sulfurized renewable oil stabilizer being a polymerized oil obtained by sulfurization, the polymer distribution having an oligomer content of from 2 wt.% to about 80 wt.%, a PDI in the range of from about 1.0 to about 5.0, and a sulfur content in the range of from about 0.001 wt.% to about 8 wt.%, based on the total weight of the sulfurized renewable oil stabilizer.

[0004] In one aspect, the present technology provides for the use of the asphalt additives described herein to reduce or prevent spalling in asphalt applications.

[0005] In another aspect, the present technology provides for the use of the asphalt additives described herein as compaction aids in asphalt applications.

[0006] In another aspect, the present technology provides for the use of the asphalt additives described herein as adhesion promoters in asphalt applications.

[0007] In yet another related aspect, the present technology provides the use of the asphalt additive described herein as a warm mix asphalt additive or a hot mix asphalt additive in asphalt applications. For example, the use of the asphalt additive is as a warm mix asphalt additive. In another example, the use of the asphalt additive is as a hot mix asphalt additive.

[0008] In another aspect, the present technology provides an asphalt binder comprising bitumen and any of the asphalt additives described herein.

[0009] In yet another aspect, the present technology provides an asphalt concrete comprising about 0.25 wt % to about 8.0 wt % (based on the total weight of the asphalt concrete) of an asphalt binder described herein in any aspect, and about 92.00 wt % to about 99.75 wt % (based on the total weight of the asphalt concrete) of a mineral aggregate, as described herein, wherein the asphalt binder comprises bitumen and an asphalt additive.

[0010] In another aspect, the present technology provides a method for preparing a stable asphalt additive blend. The method for preparing a stable asphalt additive blend includes: The method includes blending a phospholipid material, an epoxidized renewable oil or fat having an oxirane content of about 1.0% to about 15.0%, and a sulfurized renewable oil stabilizer to obtain an asphalt additive blend, wherein the sulfurized renewable oil stabilizer has a polymer distribution having an oligomer content of about 2 wt% to about 80 wt%, and a sulfur content ranging from about 0.001 wt% to about 8 wt%, based on the total weight of the sulfurized renewable oil stabilizer. The sulfurized renewable oil stabilizer may further have a PDI of about 1.0 to about 5.0. For example, the sulfurized renewable oil stabilizer has a polymer distribution having an oligomer content of about 2 wt% to about 80 wt%, a PDI ranging from about 1.0 to about 5.0, and a sulfur content ranging from about 0.001 wt% to about 8 wt%, based on the total weight of the sulfurized renewable oil stabilizer.

[0011] In another aspect, the present technology provides a method for reducing or preventing spalling, promoting adhesion, aiding compaction, and / or improving durability of asphalt concrete, comprising: adding an asphalt additive as described herein to bitumen to obtain an asphalt binder; combining the asphalt binder with the mineral aggregate to obtain asphalt concrete; The method provides that the asphalt concrete comprises between about 0.25 wt% and about 8.0 wt% asphalt binder and between about 92.00 wt% and about 99.75 wt% mineral aggregate. DETAILED DESCRIPTION OF THE INVENTION

[0012] Reference will now be made in detail to particular embodiments of the disclosed subject matter. While the disclosed subject matter will be described in conjunction with the enumerated claims, it will be understood that the illustrated subject matter is not intended to limit the scope of the claims to the disclosed subject matter. An embodiment described in conjunction with a particular embodiment is not necessarily limited to that embodiment and may be practiced in conjunction with any other embodiment.

[0013] Throughout this document, particularly in terms of providing a written description, all values ​​expressed in range format should be interpreted flexibly to include not only the numerical values ​​explicitly recited as the limits of the range, but also all individual numerical values ​​or subranges subsumed within that range, as if each numerical value and subrange were explicitly recited. Any recited range can be readily recognized as fully descriptive and allowing for the same range to be divided into at least two equal parts, three equal parts, four equal parts, five equal parts, ten equal parts, etc. For example, the range "about 0.1% to about 5%" or "about 0.1% to 5%" should be interpreted to include not only about 0.1% to about 5%, but also individual values ​​(e.g., 1%, 2%, 3%, and 4%) and subranges (e.g., 0.1% to 0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the recited range. Additionally, as will be understood by those skilled in the art, all terms such as "up to," "at least," "greater than," and "less than" refer to ranges that include the recited numbers and can subsequently be divided into subranges as described above. Finally, as will be understood by one skilled in the art, a range includes each individual member.

[0014] As used herein, the singular forms "a," "an," and "the," and similar referents in the context of describing elements (particularly in the context of the claims that follow), include plural referents unless the context clearly dictates otherwise. For example, reference to "a substituent" encompasses two or more substituents in addition to a single substituent, and so forth. Unless otherwise indicated herein or clearly contradicted by context, it is understood that any term in the singular may include its plural counterpart, and vice versa.

[0015] Furthermore, it should be understood that phrases or terms used herein and not otherwise defined are for purposes of description only and not of limitation. The use of any section headings is intended to aid in the reading of this document and should not be construed as limiting. The information associated with a section heading may be found within that particular section or outside of that section. In the event of inconsistent usage between this document and documents so incorporated by reference, the usage in the incorporated references should be construed as supplementary to the usage in this document. In the case of irreconcilable discrepancies, the usage in this document shall prevail.

[0016] As used herein, the terms "for example," "for instance," "such as," or "including" are meant to introduce examples that further clarify a more general subject matter. Unless otherwise specified, these examples are provided only as an aid in understanding the applications illustrated in this disclosure and are not meant to be limiting in any way.

[0017] In the methods described herein, the acts may be performed in the particular order described herein. Alternatively, in any aspect disclosed herein, unless a temporal or operational order is explicitly recited, certain acts may be performed in any order without departing from the principles of the disclosure. Furthermore, specified acts may be performed simultaneously unless an explicit claim recitation dictates that they be performed separately or unless the plain meaning of the claim requires so. For example, a claimed act of doing X and a claimed act of doing Y may be performed simultaneously in a single operation, and the resulting process would still fall within the literal scope of the claimed process.

[0018] As used herein, "about" will be understood by those of ordinary skill in the art and will vary to some extent depending on the context in which it is used. If uses of the term are not clear to persons of ordinary skill in the art, "about" will mean up to plus or minus 10% of the particular term, given the context in which it is used.

[0019] As used herein, the term "substantially" refers to the majority or most, such as at least about 85%.

[0020] As used herein, the following terms have the following meanings unless expressly stated otherwise.

[0021] As used herein, the term "renewable oil or fat" refers to an oil or fat obtained from a plant, animal, or microbial source. The term "renewable oil or fat" includes renewable oils and fatty derivatives unless otherwise indicated. Typically, renewable oils or fats are triacylglycerides. Examples of renewable oils include, but are not limited to, vegetable oils, algae oil, animal fats, tall oil, derivatives of these oils, combinations of any of these oils, and the like. Representative, non-limiting examples of vegetable oils include canola oil, rapeseed oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower oil, linseed oil, palm kernel oil, tung oil, jatropha oil, mustard oil, camelina oil, pennycress oil, hemp oil, algal oil, jojoba oil, and castor oil. Representative, non-limiting examples of animal sources include animal fats such as lard, tallow, poultry fat, yellow grease, and fish oil. Tall oil is a by-product of wood pulp production. As used herein, "vegetable oil" refers to oil derived from vegetables and / or oil seeds. Typically, renewable oils or fats may be refined, bleached, and / or deodorized. Renewable oils or fats may exist individually or as mixtures thereof. Renewable oils or fats may be modified, for example, they may be epoxidized, hydrogenated, and / or fractionated renewable oils or fats. Renewable oils or fats may also be polymerized renewable oils or fats ("polymerized oils") as described herein in any embodiment.

[0022] The term "epoxidized" or "oxirane" refers to the presence of an epoxide (or epoxy) ring, as shown below.

[0023] [ka]

[0024] The term "epoxidized renewable oil or fat" refers to a renewable oil or fat described herein that has epoxide ring functionality along the fatty acid hydrocarbon chain. Typically, the epoxidized renewable oil or fat described herein can be obtained by modifying a renewable oil or fat with a high content of unsaturated fatty acids or fatty acid derivatives (i.e., polyunsaturated fatty acids (PUFAs), monounsaturated fatty acids (MUFAs), etc.). Exemplary renewable oils or fats with high PUFA and / or MUFA content can include, but are not limited to, soybean oil and linseed oil. For example, renewable oils and fats can be epoxidized by treatment with peracid. The renewable oil or fat can also be epoxidized and fractionated to increase the epoxide content so that the renewable oil or fat has a high concentration of diepoxy and triepoxy fatty acid chains.

[0025] The term "oxirane content" or "epoxy oxirane content" (EOC) refers to the ratio of the sum of all oxirane functional groups in a molecule to the total molecular weight, expressed as percent EOC (%). The American Oil Chemist's Society (AOCS) maintains analytical methods for a wide variety of tests performed on vegetable oils. As used herein, EOC is determined by AOC Standard Procedure Cd 9-57.

[0026] "Acylglyceride" refers to a molecule having at least one glycerol moiety with at least one fatty acid residue linked via an ester bond. For example, acylglycerides can include monoacylglycerides, diacylglycerides, and triacylglycerides. The group of acylglycerides can be further narrowed by additional descriptive terms and can be modified to explicitly exclude or include particular subsets of acylglycerides.

[0027] "Monoacylglyceride" refers to a molecule having a glycerol moiety with a single fatty acid residue linked via an ester bond. The terms "monoacylglycerol," "monoacylglyceride," "monoglyceride," and "MAG" are used interchangeably herein. Monoacylglycerides include 2-acylglycerides and 1-acylglycerides.

[0028] "Diacylglyceride" refers to a molecule having a glycerol moiety with two fatty acid residues linked via an ester bond. The terms "diacylglycerol," "diacylglyceride," "diglyceride," and "DAG" are used interchangeably herein. Diacylglycerides include 1,2-diacylglycerides and 1,3-diacylglycerides.

[0029] "Triacylglyceride" refers to a molecule having a glycerol moiety linked to three fatty acid residues via ester bonds. The terms "triacylglycerol," "triacylglyceride," "triglyceride," and "TAG" are used interchangeably herein.

