Adhesion promoters comprising phenolic compounds and methods of using the same

Abstract

Non-amine. bio-based antistrips are described herein. Exemplary applications include the use of novel antistrips to enhance the adhesion of asphalt binders to aggregates.

Description

[0001] ADHESION PROMOTERS COMPRISING PHENOLIC COMPOUNDS AND

[0002] METHODS OF USING THE SAME

[0003] PRIORITY CLAIM TO RELATED APPLICATIONS

[0004] This application claims the right of priority to U.S. Provisional Patent Application number 63 / 574,925 filed on April 5, 2024, which is hereby incorporated by reference herein in its entirety.

[0005] FIELD

[0006] The present disclosure relates to phenolic compounds and compositions, and the use of phenolic compounds as adhesion promoters. Exemplary uses include, but are not limited to, the treatment of mineral aggregates with phenolic-based compounds to promote adhesion of asphaltic compounds.

[0007] BACKGROUND

[0008] A wide variety of petroleum compounds have been used for the impregnation and surface treatmen t of aggregates to improve adhesion of other materials, such as asphal t binders.However, there are very few, if any, biobased adhesion promoters. Accordingly, there remains a need to develop improved, biobased adhesion promoters.

[0009] SUMMARY

[0010] Described herein are compositions comprising phenolic analogs (e.,g., phenolic esters) and a substrate. In certain embodiments, the substrate is an aggregate material, and a phenolic compound can permit better adhesion of bituminous materials to the aggregate for use in asphalt applications. Moreover, in certain embodiments, such phenolic compounds may be particularly suitable for improving the adhesion of bituminous materials to wet substrates, such as aggregates having water content. Additional embodiments of the invention, as well as features and advantages thereof, will be apparent from the descriptions herein. BRIEF DESCRIPTION OF THE DRAWINGS

[0011] Fig. 1 shows a drawing of the chemical structure of lauryl gallate.

[0012] Fig. 2 shows digital images of limestone aggregates coated with lauryl gallate-treated asphalt binder after Texas boil tests. Fig. 3 shows a digital image of non-additized (left) and lauryl gallate modified (right) pills for comparison of fine-graded aggregate mixes coated at 180ºC (5.8% and 5.5% moisture, respectively).

[0013] Fig. 4 shows a digital image of loose fine-graded mix coated with lauryl gallate-modified emulsion. Fig. 5 shows a digital image of a compacted pill of lauryl gal late-modified emulsion with fine-graded mix.

[0014] Fig. 6 shows a gradation curve showing aggregate particle size distribution for a representati ve dense-graded mix.

[0015] DETAILED DESCRIPTION

[0016] For the purposes of promoting an. understanding of the principles of the invention, reference wi ll now be made to certain embodiments and specific language will be used to describe the same. It will nevertheless be understood that no limitation of the scope of the invention is thereby intended, such alterations and further modifications, and such further applications of the principles of the invention as described herein being contemplated as would normally occur to one skilled in the art to which the invention relates.

[0017] As used in the present specification, the following words, phrases and symbols are generally intended to have the meanings as set forth below, except to the extent that the context in which they are used indicates otherwise. The following abbreviations and terms have the indicated meanings throughout:

[0018] "Asphalt" refers to a composite material comprising a bituminous binder and aggregate, which is generally used for paving applications. Such asphalt is also known as "asphalt concrete. " Examples of asphalt grades used in paving applications include stone mastic asphalt, soft asphalt, hot rolled asphalt, dense-graded asphalt, gap-graded asphalt, porous asphalt, mastic asphalt, and other asphalt types. Typically, the total amount of bituminous binder in asphalt is from 1 to 10 wt.% based on the total weight of the asphalt, in some cases from 2.5 to 8.5 wt.% and in some cases from 4 to 7.5 wt.%,

[0019] "Aggregate" (or "construction aggregate") is particulate mineral material suitable for use in asphalt. It generally comprises sand, gravel, crushed stone, and slag. Any conventional type of aggregate suitable for use in asphalt can be used. Examples of suitable aggregates include granite (siliceous), limestone (calcareous), gravel, and mixtures thereof

[0020] "Bitumen" or (or a material described as ‘'bituminous”) refers to a mixture of viscous organic liquids or semi-solids from crude oil that is black, sticky, soluble in carbon disulfide, and composed primarily of condensed aromatic hydrocarbons. Alternatively, bitumen refers to a mixture of maltenes and asphaltenes. Bitumen may be any conventional type of bitumen known to the skilled person. The bitumen may be naturally occurring. It may be crude bitumen, or it may be refined bitumen obtained as the bottom residue from vacuum distillation of crude oil, thermal cracking, or hydrocracking. The bitumen may be commercially available virgin bitumen such as paving grade bitumen, e.g., bitumen suitable for paving applications. Examples of commercially available paving grade bitumen include, for instance, bitumen which in the penetration grade (PEN) classification system are referred to as PEN 10 / 20, 20 / 30, 30 / 45, 35 / 50, 40 / 60 and 70 / 100 or bitumen which in the performance grade (PG) classification system are referred to as PG 64- 22, 58-22, 70-22 and 64-28.

[0021] Such bitumen is available from, for instance, Shell, Total, and British Petroleum (BP). In the PEN classification, the numeric designation refers to the penetration range of the bitumen as measured with the EN 1426 method, e.g., a 40 / 60 PEN bitumen corresponds to a bitumen with a penetration which ranges from 40 to 60 decimillimeters (dmm). In the PG classification (AASHTO MP 1 specification ), the first value of the numeric designation refers to the temperature performance and the second value refers to the low -temperature performance as measured by a method which is known in the art as the SuperpaveSMsystem. The bitumen may also be contained in or obtained from reclaimed asphalt shingles or reclaimed asphalt pavement, and is referred to as bitumen of RAS or RAP origin, respectively,

[0022] "Binder" refers to a combination of bitumen and, optionally, other components such as elastomers, non-bituminous binders, adhesion promoters, softening agents, or other suitable additives. Useful elastomers include, for example, ethylene-vinyl acetate copolymers, polybutadienes, ethylene-propylene copolymers, ethylene-propylene-diene terpolymers, butadiene-styrene block copolymers, butadiene-sly rene-btrtadiene (i.e., butadiene end-capped) (BSB) copolymers, slyrene-butadiene-styrene (SBS) block terpolymers, isoprene-styrene block copolymers and styrene-isoprene-styrene (SIS) block terpolymers, or the like. Exemplary polymeric materials Include radial and linear block copolymers, such as those described in U.S. Patent No. 8,580,874, which is incorporated by reference in its entirety for all purposes. Cured elastomer additives may include ground tire rubber materials. In one embodiment, the additional additives may be added to an asphalt binder in amounts ranging from about 0.1 wt.% to about 10 wt.%. The term bitumen is sometimes used interchangeably with binder.

