Hydrogen sulfide scavengers for asphalt

Abstract

Scavenging compounds and compositions useful in reducing sulfide emissions from asphalt, such as polymer-treated asphalt, are disclosed. The scavenger compositions may include sulfide-scavenging agents. The scavenger compositions also include a metal-containing compound and optionally a solvent. Any of the compositions, sulfide-scavenging agents and metal-containing compounds may be anhydrous. Methods of using the compositions to reduce hydrogen sulfide emissions from asphalt are also disclosed.

Claims

1. A composition for reducing hydrogen sulfide emission from asphalt, comprising: (a) a metal-containing compound comprising a member selected from the group consisting of a metal carboxylate, a metal carbonate, and any combination thereof; and (b) a sulfide-scavenging agent selected from the group consisting of hexamethylenetetramine and a 1,3,5-triazine derivative of Formula I: ##STR00007## wherein each of R.sup.1, R.sup.2, and R.sup.3 is independently selected at each occurrence from hydrogen, straight or branched C.sub.1-C.sub.30 alkyl, hydroxyl substituted straight or branched C.sub.1-C.sub.30 alkyl, and straight or branched C.sub.1-C.sub.30 alkyl substituted with straight or branched C.sub.1-C.sub.30 alkoxy, wherein the metal-containing compound does not comprise zinc.

2. The composition of claim 1, further comprising asphalt.

3. The composition of claim 2, wherein the asphalt is polymer-treated asphalt.

4. The composition of claim 2, wherein the asphalt comprises polyphosphoric acid.

5. The composition of claim 1, wherein the sulfide-scavenging agent comprises Formula I, and each of R.sup.1, R.sup.2, and R.sup.3 is independently selected from straight or branched C.sub.6-C.sub.30 alkyl, hydroxyl substituted straight or branched C.sub.6-C.sub.30 alkyl, and straight or branched C.sub.6-C.sub.30 alkoxy substituted with straight or branched C.sub.1-C.sub.30 alkoxy.

6. The composition of claim 1, wherein the sulfide-scavenging agent comprises Formula I, and each of R.sup.1, R.sup.2, and R.sup.3 is selected from C.sub.1-C.sub.9 straight or branched alkyl.

7. The composition of claim 1, wherein the sulfide-scavenging agent comprises Formula I, and each of R.sup.1, R.sup.2, and R.sup.3 is the same substituent.

8. The composition of claim 1, wherein R.sup.1 is CH.sub.2CH.sub.2OH, R.sup.2 is CH.sub.2CH.sub.2OH, and R.sup.3 is-CH.sub.2CH.sub.2OH.

9. The composition of claim 1, wherein the sulfide-scavenging agent is hexamethylenetetramine.

10. The composition of claim 1, further comprising a polar solvent selected from the group consisting of diethylene glycol, 2-butoxyethanol, propylene glycol, monoethanol amine, and any combination thereof.

11. The composition of claim 1, wherein the composition comprises the following weight percentages of each component based on the total weight of the composition: about 10 weight % to about 90 weight % of the sulfide-scavenging agent, about 1 weight % to about 50 weight % of the metal-containing compound, and optionally about 10 weight % to about 90 weight % of a solvent.

12. The composition of claim 3, wherein the asphalt comprises about 0.1 weight % to about 10 weight % of the polymer based on the total weight of the asphalt.

13. The composition of claim 1, wherein the metal of the metal-containing compound is selected from the group consisting of Cu (II), Fe (II), Ni (II), Co (II), Mn (II), Ca (II), Mg (II), and any combination thereof.

14. The composition of claim 1, wherein the metal-containing compound is selected from the group consisting of copper acetate, copper bis-glycinate, copper 2-ethylhexanoate, iron 2-ethylhexanoate and any combination thereof.

15. The composition of claim 1, wherein the composition, the metal-containing compound and/or the sulfide-scavenging agent is anhydrous.

16. A method of reducing hydrogen sulfide emission from asphalt, comprising: combining asphalt with a composition, the composition comprising a metal-containing compound comprising a member selected from the group consisting of a metal carboxylate, a metal carbonate, and any combination thereof, and a sulfide-scavenging agent selected from the group consisting of hexamethylenetetramine and a 1,3,5-triazine derivative of Formula I: ##STR00008## wherein each of R.sup.1, R.sup.2, and R.sup.3 is independently selected at each occurrence from hydrogen, straight or branched C.sub.1-C.sub.30 alkyl, hydroxyl substituted straight or branched C.sub.1-C.sub.30 alkyl, and straight or branched C.sub.1-C.sub.30 alkyl substituted with straight or branched C.sub.1-C.sub.30 alkoxy.

