Antimicrobial polysiloxane materials containing metal species

• US 8,709,394 B2
• Filed: 03/25/2010
• Issued: 04/29/2014
• Est. Priority Date: 09/28/2007
• Status: Active Grant

• Current Assignee: Ndsu-Research Foundation
• Original Assignee: Ndsu-Research Foundation
• Inventors: Chisholm, Bret Ja, Majumdar, Partha
• Primary Examiner(s): DICKINSON, PAUL W
• Application Number:
  US12/661,902
• Publication Number:
  US 20110236343A1
• Time in Patent Office: 1,496 Days
• Field of Search: None
• US Class Current: 424/78.08
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/04 Dispersions, emulsions, suspoemulsions, suspension concentrates or gels foams A01N25/16
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 25/28 Microcapsules or nanocapsules
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: A01N 55/00 Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing organo-phosphorus compounds A01N57/00
• CPC Class Codes: A01N 59/16 Heavy metals; Compounds thereof

Abstract

Polysiloxane-based materials, which include metal species, are provided. The polysiloxane-based compositions and materials generally include (i) amino-functional polysiloxane material and (ii) a plurality of metal species distributed within the polymeric material. Polymer based compositions in which the amino-functional polysiloxane material includes quaternary ammonium groups, e.g., tetraalkyl ammonium groups, are examples of suitable materials which may be used to form the present compositions. The metal species, which may be in an oxidized and/or neutral state, may be bonded, coordinated, chelated, suspended, and/or dispersed within the polymeric material.

Claims

1. An antimicrobial polymer-based composition comprising:

(A) quaternary amino functionalized cross-linked polysiloxane; and

(B) an antimicrobially-effective amount of metal species distributed within the crosslinked polysiloxane;

wherein the quaternary amino functionalized cross-linked polysiloxane has a structure corresponding to a reaction product of reactants consisting essentially of

alkoxysilyl functionalized quaternary amine and tetra-functional silane and/or trifunctional silane; and

silanol terminated polysiloxane having a molecular weight of about 10,000 to 75,000;

where the alkoxysilyl functionalized quaternary amine is represented the formula

trimethoxysilyl-R′

—

N⁺R₁R₂R X⁻

in which R′

is ethylene and/or propylene, R₁ and R₂ are methyl, benzyl and/or ethyl, X is chloride and/or bromide, and R is an n-alkyl group having 12 to 20 carbon atoms; and

the silanol terminated polysiloxane is represented by the formula

2. The polymer-based composition of claim 1, further comprising a plurality of metal species distributed within the crosslinked polysiloxane, wherein the metal species include silver, zinc, cadmium, mercury, antimony, gold, aluminum, copper, platinum, titanium, or palladium species, or a combination thereof.

3. The polymer-based composition of claim 1, further comprising an antimicrobial agent selected from chlorohexidine, triclosan, gramicidin, levofloxacin, polymixin, norfloxacin, sulfamylon, polyhexamethylene biguanide, alexidine, minocycline, iodine, benzalkonium chloride, or rifampicin, or a combination thereof.

18. The polymer-based composition of claim 1, wherein

the silanol terminated polysiloxane comprises silanol terminated polydimethylsiloxane and

the reactants contain at least 0.015 moles of the alkoxysilyl functionalized quaternary amine per 100 gm of the silanol terminated polysiloxane.

19. The polymer-based composition of claim 18, wherein the trialkoxysilyl functionalized quaternary amine includes a quaternary N—

(C₁₆-C₂₀)-n-alkyl-N,N-dimethylamino group; and

the composition is formed by treating the quaternary amino functionalized cross-linked polysiloxane with a solution of a soluble silver salt such that the polymer-based composition contains about 0.05 to about 0.2 wt. % of a cationic silver species.

4. An antimicrobial polymer-based composition comprising:

(A) quaternary amino functionalized cross-linked polysiloxane; and

(B) an antimicrobially-effective amount of silver species distributed within the polysiloxane;

wherein the quaternary amino functionalized cross-linked polysiloxane has a structure corresponding to a reaction product of reactants consisting essentially of

alkoxysilyl functionalized quaternary amine and tetra-functional silane and/or trifunctional silane; and

silanol terminated polysiloxane having a molecular weight of about 10,000 to 75,000;

wherein the alkoxysilyl functionalized quaternary amine is represented by the formula

trimethoxysilyl-R′

—

N⁺R₁R₂R X⁻

in which R′

is ethylene and/or propylene, R₁ and R are methyl, benzyl and/or ethyl, X is chloride and/or bromide, and R is an n-alkyl group having 12 to 20 carbon atoms; and

the silanol terminated polysiloxane is represented by the formula

5. The polymer-based composition of claim 4, wherein the silver species include silver(I) ions.

6. The polymer-based composition of claim 4 wherein the silver species include silver nanoparticles.

7. The polymer-based composition of claim 4, comprising an antimicrobially-effective amount of the silver species.

8. The polymer-based composition of claim 7, wherein the silver species are in releasable form.

9. The polymer-based composition of claim 7, further comprising a second antimicrobial agent.

10. The polymer-based composition of claim 9, wherein the second antimicrobial agent comprises chlorhexidine, triclosan, gramicidin, polymixin, norfloxacin, sulfamylon, polyhexamethylene biguanide, alexidine, levofloxacin, minocycline, iodine, benzalkonium chloride, rifampicin, or a combination thereof.

11. The polymer-based composition of claim 4, further comprising an antifungal agent.

12. The polymer-based composition of claim 4, wherein the silver species are distributed throughout the polysiloxane.

13. The polymer-based composition of claim 4, wherein the quaternary amino functionalized cross-linked polysiloxane comprises a quaternary ammonium salt of a polyamine cross-linked polysiloxane.

14. The polymer-based composition of claim 4, wherein the quaternary amino functionalized cross-linked polysiloxane is a reaction product of reactants which include alkoxysilyl functionalized quaternary amine and silanol terminated polysiloxane;

and the silver species include silver nanoparticles.

15. The polymer-based composition of claim 14, further comprising a second antimicrobial agent.

16. The polymer-based composition of claim 4, wherein the silver species include silver nanoparticles.

17. The polymer-based composition of claim 4, wherein the composition further comprises a plurality of additional metal species distributed within the crosslinked polysiloxane, wherein the additional metal species include zinc, cadmium, mercury, antimony, gold, aluminum, copper, platinum, titanium or palladium species, or a combination thereof.