[0023] "Virgin binder" is binder that has not been used previously for road paving or

[0024] "Virgin bitumen" (also known as "fresh bitumen") refers to bitumen that has not been used, e.g., bitumen that has not been recovered from road pavement or reclaimed shingles. Virgin bitumen is a component of virgin binder,

[0025] "Virgin asphalt" refem to a combination of virgin aggregate with virgin bitumen or virgin binder. Virgin asphalt has not been used previously forpaving. "Reclaimed asphalt” generally includes reclaimed asphalt shingles (RAS), reclaimed asphalt pavement (RAP), reclaimed asphalt from plant waste, reclaimed asphalt from roofing felt, and asphalt from o ther applications.

[0026] "Reclaimed asphalt shingles” (RAS) are asphalt compositions that have been used previously as roofing material or have been recovered as waste from shingle manufacturing. RAS recovered from these sources is processed by well-known methods, inchiding milling, ripping, breaking, crushing, and / or pulverizing.

[0027] "Reclaimed asphalt pavement" (RAP) is asphalt that has been used previously as pavement. RAP may be obtained from asphalt that has been removed from a road or other structure, and then has been processed by well-known methods. Prior to use, the RAP may be inspected, sized and selected, for instance, depending on the final paving application.

[0028] A dash ("-") that is not between two letters or symbols is used to indicate a point of attachment for a substituent. For example, -C(O)NH2is attached through the carbon atom.

[0029] “Alkoxy” by itself or as part of another substi tuent refers to a radical -OR31where R31is alkyl, cycloalkyl, cycloalkylalkyl, aryl, or arylalkyl, which can be substituted, as defined herein. In some embodiments, alkoxy groups have from 1 to 8 carbon atoms. In some embodiments, alkoxy groups have 1 , 2, 3, 4, 5, 6, 7, or 8 carbon atoms. Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, butoxy, cyclohexyloxy, and the like.

[0030] “Alkyl” by itself or as part of another substituent refers to a saturated or unsaturated, branched, or straight-chain (linear) monovalent hydrocarbon radical derived by the removal of one hydrogen atom from a single carbon atom of a parent alkane, alkene, or alkyne. Examples of alkyl groups include, but are not limited to, methyl; ethyls such as ethanyl, ethenyl, and ethynyl; propyls such as propan-l-yl, propan-2-yl, prop-1-en-l-yl, prop-1 -en-2-yl, prop-2-en- 1-yl (allyl), prop- 1 -yn-1 -yl, prop-2-yn- 1-yl, etc. ; butyls such as butan-l -yl, butan-2-yl, 2-methyl-propan-l -yl, 2-methyl-propan-2-yI, but-l -en-l -yl, but- 1 -en-2-yl, 2 -methyl-prop- 1 -en- 1 -yl, but-2-en - 1 -yl , but-2-en-2-yl, buta- 1 ,3-dien- 1 -yl , buta-1,3-dien-2-yl, but-l-yn- l -yl, but-l-yn-3-yl, bul-3-yn-l-yl, etc. ; and the like.

[0031] Unless otherwise indicated, the term “alkyl” is specifically intended to include groups having any degree or level of saturation, i.e., groups having exclusively single carbon-carbon bonds, groups having one or more double carbon-carbon bonds, groups having one or more triple carbon-carbon bonds, and groups having mixtures of single, double, and triple carbon-carbon bonds. Where a specific level of saturation is intended, the terms “alkanyl,” “alkenyl,” and “alkynyl” are used. In certain embodiments, an alkyl group comprises from 1 to 40 carbon atoms, in certain embodiments, from 1 to 22 or 1 to 18 carbon atoms, in certain embodiments, from 1 to 16 or 1 to 8 carbon atoms, and in certain embodiments from 1 to 6 or 1 to 3 carbon atoms. In certain embodiments, an alkyl group comprises from 8 to 22 carbon atoms, in certain embodiments, from 8 to 18 or 8 to 16, In some embodiments, the alkyl group comprises from 3 to 20 or 7 to 17 carbons. In some embodiments, the alkyl group comprises 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , or 22 carbon atoms.

[0032] “Aryl” by itself or as part of another substituent refers to a monovalent aromatic hydrocarbon radical derived by the removal of one hydrogen atom from a single carbon atom of a parent aromatic ring system. Aryl encompasses 5- and 6-membered carbocyclic aromatic rings, for example, benzene; bicyclic ring systems wherein at least one ring is carbocyclic and aromatic, lor example, naphthalene, indane, and tetralin; and tricyclic ring systems wherein at least one ring is carbocyclic and aromatic, for example, fluorene. Aryl encompasses multiple ring systems having at least one carbocyclic aromatic ring fused to at least one carbocyclic aromatic ring, cycloalkyl ring, or heterocycloalkyl ring. For example, aryl includes 5- and 6-membered carbocyclic aromatic rings fused to a 5- to 7-membered non-aromatic heterocycloalkyl ring containing one or more heteroatoms chosen from N, O, and S. For such fused, bicyclic ring systems wherein only one of the rings is a carbocyclic aromatic ring, the point of attachment may be at the carbocyclic aromatic ring or the heterocycloalkyl ring. Examples of ary! groups include, but are not limited to, groups derived from aceantbrylene, acenaphthylene, acephenanthrylene, anthracene, azulene, benzene, chrysene, coronene, fluoranthene, fluorene, hexacene, hexaphene, hexalene, as-indacene, s- indacene, indane, indene, naphthalene, octacene, oclaphene, oclaiene, ovalene, penta-2,4- diene, pentacene, pentalene, pentaphene, perylene, phenalene, phenanthrene, picetie, pletadene, pyrene, pyranthrene, rubicene, triphenylene, trinaphthalene, and the like. In certain embodiments, an aryl group can comprise from 5 to 20 carbon atoms, and in certain embodiments, from 5 to 12 carbon atoms. In certain embodiments, an aryl group can comprise 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms. Aryl, however, does not encompass or overlap in any way with heteroaryl, separately defined herein. Hence, a multiple ring system in which one or more carbocyclic aromatic rings is fused to a heterocycloalkyl aromatic ring, is heteroaryl, not aryl, as defined herein. “Arylalkyl" by itself or as part of another substituent refers to an acyclic alkyl radical in which one of the hydrogen atoms bonded to a carbon atom, typically a terminal or sp3carbon atom, is replaced with an aryl group. Examples of arylalkyl groups include, but are not limited to, benzyl, 2-phenylethan-l -yl, 2-phenylethen-l -yl, naphthylmethyl, 2-naphthylethan-l-yl, 2-naphthyletben-l -yl, naphthobenzyl, 2-naphthophenylethan-l -yl, and the like. Where specific alkyl moieties are intended, the nomenclature arylalkanyl, arylalkenyl, or arylalkynyl is used. In certain embodiments, an arylalkyl group is C7-30arylalkyl, e.g., the alkanyl. alkenyl, or alkynyl moiety of the arylalkyl group is C1-10and the aryl moiety is C6-20, and in certain embodiments, an arylalkyl group is C7-20arylalkyl, e.g., the alkanyi, alkenyl, or alkynyl moiety of the arylalkyl group is C1-8and the aryl moiety is C6-12.