17. The method of claim 16, wherein the sulfide-scavenging agent comprises Formula I, and each of R.sup.1, R.sup.2, and R.sup.3 is independently selected from straight or branched C.sub.6-C.sub.30 alkyl, hydroxyl substituted straight or branched C.sub.6-C.sub.30 alkyl, and straight or branched C.sub.6-C.sub.30 alkoxy substituted with straight or branched C.sub.1-C.sub.30 alkoxy.

18. A composition, comprising: (a) asphalt; (b) a metal-containing compound comprising a member selected from the group consisting of a metal carboxylate, a metal carbonate, and any combination thereof; and (c) a sulfide-scavenging agent selected from the group consisting of hexamethylenetetramine and a 1,3,5-triazine derivative of Formula I: ##STR00009## wherein each of R.sup.1, R.sup.2, and R.sup.3 is independently selected at each occurrence from hydrogen, straight or branched C.sub.1-C.sub.30 alkyl, hydroxyl substituted straight or branched C.sub.1-C.sub.30 alkyl, and straight or branched C.sub.1-C.sub.30 alkyl substituted with straight or branched C.sub.1-C.sub.30 alkoxy.

19. The composition of claim 18, wherein the metal-containing compound is copper acetate.

Description

DETAILED DESCRIPTION

(1) The present disclosure relates to sulfide-scavenging compositions for use with asphalt. The compositions are particularly efficient at reducing hydrogen sulfide emissions of asphalt, including polymer-treated asphalt, such as PPA-treated asphalt. The present disclosure relates to compositions comprising a metal-containing compound, a sulfide-scavenging agent, and optionally asphalt, including polymer-treated asphalt, such as PPA-treated asphalt. The present disclosure also relates to methods of using the compositions to reduce hydrogen sulfide emission from asphalt, including polymer-treated asphalt, such as PPA-treated asphalt.

(2) In accordance with the present disclosure, the term alkyl as used herein, refers to a hydrocarbon radical with a defined number of carbon atoms (i.e., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, and 30 carbons). Branched alkyl groups include, but are not limited to, sec-butyl, tert-butyl, isobutyl, isopentyl, neopentyl, 1-methylbutyl, 2-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-ethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1,1-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl, 1,4-dimethylpentyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 3,3-dimethylpentyl, 3,4-dimethylpentyl, 4,4-dimethylpentyl, 1,1,2-trimethylbutyl, 1,1,3-trimethylbutyl, 1,2,2-trimethylbutyl, 1,2,3-trimethylbutyl, 1,3,3-trimethylbutyl, 2,2,3-trimethylbutyl, 2,3,3-trimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, 1-ethyl-1-methylbutyl, 1-ethyl-2-methylbutyl, 1-ethyl-3-methylbutyl, 2-ethyl-1-methylbutyl, 2-ethyl-2-methylbutyl, 2-ethyl-3-methylbutyl, 1-propylbutyl, 1,1-diethylpropyl, etc.

(3) In some embodiments, the number of carbon atoms for the alkyl group is between 6 and 30. In some embodiments, the number of carbon atoms for the alkyl group is between 6 and 20. In some embodiments, the number of carbon atoms for the alkyl group is between 6 and 15. In some embodiments, the number of carbon atoms for the alkyl group is between 6 and 10. In some embodiments, the number of carbon atoms for the alkyl group is between 6 and 8.