[0030] As used herein, the term "fatty acid" may refer to a molecule comprising a hydrocarbon chain and a terminal carboxylic acid group. As used herein, the carboxylic acid group of a fatty acid may be modified or esterified, such as occurs when the fatty acid is incorporated into a glyceride or another molecule (e.g., COO-R, where R represents, for example, a carbon atom). Alternatively, the carboxylic acid group may be present in the free fatty acid or in the form of a salt (i.e., COO-R). ”or COOH). The "tail" or hydrocarbon chain of a fatty acid may also be referred to as a fatty acid chain, a fatty acid side chain, or a fatty chain. The hydrocarbon chain of a fatty acid is typically a saturated or unsaturated aliphatic group. A fatty acid having N carbon atoms typically has a fatty acid side chain with N-1 carbon atoms. However, the present application also relates to modified forms of fatty acids, such as epoxidized fatty acids, and thus the term fatty acid may be used in the context where the fatty acid has been substituted or otherwise modified as described.

[0031] A "fatty acid residue" is a fatty acid in acyl or esterified form.

[0032] "Saturated" fatty acids are fatty acids that do not contain any carbon-carbon double bonds in the hydrocarbon chain. "Unsaturated" fatty acids contain one or more carbon-carbon double bonds. "Polyunsaturated" fatty acids contain two or more such carbon-carbon double bonds, while "monounsaturated" fatty acids contain only one carbon-carbon double bond. The carbon-carbon double bond can be in one of two configurations, designated cis and trans. Naturally occurring unsaturated fatty acids are generally in the "cis" form. Epoxidized renewable oils or fats can contain one or more epoxide rings formed from cis or trans carbon-carbon double bonds.

[0033] Non-limiting examples of fatty acids include C8, C10, C12, C14, C16 (e.g., C16:0, C16:1), C18 (e.g., C18:0, C18:1, C18:2, C18:3, C18:4), C20, and C22 fatty acids. For example, the fatty acids can be caprylic (8:0) acid, capric (10:0) acid, lauric (12:0) acid, myristic (14:0) acid, palmitic (16:0) acid, stearic (18:0) acid, oleic (18:1) acid, linoleic (18:2) acid, and linolenic (18:3) acid.

[0034] The fatty acid composition of an oil can be determined by methods well known in the art. Hydrolysis of oil components to produce free fatty acids, conversion of the free fatty acids to methyl esters, and analysis by gas-liquid chromatography (GLC) is a generally accepted standard method for determining the fatty acid composition of an oil sample. AOCS (2009) Ce 1-62 describes the procedure used.

[0035] The terms "sulfurized renewable oil stabilizer," "sulfurized renewable oil," or "sulfurized oil" refer to renewable oil that has undergone polymerization by a sulfurization process. Sulfurized renewable oil may generally be referred to as "polymerized renewable oil" or "polymerized oil" having a specific sulfur content. In various embodiments, polymerization of renewable oils or fats by sulfurization may be achieved by crosslinking fatty acid chains and / or glyceride fractions of triglyceride molecules contained in the renewable oil or fat using sulfur-containing compounds, such as sulfur-containing compounds that may be in reduced form. Typically, the polymerized oil is the polymerization product of a reaction mixture containing a starting renewable oil or fat and a sulfur-containing compound. The starting renewable oil or fat may be any suitable renewable oil or fat described herein. Additionally or alternatively, the starting renewable oil or fat may contain non-naturally occurring triacylglycerols or other oil components, such as acylglycerols with non-naturally occurring chain lengths (i.e., TAG, DAG, or MAG).

[0036] In some embodiments, the polymerized renewable oil or fat can be obtained by a method comprising: (a) heating the starting renewable oil or fat; (b) adding a sulfur-containing compound to the heated oil or fat; and (c) reacting the sulfur-containing compound with the oil to produce a polymerized oil having a polymer distribution of about 2 wt% to about 80 wt% oligomer content and a sulfur content of about 0.001 wt% to about 8 wt%. For example, the polymerized oil obtained according to the method described in this paragraph can further have a PDI of about 1.0 to about 5.0.

[0037] In the first step, the renewable oil or fat is heated to at least 100°C, preferably at least 115°C, in a vessel equipped with an agitator. The sulfur-containing compound is gradually added to the heated renewable oil or fat and can be added in either solid or molten form, although it should be understood that the sulfur-containing compound can be added before or simultaneously with the renewable oil or fat. The sulfur-containing compound can be, but is not limited to, elemental sulfur. The reaction of sulfur with the renewable oil or fat can increase the temperature of the renewable oil or fat-sulfur mixture. Preferably, the reaction mixture is maintained at a temperature of about 130°C to 250°C, more preferably about 130°C to about 220°C, and even more preferably about 160°C to about 200°C during the course of the reaction.

[0038] During the polymerization reaction of renewable oils or fats with sulfur, a gas-containing stream can be continuously sprayed onto the oil-sulfur mixture. The gas-containing stream can be selected from the group consisting of nitrogen, air, and other gases. The gas-containing stream can help promote the reaction and reduce odors (HS and other sulfides) associated with the reaction in the final product. The use of air can be useful because it can lead to oxidative polymerization of the renewable oils or fats in addition to the sulfurization process. Optionally, an accelerator can be used to increase the reaction rate. For example, suitable accelerators can include, but are not limited to, zinc oxide, magnesium oxide, and dithiocarbamates. Sulfurized renewable oils suitable for use in the present invention and methods for preparing them are described in International Application PCT / US2016 / 019767, entitled "POLYMERIZED OILS & METHODS OF MANUFACTURING THE SAME," filed February 26, 2016, the entire contents of which are incorporated herein by reference for the background information and methods described therein. Preferably, the sulfurized renewable oil can be a blend of sulfurized renewable oil and non-sulfurized renewable oil. Preferably, the sulfurized renewable oil is not diluted with non-sulfurized renewable oil, for example, more than 85 wt%, preferably 90 wt%, more preferably 95 wt%, even more preferably 99.5 wt%, and most preferably 99 wt% to 100 wt%, based on the total weight of the sulfurized renewable oil.

[0039] The term "flash point" or "flash point temperature" refers to a measure of the lowest temperature at which a material will first ignite with a brief flame. It is measured using a Cleveland open cup according to ASTM method D-92 and is reported in degrees Celsius (°C).

[0040] The term "oligomer" refers to polymers with a number average molecular weight (Mn) greater than 1000. Monomers make up everything else, including monoacylglycerides (NAG), diacylglycerides (DAG), triacylglycerides (TAG), and free fatty acids (FFA).

[0041] The term "polydispersity index" (PDI) (also known as "molecular weight distribution") refers to the ratio of weight average molecular weight (Mw) to number average molecular weight (Mn). Polydispersity data are collected using a gel permeation chromatography system equipped with a Waters 510 pump and a 410 differential refractometer. Samples are prepared at approximately 2% concentration in THF solvent. A flow rate of 1 ml / min and a temperature of 35°C are used. The columns consist of a Phenogel 5 micron linear / mixguard column and 300 x 7.8 mm Phenogel 5 micron columns (styrene-divinylbenzene copolymer) of 50, 100, 1000, and 10,000 Angstroms. Molecular weights were determined using the following standards:

[0042] [Table 1]

[0043] The terms "anti-strip" or "anti-strip" refer to an additive that improves the adhesion between the asphalt binder and the mineral aggregate. The use of an anti-strip additive results in a more durable bond between the asphalt binder and the mineral aggregate in the presence of moisture, making the combination more resistant to "stripping" or loss of the asphalt coating on the mineral aggregate.

[0044] The term "iodine number" (commonly abbreviated IV) as used herein is the mass in grams of iodine consumed by 100 grams of a chemical. Iodine numbers are often used to determine the amount of unsaturation in fats, oils, and waxes. In fatty acids, unsaturation occurs primarily as double bonds, which are highly reactive to halogens, in this case iodine. Thus, the higher the iodine number, the more unsaturation is present in the sample. The iodine number of a material can be determined by the standard, well-known Wijs method (AOCS (1993) Cd 1-25).

[0045] Warm mix asphalt (WMA) additives are used to reduce the temperatures required for the manufacture and compaction of asphalt pavements. These additives often serve to improve the asphalt binder's ability to coat the mineral aggregates in the asphalt mix, allowing the mix to be more easily compacted under a roller with lower mechanical or thermal energy requirements. It is often desirable for such additives to also improve the adhesion between the asphalt and the aggregate and the coating's ability to resist delamination in the presence of moisture. The impact of WMA additives can be demonstrated by their ability to modify the compaction rate and density attainment of the asphalt mix. These additives are often blended into bitumen as part of the asphalt binder.

[0046] Various theories have been proposed to explain the mechanism of action of various WMA additives, including binder plasticization and reduction of internal friction between aggregates, but the exact nature of the mechanism is difficult to conclusively determine. Therefore, the discussion of WMA properties is made without being bound to any particular mechanistic theory.

[0047] The durability and quality of asphalt concrete depend on the adhesion that exists at the interface between bitumen and mineral aggregate. The bond between bitumen and mineral aggregate can weaken over time due to many factors, including repeated traffic loads, weathering, and moisture damage, which can manifest in various forms, including fatigue cracks and distortions, such as rutting in the pavement mix. Moisture sensitivity of pavements is one of the major contributing factors to the deterioration of asphalt concrete pavements. Moisture can penetrate the pores of the mineral aggregate and cause delamination by displacing the bitumen film from the mineral aggregate surface. Delamination due to loss of adhesion can ultimately lead to premature pavement failure.

[0048] Asphalt additives containing a combination of epoxidized renewable oils or fats and phospholipid materials have been shown to exhibit improved adhesion promotion. Asphalt additive blends containing epoxidized renewable oils and a combination of fats and phospholipid materials tend to form oleogel, increasing the viscosity of the asphalt additive. Such oleogel can also cause storage stability issues unless the blend is prepared under sufficiently high shear mixing conditions. However, the high shear mixing requirements can create significant operational and manufacturing challenges. Furthermore, the inclusion of lower viscosity minor components (such as vegetable oils) as diluents or compatibilizers has resulted in storage stability issues due to the separation of the minor components.

[0049] Surprisingly, the inventors have discovered that the use of high viscosity vegetable oils (i.e., polymerized by sulfurization) as a minor phase additive to epoxidized renewable oil or fat and phospholipid material combinations shows unexpected improvements in blend stabilization, allowing for improved production of stable blends at low shear (e.g., mixing at 1500 rpm or less). The present invention includes sulfurized renewable oil stabilizers that do not affect the performance of asphalt additives in asphalt applications.

