Hydrophobic monomers, hydrophobically-derivatized supports, and methods of making and using the same

Abstract

A composition is disclosed comprising a hydrophobic monomer having the structure: CH 2 ═CR 4 C(O)NHC(R 1 R 1 )(C(R 1 R 1 )) n C(O)XR 3 wherein n is an integer of 0 or 1; R 1 is independently selected from at least one of: a hydrogen atom, alkyls aryls, and alkylaryls, wherein the alkyls, aryls, and alkylaryls have a total of 10 carbon atoms or less; R 3 is a hydrophobic group selected from at least one of: alkyls, aryls, alkylaryls and ethers, wherein the alkyls, aryls, alkylaryls and ethers have a total number of carbon atoms ranging from 4 to 30; R 4 H or CH 3 ; X is O or NH. In some embodiments the hydrophobic monomer is derived from an amine or an alcohol (HXR 3 ) that has a hydrophilicity index of 25 or less. A polymerizable composition comprising the hydrophobic monomer is disclosed, which optionally may comprise a cross-linking monomer and/or a non-cross-linking monomer. This polymerizable mixture may be used to from hydrophobically-derivatized supports, which may be used in applications such as hydrophobic interaction chromatography.

1 . A composition comprising a hydrophobic monomer having the structure:
   CH 2 ═CR 4 C(O)NHC(R 1 R 1 )(C(R 1 R 1 )) n C(O)XR 3  
   
       wherein n is an integer of 0 or 1; R 1  is independently selected from at least one of: alkyls, aryls, and alkylaryls, wherein the alkyls, aryls, and alkylaryls have a total of 10 carbon atoms or less; R 3  is a hydrophobic group selected from at least one of alkyls, aryls, alkylaryls and ethers, wherein the alkyls, aryls, alkylaryls and ethers have a total number of carbon atoms ranging from 4 to 30; R 4  is H or CH 3 ; and X is NH; wherein the hydrophobic monomer is derived from an amine or an alcohol (HXR 3 ) that has a hydrophilicity index of 25 or less. 
     
     
         2 . The composition of  claim 1  wherein R 1  is independently selected from at least one of: methyl, ethyl, phenyl, or combinations thereof. 
     
     
         3 . The composition of  claim 1  wherein R 3  is selected from at least one of: benzyl, phenethyl, phenoxyethyl, phenylpropyl, butyl, pentyl, hexyl, octyl, dodecyl, octadecyl, phenylbutyl, or combinations thereof. 
     
     
         4 . The composition of  claim 1  wherein the hydrophobic monomer has a structure selected from at least one of:
 CH 2 ═CHC(O)NHC(CH 3 )(CH 3 )C(O)NH(CH 2 ) 4 C 6 H 5 ; 
 CH 2 ═CHC(O)NHC(CH 3 )(CH 3 )C(O)NHCH 2 C 6 H 5 ; 
 CH 2 ═CHC(O)NHC(CH 3 )(CH 3 )C(O)NH(CH 2 ) 2 C 6 H 5 ; 
 CH 2 ═CHC(O)NHC(CH 3 )(CH 3 )C(O)NH(CH 2 ) 2 OC 6 H 5 ; 
 CH 2 ═CHC(O)NHC(CH 3 )(CH 3 )C(O)NH(CH 2 ) 3 C 6 H 5 ; 
 CH 2 ═CHC(O)NHC(CH 3 )(CH 3 )C(O)NH(CH 2 ) 3 CH 3 ; 
 CH 2 ═CHC(O)NHC(CH 3 )(CH 3 )C(O)NH(CH 2 ) 5 CH 3 ; 
 CH 2 ═CHC(O)NHC(CH 3 )(CH 3 )C(O)NH(CH 2 ) 7 CH 3 ; 
 CH 2 ═CHC(O)NHC(CH 3 )(CH 3 )C(O)NH(CH 2 ) 11 CH 3 ; 
 CH 2 ═CHC(O)NHC(CH 3 )(CH 3 )C(O)NH(CH 2 ) 17 CH 3 ; or combinations thereof. 
 
