Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Patent
1990-09-04
1991-04-16
Schofer, Joseph L.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
52629295, 526328, 5263294, C08F 1216, C08F 2200, C08F 2018, C08F22218
Patent
active
050083589
DESCRIPTION:
BRIEF SUMMARY
The invention relates to polymer compositions particularly, but not exclusively, suitable for use in the preparation of supports for affinity chromatography.
Known polymeric supports include crosslinked labile hydroxy group-containing polymers. For example, U.S. Pat. No. 4,330,440 describes polymer supports for affinity chromatography comprising poly(hydroxyethyl methacrylate). The support is activated by reaction with a carbonylating agent to facilitate the coupling of a ligand to the support. The ligand is a substituent selected to be specifically interactive with a compound to be immobilised on the polymer support. For example, the ligand may be a protein.
A number of crosslinking agents are known for producing the crosslinked polymers. The crosslinking agents are low molecular weight compounds e.g. glutaraldehyde and epichlorohydrin. For a range of applications, the presence of residual unreacted or partly reacted crosslinking agent introduces a variety of problems in the manufacture and use of the polymers. The problems include the gradual leaching of the crosslinking agent from the polymer and the inactivation of ligands e.g. proteins in affinity separation systems.
The invention aims to overcome these problems by providing copolymers incorporating a monomer unit which can generate crosslinks without resort to added low molecular weight crosslinking agent.
More particularly, the invention provides a hydrophilic crosslinkable copolymer comprising monomer units derived from an ester of an ethylenically unsaturated carboxylic acid wherein the ester group contains a labile primary hydroxyl group and monomer units derived from a halohydroxyalkyl ester of an ethylenically unsaturated carboxylic acid.
The invention also provides a method of making a hydrophilic crosslinkable copolymer which method comprises forming a composition comprising an ester of an ethylenically unsaturated carboxylic acid wherein the ester group contains a labile primary hydroxyl group, a halohydroxyalkyl ester of an ethylenically unsaturated carboxylic acid and a polymerisation initiator and subjecting the composition to conditions which generate free radicals from the polymerisation initiator.
In another aspect, the invention provides an element for use in the removal of a chemical species from a fluid comprising a support coated with a layer of a copolymer of the invention.
A method of removing a chemical species from a fluid comprises contacting the fluid with a polymer of the invention having a ligand for the species bound thereto.
All polymers of the invention are expected to be of use in affinity separation systems because of the presence of the labile hydroxy group.
The labile hydroxy group-containing monomer units may be present in an amount up to 95 mole percent based on the polymer. Preferably, the monomer units represent the major monomer component of the copolymer and may be present in an amount from 60 to 95 mole percent, more preferably from 75 to 90 mole percent.
Preferred labile hydroxy group-containing monomers include hydroxyalkyl-containing monomers such as hydroxyalkyl acrylates and methacrylates. A particularly preferred monomer is hydroxyethyl methacrylate.
The halohydroxyalkyl ester monomer units enable the copolymer to be crosslinked. The amount of the units present in the copolymer will depend on the degree of crosslinking desired. The monomer units will normally be present as a minor component of the polymer, for example, in an amount from 5 to 40 mole percent, preferably from 10 to 25 mole percent.
In a preferred embodiment, the halohydroxyalkyl ester is an acrylate or a methacrylate.
Preferably, the halohydroxyalkyl group contains from 2 to 6, more preferably 3, carbon atoms and the halo and hydroxy substituents are on adjacent carbon atoms. The preferred halo substituent is a chloro substituent. The most preferred monomer is 3-chloro-2-hydroxypropyl methacrylate.
An improvement in the hydrophilicity of the copolymer may be achieved by the incorporation of additional monomer units derived from an ester of
REFERENCES:
patent: 4016133 (1977-04-01), Hyosu et al.
P. Bajaj and M. Padmanaban, Copolymerization of Acrylonitrile with 3-Chloro, 2-Hydroxy-Propyl Acrylate and Methacrylate, Journal of Polymer Sciences: Polymer Chemistry Edition, 21, 2261-2270 (1983).
Anderson Larry
Batts Gregory N.
Jones Stephen A.
Purbrick Malcolm D.
Scriven Clare E.
Cheng Wu C.
Eastman Kodak Company
Schofer Joseph L.
Wells Doreen M.
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