[0050] Asphalt Additives In one aspect, the present technology provides an asphalt additive comprising a phospholipid material, an epoxidized renewable oil or fat having an oxirane content of about 1.0% to about 15.0%, and a sulfurized renewable oil stabilizer. The sulfurized renewable oil stabilizer comprises a polymer distribution having an oligomer content of 2 wt% to about 80 wt% and a sulfur content of about 0.001 wt% to about 8 wt% based on the total weight of the sulfurized renewable oil stabilizer. The sulfurized renewable oil stabilizer may further have a PD of about 1.0 to 5.0. For example, the sulfurized renewable oil stabilizer may comprise a polymer distribution having an oligomer content of 2 wt% to about 80 wt%, a PDI of about 1.0 to about 5.0, and a sulfur content of about 0.001 wt% to about 8 wt% based on the total weight of the sulfurized renewable oil stabilizer.

[0051] The asphalt additive can have a weight ratio of phospholipid material to epoxidized renewable oil or fat of about 5:1 to about 1:5. For example, the weight ratio can be about 5:1 to about 1:5, about 3:1 to about 1:3, about 2:1 to about 1:2, or about 1:1. Suitable weight ratios can include about 5:1, about 4.5:1, about 4:1, about 3.5:1, about 3:1, about 2.5:1, about 2:1, about 1.5:1, about 1:1, about 1:1.5, about 1:2, about 1:2.5, about 1:3, about 1:3.5, about 1:4, about 1:4.5, about 1:5, or any ranges inclusive of and / or between any two of the foregoing values.

[0052] The asphalt additive of the present technology may include the phospholipid material in an amount of about 10.0 wt% to about 80.0 wt%. For example, the phospholipid material may be present in an amount of about 10.0 wt% to about 80.0 wt%, about 10.0 wt% to about 60 wt%, about 40.0 wt% to about 60.0 wt%, or about 45.0 wt% to about 55 wt%. The phospholipid material can be present in an amount of about 10.0 wt%, about 15.0 wt%, about 20.0 wt%, about 25.0 wt%, about 30 wt%, about 35 wt%, about 40.0 wt%, about 45.0 wt%, about 50.0 wt%, about 55.0 wt%, about 60.0 wt%, about 65.0 wt%, about 70.0 wt%, about 75.0 wt%, about 80.0 wt%, or any range including and / or between any two of the foregoing values.

[0053] As used herein, the term "phospholipid material" refers to a material containing phospholipids. Phospholipids are generally characterized as lipids having a glycerol or sphingosine backbone esterified to two fatty acids and phosphoric acid or a phosphate ester. The phospholipids of the phospholipid material may further comprise phospholipid derivatives. For example, suitable phospholipid derivatives may include hydrolyzed phospholipids, acetylated phospholipids, epoxidized phospholipids, hydroxylated phospholipids, or mixtures thereof. Typically, the phospholipid material described herein may comprise at least about 50 wt% to 100 wt% phospholipids, based on the total weight of the phospholipid material. For example, the phospholipid material may comprise at least about 50 wt% to 100 wt%, at least about 60 wt% to 100 wt%, at least about 70 wt% to 100 wt%, at least about 80 wt% to 100 wt%, or at least about 90 wt% to 100 wt% phospholipids.

[0054] Phospholipids can be natural phospholipids, synthetic phospholipids, or combinations thereof.As described herein, natural phospholipids can be derived from plant, animal, or microbial sources.For example, phospholipids can include, but are not limited to, phosphatidylcholine, phosphatidylinositol, phosphatidylethanolamine, phosphatidic acid, or combinations thereof.

[0055] The phospholipid material may include a lecithin material as a phospholipid source. As used herein, the term "lecithin" or "lecithin material" refers to a complex mixture of acetone-insoluble phospholipids, alone or with various other compounds, including, but not limited to, fatty acids, triglycerides, sterols, carbohydrates, glycolipids, and water. Lecithin can be obtained from a variety of sources, including, but not limited to, plant sources (such as vegetable oils), animal sources (such as eggs and bovine brain), or microbial sources. For example, suitable lecithin sources can include, but are not limited to, soybean lecithin, rapeseed lecithin, sunflower seed lecithin, egg lecithin, peanut lecithin, corn lecithin, bovine brain lecithin, jojoba lecithin, or mixtures thereof. Regarding the aforementioned lecithin sources, the phospholipid material can be obtained from a crude refinery stream containing fatty acids and phosphatidyl materials, as described in U.S. Pat. No. 10,689,406, the entire contents of which are incorporated herein by reference. Additionally or alternatively, the lecithin may be a modified lecithin, for example, modified lecithin may include, but is not limited to, hydrogenated lecithin, epoxidized lecithin, deoiled lecithin, or mixtures thereof.

[0056] The lecithin material may comprise about 5 wt% to 100 wt% of acetone-insoluble material, based on the total weight of the lecithin material. Suitable amounts of acetone-insoluble material include about 5 wt% to 100 wt%, about 5 wt% to about 75 wt%, about 30 wt% to about 70 wt%, or about 40 wt% to about 65 wt%. For example, the lecithin material can contain about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, about 95 wt%, 100 wt%, or any range of values ​​between and including any two of the foregoing values. The phospholipid content in the lecithin composition is measured using an acetone insolubility test method known to those skilled in the art (e.g., AOCS (2017) Method Ja 4-46).

[0057] The asphalt additive may comprise from about 10.0 wt% to about 80.0 wt% of the epoxidized renewable oil or fat, based on the total weight of the asphalt additive. For example, the epoxidized renewable oil or fat may be present in an amount of from about 10.0 wt% to about 80.0 wt%, from about 10.0 wt% to about 60.0 wt%, from about 40.0 wt% to about 60.0 wt%, or from about 45.0 wt% to about 55 wt%. Typically, the asphalt additive may include epoxidized renewable oils or fats in an amount of about 10.0 wt%, about 15.0 wt%, about 20.0 wt%, about 25.0 wt%, about 30 wt%, about 35 wt%, about 40.0 wt%, about 45.0 wt%, about 50.0 wt%, about 55.0 wt%, about 60.0 wt%, about 65.0 wt%, about 70.0 wt%, about 75.0 wt%, about 80.0 wt%, or any range of amounts including and / or between any two of the foregoing values.

[0058] The epoxidized renewable oil or fat may have an oxirane content of about 1.0% to about 15.0%, about 4.0% to about 12.0%, about 6.0% to about 10.0%, about 8.0% to about 10.0%, or any range inclusive and / or between any two of the foregoing values. Suitable oxirane contents of the epoxidized renewable oil or fat may include about 1.0%, about 2.0%, about 3.0%, about 4.0%, about 5.0%, about 6.0%, about 7.0%, about 8.0%, about 9.0%, about 10.0%, about 11.0%, about 12.0%, about 13.0%, about 14.0%, about 15.0%, or any range inclusive and / or between any two of the foregoing values. The oxirane content may be determined by AOCS Cd 9-57.

[0059] The epoxidized renewable oil or fat includes an epoxidized fatty acid or an epoxidized fatty acid derivative, which may include, but is not limited to, an epoxidized vegetable oil, an epoxidized acetylated acylglyceride, an epoxidized fatty acid ester, an estolide, or a combination thereof.

[0060] The epoxidized renewable oil or fat may include epoxidized soybean oil, epoxidized canola oil, epoxidized linseed oil, epoxidized soybean methyl ester, epoxidized linseed methyl ester, epoxidized tall oil fatty acid (TOFA), epoxidized acetylated triacylglycerol, epoxidized acetylated diacylglycerol, epoxidized acetylated monoacylglycerol, epoxidized 2-ethylhexyl soyate, epoxidized 2-ethylhexyl TOFA, epoxidized isoamyl soyate, epoxidized isoamyl palm stearin, epoxidized isoamyl TOFA, epoxidized isoamyl soyate, epoxidized soybean methyl ester acetate estolide, epoxidized jojoba oil, or a mixture thereof. Typically, the epoxidized renewable oil or fat may include epoxidized soybean oil, epoxidized linseed oil, epoxidized canola oil, or a mixture thereof. For example, the epoxidized renewable oil or fat may be epoxidized soybean oil. In another example, the epoxidized renewable oil or fat may be epoxidized linseed oil.

[0061] The epoxidized renewable oil or fat may be subjected to fractionation or may be a fractionated epoxidized renewable oil or fat. As used herein, the term "fractionation" refers to the process of separating a renewable oil or fat into several fractions having different properties, including hardness and melting point.

[0062] The asphalt additive can include any amount of sulfurized renewable oil stabilizer, provided that the sulfurized renewable oil stabilizer constitutes a minor asphalt additive component relative to the phospholipid material and epoxidized renewable oil or fat. In any embodiment, the asphalt additive can include up to about 35 wt% of sulfurized renewable oil stabilizer, based on the total weight of the asphalt additive. For example, suitable amounts of sulfurized renewable oil stabilizer in the asphalt additive include about 1 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, about 10 wt%, about 11 wt%, about 12 wt%, about 13 wt%, about 14 wt%, about 15 wt%, about 16 wt%, about 17 wt%, about 18 wt%, about 19 wt%, about 20 wt%, about 21 wt%, about 22 wt%, about 23 wt%, about 24 wt%, about 25 wt%, about 26 wt%, about 27 wt%, about 28 wt%, about 29 wt%, about 30 wt%, about 31 wt%, about 32 wt%, about 33 wt%, about 34 wt%, about 35 wt%, about 36 wt%, about 37 wt%, about 38 wt%, about 39 wt%, about 40 wt%, about 41 wt%, about 42 wt%, about 43 wt%, about 44 wt%, about 45 wt%, about 46 wt%, about 47 wt%, about 48 wt%, about 49 wt%, about 50 wt%, about 51 wt%, about 52 wt%, about 53 wt%, about 54 wt%, about 55 wt%, about 56 wt%, about 57 wt%, about 58 The sulfurized renewable oil stabilizer may be about 5 wt%, about 20 wt%, about 21 wt%, about 22 wt%, about 23 wt%, about 24 wt%, about 25 wt%, about 26 wt%, about 27 wt%, about 28 wt%, about 29 wt%, about 30 wt%, about 31 wt%, about 32 wt%, about 33 wt%, about 34 wt%, about 35 wt%, or any range including and / or between any two of the foregoing values. In any embodiment, the asphalt additive may comprise about 5 wt% to about 35 wt% of the sulfurized renewable oil stabilizer. In any embodiment, the asphalt additive may comprise about 10 wt% to about 25 wt% of the sulfurized renewable oil stabilizer. In any embodiment, the asphalt additive may comprise about 12 wt% to about 24 wt% of the sulfurized renewable oil stabilizer. In any embodiment, the asphalt additive can include from about 16 wt % to about 22 wt % of the sulfurized renewable oil stabilizer.

