Antimicrobial polymeric compositions

Patent metadata

Field	Value
Publication number	US-10117436-B2
Application number	US-201615080567-A
Country	US
Kind code	B2
Filing date	Mar 24, 2016
Priority date	Oct 27, 2011
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

A compound having the formula:

wherein n, y, R 1 and R 2 are defined herein, and others, methods of making of and using, and compositions made thereby which have an antimicrobial resistance effect are described.

First claim

The invention claimed is:

1. A compound having the formula:

wherein n is 0 to 1;
wherein y is an integer of 1-1000; and
wherein R 1 and R 2 are not identical and are each independently —OCH 2 CF 2 H, —OCH 2 CF 2 CF 2 H, —OCH 2 CF 2 CF 2 CF 2 H, —Br, —(OC 2 H 4 ) x —O—CH 3 , wherein x is 0-11, alkoxy, —CF 2 H-terminated-fluoroalkoxy, alkoxycycloalkyl, or a group having one of the following formulas:

wherein a is 5-15;
wherein b is 0-5
wherein X is Cl, Br, I, OH, or NO 3 ; and
wherein A is —CO 2 or —SO 3 .

2. The compound of claim 1 , having one of the following formulas:

3. A composition, comprising a polymerization product of:
(A) the compound of claim 1 ;
(B) one or more bis(trialkoxysilyl)alkanes having the formula:

wherein R D is —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , or —CH 2 CH 2 CH 2 CH 3 ; and wherein r is an integer of 1-10;

or one or more polydialkoxysiloxanes having the formula:

where R is —CH 3 or —C 2 H 5 ;
(C) one or more of an isocyanate, diisocyanate, or combination thereof;
(D) optionally, a diol or diamine chain extender; and
(E) optionally, a soft block diol selected from the group consisting of polydimethylsiloxane diol, polytetramethylene oxide diol, polypropylene oxide diol, polyethylene oxide diol, or a combination of two or more thereof.

4. The composition of claim 3 , wherein (B) is a bis(trialkoxysilyl)alkane having the formula:

5. A composition, comprising:
(a) a reaction product of:
(A) the compound of claim 1 ; and
(B) one or more bis(trialkoxysilyl)alkanes having the formula:

wherein R D is —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , or —CH 2 CH 2 CH 2 CH 3 ; and wherein r is an integer of 1-10;

or one or more polydialkoxysiloxanes having the formula:

where R is —CH 3 or —C 2 H 5 ;
and
(b) a polymerization product of:
(C) one or more of an isocyanate, diisocyanate, or combination thereof;
(D) optionally, a diol or diamine chain extender; and
(E) optionally, a soft block diol selected from the group consisting of polydimethylsiloxane diol, polytetramethlene oxide diol, polypropylene oxide diol, polyethylene oxide diol, polydimethylsiloxane dipropylamine, or a combination of two or more thereof.

6. The composition of claim 5 , which is a blend of (a) and (b).

7. An article or device, comprising the composition of claim 3 on a surface thereof.

8. An article or device, comprising the composition of claim 5 on a surface thereof.

9. A method for killing a microbe, comprising contacting said microbe with the composition of claim 3 .

10. A method for killing a microbe, comprising contacting said microbe with the composition of claim 5 .

11. The compound of claim 1 , wherein R 1 and R 2 are not identical and are each independently —OCH 2 CF 2 H, —OCH 2 CF 2 CF 2 H, —OCH 2 CF 2 CF 2 CF 2 H, —Br, —(OC 2 H 4 )x-O—CH 3 , wherein x is 0-11, —CF 2 H-terminated-fluoroalkoxy, or a group having one of the following formulas:

12. The compound of claim 1 , wherein R 1 and R 2 are not identical and at least one is —OCH 2 CF 2 H, —OCH 2 CF 2 CF 2 H, —OCH 2 CF 2 CF 2 CF 2 H, —Br, —(OC 2 H 4 ) x —O—CH 3 , wherein x is 0-11, or —CF 2 H-terminated-fluoroalkoxy.

13. The compound of claim 1 , wherein R 1 and R 2 are not identical and at least one is —OCH 2 CF 2 H, —OCH 2 CF 2 CF 2 H, —OCH 2 CF 2 CF 2 CF 2 H, —(OC 2 H 4 ) x —O—CH 3 , wherein x is 0-11, or —CF 2 H-terminated-fluoroalkoxy.

14. The compound of claim 1 , wherein R 1 and R 2 are not identical and at least one is a group having one of the following formulas:

15. The compound of claim 1 , wherein R 1 and R 2 are not identical and at least one is a group having the following formula:

16. The compound of claim 1 , wherein R 1 and R 2 are not identical and at least one is a group having the following formula:

17. The compound of claim 1 , wherein R 1 and R 2 are not identical and at least one is a group having the following formula:

18. The compound of claim 1 , having the following formula:

19. The compound of claim 1 , having the following formula:

20. A method, comprising:
reacting a compound having the formula:

wherein n is 0 to 1;
wherein y is an integer of 1-1000; and
wherein R 1 and R 2 are not identical and are each independently —OCH 2 CF 2 H, —OCH 2 CF 2 CF 2 H, —OCH 2 CF 2 CF 2 CF 2 H, —Br, —(OC 2 H 4 ) x —O—CH 3 , wherein x is 0-11, alkoxy, —CF 2 H-terminated-fluoroalkoxy, alkoxycycloalkyl, or a group having one of the following formulas:

wherein a is 5-15;
wherein b is 0-5
wherein X is Cl, Br, I, OH, or NO 3 ; and
wherein A is —CO 2 or —SO 3 ;

with one or more isocyanates having the formula:

to produce the compound of claim 1 .

Assignees

• Univ Virginia Commonwealth

Inventors

• Wynne Kenneth J
• Chakrabarty Souvik
• Zhang Wei
• Chakravorty Asima
• Oyesanya Olufemi O

Classifications

• C08G18/5066

  having halogens in addition to nitrogen · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C08G18/6674

  with compounds of group C08G18/3203 · CPC title

• C08G2650/38

  containing oxygen in addition to the ether group · CPC title

• C08G18/4862

  containing at least a part of the ether groups in a side chain · CPC title