ANTIMICROBIAL POLYURETHANE FOAMS

1 . An antimicrobial foamed polyurethane comprising at least one group X; wherein:

X comprises a group [R—([V m+ —R 1 —R 2 ] q[Y p− ]) n ];

R is independently selected from divalent hydrocarbon radicals having 1-30 carbon atoms, optionally substituted on the carbon backbone with one or more groups selected from COOH, COO(C 1-6 alkyl), COO(C 6-20 aryl), halo, O(C 1-6 alkyl), O(C 6-20 aryl), O(C 7-20 alkaryl), O(C 7-20 aralkyl), ═O, NH 2 , NO 2 , CN and L;

L is selected from the group consisting of —OH, leaving group and mixtures thereof;

V comprises a positively charged moiety;

m represents an integer of 1-10;

n represents an integer of 1, 2, 3 or 4;

R 1 is independently selected from divalent hydrocarbon radicals having 1-30 carbon atoms;

R 2 is independently selected from the group consisting of —H, —CH 3 , —SH, —F, —Cl, —Br, —I, —OR 3 —HN(O)CR 4 , or —O(O)CR 5 , wherein R 3 , R 4 and R 5 are independently selected from the group consisting of —H and monovalent hydrocarbon radicals having 1-30 carbon atoms;

Y represents an anion;

q represents m/p; and,

p represents an integer of 1-10.

2 . An antimicrobial foamed polyurethane according to claim 1 , wherein X is linked to the polyurethane via a carbon atom of the backbone of group R or via a substituent on the backbone of group R.

3 . An antimicrobial foamed polyurethane according to claim 1 , wherein R is selected from the group consisting of C 1-20 alkanediyl, C 2-20 alkenediyl, C 2-20 alkynediyl, C 3-30 cycloalkanediyl, C 3-30 cycloalkenediyl, C 5-30 cycloalkynediyl, C 7-30 aralkylenediyl, C 7-30 alkarylenediyl and C 5-30 arylenediyl, any of which is optionally substituted on the carbon backbone with one or more groups selected from COOH, COO(C 1-6 alkyl), COO(C 6-10 aryl), halo, O(C 1-6 alkyl), O(C 6-10 aryl), O(C 7-10 alkaryl), O(C 7-10 aralkyl), ═O, NH 2 , NO 2 , CN and L.

4 . An antimicrobial foamed polyurethane according to claim 1 , wherein R is selected from methylene, 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,2-butylene, 1,3-butylene, 1,4-butylene, 1,5-pentylene, 1,6-hexylene, 1,8-octylene, 1,10-decylene and 1,12-dodecylene, any of which is optionally substituted on the carbon backbone with one or more groups selected from OH and leaving groups.

5 . An antimicrobial foamed polyurethane according to claim 1 , wherein R 1 is selected from the group consisting of C 1-30 alkanediyl, C 2-30 alkenediyl, C 2-30 alkynediyl, C 3-35 cycloalkanediyl, C 3-35 cycloalkenediyl, C 5-35 cycloalkynediyl, C 7-35 aralkylenediyl, C 7-35 alkarylenediyl and C 5-35 arylenediyl.

6 . An antimicrobial foamed polyurethane according to claim 1 , wherein R 1 is selected from the group consisting of a straight chain C 7 alkanediyl, C 8 alkanediyl, C 9 alkanediyl, C 10 alkanediyl, C 11 alkanediyl, C 12 alkanediyl, C 13 alkanediyl, C 14 alkanediyl, C 15 alkanediyl, C 16 alkanediyl and C 17 alkanediyl.

7 . An antimicrobial foamed polyurethane according to claim 1 , wherein R 1 is a —(CH 2 ) 15 — group or a —(CH 2 ) 11 — group.

8 . An antimicrobial foamed polyurethane according to claim 1 , wherein R 2 is —H or CH 3 .

9 . An antimicrobial foamed polyurethane according to claim 1 , wherein n is 1.

10 . An antimicrobial foamed polyurethane according to claim 1 , wherein R 3 , R 4 and R 5 are independently selected from the group consisting of —H, C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 3-30 cycloalkyl, C 3-30 cycloalkenyl, C 4-30 cycloalkynyl, C 7-30 aralkyl, C 7-30 alkaryl, C 5-30 aryl, C 3-30 heteroaryl, and C 3-30 heterocyclyl.

11 . An antimicrobial foamed polyurethane according to claim 1 , wherein moiety V comprises a group (A):

wherein a, b and c independently represent 1-10.

12 . An antimicrobial foamed polyurethane according to claim 1 , wherein n=1 and the —[R—([V m+ —R 1 —R 2 ] moiety comprises the structure (1):

wherein h represents 1-10;

i represents 7-17; and

a, b, and c independently represent 1-10.

13 . An antimicrobial foamed polyurethane according to claim 1 , wherein n=1 and the —[R—([V m+ —R 1 —R 2 ] moiety has the structure (4):

14 . An antimicrobial foamed polyurethane according to claim 1 , wherein n=2 and the —[R—([V m+ —R 1 —R 2 ] moiety has the structure (5):

wherein (5) is attached to the polyurethane polymer via the —(CH)—* group;

j represents 1-17;

k represents 1-17;

r represents 0-10;

l represents 0-10;

s represents 0-10;

t represents 1;

L is selected from the group consisting of an OH group or a leaving group, or a mixture thereof; and

a, b, and c independently represent 1-10.

