Bitumen composition including amidoamine

Abstract

A bitumen composition includes bitumen, an amidoamine that is the reaction product of a dialkyl aminoalkylamine and an oil wherein the oil includes three fatty acid residues each independently having from about 12 to about 22 carbon atoms and also includes a glycerol residue; and wherein at least about 80 mol% of a total of the fatty acid residues is free of a carbon-carbon double bond.

Description

PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCBITUMEN COMPOSITION INCLUDING AMIDOAMINECROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of U.S. Provisional Application No. 63 / 790,182, filed April 17, 2025, the entirety of which is expressly incorporated herein by reference.TECHNICAL FIELD

[0002] The present disclosure generally relates to a bitumen composition that includes bitumen and a particular amidoamine. More specifically, the amidoamine is the reaction product of a dialkyl aminoalkylamine and a certain oil.BACKGROUND

[0003] Bituminous or asphalt paving materials are commonly used in road construction and maintenance due to their durability, flexibility, and cost-effectiveness. Traditional hot mix asphalt (HMA) relies on high temperatures, typically from about 140°C to about 180°C, e.g. to achieve a certain level of workability, compaction and physical performance. However, these high temperatures can lead to increased energy consumption, emissions of volatile organic compounds (VOCs), and oxidative aging of the asphalt binder, i.e. bitumen, which can negatively impact pavement performance.

[0004] To address these concerns, warm mix asphalt (WMA) technologies have been developed which can allow asphalt mixtures to be produced and utilized at lower temperatures than typical HMA. One strategy for achieving WMA includes foaming, which introduces water into HMA thereby expanding the HMA such that its viscosity temporarily decrease, allowing mixing with aggregates and paving at a lower temperature. However, foaming utilizes specialized equipment in the field and even with precise water control, pavement durability may be compromised. Alternatively, various additives may be utilized to enhance asphalt workability at warm mix temperatures. For example, chemical additives, such as those derived from synthetic wax, e.g. wax from coal or natural gas processing, etc., may be used. However, certain chemical additives can affect asphalt binder properties, leading to issues in compact performance, which can reduce density, strength, durability, etc. of the asphalt.

[0005] Despite the advantages of existing WMA technologies, there is a continuing demand for innovative additives that optimize the balance between reduced mixing temperatures and asphalt performance. Accordingly, there remains opportunities for improvement.PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCBRIEF SUMMARY

[0006] This disclosure provides a bitumen composition including bitumen and an amidoamine that is the reaction product of a dialkyl aminoalkylamine and an oil. More specifically, the oil includes three fatty acid residues each independently having from about 12 to about 22 carbon atoms and also includes a glycerol residue. Moreover, at least about 80 mol% of a total of the fatty acid residues is free of a carbon-carbon double bond.

[0007] This disclosure further provides a paving material including the aggregate and the bitumen composition.

[0008] This disclosure also provides a method of forming the paving material. The method includes the steps of providing the aggregate, providing the bitumen composition, and combining the aggregate and the bitumen composition at a temperature of from about 100 to about 150 °C to form the paving material.DETAILED DESCRIPTION

[0009] The following detailed description is merely exemplary in nature and is not intended to limit compositions described herein. Furthermore, there is no intention to be bound by any theory presented in the preceding background or the following detailed description.

[0010] Embodiments of the present disclosure are generally directed to chemical compounds, compositions including the same, and methods for forming the same. For the sake of brevity, conventional techniques related to making chemical compounds and such compositions may not be described in detail herein. Moreover, the various tasks and process steps described herein may be incorporated into a more comprehensive procedure or process having additional steps or functionality not described in detail herein. In particular, various steps in the manufacture of chemical compounds and associated compositions are well-known and so, in the interest of brevity, many conventional steps will only be described briefly herein or will be omitted entirely without providing the well-known process details.

[0011] In this disclosure, the terminology “about” can describe values ±0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10%, in various embodiments. Moreover, it is contemplated that, in various nonlimiting embodiments, it is to be appreciated that all numerical values as provided herein, save for the actual examples, are approximate values with endpoints or particular values intended to be read as “about” or “approximately” the value as recited. It is also contemplated that allPCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCisomers and chiral options for each compound described herein are hereby expressly contemplated for use herein in various non-limiting embodiments.

[0012] Throughout this disclosure, the terminology percent "actives" is well recognized in the art and means the percent amount of active or actual compound or molecule present as compared to, for example, a total weight of a diluted solution of a solvent and such a compound. Some compounds, such as a solvent, are not described relative to a percent actives because it is well known to be approximately 100% actives. Any one or more of the values described herein may be alternatively described as percent actives as would be understood by the skilled person.

[0013] In various embodiments, the terminology “free of’ describes embodiments that include less than about 5, 4, 3, 2, 1, 0.5, or 0.1, weight percent (or weight percent actives) of the compound or element at issue using an appropriate weight basis as would be understood by one of skill in the art. In other embodiments, the terminology “free of’ describes embodiments that have zero weight percent of the compound or element at issue.

[0014] The terminology “consists essentially of’ may describe various non-limiting embodiments that are free of one or more optional compounds described herein and / or free of one or more chemical compounds, surfactants, additives, solvents, etc.

[0015] The chemical compounds and compositions disclosed herein may suitably comprise, consist of, or consist essentially of the components, elements, and process delineations described herein. The embodiments illustratively disclosed herein suitably may be practiced in the absence of any element which is not specifically disclosed herein.