[0063] The sulfurized renewable oil stabilizer is the polymerized renewable oil described herein in any embodiment. The polymerized renewable oil can be the polymerization product of a reaction mixture containing a starting renewable oil or fat and a sulfur-containing compound when the polymerization is sulfurization. Suitable starting renewable oils or fats can include the aforementioned renewable oils or fats, including, but not limited to, palm oil, sunflower oil, corn oil, soybean oil, canola oil, rapeseed oil, linseed oil, tung oil, castor oil, tall oil, cottonseed oil, peanut oil, safflower oil, corn stillage oil (recovered corn oil, typically the bottoms from the corn ethanol production process), other low-cost waste oils (e.g., waste cooking oil or other used oils), or combinations thereof. Suitable sulfur-containing compounds can include reduced forms of sulfur. For example, sulfur-containing compounds can include, but are not limited to, elemental sulfur.

[0064] The sulfurized renewable oil stabilizer may have a polymer distribution of about 2 wt% to about 80 wt% oligomer content (about 20 wt% to about 98 wt% monomer), about 15 wt% to about 60 wt% oligomer content (about 40 wt% to about 85 wt% monomer), about 20 wt% to about 60 wt% oligomer content (about 40 wt% to about 80 wt% monomer), about 55 wt% to about 75 wt% oligomer content (about 25 wt% to about 45 wt% monomer), about 50 wt% to about 75 wt% oligomer content (about 25 wt% to about 50 wt% monomer), or any range including and / or between any two of the foregoing values.

[0065] The sulfurized renewable oil stabilizer can have a PDI of from about 1.0 to about 5.0, from about 1.30 to about 2.20, from about 1.50 to about 2.05, or any range including and / or between any two of the foregoing values.

[0066] The sulfurized renewable oil stabilizer can have a sulfur content of less than about 8 wt%. For example, the sulfur content of the sulfurized renewable oil stabilizer can be about 0.001 wt%, about 0.005 wt%, about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.5 wt%, about 1 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, or any range including and / or between any two of the foregoing values.

[0067] The sulfurized renewable oil stabilizer can have a flash point, as measured by the Cleveland Open Cup Method, of about 100°C to about 400°C, about 200°C to about 350°C, about 220°C to about 300°C, about 245°C to about 275°C, or any range including and / or between any two of the foregoing values. The viscosity of the sulfurized renewable oil stabilizer can be about 1 cSt to about 100 cSt at 100°C.

[0068] The asphalt additive can have a weight ratio of phospholipid material, epoxidized renewable oil or fat, and sulfurized renewable oil stabilizer that can be from about 1:1:1 to about 45:45:1. In some embodiments, the weight ratio can be from about 1:1:1 to about 20:20:2. In some embodiments, the weight ratio can be from about 1:1:1 to about 10:10:2. In some embodiments, the weight ratio can be from about 10:10:2 to about 2:2:1. In some embodiments, the weight ratio can be from about 2:2:1 to about 1:1:1. In some embodiments, the weight ratio can be from 20:20:2 to 2:2:1. The weight ratio of the phospholipid material to the epoxidized renewable oil or fat can be a weight ratio as described herein (e.g., from about 5:1 to 1:5), in which case the sulfurized renewable oil stabilizer is a minor component (by weight) relative to the phospholipid material and the epoxidized renewable oil or fat.

[0069] The asphalt additives described herein may further comprise a fatty acid material, such as soybean oil, linseed oil, canola oil, or mixtures thereof. Typically, the asphalt additive may comprise from about 0.1 wt% to about 40.0 wt% of the fatty acid material, based on the total weight of the asphalt additive. Suitable amounts of the fatty acid material may include about 0.1 wt%, about 1.0 wt%, about 5.0 wt%, about 10.0 wt%, about 15.0 wt%, about 20.0 wt%, about 25.0 wt%, about 30.0 wt%, about 35.0 wt%, about 40.0 wt%, or any ranges inclusive and / or between any two of the foregoing claims. For example, the fatty acid material may be a fractionated fatty acid material.

[0070] The asphalt additives described herein, for example, when the asphalt additives are preblended prior to use in asphalt applications, typically have a viscosity of about 20 cSt to about 10,000 cSt at 25° C. Suitable viscosities at 25° C. include about 20 cSt, about 30 cSt, about 40 cSt, about 50 cSt, about 60 cSt, about 70 cSt, about 80 cSt, about 90 cSt, about 100 cSt, about 200 cSt, about 300 cSt, about 400 cSt, about 500 cSt, about 600 cSt, about 700 cSt, about 800 cSt, about 900 cSt, about 1,000 cSt, about 1,500 cSt, about 2,000 cSt, about 2,500 cSt, about 3,000 cSt, The viscosity may be about 3,500 cSt, about 4,000 cSt, about 4,500 cSt, about 5,000 cSt, about 5,500 cSt, about 6,000 cSt, about 6,500 cSt, about 7,000 cSt, about 7,500 cSt, about 8,000 cSt, about 8,000 cSt, about 8,500 cSt, about 9,000 cSt, about 9,500 cSt, about 10,000 cSt, or any ranges inclusive of and / or between any two of the foregoing values.

[0071] The inventors have discovered that asphalt additives according to the present technology unexpectedly improve one or more performance characteristics when incorporated into asphalt applications. For example, the asphalt additives described herein demonstrate surprising improvements in the overall performance of asphalt or asphalt concrete, including adhesion promotion, anti-stripping, warm mix asphalt additives, hot mix asphalt additives, compaction aids, and durability of the asphalt mix.

[0072] The asphalt additives described herein typically exhibit improved adhesion promotion in asphalt applications.

[0073] The asphalt additives described herein typically exhibit improved anti-stripping properties in asphalt applications.

[0074] The asphalt additives described herein typically improve compaction in asphalt applications.

[0075] The asphalt additives described herein typically improve the durability of the asphalt mix in asphalt applications.

[0076] The asphalt additives described herein are typically warm mix asphalt additives.

[0077] Alternatively, the asphalt additives described herein may be hot mix asphalt additives.

[0078] The asphalt additives of the present technology surprisingly exhibit improved stability, for example, compared to asphalt additives that do not include one or more of a phospholipid material, an epoxidized renewable fat or oil, or a sulfurized renewable oil stabilizer.

[0079] In one aspect, the present technology provides for the use of the asphalt additives described herein to reduce or prevent spalling in asphalt applications.

[0080] In another aspect, the present technology provides for the use of the asphalt additives described herein as compaction aids in asphalt applications.

[0081] In another aspect, the present technology provides for the use of the asphalt additives described herein as adhesion promoters in asphalt applications.

[0082] In yet another related aspect, the present technology provides the use of the asphalt additive described herein as a warm mix asphalt additive or a hot mix asphalt additive in asphalt applications. For example, the use of the asphalt additive is as a warm mix asphalt additive. In another example, the use of the asphalt additive is as a hot mix asphalt additive.

[0083] Asphalt binder In another aspect, the present technology provides an asphalt binder comprising bitumen and any of the asphalt additives described herein. For purposes of the present technology, the terms "bitumen" or "asphalt" refer to the binder phase of asphalt concrete and are a class of natural, recycled, or manufactured black or dark-colored, solid, semi-solid, resinous, or viscous cementitious substances composed primarily of high-molecular-weight polar hydrocarbon species (e.g., asphaltenes), of which asphalt, tar, pitch, and asphaltite are typical. (Asphalt, Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons Inc.)

[0084] The asphalt binder can include from about 0.1 wt% to about 3.0 wt% of the asphalt additive described herein, based on the total weight of the asphalt binder. For example, the asphalt additive can be present in the asphalt binder in an amount of from about 0.1 wt% to about 3.0 wt%, from about 0.1 wt% to about 2.0 wt%, from about 0.1 wt% to about 1.5 wt%, from about 0.3 wt% to about 1.0 wt%, or from about 0.3 wt% to about 0.7 wt%. Suitable amounts of asphalt additive can include about 0.1 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.6 wt%, about 0.7 wt%, about 0.8 wt%, about 0.9 wt%, about 1.0 wt%, about 1.5 wt%, about 2.0 wt%, about 2.5 wt%, about 3.0 wt%, or any ranges inclusive of and / or between any two of the foregoing values.

[0085] The asphalt binder can comprise about 97.0 wt% to about 99.9 wt% bitumen, based on the total weight of the asphalt binder. Suitable amounts of bitumen present in the asphalt binder can include about 97.0 wt%, about 97.5 wt%, about 98.0 wt%, about 98.5 wt%, about 99.0 wt%, about 99.1 wt%, about 99.2 wt%, about 99.3 wt%, about 99.4 wt%, about 99.5 wt%, about 99.6 wt%, about 99.7 wt%, about 99.8 wt%, about 99.9 wt%, or any ranges including and / or between any two of the foregoing values.

[0086] The asphalt binders described herein may further comprise one or more additional additives suitable for asphalt applications. For example, the one or more additional additives may include, but are not limited to, thermoplastic elastomer and thermoplastic plastomer polymers (such as styrene-butadiene-styrene, ethylene vinyl acetate, functionalized polyolefins, etc.), polyphosphoric acid (PPA), anti-stripping additives (such as amine-based, phosphate-based, etc.), warm mix additives, emulsifiers, fibers, or mixtures thereof.

[0087] The asphalt binders described herein may further comprise a PPA. Typically, the asphalt binder may comprise from about 0.1 wt% to about 5.0 wt% of the PPA, based on the total weight of the asphalt binder. For example, the asphalt binder may comprise about 0.1 wt%, about 0.5 wt%, about 1.0 wt%, about 1.5 wt%, about 2.0 wt%, about 2.5 wt%, about 3.0 wt%, about 3.5 wt%, about 4.0 wt%, about 4.5 wt%, about 5.0 wt%, or any range of amounts including and / or between any two of the foregoing values.

[0088] Asphalt concrete In yet another aspect, the present technology provides an asphalt concrete comprising about 0.25 wt % to about 8.0 wt % (based on the total weight of the asphalt concrete) of an asphalt binder described herein in any aspect, and about 92.00 wt % to about 99.75 wt % (based on the total weight of the asphalt concrete) of a mineral aggregate, as described herein, wherein the asphalt binder comprises bitumen and an asphalt additive.