[0033] “Compounds” refers to compounds and residues encompassed by structural Formula I-II herein and includes any specific compounds within the formula whose structure is disclosed herein. Compounds may be identified either by their chemical structure and / or chemical name. When the chemical structure and chemical name conflict, the chemical structure is determinative of the identity of the compound. The compounds described herein may contain one or more chiral centers and / or double bonds and therefore may exist as stereoisomers such as double-bond isomers (i.e., geometric isomers), enantiomers, or diastereomers. Accordingly, any chemical structures within the scope of the specification depicted, in whole or in part, with a relative configuration encompass all possible enantiomers and stereoisomers of the illustrated compounds including the stereo isomerically pure form (e.g., geometrically pure, enantiomerically pure, or diastereomerically pure) and enantiomeric and stereoisomeric mixtures. Enantiomeric and stereoisomeric mixtures may be resolved into their component enantiomers or stereoisomers using separation techniques or chiral synthesis techniques well known to the skilled artisan.

[0034] For the purposes of the present disclosure, “chiral compounds” are compounds ha ving at least one center of chirality (i.e. at least one asymmetric atom, in particular at least one asymmetric C atom), having an axis of chirality, a plane of chiral ity or a screw structure. “Achiral compounds” are compounds which are not chiral.

[0035] Compounds and residues of Formula I-II include, but are not limited to, optical isomers of compounds and residues of Formula I-II, geometrical isomers of compounds and residues of Formula I-II, racemates thereof, and other mixtures thereof. In such embodiments, the single enantiomers or diastereomers, i.e., optically active forms, can be obtained by asymmetric synthesis or by resolution of the racemates. Resolution of the racemates may be accomplished by, for example, chromatography, using, for example a chiral high-pressure liquid chromatography (HPLC) column. However, unless otherwise stated, it should be assumed lhai Formula I-Il cover all asymmetric variants of the compounds described herein, including isomers, racemates, enantiomers, diastereomers, and other mixtures thereof. In addition, compounds of Formula I-II include Z- and E-forms (e.g., cis- and trans-forms) of compounds with double bonds. The compounds of Formula I-II may also exist in several tautomeric forms including the enol form, the keto form, and mixtures thereof. Accordingly, the chemical structures depicted herein encompass all possible tautomeric forms of the illustrated com po unds.

[0036] “Cycloalkyl” by itself or as part of another substituent refers to a saturated or unsaturated cyclic alkyl radical. Where a specific level of saturation is intended, the nomenclature “cycloalkanyl” or “cycloalkenyl” is used. Examples of cycloalkyl groups include, but are not limited to, groups derived from cyclopropane, cyclobutane, cyclopentane, cyclohexane, and the like. In certain embodiments, a cycloalkyl group is C3-15cycloalkyl, and in certain embodiments, C3-12cycloalkyl or C5-12cycloalkyl. In certain embodiments, a cycloalkyl group is a C5, C6, C7, C8, G9, C10, C11, C12, C13, C14, or C15cycloalkyl, “Cycloalkylalkyl” by itself or as part of another substituent refers to an acyclic alkyl radical in which one of the hydrogen atoms bonded to a carbon atom, typically a terminal or sp3carbon atom, is replaced with a cycloalkyl group. Where specific alkyl moieties are intended, the nomenclature cycloalkylalkanyl, cycloalkylalkenyl, or cycloalkylalkynyl is used. In certain embodiments, a cycloalkylalkyl group is C7-30cycloalkylalkyl, e.g., the alkanyl, alkenyl, or alkynyl moiety of the cycloalkylalkyl group is C1-10and the cycloalkyl moiety is C6-20, and in certain embodiments, a cycloalkylalkyl group is C7-20cycloalkylalkyl, e.g., the alkanyl, alkenyl, or alkynyl moiety of the cycloalkylalkyl group is C1-8and the cycloalkyl moiety is C4-20or C6-12. “Halogen” refers to a fluoro, chloro, bromo, or iodo group.

[0037] “Heteroaryl” by itself or as part of another substituent refers to a monovalent heteroaromatic radical derived by the removal of one hydrogen atom from a single atom of a parent heteroaromaiic ring system. Heteroaryl encompasses multiple ring systems having at least one aromatic ring fused to at least one other ring, which can be aromatic or nonaromatic in which at least one ring atom is a heteroatom. Heteroaryl encompasses 5- to 12- membered aromatic, such as 5- to 7-membered, monocyclic rings containing one or more, for example, from 1 to 4, or in certain embodiments, from 1 to 3, heteroatoms chosen from N, O, and S, with the remaining ring atoms being carbon; and bicyclic heterocycloalkyl rings containing one or more, for example, from 1 to 4, or in certain embodiments, from 1 to 3, heteroatoms chosen from N, O, and S, with tire remaining ring atoms being carbon and wherein at least one heteroatom is present in an aromatic ring, for example, heteroaryl includes a 5- to 7-membered heterocycloalkyl, aromatic ring fused to a 5- to 7-membered cycloalkyl ring. For such fused, bicyclic heteroaryl ring systems wherein only one of the rings contains one or more heteroatoms, the point of attachment may be at the heteroaromatic ring or the cycloalkyl ring. In certain embodiments, when the total number of N, S, and O atoms in the heteroaryl group exceeds one, the heteroatoms are not adjacent to one another. In certain embodiments, the total number of N, S, and O atoms in the heteroaryl group is not more than two. In certain embodiments, the total number of N, S, and O atoms in the aromatic heterocycle is not more than one. Heteroaryl does not encompass or overlap with aryl as defined herein.