(4) The term alkoxyl as used herein, refers to a ether radical with a defined number of carbon atoms (i.e., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, and 30 carbons). Branched alkyl groups include, but are not limited to, sec-butoxy, tert-butoxy, isobutoxy, isopentoxy, neopentoxy, 1-methylbutoxy, 2-methoxybutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-ethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1-methylhexoxy, 2-methylhexoxy, 3-methylhexoxy, 4-methylhexoxy, 5-methylhexoxy, 1,1-dimethylpentoxy, 1,2-dimethylpentoxy, 1,3-dimethylpentoxy, 1,4-dimethylpentoxy, 2,2-dimethylpentoxy, 2,3-dimethylpentoxy, 2,4-dimethylpentoxy, 3,3-dimethylpentoxy, 3,4-dimethylpentoxy, 4,4-dimethylpentoxy, 1,1,2-trimethylbutoxy, 1,1,3-trimethylbutoxy, 1,2,2-trimethylbutoxy, 1,2,3-trimethylbutoxy, 1,3,3-trimethylbutoxy, 2,2,3-trimethylbutoxy, 2,3,3-trimethylbutoxy, 1,1,2,2-tetramethylpropoxy, 1-ethylpentoxy, 2-ethylpentoxy, 3-ethylpentoxy, 1-ethyl-1-methylbutoxy, 1-ethyl-2-methylbutoxy, 1-ethyl-3-methylbutoxy, 2-ethyl-1-methylbutoxy, 2-ethyl-2-methylbutoxy, 2-ethyl-3-methylbutoxy, 1-propylbutoxy, 1,1-diethylpropoxy, etc.

(5) In some embodiments, the number of carbon atoms for the alkyl portion of the alkoxy group is between 6 and 30. In some embodiments, the number of carbon atoms for the alkyl group is between 6 and 20. In some embodiments, the number of carbon atoms for the alkyl group is between 6 and 15. In some embodiments, the number of carbon atoms for the alkyl group is between 6 and 10. In some embodiments, the number of carbon atoms for the alkyl group is between 6 and 8.

(6) As used herein, the term asphalt refers to any of a variety of materials that are solid or semisolid at room temperature and which gradually liquefy when heated, and in which the predominant constituents are naturally occurring bitumens (or kerogens) or which are bitumen like materials obtained as residue in petroleum refining. It is expressly contemplated that asphalt as used herein includes what ASTM defines as asphalt: a dark brown to black cementitious material in which the predominant constituents are bitumens that occur in nature or are obtained in petroleum processing. Asphalts characteristically contain very high molecular weight hydrocarbons called asphaltenes. These are essentially soluble in carbon disulfide, and aromatic and chlorinated hydrocarbons. Bitumen is a generic term defined by the ASTM as a class of black or dark-colored cementitious substances, natural or manufactured, composed principally of high molecular weight hydrocarbons, of which asphalts, tars, pitches and asphaltenes are typical. The ASTM further classifies asphalts or bituminous materials as solids, semi-solids, or liquids using a penetration test for consistency or viscosity. In this classification, solid materials are those having a penetration of not more than 1 millimeter when a load of 100 grams is applied for 5 seconds while at 25? C., and semi-solids are those having a penetration of more than 1 millimeter when a load of 50 grams is applied for 5 seconds while at 25? C. Semi-solid and liquid asphalts predominate in commercial practice today. For example, any asphalt bottoms fraction, as well as naturally occurring asphalts, tars and pitches and may be used interchangeably herein with the term bitumen. The term asphaltic concrete means asphalt used as a binder with appropriate aggregate added, typically for use as a paving material.

(7) The term bottoms fraction refers to a crude fraction having a flash point of about 70? F. or greater.

(8) The term anhydrous as used herein, refers to compositions where the amount of water present is less than about 10 weight %, such as less than about 7 weight %, less than about 5 weight %, less than about 4 weight %, less than about 3 weight %, less than about 2 weight %, less than about 1 weight %, or about 0 weight %.

(9) Compositions

(10) The compositions disclosed herein comprise a metal-containing compound and a sulfide-scavenging agent. In some embodiments, the compositions comprise asphalt, which could be polymer-treated asphalt, such as PPA-treated asphalt. The compositions may further comprise a solvent. In some embodiments, the composition is anhydrous. In some embodiments, the metal-containing compound is anhydrous. In some embodiments, sulfide-scavenging agent is anhydrous.

(11) The sulfide-scavenging agent is selected from the group consisting of hexamethylenetetramine and 1,3,5-triazine derivatives of Formula I

(12) ##STR00004##
where each of R.sup.1, R.sup.2, and R.sup.3 is independently selected at each occurrence from hydrogen, straight or branched C.sub.1-C.sub.30 alkyl, hydroxyl substituted straight or branched C.sub.1-C.sub.30 alkyl, straight or branched C.sub.1-C.sub.30 alkyl substituted with straight or branched C.sub.1-C.sub.30 alkoxy. In some embodiments, the 1,3,5-triazine derivative is anhydrous.