[0089] The asphalt concrete described herein can contain from about 0.25 wt% to about 8.0 wt%, from about 0.25 wt% to about 6.5 wt%, from about 0.25 wt% to about 5.0 wt%, from about 0.30 wt% to about 4.0 wt%, or from about 0.5 wt% to about 3.5 wt% asphalt binder, based on the total weight of the asphalt. For example, the asphalt binder can be present in the asphalt concrete in an amount of about 0.25 wt%, about 0.30 wt%, about 0.40 wt%, about 0.50 wt%, about 0.60 wt%, about 0.70 wt%, about 0.80 wt%, about 0.90 wt%, about 1.0 wt%, about 1.5 wt%, about 2.0 wt%, about 2.5 wt%, about 3.0 wt%, about 3.5 wt%, about 4.0 wt%, about 4.5 wt%, about 5.0 wt%, about 5.5 wt%, about 6.0 wt%, about 6.5 wt%, about 7.0 wt%, about 7.5 wt%, about 8.0 wt%, or any range including and / or between any two of the foregoing values.

[0090] "Mineral aggregate" refers to a solid, generally inert, load-bearing component of asphalt concrete, including, but not limited to, clay, sand, gravel, crushed stone, slag, or rock dust. Mineral aggregate may be further characterized by its calcium carbonate content. For purposes of the present technique, the calcium carbonate concentration of a mineral aggregate can be determined to classify the aggregate's chemistry. The primary component of limestone is calcium carbonate, which can be determined by back titration, which involves adding an excess amount of acid to an unknown basic aggregate and then titrating to an endpoint with standardized NaOH. Typically, mineral aggregate used in asphalt applications may be the result of one or more sources of aggregate described herein (e.g., stone, rock, gravel, etc.), each of which may be further crushed, sieved, or graded to conform to various mineral aggregate grades. Mineral aggregate grades used in asphalt applications are generally classified by terms such as "high density grade," "gap grade," "high grade," and "low grade," depending on the application. Mineral aggregate grades in asphalt applications are typically defined by the largest sieve opening size that will retain a portion of the grade, for example, maximum sizes may include, but are not limited to, 1.5 inch, 1 inch, 3 / 4 inch, and 1 / 2 inch sieve sizes.

[0091] The asphalt concrete may comprise mineral aggregate in an amount of about 92.00 wt%, about 92.50 wt%, about 93.00 wt%, about 93.50 wt%, about 94.00 wt%, about 94.50 wt%, about 95.00 wt%, about 95.50 wt%, about 96.00 wt%, about 96.50 wt%, about 97.00 wt%, about 97.50 wt%, about 98.0 wt%, about 98.5 wt%, about 99.0 wt%, about 99.25 wt%, about 99.50 wt%, about 99.75 wt%, or any range of amounts including and / or between any two of the foregoing values.

[0092] The asphalt concrete may further include recycled materials, such as recycled bituminous materials, recycled aggregate, reclaimed asphalt pavement (RAP) pulverized material, recycled asphalt shingles (RAS), or mixtures thereof.

[0093] method In another aspect, the present technology provides a method for preparing a stable asphalt additive blend. The method for preparing a stable asphalt additive blend includes: The method includes blending a phospholipid material, an epoxidized renewable oil or fat having an oxirane content of about 1.0% to about 15.0%, and a sulfurized renewable oil stabilizer to obtain an asphalt additive blend, wherein the sulfurized renewable oil stabilizer has a polymer distribution with an oligomer content of about 2 wt% to about 80 wt% and a sulfur content of about 0.001 wt% to about 8 wt%, based on the total weight of the sulfurized renewable oil stabilizer. The sulfurized renewable oil stabilizer may further have a PDI of about 1.0 to about 5.0. For example, the sulfurized renewable oil stabilizer may have a polymer distribution with an oligomer content of about 2 wt% to about 80 wt%, a PDI of about 1.0 to about 5.0, and a sulfur content of about 0.001 wt% to about 8 wt%, based on the total weight of the sulfurized renewable oil stabilizer.

[0094] The method may further include heating the epoxidized renewable oil or fat, the sulfurized renewable oil stabilizer, and the phospholipid material prior to mixing; combining the epoxidized renewable oil or fat with the sulfurized renewable oil stabilizer to obtain a first blend; mixing the first blend; combining the first blend with the phospholipid material; and mixing the first blend with the phospholipid material.

[0095] The inventors have surprisingly discovered that the method of the present invention is a scalable method for producing homogeneous, storage-stable asphalt additive blends from epoxidized renewable oils or fats and phospholipid materials in the presence of a sulfurized renewable oil stabilizer when prepared under low shear. Low shear mixing can be carried out according to any suitable method known in the art, including methods suitable for plant (or large-scale) manufacturing. For example, mixing can be carried out using any suitable manufacturing equipment sufficient to obtain a homogeneous mixture under low shear to produce the asphalt additive system of the present invention.

[0096] In one example, low shear mixing can include blending the phospholipid material, epoxidized renewable oil or fat, and sulfurized renewable oil stabilizer at a shear rate of, but not limited to, about 500 rpm to about 1500 rpm, about 600 rpm to about 1500 rpm, about 750 rpm to about 1500 rpm, about 1000 rpm to about 1500 rpm, or any range between and / or including any two of the foregoing values. Alternatively, mixing can include blending at a high shear rate, such as a shear rate of greater than 1500 rpm up to about 3500 rpm. Suitable high shear rates can include, but are not limited to, about 1600 rpm to about 3500 rpm, about 2000 rpm to about 3500 rpm, about 2500 rpm to about 3000 rpm, about 3000 rpm to about 3500 rpm, or any range between and / or including any two of the foregoing values.

[0097] The resulting asphalt additive blend is consistent with the asphalt additives described herein in any embodiment.

[0098] The method can be carried out for batch or continuous preparation of asphalt additive blends.

[0099] In one embodiment, the present technology provides a method for preparing an asphalt binder, comprising blending a phospholipid material, an epoxidized renewable oil or fat having an oxirane content of about 1.0% to about 15.0%, and a sulfurized renewable oil stabilizer to obtain an asphalt additive blend, wherein the sulfurized renewable oil stabilizer comprises a polymer distribution having an oligomer content of about 2 wt% to about 80 wt%, and a sulfur content ranging from about 0.001 wt% to about 8 wt%, based on the total weight of the sulfurized renewable oil stabilizer. The sulfurized renewable oil stabilizer may further comprise a PDI of about 1.0 to about 5.0. For example, the sulfurized renewable oil stabilizer may comprise a polymer distribution having an oligomer content of about 2 wt% to about 80 wt%, a PDI ranging from about 1.0 to about 5.0, and a sulfur content ranging from about 0.001 wt% to about 8 wt%, based on the total weight of the sulfurized renewable oil stabilizer.

[0100] In another aspect, the present technology provides a method for reducing or preventing spalling, promoting adhesion, aiding compaction, and / or improving durability of asphalt concrete, comprising: adding an asphalt additive as described herein to bitumen to obtain an asphalt binder; combining the asphalt binder with the mineral aggregate to obtain asphalt concrete; The method provides that the asphalt concrete comprises between about 0.25 wt% and about 8.0 wt% asphalt binder and between about 92.00 wt% and about 99.75 wt% mineral aggregate.

[0101] The invention thus generally described will be more readily understood by reference to the following examples, which are provided by way of illustration and are not intended to limit the invention. [Example]

[0102] General Methods and Materials. Sulfurized refined soybean oil (Sf.SBO) was prepared as described in International Application PCT / US2016 / 019767. Specifically, when prepared in the laboratory, an amount of precipitated sulfur is added to a 1-liter round-bottom flask containing 650 grams of vegetable oil. The reactor is then heated to the target reaction temperature using a heating mantle, taking care not to overshoot the target temperature by more than 5°C. The reaction mixture is stirred using an electric stirrer equipped with a stirring shaft and blades. The reaction is continuously sparged with nitrogen at 2 to 12 standard cubic feet per hour (SCFH). A condenser and receiving flask are used to collect all distillate.

[0103] The reaction foams at a temperature of approximately 110-115°C, where sulfur dissolves in the oil. The reaction is monitored using GPC to measure oligomer content and distribution, and viscosity is measured at 40°C using ASTM D445. The reaction is considered complete when the desired oligomer content is reached. The reactor is then cooled to 60°C.

[0104] In the following examples, Sf.SBO samples were prepared by reacting refined soybean oil with 7.0 wt.% elemental sulfur at 175-185°C for approximately 33 hours with nitrogen sparging, resulting in a polymerized oil (due to sulfurization) having an oligomer content of approximately 70.0 wt.% and a sulfur content of 7.0 wt.%. While it is possible to dilute the sulfurized oil with additional vegetable oil or derivative (i.e., non-sulfurized oil), it has been found that undiluted sulfurized oil is preferred for the blends described in these examples due to improved storage stability.

[0105] Blending Process For laboratory batch production, an overhead drill mixer was used for low shear blending at either 600 or 1500 rpm. High shear mixing was performed using an IKA Ultra Turrax T50 model equipped with an R1402 dissolver and a rotor / stator G45-G at shear rates of 3000-3500 rpm.

[0106] All ingredients were heated to 50°C to achieve a lower viscosity, but not so high as to exceed the phospholipid decomposition temperature. For blends containing Sf.SBO, Sf.SBO was first blended with epoxidized linseed oil (ELO) at the target concentration. Soy lecithin (SL) was added slowly to the Sf.SBO / ELO mixture at either low or high shear rates.

[0107] Stability test method Centrifugation: To evaluate the long-term storage stability of the different mixtures, samples were centrifuged at 2300 rpm for a total of 40 minutes. The test method mimics static storage over a period of 8 to 10 weeks to evaluate phase separation of the asphalt additives.

[0108] Visual evaluation was performed at different time intervals of 10, 20, and 40 minutes. The phase behavior of the blends was evaluated at each time interval at room temperature. The results were recorded as the volume percentage of "supernatant" and "sediment" based on the scale on the vial.

[0109] The "supernatant" is defined as the translucent layer when the vial is exposed to light, and the "precipitate" is defined as the bottom muddy layer that separates and adheres to the bottom of the vial immediately after inverting the vial.

[0110] Lower supernatant and precipitate values ​​indicate greater stability and are more desirable.

[0111] In this study, the key elements of phase behavior evaluation were determined to be the extent of precipitated material and supernatant (clear top layer). Both the precipitate and supernatant were selected as qualitative measures of storage stability. The precipitated material and supernatant were measured in milliliters and converted to a volume percentage of the total volume of the mixture.

[0112] Example 1 - Effect of shear rate and type on asphalt additive blend stability. Following the blending process described herein, low shear blends were prepared at 600 and 1500 rpm, and high shear blends were prepared at 3250 rpm. The relative ratio of SL to ELO remained 1:1, but the minor component accounted for 20 wt% of the final blend. The overall blend ratio of SL / ELO / Sf.SBO was 2:2:1 by weight. The blend ratios and stability test results are shown in Table 1.