[0038] Examples of heteroaryl groups include, but are not limited to, groups derived from acridine, arsindole, carbazole, β-carboline, chromane, chromene, cinnoline, furan, imidazole, indazole, indole, indoline, mdolizine, isobenzofuran, isochromene, isoindole, isoindoline, isoquinoline, isothiazole, isoxazole, naphthyridine, oxadiazole, oxazole, perimidine, phenanthridine, phenanthroline, phenazine, phthalazine, pteridine, purine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolizine, quioazoline, quinoline, quinolizine, quinoxaline, telrazole, thiadiazole, thiazole, thiophene, triazole, xanthene, and the like. In certain embodiments, a heteroaryl group is from 5- to 20-membered heteroaryl, and in certain embodiments from 5- to 12-membered heteroaryl or from 5- to 10-membered heteroaryl. In certain embodiments, a heteroaryl group is a 5-, 6-, 7-, 8-, 9-, 10-, 11 -, 12-, 13-,

[0039] 14-, 15-. 16-, 17-, 18-, 19-, or 20-membered heteroaryl. In certain embodiments heteroaryl groups are those derived from thiophene, pyrrole, benzothiophene, benzofuran, indole, pyridine, quinoline, imidazole, oxazole, and pyrazine.

[0040] “Heteroarylalkyl” by itself or as part of another substituent refers to an acyclic alky l radical in which one of the hydrogen atoms bonded to a carbon atom, typically a terminal or sp3carbon atom, is replaced with a heteroaryl group. Where specific alkyl moleties are intended, the nomenclature heteroarylalkanyl, heteroarylalkenyl, or heteroarylalkynyl is used. In certain embodiments, a heteroarylalkyl group is a 6- to 30- membered heteroarylalkyl, e.g., the alkanyl, alkenyl, or alkynyl moiety of the heteroarylalkyl is 1 - to 10-membered and the heteroaryl moiety is a 5- to 20-membered heteroaryl, and in certain embodiments, 6- to 20-membered heteroarylalkyl, e.g., the alkanyl. alkenyl, or alkynyl moiety of the heteroarylalkyl is 1- to 8-membered and the heteroaryl moiety is a 5- to 12 -membered hetero aryl .

[0041] “Heterocycloalkyl” by itself or as part of another substituent refers to a partially saturated or unsaturated cyclic alkyl radical in which one or more carbon atoms (and any associated hydrogen atoms) are independently replaced with the same or different heteroatom. Examples of heteroatoms to replace the carbon atom(s) include, but are not limited to, N, P, O, S, Si, etc. Where a specific level of saturation is intended, the nomenclature “heterocycloalkanyl” or “heterocycloalkenyl” is used. Examples of heterocycloalkyl groups include, but are not limited to, groups derived from epoxides, azirines, thiiranes, imidazolidine, morpholine, piperazine, piperidine, pyrazolidine, pyrrolidine, quinuclidine, and the Iike.“Heterocycloalkylalkyl” by itself or as part of another substituent refers to an acyclic alkyl radical in which one of the hydrogen atoms bonded to a carbon atom, typically a terminal or sp3carbon atom, is replaced with a heterocycloalkyl group. Where specific alkyl moieties are intended, the nomenclature heterocycloalkylalkanyl, heterocycloalkylalkenyl, or heterocycloalkylalkynyl is used. In certain embodiments, a heterocycloalkylalkyl group is a 6- to 30-membered heterocycloalkylalkyl, e.g., the alkanyl, alkenyl, or alkynyl moiety of the heterocycloalkylalkyl is 1 - to 10-membered and the heterocycloalkyl moiety is a 5- to 20-membered heterocycloalkyl, and in certain embodiments, 6- to 20-membered heterocycloalkylalkyl, e.g., the alkanyl, alkenyl, or alkynyl moiety of the heterocycloalkylalkyl is 1- to 8-membered and the heterocycloalkyl moiety is a 5- to 12-membered heterocycloalkyl.

[0042] “Mixture” refers to a collection of molecules or chemical substances. Each component in a mixture can be independently varied. A mixture may contain, or consist essentially of, two or more substances intermingled with or without a constant percentage composition, wherein each component may or may not retain its essential original properties, and where molecular phase mixing may or may not occur. In mixtures, the components making up the mixture may or may not remain distinguishable from each other by virtue of their chemical structure.

[0043] “Parent aromatic ring system” refers to an unsaturated cyclic or polycyclic ring system having a conjugated π (pi) electron system. Included within the definition of “parent aromatic ring system” are fused ring systems in which one or more of the rings are aromatic and one or more of the rings are saturated or unsaturated, such as, for example, fluorene, indane, indene, phenalene, etc. Examples of parent aromatic ring systems include, but are not limited to, aceanthrylene, acenaphthylene, acephenaathrylene, anthracene, azulene, benzene, chrysene, coronene, fluoranthene, fluorene, hexacene, hexaphene, hexalene, a$-indacene, s-indacene, indane, indene, naphthalene, octacene, octaphene, octalene, ovalene, penta-2,4-diene, pentacene, pentalene, pentaphene, perylene, phenalene, phenanthrene, picene, pleiadene, pyrene, pyranthrene, rubicene, Iriphenylene, trinaphthalene, and the like, “Parent heteroaromatie ring system” refers to a parent aromatic ring system in which one or more carbon atoms (and any associated hydrogen atoms) are independently replaced with the same or different heteroatom. Examples of heteroatoms to replace the carbon atoms include, but are not limited to, N, P, O, S, Si, etc. Specifically inchided within the definition of “parent heteroaromatic ring systems” are fused ring systems in which one or more of the rings are aromatic and one or more of the rings are saturated or unsaturated, such as, for example, arsindole, benzodioxan, benzofuran, chromane, chromene, indole, indoline, xanthene, etc. Examples of parent heteroaromatic ring systems include, but are not limited to, arsindole, carbazole, β-carboline, chromane, chromene, cmnoline, furan, imidazole, indazole, indole, indoline, indolizine, isobenzofuran, isochromene, isoindole, isoindoline, isoquinoline, isothiazole, isoxazole, naphthyridine, oxadiazole, oxazole, perimidine, phenanthridine, phenanthroline, phenazine, phthalazine, pteridine, purine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolizine, quinazoline, quinoline, quinolizine, quinoxaline, tetrazole, thiadiazole, thiazole, thiophene, triazole, xanthene, and the like.

