US2013183262A1PendingUtilityA1

Antimicrobial polymeric compositions

47
Assignee: WYNNE KENNETH JPriority: Oct 27, 2011Filed: Oct 31, 2012Published: Jul 18, 2013
Est. expiryOct 27, 2031(~5.3 yrs left)· nominal 20-yr term from priority
C08G 2650/04C08G 2650/38A01N 55/00C08G 18/61C08G 65/18C08G 65/22C08G 18/718C07F 7/1804C08G 65/226C08G 18/6674C08G 65/336C08G 2650/50C09D 175/04C08G 18/4862C08G 2650/48C08G 2650/64C08G 18/758C08G 18/5066
47
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Claims

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.

Claims

exact text as granted — not AI-modified
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, 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 polymer, comprising a polymerization product of:
 (A) the compound of  claim 1 ;   (B) one or more of an isocyanate, diisocyanate, or combination thereof;   (C) optionally, a diol or diamine chain extender; and   (D) optionally, a diol selected from the group polydimethylsiloxane diol, polytetramethylene oxide diol, polypropylene oxide diol, polyethylene oxide diol, polybutadiene diol, polyisobutylene diol, perfluorinated diol or a combination of two or more thereof.   
     
     
         4 . A method, comprising:
 reacting the compound of  claim 1  with one or more isocyanates having the formula:   
       
         
           
           
               
               
           
         
         to produce a compound having the formula: 
       
       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, 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 . 
       
     
     
         5 . 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, 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 . 
       
     
     
         6 . The compound of  claim 5 , having one of the following formulas: 
       
         
           
           
               
               
           
         
       
     
     
         7 . A composition, comprising a polymerization product of:
 (A) the compound of  claim 5 ;   (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. 
       
     
     
         8 . The composition of  claim 7 , wherein (B) is a bis(trialkoxysilyl)alkane having the formula: 
       
         
           
           
               
               
           
         
       
     
     
         9 . A composition, comprising:
 (a) a reaction product of:
 (A) the compound of  claim 5 ; 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, polytetramethylene oxide diol, polypropylene oxide diol, polyethylene oxide diol, polydimethylsiloxane dipropylamine, or a combination of two or more thereof. 
 
       
     
     
         10 . The composition of  claim 9 , which is a blend of (a) and (b). 
     
     
         11 . A compound having the formula: 
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3 , R 6 , R 7 , R 8  are each independently hydrogen, alkyl, alkenyl, cycloalkyl, or aryl; 
         wherein each R 4  is independently a —CR 9 R 10 — group wherein R 9  and R 10  are each independently hydrogen or alkyl; 
         wherein each R 5  is independently a —CR 9 R 10 — group wherein R 9  and R 10  are each independently hydrogen or alkyl; 
         wherein X is anion, Cl, Br, I, OH, or NO 3 ; 
         wherein n is 1-20; and 
         wherein m is 1-20. 
       
     
     
         12 . The compound of  claim 11 , having the formula: 
       
         
           
           
               
               
           
         
       
     
     
         13 . A method of making the compound of  claim 11 , comprising reacting a compound having the formula: 
       
         
           
           
               
               
           
         
       
       with a compound having the formula: 
       
         
           
           
               
               
           
         
       
       to produce the compound of  claim 11 . 
     
     
         14 . The method according to  claim 13 , wherein the compounds have the respective following formulas: 
       
         
           
           
               
               
           
         
       
     
     
         15 . A polymer, comprising a polymerization product of:
 (A) the compound of  claim 11 ;   (B) a soft block diol selected from the group polydimethylsiloxane diol, polytetramethylene oxide diol, polypropylene oxide diol, polyethylene oxide diol, polybutadiene diol, polyisobutylene diol, perfluorinated diol, or a combination of two or more thereof; and   (C) optionally, 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 . 
       
     
     
         16 . The polymer of  claim 15 , wherein:
 (A) is a compound having the formula:   
       
         
           
           
               
               
           
         
         (B) is a polydimethylsiloxane diol; and 
         (C) is a compound having the formula: 
       
       
         
           
           
               
               
           
         
       
     
     
         17 . A polymer, comprising a polymerization product of:
 (A) a compound having one of the following formulas:   
       
         
           
           
               
               
           
         
         wherein k is 1-4; and 
         A is —CO 2  or —SO 3 ; 
         (B) a soft block diol selected from the group polydimethylsiloxane diol, polytetramethylene oxide diol, polypropylene oxide diol, polyethylene oxide diol, polybutadiene diol, polyisobutylene diol, perfluorinated diol, or a combination of two or more thereof; and 
         (C) optionally, 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 . 
       
     
     
         18 . The polymer of  claim 17 , wherein:
 (B) is a polydimethylsiloxane diol; and   (C) is a compound having the formula:   
       
         
           
           
               
               
           
         
       
     
     
         19 . A method, comprising:
 contacting:
 (a) at least one selected from the group consisting of polyurethane polymer, polyurethane copolymer, or a combination thereof; and 
 (b) at least one selected from the group consisting of non-polar solvent, pentane, cyclopentane, hexane, cyclohexane, benzene, toluene, 1,4-dioxane, chloroform, diethyl ether, polar aprotic solvent, tetrahydrofuran, dichloromethane, ethyl acetate, acetone, dimethylformamide, acetonitrile, dimethyl sulfoxide, propylene carbonate, or a combination thereof; and 
 (c) at least one selected from the group consisting of polar protic solvent, water, methanol, ethanol, propanol, isopropanol, n-butanol, formic acid, or a combination thereof; 
   and thereafter separating, to produce a purified polyurethane polymer, polyurethane copolymer, or a combination thereof.   
     
     
         20 . A method for making a polymer, comprising the method of  claim 19 . 
     
     
         21 . A polymer, produced by the method of  claim 19 . 
     
     
         22 . An article or device, comprising the polymer of  claim 3  on a surface thereof. 
     
     
         23 . An article or device, comprising the composition of  claim 7  on a surface thereof. 
     
     
         24 . An article or device, comprising the composition of  claim 9  on a surface thereof. 
     
     
         25 . An article or device, comprising the polymer of  claim 15  on a surface thereof. 
     
     
         26 . A method for killing a microbe, comprising contacting said microbe with the polymer of  claim 17 . 
     
     
         27 . A method for killing a microbe, comprising contacting said microbe with the polymer of  claim 3 . 
     
     
         28 . A method for killing a microbe, comprising contacting said microbe with the composition of  claim 7 . 
     
     
         29 . A method for killing a microbe, comprising contacting said microbe with the composition of  claim 9 . 
     
     
         30 . A method for killing a microbe, comprising contacting said microbe with the polymer of  claim 15 . 
     
     
         31 . A method for killing a microbe, comprising contacting said microbe with the polymer of  claim 17 .

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