(13) In some embodiments, the sulfide-scavenging agent is hexamethylenetetramine (HMTA), which has the structure:

(14) ##STR00005##

(15) In some embodiments, the sulfide-scavenging agent is a 1,3,5-triazine derivative of Formula I

(16) ##STR00006##
having the substituents for R.sup.1, R.sup.2, and R.sup.3 defined above. In some embodiments, the 1,3,5-triazine is anhydrous. In some embodiments, each of R.sup.1, R.sup.2, and R.sup.3 is independently selected from hydrogen or straight or branched C.sub.1-C.sub.30 alkyl. In some embodiments, each of each of R.sup.1, R.sup.2, and R.sup.3 is independently selected from straight or branched C.sub.6-C.sub.30 alkyl. In some embodiments, each of R.sup.1, R.sup.2, and R.sup.3 is CH.sub.2CH.sub.2OH. In some embodiments, each of R.sup.1, R.sup.2, and R.sup.3 is H.

(17) In some embodiments, each of R.sup.1, R.sup.2, and R.sup.3 is independently hydroxyl substituted straight or branched C.sub.1-C.sub.30 alkyl. In some embodiments, each of R.sup.1, R.sup.2, and R.sup.3 is independently hydroxyl substituted straight or branched C.sub.6-C.sub.30 alkyl.

(18) In some embodiments, each of R.sup.1, R.sup.2, and R.sup.3 is independently straight or branched C.sub.1-C.sub.30 alkyl substituted with straight or branched C.sub.1-C.sub.30 alkoxy. In some embodiments, each of R.sup.1, R.sup.2, and R.sup.3 is independently straight or branched C.sub.6-C.sub.30 alkyl substituted with straight or branched C.sub.1-C.sub.30 alkoxy. In some embodiments, each of R.sup.1, R.sup.2, and R.sup.3 is independently straight or branched C.sub.6-C.sub.30 alkyl substituted with straight or branched C.sub.6-C.sub.30 alkoxy.

(19) In some embodiments, each of R.sup.1, R.sup.2, and R.sup.3 is the same. In some embodiments, R.sup.1 is different from R.sup.2 and R.sup.3. In some embodiments, R.sup.1 and R.sup.2 are the same. In some embodiments, R.sup.1 and R.sup.2 are the same and are also different from R.sup.3. In some embodiments, R.sup.1 is different from R.sup.2 and R.sup.3, and R.sup.2 is different from R.sup.3.

(20) The metal-containing compound of the presently disclosed compositions is not particularly limited. In some embodiments, the metal-containing compound comprises a metal carboxylate, a metal oxide, a metal carbonate, and any combination thereof.

(21) For example, in some embodiments, the metal-containing compound may comprise one or more metal carboxylates, such as a copper carboxylate, a zinc carboxylate, an iron carboxylate, and any combination thereof. In some embodiments, the metal-containing compound may comprise one or more metal carboxylates and one or more metal oxides. In some embodiments, the metal-containing compound may comprise one or more metal carboxylates, one or more metal oxides, and one or more metal carbonates. In some embodiments, the metal-containing compound may comprise one or more metal carboxylates and one or more metal carbonates.

(22) In additional embodiments, the metal-containing compound may comprise one or more metal oxides, such as zinc oxide, copper oxide, iron oxide, and any combination thereof. In some embodiments, the metal-containing compound may comprise one or more metal oxides and one or more metal carbonates. In other embodiments, the metal-containing compound may comprise one or more metal carbonates, such as zinc carbonate, iron carbonate, copper carbonate, and any combination thereof.

(23) The metal of the metal-containing compound is not particularly limited. In some embodiments, the metal comprises a divalent ion selected from, but not limited to, Cu (II), Zn (II), Fe (II), Ni (II), Co (II), Mn (II), Ca (II), Mg (II), and any combination thereof. In some embodiments, the metal-containing compound comprises a member selected from the group consisting of copper, zinc, iron, and any combination thereof.

(24) In some embodiments, the metal-containing compound comprises copper acetate, copper bis-glycinate, zinc acetate, zinc bis-glycinate, zinc 2-ethylhexanoate, copper 2-ethylhexanoate, iron 2-ethylhexanoate and any combination thereof. In some embodiments, the metal-containing compound comprises zinc octoate. In particular embodiments, the molar ratio of zinc complexed with octanoic acid is not 1:2. In some embodiments, the ratio is from about 2.1:3 to about 1.97:3 (see, for example, U.S. Pat. No. 8,246,813, the entire contents of which are incorporated into the present disclosure in their entirety).

