Biosolvents useful for improved asphalt products utilizing recycled asphalt pavement or other brittle asphalt binders such as vacuum tower bottom

Abstract

The present application is directed to an asphalt binder composition comprising:an asphalt binder;a compound of formula (I):wherein R, A, n, and m are as described herein,a compound of formula (II):wherein R′, A′, n′, and m′ are as described herein. The present application is also directed to further compositions, methods of producing an asphalt binder composition, and methods of paving.

1 .- 33 . (canceled) 
     
     
         34 . A method of producing an asphalt binder composition comprising:
 providing an asphalt binder;   providing a polymer comprising two or more units of monomer A, wherein monomer A has a molecular weight of less than 500 Da;   providing sulfur;   providing a compound of formula (I):   
       
         
           
           
               
               
           
         
         
           wherein: 
           each A is selected independently at each occurrence thereof from the group consisting of 
         
       
       
         
           
           
               
               
           
         
         
            and 
           wherein at least one A is 
         
       
       
         
           
           
               
               
           
         
         n=1-12;
 m is 1, 2, or 3; 
 each 
 
       
       
         
           
           
               
               
           
         
         
            represents the point of attachment to a —CH 2 — group; 
           R is selected from the group consisting of H, C 1 -C 23  alkyl, and benzyl, wherein the C 1 -C 23  alkyl can be optionally substituted with an aryl, heteroaryl, or heterocyclyl; 
           R 1  and R 2  are independently selected from the group consisting of H, C 1 -C 23  alkyl and benzyl, wherein the C 1 -C 23  alkyl can be optionally substituted with an aryl, heteroaryl, or heterocyclyl; 
           wherein the compound of formula (I) has a mass content of oxirane greater than 0.1 and less than 15%; and 
         
         mixing the asphalt binder with the polymer comprising two or more units of monomer A, the sulfur, and the compound of formula (I) under conditions effective to produce an asphalt binder composition. 
       
     
     
         35 . An asphalt binder composition comprising:
 an asphalt binder;   a polymer comprising two or more units of monomer A, wherein monomer A has a molecular weight of less than 500 Da;   sulfur; and   a compound of formula (I):   
       
         
           
           
               
               
           
         
         
           wherein: 
           each A is selected independently at each occurrence thereof from the group consisting of 
         
       
       
         
           
           
               
               
           
         
         
            and 
           wherein at least one A is 
         
       
       
         
           
           
               
               
           
         
         
           n=1-12; 
           m is 1, 2, or 3; 
           each 
         
       
       
         
           
           
               
               
           
         
         
            represents the point of attachment to a —CH 2 — group; 
           R is selected from the group consisting of H, C 1 -C 23  alkyl, and benzyl, wherein the C 1 -C 23  alkyl can be optionally substituted with an aryl, heteroaryl, or heterocyclyl; 
           R 1  and R 2  are independently selected from the group consisting of H, C 1 -C 23  alkyl and benzyl, wherein the C 1 -C 23  alkyl can be optionally substituted with an aryl, heteroaryl, or heterocyclyl; 
           wherein the compound of formula (I) has a mass content of oxirane greater than 0.1 and less than 15%. 
         
       
     
     
         36 . The method of  claim 34 , wherein the mass content of oxirane in the compound of formula (I) is greater than 0.1 and less than 5%. 
     
     
         37 . The method of  claim 34 , wherein the compound of formula (I) is selected from the group consisting of epoxidized methyl soyate, epoxidized benzyl soyate, and epoxidized isoamyl soyate. 
     
     
         38 . The method of  claim 34 , wherein the asphalt binder is selected from the group consisting of unaged asphalt binder, aged asphalt binder from recycled asphalt pavement, vacuum tower distillation bottom binder, aged asphalt binder from recycled asphalt shingles, de-asphalting bottoms, residuum oil supercritical extraction unit bottoms, and mixtures thereof. 
     
     
         39 . The method of  claim 34 , wherein the Monomer A is selected from the group consisting of vinyl, acrylic, diolefin, nitrile, dinitrile, acrylonitrile monomer, monomer with reactive functionality, and crosslinking monomer. 
     
     
         40 . The method of  claim 34  further comprising:
 mixing the asphalt binder composition with a carboxyl additive. 
 
     
     
         41 . The product of the method of  claim 34 . 
     
     
         42 . The asphalt binder composition of  claim 35 , wherein the mass content of oxirane in the compound of formula (I) is greater than 0.1 and less than 5%. 
     
     
         43 . The asphalt binder composition of  claim 35 , wherein the Monomer A is selected from the group consisting of vinyl, acrylic, diolefin, nitrile, dinitrile, acrylonitrile monomer, monomer with reactive functionality, and crosslinking monomer. 
     
     
         44 . The asphalt binder composition of  claim 35 , wherein the compound of formula (I) is selected from the group consisting of epoxidized methyl soyate, epoxidized benzyl soyate, and epoxidized isoamyl soyate. 
     
     
         45 . An asphalt product composition comprising:
 the asphalt binder composition of  claim 35 , and   a mineral aggregate.   
     
     
         46 . The asphalt product composition of  claim 45 , wherein the mineral aggregate is selected from the group consisting of sand, gravel, limestone, quartzite, granite, crushed stone, recycled asphalt pavement (RAP), recycled asphalt shingles (RAS), and combinations thereof. 
     
     
         47 . The asphalt product composition of  claim 45 , wherein the asphalt product composition is in the form of asphalt concrete. 
     
     
         48 . The asphalt product composition of  claim 45 , wherein the asphalt product composition is in the form of an asphalt mixture. 
     
     
         49 . An asphalt product composition comprising:
 the asphalt binder composition of  claim 35 ;   fiberglass; and   a mineral aggregate.   
     
     
         50 . A roofing shingle comprising the asphalt binder composition of  claim 35 . 
     
     
         51 . A recycled asphalt pavement aggregate comprising the asphalt binder composition of  claim 35 . 
     
     
         52 . The asphalt binder composition of  claim 35  further comprising:
 a carboxyl additive. 
 
     
     
         53 . A method of forming a pavement comprising:
 (a) providing the asphalt binder composition of  claim 35 ;   (b) mixing the composition with a mineral aggregate to form a mixture;   (c) applying the mixture to a surface to be paved to form an applied paving material, and   (d) compacting the applied paving material to form the pavement.