Antimicrobial compositions
The present invention is directed to providing antimicrobial surfaces containing 1,4-diazoniabicyclo[2.2.2]octane and hydrocarbon groups and/or chains. More specifically, the present invention is directed to antimicrobial compositions wherein the hydroxyl groups on polyols are replaced by 1,4-diazoniabicyclo[2.2.2]octane. The invention is also directed to methods of making antimicrobial compositions containing polyols.
1 . An antimicrobial composition comprising a carrier and a chemical compound having the following formula (1):
R 1 —Y 1 —X—Y 2 —R 2
wherein:
X represents 1,4-diazoniabicyclo[2.2.2]octane;
Y 1 and Y 2 independently represent hydrocarbon chains comprising a minimum of 10 carbon atoms and a maximum of 24 carbon atoms;
R 1 and R 2 independently represent H, halo, or OR 3 ;
R 3 represents H or R 4 ;
R 4 represents —C(O)R 5 or R 6 ;
R 5 represents H or a hydrocarbon group comprising a minimum of 1 carbon atom and a maximum of 4 carbon atoms; and
R 6 represents a hydrocarbon group comprising a minimum of 1 carbon atom and a maximum of 4 carbon atoms.
2 . An antimicrobial composition according to claim 1 , wherein the composition is a pharmaceutical and the carrier is a pharmaceutically acceptable carrier suitable for topical administration.
3 . An antimicrobial composition according to claim 1 , wherein R 1 and R 2 represent H, Cl, or OH.
4 . An antimicrobial composition according to claim 1 , wherein R 1 and R 2 represent H.
5 . An antimicrobial composition according to claim 1 , wherein Y 1 and Y 2 comprise a hydrocarbon chain having 12 carbon atoms.
6 . An antimicrobial composition according to claim 1 , wherein Y 1 and Y 2 comprise a hydrocarbon chain having 16 carbon atoms.
7 . An antimicrobial composition according to claim 1 , wherein Y 1 comprises a hydrocarbon chain having 12 carbon atoms and Y 2 comprises a hydrocarbon chain having 16 carbon atoms.
8 . An antimicrobial composition according to claim 1 , wherein Y 1 and Y 2 each represent a mixture of hydrocarbon chains.
9 . An antimicrobial composition according to claim 8 , wherein at least 50% of the hydrocarbon chains represented by Y 1 comprise 12 carbon atoms and at least 50% of the hydrocarbon chains represented by Y 2 comprise 16 carbon atoms.
10 . An antimicrobial composition according to claim 8 , wherein at least 75% of the hydrocarbon chains represented by Y 1 comprise 12 carbon atoms and at least 75% of the hydrocarbon chains represented by Y 2 comprise 16 carbon atoms.
11 . An antimicrobial composition according to claim 8 , wherein at least 90% of the hydrocarbon chains represented by Y 1 comprise 12 carbon atoms and at least 90% of the hydrocarbon chains represented by Y 2 comprise 16 carbon atoms.
12 . An antimicrobial composition according to claim 1 , wherein the pharmaceutical composition is a gel.
13 . An antimicrobial composition according to claim 1 , wherein the pharmaceutical composition is a paste, lotion or spray.
14 . An antimicrobial composition comprising a chemical compound having the following formula (2):
R 1 —Y 1 —X—Z—(X—Y 2 —R 2 ) n
wherein:
Z represents a polyol having more than one primary hydroxyl group wherein at least two of the primary hydroxyl groups have been replaced by R 1 —Y 1 —X or R 2 —Y 2 —X groups;
X represents 1,4-diazoniabicyclo[2.2.2]octane;
Y 1 and Y 2 independently represent hydrocarbon chains comprising a minimum of 10 carbon atoms and a maximum of 24 carbon atoms;
R 1 and R 2 independently represent H, halo, or OR 3 ;
R 3 represents H or R 4 ;
R 4 represents —C(O)R 5 or R 6 ;
R 5 represents H or a hydrocarbon group comprising a minimum of 1 carbon atom and a maximum of 4 carbon atoms;
R 6 represents a hydrocarbon group comprising a minimum of 1 carbon atom and a maximum of 4 carbon atoms; and
n represents any number up to m−1 wherein m represents the number of primary hydroxyl groups in the polyol.
15 . An antimicrobial composition according to claim 14 , wherein the polyol is an alkane polyol.
16 . An antimicrobial composition according to claim 15 , wherein the alkane polyol is glycerol, mannitol, ethylene glycol, or polyethylene glycol.