[0016] This disclosure provides a bitumen composition including bitumen and an amidoamine that is the reaction product of a dialkyl aminoalkylamine and an oil. In various embodiments, the bitumen composition includes bitumen and the amidoamine. In various other embodiments, the bitumen composition consists of bitumen and the amidoamine. In yet other embodiments, the bitumen composition consists essentially of bitumen and the amidoamine. The bitumen composition may be further described as an asphalt composition, and may be used for various applications, e.g. as a binder for aggregate in hot mix asphalt, warm mix asphalt, or cold mix asphalt for road construction, pavement repair, and other surfacing applications, etc. In various embodiments, the bitumen composition is further described as bitumen for warm mix asphalt.PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCBitumen:

[0017] The bitumen composition includes bitumen. The terminology “bitumen” may be used to describe a dark brown to black cementitious material that can occur in nature or are obtained in petroleum processing, e.g. derived from crude oil. Bitumen may be further described as asphalt, asphalt binder, etc. Bitumen can typically include asphaltenes, maltenes, resins, saturates, aromatics, etc.

[0018] The bitumen herein is not particularly limited and may be any known in the art. The bitumen may be or include conventional bitumen and / or modified bitumen, e.g. modified with SBS, SBR, etc. The bitumen may be naturally occurring, synthetically manufactured, and / or derived from recovered materials. Naturally occurring bitumen may include native rock bitumen, lake bitumen, etc. Synthetically manufactured bitumen may include a byproduct of petroleum refining or post refining operations and includes air-blown bitumen, blended bitumen, cracked or residual bitumen, petroleum bitumen, propane bitumen, straight-run bitumen, thermal bitumen, etc. Modified bitumen may be or include neat bitumen, e.g. unmodified bitumen that can be naturally occurring or synthetically manufactured, modified with various components. Recovered materials can include, or be free of, bitumen from reclaimed asphalt pavement (RAP), recycled asphalt shingle (RAS), recycled roofing, and / or waterproofing membranes, etc.

[0019] The bitumen may be further described in terms of a penetration grade, a viscosity grade and / or a performance grade (PG), which can describe conditions under which the bitumen can be used. These conditions can typically include climate conditions, aging conditions, etc. In various embodiments, the PG can be assessed using various tests and the bitumen can pass a test at a specific temperature, a specific climatic condition, etc.

[0020] In various embodiments, the bitumen has a PG grade of PG 64-22, i.e. bitumen passes performance tests at a temperature of from about -22 °C to about 64 °C and may be graded for use in moderate climates having cold winters and hot summers. In other embodiments, the bitumen has a PG grade of PG 58-28, PG 76-22, PG 52-34, and / or PG 70-28, etc. Alternatively, the bitumen may pass a PG performance test at a temperature of from about -50 to about 100 °C, alternatively from about -40 to about 90, about -30 to about 80, about -20 to about 70, about -10 to about 60, about 0 to about 50, about 10 to about 40, or about 20 to about 30, °C. InPCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCvarious non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0021] A PG performance test may be performed using any method known in the art, e.g. using an aging simulation test including but not limited to a rolling thin film oven, pressure aging vessel, a resistance to thermal cracking test, e.g. using a bending beam rheometer, a direct tension test, etc., a resistance to fatigue cracking test, e.g. using a dynamic shear rheometer, a pressure aging vessel, etc., a resistance to rutting test, e.g. using a rotational viscosity test, a dynamic shear rheometer, etc. The test may be performed at a temperature in one or more ranges as described above.

[0022] The PG performance test may be performed according to a standardized method, including but not limited to AASHTO M320, AASHTO M332, AASHTO T316, AASHTO T315, AASHTO T313, AASHTO T314, AASHTO T240, AASHTO R28, etc., each as published in 2025. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0023] The bitumen is typically present in the bitumen composition in an amount of from about 90 to about 99.9, wt% based on a total weight of the bitumen composition. In various embodiments, the bitumen is present in an amount of from about 90 to about 99.9, about 90 to about 99.5, about 90 to about 99, about 90.5 to about 98.5, about 91 to about 98, about 91.5 to about 97.5, about 92 to about 97, about 92.5 to about 96.5, about 93 to about 96, about 93.5 to about 95.5, or about 94 to about 95, wt% based on a total weight of the bitumen composition. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.Amidoamine:

