US2013183262A1PendingUtilityA1
Antimicrobial polymeric compositions
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-modified1 . 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 .Cited by (0)
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