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US 2003/0216581 A1Published application
N-halamine vinyl compounds and their polymeric biocides
AssigneeThe Regents of the University of California
InventorsGang Sun, Yuyu Sun
Life of this patent
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Abstract
The present invention provides heterocyclic vinylic compounds that can be used to form biocidal polymers. The polymers thus generated can used alone or can be grafted onto textiles, fabrics and polymers. The polymers are readily converted to N-halamine structures on exposure to a halogen source such as commercially available chlorine bleach. The N-halamine derivatives exhibit potent antibacterial properties against microorganisms and these properties are durable and regenerable.
Claims56
A compound having the formula:
- 12
- wherein:
- A is a member selected from the group consisting of NH, N—R8 and CR1R2, wherein R8 is a halogen;
- R1 and R2, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R1 and R2 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- Q is a member selected from the group consisting of C(O), NH, N—R9 and CR3R4, wherein R9 is a halogen;
- R3 and R4, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R3 and R4 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- X is a member selected from the group consisting of C(O), C(O)—NR5 and CR6R7, wherein R5 is a member selected from the group consisting of hydrogen, halogen, optionally substituted (C2-C6)alkenyl and optionally substituted (C1-C6)alkyl;
- R6 and R7, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R6 and R7 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- and
- Z is a member selected from the group consisting of optionally substituted (C1-C3)alkylene, C(O), or a single bond.
10 more elements
A polymer comprising a mixture of monomeric units having the formulae:
- 15
- wherein:
- A is a member selected from the group consisting of NH, N—R8 and CR1R2, wherein R8 is a halogen;
- R1 and R2, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R1 and R2 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- Q is a member selected from the group consisting of C(O), NH, N—R9 and CR3R4, wherein R9 is a halogen;
- R3 and R4, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R3 and R4 and the carbon to which they are bound, join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring.
- X is a member selected from the group consisting of C(O)—NR10 and CR6R7, wherein R10 is a member selected from the group consisting of hydrogen, halogen, optionally substituted (C2-C6)alkenyl and optionally substituted (C1-C6)alkyl;
- R6 and R7, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R6 and R7 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- Z is a member selected from the group consisting of optionally substituted (C1-C3)alkylene, C(O), or a single bond;
- R11 is a member selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)alkoxy, (C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, aldehydo, amido, aryl and heterocyclyl;
- R12 is a member selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)alkoxy, (C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, aldehydo, amido, aryl and heterocyclyl;
- R13 is a member selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)alkoxy, (C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, aldehydo, amido, aryl and heterocyclyl;
- R14 is a member selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)alkoxy, (C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, aldehydo, amido, aryl and heterocyclyl;
- and
- n and y are each independently an integer from 1 to 250 inclusive.
15 more elements
A method for making a polymer, said method comprising:
- admixing a compound having the formula:
- 17
- wherein:
- A is a member selected from the group consisting of NH, N—R8 and CR1R2, wherein R8 is a halogen;
- R1 and R2, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R1 and R2 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- Q is a member selected from the group consisting of C(O), NH, N—R9 and CR3R4, wherein R9 is a halogen;
- R3 and R4, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl.
- or, R3 and R4 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- X is a member selected from the group consisting of C(O), C(O)—NR5 and CR6R7, wherein R5 is a member selected from the group consisting of hydrogen, halogen, optionally substituted (C2-C6)alkenyl and optionally substituted (C1-C6)alkyl;
- R6 and R7, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R6 and R7 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- and
- Z is a member selected from the group consisting of optionally substituted (C1-C3)alkylene, C(O), or a single bond,
- with a vinyl monomer in a reaction mixture thereby making said polymer.
12 more elements
A method for chemically modifying a polymer, said method comprising:
- admixing said polymer in a reaction mixture with a compound having the formula:
- 18
- wherein:
- A is a member selected from the group consisting of NH, N—R8 and CR1R2, wherein R8 is a halogen;
- R1 and R2, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R1 and R2 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- Q is a member selected from the group consisting of C(O), NH, N—R9 and CR3R4, wherein R9 is a halogen;
- R3 and R4, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R3 and R4 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- X is a member selected from the group consisting of C(O), C(O)—NR5 and CR6R7, wherein R5 is a member selected from the group consisting of hydrogen, halogen, optionally substituted (C2-C6)alkenyl and optionally substituted (C1-C6)alkyl;
- R6 and R7, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R6 and R7 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- and
- Z is a member selected from the group consisting of optionally substituted (C1-C3)alkylene, C(O), or a single bond,
- with a vinyl monomer thereby chemically modifying said polymer.
12 more elements
A polymer comprising a monomeric unit having the formula:
- 19
- wherein:
- A is a member selected from the group consisting of NH, N—R8 and CR1R2, wherein R8 is a halogen;
- R1 and R2, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R1 and R2 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- Q is a member selected from the group consisting of C(O), NH, N—R9 and CR3R4, wherein R9 is a halogen;
- R3 and R4, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R3 and R4 and the carbon to which they are bound, join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring.
- X is a member selected from the group consisting of C(O)—NR10 and CR6R7, wherein R10 is a member selected from the group consisting of hydrogen, halogen, optionally substituted (C2-C6)alkenyl and optionally substituted (C1-C6)alkyl;
- R6 and R7, are each independently selected from the group consisting of optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted cycloalkyl, optionally substituted (C1-C6)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
- or, R6 and R7 and the carbon to which they are bound join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;
- Z is a member selected from the group consisting of optionally substituted (C1-C3)alkylene, C(O), or a single bond;
- and
- n is an integer from 1 to 250 inclusive.
11 more elements
Dependencies are inferred from the claim text.