[0024] The bitumen composition further includes the amidoamine. The amidoamine may be further described as a bitumen additive, and asphalt additive, a warm mix additive, etc. The amidoamine may be used for various purposes, e.g. to improve adhesion of the bitumen composition and aggregate materials, improve water resistance of pavements, to modify working conditions of the bitumen, etc. For example, in various embodiments, the amidoamine is utilized to decrease mixing and / or paving temperatures of HMA by about 10 to about 50 °C,PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCthereby reducing energy consumption and improving workability of paving materials. In various embodiments, the amidoamine is utilized to decrease mixing and / or paving temperatures of HMA by about 10 to about 50, about 15 to about 45, about 20 to about 40, about 25 to about 35, or about 25 to about 20, °C. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0025] The amidoamine is the reaction product of a dialkyl aminoalkylamine and an oil. The dialkyl aminoalkylamine is not particularly limited and may be any known in the art. Typically, the dialkyl aminoalkylamine has a dialkyl residue having from about 1 to about 18 carbon atoms, e.g. from about 2 to about 17, about 3 to about 16, about 4 to about 15, about 5 to about 14, about 6 to about 13, about 7 to about 12, about 8 to about 11, or about 9 to about 10, about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms carbon atoms. Additionally, the dialkyl aminoalkylamine can have an aminoalkyl residue having from about 2 to about 4 carbon atoms, e.g. about 2 to about 3, about 3 to about 4, about 2, about 3, or about 4, carbon atoms. In various embodiments, the dialkyl aminoalkylamine is or includes dimethyl aminopropyl amine (DMAPA). In other embodiments, the dialkyl aminoalkylamine is or includes diethyl aminopropyl amine, diisopropyl aminopropyl amine, dibutyl aminopropyl amine, dimethyl aminoethyl amine, diethyl aminoethyl amine, diisopropyl aminoethyl amine, dibutyl aminoethyl amine, etc. and combinations thereof. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0026] The oil typically includes a glycerol residue and three fatty acid residues. Each fatty acid residue independently has from about 12 to about 22 carbon atoms, e.g. from about 13 to about 21, about 14 to about 20, about 15 to about 19, about 16 to about 18, about 16 to about 17, or about 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22 carbon atoms. Each fatty acid residue may independently be derived from various natural and / or synthetic fatty acids known in the art. For example, each fatty acid residue may be derived from a fatty acid chosen from lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, palmitoleic acid, oleic acid, gondoic acid, erucic acid, linoleic acid, etc. and combinations thereof. In various embodiments, one or more of the fatty acid residue is a stearic acids residue. In various non-PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PClimiting embodiments, all values and ranges of values, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0027] Each fatty acid residue may include, or be free of, a carbon-carbon double bond, so long as at least about 80 mol% of a total of the fatty acid residues is free of a carbon-carbon double bond. It is contemplated that the aforementioned amount of carbon-carbon double bonds, or lack thereof, when utilized the bitumen composition, can increase the workability of the bitumen, allowing for mixing with aggregates and compacting for various paving applications to be performed at a lower temperature compared to HMA conditions.

[0028] In various embodiments, about 80 to about 100 mol% of a total of the fatty acid residues is free of a carbon-carbon double bond. In other embodiments, from about 81 to about 99, alternatively from about 82 to about 98, about 83 to about 97, about 84 to about 96, about 85 to about 95, about 86 to about 94, about 87 to about 93, about 88 to about 92, about 89 to about 91, or about 89 to about 90, mol% of a total of the fatty acid residues is free of a carboncarbon double bond. The fatty acid residue and / or the oil may be further described as being hydrogenated, hardened, etc. The oil may naturally include the at least about 80 mol% of a total of the fatty acid residues that is free of a carbon-carbon double bond. Alternatively, the oil may or may not undergo hydrogenation, i.e., reaction with H2, e.g. to reduce the number of carbon-carbon double bonds. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0029] The oil may be, include, or be free of, an oil derived from plants, e.g. rapeseed oil, peanut oil, avocado oil, flaxseed oil, soybean oil, etc. from animal fat, e.g. lard, tallow, duck fat, etc. In various embodiments, the oil is rapeseed oil. In other embodiments, the rapeseed oil is further described as hardened rapeseed oil.

[0030] The reaction of the oil and the dialkyl aminoalkylamine can be performed using any reaction condition, e.g. reaction temperature, reaction pressure, the oil to the dialkyl aminoalkylamine molar ratio, etc., as chosen by the skilled person. In various embodiments, the reaction of the oil and the dialkyl aminoalkylamine is performed at a temperature of from about 100 to about 300, about 110 to about 290, about 120 to about 280, about 130 to about 270, about 140 to about 260, about 150 to about 250, about 160 to about 240, about 170 to about 230, about 180 to about 220, about 190 to about 210, or about 190 to about 200, °C. In otherPCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCembodiments, the reaction of the oil and the dialkyl aminoalkylamine is performed at a pressure of from about 1 bar, i.e. ambient pressure, to about 10 bar, e.g. about 1 to about 9, about 2 to about 8, about 3 to about 7, about 4 to about 6, or about 4 to about 5, bar. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0031] In various embodiments, the reaction of the oil and the dialkyl aminoalkylamine may be performed at a molar ratio of actives of the oil to the dialkyl aminoalkylamine of from about 9:1 to about 1:9, alternatively from about 8:2 to about 2:8, about 7:3 to about 3:7, about 6:4 to about 4:6, or about 6:4 to about 5:5. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0032] In various embodiments, the reaction of the oil and the dialkyl aminoalkylamine can follow the reaction scheme (I) as set forth below. For convenience and ease of illustration, the reaction scheme includes DMAPA as the dialkyl aminoalkylamine. The skilled person appreciates that any dialkyl aminoalkylamine may be used to form the reaction product, i.e. the amidoamine.wherein each of R1, R2and R3is a fatty acid residue, e.g. as first described above, and each of R1, R2and R3may be the same as, or different from, one another.

