IP Library › Granted Patent US 11,377,512
Granted Patent B2
US 11,377,512 · App. 16/282,929 · Granted Jul 5, 2022

Hydrophilic copolymer and medical device

Inventors: Masanori Kuramoto (Kanagawa, JP); Takao Anzai (Kanagawa, JP)
Assignee: TERUMO KABUSHIKI KAISHA
C08F220/58A61L29/08A61L29/085A61L31/10C08F220/387C08F220/585C10M107/46C10M107/48A61L2400/10C08F220/382C08F2800/10C10M2221/025C10M2225/025C10N2040/50
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Quick Facts
Patent No.
US 11,377,512
App. No.
16/282,929
Granted
Jul 5, 2022
Kind
B2
Abstract

A hydrophilic copolymer that can form a surface lubricious layer exhibiting superior lubricating property and durability (lubrication retaining property), is provided. A hydrophilic copolymer having a good solvent solubility is provided. A hydrophilic copolymer is provided containing: structural units derived from a polymerizable monomer (A) having a sulfobetaine structure; structural units derived from a polymerizable monomer (B) having at least one group selected from the group consisting of a sulfonic acid group (—SO 3 H), a sulfuric acid group (—OSO 3 H), a sulfurous acid group (—OSO 2 H), and groups of salts thereof; and structural units derived from a polymerizable monomer (C) having a photoreactive group.

Claims (40)

1. A medical device comprising:

a substrate layer; and

a surface lubricious layer that is formed on at least a part of a surface of the substrate layer, wherein the surface lubricious layer contains a hydrophilic copolymer comprising:

structural units derived from a polymerizable monomer (A) having a sulfobetaine structure;

structural units derived from a polymerizable monomer (B) having at least one group selected from the group consisting of a sulfonic acid group (—SO 3 H), a sulfuric acid group (—OSO 3 H), a sulfurous acid group (—OSO 2 H), and groups of salts thereof; and

structural units derived from a polymerizable monomer (C) having a photoreactive group,

wherein the polymerizable monomer (B) is represented by the following formula (2):

wherein

R 21 is a hydrogen atom or a methyl group,

Z 2 is an oxygen atom or —NH—,

R 22 is a straight chain or branched chain alkylene group having 1 to 20 carbon atoms, and

X is a group selected from the group consisting of a sulfonic acid group (—SO 3 H), a sulfuric acid group (—OSO 3 H), a sulfurous acid group (—OSO 2 H), and groups of salts thereof.

2. A medical device comprising:

a substrate layer; and

a surface lubricious layer that is formed on at least a part of a surface of the substrate layer, wherein the surface lubricious layer contains a hydrophilic copolymer comprising:

structural units derived from a polymerizable monomer (A) having a sulfobetaine structure;

structural units derived from a polymerizable monomer (B) having at least one group selected from the group consisting of a sulfonic acid group (—SO 3 H), a sulfuric acid group (—OSO 3 H), a sulfurous acid group (—OSO 2 H), and groups of salts thereof; and

structural units derived from a polymerizable monomer (C) having a photoreactive group,

wherein the surface lubricious layer is bound to the substrate layer via the photoreactive group of the hydrophilic copolymer.

3. The medical device according to claim 1 , which is a catheter, a stent, or a guide wire.

4. The medical device according to claim 1 , wherein the polymerizable monomer (A) is represented by the following formula (1):

wherein

R 11 is a hydrogen atom or a methyl group,

Z 1 is an oxygen atom or —NH—,

R 12 and R 15 are each independently a straight chain or branched chain alkylene group having 1 to 20 carbon atoms, and

R 13 and R 14 are each independently a straight chain or branched chain alkyl group having 1 to 20 carbon atoms.

5. The medical device according to claim 1 , wherein in formula (1):

Z 1 is an oxygen atom,

R 12 and R 15 are each a straight chain alkylene group having 1 to 3 carbon atoms, and

R 13 and R 14 are each independently a methyl group.

6. The medical device according to claim 1 , wherein the polymerizable monomer (A) includes {2-[(meth)acryloyloxy]ethyl}dimethyl-(3-sulfopropyl)ammonium hydroxide, [3-(methacryloylamino)propyl]dimethyl(3-sulfopropyl)ammonium hydroxide, or a combination thereof.

7. The medical device according to claim 1 , wherein in the formula (2):

Z 2 is —NH—,

R 22 is a branched chain alkylene group having 3 to 5 carbon atoms, and

X is a sulfonic acid group or a group of a salt thereof.

8. The medical device according to claim 1 , wherein the photoreactive group is an azide group, a diazo group, a diazirine group, a ketone group, or a quinone group.

9. The medical device according to claim 1 , wherein the polymerizable monomer (C) includes, in addition to the photoreactive group, an ethylenically unsaturated group.

10. The medical device according to claim 2 , wherein the photoreactive group is an azide group, a diazo group, a diazirine group, a ketone group, or a quinone group.

11. The medical device according to claim 2 , wherein the polymerizable monomer (C) includes, in addition to the photoreactive group, an ethylenically unsaturated group.

12. The medical device according to claim 1 , wherein the surface lubricious layer is bound to the substrate layer via the photoreactive group of the hydrophilic copolymer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2019
From: KURAMOTO, MASANORI; ANZAI, TAKAO
To: TERUMO KABUSHIKI KAISHA
Reel/Frame 048411/0570 →
Priority Claims (1)
JP JP2016-164815 · Aug 25, 2016 · national
Continuity (2)
Continuation PCTJP2017029825 · Aug 21, 2017
Related Publication 20190185776A1 · Jun 20, 2019
Cited By (5)
US 12,403,296 US 12,478,775 US 12,576,263 US 12,589,237 US 12,599,749