# US 2014/0155510 A1 · Surface-modified elastic body

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- Number: US 2014/0155510 A1
- Document ID: US20140155510A1
- Status: Published application
- Kind: A1
- Application number: 14/077,829
- Filed: 2013-11-12
- Published: 2014-06-05
- Earliest claimed: 2012-11-30
- Assignees: Sumitomo Rubber Industires Ltd.
- Applicants: Sumitomo Rubber Industries, Ltd.
- Inventors: Yasuhisa MINAGAWA
- Web page: https://patentgrep.com/patent/US20140155510A1

## CPC

- C08J 7/18: using wave energy or particle radiation
- A61L 29/042: {Rubbers}
- A61L 29/06: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 29/08: Materials for coatings
- A61L 29/085: {Macromolecular materials}
- A61L 29/14: Materials characterised by their function or physical properties {, e.g. lubricating compositions}
- A61M 3/00: Medical syringes, e.g. enemata; Irrigators (A61M5/00 takes precedence; pistons A61M5/315)
- A61M 5/178: Syringes
- A61M 25/00: Catheters; Hollow probes (dilators A61M29/00; {peritoneal catheters A61M1/285; tracheal tubes A61M16/04; for drainage A61M27/00; for uterus, vagina or rectum A61M31/00} ; for measuring or testing A61B; {materials for catheters A61L29/00})
- A61M 25/0009: {Making of catheters or other medical or surgical tubes}
- A61M 25/0045: {multi-layered, e.g. coated (coating materials A61L29/08)}
- B05D 3/067: {Curing or cross-linking the coating}
- C08F 2/48: by ultraviolet or visible light
- C08F 36/18: containing chlorine
- C08F 220/56: Acrylamide; Methacrylamide
- C08F 291/02: on to elastomers
- C08F 291/04: on to halogen-containing macromolecules
- C08J 3/28: Treatment by wave energy or particle radiation
- C08J 7/12: Chemical modification
- A61L 2400/18: Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
- A61M 5/31513: {Piston constructions to improve sealing or sliding}
- A61M 2025/0046: {Coatings for improving slidability}
- A61M 2025/0056: {provided with an antibacterial agent, e.g. by coating, residing in the polymer matrix or releasing an agent out of a reservoir}
- A61M 2025/0062: {having features to improve the sliding of one part within another by using lubricants or surfaces with low friction}
- C08J 2323/28: by reaction with halogens or halogen-containing compounds (C08J2323/32 takes precedence)
- C08J 2433/26: Homopolymers or copolymers of acrylamide or methacrylamide
- Y10T 428/1352: Polymer or resin containing [i.e., natural or synthetic]
- Y10T 428/139: Open-ended, self-supporting conduit, cylinder, or tube-type article
- Y10T 428/1393: Multilayer [continuous layer]
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61M: DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY (introducing media into or onto the bodies of animals A61D7/00; means for inserting tampons A61F13/26; devices for administering food or medicines orally A61J; containers for collecting, storing or administering blood or medical fluids A61J1/05); DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY (surgery A61B; chemical aspects of surgical articles A61L); DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR {(Electrotherapy, e.g. producing anaesthesia by the use of alternating or intermittent currents A61N1/36021)}
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Provided are surface-modified elastic bodies (e.g. gasket for syringes) each obtained by a surface modification method for modifying a rubber vulcanizate or a thermoplastic elastomer, the method being capable of providing surfaces with excellent properties such as excellent sliding properties, excellent durability against repeated sliding motion, and excellent performance in preventing adsorption and aggregation of proteins, and allowing the surfaces to maintain the sealing properties, without using expensive self-lubricating plastics. The invention relates to surface-modified elastic bodies (e.g. gasket for syringes) at least partially having a surface modified by a surface modification method including: step 1 of forming polymerization initiation points on a surface of an object to be modified that includes a rubber vulcanizate or thermoplastic elastomer, and step 2 of radically polymerizing a monomer containing a C—N bond in a molecule thereof, starting from the polymerization initiation points, to grow polymer chains on the surface of the object.