[0033] The bitumen composition may include, or be free of, a salt of the reaction product. For example, the salt may be formed by further reacting the reaction product with an acid, e.g. via a neutralization reaction. The acid used can be any acid known in the art. For example, the acid may be an organic acid and / or an inorganic acid. In various embodiments, the acid is aPCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCbiobased acid. In other embodiments, the acid is an organic acid. The acid may have from about 1 to about 22 carbon atoms. In various embodiments, the acid has 1 to 22, 2 to 21, 3 to 20, 4 to 19, 5 to 18, 6 to 17, 7 to 16, 8 to 15, 9 to 14, 10 to 13, or 11 to 12 carbon atoms. In other embodiments, the acid is chosen from lactic acid, glycolic acid, tartaric acid, malic acid, citric acid, and combinations thereof. In one embodiment, the acid is lactic acid. In another embodiment, the acid is citric acid. In various non-limiting embodiments, all values and ranges of values, including and between those set forth above are hereby expressly contemplated for use herein.

[0034] In various embodiments, the dialkyl aminoalkylamine is dimethyl aminopropylamine and the reaction product, i.e. the amidoamine, has the structure (II):O R5R4N R6H (II)wherein R4is CnH(2n+i) and n is about 13 to about 21, and each R5and R6is independently a fatty acid residue having of from about 1 to about 18 carbon atoms. In various embodiments, R4is a residue of 11-hydroxy-heptadecyl. Alternatively, R4may be a radical derived from a non-hydrogenated triglyceride. In various embodiments, n is from about 13 to about 21, about 14 to about 20, about 15 to about 19, about 16 to about 18, or about 17 to about 18. In other embodiments, n is 13, 14, 15, 16, 17, 18, 19, 20, or 21. In various non-limiting embodiments, all values and ranges of values, including and between those set forth above are hereby expressly contemplated for use herein.

[0035] In one non-limiting embodiment, the reaction conditions are as follows: about 0.35 mole of the hydrogenated oil and about 1.05 moles of the dialkyl aminoalkylamine are added to flask fitted with a reflux condenser, a mechanical stirrer, a thermometer, nitrogen inlet and a heating mantel to form a reaction mixture. The reaction may be performed at a temperature of from about 200 to about 210 °C, e.g. about 200 to about 205, or about 205 to about 210, °C. The reaction may be performed for a time duration of from about 5 to about 20 hours, e.g. about 5 to about 10, about 10 to about 20, or about 5 to about 15, hours. Subsequently, the reaction can be stopped and cooled to a temperature of from about 90 to about 110 °C, e.g. about 95 to about 105, about 90 to about 100, or about 90 to about 95, about 100 to about 110, °C. ThePCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCproduct can be analyzed using any method known in the art, typically usingXH NMR,13C NMR, IR spectroscopy, etc. The product can have an appearance of a beige solid. The product can exhibit a melting point of from about 50 to 80, about 55 to 75, or about 60 to about 65, °C. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those set forth above are hereby expressly contemplated for use herein.

[0036] The amidoamine may be utilized in various amounts, typically depending on the type of bitumen, weather conditions, etc. In various embodiments, the amidoamine is present in the bitumen composition in an amount of from about 0.1 to about 5 wt%, based on a total weight of the bitumen composition. In other embodiments, the amidoamine is present in an amount of from about 0.1 to about 5, about 0.5 to about 4.5, about 1 to about 4, about 1.5 to about 3.5, about 2 to about 3, or about 2 to about 2.5. In yet other embodiments, the amidoamine is present in an amount of from about 0.1 to about 1, about 0.2 to about 0.9, about 0.3 to about 0.8, about 0.4 to about 0.7, or about 0.5 to about 0.6, wt%, based on a total weight of the bitumen composition. In various non-limiting embodiments, all values and ranges of values, including and between those set forth above are hereby expressly contemplated for use herein.Physical Properties of the Bitumen Composition:

[0037] The bitumen composition may exhibit various physical properties, which can be customized for various paving applications. The presence of the amidoamine can decrease viscosity of the bitumen composition such that the bitumen composition can have a particular workability, adhesion, etc. at a reduced temperature compared to a typical working temperature range of a hot mix asphalt.

[0038] In various embodiments, the bitumen composition exhibits a viscosity of from about 50 to about 500 cP, typically measured at a temperature of from about 100 to about 150 °C. The viscosity of the bitumen composition may be measured using any method known in the art, such as using a rotational viscometer, using a dynamic shear rheometer, using a capillary viscometer, etc., at a temperature of from about 100 to about 150 °C, alternatively from about 110 to about 140, or about 120 to about 130, °C, at a shear rate of from 0.1 to about 100 s’1, alternatively from about 0.1 to about 100, about 0.1 to about 10, about 1 to about 10, or about 10 to about 100, s’1. In various non-limiting embodiments, all values and ranges of values, including and between those set forth above are hereby expressly contemplated for use herein. The viscosity of the bitumen composition may be measured according to a standardized method,PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCe.g. ASTM D4402, AASHTO T316, ASTM D7175, AASHTO T315, ASTM D2171, ASTM D36, AASHTO T53, ASTM D5, AASHTO T49, each as published in 2025.

[0039] In various embodiments, the viscosity of the bitumen composition, measured using any one of the aforementioned methods, at a temperature and / or shear rate in the ranges described above, is from about 50 to about 500 cP, alternatively from about 100 to about 450, about 150 to about 400, about 200 to about 350, or about 250 to about 300, cP. In other embodiments, the viscosity is from about 50 to about 100, about 55 to about 95, about 60 to about 90, about 65 to about 85, about 70 to about 80, or about 75 to about 80, cP. In various non-limiting embodiments, all values and ranges of values, including and between those set forth above are hereby expressly contemplated for use herein.Paving Material

[0040] This disclosure also provides a paving material. The paving material may be further described as an asphalt mix, an asphalt concrete, a hot mix asphalt, a warm mix asphalt, a cold mix asphalt, a blacktop, etc. The paving material includes an aggregate and the bitumen composition.