[0044] “Substituted” refers to a group in which one or more hydrogen atoms are independently replaced with the same or different substituent(s). Examples of substituents include, but are not limited to, -R64, -R60, -O-, -OH, =O, -OR60, -SR60, -S-, -S, -NR60R61, -NR60, -CN, -CF3, -OCN, -SCN, -NO, -NO2, -N2, -N3, -S(O)2O-, -S(O)2OH, -S(O)2R60, -OS(O3)O-, -OS(O)2R60, -P(O)(O-)2, -P(O)(OR60)(O-), -OP(O)(OR60)(OR61), -C(O)R60, - C(S)R60, -C(O)OR60, -C(O)NR60R61, -C(O)O-, -C(S)OR60, -NR62C(O)NR60R61, - NR62C(S)NR60R61, -NR62C(NRw)NR60R61, -C(NR62)NR60R61, -S(O)2, NR60R61, - NR63S(O)2R60, -NR63C(O)R60, -S(O)R60, and residues of Formula III as described herein; wherein each -R64is independently a halogen; each R60and R61are independently alkyl, substituted alkyl, alkoxy, substituted alkoxy, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, substituted arylalkyl, heteroaiylalkyl, or substituted heteroarylalkyl, or R60and R61together with the nitrogen atom to which they are bonded form a heterocycloalkyl, substituted heterocycloalkyl, heteroaryl, or substituted heteroaryl ring, and R62and R63are independently alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl. substituted cycloalkyl. heterocycloalkyl. substituted beterocycloalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, or substituted heteroarylalkyl, or R62and R63together with the atom to which they are bonded form one or more heterocycloalkyl, substituted heterocycloalkyl, heteroaryl, or substituted heteroaryl rings; wherein the “substituted” substituents, as defined above for R60, R61, R62, and R63, are substituted with one or more, such as one, two, or three, groups independently selected from alkyl, -alkyl-OH, -O-haloalkyl, -alkyl-NH2. alkoxy, cycloalkyl, cycloalkylalkyl, beterocycloalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, O-, - OH, = O, -O-alkyk -O-aryl, -O-heteroarylalkyk -O-cycloalkyl, -O-heterocycloalkyl, -SH, - S-, =S, -S-alkyl, -S-aryl, -S-heteroarylalkyl, -S-cycloalkyl, -S-heterocycloalkyl, -NH2, =NH, -CN, -CF3, -OCN, -SCN, -NO, -NO2, =N2, -N3, -S(O)3O-, -S(O)2, -S(O)2OH, -OS(O2)O-, -SO2(alkyl), -SO2(phenyl), -SO2(haloalkyl), -SO2NH2, -SO2NH(alkyl), -SO2NH(phenyl), - P(O)(O-)2, -P(O)(O-alkyl)(O-), -OP(O)(O-alkyI)(O-alkyl), -CO2H, -C(O)O(alkyl), -CON(alkyl)(alkyl), -CONH(alkyl), -CONH2, -C(O)(alkyl), -C(O )(phenyl) , -C(O )(haloalkyl), -OC(O)(alkyI), -N(alkyl)(alkyl), -NH(alkyl), -N(alkyl)(alkylphenyl), -N H(alkylphenyl), -NHC(O)( alkyl), -NHC(O)( phenyl), -N(alkyl)C(O)(alkyl), -N(alkyl)C(O)(phenyl) and residues of Formula III as described herein.

[0045] As used in this specification and the appended claims, the articles “a,” “an,” and "the" include plural referents unless expressly and unequivocally limited to one referent. All numerical ranges herein include all numerical values and ranges of all numerical values within the recited range of numerical values.

[0046] Described herein are compositions comprising a phenolic compound and a substrate. In certain embodiments, the substrate is an aggregate material, and the phenolic compound can permit better adhesion of bituminous materials to tire aggregate for use in asphalt applications.

[0047] Phenolic compounds, including phenolic esters, may be made according to any methods known in the art, including condensation reactions between alcohols and carboxylate residues. Exemplary methods include the production of gallate esters, including lauryl gallate:

[0048]

[0049] Other exemplary phenolic esters include those derived from diols, poloyols, or alcohol- containing oligomers or polymers such as poly(styrene-co-allyl alcohol): Other exemplary phenols and phenolic acids that can be used to create phenolic esters include, but are not limited to, monolignols such as p-comnaryl alcohol, p-coumaric acid, coniferyi alcohol, ferulic acid, siaapyl alcohol, caffeyl alcohol, 5-hydroxyconiferyl alcohol, dihydroconiferyl alcohol, and sinapic (sinapinic) acid. Using the processes described herein, a variety of lignin-derived compounds can be created including, but not limited to, the following exemplary compounds:

[0050]

[0051] In certain embodiments, the compounds the monolignols described herein may be processed to their demethylated state to provide phenolic compounds having a plurality of hydroxyl groups. For example, sinapic acid can be demethylated to provide the three tree hydroxyl groups, while ferulic acid can be demethylated to provide two free hydroxyl groups. In some embodiments, the compounds of Formula I can include ester residues to impart increased polarity, which may be desired depending on the nature of (he aggregate and / or asphalt binder. In such embodiments, this may be reflected in Formula 1 when W3is O and

[0052] W2is -C(=O)- or Y is -C( =O)R6. Such compounds can be prepared from the monolignols described herein. In other embodiments, the compounds of Formula I comprised alkylated catechols that do not comprise such functional groups in the side chain. In these embodiments, W3is absent, W2is not -C(=O)- and Y is not -C(=O)R6. Such compounds may be prepared, tor example, by alkylating pyrogallol or catechols via Friedel-Crafts or aeid / alkene alkylation. In certain embodiments, the phenolic compounds of the present disclosure are selected from Formula I: wherein

[0053] R1, R2, R3, R4, R5and R6are each independently selected from hydrogen, optionally substituted alkyl, optionally substituted alkoxy, and hydroxyl, provided that at least one of R1, R2, R3, R4or R5is hydroxyl.

[0054] X is absent or selected from C1-C5 akanyl or C2-C5 alkenyl;

[0055] W2is selected from C1 -C5 akanyl, C2-C5 alkenyl, and -C( =O)-;

[0056] W3is absent or O; and

[0057] Y is selected from an optionally substituted alkyl, optionally substituted alkenyl, and -C(=O)R6.

[0058] In certain embodiments, the compounds described herein may include embodiments where Y is an optionally substituted alkyl, wherein Y is derived from an alcohol such as a polyol. In such embodiments, the alkyl group comprises one or more substituents, such as other akyl groups, hydroxyl groups, aryl groups, or residues of Formula Ill (as disclosed below). In certain embodiments, such compounds may include those represented by Formula ll below.

