Ketal amide compounds, methods of making, and applications

Abstract

Disclosed herein are ketal amide compounds. The ketal amide compounds are synthesized by the reaction of ketal acids or ketal esters with amine functional compounds. Also disclosed are methodologies useful to make the ketal amide compounds. Also disclosed herein are formulations and articles containing the ketal amide compounds.

1 . A compound having structure I: 
       
         
           
           
               
               
           
         
       
       wherein
 R 1  is a linear, branched, or cyclic alkyl, alkenyl, or alkynyl group, or an aryl or alkaryl group, or a polymeric group comprising a polyethylene having multiple amino residues, a poly(ethyleneimine), a polyoxyalkyleneamine, or a branched polyurea having primary amide groups, wherein the alkyl, alkenyl, aryl, alkaryl, or polymeric groups can have one or more heteroatoms; 
 R 2  is hydrogen or an alkyl group having 1 to 6 carbon atoms, wherein each R 2  may be the same or different; 
 R 3  and R 4  are independently hydrogen, halogen, amine, mercapto, phosphate, phosphonooxy, silyl, siloxane, alkynyl, or a linear, branched, or cyclic alkyl or alkenyl groups having 1 to 18 carbon atoms, or an aryl or alkaryl group, wherein the alkyl, alkenyl, aryl, or alkaryl groups can have one or more heteroatoms, and wherein each R 3  and R 4  may be the same or different; 
 R 5  is hydrogen, alkynyl, or a linear, branched, or cyclic alkyl or alkenyl group having 1 to 18 carbon atoms, or an aryl or alkaryl group, wherein the alkyl, alkenyl, aryl, or alkaryl groups can have one or more heteroatoms, and wherein each R 5  may be the same or different; 
 R 6 , R 8 , and R 9  are independently hydrogen, halogen, or an alkyl group having between 1 and 6 carbon atoms and optionally one or more heteroatoms, and wherein each R 6 , R 8 , and R 9  may be the same or different; 
 R 7  is —CH 2 OH, —NH 2 , —CH 2 NH 2 , —CH 2 SH, —CH 2 Br, 
 
       
         
           
           
               
               
           
         
         wherein
 A, B, and D are independently linear, branched, or cyclic alkyl, alkenyl, or alkynyl groups, or aryl or alkaryl groups, wherein the alkyl, alkenyl, alkynyl, aryl, or alkaryl groups have 1 to 36 carbon atoms and can further have one or more heteroatoms; and 
 X is O, S, or NH; and
 wherein each R 7  may be the same or different; 
 
 
         a is 0 or an integer of between 1 and 12, and each a is the same or different; 
         b is 0 or 1, wherein b=0 indicates a five membered ring, 
       
       
         
           
           
               
               
           
         
       
       and b=1 indicates a 6 membered ring, 
       
         
           
           
               
               
           
         
       
       and each b is the same or different; and
 α is an integer of 2 or more. 
 
     
     
         2 . The compound of  claim 1  wherein the one or more heteroatoms are independently halogen, nitrogen, oxygen, sulfur, silicon, or phosphorus. 
     
     
         3 . The compound of  claim 2  wherein the one or more heteroatoms are in a functional group that is amino, carbonate, imide, amide, sulfone, sulfonamide, urethane, mercapto, disulfide, ether, ester, phosphate, phosphonooxy, silane, or silyl functional groups, or a combination thereof. 
     
     
         4 . The compound of  claim 1  wherein the polymeric group comprises a surface, a layer on top of a surface, a particle surface, or a porous particle interior. 
     
     
         5 . The compound of  claim 1  wherein α is 2 and R 1  is —(CH 2 ) 3 —, 1,2-cyclohexyl, —(CH 2 ) 6 —, —CH 2 CH 2 CH(CH 3 )CH 2 C(CH 3 ) 2 CH 2 —, or —CH 2 CH 2 C(CH 3 ) 2 CH 2 CH(CH 3 )CH 2 —. 
     
     
         6 . The compound of  claim 1  wherein all values of a are 0, 1, or 2. 
     
     
         7 . The compound of  claim 6  wherein all values of a are 2 and all R 3  and R 4  are hydrogen. 
     
     
         8 . The compound of  claim 1  wherein all R 5  are methyl. 
     
     
         9 . The compound of  claim 1  wherein all b are 0 and all R 6  and R 8  are hydrogen. 
     
     
         10 . The compound of  claim 1  wherein all b are 1, all R 7  are —CH 2 OH, all R 8  are CH 2 CH 3  or CH 3 , and all R 6 , R 9  are H. 
     
     
         11 . The compound of  claim 1  wherein R 7  is —CH 2 —OH 
     
     
         12 . The compound of  claim 1  wherein α is 2. 
     