17 . An antimicrobial composition according to claim 14 , wherein the polyol is a carbohydrate.
18 . An antimicrobial composition according to claim 14 , wherein the polyol is a protein.
19 . An antimicrobial composition according to claim 14 , wherein the polyol is a gelling agent.
20 . An antimicrobial composition according to claim 19 , wherein the gelling agent is a polysaccharide.
21 . An antimicrobial composition according to claim 20 , wherein the polysaccharide is a gum, a pectin, agar, alginic acid or a salt thereof, or carrageenan.
22 . An antimicrobial composition according to claim 19 , wherein the gelling agent is a protein.
23 . An antimicrobial composition according to claim 22 , wherein the protein is a gelatin or collagen.
24 . An antimicrobial composition according to claim 14 , wherein Y 1 and Y 2 comprise a hydrocarbon group having 12, 14, 16, or 18 carbon atoms.
25 . An antimicrobial composition according to claim 14 , wherein Y 1 and Y 2 represents a mixture of hydrocarbon chains.
26 . An antimicrobial composition according to claim 14 , wherein the mixture of hydrocarbon chains comprises a hydrocarbon chain having 12 carbon atoms and a hydrocarbon chain having 16 carbon atoms.
27 . An antimicrobial composition according to claim 14 , wherein at least 25% of the hydrocarbon chains have 12 carbon atoms and at least 25% of the hydrocarbon chains have 16 carbon atoms.
28 . An antimicrobial composition according to claim 14 , wherein at least 75% of the hydrocarbon chains have 12 carbon atoms or 16 carbon atoms.
29 . An antimicrobial composition according to claim 14 , wherein at least 90% of the hydrocarbon chains have 12 carbon atoms or 16 carbon atoms.
30 . An antimicrobial composition according to claim 14 , wherein R 1 and R 2 independently represent H, Cl, or OH.
31 . An antimicrobial composition according to claim 30 , wherein R 1 and R 2 represent H.
32 . An antimicrobial composition according to claim 14 , wherein the composition is a paint.
33 . An antimicrobial composition according to claim 14 , wherein the composition is a fabric.
34 . An antimicrobial composition according to claim 14 , wherein the composition is a pharmaceutical composition.
35 . An antimicrobial composition according to claim 34 , wherein the pharmaceutical composition is a gel.
36 . An antimicrobial composition according to claim 35 , wherein the gel consists essentially of the chemical compound and water.
37 . An antimicrobial composition according to claim 34 , wherein the pharmaceutical composition is a paste, lotion or spray.
38 . A method of making an antimicrobial composition comprising a chemical compound having the following formula (2):
R 1 —Y 1 —X—Z—(X—Y 2 —R 2 ) n
wherein:
Z represents a polyol having more than one primary hydroxyl group wherein at least two of the primary hydroxyl groups have been replaced by R 1 —Y 1 —X or R 2 —Y 2 —X groups;
X represents 1,4-diazoniabicyclo[2.2.2]octane;
Y 1 and Y 2 independently represent hydrocarbon chains comprising a minimum of 10 carbon atoms and a maximum of 24 carbon atoms;
R 1 and R 2 independently represent H, halo, or OR 3 ;
R 3 represents H or R 4 ;
R 4 represents —C(O)R 5 or R 6 ;
R 5 represents H or a hydrocarbon group comprising a minimum of 1 carbon atom and a maximum of 4 carbon atoms;
R 6 represents a hydrocarbon group comprising a minimum of 1 carbon atom and a maximum of 4 carbon atoms; and
n represents any number up to m−1 wherein m represents the number of primary hydroxyl groups in the polyol,
the method comprising:
(a) providing a solution of a polyol that has more than one primary hydroxyl group;
(b) converting at least two primary hydroxyl groups of the polyol to leaving groups; and
(c) adding R—Y-Q,
wherein R represents H, halo, or OR 3 ;
Y represents a hydrocarbon chain comprising a minimum of 10 carbon atoms and a maximum of 24 carbon atoms; and
Q represents 1-azonia-4-azabicyclo[2.2.2]octane.
39 . The method according to claim 38 wherein the leaving groups are sulfonate ester groups or halo groups.
40 . The method according to claim 39 wherein the leaving groups are sulfonate ester groups selected from the group consisting of p-toluenesulfonate, benzenesulfonate, and methyl sulfonate.
41 . The method according to embodiment 39 wherein the leaving groups are halo groups selected from the group consisting of chloro and bromo.