[0059] In certain embodiments, the phenolic compounds of the present disclosure are selected from compounds of Formula 11:

[0060] wherein

[0061] R1, R2, R3, R4and R5are each independently selected from hydrogen, optionally substituted alkyl, optionally substituted alkoxy, and hydroxyl;

[0062] R10and R11are each independently selected from hydrogen, optionally substituted alkyl, optionally substituted alkoxy, and hydroxyl;

[0063] X is absent or selected from C1-C5 akanyl or C2-C5 alkenyl;

[0064] W2is, independently for each occurrence, selected from CH2- and -C( =O)-;

[0065] W3is, independently for each occurrence, absent or O; n, m and ns are, independently for each occurrence, an integer selected from 0 to 10; z is an integer selected from 1 to 300; y is an integer selected from 0 to 300; and W1aand W1bare, independently for each occurrence, selected from hydrogen, optionally substituted alkyl optionally substituted aryl, and a residue of Formula III :

[0066]

[0067] In certain embodiments, the compounds of Formula II are derived from a polyol reacted with two or more molar equivalents of reactive phenolic intermediates. Thus, in certain embodiments, the compounds of Formula II comprise those compounds where at least one of W1aor W1bis a residue of Formula III. In certain embodiments, y is an integer selected from 1-300. In certain embodiments, n, n1and n2are 0.

[0068] In certain embodiments, it has been surprisingly discovered that the compounds described herein (i.e., compounds of Formulae I and II) may be particularly suitable for promoti ng the adhesion of certain materials to a variety of substrates including materials with residual water content. For example, in certain embodiments the compounds described herein may effectively promote the adhesion of bituminous binders to aggregates having a moisture content.

[0069] Moisture -induced stripping is a failure mode of asphalt pavements that occurs when asphalt binders lose adhesion with aggregate substrates. When this failure occurs, pavement issues like raveling, loss of strength, cracking, and pothole formation may be observed. Aggregates vary in their moisture susceptibility, with limestone aggregates being less susceptible and acidic / siliceous aggregates like granite being more likely to strip. The paving industry addresses this issue through the use of anti-strip additives including hydrated lime, polymers, or cationic liquids including, but not limited to, fatty amines. Exemplary test methods used to assess stripping tendency include tensile strength ratio (TSR), Hamburg wheel tracking (HWT), and the Texas boil test.

[0070] Historically, liquid anti-strips like amines have been used instead of hydrated lime due to ease of use. However, amine anti-strips are known to exhibit some level of toxicity and the mechanism of adhesion modification limits their use to acidic substrates. Aminebased anti-strips can also cause equipment corrosion and compatibility issues with other asphalt modifiers like polyphosphoric acid (PPA). Moreover, the usefulness of amine-based anti-strips can be limited by the moisture content of the aggregate materials, where adhesion of the anti-strips and binder to the aggregates can be negatively impacted by water content. In some studies, it has been shown that amine and other antistrips are most typically applied to aggregates having a moisture content of 0.1 wt. % or less. In certain embodiments described herein, it has been surprisingly discovered that the compounds described herein may serve as anti-strip materials that can be effectively applied to aggregates having a moisture content >0. 1 wt. %, such as >0.5 wt. % or higher. In certain embodiments, the compounds described herein may coat aggregates having a moisture content up to 10 wt. %, such as about 1 to about 5 wt. %.

[0071] In certain embodiments it has been discovered that the phenolic compounds described herein are “amphiphilic'' in nature and can facilitate the adhesion of an additized asphalt binder to wet aggregates. In certain embodiments, this property may be highly desirable for lower temperature production processes like cold mix, part warm mix, and warm mix, where stockpile aggregate moisture is still present or has been only partially dried at these reduced temperatures. The additives described herein may be applied as a discrete additive or in combination with additives or processes that facilitate lower temperature coating and mix production. These technologies may be additional chemical additives, but may also include water-based viscosity reduction methods like asphalt emulsion or foaming. Hot mix asphalts are typically produced between 150-200°C and warm mix technologies like these can reduce production temperatures by 50- 100°C, resulting in significant energy savings and reduction in emissions associated with production.

[0072] In certain embodiments, other envisioned applications tor adhesion promoter compounds described herein include pavement recycling, adhesion of asphalt binder to bo th fiberglass and granules in used in shingle production, tack coats, void reducing asphalt membranes, lane markings, rejuvenators, self-healing asphalt membranes, asphalt preservation products like chip seals, and application of asphalt binders to non-aggregate substrates like rail ties for waterproofing or sealing purposes. Similarly, envisioned applications of the compounds described herein (with or without an asphalt binder constituent) may include construction adhesives, rubber additives (e.g., compositions comprising compounds of Formula I or II and at least one rubber and / or elastomeric material), cement modifiers, or soil stabilization agents. Methods for obtaining the novel compounds and compositions described herein will be apparent to those of ordinary skill in the art, suitable procedures being described, for example, in the examples below, and in the references cited herein.

[0073] In all of the examples, and throughout the disclosure, the compounds described may be useful alone, as mixtures, or in combination with other compounds, compositions, and / or materials.

[0074] EXAMPLES

[0075] In order to promote a further understanding of the present invention and its various embodiments, the following specific examples are provided. It will be understood that these examples are illustrative and not limiting of the invention.

[0076] Example 1

[0077] Samples With Phenolic Ester Adhesion Promoter

[0078] In the first iteration, lauryl gallate (PIG. 1) was added to 64-22 asphalt binder (1% by weight) and used to coat INDOT #11 limestone measured at 4% moisture content. Moisture was produced by water addition back to oven-dried aggregate. Lauryl gallate is commonly used as an antioxidant food additive, but Applicant theorized the polyhydroxyl compound modified with a waxy tail would allow incorporation into the binder and promote adhesion analogous to the amphiphilic mechanism of amine-based antistrip additives. Resistance to moisture-induced stripping was confirmed by subjecting the coated aggregate to a Texas Boil stripping test, a 10 minute test run in boiling water with periodic agitation and removal of stripped binder. The post-boil material showed significantly improved adhesion compared to a non-addiiized control as determined by wt. % of binder retention to the substrate (FIG. 2).

[0079] In a second iteration, lauryl gallate was added to 58-28 asphalt binder (1% by weight) in preparing a fine-graded hoi mix aggregate blend measured ai 5.5% moisture content. Final moisture in this iteration was produced by saturating the aggregate mix with 12% water addition (w / w) in a plastic bag, allowing moisture to incorporate overnight, then drying in a 5 gallon bucket mixer with an open flame to an aggregate temperature of 200°F. This drying approach was used to imitate more closely what is happening to aggregate in a hot mix plant. Additized asphalt was introduced after the heating step for an effective coating temperature of 180°F. Mix was compacted to 75 gyrations and compared to a non-additized control where aggregate was partially dried to 5.8% moisture. Inclusion of the lauryl gallate significantly improved coating and adhesion relative to control (FIG. 3).

