Nitroxylradical-containing copolymer which has phosphoric acid residue, and the use of the same

Patent metadata

Field	Value
Publication number	US-10398803-B2
Application number	US-201615779654-A
Country	US
Kind code	B2
Filing date	Nov 29, 2016
Priority date	Nov 30, 2015
Publication date	Sep 3, 2019
Grant date	Sep 3, 2019

Abstract

Provided is a coating agent which can be stably immobilized on metal surface, and which can give blood compatibility. Provided is a copolymer which is usable as the above-mentioned coating agent that comprises PEG segment and a segment which has a phosphoric acid residue (PO(—OH) 2 ) and a cyclic nitroxideradical randomly as a side chain or a pendant group.

First claim

The invention claimed is:

1. A copolymer of the following formula (I):

wherein:
A is a hydrogen atom, an unsubstituted or substituted C 1-12 alkyl, wherein when the alkyl is substituted, the substituent is a formyl group or a group of the formula R 1 R 2 CH— wherein R 1 and R 2 independently represent C 1-4 alkoxy or when put together, represent —OCH 2 CH 2 O—, —O(CH 2 ) 3 O— or —O(CH 2 ) 4 O—;
L is either a bond or a linker selected from the group consisting of the following formulae:

—(CH 2 ) c S—, —CO(CH 2 ) c S—, —(CH 2 ) c NH—, —(CH 2 ) c CO—, —CO—, —COO—, and —CONH—;
X 1 is selected from the group consisting of the following formulae:

and

wherein the formulae are covalently bonded via a group of the formula —(CH 2 ) a —NH—(CH 2 ) a — or —(CH 2 ) a —O—(CH 2 ) a —;
X 2 is PO(—OH) 2 ;
Y is H, SH or S—C(═S)-Ph wherein Ph is a phenyl which may be substituted by one or two methyl or methoxy groups;
a's independently are an integer of 0 to 5;
b is an integer of 2 to 6;
c's are an integer of 1 to 5;
m is an integer of 2 to 10,000;
n is an integer of 1 to 360; and
k is an integer of 1 to 480;
provided that up to 50% of n X's or up to 50% of k Y's may respectively be H, halogen or hydroxyl; and also provided that n units in the corresponding repeating units and k units in the corresponding repeating units are randomly present.

2. The copolymer of claim 1 wherein n+k is an integer of 5 to 600, n/(n+k) is 0.2 to 0.8, k/(n+k) is 0.2 to 0.8, wherein, in principle, 100% of n and k repeating units are groups as defined above with respect to X 1 and X 2 , in the definitions of n and k of the above-mentioned formula.

3. The copolymer of claim 2 wherein k is an integer of at least 3, and n is an integer of at least 3.

4. The copolymer of claim 1 wherein L is paraxylylene or methaxylylene.

5. A surface of metal material which supports the copolymer of claim 1 .

6. The surface of metal material of claim 5 wherein metal material is stainless steel, titanium or titanium alloy.

7. The surface of metal material of claim 5 which is selected from the surface of stent, auxiliary artificial heart, artificial joint, cell culturing device, cell analyzing device and cell separating device or parts thereof.

8. A device which has on its surface a coating film originated from the copolymer of claim 1 , wherein said surface is selected from the surface of metal material of stent, auxiliary artificial heart, artificial joint, cell culturing device, cell analyzing device and cell separating device and the parts thereof.

Assignees

• Univ Tsukuba

Inventors

• Nagasaki Yukio
• Ikeda Yutaka
• Akasaka Kouya

Classifications

• C09D171/02

  Polyalkylene oxides · CPC title

• C09D153/005

  Modified block copolymers · CPC title

• C08G65/337

  containing other elements (organic compounds containing halogens only as halides of a carboxyl group C08G65/332) · CPC title

• C08G65/334

  containing sulfur · CPC title

• C08F8/32

  by reaction with amines · CPC title