# US 12,109,332 B2 · Biofouling resistant coatings and methods of making and using the same

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- Number: US 12,109,332 B2
- Document ID: US12109332B2
- Status: Granted
- Kind: B2
- Application number: 18/386,896
- Filed: 2023-11-03
- Published: 2024-05-02
- Granted: 2024-10-08
- Earliest claimed: 2019-06-05
- Assignees: The Regents of the University of California; Silq Technologies Corporation
- Applicants: The Regents of the University of California; Silq Technologies Corporation
- Inventors: Brian T. McVerry; Ethan Rao; Richard B. Kaner; Na He
- Web page: https://patentgrep.com/patent/US12109332B2

## CPC

- A61L 31/00: Materials for other surgical articles {, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices (shape or structure of stent-grafts A61F2/07, of stents A61F2/82, of surgical gloves A61B42/00, of surgical drapes A61B46/00, of occluding devices A61B17/12022)}
- C09D 5/1668: {Vinyl-type polymers}
- A61L 29/085: {Macromolecular materials}
- A61L 29/16: Biologically active materials, e.g. therapeutic substances {(A61L29/048 takes precedence)}
- A61L 31/10: Macromolecular materials
- A61L 31/16: Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)}
- C08F 220/30: containing aromatic rings in the alcohol moiety
- C08F 220/34: Esters containing nitrogen {, e.g. N,N-dimethylaminoethyl (meth)acrylate}
- C08F 220/382: {and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate}
- C08F 220/585: {and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]}
- C08F 293/005: {using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent}
- C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes
- C09D 153/00: Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- A61L 2300/606: Coatings
- A61L 2420/02: Methods for coating medical devices
- C08F 2438/01: Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
- 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)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

Disclosed herein are compositions to use in biofouling-resistant coatings, biofouling-resistant coatings, methods of making biofouling-resistant coatings, biofouling-resistant devices, and methods of making biofouling-resistant devices.

## Claims

### Claim 1

A medical device coated with a compound comprising:
a) a repeating unit of Formula (VII):
wherein
each R1a and R1b is independently selected from hydrogen and halogen;
each R2a and R2b is independently selected from halogen, —CN, and optionally substituted C1-C6 fluoroalkyl;
each A1 and A2 is independently selected from —C(═O)—, —S(═O)—, —S(═O)2—, and —S(═O)(=NR3c)—;
each B1 and B2 is independently selected from —O— and —NR3c—;
Z1 is —(CR6cR6d)s—;
each R4c, R4d, R5d, R5e, R5c, and R5d is independently selected from hydrogen, halogen, —CN, —OR9a, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 fluoroalkyl,
optionally substituted C2-C6 alkenyl, —NR3cCR3d, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, and —C(═O)OR9a;
each R3c and R3d is independently selected from hydrogen, optionally substituted C1-C4 alkyl, —X-optionally substituted C1-C4 alkyl, optionally substituted C2-C6 alkenyl, and optionally substituted aryl;
X is —C(═O)—, —S(═O)—, or —S(═O)2—;
each R9a, R11a, R11b, and R11c is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted aryl;
n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; and
s is an integer selected from 1, 2, 3, 4, and 5;
b) a repeating unit of Formula (VIII):
wherein,
A3 is —C(═O)—, —S(═O)—, —S(═O)2—, or —S(═O)(=NR3c)—;
B3 is —O— or —NR3c—;
D is —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, or —C(═O)OR9a;
Z2 is —(CR6cR6d)t—;
Z3 is —(CR6cR6d)p—;
each R3a and R3b is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted benzyl;
each R6c and R6d is independently selected from hydrogen, halogen, —CN, —OR9a, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 fluoroalkyl, optionally substituted C2-C6 alkenyl, —NR3cR3d, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, and —C(═O)OR9a;
each R3c and R3d is independently selected from hydrogen, optionally substituted C1-C4 alkyl, —X-optionally substituted C1-C4 alkyl, optionally substituted C2-C6 alkenyl, and optionally substituted aryl;
X is —C(═O)—, —S(═O)—, or —S(═O)2—;
each R9a, R12a, R12b, and R12c is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted aryl;
t is an integer selected from 1, 2, 3, 4, or 5;
p is an integer selected from 1, 2, 3, 4, or 5; and
wherein the repeating unit of Formula (VIII) is charged or zwitterionic; and
c) a repeating unit of Formula (IX):
A4 is —C(═O)—, —S(═O)—, —S(═O)2—, or —S(═O)(=NR3c)—;
B4 is —O— or —NR3c—;
Z4 is —(CR6cR6d)k—;
E is —CN, —OR9a, —NR9aR9b, —NR9aR9bR9c+, optionally substituted C1-C4 alkyl, optionally substituted C1-C6 fluoroalkyl, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, or —C(═O)OR9a;
each R6c, and R6d is independently selected from hydrogen, halogen, —CN, —OR9a, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 fluoroalkyl, optionally substituted C2-C6 alkenyl, —NR3cR3d, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, and —C(═O)OR9a;
each R3c and R3d is independently selected from hydrogen, optionally substituted C1-C4 alkyl, —X-optionally substituted C1-C4 alkyl, optionally substituted C2-C6 alkenyl, and optionally substituted aryl;
X is —C(═O)—, —S(═O)—, or —S(═O)2—;
each R9a, R9b, R9c, R13a, R13b, and R13c is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted aryl; and
k is an integer selected from 1, 2, 3, 4, or 5.