[0080] In a third iteration, lauryl gallate was added to a 64-22 binder (1% addition relative to binder) and used to make an emulsion with water, sodium hydroxide, and an anionic surfactant. The additive did not affect emulsion stability and was subsequently used to coat a fine-graded mix, with 4% moisture added to dry aggregate before coating. Full coating was observed in this trial where 80ºC aggregate was coated with 60ºC emulsion (FIG. 4), and compacted (FIG. 5). The mix was also noted to remain workable during the mixing period. Dense-graded mixes (FIG. 6) were selected for the second and third iterations to test antistrip efficacy towards a range of aggregate particle sizes and effects of residual moisture content on volumetries post-compaction.

[0081] Further Embodiments

[0082] Embodiment I ; A compound of Formula I: wherein

[0083] R1, R2, R3, R4, R5and R6are each independently selected from hydrogen, optionally substituted alkyl, optionally substituted alkoxy, and hydroxyl, provided that at least one of R1, R2, R3, R4or R5is hydroxyl:

[0084] X is absent or selected from C1-C5 akanyl or C2-C5 alkenyl;

[0085] W2is selected from C1-C5 akanyl, C2-C5 alkenyl, and -C( =O)-;

[0086] W3is absent or O; and

[0087] Y is selected from an polymeric residue, an oligomeric residue, optionally substituted alkyl, optionally substituted alkene, and -C( =O)R6. Embodiment 2: The compound of Embodiment 1, wherein at least two of R1, R2, R3, R4and R5are hydroxyl.

[0088] Embodiment 3: The compound according to any one of Embodiments 1 -2, wherein R2and R4are hydroxyl .

[0089] Embodiment 4: The compound according to any one of Embodiments 1-3, wherein R3is hydroxyl.

[0090] Embodiment 5: The compound according to any one of Embodiments 1-4, wherein R1is hydrogen.

[0091] Embodiment 6; The compound according to any one of Embodiments 1 -5, wherein R5is hydrogen.

[0092] Embodiment 7: The compound according to any one of Embodiments 1 -6, wherein X is absent:

[0093] Embodiment 8: The compound according to any one of Embodiments 1-6, wherein X is selected from C1 -C4 alkyl and C2-C4 alkenyl.

[0094] Embodiment 9: The compound according to any one of Embodiments 1-6, wherein X is C2 alkenyl.

[0095] Embodiment 10: The compound according to any one of Embodiments 1 -9, wherein Y is an optionally substituted C1 -C40 alkyl or C2-C40 alkenyl.

[0096] Embodiment 1 1 : The compound according to any one of Embodiments 1-9, wherein Y is an optionally substituted C1-C20 alkyl or C2-C20 alkenyl.

[0097] Embodiment 12: The compound according to any one of Embodiments 1-11 , wherein Y is imsubstituted.

[0098] Embodiment 13: The compound according to any one of Embodiments 1 -9, wherein Y is a polymeric or oligomeric residue.

[0099] Embodiment 14: The compound according to Embodiment 13, wherein Y is derived from a polymeric or oligomeric alcohol.

[0100] Embodiment 15: The compound according to Embodiment 14, wherein Y is derived from poly(styrene-co-allyl alcohol).

[0101] Embodiment .16: The compound according to any one of Embodiments 1-15, wherein

[0102] W3is O.

[0103] Embodiment 17: The compound according to any one of Embodiments 1-15, wherein

[0104] W2is C( =O),

[0105] Embodiment 18: The compound according to any one of Ein bodimen ts 1-15, wherein

[0106] W2is O.

[0107] Embodiment 19: The compound according to any one of Embodiments 1-15, wherein

[0108] W3is C(=O).

[0109] Embodiment 20: The compound according to any one of Embodiments 1-15, wherein

[0110] W3is O.

[0111] Embodiment 21: The compound according to Embodiment 1, wherein at least three of R1, R2, R3, R4or R5are hydroxyl.

[0112] Embodiment 22: A compound of Formula 11:

[0113] wherein

[0114] R1, R2, R3, R a4nd R5are each independently selected from hydrogen, optionally substituted alkyl, optionally substituted alkoxy, and hydroxyl;

[0115] R10and R11are each independently selected from hydrogen, optionally substituted alkyl, optionally substituted alkoxy, and hydroxyl; X is absent or selected from C1-C5 akanyl or C2-C5 alkenyl; W1is selected from optionally substituted alkyl and optionally substituted aryl;

[0116] W2is, independently for each occurrence, selected from --CH2- and -C(=O)-;

[0117] W3is, independently for each occurrence, absent or O; n, n1and n2are each, independently for each occurrence, an integer selected from 0 to 10; z is an integer selected from 1 to 300; y is an integer selected from 0 to 300; and W1aand W1bare, independently for each occurrence, selected from hydrogen, optionally substit uted alkyl optionally substituted aryl, and a residue of Formula III:

[0118]

[0119] Embodiment 23: The compound according to Embodiment 22, wherein at least one of

[0120] R1, R2, R3, R4or R5is hydroxyl.

[0121] Embodiment 24: The compound according to any one of Embodiments 22-23, wherein at least two of R1, R2, R3, R4or R5are hydroxyl

[0122] Embodiment 25: The compound according to any one of Embodiments 22-24, wherein R2and R4are hydroxyl.

[0123] Embodiment 26: The compound according to any one of Embodiments 22-25, wherein R3is hydroxyl.

[0124] Embodiment 27: The compound according to any one of Embodiments 22-26, wherein R1is hydrogen.

[0125] Embodiment 28: The compound according to any one of Embodiments 22-27, wherein R2is hydrogen.

[0126] Embodiment 29: The compound according to any one of Embodiments 22-28, wherein X is absent.

[0127] Embodiment 30: The compound according to any one of Embodiments 22-28, wherein X is selected from C1 -C4 alkanyl and C2-C4 alkenyl.

[0128] Embodiment 31: The compound according to any one of Embodiments 22-28, wherein X is C2 alkenyl.

[0129] Embodiment 32: The compound according to any one of Embodiments 22-31 , wherein W1ais selected from optionally substituted alkyl and optionally substituted aryl.

[0130] Embodiment 33: The compound according to any one of Embodiments 22-32, wherein W1ais phenyl and is hydrogen.

[0131] Embodiment 34: The compound according to any one of Embodiments 22-33, wherein n is 1 .

[0132] Embodiment 35: The compound according to any one of Embodiments 22-34, wherein W2is -C(=O)-.