(25) In accordance with the present disclosure, carboxylates may be derived from various carboxylic acids. In some embodiments, the carboxylic acids may comprise from 1 to about 20 carbon atoms. The carboxylic acids include various hydroxyl acids and amino acids, such as glycine, aspartic acid, citric acid, etc. In some embodiments, the carboxylic acid is selected from the group consisting of carbonic acid, methanoic acid, ethanoic acid, propanoic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, 2-ethyhexanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, icosanoic acid, and any combination thereof.

(26) In additional embodiments, the carboxylic acid is selected from branched neo-acids, such as neodecanoic acid. In some embodiments, the carboxylic acid is selected from an aromatic acid, such as benzoic acid and/or naphthoic acid, wherein the aromatic rings may include alkyl and alkoxy groups attached to them.

(27) The asphalt disclosed herein may be, but does not need to be, polymer-treated asphalt. Depending upon the desired application of the asphalt, one or more polymers may be added thereto to modify certain performance characteristics. The polymers include, but are not limited to, various rubbers, thermoplastic elastomers, elastomeric polymers, and any combination thereof. Elastomeric polymers include synthetic and/or natural rubbers, such as, but not limited to, polybutadiene, ethylene/vinyl acetate copolymers, polyacrylates, styrene-butadiene copolymers, polyolefins, and styrene-isoprene copolymers. In some embodiments, the polymers comprise conjugated diene units and/or aromatic monovinyl hydrocarbon units. In certain embodiments, the polymer is PPA.

(28) The polymers may be crosslinked or may be free of crosslinks. One of ordinary skill in the art understands the types of agents that can be used to crosslink polymers such as, but not limited to, organic sulfur-containing crosslinkers, elemental sulfur crosslinkers, etc.

(29) The asphalt may comprise from about 0.1 weight % to about 10 weight % of the polymer. In some embodiments, the asphalt comprises from about 0.1 weight % to about 5 weight % of the polymer. In certain embodiments, the asphalt comprises about 1 weight % of the polymer.

(30) In accordance with certain embodiments of the present disclosure, PPA is added to the asphalt. Acid modification of the asphalt generally results in asphalt compositions that exhibit improved low temperature performance. The asphalt composition may include less than or equal to about 10 wt. % acid. In some embodiments, the asphalt composition includes less than or equal to about 5 wt. % acid. In some embodiments, the asphalt composition includes less than or equal to about 3 wt. % acid. In some embodiments, the asphalt composition includes less than or about 1 wt. % acid and may include from about 0.01 wt. % to about 1 wt. % acid, from about 0.05 wt. % to about 1 wt. % acid, or from about 0.1 wt. % to about 1 wt. % acid, for example.

(31) The compositions disclosed herein can optionally include one or more solvents. The solvent may be a polar solvent, for example. In some embodiments, the solvent is selected from the group consisting of diethylene glycol, 2-butoxyethanol, propylene glycol, monoethanol amine, and any combination thereof.

(32) The compositions disclosed herein can optionally include one or more additives. Suitable additives include, but are not limited to, asphaltene inhibitors, paraffin inhibitors, corrosion inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, gas hydrate inhibitors, biocides, pH modifiers, surfactants, and combinations thereof. Additional additives include sulfonating agents, crosslinking agents or combinations thereof. The asphalt composition may include from about 0.001 wt. % to about 5 wt. % of total additives or from about 0.01 wt. % to about 3 wt. % of total additives, for example.

(33) The crosslinking agents may be activators (e.g., zinc oxide), accelerators, such as sulfur compounds (e.g., mercaptobenzothizole (MBT)) or both accelerators and activators, such as a zinc salt of MBT, for example.

(34) The additives may further include unsaturated functional monomers, unsaturated carboxylic acids, unsaturated dicarboxylic acids, unsaturated anhydrides, unsaturated esters, unsaturated amides or combinations thereof, for example.