### Claim 2 (depends on 1)

The medical device of claim 1, wherein each of R1a, R1b, R2a, and R2b is F.

### Claim 3 (depends on 1)

The medical device of claim 1, wherein D is —S(═O)2O− or —C(═O)O−.

### Claim 4 (depends on 1)

The medical device of claim 1, wherein A1 is —S(═O)2— and each A2, A3, and A4 is —C(═O)—.

### Claim 5 (depends on 1)

The medical device of claim 1, wherein each B1, B2, and B3 is independently —O— or —NR3c—.

### Claim 6 (depends on 1)

The medical device of claim 1, wherein the compound has a number-average molecular weight of between about 10,000 and about 250,000.

### Claim 7 (depends on 1)

The medical device of claim 1, wherein the medical device comprises a silicon-based device or a carbon-based device.

### Claim 8 (depends on 7)

The medical device of claim 7, wherein the silicon-based device comprises a siloxane polymer moiety, a sesquisiloxane polymer moiety, a siloxane-silarylene polymer moiety, a silalkylene polymer moiety, a polysilane moiety, a polysilylene moiety, or a polysilazane moiety.

### Claim 9 (depends on 7)

The medical device of claim 7, wherein the carbon-based device comprises a polyolefin moiety, a polyethylene (PE) moiety, a polypropylene (PP) moiety, a polyamide (PA) moiety, a polytetrafluoroethylene (PTFE) moiety, a polyvinylidene fluoride (PVdF) moiety, or a polyvinyl chloride (PVC) moiety.

### Claim 10 (depends on 7)

The medical device of claim 7, wherein the medical device is a silicon-based device comprising a silicon surface.

### Claim 11 (depends on 10)

The medical device of claim 10, wherein the compound is covalently bound to the silicon surface.

### Claim 12 (depends on 11)

The medical device of claim 11, wherein the medical device comprises an implant, an IV, a prosthesis, suturing material, valve, stent, catheter, rod, shunt, scope, a contact lens, tubing, wiring, electrode, clip, fastener, syringe, container, bandage, patch, or a combination thereof.

### Claim 13 (depends on 12)

The medical device of claim 12, wherein the medical device is a catheter.

### Claim 14 (depends on 13)

The medical device of claim 13, wherein the catheter comprises an indwelling catheter, uretic catheter, permeath, or Foley catheter.

### Claim 15 (depends on 12)

The medical device of claim 12, wherein the medical device is a shunt.

### Claim 16 (depends on 15)

The medical device of claim 15, wherein the shunt comprises a cardiac shunt, a cerebral shunt, a lumbar-peritoneal shunt, a peritoneovenous shunt, a pulmonary shunt, a portosystemic shunt (PSS), a portacaval shunt, or a vesico-amniotic shunt.

### Claim 17 (depends on 15)

The medical device of claim 15, wherein the shunt is a cerebral shunt.

### Claim 18 (depends on 12)

The medical device of claim 12, wherein the medical device is a stent.

### Claim 19 (depends on 18)

The medical device of claim 18, wherein the stent comprises a coronary stent, a vascular stent, or a biliary stent.

### Claim 20 (depends on 12)

The medical device of claim 12, wherein the scope comprises a scope utilized in an image-guided surgery including endoscopy or laparoscopy.

### Claim 21 (depends on 1)

The medical device of claim 1, wherein the medical device comprises an auditory prosthesis, artificial larynx, an artificial bone, an artificial joint, an artificial organ, dental implants, mammary implants, penile implants, cranio/facial tendons, tendons, ligaments, menisci, or disks.

### Claim 22 (depends on 21)

The medical device of claim 21, wherein the medical device is an auditory prostheses.

### Claim 23 (depends on 21)

The medical device of claim 21, wherein the medical device is a mammary implant.

### Claim 24 (depends on 1)

The medical device of claim 1, wherein the medical device is a pacemaker.