15 . A method for the production of an antimicrobial foamed polyurethane comprising:

(i) mixing a C 1-3 alcohol solution comprising a compound having the formula L 1 -X wherein:

X comprises a group —[R—([V m+ —R 1 —R 2 ] q[Y p− ]) n ];

R is independently selected from divalent hydrocarbon radicals having 1-30 carbon atoms, optionally substituted on the carbon backbone with one or more groups selected from COOH, COO(C 1-6 alkyl), COO(C 6-20 aryl), halo, O(C 1-6 alkyl), O(C 6-20 aryl), O(C 7-20 alkaryl), O(C 7-20 aralkyl), ═O, NH 2 , NO 2 , CN and L;

V comprises a positively charged moiety;

m represents an integer of 1-10;

n represents an integer of 1, 2, 3 or 4;

R 1 is independently selected from divalent hydrocarbon radicals having 1-30 carbon atoms;

R 2 is independently selected from the group consisting of —H, —CH 3 , —SH, —F, —Cl, —Br, —I, —OR 3 , —HN(O)CR 4 , or —O(O)CR 5 , wherein R 3 , R 4 and R 5 are independently selected from the group consisting of —H and monovalent hydrocarbon radicals having 1-30 carbon atoms;

Y represents an anion;

q represents m/p; and,

p represents an integer of 1-10; and,

L 1 is an —OH group or a leaving group;

L is selected from the group consisting of —OH, leaving group and mixtures thereof;

with an isocyanate-containing, polyurethane-forming prepolymer; and

(ii) adding an acrylate containing compound and water to the mixture of (i).

16 . A method according to claim 15 , wherein compounds having the formula L 1 -X are selected from the group consisting of:

wherein h represents 1-10;

i represents 7-17;

j represents 1-17;

k represents 1-17;

r represents 0-10;

l represents 0-10;

s represents 0-10;

w is 1, 2, 3 or 4; and

a, b, and c independently represent 1-10.

17 . A method according to claim 15 , wherein the C 1-3 alcohol is selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol and mixtures thereof.

18 . A method according to claim 15 , wherein the ratio of the compound having the formula L 1 -X to the C 1-3 alcohol is in the range of about 1:10 to about 2:1.

19 . A method according to claim 15 , wherein the compound L 1 -X is added to the C 1-3 alcohol in an amount of 20%-50% by weight of the alcohol.

20 . A method according to claim 15 , wherein the solution of the compound having the formula L 1 -X in the C 1-3 alcohol is added to the prepolymer in the ratio of about 1:20 to about 1:3 by weight.

21 . A method according to claim 15 , wherein the alcoholic solution of L 1 -X is added to the prepolymer in an amount of 10%-20% by weight of the prepolymer.

22 . A method according to claim 15 , wherein the prepolymer used in step (i) of the present invention is a diisocyanate terminated oligomer selected from the group selected from diisocyanate terminated polyethylene oxide, diisocyanate terminated polypropylene oxide, diisocyanate terminated polyethylene oxide/polypropylene oxide copolymers, diisocyanate terminated polytetramethylene oxide, diisocyanate terminated polyisobutylene, diisocyanate terminated polyethylene adipate, diisocyanate terminated polycaprolactone and diisocyanate terminated polydimethylsiloxane.

23 . A method according to claim 15 , wherein the prepolymer is an diisocyanate-terminated polyether.

24 . A method according to claim 15 , wherein the ratio of the acrylate to water is in the range of about 1:5 to about 1:1 by weight.

25 . A method according to claim 15 , wherein acrylate compounds are selected from the group consisting of (meth)acrylic monomers such as (meth)acrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, phenyl (meth)acrylate, toluoyl (meth)acrylate, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, stearyl (meth)acrylate, glycidyl (meth)acrylate, 2-aminoethyl (meth)acrylate, γ-(methacryloyloxypropyl)trimethoxysilane, trifluoromethylmethyl (meth)acrylate, 2-trifluoromethylethyl (meth)acrylate, 2-perfluoroethylethyl (meth)acrylate, 2-perfluoroethyl (meth)acrylate, perfluoromethyl (meth)acrylate, diperfluoromethylmethyl (meth)acrylate, 2-perfluoromethyl-2-perfluoroethylmethyl (meth)acrylate, 2-perfluorohexylethyl (meth)acrylate, 2-perfluorodecylethyl (meth)acrylate, 2-perfluorohexadecylethyl (meth)acrylate and mixtures thereof.

26 . A polyurethane foam obtainable by a method according to claim 15 .

27 . A pharmaceutical composition comprising an antimicrobial foamed polyurethane according to claim 1 .

28 . An article selected from clothing, footware inserts, bandages, sutures, protective gear and containers, comprising an antimicrobial foamed polyurethane obtainable by a method according to claim 15 .

29 . A medical device comprising an antimicrobial foamed polyurethane according to claim 1 .

30 . A medical device according to claim 29 , wherein the device is a wound dressing.

31 . A medical device according to claim 29 , wherein the device further comprises a therapeutic agent.

32 . A kit of parts, comprising:

(i) a C 1-3 alcohol;

(ii) a compound having the formula L 1 -X;

(iii) an isocyanate-containing, polyurethane-forming prepolymer; and

(iv) an acrylate containing compound;

wherein components (i), (ii), (iii) and (iv) are as defined in claim 15 .

33 . A kit of parts according to claim 32 , further comprising water.

34 . (canceled)