[0041] The aggregate is not particularly limited and may be any known in the art. The terminology “aggregate” may be used to describe mineral materials, typically in a granulated form, e.g. sand, gravel, or crushed stone that are combined with the asphalt binder to form the asphalt paving material. The aggregate may be or include natural aggregate, manufactured aggregate, or a combination thereof. Natural aggregate is typically extracted rock from an open excavation, e.g. a quarry, that is reduced to customized sizes by mechanical crushing. Manufactured aggregate can be a byproduct of other manufacturing processes such as slag from metallurgical processing (e.g. steel, tin, and copper production). Manufactured aggregate also includes specialty materials that are produced to have a particular physical characteristic not found in natural rocks. The aggregate may optionally include a recycled asphalt pavement (RAP), which can help reduce costs and environmental impact by reusing existing materials. In various embodiments, the aggregate may be or include crushed stone, gravel, sand, recycled pavement (rap), granite, limestone, slate, basalt, river rock, porous aggregates, quarry dust, concrete rubble, blast furnace slag, cinder, expanded clay aggregate, or combinations thereof.

[0042] In various embodiments, the RAP is present in the aggregate in an amount of from about 0 to about 100 wt%, based on a total weight on the aggregate. In various embodiments ,PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCthe RAP is present in an amount of from about 0.1 to about 99.9, about 0.5 to about 99.5, about 1 to about 99, about 5 to about 95, about 10 to about 90, about 15 to about 85, about 20 to about 80, about 25 to about 75, about 30 to about 70, about 35 to about 65, about 40 to about 60, about 45 to about 55, or about 45 to about 50, wt%, based on a total weight of the aggregate. In other embodiments, the RAP is present in an amount of from about 0 to about 30, about 1 to about 25, about 2 to about 20, about 3 to about 15, about 4 to about 10, about 5 to about 9, about 6 to about 8, or about 7 to about 8, wt%, based on a total weight of the aggregate. In various nonlimiting embodiments, all values and ranges of values, including and between those set forth above are hereby expressly contemplated for use herein.

[0043] In various embodiments, the aggregate is present in the paving material, in an amount of from about 90 to about 99, wt%, based on a total weight of the paving material. In other embodiments, the aggregate is present in an amount of from about 90 to about 99, about 90.5 to about 98.5, about 91 to about 98, about 91.5 to about 97.5, about 92 to about 97, about 92.5 to about 96.5, about 93 to about 96, about 93.5 to about 95.5, or about 94 to about 95, wt%, based on a total weight of the paving material. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, both between and including each of the above, are hereby expressly contemplated for use herein.Additives

[0044] The bitumen composition and / or the paving material may include, or be free of, one or more additives. For example, the additive may be or include a filler such as hydrated lime, cement, fly ash, calcium carbonate, silica, clay, etc., which may enhance adhesion between the bitumen and the aggregate, improve moisture resistance, increase resistance to stripping, etc. In addition, the additive may be, or include, a polymer that can improve flexibility, elasticity, etc. of the bitumen, such as styrene-butadiene-styrene (SBS), ethylene-vinyl acetate (EVA), etc. The additive may be provided separately, and / or as a part of another component.

[0045] In various embodiments, the additive is present in the bitumen composition in an amount of from about 0 to about 10 wt%, based on a total weight of the bitumen composition. In other embodiments, the additive is present in an amount of from about 0.1 to about 10, about 0.5 to about 9, about 1 to about 8, about 2 to about 7, about 3 to about 6, or about 4 to about 5, wt%, based on a total weight of the bitumen composition. In various non-limiting embodiments,PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCall values and ranges of values, both whole and fractional, both between and including each of the above, are hereby expressly contemplated for use herein.Method of Forming the Paving Material:

[0046] This disclosure further includes the method of forming the paving material. The method includes the steps of providing the aggregate, providing the bitumen composition, and combining the aggregate and the bitumen composition at a temperature of from about 100°C to about 180°C, e.g. about 100°C to about 150°C to form the paving material. The steps may be performed in any order as deemed appropriate by the skilled person. Furthermore, the steps may be performed sequentially or concurrently.

[0047] The step of providing the aggregate is not particularly limited and may be any known in the art. The aggregate may be acquired from an external source and / or manufactured inhouse. In various embodiments, the step of providing the aggregate may be further described as loading the aggregate into a mixing equipment, e.g. a mixing drum or a pugmill, etc. The aggregate may be provided in whole or in part.

[0048] Referring back, the aggregate may include RAP. Accordingly, the step of providing the aggregate may further include, or be free of, the step of sourcing the RAP, processing the RAP, which may include crushing the RAP, e.g. to form small uniform particulates, combining the RAP with another aggregate, etc.

[0049] The method further includes the step of providing the bitumen composition. The step of providing the bitumen composition is not particularly limited. In various embodiments, the step of providing the bitumen composition may include the step of forming the bitumen composition, e.g. by combining the bitumen, the amidoamine and / or any additive. In various embodiments, the step of providing the bitumen composition is further described as loading the aggregate into a mixing equipment, e.g. a mixing drum or a pugmill, etc. The bitumen composition may be provided in whole or in part.

