Chemistry: molecular biology and microbiology – Carrier-bound or immobilized enzyme or microbial cell;... – Enzyme or microbial cell is immobilized on or in an organic...
Reexamination Certificate
1995-06-06
2003-03-04
Henderson, Christopher (Department: 1713)
Chemistry: molecular biology and microbiology
Carrier-bound or immobilized enzyme or microbial cell;...
Enzyme or microbial cell is immobilized on or in an organic...
C525S054100, C525S333300, C530S408000, C530S409000, C530S410000, C536S001110
Reexamination Certificate
active
06528292
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention is directed to supports utilized for making spectroscopic measurements and other studies which utilizes polystyrene or other aromatic containing polymers which are derivatized in such a manner so as to maintain the spectroscopic clarity of the support.
Polystyrene is one of the most used of all polymers. It is utilized either as pure polystyrene or in conjunction with a copolymer. Further, derivatives of polystyrene are known, such as chloromethylated polystyrene.
Polystyrene and its copolymers are soluble in most of the normal organic solvents with the exception of the lower alcohols. Other solvents swell or gel polystyrene and copolymers of polystyrene. The swelling action of many solvents on polystyrene allows for the use of polystyrene as the support matrix for resirs utilized for chromotography, ion exchange and the like.
Appropriate functional groups can be introduced into the aromatic rings of the polystyrene by one of two methods. The first is the actual polymerization of monomers which incorporate these functional groups. U.S. Pat. No. 3,872,067 describes a process for preparing a chloro-methylated polystyrene divinyl benzene copolymer utilizing appropriate polymerization of the preformed chloro-methylated polystyrene monomer.
For preparing derivatives of polymerized polystyrene, it is necessary to swell the polystyrene matrix such that pores and the like are formed in the polystyrene matrix allowing for introduction of the appropriate functional groups within the interior of the polystyrene bead or the like. U.S. Pat. No. 3,956,219 describes this process arid discusses the problems with regard to the same. In this patent the polystyrene is being substituted with certain peptide functionalities which have different solvent properties compared to the polystyrene. As the patent describes, in utilizing certain solvents such as methylene chloride, the polystyrene is extended, but the peptide functionalities are not soluble in this solvent or other similar solvents. The solution of U.S. Pat. No. 3,956,219 is in the use of N-methyl-2-pyrrolidone which acts both as a swelling agent for the polystyrene and as a solvent for the peptide groups.
U.S. Pat. No. 3,8860,486 describes the use of polymethylated styrene as a matrix for insolubilizing certain enzymes by reacting the chloromethyl groups with 2,5-dioxo-4-oxazolidine. The water soluble enzymes react with the oxazolidine group to insolubilize the same. This patent is characteristic of certain procedures wherein biological molecules can be manipulated by the absorption, attachment or reaction of the same with a suitable insoluble matrix such as a derivatized polymer or the like.
Both U.S. Pat. Nos. 3,974,110 and 3,995,094 discuss Freidel-Crafts substitution reactions for the introduction of chloromethyl groups onto the aromatic ring of polystyrene. In the body of U.S. Pat. No. 3,995,094 discussion is set forth as to problems with regard to solvents which can be utilized for such Freidel-Crafts modifications of polystyrene. Organic solvents such a benzene, toluene, zylene and the like themselves would undergo the halomethylation reaction and thus are not useful as solvents. The alcohols, diols and the like deactivate the normal Lewis acids utilized as catalysts in these reactions. Noted as acceptable solvents for the halomethylation of polystyrene are carbon disulfide and nitroalkanes and nitroaranes and the lower haloalkanes.
The above patents are directed to the reactions specified. therein with little consideration given to the actual final use of the polystyrene article. Thus, while carbon disulfide and chloroform might be suitable for Freidel-Crafts reactions on polystyrene, they could not be utilized if a polystyrene article was to be maintained in the same physical form after the reaction as it was before the start of the reaction.
U.S. Pat. No. 4,226,958 converts polystyrene to bromopolystyrene by bromination with bromine in carbon tetrachloride. The brominated polystyrene is then further reacted in other solvents to form certain organo-arsenic derivatives of the polystyrene. Again, as with the reactions discussed above, during the bromination step utilizing carbon tetrachloride little consideration is given to maintaining certain physical properties of the polystyrene such as optical clarity, optical surfaces and the like during the reaction thereon.
Because polystyrene can be derivatized such as by the formation of chloromethylated polystyrene, and because it is a transparent solid, it has been determined that polystyrene, polystyrene plus other copolymers, or other aromatic moiety containing polymers which also are optically clear, could be useful for support mediums for certain spectroscopic studies. However, in order to so utilize these polymers for this purpose, consideration must be given to maintaining the optical clarity of these supports and preventing salvation, geling, swelling, etching, or other physical changes to the support medium during any reaction on the polystyrene itself or on subsequent derivatives of polystyrene. It is to this end that this invention is directed.
BRIEF DESCRIPTION OF THE INVENTION
It has been determined that, by reacting polystyrene with suitable chemical reactants under certain conditions the optical properties of a polystyrene article can be maintained. Furthermore, it has been determined that by reacting polystyrene with certain reactants in the presence of certain solvents that reaction of the polystyrene in a preformed article can be limited to the surface of the article. This avoids derivatizing the total matrix of the polystyrene such that upon further reaction of the derivatized polystyrene with large molecules which are unable to penetrate the polystyrene matrix, the derivative groups to which the large molecules are attached also do not interfere with the spectroscopic properties of the polystyrene article.
In view of this it is a broad object of this invention to provide a process for initially introducing a functionality onto polystyrene or other aromatic group containing polymers utilizing a solvent system which maintains the optical integrity of the polystyrene and by not solvating, swelling, gelling or otherwise interacting with the main body of the polymetric article, limits the derivation of the aromatic moieities of the polymer to the surface of the article. It is a further object of this invention to provide support surfaces formed of polystyrene or other like polymers which contain aromatic moieties which are useful in supporting or holding biologically interesting molecules or useful in attaching those molecules to a support surface such that the molecules can be further derivatized and/or spectroscopically tagged, i.e. made to flouresce and the like, in order to study these molecules.
These, and other objects, as will be evident from the remainder of this specification are achieved in a process of derivatizing only the surface of an article formed of a polymer containing an aromatic moiety by introducing a substituent group onto said aromatic moiety which comprises: contacting said surface of said article with a reaction mixture wherein said reaction mixture contains tetramethylene sulfone as the solvent of said reaction mixture and further includes a reagent containing said substituent group; maintaining said reaction mixture in contact with said surface of said article to introduce said substituent group onto at least a portion of said a romatic moieties of said polymer located on said surface of said article; isolating said article from said reaction mixture.
The article of the preceding paragraph can be additionally reacted on wherein said substituent group is chosen from the group consisting of halo, haloalkyl, acyl and formyl and further including; contacting said isolated article with a further reaction mixture wherein said further reaction mixture contains one of the group consisting of tetramethylene sulfone, dimethyl disulfoxide or aqueous media as the solvent in said further reaction mixture and said fu
Aventis Pharmaceuticals Holdings Inc.
Henderson Christopher
Morrison & Foerster / LLP
LandOfFree
Derivatized polystyrene and other polymer supports for... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Derivatized polystyrene and other polymer supports for..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Derivatized polystyrene and other polymer supports for... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3076836