[0113] [Table 2]

[0114] As shown in Table 1, blends containing Sf.SBO as a minor component stabilizer showed significant improvement compared to blends with only SL / ELO. Thus, the SL / ELO / Sf.SBO blends showed improved blend stability with respect to supernatant and sediment separation compared to the binary SL / ELO blends.

[0115] Example 2 - Effect of adding different minor ingredients during the blending process of ELO and SL. Blends were prepared under low shear at 600 rpm according to the blending procedure described above. In each blend, the relative ratio of SL to ELO remained 1:1, but the minor component accounted for 20% of the final blend. The overall blend ratio of SL / ELO / minor component can be expressed as 2:2:1 by weight. The minor components compared were selected from Sf.SBO, refined bleached deodorized soy (SBO), and fuel-grade soy methyl ester (SME). The blend ratios and stability test results are shown in Table 2.

[0116] [Table 3]

[0117] As shown in Table 2, blends containing Sf.SBO as the minor stabilizer exhibited significantly improved stability with respect to supernatant and sediment compared to the SL / ELO blend and the ternary blends with SME and SBO as the minor components, respectively. In particular, blends containing SBO and SME as low-viscosity diluents exhibited significantly reduced stability compared to the SL / ELO blend and the SL / ELO / Sf.SBO blend.

[0118] Example 3A - Effect of Sf.SBO concentration on asphalt additive stability. Blends were prepared under low shear at 600 rpm according to the blending procedure described above. The relative ratio of SL to ELO remained 1:1, but the minor components were gradually varied from 5% to a maximum of 33.3% of the final blend. The blend ratios and stability test results are shown in Table 3.

[0119] [Table 4]

[0120] As shown in Table 3, increasing the Sf.SBO concentration continuously improved stability for the supernatant up to a concentration of 20%. Further addition of Sf.SBO (33 wt%) showed improved stability over the binary SL / ELO blend alone. With regard to sediment, the maximum effect was achieved at 5% inclusion, and further increases did not result in further improvement. Overall, the results showed that the inclusion of Sf.SBO improved stability compared to the SL / ELO blend under low shear.

[0121] Example 3B - Effect of Sf.SBO on the stability of 1:1 SL / ELO blends. Blends were prepared under high shear at 2000 rpm according to the blending procedure described above. For the two blends shown in Table 4, the relative ratio of SL to ELO remained 1:1, but a minor component was added to the second blend during the mixing process to make up 20% of the final blend. The blend ratios and stability test results are shown in Table 4.

[0122] [Table 5]

[0123] Example 3C-2: Effect of Sf.SBO on the stability of 7 SL / ELO blends. Blends were prepared under high shear at 2000 rpm according to the blending procedure described above. The relative ratio of SL to ELO remained 2:7, but the minor component accounted for 10% of the final blend. The 2:7 SL / ELO blend, with a higher proportion of ELO, exhibited significantly lower stability than the 1:1 SL / ELO blend, but significant improvement was observed by adding Sf.SBO at 10% of the final blend during the mixing process. The blend ratios and stability test results are shown in Table 5.

[0124] [Table 6]

[0125] As shown in Tables 4 and 5, the incorporation of Sf.SBO under high shear at 2000 RPM significantly improved stability compared to the binary SL / ELO blends, as indicated by the level of sediment after 15 and 30 minutes of centrifugation at 2300 RPM. The addition of 20% by weight of the minor component of the final blend to a 1:1 relative ratio SL / ELO blend resulted in a 9.2% and 15.6% improvement in sediment at 15 and 30 minutes of centrifugation, respectively, compared to the binary blend system.

[0126] Addition of minor components to the 2:7 SL / ELO resulted in surprisingly significant improvements in sediment at 15 and 30 minutes of centrifugation, 66% and 66.7%, respectively, compared to the SL / ELO blend.

[0127] Overall, the results showed that the inclusion of Sf.SBO improved stability compared to SL / ELO blends under high shear. The 2:7:1 SL / ELO / Sf.SBO blend surprisingly showed significantly improved stability compared to the binary SL / ELO blends.

[0128] Example 4 - Evaluation of the synergistic anti-stripping properties of Sf.SBO addition to SL / ELO asphalt additives in asphalt applications. The shaker table stripping test was used to evaluate the compatibility between the bitumen-coated aggregate and bitumen after conditioning the aggregate in 60°C water for a set period of time with variable speed orbital agitation. The test method was adapted from the Quebec DOT method ("The Evaluation of Binder Resistance to Stripping for a Given Aggregate Surface," Quebec Department of Transportation, 2002). A suitable orbital agitation speed can be 1 to 300 rpm, e.g., 100 to 200 rpm. A suitable test time can be 1 to 48 hours, e.g., 6 to 24 hours. Mix agitation simulates potential water damage in paving mixtures and accounts for the mechanism of water-induced migration and potential stripping of the bitumen-coated aggregate. The percentage of bitumen coating retained on the aggregate was then visually assessed by quantifying the bitumen-coated rock, where 90% coated rock is considered a pass, as opposed to uncoated rock. In this example, a stirring speed of 200 rpm, a test temperature of 60° C., and a test time of 25 hours were used on a 75 gram asphalt mix sample prepared as described.

[0129] In this example, all mineral aggregates used were graded to a size range of 4.75 mm to 9.5 mm. The aggregates were washed under running water on a sieve to remove any debris and dust that could interfere with the aggregate's surface coverage, and then dried in a forced-draft oven at 100°C. These processes were followed to reduce variability in the test results recorded by the Quebec DOT method. This procedure is an improvement over the current Quebec DOT stripping test. The prepared asphalt binder contained 99.5 wt% bitumen and 0.5 wt% warm-mix additive blend (asphalt additive blend). The asphalt binder blend was prepared by heating the binder to 150°C in a forced-draft oven, adding the appropriate weight of room-temperature additives, and blending for 30 seconds using a metal spatula. 3.2 wt% asphalt binder, based on the weight of the aggregate, was further combined with the mineral aggregate and blended for 2 minutes. The additive dosage level may depend on the aggregate's mineral properties, such as its surface chemistry and grade. The asphalt binder-aggregate mix was then placed in a forced-air oven at 150°C to ensure uniform coating of the aggregate. This procedure was repeated 4-5 times until the mix was uniformly dispersed. The completed blend was then transferred to a flat surface, spread evenly, and allowed to cure for 24 hours. Approximately 75 g of material and 100 g of water were transferred to a 120 mL bottle and placed on an orbital shaker table to evaluate the asphalt mix's strippability.

[0130] The asphalt binder used in this example was a standard paving grade binder called PG 64-22. The aggregate used contained 53.97% CaCO3. Table 4 shows the measured results from two replicate tests, along with the associated average. For blends, the "predicted" performance was calculated as a weighted linear average of the performance of each individual component in the asphalt mix. If no synergistic interactions occurred as a result of blending the components, the measured results would be expected to be statistically similar to the predicted results.

[0131] As shown in Table 6, the 1 / 1 SL / ELO additive exhibited anti-stripping performance greater than the linear average of the individual performances of the SL and ELO additives. Surprisingly, the 2:2:1 SL / ELO / Sf.SBO blend exhibited comparable anti-stripping performance (i.e., no statistically significant loss) compared to the 1:1 SL / ELO blend, both in the low-shear and high-shear blend versions. This is an unexpected but important result, demonstrating that the addition of Sf.SBO not only enabled the preparation of low-shear stable blends of SL and ELO, but also did so without any degradation in performance or product efficiency.

[0132] [Table 7]

[0133] Example 5 - Evaluation of the synergistic anti-stripping properties of Sf.SBO addition to SL / ELO asphalt additives in asphalt applications. Anti-stripping performance was evaluated using a shaker table peel test as previously described. As shown in Table 7, both the 1:1 SL / ELO and 2:7:1 SL / ELO / Sf.SBO additives exhibited anti-stripping performance greater than the linear average of the individual performances of the SL, ELO, and / or Sf.SBO additives. This is an unexpected but important result, demonstrating that the addition of Sf.SBO not only enabled the preparation of stable SL and ELO blends with high ELO content at high shear, but also did so without compromising performance or product efficiency.

[0134] Overall, Sf.SBO was added without affecting the performance efficiency of the asphalt additive in asphalt applications.

[0135] [Table 8]

[0136] As shown in Examples 3A-3C, 4, and 5, the incorporation of Sf.SBO not only demonstrated the additive's performance efficiency in asphalt applications, but also significantly improved stability compared to that of the binary blends.

