# US 11,077,234 B2 · Antimicrobial coatings for medical implements and medical devices

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- Number: US 11,077,234 B2
- Document ID: US11077234B2
- Status: Granted
- Kind: B2
- Application number: 15/938,417
- Filed: 2018-03-28
- Published: 2018-10-04
- Granted: 2021-08-03
- Earliest claimed: 2017-03-28
- Assignees: Allied Bioscience, Inc.
- Applicants: Allied Bioscience, Inc.
- Inventors: Craig Grossman; Gavri Grossman; Daniel Moros; Misagh Alipour; Jie Fang
- Web page: https://patentgrep.com/patent/US11077234B2

## CPC

- A61L 29/16: Biologically active materials, e.g. therapeutic substances {(A61L29/048 takes precedence)}
- A01N 55/00: Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00)
- A61L 29/02: Inorganic materials
- A61L 29/06: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 29/08: Materials for coatings
- A61L 31/08: Materials for coatings
- A61L 31/16: Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)}
- A61L 2300/202: with halogen atoms, e.g. triclosan, povidone-iodine
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- A61L 2300/606: Coatings
- A61L 2300/802: Additives, excipients, e.g. cyclodextrins, fatty acids, surfactants
- A61L 2420/02: Methods for coating medical devices
- A61L 2420/06: Coatings containing a mixture of two or more compounds
- 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)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

The present disclosure provides antimicrobial coating compositions that are used to form residual antimicrobial coatings on medical implements and medical devices including the components of medical equipment such as CPAP/BiPAP machines. Antimicrobial coating compositions comprise at least one of an organosilane (R1O)3Si—R2—Z, an organic amine R9R10R11N, a titanium (IV) species, a 1,2-diol, an α-hydroxy acid, β-hydroxy acid, and an organosilane grafted parylene polymer, wherein R1 is H, alkyl, substituted alkyl, aryl or substituted aryl, R2 is a bivalent linker, Z is a nucleophile, leaving group, or quaternary nitrogen substituent, and R9, R10, and R11 are independently H, alkyl, substituted alkyl, aryl, substituted aryl or cyclic.

## Claims

### Claim 1

A method of coating an implantable medical device, the method comprising:
immersing the implantable medical device in an aqueous composition comprising octadecyldimethyl-(3-trimethoxysilylpropyl) ammonium chloride, 3-chloropropyltrimethoxysilane, triethanolamine and water;
drying the implantable medical device under ambient conditions to produce a coating on the implantable medical device; and
curing the coating on the implantable medical device by heating the implantable medical device at between about 100° C. to about 1000° C. to produce a cured coating on the implantable medical device;
wherein the aqueous composition is of the formulation: 0.75 wt. % octadecyldimethyl-( 3-trimethoxysilylpropyl) ammonium chloride, 0.12 wt. % 3-chloropropyltrimethoxysilane, 0.045 wt. % triethanolamine, and 99.085 wt. % water; and
wherein the cured coating on the implantable medical device exhibits a residual antimicrobial efficacy against at least one of S. epidermidis or E. aerogenes.

### Claim 2 (depends on 1)

The method of claim 1, wherein the implantable medical device comprises a Nitinol stent, an artificial joint, a pin, or a bone screw.

### Claim 3 (depends on 1)

The method of claim 1, wherein the coating on the implantable medical device is cured by heating at about 100° C.

### Claim 4 (depends on 1)

The method of claim 1, wherein the implantable medical device comprises 316 stainless steel or Nitinol and wherein, after the immersing, the implantable medical device is: (a) allowed to dry under ambient conditions, (b) annealed at from about 100° C. to about 1000° C., and (c) sterilized by autoclaving for 20 minutes at 121° C.

### Claim 5 (depends on 4)

The method of claim 4, wherein the cured coating on the implantable medical device exhibits a reduction of S. epidermidis ATCC 12228 of from about 3.14 log10 to about 3.79 log10 2 hours after initial inoculation of the coated medical implement with S. epidermidis ATCC 12228.

### Claim 6 (depends on 4)

The method of claim 4, wherein the cured coating on the implantable medical device exhibits a reduction of S. epidermidis ATCC 12228 of from about 3.56 log10 to about 4.52 log10 4 hours after initial inoculation of the coated medical implement with S. epidermidis ATCC 12228.

### Claim 7 (depends on 4)

The method of claim 4, wherein the cured coating on the implantable medical device exhibits a reduction of E. aerogenes ATCC 13048 of from about 2.05 log10 to about 2.94 log10 2 hours after initial inoculation of the coated medical implement with E. aerogenes ATCC 13048.

### Claim 8 (depends on 4)

The method of claim 4, wherein the cured coating on the implantable medical device exhibits a reduction of E. aerogenes ATCC 13048 of from about 2.06 log10 to about 2.51 log10 4 hours after initial inoculation of the coated medical implement with E. aerogenes ATCC 13048.

### Claim 9 (depends on 1)

The method of claim 1, wherein the implantable medical device comprises Nitinol, stainless steel or silicone rubber.

### Claim 10 (depends on 1)

The method of claim 1, wherein the implantable medical device comprises a coronary stent or an indwelling urinary catheter.

### Claim 11

A method of providing a residual antimicrobial coating on a portion of a surface of a CPAP or BiPAP machine component, the method comprising:
immersing the portion in an aqueous composition comprising octadecyldimethyl-( 3-trimethoxysilylpropyl) ammonium chloride, 3 -chloropropyltrimethoxysilane, triethanolamine and water;
drying the portion under ambient conditions; and
thermally curing the portion at between about 100° C. to about 1000° C. to produce a cured coating on the portion,
wherein the aqueous composition is of the formulation: 0.75 wt. % octadecyldimethyl-( 3-trimethoxysilylpropyl) ammonium chloride, 0.12 wt. % 3 -chloropropyltrimethoxysilane, 0.045 wt. % triethanolamine, and 99.085 wt. % water; and
wherein the portion exhibits a residual antimicrobial efficacy against at least one of S. epidermidis or E. aerogenes.

### Claim 12 (depends on 11)

The method of claim 11, wherein the surface comprises silicone rubber.

### Claim 13 (depends on 11)

The method of claim 11, wherein the CPAP or BiPAP machine component comprises a mask, a mask part, a filter, a hose, a machine part or a humidifier part.

### Claim 14 (depends on 13)

The method of claim 13, wherein the mask comprises a nasal mask, a full face mask, a nasal pillow mask, a nasal prong mask, a hybrid mask, or an oral mask.

### Claim 15 (depends on 13)

The method of claim 13, wherein the mask part comprises a mask kit, a cushion, a pillow, headgear, headgear clips, or a chinstrap.