(35) The inventors discovered that certain components of the compositions display synergy when used to scavenge hydrogen sulfide from asphalt, including polymer-treated asphalt, such as PPA-treated asphalt. Specifically, the inventors discovered synergy between certain sulfide-scavenging agents and certain metal-containing compounds. For example, synergy was discovered when the metal-containing compound comprised a metal-carboxylate and when the sulfide-scavenging agent comprised the 1,3,5-triazine derivative of Formula I, where each of R.sub.1, R.sub.2 and R.sub.3 were a functionalized alkyl group.

(36) Preparation Methods

(37) In accordance with certain embodiments of the present disclosure, the compositions are made with anhydrous sulfide-scavenging agents to facilitate handling of PPA-treated asphalt and asphalt mixtures at temperatures around 250? C. In some embodiments, the temperature of the asphalt or asphalt mixture is less than about 200? C. In some embodiments, the temperature of the asphalt or asphalt mixture is less than about 150? C. In some embodiments, the temperature of the asphalt or asphalt mixture is less than about 100? C. In some embodiments, the temperature of the asphalt or asphalt mixture is less than about 90? C.

(38) Illustrative, non-limiting methods of forming such asphalt compositions are described below. For example, in one embodiment, asphalt is heated in a first mixing vessel to a temperature of from about 140? C. to 205? C. The asphalt concentrate may then be transferred to a second mixing vessel or remain in the first mixing vessel.

(39) PPA (or any other polymer disclosed herein) may be added to the mixing vessel. The polymer is added in a timed release sufficient to avoid foaming, such as from about 20 minutes to about 1 hour, for example. The polymer, however, can be added at any point in the process and to any vessel or conduit in the process. For example, the polymer can be added to a first or second mixing vessel or to a conduit operably connecting the first and second mixing vessels.

(40) The sulfide-scavenging agent may then be added. The metal-containing compound may be added before, after, and/or with the sulfide-scavenging agent. The sulfide-scavenging agent and/or metal-containing compound can be added before, after, and/or when the polymer is added. The addition of the sulfide-scavenging agent and/or the metal-containing compound may occur with mixing for about 15 minutes to about 10 hours.

(41) Product Applications

(42) The asphalt compositions described herein can be used for many applications, such as road paving, sealing, water proofing, asphalt cement and/or roofing, for example.

(43) The compounds, compositions, methods, and processes will be better understood by reference to the following examples, which are intended to be illustrative, and not limiting upon the scope of the present disclosure.

EXAMPLES

(44) Sulfide emissions from PPA-treated asphalt were measured to examine the effectiveness of various sulfide scavengers. All H.sub.2S levels reported below and observed were measured by modified ASTM D5705 at annotated temperature and residual time.

(45) The H.sub.2S testing was conducted by adding 1 wt. % PPA to asphalt and keeping the mixture at 150? C. for 24 hours to allow any H.sub.2S release. At the end of this 24 hour period, the vapor phase H.sub.2S concentration of sample was determined and recorded as initial H.sub.2S. The composition comprising the sulfide-scavenging agent and metal-containing compound was then added to this PPA-treated asphalt sample, and the sample was kept at 150? C. for another 24 or 48 hours. The vapor phase H.sub.2S after this 24 or 48 hour period was measured and reported as final H.sub.2S.

(46) In a first set of experiments, the composition comprised copper acetate and a 1,3,5-triazine derivative of Formula I, where each of R.sub.1, R.sub.2 and R.sub.3 were CH.sub.2CH.sub.2OH. Results are shown in Tables 1-3.

(47) TABLE-US-00001 TABLE 1 95 weight % solvent diluted triazine with 5 weight % copper acetate After PPA RXN Dosage Final H2S Sample H2S Level/ppm Ratio ppm ppm Reduction 1 5000 0 0 5000 0% 2 5000 0.4 2000 1900 62% 3 5000 0.8 4000 800 84% 4 5000 1.2 6000 300 94% 5 5000 1.6 8000 0 100%

(48) TABLE-US-00002 TABLE 2 92.5 weight % solvent diluted triazine with 7.5 weight % copper acetate After PPA RXN Dosage Final H2S Sample H2S Level/ppm Ratio ppm ppm Reduction 1 5500 0 0 5500 0% 2 5500 0.4 2200 1800 67% 3 5500 0.8 4400 480 91% 4 5500 1 5500 0 100% 5 5500 1.2 6600 0 100% 6 5500 1.4 7700 0 100%

(49) TABLE-US-00003 TABLE 3 90 weight % solvent diluted triazine with 10 weight % copper acetate After PPA RXN Dosage Final H2S Sample H2S Level/ppm Ratio ppm ppm Reduction 1 5500 0 0 5500 0% 2 5500 0.4 2200 2100 62% 3 5500 0.6 3300 730 87% 4 5500 0.8 4400 150 97% 5 5500 1 5500 0 100% 6 5500 1.2 6600 0 100%

(50) Similar experiments to those above were carried out using the triazine without the copper acetate. Results are shown in Table 4. As can be seen, the mixture of the triazine and copper acetate outperformed triazine alone.