[0050] The step of combining is not particularly limited. For example, the aggregate, the bitumen composition and / or any additive may be combined in part or in whole. The step of combining may be performed continuously or batches. In various embodiments, the step of combining can be in a central plant, e.g. batch plant or continuous mix plant. In other embodiments, the step of combining may be performed directly on-site using a mobile mixing unit and / or manually.PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PC

[0051] The step of combining may be performed at a temperature of from about 100 to about 180 °C. The temperature of the paving material may be measured using any known method in the art, e.g. using an infrared thermometer, a thermocouple, etc. In various embodiments, the step of combining is performed at a temperature of from about 100 to about 175, about 100 to about 170, about 100 to about 165, about 100 to about 160, about 100 to about 155, about 100 to about 150, alternatively from about 105 to about 145, about 110 to about 140, about 115 to about 135, about 120 to about 130, or about 120 to about 125, °C. In various nonlimiting embodiments, all values and ranges of values, both whole and fractional, both between and including each of the above, are hereby expressly contemplated for use herein.

[0052] The step of combining may be further described as mixing the aggregate, the bitumen composition and / or any additive, which may be performed for various amounts of time, e.g. depending on the temperature of the paving material, amount of RAP, additives included, type of mixing plant used, etc. Typically, the step of mixing may be performed for a time period of from about 1 to about 100 s, alternatively, from about 2 to about 90 s, about 3 to about 80 s, about 4 to about 70 s, about 5 to about 60 s, about 6 to about 55 s, about 7 to about 50 s, about 8 to about 45 s, about 9 to about 40 s, about 10 to about 35 s, about 10 to about 30 s, about 15 to about 25 s, or about 15 to about 20 s. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, both between and including each of the above, are hereby expressly contemplated for use herein.

[0053] In various embodiments, the method further includes, or is free of, the step of adjusting the paving material, e.g. to achieve a certain physical performance. In yet other embodiments, the method includes, or is free of, the step of heating and / or maintaining a temperature of the paving material to or at a temperature of from about 100 to about 180, about 100 to about 175, about 100 to about 170, about 100 to about 165, about 100 to about 160, about 100 to about 155, about 100 to about 150, about 110 to about 140, or about 120 to about 130 °C, etc. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, both between and including each of the above, are hereby expressly contemplated for use herein.Physical Properties of the Paving Material:

[0054] The paving material is not particularly limited regarding physical properties. For example, the bitumen composition and the paving material may have any physical properties,PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCsome of which may be described herein. However, the bitumen composition and paving material are not required to have any of the physical properties described herein.Compaction:

[0055] Paving performance of the paving material may be determined using a compaction test. The compaction test may be used to measure how well the paving material can be compacted, which can affect its density, strength, and durability. Generally, successful compaction can be identified by an increase in density of compacted paving material. Compaction tests may be performed at WMA and / or HMA conditions, as deemed fit by the skilled person.

[0056] The density of the paving material may be determined using any method and / or instrument known in the art. For example, the density may be measured using a superpave gyratory compactor, a nuclear density gauge, ground penetrating radar, infrared thermography, volumetric measurement, etc. In other embodiments, one or more standardized may be used, e.g. EN 12697, ASTM D2726, ASTM D2950 / D2950M-22, etc., each as published in 2025. In various embodiments, the density is measured using a gyratory compaction test.

[0057] Results of gyratory compaction tests may depend on various conditions / parameters of testing. For example, results may vary depending on height and / or diameter of bitumen samples, the type / model of the compactor, its rotational speed, number of gyro rotational cycles, angle of incline, temperature of compaction, etc.

[0058] In various non-limiting embodiments, the gyratory compaction test is performed by first preparing the paving material by pouring aggregate (heated at or to a temperature of from about 100 to about 180 °C) into a pug mill and mixed for 30 seconds followed by addition of the bitumen composition and blended for about 30 s to form the paving material. The pavement material may be divided into tins and baked in the oven at about 100 °C for about 2.5 hours before compacting. A gyro mold may also be baked at 100 °C and loaded with the paving material and compacted at 100°C with 200 gyro rotation cycle at about 0.6 MPa and at an angle of about 1.24 degree of the angle.

[0059] In various other embodiments, the gyratory compaction test is performed by first heating the aggregate to reach a temperature of from about 100 to about 180, about 100 to about 160 °C, about 110 to about 150, about 120 to about 140, or about 120 to about 130, °C, and mixing for a time duration of from about 10 to about 60 s, about 10 to about 50, about 20 toPCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCabout 40, or about 20 to about 30, s. In other embodiments, the bitumen composition is combined with the aggregate and blended for a time duration of from about 10 to about 60 s, about 10 to about 50, about 20 to about 40, or about 20 to about 30, s. In yet other embodiments, the paving material is baked in the oven at a temperature of from about 70 to about 180, about 70 to about 150, e.g. about 80 to about 140, about 90 to about 130, about 100 to about 120, or about 100 to about 110, °C for a time duration of from about 1 to about 5 hours, about 2 to about 4, about 2 to about 3, about 2.5 to about 3, hours before compacting. In still other embodiments, the paving material is compacted into a gyro mold heated at or to a temperature of from about 70 to about 180, about 70 to about 150, e.g. about 80 to about 140, about 90 to about 130, about 100 to about 120, or about 100 to about 110, °C. In various embodiments, the gyratory compaction test is performed at a force of from about 0.2 to about 1 mPa, e.g. about 0.3 to about 0.9, about 0.4 to about 0.8, about 0.5 to about 0.7, or about 0.6 to about 0.7, MPa, and at an angle of incline of from about 1 to about 2 degree, e.g. about 1.1 to about 1.9, about 1.2 to about 1.8, about 1.3 to about 1.7, about 1.4 to about 1.6, about 1.4 to about 1.5, degree. Depending on the force of the gyratory compaction test and components included in the paving material, the gyratory compaction test can be performed for a total of from about 10 to about 500 cycles, about 50 to about 450, about 100 to about 400, about 150 to about 350, or about 200 to about 300 cycles. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, both between and including each of the above, are hereby expressly contemplated for use herein.

