IP Library Patent Application 13258018
Patent Application
App. No. 13/258,018

HYDROPHOBIC MONOMERS, HYDROPHOBICALLY-DERIVATIZED SUPPORTS, AND METHODS OF MAKING AND USING THE SAME

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Patent No.
US None
App. No.
13/258,018
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.

Claims (50)

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)

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 21, 2011
From: RASMUSSEN, JERALD K.; KIPKE, CARY A.; HEMBRE, JAMES I.; WICKERT, PETER D.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 026939/0671 →