(51) TABLE-US-00004 TABLE 4 95 weight % solvent diluted triazine Initial Rxn Dosage/ Final Sample Additives H2S/ppm Ratio ppm H2S/ppm Reduction 1 Blank 7500 0 0 9500 ?27% 2 7500 0 0 7500 0% 9 Solvent 7500 1 7500 400 95% 10 diluted 7500 1 7500 620 92% 11 triazine 7500 2 15000 315 96% 12 7500 2 15000 390 95% 13 7500 3 22500 85 99% 14 7500 3 22500 100 99% 15 7500 3.5 26250 65 99%

(52) In an additional set of experiments, one-gallon containers containing asphalt samples were placed in an oven at around 300? F. for at least about 10 hours to allow the samples to flow. Once the samples were sufficiently heated, a mechanical shaker agitated each sample for about 3 minutes to ensure thorough mixing.

(53) Each testing sample was then prepared by transferring about 500 ml asphalt into a quart metal can, which was already pre-dosed with about 0.5 ml of PPA. After the transfer, each can was immediately capped and shaken rigorously to mix the asphalt with the PPA.

(54) The sample cans were then placed back into an oven for at least about 30 minutes to improve the flowability of the asphalt. After reheating, one can was taken out and hand-shaken for about 50 counts followed by measuring of the H.sub.2S amount with a Draeger tube. This amount was recorded as initial H.sub.2S. The rest of the cans were then treated with different amounts of additives according to the initial H.sub.2S. The dosage of copper acetate was determined by matching the same amount of copper acetate in the blended product.

(55) The treated sample cans were then stored at about 300? F. for about 24 hours. At the end of this period, each can was removed from the oven and hand-shaken for about 50 counts followed by measuring of the H.sub.2S content. This H.sub.2S level was recorded as Final H.sub.2S. Results are depicted in Tables 1 and 2.

(56) TABLE-US-00005 TABLE 1 Initial H2S/ .sup.1Rxn Final H2S/ Reduction Sample ppm Additives Ratio Dosage ppm % 1 2500 Blank N/A N/A N/A N/A 2 2500 10% copper acetate + 0.5 1250 590 76% 90% water free ppm triazine 3 2500 10% copper acetate + 1 2500 0 100% 90% water free ppm triazine 4 2500 100% copper N/A .sup.20.0625 g 1720 31% acetate 5 2500 100% copper N/A .sup.20.125 g 880 65% acetate .sup.1The Rxn Ratio was presented as the volume of additive vs Initial H.sub.2S. E.g., Rxn Ratio = 1 means 1 vppm additive was added for 1 ppm initial H.sub.2S. .sup.2The dosage of 100% copper acetate was determined by matching the same amount of copper acetate in the blended product. The detailed calculation was as follows: Density (10% copper acetate + 90% water free triazine) = 1.204 g/ml $\mathrm{Copper}\mathrm{acetate}\mathrm{for}\mathrm{Sample}3=\frac{1250\mathrm{ppm}}{1\mathrm{ppm}.Math.L\text{/}?L}?0.5L?\frac{1.204g\text{/}\mathrm{ml}}{1000\mathrm{?l}\text{/}\mathrm{ml}}?10\%=0.0625g$$\mathrm{Copper}\mathrm{acetate}\mathrm{for}\mathrm{Sample}4=\frac{2500\mathrm{ppm}}{1\mathrm{ppm}.Math.L\text{/}?L}?0.5L?\frac{1.204g\text{/}\mathrm{ml}}{1000\mathrm{?l}\text{/}\mathrm{ml}}?10\%=0.125g$