[0060] The compaction results may be described as density of the paving material achieved after a certain number of gyro rotation cycle(s). A greater density can indicate a more effective compaction performance. The presence of the amidoamine in the bitumen composition can improve the density of the paving material produced and compacted at WMA conditions. In various embodiments, the density measured using the aforementioned method, after 200 gyro rotation cycles, is from about 1800 to about 2500 g / m3. In various embodiments, the density is from about 1850 to about 2450, about 1900 to about 2400, about 1950 to about 2350, about 2000 to about 2300, about 2050 to about 2250, about 2100 to about 2200, g / m3. In various nonlimiting embodiments, all values and ranges of values, both whole and fractional, both between and including each of the above, are hereby expressly contemplated for use herein.PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PC

[0061] In the alternative, the compaction results may be described as a rate of densification, which measures changes in density achieved after a certain number of gyro rotation cycle(s). In various embodiments, the rate of densification achieved from cycle 4 to cycle 8, i.e. initial compaction phase, is from about 10 to about 15 %, about 10.5 to about 14.5, about 11 to about 13.5, about 11.5 to about 13, or about 12 to about 13, %. In other embodiments, the rate of densification achieved from cycle 8 to cycle 50, i.e. primary compaction phase, is from about 1 to about 5 %, about 1.5 to about 4.5, about 2 to about 4, about 2.5 to about 3.5, or about 3 to about 4, %. In yet other embodiments, the rate of densification achieved from cycle 100 to cycle 160, i.e. final compaction phase, is from about 0.1 to about 1 %, about 0.2 to about 0.9, about 0.3 to about 0.8, about 0.4 to about 0.7, or about 0.5 to about 0.6, %. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, both between and including each of the above, are hereby expressly contemplated for use herein.

[0062] The presence of the amidoamine may further improve compaction performance by limiting air trapped in the paving material, i.e. air void, during and / or post compaction, while still including enough air void to allow material expansion from weather and pavement usage. Air void may be tested using any one of the methods described above. Typically, the paving material may have an amount of air void of from about 3 to about 8 volume %, about 3.5 to about 7.5, about 4 to about 7, about 4.5 to about 6.5, or about 5 to about 6, volume %, based on a total volume of the paving material after compaction.

[0063] The skilled person appreciates that measuring the density, densification rate, amount of air void, etc. of the paving material during the compaction process, i.e. at an earlier gyro rotational cycle, e.g. after cycle 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 20, 30, 40, 50, 100, 150, 160, 170, etc. may help monitor / determine the performance at different compaction phases, i.e. initial, primary, and final compaction phase. Compaction results may change as more gyro rotational cycles are performed, and therefore, it is also contemplated that the density, densification rate, etc. may have a value outside the ranges described above.EXAMPLESFormation of the Paving Materials (PM)

[0064] Various paving materials (PM) were formed using aggregate (ABT 11 asphalt concrete formed at the Swedish National Road and Transport Research Institute VTI withPCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCSkarlunda granite in Norrkbping, Sweden, stored at 130 °C) and bitumen (penetration bitumen commercially obtained as Nynas 70 / 100 from Nynas AB, store at 160°C).

[0065] To form PM 1, i.e. an exemplary embodiment, about 0.6 wt% of amidoamine was combined with bitumen to form a bitumen composition, followed by combining about 6.0 wt% of the bitumen compositions with the aggregate, followed by a stirring step performed for about 30 seconds and a baking step about at 160 °C for about 30 minutes. More specifically, the aggregate was poured in a pug mill and mixed for 30 seconds before the bitumen composition was added. When all bitumen had been combined, the mixture of the aggregate and the bitumen composition were blended for 30 seconds more to form the paving materials. PM 2, i.e. a comparative example / a reference, was formed using the same protocol as PM 1 but no additive is included. The amidoamine used for PM 1 is reported in Table 1 below.Table 1. Additives included in the paving materialsPM Additive1 amidoamine derived from DMAPA and C18 fatty acid2 N / AGyratory Compaction Test:

[0066] PM’s 1 and 2 were utilized for gyratory compaction test. Prior to the compaction test, the pug mill was emptied, and the asphalt mix was put on a tray and divided into tins, each having about 1600 g of paving material. The tins were baked at about 100°C for about 2.5 hours. Additionally, a 150 mm gyro mold was baked at about 100 °C and was loaded with about 1192 g of the paving material and compacted by 200 gyro rotations, 0.6 MPa and 1.24 degree of the angle, at about 100 °C.