     
     
         5 . A polymerizable mixture comprising the hydrophobic monomer of  claim 1 . 
     
     
         6 . A polymerizable mixture of  claim 5  further comprising a cross-linking monomer. 
     
     
         7 . The polymerizable mixture of  claim 6 , wherein the cross-linking monomer is selected from at least one of: N,N′-alkylenebis(meth)acrylamides, alkylenebis(meth)acrylates, divinylaromatics, polyallylesters, or combinations thereof. 
     
     
         8 . The polymerizable mixture of  claim 5 , further comprising a non-cross-linking monomer. 
     
     
         9 . The polymerizable mixture of  claim 8 , wherein the non-cross-linking monomer is selected from at least one of: dimethylacrylamide, acrylamide, methacrylamide, hydroxyethyl(meth)acrylate, or combinations thereof 
     
     
         10 .- 11 . (canceled) 
     
     
         12 . The polymerizable mixture of  claim 5 , further comprising a porogen. 
     
     
         13 . (canceled) 
     
     
         14 . An article comprising a reaction product of the polymerizable mixture according to  claim 5 . 
     
     
         15 . The article of  claim 14 , wherein the article is a hydrophobically-derivatized support. 
     
     
         16 . The article of  claim 14 , wherein the hydrophobic monomer is uniformly distributed throughout the article. 
     
     
         17 . A method of using the article of  claim 14 , wherein the article is used to purify at least one of: proteins, antibodies, fusion proteins, vaccines, peptides, enzymes, DNA, RNA, or combinations thereof. 
     
     
         18 . A method of making a hydrophobically-derivatized support comprising:
 (a) providing a mixture comprising:
 (ii) a hydrophobic monomer having the structure:
   CH 2 ═CR 4 C(O)NHC(R 1 R 1 )(C(R 1 R 1 )) n C(O)XR 3  
 
 
   
       wherein n is an integer of 0 or 1; R 1  is independently selected from at least one of: a hydrogen atom, alkyls, aryls, and alkylaryls, wherein the alkyls, aryls, and alkylaryls have a total of 10 carbon atoms or less; R 3  is a hydrophobic group selected from at least one of: alkyls, aryls, alkylaryls and ethers, wherein the alkyls, aryls, alkylaryls and ethers have a total number of carbon atoms ranging from 4 to 30; R 4  is H or CH 3 ; and X is O or NH;
   (ii) a cross-linking monomer; and   (iii) optionally, a non-cross-linking monomer; and   
 (b) polymerizing the mixture; and 
 (c) confining the polymerized mixture to generate a chromatography medium or a filtration medium. 
 
     
     
         19 .- 20 . (canceled) 
     
     
         21 . The method of  claim 18 , wherein the polymerized mixture are particles. 
     
     
         22 . The method of  claim 18 , wherein the polymerized mixture is coated, or grafted onto at least one of: a woven web, non-woven web, microporous fibers, microporous membranes, film, or combinations thereof. 
     
     
         23 . A method of making a hydrophobically-derivatized support comprising:
 (a) providing a hydrophobic monomer having the structure:
   CH 2 ═CR 4 C(O)NHC(R 1 R 1 )(C(R 1 R 1 )) n C(O)XR 3  
 
   
       wherein n is an integer of 0 or 1; R 1  is independently selected from at least one of: a hydrogen atom, alkyls, aryls, and alkylaryls, wherein the alkyls, aryls, and alkylaryls have a total of 10 carbon atoms or less; R 3  is a hydrophobic group selected from at least one of: alkyls, aryls, alkylaryls and ethers, wherein the alkyls, aryls, alkylaryls and ethers have a total number of carbon atoms ranging from 4 to 30; R 4  is H or CH 3 ; X is O or NH;
 (b) providing a substrate; 
 (c) contacting the hydrophobic monomer to the substrate; and 
 (d) polymerizing the hydrophobic monomer. 
 
     
     
         24 . The method of  claim 23 , wherein the polymerizing results in a coating on the substrate. 
     
     
         25 . The method of  claim 23 , wherein the polymerizing results in a grafting from the substrate. 
     
     
         26 . (canceled)