Zwitterionic polymer, method for producing same and protein stabilizer containing zwitterionic polymer

Patent metadata

Field	Value
Publication number	US-11168159-B2
Application number	US-201816955375-A
Country	US
Kind code	B2
Filing date	Dec 26, 2018
Priority date	Dec 27, 2017
Publication date	Nov 9, 2021
Grant date	Nov 9, 2021

Abstract

Provided is a zwitterionic polymer that has a zwitterion that includes an effect of improving the stability of proteins. This zwitterionic polymer is a polymeric protein stabilizer that exhibits a protein stabilizing effect even at a small addition amount of addition, and at the same time has an antioxidant capability. Also provided is a method for producing this zwitterionic polymer. This problem is solved by a zwitterionic polymer containing a repeating unit represented by formula (1) and having a number-average molecular weight of 1,000 to 1,000,000. On formula (1), R1 and R2 are each independently selected from a hydrogen atom; linear, branched or cyclic alkyl groups having 1 to 6 carbons; aromatic groups having 6 to 20 carbons; or alkylene groups having 1 to 6 carbons and formed by linking R1 to R2. R3 represents a hydrogen atom or a methyl group).

First claim

The invention claimed is:

1. A zwitterionic polymer comprising a repeating unit represented by Formula (1) below and having a number-average molecular weight of 1,000-1,000,000,

wherein R 1 and R 2 is each independently selected from a hydrogen atom, a linear, branched or cyclic C1-C6 alkyl group, a C6-C20 aromatic group or a C1-C6 alkylene group in which R 1 and R 2 are linked to each other, and R 3 represents a hydrogen atom or a methyl group.

2. The zwitterionic polymer according to claim 1 , wherein R 1 and R 2 in Formula (1) are both hydrogen atoms.

3. The zwitterionic polymer according to claim 1 , further comprising a structural unit derived from (meth)acrylate ester, wherein the ratio of the mole number x of the repeating unit represented by Formula (1) above and the mole number y of the structural unit derived from (meth)acrylate ester is in a range of x:y=10:90-95:5.

4. A method for producing the zwitterionic polymer according to claim 1 , the method comprising A) and B) below in this order:
A) radically polymerizing a sulfide acrylamide monomer represented by Formula (2) below;

wherein R 1 represents a hydrogen atom, a linear, branched or cyclic C1-C6 alkyl group or a C6-C20 aromatic group, and R 3 represents a hydrogen atom or a methyl group); and
B) allowing the polymer obtained in A) above to react with a sulfide-reactive compound represented by Formula (3) below,
X—CH 2 —R 2   (3)

wherein X represents a chlorine atom, a bromine atom, an iodine atom, a mesyl group (methanesulfonyl group), a tosyl group (p-toluenesulfonyl group) or a trifluoromethanesulfonyl group, and R 2 represents a hydrogen atom, a linear, branched or cyclic C1-C6 alkyl group or a C6-C20 aromatic group).

5. A method for producing the zwitterionic polymer according to claim 1 , comprising
radically polymerizing a zwitterionic monomer represented by Formula (4) below in an aqueous solvent at 60° C. or lower,

wherein R 1 and R 2 each independently represents a hydrogen atom, a linear, branched or cyclic C1-C6 alkyl group, a C6-C20 aromatic group or a C1-C6 alkylene group in which R 1 and R 2 are linked to each other, and R 3 represents a hydrogen atom or a methyl group.

6. A zwitterionic monomer represented by Formula (4) below,

wherein R 1 and R 2 each independently represents a hydrogen atom, a linear, branched or cyclic C1-C6 alkyl group, a C6-C20 aromatic group or a C1-C6 alkylene group in which R 1 and R 2 are linked to each other, and R 3 represents a hydrogen atom or a methyl group.

7. A protein stabilizer comprising the zwitterionic polymer according to claim 1 .

8. A protein stabilizer comprising the zwitterionic polymer according to claim 2 .

9. A protein stabilizer comprising the zwitterionic polymer according to claim 3 .

Assignees

• Univ Yamagata Nat Univ Corp
• Nof Corp

Inventors

• Mori Hideharu
• Imamura Ryutaro

Classifications

• C08F120/58 Primary

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-acryloyl morpholine} · CPC title

• C07C321/18

  of an acyclic unsaturated carbon skeleton · CPC title

• C08F220/1804

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title

• C08F220/286

  and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate · CPC title

• C08F20/58 Primary

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-acryloylmorpholine} · CPC title