[0137] Exemplary Embodiments The following exemplary aspects of the present invention are set forth in the following sections, the numbering of which is not to be construed as designating a level of importance: 1. An asphalt additive comprising: a phospholipid material; an epoxidized renewable oil or fat having an oxirane content of about 1.0% to about 15.0%; and a sulfurized renewable oil stabilizer, wherein the sulfurized renewable oil stabilizer is a polymer distribution having an oligomer content of from about 2 weight percent (wt%) to about 80 wt%, and a sulfur content ranging from about 0.001 wt% to about 8 wt%, An asphalt additive, wherein the sulfurized renewable oil stabilizer is a polymerized oil obtained by sulfurization. 2. The asphalt additive according to item 1, wherein the asphalt additive comprises a weight ratio of the phospholipid material to the epoxidized renewable oil or fat of about 5:1 to about 1:5. 3. The asphalt additive according to item 1 or 2, wherein the asphalt additive comprises a weight ratio of the phospholipid material to the epoxidized renewable oil or fat of about 3:1 to about 1:3. 4. The asphalt additive according to any one of items 1 to 3, wherein the asphalt additive comprises a weight ratio of the phospholipid material to the epoxidized renewable oil or fat of about 2:1 to about 1:2. 5. The asphalt additive according to any one of paragraphs 1 to 4, wherein the asphalt additive comprises a weight ratio of about 1:1 phospholipid material to epoxidized renewable oil or fat. 6. The asphalt additive according to any one of items 1 to 5, wherein the asphalt additive comprises from about 10.0 wt% to about 80.0 wt% of the phospholipid material, based on the total weight of the asphalt additive. 7. The asphalt additive according to any one of paragraphs 1 to 6, wherein the asphalt additive comprises from about 10.0 wt% to about 60.0 wt% of the phospholipid material, based on the total weight of the asphalt additive. 8. The asphalt additive according to any one of paragraphs 1 to 7, wherein the phospholipid material comprises at least about 50 wt% to 100 wt% phospholipid, based on the total weight of the phospholipid material. 9. The asphalt additive according to any one of paragraphs 1 to 8, wherein the phospholipid material comprises at least about 80 wt% to 100 wt% phospholipid, based on the total weight of the phospholipid material. 10. The asphalt additive according to any one of items 1 to 9, wherein the phospholipid comprises a natural phospholipid, a synthetic phospholipid, or a combination thereof. 11. The asphalt additive according to item 10, wherein the natural phospholipids include phospholipids derived from plant, animal, or microbial sources. 12. The asphalt additive of any one of paragraphs 1 to 11, wherein the phospholipid material comprises phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidic acid, or a combination thereof. 13. The asphalt additive according to any one of items 1 to 12, wherein the phospholipid material comprises a lecithin material. 14. The asphalt additive of claim 13, wherein the lecithin material comprises about 5 wt% to about 100 wt% acetone-insoluble matter. 15. The asphalt additive according to any one of paragraphs 1 to 14, wherein the lecithin material comprises soybean lecithin, rapeseed lecithin, sunflower seed lecithin, egg lecithin, peanut lecithin, corn lecithin, bovine brain lecithin, jojoba lecithin, or a mixture thereof. 16. The asphalt additive of any one of paragraphs 1 to 15, wherein the additive comprises from about 10.0 wt% to about 80.0 wt% of an epoxidized renewable oil or fat, based on the total weight of the asphalt additive. 17. The asphalt additive of any one of paragraphs 1 to 16, wherein the epoxidized renewable oil or fat has an oxirane content of about 4.0% to about 12.0%. 18. The asphalt additive of any one of paragraphs 1 to 17, wherein the epoxidized renewable oil or fat has an oxirane content of about 6.0% to about 10.0%. 19. The asphalt additive of any one of paragraphs 1 to 18, wherein the epoxidized renewable oil or fat has an oxirane content of about 8.0% to about 10.0%. 20. The asphalt additive according to any one of items 1 to 19, wherein the epoxidized renewable oil or fat comprises an epoxidized fatty acid or fatty acid derivative. 21. The asphalt additive according to paragraph 20, wherein the epoxidized fatty acid or fatty acid derivative comprises an epoxidized vegetable oil, an epoxidized acetylated acylglyceride, an epoxidized glycidyl ether, an epoxidized fatty acid ester, an estolide, or a mixture thereof. 22. The asphalt additive according to any one of items 1 to 21, wherein the epoxidized renewable oil or fat is selected from the group consisting of epoxidized soybean oil, epoxidized canola oil, epoxidized linseed oil, epoxidized soybean methyl ester, epoxidized linseed methyl ester, epoxidized tall oil fatty acid (TOFA), epoxidized acetylated triacylglycerol, epoxidized acetylated diacylglycerol, epoxidized acetylated monoacylglycerol, epoxidized jojoba oil, epoxidized 2-ethylhexyl soyate, epoxidized 2-ethylhexyl TOFA, epoxidized isoamyl soyate, epoxidized isoamyl palm stearin, epoxidized isoamyl TOFA, epoxidized isoamyl soyate, epoxidized soybean methyl ester acetate estolide, and mixtures thereof. 23. The asphalt additive of any one of paragraphs 1 to 22, wherein the epoxidized renewable oil or fat comprises epoxidized linseed oil, epoxidized soybean oil, or a mixture thereof. 24. The asphalt additive according to any one of paragraphs 1 to 22, wherein the epoxidized renewable oil or fat comprises epoxidized linseed oil. 25. The asphalt additive according to any one of paragraphs 1 to 22, wherein the epoxidized renewable oil or fat comprises epoxidized soybean oil. 26. The asphalt additive according to any one of paragraphs 1 to 25, wherein the epoxidized renewable oil or fat has undergone fractionation. 27. The asphalt additive of any one of paragraphs 1 to 26, wherein the asphalt additive comprises up to about 35 wt. % of a sulfurized renewable oil stabilizer, based on the total weight of the asphalt additive. 28. The asphalt additive of any one of paragraphs 1 to 27, wherein the asphalt additive comprises about 1 wt. % to about 35 wt. % of the sulfurized renewable oil stabilizer, based on the total weight of the asphalt additive. 29. The asphalt additive of any one of paragraphs 1 to 28, wherein the asphalt additive comprises about 16 wt% to about 22 wt% of the sulfurized renewable oil stabilizer, based on the total weight of the asphalt additive. 30. The asphalt additive of any one of paragraphs 1 to 29, wherein the sulfurized renewable oil stabilizer has a polymer distribution of about 55 wt% to about 75 wt% oligomer content. 31. The asphalt additive of any one of paragraphs 1 to 30, wherein the sulfurized renewable oil stabilizer has a sulfur content of about 2 wt% to about 6 wt%. 32. The asphalt additive according to any one of paragraphs 1 to 31, wherein the sulfurized renewable oil stabilizer further has a PDI of about 1.0 to about 5.0, preferably about 1.30 to about 2.20. 33. The asphalt additive according to any one of paragraphs 1 to 32, wherein the sulfurized renewable oil stabilizer has a flash point in the range of about 100°C to about 400°C. 34. The asphalt additive according to any one of claims 1 to 33, wherein the sulfurized renewable oil stabilizer is a polymerization product of a reaction mixture comprising a sulfur-containing compound and a starting renewable oil or fat, and the polymerization is sulfurization. 35. The asphalt additive of paragraph 34, wherein the starting renewable oil or fat is selected from the group consisting of palm oil, sunflower oil, corn oil, soybean oil, canola oil, rapeseed oil, linseed oil, tung oil, castor oil, tall oil, cottonseed oil, peanut oil, safflower oil, corn stillage oil, and combinations thereof. 36. The asphalt additive according to paragraph 34 or 35, wherein the sulfur-containing compound comprises elemental sulfur. 37. The asphalt additive of any one of paragraphs 1 to 35, wherein the asphalt additive comprises a weight ratio of phospholipid material, epoxidized renewable oil or fat, and sulfurized renewable oil stabilizer of 45:45:1 to 1:1:1. 38. The asphalt additive of any one of paragraphs 1 to 36, wherein the asphalt additive comprises a weight ratio of phospholipid material, epoxidized renewable oil or fat, and sulfurized renewable oil stabilizer of 10:10:2 to 2:2:1. 39. The asphalt additive of any one of paragraphs 1 to 38, further comprising a fatty acid material, wherein the fatty acid material comprises soybean oil, linseed oil, canola oil, or a mixture thereof. 40. The asphalt additive of paragraph 27, wherein the additive comprises from about 0.1 wt% to about 40 wt% of the fatty acid material, based on the total weight of the additive. 41. The asphalt additive of paragraph 39 or 40, wherein the fatty acid material has undergone fractionation. 42. The asphalt additive of any one of paragraphs 39 to 41, wherein the additive comprises from about 1 wt. % to about 35 wt. % of the fatty acid material, based on the total weight of the additive. 43. The asphalt additive according to any one of items 1 to 42, wherein the asphalt additive is a warm mix asphalt additive. 4. The asphalt additive according to any one of items 1 to 43, wherein the asphalt additive is a hot mix asphalt additive. 45. The asphalt additive of any one of paragraphs 1 to 44, wherein the asphalt additive improves one or more performance characteristics in asphalt applications, including adhesion, compaction, durability, anti-stripping, or a combination thereof. 46. ​​The asphalt additive of any one of paragraphs 1 to 45, wherein the asphalt additive exhibits improved stability compared to an asphalt additive that does not contain one or more of a phospholipid material, an epoxidized renewable fat or oil, or a sulfurized renewable oil stabilizer. 47. Use of an asphalt additive according to any one of paragraphs 1 to 46 to reduce or prevent spalling in asphalt applications. 48. Use of the asphalt additive according to any one of paragraphs 1 to 46 as a compaction aid in asphalt applications. 49. Use of an asphalt additive according to any one of paragraphs 1 to 46 to promote adhesion in asphalt applications. 50. Use of the asphalt additive according to any one of paragraphs 1 to 46 as a warm mix asphalt additive or a hot mix asphalt additive in asphalt applications. 51. Bitumen and Item 47. An asphalt binder comprising the asphalt additive according to any one of Items 1 to 46. 52. The asphalt binder according to paragraph 51, wherein the asphalt binder comprises from about 0.1 wt% to about 3.0 wt% of the asphalt additive, based on the total weight of the asphalt binder. 53. The asphalt binder according to paragraph 51 or 52, wherein the asphalt binder comprises about 0.3 wt% to about 0.7 wt% of the asphalt additive, based on the total weight of the asphalt binder. 54. The asphalt binder of any one of paragraphs 51 to 53, wherein the asphalt binder comprises about 97.0 wt% to about 99.9 wt% bitumen, based on the total weight of the asphalt binder. 55. The asphalt binder of any one of paragraphs 51 to 54, further comprising one or more additional additives. 56. The asphalt binder according to any one of items 51 to 55, further comprising polyphosphoric acid. 57. Asphalt concrete, About 0.25 wt% to about 8.0 wt% asphalt binder, based on the total weight of the asphalt concrete, Bitumen and An asphalt binder comprising the asphalt additive according to any one of items 1 to 46; and an asphalt concrete comprising: a mineral aggregate; 58. The asphalt concrete of paragraph 57, wherein the asphalt concrete comprises about 92.0 wt% to about 99.75 wt% mineral aggregate, based on the total weight of the asphalt concrete. 59. A method for preparing a stable asphalt additive blend, comprising: mixing a phospholipid material, an epoxidized renewable oil or fat having an oxirane content of about 1.0% to about 15.0%, and a sulfurized renewable oil stabilizer to obtain an asphalt additive blend; Sulfurized renewable oil stabilizer a polymer distribution having an oligomer content of from about 2 weight percent (wt%) to about 80 wt%; Optionally, a polydispersity index (PDI) in the range of about 1.0 to about 5.0, and a sulfur content ranging from about 0.001 wt% to about 8 wt%, The method wherein the sulfurized renewable oil stabilizer is a polymerized oil obtained by sulfurization. 60. The method of claim 59, wherein the asphalt additive comprises a weight ratio of phospholipid material, epoxidized renewable oil or fat, and sulfurized renewable oil stabilizer of 45:45:1 to 1:1:1. 61. The method of paragraph 59 or 60, wherein the asphalt additive blend comprises a weight ratio of phospholipid material, epoxidized renewable oil or fat, and sulfurized renewable oil stabilizer of 10:10:2 to 2:2:1. 62. The method of any one of paragraphs 59 to 61, wherein mixing comprises blending at a shear rate of about 600 rpm to about 1500 rpm. 63. The method of any one of paragraphs 59 to 61, wherein the mixing comprises blending at a shear rate of greater than 1500 rpm. 64. The method of any one of paragraphs 59 to 61, wherein mixing comprises blending at a shear rate of greater than 1500 rpm to about 3500 rpm. 65. The method of claim 64, wherein the mixing comprises blending at a shear rate of about 3000 rpm to about 3500 rpm. 66. The method of any one of paragraphs 59 to 65, wherein the asphalt additive blend exhibits improved stability compared to an asphalt additive that does not include one or more of the phospholipid material, the epoxidized renewable fat or oil, or the sulfurized renewable oil stabilizer. 67. The asphalt additive of any one of paragraphs 59 to 66, wherein the asphalt additive blend improves one or more performance characteristics in asphalt applications, including adhesion, compaction, durability, anti-stripping, or a combination thereof. 68. The method of any one of paragraphs 59 to 67, wherein the asphalt additive blend is a warm mix asphalt additive. 69. The method of any one of paragraphs 59 to 67, wherein the asphalt additive blend is a hot mix asphalt additive. 70. A method for preparing an asphalt binder, comprising: 47. A method comprising combining bitumen with the asphalt additive of any one of paragraphs 1 to 46. 71. The method of paragraph 70, further comprising combining one or more additional additives with the bitumen and asphalt additive. 72. A method for reducing or preventing spalling, promoting adhesion, aiding compaction, and / or improving durability of asphalt concrete, comprising: Combining the asphalt additive according to any one of items 1 to 46 with bitumen to obtain an asphalt binder; combining the asphalt binder with the mineral aggregate to obtain asphalt concrete; The method, wherein the asphalt binder comprises from about 0.25 wt% to about 8.0 wt% of the asphalt concrete.

