# US 2019/0313641 A1 · Antimicrobial compound

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- Number: US 2019/0313641 A1
- Document ID: US20190313641A1
- Status: Published application
- Kind: A1
- Application number: 16/375,045
- Filed: 2019-04-04
- Published: 2019-10-17
- Earliest claimed: 2018-04-12
- Assignees: Physical Sciences, Inc.
- Applicants: Physical Sciences, Inc.
- Inventors: Dorin V. Preda; Aaron R. Rathmell; Colin M. Hessel; John D. Lennhoff; Mitchell T. Antalek
- Web page: https://patentgrep.com/patent/US20190313641A1

## CPC

- A01N 37/48: Nitro-carboxylic acids; Derivatives thereof
- A01N 33/12: Quaternary ammonium compounds
- A01N 43/50: 1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N 43/66: 1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N 47/28: Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< (isoureas, isothioureas A01N47/42)
- D06M 15/564: Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M 15/61: Polyamines {polyimines}
- D06M 16/00: Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
- 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
- D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS

## Abstract

An antimicrobial composition including low molecular weight dendrimers of formula (I): Q is an antimicrobial moiety in monomer or dendritic form, N is a nitrogen atom, L2 is a linker linking each Y1 molecular spacer to the nitrogen atom, is a molecular spacer spacing each antimicrobial moiety Q from the L2 linker, there are two or more chains of antimicrobial moieties and molecular spacers, X is a linker configured to covalently bond to surface functionalities of the substrate, and Y2 is a molecular spacer between the linker X and the nitrogen atom.

## Claims

### Claim 1

A composition providing antimicrobial properties to a substrate, the composition comprising:
low molecular weight dendrimers of formula (1):
Where:
Q is an antimicrobial moiety in monomer or dendritic form,
N is a nitrogen atom,
L2 is a linker linking each Y1 molecular spacer to the nitrogen atom,
Y1 is a molecular spacer spacing each antimicrobial moiety Q from the L2 linker, there are two or more chains of antimicrobial moieties and molecular spacers,
X is a linker configured to covalently bond to surface functionalities of the substrate, and
Y2 is a molecular spacer between the linker X and the nitrogen atom.

### Claim 2 (depends on 1)

The composition of claim 1 in which the molecular spacer Y2 includes a ring structure.

### Claim 3 (depends on 2)

The composition of claim 2 in which said ring structure is an aromatic ring.

### Claim 4 (depends on 1)

The composition of claim 1 in which the antimicrobial moiety includes positively charged quaternary ammonium cations.

### Claim 5 (depends on 4)

The composition of claim 4 in which the quaternary ammonium cations are chosen from: tetrasubstituted nitrogen of type +NR1R2R3R4 where R1-R4 can independently be alkyl, aryl, alkenyl or other carbon moieties and trisubstituted nitrogen of type Z1Z2N+=CA1A2, where Z1, Z2 can independently be alkyl, aryl, alkenyl or other carbon moieties and A1 and A2 are carbon or heteroatom moieties that may form a ring structure with Z1 or Z2.

### Claim 6 (depends on 5)

The composition of claim 5 in which the quaternary ammonium cations are chosen from substituted dimethyldodecylammonium cation, didodecylmethylammonium cation, and dimethyloctylammonium cation, and substituted 2-methyl-1-decylimidazolium.

### Claim 7 (depends on 1)

The composition of claim 1 in which the linker X is chosen from: amino groups, dichlorotriazine, phosphonic acid, azide or other linkers specific to the surface of choice.

### Claim 8 (depends on 1)

The composition of claim 1 in which the linker L2 includes substituted N propyl-propionamide.

### Claim 9 (depends on 1)

The composition of claim 1 in which the spacer Y1 includes substituted N-ethylurea.

### Claim 10

A composition providing antimicrobial properties to a substrate, the composition comprising:
an antimicrobial moiety in monomer or dendritic form;
a nitrogen atom;
a linker L2 linking a molecular spacer Y1 to the nitrogen atom, the molecular spacer Y1 spacing each antimicrobial moiety from the L2 linker;
two or more chains of antimicrobial moieties and molecular spacers;
a linker X configured to covalently bond to surface functionalities of the substrate; and
a molecular spacer Y2 between the linker X and the nitrogen atom.

### Claim 11 (depends on 10)

The composition of claim 10 in which the molecular spacer Y2 includes a ring structure.

### Claim 12 (depends on 11)

The composition of claim 11 in which said ring structure is an aromatic ring.

### Claim 13 (depends on 10)

The composition of claim 10 in which the antimicrobial moiety includes positively charged quaternary ammonium cations.

### Claim 14 (depends on 13)

The composition of claim 13 in which the quaternary ammonium cations are chosen from: tetrasubstituted nitrogen of type +NR1R2R3R4 where R1-R4 can independently be alkyl, aryl, alkenyl or other carbon moieties and trisubstituted nitrogen of type Z1Z2N+=CA1A2 where Z1, Z2 can independently be alkyl, aryl, alkenyl or other carbon moieties and A1 and A2 are carbon or heteroatom moieties that may form a ring structure with Z1 or Z2.

### Claim 15 (depends on 14)

The composition of claim 14 in which the quaternary ammonia cations is chosen from substituted dimethyldodecylammonium cation, didodecylmethylammonium cation, and dimethyloctylammonium cation, and substituted 2-methyl-1-decylimidazolium.

### Claim 16 (depends on 10)

The composition of claim 10 in which the linker X is chosen from: amino groups, dichlorotriazine, phosphonic acid, and azide.

### Claim 17 (depends on 10)

The composition of claim 10 in which the linker L2 includes substituted N propyl-propionamide.

### Claim 18 (depends on 10)

The composition of claim 10 in which the spacer Y1 includes substituted N ethylurea.