## Claims

### Claim 1

A gasket for syringes, at least partially having a surface modified by a surface modification method comprising:
step 1 of forming polymerization initiation points on a surface of an object to be modified that comprises a rubber vulcanizate or a thermoplastic elastomer, and
step 2 of radically polymerizing a monomer containing a C—N bond in a molecule thereof, starting from the polymerization initiation points, to grow polymer chains on the surface of the object to be modified.

### Claim 2

A tire, at least partially having a groove surface modified by a surface modification method comprising:
step 1 of forming polymerization initiation points on a surface of an object to be modified that comprises a rubber vulcanizate or a thermoplastic elastomer, and
step 2 of radically polymerizing a monomer containing a C—N bond in a molecule thereof, starting from the polymerization initiation points, to grow polymer chains on the surface of the object to be modified.

### Claim 3

A catheter, at least partially having a surface modified by a surface modification method comprising:
step 1 of forming polymerization initiation points on a surface of an object to be modified that comprises a rubber vulcanizate or a thermoplastic elastomer, and
step 2 of radically polymerizing a monomer containing a C—N bond in a molecule thereof, starting from the polymerization initiation points, to grow polymer chains on the surface of the object to be modified.

### Claim 4

A low protein adsorption material, at least partially having a surface modified by a surface modification method comprising:
step 1 of forming polymerization initiation points on a surface of an object to be modified that comprises a rubber vulcanizate or a thermoplastic elastomer, and
step 2 of radically polymerizing a monomer containing a C—N bond in a molecule thereof, starting from the polymerization initiation points, to grow polymer chains on the surface of the object to be modified.

### Claim 5 (depends on 4)

The low protein adsorption material according to claim 4,
wherein the rubber vulcanizate or thermoplastic elastomer contains an allylic carbon atom which is a carbon atom adjacent to a double bond.

### Claim 6 (depends on 4)

The low protein adsorption material according to claim 4,
wherein the polymerization initiation points are formed by adsorbing a polymerization initiator on the surface of the object to be modified.

### Claim 7 (depends on 6)

The low protein adsorption material according to claim 6,
wherein the polymerization initiator is at least one of a benzophenone compound and a thioxanthone compound.

### Claim 8 (depends on 6)

The low protein adsorption material according to claim 6,
wherein the adsorbed polymerization initiator is further chemically bonded to the surface of the object to be modified by light irradiation.

### Claim 9 (depends on 4)

The low protein adsorption material according to claim 4,
wherein the radical polymerization is photo-radical polymerization.

### Claim 10 (depends on 9)

The low protein adsorption material according to claim 9,
wherein the photo-radical polymerization comprises irradiation with light having a wavelength of 300 to 450 nm.

### Claim 11 (depends on 4)

The low protein adsorption material according to claim 4,
wherein the radical polymerization comprises insertion of an inert gas into a reaction container and a reaction solution during or before light irradiation, to polymerize the monomer in an atmosphere replaced with the inert gas.

### Claim 12 (depends on 4)

The low protein adsorption material according to claim 4,
wherein the monomer containing a C—N bond in a molecule thereof is at least one selected from the group consisting of (meth) acrylamide, dimethyl(meth)acrylamide, diethyl(meth)acrylamide, isopropyl(meth)acrylamide, hydroxy(meth)acrylamide, and (meth)acryloyl morpholine.

### Claim 13 (depends on 9)

The low protein adsorption material according to claim 9,
wherein the photo-radical polymerization comprises contacting the monomer containing a C—N bond in a molecule thereof or a solution of the monomer with the surface of the object to be modified or the surface of the object to be modified to which a polymerization initiator is adsorbed or covalently bonded, and then irradiating the surface with light to polymerize the monomer.

### Claim 14 (depends on 13)

The low protein adsorption material according to claim 13,
wherein the monomer containing a C—N bond in a molecule thereof or the solution of the monomer includes a polymerization inhibitor, and the monomer is polymerized in the presence of the polymerization inhibitor.

### Claim 15 (depends on 14)

The low protein adsorption material according to claim 14,
wherein the polymerization inhibitor is 4-methylphenol.

### Claim 16 (depends on 4)

The low protein adsorption material according to claim 4,
wherein the polymer chains each have a length of 10 to 50,000 nm.