     
         13 . The compound of  claim 1  wherein R 7  is 
       
         
           
           
               
               
           
         
       
       and each A group is A′-NH—, wherein A′ is a linear, branched, or cyclic alkyl, alkenyl, or alkynyl group; an aryl group; or an alkaryl group. 
     
     
         14 . The compound of  claim 1  wherein R 7  is 
       
         
           
           
               
               
           
         
       
       and each A group is the residue of a fatty acid ester. 
     
     
         15 . The compound of  claim 14  wherein the A groups comprise a mixture of saturated and unsaturated fatty acid ester groups. 
     
     
         16 . A formulation comprising the compound of  claim 1 . 
     
     
         17 . The formulation of  claim 16  wherein the compound of  claim 1  is a plasticizer, a coalescing solvent, a cosolvent, a phase transfer agent, a compatibilizing agent, a nucleating agent, a surfactant, or an interfacial modifier. 
     
     
         18 . An article comprising the compound of  claim 1 . 
     
     
         19 . A compound having one or more fragments corresponding to structure II: 
       
         
           
           
               
               
           
         
       
       wherein
 R 1  is a divalent linear, branched, or cyclic alkyl, alkenyl, or alkynyl group, or an aryl or alkaryl group, or a polymeric group comprising a polyethylene having multiple amino residues, a poly(ethyleneimine), a polyoxyalkyleneamine, or a branched polyurea having primary amide groups, wherein the alkyl, alkenyl, aryl, alkaryl, or polymeric groups optionally comprise one or more heteroatoms; 
 R 2  is hydrogen or an alkyl group having 1 to 6 carbon atoms, wherein each R 2  may be the same or different; 
 R 3  and R 4  are independently hydrogen, halogen, amine, mercapto, phosphate, phosphonooxy, silyl, siloxane, alkynyl, or a linear, branched, or cyclic alkyl or alkenyl groups having 1 to 18 carbon atoms, or an aryl or alkaryl group, wherein the alkyl, alkenyl, aryl, or alkaryl groups optionally comprise one or more heteroatoms, and wherein each R 3  and R 4  may be the same or different; 
 R 5  is hydrogen, alkynyl, or a linear, branched, or cyclic alkyl or alkenyl group having 1 to 18 carbon atoms, or an aryl or alkaryl group, wherein the alkyl, alkenyl, aryl, or alkaryl groups optionally comprise one or more heteroatoms, and wherein each R 5  may be the same or different; 
 R 6 , R 8 , and R 9  are independently hydrogen, halogen, or an alkyl group having between 1 and 6 carbon atoms and optionally comprise one or more heteroatoms, and wherein each R 6 , R 8 , and R 9  may be the same or different; 
 X is O, S, or NH; 
 a is 0 or an integer of between 1 and 12, and each a is the same or different; 
 b is 0 or 1, wherein b=0 indicates a five membered ring, 
 
       
         
           
           
               
               
           
         
       
       and b=1 indicates a 6 membered ring, 
       
         
           
           
               
               
           
         
       
       and each b is the same or different;
 β is an integer of at least 1; 
 γ is either 0 or 1, wherein γ=0 denotes a covalent bond, and each γ is the same or different; and 
 E is a linking group selected from the divalent residue of phosgene or an organic bicarbonate; the divalent residue of a diisocyanate reacted with a diol, diamine, dithiol, aminoalcohol, or thioalcohol; or the divalent residue of a diacid, diester, anhydride, or diacid chloride; and E is the same or different for each β. 
 
     
     
         20 . A compound having structure III: 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  is a linear, branched, or cyclic alkyl, alkenyl, or alkynyl group, or an aryl or alkaryl group, wherein the alkyl, alkenyl, aryl, alkaryl groups optionally comprise one or more heteroatoms; 
 R 2  is hydrogen or an alkyl group having 1 to 6 carbon atoms and optionally comprise a hydroxyl group; 
 R 3  and R 4  are independently hydrogen, halogen, amine, mercapto, phosphate, phosphonooxy, silyl, siloxane, alkynyl, or a linear, branched, or cyclic alkyl or alkenyl groups having 1 to 18 carbon atoms, or an aryl or alkaryl group, wherein the alkyl, alkenyl, aryl, or alkaryl groups optionally comprise one or more heteroatoms, and each R 3  and R 4  may be the same or different; 
 R 5  is hydrogen, alkynyl, or a linear, branched, or cyclic alkyl or alkenyl group having 1 to 18 carbon atoms, or an aryl or alkaryl group, wherein the alkyl, alkenyl, aryl, or alkaryl groups optionally comprise one or more heteroatoms; 
 R 6 , R 8 , and R 9  are independently hydrogen, halogen, or an alkyl group having between 1 and 6 carbon atoms and optionally comprise one or more heteroatoms; 
 a is 0 or an integer of between 1 and 12; and 
 b is 0 or 1, wherein b=0 indicates a five membered ring, 
 
       
         
           
           
               
               
           
         
       
       and b=1 indicates a 6 membered ring,