[0133] Embodiment 36: The compound according to any one of Embodiments 22-34, wherein

[0134] W2is -CH2-.

[0135] Embodiment 37: The compound according to any one of Embodiments 22-34, wherein

[0136] W2is selected from C1-C5 akanyl and C2-C5 alkenyl.

[0137] Embodiment 38: The compound according to any one of Embodiments 22-37, wherein

[0138] Y is C(=O)R6.

[0139] Embodiment: 39: The compound according to any one of Embodiments 22-38, whereinR6is an optionally substituted alkyl.

[0140] Embodiment 40: A composition comprising at least one compound according to any of the preceding Embodiments.

[0141] Embodiment 41 : A composition comprising at least one compound according to any one of Embodiments 1 -39, and at least one substrate having a surface.

[0142] Embodiment 42: The composition of Embodiment 41 , wherein the substrate comprises an aggregate.

[0143] Embodiment 43: The composition of Embodiment 42, wherein the aggregate has a diameter of about 2 mm to about 50 mm.

[0144] Embodiment 44: The composition of Embodiment 42, wherein the aggregate has a diameter of abo ut 5 mm to about 30 mm.

[0145] Embodiment 45: The composition according to any one of Embodiments 41-44, wherein the at: least one compound is disposed on the surface of the substrate.

[0146] Embodiment 46: The composition according to Embodiment 45, wherein the composition further comprises a bituminous binder.

[0147] Embodiment 47: The composition according to Embodiment 45, wherein the bituminous binder is disposed over the at least one compound.

[0148] Embodiment 48: The composition according to any one of Embodiments 42-47, wherein the aggregate comprises a moisture content of 0.01 to about 10.0 wt. % of the aggregate.

[0149] Embodiment 49: The composition according to any one of Embodiments 42-47, wherein the aggregate comprises a moisture content of 0.2 to about 8.0 wt. % of the aggregate.

[0150] Embodiment 50: The composition according to any one of Embodiments 42-47, wherein the aggregate comprises a moisture content of 1.0 to about 5.0 wt. % of the aggregate.

[0151] Embodiment 51 : The compound according to any one of Embodiments 46-50, wherein the bituminous binder comprises about 0.5 to about 5 wt. % of the composition. Embodiment 52: The compound according to any one of Embodiments 40-51, wherein the at least one compound comprises about 0.05 to about 5 wt. % of the composition.

[0152] Embodiment 53: The composition of Embodiment 52, wherein the at least one compound comprises about 0.1 to about 2.5 wt. % of the composition.

[0153] Embodiment 54: The composition of Embodiment 52, wherein the at least one compound comprises about 0.25 to about 1.0 wt. % of the composition.

[0154] Embodiment 55; The composition according to any one of Embodiments 42-54, wherein the aggregate comprises a calcareous material.

[0155] Embodiment: 56: The composition according to any one of Embodiments 42-54, wherein the aggregate comprises a siliceous material.

[0156] The uses of the terms "a" and "an" and "the" and similar references in the context of describing the invention (especially in the context of the following claims) are to be construed to cover both the singular and the plural unless otherwise indicated herein or clearly contradicted by context. Recitation of ranges of values herein are merely intended to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. The use of any and all examples, or exemplary language (e.g., "such as” ) provided herein, is intended merely to better illuminate the invention and does not pose a limitation on the scope of the invention unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the invention.

[0157] While the invention has been illustrated and described in detail in the drawings and the foregoing description, the same is to be considered as illustrative and not restrictive in character, it being understood that only the preferred embodiment has been shown and described and that all changes and modifications that come within the spirit of the invention are desired to be protected. In addition, all references cited herein are indicative of the level of skill in the art and are hereby incorporated by reference in their entirety.

Claims

CLAIMS:1 . A composition comprising an aggregate having a surface; wherein an anti-strip material is disposed on the surface of the aggregate, wherein said anti-strip material comprises at least one compound of Formula 1:whereinR1, R2, R3, R4, R5and R6are each independently selected from hydrogen, optionally substituted alkyl, optionally substituted alkoxy, and hydroxyl, provided that at least one of R1, R2, R3, R4or R5is hydroxyl;X is absent or selected from C1-C5 akanyl or C2-C5 alkenyl;W2is selected from C 1-C5 akanyk C2-C5 alkenyl, and -C(=O)-;W3is absent or O; andY is selected from an optionally substituted alkyl, optionally substituted alkenyl, and -C(=O)R6.

2. The composition of claim 1, wherein at least two of R1, R2, R3, R4and R5are hydroxyl .

3. The composition according to claim 1 , wherein R2and R4are hydroxyl.

4. The composition according to any of the preceding claims, wherein R3is hydroxyl.

5. The composition according to any of the preceding claims, wherein R1is hydrogen.

6. The composition according to any of the preceding claims, wherein R5is hydrogen.

7. The composition according to any of the preceding claims, wherein X is absent.

8. The composition according to any of claims 1 -6, wherein X is selected from C1-C4 alkanyl and C2-C4 alkenyl,9. The composition of claim 8, wherein X is C2 alkenyl.

10. The composition according to any of the preceding claims, wherein Y is an optionally substituted C1-C40 alkyl or optionally substituted C2-C40 alkenyl, each of which are branched or unbranched.1 1. The composition according to any of the preceding claims, wherein Y is unsubstituted.

12. The composition according to any one of the preceding claims, wherein Y is an unbranched C6-C16 alkyl.

13. The composition according to any one of the preceding claims, wherein W3is O.

14. The composition according to any one of the preceding claims, wherein the composition further comprises a bituminous binder,15. The composition according to claim 14, wherein the bituminous binder is disposed over the at least one compound.

16. The composition according to claim 14, wherein the bituminous binder comprises an admixture with the anti-strip material,17. The composition according to any one of the preceding claims, wherein the aggregate comprises a moisture content of about 0.2 to about 8,0 wt. % of the aggregate.

18. The composition of any one of claims 14-16, wherein the bituminous binder comprises about 0.5 to about 5 wt, % of the composition.

19. The composition of any one of claims 1-17, wherein the a t least one compound comprises about 0.05 to about 5 wt. % of the composition.

20. The composition of claim 18, wherein the at least one compound comprises about 0. 1 to about 2,5 wt. % of the composition.

21. The composition according to any one of the preceding claims, wherein the aggregate has a diameter of a bout 5 mm to about 30 mm.

22. The composition according to any one of the preceding claims 1 -15, wherein the aggregate comprises a moisture content of about: 0 to about 8,0 wt. % of the aggregate.

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