[0138] Thus, the examples provided herein demonstrate that the asphalt additives of the present technology exhibit improved storage stability compared to asphalt additives that do not contain the combination of a phospholipid material, an epoxidized renewable oil or fat, and a sulfurized renewable oil stabilizer. Additionally, the asphalt additives of the present technology exhibit synergistic anti-stripping properties.

[0139] Each of the above non-limiting aspects may stand alone or may be combined in various permutations or combinations with one or more of the other aspects or other subject matter described herein. While the present invention has been illustrated and described in certain aspects, those skilled in the art may, after reading the foregoing specification, make modifications, equivalent substitutions, and other types of alterations to the technology described herein. Each of the above aspects may also include or be incorporated with variations or aspects as disclosed with respect to any or all of the other aspects.

[0140] The present technology should also not be limited in terms of the specific embodiments described herein, which are intended as single examples. As will be apparent to those skilled in the art from the foregoing description, many modifications and variations of the present technology can be made without departing from the spirit and scope of the technology. Such modifications and variations are intended to fall within the scope of the appended claims. It is understood that the present technology is not limited to particular methods, reagents, compounds, or compositions, which may, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only, and is not intended to be limiting. Therefore, it is intended that the specification be considered only as exemplary, with the breadth, scope, and spirit of the technology being indicated only by the appended claims, the definitions therein, and any equivalents thereof.

[0141] The embodiments illustratively described herein may suitably be practiced in the absence of any element(s), limitation(s) not specifically disclosed herein. Thus, for example, terms such as "comprising," "including," and "containing" shall be read expansively and without limitation. Furthermore, the terms and phrases used herein are used as terms of description and not of limitation, and the use of such terms and phrases is not intended to exclude any equivalents of the shown and described features or portions thereof, but recognizes that various modifications are possible within the scope of the claimed technology. Furthermore, the phrase "consisting essentially of" is understood to include the elements specifically recited and additional elements that do not materially affect the basic and novel characteristics of the claimed technology. The phrase "consisting of" excludes any elements not specified.

[0142] Furthermore, when features or aspects of the present disclosure are described in terms of a Markush group, one of skill in the art will recognize that the present disclosure is also described in terms of any individual member or subgroup of members of the Markush group. Each of the narrower species and subgeneric groupings falling within the generic disclosure also form part of the invention. This includes generic descriptions of the invention with conditions or negative limitations that remove any subject matter from the genus, whether or not the deleted material is specific.

Claims

1. An asphalt additive comprising: a phospholipid material; an epoxidized renewable oil or fat having an oxirane content of from about 1.0% to about 15.0%; and a sulfurized renewable oil stabilizer, wherein the sulfurized renewable oil stabilizer is a polymer distribution having an oligomer content of about 2 weight percent (wt%) to about 80 wt%, and a sulfur content ranging from about 0.001 wt % to about 8 wt %; An asphalt additive, wherein the sulfurized renewable oil stabilizer is a polymerized oil obtained by sulfurization.

2. 10. The asphalt additive of claim 1, wherein the asphalt additive comprises a weight ratio of the phospholipid material to the epoxidized renewable oil or fat of from about 5:1 to about 1:5, preferably from about 3:1 to about 1:3, more preferably from about 2:1 to about 1:2, and most preferably about 1:

1.

3. 3. The asphalt additive of claim 1 or 2, wherein the asphalt additive comprises from about 10.0 wt % to about 80.0 wt %, preferably from about 10.0 wt % to about 60.0 wt %, of the phospholipid material, based on the total weight of the asphalt additive.

4. The asphalt additive of any one of claims 1 to 3, wherein the phospholipid material comprises a lecithin material.

5. 5. The asphalt additive of any one of claims 1 to 4, wherein the lecithin material comprises soybean lecithin, rapeseed lecithin, sunflower seed lecithin, egg lecithin, peanut lecithin, corn lecithin, bovine brain lecithin, jojoba lecithin, or mixtures thereof.

6. 6. The asphalt additive of any one of claims 1 to 5, wherein the additive comprises from about 10.0 wt% to about 80.0 wt% of the epoxidized renewable oil or fat, based on the total weight of the asphalt additive.

7. 7. The asphalt additive of any one of claims 1 to 6, wherein the epoxidized renewable oil or fat has an oxirane content of from about 4.0% to about 12.0%, preferably from about 6.0% to about 10.0%, and most preferably from about 8.0% to about 10.0%.

8. 8. The asphalt additive of any one of claims 1 to 7, wherein the epoxidized renewable oil or fat comprises epoxidized soybean oil, epoxidized canola oil, epoxidized linseed oil, epoxidized soybean methyl ester, epoxidized linseed methyl ester, epoxidized tall oil fatty acid (TOFA), epoxidized acetylated triacylglycerol, epoxidized acetylated diacylglycerol, epoxidized acetylated monoacylglycerol, epoxidized jojoba oil, epoxidized 2-ethylhexyl soyate, epoxidized 2-ethylhexyl TOFA, epoxidized isoamyl soyate, epoxidized isoamyl palm stearin, epoxidized isoamyl TOFA, epoxidized isoamyl soyate, epoxidized soybean methyl ester acetate estolide, or mixtures thereof.

9. 9. The asphalt additive of any one of claims 1 to 8, wherein the asphalt additive comprises up to about 35 wt%, preferably from about 1 wt% to about 35 wt%, and most preferably from about 16 wt% to about 22 wt% of the sulfurized renewable oil stabilizer, based on the total weight of the asphalt additive.

10. Item 10. The asphalt additive according to any one of items 1 to 9, wherein the sulfurized renewable oil stabilizer further has a PDI of about 1.0 to about 5.0, preferably about 1.30 to about 2.

20.

11. 11. The asphalt additive of any one of claims 1 to 10, wherein the asphalt additive comprises a weight ratio of the phospholipid material, the epoxidized renewable oil or fat, and the sulfurized renewable oil stabilizer of from 45:45:1 to 1:1:1, preferably from 10:10:2 to 2:2:

1.

12. The asphalt additive of any one of claims 1 to 11, wherein the asphalt additive is a warm mix asphalt additive or a hot mix additive.

13. 13. The asphalt additive of any one of claims 1 to 12, wherein the asphalt additive improves one or more performance characteristics in asphalt applications, including adhesion, compaction, durability, anti-stripping, or a combination thereof.

14. 14. The asphalt additive of any one of claims 1 to 13, wherein the asphalt additive exhibits improved stability compared to an asphalt additive that does not include one or more of the phospholipid material, the epoxidized renewable fat or oil, or the sulfurized renewable oil stabilizer.

15. Use of the asphalt additive of any one of claims 1 to 14 to reduce or prevent delamination in asphalt applications, as a compaction aid in asphalt applications, to promote adhesion in asphalt applications, as a warm mix asphalt additive in asphalt applications, or as a hot mix asphalt additive in asphalt applications.

16. An asphalt binder, Bitumen and and the asphalt additive of any one of claims 1 to 14, preferably in an amount of from about 0.1 wt% to about 3.0 wt%, and most preferably from about 0.3 wt% to about 0.7 wt%, based on the total weight of the asphalt binder.

17. 17. The asphalt binder of claim 16, wherein the asphalt binder comprises from about 97.0 wt% to about 99.9 wt% bitumen, based on the total weight of the asphalt binder.

18. Asphalt concrete, about 0.25 wt % to about 8.0 wt % asphalt binder, based on the total weight of the asphalt concrete; Bitumen and An asphalt binder comprising the asphalt additive according to any one of claims 1 to 14; and about 92.0 wt % to about 99.75 wt % mineral aggregate, based on a total weight of the asphalt concrete.

19. 1. A method for preparing a stable asphalt additive blend, comprising: mixing a phospholipid material, an epoxidized renewable oil or fat having an oxirane content of about 1.0% to about 15.0%, and a sulfurized renewable oil stabilizer to obtain the asphalt additive blend; The sulfurized renewable oil stabilizer is a polymer distribution having an oligomer content of from about 2 weight percent (wt%) to about 80 wt%; optionally, a polydispersity index (PDI) in the range of about 1.0 to about 5.0; and a sulfur content ranging from about 0.001 wt % to about 8 wt %; The method wherein the sulfurized renewable oil stabilizer is a polymerized oil obtained by sulfurization.

20. 20. The method of claim 19, wherein said mixing comprises blending at a shear rate of from about 600 rpm to about 1500 rpm, or greater than 1500 rpm, preferably greater than 1500 rpm to about 3500 rpm, and most preferably from about 3000 rpm to about 3500 rpm.

21. 1. A method for preparing an asphalt binder, comprising: A method comprising combining bitumen with the asphalt additive of any one of claims 1 to 14.

22. 1. A method for reducing or preventing spalling, promoting adhesion, aiding compaction, and / or improving durability of asphalt concrete, comprising: Combining the asphalt additive of any one of claims 1 to 14 with bitumen to obtain an asphalt binder; combining the asphalt binder with mineral aggregate to obtain asphalt concrete; The method, wherein the asphalt binder comprises from about 0.25 wt % to about 8.0 wt % of the asphalt concrete.

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