(57) TABLE-US-00006 TABLE 2 Initial H2S/ .sup.1.Rxn Final H2S/ Reduction Sample ppm Additives Ratio Dosage ppm % 1 600 Blank N/A N/A N/A N/A 2 600 10% copper 0.5 300 ppm 130 78% acetate + 90% water free triazine 3 600 10% copper 1 600 ppm 0 100% acetate + 90% water free triazine 4 600 100% copper N/A .sup.20.0181 g 460 23% acetate 5 600 100% copper N/A .sup.20.0361 g 230 62% acetate .sup.1.The Rxn Ratio was presented as the volume of additive vs Initial H.sub.2S. E.g., Rxn Ratio = 1 means 1 vppm additive was added for 1 ppm initial H.sub.2S. .sup.2The dosage of 100% copper acetate was determined by matching the same amount of copper acetate in the blended product. The detailed calculation was as follows: Density (10% copper acetate + 90% water free triazine) = 1.204 g/ml $\mathrm{Copper}\mathrm{acetate}\mathrm{for}\mathrm{Sample}4=\frac{300\mathrm{ppm}}{1\mathrm{ppm}.Math.L\text{/}?L}?0.5L?\frac{1.204g\text{/}\mathrm{ml}}{1000?l\text{/}\mathrm{ml}}?10\%=0.0181g$$\mathrm{Copper}\mathrm{acetate}\mathrm{for}\mathrm{Sample}5=\frac{600\mathrm{ppm}}{1\mathrm{ppm}.Math.L\text{/}?L}?0.5L?\frac{1.204g\text{/}\mathrm{ml}}{1000?l\text{/}\mathrm{ml}}?10\%=0.0361g$

(58) All of the compositions and methods disclosed and claimed herein can be made and executed without undue experimentation in light of the present disclosure. While this invention may be embodied in many different forms, there are described in detail herein specific preferred embodiments of the invention. The present disclosure is an exemplification of the principles of the invention and is not intended to limit the invention to the particular embodiments illustrated.

(59) Unless expressly stated to the contrary, use of the term a is intended to include at least one or one or more. For example, a metal-containing compound is intended to include at least one metal-containing compound or one or more metal-containing compounds.

(60) Any ranges given either in absolute terms or in approximate terms are intended to encompass both, and any definitions used herein are intended to be clarifying and not limiting. Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the invention are approximations, the numerical values set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard deviation found in their respective testing measurements. Moreover, all ranges disclosed herein are to be understood to encompass any and all subranges (including all fractional and whole values) subsumed therein.

(61) As used herein, the term about refers to the cited value being within the errors arising from the standard deviation found in their respective testing measurements, and if those errors cannot be determined, then about refers to within 10% of the cited value.

(62) The terms comprise(s), include(s), having, has, can, contain(s), and variants thereof, as used herein, are intended to be open-ended transitional phrases, terms, or words that do not preclude the possibility of additional acts or structures. The singular forms a, and and the include plural references unless the context clearly dictates otherwise. The present disclosure also contemplates other embodiments comprising, consisting of and consisting essentially of, the embodiments or elements presented herein, whether explicitly set forth or not.

(63) For example, in some embodiments, a composition as disclosed herein consists essentially of (or consists of) a metal-containing compound and a sulfide-scavenging agent. In some embodiments, a composition as disclosed herein consists essentially of (or consists of) a metal-containing compound, a sulfide-scavenging agent and a solvent. In some embodiments, a composition as disclosed herein consists essentially of (or consists of) a metal-containing compound, a sulfide-scavenging agent, and asphalt. In some embodiments, a composition as disclosed herein consists essentially of (or consists of) a metal-containing compound, a sulfide-scavenging agent, and polymer-treated asphalt. In some embodiments, a composition as disclosed herein consists essentially of (or consists of) a metal-containing compound, a sulfide-scavenging agent, polymer-treated asphalt, and a solvent.

(64) In accordance with the present disclosure, the phrases consist essentially of, consists essentially of, consisting essentially of, and the like limit the scope of a claim to the specified materials or steps and those materials or steps that do not materially affect the basic and novel characteristic(s) of the claimed invention.

(65) Furthermore, the invention encompasses any and all possible combinations of some or all of the various embodiments described herein. It should also be understood that various changes and modifications to the presently preferred embodiments described herein will be apparent to those skilled in the art. Such changes and modifications can be made without departing from the spirit and scope of the invention and without diminishing its intended advantages. It is therefore intended that such changes and modifications be covered by the appended claims.