[0067] The paving materials were produced and compacted at the same temperature at a WMA condition of about 130 °C for production and at about 100 °C for compaction. Additionally, PM 2, which included no additive and served as a reference, was also tested at a HMA condition of about 160 °C for production and about 130 °C for compaction. The density of the paving material at various stages, i.e. gyro rotational cycles, are measured and recorded in Table 2.Table 2. Densities of paving materials at various gyro rotational cycles.PM 2 PM 2 Cycles PM 1 (g / m3)(WMA condition) (HMA condition)PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PC4 2000 + 11 1991 + 8 1997 + 128 2052 + 11 2043 + 8 2046 + 11 50 2202 + 11 2189 + 12 2192 + 10100 2254 + 12 2240 + 12 2246 + 9 160 2285 + 13 2272 + 12 2280 + 9200 2298 + 13 2286 + 13 2294

[0068] The densities obtained at a specified cycle in Table 2 are used to compare performance of PM 1 which includes the amidoamine and PM 2, which is free of the amidoamine, at both WMA and HMA conditions. PM 1, produced and compacted at WMA conditions, exhibited greater density values compared to PM 2, which were produced and compacted at both WMA and HMA conditions, across all cycles.Volumetric Test:

[0069] The densities of PM’s 1 and 2 were also measured using a volumetric test, according to SS-EN 12697-6, as published in 2025.Table 3. Densities of paving materials measured using volumetric test.Paving Material (PM) Mean (kg / m3) Stdev2 (WMA condition) 2.327 0.0082 (HMA condition) 2.326 0.0041 2.333 0.009

[0070] Overall, the density of PM 1 is greater than the density of PM 2 at each cycle examined, at both WMA and HMA conditions, whether measured using the gyratory compaction testing method or the volume testing method. The results in Tables 2 and 3 demonstrate that while the presence of the amidoamine, e.g. amidoamine derived from DMAPA and C18 fatty acid, enhances the densification of the paving material and demonstrates potential of the amidoamine as a warm mix additive, e.g. to improve compaction performance for various paving applications.

[0071] While at least one exemplary embodiment has been presented in the foregoing detailed description, it should be appreciated that a vast number of variations exist. It should also be appreciated that the exemplary embodiment or exemplary embodiments are only examples, and are not intended to limit the scope, applicability, or configuration in any way. Rather, the foregoing detailed description will provide those skilled in the art with a convenient road mapPCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCfor implementing an exemplary embodiment. It being understood that various changes may be made in the function and arrangement of elements described in an exemplary embodiment without departing from the scope as set forth in the appended claims.

Claims

PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCCLAIMSWhat is claimed is:

1. A bitumen composition comprising:bitumen; andan amidoamine that is the reaction product of a dialkyl aminoalkylamine and an oil;wherein the oil comprises three fatty acid residues each independently having from about 12 to about 22 carbon atoms and also comprises a glycerol residue; andwherein at least about 80 mol% of a total of the fatty acid residues is free of a carbon-carbon double bond.

2. The bitumen composition of claim 1 wherein any one or more of the three fatty acid residues has from about 16 to about 18 carbon atoms.

3. The bitumen composition of claim 1 or 2 wherein the bitumen is present in an amount of from about 90 to about 99.9 wt%, based on a total weight of the bitumen composition.

4. The bitumen composition of any one of the preceding claims wherein the amidoamine is present in an amount of from about 0.1 to about 5 wt%, based on a total weight of the bitumen composition.

5. The bitumen composition of any one of the preceding claims wherein the dialkyl aminoalkylamine is dimethyl aminopropyl amine.

6. The bitumen composition of any one of the preceding claims wherein the oil is chosen from rapeseed oil, peanut oil, avocado oil, flaxseed oil, soybean oil, lard, tallow, duck fat, and combinations thereof.

7. The bitumen composition of any one of the preceding claims wherein the oil is rapeseed oil.PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PC8. The bitumen composition of any one of the preceding claims wherein any one or more of the three fatty acid residues is a stearic acid residue.

9. A paving material comprising:an aggregate; anda bitumen composition comprising:bitumen; andan amidoamine that is the reaction product of a dialkyl aminoalkylamine and an oil;wherein the oil comprises three fatty acid residues each independently having from about 12 to about 22 carbon atoms and also comprises a glycerol residue; andwherein at least about 80 mol% of a total of the fatty acid residues is free of a carbon-carbon double bond.

10. The paving material of claim 9 wherein the aggregate comprises a reclaimed asphalt pavement material.

11. The paving material of any one of claims 9 to 10 wherein the aggregate is present in an amount of from about 90 to about 99 %, based on a total weight of the paving material.

12. The paving material of any one of claims 9 to 11 wherein the dialkyl aminoalkylamine is dimethyl aminopropyl amine.

13. The paving material of any one of claims 9 to 12 wherein the oil is rapeseed oil.

14. A method of forming a paving material, said method comprising the steps of:providing an aggregate;providing a bitumen composition comprising:bitumen; andan amidoamine that is the reaction product of a dialkyl aminoalkylamine and an oil;PCT PATENT APPLICATIONATTORNEY DOCKET NO. 364.1761PCwherein the oil comprises three fatty acid residues each independently having from about 12 to about 22 carbon atoms and also comprises a glycerol residue; andwherein at least about 80 mol% of a total of the fatty acid residues is free of a carbon-carbon double bond.combining the aggregate and the bitumen composition at a temperature of from about 100 to about 160 °C to form the paving material.

15. The method of claim 14 wherein the aggregate comprises a reclaimed asphalt pavement material.

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