# US 5,534,597 A · Water insoluble cross-linked acid compositions

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- Number: US 5,534,597 A
- Document ID: US5534597A
- Status: Granted
- Kind: A
- Application number: 08/459,252
- Filed: 1995-06-02
- Granted: 1996-07-09
- Earliest claimed: 1992-04-30
- Assignees: Affinity Technology, Inc.
- Inventors: John Krupey
- Web page: https://patentgrep.com/patent/US5534597A

## CPC

- C12N 7/00: Viruses; Bacteriophages; Compositions thereof; Preparation or purification thereof (preparing medicinal viral antigen or antibody compositions, e.g. virus vaccines, A61K39/00)
- C08F 8/12: Hydrolysis
- C08F 2810/20: leading to a crosslinking, either explicitly or inherently
- C08F 2810/50: wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
- C12N 2710/10351: Methods of production or purification of viral material
- C12N 2795/14143: viral genome or elements thereof as genetic vector
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

There is provided water insoluble cross-linked polyhydroxy polycarboxylic acid having at least two strands each having a strand skeleton of the formula: ##STR1## wherein one carbonyl group of at least one maleoyl moiety thereof in each strand is covalently linked to a --HN.[(H).sub.p (CH).sub.z.(OH).sub.m ].NH-- moiety to provide the presence therein of at least one cross linking moiety of the formula: ##STR2## wherein R is hydrogen or lower alkylene or lower alkoxy of 1-4 carbon atoms, or phenyl, z is an integer of 1-4, p is 0 or an integer up to z-1, m is 1 or an integer up to z, wherein the ratio of cross-links to poly (alkylene carbonic acid) strands is between about 1 and about 200 to 2. There is disclosed a method of making such polyhydroxy polycarboxylic acid as well as methods of utilizing same to remove proteins from aqueous media containing same to provide a matrix. Methods are disclosed for recovering proteins from said matrix without denaturing them and methods for recovering the polyhydroxy polycarboxylic acid from said matrix.

## Claims

### Claim 1

A water insoluble cross-linked polyhydroxy polycarboxylic acid obtained by cross-linking a polymer of the formula: ##STR10## wherein R is hydrogen or lower alkylene or lower alkoxy of 1-4 carbon atoms, or phenyl,and q is an integer of 7 to 10,000, with an alpha, omega diaminohydroxy alkane of the formula:
H.sub.2 N.[(H).sub.p (CH).sub.z.(OH).sub.m ].NH.sub.2
wherein z is an integer of 1-4, p is 0 or an integer up to z-1, m is 1 or an integer up to z, and hydrolyzing the unreacted anhydride groups, wherein the ratio of the initially charged diaminohydroxyalkane to the initially charged poly (alkylene maleic anhydride) is between about 1 and about 200 to 1 mol/mol, said water insoluble cross-linked polyhydroxy polycarboylic acid being selected from the group consisting of such acids having at least two strands each having a strand skeleton of formula III: ##STR11## wherein one carbonyl group of at least one maleoyl moiety thereof in each strand is covalently linked to a
--HN.[(H).sub.p (CH).sub.z.(OH).sub.m ].NH--
moiety to provide the presence therein of cross linking moieties of the formula: ##STR12## wherein R, z, p and m are as defined above, and y is an integer up to m, and the esters thereof with the anhydride corresponding to the skeleton of formula III, wherein the ratio of cross-links to poly (alkylene carbonic acid) strands is between about 1 and about 200 to 2.

### Claim 2 (depends on 1)

The product obtained by treatment of the water insoluble cross-linked polyhydroxy polycarboxylic acid of claim 1 with aqueous alkali.

### Claim 3

A water insoluble cross-linked polyhydroxy polycarboxylic acid having at least two strands each having a strand skeleton of formula III: ##STR13## wherein one carbonyl group of at least one maleoyl moiety thereof in each strand is covalently linked to a
--HN.[(H).sub.p (CH).sub.z.(OH).sub.m ].NH-- moiety
to provide the presence therein of cross linking moieties of the formula: ##STR14## wherein R is hydrogen of lower alkylene or lower alkoxy of 1-4 carbon atoms, or phenyl, y is an integer up to m, z is an integer of 1-4, p is 0 or an integer up to z-1, m is 1 or an integer up to z, and the esters thereof with the anhydride corresponding to the skeleton of formula III, wherein the ratio of cross-links to poly (alkylene carbonic acid) strands is between about 1 and about 200 to 2.

### Claim 4 (depends on 1)

A method of making insoluble cross-linked polyhydroxy polycarboxylic acid containing of claim 1 which compromises a) cross-linking a polymer of the formula: ##STR15## wherein R is hydrogen or lower alkoxy or lower alkylene of 1-4 carbon atoms, or phenyl, q is an integer of 7 to 10,000, with an alpha, omega diaminohydroxy alkane of the formula:
H.sub.2 N.[(H).sub.p (CH).sub.z.(OH).sub.m ].NH.sub.2
wherein z is an integer of 1-4, p is 0 or an integer up to z-1, m is 1 or an integer up to z, and b) hydrolyzing the unreacted anhydride groups, wherein the ratio of initially charged diaminohydrxyalkane to initially charged poly (alkylene maleic anhydride) is between about 1 and about 200 to 1 mol/mol.

### Claim 5 (depends on 3)

A method of hydrolyzing the water insoluble cross-linked polyhydroxy polycarboxylic acid compound of Formula VI of claim 3 which compromises treating said compound of Formula VI with dilute aqueous alkali.