Anti-microbial polymer incorporating a quaternary ammonium group

a technology of quaternary ammonium and polymer, applied in the field of anti-microbial polymers and polymer composites, can solve the problems of adverse effects on human health, the environment or the intended application and material performance, and achieve the effects of preventing the addition of biocidal agents, preventing the decay of containers, and preventing decay

Inactive Publication Date: 2021-08-26
CHEMGREEN INNOVATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present patent is about creating new anti-microbial polymers that can be used to make medical devices and other objects with a reduced risk of microbial infection. The polymers have a repeating unit that contains a cyclic moiety that forms part of the polymer backbone and also contains an anti-microbial moiety. These polymers can be used to coat medical devices or make them from scratch, providing a safer alternative to traditional materials. The anti-microbial activity of the polymers is achieved through the use of quaternary aromatic ammonium salts, quaternary cyclic aromatic ammonium salts, or quinone or quinone derivatives.

Problems solved by technology

In both instances the antimicrobial compounds leach out over time, depleting the effectiveness of the material, and in the case of toxic biocides can lead to adverse outcomes for human health, the environment or the intended application and material performance.

Method used

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  • Anti-microbial polymer incorporating a quaternary ammonium group
  • Anti-microbial polymer incorporating a quaternary ammonium group
  • Anti-microbial polymer incorporating a quaternary ammonium group

Examples

Experimental program
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example 1

on of Anti-Microbial Polymer Using Acrylic Acid and Benzyldimethyltetradecylammonium Chloride

[0171]In a three neck flask, 8 ml of Acrylic Acid (PAA) and 12 g of Benzyldimethyltetradecylammonium chloride (Bz) were mixed under magnetic stirring and gentle heating (less than 60° C.) until the Bz was completely dissolved in AA. The mixture was then heated to 60° C. and the heat was turned off, but magnetic stirring continued. 0.5 g of the initiator 2,2′-Azobis(2-methylpropionitrile) (AIBN) was immediately added to the reaction mixture and the polymerization was initiated. The resulting reaction is schematically depicted below in Scheme I below, showing the reaction and product of the PAA-BZ polymerization, where m, n and p may be equal or an integer between 1 and 1,000,000 and R represents a long alkyl chain, in this particular reaction R is a C14H29 alkyl chain. As the reaction is exothermic, the temperature of the mixture continued to rise until the reaction was complete and only soli...

example 2

on of Anti-Microbial Polymer Using Acrylic Acid and Benzyldimethyltetradecylammonium Chloride and Cellulose

[0172]In a three neck flask, 8 ml of Acrylic Acid (PAA) and 12 g of Benzyldimethyltetradecylammonium chloride (BZ) and 0.03 g cellulose (CELL) were mixed under magnetic stirring and gentle heating (less than 60° C.) until the BZ was completely dissolved in AA. The mixture was then heated to 60° C. and the heat was turned off, but magnetic stirring continues. 0.5 g of the initiator 2,2′-Azobis(2-methylpropionitrile) (AIBN) was immediately added to the reaction mixture and the polymerization was initiated. As the reaction is exothermic, the temperature of the mixture continued to rise until the reaction was complete and only solid polymer remains. Alternatively the reaction can also be performed wherein the AIBN is added to the initial mixture of CELL, BZ and PAA, and once BZ and AIBN are completely dissolved into the AA, the solution can be heated to 60° C. to initiate the polym...

example 3

on of Anti-Microbial Polymer Composed of Sodium Acrylate and Benzyldimethyltetradecylammonium Chloride

[0174]PAA-BZ as previously synthesized was dissolved in water at a high concentration (0.22 g / ml). A solution of 6M sodium hydroxide (NaOH) was then slowly added drop wise into the dissolved solution of PAA-BZ forming a solid polymeric precipitate, which is the Sodium polyacrylate form (NAPAA) of the PAA-BZ polymer to form NAPAA-BZ. This precipitate was characterized by FTIR (FIG. 6). The polymer was then dissolved in Dimethylformamide (DMF) and a UV / Vis spectrum of the sample was taken (FIG. 7). The proposed reaction scheme of the product is similar to that of PAA-BZ with the final product being depicted below in Scheme III, showing the reaction product of the PAA-BZ+NaOH to form NAPAA-BZ, where m, n and p may be equal or an integer between 1 and 1,000,000 and R represents a long alkyl chain, in this particular reaction R is a C14H29 alkyl chain. This salt form of the product can a...

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Abstract

The present disclosure relates to anti-microbial polymers comprising a polymerizable cyclic moiety which forms part of the backbone of the polymer.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]The present application is a divisional application of U.S. patent application Ser. No. 14 / 418,549 filed on Jan. 30, 2015, which claims priority from PCT / CA2014 / 000505 filed on Jun. 18, 2014 which claims the benefit of priority from U.S. provisional application No. 61 / 836,360 filed on Jun. 18, 2013, the contents of which are incorporated herein by reference in their entirety.FIELD[0002]The present disclosure relates to anti-microbial polymers and polymer composites comprising a polymerizable cyclic moiety which forms part of the backbone of the polymer.INTRODUCTION[0003]Antimicrobial compounds and materials are chemicals capable of reducing or inhibiting the growth and development of microbial organisms such as fungi and bacteria. Such compounds play an important role in a variety of applications and fields including human health, by helping the prevention and treatment of microorganism linked diseases, fish and animal farming, preventing...

Claims

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Application Information

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Patent Type & AuthorityApplications(United States)
IPC IPC(8): A01N33/12A61L31/10A01N43/90A61L27/34A61Q17/00A61K8/81D21H21/36A61L31/16A61L29/16D21H17/45A61Q19/10A61K8/02A61L27/54A61L29/08C08F232/00C08F32/02C08F32/00A01N37/44A01N43/40B65D65/42B65D81/24C08G73/02C08G73/06
CPCA01N33/12A01N43/48A01N43/90A61L27/34A61Q17/005A61K8/817D21H21/36A61L31/16A61L29/16D21H17/45A61Q19/10A61K8/0208A61L27/54A61L29/085C08F232/00C08F32/02C08F32/00A01N37/44A01N43/40B65D65/42B65D81/24C08G73/026C08G73/0627A61L2300/208A61L2300/404A61L31/10A01N43/38A01N43/46A01N43/42A01N43/50
InventorGHANDI, KHASHAYARMAHIMWALLA, ZAHID SHABBIRBAERLOCHER, FELIX
OwnerCHEMGREEN INNOVATION